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Crossdressing

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29

Becoming Chloe - Part 3

Chloe gets her name - and much more...

When we arrived home, I was desperate to change, but Vickie said no, much to my frustration. The rest of the afternoon went like any other Saturday, and after dinner, we sat and watched tv for a while. Around nine o'clock, Vickie got up and suggested that we have an early night. By now my frustration had almost abated, so I followed her upstairs and we both got ready for bed. I was delighted...Read On

21

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

21

Crossing A Different Line

A married family man's growing interst in female lingerie leads to his being taken as a woman.

In my personal journey from straight, married heterosexual to bi male, I discovered, along the way, that I was aroused by women’s lingerie. It started with trying on a pair of my wife’s nylon panties. The feel of the silky material, and the sight of how it fit, quickly brought on an erection. I used another silky pair in my hand to jack myself off, being careful not to get any cum on the...Read On

21

The Day My Secret Was Discovered

My wife surprises me.

My wife and I have been happily married for four years. She is the dominant one in this marriage. Just recently I have discovered how much I enjoy wearing women's clothes. I love how the panties feel between my ass cheeks. The silkiness of the nylons on my legs as I slide them causes an erection every time.  My wife had no idea until one day when I had Friday off from work. As soon as she...Read On

20

Roomate

An introduction to a new side of my roomate

Roommate It had been a hell of a year with a divorce, a new job that had me traveling more and having to move into shared housing because my ex was sucking my bank account dry. Carl, my roommate, was a decent enough guy. I found the room on dougslist.org and we seemed to be compatible. He was neat without being compulsive about it, was a working student and was not inclined to throw...Read On

20

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

19

My birthday treat

After months of helping me dress, my neighbour plans a special night.

My next door neighbour had begun helping me with my crossdressing by buying me my own clothes, and despite her initial stipulation that I continue to dress in secret, we had experienced a moment where that had all changed. Once that day had passed, Ellie and I became almost inseparable. If we weren't together, we were texting or talking on the phone. We would do everything an ordinary pair...Read On

19

My Parents Friend

Get's Me Hot Every Time I think About It

The year was 1987 and I was home on leave from the military. One particular Saturday night my parents were haveing a get together with some friends so I decided to go out and try and find someone to have fun with. I couldn't decide what to wear until I just decided on what I thought would make me look sexy. I grab my things and head into the bathroom and put on my sexiest black...Read On

19

The Compromise - Part 2

The fantasy compromise comes with an unexpected twist.

Andre and his three girls, me being one of them, piled into his car. Andre assumed his role as the driver, Mikayla grabbed shotgun, and my wife, Ally, and I got into the back seat. My heart pounded in my chest with nervousness, as this was my first time going out en femme. Ally no doubt saw the fear in me and scooched closer, taking my hand in hers. "Baby, don't be scared. We're just a...Read On

18
SxyJackyLeggs
online

My wife finally indulges in my fantasy

This story is a work of fiction I wrote for my wife.

I come home from work to find you dressed in your sexy jeans, a tighttee shirt, and a pair of heels. I can tell you are horny by the way you tell me to get into the shower and that my clothes are laid out for me after I finish cleaning up. My cock throbs as I shower and lather my body up with some scented soap. I know you want me squeaky clean so I insert a soapy finger into my ass,...Read On

18

Now Or Never

Now or never, he thought as he dressed in the sexy, girly lingerie.

He was nervous as he drove to the mall. He had to remind himself that nobody knew what was really going on, and that men purchased lingerie all the time for the wives and girlfriends. Except his purchases wouldn’t be for his wife, who had unceremoniously left him two years earlier with little explanation. He had revealed a few of his fetishes and kinks to her, which she had given off...Read On

18

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

18

Jenny and Mike: Date Night

A loving husband and wife begin a long weekend of crossdressing and pegging.

It’s Friday night, but for me and my wife it’s Date Night. Most couples have date nights on Saturday, but we have it on Friday nights to get an early start on the weekends. Michelle and I have been married for a little over two years now and we live a very happy life. I was not always so happy because I am a crossdresser and have been dressing up ever since I was 16. I met Michelle when we...Read On

54

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

45

The Party

It happened one halloween

I am a closet cd. It was Halloween. My wife called from work and said she wanted to go to a party at a friends house. It was a costume party. She said she had a costume and I was to wear one as well. What, I don’t have one. Yes you do, your going as a girl. But I’ve never done this. Well you’re going to tonight. No one will care because it’s a costume party so get dressed...Read On

36

Six Months

A girl's dreams cum true

After all those years of longing to be free, stuck in relationships with women that frowned upon my cross dressing, I was still very much relishing my freedom. I was dressing every moment I could, the minute I got home from work every single day; a mini dress, heels and stockings were what I craved so desperately. I had been living alone now for a couple of years and would have thought he...Read On

35

Old Friend, New Relationship-Part 1

As it turns out, I confided my crossdressing desires in just the right person

Old Friend, New Relationship-Part 1 I met Karen in my divorce support group while I was dealing with my second divorce and she was trying to cope with her first. About the only thing that we had in common was that both our spouses had cheated with good friends of ours. She was a couple years older and very attractive. I remember that she always dressed so well for our group meetings. We...Read On

34

Can't I Have Them Both?

