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Just For The Taste Of It

Vanessa is trained to love the taste of cum

Many years ago, before I was the experienced sissy girl I am now, I was living with a man named Jake. Jake took me under his wing. He wanted to help me become as girly as I could be. One of the things that he wanted to get me used to was the taste of cum. I had tasted it before, but only my own and his. Jake wanted to make sure that I was a cum expert. He said to me, “A true sissy...Read On


Allen's Sweet Surprise Part One

Seeing my boyfriend in ladies clothing is sweeter than I expected.

My pussy was dripping as I zipped my car into the parking spot in front of the mall. I was having another secret meeting with my boyfriend, Allen. Only, this time we'd arranged a little twist to our usual tryst. After years of Allen and I seeing each other, I'd finally worked up the nerve to share my fantasy of him dressing up like a woman for me. It wasn't easy for me to do. I'm a...Read On


Fucked in the Fitting Room Part Two: The Explosive Conclusion

When my lover finds a dress on the sales rack, I get more than I bargain for.

I took Allen's hard cock in my mouth and began to suck it slowly. "Oh, God," said Allen. I rolled my tongue around the tip of his cock and then ran it up and down the sides. "Suck it faster, babe," said Allen. I happily complied, bobbing my head up and down on his cock as fast as I could. I grabbed his balls in my hand and stroked them gently with my fingers. "Oh, baby, that feels...Read On


Fucked in the Fitting Room Part One

When my lover finds a dress on the sales rack, I get more than I bargain for.

My boyfriend, Allen, loves to wear women's clothing. It's something he's been doing awhile now, probably three or four years. We both get very excited about going to our local department store to hunt for new additions to Allen's wardrobe. Last night we had one such shopping trip and we both had a luscious time. "Grab a buggy," said Allen when we entered the store. "I plan to load up tonight."...Read On


My First Time Final Chapter

The conclusion of this story

The Friday that Lydia told me about had finally arrived and she would be bringing some of her friends over for drinks after work, and I was to serve them as Melissa. Lydia had also advised me that unlike the dominatrix persona I used during my first outing on Halloween, Melissa the maid, was totally subservient. That morning after my usual visit to the gym I cleaned the house and set up...Read On


Steve the Crossdressing Cat Lover

Cat lovers are a breed of their own and my boyfriend, Steve, is one of them.

My boyfriend, Steve, has a lot of cats. I can't tell you exactly how many because the little critters come and go out the pet door and scatter as their furry little paws please. Steve lives on a farm. Well, it's kind of a farm. I mean, he has a lot of land, but he doesn't exactly grow anything on it except cats from what I've seen. And he has a barn, too. You'd think with all that land...Read On


My Boyfriend's Blue Silk Panties

a crossdressing shortie

My boyfriend, Allen, is a man's man. Let's get that straight from the start. He rides a Harley and he scoops me up in his big strong arms like I'm light as a feather (which I'm not...let's get that straight from the start, too). So it was a big stretch for me to ask my masculine lover to slip into a pair of silk panties just for me. It was a secret fantasy I'd harbored for years but had...Read On


First time sex with a man!

How my first time anal started and happened.

So there is this guy who I've been talking with for awhile. I wasn't too interested because I was still on the edge about meeting up dressed with another person. At the time I was under the influence and I sent him this message.   "I have recently been dressing up more as a woman as my family have been busy. I have been eating my cum all dressed up like a sissy! I have been eating my...Read On


The Wedding Present

Chardonnay wants to show her boyfriend and lover how committed she is to him.

Chardonnay had been Phil’s live in sissy lover and constant companion for just coming up to two years. She wanted to do something very special for him and had saved enough money at last. She phoned an exclusive hotel, giving great detail into what she required. She made a few more calls that afternoon while Phil was working. As she finished the last call, she gave a huge grin to herself in...Read On


The Neighbour's Knickers - Part 1

A man who just can't resist the opportunity to get into his neighbour's knickers

It was a sultry summer night but it wasn’t the muggy air that was making me hot. It was my clothes. I’d felt the urge to dress up in a very sexy outfit. My preparations had started much earlier in the day, and they had been thorough: my whole body was clean and smooth, shaved so that there was not the slightest hint of hair anywhere other than on my head. My heart thumped wildly as I...Read On


After the Show

An invitation to a drag show proved to be an invitation to more.

