Originally Posted by
sweet_boy
She straddled me, sitting on my lap facing me and started grinding against me with her arms wrapped around me. She was giving me a lap dance, and the feeling of her ass moving against my cock, even if it was through my pants, was a feeling I welcomed happily. I put aside all of my fears and went along with it excitedly.
Eventually, she turned around, her back facing me and continued grinding up against me. She leaned forward some, giving me a perfect view of her beautiful ass, it did not look like a man's ass at all, and that was for sure. She even let me touch her, and her cheeks were just as smooth as a real woman would be.
She went back to facing me, and then she closed the gap between us and I felt her soft, warm lips press against mine. Her tongue probed at my mouth, until I opened my lips granting her access. My tongue and hers were now locked in a wrestling match, our soft moans filled the room as we explored one another.
We broke the kiss and she went right for my neck, licking, sucking and kissing, leaving a very, obvious hickey in the place of her lips.
Eventually Lisa slid off of my lap nice and slow onto her knees between my legs. She started rubbing me through my jeans and I felt my cock stiffen even more than it already had. Slowly, she unzipped me and reaching inside, freed my throbbing erection from its restricting confines.
She took me in her grip, a very firm and perfect grip, moving her hand up and down the length of my shaft to start. With her other hand, she started massaging my balls and I sighed, leaning my head back and giving in to the wonderful feeling.
Up and down, she moved her hand, stroking me and playing with my balls, until finally I felt Lisa's warm wet tongue flicking the head of my shaft.
I jumped at first, but then groaned as she flicked it once again. Almost as though she were getting a taste test, she licked the head like it was a lollipop, and I absolutely loved the feeling of her work.
Finally, she took me in her mouth, and I was in heaven. Up and down her head bobbed, her warm wet lips gliding back and forth over my cock. She could deep throat like a true expert, gagging only a little. She took me all the way into her throat, and it felt as if she were trying to swallow, the muscles in her gullet massaged my cock and it was the best feeling in the world.
This had to be probably the best blowjob I had ever received,
She started working me a little faster now, and I could feel the old familiar feeling of pressure building up in my balls, she sensed it coming to. Just as I was about to unload, she stopped, and I looked down at her surprised and almost disappointed, and she simply smiled back up at me.
"Why... why'd you stop?"
"I wouldn't want you to cum to soon, now would I?"
I sighed, as I felt the pressure decreasing, and when she realized I had recovered, she went right back to sucking my cock again. She started out the same as before, moving slowly, working me up to that agonizing feeling of pressure, and then once more as I was about to blow... she stopped.
It was like torture, she had me right where she wanted me the whole time,
Finally, the torture stopped though when she stood up and reached for her purse. Out of her purse, she pulled a Lifestyle Condom, along with a bottle of Astro-Glide. If this meant what I thought it meant, then I was very happy that she had not made me cum too soon, because I was certain it would be great. I had never actually fucked a girl in the ass before, though I had always wanted to try it at some point.
None of the girls I had dated in the past were open to the mere suggestion, and so I had been forced to forget that desire...until now. Maybe Rob was right, maybe this was a very good thing indeed.
She slowly pulled her skirt down, along with her silk white panties and for the first time I actually got to see another cock besides my own, she was not actually very big to be honest. Maybe around six inches, she wasn't one hundred percent hard yet, but it still was not such a bad sight.
As she started to kiss me though, I felt her cock responding, growing harder against me and when we broke apart and I looked down I was surprised to see she was a little bigger then I originally thought. She must have actually been about seven inches, pretty impressive really... but I still was not looking to do anything sexual towards her when it came to her cock.
"Don't worry about that," Lisa said motioning down to her member. "Like I said, nothing you don't want to do, you have my word."
"I trust you on that,"
"Good... I'm glad. Now, let's have some real fun."
She handed me the condom and I tore open the package, unrolling the latex over my hard cock while she poured a glob of lube into the palm of her hand and reached behind her to smear it all over her asshole. She turned around to face me, giving me a good view of her ass.
She bent over some, spreading her cheeks with one hand and let me watch as she smeared the lube all over her hole. She inserted a finger into her ass, and started fingering herself.
After a minute, I watched as she carefully inserted a second, and a few minutes later, she had worked at third one into her hole. My cock was as hard as a rock at this point, watching her slide her fingers in and out of her wet asshole, glistening with lube.
She pulled them out finally, and applied an extra amount before handing me the bottle.
"Put some on just for good measure," she said motioning towards my cock. I got the hint, and poured some over my shaft, rubbing it in real good. The condom already had lube on it, but a little extra would not hurt I figured.
When we were both ready, Lisa stepped forward and once again straddled me, sitting down towards me. I felt my cock probing at her asshole as she draped her arms over my shoulders and kissed me passionately.
