Jack and Jill

by Vickie Tern

 

CHAPTER FOUR

I started walking to the corner and then back, more or less the way Jill had suggested, trying to think this through. There I was, finally on the street dressed like a woman, in full makeup, no place to hide from anyone who might recognize me, and my heels were clicking on the sidewalk and I wasn't even aware of it. It no longer seemed so important, and I didn't feel at all feminine anyhow. If I were to meet some neighbor walking his dog before I got to the corner and turned back, I realized that I'd just nod and pass by. This was not good. I shortened my stride and tucked my elbows in and waggled my hips a little—that ought to remove any suspicions I thought. In the dark who could recognize me anyhow?

It began to be obvious that she had planned this whole evening for her own amusement. It was revenge for my affair with Darlene. She knew that right now I'd be thinking exactly what I was thinking, that there was nothing for me to do but grit my teeth, make no fuss, follow her plan, re-enter the house, and make ladylike conversation with her and her lover, all the while pretending I knew nothing about their relationship, and seething inside.

No, I then realized, I'm wrong. She doesn't know I know anything. She doesn't know that I saw them together at the front door. I was supposed to be out the back door and half a block away. They were not going to signal anything to me about their real relationship, I realized. She's doing this to get even, for her own private amusement, and maybe his too. I'm supposed to come back into the house and have a friendly dinner the way she set it up, acting like an old girlfriend of hers helping her entertain a single guy from work. And I'm supposed to be as convincing as possible because I'm already a husband worried that he might try to come on to me, and ready to blame only myself if he catches on that I'm a man in drag. That's the scenario.

But does he know about me? Maybe she told him that her husband was going to show up in a dress, and that he should try to keep a straight face and play along, helping her to humiliate me and watching me humiliate myself? No, I decided, she's devious, but she wouldn't trust anyone else to carry on this kind of deception. She's got special reason to want to get even with me, and that's why she's doing this. But he doesn't have any special reasons. He might even be feeling a little guilty he's carrying on with a married woman. She couldn't be sure that he'd play along convincingly.

I arrived at our front door ready to play along and I rang the doorbell. I heard the chimes sound inside the house. Funny, I thought, in all these years I've never rung this doorbell.

The door opened, and Jill delivered yet another surprise to me, in a way a kind of death blow. "Jane!" she said with enormous warmth and enthusiasm. "Come in, come in at once. Here, let me take your coat. That's fine, you can leave your purse over there in the hallway, noone will bother it. Now come in and meet Tom." I was a little taken aback—she was being much too effusive. A tall, thin, gentle and capable-looking man with hair just starting to gray was standing just inside, looking at me with a mildly friendly smile, one hand in his pocket and the other reaching toward me, strangely at his ease in my house.

"Jane, this is Tom. I've told you so much about him I'm sure you feel you've known him for a long time. Tom, this is Jane, my best friend. I'm so glad that you two finally have a chance to meet each other. The two people I care most about in the world."

She smiled a beaming welcome at me, and looked up at Tom, and her eyes actually nearly misted over when she made that last statement.

I was flabbergasted. But there was more. She turned to Tom. "When Jack died last year," she told him, "in that awful car crash, I don't know what I would have done without Jane. She was with me night and day until I got over the worst of it." She went to Tom's side and then turned toward me again, still grinning broadly, and put her arm around Tom's waist. He in turn reached his long arm over her shoulder and gave her a hug, then touched his lips to her hair. He turned back toward me, still with that relaxed smile, his possession of her complete. She acknowledged it by placing her hand over his, still on her shoulder. "But I did get over it finally," Jill said,"and I'm so grateful to you, Jane, for being a true friend during that difficult time. Now that I have Tom," she turned to look up at him, and he bent down and kissed her, and she turned back toward me, "I hope you know I still treasure you as the dearest of my friends."

She may have meant it. There I was. Dead, replaced by another man, but acceptable to Jill as a woman, as her girlfriend, because the man I once was was dead. I felt a flutter in my stomach—for years I had wanted her to think of me as a girlfriend, the way Doreen did without thinking about it at all. Now, it seems, that's what we are. Is she also telling me in her bizarre way that that's all we can be? "Can I sit down for a moment?" I asked her in a low voice.

"Come into the living room Jane, dear, please," Jill said to me. "Tom, do get Jane a drink—bourbon on rocks isn't it dear—while she has a chance to catch her breath." Tom went over to the glasses and bottles I'd set out not fifteen minutes earlier, and Jill turned and fired off at me point blank the most delighted, devastating smile I have ever seen. Her eyes crinkled and gleamed, and her mouth stretched across her face and her lips parted joyously, the same brilliant scarlet as her blouse. I near-collapsed into an easy chair, and she said with great concern, "You don't look well dear. Is anything wrong?" Then with Tom out of the room, she threw back her head and started laughing uncontrollably.

Tom came back with my drink and looked puzzled at my wife—my former wife it now seemed, at least as he saw it, that is, my widow. She saw his raised eyebrow. "I'm sorry dear, but Jane is in such a funny predicament, she tells me. It's a little hard to explain." She started giggling again, then tried to smother it. Her shoulders shaking, she choked out "Maybe....some...day I can tell you dear." I knocked back the bourbon in two swallows, Tom took my glass, and with his face impassive returned to me with the glass refilled to the top. Jill turned away. "I'd better see to dinner," she said, and in a minute, from the kitchen two rooms away, I heard yet another explosive guffaw. "We're ready!" she called out. I drained the second glass, stood with a slight teeter on my heels, Tom took my elbow, and we went into the dining room.

Dinner conversation was a little odd. I was angry with Jill, feeling set up and trapped all these weeks, even though I guess I deserved it. In a way I had asked for it. I was jealous of Tom, with his easy appropriations of my rights in the house, and my privileges with Jill. And I was embarrassed for myself, fearful that I'd make some odd move to raise Tom's suspicions. Jill meanwhile maintained her displays of intimate affection with Tom, touching him, gently squeezing his arm when she wanted to make a point, glancing at him I thought adoringly. It was all very depressing. Tom kept refilling my wine glass, and I kept sipping from it without noticing how much.

But Jill reminded me to count one of my blessings, the one that had gotten us here to begin with. I was out as a woman, and passing in front of a stranger. "What a lovely skirt Jane," Jill said as we sat down. "I remember you'd said you were looking for an occasion to wear it. How nice that you're wearing it here, tonight! I'm so pleased!"

I knew what she meant, and tried to feel grateful to her, and tried to think of something to say that didn't sound stupid and wouldn't give me away. "Thank you" was all I came up with.

But she wouldn't let go. "And that green print blouse goes so well with it. You look just lovely!" She turned to Tom. "Jane hasn't been going out much since her divorce...is it two years ago now?" I nodded.

We worked our way through a platter of hor doeuvres, and then some kind of beef on noodles. I kept my voice up in femme range, and answered whenever I had to in monosyllables. Then to keep from seeming utterly grouchy I smiled a lot. At Jill. At Tom. At any request to pass the salt, or the salad. Tom asked me if I meant to remarry, or was seeing anyone, and other questions like that, making the kind of polite conversation people make when they are being hospitable. I told him I didn't know, or wasn't sure, no matter what he asked me. I didn't. I wasn't.

I wasn't even sure I'd seen everything Jill had in store for me this evening. This seemed an elaborate way for Jill to announce to me that she was now having an affair, and to gloat over it. Every time she kissed him, or leaned over him, she was telling me she didn't need me for love and affection. Ok, I heard her. But why all the preparation, these different stories, her seeming to please me by planning a dinner for me to come in in drag, then showing me her lover when I couldn't do anything about it. It all sounded like simple spite, and Jill could be spiteful, but far more than spiteful she was devious. There was something else.

What else there was turned up as she cleared the plates and readied the table for dessert. "Well," she said, turning toward me, and speaking in the most gentle, earnest tones I had ever heard from her, "Jane, I've talked to Tom about it. He's willing. In fact, he'd love to do it."

"What?" I asked. "Do what?"

"Oh, Jane, I'm so filled with this little surprise gift for you that I'm not telling it to you properly. You remember when we were so tipsy together a few weeks ago, and we were telling each other our most intimate secrets about our husbands, our former husbands, what they liked to do with us, and what we liked doing with them, wonderful things and silly things?"

Tom refilled my wine glass, and then his own. The world was starting to swim a little, but I kept my head very still, and it stopped moving. "Tipsy?" I asked. "What?"

I had drunk enough so that my voice suddenly cracked out of its customary high femme mode, where I was trying to keep it, into pure falsetto. I had better watch it, I thought.

"You know," she said, smiling encouragingly, as if I already knew where she was leading this conversation "What you told me you missed most about having a man in your bedroom, since your divorce." She paused, as if waiting for me to reply.

I tried to fill the silence. "You mean snoring?" I couldn't think of anything else to say.

She smiled indulgently. "No, not snoring Jane. Much more intimate." She grinned. "Sexier." She looked at me intently. Then she let her eyes drift down, until she seemed demure, even too shy to go on. What a woman!

"This is so embarrassing for me to talk about, dear, because I've never done it myself, and don't know that I'd want to. I don't think its my kind of thing. But you remember, when we were talking together and feeling especially close, and you spoke of it so wistfully, with such tenderness, with such longing, and such eagerness, that my heart just went out to you. I thought, how can I help my dearest friend Jane in some way, and somehow thank her for all the loving care she's given me? How can I give you the greatest gift you desire? And then I thought of Tom." Jill looked at Tom devotedly. "And I asked Tom, and he thought it a strange request at first. He didn't want to at first. But finally he agreed. For me. But above all for you." She leaned over to kiss him, yet again.

Tom broke in, as if he had to reassure me of something. "It's not something Jill and I ever do with each other," he explained, "So it's not a kind of intrusion into our relationship," he commented. "It's quite apart from us. Except," and he looked fondly at Jill, "Jill asked me to, and I want her to be happy."

I couldn't make any sense of this conversation, but I decided not to force it. Maybe it was the wine. "Oh," I replied.

"Don't worry, Jane," Tom said. He now spoke with the same gentle, concerned voice Ellyn was using "I understand how some things are hard to talk about. You don't have to say anything at all if you don't want to."

I held my head very still to hold the room still.

"Tom, you said you'd help Jane past any shyness she might feel. I hope you will," Jill said to him, taking his hand and giving it a tight squeeze. "Now I'm going into the kitchen, to clean up everything, and I have a wonderful dessert to prepare. It'll take maybe a half hour, longer if it needs to. You two go into the living room. I promise I won't peek."

I was getting a funny feeling about all this, but I kept quiet. Maybe it was the wine.

"Jane," Jill said, leaning earnestly over me, "You remember when we were talking about losing our husbands, what we most missed ? You said it wasn't sleeping with him that made you feel most like a woman. It was something else. It was something you did with him you'd never done for anyone else. You said it was so satisfying you wished you'd started when you were still a teenager and all the boys wanted you to do it. You were so ashamed to say it. But finally you did say it! You said you couldn't get enough of it! And I've remembered that you said it, because you were so sweet to me in those months when I found I had to live alone, and life seemed so unbearable!"

Jill smiled as if through tears. I stared back, trying to look as if I understood her. "Well, Tom is yours for the next half hour or so, and I want you to do what you said you most loved to do with your husband. Don't think about me at all." Her voice then took on an edge. "And don't disappoint me, or I just don't know what I'll do." I could tell from her tone she know precisely what she would do. I had no option. Then she came out with it.

"You go into the living room and enjoy Tom's cock with your mouth. Suck on it to your heart's content. I want you to. Really. And I want you to enjoy the taste of his cum. I remember how you especially talked about the peculiar, delicate, complicated taste and feel of a man's cum, sweet yet salty, creamy yet winey, and how you missed it." Jill giggled. "We were so silly that night. And you talked about the feeling of control you had over your man, when he was helpless with desire for you to lick him and throat him, and how when he was in your mouth you could bring him anywhere you wanted. About how you missed that feeling."

