Sissy Tim Stories

12,400 results
Orientation
Length
Source
Infinite Scroll

The Tax Divorce

by taylorsam on Apr 22, 2020
Loving Wives

It was a close friend who clued me in that my wife of twenty-one years was cheating on me. My buddy Bruce called me at work tell me that he has just seen my wife Libby walking hand in hand into a cheap hotel on the outskirts of our tow. He said he took some pictures on his phone. Of course, I didn't believe it at first. I figured there had to be a logical ex...

Mistaken Identity Ch. 01

by Lovinhose on Apr 13, 2020
Transgender & Crossdressers

Another work of fiction, hope you enjoy. Many years ago I had a regular. I lived about 40 minutes south of him, but he lived only five minutes from where I worked. I would go to his house after work, often dressing up ahead of time in my pickup truck in the parking lot at work, then heading over for a good screwing. This spanned over a ten year period and...

The Love of My Life Pt. 06

by DrJen on Jul 13, 2020
Erotic Couplings

In this part, I discover the joys of oral lovemaking after a surprise session with the Chair of Psychiatric Medicine. ******* On Monday afternoon, I was still confused and reeling about my lovemaking with Rob over the weekend. I felt I had crossed a boundary and was worried that there could be no turning back. I had actually enjoyed being spanked at the he...

Who Needs a Protein Shake?

by spacecowboy36 on Sep 28, 2020
Erotic Couplings

One of the worst parts of living in a major city is the amount of people. After a while it becomes somewhat normal, but when you get outside of the city it shows just how abnormal this truly is. When you live in New York City, you feel more like sardines packed into a container than people living in close relation to one another. These thoughts were racing...

What's Your Fantasy Ch. 04

by Optimus9812 on Sep 19, 2017
Fetish

After three rings Jessica heard the familiar voice of her best friend, Kate, on the other end of the phone. "Hey girl, what's up?" she answered. "Hey, so...you remember how I was telling you about things I wanted to try with Stephen? Well, I did one of them!" Jessica told her. "No shit?! What did y'all do?" She told her friend about the events of the pa...

Slave Ch. 10

by slaveheathen on Sep 25, 2017
Fetish

Note: I refer you to the notes in previous chapters concerning the fact that this follows a bisexual submissive male. To the anonymous commenter who keeps insisting this should be in Gay Male, sorry, but there's a lot more going on than just dude on dude sex. This story covers multiple categories, all of which are fetishes of one kind or another. If I ever w...

Steel Heaven

by LockedDarius on Sep 11, 2017
BDSM

I stood in the shower, allowing the hot water to caress my body in an attempt to wake myself up. The thought of another long day at work wasn't helping the situation, but at least it was Friday. "Get through today and enjoy the weekend," I thought. I stepped out of the shower and immediately realized I had forgotten to bring a towel into the bathroom from t...

Auntie's New Tenant Ch. 03

by BrettJ on Sep 15, 2017
Novels and Novellas

For some young men, hearing that they would have to move in with their aunt might have seemed like a death sentence. For young Daniel Talbot, it had been nothing of the kind. In fact, it was almost the polar opposite - it was the start of an entire new life, one filled with unending joy and incredible sex. Only a short time after moving in with Katrina Pear...

Sissy Gets His Wish

by Tinydickthongboy88 on Sep 18, 2017
Transsexuals & Crossdressers

I should've guessed something was up when my boss Victoria winked at me on our way into the office. She's about 5'9", 130lbs, she just got a boob job last winter, and as she walks by her ass bounces in the sexiest way I've ever seen. Work started normal enough. Our company was in the testing phase of software for a military application. I wasn't clear on i...

Solo Submission Pt. 03

by Subkoksukr4u on Sep 23, 2019
Fetish

Debbie awoke the next morning refreshed. She was alone in the large California king bed. Cindy, already up but let Debbie sleep in a bit. It was Saturday and neither of them had anything to do but relax. Images of her husband sucking dildos and eating his own cum popped into some of her first thoughts. Having sex with Cindy convinced Debbie that someth...