transsexuals stories and histories

Jenn and Taylor Are Bed Partners
This story has been posted to Literotica. com with the full knowledge of the original author under my pen name, NikkijMaadison. No part or whole of this story may be reprinted in any other format or on any other website without the express written consent of the original author. I edited this story using Microsoft for spellchecking, flagging punctuation, grammar review, and as a dictionary. I use any other suggestions only as a guide. You may discover mistakes. That will ...

I had developed a steady relationship with Rick in a daddy sissy dynamic. He had forgiven me and we were elated at my clean test results. I would spend several nights a week there. Dressed up cuddling and playing. We would also go out as men together and enjoy each others company. Most people assuming we were father and son....

Magic Dress - Sanjit's Sister
CHAPTER 1
For an academic there is one big no-no. Sexual relations with a student. If you can give them marks, or affect the outcome of their degree, then it creates a conflict. So don't do it.
Which in principle is fine.
But for a young male lecturer with so many young women at the peak of sexual attractiveness and often dressing to show it, it can sometimes be very hard, if you know what I mean....

Hello! This is the 2nd installment in the "One of Those Nights" series. I'm sure you can skip that story and still enjoy this one, but feel free to check it out. You can also skip the first part of THIS story if you want to get straight to the action. I've added a TL: DR just before Part 2, (Another) One of Those Nights. Enjoy!...

So it's next weekend. Tyra has been sexting my girl every single day.
She seems to be a very prolific personal coach for the biggest celebrities and richest people. She actually has a big following, and we've started watching her stuff.
She's sent her dick pics in houses of people I should not name, but it's crazy. Good night jerk offs videos were also sent. Ava's masturbated in bed right next to me while on the phone with her....

My wife's father had to take early retirement as his health was failing, so she became the boss of the family firm. They had about 20 employees and the business was doing very well. She was bringing home more income than I was.
Meanwhile, the company I was working for was struggling and eventually I was made redundant. There was a decent payoff, so I didn't need to worry about getting another job straight away....

Michelle looked around to make sure none of Sandra's neighbors were out and about as she pulled in to the drive. She'd texted Sandra that she was on her way so Sandra would unlock the door for her.
She felt both slutty and sexy arriving back at Sandra's house in the same dress and heels she'd left in last night. She'd heard girls talk about doing the "Walk of Shame" after a date, but this was the first time she'd done it....

I made it back to my dorm room without issue. My sissy initiation was intense. I thought about how I've taken more cock in the last 48 hours than my entire life. Instead of shame I felt aroused. I cleaned myself up. Washing the word "SLUT" off my forehead was difficult. The permanent marker had stained my skin and I had to scrub hard to remove it. I didn't bother washing the word "CUMSLUT" off my ass. I figured the effort wasn't worth it. I went to bed and slept like a baby....

This is the second story in the Sugar Journals series. Every story is a stand-alone work. All characters are over 18. Please leave feedback and vote. I hope you enjoy the story.
***
"You should really consider this, Jessy."
I put away my phone and took off my earbuds when I heard my roommate Cindy speak, but didn't exactly hear what she was saying....

Jason was a football star in high school. Being dedicated to the sport, he spent as much time in the gym as he could working out. By the time he graduated, he had become a big, muscled guy. He earned the nick name big jake because he had the biggest cock on the team. Unable to afford college, he got a job with a contractor. It was hard work, but the pay was very good....

We layed together in my hotel bed just holding each other, she gently rubbed my chest with her fingers as I stroke her head on my shoulder. The past 36 hours had been an incredible journey of life changing love and passion. I tried to let it all sink in, everything that had happened the past day and a half was so incredible, I still couldn't believe it was all real. We had shared our bodies with one another, but we connected on a much deeper level. In a strange way I felt like for the first time in my life ...

Hi, I'm Gwen. I'm a twink crossdresser. I'm pretty passable; no one questions I'm a girl. Right now I'm wondering, how the fuck did I get out here? As far as I can see, not one damn house. I've been walking for 20 minutes, and not even a fucking car. Finally, a car, far off. I need to get him to stop. He has to stop. I'm wearing tight little jean cutoffs, sneakers, and a halter. As the car approaches, I see two males in the front seats. They see me. I pull my halter all the way up over my titties. This is n...

Hi! Thank you for the nice comments on this series! ALL CHARACTERS ARE OVER 18.
I returned to the Spurge household the next morning, as requested. Mrs. Spurge rolled her eyes and shook her head when she saw me, then turned without saying a word. She had a cigarette gripped between the fingers of the same hand she was carrying her coffee with, her phone in the other. I heard the screen door to the patio and pool open and close. I sat at the breakfast nook....

My last experience that I wrote about was my visit with Chuck and then with his neighbor James. I am quite sure that both Chuck and James talked to each other about our little romps in the hay. Chuck and James have my telephone number, I told them if they ever want to get together again to call.
It was a Friday afternoon and I was at the office working. My cell phone rings, the caller ID stated "James."...

I returned home after my night with Rick. I was no longer wearing that pink chastity cage, but my ass was still full of his cum. I was so horny and was excited to be able to jerk off.
I got slipped out of all my clothing and got into bed. I started fondling my sissy cock and balls. I grabbed my phone and decided to check my emails for any sexy messages. I seen a new email from an unrecognized address. It was titled "whore" and it had an attachment....