And Jill then looked me straight in the eye. "Jane," she said, obviously enjoying each word, "This is your big moment. Tom is yours for a half hour, or more if you'd like, as my gift to you. Please take him as a token of what I think of you. Tonight I want you to have your deepest heart's desire. Be all the woman you can be! Suck Tom off! For me!" And she went through the kitchen door and closed it behind her.

I stood up, and the walls really did swim. Holding onto the edge of the table as far as I could, I went into the living room. There was Tom already, seated in our big, overstuffed easy chair, legs apart, smiling to encourage me, both hands outstretched toward mine in reassurance. How could I get out of this? I thought of running outside, or upstairs. I thought wildly of claiming I was having a period. Did Jill think I was going to give Tom a blow job and enjoy it? No, not enjoy it. That's the point! I had to pretend to enjoy it while feeling trapped and demeaned, doing something she herself never did with me, nor it seems with Tom either.

And I couldn't make a fuss about it. Not without giving myself away. I was a little drunk, but that was clear enough. Which would be more humiliating to me? Confessing to Tom that I'm Jill's husband in drag, and trying to order him out of the house? Or staying and sucking his cock? Which would cost me more? Which was easier? My thinking was as blurry as my vision, but it was clear to me which would cost me my wife. I still wanted her back. I had promised her I'd do anything she suggested. This was her revenge, one more ordeal she had schemed for me because of Darlene. I would somehow get through it.

I took hold of the soft arms of the chair, one on either side of him, and leaned on them, and lurched to my knees between his knees. In a single swift motion Tom undid his buckle and pants, unzipped his fly, slipped his pants and underwear out from under him and down to his ankles, gently put his hands on either side of my head, and pulled my face toward his crotch. His cock rose up toward me as I approached, still tipsy and fascinated and horrified, unable to do anything about it. The thing wasn't that impressive in size, but respectable. To me at that moment it looked like the Eiffel Tower. "Jane honey," he said, "Jill tells me it's been a while since you've done a man, so take your time. I'll help you." He leaned back. "Just put your hands under my balls and cup them gently, Then kiss the tip of my prick, right where you see that little drop of clear fluid. Lick it with your tongue. That's it. What does it taste like?"

I thought, here goes nothing, and leaned forward, and touched my tongue to the tip of his penis, where he had directed me. "A little salty," I said, not wanting to say more, wondering if I was going to retch if I said more.

"That's it," he said, "Think about each taste, each feeling, so you'll remember. If you pay close enough attention to everything, your mouth will remember. And I want your mouth to remember. Now, just open up, and form an "O" with your lips, and slide it over the pinky-purple head of my cock. It feels silky, doesn't it. That's it. Lift your head up and tell me how it feels."

"Silky," I said. I was trying not to notice, to close off my mind, to put my attention somewhere else.

"Yes," he said. Now slide your "O" mouth down onto my cock head again, this time a little further, until you can feel the soft ridge it ends in, all around. Do you feel it? Clamp down a little just below the ridge with your lips."

I did as he asked. I felt the ridge with the moist inside of my lips. I tried not to.

"Now open your jaw wide. Wider. We don't want your pretty teeth interfering with our pleasure, do we. But keep the "O" nice and tight below the ridge. Stay still a moment, and notice how it feels. Now pull back against the ridge slightly, then tuck your lips under it again."

I did that.

"Now slide your lips over the ridge by tightening your lip muscles on it a little bit, like kissing it all around with your mouth open. Ah, that's right. Let a little saliva lubricate everything. Lovely. Now very gently, make a slight suction with your mouth."

My wet lips slid a little bit down the shaft of his penis as the suction pulled him into my mouth. I noticed that his hands on my head kept up their gentle pressure, so I couldn't back off as the main part of his penis entered my mouth.

"Feels delicious, doesn't it. Slide your mouth up and tell me, but do it slowly, so the "O" stays snug, and when your lips reach the tip, kiss it. Aw, that's sweet. Kiss it again. Ah. You feel now that your lips are empty, don't you, and you want to refill them with something for your lips to squeeze. Is that right? Tell me I'm right, dear."

His hands twisted each side of my head gently, turning my face up toward his, and I saw he was looking mildly into my eyes, waiting for an answer. I looked back at him, still whirling a little—that wine. I couldn't look away. My mouth was still pursed from kissing his prick, and I could still feel the his cock-head ridge on my lips, and I could still sense his pre-cum in my nose when I exhaled. Would I ever be able to forget this?

"Oh, God!" I said.

"That's right," he replied. "It is heavenly, isn't it. If you'd like, lick me and kiss me anywhere you want. From the base to the tip. Underneath especially. Yes. Yes. That's right. Now make your little "O" again and wrap your mouth around me again, and pull me in. Only this time, deeper. I'm getting eager to fuck that dainty little mouth of yours. This time we'll go all the way. But don't worry, I'll tell you what to do. I'll remind you what to do."

Before my head went back down on him I started to say something, but it didn't get very far. I don't know what I would have said next anyhow. My head once again facing the tip of his cock, I made my "O" and opened my jaw just in time as he thrust it back in.

"That's it, dear. Suck. Slide. Again. If you need to come up for air every now and then, or to ease your jaw muscles, do. I'll feel your head pressing on my hands, and I'll ease off. Suck. But each time you leave my head behind, I want you to kiss the tip. Kiss it passionately. Devotedly. Lovingly. Try to stick your tongue into that little hole at the end. Slide. I want to feel you can't get enough of kissing me. I want you to know you can't get enough. I want your lips to feel they can't wrap tightly enough around me. I want you to slide me all the way into your mouth until my tip bumps on the back of your throat, on your gullet, and maybe slides down into your throat. Suck. Press your tongue flat against me and slide. Lick my head and down again. Ah. More. Suck. Again. Slide. Now. Again."

He kept pumping my head against his crotch, slowly and gently, and kept up his steady chatter, while I formed my "O" and held my jaws wide open and felt more and more of his meat fit into my mouth, and each plunge brought my nose closer to the base of his shaft, and sucked him in and slid him away. Now and then when I came up, my head would writhe on his tip as if it were the lips of the most gorgeous woman imaginable, my lips pressing on him and caressing him and my tongue flicking the delicate hole at the end until again I opened up wide and took him back into my mouth, and slid my lips down his shaft as far as I could reach, and pulsed them at the bottom. His hands held me and moved me, and his hips began bucking up toward me, and he was plainly getting hot. My nose was now getting down into his hairs, and his cockhead kept cramming against my throat then backing away, and I worried about gagging. I realized that at this angle there was no way I could bring him all the way in to relieve that pushing at the back of my neck, so I concentrated on bringing him off as soon as I could. He pumped me while I pumped him, and my lips compressed and pulled and puckered and tightened and loosened around the "O" they formed, and my tongue swiped his underside on my upswings, and danced over the helmet-shaped head. I realized irrelevantly that I couldn't have much lipstick left on, and I realized I should have hauled out a compact to repair my makeup after dinner. But I had got too drunk, and this had followed too soon.

I found that except for the back of my throat, it wasn't too bad. Some odd sensations, certainly very different. I took his advice and began paying attention to the alternating slippery, satiny, bumpy ride my lips were making. It was interesting, that sensation, and I did find I could enjoy my power over him when every now and then he moaned slightly, and I tried to make him moan again. If he's turned on because I seem to love this, I thought, I'm going to seem to love it like crazy, and we'll get it over with. I concentrated on satisfying him, and began to let my fingertips fly over his balls and squeeze them gently, and sometimes I let them caress the base of his cock. Every now and then I gave a kind of pathetic muffled cry deep in my throat, "Ohhh!", "Oooohhh!", as if I couldn't get enough. Suck, slide, suck, slide.

Suddenly he said,"Oh Jane, darling, I'm going to come. Hold me deep and start swallowing as fast as you can! Hold me! Deeper! Don't spill me. Don't let me spill on the chair, or the rug, or your blouse, or my pants, or AHH, AHH, AHHH, AHHH!" And hot cum splashed against the back of my throat with each pulsation. He shot his load into me, and I swallowed, and I held him sealed in my mouth and swallowed, and I reached into my throat with the back of my tongue and swallowed, and I rolled his thick liquid forward in my mouth and swallowed, and each time I thought it would overflow my mouth I swallowed. Meanwhile his hands crushed my face into his crotch, deep into its hairs, and he bucked against it, and I couldn't breath. His climax seemed interminable. He kept pulsing. My mouth filled with something sort of slick and creamy, a little like mucous, and a little salty, and a little bit sweet. Not too bad I thought, as he pulsed on and I kept swallowing. I'm surviving this, I said to myself. I leaned in and sucked the last of his cum out of him as if his prick were a straw.

He let go of my head, still breathing heavily. I looked up, and he grinned at me. I remembered that I was supposed to be passionate and conspiratorial and grateful about all this, and grinned back. Then I leaned back off my knees and sat down on the floor. For a moment I couldn't look at him. I kept working my tongue around my mouth and swallowing, trying to get the last squeezes of his cum off my teeth and out from the crevices of my cheeks, and off from where some of it had coated my lips. "You really do love that stuff," he said as he watched me licking my lips and working my mouth, his breathing almost back to normal. I didn't say anything. "Clean me up, dear," he said. "Lick me until you have it all." I got back on my knees and licked his prick, up and down and all over, then stood up.

"You know Jane, that was pretty good for a first time," he said. "You have a talent."

This stopped me for a moment. What did he mean by "first time"? What did he know about me? Was he in on Jill's plot after all? But as I got to my feet I decided he meant my first time with him, which would matter I suppose if the only blow jobs I'd ever given before were to my husband. I realized that this guy was something of an artist, the way he had talked me down onto him and through it. If I were gay, or a real woman, it really would have been enjoyable. "Thank you. It was very special!" I said with as much ardor as I could muster. What else could I say?

I thought I'd better say something more, so I added, as if we were now lovers of sorts, "But won't Jill feel jealous?" It suddenly flashed over me that I had just been blackmailed by my wife and raped by Tom, even though I'd brought it on myself. But I couldn't help it, and now I was trying to simulate post coital chit-chat. This was much too civilized. I tried to change the subject in my head, and began wondering what would get rid of his cum-flavor in my mouth. It really was rather creamy, and slick in texture. Gawd!

"No not at all," he said. "She isn't jealous at all. This is her gift to you. Jill doesn't do oral sex with me. Now vaginal sex, that's different." He smiled to himself, and I felt a sudden shock and jealousy—he had just admitted to me he was fucking her! Well, what else did I think they were doing? I decided to change the subject . He was right, of course. Jill had always been turned off by oral sex, and after a while I had reluctantly stopped raising the subject.

He pulled his pants back up and sauntered back into the dining room. I remembered that I must look a mess, and had better act as if I knew it, and headed for the bathroom, where I knew Jill kept a lipstick and hairbrush, maybe more. It took me ten minutes to get my face back to some semblance of order after that workout. Then still feeling a little frazzled, I headed back into the dining room.

Jill was already there, with our silver coffee pot, setting out bone china cups with an innocently pleased look on her face. "Oh, Jane," she said, "Here you are. You look like the cat that swallowed the canary. Are you still hungry for dessert?"

I decided not to answer her. Let her enjoy her triumph. She set before each place a desert dish full of a custard of some sort, with streaks on top. "See, I promised you a special treat tonight, didn't I?," she said. "I want you to feel pampered. I decided on this Creme dessert especially for you, when Tom said he'd help you feel like a woman. I just finished making it while you and Tom were enjoying yourselves in the living room. I thought you'd especially like the texture, a little sticky, and satiny smooth, and it fills your whole mouth." She paused, and then added, "Of course some people prefer it with a dash of salt, to remind them of times gone by. Would you?"

