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Telling Mom I m A Crossdresser Part 12 Tow Truck Driver s Big Score

Sorry it has been so long since my last story. I have been busy with alot of things and I thank you for your patience.Lately, I’ve been working part time at a restaurant to make a little extra cash on the side along with my nights as Missy. I was saving up for a cruise I wanted to go on that I heard was for like minded people such as Missy. When people ask me about what I want to do with the money I am saving I just tell them I am thinking of getting a new car or something, but that’s not the...

Crossdressing

Telling Mom I m A Crossdresser Part 11 Girl time

Part 11It had been a while since my last time as Missy. I had been doing some jobs for people, nothing special mostly working on decks and mowing lawns for neighbors to not only keep up appearances so as to not give to much suspicion of where my money was coming from. This continued for what seemed like 2 weeks before and started to wonder if my fun as Missy had ended.I walked in the door to find mom on the phone. I decided to go to get a drink before I got in the shower to cool off so I got...

Crossdressing

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 the door to the outbuilding and pulled down the dressing up trunk from the roof rafters, my heart was beating...

Crossdressing

Girlfriend Ne Crossdresser Bana Diya 8211 Part I

I’m ricky sharma frm delhi and now i am 25 year old. ye meri pelhi story hai agar galti hui ho to plz maaf karna aur mail bejh kar suggetion jarur dena. ye mera real life experience hai… lets start the storyMeri famly me papa-mummy chota bhai aur 2 sal badi sister hai. So story start karta hu apni cd life se. Ye stry aj se 4 sal pelhe se start hui ki kaise mein cd bana. Jab mein 21 ka tha tab meri neha naam ki gf thi. Us ka kadh lagh bagh mere jitna hi hai 5’6. Figure 34 30 32 tha ek dam...

Telling Mom I m A Crossdresser Part 8 5 Cops and Prostitutes

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 record.” Mom said as she gave a sigh of relief.We started to talk about the sybian that mom had bought and some...

Crossdressing

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

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 was sitting at the back of the bus and saw how there wasn’t any other person on the bus besides me and the bus...

Crossdressing

Telling Mom I m A Crossdresser Part 7 5 Amateur Pole Dancers

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 spending long hours with them. Once I was finished, I had to stop to rest as they had left me completely...

Crossdressing

Telling Mom I m A Crossdresser Part 7 The Spa

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. I packed the essentials including a mini dress, a few different pairs of bras and panties, a very sexy and...

Crossdressing

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

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 the kitchen table. I instantly knew that Missy had been hired for another job.I sat down next to my...

Crossdressing

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

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 had experienced since I came out to my mother, but I guess I have her to thank for all my new wonderful clothes...

Crossdressing

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

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 pink with white stockings and long lace gloves that went up to my shoulders. Finally the top was like satin...

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Telling Mom I m A Crossdresser Part 3 Missy s Weekend

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 what was to happen. She told me that I was to live with a couple this weekend and do everything they say....

Crossdressing

Gang banged at a private club

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 arrived and that day at work could not have been any longer. I rushed home and followed my Friday routine of...

Crossdressing

The Slut Within part 2

As I continued on my knees, I felt my little thong riding up my tight little butt. My skirt got in the way of spreading my legs and my tube top and my skin was all sticky with cum. Thankfully, I wouldn’t be wearing any of this much longer. Their watching eyes so aroused my slutty nature. I took off my tube top and skirt leaving my fishnets and six inch heels. I also wore a black thong and bra with the pink mesh that made me feel hot and sexy. I made a conscious effort to shake my hips and moan...

Crossdressing

Old Friend New Relationship Part 1

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 both attended regularly for almost a year, in which time several of us formed a sort of loose union. Among...

Crossdressing

Bo Peep and the neighbor

It had been a hot summer and I had no luck finding a job. My parents did not seem to understand that there just weren't that many companies hiring that year due to the economy so they had really been pressuring me to find a job. They all wanted someone with experience but having just graduated high school I had none. I was nearly at my wits end so when I was asked to house sit for my uncle I jumped at the chance. He lived a half an hour out of town in a nice quiet neighborhood and had a nice...

Crossdressing

Mom s Boyfriend

Once mom and dad's divorce was final I moved back in with mom into our house. Dad had purchased a townhouse a few miles down the road. Being 17 and staying with my aunt and uncle had given me the freedom to do and act as I pleased, so I made no bones about telling mom that her son was a crossdresser and enjoyed sex with men. She really didn't say much and pretty much told me that as long as I was happy, she didn't care.One night mom went out to a bar and met a gentleman, who was about 10 years...

Crossdressing

Confessions of a Sex Crazy Crossdresser Part 9

Hi all, hope you enjoy Sandy's adventures. Chapter 17: Viva Las Vegas Peggy and I woke up in each others arms around 5 AM and we made love again. Then at 6AM when we both had to get up we showered and made love again under the water in the shower. We were avoiding the subjects of me leaving for Las Vegas today and her having to be at work at 8:00. I drove Peg to her apartment on the Northwest section of Phoenix and we exchanged phone numbers. I told her I would call her from Las Vegas and...

