During the 70’s, I spent a lot of time hanging around NYC’s Greenwich Village. I was young and the city seemed an altogether safer place to indulge in crossdressing activities than my suburban home, so I frequented many of the vintage clothing shops in search of feminine apparel. I did, in fact, visit the shop in this story (the name is made up; I can’t remember what it was really called) but the lovely young man who helped me never received more than my sincere thank you as I left the shop. For years after, I wondered at what might have been and, thus, constructed this fantasy.

WARNING: There are some very strong humiliation elements in this story (including watersports) so if that sort of thing bothers you, best to back away now!

Otherwise, I do hope you’ll join me as we get...

 

Out of the Rain                 by: Cissy Gaye

 

Sometimes trying to get dry brings you closest to drowning.

I was on my way back to the bus stop when the heavens opened up and the deluge began. I had no umbrella with me, because the skies hadn’t seemed threatening when I left the house, so I dashed under the cover of the nearest storefront awning. The rain was pounding down, big drops packed tightly together. It was clear I wouldn’t be going anywhere for a while.

I noticed that I was just a few doors down from a vintage clothing store I’d often seen but never visited. I wasn’t exactly equipped for buying female clothes on this particular day, having left my foundation garments off to make book-hunting in the city a more comfortable endeavor, but I knew how much the corset took off my waist, so I could probably fudge it if a skirt caught my eye. Besides, I thought, the book-hunt was a bust, so it can’t hurt just to browse a little.

The shop was located on the second floor of the corner building at Second Avenue, over a combination soda fountain and smoke shop. I got wetter as I ran from awning to awning and by the time I reached the door to the stairs that led up to the shop, I was drenched. I stood just inside the doorway for a few minutes, letting the excess rain drip off me as I watched the Village traffic hiss by, then I went upstairs and opened the stout wooden door that led into Goldie’s Vintage Threads.

A little bell tinkled near my ear as I entered. I looked up and saw one of those hanging bells that is tweaked to ring by the door as it opens. Put there so no one could sneak in and rob the place while the salesperson’s in the back, I supposed. A full length mirror was mounted on the wall to my left as I entered. I caught a glimpse of myself as I went by, five foot ten, 170 pounds, long strawberry blonde hair, pale white skin and a soft, not quite pretty face. Not a very impressive picture of a man, I suppose, but as a crossdresser I was grateful for the fact that my genes hadn’t cursed me with an overly masculine look. I didn’t look especially fem either, so I never got hassled; I was of a more neutral type, which suited me fine.

The biggest problem with vintage clothing stores, at least in NYC, is the size issue. Most of the clothes have long since lost the tags that indicate their size, which in many cases would be the old sizing formulas anyway, none of which I could translate. In addition, the clerks are always too busy - or too cool - to be bothered trying to assemble the clothes in any sort of size order. So, you pretty much have to check everything and hold it to yourself in the mirror, before you even bother heading for a dressing room. For that reason, I rarely shop for drag unless it’s close to Halloween, a time when I feel a bit less uneasy making it so obvious that I’m buying women’s clothes for myself. But at the same time, I’m a submissive and I love the feeling of personal humiliation, so after establishing that I was alone in the store except for a bored-looking male clerk dozing behind the cash register, I figured what the hell and I started holding things up to myself in the mirror if they looked anywhere close to my size.

I was just thinking that the white crepe blouse with the big, floppy, chiffon neck and cuff ruffles would probably fit me, when I heard a soft voice at my side.

"That’s a very pretty blouse and it should fit you nicely."

I was so startled, I almost dropped the blouse. I looked over to see the male clerk, a tall, slender, somewhat fey young man, perhaps five years my senior, standing next to me with his hip cocked in a very feminine stance. His brown hair flopped down over his left eye and he brushed it back with long, narrow fingers that seemed to have exceptionally shiny nails.

"Oh, dear, I’m so sorry," he said. "I didn’t mean to startle you."

"That’s alright," I said. "I didn’t notice you walk over."

"I just had to. Because if you like that blouse, I think I have a skirt in your size that would go perfectly with it."

"Really? Oh, I’d like to see that." I told him. He turned to go to the next aisle and with a languid hand motion, he indicated I should follow him. He had lovely slim hips and a slight swish to his walk that I found strangely sexy.

When I realized the effect he was having on me, I was more than a little surprised. I was, as far as I knew, straight. I’d never found men attractive before. In fact, as a child, I’d worried about that, since the one book I’d found that explained my need to dress in women’s clothing had made it quite clear that dressing in drag meant I was a homosexual. It made me more confused than ever, because men did not turn me on in the least. Bad enough, in the mind of an eight year old in the 1960’s, to believe he was gay, but how much worse to be gay and yet not like men! I was a sexual failure in my own mind before I’d even had my first orgasm. I bet a shrink would have a field day with that little revelation!

But lately, I’d begun to fantasize about men. Not big, barrel-chested hairy guys with muscles and sweat, but rather feminine men, slim, pale, soft men with gentle voices and tender eyes. They found their way into my masturbation fantasies as extensions of the punishment I would endure under the guidance of a dominant woman who would dress me up in drag and then force me to pleasure her slave boys orally and, in fantasies even more recent, anally.

It wasn’t as though I found them necessarily attractive, it was strictly for the humiliation value, I thought. Although, to be fair, I chose to fixate on the femmy ones because they were less repulsive to me than the hairy slob types. But it was all about humiliation, I believed. Forced to suck dick or get buttfucked by a man at the hands of a merciless bitch goddess was the most profound humiliation I could imagine, even more humbling than receiving a Golden Shower, which had been my previous year’s escalation in fantasies. It was the last resort I could turn to when my fantasies of dressing up and being humiliated by women proved insufficient to bring me to orgasm, a situation that was happening more and more, much to my concern.