Then as an afterthought, as she started pouring the coffee, she said without looking up, "I've been planning this dinner for a long, long time, down to the last detail. It seems to be working out beautifully. I hope you're enjoying it. Because this isn't the end yet. There's more." She looked up at me, and her smile was blissful. What could I say? I'd promised her I'd go along with any of her plans for me. I had better be a good sport about it. She'd gotten me and gotten me good. I did wish she'd feel the score was even and settled, so we could be done now with these games.

No such luck. When we finished dessert and coffee Jill went over to Tom and pressed her cheek against his, while she cleared the last dishes. He seized her hand for a moment and then let it go. Things were now a little unpredictable. What next? Should I stay on, and wait until Tom had to leave, though obviously he wanted to stay? When he was gone, could I go upstairs and change into something more suitable, and assert my dignity, and have it out with Jill? Or was he planning to spend the night here, and waiting for me to leave? I noticed a stain on my blouse, and I realized it was a dab of his semen, still a little sticky. My mouth puckered slightly when I recognized it. Jesus!

But Jill settled the matter. Tom appeared in the doorway holding the topcoat Jill had given me, and Jill handed me the same purse she had handed me earlier when she pushed me out the back door. "Here you are dear. I'm sorry you have to leave so soon. I'll call you tomorrow. Or you can call me. I think you'll find everything you need in your purse; I tucked a few things there." And for the second time that night I was thrust out of my own house, this time through the front door. She slammed it closed.

I stood on the front steps, and I noticed that the porch light was still on, as if still lighting Tom's arrival and mine. I was wearing a skirt, and was visible to anyone. I glanced up and down the street. Noone. Then the porch light went off.

 

Jack and Jill

CHAPTER FIVE

Still standing by my front steps, near a dim street light, I opened my purse. There was the makeup I had used earlier. There was a folded piece of paper. There was a Motel key, with a huge weighted fob attached imprinted with a name and a room number. There was what I recognized as the spare set of car keys, with a small flashlight attached on a chain. There was a packet of condoms. There was a 3-pak of tampons. I opened the piece of paper. It was a note from Jill, typewritten, meaning that she written it some time before this whole awful evening had begun. When she wrote it she was already imagining me reading it right now. And now here I was.

"I want you to think about me and Tom here tonight, in our beautiful bed. Are you thinking about it, and about marital fidelity, and about being honest with each other, at this very moment? Good! If you want to resume our marriage, go to the motel room printed on the big key, and you'll find out what else I want. You'll be there for two nights. But you won't have to feel lonely. You'll find there's a beautiful blonde young man who hangs out with the night clerk and provides whatever services guests may require. He's very good, very gentle with first-timers, I've been told. He's very attentive. But I didn't arrange anything with him for you for tonight, so if you miss Tom's prick and want some more lovemaking before bedtime you'll have to talk to him yourself. Sleep well, dear."

I looked back at our house. A light in the bedroom had gone on. There was nothing more I could do.

So I went around in back, got in the car, and drove myself to the motel indicated on the key, not too far away. It felt odd driving the car in a dress, pressing on the accellerator and the brake in high heels, and I drove very carefully so there would be not the slightest risk of a policeman stopping me. When I had parked in the motel parking lot I sat still for a few minutes, to psych myself up to meet yet another stranger while dressed as a woman. Could I pass? I checked my hair and my makeup, and walked across the lot and into the lobby with what I hoped was a persuasive woman's walk, short steps, elbows in, mincing slightly. At the front desk a night clerk looked up at me without changing expression.

"Can you tell me where is Room 244. My wife made these arrangements." I realized that I had just blown my cover! He didn't blink, but merely checked his register.

"Yes. Room 244, prepaid for two nights. One flight up and to the left. The elevator is just behind you. Have you any luggage, ma'am?"

"No." I felt foolish standing there in a dress and I wanted to get out of the clerk's sight, so I hobbled down the corridor as I fast as I could, realizing that I'd been wearing heels for many hours now, and they were beginning to hurt. The clerk had confirmed what Jill's letter said, that I was here for "two nights." Why? So she could play house with Tom for the weekend? So I'd think that's what she's doing, whether she is or not? I felt a pang of jealousy. That's what she wants me to feel, I thought, but I owe her, so I have to pay her. At the same time I felt an odd twist of excitement at the thought of Jill and Tom romping together tonight, and all day tomorrow, and tomorrow night. It didn't seem like the same Jill. I wondered if she was more imaginative in her lovemaking with Tom than she'd been with me. During the past few months, I realized, she had changed from the girl I had married. She had always been assertive, but now she was domineering. And cunning! Tricking me into sucking Tom's cock! Does she just do straight screwing with Tom, then go to sleep? Does she let him know whether she enjoys it, or does she keep that a secret too? I suppose the two of them have a different kind of lovemaking, anyhow. Then I realized I was beginning to picture them wrapped around each other, arms and legs tangled together, and I realized I had better stop thinking about it.

I entered Room 244, and saw immediately someone had been there. The closet had clothing in it, women's clothing, a suit, a few dresses, a skirt and blouse or two, and a terrific-looking cocktail dress. I thought at first this was a hideaweay Jill kept for herself, but I looked again, and saw that everything was was in my sizes. In the bathroom was an elaborate makeup kit. I checked the drawers. One had a few bras and panties in it, again my sizes, and that one of the panties was crotchless, with ribbons to tie together the bottom seam. There were several magazines on the night stand, Cosmo and Vanity Fair I noticed, and when I looked for a Time Magazine or a Newsweek, I saw that another was Seventeen. Only girls' or women's magazines. Jill had thought of everything. I started to get undressed. It had been a long night since I had put on this very blouse and skirt, Jill urging me to look especially pretty for this guy she worked with, and me without a clue about what she really had in mind. He did come on to me after all, I realized, and I had made love to him after all. A long night. I set my slip aside to use as a nightgown, then saw that Jill had left a lovely, frilly nightgown across my pillow. For me. Well, that was something.

I didn't know how this room figured into her plans. Did Jill feel guilty about putting me out of my own home? I doubted it. Was she setting me up to live separate from her, with this clothing a kind of payoff she knew I'd like? No, she'd have told me about it beforehand. She always wanted me to understand clearly what her rules were, and why. I didn't know what I was doing here. Being out of her way while her boy friend fucks her, I supposed. The nightgown felt silky smooth as it slipped over my chest and hips. It had sexy lacework circling each breast. I looked at it in the mirror, and for the first time that night felt nice. I was pretty. I was myself. This was all too confusing. I turned out the light, and fell asleep at once.

I was awakened the next morning by the sound of a key jiggling in the door. Terrified, I called out "Who's there?" as I ducked under the covers to hide my nightgown's frilly shoulders. The door swung open, and a thin blonde young man entered with a rolling cart filled with a Room Service breakfast.

"I knocked, but noone answered," he said deferentially. "I hope you don't mind my using a key to come in, but that was listed as one of the things I could do during your stay. I'm pleased to make your acquaintance. I'm Carl."

"Let me see," he said, looking at a list on his clipboard. "Yes. 'Well, uh, Jane, if I may call you Jane. Your wife advises that you spend the day here. We have an excellent restaurant, and a pool area for swimming or sunbathing—you'll find a swimsuit and wraparound here in the room. If you need anything else, the pool shop will have something that would fit you. I'll be back tonight at around eight, to let you know about the wonderful things she has planned for this evening. Oh, yes. The hotel beauty salon has an appointment for you for this morning at 10:00 am. A complete makeover—expect to stay about three hours." As he opened the door to leave he gave me a warmly reassuring look, and then a charming smile. "Don't worry, Jane. Everything has been arranged and paid for. You don't have to do a thing. Just enjoy yourself."

He left. I noticed that while he was talking my nightgown's frilly sleeves had come fully visible to him. But it doesn't seem to have mattered, I thought, since he seems to be better briefed about me than I am. I was glad to have breakfast in the room, anyhow. It delayed the moment when I had to go out by daylight.

Then I thought, enough of this. I'll talk to Jill directly. I called home, and as the phone began ringing I suddenly wondered who would pick it up. Whose voice would I hear? After the third ring I heard Jill pick up and say "Yes, hello?".

I started speaking before she could decide to hang up. "Jill I want to come home. Is Tom still there?"

"Who?"

"Tom, your boyfriend."

"O yes, Tom, that was his name. No, he left early this morning; he had another woman to attend to."

"Your boyfriend?"

"But dear, he's not my boyfriend! I'm married. You remember."

"No? I saw you kissing. I saw the way you greeted him at the door."

"Oh, you did! I was so hoping you'd sneak around and catch that little drama! So that's why you lookled so strange when you came in and I began telling you the story of your death. Oh Jack dear, that was all a show for you. So was all that lovey dovey during dinner. All for you. No, Tom was my escort for the evening, and for other things. I hired him and told him what I was planning, and what I wanted him to do, and he did it all very well."

My head began to whirl again. I couldn't keep up with her. "Did he know about me? Did he know I wasn't your woman friend?" "

Her voice sounded marvelously good-natured. "Why darling, of course he knew about you. I told him you were a closet fairy. I told him that my husband would show up wearing a dress and pretend to be my best girlfriend, and that we should go along with it. I told him that all your life you have wanted to give a man a blow job while wearing a dress, because that's what real women do, but that you were too embarrassed to set it up for yourself. I told Tom it was your birthday and that he was my present to you, a real man you could suck on like a lollipop, to your heart's content. I told him you'd go down on him without any problem, and you certainly did my darling. And I told him he should help you with it, your very first time, without letting on that he knew you weren't just one more slut who blows cock every night.

"I knew you'd do anything to keep him from finding out you were just another pansy in a dress. I knew you'd go along with it no matter how humiliating." Her voice grew triumphant. "So sweetheart, I turned you into a pansy in a dress!"

I remembered how helpless I had felt as I sank down on my knees between his legs last night. For nothing! I felt mortified. Tears came into my eyes. She had set me up! From the very beginning! She had even advised me what blouse and skirt a well-dressed husband should wear to his first blow job. I tried to say "Very clever!" with acid irony, but all that came out of my mouth was a little strangled sound.

Jill continued. "But I was very considerate, dear. I told him that I wanted it to be wonderful for you, unforgettable, so that you would always remember it, your very first. I wanted him to teach you how to enjoy every moment. I told him I wanted your mouth to remember it even if you tried to forget it. And your mouth does remember now, doesn't it?" She paused, then she went on. "I could tell that your mouth was learning, love. I could see by the way your lips kept their sweet little pucker, their little cupid bow shape, and couldn't stop kissing the tip of his prick whenever you came up for air, and then how they made that pretty "O" whenever you went back down on him. You really do have a talent for it, love, don't you."

"You could see that?" I broke in, shocked. "You said you were in the kitchen."

"Oh, no! See that? Why love, I was there! There was no way I was going to miss the sight of my darling husband in a dress sucking cock like a ten dollar whore and pretending to like it. You were so busy head-fucking that man's dick you never noticed me! You must've really gotten into it! Was it that great? I took picture after picture of you slurping Tom's prick like a big purple ice cream cone! It looked really wonderful for you. So that's what you guys do when you get together! That's what male bonding is all about!"

She paused again. "When I heard him tell you how to feel every nuance of his prick in your mouth, he made it seem so attractive I thought of giving it another try myself. I told you on our honeymoon it just wasn't my thing, didn't I. Well, maybe I just never had as as good a teacher as you just had. You did so enjoy it! Dear heart, you make such a darling little cocksucker!"

