Thirty Days to Jenny

by Monika Ikon

 

day one

Nothing happened. In fact, it was downright disappointing. The first time Jeff had listened to the tape he pulled off the earphones of his walkman after 30 seconds and said: "What the hell is that? It's awful. Sounds like some kind of new age crap."

Alison was disappointed. She had expected something to happen; ok, she didn't expect it to be "poof" instant girl, but she had hoped for some kind of sign. At the very least, she thought Jeff would feel compelled to listen to the tape. How could it possibly work if he didn't even listen to it? Walking off to the bedroom, she chalked it up to just another internet hoax. How could she have been so stupid? There was no tape that could turn a man into a girl in 30 days. What a fucking rip-off.

She had found the sissification site by following the links backward from a site address left on a message board devoted to women dealing with "problem men." Unlike many of the men under discussion, Jeff hadn't cheated, hadn't abused her, hadn't really done much of anything. Actually, that was kind of the problem. He was one of those guys who just didn't seem to be going anywhere. He was lazy, out-of-shape, inconsiderate, clueless, insensitive, and, worst of all, bad in bed.

She had tried to dump him, without much success; he never quite got the hint and Alison didn't have the heart to just throw him out. What she really wanted was for Jeff to be motivated to become something. So when she came upon the site titled "30 Days to Jenny" she figured she'd found just the right solution to both of their problems. The program promised to shape the right kind of man into a perfectly pliant, perfectly submissive young woman eager to please.

Alison wasn't certain if Jeff were the "right kind of man.," She hadn't ever considered Jeff as a girl before she came across the site, but something about it intrigued her. Something about it made perfect sense. She imagined Jeff as a pretty, submissive girl and felt something stir in her. It was worth a try.

Well, she had tried it and she had wasted $69.95, not counting rush shipping and handling.

 

day two

Usually, Alison had to hound Jeff out of bed in the morning. But he was up and getting ready before she hit the snooze button on the radio for the third time. He seemed to be in an unusually good mood. Alison didn't think anything in particular of the uncharacteristic behavior. Certainly, she didn't connect it to the tape she had played Jeff the night before. After all, his getting up early had nothing to do with becoming Jenny.

Later that day, however, she did note that Jeff called her twice from work just to say "hi." Jeff never called her at the office. He always claimed he was too busy. Too busy--working at a video store? It's probably just a coincidence, she figured, as she dialed the number of the video store to return his call.

That evening, he came straight home from work and was waiting for her with take-out from their favorite Chinese place. He gave her a warm romantic kiss at the door.

As they ate together, Jeff actually told her about his day. Another first. He recounted all the oddball characters and goofy requests he'd encountered. Alison had to admit, Jeff was pretty funny and entertaining when he wanted to be. After dinner, Jeff cleaned up the paper plates and cartons, and packed up the leftovers in tupperware containers. Alison was nothing short of thunderstruck. She didn’t even think he knew where the tupperware was! Still, she didn't make the connection.

Later, feeling tender over his sweet behavior, Alison came into the living room where Jeff was sitting on the couch watching a basketball game. She had brought him a beer. She noticed, however, that the one on the coffee table was untouched.

"Who's winning?" she asked, trying to seem interested.

Jeff started a bit. "I'm sorry?"

"Who's winning the game?"

"Umm…I don't know," he said. "I guess I'm not really watching." He looked at the television as if seeing it for the first time. He shrugged as if dismissing the players running back and forth, throwing balls, all that.

Alison sat down on the couch next to him. She took a sip from the bottle herself and looked him curiously. He seemed different somehow.

Jeff smiled and pulled Alison's bare feet onto his lap. He started slowly massaging them.

"Hey," he said, "can I listen to that tape again?"

 

day three

Alison woke up to the deliciously sensual luxury of having her toes licked. She sighed, stretched, and stared down the length of the bed. At the bottom, Jeff was lying at her feet, slowly and lovingly sucking her toes. He looked up and smiled a little sheepishly.

"That feels so good, sweetheart," she said.

