Dressing Up indian porn

The Feminisation of Michael Chapter 7

The Feminisation of Michael. Chapter 7 I settled in at Stanmore House quickly and Sam helped a lot and we would spend most days together with her showing me around the estate. I soon persuaded Sam to wear prettier things and we were often seen., me blonde, her brunette, rushing around giggling in little floral dresses. Alternatively we would ride the beautiful horses in our jodhpurs and white lace blouses. I got very fond of a jet black horse called “Star” that moved like a racehorse. ...

Crossdressing

Adventures of Kristof and Marci Part 1

ADVENTURES OF KRISTOF AND MARCI PART I The Meeting I sat on the chair in front of the computer, wearing a tiny black swing skirt, black nylons and red high heels. Beneath the skirt I wore a little pale pink lycra thong and I was naked from the waist up, save for the chain that hung at my chest, the ends connected to each nipple by a little clip. ‘I really need to pee’ I said. ‘Mmmm. Go on then, you know you like it. I think I will, too.’ Marci responded. ‘I can just...

Crossdressing

Son s Bikini

It was a hot day. I told my mom, “I'm going to cool off in the pool.” My sister, Jan, was already out there sunning herself.Mom eyed me over. “You know, Mark, that swimsuit of yours is getting kind of old. You should get a new one. I'll look online to see what I can find for you.”Mom and Dad divorced several years back, but the split was amicable. Jan and I stayed with our mother as Dad traveled a lot. Mom did well working as an executive in a local company. Jan and I each had jobs elsewhere. I...

Crossdressing

Hidden in Plain Sight

It was his own fault. He had spent far too long admiring himself in the mirror and revelling at the sight of the erotic garments he had donned and time had slipped away from him. Just the feeling of these silky garments against his skin made him hard as they always did and a masturbation session would soon follow.The mirror on one side of his sliding closet doors reflected the image of a tall and tanned young man with long dark hair and slightly feminine features. If he had been born a girl,...

Crossdressing

The Compromise Part 1

My wife, Ally, and I have been married for eight years. What once could be considered a torrid love affair had subsequently lost its sexual passion. We don’t have any children, both being career focused, but our sex life had become quite stagnant from the steady grind of life and over-familiarity we had with one another’s sexual tastes. That is, until one crazy night changed everything. About one year ago, we were fighting constantly. We didn’t know why, but we were both at our wits end with...

Crossdressing

Carolyn Makes Her Way part 3

Once I dragged my tenderized ass out of bed, tender because Mike had used a cane on me last night, I dressed in pantyhose, a navy blue, loose skirt, a cream colored satin blouse, black pumps with four inch heels, and a bra. After applying my makeup I took a look at myself in the mirror, making sure I looked good enough to conduct an interview at the leather goods store we were opening in just a few days. I decided I looked business like enough. My first order of business today was a stop at the...

Crossdressing

From Anton to Antonia

The first sex I had with a couple was my boss and some woman we just met in a hotel bar. I liked it, so the boss told me to put out an ad. An advert in Craigslist for my area was all it took. Posted in the casual section under M4WM and a photo of me from the shoulder down, I had a flood of answers. I chose Julian and Rosemary, they were mid- thirties, still twice my age and arranged to meet. Nervously I sat in the bar and looked around; we had only sent each other photos of cocks and pussies,...

Crossdressing

How to Treat a Lady

Being a pretty, petite, believably passable crossdresser makes me a very happy person. I have been dressing up as a sexy girl while daring to go out in public for the past two years since I was sixteen. I have had this urge and desire to dress as a female for as long as I can remember so I have gradually come to accept that I have a feminine side that needs to be nurtured and encouraged.I have managed to accrue several wigs, dozens of dresses, many pairs of high heels and enough makeup to last...

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

All The Way Part 3

When I awoke it was later than usual but considering the fact that I'd been through back to back fuck marathons in as many nights, I thought it wasn't bad. Slipping out of bed I stepped into a robe and went to the potty, before looking at myself in the mirror. I was a mess so I took the time to freshen up my makeup, washing some off before putting any more back on. Satisfied with how I looked, I padded to the kitchen and started the coffee before taking out the eggs and breakfast steaks. I was...