Crossdressing

Confessions of a Sex Crazy Crossdresser Part 7

Chapter 13: One Hour Photo I checked in at the motel and went to my room. It was a standard motel near the freeway, two levels tall and I was on the lower level in the room farthest from the office and facing away from the freeway. I opened the door and turned on the air conditioner. It was still about 85 degrees and it was after 5:00. After a quick shower, I picked up my voice mails from home and returned a couple of calls for work and then got dressed into some nicer clothes. I knew there...

Crossdressing

Confessions of a Sex Crazy Cross Dresser

The Confessions of a Sex-Crazy Cross Dresser Book I: The incredible first few weeksChapter 1: Panties Thief and the Late Night Swim My name is Sandy. My name is Tony. I know it sounds confusing, but when you are a cross dresser life is always confusing. Just the terminology alone to describe you…crossdresser or cross dresser? Transvestite, tranny, she-male and many other names used to describe people like me can make you confused. I prefer to be called a cross dresser and yes you can call me...

Crossdressing

Becky s Video

I suppose I was the one that first mentioned porn to Nikki. We'd been chatting on a girls' night out and laughed abut how I'd never found any porn in the house. She giggled and said I was bound to find some sooner or later – all men had some, somewhere. A few days later, I'd completely forgotten our drunken conversation and so when Nikki showed up at mine after you'd gone out with your friends, I was surprised when she mentioned it. We'd both had a few glasses of wine at that point and when...

Crossdressing

Working It

I’ve needed some repairs and painting done in a bedroom for a long time and decided to get some estimates. I had a water leak in the ceiling, and there was a hole there since it was fixed a month ago. Several professional painters came in and they all wanted $700 or more to do the job. I decided to ask my friends if they knew someone who might do it for less. One of my friends told me about Jim, a young guy going to college, who also has a painting business on the side. She told me that he...

Crossdressing

Loverboy Ricky

It’s been some time since I wrote about my crazy life as a slutty crossdresser so with some free time right now I thought I might tell you about Ricky, one of my early boyfriends when I was a teenager…. Ricky moved into our neighborhood when I was 17 and he was 18 and I had a crush on him right away. He was so damn good looking with dark brown hair, brown eyes and strong athletic body and fantasizing about his cock between my lips made me dizzy every time I saw him. It...

Crossdressing

indian crossdresser

hiiiiiiiiii every one here's kiran from india ,punjab first of all its not a fictitous story ,it is a real part of my life my actual name is rahul and me a guy now of 20 yrs old. so lets start frm my age of 12 yrs............................... me frm starting was very likely to kiddish me always remain at home .not to go any where else than in my street. in mid of june when our holidays were going on my parents were with at home ,i asked them about there relationship .they bit were not happy...

Crossdressing

Doing the landlord Do It In Mexico 2

...........I got home from my first day gone public fully dressed as a lady. It was late in the afternoon, I filled my bathtub with warm water , put in scented bathoil in it , laid in there for an hour and 20 min. Thinking of that day in town , when I was getting fucked by FRANKLIN . Just thinking of that whole scenerio made me horny . I started slightly fingering my asshole, but that could not compare to the hard cock FRANKLIN drove inside me with such TLC. My cock was so...

Crossdressing

First Time In 19 years

I met my wife in 1989 and we were married 2 years later. Since the day I met her,I gave up my sexual encounters with men and focused on her. We have a great relationship and a beautiful daughter who is on her way to college. Two weeks ago my wife went away on a business trip to San Diego and my daughter went to Arizona to spend time with the grandparents before she left for school. I never gave up my passion for lingerie and kept most of my things from early on and still bought new ones to...

Crossdressing

The Young Crossdresser Part 3

So the next night arrives and once again I find myself dressing up to head back to mom and dad's porn store to see if my lover from last night might be there. We had scheduled to be there around 8:00pm. I arrive in my car,check myself in the mirror and go inside. I see him instantly standing in the front looking at magizines and walk over to him and say hi. He smiles and looks me up and down and tells me I look hot tonight. He asks me if we could go back to my place since my folks were still...

Crossdressing

The Young Crossdresser Part 2

So after my little adventure at mom and dad's bookstore,the next couple of years were uneventful. I did have sex a couple of times with Phylis,the older lady that was part of mom and dad's swinger group. I knew that I was wanting something more,something was still missing and I kept thinking back to how the guy's cock felt as it spewed cum into my panty covered ass. Now I was 15 and one weekend my parents went away with some friends and I knew that this would be the perfect oppurtunity to...

Crossdressing

My Story

This is my story in a short form of how I became me a 22 year old black gay crossdresser. I've always had gay tendasies from as long as I can remember but at age 17 I met a guy who house I use to walk by after school and we would chat, after a while I told him about me and he said he always thought I would make a cute girl, now he was white and a bit older than me at 30. After a couple weeks he talked me into comming in his place said he had a present for me, well what it was several girl...

Crossdressing

First Time Out

This is a true story about my first time I went out dressed at a club I had been in the closet for years and up until this point only a few people had ever seen me dressed my freind Bill and some guys I went to an adult book store. I had been dressing for Bill alot in mine and his apartment but I had this erge to go out clubbing dressed I had asked Bill several times but it seemed he enjoyed just what we were doing in our apartments but I needed more so I decided to do it without him, I made...

