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4

Girlyboy Gone Wild - Part Five

After being a sexy school girl, I become a sexy Frenchmaid.

Having my clitty dick sucked by Dan really did make me feel pretty and sexy. He was really good and was able to swallow all seven inches. While he sucked me, I played with my titties while he looked up at me. I was looking down at his big 11 inch cock sticking out of my white cotton panties he was wearing. It was all so kinky, it thrillled me to be having so much fun at my all-weekend...Read On

12

Vicky's Mrs. Robinson Moment

My wife the company cougar.

  I had heard my wife Vicky mention the name Scott a few times over the last couple of months, and by her account, he was a polite, good-looking young salesman. I remember asking her if he was fuckable, and her reply was "Yeah! If I was twenty years younger." My wife Victoria is at the wrong end of her fifties. In truth, she could pass for mid-forties and is considered a 'cougar' by...Read On

7

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

3

Girlyboy Gone Wild - Part Six

After being a sexy school girl, I become Fifi, a sexy French maid.

With both of my hands wrapped around Dan's big 11 inch cock, I felt just like a little girl in his classroom. I jerked him off with both hands while I sucked on the head of his cock, getting it ready for him to put in my tight little girly ass. I licked around the big head of his cock, smelling my sticky-wet, cum-soaked white cotton panties he was wearing. Oh, it was all so kinky and fun...Read On

4

My 2 AM Phone Call (Part Five)

The night got more exciting when they strapped me in

Bondage means different things to different people.  To some, it just means being tied up, but I always felt that true bondage means a lot more.  It can mean total surrender to the situation I find myself in and total embracing of the situation, knowing I can't do anything about it. When I looked more carefully at the machine that was in front of me, I realized that this was to be a...Read On

9

How to Treat a Lady

A pretty crossdresser learns how to please a man.

Being a pretty, petite, believably passable crossdresser makes me a very happy person. I have been dressing up as a sexy girl while daring to go out in public for the past two years since I was sixteen. I have had this urge and desire to dress as a female for as long as I can remember so I have gradually come to accept that I have a feminine side that needs to be nurtured and encouraged. I...Read On

6

A Friend With Something Extra Part 5

Ian's meeting with Lorna.

The weekend had come to a close and Grant and Ian returned to school. There were only a few more weeks before Summer vacation started and that's when Ian noticed changes in his behavior. He found himself staring at Grant whenever he could do so and not get caught. Dressed in his everyday clothes Grant bore no resemblance to the sexy girl he becomes. Secondly, he stopped playing the online...Read On

9

Becoming Chloe - Part 18

Chloe goes home and gets a seeing to...

I have no idea how I managed to drive home with my skirt soaking with cum and my cunt full of the plug that Tina had slid into me. The scent of sex filled the car, and the fear of having an accident or having to stop kept me on my toes enough to drive more carefully than I ever had. The spunk on my skirt started to dry as it stuck to my legs, making me a little uncomfortable as I weaved...Read On

6

Derek and Amy

Derek and Amy enjoy some time alone.

We're holed up in a nice little hotel room in the middle of nowhere. No one around here knows us and no one will bother us. Tonight's all about us. Once we get settled in I send him off to take a shower. Now that I'm sure he's busy it's time to get to work. Digging out my bag I lay out the outfit I've had prepared for a long time. The panties are black silk, as soft as butter. There's a...Read On

4

Sissy Blane and the Hydraulic Inevitable

Blane finally has an encounter with Mr. Plumrose, the first installment to pay off a debt .

The story so far: debt-ridden Sissy Blane's first obligatory date with Mr. Plumrose is about to take place.   '...there's nothing good or bad, but thinking makes it so.' The truth of the old saying occurred to me as I awoke on the fateful Friday and was surprised to discover that I was looking forward to the events of the coming evening. Arising from my bed feeling energized I...Read On

6

Carolyn Makes Her Way (part 2)

Mike paddles Carol - Hard!