Her affability faded. "And now, you're my darling little cocksucker, Jack dear. I have snapshots of you dressed up with Darlene, and dressed up with Jack, dressed up and going down on that stud, and now you little faggot I've got you where I want you." She stopped and caught her breath. "Not that I didn't before. I think we understand each other. Stay another night at that motel. It's all arranged and paid for. I need one more night by myself. Then you can come home and we'll see what we'll see. I think starting tomorrow we may be able to live together again darling. Maybe happily. Even joyously. On my terms. But not if you're still the way you are. If you'll do what I say, maybe. Spend the whole day being a woman, Jack. That's what you say you want and that's what I've arranged for you. I bought those bras and dresses for you, and made all of your appointments for today. You should feel grateful. Spend one more night. Otherwise don't come home at all, and I'll think about how I want to share the pleasures of my new photograph album."

The line went dead. I hung up at my end, and sat there a while. Then I picked up the copy of Vanity Fair. A gorgeous young woman looked back at me, smiling with approval and congratulating me on becoming a darling little cocksucker, maybe even as good with the guys as she was. The magazine cover promised an article inside on four new male film stars worth masturbating over, and another on how to keep your man by fucking his brains out. I wasn't ready for this. I picked up Cosmopolitan. A randy lady on the cover in an undersized red evening gown, her breasts and shoulders exposed wherever they bulged out from the material. Inside, three ways to apply the new Spring lipsticks, and advice for girls who like to seduce other girls, not men. I started trying to read about lipsticks, but couldn't find the article among all the ads.

So I read the ads. My spirits picked up a little. Today I would be Jill's kind of woman. She had bought me clothing to wear. I thought about Medea, the jilted woman of Greek mythology who poisoned her husband with an impregnated cloak. No, Jill wanted me to change, by spending the day dressed up. By going to the beauty parlor? There were worse things than trying to be one of those drop-dead beauties in the perfume ads. Well, she seemed to be meeting me half-way even while rejecting me. I got up and looked more closely at the clothes hanging in the closet.

First off, I would try to pass without attracting attention. There was a pair of stone-washed blue jeans, and a shirt. I took them down, checked the underwear drawer for a bra and plain pair of panties, and put everything on. So far, fine. Everything a little snug, but basic. They fit. The bra gave me a little bulge in the chest when I set my shoulders back, but nothing noticeable. The pants were very tight in my buttocks, but glimpsing the curves in the mirror, and the sharp separation of cheeks they gave to my ass, I thought, not too bad. A pair of flats on the closet floor I recognized as mine, and I put them on—no way they could be thought to be men's shoes, but I loved the way they curved on my instep. I went into the bathroom and shaved twice, then again, and started to think about how how much makeup I needed to get through the morning without seeming to be a man in women's clothes, when I suddenly realized it was ten minutes to ten. My first ever visit to a beauty salon as a woman! But of course they'd know at a glance that I was a man! But Jill had arranged it—of course they already knew. My heart began to pound. I picked up my purse, checked that I had my room key, headed out the door, and saw a sign pointing to the Salon off the pool patio at the end of the corridor. I walked as rapidly as I could, hoping noone would see me and wonder what I was. Noone did.

A woman in a pale purple smock looked up from arranging bottles on a work table when I came in. I glanced around—there was noone else there. "I'm Jane," I said, in what I hoped was a persuasively high voice. She looked at me without changing expression. I almost added "My wife made an appointment for me...," but I choked it off, and just looked back at her, thinking that maybe I could get away with this. "Yes," the woman said, "How are you, Jane? Your wife wasn't sure your hair would be long enough for a really feminine style, but I think we can manage. Sit over here, dear, and we'll think about you for a while." I sat down. "Tell me, something your wife couldn't answer for you. Will you want a hairdo you can just comb out each morning and forget about all day, or do you like to primp and shape it with rollers and mousse and curlers and things? Some women like to fuss, and some hate it. Which kind are you?"

I loved fussing, but there was no way I could say so. "Is there a style I can sometimes wear, uh, plain?" I asked, meaning one that could look like a man's cut but still look feminine when combed right.

"Well, yes, Jane, but not for you. Your face is too large for a gamin cut. You could look really lovely if you had masses of hair framing your whole head, but that needs longer hair than you've got, I think. Besides, my instructions are, make you look as pretty as you can be right now. I tell you what. Leave it to me. I think for now a curlytop barely covering your ears on the sides, high on top, with just a wisp of bangs, and you'll be just fine. Your earrings can just peek out. Not too hard to take care of, either. And as it grows out, it'll still look pretty. Different of course. But you can always have me do it again if you want to keep it the way it is. The way we're doing it now, I mean."

As she led me over to a sink, slipped a smock over me, and leaned me back for a shampoo, she asked "Tell me, honey, why is it you want to go all the way? I can understand a makeover for a costume party and then back to business as usual the next day, sometimes men come in for those, but your wife tells me you'll want to look feminine for the whole forseeable, no compromises, the more like a woman the better. She said she doesn't want anyone thinking you're anything else but, so you won't embarrass her when you're out together. Why is that? Did you lose a bet? Are you planning on an operation to change your sex? Or is she planning on being the one who wears the pants in the family?" She smiled at her little joke.

Well, there was news! That explained a lot about what was happening. Jill was willing to accept my dressing as a woman if there was no risk of embarrassment to her. I just had to do it better, "all the way." Not look like a man playing a role in drag, or a feminized man, but look like a real woman. For the first time that day I started to feel hopeful. Maybe our marriage would survive after all. Maybe it was worth my trying to help it survive. Jill had some kind of plan in mind, and if it allowed me to cross-dress at times I'd go along with it gladly. But "the whole foreseeable" wasn't "at times." "I think I may have won a bet," I replied. "But can I wear it sometimes to look like a man?"

"Well, yes, dear, but you'll look like a man with a lady's hair style if you try it. I mean to give you a perm, and some clusters of really cute curls. If you want, you can set them, and if you don't, you can reshape them with a little comb. I'll show you how. But even if you brush everything out straight, this hairdo won't be too easy to mistake for a man's."

I decided to deal with passing as a man another time. "Your name is Marianne?" I asked, reading off her name tag, trying to change the subject.

"Yep, Marianne. That's what it says, that's what it is, honey. Mari to my regulars. Are you saying you're going to be a regular from now on? Because with what we'll do with you today, you won't need to come in very often any more, or not for too long anyhow. Maybe a half-hour a week. Touch up, re-curling, fix your nails, change of color, little things like that. Maybe even every other week. Depends how perfect you want to look." She warmed to her topic. "You watch. Your wife is going to love this." She sat me back in her cutting chair, and pulled strands of my wet hair this way and that. "You know, you have real possibilities...."

Three hours later Mari had remade me. My hair was no longer a mousy dark brown but a gleam or so lighter, with a hint of blonde or reddish highlights, though still brown. It was no longer straight, turned under at the ends, but looked like a cap full of darling curls, with sweet little bangs coming down in front, and extending much further in back, so my nose no longer a little large, but just right. I was delighted with it when she took out the rollers and showed me how a touch of a comb here and there was all I'd need after sleeping on it, and how to reshape it into springy curls with just a brush and mousse after a shower, and so forth. In fact I was so pleased that I said "Now's fine," without thinking, then realized she had been saying that little studs would look much nicer than clipons until my hair grew out a little, and had just asked if she should do the piercing now or wait till next time. It was done before I could realize what I'd said. But my sudden worry when I saw little gold studs in my earlobes wasn't enough to break my cheerful mood. I really looked attractive! For me, anyhow.

My nails were deep pink, a shade she said would go with anything and never look trashy, though she told me I'd need a deeper red if I was planning to go out formal some time in a long gown. She laughed when she said this, and I asked her why. She replied that the thought of me in an evening gown had put in her mind an image of my wife in a tuxedo. She plucked my brows to their previous fine arch, darkened my lashes, and she put very light "daytime" makeup on my eyes and cheeks, hardly any. "You'll do," Mari finally said. I saw I was no smashing beauty, but as she looked me over Mari said she felt very good about me. So did I. My wife had tipped her heavily to make me look feminine, in no way a man, she told me. Now I not only looked no way a man, I looked like a very passable woman, pleasant to look at. "From the neck up," she added. I thanked her for the compliment, and could think of nothing more to say. She said she'd call me at home for another session in about two weeks' time. That sounded promising too. When I left the salon I felt better than I had in weeks, maybe even months, maybe even more.

Without a worry in the world I strolled down the pool patio toward the restaurant. Immediately I caught my reflection in a glass door, hunched over, defensive, and I realized that was how I had walked into the motel last night. So I paused, and took some deep breaths. I lifted my head high, straightened up, threw my shoulders as far back as I could get them, and was pleased to see two little bumps hinted under my shirt. Then when I next glimpsed my reflection I saw a cute looking woman with not much waistline and a kind of poodle cut and a bounce in her step. I had a cottage cheese salad for lunch, went back to my room to get my magazines, and had a new thought. For the first time I might be able to get away with wearing a swimsuit in public, without looking like a freak. I shaved all over again, but everywhere, my legs, chest, underarms, and arms, places I had learned not to look at when I was dressing for myself and my mirror. Then I put on the brand new one-piece bathing suit Jill had left in my room, looked at myself, took it off, and trimmed last night's bikini cutting on both sides of my pubic area. Then I put it back on. With its built-in padded bra I didn't need anything else. Even so, I slipped on the coverup and spent the afternoon at poolside reading beauty advertisments. Every now and then I got impatient with them, but even turning pages with my deep pink nails was a privilege, and I felt grateful for some reason. I needed to know what every girl knows about being attractive, alluring, ravishing, gorgeous, so I could try. Like every girl I would find my own compromises with these impossible ideals, my own style of femininity, a way to be poised, gracious, and beautiful in my own mind.

People came and went, and glanced at me, or looked casually while listening to someone talk to them, paying me no real attention at all. It was a warm afternoon, and I lay in the sun awhile, then fell asleep. When I awoke I was stretching luxuriously, like a huge cat. I realized why. The bathing suit pulled and stretched and shaped me in a way that would make any woman feel catlike when wearing it. It said as much on a tag still attached when I took it off its hangar. By the time I returned to my room it was 5:30. I ordered a sandwich from room service, and tried on the different dresses Jill had put in the closet. There was that darling cocktail dress, high-necked, black, subtly beaded, almost calling for those red nails Mari had mentioned. Whatever the evening activities Carl had mentioned, this would do. By 7:30 I was wearing it, had adjusted my makeup for the evening, and was back studying the magazine ads, waiting for Carl to show up with my schedule. I wondered if he was supposed to be my gentleman escort for the evening, and where he would take me, and whether there would be other women there to help me polish my movements and manners, to perfect my behavior the way Marianne had perfected my hair, face, and fingernails. Whatever lay in store, I intended to be a lady, and unashamed to be a lady. I wanted my wife to be proud of me.

 

Jack and Jill

by Vickie Tern

CHAPTER SIX

There came a knock on the door promptly at eight, and there was Carl. But he wasn't wearing his room sevice white jacket—instead he was wearing a casual shirt, slacks, and a light sport jacket, resort wear. As he came in he looked at me with an appreciative half-smile, and said "My but you look lovely. That dress is very becoming. I saw you lying by the pool this afternoon, and thought Mari had done wonderful things with you." He was carrying a clipboard, as earlier.

"Thank you," I replied, thinking that this was my first compliment from a gentleman, and thinking that if I weren't the lady of the house I would have felt an impulse to curtsy. "I think so too. But tell me, Carl, what's the schedule for me for this evening."

Carl smiled and looked into my eyes. "Me," he replied. His smile and his gaze remained fixed on me, unwavering.

"What's that?" I asked. I felt a twinge of fright. I suddenly remembered my wife's note from last night, when she was gloating over trapping me into sucking Tom's cock, and had told me if I wanted more before bedtime I should ask the blond young man. This one.

