Current rating: 4.13 of 5
Rate by The Naughty Meter
Categories: Transvestites, Other men, Oral Sex, Anal Sex
Fulfillment: I will tell you later
Nature: I will tell you later
There was this beautiful girl that I went to school with who I still talk to sometimes. Very much a case of one of these hot girls who you would like to fuck, but through some unfortunate circumstances, you're trapped in a platonic relationship with. And she knew that much, as I'm not the kind to hide my intentions--regardless of whether not the ship has sailed.
Now this girl is a slight oddball, which is part of why I was attracted to her. She liked comics and videogames, which made her a lot of fun to hang out with since our interests matched up, but there was one thing that we were never able to see eye to eye over: she had a particular preference for gay porn.
Now, at the time, I didn't consider myself to be homophobic. But I was pretty...uncomfortable with anything in that regard. Didn't want anything to do with it, and found the idea of two big hairy construction-worker looking dudes to be the furthest thing from my mind when it came to sexy. And she apparently took a great interest in my distaste and took every opportunity she could to prod me about it. She apparently didn't believe that anyone was really 100% gay or straight. These conversations really didn't go anywhere, as my argument generally consisted of "I think dudes are gross to look at, that's why," but hearing her talk about her own lesbian experiences was enough of a turn on that I indulged her.
One day, though, things took an interesting turn.
"I bet I could get you to sleep with a guy." I looked at her like she'd gone insane. "I'm so sure that if I set you up with this guy, and you don't end up fucking him...then I'll fuck you."
Now this, of course, was an offer too good to pass up. And being relatively secure in my sexuality, I knew that this was gonna be an easy win. Or at least I thought so until I dropped by the house of the--what I had assumed--poor shlubb she was trying to pawn me off on.
The person who cheerfully answered the door was...I mean, it was almost unfair. She was tall blonde with shoulder length hair, and striking blue eyes, wearing a blue skirt (!) and long, smooth legs. I was pretty sure I had the wrong house when she asked me (in the sweetest voice) to come in.
"You're...not quite...what I was expecting..." I said, somewhat unable to tear my eyes away.
She smiled. "What were you expecting?"
"I dunno...less Gwynyth Paltrow and more..." my mind wandered as I watched her (her??) ass as she walked across the room. I could feel my physical arousal mix with my mental confusion and I furrowed my eyebrow trying to reconcile what I was seeing.
"Well you're exactly what I expected," she walked in close and looked up at me. She was tall for a girl (!?) but I was still a pretty towering 6'4". She smiled and I notice the soft pink color of her lips.
"Uh, so, why did you agree to this?" I asked, looking away, trying to keep focussed on why I was here. This wasn't going to work. I'm not going to fuck a guy, no matter how cute she might be. Especially when I have a delicious piece of ass I've been thinking about for weeks within my grasp.
But she put her hands on either side of my head and turned my gaze back to her face. "I told you, because you're my type. I like black guys. Big black guys..." she said, sort of blushing sheepishly and looking away slightly. I closed my eyes and let out a mental "FUUUUCK" as my mind reeled at the cuteness I was witness to. I should've masturbated before I came over. I should've asked to see a picture first. But all that amounted to shit because here I was, on the verge of leaning in and planting a lusty kiss on what was a dude (right!?)
"Look uh, I'm sorry but y'know, and you're very cute but," I stumbled over my words trying to defuse the situation but apparently she thought this was as cute as I found her to be because she leaned in and pulled me into her lips. They felt soft, warm, and not at all...greasy or...prickly or any of the other things that made me scrunch up my face in disgust at the idea of kissing a guy in the past. It was enough to get me to reciprocate, and I wrapped my toungue in hers and pulled her against me. She grabbed my ass as she put her hands around me and that was what got the first tangible reaction out of my cock. As we kissed standing in the walkway I began to press my cock into her.
"Oh!..." she said, half surprisedly half with that tone of voice that always sounds like "Just like I planned it". I felt a mix of arousal and resignation as I looked at her sly smile.
"You've got me..." I said. "But you got to understand, I've never done this before, so I'm not quite sure about..."
She kissed me again, this time reaching one hand down to caress my expanding bulge. "Just do what you normally would do," She whispered in my ear, before licking the lobe slowly. So I did, and reached my hands down to her butt and lifted her so that she was straddling me. She gave a surprised laugh, and probably wasn't used to this kind of treatment being fairly tall. We kissed as I lifted her over to a couch that sat in front of a TV in the middle of the room.
Once I was on the couch she changed positions so that she was on top of me and began to pull down my pants. She brought out my cock which she seemed particularly pleased with. Without saying a word she began to suck on it enthusiastically--it was an incredible change of pace, partly because I had been single for a while, and partly because she seemed to genuinely enjoy what she was doing. It wasn't long before my hips were moving involuntarily. "Stop," I told her breathlessly.
She unwrapped her lips around from my member and looked up disappointedly. "Don't you wanna cum?" she said, still slowly moving her hand along the length of my cock.
"Yeah but..." I sat up and put my hands on her shoulder "I'm gonna fuck you." I continued forward until I was ontop of her and had pinned her arms over her head. Her eyes went a little wide and she started to squirm as I rubbed my naked cock against her stomach. "Turn over" I told her, and she did and I lifted up the skirt to see her tight ass and white and pink striped panties. I helped her get to her knees and rubbed my cock against her ass for a bit. And it was at this point that I noticed her...his?...her cock. It was...not as offensive as I was expecting. Shaved, unlike mine, and hard as a rock. I was more worried about my own cock at the moment, and so I gradually guided it into her ass, as she took sharp breaths and moans.
"Oh yes," she said, pushing gently back against me. "Fuck me, fuck me with your big cock." We were sinking deeper into the sofa as I pumped in and out increasingly fast. I leaned over and put my arms on her chest, rubbing her nipples through the shirt she was wearing and lifted her so she was sitting up, as I kissed her neck as I continued fucking her. I then noticed that she was pulling frantically at her cock. Partly out of curiosity, partly out of wanting to reciprocate, and partly out of heated lust I reached my own hand down and grasped the length of his dick which was now slick with precum.
She gasped. "You...nnh...you don't have to," but I sshhhed her as I started fucking faster while rhthmically jerking my hand back and forth. It was a bizarre feeling but the response was worth it--she started moaning louder "FUck me! Fuck me harder! Cum for me!" I was spurred on to the point that my hand and my hips were both in frenzied spasms until I felt her hot, gooey cum spurt from his cock with a twitch which pushed me over the ledge as my own loaded emptied into her ass.
I leaned backwards, pulling her ontop of me and put my hands around her chest, feeling her rapid breat gradually slow back to normal.
After we both regained our breaths I mused..."Do you think she'll still let me fuck her?"
"Even if she doesn't" she said, curling up contentedly on my chest "You can fuck me any time."