Crossdressing

Mack and Me

I am a 36yr old black crossdresser who only came out the closet about four years ago going to cd bars and clubs to dance and so forth but this is about a dream I had reasonly about a guy I've been chatting with online, now we never have met yet but I do know its just a matter of time anyway here is my dream. I was out for a night of fun in one of my regular clubs dressed for the kill in a short red pleated skirt red top and four inch open toe shoes, I was having a drink with one of my regular...

Crossdressing

A great experience as a crossdresser

I was born and grew up for the first 27 years in England. Ever since I was 16 years old I have always had an infatuation with sexy ladies lingerie.I used to dress up in my mothers and older sisters lingerie and get very turned on and wank myself off while dressed up. I am now 53 years old and still tremendously enjoy the thrills of dressing up and wearing sexy lingerie.One of my early experiences was when I was 18 going on 19. I had been to a thrift store and purchased several items of ladies...

Crossdressing

My sexy crossdressing affair xx

When I was in my early forties I started an elicit affair with a divorced woman called Sandra. We both worked for the same company and just after our affair started the company was taken over by a company based in Leeds and we were relocated there. Several of the staff were needed to get the manufacturing process up and running including Sandra and myself. We would travel by car to Leeds on a Monday and return on a Friday. Sandra was a very attractive woman in her late forties with a great...

First Encounter Ch 7 Conclusion

I approach the bed cautiously. I can tell you still want me and I definitely desire you. How can that be so? You're not en femme, but still, I am transfixed by your waving appendage. I take my place at your side and our lips meet in an old familiar embrace. We kiss long and passionately. "Wow! I exclaim," I've never kissed a man before," I pant. "Of course you have, silly, you've been kissing one all weekend," is your breathless reply. My mind races to make sense of the situation. You are still...

Crossdressing

Dawn Visits Kansas Chapters One Six

Prologue:In an earlier story, Dan Becomes Dawn, Dan had stopped in Denver, coming out as Dawn, a crossdresser, to former neighbors. At a swinging party the next night, Dawn had met, and connected with, Patti. She accompanied Dawn to Steamboat Springs on a business trip for two nights. Dawn worked three more days, then returned to the former neighbors’ home for a second weekend before returning to Florida. Meanwhile, Patti visited her daughter in Aspen, then returned to her parents’ farm in...

Crossdressing

Night Out

"Ladies hour, you get in for free." The bouncer nodded her in as she flashed her id. It was a spur of the moment that she decided to go to the club alone. As a Saturday night, it was ripe for excitement. Yet, none of her friends were up for it.She talked herself into going alone for once, the need to escape the monotony of the week and weak hookups were too strong. She yearned to feel the music, shake her body, and meld into the crowd of dancing bodies as alcohol flooded her veins. A little...

Crossdressing

Night Out Ch 3 Talk to me

I wonder if it’s too late? I mean...it has been three days."Jamie, we have a meeting coming up around 2:15 pm. Did you get the email?"He looked up ungluing his zoned eyes that were unfocused on the screen of his work computer. Again, he was lost in his thoughts as he feigned being busy due to the inability to focus. Evy was heavily on his mind; invading his workday. He almost didn't recognize his name, which highlighted another obstacle of hesitance with reaching out to her."Uh yeah. It was...

Crossdressing

Dawn And Patti Move To Denver Part Two

Part Two: Finding a New HomePatti and I woke about the same time Tuesday morning. I got up first, undressed, showered, shaved, put on a bra and panties, applied my makeup, and cleared out of the bath. Patti then showered, applied her makeup, and dressed. We would not be wearing heels today, walking sandals would be much more appropriate, so I chose a short sleeve, coral red crinkle top with a navy midi flared skirt. Patti selected a multi-color peasant blouse with a denim mid-calf...

Crossdressing

My New BFF Part Five

Wednesday morning I woke up and took a shower before going back to my bedroom to pick out some clothes to wear. Although I was starting to accumulate a small wardrobe, I still had a long way to go and found myself with little choice for the day. Also, most of my clothes were now in need of being washed. I put on a pair of lacy pink panties, a matching padded bra, and the only clean pair of shorts and blouse remaining. It had been five days since I wore any male clothes. I thought about...

Crossdressing

Turned out and on

After 20 years of marriage she caught me in her panties I have been a cross dresser since I was 15 years old. I have always kept it a secret until I was 40 yearsold and had been married for 20 years. Then one night it all changed.My wife and her best friend were headed out for a girls night out. I was excited because it meant I would have the house to myself and would be able to play around the house in my panties. She had barely pulled from the driveway and I was pulling out some of her...

Crossdressing

Realized Fantasies Chapter 1 Exposure

Steve wasn’t sure, but he thought he heard the bathroom door close. He was in the shower and the bathroom fan was running, so he stopped for a moment to listen. Maybe one of the guys came in to use the toilet, he wondered.“Hello?” he said aloud.No reply. It was probably just one of the other guys getting something they’d left in the bathroom, he thought. Steve was one of the last to shower, and the other guys had left a variety of toiletry items at the sink. So he went on showering but hurried...

