My First Blowjob

Story Info
Cross-dresser sucks off guy he meets on Internet.
1.2k words
4.11
119.8k
13
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

I wake up early on a Wednesday morning. No work today. I've called in sick just because I don't feel like going. My live-in girlfriend is already gone to her job. I'm home alone. My first thought: turn on the computer and check out some porn.

Nothing weird. Half-naked models stripping off their lingerie. Start with still photos. Later move to video.

The longer I look, the deeper I fall into a lust trance. I started off wanting to fuck the girls in the photos. Now, I want to be them. I want to feel the G-string creeping up my ass crack, the under wire cups of a bra pushing into my chest.

I log into an AOL chat room where fags in my area meet for sex. I use my cross-dressing name, Penny, and put out my feelers: "Anyone looking for a hook-up?" I ask. No takers at first. Then a guy offers to fuck me up the ass. He says "no thanks" when I tell him I'm into wearing women's clothes. I download striptease videos while waiting for a mate.

Then comes Bob352. He sends me a private message, describing himself as a professional white male. 32 years old. Good shape.

Loves cross dressers.

"Perfect," I write. "Wanna fuck?"

He says he must be discreet because he's got a girlfriend.

"Me too," I write.

He says we should meet in public.

"Wanna do something kinky?" I ask.

Forty minutes later, my car is parked in front of a lingerie shop that's just opening. The shop is wedged between a nail salon and a pizza joint at a suburban strip mall. I'm leaning against the front of the store and watching for Bob's Honda Accord. When he pulls up and gets out, I see that the description he gave me is accurate. He's wearing a blue collared shirt and khaki pants. Wouldn't stand out in a crowd if he tried.

We shake hands like he's just sold me a car. I look him dead in the eye and say, "I'm going to let you cum in my mouth."

Bob smiles devilishly.

"I know," he says.

A bell rings as I push open the shop door. The clerk behind the counter is a young punk who is wearing a Korn T-shirt and reading a magazine. He looks up at the two men who've just walked into his shop.

"The leather masks, whips and shit like that are in the back," he says.

Bob rolls his eyes.

"Actually," I say, "we're more into bras and panties."

Bob smiles and nods vigorously.

The clerk shakes his head. He says "whatever" and goes back to reading his magazine.

We're the first customers. It's just the clerk, Bob, me and a store full of lace, leather and sheer fabric. The whole place smells like potpourri. I recognize some of the garments some mannequins are wearing. They're the same ones a few of the local strippers wear on stage. They must shop here.

Bob and I find a rack of lacy pink bras and panties. I pick out a 36a bra and matching boy-short panties. Bob nods his approval. I pay with cash and we rush to our cars.

Bob follows me to my house, a 10 minute drive. He parks in one of the spaces assigned to my apartment, making no attempt to hide his visit. We agree on an emergency plan: If my girlfriend comes home, he's going to say he's a computer tech from my company and that he's helping me install a security program.

I lead him to the office where I keep my computer. I cue up my favorite striptease and tell him to have a seat. A thin brunette with short hair gyrates to a techno beat on the screen. Bob leans back in the leather chair and watches. A bulge emerges in his pants.

I slip into a bathroom across the hall and strip out of my T-shirt and jeans. I pull the bra across my chest and clasp the wire hooks behind my back. The under wire cups press into my flesh. My cock jumps. I slide on the shoulder straps. By pulling up some flesh, I can almost fill out the cups. Not bad for a guy.

I pull up the boy-short panties. They hug my ass cheeks like a friendly set of hands. My cock and balls fit neatly up front.

When I return to the office, Bob has his pants and boxer shorts around his ankles. His stiffy is at least eight inches.

I like this guy's style: right down to business.

I kneel between Bob's legs. Our eyes lock.

"I've never done this before," I say.

"Me neither," he says. "Not with a guy."

With our eyes still held on each other, I wrap my lips around the head of his fuckstick. I slowly slide down his pole. Half of his meat enters me before I pull back. My head dips again. Bob's eyes roll back. He moans. I start to make like an oil well. Each time my head goes down, I take more of Bob's cock into my mouth. Pre-cum splashes across my tongue. Looks like I may have struck a geyser. Bob grabs the back of my head and makes me take his whole cock. I gag the first time but quickly open my throat and let him fuck my face. Each time I go down, I get a nose full of pubic hair. Bob smells like Irish Spring soap.