As day light crept through the blinds and my eyes opened, I asked myself was it all a dream?   But as my eyes focused, in the light i saw her laying there in my arms and realized this was real.
Last night had been so incredible,   the woman of my dreams just gave me the most amazing night of my life. As she lay there asleep in my arms I thought to myself what I should do. Should I gently wake her with loving touches and kisses, or do I try something different. I decided to slip my way under the sheets to...

Corey went to high school with me back in the day when I was a boy before I started transitioning. My name is Hannah, and I'm 29 years old. I stand at 5'7 and have been transitioning for 3 years now. My hips were wider, and my butt grew bigger along my with my breast. My body filled out nicely to look very feminine....

"Yo, Bro. How many followers have you got?"
Leaning back in my rocker gamer chair, I looked at the computer screen to the left and saw that I had almost one hundred followers.
"Ninety-five, Kyle. How about you?"
Kyle groaned, mumbling that he had only eighty-five, still, that wasn't bad for our first month of streaming. Other than our love of gaming, which we had shared since we were young, there was nothing special about us to help us build a following quickly; we were just two scrawny geeks who w...

Mia usually only dates guys she meets in real life. She doesn't like using apps and she really doesn't like blind dates. But her friend Tara had been so insistent that Mia and Brian would hit it off. Mia was a little bored and trusted Tara's insight on such matters. She decided to give Brian a chance. Tara showed Mia a picture and said, "Brian is really your type. He's good-looking and fit. He travels a lot, loves to have a good time, and is very, very selective on who he dates. He dates a lot, but he only ...

After their first night together Euan was no less horny. He still went to the soldiers that would fuck him senseless but he'd still beg for Andreas' cock until the knight gave in and pounded him til he was crying. Andreas had noticed a certain new attraction in his King. Euan had started going after his general. The man was even broader and more imposing than Andreas. It was no surprise he wanted him....

"Oh, at first it was just wonderful. Rico got assigned to Italy, to serve as kind of an MP at a naval base. We were so excited to move, and my baby, Marco, was 10 months old and doing fine. Italy! Imagine! The housing was OK. But after a year, Rico'd started drinking a little too much with his buddies, and spending more and more time away from me. Why would he act that way?"...

Hope you enjoy this fun and naughty little tale of two roommates whose friendship gets very interesting after a secret slips out in the sexiest way possible.
If it gives you a grin--or a tingle--leave a comment or shoot me a message. And don't be shy... check out my other stories too!
All characters are adults aged 18 or over....

This is a fantasy story of a young white man finding a new sexual awakening.
I am a new writer who's trying to add stories to this great site. If you don't like the story please move on don't leave negative comments and mark's! Just please move on?
There are themes of Sissy Clothing/Butt Plugs/Anal Black Men fucking White Man/Queen of Spades and watersports if none of these interest you please skip this story!...

I spent a week caged. I only had two filled condoms. The school week made it hard to play and Tom seemed to be avoiding me. Going to my classes caged discretely also was proving challenging. I was nearly ready to remove the cage until I seen an email from Rick.
He sent me his address and told me to come over tonight after 6 pm. My sissy heart fluttered. I packed my bag with clothes and make up and waited patiently....

Graduation was last week, and the graduation party is tonight. I'm finally glad to be out of that damn school. Turning 18 and graduating was a godsend. Being trangender and living in a small conservative town was hell.
I moved here from New York with my mom to be away from the crazy life of the big apple. I started transitioning a year ago, starting with hormone therapy. Still, the kids and parents here see me as a freak. This last year was horrible, yet I still met a couple of good friends here....

The morning sun sliced through the grimy blinds of my fifth-floor walk-up, painting streaks of gold across my pale ivory skin. I groaned, rolling outta bed, my dark wavy hair a tangled mess spilling past my shoulders, sticking to my sweaty neck from a restless night. My tiny apartment smelled of stale coffee and the curry wafting from Mrs. Patel's place downstairs, the city's hum already seeping through the cracked window--honking cabs, shouting vendors, the distant wail of a siren. My brown eyes, framed by...

Tyler moaned as he lay in his bed with his cock in his hand. It was the middle of the afternoon on a Saturday and it was raining. Tyler had woken up with a text from his sissy girlfriend telling him to edge himself before she came over. She had sent him several nudes and Tyler had gotten so very horny that he had to jerk off to them....

Part 4
Boy, did we open up a can of worms by having sex for the first time. We were like a couple of rabbits. We made love every time Kenny came over. Mostly in my bed, but I think we ended up doing it in every room of the house. I made sure that when he was there I was always in thigh highs or suspender hose, so he had easy access to by bottom. I made sure to wear skirts too, so I could just flip it up, whenever the mood struck us. I even had to go so far as to buy more panties, because I had to change ...

Thanks everyone for your comments and suggestions. They are always welcomed.
As usual nobody in this story is under 18 years old.
Cassie woke up in a silky nightgown that Dan had purchased for her. She loved the feeling of the soft fabric against her skin. Dan was sleeping next to her and she could feel his cock poking against her body....

As I think back remembering some of the crazy times and things I've done to dress up in women's lingerie I'm continually reminded of episodes that occurred over the years and how lucky I have been.
One such episode happened over a period of time when I was married to a stunning very attractive woman. We lived in a house on the east side of Vegas on the edge of civilization and open desert, close to an area of town known as the swamp where all of the water run off from Las Vegas flows to the east of the c...