Encouraged, Jeff resumed his attention to her feet, gently licking her soft soles. Alison closed her eyes and enjoyed the sensations. There was no doubt about it; the tape was having some kind of an effect. Jeff was often in the mood for sex in the mornings, but he never bothered much with foreplay. What he was doing now, it was definitely a welcome surprise.

Jeff was kissing her ankles, moving up the insides of her calves, and Alison parted her legs slightly. He spent a wonderful forever between her thighs, teasing and licking and kissing, until Alison was breathing heavily with anticipation. She was never much for morning sex, but Jeff was driving her crazy. She reached down and pulled up the hem of her cotton nightshirt.

"Please don’t stop," she murmured.

She felt his tongue trace the lips of her vagina and she shuddered with pleasure. He lingeringly licked her, seemingly perfectly content, and Alison enjoyed the sheer sensuality of it all. There was no rush toward a goal, no attempt to do anything else, no expectation of an orgasm. After some time, feeling almost self-conscious, Alison reached down and cupped his face in her hands.

"Honey…that was…wonderful…"

Jeff smiled, proudly this time, his face wet with her.

"Come here," Alison said.

She reached between his legs and felt him, hard in his pajama bottoms. She had expected that. She wasn’t in the mood for penetration but she wanted to reward him. To her surprise, Jeff got out of bed, seemingly completely oblivious to his state of arousal. He pulled of his pajama bottoms and his painfully hard erection was standing almost flat against his tummy. He looked around a moment, as if a little dazed, and then walked over to the laundry pile. He picked up a pair of blue silk panties which Alison had worn the day before.

"Can I wear these today," he said, a little shyly. "To remind me of you?"

Alison could hardly conceal her excitement. "Oh how sweet," she said, keeping her tone as matter-of-fact as possible. "Of course you can wear my panties darling. Put them on."

Jeff looked vaguely relieved. He stepped into the panties and pulled them up over his straining erection. The panties were bikini-cut and very skimpy. They barely contained

him; in fact, they seemed to be making his situation worse. Jeff didn’t seem to notice.

"Do they look okay?"

"You look perfect darling," Alison said.

"Do you really think so?"

"Definitely."

Inside, Alison was doing mental cartwheels of joy. Could it be—could it really be working? She didn’t dare believe it…but…

 

day four

The next evening Alison came from work to find the table set. There was a bottle of Chianti at the center flanked by two burning red candles. Jeff came out of the kitchen in jeans and one of her t-shirts. She noticed the apron with the frilly hem tied around his waist. He smiled, happy to see Alison, and ran over to give her a kiss. Barefoot, he was about an inch shorter than Alison in her dress pumps and had to go up a little on tiptoe to reach her lips.

"Hi honey," he said, a little breathlessly.

Alison took a look around, the set table, the sound and smell of simmering, boiling pots coming from the kitchen. Apparently, Jeff decided to take care of dinner again. Only this time he was cooking. Alison was hard-pressed to remember when he last made a bowl of cereal for himself. "What's cooking, sweetheart?"

"Spaghetti," he said. He shrugged apologetically. I’m afraid it's all I know how to make."

"That's okay, sweetie. I could go for Italian."

"Really?" Jeff beamed. "I bought some cookbooks from the place next to the videostore. I thought maybe I could learn how to, you know, cook a little better."

Alison couldn't resist. He looked so cute standing there, barefoot in an apron. She touched his cheek affectionately.

"I'd like that."

At dinner, Jeff served the food and poured the wine. He fussed over Alison, clearly nervous if she would like the dinner or not. His behavior was a far cry from all the times she'd come home dead-tired from work, put something together for dinner, and have him complain that he didn't feel like eating leftovers again!

"Would you like a little more cheese?" he offered. "More sauce. It just from the bottle, but I tried to add some of the spices you add. At least I think I put the right ones in."

"Relax honey," Alison said, amused. She had never seen him so adorably flustered. "Dinner is perfectly delicious. Thank you."

Jeff sighed with relief.

For the first time, Alison noticed her boyfriend's plate.