Crossdressing

Girls Night Out Part 2

Girls Night Out Part 2 Well everyone wants to hear about the second part of my night with Julie when I was in New Jersey. In case you didn’t read my first story, my name is Cassie, short for Cassandra (I also go by Sandy sometimes) and I am a cross dresser (CD). A while ago I was spending a hot summer night in New Jersey at a hotel with my friend Julie. We were attending a girl’s night out at a hotel bar with about 25 other t-girls and we had already made a scene with our attire and actions....

Crossdressing

Felix becomes Felicity Chapter 5

FELIX becomes FELICITY Chapter 5 ..My Mum and David had announced their impending marriage with a ceremony planned in about 6 weeks time. No guessing who was to be bridesmaids. The week before we were due to start back to school Jasmine mentioned at breakfast that Thomas wanted to take her to the cinema that night and that they had talked about a foursome me with Bradley . “Not a chance in hell,”I stated. My Mum smiled but then David butted in, “No I think you should go Felicity dear.” I...

Crossdressing

My First Real Outfit

My First Real Outfit I started completely dressing in women’s clothes shortly after high school. I didn’t really own anything of my own but I would fully dress in my mothers clothes a few times when I knew she would be gone for a few hours.. Usually it was just pantyhose, bras, and panties that I would borrow from my mom . I had experimented with it a bit when younger, stealing my mom’s pantyhose and jerking myself to incredible orgasms while wearing them or being forced to wear them from a...

Crossdressing

No Strings Attached The Reunion Chapter 25

It's the first Friday in October, and I sit in front of my dressing table, with my hair in rollers, rechecking my phone for the umpteenth time today before tossing it away in annoyance. My calls and texts haven't been returned by Justin in several months. Still, I'd hoped that today would be different with it being my birthday. Selena is also ignoring my attempts to apologise and my offering of the hand of friendship. I knew at some point that she would grow to dislike me, so I should have...

Crossdressing

Boxing Day fun

Just got home. 4.30pm and it’s already dark. I’m still wearing the stockings and little pink cardigan I put on this morning but the dress and lacy shawl are hidden in my small back pack.A guy messaged this morning asking if I would meet. I agreed and asked if he wanted me to dress as a girl. He replied, “Yes.”After showering I came back downstairs and took off my dressing gown. I walked naked to the wardrobe and took out my black lace suspender belt and stockings, a tiny pink dress that barely...

Crossdressing

Stage eight of my journey to becoming Joann

After returning home from dropping Mom and Dave off at the airport, I immediately jumped in the bathtub and took a long bubble bath. While I was in the bathtub, I shaved the stubble that was starting to form from days of neglect. When I finished my bath, I rubbed most of my body with a good lotion to restore its smoothness, followed by a badly needed pair of sexy red lace bikini panties with a matching bra. I pushed a pair of “B” cup self-adhesive breast forms into the bra. They are quick and...

Crossdressing

Dana Finds A Lover

I've been dressing since I was ten, always being careful to never be seen by anyone. The whole time I grew up I'd never had any girlie clothes of my own but I'd always worn my sister's things, even used her makeup. I always made certain that she never ran out of makeup too quickly. When I knew I had the house to myself, I would dress up and pretend I was a girl. These sessions ended in a great masturbation with something usually deep in my tight little asshole, or boy pussy or ass pussy, as...

Crossdressing

Jenny Learns Her Place Part 2

“Thank you, Master,” I said as I slowly brought myself to my feet, tears of pain rolling down my cheeks. I couldn't see my ass but it was probably purple with bruising and I was happy with that. Bobby would now know that I could withstand a hard spanking with the paddle without falling back on the safe word. “And for good measure,” Bobby said and put the clips back on my nipples. Wincing with the incredible pain, I managed to stand straight. The nipple clips hurt much more this time than the...

Crossdressing

Mistress Hannah s Pathetic Husband Part 4

The third and final day of my transformative weekend started poorly. I had aches and pains all over. My neck and back and thigh muscles were sore. I had a little irritation from body hair that was growing back. And of course, my asshole felt all stretched out and very tender. I wondered if it would ever feel tight again. I also wondered what the evening would hold. I couldn't imagine that it would be anything more humiliating and degrading than the previous evenings. I wasn't wearing a buttplug...

Crossdressing

Dressing Room

"Honey, how does this skirt look on me?" Dee asked as she swung open the door to the dressing room and stepped out of the dressing area. She spun around in the waiting area, causing the dress lift off her legs, revealing her bare legs and ass. Dee rarely wore underwear and never missed a chance to "accidentally" expose herself in public, particularly when I was watching. "I like this one better than the green one" I said as I stood from the small couch in the waiting area and approached...