So, I had all this on my mind as we rounded the corner into another aisle and the slender young man stopped rather abruptly to begin searching through the racks. Lost in my thoughts, I didn’t stop in time and I bumped into him.

Flustered, I tried to apologize.

"It’s alright, dear," he said. "You’re a bit nervous, aren’t you?"

I nodded my head silently, afraid my voice would crack if I tried to speak. I was stunned to discover how much I was attracted to this guy. The slight contact I’d experienced by bumping him had set my heart off on a wild rush of pounding beats, my face was flushing and my cock was starting to stand up and take notice. The young man before me appeared to register all that with a glance and offered me a bemused smile. He put his hand out and gently touched my shoulder. He looked carefully in my eyes, obviously ready to drop the hand immediately if I showed the slightest sign of protest, but I trembled at his touch.

"I understand perfectly, dear," he said. "It’s a bit nerve-racking when you can’t be sure if people will accept you as you really are. I’ve known a bit of that in my time. Not to worry, dear, the only things we don’t accept here are American Express and a less then perfect fit." He turned back to the racks and continued flipping through the clothes.

I watched him as he expertly made his way through a bewildering array of clothes, suddenly emerging with a long, black satin skirt on the hanger he held in his hand. He motioned me closer, then he held the skirt up to my waist. "Mmmm, a little too small around the waist," he mused.

"Oh, but I have a corset at home," I said. "I didn’t realize I would be coming in here today, otherwise I would have worn it."

He gave me an appraising glance. "How much does it take from your waistline?" he asked.

"I can lose about three inches with it," I told him. "It’s supposed to tighten more, but I can’t get it any tighter myself."

He looked at the skirt and then back at me and seemed to be trying to reach a decision. "Well," he said, "I can’t be sure. But we can give it a try."

He led me back towards the dressing rooms. He hung the skirt’s hanger from a long bar across the back of the dressing room, then took the blouse from me and put it next to the skirt.

"You’ll need a slip," he said. "And, at least to check the fit, you’ll need a bra. Are you interested in panties?"

"Well, I’m not really interested in second-hand panties," I said.

"I don’t blame you a bit," he assured me. "We don’t sell them. Too many hygiene problems. But we do have some lovely new ones we got from an old lingerie store that recently closed. Some of these panties are forty years old and they’re still in the original boxes! You owe it to yourself to at least take a look. Lingerie like this is a thing of the past."

He took out a few boxes from beneath the counter and opened them before me. The panties were beautiful, soft satiny peaches and pinks, delicate lace and intricate trim abounded. There were two pairs of each in a size the young man thought would fit me. The problem was, he explained, I couldn’t try them on. I had to buy them on faith, as it were. He measured me carefully and assured me they would fit, so I purchased one pair in pink, giving him the cash and pocketing the receipt.

"Wonderful," he said. "Now, why don’t you go in and put them on and I’ll fetch you a bra and a slip."

I went into the dressing room and removed my sneakers and socks, my jeans and my shirt and, finally, my briefs. I picked up the beautiful pink satin panties, placed my feet through the leg holes and slowly drew them up my legs. The feeling was indescribable.

"Are you decent?" he asked, pushing through the curtained opening without waiting for an answer. "Oh, yes, very nice indeed." He looked me up and down, then shoved an armload of clothes into my hands.

"There’s a nice pink bra in there somewhere," he said. "Put it on, then wait for me. I have an idea."

I found the bra, a lovely satin and lace confection in much the same shade of pink as the panties. I hooked it in front then turned it around the right way and managed to fit my arms through the straps. I saw some foam pads in the pile of things he’d brought. I placed them into the bra and they filled it out okay. I looked at the slips he’d brought, four of them, all in pink, one satin, two nylon, another in a chiffon over nylon layered effect. One was prettier than the next. But I made no move to put any of them on.

The young man returned with another armload. He deposited the items on the bench that ran along the back of the dressing room, beneath the bar that held the skirt and blouse.

"Do you have a femme name, dear?" he asked.

"Cynthia," I said.

"Mmmm, yes, it suits you," he allowed. "Let’s try this, shall we, Cynthia?"

He held up an old stretch girdle in pink. It was worn but serviceable.

"Okay, uh..."

"Oh, I beg your pardon," he said, extending his hand limply. "My name is Timothy."

I shook his hand and, again, felt the electricity. I couldn’t meet his eye, I was blushing so furiously. I raised my arms so that he could wrap the girdle around me and I concentrated on breathing as normally as possible, while he tugged and yanked and pulled until he had the garment properly positioned.

"It’s not quite as effective as a good corset, but I think it will do the trick."

Then he began attaching garter straps to the little metal hooks hanging from the girdle.

"Oh, dear," Timothy said. "I’m afraid we got a bit ahead of ourselves."

"I’m sorry..?"

He pulled his attention away from my lower body with a slight frown, but when he met my eyes, he shrugged and smiled. "If we put these on over your panties, you’d have a heck of a time taking them down to go to the bathroom," he explained. "Not that it’s a big deal, here and now, but you’ll want to remember that if you’re going out."

"Should I take off..."

"Well, it never hurts to do things the correct way...would you mind? I can wait outside..."

Before he finished, I had the panties down around my knees and was lifting one leg to get them off.

"No need," I said. "It’ll just take a second." I suspected he knew what I was doing, even if I wasn’t sure myself, but I couldn’t help it. The urge to flirt with this guy was absolutely overpowering. He made as if to turn away for my modesty, but I caught him, in the mirror, checking out my package. I’m not exactly hung like a horse, but I’ve got enough and his expression seemed to indicate approval.

He handed me the straps and said, "Can you manage with those?"

I didn’t even try. I just said, "Well, I’m not sure, but..."

That was all he needed to hear. He turned and took the straps from my hands. Then, I guess, figuring it was pointless to keep acting like my cock wasn’t standing up at half mast right there in front of him, he looked it over and with a quick glance to my eyes, muttered, "Very nice."

