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Crossdressing

27

Mike's new girlfriend - part 2

The following Monday couldn’t come round soon enough. It had been a long, difficult and very confusing seven days at home, with my wife, Amy. I had been so distant and argumentative with her and I could see how upset she was. However all I could think about was Mike and how much I wanted to be back in his arms and have him make love to me again. Again, the morning started in the usual way....Read On

14

Car Park No 1

My crossdressing dream

The Car Park No 1 The car park has always been a great place for meeting a fellow for a good time. I had been there several times over the years and felt a great satisfaction in satisfying the needs of a horny participant. It has become more of a challenge since the police seem to patrol it more often than in past years. However, I had the opportunity to have a few hours to my self as my...Read On

7

Shopping outing for lingerie

Fun time buying lingerie

Following is a true account of one of my experiences of shopping for lingerie. (nosex). This happened a couple of months ago, and as far as I remember, the conversation went like I have described below. If you have not read my earlier story 'Wonderful crossdressing shopping experience', I'd suggest reading it first. ------------------------------------------------ Following my...Read On

17

Pumped While Wearing His Pumps

Hitching A Ride with the Lothario of Lingerie

What a place to be stuck! Under a sign that says Coors Road and practically dying of thirst. I was now two-thirds of the way across the United States but perhaps the most difficult portion of my cross-country hitchhiking adventure lay ahead. It is all deserts from there on the outskirts of Albuquerque to the Pacific coast, my ultimate destination. I had left from Maine four days earlier...Read On

42

Mike's new girlfriend

It started as a typical Monday really; I waved my wife off to work and then went upstairs for a long bubble bath and shave, as I stood drying myself and rubbing baby lotion into my body my cock started to grow as I got excited about the morning ahead. I quickly put on sweat pants and then raced to the outbuilding at the back of the garden to fulfil my cross-dressing desires. I opened...Read On

14

Meeting Samantha

My first hot encounter with a cd

It had been almost two years since my first experience with Dave. That was the first time a man had sucked my cock. It was the first time I had touched another cock and the first time I had sucked a cock. That day was the birth of a new me. I no longer was a homophobe. Although, I did not look at men the same way I looked at women. I did not lust after them. What I did lust for was for a cock...Read On

11

How to please your girlfriend

When she gives me the puppy dog eyes, I can't resist....

(Some of this story may be slightly fabricated, but don't worry about what is and what isn't, just enjoy the story.) It was back in February when me and my girlfriend plus a few friends decided to go to a con. We hung out together and thought it would be fun. A friend bought my ticket and the closer it got to the con, the more we were excited. Not only did we get more excited, the closer...Read On

14

Telling Mom I'm A Crossdresser Part 8.5: Cops and Prostitutes

What Missy needs to do instead of going to jail for prostitution. (continue of part 8)

When morning came, I told mom what had happened the previous night. She had a surprised look on her face and I could tell she was feeling uneasy at the thought of me getting arrested while dressed as Missy as well. We talked for a while and she was glad as well that the police officer was a Missy fan. “We can definitely let him have a free night in exchange for not getting a criminal...Read On

11

I did not know I had a disorder

Bi man dressed for the first time to please a man

I did not know I had a disorder CindyUSA I am not sure if I should be embarrassed, ashamed, depressed about my condition. I do not look unwell; does it show? I look normal to my wife, family and co-workers. I wonder if they know about my disorder. If they had, why did they not tell me? Like most illness, they start slow and build up and suddenly, bang; right between the eyes it hits...Read On

19

Telling Mom I'm A Crossdresser Part 8: Bus Driver's and Cops

Part 8 enjoy and please comment at the bottom ;)

My mom and I spent the next few days practicing and exercising with the stripper pole until we felt confident and extremely sexy while doing it, which I have to admit did not take long. One night I came home late from my part time job I had at a local restaurant and took the bus home. I didn't have a car because I hadn’t decided on what car I wanted to get yet and what I could afford. I...Read On

