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Crossdressing

9

My first boy experience

First time cross dresser ends up with well hung guy..

It was my friend, Karly's birthday. Her choice for going out to celebrate was a drag night at a club. It wasn't so much fixed on drag as it was on gender parodies and cross-dressing for fun. I had been a closet cross-dresser for a long time, although I had told a couple of girls I knew. Everyone was going to cross-dress and have fun, but I was going to revel in it. I had never been with a...Read On

7

Carl, Carla and Hannah - Part 22

Hannah gets a promotion, and Claire pays a visit.

A couple of weeks later, Hannah came home and told me that the rumours had been true, and Claire had been promoted. As Hannah had been at the company the longest in her department, everyone expected her to apply for Claire's old job, and the general consensus was that she'd get it. Hannah was determined to get it as well, telling me that the extra money would come in handy for the wedding....Read On

9

Free Clothes

Not what I expected, but definitely what I wanted.

I guess it is something that goes through the mind of every new or closeted crossdresser. Shopping for new clothes as a guy is awkward because it is difficult to do without making it obvious it is for you. Yeah you can go online, but it’s tough if you’re not used to the sizing and the clothes never seem to look the same as the picture. Thus, when searching for playmates on Craigslist, if you...Read On

13

Mom's Old Boyfriend: Part Two

Courtney becomes an escort like her mother, after fucking Ron good like she did.

Having adopted my mother's appeal for wearing sexy clothing and turning on men, I had just sucked her rich former boyfriend's cock while she flew to Las Vegas for a long weekend with her new rich boyfriend. Mom had a love for the jet-set lifestyle and I was sure she was enjoying staying in an exclusive hotel and fucking her new boyfriend's brains out when he wasn't at the table gambling....Read On

13

My Sexual Odyssey Part III: Becoming a Slut (Continued)

A continuation of the journey described in part 2

We got to Tom’s car, and he opened the door for me, then walked around and got in himself. The drive was short and uneventful, and we parked behind the club. There were some people arriving at the same time we were, and I noticed several who looked like they could be CD’s. We approached the club’s entrance, and I began to feel more relaxed. It is always uncertainty that is anxiety-producing,...Read On

6

Carl, Carla and Hannah - Part 21

Carla spends Thursday night with Tom, while Hannah hears of a possible opening...

A few days later, I rang Tom, this time leaving my number visible. We talked for a while, and we both agreed that we'd had a good time, and would like to see each other again. Before I hung up, we'd arranged for me to go over the following Thursday, as that was Hannah's night with Claire. Hannah and I spent the next few days thinking about the wedding, looking at suitable venues for...Read On

15

Mom's Old Boyfriend: Part One

Courtney seduces her mom's old boyfriend and sleeps with him, all weekend..

It happened quite by chance and we managed to keep it a secret, ever since. I was home alone on a Friday evening wearing my mom's favorite black lace lingerie and her old boyfriend, Ron, came by to see her. He still had a key from when he was seeing my mom and he walked in without knocking on the door, startling me. And he caught me playing with myself through the sexy little black lace...Read On

4

My First Night Chapter 2

The second chapter to my night with Marie

Previously She also included in this bundle of sissy goodies, sheer black thigh high stocking and black three-inch wedges. My legs were so high and my body so curvaceous, my soft red lipstick tied in with the red baby doll. She had placed a blonde wavy wig which I tied into my hair with grips and styled with a middle part-in. Marie also supplied red nail varnish and some very...Read On

15

My Sexual Odyssey Part 2: Becoming a Slut

A continuation of the journey described in part 1

After having had a few experiences, I became slightly more comfortable with my sexuality. I decided to branch out a bit, and see what life had to offer. I wondered whether there were any bars or clubs that I could go to to meet people who were looking for someone like me, so I went online and discovered, that yes, there were quite a few such places. It is so wonderful having the internet...Read On

9

Carl, Carla and Hannah - Part 20

Carla's night with Tom continues, and then Hannah has a surprise for her.

I lay down on top of Tom, and enjoyed the feeling of his arms around as he kissed me, telling me that I was great. I lay in his arms for a while, and we chatted about this and that. He told me a little more about himself, his failed marriage and what happened with a guy he met. All the time he talked in his low, sexy voice, his hands caressed my back, occasionally wandering down to the tops of...Read On

16

Call me Julie

Never assume you have complete privacy.

Coming back to garrison, after a yearlong deployment, is one of the best things ever. Imagine having to go a year without having your favorite lingerie to change into, and not being able to shave and pamper your body as you would like. As it so happens, we just got back the day before yesterday, and after all the clean-up and inspections, we are being given a four day weekend. My...Read On

7

Once Again in Silk - Part 1

It had been many years since my time in Florida and my transformation to Melissa to please my lover, Lydia, and also my own inner desires. She grew out of her desire to see me dress up, wished for a more normal life and to date other men. I sensed that our time together was coming to an end, so I moved back North. As I still had a sizable amount of money left from my settlement. I didn't...Read On

7

My First night

A Night to remember with Marie

This is a true story that I personally have experienced and wanted to share with like minded people. Thankyou.  The evening drew closer after work which had been busy and made me rather stressed. I work as a graphic designer/illustrator in a well known and respected company. I left my studio in London and drove the twenty minute journey that I make, day in day out, to my flat which I...Read On

12

The Sexy Girl-Next-Door: Part Two

Courtney has a neighborly affair.

Once a girl gets a big hard cock in her, there is no stopping her from wanting another one in her. At least, that's how it was for me after my first fuck with my neighbor, Ben. He had just fucked me with his twelve inch cock, with a big head on it and I loved it so much I couldn't wait to do it again. Our friendship was growing like our dicks were. And I was now having an affair with my...Read On

28

Tickets please!

My life changed forever on the 07:28 from Bristol

Standing by the window, I watched as the countryside flashed by. My train had been delayed due to a dodgy signal just outside the station, but judging by the speed the driver was maintaining there shouldn't be much of a delay, thank goodness. Even though I hated my job and boss I needed the money desperately. With a sigh, I turned away from the dreary grey outside and tried to make...Read On