"Excuse me?"

"Oh, I am sorry. I was just, well, you know, admiring what wonderful shape you’re in." He smiled and I smiled and then he knelt down on one knee and began attaching the straps, turning me a little after each one was fastened, until I’d spun around completely and my tool popped back up between us.

"You’ll need to tuck that away at some point," he said, "or it’ll ruin the line of your skirt."

I made a motion to do just that, but he motioned to stop me, saying, "Not a priority yet, Cynthia."

I smiled at him and got a rakish grin in return.

"Sit," he said and, once I did, he began fitting tan silk stockings over each of my legs, running them up, driving me mad with his touch as he smoothed them up my calves and thighs and fastening them to the garter straps. "There, now," he said. "How does that feel?"

"Wonderful," I managed to say.

He stood up and moved back a bit to take me in all at once. "Oh yes," he said. "I believe the look works rather well. I suppose it’s time to tuck your friend away now."

I let him know, with my eyes, that I was as sorry about that development as he was, then I tucked my cock back between my legs and pulled my panties back on. As I straightened up, Timothy was holding the chiffon and nylon slip open for me to pull over my head. I put my arms and head through, then let it fall down over my body like a stray breeze caressing my skin. It felt exquisite!

Timothy worked the slip a bit, then stood and looked me over again. He seemed pleased. I checked the mirror. I looked nice. It would have been better with makeup, but otherwise the illusion wasn’t half bad. The blouse and skirt came next, both fitting very nicely indeed, except that the sleeves of the blouse were a shade too short, but I was used to that. The ruffles helped to disguise that fact, anyway.

Timothy produced a pair of shoes, fuck-me pumps in black with three inch heels and, miracle of miracles, they actually fit. They were a bit tight, but I could get them on and walk in them! I was ecstatic!

"Okay," said Timothy. "One last thing, just for the complete effect, okay?"

I didn’t know what he meant, but I nodded. He left the dressing room for a few moments, then returned with a small makeup bag. He took things out and went to work on my face. My facial hair was very fine and blonde and I’d shaved very close that morning from habit, so there wasn’t much of a beard shadow to cover. He gave me a bit of powder, a bit of blush and then he spent a few minutes on each eye. Last, he did my lips in a blazing shade of red.

A critical once over, then he frowned and said, "Just a sec."

He moved out of the dressing room again, returning a few seconds later with a large black and white silk scarf. He rolled it up and tied it under my hair in back and over it in front, leaving bangs hanging down below on my forehead and knotting the headband-style silk directly over my left ear, so that the ends bobbed around in my peripheral vision and tickled my ear. Then he attached a pair of dangling clip-on earrings to my lobes. Finally, a black choker went around my throat.

"There!" he said with no small amount of pride. "As pretty as a picture. Come look in a good mirror."

I followed him out to the three angled mirrors beside the counter. I turned this way and that, awestruck at the transformation he’d effected so quickly and casually. I preened like a little girl all dressed up for the first time.

"I can’t believe it," I said. "How did you make me look so good so easily? I can never get myself to look like this."

"Practice, darling," he said with a smile. "And it helps to have the right canvas to work upon. You really are quite attractive as a woman, you know."

I blushed again and said, "Thank you. You really think so?"

"Oh, indeed, I do."

"You think I’d get checked out, looking like this?" I asked.

"I think the boys would be all over you, Cynthia. I haven’t the slightest interest in girls and I think you’re more than pretty enough to kiss."

"Really?"

"Really."

"Would you care to prove that?" I asked, my heart pounding now like it wanted to burst free of my chest.

He smiled, full voltage this time, and I felt myself go faint. He stepped forward and placed his hands on my hips. Gently, he pulled me closer and, once I was hip to hip with him, he brought his hands up to cup my face and he slowly brought his lips to mine. He pressed them against my lips and I felt his tongue brush across my mouth. I opened up and let him in, moving my tongue up to meet him.

We stayed there for a moment, tongues darting around one another, and he began to touch me with light brushing motions, my back, my chest, my hips, my ass. I was melting in his arms, light-headed and feverish in the embrace, pulling him closer and opening my mouth wider to let him explore every nook and cranny. His hand brushed against my crotch and my cock sprang free, bumping out against his palm. He grasped it lightly and began to rub the underside with a soft circular motion. I moaned as I felt the friction on the tender spot just below the head.

He broke off the kiss slowly, planting little pecks on my cheeks and neck as he moved me back.

"I am sorry," he said. "That’s not like me at all. In several ways!"

"I’m not sorry," I said.

He smiled again, half-strength and I still got dizzy.

"No one has ever done anything like this to me," I said. "I’ve never looked like this, felt like this, or needed this the way I do right now. You did this. I don’t know how, but you did this. And I have to find some way to thank you."

All at once, I knew what I wanted to do. It was a drastic step, one which I’m almost certain I would never have made in the cold, gray light of reality, but this was a Technicolor dream sequence I was living with my emotions in turmoil and my cock harder than I had ever felt it and, somehow, I knew that this was my one chance to find magic in this bizarre fetish world I lived in.

‘I may go back to wanking on the couch in a ratty old nightgown as soon as I get home,’ I rationalized in my mind, ‘but I’m going to make this opportunity count today. This is going to be a day to really remember, damn it! I’m going to live my dream for a change, instead of just jerking off to it as it goes by in my imagination!’

And with that decided, I grabbed Timothy’s hand and pulled him towards the dressing room. Along the way, I saw something I’d noticed out of the corner of my eye a little earlier. It was one of those cheesey souvenir pillows from Niagara Falls, stained satin with a picture of the falls embroidered on it along with the year - 1947. I grabbed it and brought it along.

When we were both inside the dressing room, I pulled the curtain and, seeing Timothy was about to say something, I put my finger over his mouth.

