A New Experience

Story Info
A man fulfills his fantasy of being with a crossdresser.
2.3k words
4.18
32.9k
15
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
ThomX
ThomX
251 Followers

I met him at a drag queen bar called Tranz. Mind you, this was not a bar I would normally have frequented, but I had just gone through a very nasty divorce from my wife of nearly 13 years Deborah, partly because she discovered my attraction to drag queens and crossdressers and, believe me, she used that against me in the divorce. To add insult to injury, she informed all of our friends and even family members of my attraction and I lost a number of my friends and became estranged from a number of my family members as a result. So I figured I may as well indulge my fantasy since my "secret" was out.

And that was what led me to Tranz.

He told me his name was Tommy but that he also went by his other name of Tamara when he dressed up. This night he was wearing a black mesh shirt and a pair of black leather pants that were pulled down enough to expose his bright pink g-string. There were purple streaks in his jet-black hair and his was skin was pale white and he was rail-thin. There was ruby-red lipstick painted thick around his lips and dark blue mascara painted just as thick around his eyes and was also wearing blush. He didn't come right out and tell me, but I guessed his age either in his late-teens or early-twenties.

And he was just about the sexiest thing I ever laid eyes on!

After buying him a drink at the bar and engaging in the usual chit chat for a moment or so, Tommy just came right out and asked me if I wanted to go back to his place. After being stunned into silence for a brief moment, I caught myself and managed to stutter out, "S-sure. We can do that . . . if you want."

Tommy nodded as he slurped down the rest of his drink and then asked as he started walking past me, "Good, let's go."

I finished my own drink, laid down some money on the bar and followed him out. As I stood behind him, he asked without looking back at me, "You got a car or do we need to catch a cab?"

Again, I sputtered, "I . . brought my own car."

He nodded again and held his hand out in front of him, "After you."

I nodded as I stepped past him and he followed. We got in my car and he gave me directions to his place, which turned out to be a tiny two-room apartment, including the smallest bathroom I'd ever seen in someone's place. There was a dirty mattress on the floor and that was about it. There wasn't even a TV in the room. I figured Tommy didn't spend much time in his place or there would've been more stuff. Of course, how much stuff he had in his apartment wasn't my main concern at this point.

Tommy strutted his petite little ass over to his mattress and, after throwing his purse on the floor next to it, plopped down. I stood where I was finding myself unable to move. Tommy must've sensed my apprehension because he gave me this come-hither stare and patted the empty spot on the mattress next to him and said, "Come over here. Sit down. I won't bite." A sneer escaped the corner of his mouth as he added, "Not unless you want me to."

I gave him a nervous grin and slowly sat down next to him. I wasn't sure what to do at this point, seeing as how this was my first time with a drag queen and all, so I just started rambling on about, well, nothing. Tommy just sat there for a moment listening to me rambling on before he seductively placed his hand on my shoulder and cooed, "Relax."

I shook my head in embarrassment and said, "I'm sorry. This is just . . . my first time."

"Yes," he said, grinning, "I know."

I was about to ask him how he knew, but I figured it was obvious as hell. I did, however, ask why he picked me to go home with him in the bar. Before he answered, he reached into his purse and fired up the first of many cigarettes and, after exhaling a smoke-filled breath, told me in a very blunt manner, "Because I like fucking older men."

I gave another nervous grin and sputtered, "Oh . . . okay."

Before I was even aware of what was going on, Tommy grabbed my hand and placed it right square on his crotch which already had a noticeable bulge. After rubbing on his expanding crotch for I don't know how long, Tommy unzipped his pants and pulled down his pants but not his flimsy hot pink thong that was stretching beyond its capacity. My mouth started salivating at the glorious sight of his growing erection that kept stretching his thong. He pulled his thong down and his cock popped out in plain view. Surrounded by a thick lush patch of jet-black pubic hair, his dick must have been a good eight or nine inches long. It was thin and veiny with a large flushed purple head that kind of matched the purple streaks in his hair. His balls were big and full and hung down as low as a man's twice his age.

And it was the most beautiful thing I'd ever laid eyes on!

