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Crossdressing

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13

Becoming an Escort

The nights second cock spurted hot sticky cum on my face and I greedily pushed into my mouth faking my enjoyment of that bitter taste. My “lover” dressed and left the room. I lay back on the bed where two men had fucked me that night and pondered how I had got into this position. Despite myself my cock was rock hard in its silk panties stained with my own cum. 3 weeks earlier I had told...Read On

15

Caught and the Consequences Part 4

Husband caught dressing and the wife's retribution continues

Part 4   I served dinner at 7.00pm as requested and I was made to stand by the table so that I could serve wine as their glasses were emptied and attend to them as requested. I did find the whole experience satisfying in a kind of way as I knew I was pleasing my Mistress and hopefully Sir as well, although neither of them had any conversation for me.   ...Read On

10

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when...Read On

14

Lingerie and Domination

Lingerie Shopping and something more

I had answered an ad on telephone dating service. She described herself as a ‘bedroom dom’. I am not sure why I answered the ad and I did not really expect a reply. She phoned when I least expected. I did not think she would be interested but I had mentioned in my reply that I like to dress in lingerie — panties in particular. I met her for a drink. She was younger ( 38 ) than me and...Read On

12

Tennis

A panty sniffer is tamed

Sandra and I had been going out together for about six months. She was the perfect looking girl for me, with her beautiful freckled face, slim turned-up nose, pouty red lips, light green eyes, long blonde hair that she usually kept in a ponytail or braids, a great body topped with perky B-cup tits, and a cute firm ass that just screamed to be pumped. She was only 23, but Sandra already knew...Read On

10

A Gift for Daddy

A CD Sub gives her owner a new toy...

"I brought you a present, Daddy," Stephanie said, giggling, as we stood on the porch in the run-down neighborhood in the industrial part of town. The man standing inside was in the shade inside of the house and I squinted to get a look at him. "Eyes down," Stephanie hissed, elbowing me. I did as she said and smiled inwardly. She was usually very submissive and proper when we were together and...Read On

13

Losing at Strip Poker with Three Women

Oh my god, what did i get into?

Well, last night was quite a night to say the least. Three girl/friends came by with wine coolers and tequila to do a little partying. The four of us have been very tight for over fifteen years. We are very special friends that can talk about anything to each other. I should have known they were up to something when they said the tequila was all mine and the coolers theirs. They know I...Read On

10

Free Clothes

Not what I expected, but definitely what I wanted.

I guess it is something that goes through the mind of every new or closeted crossdresser. Shopping for new clothes as a guy is awkward because it is difficult to do without making it obvious it is for you. Yeah you can go online, but it’s tough if you’re not used to the sizing and the clothes never seem to look the same as the picture. Thus, when searching for playmates on Craigslist, if you...Read On

21

A Fantasy to Remember

Halloween was rapidly approaching and my girlfriend of 2 years was planning something big. She had been a stripper for 10 years and was as kinky as they come. She and I had done a lot, so only a few of her fantasies were left unfulfilled. She had already had women and men, group sex, bondage, been a submissive and a dominate. We had a no holes barred policy. I could have any hole I...Read On

19

Surprise

Aubrey greets his boyfriend home from work in a new way. Slight BDSM ahead.

Aubrey swallowed the lump in his throat as his wrists grew sore from his restraints-being handcuffed to the headboard of the bed, naturally he grew stiff. Speaking of stiff... he peered down, under the frilly black miniskirt of his maid outfit was a visible bump, straining against the panties that constricted it, said lingerie was clinging to his soft pale skin. He bit a plump bottom lip...Read On

34

The very first time....with lots more to come...

My very first sex as a crossdresser.

I guess we all remember our “first time”, and in my case the first time I was with a man while dressed was a awesome experience that I still remember vividly, and it happened by accident.   I started crossdressing when I was about 14 due to my fascination with sexy women. The first time I slipped into a bra and panties and put on mascara and lipstick I knew I was hooked. I felt...Read On

24

All by mistake

A chance encounter

It all began by mistake. I had spent the morning at home, relaxing in one of my favourite outfits. I was starting to think that work beckoned, and had begun the transition back to drab. I took off my wig and make up, but decided to keep my panties, tights and bra on, as my clothes would hide what I was wearing. My attention was caught by a news item, and I sat watching the television for...Read On

16

A Little Walk

A late night walk turns into a dream come true

I love autumn nights, the air is cool and the weather is still nice enough to allow for some late night strolls to the park and through near deserted streets.   Another bonus is that the nights are longer which means that I could escape the seclusion of my home earlier to enjoy the freedom of the outside while dressed as I so enjoy doing. For this particular outing I had decided to go with...Read On

Mistress Hannah's Pathetic Husband Part 3

I learn how manly my mistress wife can be

The first week of having a useful cock went well. For the first time since we got married, we had sex every night. After strapping my extension on, I would lick Hannah's pussy enough to get her turned on and then she'd choose a position. If I got physically worn out, she would choose another position. Because I was having sex so often and doing some research on the Internet, I was able to...Read On

42

Caught, Used and Loving it Part 2

My descent continues

It had been two weeks since I had been caught and used by the mystery woman and her boyfriend. They had left as quietly as they came, and I was left kneeling on the floor dressed in all my best female clothing, cum dripping off my face, and my own cock dribbling cum on the floor. Since then, I had had only two emails. One was sent immediately after they had left and contained ten pictures...Read On