It's clear I'm in his hands now. He has total control over my body. His strokes quicken.

Then it comes.

A tidal wave of jizz I never thought possible. Bob holds my head in place to make sure I take it all. But it's impossible. Cum dribbles out of the corner of my mouth. It flows down my chin and neck like a warm river. Bob finishes and pulls out.

I look up at him with a mouthful of jizz in my pursed lips.

"Show me," he says.

I open up and flip my tongue. More jizz runs down my cheeks.

"Now swallow," Bob says.

His warm, salty juice slides down my throat. Then I lean back against a wall and pull my cock out of my panties. It takes two strokes for me to cum all over my stomach. Bob looks at me with disgust.

"Rub it on your face," he says.

His tone leaves no doubt that it's an order. I use the edge of my hand to scrape the cum into my palm. I thoroughly facialize myself from chin to forehead, my juices mingling with Bob's juices on my skin.

Bob pulls up his underwear and pants and fastens his belt. Then he makes the most unexpected -- yet perfect-- move. He walks over to me and slaps me across the face.

"Cunt," he says.

He unhurriedly walks out of the house. I hear his car door close and his engine start. The car drives away, leaving me on the floor of the office. I feel sticky, lonely and depraved.

I'm a piece of shit, but I love it.

After I shower, I drive to a local convenience store and ditch the panties and bra in a trash can. I vow to never do this again.

A promise I know I'll never keep.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
9 Comments
AnonymousAnonymousalmost 5 years ago

I wish I could do that, really want to give a blow job and swallow cum in my bra and panties

AnonymousAnonymousabout 7 years ago
My First time at 16

When i was in Cleveland at the age of 16 ( living there ) went to my GF aunts house, she lived about 4 miles away from me, She was 36 with 4 kids, and she told me she liked young boys

so i went there to get laid, well when i got there she was in bed with a lace bra and panties, she said outright that she just started her period, and she would jack me off or blow me

she started to suck on my cock , and no matter how hard i tried to cum, i could not, she had great 36b tits, super nice nipples

It was getting late , her kids were at there fathers house for 2 days, i left around 10 PM after a few beers, went into bus stop, waited for like 30 minutes, man pulls up in a red Chevy, and said The Bus's quit running at 9.30 at this station, so i was screwed

He said let me take you home, i said OK

as we were driving I Looked he had on a red suit, white shirt and red shoes, WOW

and we were talking he ask me what i was doing this late on a school night, so bragging I told him, as he was starting to rub his cock, looked BIG, mine is only 6.5 but he looked like 8 +

so we talked and he said you ever get a man to suck you, i said no, he pulled into a place called Clark field, only baseball diamond in the whole place, about 25 acres or more

he shut off headlights, moon was full so we had a good view, i was getting worked up about him telling me how good a man's lip's felt on a cock

He said pull it out , which i did, he reached over to stroke it, then without a work started to suck it, I blew a load in about 3 minutes, he took it all in and just smiled as he got up, then he unzipped his pants, and pulled it out WOW, said would you like to feel mine, so I did, then he pushed my head down on it, in about 2 minutes he started too cum, pulled it out so I could watch it shoot cum , watch ( first Time ever ) WOW was great , I watched a Man cum he then sucked me a second time, and it took longer but I cum hard we met for like 6 months , best part he made his wife give me a bath last too times i was there WOW, we met for like 6 months

AnonymousAnonymousabout 7 years ago

I so want to do that!

chloejacobs83chloejacobs83almost 8 years ago
yum

I could almost taste the cum with him - well done!!

AnonymousAnonymousover 14 years ago
me too !!!

I want to be a cunt, too - just like you. I love sucking cock and I want Bob's cum in my mouth.

Show More
Share this Story

Similar Stories

Hotel Room Cocksucker Business traveler finds horny friends through a personal ad.in Transgender & Crossdressers
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
I Begged Him To Kiss Me! Ch. 01 A young married guy is seduced by his elderly male neighbor.in Transgender & Crossdressers
More Stories