13

Telling Mom I’m A Crossdresser Part 7.5: Amateur Pole Dancers

I thought I would try something a little different and involve more teasing to my story. enjoy :)

After our time at the spa, I spent a lot of time in my room trying out all the new sex toys we got from Richard and Monica. They were all exciting in their own ways and I came so much with each one. Some vibrated, some went deep and some felt good stretching my ass wide. The feeling of all the sensations I could get from my new plastic and electric friends were amazing and found myself...Read On

24

The feeding of sissy

I hold a prominent position in a world wide business firm and make a six figure salary and had been divorced for several years. I met Wendy through a newspaper add in the singles columns, she was a knockout looking gal. We dated for some time and she moved in with me. One night when we were out having drinks she ask what my deepest secrets were. She would share hers with me in return if I...Read On

22

Telling Mom I'm A Crossdresser Part 7: The Spa

Missy and his mom go to a spa and meet some new friends.

I could barely sit for days after Mistress Keri thoroughly tanned my hide and I had to take almost a week off so that I could heal. My mom knew this to and said we should go on a “girls” weekend to a spa for cross dressers and women, she also said that since it was for others like me then I could spend the entire trip as Missy. I loved that idea and hurried upstairs to pack Missy’s bag....Read On

24

Telling Mom I'm A Crossdresser Part 6: Missy and Mistress Keri

Missy has her first BDSM experience. Plz rate and comment

Up until now, I have enjoyed my time as Missy. My mom had kept me busy with clients and we pulled in a lot of extra income and I was able to experience a lot of different fantasies, However I had not had the chance to try anything involving BDSM, or not yet at least. One day I came home from mowing the lawn for an elderly woman when I walked in the door to find my mother smiling deviously at...Read On

59

Taking Control

Wife busted me doing some of my favorite things and then took control with some role reversal

* this is a story of how my wife busted me doing some of my favorite things and then took control of the situation with some role reversal to satisfy both her and my hidden desires - enjoy! * It was one of those rare days when I was working from home and my wife had plans to be out running around with a couple of girlfriends for most of the day. Work had been dragging me down and I was...Read On

29
Audio version available

A Hotel With Candy

originally an audio story however became a short story. plz rate and comment.

I got out of bed and looked at my sexy green camisole with bright pink fishnets, bra and panties that I liked to sleep in after I had just spent the night masturbating with my favorite dildo. I looked back at my nightstand to find it was still beside my pillow where I had left it the previous night and stilled wrapped in a condom all sticky with my favorite lube, strawberry flavored. I...Read On

30

Telling Mom I’m A Crossdresser Part 5: Movie Night and Gangbangs

5th installment of Missy, Plz rate and comment. :)

I had decided to take a few days off from being Missy after Stan and Roger had left and my mom and I were finished with our little girl time. I spent the next few days just continuing with life as normal except for the throbbing pain in my asshole and my cock from the 3 days of constant sex. I couldn’t stop thinking about all the things I had done as Missy and all the kinky fetishes I...Read On

29

Telling Mom I’m A Crossdresser Part 4: Repeat Business and Roleplays

4th installment of Missy :) please rate and comment :)

When my mom and I had gotten home, I immediately ran into the house to take a shower and change as quick as I could. I re-shaved my entire body and removed my makeup so that I could start from scratch and apply it again. Once I was finished with my makeup, I see a new outfit laid out on my bed. This was a cute nurse outfit with a short tight skirt that barely covered my ass. It was also...Read On

27

Telling Mom I'm A Crossdresser Part 3: Missy's Weekend

Part 3 of my Missy series :) enjoy and please rate and comment.