Jaq enjoys both of us

We had known Dave and Maria for a while through our various clubs, unfortunately we had not played as a foursome. It was a Friday night at one of our swingers parties, Dave, Maria, Jaq and myself found ourselves chatting together. The wine had been flowing freely and the conversation was very much revolving around sexual desires.Dave went off for a round of drinks, this is when Maria confided that Dave loved to dress as a slut with Maria but was a little shy to take it any further. We explained...

Crossdressing

my crossdressing fun

We got into her the door was unlocked. He walked straight to her dresser and opened the top drawer then pulled out a pair of hot pink undies. It was a g-string with a cute little black bow on the front and back. He then said "have you ever wondered what it would be like to wear these kind of underwear instead of what we wear." without much thought I then dropped my shorts whitey tighties I grab the thong and put them on. My friend had I shocked look on his "i didn't mean let’s put then on"...

Three nights in London Night 1 Irene s transformation

I met Gabrielle at a music festival where I played with my band. After our gig, she complimented me on our show and we started to chat. She was over from the UK and was staying with friends in Amsterdam. I was impressed by this pretty redhead, dressed in a bit of a Lolita style with ultra black makeup, a cute red tartan skirt and huge boots over fishnet boots. We directly clicked and she started telling about her life in London. It appeared she was a professional corset maker. She showed me...

Crossdressing

My First Time

The sheer thrill of what I was about to do was bursting through my body. My nipples tingled at the thought and my heart was pounding in my chest. I pinched one of my nipples until it hurt, just to prove that I was not imagining it. I simply couldn’t wait to see Mark. Three hours to go before I would stand in front of him and let him touch me, caress me and fuck me if he wanted to. All I had to do was get ready. I showered, not once but twice, making sure that every part of me was clean and...

Crossdressing

All the Way Part2

When Michael stepped inside and closed the door, he gave Kathy the same kind of kiss as his wife had. He was quite an imposing man; short cropped blonde hair, very piercing pale blue eyes, a little over six feet tall and built sturdily, weighing somewhere around two hundred pounds. My heart skipped a beat when I took in the complete picture. Now I wondered how Kathy would convince the woman to get naked while her husband was right there. Donna gave me a hug and a nice kiss and then her husband...

Crossdressing

The Seven Dressing Sins Vanity

"To recreate this scene, you will need..." John tightened his calf muscles as he watched the young woman on the TV present an untidy scrap of cloth. "One white fishnet dress." He thought he knew her, somehow - something in her voice perhaps. He didn't know anybody with a crimson streak through her long blonde hair. And he certainly didn't know anybody who'd do a porn movie. The camera remained pointed at her wonderful breasts. They were small but very firm, and semi-aroused...

Extended Vacation Chapter 3

Cassie has her first full day as a woman as she continues her seven weeks living as a woman 24/7. EXTENDED VACATION Chapter 3 I arrived at my new apartment around 5 PM, and it took me over three hours to unpack and get organized. It was very enjoyable to move in and have a fresh start. I loved looking at my closet and all of my drawers as everything was for Cassie. My bathroom was exciting as well, as I had lots of make-up and accessories for being totally feminine. Despite the enthusiasm and...

Crossdressing

my first time

I’m 28 now. I have been interested in women’s clothing as long as I can remember. I can remember when I was around 7 my sister caught me trying on a pair of her panties that I stole out of her room, I don’t think she ever told on me about that. As I grew I was always stealing pantyhose, dresses, skirts and etc from mostly my family and my friends sisters. I wasn’t really turned on by guys, but when I would slide those sexy pantyhose over my legs, I would find myself fantasizing a friend...

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

I Was Wearing Panties When I Met Her

It started when I was sixteen. I guess that's how it works for everyone, right? The girl next door; a hot, college student who was the object of my dreams, was into community theater. We'd spend afternoons helping her with her plays. Sometimes she had the boys play female roles. She even dressed us up. I guess something about it just felt right. Something stuck.Of course, a grown man in a dress isn't socially acceptable. And it's not like I ever wanted to BE a woman. I just got a charge...

Crossdressing

High and Dry Part 3 You re Gorgeous

Affairs began to hit their stride between Emma and me after that Queen’s Birthday long weekend. We had spent much of the remainder of that weekend either in or around my bed: we made love a few more times, but much of the time was spent just cuddling up under my quilt. Eventually on the Monday I dropped her off at her mother’s house, our parting kisses taking even longer than ever.While her and her sister Amber’s living arrangements reverted back to fortnight-long stretches with each parent,...