"I only want one word out of you," I told him, thrilled at my boldness, now that my mind was made up. "And that word is either yes or no. The question is: Are you healthy?"

He looked at me, amazed, but then the smile crept back to his face and he nodded as he said, "Yes."

"Good!" I exclaimed as I tossed the pillow onto the floor in front of him and, gathering my skirt up out of the way, I knelt down in front of him. I opened the snap and the zipper on his pants and tugged them down to reveal a lovely pair of satin boxers. I rubbed his crotch through the silky shorts, then I pulled them down and did my best not to faint when his cock swung out before me. It was gorgeous, about five inches soft, I guess, but it was growing and I loved the way it pulsed in my hand.

I looked up and saw the pride on Timothy’s face. He knew he had a cock to die for. I’d never imagined that there could be such a thing, but there it was before me. I felt none of the revulsion I’d always expected to feel, rather I felt the excitement I knew so well from when this moment occurred in my fantasies. I’d never actually held any cock but my own and yet, nothing I’ve ever done felt as right as it felt at that moment to put my lips to the helmet of his throbbing member and gently kiss it. As I looked down at it, I watched a hint of pre-cum flow from the slit at the end, glistening under the bare bulb hanging from the ceiling. I licked at it and was rewarded by a stickiness that seemed to have no taste.

Timothy gasped a little at that and I looked up to catch his eye. As he gazed at me, I slowly wrapped my mouth around his cock and licked it up and down with my tongue. I slid my mouth down and back, almost letting it get free, then plunging it back into my mouth, forcing it back towards my throat. I gagged a little, but I kept taking as much of it into my mouth as I could and gradually, my throat stopped rebelling. I was bobbing up and down on his cock furiously and he had his hands on either side of my head, urging me on. He was groaning the most fabulously filthy encouragements to me.

"Suck it, you bitch! Eat my cock, you little whore! You like it nasty, faggot?"

I did my best to smile and nod around the pulsing shaft I was deep throating so fiercely.

All at once, he began to tremble and shudder and his cock seemed to swell even larger and, with a blast so powerful, it nearly knocked me down, his spunk shot out in surging blasts of ropy, sticky fluid, coating the back of my throat, filling my mouth faster than I could swallow and leaking out the sides of my mouth to dribble down my cheeks to my chin. It was salty and pungent with a sort of chemically medicinal taste I couldn’t place (until someone years later mentioned ammonia and, startled, I made the connection).

He just kept pumping and it might have gone on much longer, when all of a sudden, the curtain was yanked open and some woman was standing there screaming at us!

"What the fuck do you think you’re doing!" she yelled, mostly at Timothy but also at me in a sort of secondary way. "Are you insane? Getting a blow job in the dressing room? What the fuck are you thinking? Who is this little whore, one of your club hopping bimbos?"

"Marion, wait, please, calm down and let me explain."

"Explain? You fucking idiot! I don’t want to hear you explain. I want you to get the fuck out of here right now! You’re fired!" She was mid-thirties, I figured, attractive in a hard sort of way, with too much make-up and an ass that was probably spreading faster than a flu bug. She looked like a total bitch. She bored in on Timothy again and said, "I’ll get your jacket."

Timothy just slumped against the wall, his cock dribbling the last of its discharge. I put my hand out to steady myself as I rose.

"Timothy, I’m so sorry."

"It’s okay. It’s not your fault. Oh, shit." He shook his head and just stood there.

"I’m really sorry."

"Forget it. Fuck."

"What?"

"I just remembered, my rent is due this week. That bitch Marion better give me my pay or I’ll kill her. Stupid, stupid, stupid."

I felt awful. This sweet, sweet guy had given me the most wonderful gift I could imagine, an afternoon of such delight and surprise, and how did I pay him back? I get him fired with his rent coming due! Shit!

The bitch reappeared in front of us, shoving Timothy’s suede jacket at him. "Here, asshole, take it and get out!"

She gave me dagger eyes and asked, "You still here?"

"I don’t think you’re being very fair to Timothy," I said.

"Get the hell out of my store, slut!" she hissed. I wanted to explain that I couldn’t, but at the same time, I registered the fact that she still hadn’t realized I was a male in drag. And I wasn’t sure I wanted her to realize it. But I couldn’t very well go out in the street dressed like I was. I couldn’t think. It was all happening too fast. Marion kept screaming at both of us until she finally ran out of steam and stood with her hands on her hips, waiting for us to do as she’s ordered.

I took my handkerchief from my jeans and gently wiped Timothy’s dick clean, so he could put it back in his pants. Then I said to Marion, "Would you mind? I’d like to get changed first."

"What do you mean?" she demanded, then she looked at me, looked at my regular clothes hanging there, looked at me again and the light went on in her eyes.

"I don’t believe it!" she said. "You’re a guy. A fucking faggot in a dress!" Then she turned her attention back to Timothy. "What the fuck were you thinking, Tim? A fucking drag queen? It’s not enough you sleep through half your shift, you gotta spend the rest of it getting a blow-job in the dressing room from a drag queen? I knew you were a bit light in the loafers, but for Christ’s sake, a drag queen?"

"I’m not a drag queen," I said with as much dignity as I could muster. "The correct term is transvestite."

"Oh, well, excuse the shit outta me," barked Marion. "That makes all the difference." She looked me over again and appeared to have a thought. "Those my clothes? From my shop?"

"Yes."

"You don’t look bad, you know," she mused, the professional in her peeking through for a moment. "Took me a minute to see it. ‘Course I was screaming at Tim at the time."

"Thank you."

"You two old friends?" she asked.

"Actually, we met today for the first time," I reported.

"And you wind up on your knees in the dressing room?" she cackled. "I had no idea Tim was such a charmer. Talked you right into, huh?"