Crossdressing

Missy Returns

It had been a long time from the seven days I spent with my studs, but sadly I went off to school and Missy had to go on an extended vacation. However, school did not work out as planned and I found myself in a new city and my own apartment with a small job. I had to help pay the bills. For a while I lived with a roommate who was a little homophobic and despised the ideas of trannies. He never found out that I was Missy but had come across the site once and never recognized me. Eventually, he...

Crossdressing

b Incidents in a Crossdressers Life Part 5 b

Incidents in a Crossdressers Life: Part 5After our last escapade, Sarah (a boy who grew up as a girl) went home and left her soiled Smurf printed panties behind and I snatched them up before I headed home. Buddy smiled as I sniffed the crotch. She demanded I lick the crust. I was being too playful so she walked up and forced them into my mouth. I guess I was not done for the night no matter how exhausted and cumless I felt. The panties in my mouth instantly got my eraser nipples hard and up...

Truck Stop Tranny Sluts

My girlfriend and lover Candi and I were driving back to her place for some steamy tranny sex after a night of partying at a tranny/gay bar in town when we passed a truck stop on the highway. Buzzed and horny as we were, we laughed about stopping in the lot and doing so hookin’ as a means to get us some trucker cock. After a minute or two of silence, Candi said lets do it and before I could answer she was turning back for the truck stop! Candi and I are both bisexual crossdressers and we pass...

Crossdressing

Becoming a Sissy

For the longest time I can remember loving the look of pantyhose on a woman. It made their legs look so sexy and especially when they wore heels. I would always jack off while looking at pictures of women in pantyhose in magazines. So one day after turning sixteen I got the nerve to try on a pair of my aunt's hose. OMG they felt amazing and the way they made my legs look so smooth and sexy was a huge turn on. So mush that I had to lay there and masturbate. They also made me feel feminine. I'd...

Crossdressing

Crossdressers Rush

If you have a fixed aversion to cross-dressing sissies, you may wish to go elsewhere. However, my story isn’t about that, although it provides the protagonist vehicle. It’s about control… self-control, losing control, being controlled and everything out of control. I hope you enjoy my style ….. p.s. If my humble contribution offends or annoys any readers, I sincerely apologize. My intent was merely to provide a brief moment of stimulating entertainment. Comment and ask for the saga...

Terry Gets It In The End

The converted attic was my room and it gave me loads of privacy. So as I grew up I could wear the clothes I liked, as long as I stayed in my room. By the time I was a senior in high school, I kept my toe nails painted all the time and I wore panties every day. At night I wore frilly little night gowns and more likely than not I would masturbate, always fantasizing that I was the girl and some faceless guy was fucking the shit out of me. I learned to dance and I loved the way my skirt flew up...

Crossdressing

The Change Up

Finally a break comes my way. The children are off to college, the wife has to go out of the country for two months on business. I can’t remember the last time we had sex. She used to dress in all types of lingerie for me. It helped me suppress some of my crossdressing desires. That stopped and my crossdressing started to grow again. What an opportunity for me, I can change up and dress the entire time except for when I have to go to the office. Lucky me, most times I work from home. Sunday, my...

Crossdressing

Caught in My Girlfriend s Panties

Bella was wearing a black and white checkered wrap dress. The deep-v neckline teased her ample cleavage. Without seeing it, I knew she was also wearing a half-slip and lingerie chosen to please me. I pinned her to the foyer wall as soon as we entered her house. We kissed. I grabbed her soft ass.She had a midwestern look with fair skin, dirty blond hair, and blue eyes. She was fit, but not slender, with a big sexy ass, smooth thighs, and nice bell-shaped tits. I took her hand and led her to...

Crossdressing

Taking That First Step A New Chapter Begins

The Summer was drawing to a close, and Lance would soon return to school for his senior year. As excited as he was about his final year, he was saddened that meant no more early morning rendezvous with the stunning Cassandra.It had been a great Summer. Thanks to her assistance Lance had taken his desire to crossdress to a whole new level and he became Lana. In order to complete his stunning transformation he spent many hours in his room at night working on his skill at makeup. Over...

Crossdressing

And It Begins

There seems to be a common belief, if you want to call it that, that there are basically three “levels” of Crossdressers or Crossdressing. The first of these is what is referred to as fetish dressing. These people have no intention of doing anything other than wearing items of feminine attire. They have no desire to even attempt to emulate the female persona. This is purely a very temporary thing for little more than the thrill of it. The next group that they describe are interested in...

Crossdressing

Crossdress swaps clothes and gets assfucked in pub

A few years ago I was on a weekend trip to Brussels and Amsterdam with some friends, and found out a girl I knew from Ukraine was now living in Lille, not so far away, so I decided to make a quick trip to see her the evening before we were due to fly home. I caught the train from Brussels to Lille and she and her boyfriend picked me up at the station. She was a short, curvy blonde, with equally large breasts and ass. She loved wearing sexy outfits which showed them off. This evening she was...