"No, you're mistaken," I said firmly. I realized I had just suddenly snapped into feeling and talking like a man, for the first time today. I felt a little silly to be doing it in a cocktail dress. But there was a lot at stake. I loved looking like a woman, but that didn't mean I wanted to be a woman. Not where sex is concerned. A heterosexual crossdresser is not a homosexual submissive! My body was my own! And so was my pride! "I have this note from my wife that says she made no arrangement with you. And I have no money."

Carl looked at his notepad, then turned over a few pages and smiled at me again. "No, Jane, my arrangement with your wife is quite clear. She told me to leave you alone last night, then to bring you breakfast this morning and to introduce myself. For tonight her instructions are, let me see." He glanced down the upper half of a sheet of paper, arrived at something further down, then read it aloud:

"Please see to it that by morning my husband feels like a woman in love, after a glorious night with you. I know you can do it. He's shy, and you may need to insist, and you can be as firm as you need to be. I hope he'll help, so you won't need to use force, or do any of those really punishing things you know how to do. Unless of course he wants you to."

Carl grinned up at me, then back down at Jill's instruction sheet. "Remember, he is still a virgin, as far as I know. He may let you be gentle with him, or he may not. But either way I want him to get the fucking of his life. No real damage to him, please. But if he can't sit for a week after you're finished with him, I'll understand. And months from now, if I see him smiling a secret smile and he won't tell me why, I'll know you've done for him everything I'd hoped. He wants to be a woman. Turn him into a woman. Give him the sexual experiences and reflexes and memories of a woman."

Carl read on silently a moment more, beamed at what I took to be some extravagant compliment, then looked up at me and put the note away. "An absolutely wonderful woman, your wife," he said to me. "To arrange a present like this! To arrange for you to live your deepest fantasies for a whole night! To change your very identity. And to keep it a secret until this very moment! You know, I'm quite expensive. She must love you very much."

I sat down on the edge of the bed in my cocktail dressed, stunned, all dressed up with no place to go. For some reason I felt demure at that moment, and I hated the feeling. It was so dependent, and helpless. Here I thought I knew what Jill had planned for me, and she had crossed me up again! Or rather, she was carrying out a plan of her own with a relentlessness I couldn't believe! She wanted me to submit to Carl, to be mortified, embarrassed, cheapened, and degraded by him. This was no path toward womanliness! This was pure and simple vengeance! For Darlene again. I couldn't believe it!

Carl looked at me, obviously pleased with himself, and eager to be of service. "Now," he said, "is there some special fantasy you'd like to perform with me, that you're a patient and I'm a doctor, or that you're a whore and I'm your best customer, or that you're a prisoner and I'm a prison guard, or that you're a schoolgirl and I'm a headmaster? Anything at all?"

"No," I said, "just that I'm Jill's husband, and you're the man she has hired to fuck me over."

"All right, Jane," he said. "Then let's begin. There's a beautiful peignoir in the closet. I think you saw it? And the sheer nightgown you were wearing this morning when I served you breakfast."

"Yes"

"And a makeup case in the bathroom, and more cosmetics in your purse?"

"Yes"

"A lovely word, 'yes.' It sounds so beautiful when you say it. I want you to put all those lovely things on and to make yourself especially beautiful for me. You will want me to be impressed by your efforts when I next see you. I assure you, you will. O yes, you'll also find some feminine douche kits in the medicine cabinet, and an enema kit. I want you to use them all on your pussy by the time I return, in that pretty virginal rosebud you have hidden between those gorgeous globes of your derriere. Use all of them, one after another. Clean yourself out throughly. Your first experience must be as memorable and beautiful as your wife wishes it. We musn't let anything stand in the way. Now, I've set aside a bottle of champagne for us, so we can toast everything that lies ahead of us tonight. I'll go now and get it. And I'll want to get some other things too."

He took my hand gently, and kissed it, and looked down on it as if the sight were too sweet to bear. Then with one hand he bent my fingers up, until the tendons stretched to the point of pain, and forced me to my knees. I looked up at him, a little alarmed. He looked back down with doting affection, but maintained his one-handed grip. "You're not going to be troublesome I know, because you'd only get hurt. You're going to do everything I ask. Don't worry. You'll love it. This is really a kind of honeymoon for you, and I will want you to remember it always, and to smile always whenever you remember."

I couldn't say anything. His grip on my hand was just this side of real pain, and it was obvious he wasn't exerting any pressure on me at all, yet.

"Now Jane, just three questions. Please answer each of them. It's true that your pussy is virginal? You'll cooperate with my efforts and your wife's desires for you? You expect to feel grateful to both of us afterward?"

"Yes," I said, "Yes, I will. Yes."

He stared at me, then smiled. "Good!" he said. "I won't be long, darling girl." And he was gone. The door closed.

I immediately thought about escape. But that would mean the end of my marriage, with no hope ever of a reconciliation. That was clear. Well, I thought, there is nothing for it. Jill wants to punish me, and she has found this bizarre way to do it. This guy is going to fuck me, with or without my consent, and she expects me to let him, and I have to go through with it or she won't take me back. This is sucking Tom's cock all over again, and more! But if I do go through with it, would she ever take me back anyhow? Why should she? How could she respect me as a man ever again? There'll only be my further degradation for her to mock me with. Or is she just asserting more control over me now? Is this some kind of kinky test of my obedience to her? But there has never been anything kinky about Jill. In fact, that's been one of her problems.

Then I thought. Obedience. That's an odd word for me to use. Love, honor, and obey. Maybe what she wants is for me to learn what it's like to be a married woman, since my wanting to look like a woman has so offended her, and in fact has gotten me where I am right now. Part of that is getting laid by a man. So she wants me to get laid. If I'm going to wear panties, then I should know what it's like to feel a prick in me. Then maybe, in her mind, I'd be less of a fake.

I thought some more. No, I suddenly realized. She wants more than that. She wants me to want to get laid. She has her own ideas about me. It isn't being like a woman she thinks I need to learn—she knows I've played at that all my life. And it isn't being made to do things women do, and gay men, like last night with Tom. That's just part of punishing me because she knows I don't want to have sex with other men. Not all young girls dream about sucking cock when they grow up. She doesn't suck cock herself, and she's a woman, at least she's never wanted to put her mouth on my cock, though maybe last night with Tom. No, she's devious. She wants more. She wants me to stop feeling ashamed to be seen dressing like a woman or behaving like a woman.

Good grief! She thinks that my feeling ashamed to be seen as a woman is unmanly! Only a wimp is ashamed of anything he wants to do. And to feel ashamed to be a woman is to insult all women! Does she want me to be a woman without apology? Yes. She expects me to want Carl to make love to me. And she wants me to want to make love to Carl. Her darling little cocksucker, she called me. She was mocking me then. But this is different.

I began to understand. She was mocking me because I felt humiliated when I had to suck on a cock, and she had set it up and rubbed it in. Now if I feel humiliated with Carl, she'd mock me again, and punish me even more. But I can escape her mockery by enduring whatever she dishes out without minding. Or I can escape mockery and punishment by wanting to do it, as if I were a real woman with real desires and a stud in her bed. Queers suck cock and take it in the ass and love it without feeling humiliated, because that's what they want to do. The same must be true for any woman, if she does what she wants to do. If I were the woman I claim I like to feel myself, sex with a man wouldn't feel humiliating. This isn't a punishment. In fact, it can be something beautiful.

So there's the answer. If I want to do it, then there's no humiliation. She wants me to want to do it. She's not punishing me with Carl, she's teaching me to be proud of my womanly desires, and to let Carl awaken them. She's even teaching me a kind of manhood. Real men are never ashamed of what they do. What did John Wayne say, "Never apologize, never look back." Of course the idea is disgusting.. A cock up my rear end! But I can do it. A man can be tough when he has to be. Tough enough to want to get reamed.

I decided I would submit to whatever Carl had in mind, if that was what it took to save my marriage. That wouldn't mean I really wanted to submit to Carl. Just that I wanted Jill. And I had promised Jill I'd go along with whatever she asked me to do. Here I am, fresh out of the beauty salon, and I never looked more like a woman. Now she says I should make love to Carl the way a woman woulkd, and to love it. That's what I'm going to do.

With that decision out of the way, I really did want to submit to Carl. Part of me was genuinely curious what it was like to get fucked by a man. Despite myself, I realized I was already looking forward to getting fucked, in fact beginning to feel a certain trembling excitement about it. Last night I went through the motions of cocksucking Tom's prick, trying to feel nothing, thinking it was an ordeal I had to go through so Tom would continue to think I was a woman, when in fact he was thinking what Jill had told him, that I was a shy faggot. Tonight I can actually find out what women feel when they're with men. There had to be something they find attractive. They all want to do it, most of them. And from a woman's point of view, Carl is pretty good looking.

So it's arranged. Tonight, my inviolable virgin asshole will become a much-ravished pussy. And there is nothing I can do about it. Well, since I have no choice, I decided, I will set my manhood aside for the night, somewhere where it can't be violated or touched. Then I won't feel perverse or queer or debased. They want me to be a woman. I'll be a woman. I'll try to want to be a woman. For one night, anyhow. To see what there was to see.

I got up and headed for the bathroom. Then something else unexpected happened. I should have been resenting Jill, but I started to feel grateful toward her, and the feeling spread. She had left me a pretty negligee to wear, and a swimsuit. She had arranged a complete salon makeover, something she knew I'd love but wouldn't have the nerve to arrange for myself. Now she's arranged for me to spend the night being a woman in love with her lover. She isn't denying my wanting to feel feminine, or mocking it, she's confirming it. I don't have to resent this. I can even thank her. All I have to do is go with the flow.

A whirlwind of thoughts, but I was pretty sure I'd arrived at an accurate understanding of my predicament. Whatever I was, whatever I wanted to be, Jill wanted me to proud of myself. My sneaking around was what had offended her. Of course Jill was devious. She had other things in mind as well. But this much I understood.

So I decided to go all out. I would go look for bubble bath crystals or body oils among the things laid out there, and take a bath, so when Carl came back he would find me clean and soft and perfumed. And I needed to prepare myself in other ways. This night was already a learning experience, and it hadn't even begun.

When Carl came back I was already in the bedroom, dressed in my nightgown and peignoir, my skin softened and scented like a field of flowers, looking to see how many pillows I could heap up on the bed toward whatever bliss we might find in each other. My pussy felt utterly empty, maybe too empty, and inserting so many different enema and douch nozzles into it had made me aware that the opening was a muscle I could tense or loosen. Carl extended the champagne bottle ahead of him as he came through the door, as if it were a line of defense he hoped would hold. I walked right through it. "Carl," I said, "I've been waiting for you. You took so long."

"I didn't want to hurry you, darling," Carl replied. "You had so much to do, and to think about."

"Yes, I did," I replied, "And I thought about it. But in the end you were most of what I was thinking about." I reached toward him, and grasped him, and placed my lips on his, hoping he would be able to do something to make me feel less silly.

He did. He set the champagne bottle down, and leaned forward into me, and grasped me around my waist with one arm, and around my shoulders with the other, and gave me the deepest kiss I have ever experienced. He had soft warm lips, and a warm wet mouth. I leaned back as he leaned forward, and he pulled me into him, and we melted into each other, and I felt his tongue enter me and probe, and delicately lick my tongue. I pressed my body closer to him and he lowered his arm behind me, and then gently lifted my crotch into his. He was hard. I could feel it. An hour ago I would have felt sickened. But now I rubbed myself against him, aware that I was also hard. Involuntarily, I let out a loud sigh. "Please," I said, "What can I do?"

"Well," he answered."You can bring us some glasses. We need to toast your new understanding."

