My Favorite Sexual Experience

By the time this night happened, I'd already been with a good number of men and loved bottoming. I was a crossdresser since my youth, having BOUGHT my own first pair of pantyhose at age twelve so I wouldn’t have to keep sneaking into my mom’s undie drawer. I had given up on vaginas after being with the same girl in high school twice which confirmed I was only into sex that involved a penis going into a male asshole. And I was always fantasizing it was my asshole, plugging it with so many household objects before buying my first sex toy. By ninth grade, pantyhose and a dildo had become play partners of mine for life.

Yet into my 20’s, I was still wrestling with trying to be a versatile pantyhose CD and being with other CDs. Foolishly trying not just to be a bottom, but also a top. During this period, I met another sissy boy I loved deeply. I transitioned him into a full TG and we got married. Then I quickly lost interest in him without his penis. I started sneaking with masculine men, loved it, and we soon got divorced.

But that made me single at 30. And this night, I was hoping to get laid en femme in a gay bathhouse. I was strongly considering that I wanted to go trans myself, having been compelled to secretly dress in girl’s clothes with full makeup since I was a teen. I figured trans had to be my issue since it couldn’t be I was just a full-on gay CD, right? I mean my crushes on boys in high school or even members of popular bands in my early pubescence, those were exactly that -- crushes. Ok, in my teens I started jerking off to the International Male catalog -- wishing I was with sleeping with those guys -- in addition to the usual jerking off to Frederick’s of Hollywood wishing I was one of those girls. But I had only been with one femme guy in high school, and even married another femme. And I didn’t play with manly men until college... so I couldn’t be so blatantly and simply gay if it took me that long, right?

My first manly men were chasers who I met in tranny clubs. Then I went en femme to B&D play spaces like the Power Exchange in Las Vegas or Peanuts in West Hollywood. There it was about the bondage. So hot, but I wasn't there for male beefcake. Now I did go to a gay bathhouse in male mode once -- right after I turned of age -- just to check it out. Somehow it didn’t sit right without being en femme and I left before doing anything.

But tonight would be different. It was monthly crossdresser night at a prominent New England bathhouse. And I was so excited. I had very recently taken a job on the U.S. east coast, working in Boston. I hadn’t made any friends yet as I was less than a month into my move. So I went to Club Body Center in Providence alone.

I took a travel bag packed to the brim with my things that got quick searched at the front. I got a locker and did a fast, purposeful switch from man to sissy. I put on glossy tan Wolford tights, super sensual. I put on a black thong teddy, black heel low rise boots, did my makeup as best I could in the mirror and pulled out my red wig. I looked good, but it wasn’t complete until I put the black leather jacket I had walked in with on. Beneath the jacket, I was a pretty, femme sissy, but the jacket signaled I’m not a real female and am in the right place. A gay cd male.

I couldn’t tell the crowd until I got in. There were only 2 other full CDs there besides me. It was very early in the evening though. There were definitely more typical gay guys. And the majority of them were masculine gay. Not the secret gays who are ashamed after they fuck you in a hotel room and cruise adult book stores, but guys fine with their sexuality who looked like they could be in the Village People. Mustaches. Some leather. Some boots. Daddies and subs. One obvious bottom in gold undies. A variety of bodies and ages, but a sexy sight. I didn’t know if they didn’t know or didn’t care if this was CD night. I was hoping they knew, cared, and would be interested in me.

So I went into the main play area, found a space, sat, and waited. A couple butch gays looked my way and bypassed me. As did others. Because I’ve always been a chubby cute CD, I leaned femme-looking. I was hoping I was not too fishy. Darn. I must be too fishy. I can't understand why so few like the aesthetic of a gay leather man with an obvious sissy queen because I ADORE it. But it sort of goes against same love, doesn't it?

And then HE approached me. He didn’t sit down. He came right up to me, reached down and rubbed the top of my pantyhosed thigh. A shiver went up me. He was about 50, lanky, white guy, blonde hair. Over 6 feet tall, clean-shaven. He told me I was sexy and gave me his name. He leaned over me. Wiry body, he had a decent size long package in a leather jock strap.

