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Cross-dressing Stories

cross-dressing

My Sister’s Bully Ex 3

Sophia’s adventures continue as my sister’s bully ex takes total control.

So here I am, standing in my sister's living room, wearing no underwear and having received a heavy pounding from her bully ex-boyfriend. I was in total shock and panic that my sister was upstairs, upset at what she had most definitely heard from me and Rich. What the hell would she think, finding her brother dressed like a slut in her living room? I hurry to unlock my phone and book an Uber ASAP. In my moment of panic, I...

Andy Mandy & Me

We need rules. I am not having him dressing up, watching porn and masturbating his pathetic little cock, every time I go out. No.

“Andy, I’m home!” His face appears from behind the door of his office. “Oh, hi, Alice. You’re early.” He looks surprised, perhaps worried. “Come here, now.” He hesitates but he knows he will have to do as I have said and, as he steps from behind his cover, I know why. “I was only trying them on,” he says, his hands cupped over his groin, the tiny panties visible on his hips, the suspender belt and stockings finishing the...

In the soft glow of neon lights, a cozy bar tucked away in a quiet part of town was buzzing with low conversation and the clink of glasses. The warm ambiance and chill music made it a perfect place for anyone seeking a little escape. Sitting at the far end of the bar, Karen adjusted her black lace gloves, smoothing the fabric over her wrist. She’d been coming here for a few nights in a row, always drawn to how accepting i...

An Affair With A Twist

Part One - My Latest Affair Takes An Unexpected Turn

I connected with Jim online. Although married, I enjoyed having occasional one-night flings. I’d usually connect with a married guy who came to town on business. I wasn’t interested in anyone local. It was important to get to know the guy before I met him though. The process took a while but always resulted in meeting a nice guy. Over the last couple of years, I’d fucked fifteen very nice and appreciative married men. All...

My Sister’s Bully Ex 1

My sister’s bully ex-boyfriend notices me dressed and I can't resist

My name is Sophia and I’m a twenty-one-year-old sissy girl who loves to dress femme all the time. Over the past few years, I have got more and more daring with my feminine side, going out in public dressed. It was on one of those adventures I discovered a nightclub in town that was a hotspot for the LGBTQ community. I would often go there fully dressed and make new friends, drink, dance and have some fun. It was on one of...

Trading Places

After a horrendous marital fight, Brad and Marcie wake up to a completely new perspective of their spouse's life.

Brad pulled into the garage after a grueling day at the office. His wife, Marcie, had already parked her car in her space. "I'm home," he announced, looking at her back across the kitchen at the stove. "About damn time," she said without even looking at him. "Don't even start, Marcie. I had a horrible day at the office. The Davis deal almost fell through, and I had to stay late and work my ass off to save it." "Great! Tha...

“Hi, Andy, I’m home!” I throw my bag down, and my jacket soon follows. Fucking typical, for once I get home early and he’s gone out. I glance briefly into his office, but he’s not there. But as I climb the stairs, I am conscious someone is in our bedroom. “Hello?” I say, pushing the door open. What the fuck! “Oh, shit, fuck,” and the person in stockings and heels, with a black basque and matching panties, runs for the en-...

Losing Control - Part 6

I meet up again with Alice, and I lose an argument with her.

Work-wise, I had an easy start to my new life. Having arrived at midday on a Saturday, the rest of that day was spent learning the layout of the large house and what my role was. Then, the following day, Sunday, was a free day, so I spent the time in my room or the garden, sometimes in conversation with Helen. Alice was away for the weekend and didn’t return until Sunday evening. As I was allowed to do, I chose to wear ma...

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Your Turn

Today my lover gets to be submissive

You tell me you’re feeling horny and submissive. So I say, "Go put on your stockings and panties. Lie down on the bed while I sit in the chair and watch you from across the room as you fuck yourself with a dildo." I sit and watch, idly stroking myself as you spread your legs wide and insert the dildo. You know, of course, that you're not, under any circumstances, allowed to touch your cock. While I watch, you describe how...

The Lake House - Part Two

It Gets Complicated

I awoke Sunday morning in my pink nightie. I thought about how much had happened in the previous two days. I was now Jim’s girlfriend. I had sucked off four men and swallowed a quart of semen. I became aroused. I only had to play with my clit for a minute before I started cumming. I caught most of it and fed it to myself. I looked forward to sucking Jim’s huge dick. “You better get dressed, girl,” I said out loud. I did m...

Stolen Treasure

A tale from the Sixties

Sixteen-year-old Ian West cautioned himself to remain calm and stick to his plan because detection would be disastrous. It wasn't as if he had not shoplifted before, but nothing this grand. Now long before Victoria had her secret and the shopping malls appeared, there were dozens of small specialty shops scattered across the city that carried everything in the way of lingerie. There was no internet or online shopping, thi...

The Lakehouse

How I Became My Neighbor’s Girlfriend

I’m married and we have two houses. One is in a suburb of Chicago and the other is on a lake in Wisconsin. When we first bought it, we went frequently. We became friends with the only neighbors, Jim and Barb. We had a good time with them, but after two years, it became clear that their marriage was on the rocks. Shortly, they got a divorce. After that, the three of us would get together, but it wasn’t the same. Jim is a t...

Hired For A Poker Party

I had a great time

I had been chatting off and on with a local man for a few months. A couple of weeks ago he asked me if I would be interested in being a server for his next poker party and he would pay me $200.00 plus tips. I got really excited at the thought of doing it. I told him that I had a few thousand questions first! Lol! First, how many guys would be there? Four, he responded. Second, do all of them know that I am CD? He said tha...

The Rules

From Husband to Cuckold to Property

"Well, my lover and I have become quite close over these last several months. He is single, good-looking, and an alpha male. One night, when he walked me to my car, I turned around to say goodnight, he leaned in and kissed me. It was a long and lingering kiss. He also grabbed one of my breasts, and I have never felt such a sexual energy in my life before. That one kiss got me so wet, and my head was spinning. I knew I had...

Now Jason had no plans to reveal his cross-dressing secret to Melissa, but the fates had other plans. He had been so busy tidying up his condo in preparation for Melissa's visit that he failed to see the panties that had fallen onto his bedroom floor. He didn't bother to do a double-check but raced to admit her when he heard his doorbell ring. Once behind the closed and locked door, they locked lips and allowed their tong...