I found two and brought them over. He sat on the couch and filled them. I sat next to him, as close as I could. I actually hoped he could smell my perfume! He put his arm around me, and I snuggled into its crook. It was very comfy. He handed me a glass, and I looked at him.

He looked down directly into my eyes and said, "Jane dear, look into my eyes. To the night that lies ahead of us. Now we drink, slowly, steadily, and we keep looking into each other's eyes and keep sipping. It's an old Danish custom."

My feeling for him got incredibly intense as I looked into his eyes! I began to feel eager to submit to him. Of all things, my erection got even harder. He continued to look into me with his half-smile, deeper and deeper, and neither of us said anything, and I looked back at him. His eyes were blue. Suddenly I lost it. I let out a moan and yielded up my core, and threw my arms around his neck and poured kisses onto his face. His cheeks felt slightly bristly on my lips, like any man's when freshly shaved, and I could smell some kind of after shave. But I didn't care. He was just a wonderful, lovely man! "Jane," he said gently, "Let's just sit here quietly for a moment. But I do know how you feel!" So I snuggled in against him and let a wave of deep affection for him wash through me. I had decided I would willingly let Carl make love to me. But things were moving very fast. Now I was eager to make love to him!

His first move surprised me. "Jane," he said. "I want to please you. Let me kiss you snd caress your breasts. Let me kiss your pussy and your clit. I want you to lie back and relax, and do nothing. I want you to empty yourself of yourself, then fill yourself with me. Lie back on these pillows."

I did as he asked, realizing that in my nightgown, with my beautiful nails and curled hair, I felt luxuriously feminine. He asked me to throw my arms over my head and rest them on the pillows above me, exposing my bosom (if I'd had any), certainly leaving my erogenous nipples wide open to him, and he asked me to lift my knees slightly and spread them, and he smiled. There I was, sprawled langorously like Camille waiting to receive her first lover of the evening.

He leaned over and kissed me again, first on the mouth, then on my neck. Sliding my nightgown's straps over my shoulders, he bared my chest and my nipples, and began to kiss them, oh so sweetly. I began to dissolve in erotic feeling as my nipples engorged, and he kissed each in turn. It was so sweet, so very deep, so very loving, as my nipples grew and their feelings spread through my whole body, and they yearned after his mouth. His lips circled and puckered on the very tips of my nipples, and gently began sucking them, first one then the other, and I went into a glorious trance, my eyes closed, my face glowing, and time passed and I was in heaven. I never wanted more to be a woman, and never felt more wonderfully fulfilled as a woman. After a while his lips moved down to my navel. I stretched back further and heard my throat begin to purr aloud, in a high and husky sound, feeling just lovely as his mouth worked further down, then reached my throbbing cock, and engulfed it. Magically, almost at once, I came. He swallowed me and continued as if nothing had happened, with an even greater passionate concentration. I softened, then hardened again.

He paused, got off the bed, then came around between my legs and reached to caress my breasts, and again my nipples felt an exquisite desire for ... something unnameably feminine. As his fingertips danced on my nipples, his head bent down to suck and lick and kiss my penis in ways more intricate than any Tom had told me. My feelings of joy went deeper and deeper, and he brought me off a second time. These spasms I felt deep under my mound, and I sighed aloud with the beauty of it all, then just lay there. I had never felt more sensually at ease. My arms were still sprawled luxuriously over my head. He smiled, kissed my flaccid penis tenderly one more time, and came out from between my legs to lie by my side on the pillows. On impulse I embraced himm, and then kissed him tenderly. I felt just glorious.

I was lying entwined alongside him when he spoke. "Janie," he said. "I think the moment has come. We are going to make love as man and woman." I felt a pang of fear—I knew he was heading toward it, but here it was. "There's nothing to worry about," he said. "You'll love it. Trust me. You'll love it. Just do what I say, and you'll love it."

"All right."

"Here I am lying here face up, looking at your dear face alongside me. Why don't you just straddle me while I lie here. Spread your knees as wide as you can on each side of me, and sit on my crotch."

I did. I could feel his dick was already quite hard. Mine was still slack, sucked out.

"Now raise yourself up just a bit, so I can lubricate both of us." He reached for a tube on the bedstand and did just that, working a fistfull of it on his cock and then gently, gently, reaching under me, he stroked my anus with his finger, spreading a film of jelly all around it. Then as his hand began to feel nice, a little ticklish, I felt a soft finger press on my opening and then into it. My sphincter clamped down on it, and he seemed amused. "Not yet, Janie," he said. "Be patient, love." Then he pulled out. He slathered more jelly on his finger, then re-entered me, and worked his digit in and out for a few minutes, gently, even delicately. The ring of muscle guarding my opening relaxed.

"Please, bend down. I want to kiss your breasts."

I raised myself up off his hand, but the finger and hand followed my bottom as it rose, continuing to move inside my rectum. It was beginning to feel interesting, even a little delicious. Then I leaned my chest over him, and he licked first one nipple, then the other. Then his free hand caressed one nipple while he sucked delicately on the other, tonguing it. The same wave of lovely feelings I had felt earlier returned, and again I melted. I had to kiss him, and I did, with increasing passion, while he continued to touch and lick and caress my nipple tips, and underneath me he slathered more jelly on us. Finally he lifted his prick—a long one by any standard—and tucked it straight up between my cheeks.

"Now, dear, you feel the tip of my prick on your pussy opening, don't you."

I did. I wiggled my hips just a bit to seat it more firmly between my jellied cheeks, the head pressing on my hole...my pussy...but unable to enter.

"That's perfect. Janie you have nothing to fear. You are in charge. You will deflower yourself whenever you feel ready. Just press your pretty pussy onto me as you wish, whenever you wish, more or less, more or less." He took me by the waist for a moment and raised and lowered and raised me to demonstrate the rhythm. Then as if nothing further needed to be done, he returned to kissing and caressing my nipples. Then he reached for my penis with his lubricated hand, and began to smooth and cuddle it, and my belly and all of everything inside began to feel an immense yearning. My hips surged in the rhythm he had begun, up, and down, and I rotated my pussy opening a little while pressing in on him, each movement a bit more insistent as his prick pressed more and more firmy against my hole.

"Ahhh hahhhhhh" suddenly sang out of my throat in a soft soprano voice. He was in! My outcry of ecstatic pleasure surprised me. I pressed my vulva against his cock more persistently, each time increasing my pressure on the soft head of his remarkably firm prick until it was sliding in the slickness between my cheeks, and suddenly I felt a door open in my bottom, and he slid in three or four inches. I stopped. He was well inside me, I was sure of it. I wriggled again, and was sure. I felt stretched, and I felt an intense pressure, as if I were trying to crap something too big to pass, and I eased off, and began to feel just wonderfully full. Then I began to move down and up on him again, and his hips picked up my rhythm. With each movement I took more of him into me, then lifted to let more of him slide out, until only the tip remained, and then he moved up into me and I backed down onto him again. The ring of muscle closing my anus began to spasm at the bottom of each plunge, and I took more of him in, then more still, until incredibly, I found I was sitting flat on his crotch, my weight no longer on my knees but on my buttocks, my back arched, my head thrown way back, my eyes closed, my rear end and my bowels utterly packed with his meat, mindlessly blissful.

By now he was no longer kissing my chest but lying back with a beatific smile, eyes closed, hands on my waist, helping me rise and fall over him, one hand sometimes squeezing my flaccid penis ever so gently, caressing it so it felt just wonderful though it grew only slightly tumescent. Together we moved, and the harmony was musical. I wanted to make him come, to slide and squeeze his prick with my asshole until I could feel it was a true vagina, soaked and christened in cum. We picked up the pace, and the yearning within me increased. Faster, and I felt I was flying on him, my body dancing around his pole, impaled, joyous, sensations building until suddenly they burst. "Ohhhh Gahhhhhd!" I cried out as my asshole spasmed over and over on the base of his prick and my limp dick somehow squirted out more juice with each spasm, just as his hips gave a great thrust up and into me, and his hands clamped my waist and held me in a vise grip, and he emptied his balls into my vagina in a flood of pumping, his spasms triggering even more of mine. My bowel runneth over, I thought irreverently, and I fell down on him, near-unconscious with rapture, and gasped a few times before I could breathe deeply and catch up with myself.

His breathing returned to a more normal pace much sooner than mine. "Well dear, I don't think you're a virgin any longer," he said. I smiled at him weakly in reply. "No," I said in my feminine voice, without realizing I was using it, and then with enormous satisfaction and affection I added, "I'm not." Now that the ecstasy had subsided, I began to think I must have done havoc to my rear end. His cock was still thrust way inside, showing no sign of softening, but all around him I felt sore.

He reached out his hand to the nightstand again, picked up something, and said "Now Jane, lift yourself off me." I did, feeling terribly vulnerable, my sore ass up over him feeling altogether exposed as he sat up, leaned forward, withdrew, spread a cool lotion on my labia, and then in a single move suddenly inserted something very large into me, yielding but stiff, and pushed it home.

"What's that?" I asked, startled. "Now Jane dear, trust me," he replied. "You'll want to make love to me with your pussy some more tonight, won't you? A few more times, I'm sure. So we want to take good care of it for now. It's stretched out, and we want to keep it that way for later. And you have my sperm inside you, the world's best lubricant for later. So I've just put in a medicated plug, to sooth you and to keep you open, and to keep you from leaking. We'll keep it there except when I want to enter you and make love. By morning you'll be well stretched out and won't need it. In fact you'll probably leak for a few days whenever you try to stand up, until your pussy muscles get used to being closed again. But we'll take care of that later. After this night my dear, whenever you are feeling amorous with some young man, you'll find he can enter you much more easily than I did. But right now you need a butt plug. Come, lie down next to me."

The rest of the night went as he predicted. He fucked me in the ass three more times, once with me bending over the bed while he stood pumping me from behind, and caressed my breasts, once doggy style (it was only OK I thought), and once with me on my back and my legs held high on his shoulders, my pussy wide open to whatever he desired, Carl passionately kissing my face and neck all the while he was reaming me relentlessly down below. I loved it. I loved it all. It was remarkable how each time he used me I more and more thought of my anus as a vagina, feeling not like a sodomized man but like a fulfilled woman. I didn't come again that night, though during the last fucking my prick started to get hard, rubbing against his belly. The anal sex got very exciting, my prostate restimulated whenever he re-entered me. I loved it all. I've never really preferred men to women, but that night was the most sexually satisfying I have ever spent, and after that night I knew I could swing either way sexually if desire or need took me either way. That night it occurred to me I might not be merely a crossdresser but a transexual, a real woman in a man's body. The feeling didn't last, but it seemed possible.

His performance was prodigious. Each time he fucked me he came, and just before the third time we had a reprise of my cocksucking session with Tom, and he came again. By then I wanted to suck on him, and swallow him, and eat him alive. Carl sat in an easy chair while I sank between his knees and eagerly licked and kissed and mouthed and caressed his beautiful prick while he showed me how to run my tongue along the full length of its underside, how to angle my throat to take him deeper into me, and finally how to swallow his cum even while matching my mouth's sucking rhythm to his head-fucking. By morning I had spent so much time pleasing him with my mouth and rear end, and had received so much pleasure from him, that I was half in love.

When dawn came I was sleeping curled up on him, my head on his shoulder, his earlobe still against my lips where I had been kissing it when I fell asleep, my arms and legs wrapped tightly around him. He carefully disengaged himself from me, and I woke up to hear myself make the most delicately feminine, sleepily petulant whine of protest I have ever heard from anyone. I tried to stop him by kissing his face and shoulders all over again, fawning over him. But no use. He stood up and dressed, then leaned over me and reached between my legs. For a moment I was hopeful we were beginning again, but all he did was check that his butt-plug was still in place.

