Exposing my sissy side

So ive dabbled with cross dressing before but last weekend I was feeling extra kinky. I went out and bought sexy heels, stockings, a dress, bra, wig, even makeup.

I shaved my legs to get the full experience. I was so excited to dress up and look sexy. I had fun getting dressed. I’m thin with a pretty effeminate body and face so everything fit me well and I looked hot AF.

I was drinking and jerking off watching porn and myself in the mirror. This was a lot of work, I thought, and its a shame I cant show myself off.

The thought of leaving my place like that was exhilarating and before I could debate it I was grabbing my keys. I decided to go to a neighborhood where I wouldn’t run into anyone. I parked and shyly got out of my car.

I felt so hot in my heels, red lipstick and by cock flopping freely under my short dress. I walked down the street passing people and sharing glances. My heart was pounding. I wanted to cum, but where?

A car pulled up and rolled down the window. I was terrified it was a cop but to my relief it was just some guy. He asked if he could get a date. I realized he thought I was a prostitute! I dont blame him.

Against my better judgement I got in the car. I had never done anything with a guy and was a little unsure, but also very horny.

We started driving and he asked to see my cock. I slowly lifted the bottom of my dress up revealing my half erect shaved penis. He started rubbing himself over his jeans.

He was older maybe late thirties. Looked like the working type. Fit, tan in a rough way. I reached over and touched his bulge. He pulled into a dirt parking lot and unbuttoned his jeans.

His cock was bigger than mine. Wider mostly. I whimpered unintentionally as I started to stroke it. I felt it swell in unison with my own. He didnt even ask I couldnt help myself and just started sucking it. The feeling and taste of a big strange cock in my mouth was driving me wild. I could feel my asshole begging for attention.

After a long and impassioned blowjob we moved to the back seat. I got on my knees and presented my boy pussy for fucking. He spit on it, which dropped onto my balls. I was in a sexual daze as he put a condom on.

I felt the big tip of his penis push gently onto asshole. My muscles relaxed and let that meaty cock slide in a bit. I was elated. I couldnt believe this was actually happening. He pushed deeper with each thrust, slowly opening my ass until he got balls deep. I could feel every thick inch of his cock deep in my guts. I was rock hard.

Once I was warmed up he started fucking. Harder and harder. My ass stretching and contracting with each powerful stroke. I felt like such a pretty slut getting fucked hard by a real penis. The pounding penetration overwhelmed my senses and my cock, despite not touching it once, spewed it’s load in glorious orgasm. Maybe the best Ive had.

I could tell he was about to cum too. Wait, I said pointing at my mouth, I want you to cum here.

He pulled out and I slid off the condom. With a smile I looked at him and started jerking his cock in my mouth. The head started to swell up and I put my pretty lips around it just as it unloaded warm streams of sweet gooey cum. Ive swallowed my own before, I love the taste, but never this much. It absolutely filled my mouth.

I kneeled there, asshole pulsing and used, cock dripping with satisfaction, and the sperm of a complete stranger practically coming out of my nose. Ive never been so happy. I swallowed it all down in two gulps, licking my lips and teeth for ever last drop.

When he asked how much I told him he just paid me cum. The long walk of shame back to my car, dripping with cum, was probably the best part.

Apr 15


  • newest
  • most popular
  • oldest
    • I do this at the local truck stop every Friday and Saturday night. Make about $600

    • I want to do this but don't have the nerves. Taking a huge cock up my ass and drinking his cum is on my bucket list. I'm married and want my wife to set this up. She just laughs and says I have crazy fantasies. I may but I want a big cock shoved inside me!

    • That hot. I'd love to fuck your tight little ass with my cock too. I wouldn't use a condom though. I'd bareback you and fill your ass with my cum.

    • Shove it up my asshole

Account Login
Is this post inapropriate?
Reason for reporting this post
Report this comment
Reason for reporting this comment
Delete this post?