Exchange

Published on Feb 8, 1996

Transgender

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Exchange

I saw the ad for a roomate needed in the local personals, and figured this was perfect for me: a couple in need of a third party to split rent and utilities. I had my own room, could go and come as I wished, and overall it was a fine arrangement. Unlike other roomate situations I'd been in, this was the first time I'd also shared space with a female roomie, Sarah, who was living with her boyfriend, Ron.

What made it exceptionally nice was that it gave me access to her clothes when she and Ron were out for the day (or night, as the case might be). Having always been pretty slim, I found that her stuff was generally a perfect fit for me, though some of the more exotic things were just a little too snug for comfort. I would go into her/their room and try on as many different pieces as I could find.....bras and panties and camisoles and slips and dresses, all silky and sleek.

I discovered early on that because our bedrooms were directly adjacent to one another, that it was almost impossible not to hear them having sex. Sometimes it seemed to go on for hours, the head of the bed bouncing against the wall directly opposite my bed, their moans and quiet words slipping easily through the wall. Sometimes, knowing that they usually made love Friday or Saturday nights, I would slip a pair of panties out of the hamper or her bureau, and when I would hear them start to have sex, I would pull on the panties and imagine it was me in there with Ron. Often I managed to come at the same time they did, leaving me exhausted. They were taking part in a threesome and didn't know it!

One thing that I was able to pick up through the wall was her lack of interest in anal sex. I could hear him trying to talk her into it, even trying it a little once, but each time she said no, that it hurt too much.

This went on for about six months, when everything changed. Ron and Sarah had been fighting a lot lately, and one day she just said the hell with it and left. She packed a suitcase, announced that she'd send for the rest of her things later, and split.

Ron was devastated by her departure. He would go to work in the morning, and come home to eat his dinner in silence, hardly offering a word, despite my efforts to draw him out. And he began drinking...not a lot, but enough to drown his sadness and most of his intellect.

One night, he came back after being out late and had been drinking pretty heavily.....he was drowning in his loss, mad at her for leaving, and missing her all at once. He needed her, needed to be with her. He sat heavily on the couch, nearly in tears, and slid into sleep, wearing only his robe.

I sat watching him for a moment, and decided that I knew what I had to do. I went into the other room and pulled out her hottest outfit. She'd worn it with Ron dozens of times, and it never failed to turn him on: black seamed stockings linked to a lacey garter belt, black satin panties, a black leather miniskirt, white silk blouse and black bra. I slipped into the outfit, shaking, wondering if I was doing the right thing. Digging in the closet, I found the wig she'd bought and styled like her own when she'd received a terrible short hairstyle and wanted to hide it until it grew out again. I slipped the wig on, applied a little makeup, and in a dim light, I could actually pass pretty well for Sarah.

I stepped back into the living room, and switched off all but the night light from the kitchen. Went to Ron and, after hesitating a second, nudged him awake. He took a moment to focus, through the dark and the alcohol. "Sarah...." he said, half out of it. I could see the front of his robe tenting as his erection grew at the sight of the familiar outfit.

He raised one hand and let it slide down my hip, down to my stockinged legs. "Why'd you do it?" he said, sleepily, "why'd you go? C'mon...." With that, he pulled me down onto my knees between his legs. "Why? Damn it...."

He swallowed hard, his syes closed, and pulled my head up between his thighs, where his hard cock was sticking out. Having never sucked a cock before, I opened my mouth more to hesitate or protest, but that was all the opening that he needed, and he took my head and shoved it down, sliding his cock into my open mouth. It slid past my teeth and lips and over my tongue, hitting the back of my mouth. I adjusted myself as best I could as he began raising and lowering my head, holding either side with his hands and bucking up into my/Sarah's mouth. "Do it, c'mon, baby, do it...."

I slipped my hands behind his legs for a better gripk, and began bobbing my head up and down in his lap, his cock sliding in and out of my mouth. He pushed my face down further and further, until the whole length of it was in my mouth, despite my occasional gags, and he began fucking my face in earnest. For a long time the only sound in the room was the sound of my sucking, his cock sometimes coming right out of my mouth only to shove back in again.

Then, suddenly, he pulled my mouth off his cock and pushed me back onto all fours. "Run off like that, bitch," he said, holding me down, my ass raised, "I'll show you...too good for a little butt fucking, well, that's gonna change...."

This was more than I'd expected, and more than I wanted, and I started to pull away...I'd never been butt-fucked by anything larger than my own finger...but he moved my legs aside and shoved my hips back toward him. "No more 'no's' now, bitch," he said. I struggled more, and now he leaned forward, pinning me to the floor, one of his hands gripping my arms and holding me down as the other slide aside the one of the loose satin panty legs. "Fuck you, bitch," he said, "here, take it!"

And he lowered himself on me, his cock finding my ass by instinct. I wriggled beneath him, but instead of making it harder to enter, it helped get his cock past my asscheeks into the sphincter. He shoved harder, his cock lubricated by my mouth, letting his weight slowly drive his cock into my ass. I cried out as the pain shot through me, my cries muffled by the carpet in my face. He drove down and down into me, for what seemed like forever, until I felt him relax and settle, his cock now completely inside my ass, the skirt up around my hips.

He lay on top of me for a moment, savoring the feeling, then began slowly pulling out again. He stopped just short of coming out, and slid back in again. "Yeah, baby," he said, "take it, take it all." I could feel it filling every inch of me, expanding my ass as it drove deep inside. Then he began fucking in earnest now, his hips piledriving into me, faster and faster. By now the pain had subsided, and each stroke brought pleasure, driving my own panty-encased cock against the floor. I began bucking back to meet each thrust, my moans matching his own.

After a minute or two, he pulled me back up onto all fours, grabbed my hips, and started plunging into me to the hilt, over and over, as fast as he could. If I'd thought he was large in me before, now he felt huge as he rushed toward orgasm. The sound of our thighs slapping as he fucked my ass filled the room. Finally, with a loud moan, he slammed deep into me and I could feel his cock throbbing in my ass, the sudden warmth filling me as he came. At that instant, I also came, my cock exploding with Sarah's panties.

He pulled in and out a few more times as he came, the friction eased by his cum, and then slowed, leaning forward to lie on top of me. Laying beneath him, wearing Sarah's clothes, her perfume, having given him something that Sarah never had, I felt content.

That was our first time. The others...are a long and very wonderful story...for another time.

Fin

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