26

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

45

Pamala's first adventure

This happened to me years ago when i was in the Army

I joined the army after I quit school in the 12 th grade. After joining the army it put a crimp in my dressing up as a girl. I did wear panties whenever I got the chance but I really wanted to dress up completely as a girl. I wanted to go out dressed and I have to admit I was attracted to several guys in my unit. My third year in the army I went to Viet Nam in December 1967. I was in the 101...Read On

36

Debbie's Place

A crossdresser gets more than he bargained for

My girlfriend, Linda, was kicking me out of the apartment for the night because her sister, Sandra, was coming to stay. Linda didn’t want her parents to know that she and I were living in sin together. I found it all a bit far-fetched that a girl of 23 years old either couldn’t or wouldn’t tell her parents where to stick their beliefs. But, I knew well enough not to argue with Linda over...Read On

30

Ray and the Halloween Party Part Two

Part two of my wild night at the Halloween party and with Ray...

   When Ray and I arrived at the front door at Sharon ’s house I noticed my lipstick on Ray’s lips from passing the tequila bottle and as I was wiping if off with my fingers the door sprung open. Sharon was dressed as a Playboy bunny and she looked surprised when she saw us. I thought it was because she recognized me but evidently not. “Well, well, Ray, you dirty dog....Read On

22

Aunty's New Girl

Falling into the strange world of Aunty Trixie...

This is the continuation of Tickets Please! Shakily, I keyed in the URL from Trixie's card, my mind in turmoil, heart racing as her sweet gift seeped from my aching pussy and soaked into the lacy panties I was wearing. I was wedged behind one of the 'tables' thoughtfully supplied for the busy passenger. You know the ones, if you move a fraction either way you end up concussing your...Read On

21

Halloween

Boys will be boys

This story is not to be copied or moved to another web site Well here it is Halloween and I have an idea to dress up with my older bro and take the two younger bros out to trick or treat. When the big night came I got some of my sisters things to dress up in. I took all I needed to look just like her with the panties bra and skirt and blouse with a short jacket over it all. I must say...Read On

15

the summer I became Suzie

this is my fantasy

I was 18 years old and taking estrogen for about two years. As my ass and tittles started to grow my desire to dress up became all consuming. I wore sexy panties to school everyday and the excitement about getting caught, grew as well. I was very tiny for my age and picked on by the jocks at school regularly. I'm 5foot 5inches tall, with long brunette hair and blue eyes. I had no body hair and...Read On

33

Seducing Uncle Frank

A tale of a Crossdresser seducing his attractive Uncle.

This is a story that happened some time ago, when I seduced my Uncle Frank. Uncle Frank Uncle Frank was married to my mum's sister. He was about 10 years older than Aunt May, and it was both their second marriages. Uncle Frank had an Italian father, French mother, three older sisters, loads of nephews and nieces, and had property in Kensington, the Algarve, and Telluride. You could say he...Read On

32

All the Way (Part 1)

Kathy makes Richard pay the price

I'd only been married a little over a year when my wife came home early and found me jacking off using a pair of her panties and to be sure, this wasn't the first time. There I was lying in bed with her wispy little nylon panties wrapped around my dick and cumming like nobody's business. I was so wrapped up in my own pleasure that I hadn't even noticed her standing in the doorway watching me. ...Read On

12

Violation

Michele is a closet TV and awaits her lover so they can play out their fantasy

Violation By Michele Nylons I have been home from work for over an hour; I lift my head from the brief that I have been reading by the light of a desk-lamp. The room is full of shadows. I look at the antique clock on the mantle and see it is approaching eight o'clock and I look over at the window; it is dark out. I close the file on my desk and then close the curtains in the study. I...Read On

17

my discovery

my story of becoming a crossdresser

Here are some stories about my sex life and exploration of who I am. Before I started cross-dressing, I fell in love with high heels, mainly cumming in high heels. When I was younger, my parents used to have a large walk-in wardrobe and when they would go out at night I'd search for my dads porno mags. One night when I was reading some mags and my parents were out, I got a bit too excited...Read On

24

Nights in pink satin

Forbidden desires are allowed to awaken.

It finally had happened. Paul couldn't resist the urge anymore. The urge to wear women's clothing. The urge to be degraded and humiliated. The first thing he had done was to have a shower and remove all his body hair. Gazing at his naked self in the mirror, he was pleased with the results. Forcing down a shudder of anticipation and excitement, he reached for the first garment. The feel of...Read On

15

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

7

A Fantasy Come True

My wife and I went on a four day vacation to Charleston to enjoy the sights and especially to enjoy the nights. Our first night there I was no sure how it would go. I was wandering if my wife could really get in the role of being a Dominatrix. Would she really enjoy having DD as her Slave? Could my wife become the Dominatrix that I want and need? All my questions were answered that night. ...Read On

18

The Feminization of Michael - 2

The Feminization of Michael. Chapter 2 I continued with the “weekend” clothes for another few weeks and consistently had people commenting, laughing and making things difficult when I was out shopping. I continued at work in the more feminine suits and blouses too.  The rumours increased and somehow word had got around that at the weekend I wore dresses and full make up! This couldn’t...Read On