I‘d met David through my (now ex) wife. He lived in the Twin Cities with his partner Dennis. His being gay made it very easy for me to talk openly about being Samantha. He hosted a drag show on Saturday nights at a small gay bar so he’d invited me to come along, meet the ‘girls’ and see the show. I could stay the night so I could go dressed and have a fun ‘girl’s night out’ while he MC’d...Read On


Keeping A Secret

The drive home from the Cities was always long. After work I had stopped at Kim’s to change and emerged as Samantha. I drove to the meeting and then went out for a drink (or maybe two) with some of the other ‘girls’. By the time I was half way home my eyes just wouldn't stay open any longer. I decided to pull over in a secluded wayside rest area. If I could just catch a little catnap I knew...Read On


Ready to Perform, Part Two – All Crossed Up

I get more than I bargained on!

Much happened in the next twelve months following that first session with my ex and her new partner: Ann began divorce proceedings which I didn’t contest, I financed myself into another home, and Ann, David and I met for two more sessions of torrid sex. These sessions were pretty much replays of the first; I would first screw Ann thoroughly through at least two climaxes, and then she would...Read On


A surprise ass-fucking in panties

A friend displays her kinkier side

A very curious thing happened to me the other day and I feel I need to share it with you... I have been 'mildly’ crossdressing for over a year now. I say 'mildly' because I am not into full feminization, I just love the feel and look of lace panties when they are hugging a good looking cock, not to mention the taboo. I have taken to wearing stockings too which feel amazing, it's like...Read On


What a Girl Wants

'Katie' finally fulfills her fantasy of having sex with a man.

"Come on, Katie. Give in to your desires. You've gone this far. You're almost there. You're so close to your goals and dreams of being treated like a lady. Accept it. Embrace it. Give in and complete your journey. Tell me what you want." Todd and I had been friends for years and even co-workers at one point in our respective careers. It had been almost ten years since I'd seen him and it...Read On


My First Time - Part 3

The story continues...

As Lydia had promised, on the first day of her vacation I got my first lessons in high heels. It took most of the day before I was able to walk across the room and not fall on my face, and these were only a moderate heel. I took her to dinner to celebrate and, at her request, I wore the satin thong under my jeans. Lydia could not resist reaching out and squeezing the bulge in my jeans,...Read On


July 4th Celebration

My wife Ann sets up a mini vacation over the 4th of July.

On July first I returned home from our health club. Ann was packing my suitcase for a mini vacation at a bayside resort. My suitcase was filled with all my girlie things: lubes, vibes, wrist and ankle restraints and the paddle she used on me when I was bad. She also said Ben, his brother Josh, and two others were joining us. Before continuing, I should mention how I became the man I am...Read On


The Business Trip - Part 1

A man has a wild experience on an unexpected business trip.

I work for a small web design company in northern Connecticut. We acquired a rather large account with a lawn care company in Virginia, and my boss asked me to go with him to present the design we had created, since I was the only other male at the company. My boss told me he didn’t want any of the women to think he was hitting on them. Never having been asked to go on a business trip for...Read On


Just the Two of Us, or Four

Vanessa and Greg fail at trying to spend a night alone

As time went on, the line was beginning to blur between me being Greg's girlfriend and Amber's pet. Greg decided that we needed a night alone. That didn't work out exactly as planned. He booked us into a lovely, fancy hotel in the heart of the city. Next up was going to be a nice dinner at a gourmet restaurant, and then we'd see where the night went from there. I wanted to impress, so I took...Read On



Crossdresser is caught by his flatmate and fuckec

I stood in front of my full length mirror wearing my new black heels. Not just the heels of course! I had a sexy, short black dress to go with them. Underneath, I had some incredible purple and black underwear; all silk and lace. I twisted on my heels and pulled my dress up a little, wiggling my thong covered ass at the mirror pretending somebody could see... ...And that’s when he knocked!...Read On


