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38

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

37

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

29

Meeting Carla

A friend introduces me to Carla

I hadn’t seen Mark for almost a year. His father had found a new job and subsequently his family had moved to another state. I’d known Mark since the beginning of high-school and I was really looking forward to seeing him again. We’d become friends since day one and it had come as quite a shock when he told me he was leaving. Not only had we seen each other in school each day, but we’d hung...Read On

29

The Change Up - Part 4 - Tower Chair

Deedra shows how big a slut she is and becomes a member of Elsie’s VIP club!

Looking through the sheer curtains of the cabana, I see about a dozen people looking at both of us. Some I just met tonight and others that I don't recognize. Then Emily says to me, "Since you been a naughty cum slut again, I will have you service some of the VIP members tonight! Remember don't talk to anyone and only whisper into my ear." Cuddling next to Emily, I think back to the...Read On

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

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

20

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

A Saturday Afternoon Visit to the Office

I get to let the sissy in me cum out during a Saturday afternoon visit to the office

I usually work from home as I have a very private place with a wonderful view and Lord knows I’ve put in more than my fair share of office hours over the years. But I do occasionally elect to make visits to the office both during normal office hours and off-hours to make copies, restock my home supplies and have a cup of coffee with a long-term friend or two. Usually when I do hit the office,...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

18

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

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

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

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

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

34

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

28

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 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

26

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