"That's all your eating?"

"Oh god Ally. I caught a look at how I looked in your panties today. I have to go on a diet! I was at the checkout line at the supermarket this afternoon and found one of those little lose weight fast booklets by the register. I thought I'd give it a try. I think maybe I'll even start running. Rafe, you know, the surfer dude at the video store, he runs all the time. He said he'd go with me."

Alison listened with sheer fascination. She poured herself more wine. She needed to distract herself from her own excitement. "That's just wonderful darling," she managed to say. "Just wonderful."

A moment later, she had gotten enough control of herself to ask: "Do you like wearing my panties, honey?"

Jeff looked down.

"It’s okay," Alison smiled, encouragingly. "You can tell. I’d love to hear what you think."

"Well, I really like the way they fit, so snug and skimpy. It’s like being exposed or something. They make me feel kinda sexy all day long." He seemed to catch himself and added quickly, "You know, they make me think of you."

"That’s nice sweetie. Really nice."

That evening Jeff sat in the kitchen after cleaning up and looked through his new cookbooks. Alison was down the hall, surfing the internet. She visited the testimonials on the 30 Days to Jenny bulletin board once again. She could hardly believe the claims left their by women who claimed that their husbands, boyfriends, nephews, sons, and fathers had been totally transformed into her pretty, submissive, girls. But she couldn’t deny the incredible change that had come over Jeff. And it had only been, what, four days?

Alison got up and went into the kitchen for a glass of lemonade. She stopped in the doorway for an instant and looked at Jeff sitting at the table. His head was cocked to one side, a finger to his lips, jotting down the recipe he'd found in the cookbook open in front of him. He was wearing headphones, humming along pleasantly to the tape, as he read.

 

day five

Feeling sexy, Alison lay in bed in a black negligee and watched Jeff undressing. He was wearing another of her panties, a pretty little pink silk pair, and there was very little to conceal the huge bulge Jeff's hard cock was making.

"Come here Jeff."

Jeff walked over, wearing nothing but the panties and, of course, the erection. Alison traced the outline of the hard, silk-encased cock.

"I think we should take care of this, don't you?"

Jeff seemed suddenly very embarrassed. "Oh, Ally…I…dunno…I guess it will go away…"

Jesus, will wonders never cease, Alison thought. The rest of it, up to now, had been pretty damn amazing. But the idea that her oversexed boyfriend would actually turn down sex…it was, well, impossible! She slowly traced a long-nailed finger along his swollen shaft and ended tickled his glans. A tiny drop of precum spread into the silk.

"Now look," Alison said playfully. "You're getting wet. Come on, get your panties off. We have to take care of that."

Jeff hesitated, looking around the room. Good grief, was he actually blushing?

"What's the matter, sweetie?"

"Ummm…could I have like something…something, you know, cover myself?"

Alison could hardly believe her ears. This was a guy who thought nothing of sitting around in a pair of underwear or strolling down to the kitchen in the buff for a can of beer.

"Sure darling…" Alison wondered, if--maybe. It was worth a try. "You can throw on my robe. Its right behind the door."

Jeff looked relieved. He walked to the door, which gave Alison a chance to check out his ass looked in the panties. Not bad, she thought, not bad at all. If he sticks to his diet and running regimen…

Once inside the short silk kimono, Jeff slowly stripped off the panties. He stood in front of Alison seeming a little bewildered. The kimono was so short that it hardly covered anything at all.

"Climb on the bed silly," Alison said.

"Okay."

To her surprise, Jeff immediately lay on his back, this legs slightly spread, assuming the submissive female position. Alison tried not to show any surprise as she straddled his hips. She lowered her pussy over his hard flat cock and rubbed up and down its smooth, hot length. Jeff seemed uncharacteristically composed. She ducked her head and kissed him warmly on the mouth and Jeff responded with a deep, open kiss of his own.