Girlfriend Catches Me Crossdressing

At this point I have been crossdressing for many years. I started out with my mother’s panties and bras. I would wait till she had gone to work and then go to her room and pick out one of my favorite matching bra and panties. I would lay on her bed and stroke my cock though the soft silky material, dreaming of her walking in and catching me and telling me what a little faggot I am. It never took me long to cum. This fantasy never came to be, but wanting to get caught stayed with me.A few years...

JOANNE SLAM A LIFETIME OF CROSSDRESSING hellip Almost

JOANNE SLAM - A LIFETIME OF CROSSDRESSING…..Almost!!!I have been doing this for a long time, cross dressing and my wanton ways with my transvestite fetish, my feelings of bi-sexuality and the thoughts of being “The Nasty Looking Slut” when I would look at porn magazines. This was in the late 60s and early 70’s mind you so I was seeing very cool, I thought anyway, looking back now it was that vintage lingerie and under-garments style and as a teenager it was most likely finding these kinds of...

Dan Becomes Dawn

Chapter One: The InvitationI work from home and am able to dress enfemme most days.Today I am wearing a pink flower-pattern, button front blouse, knee-length white a-line skirt, a pair of white walking sandals with a wavy, medium brown wig and clip-on earrings. Under that I am wearing a corset to flatten my gut, matching white lace panties and underwire 40-D bra to support adhesive-attached breast forms, which give me a comfortable bosom.I had just received a call from an investment group...

Crossdressing

Lunch Date With Clair

It was Tuesday morning and I had a rheumatology appointment in Maple Grove at 10:15 am. It was now about 7:30 and I thought I should start getting ready for my appointment and lunch date I had set up with Clair.When I talked with Clair on the phone last week, we decided an early lunch date would work for us. She told me to meet her at Biaggi's at 11:30 am and that she would be waiting.I jumped into the shower and shaved my body and legs. Making sure not to miss any hairs, I ran the razor over...

Crossdressing

Jenny Mike A Day out

I woke up in the morning with Michelle’s arm around me. We were spooning. She was the big spoon. I held on-to her arm stroking it gently as I recalled how ‘Mike’ and I had gotten it on in the living room the previous night. ‘Mike’ had fucked me on numerous occasions in the past, but my ass was still sore after what we had gotten up-to last night! God it was so hot! I turned my head to look at the clock on the night-stand and saw that it was 9:30 a.m. I slowly lifted Michelle’s arm from around...

Crossdressing

My First night

This is a true story that I personally have experienced and wanted to share with like minded people. Thankyou. The evening drew closer after work which had been busy and made me rather stressed. I work as a graphic designer/illustrator in a well known and respected company. I left my studio in London and drove the twenty minute journey that I make, day in day out, to my flat which I share with my loving and devoted fiancée. Marie and I have been together for three years and have known each...

Crossdressing

Crossdresser s Spanking Scene

My roommate and I were both bi and part-time cross-dressers. We were also familiar with consensual B & D and had already worked out several code words, then went a step further and wrote scenes for each other, so that when we're in the mood, we could call up the scene rather than try to explain it or coach someone through it. Sometimes we did a scene to please each other sometimes we asked for a scene because we were in a specific mood. So it was that I got an e-mail at work, which...

Crossdressing

One On The Way

Ryan arrived home from work earlier than normal thanks to lighter than normal rush hour traffic and he was quite happy. This would give him plenty of time to get ready and ensure that his mobile home was clean enough to receive visitors. Once satisfied on the condition of his place, he stripped off his work clothes and headed to the shower.He spent an extra amount of time allowing the warm soapy water to clean every inch of his body. Still dripping with warm water, he reached out of the shower...

Crossdressing

A Night to Herself in London

DISCLAIMER: This is a fantasy story depicting sexual acts involving adults. The story is intended for adult readers only.-----------------------------She'd been working hard in the lead up to this night for months. It takes alot of planning and discipline to look and feel as good as she did as she began to prepare.The day had been spent exercising, fasting and hydrating. As she stepped into the shower after finally finishing cleaning herself out, she sighed deeply since now the fun could...

Crossdressing

Being Joann

I sat in front of my computer and started surfing transgendered sites when I came across an article on psychiatrists specializing in cross-dressers, transvestites, and transsexuals. Some of their treatments included a psychological evaluation, hormone therapy, group sessions, and preoperative assistance. The mail order hormones I was taking were having some positive effects, but I read there were better and safer hormone medicines available by prescription. also really wanted to get some breast...

Crossdressing

My First Time Out On The Town All Dolled Up

It was Christmas time but still warm in Los Angeles. I was living in West LA and heard about a club called Club Sex Addict in the valley, a haven for crossdressers. I had a fairly extensive warddrobe that I bought in a Culver City lingerie shop. I just bit the bullet and went there and told the girl who worked there that I was a CD and she would help my pick out sexy slutty stuff to wear.I'm middle aged but have been dressing up in secret for years, but I really had the urge to get out in...

Crossdressing

Crossdressing Friends

I forgot about my dvd and took the picture. It was inspiration for several orgasms. A long black haired wig hung down to his shoulders and a black leather corset was squeezing his body tightly. I only wished that the picture went down further so I could see his cock. Part of me wanted to tell him that I knew. At least then, we would both have someone to share this interest with. I figured I’d talk to him about sexual interests and fetishes, see where it led. “So…Joe. What kind...