"You wanna make good use of this, don't you?" Tommy cooed again.

I did. I didn't have to say a response as I lowered my head and grabbed his cock at its base. I opened my lips wide and took at least half the length of him inside my mouth. I gently closed my mouth around his cock and started bobbing my head up and down on his erect penis, being careful not to scrape my teeth on the sensitive veiny skin of his luscious cock. I briefly took my mouth off his prick and licked on his jet-black pubes and pulled on them a little with my teeth. I took him back into my mouth and resumed sucking him off. This was my very first time tasting another man like this, and, I must say, it tasted great!

Tommy started slowly thrusting himself deeper into my mouth, causing the bulbous head to tap against the back of my throat. I thought this would make me gag, but, to my surprise, it didn't. In fact, it was a rather pleasant sensation even when he began thrusting faster. But, before he could come, he abruptly took himself out of my mouth and quickly reached for the zipper of my trousers. He took out my own erect cock and started to stroke it. My cock, admittedly, wasn't as long as Tommy's, but it was thicker and my balls hung down about as low. He wasted no time sticking it his mouth and started sucking on it gingerly. Now I could count on one hand on maybe two or three fingers how many blowjobs my prudish wife gave to me during our 13 years of rotten marriage. But here was this kid sucking my dick like there was no tomorrow!

Keeping his hand wrapped tightly around my shaft, he sucked my balls in his eager mouth and scraped them with his teeth. I threw back my head and moaned in both pleasure and a little pain as he both sucked and bit into my tender scrotum. He plopped my dick back into his mouth and began sucking on it again until I was on the verge of coming. I guess he sensed how close I was to orgasm as he abruptly took his mouth away from my throbbing aching cock and quickly pulled his leather pants and thong all the way off.

Without him saying a word or telling me what to do, I grabbed his legs behind his knees and pulled his legs back all the way up to his head and stuck my tongue as far as I could into his tight asshole. I licked around his bittersweet anus and then ran my tongue up the space between his asshole and his balls and sucked his ball-sack into my mouth like he did with mine. I pulled on his nuts and ran my tongue around each of them as they were in my mouth. I licked my tongue back down the space below his nut-sack and back down to his puckered asshole. I placed both my hands on his skinny ass and pushed my tongue back into his ass as deep as it would go. I darted my tongue in and out of his asshole as if it was my cock. After tongue-fucking him for what seemed like the longest time, Tommy abruptly grabbed my thinning hair and yanked my head up. He kissed me with surprising passion on my tainted lips before pulling his face away and telling me in a seductive half-whisper, "Now I want you to fuck me with that big cock of yours!"

Again, without me having to say a word to him, he grabbed my shoulders and pushed me down on the mattress. He positioned his ass above my cock which he grabbed and aimed it at his waiting asshole. He began to slowly insert my dick into his rectum and pushed himself down inch-by-inch until his ass was touching my waist. He leaned forward and put his hands on the mattress on either side of me and started to furiously fuck himself on my cock. I swear, I thought I was going to tear him in half he was so thin!

Keep in mind I hadn't had sex in the longest time even long before my divorce, so it didn't take no time for the pressure to build up in my aching balls and shoot the biggest load into Tommy's tight asshole. He kept pumping himself on my cock even as I was groaning and coming inside of him. He clenched his sphincter tighter around my cock like he was trying to coax more come out of my testicles if that was even possible!

I guess he realized I was finally spent as he slowly got off me and laid down next to me. Before I even knew it, he reached down and took my messy cock back in his mouth and licked and sucked the come and the taint off my subsiding erection. And, much to my surprise, he grabbed my jaw and forced it open and spit the gunk into my mouth. This time I felt like I was about to gag, but I held it in and even swallowed all of what Tommy had spit into my mouth. Tommy apparently had a sadistic streak in him as he just closed my mouth shut as he let out a rather sinister-sounding laugh. Before I even had a chance to respond, Tommy tapped me on the shoulder and said almost like a warning, "Now it's my turn." He tapped me on the shoulder again and ordered me, "Get on your stomach, bitch!"