"No, actually, it was my idea," I told her. "He was so nice helping me with the clothes and I just found him so attractive. I’m sorry. I know it was wrong, but I’m the one who started it. I don’t think you should fire him for giving in to me. I mean, it’s not like I’m Farrah Fawcett or anything, but I imagine he found me attractive enough and this kind of thing certainly doesn’t happen very often, I’m sure, so you can hardly blame him for wanting to seize the moment."

She looked at me in frank amazement. "You’re gonna stick up for him?" she said. "He convinces you to blow him in the dressing room and you want to help him keep his job? What the fuck do you care?"

"I feel responsible," I said. "He didn’t convince me. I convinced him. And I wouldn’t have put him in this position if I’d thought anything like this could happen!"

"Oh yeah? Well, let’s see now." She thought for a minute, then it was like you could see the light bulb appear over her head. She got a sort of a mean grin on her face. "Okay, I’ve got a proposition for you. You really wanna save his job for him, faggot? You really want to help poor Timothy get out from under his mean old boss lady?"

"I’ll do whatever it takes to convince you to give him another chance."

She started laughing. "No you won’t," she said. "You’re talking like you mean it but you won’t go the distance for him. You’ll punk on him like the faggot asshole you are. You don’t have the balls to save his ass."

"Just tell me what you want," I said.

She looked at me for a long beat, then she chuckled and said, "Okay. Fine. Let’s see if you mean it. What I want...what I want is for you to turn around, bend over, drop your panties and let Timothy here fuck you up the ass while I watch! How’s that, queerboy? You man enough or woman enough or screaming faggot queen enough to do that for your wispy little faggot boyfriend? I don’t think so!"

Timothy looked at me in horror, shaking his head no, tears forming in his eyes. I put my hands on his cheeks and tilted his head up to look at me. "Okay, c’mon now, lover boy. Let’s get your tool out here and I want you to give me the fucking of my life!"

"Cynthia, no," he said in despair. "I can’t let you do that. I can’t let you do it to yourself to save my stupid job."

I got real close and started whispering in his ear. "Don’t worry, Timothy. This is okay. I’m alright with this. Believe me. Her doing this to us is just the kind of humiliation that I crave when I’m dressed like this. Remember what you said before about being afraid of people not accepting you for who you are? Well, this is who I am! So, you have to accept that. And if this’ll get you your job back, then it’s not really something I should have to argue with you over, is it?" Then I tried my last trump. "Besides, don’t you think I’m cute enough to fuck?"

That got a half smile out of him but despair overtook his expression again as he spoke. "Look, you don’t know her. She’s crazy. I can’t let you do this."

"Tim, dear, you and I don’t have a choice. Now don’t make me beg you. Fuck me. Please!"

And, with that, I turned away from him and bent over, tossing my skirt and slip up over my ass. I lowered my panties and pulled my ass cheeks apart and waited.

I heard him muttering and then I heard the sounds of him lowering his pants. "I need some lube," he said.

"Use your spit," snarled Marion.

He spat on his hands a few times and then started shoving a wet finger up in my crack. He found my anus and probed at it gently with the tip of his finger, rubbing some spittle around the hole. I watched him in the mirror as he spat in his hand again and applied it to his shaft. Then I felt his shaft, slightly wet around the head, poking at my puckered tunnel. He worked it around a little, then slowly, determinedly, he pushed it in. It hurt like hell, so much so that I almost screamed. I could hear Marion’s heavy breathing as she watched. I could smell the beer on her breath, even from ten feet away. Stupid drunken bitch wants to see the faggot get poked? Okay, let’s give her a show!

Suddenly, it slid in all the way and I squealed like a pig without thinking twice. It was so painful, but so good at the same time. I’d never felt so humiliated and yet so happy. Timothy started to move it in and out slowly as the pain gradually subsided and was replaced by a feeling of contentment, fullness, satisfaction.

Marion was grinning this twisted little smile as she watched my ass get pounded. Tim was picking up speed and I was feeling fireworks start to go off, way in the back of my mind, but moving closer. I arched my back and my face turned towards Marion to see how she was enjoying the show. I saw her standing there with her mean grin and suddenly, she had a camera in her hands, a Polaroid from the look of it, and the flash went off in my eyes, blinding me! As my vision returned, I watched her pull the picture from the camera and start waving it in the air.

When it came up, she showed it to me. There I was, my mouth open in a howl of pleasure, cum still dripping down my face, Timothy buried to the hilt in my ass with his eyes closed and a look of pure pleasure on his face. It was so humiliating to see that photo in front of me as Timothy continued to fuck my ass in front of this bitch. He’d just cum, moments before, so it could well be some time before he was able to shoot again. Good thing I was enjoying my reaming.

After a few minutes, I felt the change in his cock and in his breathing and I knew I was about to get creamed inside. He shot a lot less this time, but the force with which it came out was undiminished and my ass filled with a warm wet creamy stickiness. Tim slumped over me for a moment to catch his breath, then, as he slowly pulled his cock out of my ass, Marion leaned in and took another photo, close up and personal.

Tim slumped down on the bench, weary from his exertions. Marion looked me in the eye and said, "Now, get back on your knees and suck his cock clean!"

I never even thought about disobeying her. I moved the satin pillow into position and went to work on Tim’s cock. It had a different taste this time, less appealing but interesting all the same. I cleaned it gently and thoroughly, before standing him up and getting his shorts and pants back on.

Marion took several more photos as I performed these duties and gleefully showed me the results.

"Okay," she said, when I’d finished. "You did good, faggot. You want to hit the can to clean up?"

"Yes, please."

She motioned for me to follow her. We went into the back room and she pointed out the bathroom. I went in and relieved myself, then daubed gently at my aching anus with a folded piece of toilet paper. It came out stained brown and wet, but I was pleased to see there was no blood. I stuffed another chunk up into the crack to absorb Tim’s cum as it leaked out, then put myself back together and returned to the main room.

I walked over to the dressing room to see Marion with my wallet open in one hand and my driver’s license in the other. I stopped short in horror!

