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Crossdressing

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7

Memories of Anne

Jessica's new secretary learns the consequences of mistakes

The time on the mantle clock showed 9.20pm. I sat on the sofa and slipped my heels off and tucked my stocking clad legs under me. I picked up my glass of Chardonnay and took a sip. My thoughts went to the events of today. It had actually all started a month prior. I was recruiting for a new secretary when Anne’s curriculum vitae had come across my desk and it struck a cord with me. So I...Read On

2

Growth and Admissions

In a place where everyone cares, is the perfect place for a new beginning.

My initial impression that this town resembled Mayberry turned out to be reality, and that the people here where genuinely nice. Everywhere I went people introduced themselves and seemed to want to be my friend. At first, I really wasn’t sure what to think, but after the initial shock wore off, I began to relax and accept that this might have been the best decision of my life. After a few...Read On

6

A Night of Firsts pt 2

Pam meets some new friends

I opened the door to the club and walked inside. From the outside, the older brick building looked sort of run down, but once inside I found myself in a club with large bar on one side, polished brass railings, mirrors, subdued lighting, tasteful seats at the bar, hardwood floors, tables, a few booths further away and at the very end of the club a large stage with karaoke being sung. This was...Read On

8

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

14

Jessie's Fantasy: Chapter 6 Turning the Tables

Now that Jessie fooled his friends, who will turn the table on whom?

I was floored by what Tracy had said to me. “Because, the male Jesse is no more for the time being, it is womanly Jessie that needs to go.” It seemed that my love just told me that I had to meet up with my male friends tonight. My mind was going a mile a minute. I already fooled my friends once. But can I do it again? If I do, what is going to happen? What will I let happen? My stomach felt...Read On

9

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

2

Toby: The Little Rascal

A follow up to "Toby's Story"

Annabelle's last minute phone call altered our plans for the evening. "You'd better come as yourself because Toby's fucking hanging about!" She sounded a tad perturbed. Maybe the fact that her son was encroaching on her 'me time,' explained her tone. Never mind the fact that I had already started my transformation. My two-week beard growth had gone, and I was in my wife's bra,...Read On

An Introduction to Crossdressing, Pt. 6

As our evening progresses the fun continues.

After Steven leaves me at the table with Jackie and his new friend Chandra, I start to fill them in on the details. I tell them, “It’s really Jackie’s fault that I got fucked so good; since he was being so aggressive with his dance partner, I got jealous and grabbed Steven’s ass.” Then I continued with, “This led to Steven grabbing mine beneath my skirt, and then stroking my cock and balls...Read On

15

Further Exploration

Shauna and Jerry make a video.

After Jerry kissed me goodnight and returned to his own room, I had time to reflect. Sex with him was so different than it had been with Jack. Jack took his time, slowly and steadily pumping his hard shaft in my man-pussy and making me feel like his special girl. Jerry was passionate and urgent, riding me hard and making me feel special in a whole different, slutty, way. I was Jerry’s...Read On

8

Big Green

Loosely based on true events and it is my first story so please be easy. Being a Marine for most meant traveling, working out and above all alpha males only. For me all of this was of interest but I didn't work out and I was definitely not an "Alpha Male". Slim in stature I stood all of five foot, six inches weighing in at a whopping 145 pounds. I wasn't much to look at in a uniform but out...Read On

8

Jessie And Sue's Date Continues

Sue takes Jessie shoe shopping, and more...

Sue and I had a great time in the lingerie section of the department store. Getting caught by the sales clerk was definitely not something we planned on happening, but in some strange way it added a whole new dimension to what we had done. Both of us got out of the store as quickly as possible and headed into the mall. Sue suddenly turned to the right and stopped at a shoe store. This...Read On

9

Exploring Even Further

Shauna meets Jerry's wife and things get heated.

For the rest of the week I was a total wreck, dreading, craving, anticipating, and fearing, the arrival of Jerry’s wife and Rocketman69, whose real name I'd discovered was Jim. Just thinking about all of the possibilities had me literally trembling with lust and, at times, fear. Jerry, too, was in a constant state of arousal. Neither of us could believe what a slut I was becoming. After work...Read On

12

Becoming Chloe - Part 14

The aftermath. Chloe and Vickie have a heart-to-heart.

"Shit!" I was immediately awoken by Tina's curse. I opened my eyes to see her gorgeous, naked ass fly through the door to the bathroom, so I turned to my naked wife next to me, still half asleep. "Good morning," I murmured. "What was that all about?" "She's late for work. She should be at the shop for nine and it's gone half eight." "Oh," I said as I moved to snuggle next to her. ...Read On

Saturday With Al

One of those rare days with a new lover that doesn't disappoint.

After a great night of sleep, I awoke Saturday morning thinking of spending the day making love to Al. After coffee, I drew a nice hot bath and proceeded to spend the next thirty minutes getting clean and smooth. After drying off I applied liberal amounts of a lavender-scented lotion to keep me soft and smelling nice. I also made sure that my feet were quite soft as well, since that seemed...Read On

17

Becoming Chloe - Part 9

Vickie has an 'episode' while out shopping for a bigger cock...