Without hesitating, I did as he commanded and laid down on my stomach in anticipation of whatever it was he had planned for me, although I had a pretty damn good idea! Without wasting any time, Tommy spread my ass cheeks apart and stuck his mouth and tongue into my asshole like I did with his. He both licked and tongue-fucked my asshole like he had done this many times before, of which I had absolutely no doubt that he had. My anus soon became lubed up with his saliva. He then climbed on top of me and mounted me as he shoved his cock deep inside of me until I felt his balls touching my ass. He placed his hands on the mattress on either side of me again and fucked my ass as hard and as fast as he could. He was so forceful with me he practically raped my asshole, though I certainly didn't mind!

I guess with him being younger than me he had more stamina than me as he was able to hold out longer than I did as he fucked my ass faster and faster, the sound of his balls slapping over and over again against my ass. With my face buried in his dingy pillow, I felt his hot breath striking against the side of my face as he leaned his face close to my ear and whispered, "I'm gonna come in your ass. Are you ready for it?"

"Yeah," I gave out a muffled groan, "I'm ready!"

"Okay, bitch," he groaned, "here it comes!"

With that, he practically screamed in my ear as I felt his hot come filling my ass and spilling out over my ass and down the inside of my thighs. He pumped and pumped his cock in and out of me some more until I guess he coaxed the last drop of come out of his drooping balls. He finally climbed down off of me and licked his own come and taint from off of my backside and, when he was done, he grabbed my face again and forced my mouth back open and spit his shit back into my mouth. Again, I thought I was going to throw up, but I managed to keep it all in and swallow it all down. Tommy patted me on the back like I was some kind of dog and said in an almost mocking tone, "Good bitch!"

He laid down beside me on the dirty mattress after fishing out another cigarette from his purse and, after lighting it up, asked me with surprising tenderness, "You wanna spend the night?"

I did, and I did. I kept seeing Tommy after that first intense night with him. Not wanting to see him live in that condition any longer, I invited him to come live with me, which he eagerly accepted. He got a job as a griller at a local fast food restaurant, and he became my live-in lover. I'm not sure what the future holds for me and Tommy, but I will say I wouldn't change a damn thing.

Except, of course, for my nasty divorce!

ThomX
ThomX
251 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
AnonymousAnonymousover 3 years ago
New Sissy

I always wanted to cross dress but did not know how to begin.I went on the web and went to x dressing sites and learned how to become a x dressing sissy.I bough cream to remove all my body hair.Did my eye brows eye lashes lipstick and panted my nails red.I got a bra thong garter belt stockings and high heels and a wig.I bough a short dress in red.I stayed dressed like that walking in my new heels for week around my house.But now that i was a cross dresser what do i do next to become a true sissy.Again back to the web and now i know i had to go to a adult movie and find how to do what i needed to do.Once there i now was not sure if i could do what i had to do to become a true x dressing sissy.I had to be with a man for sex both oral and anal on me.Do i weight for them to come me our do i go to them.I soon felt a man feeling me up.Telling me how sexy i looked he took me by the hand lead me in to a large booth.He dropped his shorts are was his hard in his hand.He told me to take off my dress and thong.I was pushed down on my knees and he told me to open my mouth wide and suck his cock now.Not sure how to suck his cock i just opened wide.His cock slid in a little at a time.Until i could feel it down my throat and he started to slowly pump his cock.It had a sweet taste i really liked sucking his cock.He pulled out and he bent me over and put lube on my butt and slid his hard cock in my butt .It hurt at first but soon it felt nice.That was the beginning of me taking cocks that night.Once i started i could not stop taking cock sucking them and getting fucked.

Ilovepantyhose2Ilovepantyhose2over 7 years ago
Desirable encounter to be in

I really enjoyed this hot story and feel my ass wiggling.

Share this Story

Similar Stories

The Big Mature Shemale Next Door Little guy is fed cum and seduced.in Transgender & Crossdressers
My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
Shemale Step-Sister Teen boy spies on his shemale step-sister and gets a treat.in Transgender & Crossdressers
"What Does She See in Him?" A high school boy finds the girl of his dreams is a bit more.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
More Stories