"Well, now, Philip," she said, "looks like you live in a very nice neighborhood. Be a shame if all your fancy neighbors got copies of dirty photos with you dressed in drag getting buttfucked by the Village pansy over here. Maybe you want to think about what you can do to make Marion’s day a little brighter!"

I was frozen with shock. I couldn’t let anyone find out about my sexual secrets! What did this crazy bitch want from me?

"I’ll do what you want," I muttered.

"Sorry? Couldn’t quite hear you, faggot!"

"I said, I’ll do what you want."

"Not good enough," she said. "You have to convince me you’ll be happy to do what I want."

It took several more times of saying it with an increasingly ludicrous grin on my face before she was satisfied with my efforts, then she shoved Timothy over into the corner of the dressing cubicle and, lifting her skirt above her waist and pulling her panties aside, she motioned me to go down on her.

Back to my knees on the pillow I went, moving in slowly as the aroma of her pussy reached out to me. Slowly, I began to nuzzle her hairy thatch, using my nose to work the slit open and tickle the clit enough to get a little lubrication flowing. Then, I started giving my tongue a considerable workout. I slurped and licked and stroked and teased. I gave her clit a going over it’ll never forget. I was down there for what felt like hours but was probably not much more than twenty minutes or so. Marion was one of those operatic orgasmers, bursting into an aria every time her juices started to really flow. At one point, her hands clenched and unclenched and from the corner of my eye, I saw my driver’s license flutter to the floor beneath the bench. I made a mental note to pick it up when I got free of this bush country I was slowly slurping my way through.

Despite his exhaustion and despair over the way the day had turned out, Timothy sat up a bit and started to watch as I insistently worked Marion’s pussy to the point where she slid down in her seat and finally pushed me away, sated.

"Not bad," she allowed with an evil grin.

"Yes," added Tim soberly. "Cynthia’s quite talented with her mouth."

"Yeah, she sure is. But I think we’re going to give her one more task." Marion looked me up and down, then said, "You buying that blouse and skirt?"

I nodded.

"Right. Then take them off, put them back on the hangers and place them on the counter."

I removed them and hung them neatly, but then I hesitated.

"What are you waiting for?" demanded Marion.

"I...I’m just thinking..."

"Yeah, yeah, c’mon, spit it out."

"Well, what if someone walks in while I’m out there in just my slip?"

That cracked Marion up. Even Tim had a fleeting grin cross his face.

"After what we just did, you’re worried someone’s gonna walk in and see you in your underwear? Holy shit! That’s the funniest thing I ever heard!"

Put that way, I saw the humor in it, too, and started to smile. As I pulled the curtain aside slowly, Marion said, "Forget it, I locked the door before. I didn’t want anyone coming in and spoiling our fun. Go on, put your stuff on the counter."

So I did.

She followed me out. "Now take off the slip, fold it nicely and add it to the pile."

Tim came out of the dressing room, too, and watched as I slowly disrobed and put each piece of clothing on the pile.

"What about those other slips?" Marion asked.

"Well, I didn’t try them on, yet."

"Then get to it."

So under her scornful gaze and Tim’s soft glance, I tried each of the other three slips on. They all fit very nicely and Marion took my picture in each one. I was wearing the last one, a nylon tricot number with heavenly lace trim, when Marion said, "Okay, next task!" She pointed to an old couch against the far wall. "Lay back on that and jerk off for me."

I was so humiliated by this time, I never even gave it a second thought. I reclined on the couch, pulled my cock out of my new panties and started stroking it. I used the hem of the slip to help slide my hand up and down and in a few moments, I was rewarded by the most ferocious orgasm I could ever remember having. The cum shot out and I aimed it away from me, down my leg. Marion caught a shot of my dick as it spewed jism down my thigh. I sat up slowly once I’d recovered my wind and looked around for something to wipe it off with.

At that moment, I felt the worst I’d felt all day. Unfortunately for me, cumming temporarily wiped out the delight I normally felt at being in drag and being humiliated. The ecstasy was replaced by a crushing, totally non-erotic shame that usually caused me to pull the clothes from my body and hurriedly get back to normal regular activities, so I could force the disgust I felt at my weaknesses out of my mind. But here, in front of Marion and Tim, I had no easy way out, so I hoped she was through with me now. I just wanted to be as far away from there as I could be as quickly as possible.

No such luck.

Marion pointed at the glob of cum on my thigh and said two words, "Eat it!"

I knew I had no choice, so I slowly scooped it up and licked it off my hand. Swallowing my own seed was infinitely harder than swallowing Tim’s, not only for the revulsion I felt now that the turn on was gone, but also because it was my own spunk, which somehow seemed worse. But, at last, I finished it and then I asked Marion, "May I go now?"

Marion thought about it for a minute, then said, "Yeah, sure. Go ahead and change and I’ll ring you up."

When I came back from the dressing room in my jeans and shirt, Timothy handed me a jar of cold cream and a box of tissues and pointed towards the bathroom. A few minutes of work and the makeup disappeared. I returned to the register, looking like the same guy who came in out of the rain a scant two hours before. But inside, I was someone else altogether now. I was as completely different as I could be and I knew that nothing, from this moment forth, would ever be the same.

The clothes were expensive and it nearly wiped out my cash, but I still had enough for the bus and I had a return ticket for the train. Marion was busy tacking up the photos she’d taken of me on the side of a shelving unit behind the counter, where customers couldn’t see them, but anyone working the register would have a clear view. I thought about asking her not to do that, but I knew it would only piss her off again and I did not want to do that. I hoped I could contact Tim somehow and get him to retrieve them for me.

Finally, with my purchases in a big shopping bag, I said goodbye to Marion, who gave me that nasty grin again and walked to the door with Tim, who gave me a soft kiss on the cheek as he held the door open for me and said, "I’m so sorry, Cynthia."

