Synopsis: This story is partly based on fact, partly a fantasy. It is the story of a young man on vacation with his girlfriend and the night they have sex for the first time. The girlfriend has, up to this point, been reluctant to try sex. The big night finally comes for the two of them and the young man realizes, at last, what has made her so hesitant to share herself. The story is divided into several parts - the first focusing on oral sex and the second part on anal sex. The rest . . . well, we'll see!
If you have comments, eMail me at desolation_angel_722@hotmail.com
-5-
Rebecca lay in my arms, trembling after the most incredibly orgasm she'd ever experienced. Hell, it was the most incredible orgasm I'd ever experienced and I wasn't even the one who'd had it! We held one another in the darkness, myself stripped of every article of clothing, Rebecca in nothing but her flannel pajama top. We lay together quietly, simply enjoying being together.
I guess now would be the time for a recap. My girlfriend Rebecca and I had come to Vermont with six of our friends for the weekend. Although we'd been dating for some time, Rebecca had always been reluctant to have sex with me. That night, I found out the reason. Rebecca was a shemale, a woman with male sexual organs, and assumed with good cause that I would reject her. In fact, the opposite had happened. After an amazing session of oral sex with Rebecca on the receiving end, we rested. I knew she would need to recharge a bit before we continued.
"Why don't you take off your top?" I suggested.
"No," said Rebecca sullenly.
"Why not?" I asked. She was ashamed of her small breasts, I knew, but I could hardly see how she could still feel awkward considering what had just happened.
"I don't feel comfortable," she told me. I had no choice but to relent.
"That's OK," I told her. "As long as you're comfortable, I'm happy."
She smiled up at me and nuzzled closer against my body. Although I desperately wanted to lick and fondle her sweet, tiny breasts, I was willing to make certain concessions. I also believed she would come around eventually if I gave her time. We continued to lay silently. Rebecca began rubbing her hand up and down my stomach. I could sense she was becoming horny again.
"Remember when you asked if I wanted you to eat me out?" she said into the darkness.
"Yes," I replied.
"I do," she told me. "I want you to eat me out."
"But you don't have a . . ." I said, then interrupted myself, realizing what she meant. "Oh."
"You don't have to," she added quickly. "I know all this must be weird for you. I've just heard it feels really good and, well, you DID offer."
"I know I did," I told her, "and I make good on my promises."
Rebecca and I both sat up. She waited for me to instruct her and I told her to lie down on her stomach with her head on her pillow. She obeyed quickly, putting her head on the pillow and tucking her arms underneath. I crawled over to kneel beside her legs, which I urged her to spread by gently tugging at her ankles.
When she was in position, I moved to kneel between her legs, staring down at the two lovely white globes of her ass, so round and sweet and inviting. I placed my hands firmly on her ass and began to softly knead the flesh, occasionally running my hands up her back, then down again to her thighs, before finally returning to her cute butt.
After a few minutes of this, I pressed my thumbs together and gently pried her cheeks apart, revealing the tiny pink hole. "It's so pretty," I told her, making her giggle. I gently pressed my thumb against it. It was rubbery hard and a little dry. I popped my thumb into my mouth, wetting it with my saliva, before pressing it to her hole once again. I moved my thumb in a little circle along her rim, applying only a little bit of pressure, since I knew she would need to be loosened up before I could actually get my fingers in.
Spreading her cheeks again, I slowly lowered my face to her crack, and poked my tongue out of my mouth. I touched the tip to the center of her hole and tickled it, getting the taste on the tip of my tongue. I found it wasn't nearly as bad as I'd expected. My tongue retreated into my mouth for a minute so I could wet it again, then I began to gently prod Rebecca's hole once again.
She squealed and squirmed as I licked her asshole, flicking my tongue along the sensitive rim, and occasionally pressing the tip against her, trying to wriggle in. After a few minutes of this, her entire crack was glistening with my saliva. I moved up to kiss the top of her crack before running my tongue down, over her hole, to the back of her scrotum. I kissed her balls lovingly before pulling my face away.
"How does it feel?" I asked.
"Oh God, it's wonderful," she sighed.
"Better than the blowjob?" I asked with a grin. She laughed.
"Almost," she told me.
It was time to go back to work. I put my index finger in my mouth, sucked it for a moment for lubrication, then slid it between her cheeks until I found her butthole again. I pressed firmly and the hole opened wide enough to suck the tip of my finger in. Once it was in, the rest was easy. My finger glided deeper until I was in up to my knuckle. Rebecca let out a little groan.
"Are you OK?" I asked.
"Yes," she said. "It just feels weird to have someone else do it."
"You do this to yourself?" I asked curiously.
"Sure," she said, "with my fingers or a dildo."
"Cool," I replied. It was.
I began sliding my finger in and out of her ass, each time pulling it to within a centimeter of popping out, before shoving it back in. The inside of her ass was warm and tight. As I finger fucked her, I began to wiggle my finger around, hoping to stretch her out a bit more. This apparently felt very good because she began to shiver with delight and encouraged me to keep going, despite my repeated concerns that she wasn't in pain.