Crossdressing

A guy is caught crossdressing by his wife

I have always been a cross dresser and enjoyed it. Maybe it was too much at times. I some how let the guys go too far with me. That is a different story. When I got married I put all my special clothes in the basement and lived a normal life. One day I was home from a trip early and found my wife was doing the laundry. There on the top of the pile were her pink thongs. I was taken aback and grabbed them and slipped them on and the warm rush of my past feelings came back to me. I loved the feel...

Night Trawling The Crossdresser

The streets of Pomona live two lives. Like maternal twins, they coexist in parallel, appearing as virtually identical to those merely passing through its old and storied neighborhoods. During the day, with the sun high overhead, myriads of people — whether they’re commuters traveling like drones or soccer moms distracted by their busy lives — they choke the streets in a constant pulse of life. Each person is absorbed by their own petty concerns, each oblivious to what is happening on the...

Crossdressing

A New Beginning Part 3

It’s been a while since I’ve written. For background, I’ve got a wonderful relationship with my wife Joan and an ongoing affair with my step-daughter Ellen. It’s possible since Joan’s job keeps her out of town for extended periods of time. Both of the women in my life have the same sexual tastes and to say things get kinky is an understatement. Ellen was very much in dressing me up from the start of our relationship. It’s something that Joan liked to do and I was all for it as the sex was HOT....

Crossdressing

Meeting Mistress Sarah

My heart pounded fiercely as I stood at the door to Mistress's house. I did not expect to be so nervous at meeting her again. After all I had known her for quite a while now. Mistress Sarah had been gracious enough to allow me back into her world. I was fortunate to fall under the control of such a dominant woman. She had moulded me into an obedient and submissive slave through the use of e-mail, texts, and online chat sessions. At the insistence of Mistress Sarah, the time had finally come to...

Crossdressing

Bookstore Bunny Gang Bang

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 an adult bookstore. Immediately upon checking into the motel, I got the urge to dress up in sexy...

Crossdressing

Cross Dresser Loves being used

I have cross dressed for almost fifty years. It started in the UK when I was eighteen, I had often read the various catalogs for mail order purchases and used to look at the women's lingerie pages where the ladies were wearing garter belts, girdles, panties, stockings etc., and I used to get hard and play with myself and jack off to the pictures.I was always fascinated at my older sister who used to wear stockings, garter belt, etc. and it excited me. One day when nobody was home, I went to my...

Crossdressing

Stage Ten Of My Journey To Becoming Joann

I was excited about the next soccer practice. There were no guys at the last practice due to Gurls Night. I was hoping Donny would be there this week. I stopped working at 4:00 so I would have enough to time to get ready. I went into the bathroom and filled my douche bag with a little over two quarts of warm water and special soap. I took off my shorts and panties before pushing the enema nozzle into my ass. I still get a hard-on as the warm liquid fills my bowels. I cleaned my face as I held...

Crossdressing

To the Rescue

The music was loud. The bar was crowded. Norm had a good buzz going, and hadn’t paid for a single drink all night. Actually, Natalie hadn’t paid for a drink all night, because that was the name he used – when he felt like offering it – on these little jaunts.He knew he looked good as a woman. Heads turned and men approached him relentlessly every time he dressed to kill and hit the town. There was no better cure for the sadness of a breakup than having a bar full of straight men hitting on...

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

My wife takes what she needs and wants

I'm a very lucky husband. I have an extremely sexy wife, who is open minded, and loves to please. If she has any faults, it's that she doesn't realize how sexy she is. At 37, she has extremely long red hair (which she jokingly calls stripper hair, but it's actually the truth because it's so sexy how long it is and how it falls against her backside), really fantastic legs, nice curves, lots of freckles all over, and some amazing breasts. Oh those breasts, that I not only love to enjoy but am...

Crossdressing

Tyrone s Crossdressing White Pussyboy

Submissive whiteboi becomes a sissy faggot pussyboy for his nigger master.It was to be a night of romance. My Nigger lover, Tyrone, gruntedas he pulled his glistening cock from my aching, cum filled asscunt. Hehad just shot a massive load of man slop into my steamy, grippingentrails. Our lovemaking had been a brutal affair, as it always is, which is just the way I like it. I am a subjugated fuck slave, nothing but a sissy faggot sperm receptacle for my dominant nigger lover.Tyrone is the envy...

