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Crossdressing

15
vote
ChelseyR

In Wonderland, Pt.1

Costume mandatory...

When I was in high school I was always very camp, which was probably why almost all of my friends were girls. This was definitely why I first ended up crossdressing. I was sixteen and round one of my 'girlfriends' house for a few drinks on Halloween before we went to a house party nearby. I never much cared for Halloween, so just came as myself. When I came in they all sighed since I wasn't in...Read On

Added: 07 Nov 2010 | Category: Crossdressing | Avg Score: 4.8 | Tags: alice  crossdress  party  halloween  teen   | 7 Comments

18
vote
Aimee_Cd

Halloween Fun

First time Out

My friend talked me into dressing up as a female this Halloween. It wasn't much of talking into; I was a closet cross dresser for sometime. The only person who ever knew was an old girlfriend, Mel, a few years back. It was a good thing she was bisexual because she was really into me wearing her clothes. She even mentioned that I looked better in her clothes than she did. So, I started wearing...Read On

Added: 03 Nov 2010 | Category: Crossdressing | Avg Score: 4.61 | Tags: fetish   | 7 Comments

14
vote
Amatramp

Caribean Vacation part 2

Lost luggage leads to wearing girlfriend's panties as a swim suit and more

We strolled down the hall to the elevator. I did not notice what floor we went to, as I was so pre-occupied examining my sexy self in the reflective surface of the elevator. We got off the elevator and walked down the hall to a door marked 469. “This isn’t the dining room,” I objected. “No, this isn’t,” she replied as she knocked on the door. “Who’s room is this.” I asked. Before...Read On

Added: 02 Nov 2010 | Category: Crossdressing | Avg Score: 4.86 | Tags: panties  crossdressing  anal sex  humiliation     | 3 Comments

13
vote
Markdwyer1984

Minding the House

Short true story about the fun I got up to while minding my neighbour's house

My neighbours Tom and Paula were going away on vacation and they asked me to keep an eye on the house for them. I gladly accepted as I wanted to see what their house was like on the inside but my curiosity really lay in exploring Paula's underwear collection. Paula was a 34 year old pretty mom of two kids, 5ft 7 with blue eyes and shoulder length brown hair. She possessed a slim but...Read On

Added: 13 Oct 2010 | Category: Crossdressing | Avg Score: 4.69 | Tags: crossdressing  stockings  lingerie  masturbation   | 7 Comments

25
vote
Karin

The Worm Turns-Part 1

My submissive girlfriend turns into my dominant wife

I must have read about a million of these stories and I have to confess that mine isn’t so unique--maybe only in the details, but not so much in how things started or how things ended. You can probably write the first lines yourself: “Things started out so innocently. We had a typical relationship that somewhere, some way, took a dramatic turn that I never saw coming. At first, I was all for...Read On

Added: 27 Sep 2010 | Category: Crossdressing | Avg Score: 4.70 | Tags: crossdressing  feminization  bondage  beautysalon   | 4 Comments

22
vote
Amatramp

Caribbean Vacation part 1

Lost luggage leads to wearing girlfriend's panties as a swim suit and more

Susan & I often traveledto the Caribbean for our vacations. We loved the laid back atmosphere and all the sun and gorgeous beaches. Last year though we arrived to find that the airline had lost my only bag containing all my clothing including my swim suit! Imagine arriving in the Caribbean without even having a swim suit to wear! I had just resigned myself to going down to the gift shop...Read On

Added: 25 Sep 2010 | Category: Crossdressing | Avg Score: 4.85 | Tags: panties  exhibitionism  crossdressing  lingerie     | 11 Comments

11
vote
watcherfun

All Dressed Up Part 3

The story continues...