Hmm, Alison thought, that's more like it. She kissed him some more and Jeff became more animated beneath her. She could feel his body undulating but restrained. On a hunch, she reached down and squeezed his left nipple. This elicited a clearly pleasurable little moan from her boyfriend, so she did it again. His movement became more urgent now; he wriggled around sensually beneath her.

Alison could tell from long familiarity that Jeff was ready. But curiously, he made no move to penetrate her, in spite of the fact that he was rock-hard and that her own hot, wet pussy was sliding up and down against him. It suddenly occurred what he was waiting for.

Propping herself up, she pulled herself slightly ahead of the tip of his swollen glans and then slowly, inch by inch, slid herself onto his cock. Jeff moaned with pleasure. He reached up and played lightly with Alison's nipples. No hard squeezing or twisting…just a light sensual touch, a brush with his fingernails, a playful pinch between his fingers.

Jeff usually finished rather quickly. It wasn't exactly a case of premature ejaculation…more like he just didn't have the discipline to wait for her to come. But this he was in no rush to come. Fact was, he was so engrossed in the pleasurable sensations of Alison's love-making that he seemed unconcerned about coming at all. Alison reached three leisurely orgasms before she figured it was time Jeff found relief.

"I'm going to finish you now honey," Alison whispered, sweaty, happy, sated. "I don't want you to fight it, okay?"

Jeff nodded, biting his lip.

Alison increased her strokes, her boyfriend sheathed tightly inside her. She could see Jeff's excitement building. He was trying to hold back, for some reason…modesty, perhaps? But Alison could see he was losing the battle. He was so close, she could sense it, his penis swollen inside her feeling bigger than it ever had. He needed one last thing to bring him over the edge. Alison reached down and pinched his hard little nipple.

Jeff's body moved in rhythm with hers, his eyes closed, at the end of his outstretched arms his hands balled up in fists. His brow furrowed with sensual concentration. Alison bent forward and whispered,

"I love you in panties."

Jeff gave a little cry and his body bucked beneath her.

"Oh, oh, oh…"

"It's okay honey come," Alison said, smiling down at her sexy boyfriend as he shuddered to climax.

She let him go to the bathroom first to "wash up." She noticed, with satisfaction, that he slipped on the short little kimono the moment he got out of bed.

 

day six

Off from work, Jeff volunteered to do the grocery shopping. He had made a little list after going through the refrigerator and kitchen cabinets. There were also some ingredients he needed for the new recipe he wanted to try.

Hmmm, Alison thought, even if it ends right here, I could get used to this.

At the door, she kissed her boyfriend warmly on the mouth. He was wearing a pair of sweat-shorts and an oversized football jersey, but underneath Alison knew Jeff had on a pair of her black lace panties. There hadn’t been any further discussion after that first time. Jeff was wearing panties every day now. It seemed perfectly ordinary that he do so.

On the way into the office, Alison remembered the folder she had forgot to bring with her. She had an early meeting and couldn’t turn back to get it, so she waited until lunch time to drive back home. She called him on her cell phone but there was no answer. She figured he must be at the supermarket.

Jeff’s car was still in the parking lot when she pulled up. Odd, she thought. She let herself into the apartment and heard the music turned up loud enough to swallow the sound of the ringing phone. He must have brought the boom-box into the bathroom. He was playing one of her old Madonna cd’s, of all things!

Alison walked down the hall. The door was partially open and she could hear him humming along to the music. But it wasn’t the Madonna song he was humming.

"Jeff?"

Alison pushed the door open and there was her boyfriend in the bathtub, one foot propped up on the faucet, shaving his leg with her pink razor. He had the headphones on and was listening to the tape on his walkman which sat on the edge of the tub. She stood there for a moment, stunned, and Jeff looked up at the same time, mistaking the look on her face entirely.

"Oh god, Ally…I can explain…I…"

He sat up and fumbled for the tub drain. The poor darling was frantic. He almost pulled his walkman into the water with him.

"It’s okay, sweetie," Alison said, forcing herself to appear composed. She didn’t want to scare him.

Jeff still thought it necessary to come up with a plausible explanation. She let him try.