Seducing Uncle Frank

This is a story that happened some time ago, when I seduced my Uncle Frank. Uncle FrankUncle 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 was quite wealthy.They had met in the early 1970's, and spent their wild and wonderful life traveling the...

Crossdressing

My Lesbian Lover

My wife was trying to come to grips with the realization that I cross dressed, with marginal success. Part of her plan was for me to meet in the Twin Cities with other CDs so I could have a ‘safe’ place to dress up, away from our small town. To be safe, I was to drive up, change clothes there, meet with my friends and then change again for the drive home. A good plan … a safe plan … but not one I particularly liked (so I changed it a bit!) Kim was a mutual friend who lived in town. Although she...

Crossdressing

Karren Gets Fucked and Sucked

Adventure in Nylon 3 Part 1 Karren gets Fucked and Sucked He was all dressed up in his finest outfit. Starting with the prettiest white lace panties he owned. A white lace teddy with attached garters, a built in under wire bra that was filled with breast shaped silicone pads to look and feel like the real thing. He covered these with a silky smooth full white nylon slip. His shaved legs were covered in lace embroidered, white nylons. He had on a striking hounds tooth check; two piece knit...

Crossdressing

My first time with a man

I had been into dressing in kinky little latex skirts and dresses for years. I loved the way they felt against my skin. Playing on my own had been enough until now, I had toys and vidoes to amuse me but the thrill of being fondled and fucked by a real guy was now too much to resist. I decided to try the online sex sites to find someone and find someone I did. He had looked at the pictures I had placed on the site and was bursting to get his hands on me, a thought that made me tingle with...

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

No Strings Attached Sweetness and Lace Chapter 20

I wake up the next day curled up against my beau's firm, muscular chest, and my manhood locked away again. Its morning stretch is uncomfortable with it being unable to become fully aroused, but I feel less frustrated after yesterday. Liam had made love to me, and we're both on the same page about where our relationship is going.After our lovemaking yesterday, we'd bathed together, ate a delicious dinner Liam had cooked, and then spoke for hours about what had transpired in the playroom. We'd...

Crossdressing

My Crossed Life Chapter 1 This is Jenni

Like many sixteen-year-old boys, I was at that age where I had moved on from department store magazine bra and panties pages to the pages of Playboy magazine. There was not much left to the imagination in these pictures, and I quickly became fascinated by the female form. As much as I admired the female body, I couldn't help but be drawn to their makeup, hair, and everything satin, lacy, and sexy that gave them that alluring look. I started imagining what it would be like to wear some of the...

Crossdressing

Forced to Dress II

This is a sequel to my first story, "Forced to Dress up!" For a couple of months I had been meeting Nancy at her house to dress when everyone else was gone. On this particular day my best friend, David, was away for weekend with his father and Mrs. Jennings wasn't going to be back home until late that evening. That meant an entire day to lounge around in women's clothes and act girlish. Why Nancy let me dress in her clothes I don't really know. She had her reason and I didn't ask for...

Pleasures at Dressing Manor 5

Pleasures at Dressing Manor - part 5 of 7 by PRIM The story so far: Young teacher Miles Johnson receives a letter from his pupil, Lyndon Blonding, 18, telling how his spiteful stepmother is keeping him prisoner and dressing him childishly. He takes the letter to his Headmistress, Alison Forceman, who secretly feeds Miles the feminizing drug Fem-Agra, so that he becomes addicted to girls' clothing and suffers embarrassing changes to his body, before accompanying him in his bid to...

The Dressing Room

My boyfriend and I had a date coming up. Lately our dates had been ending up with steamy sex, so I wanted to buy a sexy outfit and some new lingerie for our date. I had visited several stores, before I finally found a few things I liked. I wanted something sexy and just a little bit slutty. It had to be just right. I dressed with sex in mind when I left the house. I’m not a stick thin model. I have curves. Maybe more than most men would like, but my boyfriend loves having something to grab onto...

Quickie Sex

Quarantine Queers Part 3

Our weird Quarantine rules had been in place for two weeks. A few times a day, Paul and I would switch our flatscreen over to Pornhub and suck each other dry. Yeah, we told ourselves it was only because of the quarantine, just like I told myself I only sucked Paul so eagerly because I wanted him to do the same. But there was more to it than that…Since we were able to freely admit our desires, our tastes had gotten more extreme. Cross-dressing and trap porn became pretty common entertainment,...