A few weeks later, Chloe was a regular weekend resident in our house. Once I was home on Friday evening, I would shower and shave, and then spend the rest of the weekend as Chloe. This included going out shopping and even the occasional meal out. I'd worked hard on my appearance, and especially on my voice, and now I felt confident that I could pass even close scrutiny by anyone. Of course,...Read On

13

A Nanny Femtastic - 7

A NANNY FEMTASTIC! Chapter 7 After that first dinner Bradley and Felicity retired to their bedroom. And even though they were in a separate wing of the sprawling villa I could hear them making love! I thought of what Felicity felt as a transsexual woman having had a vagina created out of what was her penis. To feel Bradley rigid penis inside her. I wondered how nice it would be to put on...Read On

10

Soldier Standing to Attention

A soldier and the slutty nurse

I had been flirting with a soldier that I had met online for a while. He was a lot younger than the guys I normally go for, but surprisingly open minded for his age. He was also really hot and had a nice body, so I agreed to meet. We toyed with the idea of some roleplay during our online chats. My favorite was the wounded soldier and the slutty nurse; it made me very hot. I got myself a...Read On

8

My Sexual Odyssey Part VII: Turning Tricks

A continuation of the journey described in part 6

The next day I went to work as usual, but skipped my noon time ‘date’ with Brad. When I got home, I called Candy and confirmed the party invitation. Then I called Trixie and asked if she could use me at the club. “Of course! Are you kidding? Anytime!” “Well great, what time should I come by?” “How early can you make it? We open at nine, as you know, but although nothing much...Read On

6

Girlyboy Gone Wild - Part Seven

Fifi, the sexy French maid, gets to do 69 with her handsome boss.

After getting Rich big and hard with my sexy outfit, I was now ready to put on a show for him Whenever men see me in my panties, they want me like a girl. It follows that whoever wears sexy little panties also likes big hard cocks to suck on and play with. My sexy French maid outfit was especially good at making me feel like a slut for a man. Since so many men had fantasized about being with...Read On

3

A Weekend away

A weekend in a hotel turned out to be more that was expected.

Stevie had always wanted to have a weekend away with a load of like minded people, i.e. trannies and admirers. He decided to find a place where he could do this and be the real Stevie, or his girly name, Lucy Lou. He searched the net and found a place about two hours drive away. He booked it and counted down the days to be there. He had bought some new stuff and had practised his makeup....Read On

7

A Nanny FEmtastic - 9

A NANNY FEMTASTIC! Chapter 9 Thomas quickly pulled his hand from under my skirts, and stood up abruptly. “Fucking hell I don’t believe it!” he blurted out. Felicity was suddenly by my side. “What’s wrong?” she said. “forget it!” Thomas said, and stormed back inside, knocking over the table and drinks as he went. Bradley chased after him. I burst into tears and Felicity put her...Read On

5

Derek and Amy: Derek's Turn

Derek takes control

As I walked into the hotel room hours in advance, my cock was rock hard with anticipation. The last time me, my lover Amy, and her husband Matt were all together, it was my dear love Amy's turn to be in charge. Amy had Matt and I dress like two Fifties sluts. The kind of girls uptight parents used to believe would cause the downfall of society. It was both Matt and I's first times with...Read On

7

Carl, Carla and Hannah - Part 24

Carl and Hannah's big day, and after...

At last, the big day was just a few hours away. At ten o'clock the following morning, Hannah and I were to be man and wife. Or at least, that's what the outside world would see. The reality was that, after our honeymoon, I would live almost totally as a woman. Now that Hannah was settled into her new job, she became even more bossy and dominant at home, although I never let her get it all her...Read On

6

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

6

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

12

Becoming Chloe - Part 39

The Final Chapter.

The following week, I found myself leaving home for the last time as the person I was. When I returned, in a few days time, I would be a total woman. All semblance of my being a man would be gone, and I would finally be my true self. To help prepare my body for what was to come, Colin and I had abstained from sex since the evening when I got home from Tina and Vickie's house. That night,...Read On

5

Special Soiree

The two sissies meet for their special party

“Amanda” was fully dressed when “she” opened the door. She almost shyly greeted her close friend “Suzette.” “Hi Suzette. It’s been a while,” Amanda said. Suzette had an unhappy expression on her face. “I know, too long.” Then she looked around clearly nervous. Amanda knew that sensation, and opened the door wider. “Please, come in.” “Thank you, Amanda,” Suzette said her confidence...Read On

4

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

4

Jenny Learns Her Place (Part 2)

Jenny prepares to accept her Master

“Thank you, Master,” I said as I slowly brought myself to my feet, tears of pain rolling down my cheeks. I couldn't see my ass but it was probably purple with bruising and I was happy with that. Bobby would now know that I could withstand a hard spanking with the paddle without falling back on the safe word. “And for good measure,” Bobby said and put the clips back on my nipples. Wincing...Read On

12

Unexpected Turn of Events

Jessica meets a neighbour at a bar

I sat in my favourite bar sipping at my glass of Chardonnay; I had been coming to ‘The R Lounge’ for a couple of years. I watched the guy talking to his friends across the room. They were all dressed with a bit if style but he had caught my attention. He was wearing trousers with a casual blue and black stripped shirt. He was probably five feet nine inches tall. He had an average build; not...Read On