Another Road Trip Story

With trembling fingers, he began to pack his large suitcase. First, he started with some of the silkiest and sexiest lingerie in his extensive collection. At least a half dozen silk and lace bikini panties along with tiny silky thongs were placed inside first along with their matching bras.Garter belts made of satin and silk came next. A half a dozen pairs of black nylons that were either seamed or patterned shared a spot along with crotchless pantyhose. Four long silky full slips each boasting...

Crossdressing

Being a Bride

The alarm went off and I turned over in bed, I could not believe the day had finally come. I slipped out of bed and adjusted my satin night dress, fixed one of the spaghetti straps on my shoulder and covered one of my breasts that was exposed.In the kitchen I got myself a juice and croissant and sat at the table.My thoughts went back several months to my first meeting with Steve, I had signed up to a website that helped crossdressers like me hook up with men who wanted to be with people like...

Crossdressing

Further Exploration

After Jerry kissed me goodnight and returned to his own room, I had time to reflect. Sex with him was so different than it had been with Jack. Jack took his time, slowly and steadily pumping his hard shaft in my man-pussy and making me feel like his special girl. Jerry was passionate and urgent, riding me hard and making me feel special in a whole different, slutty, way. I was Jerry’s special little slut, and I loved every second of being pummeled by his big thick cock. There was no doubt that...

Crossdressing

Sissy Blane and the Hydraulic Inevitable

The story so far: debt-ridden Sissy Blane's first obligatory date with Mr. Plumrose is about to take place. '...there's nothing good or bad, but thinking makes it so.' The truth of the old saying occurred to me as I awoke on the fateful Friday and was surprised to discover that I was looking forward to the events of the coming evening.Arising from my bed feeling energized I bounced downstairs to make a breakfast of oatmeal and raisins and some french-press coffee. I decided that would be it,...

Crossdressing

A Young Crossdressers Beginnings

( . Y . )I just found out my Mom told a whole group of parents about an incident when she caught me in her cloths. Specifically, she caught me in her bra, panties, panty hose, and makeup. I am approaching thirty-five years old now and the individual that told me must have heard it from his mother, who was one of the other parents. We used to go camping every year and one night when the k**s were playing or sleeping the parents were talking. She let it slip that she caught me in her room with...

Night at the Video Store part 3

There I was a sissy bimbo dressed like a slut in a short black micro mini skirt, spike heels, lots of junk jewelry, huge platinum blonde wig, shoulder strap white fur purse and, of course, perfect make up.I had never been to this video theatre before and was nervous at first, but I waited for my eyes to adjust to the darkness and then moved into the theatre area. Screen five was recommended to me by the door girl, who I knew from other theatres. She knew I was a cross dresser and a bimbo slut...

Crossdressing

My first crossdressed cocksucking true story

It happend few years ago. My ex gave me a "hall pass" to explore my sexuality although she didn't like me dolled up and looking like a cheap slut.I was chatting for some time with this man on the IRC. He liked crossdressers, boys on the way to become fem sluts. He was mature, around 50. And he was also travelling through Europe.One day, he caught me online and told me that he will be passing my town and stopping by in the hotel. I was supposed to meet him on friday night at the hotel. He gave...

Crossdressed And Became A Complete Girl

Hello everyone..I’m harsh aka ayesha..I’m a regular reader of Indian sex stories and always search for stories of gay crossdressers.Before starting my first real life gay experience let me introduce myself..I’m a 24-year-old boy who wants to be treated like a teenage girl..Wants to be pampered.Wanna be treated as a wife for my man at home.His girlfriend when we are outside and as his slut when we are in bed.. I come from ranchi..I am slim, fair and height 5’8″..I m very curious about sex.I...

crossdressers first time

i first started to wear tights when i was 18,i was shocked when i first realised i loved tight panties and sheer tights. i was staying with my friends mother who was 65 at the time,she wore the sexiest lingerie i had ever seen,especially on a woman that age,but i felt drawn to the sheer stockings. the next day i was taking a bath when i noticed them on the wash basket,i had an urge to wear them,i was very shocked by this desire but had to!i slipped them on taking care not to rip them,they were...

Toni Encounters Greg

Anthony Lorimer was aged in his early thirties. Over the last year or so, he had progressed from occasionally putting on his now estranged wife's underwear when she was not at home, to the stage that he was now at of going out fully dressed and made up as a woman. When dressed Anthony became Toni and, in part due to his build and bone structure, he became a very attractive female.In the early days, he would wank whilst wearing his wife's knickers but now he had become so adept at becoming 'she'...

Crossdressing

Second Encounter Ch 4

I awaken at the first rays of light streaming through the curtains. I slip out of bed, freshen up in the bathroom, and make my way to the kitchen. I start the coffee pot, and soon the rich aroma fills the cottage. I hear you in the bathroom, and soon you make an entrance into the kitchen. "Good morning, Sunshine," I quip, " How did you sleep?""Solid as a rock," you say as you rub your eyes."Coffee?" I ask."Absolutely!" you say with gusto."What would you like in it?" I ask."Cream, and lots of...