"Ally I just thought with me running and all, my legs would just look better, you know, without the hair…"

"Jeff I think they look just wonderful."

She did, too. His legs looked long and sexy like this. Alison smiled and her boyfriend looked somewhat relieved. She knelt down by the side of the tub and picked up the pink razor floating in the soapy water.

He looked up at her shyly.

"You’re not mad?"

"Mad? Why would I be mad?"

"Or think its weird or anything…"

"Ssssh…don’t be silly sweetheart." She pushed him gently back into the tub. "Here let me finish for you."

He had pulled his headphones off trying to get out of the tub and now Alison replaced them. She told him to lean back, close his eyes, and relax to the pretty music. She then slowly and carefully finished shaving her boyfriend’s legs.

 

day seven

After the first night, Jeff no longer watched sports on television. If he happened to click passed some kind of game with the remote, he didn’t even pause to show the least interest. Instead, he and Alison watched television together, mostly the situation drams and trendy relationship-oriented comedies that Alison enjoyed.

Fresh from the shower, Jeff sat on the couch in a pair of green silk panties and Alison’s pale green bathrobe. Alison’s feet were in his lap and he was happily giving her the best foot massage she’d had since forever. That evening he’d brought home a bag of videos after his shift at the store. In spite of the progress made over the last week Alison expected her boyfriend ad brought home the usual fare of action-adventure, horror, and crudely sophomoric "comedies" he usually watched. She was shocked when after dinner he asked her if she wanted to watch Pretty Woman with him.

"Honey, what else did you bring home?"

Alison watched in amazement as Jeff pulled the videos from the bag.

"Ummm, I have Titanic, Romeo & Juliet, Thelma and Louise…would you rather watch one of them?"

Alison was speechless. The old Jeff would never have dreamed of watching any movie that didn’t have an explosion or a girl in a bikini on the cover. He would never watch a "chick flick" with her if the alternative was watching paint dry. Now they were sitting there watching Chasing Amy and sharing a bowl of unbuttered popcorn.

At one point, her boyfriend looked up, perplexed and troubled, and said, "Why are guys such jerks sometimes?"

"I don’t know sweetie," Alison said, carefully choosing her words. "They can just be very inconsiderate. They don’t understand how sensitive a girl can be."

"I know," her boyfriend said. God, was he pouting? Today was Rafe’s day off but he said he was coming by the store for lunch and he never showed. And he didn’t even call."

"Oh honey, I’m sorry."

Alison put on a sorry face, but she wanted to clap her hands in delight. The changes he was making in his appearance were awesome, but the way her boyfriend’s behavior was readjusting itself was what really excited her. He was already distancing himself from his gender and identity and adopting a girl’s point of view. How long would it be before the idea of boys were completely alien to him?

 

day eight

For breakfast Jeff ate a half of peach and a tiny mound of cottage cheese. He was really taking his new diet seriously.

When he was finished, he cleaned up after himself. He poured Alison some more coffee and stood by the sink. She could tell that he was fussing over something in his mind. He had taken to chewing his bottom lip when he was worried. Alison thought he look simply adorable doing that.

"What is it honey?"

"I was thinking…"

"Oh how cute," Alison said. She sipped her coffee. Jeff had no idea how literally she meant that.

Jeff smiled, looking a little uncertain if she were making fun of him or not. He let it pass.

"I don’t think I like these shorts."

Jeff was wearing a pair of gray sweat shorts that he sometimes wore cycling or playing basketball. Lately, he didn’t use them much except to lie around the house watching television or for sleeping. Alison hated them.

"Really?"

She took a deliberate sip of her coffee and watched her fidgeting boyfriend over the rim of the cup. She was very interested to see where this was going.

"Yes…well, what I was thinking was that…the thing is…I was trying on your running shorts…kinda by mistake…"

Jeff looked up from the floor as if to check the expression on Alison’s face. She tried to look as neutral as possible.

"So?"

Jeff looked relieved. "Well they just felt more comfortable."

"Of course they do silly. They are much more lightweight than those horrible things you’re wearing. And they’ll probably help you run better."

