The Parade

I was down Center City on a warm June afternoon with a group of my friends, just walking around and enjoying ourselves. I had not been out of the house much lately so when they called me up and asked if I wanted to come down here with them, I jumped at the opportunity.

I knew of course what today was; it was the day of the Philadelphia gay pride parade. Two of my friends happened to be lesbians, one of them was gay and one of them was bisexual so I was assuming their main objective for coming here was to attend the parade. I didn't' mind, so long as I was out of my house. Not to mention I obviously was not against that lifestyle if they were my friends. Sure enough, after walking around for a while we found ourselves on South Street where the parade was taking place.

My friend Jess, the bisexual girl turned around and smiled at me.

"You're okay with this right? Sorry we didn't tell you,"

"Yeah it's' fine don't worry about it," I replied.

"I'm just glad to be outside."

I was drawn in by the wide variety of different people that were here and how they seemed to have their own cultures about them all; it was nice to see so many people gathering here to stand up for what they believed in and have fun.

There were gay men, the ones who were a bit flamboyant and obvious about it and there were dudes like' Jimmy who I never would have suspected was gay until we started talking to him and he told us that he was.

There were girls that were together, lesbians and plenty of people that were bisexual too but most importantly, I realized I was not the only straight heterosexual person attending this yearly parade.

There were also quite a few transsexuals, cross-dressers and the like walking about. They were perhaps the most interesting to me; the transvestites and' cross-dressers with their crazy costumes and outfits or maybe they would have been labeled as drag queens? I didn't' really know the difference and I did not exactly care either so I shrugged it off. The transsexual women did not dress that way' at all; they were not cross-dressers and that was why.

I understood that much at least, that transsexuals were men who felt as if they had been born in the wrong body and chose to female hormones to become women, the way they felt they should have been born.

I had a lot of respect for them; it took a lot of courage to make decisions like that. If I had ever been faced with such a choice I wasn't' sure I would be able to figure out the right decision. We made our way down South Street from 2nd' all the way up to about 15th street in the area that was known as the Gay district.

They called it such as it was the one section that had the most gay clubs and' bars. As we continued walking, I noticed a transvestite a few feet away from me kept looking back at me and smiling and winking at me.

She was obviously a man dressed as a woman; it was not hard to tell. A simple look at her face and though she looked feminine, you could still see the masculinity if you paid close attention. She had black curly hair that went down just past her shoulders, and her arms were bigger then a real woman's arms would likely be.

That was another dead give away to me anyway, I could not deny I was getting' a little freaked out at how she kept checking me out but I did my best to pay it any attention. I didn't' want to come off seeming like some homophobic asshole just because someone was sizing me up a bit.

After the parade ended, we all made our way into a nearby club to continue the fun and it seemed as though that was where everyone involved in the parade was heading; including my admirer. As I sat at the bar sipping a glass of Jack and Coke I watched my friends on the dance floor enjoying themselves together. It was nice to see, and I would be out there with them; but I didn't' have anyone to dance with.

I would rather sit here and watch them then go out there and dance by myself. I jumped in surprise at the feeling of a hand on my shoulder and turned around to see my admirer was now standing over me smiling; this was awkward,

"Hey there," she said. Her voice sounded strangely high, not as masculine as I had expected it would sound. But' there was still that hint of flamboyance there that reminded me, on top of the masculine facial features, that this was not a real woman.

"H-Hi,"

"Mind if I take a seat?"

Reluctantly, I shook my head and even went as far as to pull out a seat for her trying to be a' gentlemen'. I realized then maybe that had not been a good move. I might have given her the impression that I was interested; no, I shrugged it off trying not to be such a douche bag anymore now.

"So what's a cutie like you doing here all alone?"

"Uh...well, I'm not here with a date. Just some friends,"

"Oh I see,"

Hell, nothing wrong with having a little conversation right, I had no problem with talking to this person. We continued talking for a while and I learned her name was Leslie as a cross-dresser and Lenny as a man; she was 37-years old, a lot older than I was and had been cross-dressing a very long time.

I noticed she kept making the occasional move on me here and there but it was no big deal really. I told her my name was Tom,

I explained to her my current dating situation; I was single, but only after having recently ended a two' year relationship with a girl I thought had loved me. I had given up a lot for this person in the time we had been together, but apparently she'd' had no gratitude because I had walked in on her having sex with another man about a month ago. It hurt like hell; but I was not going to linger on it because life was too short. I was trying to move on with my life,

"That's a shame," she said as I finished my story.

"You're a very nice man, very cute too; anyone who cheats on a guy like you is undeserving."

"Thanks," I smiled. She slid off' of her stool and I was a bit shocked when she suddenly sat on my lap and leaned in closer to me. I could smell cigarettes and alcohol on her breath as she leaned in to kiss me and before I could protest she was sliding her tongue between my lips.

I finally pulled away and pushed her off' walking towards the bathroom to wash my face and try to forget that had just happened. As I walked into the rest room and turned on the sink, I sighed, trying to erase the image from my memory. The bathroom door opened and in she walked, taking me completely by surprise; I opened my mouth to remind her she could not be in the men's room only to remember that she technically was a man so she was' allowed to go in here if she wanted.

In fact, she would probably get in trouble if she went into the woman's bathroom before she'd' get in trouble for coming into this room.

