My Transexual Girlfriend
(M/?, oral, anal)
by Anonymous Author
Image, courtesy LADYBOY69.com,
I'd only moved into town a few weeks before, and so far hadn't met many people in Los Angeles. The first person I noticed right off was the Hispanic woman who lived upstairs and across two apartments from my own place. She had long brown hair, and a slender build, and she was attractive in a way I couldn't quite pin down.
I would watch her come and go on nights when I was stuck in my apartment. She had friends, and lots of them, and sometimes they would come over, or she would go out with them, sometimes all night.
One Saturday night, it must've been about midnight when I heard a knock at my door. I opened the door, wearing only a pair of running shorts, and it was her. She explained that she'd locked herself out, and needed to call the manager, who didn't live at the complex, to come let her in. "Can I use your phone?" she asked.
I of course said yes, and let her inside. She was wearing a long black skirt, practically to her ankles, soft and of some material like crushed velvet, only lighter. It outlined her features perfectly. I could tell when she passed that she'd been out drinking. She was tipsy as she went across the room.
As she bent over the phone to dial, I felt myself getting hard, though I tried to suppress it. Figuring that she would take a minute or two on the phone, I gently rubbed at it through the fabric of my running shorts as I stood behind her.
To my chagrin, though, she hung up without talking to anyone at the other end. "I guess no one's home," she said. "I'll have to try later." Her gaze fell on the bulge in my running shorts, and she smiled, a little drunkenly, I thought.
"My," she said, "is that for me?" She came over to me and, to my astonishment, began rubbing at it through my shorts. "You know, I've seen you watching me," she said. She said she didn't mind, that she'd been watching me, too.
She kissed me, and my hands went to her breasts, kneading them as she rubbed my crotch. They were soft and warm in my hands, and she moaned as I touched them. I parted her blouse, and ran my hands directly over her breasts, pinching the nipples. She knelt down in front of me, and my shorts were off in a second, my cock pointing straight at her.
She licked the head several times, flicking her tongue over it before sliding it into her mouth. Soon her head was bobbing at my crotch, swallowing every inch of me. Her mouth was soft and wet, and she worked it like there was no tomorrow. It was wet with both our juices in no time. I reached down toward her skirt, but she pulled me to the floor.
"Down here," she said, and laid me on my back. She pulled her blouse aside to reveal more of her breasts, and then straddled my hips, her long skirt rising up before me. She slowly lowered herself, letting the skirt pile up all over me as she descended. I briefly felt the part of fabric -- crotchless undies, I assumed -- and then she reached back behind her and took hold of my cock. I figured she'd continue to lower herself slowly, but to my surprise, after sliding her hand up and down my cock a few times, she dropped down onto it fairly quickly. Before I really knew what was happening, I was inside.
It felt wonderfully tight, and the fact that I couldn't see anything, that it was all invisible under her soft skirt, somehow added to the experience. With her hands on my chest for balance, she began to raise and lower herself onto me. I lay back and enjoyed the sensations. Her own head was thrown back as she rode my cock. I started to reach under the skirt to massage her pussy when she took my hands and placed them on her breasts, telling me to squeeze them. I did, hard.
She moaned, and began to sit on my cock harder and faster. Now, though, I began to notice that the angle felt wrong somehow. It felt no less wonderful, but she was too far up for me to be in her pussy. I slid my hands up her legs and, before she could react, found her pussy...only to find a cock instead.
She instantly stopped, sitting without moving, waiting for my reaction. I didn't know what to say, which must have been the right thing, because she slowly lifted her skirt to reveal the swollen cock beneath. It was clear that she had slipped me into her ass as she had first descended.
She was, she explained quickly, a pre-op transsexual, that she had tried to avoid having sex with anyone until she had the final stage of the operation, but it was taking a long time to get all the money in hand for the procedure, and she was going crazy without sex, and that if I was really turned off, we'd stop.
But the truth was that ever since I found out, my cock had gotten harder in her, not softer. Tentatively, never having touched one before, I reached out and stroked her cock, which was hard to the touch. Noting my acceptance, she began to move up and down on me again, finding her rhythm again. I'd never thought of myself as particularly gay, but somehow this was okay; she was mostly a woman, after all. Not that I really needed much of a rationalization; it felt too good for much thinking.
She continued riding me, harder and faster, stroking her own cock until suddenly my hips arched and I came within her. She gasped as I came, her face flush. She slowed, then stopped, sitting on me as I slowly softened inside her.
All the while, she kept stroking her cock. I watched it, fascinated. She hesitated, then finally asked, "Do you mind?"
I knew what she was asking, and after a moment, I nodded. She got me onto all fours, and moistened her cock with some hand-cream from her purse. She was still wearing her skirt, and raised it, letting it fall over my back as she positioned herself behind me. I could see our reflection in the hall mirror, and marveled at the sight of the gorgeous woman, with a secret beneath her skirt, moving up against me, her cock nudging at my ass.
Because it wasn't very big, her cock slipped in with surprising ease. Once past the sphincter, it slid softly into my ass until it was buried to the hilt. Then, slowly, she began to move back and forth, her long nails brushing my back as she stroked in and out of me. I lay flat on the floor and she covered me, her breasts warm on my back, her cock hot in my ass, moving slowly and sensuously as she fucked me.
She hadn't been in me more than a few minutes when suddenly her whole body spasmed, and I could feel her cock twitching in me as she came. She bit my shoulder as it filled me. She wriggled it back and forth a few times as it softened, then finally pulled out, then lay down beside me.
That was a year ago. Tomorrow, we move in together....