One day while watching T.V, my mother had come in and told me Missy’s services had been requested for the entire weekend and we needed to go shopping. I smiled as we got into the car and went to the store to buy lots more sexy clothing for me to play in. After we had bought all the clothes and makeup needed for the weekend, my mother and I went home so that she could give me the details of...Read On

42

Telling Mom I'm A Crossdresser Part 2: The Adult Store

Missy goes out and meets her first gloryhole. Please comment and rate all of my stories. :)

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived.   It was just past 9am when I heard...Read On

52

Telling Mom I'm A Crossdresser

A story of me being open with my mom as a crossdressing slut andher becoming my pimp. Plz comment :)

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first...Read On

40

A new friend

As I had a nice, big empty house I did what any good 17 year old would do. That first weekend I had a massive house party! I took a night off from dressing up and invited everyone I knew and when it came to the big night there were plenty of people, including a few I didn't know. I chatted to people and made new friends, sharing drinks and having fun. There was one girl there in particular...Read On

14

My First Boyfriend Part Five

I step out on my boyfriend and end up getting gangbanged

Things had pretty much gotten back to normal after our wildweekend a week or so before. My boyfriend Steve and I had our unofficial “honeymoon” where I had dressed in a wedding dress and we made love. I had been out dressed as a girl for the first time and had gone to a party where I sucked off a bunch of guys for money. Steve and I had taken two of those guys home with us and they all banged...Read On

27

My Girly Fantasy

A night with my friend changes everything between us

I wake up and smile, remembering where I am and who I'm with. I'm warm and comfortable, wrapped in your arms as you sleep. I think back to last night, finally showing you my girly side. We've been best friends for ages but I always had a crush on you. Finally, drunk on wine, I decided to do something about it. I came into the living room we share and straddled you; taking off my robe to...Read On

52

Becoming Ginna

First time sucking cock, first time fucked, first time girl !

We were just over 16 years old when I and my childhood best friend Tim, discovered masturbation. And once we did, we couldn't have enough of it. More often than not we would be at secluded places jerking off over porn magazines. From then onwards I realised I was getting more excited watching Tim masturbating rather than the porn, and soon I started wondering rather intensively how would his...Read On

16

My First Boyfriend Part Four

I suck off a bunch of guys at a party and take two home to have a foursome

The drive home from the party was quiet because I had sucked off ten guys at the party and my mouth was sore and we were pretty drunk too. Two of his friends were following us home I assumed to have sex and party. I lay on the seat with my head in Steve's lap and rested while we listened to the radio. I asked Steve how were going to keep those two from finding out I wasn’t a real girl and...Read On

19

My First Boyfriend Part Three

My boyfriend pimps me out to his friends

Steve and I had spent our first night together as a realcouple and in a real bed and it was wonderful. I had intended to wake him up with a blow job but he was already gone when I woke up so I had the whole day to wait for him to return from work. I spent the day just like a housewife would. I wore a house coat and some fuzzy slippers and after cleaning up the place sat down and watched...Read On

33

Gang banged at a private club

This is what happened when a friend took me to a private members only gay, bi, and transgender party

After yet another hot weekend at my friend Heberto’s house, I was packing up and getting ready to go home when he told me he had something “special" in mind for us next weekend. I begged him to tell me what he had in mind but he refused. So I left. My curiosity was peaked. The week dragged on thinking about all of the possibilities. The anticipation was killing me. Finally Friday...Read On

29

Friend Becomes My First Part 1

The true story of one my best friends becoming my first

*This is a true story of my first time having sex dressed a girl* It finally happened, and it was a dream come true. I started dressing as a girl when I was 17. For me, it started with a thong I stole from my mom's drawer which eventually went on to lingerie, to normal clothes, and all the way to dressing fully. Im now 24, and all I wanted to do was to show myself to a man and be the little...Read On

79

Vicky's First Time

My first time having sex as Vicky

I was very open about crossdressing when I met my wife when we were in our 20s. She has been very supportive and helpful. She helps me with my hair, makeup, and picking outfits. We started having sex with me dressed up as Vicky. This soon escalated to her taking me with a strap on. I loved the times she would fuck my ass with her cock. I had never considered myself gay or bisexual but the...Read On