"What are you doing," I asked as she pushed me away from the sink and turned it off before backing me up against the wall.

"I really like you; and I would love to show you how good I can make you feel in comparison to that bitch who' cheated on you."

I had no room to protest before she once again crushed her lips against mine, and sliding her tongue into my mouth. I felt her sliding her hand up under my shirt and teasing my nipples while squeezing my cock through my pants with her other hand. She broke the kiss and I was about to try and' push her off again when she started kissing, licking and sucking my neck; my weak spot.

I groaned at the feeling of her lips and tongue against my neck as she sucked and bit, leaving a rather large hickey in the place of her lips. I couldn't' believe it but my cock was actually getting hard now to my own surprise.

She backed away now and pulled me towards one of the stalls, pushing me in and shutting the door behind us. I could not believe I was about to have sex in a bathroom stall, let alone with a cross-dresser. Couldn't' even blame the alcohol since I really was hardly even' buzzed at this point. She pulled shirt over my head and hung it on the hook on the door before pushing me against the wall and licking my nipples.

I moaned as she licked and sucked on them for a few seconds while undoing my belt and pulling my pants down to my ankles. Now, she was sucking on my right nipple while teasing the other' which was wet from saliva, then running that hand down to stroke my cock while keeping her mouth trained on my right nipple. She seemed to enjoy the reaction she was getting from me by licking it,

When she finally stopped, I watched as she started to slip out of her pants and underwear and exposed her rather large cock; damn was she big. Not exactly long really, but she was thick; she had to be about six inches long and very thick. She placed both hands on my shoulders and pushed me down to the floor on my knees so that her cock was right in front of my mouth now.

She moved one hand to my head and pulled me towards her, her dick pressing against my lips; I opened wide and she thrust right down my throat making me gag a little. She wasted no time, throat fucking me and I was making the sounds that I was use to hearing from girls who were sucking my cock, it felt weird to know that I was the one sucking dick rather than someone sucking mine.

I acknowledged the strange sensation that came with performing a blowjob for the very first time; her cock head was hot and spongy and tasted like urine but the taste was not really off putting. I could feel her balls against my chin and saliva running down my chin and over her balls.

She pulled her dick from between my lips and I gasped for air as she pulled me to my feet and pushed me face first against the wall. She started running her hands up and down my back while kissing me between the shoulder blades and I could feel her cock rubbing against my asshole.

"Y-You're supposed to use lube; aren't you?"

"Don't worry baby," she whispered.

She backed away and grabbed her purse off the floor reaching into it and digging around then stopped and sighed.

"Damn it, I must have forgotten to bring it."

I sighed in relief, seeing this as my chance to get out of this unscathed with my butt-virginity still intact, safe and' sound.

"Guess we can't do it then," I said trying to sound disappointed and waiting for her to back away from me so I could pull my pants up.

It didn't' happen though; she smiled and laughed before kissing my neck.

"Honey, you think that would stop me? It's called improvising, I know how to do it don't you worry."

"Shit," I thought. I wasn't' getting out of this I realized as she spit on her hand a couple of times and started rubbing her saliva all over her cock. She got down on her knees and spread my ass cheeks and I felt her tongue diving into my asshole. I jumped in shock; she was giving me a rim job. It felt surprisingly good but still very awkward and I wished there were a way out,

When she stopped, she stood up and spit on her hand again rubbing her cock again before pushing it against my hole again.

"Ready?"

"Do I have a choice?"

"Now, now try to act like you're interested; I'll make it feel good I promise,"

With that, she slammed right into me and I bit my lip trying not to scream as I reached up over the top of the stall and grabbed the sides of it squeezing until my hands turned red and sore. My asshole felt as if it was on fire, burning as she pushed her entire length deep into me until I could feel her hips against me and I knew she was all the way in.

"Oh fuck," I groaned in pain as she pulled about halfway out and then thrust right back into me again. What little preparation she had done had done me good, it still hurt though; real lubrication would have helped a lot more.

As she fucked my ass nice and hard I felt myself adjusting to the feeling of fullness and soon enough the pain had subsided enough that it was starting to actually feel really' good. I felt my own dick beginning to rise, pushed between me and' the wall and the head was starting to swell. I started moaning and breathing heavily as she continued ramming me harder and harder.

I felt my cock spasm and my entire body went into a fit of shakes as I started to cum, long ropes of semen spurting from my cock all over the wall and the floor. I was a bit surprised at how hard I had came but I had to admit it had probably been the most intense orgasm I had ever experienced in my life.

Leslie continued fucking me, grunting and' moaning louder now and as she drove herself balls deep inside of me one last time I felt her explode as she began to pump he full of her thick hot semen. She leaned into me, breathing in my ear and resting her head on my shoulder as I remained pinned to the wall waiting for her to back off. We were both sweating very heavily,

She kissed me on the neck and pulled out and I could feel her semen running down the back of my legs. She fixed herself up a bit and I sat down on the toilet, trying to catch my own breath as she headed for the stall door. She stopped and turned around to face me, smiling at me.

"Thanks for the fuck sweetie," she said before blowing me a kiss and then walking out of the bathroom, leaving me there feeling embarrassed and humiliated; but strangely relieved.