Finally, my finger began to feel looser inside her, so I licked my index and middle fingers, and began the process again, shoving both fingers gently through her sphincter until they slid easily down deeper into her hot bowels.
As my pace quickened, Rebecca's back arched with pleasure as she thrust her butt back to meet my hand, developing a synchronized rhythm with me. She pulled her hands out from under the pillow and pushed herself up so she was on all fours. I never stopped ramming her as she moved. Finally, she was on her hands and knees, thrusting her body backwards violently as I penetrated her.
Her semi-erect cock was dangling down between her legs, so I reached around her thigh and began to jerk it as my fingers went deeper and deeper into her sweet ass, tugging her cock roughly and occasionally cupping her balls.
Finally, I could take no more. I moved behind her, pulling out my fingers, and then positioning my hands so I was on all fours as well. She waited patiently as I moved closer, then buried my face in her delicious ass, forcing my nose and mouth between her cheeks, savoring the exquisite smell before poking my tongue through her hole.
Rebecca began to rock again as I tongue fucked her ass, keeping my hands on the mattress, doing all the work with my mouth. My tongue traced the inside of her rim and occasionally I would stop to kiss one of her cheeks or nibble on the soft flesh.
I lapped eagerly at her crack like a dog. I was so in love with her and with the unimaginable delights of her shemale body. She let out an explosive groan and fell forward on her face, shaking again. Exhausted by my efforts, I fell next to her.
She quickly climbed on top of me and began to kiss me fervently, our dicks mingling together once again in that exquisite sensation of warm, soft cock on cock. Rebecca shoved her tongue down my throat, grinding her crotch against mine.
-6-
We broke the kiss and looked lovingly into one another's eyes. Even though she lay on top of me, she was such a tiny girl that I could barely feel her weight. I cupped her ass with my hands and slowly rocked her against my body.
"I love you, baby," she said. "Thank you for all of this."
"It's my pleasure," I told her, "really."
"Have you ever done that before?" she asked. "Give someone head or a rimjob, I mean."
"No, never," I told her truthfully.
"You were very good," she said.
"It was like sucking the penis of a goddess," I said, smiling. "You tasted so wonderful. I just wish I could convince you to take off this top and let me see your pretty breasts."
"Not yet," she said. "Maybe later."
"OK," I relented. "So what now?
"I think you know what," she said, smiling mischievously and sitting up with her back leaning against my crooked knees, her testicles resting near my belly button.
"Are you sure?" I asked.
"Positive," was her reply. "I've wanted to feel your dick in my butt since high school."
"You should have told me then!" I said, laughing.
She giggled, then leaned over to kiss me. I drank deeply of her lips before finally she rolled off me and on to her back in the center of the bed. I took the pillows from the bed and propped them under her ass so her hips would have higher elevation. Then I spread her legs and knelt between them.
Lying on her back, biting the end of her thumb, with her cock laying semi-erect against her stomach, Rebecca looked as beautiful and innocent as a baby. Yet the sight of her filled with me a lust unlike any I'd ever known before.
I pulled her legs up and placed her ankles against my shoulders. Then I spit on to my hand and rubbed it over my cock, both to get it hard again and to provide lubrication. Then, gripping my shaft, I slid the tip of my cock into her crack, probing for the hole. It wasn't hard to find. As the tip pressed against it, Rebecca gave a soft gasp, and I knew I'd hit my mark.
She was still loose from the tongue-fucking I'd given her earlier, so my dick eased gently into her tight, warm bowels. She groaned sexually as her hungry butt eagerly swallowed every inch of my rod until my balls were mashing against her cheeks and my pubic hair was bristled as it rubbed against the bottom of her sack.
Next began the slow, sweet process of making love. Careful not to hurt Rebecca, and responsive what elicited moans of pleasure or squeals of delight from her, I began withdrawing my dick slowly, almost to the point of popping out, before gently pushing it back in. With each penetration, I became harder and harder, to the point where it was almost painful, but I would not stop.
As the minutes floated by, my pace increased. Soon, I was sliding in and out of her effortlessly, thrusting myself deeper into her as her entire body shook and trembled with passionate delight. Occasionally, I would glance down to see my cock penetrating her sweet, pink hole. As our love making continued, I leaned forward, pushing her back on to her shoulders, and took up a missionary position. I found in this way I could fuck her even harder.
Finally, after nearly half an hour, she placed her hands on my stomach, and gently pushed me away. I pulled my cock out and waited patiently on my knees as Rebecca rolled over on to her stomach and lifted her back, presenting her ass to me.
I took up my position again and guided my dick into her butt. Once I was inside, I placed my hands on her hips, and pulled her towards me, feeling my dick burrow deeper inside her. She moaned loudly and I had to smile. She had been a virgin when she woke up and now she was my private shemale slut.
