Cross dresser.. Twink.. Tranny?

First off, I identify as a closeted gay, I love twinks, I get so turned on, especially when they fit my fantasy. I like ‘em, thin and lanky, 125 pounds or less, not too tall 5’10” or so, little or no body fat. I like to be able to see ribs and abs the distinctive “V” shape leading into his underwear waistband, I like tight but squeezable ass cheeks that are defined by narrow, slim hips, I want to see ass dimples between the cheeks and backbone, prefer blondish hair, clean shaved all over preferably hairless body and face, young, barely legal, but legal. I love nice size hairless white dicks with big uncut purple head on top, beautiful tight pink ball sack squeezing his balls upward into his abdomen, so I can fit it all in my mouth, both balls. I have an abnormal oral fetish for dick and cum as well. How well does that describe me?

I was in Key West visiting my buddy on vacation, he and I were driving through the Duval St area bars, when I saw a very tall, and I mean about 6’8” or 9” tall girl, I said to my buddy, “Christ that girl is tall”, he said “boy that ain’t no girl”, he explained we were driving through a gay section and she was a he, streetwalking. I said “No way, go back around, I got to take another look”. Instead we parked nearby as there was a spot, and my buddy said, better yet, we’ll walk by on our way back to Duval St.

We jumped out, now, keep in mind, my buddy doesn’t yet know I’m gay, at least I don’t think he does. As we approached, the cross dressed guy eyed us as we were both eying him err her, and he dropped shuttle hints to approach if we were interested. We both giggled and continued past him. My buddy asked if I’d “ever been inside one of these places”, meaning a gay bar, and I lied and said no. He said fuck Duval St were going in here then you gotta see this, he grabbed my arm and pulled me toward the door. I acted reluctantly, but was enthused by his determination and I could get to scope out the place as well.

Once inside he pointed out and we discussed the different types of personalities, oddly he wasn’t overly critical of them, I thought he be more homophobic about it. He even approached some with pretty decent pick up lines, and returned interested replies to others, he seemed quite outgoing toward them. I began to second guess his intentions, as he really seemed interested, unless he was fooling me.

I asked what he was doing, and to stop leading them on, when he replied, “Who’s leading them on”? Wait, what? I thought he was serious? He wanted to pick up something?, I wasn’t quite sure yet, a tranny, a cross dresser or just a gay guy, maybe a lesbian or 2, I was confused and asked his intentions. He replied he was bi and he could take guys or girls, in fact he often enjoyed guys sometimes better than girls. My mouth just opened wide, as I was finding this out for the first time, and he was yet so open about it, and here I am hiding myself from him all these years. I then came out to him and told him I was Gay, when he replied “Yeah, I thought so, I came to this section of town just to find out once and for all”. Embarrassed I apologized; he replied “What for”? We all got urges and frankly I’ve had somewhat of a crush on you, but was afraid of how it could affect our friendship. “Now let’s go pick up some sweet guys”.

He darted off and found some bear of a guy with a leather vest, definitely not my type, leaving me at the bar. As I glanced around the room I was intrigued by the cross dressers as I didn’t get much exposure to them at home. Then I saw my weakness, a really cute blonde “kid” short parted hair on his head, no stubble or even sideburns, smooth skinned baby face, blue eyes and a blue V neck t shirt, he was sitting on a stool at a high top table, sipping a drink, and he appeared to be alone, maybe? Hopefully? I quickly didn’t want to miss my chance and approached with my beer in hand, said “Hi”, and asked if I could borrow a corner of his table for a while. He said sure, and made some small talk with me, he was from out of town too, and his friend was off trying to pick someone up on the other side of the bar. We laughed when I told the same story about my buddy. I became infatuated with him, and his cuteness, he filled my fantasy 100 percent.

He suddenly asked if I wanted to head outside for some air, and I agreed and tried to guzzle the remaining beer, he said oh no, take it with you, you can drink on the streets here, so we stopped at the bar and got a second drink to go as well.

As we walked and talked, my fantasy was within reach, I was rock hard in my jeans and we finished our drinks and he suggested a dark area, not quite an alley, where we began passionately kissing. I was in heaven, ready to come in my jeans. He said I don’t usually do this but I find you pretty attractive, and I feel very comfortable with you. My brain was turning over control to the little brain in my pants. As he reached for my swollen bulge in my pants, I was in heaven. Anything he said I was willing and able to do. He suggested we head toward his hotel only a block or so further, I again willingly followed along.