"I know, Tim, it’s okay. Really, it is. Can I call you or something? I was hoping maybe you could get the pictures for me somehow, maybe in a few days when this blows over a bit?"

He took a store business card and a pen from his shirt pocket and scrawled his name and number on the back, put it into my shirt pocket and kissed my cheek again. "I’ll see what I can do, but don’t get your hopes up. You can see I wasn’t kidding when I told you what a crazy bitch she was," he said

Marion yelled from the other end of the room, "Enough with the whispering, you two lovebirds. We have work to do, Tim. Get moving."

Tim unlocked the door, the little bell tinkled and I went through it into the stairwell, thinking I’d probably never see him again.

At street level, I stopped a second to compose myself and that was when I realized I’d never retrieved my license from the floor where Marion had dropped it.

"Oh, fuck!" I said and, with dread, I started the climb back up the stairs.

When I reached the landing, I stood there for a moment, trying to figure out how to handle the situation. If I went in and she saw me, I’d have to say what I came back for and she might grab the license and refuse to give it to me. That would really suck. So, I decided I’d try to sneak in as quietly as I could and retrieve it without Marion knowing I was there. If Tim spotted me, I felt certain he’d understand and keep quiet - even help me if he could. But to get in quietly, I’d need to deal with that damn bell.

I opened the door as quietly and slowly as I could and I reached up and silenced the bell with my hand. Thank God for these old buildings with doors built to accomodate the shorter people of an earlier age. I slipped through and peered around the rack of sale clothes by the door to see if Tim was at the counter. He wasn’t. I left my shopping bag by the door and slipped along the wall to the dressing room. Inside, I crouched down and found my license, lying on the floor beneath the bench. I grabbed it and shoved it into my pocket. As I slipped out, I heard noise from the back room. My curiosity got the better of me and I moved along to the door that led to the back, ever so slightly ajar, and listened. What I heard made my blood run cold!

Tim was laughing his head off, then he said, "And when you told him to eat you out, I was dying. I was so afraid I wouldn’t be able to keep a straight face."

"You?" howled Marion in response. "Are you kidding? You should have seen the look on his face when I pulled the curtain open and he’s there on his knees with a gallon of your spunk all over his face. I nearly pissed my panties."

"You were great," Tim said, choking back tears of glee. "I thought he was going to shit."

"Best one yet," Marion laughed.

"Oh, he was so into it," said Tim. "I didn’t have to say or do a thing. He really did lead me back to the dressing room himself. I never mentioned a blowjob, that really was his own idea."

"Serves the little faggot right," said Marion with savage satisfaction.

I was horrified. I’d been set up and I’d fallen into their trap like a complete and utter fool. A wave of the most profound humiliation I’d ever felt washed over me and I did the only thing I could. I pushed the door open and stood there looking at them. They turned and, with less than a second of surprise on their faces, they just laughed their heads off at me, knowing I’d heard what they said and not caring a bit.

I was hot with shame and I stood there listening to them laugh at me.

"Come back for more abuse, faggot?" asked Marion.

I couldn’t move. I felt paralyzed.

"Want to suck a little more dick, Cynthia darling?" asked Tim cruelly.

"Poor little faggot’s just realizing what a total fool we made of him, isn’t that right, sissyboy?"

I nodded dumbly and realized, to my unending humiliation, that my cock was straining at my briefs. Marion and Tim noticed it at the same time.

"Look," squealed Marion in delight. "He’s getting hard thinking about how we fucked him over."

"Actually, Marion, I’m the one who fucked him over. Over and through and inside and out. Right, Cynthia? You just got your pussy licked, Marion."

She walked over to me and slapped me across the face, a vicious stinging slap that echoed in the room. "Take off your clothes, faggot," she ordered. "I’m going to have some more fun with you!"

I scrambled out of my clothes quickly. Inside, my common sense was screaming at me to grab my stuff and get out, but I couldn’t do it. I had to put myself through this. I had to follow this through to the very end.

I stood before her naked and she snickered at me.

"Find this sissyboy something to wear, Tim, would you?"

He rooted around in a pile of clothes and pulled out a black satin slip and a pale yellow satin blouse. He handed them to me and I put them on, stuffing the cups of the slip with some rolled up gym shorts. He found me a silk scarf, which I tied around my head the way he done earlier. Then I was handed some old pantyhose with runs down both legs, which I climbed into.

Marion pushed me back into an old wooden swivel chair. She went to her desk and opened a box of Dunkin’ Donuts sitting beside the phone. She pulled out a donut and brought it over to me. It appeared to be a jelly donut. She poked her finger into the little hole on the side that was used to pump the jelly in. She widened the hole with her finger.

"Lift up your slip, faggot and pull down your pantyhose."

I did and my cock was exposed. It was getting hard. She took my cock in one hand and the donut in the other and slowly, inserted my cock through the hole in the side of the donut. When she removed her hands, the donut was impaled on my tool. She took a picture.

"Now," she said with glee. "Fuck the donut."

I grabbed the donut in my hand and slowly slid it up and down the shaft of my dick, feeling the slimy, sticky goo rub against my skin. I was so horny and humiliated, it only took a few minutes before I was arching my back and grimacing as my jism shot out from the tip, into the donut’s insides.

Marion took the donut and held it in front of Tim’s crotch. He lowered his pants and I knelt before him and jerked him off with the donut as well. Then I licked his cock clean.

Marion took the donut and, hacking up a large green glob of phlegm, she drooled it into the hole of the donut. Then she passed it to Timothy, who did the same. I knew what was coming and, as much as the thought disgusted me, I knew I would do as I was told. Sure enough, she handed the donut to me.

And said, "Eat it."

"I’d rather not."

Tim laughed nastily. "I’m not surprised. What’s the matter, Cynthia darling, don’t you like donuts with a cum, spit and snot filling?"

"Actually," I said, "it’s the jelly I’m not fond of."