I spent the next few days thinking over what had happened to me. Had I really enjoyed it? Over time however I began to forget about my little 'excursion'. Months past and my trip had lodged itself at the back of my memory to be forgotten. The story doesn't end there though... There came a time a few months later, where I was running low on cash. I had spent too many nights out...Read On

Added: 17 Sep 2010 | Category: Crossdressing | Avg Score: 4.82 | Tags: office  crossdress  teen  young  crossdresser  mini  skirt   | 4 Comments

15
vote
Markdwyer1984

Phoenix Park Night

My first time getting a blowjob from another man while wearing lingerie

I am a 32 year old married guy who happens to like wearing ladies' lingerie. My fondness for wearing lingerie goes back to my late teen years when I would wear my mother's clothes and underwear. I went on to wear my sister's undies and this continued into adult life where I have worn the undies of many ladies (without them knowing it). Until the time of this story, I never ventured...Read On

Added: 17 Sep 2010 | Category: Crossdressing | Avg Score: 4.73 | Tags: crossdressing  first time  bi  tights  blowjob   | 6 Comments

27
vote
Cdashlynninsc

Two girlfriends have a couple over for a fun night

Wife sets up night for us to be girlfriends, then invites another couple over for fun

My wife Dawn had surprised me by saying we were spending the night in as two girlfriends, laying out my clothes so we matched. Then after having amazing sex, Dawn surprised me by telling me that she had invited her friend, Maria, and Maria’s husband, Mark, over for some fun with the two of us and to fulfill the fantasies of all of us. So I was standing there with my red plaid skirt,...Read On

Added: 05 Sep 2010 | Category: Crossdressing | Avg Score: 4.84 | Tags: crossdressing  oral  girlfriends  wife   | 7 Comments

18
vote
Adelleda

My First Time

I'll never forget the day I lost my virginity as a cute crossdresser...

I remember I was 16 when I first started becoming interested in girl's clothes. When my parents would go out I would try on my mom's sexy panties and nylon stockings. They would fit right over my slender teenage body. I had always kind of been interested in guys but it wasn't until I started crossdressing that I started jerking off to gay porn. The idea of being fucked in the ass used to turn...Read On

Added: 27 Aug 2010 | Category: Crossdressing | Avg Score: 4.61 | Tags: crossdresser  teenage  first  time   | 7 Comments

39
vote
Cdashlynninsc

Two girlfriends stay in for the night

Wife pleases her girlfriend then tells her whats going to happen next

The other day I came home from work and was looking forward to spending the evening with my wife. We had the next day off, and it was going to be great to just get some time with her. After I was home and settled my wife Dawn came and found me and told me she wanted to spend the evening with a girlfriend and have some fun. I was a little disappointed, but a few seconds later, she told me...Read On

Added: 17 Aug 2010 | Category: Crossdressing | Avg Score: 4.76 | Tags: crossdress  wife     | 8 Comments

5
vote
dawnforever

My Live-in Partner

Post-operational care never involved so much caring.

Eight days after the surgery, the hospital released me to go home. The bus ride back to my place seemed to take forever as the dull ache in my crotch fluctuated with a mind of its own. I had taken medication for the first four or five days after the surgery, but weaned myself off of them to the point where I could deal with the ache by the time I left. The cleaning regiment that I had to...Read On

Added: 17 Aug 2010 | Category: Crossdressing | Avg Score: 4 | Tags: dawn summer  meghan dahl   | 1 Comment

2
vote
dawnforever

An Original Woman

Sometimes things just need a little boost for a new friend.

Ever since I was young, running always exhilarated and calmed me at the same time. Then, more than ever, I really needed those feelings, so I ran. By the time I finished, I felt as though I had nothing left in the world to worry about, until I realized that I needed to get to my first class of the summer. I sprinted to my apartment, and took a quick shower before getting dressed for English 101....Read On

Added: 14 Aug 2010 | Category: Crossdressing | Avg Score: 5 | Tags: dawn summer  total transformation   | 1 Comment

2
vote
dawnforever

A Break in Action

Settling into a new life is easier than first imagined.

I took a good long look at my now shoulder length hair. It still looked very straight and masculine in contrast to my wig, but at least I had something to work with now. I decided that it was about time to start wearing my natural hair instead of the very nice, but still uncomfortable wig I’d used for four months now. Since I’d left my old life, my chest had grown between an A and B cup...Read On

Added: 12 Aug 2010 | Category: Crossdressing | Avg Score: 4.5 | Tags: dawn summer  job  progress   | 1 Comment

2
vote
dawnforever

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

Added: 11 Aug 2010 | Category: Crossdressing | Avg Score: 3.5 | Tags: dawns summer   | 2 Comments

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