After I left the office of my former employer I went immediately to see an attorney. There were two things I had to do: one see about suing the hell out of my former employer and two: I needed to get my name changed legally to Carolyn instead of Carl. I chose this attorney because I already knew him, very well in fact, right down to the birthmark above his nice cock. He wasn't surprised to...Read On

6

Jessie's Fantasy Chapter 8: A New Beginning

Jessie finishes having fun with her male friends, So what does Tracy have in store for her?

I sat in stunned silence after the love of my life gave up my little secret to all of my friends. After losing a bet with John, I had to dress up as a woman and try to hook up with a guy as payment. Tracy and her friends did such a good job making me look like a woman, that I was able to fool all of my friends into having unplanned, but very much enjoyed, sex with me. It wasn’t until Ross...Read On

10

Becoming Chloe - Part 20

Chloe receives two invites for the weekend...

Unsurprisingly, I was very tired the next day, so I tried to keep busy to help me stay awake. Of course, the thought of a phone call from Colin certainly perked me up, and it must have showed. Around midday, Tina came in just to check on things. Nowadays I saw less and less of her at the shop because I virtually ran it on my own, plus she'd had a bad time with her morning sickness, so her...Read On

6

Three nights in London, night 3, Irene rocks!

Cute Dutch Tgirl goes for it

I woke up looking into the smiling face of a pretty redhead. Sunlight was streaming through the curtains of her bedroom. "Good morning, Irene," she said, and she kissed me on my nose. I smiled back and slowly remembered my adventures of yesterday. When I moved my legs it dawned on me that I was still fully dressed. I even had my high heeled boots on. My skimpy black dress was pulled up...Read On

13

Becoming Chloe - Part 17

Chloe starts work, and receives an unexpected bonus...

Two weeks after the agreement between Vickie, Tina and me, I was a different woman. I'd told my parents about my planned transition. As I thought, it wasn't easy, but I felt so much better once it was out of the way. Mum took it fairly well, but I'll never forget the hurt look on my father's face as I explained how I felt, and how I wanted to be a female. Despite that, he still gave me a hug...Read On

13

My first time in a bar

The first time I met a guy in a public bar for a drink

For a while now I had been chatting with a sweet guy named Allen, who was bisexual and was eager to meet a crossdresser. He was very muscular and handsome, a hard body but with friendly eyes. He seemed to really like my pictures and said he had cum, stroking himself, while looking at them several times, and was eager to meet me in person. He wanted to meet in a bar which is something I had...Read On

4

Jaime's Way (Part 3)

Jaime gets uncaged and left alone for a week - she doesn't lack for company.

As Jeff closed the door he grabbed me by the hand and spun me around, pulling my nude body close to his, breathing in my perfume before locking his lips over mine. My fingers found the button on his jeans and opened them with urgency, more than a little pleased when his huge cock sprung out. “Damn, I want you so badly, Jaime,” Jeff moaned when he broke the kiss. “I'm yours to do with as...Read On

5

Being Christy - Part 3

Christy finds release after moving to university

My experiences with Jenny and James had been amazing, but summer drew to an end and it was time for me to take up my place at university. I didn’t need much and only took a couple of bags with me, but the move did mean saying goodbye to my sister’s wardrobe. My parents gave me a lift to my student digs and after some typically over the top parental farewells, I was left alone three hundred...Read On

4

Happy to be Used (Pt. 5)

I finish my day of private booth service.