They cracked up and, while they watched with delight, I slowly consumed the donut, doing my best to make each disgusting bite look like a sexual paradise, letting the cum drip over my lips and the snot hang off the tip of my tongue. My cock was hard again already and I hadn’t even noticed my usual post-coital funk. I was being humiliated beyond my wildest dreams by a pair of cruel dominators and I was loving it.

"Now," she said. "I have one last thing I want you to do."

"Alright."

"Don’t you even want to know what it is?"

"Whatever," I said.

Marion laughed and once again lifted her skirt and pulled her panties aside. "Face right here," she said, pointing at her crotch.

I looked around, then went back to the dressing room to retrieve the pillow. I placed it on the floor at her feet and knelt before her.

"You thirsty?" she asked with that wicked grin.

I knew then what she was planning. I wanted to leap to my feet and scream no and leave, but she knew my name and address, so I no longer had that option. Resigned, I planted my mouth over her pussy and nodded I was ready. She let loose with a stinging blast of piss, steaming hot and acrid, like a bitter medicine the doctor forces on a recalcitrant patient. It came out so fast, I couldn’t swallow quickly enough and some leaked out of my mouth and dripped down onto my chest. Then, all at once, Marion shoved my head back so that I lost the seal on her cunt and the piss splashed all over my face, in my hair, down my front, into the front of my slip and blouse. It just kept shooting out like gas from a pump, no end to it and I was quickly drenched from head to toe.

Finishing finally, Marion motioned for me to bring my face back in close. "Lick me clean, faggot."

I did, utterly humiliated now, beyond any feeling I’d ever experienced. Then, she said, "Now it’s Tim’s turn."

I looked up at her and saw only that death’s head grin. Tim was grinning, too.

I moved myself and my pillow over to Tim and pulled his pants and shorts down. I put his cock in my mouth and nodded. It took him a moment or so to get the flow started, but it came out strong and when Marion gave me the signal to move back and let it wash over me, the stream pounded my face. It went up my nose, in my eyes - burning furiously - and down the entire front of me. I was utterly piss-soaked from top to bottom.

"Good," said Marion. "Now, let’s get your things put away." She took my clothes and put them into another shopping bag. She sent Tim to retrieve my other bag by the door, from which she removed the fuck-me pumps. "Put them on."

She looked through a pile of clothes and pulled out a silky calf-length polyester skirt in black with a floral pattern. "Put this on, too." She took the makeup bag from the table and sat me down, doing a quicker and altogether less flattering job on me. Then she gave me the shopping bag with my purchases and said, "You are to go out and walk once around the block. Then you’ll stand in front of the store on Second and look up at this window." She pointed to the window by her desk.

"When you see the curtains get pulled back, you can come back up and we’ll give you your own stuff back and you can change and leave, okay?"

"Alright."

Tim walked over with another scarf, which he folded into a triangle, draped over my head and tied beneath my chin. I looked like one of the Monty Python British housewives. I felt a total fool. Marion thought for a second, then she got the donut box off the table. She opened it and showed me what was left –four more jelly donuts.

"Lift your skirt," she said. I did as I was told. Tim pulled out the waistband of my pantyhose and Marion dropped the donuts down into my pantyhose, two down my crotch and two down my ass, one at a time, pausing in between to mush them in. Satisfied with the mess she’d made, she let me release my skirt. They led me to the door, but before she opened up to let me out, Marion stopped me and looked me over.

"Oh yes," she said. "One last touch."

She hawked up another load of phlegm and spat it out on my face. It hit me on the forehead and slowly oozed down over my brow. Tim moved up alongside her and did the same. His hit me on the cheek. Marion scraped up another and hit me in the left eye, effectively closing it. Tim’s second caught me with my head tilted back, so it went partially up my nostril. They kept taking turns until each of them had spit on me at least a dozen times.

"Now, you can’t wipe any of it off until we let you back in, got it?"

"Yes," I said and a trickle of snot-laced spit dripped into my mouth while it was open.

I walked down the stairs carefully, mortified beyond belief that I was allowing myself to be degraded in such a fashion. But I was powerless to resist. She knew who I was and could ruin my life, but what was far worse was the realization that I’d probably have gone along with them anyway, even without the threat. I wondered if they knew that.

I got to the street and slowly started walking around the block. I was taunted by a bunch of young guys on the corner until they saw the mess on my face and they turned away in disgust. The smell of piss wafted from me like an open toilet that hadn’t been flushed. People stepped aside to avoid brushing against me and looks of disgust and revulsion were all I saw. It took an eternity to circle the block and I knew I was being stared at and laughed at and worse. I could feel the sticky goo of the donuts working up into the crack of my ass. Finally, I got back to the front of the store and I stared up at the window. It seemed dark but I knew when they moved the curtain aside, I’d see the light. The sun had set and night traffic was on the streets, the bustle of early autumn rush hour in full swing. People kept staring at me, the obvious drag queen with the poor makeup job and the torn pantyhose and the smell of piss around me and the green snot all over my face.

I stood there patiently, waiting for my tormentors to tire of my humiliation and let me back in to get my clothes back, my wallet back, my life back. I needed to piss so badly, but I was afraid if I moved, I’d miss the signal from the window. I hopped from one leg to the other for as long as I could, then figuring it couldn’t really make much more of a difference to how I smelled, I pissed in my pantyhose, the warm urine running down my legs and puddling at my feet. People walking by were commenting on my disgusting appearance and my filthy habits. I didn’t move. I couldn’t. I prayed they’d let me in before I needed to shit. Shitting myself out here, that would be too much to bear.

It couldn’t be long now, I thought. They’ll want to close up and go home. No, it couldn’t be much longer now. And then, it started raining again.

 

THE END

 

 

© 2000
The above work is copyrighted material. Anyone wishing to copy, archive, or re-post this story must contact the author for permission.