Can I Make This Work?

Waking up to the sound of my alarm blaring, I roll over and slam on it. Of course it doesn't go off, just crashes to the floor. I know I shouldn't have stayed up so late last night playing video games, but what can I say? Too late now, I suppose. I reach down to pick up the clock, seeing the time blinking at me. Getting out of bed, I grab the shower before anyone else can. I know what...Read On

28

Becoming Chloe - Part 2

Their first shopping trip, and a changing room revelation...

As I lay there, my heart racing, I wondered what my wife would say. After all, she'd just caught me cross-dressing for the first time. So far, it had turned her on and we'd had the most fantastic sex since we first got married, a few years ago. Now that we were both spent, I started to get nervous about what she would think of me. Vickie rolled off me and then snuggled up as I put my arm...Read On

27

Date with my wife

It started with my love of sexy lingerie. I planned a date with my wife. She was to come home from work and go up stairs to clean up. Once all cleaned up she was to put on the outfit I laid out. She had lots of questions that I wasn't answering. She wasn't to come into the rest of the house until she was dressed. Well my day started by going to the store shopping for dinner and an outfit....Read On

27

Meeting my Ex-Girlfriend's New Boyfriend

being seduced at the bar

Not long after I got out of the service, I met Trish at a house party. She was a hot little brunette with a great body and we hit it off right away. After a few months of dating we ended up moving in together and she was a great lover...with one little quirk. She always wanted me to wear a pair of her panties while we were having sex. I readily obliged because she was so good on her back and...Read On

27

becoming a cock worshipper

I first realized I was bi the summer after high school. Up until then I had only been really interested in girls. Like any high school guy I watched a lot of porn and soon realized that I really liked really nasty deep throat blow job scenes.  I especially enjoyed watching a girl choke and gag and cover a hard cock in her spit. I also realized that my favorite scenes always involved a...Read On

17

Been A Long Time

Once I got married I pretty much gave up my crossdressing lifestyle to lead a more "normal" life.You know,settle down,have a couple of kids. I was a happily married man with two kids,what could be missing? Well one day while at work,I was on the internet and stumbled onto a crossdressing website,and all kinds of memories came rushing back to me. The feeling of sexy panties,bras...Read On

17

A Friend With Something Extra.Part 3

Grant collapsed on carpeted floor of the living room. The ropes of semen his friend shot on his chest were beginning to crawl down to his bra. The ones on his bra were slowly moving down toward his belly. His tiny silky bikini panties were filled with his own cum as the sight of his friend's cock shooting on him had gotten him off. He looked up at Ian who was still sitting on the couch with...Read On

16

I am Suzie

This is my fantasy.

The coach was lubing up his cock. It actually was getting bigger. The veins along the shaft were thick and gorged. I could not take my eyes off it. Then he started humping the crack of my ass. I knew he was letting me feel how huge he was against my ass. I was so turned on that I started to wiggle my ass and grind his cock. He enjoyed that so much, he stopped humping me and let me do all...Read On

16

Bookstore Bunny Gang Bang

Dressing as a Playboy bunny at the bookstore lands Courtney four big cocks.

Dressing as a sexy girl is my favorite way to meet men and have fun. There are so many different sexy outfits a girl can wear to attract men and turn them on, they ensure it never gets boring for a man. Every girl wants to be her sexiest when wearing lingerie and I am no different. Recently, I was on a business trip which included spending the night in a motel located across the street from...Read On

16

While the Cats are Away

Kelly's best friend catches him dressed up

Thursday night, mom is going to visit relatives out of town; dad is away on a business trip and not supposed to be back until Saturday. It took a lot of convincing that being sixteen is old enough to be able to stay home by myself and not have to go with mom to visit relatives. Dad was going to be home in two days and I would be going with him to the family ranch. Finally my mom relented and...Read On

61

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

49

Mom made me a Fluffer

another story between Missy adventures. Enjoy and please rate and comment all stories. :)

For most of my life I never knew exactly what my mom had done for work, neither did I know who my dad was. As such I just continued with life and thought to myself that I would find out what she did in time. My curiosity first peaked when I was 16, I was looking for my moms purse so I could exchange some of the money I got mowing lawns for people around my neighborhood for different bills....Read On

25

Switching roles

She dresses up as a policewoman and plays the dominant part

In most play I tend towards the dominant side but I do like to switch from time to time. One of the most intense experiences of my life, not so very long ago, was an unexpected switch. Halloween night. I traveled by train to visit with my lover. She'd made all the arrangements for costumes for us to attend a party later that evening. I didn't know what she chosen or anything about the...Read On