"Really?" Jeff brightened.

"Sure. Why don’t you go run and put them on for me. And throw those ugly old sweat things in the garbage."

"Oh, okay!" Jeff was smiling. "Thanks Ally. You’re the coolest!

He was in such a hurry to put on her running shorts he nearly skipped from the room.

Alison pumped her fist in front of her face.

"Yes!" she said under her breath.

A minute or two later Jeff came back in the kitchen. Alison felt a little dip of disappointment. Her boyfriend had chosen a pair of her blue mesh running shorts. They had a thin pink piping along each leg, and although they were definitely women’s shorts, he had picked out her least femme pair. On top of that, Jeff was wearing an oversized cotton baseball jersey pulled outside the shorts so that they were almost completely hidden from view. His shaved legs were smooth and shiny looking but he was still wearing his sweatsocks and clumpy guy sneakers…

Alison checked herself. Jeez, she was getting greedy! What did she expect? It had only been 8 days, after all!

"How do I look?"

"You look great, really honey."

Jeff seemed happy. He gave Alison a little peck on the cheek. Then he slipped his headphones on and hooked the walkman to the waistband of Alison’s running shorts. He listened to the tape and did some warm-up stretches before his friend Rafe came.

Alison watched her boyfriend sitting on the kitchen floor in her panties and shorts doing hurdle stretches. To think, he’d come this far was a miracle. Who would have thought Jeff would be wearing women’s panties and running shorts after scarcely more than a week? She had almost taken for granted how big a step this really was…wearing girl clothes out in public, even if they were mostly hidden.

But seeing Jeff in her running shorts made her impatient. Suddenly, the idea of turning her boyfriend into Jenny seemed incredibly real. She could hardly wait to see what came next.

 

day nine

They went out for the first time since Jeff began listening to the tapes. To her pleasant surprise, it was Jeff who suggested the romantic little French bistro he’d always balked at in favor of steakhouses and fast food restaurants.

Having taken four years of French in college, it seemed only natural that Alison order for the both of them. As she and the cute waiter flirted in French, Jeff sat smiling politely, unable to understand a single word they were saying. When the food finally came, she explained to Jeff what she’d ordered for him. Alison enjoyed herself immensely. Jeff listened with interest as Alison talked about the politicking going on in her office. He even made a few unexpectedly thoughtful and insightful comments. Jeff had never worked in an office and with his high-school education and limited skills he wouldn’t be qualified for much more than a job in the mailroom or as a receptionist or secretary, but he did seem to have a lot more "people skills" since listening to the tape.

"More wine, mademoiselle?" The cute waiter asked.

"No thanks," Alison said. "But you can give some to mon petit ami."

"Ally," Jeff said, looking embarrassed. She thought he was blushing over the affectionate sobriquet, although she doubted he could understand it. Instead he said. "You’re going to get me tipsy."

"That’s okay dear. You look cute when you’re tipsy."

The waiter, who understood that a seduction of some sort was taking place, winked at Alison as Jeff sipped at his wine. They laughed together and Jeff covered his confusion with a pretty smile.

When it was time for desert, Alison had to reassure Jeff that it was okay to break his diet just for tonight. They shared a chocolate crème brulee that Jeff agreed was just scrumptious. He actually said that word, "scrumptious." Jeff really did look cute flushed with wine and his dark hair spiky with gel. The knowledge that underneath his regrettably still boy khakis that his legs were shaved and he was wearing a pair of red panties trimmed with delicate lace gave Alison a strange rush of excitement. She looked at the bored-looking boyfriends and husbands of the women at the other tables and felt especially proud of her already greatly improved and soon-to-be perfect sissy boyfriend.