Caught By My Girlfriend

Hitting puberty late in high school had its disadvantages. A slender, almost feminine body and a small dick was not something a lot of women tended to go for, however, I was lucky enough to find Adrian. We hit it off right away, shared many things in common and we couldn’t get enough of each other. She was gorgeous, standing at six feet, she was just as tall as me. Her beautiful crystal blue...Read On


An Uneven Romance - Part Two

He's taken further into her strange, kinky world

“Hey, Sam.” I jumped and spun around, startled. One of my housemates, Mark, had walked into the kitchen where I was preparing breakfast for Sarah, the incredible girl I’d brought home the night before. Sarah was a pretty special girl; after a night spent with my head between her legs she had eventually let me cum this morning. She’d somehow coaxed me into wearing her wet panties from...Read On


An Uneven Romance

He picks up the girl of his dreams only to find himself being used

I couldn’t believe I’d gotten her home with me. We’d met in a bar when I was drinking with my friends, I spotted her early in the night but didn’t have the courage to talk to her. She looked perfect. She was slim, with long red hair that came down to a tight, round ass. When she turned around, I saw she had a truly beautiful face but there was a sexy, dangerous look in her eyes that scared...Read On


Anonymous Encounter

An Anonymous Encounter of a Crossdresser with someone from Adult Friend Finder!

Well it was a boring day. It was fairly hot outside,somewhere around 93 degrees. The sun was shining, there were very few puffy clouds in the sky, and I was home alone. As usually happens when I am bored and home alone, I was horny as hell. I wanted to jerk myself off, but I wanted to do it to something different than the normal porn that I usually watch. I figured since no one would be back...Read On


film fun

I get fucked while her husband films it

I met Lucy on the net, she was a married BBW with massive breasts (46g) and ass to match and loved to dress how I like my ladies to. That means mini skirt, high heels, stockings and suspenders and a low cut top.  We had met a couple of times before I got to meet her husband Ray.  Lucy and Ray had arranged to come to my house one Saturday night for some food , drink and fun, but I had no...Read On


From Shock to Awe...some

The day my sex life was unexpectedly changed forever by a loving wife

To this day, I don't know what caused my wife to come home early from work that morning, and although at the time I was sick to my stomach with dread and fear when she walked in on me, I'm now glad that it happened. For the first time in over ten years of marriage, we can now finally talk about what sexual desires we have. But I'm getting ahead of myself. Let me back up a bit. I met my...Read On


First Night Nerves - Part 2

Tina agrees to meet Barry without 'the girls'

I sat by myself on the bus, my briefcase on my knees, counting the stops and wishing it would go faster. Since Barry’s text message last night and his surreptitious call to my mobile that morning, I had been so excited, planning what I would wear to please him most. Debbie hadn’t heard the beep on my phone so didn’t know that I would be meeting him without her that afternoon. So far I had...Read On


Starting to Have Fun as a Slave Girl

Vanessa is won at an auction to do one man's bidding for the night

Greg and I had resumed our relationship as normal after my experience at Mistress Amber's. I was enjoying being his girlfriend. He treated me so nicely, and we enjoyed our time together. It was the most intense sex life I had ever had with anyone. For the most part he enjoyed being the dominant one, and he was happy to make me his little fucktoy after a nice night out. But it was that line...Read On


My New Sissy Life

A sissy lives out her ultimate dream.

I was so stunned I was unable to speak. I only thought things like this existed in my fantasies and could never actually exist in the real world. It had been three weeks since I found an ad posted online seeking two submissive males for "training." I read the description which said, "Attention sissy boys! Have you ever wished that you were a trained sissy slut? Of course we both know the...Read On


First Night Nerves

Nervous Tim becomes Tina and loses her virginity

My name is Timothy. I live in a large city in the English Midlands with my girlfriend Debbie. We are both 22 years old and have lived very happily together for over three years. We both work in a call centre for a large financial organisation. I am not tall – 5' 4" on a good day – and have always been very slim. I am blonde with blue eyes and very fair skin. Debbie is two inches shorter than...Read On