I wasn’t sure how to engage him, so I stood up. I ran my finger down the middle of his bare chest peeking out from underneath his leather vest and tried to make conversation. Suddenly, he spanked my ass with a loud slap. I liked it, but it seemed TOO forward… so I started walking away from him. If he wanted me, he would follow me. Make the effort. And he did. But so did another guy whom he clearly knew. His buddy was thick, beefy, shorter, much younger (closer to my age), a mustache, leather cap, wearing boots, gloves, and a fishnet top above his chaps that exposed his thick cock (and a muscular ass that I would later be eating).

Suddenly I was walking around the bathhouse with two horny, sexy guys following me. And more horny guys watching me. Their dicks were either all hanging out or really easy to get at.

The hallway of the club was lit darkish with some red light. I passed a couple of side rooms that were mainly closed doors. I walked to a corner wall and did a courage check – oh my, yes, I wanted whatever this night brings. I had snuck two bottles of poppers in with me, unsealing one right before arriving so they would be fresh. The other ready to be a backup if there was a spill, lol. I took a hit from the bottle deep in each nostril as my guys following cornered me. I was a piece of meat, but one WORTH following. I felt so submissive and feminine in that instant. Making men never look so good.

Libido engorged by the poppers, I fell to my knees. I’ve probably never unwrapped anything as fast in my life as I pulled Mr. Assgrabber’s cock from out of his jockstrap and got it in my mouth. And I began sucking hard. Right there on the floor.

As I was doing it, a group of guys gathered around. As if to watch. Or if waiting for their turn. I got so excited and yet fearful it could be the latter. I had never been with more than two masculine play partners in the same event before.

I sucked Mr. Assgrabber really hard for a couple minutes. When I stopped and took a breath of air, his mustache buddy moved in. Mr. Mustache grabbed my hand and commanded me to follow him. Said we were all going to a playroom. Mr. Mustache had a strong gloved hand. It was a turn on. And they both had smiles that made me say yes. They took me away from the others into an adjacent playroom. Not guiding me, pulling me. But I would have run there if I knew where to go.

When they brought me in, there was a bench in the middle of the room. Mr. Mustache asked if I had ever been to Club Body Center before. I said no. Mr. Assgrabber said: "leave the door open." And in an instant, Mr. Assgrabber bent me over the bench which would become my perch for much of that evening. He put me on it with my ass up for easiest entry. Mr. Assgrabber took my poppers out of my hand. He took deep hits, then handed the bottle to Mr Mustache. While Mr. Assgrabber fondled my pantyhosed ass, Mr. Mustache took deep hits. Then I was given the deepest hits. Repeat. My response was I quickly unbuttoned the crotch of my teddy with the strongest desire I’ve ever had for anal. I begged them to please rip a small hole in the ass of my tights so I could keep them on without pulling them down.

Mr. Assgrabber ripped open a hole, then lubed my crack up. He put a condom on while Mr. Mustache came around the bench to put his dick in my face, slapping me with it teasingly. I tried to get it in my mouth, but he kept teasing my face with it.

Then they spit-roasted me.

I was in heaven. Poppered, filled with cock. The scent of cock in my face with man sweat in the air.

I sucked their dicks, swallowed, and had my ass loved in every way imaginable for the next couple of hours. Fingers, dicks, tongues, nearly a fist (not quite). I was spit roasted like a pig over and over. Because they KEPT guys cycling into the room. Multlple took turns with Mr. Assgrabber and Mr. Mustache directing the action. And taking their own turns. How they kept going! I can describe most of the guys in front of me whose dicks I sucked, or when I got turned over and saw them, but I also had anonymous cocks in my ass.

Mr. Assgrabber and Mr. Mustache also figured out my Kryptonite. They would hit me with poppers and I would lose all inhibitions to eat manly male ass.

I ate so much male ass and licked so many balls. And these were nearly all gay masculine men. Beefy, thin, fat-assed, and all points in between. But I was their sissy for this night and these studs wanted me not as a pretend woman like those curious chasers, but as a gay queen. My pantyhose got destroyed quickly but hilariously never to the point they completely came off. I was frotted in my hose before it got ripped open and then frotted exposed after. It was incredible. So many hits of poppers. So much GAY sex. Cum in my butt. Even unprotected (how f'ing stupid of me - i never did such again!!!) over and over. Mouth. Face. Wig. I even shot multiple loads. I knew that night what my sexuality was with perfect clarity.

It was the best sex I've had.

I've had many hot playtimes since. I could not be kept on the farm after seeing Paris.

And while I don't think it can be topped because it came at too formative a period, if I can ever find some of that rush again, I welcome it.