Transsexuals & Crossdressers Stories

15,868 results
Orientation
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Infinite Scroll

EMP Attack

by Writewinger on Sep 26, 2017
Loving Wives

As usual I welcome constructive comments but if you are obsessed with punctuation and sentence structure this might not be for you. I write chiefly for my own pleasure and hope that some others will enjoy my efforts. Also, I'm neither a doctor or an engineer so my efforts in the parts of this story that encompass those fields of endeavor are probably not tec...

Hotel Encounter Pt. 03

by Jay876 on Sep 24, 2019
Transgender & Crossdressers

Jay gets on a bus and prepares to head back into town. Kyle had yet to respond and Jay was feeling lonely he needed some comfort. He didn't have any friends in Derby and Kyle was the only person he could turn to. As he sat on the bus, he felt like crying in the bus on the way into the city center. Jay got off the bus and headed back to the hotel it was onl...

Hotel Encounter Pt. 02

by Jay876 on Sep 24, 2019
Transgender & Crossdressers

Jay awoke his body being spooned by his Daddy. It's 3 in the morning. Jay can feel Kyle's hard cock pressing against his ass. He needed Kyle inside of him again. So, Jay turns around and kisses Kyle on his forehead. He smiles at Jay. "How was last night?" "Fun." Jay says smiling back. "You know I've never been with an Indian before." "How was it." "Best...

Friends to Lovers

by awpbmn on Oct 22, 2019
Transgender & Crossdressers

All characters depicted are over 18 years old. *** She enters, stripped to her bra and panties, and sees him sitting at the edge of the bed in only his boxers. He admires her supple, athletic body, her womanly hips, and her large breasts. He had imagined her body so many times. He had known her since childhood, he had watched her develop alongside him, had...

Truth or Fantasy 07: Photos

by 1sfshermale on Sep 24, 2019
Transgender & Crossdressers

At the local scenic look out, I held up my new white phone "Would you mind taking a few photos of me for my collection?" I asked the handsome gentleman wearing a red Titleist golf cap. "Not at all, in fact, I was trying to figure out what to say to you." he replied eagerly. "When I saw you in your pink dress, I knew I wanted to meet you. You are gorgeous....

Don't Come

by AlinaX on Apr 3, 2019
Transgender & Crossdressers

"Don't come," she orders, and I sigh audibly with frustration. I'm all for a bit of orgasm denial - the resulting climax can be spectacular, true, but also it's exhilarating to linger on the precipice, every fibre of my being exquisitely tense with need. Her delicate, lingering, teasing kisses make me burn. Her mouth descends on my breast and I writhe in an...

Leftover Lusts

by allourdesires on Jun 19, 2019
Transgender & Crossdressers

She found you there, tied over the desk, stained face betraying your recent history. A pair of satin panties formed a delicate puddle around the knot connecting your stocking'd ankles. None of your "companions" had bothered to undress you more interested, no doubt, in taking advantage and likely entranced by the lascivious sight of a bare bottom beneath your...

Discovering Stephanie

by CumInMyBum on Jan 16, 2019
Transgender & Crossdressers

I knew i was different but did not know why. I could not put my finger on it. I was definitely attracted to girls and many of my early kisses and fondles were with girls at clubs and bars, but I would also find certain older guys attractive to. I would occasionally feel a twitch in my boxer shorts if an older guy looked at me. At that time I started to disco...

My First Time

by ElephantJuice on Jul 15, 2020
Transgender & Crossdressers

My very first time sucking cock was with a beautiful blonde trans-girl with a big tasty dick. Firstly, I guess you should know a little about myself. I'm approaching 40, married and consider myself straight, I know technically I'm not but it's the category that best fits me if you have to categorise. I don't particularly find men attractive and have no urge...

The Sleepover

by lynntg0444 on Jan 22, 2019
Transgender & Crossdressers

When I was in college, I would spend the night at a friend's house whose parents lived close to the university. One very hot night we were sleeping only in undershorts in the same bedroom. We were both virgins and started talking about girls and both got a little hard. One of us suggested that we "practice" how we would fuck a girl, so we took turns being on...