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Crossdressing

22

Aunty's New Girl

Falling into the strange world of Aunty Trixie...

This is the continuation of Tickets Please! Shakily, I keyed in the URL from Trixie's card, my mind in turmoil, heart racing as her sweet gift seeped from my aching pussy and soaked into the lacy panties I was wearing. I was wedged behind one of the 'tables' thoughtfully supplied for the busy passenger. You know the ones, if you move a fraction either way you end up concussing your...Read On

7

Carl, Carla and Hannah - Part 23

The stag night, and the morning after...

There was two weeks to go before Hannah and I would become man and wife. And then, although nobody else knew, we planned to live as wife and wife. In the meantime, the final touches were being made to prepare for the big day. I decided to have my stag night a couple of weeks before the wedding, and I included Tom and one of his friends in the party. Graham, like Tom, was bisexual, but it...Read On

14

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

8

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

10

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

15

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

17

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

7

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

16

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

8

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

17

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

12

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 soon grew out of her desire to see me dress up and wanted a normal lifestyle and to date other men. It seemed that our time together had come to an end. I gave up my apartment and I moved back North. As I still had a sizable amount of money left from...Read On

9

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

14

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

26

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

7

Carl, Carla and Hannah - Part 19

Carla finally meets Tom, and discovers herself

The next day, I was a bag of nerves the whole day. Hannah got up and made breakfast for us, and then I had my weekly depilation, although the need for it seemed to be lessening. The hair on my body seemed finer and less inclined to grow, so after I washed the cream off, my skin felt really soft as well as smooth. I did my face while Hannah did my hair, then we looked for something for me to...Read On

18

The Sexy Girl-Next-Door: Part One

Wearing too many sexy clothes gets Courtney a big cock inside her.

As a sweet sixteen-year-old boy, I started my life of having transvestite proclivities. Being sexy for men and making their cocks hard for me became my favorite thing to do for pleasure. I already had a boyfriend, the blonde college boy lifeguard at my community swimming pool. He had seen me wearing some sexy little hot pants and come on to me, one day. The fact that he was handsome and all...Read On

8

Carl, Carla and Hannah - Part 18

An online meeting with Tom opens possibilities, and Bill shows Carla what to expect..

As the weeks went by, we got into a sort of routine. At work and for maybe a night or two during the week or when out visiting friends or family, I would be Carl, but for the rest of the time, Carla would be Hannah's live-in girlfriend. My hair grew slowly, and Hannah would style it with extensions so that I could still look fairly convincing without having to wear a wig, which pleased me no...Read On

26

Being Sissy To My Brother In Law

Caught in panties, bsque and stockings.

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are...Read On

6

Christina and Cheryl - Part 3

Christina encourages Cheryl to go out with a little help from her friends...

I woke up naked being spooned by Christina. Her smooth arms held me tight against her. I turned around and woke her up with a kiss. She opened her eyes and kissed back before pushing my head down. I kiss down her body and slipped her pink panties off. I kissed up her thigh and edged closer towards her clitoris, this is how we spent most mornings. "No, my ass." I lifted her legs allowing...Read On

10

Carl, Carla and Hannah - Part 17

Luke takes Carla to the cinema

As the week progressed, I looked forward to my date with Luke. I even found myself thinking about him when I was at work, and more than once found that I started to speak in my female voice before I'd realised it in the office. As Claire was 'unavailable' for a few days, Hannah went out of her way to make her life difficult at work. One lunch-time she went into her office, locked her door...Read On

16

A Sweet College Girl In Love

As a sweet college girly boy, I dated a real big hunk with a ten inch cock.

I went to college in a beach town in California where all of the girls wore their little thong bikinis to the beach and showed off their asses for boys with very friendly results. I noticed that when the girls were bending over while playing volleyball in their little thong bikinis, the boys all looked at them with hungry eyes that I liked a man to have for me.  The sweet little college...Read On

6

Carl, Carla and Hannah - Part 16

Carl realises something, Hannah and Carla have an evening in, and Carla has a date with Luke.

The alarm woke me from a strange dream. Bleary eyed, I reached over and silenced the noise. Hannah sleepily moved over to cuddle up to me as I lay there, thinking. The bet was won, and now the terrifying abyss of the future stood before me. What was going to happen now? I mulled it over in my mind, and then leaned over and kissed my beautiful Hannah before wearily getting out of bed....Read On

16

Wedding Night For Ken And Barbie: Part One

Catching the garter at my cousin's wedding gets me a honeymoon fuck like the bride.

When I went to my cousin's wedding in Monterey, California stag, at the reception dinner she had me seated next to the only other male stag invitee, the photographer. He was my age and tall and we hit it off, immediately. Ken was a sports car enthusiast and he told me about the thrilling rides he took along the Pacific Coast Highway. He talked about the beautiful views at scenic lookout...Read On

12

Explorations beyond my expectations

My introduction to pegging, cross dressing and so much more

I was nineteen at the time and Lili was my first college girlfriend. She was a virgin when we met. I had only had one intimate girlfriend before her. We loved to explore together and every weekend her roommate would leave town on Friday night and wouldn't return until Sunday evening, giving us plenty of time to explore and play. She knew I liked ass play from conversations about things...Read On

8

Carl, Carla and Hannah - Part 15

Carla's reward, and the morning after...

Just before we got to our bedroom, Hannah stopped and kissed me full on. We she broke the kiss, she told me that tonight was her way of saying thank you to me, and that I should enjoy myself. Finally, she explained that Claire was almost exclusively into women, but she was also besotted with Hannah, and was totally submissive to her. If my male urge to have sex with Claire took over, I...Read On

7

Carl, Carla and Hannah - Part 14

Hannah paid the driver and then took my arm as we headed towards the hotel. After dropping our coats at the cloakroom, we breezed through the lobby and headed for the restaurant. I felt so good in my new red dress and lingerie, but I was still a little uneasy on the high heels. Hannah gave her name to the maitre'd, and he showed us to our table. Fortunately for me, we were placed near the...Read On

9

Carl, Carla and Hannah - Part 13

Carla goes shopping and Vivien gets a surprise...

When I awoke the next morning, Hannah was already in the shower. I stripped off and joined her, and we kissed hungrily under the steaming water, our bodies sliding deliciously together. My hand slid between her smooth thighs, finding her aroused and ready. Slipping first one, then two and then three fingers inside her, I fingered her quickly to orgasm. She clung on to me as I continued to...Read On