52346 Stories
538711 Comments

New Stories 52346

Fiction 24743

Blowjob 12657

Consensual Sex 10052

Anal 9906

Fantasy 9440

True Story 9296

Incest 6233

Cum Swallowing 5612

Dark Fantasy 5126

Male / Female 5115

BDSM 4442

First Time 3801

Bi-sexual 3765

Teen 3112

Cheating 2884

Erotica 2650

Lesbian 2576

Domination/submission 2553

Gay 2377

Ass to mouth 2310

Oral Sex 2005

Exhibitionism 1863

Bestiality 1862

Authoritarian 1857

Romance 1824

Group Sex 1750

Fantastic 1667

Masturbation 1602

Female solo 1600

Diary 1500

Hardcore 1474

Boy 1356

Coercion 1325

Black 1309

Blackmail 1251

Cruelty 1233

Asian 1188

Humiliation 1012

Body modification 890

Job/Place-of-work 855

Young 847

Interracial 823

Female Domination 818

Rape 765

Mature 746

Discipline 689

Sex Joke 668

Drug 661

Non-consensual sex 644

School 605

Death 599

Non-Erotic 579

Written by women 544

Cuckold 539

Extreme 531

Virginity 487

Threesome 472

Reluctance 470

Poem 426

Mind Control 423

Wife 416

Voyeurism 404

Pregnant 336

Male Domination 328

Violence 282

Spanking 227

Fisting 207

Foot or shoe fetish 205

Transsexual 195

Prostitution 191

Monster 190

Slavery 162

Lactation 161

Toys 150

Gothic 147

Murder 141

massage 138

Latina 134

Water Sports/Pissing 130

Enema 103

Torture 93

Stories in DB: 52346
Comments: 538711

First tranny

Categories True Story

Author: The mail man

Published: 31 October 2018

  • Font:

Let me begin by saying that this is a true story.

I’d been single for a few months and having the shittyist of luck on dating sites.

I was unemployed and making some deliveries to the gay community for some extra cash.

One of my regular stops was to a tranny named Tory she wasn’t bad looking and she never made a move on me other than asking if I’d like to hangout for a few minutes.

Anyway I’d seen her on one of the chat rooms on a dating site... now I’d been without sex for at least a few weeks and I got a little curious. I started going through her profile, checking her out and eventually I was stroking myself to her pictures. She had a white complexion her breast were large, her ass looked great and most of her pictures were in stripper looking outfits like costumes.

So I’d make my regular stop at her place almost everyday and everyday I would see her I’d fantasize about her offering me a blow job or sex. It never happened but I’d see her try to get “clients” as she would call them in the chat rooms. When I’d get home I’d lay in bed with my hand in my pants while I browsed the chat room and come 2am all the trannies and what not would get in public chat and start asking for company.

This one night I had a few guys offer to suck my dick I refused them without hesitation but the sound of a sloppy blowjob was getting me hard. I started looking through profile pictures of some of the trannies and I found one named Carol, I remember her being on her knees wearing a cowboys jersey a pink thong. She looked more like an actual female then 98% of the other trannies I’d seen; so I sent her a message asking how her day was.

She quickly replied asking me for a picture of my member. I sent her a picture and asked for one in return. She sent me one of her ass, she was bent over in a thong and she had a bulge hanging there. And even now the thought of it gets me hard like it did then.

So we traded pictures for a few minutes and she ended up asking me to go over. Okay at this point it was near damn 5 am. I’m tired and horny but I ask for her address, it was about a 45 minute drive. I thought about it for a while and said okay. So I make the drive I show up to some apartments, call her and she gives me the room number.

So I got to the door, she greeted me and we made our way in to her bedroom. The place was dark. Like blacks greys and purples everywhere.

So we’re in her room and she gets me on her bed, we start making out and feeling each other. Shes in a black tank top and short shorts grinding on me as she takes off my shirt.

I start to lay down and get comfortable and she crawls up to me kissing my torso up to my neck and lips. I strip her of her top and she undoes the button to her shorts. I reach down and feel her cock under a soft layer of panties as she moans. She asked if I liked what I was doing. I didn’t say anything, I just pulled her closer and kissed her lips while I stroked her penis. Her moans were getting stronger as she breathed into me.

My cock was rock hard now and she felt it pressing on her. She started her way down removing my jeans. And demanded me to sit at the edge of the bed; as I positioned my self she stripped completely. He chest was more of a boys than a mans, having nothing much to call breast but nothing to complain about. She quickly got on her knees and started sucking me. I was really enjoying myself while she stroked my shaft and bopped her head up and down the head. I could’ve gone all night with her just doing that when she asked if I was ready to take her ass.

I said yes and just like before she took the lead, she handed me a condom and positioned her self on all fours at the edge of the bed. I put the rubber on and she said to go right ahead and slide it in. So I did as I was told and she screamed as I rammed my cock into her asshole. Her ass stayed up as the rest of her collapsed onto the mattress. I continued as she moaned repeatedly for more begging me not to stop. She could take it all day. I fucked her for an hour rotating from doggy to cowgirl watching her cock bounce up and down as she rode me and strocking her shaft as I fucked her ass. We finally finished in doggy she was screaming begging me not to cum until she did. I was at me end so I got up over her in a squatting position and fucked her ass as hard as I could at this point she could hardly speak, and I felt her trembling as she came under me. I didn’t feel like coming anymore realizing that I’ve completely dominated her had given me a second wind. I had to change positions so I sat down, she then grabbed my cock and started sucking me and asked if she could have a turn. Sadly I refused I didn’t know what I’d just done I questioned my sexuality but I couldn’t let myself be fucked. I said no.

In the end I came after she fingered my ass while giving me head.

But it’s something I’ll never forget. I enjoyed myself and I’d do it again if I had a chance.

I hope y’all enjoyed it

Views: 4276     Rated: +8.84

Add to favorites
  • Abuse on a story

    * Required field

First tranny

Rate this story:

  • Comment story

    * Required field