The second time

[Billy Blueballs]

So this was my second time.
Determined, I lubed my mind with several drinks and made my way to the part of town best known for gay bars, TS hookers and general deviancy. I walked up the stairs to a bar where it was immediately clear that this was a gay bar - no doubt about it, an absolute cock forest. Not to be deterred I strolled as confidently as I could to the bar, aware that there were eyes on me - was it because I was so obviously out of place, their gaydar in enemy detection mode? Or was I possibly the image of fresh meat in a club that probably was mostly regulars? Either way, I noticed it and couldn't help but wonder "is this what women feel like walking into a bar full of dudes?"

I ordered my drink, and before long as luck would have it, in she walked. Tall, slim, brown skinned wearing a white one piece dress and high heels. No breasts, they were still a rarity in those days, but still as feminine and sexy as most women. She took immediately to the dance floor and I immediately saw an empty couch nearby with a perfect view. And the view was perfect. She moved sensually like a cat in heat and I sat transfixed, not caring that by this point half the crowd had probably spotted me as a "tranny chaser". Eventually she noticed me admiring her, she smiled coyly and I raised my drink and smiled back.
To my absolute surprise that was all that was required and she strutted toward me and sat down on the couch right next to me. I don't even recall what we said but it was enough that next thing I knew, we were walking back down the stairs hand in hand. There were few cell phones back then, and none with cameras...thank fuck for that!

We jumped in a cab to her apartment, to her room, where she asked if there was anything I would like her to wear. "Holy shit - is this really going this well?" I wondered. I asked if she had any leather or bondage type gear and sure enough, she returned from behind her closet door in a leather strap type outfit. She was smooth, shaved, sleek and I'm sure gasped when I saw her cock dangling beneath. This was already beyond any expectation I had. "Anything else?" she asked. I asked if she would tie me up. There was no headboard, but she obliged as best she could by tying my hands behind my head with a scarf. And then it began.

She straddled my chest and shuffled up until she brought her then semi hard cock to my mouth, which took it in with an eagerness that signaled that yes, this was really happening. As amateur as I was, she soon grew hard and her cock was everything I could have hoped for - about 7 inches not too thick, cut and delicious. My desire to please was matched by her increasingly enthusiastic thrusting and yes I did gag a bit - this was new territory to me. Trying to find my breath I slurped her cock out of my mouth and found myself licking my way down her shaft, enjoying the visual display of her above me and with sheer instinct I found myself licking all the way down to her balls. She writhed a wee bit and that was all I need to venture further. Yep, I let my tongue carry on down past those beautiful shaved balls and found an equally smooth asshole. I saw it, I licked, and she moaned and squirmed in such a way that I felt at that moment like a fucking pro - even if I couldn't take much of her cock without gagging, I was going to give this my best. I worked my way back up her shaft, took her in my mouth again and after some more vigorous face-fucking and gagging, she was ready to take my ass.
Still on my back, she brought my legs up, massaged some lube from god-knows-where...I was to delirious by this stage to be aware of every detail. Next thing I know she had my legs over her shoulders and she is began to enter me. She was very much aware and careful but I remember the dull pain - not unbearable, not even comfortable, but definitely sensual. Oh how I wish I could go back and enjoy it more...
So there I am, on my back, legs in the air with a beautiful transexual pounding me, and despite the discomfort, feeling as natural and turned on as any sexual experience I had ever had. She gave me a fucking that seemed to last for hours, in reality it may have been 15 - 30 minutes, who knows when you're in the throws of one the most mind bending sexual experiences of your life? Her pace quickened, she drove in deeper and her breathing became panting to where it was obvious that she was close to coming. "I want to see you come" I found myself purring. To my surprise, she pulled out and began to move up to me, jacking her cock all the way until she shoved her cock back into my mouth. Now I had never even heard of the phrase "ass to mouth" back then, and if you had explained it to me and asked if I would do it, I would have said hell no, but at this moment, in this situation, living this experience I did not resist. She face fucked me again - hard, I gagged again, and then sure enough she pulled out and jacking that beautiful cock she began to come and as soon as I spotted that creamy elixir I...shut my eyes! It looked so close to getting in my eyes I instinctively shut them. I had once shot a load into a girlfriends eyes before and saw firsthand how painful it was, so I sadly didn't get to see her come as I had hoped although I did see that first spurt coming at me like the old 3D movies. I didn't even get it on my face as far as I know, maybe I did? All I know is that she was very satisfied and I lived a fantasy that I thought was second to winning the lottery.
After catching our breath she got on all fours and offered me her ass which to this day I think would be my request for a last meal, but alas it was the very early hours by then. The alcohol, the hours, the pounding had taken its toll and I was far too exhausted to even muster a semi. To be honest, even years later I struggle to maintain an erection after any anal play, so maybe that was a factor too.
I had to leave regardless, with things to attend to that day but as she walked me to her front door I couldn't help myself and dropped to my knees and had one last lingering suck on her now flaccid and to me irresistible cock. She asked if I would see her again, I said I would but neither of us thought to exchange information and being from out of town, that was that.
I kick myself to this day for not getting her contact details. But those memories will last forever as will the changes that night made to me.
sigh

[Steveo10]

What bar did you go to ?

[Billy Blueballs]

I honestly don't remember. It was years ago