I was walking gingerly in my heels and panties from the assault my ass had just received. While it likely looked like I was just trying to be more effeminate, my ass hurt so bad it was the only way I could walk. When I reached the front of the store I saw Sir talking to an older man who was behind the counter with him. The man appeared to be in his early sixties.  I looked at him and Sir...Read On

2

Sissy Blane in the Hart of the Valley

Having had the first date with Plumrose, Blane visits a t-girl club with Cindy

When I got home from the Hollywood Hills I barely had the strength to remove my makeup. I was so exhausted I just wanted to flop on the bed and pass out, but I persevered and undressed properly, removed all makeup and even put my wig back on its wig head. But when I was finally between the covers my brain refused to cooperate, rethinking the night's events, imagining how they may have looked...Read On

3

Derek and Amy: Matt makes three

Amy's husband Matt joins the fun

My lover and my husband are in separate rooms changing into the clothing I've laid out for them. When they're finished they'll come into the library where I'm sitting waiting for them. This will be the first time they've touched each other and I'm not going to miss a minute of it. I'm sitting in a big padded chair diagonal to the door. My husband, Matt, comes in first. He looks...Read On

8

Cum Ahead If You Think You're Hard Enough

A tale of two old folk fucking.

"You don't get as hard as you used to!" I thought my wife's assessment of my current condition a tad harsh, especially on my 63rd birthday. We had been celebrating the occasion at a local luxury spa hotel. The evening had been a success so far, with copious amounts of alcohol consumed by both parties. I had stuck to wine, but Victoria's tipple list consisted of grape, and grain, and more than...Read On

2

Have A Good Feel, She Loves It! Part Three

The action moves to the dance floor and the delicious Linzey!

After half an hour I was ready to go again. I looked back to the days before I got onto the scene whilst I prepared to rejoin the party. I would watch the likes of Bukkake porn and say to myself “I’d love to do that” thinking that in reality I would never even get the opportunity to try it. And there I was washing my cum covered face after having two guys wank over it in the middle of a hotel...Read On

7

My Sexual Odyssey Part V: A Real Whore

A continuation of the journey described in part 4

The next morning as I awoke, I realized that in just a few hours I was to re-experience the previous day’s activities. This seemed too much too soon, but I had agreed. Of course I could always cancel, but then if I did so I would wonder how much I’d miss it and whether I would have acclimated to the frequency and intensity. I decided to just forge ahead and so I got dressed and left for...Read On

4

Mistress Sarah plays mind games

The continuing story of Mistress Sarah and Evie

I woke up at 7am when my alarm went off, I was wrapped up in a pink quilt, Mistress Sarah had obviously thrown it over me as I slept. It was soft and comforting despite the fact that I had been sleeping on the floor in the hallway. I had been banished from the bedroom after I had cleaned her strap-on. I had stayed close to the door listening to the sexual tones of Mistress Sarah. I...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

8

Becoming Chloe - Part 25

Chloe pays the price for losing her virginity.

The next morning, I awoke to the sound and smell of Colin bringing us coffee and toast. The smile on his face was lovely, and I couldn't wait for him to put the tray down and kiss me. Once he'd leaned over and gave me the most wonderful kiss, he took off his dressing gown and slipped in beside me. We sat and ate our toast and sipped on our coffee, saying little, but just happy to be in...Read On

8

Discovery Part 2

It had been an amazing year for Kyle. At eighteen he attended his first get together for those that cross dressed and their supporters. It the first time since the urge to dress up came upon him he finally felt safe and accepted. Over the following months, he perfected his skills at makeup along with dressing, walking and talking like a female. Soon he was one hundred percent passable in...Read On

10

Becoming Chloe - Part 16

Chloe makes her feelings known to Tina

Tina stayed the night, but I couldn't sleep with three of us in the bed, so I got up around two in the morning and went to sleep in the spare room. I didn't mind leaving Vickie and Tina alone together. Besides, I knew I would have to get used to at least a couple of nights a week on my own anyway, and my mind was still in a whirl with everything that was going on. I tossed and turned as...Read On

11

Becoming Chloe - Part 22

Chloe and Colin have a date...

We must have all slept soundly because the only thing I can remember is waking to the sound of Vickie getting up to go to the bathroom, her cock still jutting out in front of her. Later still, I awoke feeling the need to pee, so I got up as carefully as I could and headed for the bathroom. When I returned, I felt a little cool so I slid under the duvet before flaking out again. The next...Read On