As I continued banging her doggystyle, I began to grope her ass, then I rubbed my hands up and down her back, even under her shirt. I put my hand against her stomach and, as I did, I felt her erect penis smacking against my hand with each thrust. I gripped it in my fist and began to stroke her, timing the rhythm so I could keep her hard without making her cum just yet.
"Can we . . . change . . . positions?" she asked as I fucked her.
"To what?" I asked, not breaking the pace.
"I wanna . . . be on . . . top," she said.
"OK," I agreed.
I withdrew again with great emotional reluctance. Fucking her was so wonderful I never wanted it to stop, even for a moment. But what my girl wanted, my girl got. I lay down on the bed, on my back, with my cock pointing straight up.
Rebecca walked, on her knees, over to me, then swung her left leg over my stomach. She smiled at me as she scooted back into position. I could feel my cock pressed against her ass crack. She leaned forward and reached back to grip my shaft, then guided into position. As she eased back, my dick slid back inside her again and she sighed, closing her eyes to maximize pleasure.
She rode me hard, her body bouncing up and down as she took every inch of my shaft into her ass. Sometimes, she sat straight up with her cock pointing towards me, rubbing her breasts over her tank-top and squeezing her nipples through the fabric. At other times, she would lean forward, resting her hands on my shoulders and bouncing my crotch so hard I was afraid something might break.
Occasionally, she paused to grind her ass against my groin, torturing my poor dick, which was already engorged to capacity. Mercilessly, she forced my dick deeper into her, letting her asshole swallow every inch of me over and over again.
Finally, I couldn't take it any longer. My hips bucked and heaved. I clutched on to her thighs, squeezing tightly, knowing my orgasm was imminent. Moments before I came, she grabbed the bottom of her tank top, and with one savage motion, pulled it off and threw it away, letting her breasts bounce freely in the exposed air.
With a final thrust, I shot a hot stream of cum deep into her ass. As I did, Rebecca was leaning back, squeezing each nipple with the thumb and forefinger of each hand. As she did, she gave a hoarse cry, and her own hot stream of cum shot out from her dick, splashing across my stomach.
For a minute and a half, we continued, gradually slowing down. Both of our cocks went limp reluctantly until, with a mix of reluctance and relief, my dick popped out of her. Feeling her ass empty, Rebecca climbed off me, and lay down by my side.
She ran her finger through the puddles of her semen on my chest and stomach, then brought her finger to my mouth. Eagerly, I sucked at it, tasty the salty sweetness of her jizz. She fed me the rest of her cream in this manner before licking me clean.
Leaning on my elbow, I stroked her stomach and her breasts. When I touched them, she sucked in air nervously. I couldn't understand why she was so ashamed of them. They were small, but beautiful, with puffy, pink nipples I wanted to suck more than anything in the world. Well, almost more than anything.
"Why are you so shy about them?" I asked.
"I don't know," she replied. "I guess they are a disappointment. I had hoped hormone therapy would give me bigger breasts. They make me feel so . . . boyish. I want to look like a hot chick."
"You do," I told her.
"Shut up," she said, blushing.
"I'm serious," I said. "You are the hottest woman I've ever seen. I wouldn't change you at all. You are perfect."
"Really?" she asked, biting her lip. "You wouldn't like me more with bigger breasts and a vagina?"
"You are perfect," I repeated.
She pulled my face towards hers and kissed me. We held the kiss for a long time. It was more than a sexual thing. It was a symbol of real love between us. We'd just shared the most intimate experience of our lives and this was the final seal of our devotion.
"Let's get cleaned up," she said.
I agreed. We both climbed out of bed and walked, still nude, into the bathroom. We stood side-by-side before the large mirror and cleaned ourselves up. I washed off my cock and my stomach. Rebecca did the same. We took our time, teasing one another by grabbing the other's butt or dick
Suddenly, she giggled.
"What?" I asked, grinning.
"Want to do something kind of weird?" she asked me.
"Like what?" I asked.
"Well," she said, "I have to pee."
Laughing, she pulled me over to the toilet. She pulled up the toilet seat and pointed her dick at the water in the bowl. Shrugging, I did the same. Simultaneously, twin jets of piss streamed from our cocks, filling up the bowl and turning it a pale yellow. Once we were done, we both shook off the last few drops, and I flushed the toilet.
Giddy with the things we'd just done, we stepped out of the bathroom, back into our bedroom, and stopped dead in our tracks.
Kate, another friend of ours who had come on the trip, stood in our room. Rebecca and I froze before her, completely exposed. After a moment of shock, Rebecca ducked behind me, concealing her secret. But, of course, it was too late. There was no way Kate hadn't seen.
We waited, breathlessly, for her to speak.
To be continued . . .
For more shemale fiction, check out my Bethany's Secret series and my Alpha Gamma's Secret series. I appreciate comments and criticism so send me lots!