Crossdressing

Noodles Part 2

Mark and I were still smiling and reveling from our exciting private dance with Amber, as he pointed the car towards my neighborhood. Ever since Mark mentioned that Sunday nights are Ladies Night, I wanted to know more. I prodded him, "What's so crazy about it?""OK," Mark began. "For starters, 'ladies' don't pay cover. They get free champagne for the first hour. And their private shows are half-price. So when I say it's 'crazy', dude, it's packed. Mostly T-girls and crossdressers. They...

Crossdressing

Second Encounter conclusion

We grab a blanket and step out into the cool evening. The ocean breeze feels great and the sky is beginning to lighten in the east. We walk naked down the beach, delighting in each other's company. We chat like schoolgirls, and I am overcome with a feeling of happiness and joy. We soon reach the secluded cove we had visited the night before. As we approach it, we hear the unmistakable sound of sexual ecstasy. We top the dune and behold Jill and Jasmine locked in a passionate sixty-nine...

Crossdressing

Noodles Part 7

Lori is coming back home tonight, I had to remind myself. Mark and I slept together last night, then I had to tell him goodbye this morning. That was a bittersweet ending to an amazing weekend. I washed all the laundry and sheets, putting everything back the way it was before my wife went out of town. I hadn't heard anything from Mark since he left this morning. That's probably for the best anyway, I reasoned. I need to get my head right and remember my masculine identity. Lori will be...

Crossdressing

Crossdressing Porn Story 2

Jack let himself in the front door. It had been a long day at the store. He’d noticed Ray’s Porsche in the garage. “Honey, I’m home.” From the kitchen came a sweet “Hi Janice how was your day.” “Pretty rough.” “Well just sit down on the couch and relax. I’ll have dinner ready in jiff.” They had divided up the house chores and Jack was glad that Ray had taken over the cooking. The meals were always delicious. Ray walked in...

Crossdresser s Surprise

A Crossdresser' s Surprise - by: by Deborah Pinto I guess I should have seen it coming. My wife, Virginia, and I were drifting apart sexually, and I should have suspected that she was having an affair. Afterall, we had not made love in over a year except for one night she had come home a little drunk from her office Christmas party and had virtually raped me in the middle of the night. I remember her laughing and saying, "Tim, what's wrong with you tonight? You feel so tiny inside...

My first Forced Femme Crossdressing experience wit

Forced Femme CrossdressingForced Femme Crossdressing had never crossed my mind. Certainly not that day. I had been lounging in my PJs one evening early last December. My fiancé Melissa was working 2nd shift rotation. When her best friend Dawn showed up at our front door. She invited herself in when I opened it. When Dawn and I are alone, she always teases me about my bisexual tendencies. It was my own fault for letting them slip one night when I had way too much to drink. Which Melissa had...

Caught Crossdressing by Aunt Sharon

Caught Crossdressing by Aunt Sharon Story by Kresha Matay "I wonder where Brad is? He knows you're coming, you'd think he'd stick around. Oh, I hope he'll turn up soon, otherwise you'll have to drive back in the dark." "Rita, don't worry about the boy so much. Brad is like every other sixteen year old boy. He's probably driving around with his friends looking for girls and forgot I was coming!" "Well, aah, I don't think so!" His mother stumbled to say. "That's something you and I...

The Photographer And The Sissy

I was 2twenty-two, closeted fully and living out my sex life in fantasy and on the internet. I had discovered my love of dicks in my teens, followed a few years later by my fetish for dressing up like a girl. I have no idea why, but the sight of my own body in tights, knickers, stockings and heels made my boy pussy (dick) wetter (harder) than anything else, straight or gay.Luckily, I lived alone (in a private studio apartment, in a major city in the Netherlands), so I could basically live out...

Crossdressing

Crossdressing With My Mami

Hii, mere naam ankit hai. Main mumbai ka rahnewala hoo. Yeh kahani meri or meri mami ki hai jab hum sath me crossdressing kiya karte hai. Meri mami ma naam sabita hai. Unki lambai 5ft or woh thodi moti type ki hai. Unka koi baby nhi. Lekin fashion ke mamlo me save age rahti hai. Jab mai 10std me padta tha tab meri mami or mama culcutta se mumbai aaye. Yaha aane ki unki ek hee wajah thi paisa. Mujhe pahle se hee porn video dekhna achcha lagta tha. Mujhe femdom, bdsm, bondage jaisi porn bahut...

A Paper to The Society of Crossdressing Hardware Engineers

SOME NOTES ON THE DESIGN OF CROSSDRESSING HARDWARE There are several difficulties to be overcome in the design of self-crossdressing hardware. This paper will enumerate them and offer suggestions to remediate the problems. 1) Determining the sex of the hardware. Actually, determining the sex of the hardware is not a formidable task. The primary problem occurs because design engineers have no discernible knowledge of sex. After all, anyone who spends their day in front of a...

