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Crossdressing

9

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

13

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

11

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

17

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

7

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

14

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

13

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

9

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

7

Carl, Carla and Hannah - Part 12

Hannah has lunch with Claire, while Carla finally comes to terms with things...

After Hannah had left for work, I lay in bed thinking, my head now just a dull ache. I went through the last ten days of adventure we'd shared, comparing the highs and the lows, the rough and the smooth. I went over what I'd, at first, been 'persuaded' to do, and then willingly done, and I thought about how much I'd changed in those ten days. I also considered how things might go, one way or...Read On

3

A Terrific Threesome: Part Three

The first of many nights together with our big stud was wonderful.

Before I met Sherry, she had been having affairs with other girls. That was why she had a strap-on dildo to wear. She told me about the sex parties she would have with three or four lesbians that would last all weekend long. The girls would all get together on a Friday night and drink some wine and get naked and have all-female orgies for the entire weekend. Sherry had licked a lot of...Read On

19

From dream to reality

The ladies find out I wear their lingerie

My name is William. I am the eldest of a family of four kids, two boys and two girls. At the time I was seventeen. We lived in a small town, and my parents were well respected. I did well at school, played and succeeded in sports. I was and still am living an intense inner life fantasising on my sporting exploits and sensual encounters. In those days, it was just as normal for teenage...Read On

10

A Terrific Threesome: Part Two

The fun threesome gets kinky in the bedroom.

When I told Sherry about the handsome maintenance man with the thirteen inch cock, she said, "He sounds delicious." I explained how he caught me wearing her panties and wanted a blow job right away. How I offered him a beer and a blow job and what a good fuck he gave me, too. We felt like two girlfriends talking about a big stud we both wanted badly and we were both very happy. "Oh,...Read On