The conversation turned slightly odd, when he asked if I preferred top or bottom, I didn’t really care at this point, but I said Top, definitely Top, he said that’s good because I only bottom. Not continuing or caring we just continued toward the hotel.

We got into the room, he asked if I wanted anything, and I replied “Just Your Ass” he turned out the lights and led me to the bedroom. We began by necking, and he began to slowly undress me, all the while kissing my body and feeling me up. Eventually he began sucking my cock and playing with my balls. I was about 8 steps ahead of him, as I only managed to get his t shirt off. I could feel his firm tight chest, touching each rib as I went, I squeezed each firm and hard nipple, rolling them in my fingers, I could only imagine every part of him that I was touching me, as it was so pitched black, but I didn’t care my ultimate fantasy was being fulfilled, and who knows maybe I would have been disappointed if I did see what I was touching, but we continued. I tried and began to make my move to his crotch abut he managed to pull away and change positions each time, so I continued to move slower on him than he was on me, but I liked what was happening none the less. I grabbed his ass through his jeans and again fantasized it naked as I imagined what it must look like according to my dreams. He was blowing me so well I had to pull him off so as not to cum, he then started talking dirty like to me, “You really want to fuck me”? he asked, “Go on tell me you want to fuck my tight little ass”. And so on and so forth. I replied I really did, “I really want to fuck your tight little ass, and cum all over your butt cheeks”, I said but I can’t seem to get you out of those jeans, and he said, “Ok then but promise you won’t be disappointed at anything from this point on”. I promised, it didn’t even dawn on me what he was saying, I just needed to get off.

He stood, removed his pants and came close to me again, pulling my hands to inside his backside, letting me feel his tight twinky ass, and he allowed me to finger it as I kissed his stomach, with longing ecstasy realizing the finale was within my reach. As I started to pull closer to his crotch he grabbed my hands quickly and turned around ass toward my face as he pulled off his Lacey underwear and sat on me sliding my harder than hard dick up and down his ass crack, grinding me like a lap dancer until I yelled stop, and he did, I thought I was going to lose it as I pulled my hands off his hips and went for the final grab of his dick, to return the favor.

OH God, I exclaimed, as I felt around, there was no dick where there should be a dick, feeling around very startled, I felt a smoothly shaved, wait…. What…. That’s a Virginia!!! As he said please keep going now, remember you promised not to be disappointed, as he errr she lifted her ass placing onto my dick and began riding me. Still dark, still I was imagining my fantasy twink, I was so close to cumming as she placed my fingers in her pussy, I realized she was getting off as I was. We both came together, me in her ass, and she on my fingers. I hadn’t ever fucked a girl in the ass before, and it’s been 5 or 6 years since I touched a pussy, now I suddenly felt like I was duped. We lay recovering and began to talk.

She said shes trans and has had her top surgery to remove her breasts, which I have to say really looked good in the light, once she turned it on, although slightly larger than I had imagined with my touch. She was about a year away from the complex bottom surgery, and has had a lot of issues with hookups, being kind of half way. She said tonight was the best she’s had ever, but she didn’t want to ruin it like has happened so many times before, I told her, I loved it very much and wouldn’t mind doing it again sometime, she fulfilled my twink fantasy and didn’t even have that long hard dick with the nicely shaped knob on it, and the cum, that I thought I really needed as part of my requirement, but obviously didn’t.

We returned to the bar, I got my buddy we went back to his place, and I told him everything, that I being gay, picked up a girl dressed as my fantasy guy in a gay bar, and fucked her ass raw, and loved it. He told me I’m all screwed up in my head, but the story was hot.

We left and went back to his house, where we wound up fucking each other in his bed. A fantasy I never imagined would ever come about, I was fucking my buddy who I thought was straight……uh oh but he thinks he’s bi, that’s right. But now am I bi because of me getting it on with that tiny butch girl?

The next night we went back, and she was there, hoping I’d be back, so we went at it again, this time she allowed me the lights on, and my Buddy joined in. the three of us had a great time, and my twink girl was more of a guy than a girl, the pussy was just a side show, we had 3 people and 2 dicks with plenty of mouths and ass to go around.