"Didn't I tell you this would happen?" he said, mildly amused. "You aren't the first husband I've helped to discover the joys of being a doting wife, and you aren't the first who now, sadly, needs to be reminded that you are not my doting wife. You are your wife's." He said these things while gathering up his various implements and articles of clothing. I watched him a bit dismayed. I then felt dismayed that I felt dismayed.

Fully packed, he went to the door and blew me a kiss. "Goodbye love! O yes, your pussy is stretched, and it will leak for a day or two. When you take out the plug, I suggest you wear a tampon. You'll find some in your purse, where your wife put them before you came here. She knew you'd appreciate her thoughtfulness. I wish you a long and happy life Jane. We won't meet again."

He smiled at me reassuringly. "I loved it," he said. "You are a wonderful lover. You have nothing to be ashamed of." And while I tried to figure what he meant by this, he was out the door and gone.

Obviously, the way I felt now was the way Jill had wanted me to feel when I came home. Sore and complete, and a bit wistful. Satisfied, with no apologies. A woman fulfilled. I stretched back luxuriously, my arms again flung above my head like a houri whose Sultan has just left her, my eyes closed, smiling to myself. It was time to go home.

 

Jack and Jill

by Vickie Tern

CHAPTER SEVEN

 

I sat up in bed for a moment, musing, looking at the door where Carl had just disappeared, and realized I was still smiling in almost feline contentment. The night just past, my sense of entrapment, my acceptance of the inevitable, my conversion to desire for a man, my deep satisfaction at being reamed, and my joy while giving my lover passionate head, all this had gone further than I had ever dreamed possible. I felt...well...lovely! I pushed myself up from the bed and stood up, my weight on one leg for a moment, twisting my hips as I rose, all in a single, gracefully sinuous movement I recognized as intimately feminine. That was how I felt! My smile broadened. This went far deeper than the pleasure I usually felt wearing women's clothing. I glimpsed myself in the mirror, my hair still set in Marianne's mop of curls. How could I have ever wanted to comb them out to look like a man? Despite the night's ravages it looked darling. I looked well-fucked. I felt it, too.

Time for a shower and change. I took out Carl's butt-plug, thinking I'd keep it as a souvenir. But now I was leaking! Carl's precious cum was escaping! I had to stop it and absorb it all was my immediate impulse, and I grinned even more broadly when I realized that was the silly instictual sentiment of a smitten schoolgirl. Still, I wanted to absorb it all. I hopped over to my purse, got one of the tampons Jill had put there, and quickly inserted it—I thanked my stars there were no cardboard or plastic plungers to learn to insert, just a pure tampon ready to expand inside me. Again a full feeling, but satisfying, and I felt proud to think of the string now hanging out of my butt as a symbol of my new womanhood. I had earned it, with all sorts of feelings of love and loss, and desire and regret

In the bathroom I noticed a jar of Nair, and thought why not? Though I was still clean shaven I spread the pink stuff all over me, waited until the itching was intense, then showered it all off. Now I felt like a baby's behind, and I wanted to maintain the momentum, hellbent to become all woman! My new curls held up beautifully. I toweled them off and fingered them into shape, and touched them with air from the blow dryer. My makeup took longer, but I kept to Mari's daytime light tones and remembered her instructions, not much of anything much, but never ignore eyes and cheeks. A little more grey on my lids and I felt fit to look at the world. I saw in the mirror that the studs in my ears were neat, the holes healing. I had thought yesterday that they were a too hasty impulse I'd regret. Now I was quite pleased with them. I felt like a woman. I loved it!

Back in the room I picked out a beige tailored suit that had been hanging in the closet this whole time, and found a purple silk blouse on the same hangar under the jacket. Jill had thought of everything. This was the coming home outfit she had planned for me, I was sure of it. I thought I had better call her.

The phone rang twice, and Jill's voice answered with her polite but neutrally brisk inquiry, "Hello, yes ?" I realized that today was a working day, and that she was probably off to the office in a few minutes.

"Hello," I said in a relaxed, friendly voice, sounding the way I felt, "This is your darling little cocksucker speaking. Just checking in to find out what you have planned for me for today."

"How was last night?" she asked a little cautiously. "Did it go well?"

"It went beautifully Jill. Really well. I loved it! Really!"

She sounded relieved for some reason. "Darling, that's wonderful. I was hoping you'd say something like that. Carl called a few minutes ago and said you couldn't have been more loving. But you never know. You sound just fine. Please come home now, and tell me all about it. I want you to come home, Jack."

"I'm Jane, Jill. I'm not sure where Jack is right now."

"Oh darling," she practically exploded into the phone, "I did so want you to feel that way! Do come home as quickly as you can!" She paused, then said in an amused tone, "Jack can come with you if you like. It's his home too. He can live here with us. But we have so much we can talk about now, Jane! I'll be here. I'm much too excited to go to work today." She hung up.

Well! She did have a plan the whole time, and I had changed right on schedule! Jack had left the house in sneaking shame, a cuckold abandoning his wife to a stranger, a wimp transvestite entrapped cocksucker, and now Jane returns a satisfied and un-selfconscious woman. There it was. Contempt for Jack the crossdresser, the fearful husband terrified to be found out. Admiration for Jane, a woman inside Jack at ease with her femininity and unashamed to be whoever she is. If Jack had not become Jane before Carl started in on him, then Jack would have been cornholed and fucked and humiliated some more, like the previous night, and he would have deserved it. But instead he had become Jane, pleasured and loved and transported into the joys of loving, and as Carl had promised she had loved it, and would cherish the memories. Jill wanted to live with Jane. She was willing to let Jack hang around, but it was as if she was married to Jane! Could there be a little lesbian in her? Could that be why she never really warmed up to Jack? What am I saying? I'm still Jack too, but I'm not what he was, for sure!

I felt confused and excited at the same time. What a woman! Devious isn't the half of it! I packed everything up in a valise I found in the corner of the closet, as I knew I would, and carried it out. On my way I saw that the front desk was manned by the same impassive clerk I had met when I first arrived. "Goodbye, dear," I said to him, my voice as musical as my mood, "It's been a lovely stay. I believe my bill's been settled." He looked up.

"That's right Miss," he said. "Have a nice day."

This time when I reached the car I sat down in my skirt, twisted into the driver's seat, and drove home with brisk efficiency. If a cop stopped me and saw Jack's license, so what! None did. I parked the car in our driveway and sat there a moment, then opened the door. There was Jill standing on the steps waiting for me, smiling. I turned carefully, put both feet together on the driveway, and then stood up. My butt was indeed feeling sore! And my pussy felt full, but the full feeling was nice in a new way. I realized I sort of liked it. I felt fulfilled!. Or maybe what I liked was what it reminded me of. My night of love. I took my purse and started walking carefully toward the steps.

"How are you, dear?" she asked, as I came toward her. "I see you've met Marianne. She gave you a wonderful hairdo. It suits you beautifully."

"Thank you," I said. "I think so too. I'm very well, Jill."

"Oh, and I see she's pierced your ears. Do you like them that way?"

"Yes," I said, "I like them." I meant to sound evasive, to yield her nothing, but it came out sounding a little smug. She heard it, and smiled again.

"Well, darling, welcome home. Why don't you go right upstairs and take a hot bath. You'll feel better. You'll find a fresh tampon on the upper shelf in the bathroom, if you need one. Or perhaps you'd prefer a pad?"

"No," I said, "a tampon will be fine."

She was visibly pleased by that answer. "That beige suit looks just darling on you, nicer than I'd thought it would be. But you'll want to change to something more comfortable now. I've lay out some clothes on our bed, and when you're ready to come down we'll have a long talk. Oh, we have so much to talk about!"

I walked past her holding myself a little stiff, trying not to limp. I heard her. "Our" bed. Well! A hot bath sounded just right. I went upstairs to the bathroom, ran the tub, and added a touch of bath oil without thinking, amused to discover it when the fragrance reached my nose. Then I stripped down and got in. After a long soak I stood up again, feeling very much at ease, and got out. Did I still leak? Better be safe. I found the box of tampons, changed my soiled one for a fresh one, and went into "our" bedroom feeling .. well...pretty neat. Nice. Dainty. Together.

I saw two outfits laid out on the bed, a man's blue polo shirt and slacks, jockey shorts, socks, and sneakers, and another stack of clothes a foot or so away, a white cotton blouse with plaid skirt, bra, panties, and flats. Well, well. One more test? Feeling just a touch defiant, I dressed in the blouse and skirt, touched up my lipstick, and went back down, still walking slowly. For some reason her face lit up when she saw what I was wearing. She was glad to see me. This was not the old Jill, not at all. But then I was not the old Jack. I was Jane. My own woman. And to my own astonishment, that's exactly who I was!

I knew she'd take charge of the conversation by sheer habit if I didn't get there first, so I started speaking from the stairway as soon as I saw her.

"Jill, I know what you were doing," I said. "It worked. I do appreciate it. But it worked better than you think. You wanted me to act like a man, to quit with the women's clothes. I couldn't. Then you wanted me to stop pretending I was a man, to acknowledge I was the woman I've been dressing up all these years. Now I've done it. Carl pushed me over. Before I was a man obsessed to look like a woman, but terrified to be discovered and disgraced. When you fixed me up with Tom, you didn't disgrace me, I did. I felt disgraced in my own eyes, because I was ashamed of who I was. But not now. Now I'm a woman and pleased to be a woman, in a man's body, but with the look of a woman, and I have access to my male identity when it suits me, so nothing's lost and nothing's at risk. But Jill, I feel like more of a woman than you were when you married me, because last night I wanted to do more than you have ever done or wanted to do to give pleasure to the man I loved, the man I loved last night, anyhow. You never felt that way about me."

That was the zinger! But Jill never winced. She simply sat in our large easy chair and looked at me as if I were a birthday present she hadn't yet opened. I sat down on the couch, slipped off my flats, tucked my legs up alongside me, straightened my skirt over them, looked at her, and waited.

She leaned forward and began an address to the jury. "Dear, from the moment I saw you walking toward me, so weary in your rear end but so comfortable and well-poised, wearing your new hairdo and new suit without any self-consciousness at all, your pierced ears telling me you're proud to look female and don't care who knows it, I knew my plan had worked. You're right. Before you weren't a man at all. You were unfaithful to your own manhood and to me, and you were sneaky and ashamed of the woman inside you. I wanted to punish you for all those betrayals, or else straighten you out, one or the other, once and for all. So I trapped you into a situation your manhood would find intolerable but your femininity would find intriguing, even delightful. You had to learn what every woman has to learn sooner or later, to submit to a man and her own desires without loss of self respect. You male ego thought getting fucked by Carl would be a catastrophe, and it would have been, to your male ego. So it went howling in terror from Carl's prick! But that allowed you to become what you are now! As I hoped, you committed to the woman in you, the woman you've always claimed was inside you, and you became that woman, someone able to enjoy a handsome stud like Carl. So you escaped from my trap, and now you're more of a whole person than you've been since I've known you. I think much happier too." Then she added, "Even though your tush probably feels a little used right now. But not ill-used I'll bet!"

Her voice became more thoughtful, as if she were talking to somene like herself. "When we married we were both mistaken. You thought you wanted a wife, and I thought I wanted a husband. Well, maybe we did. Maybe in some ways we still do. I was so proper and innocent. But I'm not the same person I was. I've learned a lot about what I want. We can live together as husband and wife if you want, the two of us, if you really want to wear Jack's clothes and masquerade as Jack. But then we won't be husband and wife. I don't think either of us wants that, really, anyhow. You've always wanted to look like a woman and now you do, and you feel like one too, don't you love, and it isn't too bad, is it? Now you're a woman in your heart. I love what you are now. I think we can live together very happily as woman and wife. That's what I want."