As we kissed, I felt her pushing down on to me, and then I felt myself glide right into her. God she was so fucking tight! I moaned into her kiss and she reacted with a similar sound to my own.
My hands moved down from her breasts to her hips, taking hold of her love handles and holding on tightly as she started to ride me. She moved up and down on my hard cock, sliding in and out of her hole, leaning in closer to me. I took in the sweet scent of this beautiful girl, loving every second of what we were doing.
I could feel her own throbbing erection mashed between our bodies against my stomach, it was an odd feeling, but I overlooked it.
After a few minutes, she lifted herself off of me, turning around as she bent over, and I stood up behind her. I took hold of her hips again, pushing my cock right back into her gaping hole and continued to pound her with long hard strokes.
Standing up now, she was moaning louder, her cock swinging back and forth between her legs with every thrust and her breasts jiggling each time I slammed into her. Something came over me, and I found myself reaching around and taking her erection in my hand. I gave it a firm squeeze and she practically cried out in pleasure.
I pushed deep into her and squeezed her cock at the same time, and I loved the reaction I got. Lisa's body seemed to tremble beneath me, and her anal muscles clenched my dick tighter.
"Oh, fuck Jay, fuck yeah... fuck me harder!"
I was not going to say no to that, so I started ramming in and out of her, pumping her cock in rhythm with my thrusts. We were both panting, breathing heavy, sweating and moaning. The smell of sex filled the room. I could feel myself building up to what was sure to be a very intense orgasm. I could feel her dick starting to pulsate in my hand and I knew she was just as close as I was getting.
I pulled out, threw her on to the mattress in the corner of the room and climbed onto the bed with her.
I lifted her legs, wrapped them around me and pushed straight back into her. In missionary now, I pounded her ass as hard as I could with every bit of strength I had in me. The bed shook beneath us, and we both started getting louder as our impending orgasms finally overtook the both of us together. It hit her first, and I loved the sounds that she made as it washed over her.
"Oh, oh fuck, oh god, yes, yes, oh yeah!"
I felt something hot and sticky splash against my stomach, and as she writhed around underneath me moaning and squealing in pleasure, I knew she had cum. Now, it was my turn. A few more powerful thrusts and I buried myself balls deep inside of her ass and exploded.
I gave a sort of animalistic growl as my whole body shuddered and my cock spewed cum into her rectum. The condom held it all back though, but it still felt just as good to her I could tell.
When I was finished, I pulled out and collapsed at her side, both of us panting as she laid her head on my chest and we stayed there for a few moments. I started trying to register what I had just done.
I had just had sex with a transsexual... a man? No a woman who just happened to have a cock, instead of a pussy... but that was okay with me. At this point, it had to be, hell I had just jerked her off while I was fucking her in the ass.
"So, what did you think," Lisa asked finally.
"That... that was fucking hot," I replied. She laughed and reached down, pulling the condom from my dick and tossing it in a trashcan next to the mattress.
She climbed on top of me and rubbed her gaping asshole against my now flaccid dick again, until I felt myself starting to get hard again. Just when I thought we were going to have another round, she slid down my waist a little and started licking her cum up from my stomach. I only just then realized, she had cum all over me. Not that it bothered me, but it was funny to think.
Once she had licked it all up though, she moved back up and kissed me on my lips, sliding her tongue into my mouth and letting me taste her semen. We parted our kiss and Lisa smiled seductively at me.
"How's it taste? It's all because of you, so I figure you have a right to see what I taste like."
"It's not bad," I chuckled. "There's not much taste really."
"Well, how about next time... you can try sucking me off?"
"Oh... uh... I don't know,"
"Oh, come on," she begged. Lisa now sounded strangely like Rob, as I couldn't help but laugh at that, and so did she.
"It's not like I'm asking you to bend over for me or anything, wouldn't you eat pussy?"
"Yeah... and I have... plenty of times."
"So your basically still orally pleasuring a girl, it's just a little different than it normally would be. Give it some thought, and we'll see what happens."
"Yeah," I replied honestly. "I'll think about it."
We got up and started to dress, and I took note of how patient Lisa really was being with me about everything. She had led me through a very sexual fun adventure, at a steady pace that was comfortable for me. And even though she was requesting a little more from me next time, she was making it clear to me that she would not be angry if I said I didn't want to do that.
Truth be told, I did not know if I wanted to do that or not yet. However, I would definitely put some thought into it, as I had promised her I would.
When I left the club that night with Rob, I told him that he was right. I had a lot of fun, and so far, I had no regrets. I told him about the incident with Kendra and he found it hysterical. That was typical Rob though.
I couldn't wait to come back to The Raven next week.