After dinner, they went to a movie that Jeff had picked out himself: Riding in Cars with Boys. They sat near the back and as the movie started Alison put her arm around Jeff’s shoulders. He snuggled in cozily and seemed really absorbed in the story. She slipped her hand into his lap during the sweet parts and made out with him a little, pulling down his zipper and fingering his penis through his panties. He wriggled around a bit and seemed concerned that someone might see them, but otherwise he pretty much let her do whatever she wanted with him. He responded to her caresses by getting hard as marble inside his panties, although he didn’t show any of his usual concern for achieving relief from his uncomfortable condition. On the way out, Jeff was gushing happily about what a great movie it was. To be honest, he liked it much more than Alison, who found it somewhat boring.

Her boyfriend was still talking about the movie later at a table at TGI Fridays. Alison pretended to listen as she worked on getting him drunk. She succeeded eventually. On the drive home, as Jeff dozed lightly in the seat beside her, she slipped the tape into the car radio. The website had explained that the personalized cues worked into the tape would assure that it could only affect the intended victim. As Jeff slept, Alison watched his soft mouth make cute little o-shapes.

She got her boyfriend home and into the bedroom where she set about undressing him. She pulled off his slip-on shoes, thinking she couldn’t wait until Jeff was wearing sexy little strap sandals. Then she removed his socks, wondering how long it would be until she’d see him sitting on the edge of the bed, carefully unrolling a pair of seamed stockings down his long smooth legs. She wiggled her way up on the bed and unbuttoned his blouse. Yes, she referred to his shirt as his blouse. She had even done so in front of him earlier in the evening and he didn’t blink a pretty eye. She rubbed her hand over his smooth chest and pictured a soft, plump, B-sized breast there. His pants came last and as she pulled them down his shaved legs Alison could hardly wait for the day when her boyfriend would never think to wear pants on an evening date. Maybe capris, or a pair of sexy girl’s designer jeans if it was informal, but definitely no more pants from the Gap.

Jeff lay there now, naked except for the red panties, only barely conscious. He looked so sexy like this, pale and defenseless, his hard penis barely contained in the skimpy underwear. She had brought the tape in from the car and had put it inside his walkman. She slipped the earphones over his head and pressed the play button. Jeff smiled a little and resumed making the little o-shape movements with his lips. Someday soon, she resolved, those lips would be painted red.

Alison stood by the bed and watched Jeff as she undressed, growing hotter by the second. She knew what she was doing amounted to a kind of rape; at the very least, she was taking advantage of her boyfriend, but that thought only served to get her that much more excited. Naked, she climbed onto the bed and straddled Jeff’s body, slowly inching down his damp red panties and releasing his hard little cockette. She licked her finger and rubbed the darling little thing and ached at the way it strained towards her. Unable to hold back any longer, she fed it inside her hot pussy and watched the delicious reactions crossing her boyfriend’s mesmerized face.

"I’m turning you into a girl honey," Alison said huskily, turning herself on. "Pretty soon this kind of sex will be impossible for you. Oh god, darling, just look at you…lying there…so sweet and passive…you’re going to make a perfect girl…I can’t wait…this little cockette inside me…its mine darling…mine…mine…mine…"

Alison was sure Jeff couldn’t hear her over the tape, but that made no difference. Her orgasm came suddenly and explosively. Afterwards, she lie beside her boyfriend, having pulled his panties up over his still straining erection. She fingered the dark spot on the front of the red silk and looked lovingly at her soon-to-be ex-boyfriend. She ran her hand slowly up and down his shaft and saw his body tremble.

Alison decided that an orgasm would be good for him so she increased the tempo of her hand. Jeff seemed to be dreaming a particularly vivid dream under the headphones. He had the cutest, most pleading look on his face as he neared orgasm. His toes spread and his back arched a little and Alison knew his time had come. She watched, fascinated, as the wet spot on the front of his panties grew and grew and grew.

 

day ten

Jeff woke up the next morning with the sun streaming in the window and a slight headache. He sat up and ran his fingers gingerly through his tousled hair.

"Woo…I really tied one on last night."

Alison set a tray with a glass of orange juice and a plate of toast on the nightstand. She was wearing a little pink teddy under her silk robe. It was her hope that Jeff would be wearing a similar outfit before too long.

He picked up a piece of toast and nibbled it.

"What’s this," he said. "Breakfast in bed?"