Now she began to sound a little uncertain, even vulnerable. It was very appealing. "I'm not sure what we'll be with each other. Maybe sisters. Maybe girlfriends. Lovers, I think. Or all of these. But we'll live together as women, in every respect, and then we can respect each other in everything. Are you willing to accept this?"

I was overwhelmed. If she had waited a few days to ask me, when the passion I felt for Carl had faded, and undeniable physical thrill of getting reamed in the ass was finally understood as no more than that, and the novelty of feeling myself unashamed to be a woman had lost its novelty, I might have given her a more carefully considered answer. Maybe a different one. As it turned out, the man in me was still very much alive and well, though I didn't know it just then. I think she knew it, and wanted to move fast, with her lawyer's sense of timing. But I was so overwhelmed that she wanted me at all, especially wanted me to be that marvelous thing I was feeling myself to be, a woman newly liberated from feeling ashamed of it, that my eyes filled with tears. I nodded to her, unable to speak.

"You're sure, dear? A woman? No backtracking? No second thoughts? You'll be a woman with me? You want to? Really?"

"I do." It sounded a little like a wedding ceremony, but she seemed to want to hear the words. In a way it was a wedding ceremony. We were re-marrying each other. And once I said the words, there was no pulling back. Then suddenly a wicked impulse possessed me. "Wait a minute. If I move back here with you, do I get to keep my own bedroom?"

She looked surprised. "O yes, dear. If you want. But I hope you won't want it."

"Oh, no," I replied. "Not at all. This will be interesting."

Now it was her turn to look at me with a wicked grin. "It'll be more than interesting, dear. It'll be fun! Something we haven't had much of lately. In fact, not much at all!"

She stood and came over to me, and kneeled by the couch and hugged me, and then kissed me with more passion than I had ever seen in her. "We're going to have such a wonderful life together, sweetheart. Darling, now that I know who you are, and you know who you are, I want to make it all up to you. I love you."

And to my amazement she lifted back my skirt, and pulled down my panties, and as my prick rose to meet her mouth she went down on me. She started to suck me with her lips shaped in a large sweet "O", devotedly kissing the head of my prick every time her lips touched it. "I see that Tom taught you a few things too, didn't he, dearest," I said. She nodded, I think, though it was hard to tell from the way her head was bobbing. So I showed her how to lick the underside from root to crown, and how to angle her head to take me deep into her throat. When I came, she swallowed almost all of it, and looked up at me in triumph. I bent over and kissed her, my cum still on her lips. "Happy Birthday to both of us, darling," I said. "Yes," she murmured, our open mouths pressed tightly against each other. Her tongue pushed some cum still in her mouth over into mine, and it seemed to me a sweet sharing of our new life together. And so it was. But now I know she was also getting on with the next phase of her plans for me, with as little delay as possible..

 

The next few weeks were the happiest I had ever had, worth all the humiliation and misery I had felt earlier. My wife loved me, openly and with joy, with none of the judgmental reserve, sometimes even the hint of scorn, I had sensed in her even before we were married. As she told me, she now knew what she wanted, and that was me.

That is, she wanted the womanly me, me as a woman. I had no problem with that, because after all the suppression Jane had endured that was what I wanted too. We returned to many of our old ways, taking turns fixing dinner, sleeping snug together in our old bedroom, but with a playfulness that was missing earlier. Our first night after my return from the motel I took out my most delicately feminine nightgown, all emroidered pink satin delicately edged in black lace, and put it on, and touched perfume behind my ears and on the pulse points of my wrists, not sure how she'd react to such blatant self-presentation. Then while she readied herself in the bathroom I began moving my undies from my former bedroom back to our bedroom, reclaiming my old bureau drawers, determined she should see me standing full length in the finery I intended to wear to bed that night, previously absolutely forbidden. I wanted her to see my lingerie as also an inaleinable part of me. She came in and looked at me, and the sweetest smile lit up her face, and she opened her arms wide.

"Oh, dearest, you look just lovely. Are you wearing that beautiful gown for me? I love it! You look so darling! Come, give me a kiss!"

So I came over to her, and she enfolded me, and I melted into her mouth, and her lips were as soft as Carl's had been. It was wonderful. I felt like her delicate, demure, cherished lover, as she swept me over to the bed while still kissing me, and lay me down gently, and settled herself on top of me with even greater gentleness, and tucked my risen penis into her crotch and snuggled down onto it, and leaned over so I could kiss and lick and suck on each of her breasts in turn, each a delight, each rapturous, while we moved against each other and I felt myself grow harder, sliding inside her with more and more firmness and lunging into her with greater determination, as she grew more frantic, and cried out "Oh!" "Oh!" and "Oh!" repeatedly, until we both peaked and orgasmed together.

Then we lay there marvellously at our ease, smiling tenderly at each other.

"Tell me, what did Carl do to you that made you most feel like a woman," Jill asked in a quiet voice, as if she didn't want either of us to wake up.

"You know," I replied, not sure whether she did.

"Yes I do," she said complacently. "And you are going to be my woman the same way, darling. But was there anything else? Did he find any little secret places to make you go all soft and feminine and loving and doting?"

"Yes," I said. She waited, a half-smile on her face. Then very shyly I told her. "My breasts. He kissed my breasts, on the nipples. It was heavenly."

"Oh?" she asked. "Like this?" And her head tucked under my neck and her tongue began to lick my nipples, one after another, and then she pursed her soft, billowy lips and began to nurse on them. My back arched up to sink my nipple into her mouth in ecstasy! "Oh God!!" I cried in joy. She took hold of my penis and squeezed and caressed it delicately, and even before I had gotten fully hard I came yet again. Then we fell asleep wrapped up in each other.

In the morning the same thing again, this time with me sprawled on top between her legs, pumping sweetly into her and passionately kissing her neck while she squirmed in delight and caressed my chest until her fingers found my nipples, and she gently tweaked them, then sucked on them. I felt then that I would do anything for her, anything! "Oh, fuck me, fuck me," she said quietly as I humped her over and over and she pressed eagerly back onto me on each stroke, until we both came again. I was in heaven, and lay there floating as Jill got up. "I'll fix breakfast this time," she said as she slipped on a robe, kissed me, said "Don't forget your tampon," grinned sideways at me, and disappeared out the door.

And of course I went out dressed whenever I needed to do so. Back to the motel so Marianne could touch me up. Shopping. With my hairdo and my ears pierced and casual clothing and feminine shoes and the movements Jill had taught me earlier, I looked like a woman at first glance, and noone I encountered bothered to look more closely. In a hardware store a young clerk explained solicitously to me how to tell a pipe wrench from an adjustable end-wrench, because of course no woman could know. Salesgirls asked if I had seen the new silk camp shirts yet, just in, when I was browsing for a blouse. Other women smiled at me when they noticed I was glancing at their hair and clothing in passing, checking out how they did themselves up, and I smiled at them in turn. We belonged together. Much of the time I was unaware I was cross-dressed at all, and just went about my business and then came home.

After a few weeks of this bliss, Jill came home late one night, having phoned earlier with apologies for the sudden emergency come up that needed tending. I waited up wearing a short waltz gown, demure and pretty, checking my makeup now and then. I wanted to be truly beautiful for her when she saw me. I suppose I was, because she came through the door, and set her briefcase down, and we swept into bed clasped together, barely pausing to strip Jill of her pantyhose. She dove for my breasts like a starved infant, first with her fingers and then with her mouth and tongue, and I was transported to paradise. I suckled her with a sweet tender feeling in my belly I'd never felt before, cradling her head lovingly. Then I entered her, and came almost at once. She hid any disappointment she felt at being denied her orgasm, but when I had softened but not yet slipped free from her she asked if I would mind kissing her down below, just once. She knew I had once wanted to, and she hadn't let me, but now she would love to know what it felt like. Another wish fulfilled! I kissed her by way of reply, then quickly reversed myself on her body, pressed my head between her legs and began to tongue and suck and mouth and lick her slit with an impassioned ardor I had never felt for any part of her before.

Almost at once she clenched my head between her two powerful thighs until I could hardly breath, and wrapped her arms around my own thighs with her head buried deep in my damp crotch, and rolled us over, so my face was beneath her. Then she began grinding her cunt into my mouth, and as I licked she began pulsing in orgasm. Immediately my mouth filled and my nose and face and chin were coated with a sticky substance. I realized it was partly her juices, but mostly my own fresh cum draining out of her. Again it tasted sweetly salty, as with Carl, and as with Tom, but creamier. I supposed that was my unique flavor, tasted in her. I loved it that I could taste myself inside her, and I tongued and lipped her so devotedly that she began moving over me again, then moaning, and writhing, and with great cries of "Ahhh! Ahhh!" she came yet again. As she calmed down and her breathing grew steady I rolled us over, turned myself again to look into her eyes, and again kissed her face.

She took mine in both hands and held it. "I hope its all right," she said. "I didn't mean for you to be tasting cum just yet, again, other than your own, if you didn't want to. But I loved what you were doing! I just loved it! I couldn't get enough."

What she said puzzled me a little, but I assured her that women love the flavor of a man, or should, and that I loved being a woman with her as well as a man, and if I could taste myself as a man inside her I loved that too. "Oh darling," she said, "then please, let's always do this afterward, whenever we make love? I do so love the thought of you drinking cum out of me. It tells me you're a woman with me even when you're a man." I told her I was delighted to oblige. And I was. And thereafter that's what we did. I got so I couldn't tell her taste from my own.

A few days later Jill resumed with her plan to make me into the girl of her dreams, as it seemed. It began innocently enough. "Well," she said as she got out of bed one morning, "Let's see what kind of a woman I'm married to." She looked at me closely, benign but critical. "Your hairdo is perfect for now, but we'll think more about it as it grows out. Your face needs attention, dear—you've got to begin electrolysis." She looked over the rest of me carefully. "You know Jane, I never realized that Jack had such potential when he wanted to look female. You're marginal right now, and need more work, but I think you're going to look very nice, really beautiful in a way. Especially after you begin your hormone therapy."

"Jill," I said, "I already look nice, I think. And what hormone therapy?"

"Another ten pounds lighter would be nicer too I guess," she said, ignoring my question, still checking me out. "You're beginning to have a lovely figure, too, but it's time we thinned your waist down some more and rounded you out. We both start dieting this morning. Really. You shower first, honey, and then get dressed. A simple daytime dress, or blouse and skirt, nothing fancy, but pantyhose, and whatever shoes are comfortable and pretty. Just casual shopping this morning, and a stop or two. I want to make a few calls."

With her return to thinking about my practical improvement I realized that the past few weeks had been our new honeymoon, more rapturous than the original one by far. Then we were both more inhibited sexually, and had different ideas about who we each were and what we each needed. Now we knew. Or I did, anyhow. I was still feeling exalted. The more openly I allowed myself to dress and look like a woman, the happier I felt, I realized, first with Marianne, then with Carl, and now with my very own wife. I mentioned this to Jill, and she hugged me and said "I know, darling, I know. It's true. I'm so happy that you think so too."

I slipped out of my nightgown and into the shower, letting the hot water wash away all of the juices from our lovemaking. When I stepped out I saw a large bottle of body lotion waiting for me on the bathroom stool. While rubbing it all over and feeling it soften me, I remembered to check my tampon. At Jill's suggestion I had taken to wearing one all the time, "for the time being," she said. It was beginning to feel more natural for my pussy—my rear end—to be stuffed with something soft and comfortable. I kind of liked it. I slipped into a plain underwire bra and pantihose, a flowered shirt and a plain dark flared skirt, and my nicest black flats. I decided to do my hair and face after breakfast, and I headed down. When I arrived in the kitchen Jill was just hanging up the phone. "Well, there we are," she said, making an entry in her appointment book. "You're a busy girl today. But I think you're going to be a happy one." I kissed my wife. "I'm happy now," I said. And I was.

 

(continued)

  

  

  

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