Sissy Tattoo Stories

17,774 results
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A Night of Makeup, Cock and Cum

by mikhaylacumme on Sep 13, 2017
Transsexuals & Crossdressers

It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further, I had always wondered what it would be like to be with one a...

Emily: Snowbunny Ch. 01

by rubbing1out on Sep 25, 2017
Interracial Love

As Emily spoke Brad double-checked the Find My iPhone app and sure enough she and her phone were still at the office. He mentally admonished himself for doubting her. "Well don't worry," he said. "I'll get dinner ready before you get home. What time do you think you'll be back?" Emily stopped sucking Damien's cock and leaned toward the speakerphone where i...

Turning Summer Ch. 2

by monika ikon on Sep 12, 2017
Transsexuals & Crossdressers

It was the week before the 4th of July and summer had officially begun. Two months before my wife Kathy had given me my first bikini. She said she wanted to put some new life into our relationship and I wanted to do whatever I could to make her happy. My appearance had changed a lot since then but it didn't occur to me that anything was out of the ordinary....

The Teamviewer Mature Files

by jothesmo on Apr 23, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. * The computer screen shone light upon my plain-white panties and bra, making them glow obscenely atop my peachy white skin. Since the divorce, I'd become brave in private and crossdressed on occasion. That sometimes ended up all day. The webcam was on, but I wasn't in any kind o...

My Life with Little Sparrow

by DomAlphamann on May 11, 2020
Fetish

I almost never come home early unless it's for a good reason. I have two reasons today; one of those being to keep you on your toes, of course, the other one is to give you news. If you followed the rules, as you should always, you might have heard the car pull up, but just in case you were busy doing anything for your own sake and enjoyment and didn't hear...

Just the Way You Are

by Sandwiches_Are_Good_Too on Sep 16, 2017
Transsexuals & Crossdressers

"No! You are not taking my babies from me!" "This isn't about you! Its about providing my sons with the best home environment, and that's not with the woman who may be high as a kite at any given moment!" "If you had paid an ounce of attention to anything that was going on in your 'home environment,' you would have noticed that I've been clean for twelve...

Weekend Games

by SissyAndi on Sep 16, 2017
Transsexuals & Crossdressers

I was 42 and working at a dead end textile job. The only bright spot was that I worked with a woman named Tammy, she was a hot red head with a great body. I figured I never had a legitimate chance of getting Tammy to go out with me but a guy could dream, or in my case it was more of a fantasy. Tammy and I lived close to each other and one day she asked me...

How We Became An "Owned Couple" Ch. 12

by watchdwag on Sep 26, 2017
Loving Wives

The Conclusion It was strange coming home to Lee instead of my wife but over the next few days I became more accustomed to my new mistress. It took some time to adjust to the chastity device that had been installed but eventually I accepted the fact it was there to stay. I also no longer took issue to the panties Lee had me wear. I resigned myself to the fa...

Remaking a Boyfriend Pt. 06: The Big Decision

by her_every_command on Dec 3, 2019
Transgender & Crossdressers

The next day, Sunday, was much more relaxed. Ray again got dressed up in an outfit of Allison's choosing, this time a pencil skirt and blouse. Allison had him do some of his own makeup as he continued to learn how to apply everything. They went to brunch, where the waiter flirted shamelessly with them and gave them a free round of drinks. Ray tried out his g...

Tyler and Candace

by wantajerseyboy on Sep 16, 2017
Interracial Love

Wake up! Wake up! Mommy I'm hungry ok just give me a few more minutes ok mommy that was the sweet sound of Candace's 3 year old Tyler Allen Jr., named after his daddy. I am a teen mom I let a boy talk me into having sex after homecoming my junior year of high school, he wasn't just any boy though, he was the boy I was in love with forever I have known him...