Humor

Crossdressed in public

hi ppl i m rohit….i m 16 yrs old and i live in delhi…i love to crossdress when i m all alone. i hv been doing this sicne i was 13 yrs old.i used to wear my mom’s clothes n gaze myself at mirror. though i was not a gay but i wanted to try gay sex once by turning to a women. it was in d month of june when my parents had to go to noida for some work and i was left all alone at home for a week. one evening i thought i should try crossdressing and go out to enjoy in public n tease some ppl.i...

Gay Male

A Maid Story

It had been a long day and Paul was tired. After a week of traveling and a full day of meetings, Paul was ready to unwind with his wife, Marie. They were what many people might describe as soul-mates. They were best friends who shared their deepest, darkest secrets with one another and who regularly consulted with one another on a wide variety of topics. Their love life had suffered lately and had grown somewhat predictable but that didn’t bother Paul too much. There was so much...

Crossdressing

We All Have Our Stories

I want to present a few short vignettes concerning crossdressing. A most interesting and individual form of sexual gratification and fulfillment. The first story concerns a strong man, happily married and happy with the sex he is getting from his wife, but something seems missing in his life. He often walks the streets and window shops, but seems to be drawn to the windows displaying ladies' wear, from dresses, to frilly underwear, to stylish shoes. He is drawn to it all. And he forms the...

Crossdressing

If the Crossdress fits

If the Crossdress fits... I didn't know what to expect when Maxine opened the door to her loft. I hadn't really thought about it, but there she was, holding it open for me. Her place looked like the hideout of a very stylish, sophisticated thief, who had just robbed a Sanrio store. That is to say all the furniture was sleek and minimalistic, classy even, but it was piled high with cute Japanese toys. A large window overlooking the arts district dominated the loft's main room. I...

Ray and the Halloween Party

I have had sex with a few guys since my last story but there nothing much worth writing about so I thought I would “go retro” and tell you about a hot experience I had in my senior year of high school. At that time I kept my crossdressing pretty much private and only a handful of people knew about my slutty side as Lisa. Even most of my best friends had no clue. (At least that’s what I thought at the time.) One of my best friends was a good looking guy named Ray. Ray lived...

Crossdressing

It s A Family Affair

It wasn't unusual to receive a phone call from Rebecca at eleven o'clock in the evening. Since her recent divorce, she often called for a chat with my wife Linda. "Hey, gorgeous!" I answered the call on the landline.Rebecca, aka Becky, aka Bex is a "special" friend. She has known of my crossdressing for over twenty years, during which time she has been a major contributor to my wardrobe. She's an attractive brunette, has a great figure, and her shoe size is the same as mine. Only a week ago...

Crossdressing

Friday night crossdressing fun part two

Friday night crossdressing. Doing a favor for a gay neighbor gets me more exposure when a friend finds out I like crossdressing. Continued… Gail walks up to Candice, leans over and they start making out. Before I knew it everyone had a partner and they were all making out except Mark and I. As I said before, Mark and I have known eachother since grade four. I heard he made a pass to another guy once but I thought it was just a rumor. I've always liked crossdressing but didn't consider...

First Time Full Dressed Up

I had always wondered what it was like to get dressed up as a woman and go outside. One day the opportunity came. I didn’t go crazy, nothing super public, but outside nonetheless.My wife was out of town on business and there was a bag of clothes we were going to donate, and inside was a pink office-type suit: skirt, white blouse, and pink jacket. I had bought a pair of pantyhose earlier and had access to wigs and costume jewelry. I find pantyhose very sexy and had beat off and cum in them...

Crossdressing

Where Did My Damn Key Go Part 3

Four days; I've dealt with four grueling days of not being able to touch myself. Jesus, how can anyone even do this without even going insane?!Ever since I crossed paths with that dominating bimbo, my entire routine had changed. And to be honest, I was surprised at how much sex was in my life. From the moment I woke up to the second I crashed and fell asleep, my mind was very frequently in the gutter, wondering when I was going to get some ass or where can I go to beat one off real quick....

Crossdressing

576 Shadow Oak Drive Part 1

I met Molly on a seemingly random day. How could I ever have known she would change me forever? It was late April and I was working behind the cash register of a local department store. I was eighteen, just out of high school, and didn't have any sort of plan for my future. I figured that I would take a least a year off before applying to any universities. I liked working at the department store not only because of the discounts, but because I had figured out a way to sneak some of the clothes,...

Crossdressing

Not Crossing The Line

When I was a kid I had a book called, ‘What Do People Do All Day?’ It made a start at teaching me about the variety of jobs that exist in the world. As an adult I feel it would be equally beneficial if there was a book as simple as that one which answered the question, ‘Why do people do the things they do?’ Part of the trouble is that I often do not even understand my own motivation, particularly for those things I feel uneasy about sharing with others. For my normal side, I married an...

Crossdressing

The Bodysuit

“The process is actually very simple Mr. Smith,” she said.“It is very much like 3D printing, just using different materials and in a printer that prints on your body. We can print anything on top of your body to make you look however you want. The technology was originally developed for use in movie special effects, but we have seen there are, well, more personal uses that some of our clients like to use the service for.”How could I pass on this I thought. The chance to have a body in effect...

Crossdressing

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