"You were so sweet last night."

"Really? I don’t remember much."

"Check your panties."

Alison smiled when Jeff looked under the covers and discovered the mess he’d made of his panties.

"Oh…" he said, blushing. "I’m sorry."

"Don’t be silly," Alison said. "But, just for the record, I can’t be having you cumming in my panties like that. I think we’re going to have to buy you panties of your own."

Alison watched Jeff’s reaction. So far, so good, she thought. He’d initially begun wearing the panties to remind him of her. Or at least, that was the reasoning he’d given. Now he just accepted that it was quite natural for him to wear panties.

He swallowed the two aspirin she gave him with some of the orange juice.

"What time is it?" he said.

"Ten thirty."

"Ten thirty!" Jeff sputtered, throwing off the covers. "God, it was my turn to open the store. Why didn’t you wake me up? I’ve got to get down there!"

"Don’t worry honey," Alison said calmly. "I already called Rafe. I explained everything. He’s covering for you today."

Jeff stopped, his smooth bare legs hanging down the side of the bed. He was staring down at his feet, his toenails painted with grape glitter polish. After she had made him cum the night before, Alison, on a whim, had painted his toes while he slept.

"What’s the matter honey?"

"Did I do that?" Jeff asked, tremulously.

"Do what?"

"My toes…paint them…like that…"

"Yes. You were a bit drunk, I’m afraid."

Her boyfriend stared thoughtfully at his feminized feet. Alison stood beside him and looked down at them, too.

"I guess I should get some nail polish remover…or something…and take it off."

"Why?"

"Why?…because…"

"I like the way they look."

"Really?"

"Yes, I do. I think they look sexy with your smooth legs and panties. Don’t you?"

Alison sat on the bed next to Jeff and put her arm around his shoulders. She rested her other hand on the crotch of his soaked panties and casually played with the nub of his little cockette.

"It’s okay sweetie," she said. "I promise."

"I do like the way they look," Jeff admitted, pointing his painted toes down, like a girl putting on stockings or having an orgasm. "They look sorta cute."

"Oh baby they are cute." Alison could feel him getting hard beneath her thumb. "Tell me, you like Rafe, don’t you?"

"Yes," Jeff said. "He’s a great guy."

"I mean you really like him…"

"Yeah sure…"

"He’s really cute, isn’t he?"

"What?"

Jeff jumped up from the bed. He stood there with his head cocked to the side, a hand on his hip. "I know what you are trying to do. You’re trying to say that I’m gay because I’ve been wearing panties and I painted my toes. But I’m not. I’m not gay!"

Alison didn’t say anything. She watched as her boyfriend thrust his arms to his sides and turned away in frustration. He marched over to his dresser and looked through his drawer for a pair of white cotton briefs. He looked at the underwear he’d pulled out for a moment and put them back. Then he walked to her dresser.

"Do you mind," he said petulantly, "if I wear these?"

He held up a midnight blue satin pair of bikini cut panties with black lace trim.

"No," Alison said, nonchalantly. "Go ahead."

Jeff tilted his chin a little in the air and marched off into the bathroom. A few minutes later, he came out dressed in her little blue running shorts and an oversized hockey jersey.

"I’m too wasted to run," he announced, slipping on the earphones of his walkman. "But I’m going for a walk. I need some air."

A few seconds after the front door closed, Alison logged onto the 30 Days to Jenny site. She wrote an email to the support team explaining the mistake she had made in rushing things along too fast. She thought it a good sign that Jeff was still wearing panties, but she couldn’t help feeling concerned. She waited anxiously for a response. That evening, she got a return email. Alison sighed with relief as she scrolled down and read the message.

"Don’t be discouraged," the email read in part. "Resistance is normal—even desirable. Such ‘setbacks’ often signal that your sissy is about to take the next major step towards his new life as a girl. He’s losing. Just be patient. Some very dramatic changes are about to come.—Sincerely, The Staff at 30 Days to Jenny

 

 

 

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© 2002 by Monika Ikon. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.