Crossdressing

Taking That First Step A New Chapter Begins Part 2

September had arrived and Lance returned to high school for his final year. He still found himself attracted to and flirting with all the girls and not the guys. He surmised that it was only when he was dressed as Lana did his choices change. He couldn't see Cassandra during the week as he worked out after school and then went to his part-time job.He got home in time to join his family for dinner. Afterwards there was studying and homework that needed attending. They did, however, talk on the...

Crossdressing

How It Started

At twenty five and being a blonde haired blue eyed light skinned guy, I had little hair except on my head. So, it didn't take long to achieve the smooth feminine look that I wanted. Of course, I left some "down below" because I looked young and if I shaved it all off I feared looking underage. My blonde hair was long, during the week I wore it in a guy style. On the weekends it was different, it was curly and girly.So, I was preparing for my weekly encounter. I had my hair looking pretty and my...

Crossdressing

Confessions of a Ladyboy Part 1

I was eighteen and new in the boy's hostel. No one had wanted me at home. I had never known my father. I saw my mother go out with a different man almost every night ever since I was old enough to remember such things. She taught me some valuable lessons - how to be attractive, how to carry myself, how to be seductive, how to do my makeup.She always said, "You are such a cute boy, you were meant to be a girl."She caught me one day, dressing as a girl in front of the mirror when I was very young...

Crossdressing

Carolyn Makes Her Way Part 1

After tucking my penis and balls away, I started dressing with the basics: panties first, a sheer yellow thing, then my bra with the silicon helpers we girls so love and then a pair of black stay up stockings. Next, I stepped into a short green miniskirt which I loved primarily because of how it would reveal my bottom when I bent over and shot pool. After that came my blouse, a long sleeve silky cream colored number that I left the top two buttons open.Dressed now, I went to the vanity and...

Crossdressing

Carolyn Makes Her Way

After tucking my penis and balls away, I started dressing with the basics, panties first, a sheer yellow thing, and then my bra with the silicon helpers we girls so love, and then a pair of black stay up stockings. Next, I stepped into a short green miniskirt which I loved primarily because of house it would reveal my bottom when I bent over and shot pool. After that came my blouse, a long sleeve silky cream colored number that I left the top two buttons open. Dressed now, I went to the vanity...

Crossdressing

Caught crossdressing

The below is a true story so naturally names and places changed but the rest of it remains to be one of my memorable moments!!What seems like many years ago now when I finished university my then girlfriend Lexy and I went down to Cornwall to stay in her parents holiday home for the summer while we worked out what to do. To be honest at this point we both know that we aren’t “the one” for each other but I think we both had the same thought, see what happens over the summer and then make...

The Day My Secret Was Discovered

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 left for work, I went to our bedroom. There, I quickly stripped off my t-shirt and shorts. Glancing at the...

Crossdressing

Caught CrossDressing by Neighbour

I was enjoying a day at home doing some chores and cleaning. I couldn’t resist the urge to dress up, and was soon wearing stockings, high heels, garter belt, bra and g-string. I completed the dressing with full make up, wig and a Sexy satin French maids uniform. I put on some music, had a couple of drinks, and began to do vacuuming and the like. I was having a fun sexy time, dancing about, wearing the little maids dress. I heard my phone buzz and picked it up. There was a sms message from my...

Dressed for Disaster The Prequel

Dressed for Disaster: The Prequel (c) 2002 by Nom de Plume Pat Summers put his suitcases on the bed, and made a quick survey of his room. He noted with approval the full-length mirror on the back of the closet door, and he poked his head into the bathroom to inspect the bathtub and vanity. Not overly luxurious, but they would do. First things first. He opened his computer case and turned on his laptop computer, plugging the modem cord into the data port on the desk telephone....

Mistress Hannah s Pathetic Husband Part 9

When we returned home, we had a big late lunch because Mistress informed me that we might want only a light dinner and then a late snack. I spent the afternoon preparing as best I could for an unknown special night. This meant hair removal, nails, wig, makeup, enemas, buttplug, lotions, powders, perfumes, the whole works. When I finished, she laid out the clothes and jewelry I would be wearing. My eyes were drawn immediately to a brand new pair of lace panties for me. By the time I was done,...

Crossdressing

Mistress Hannah s Pathetic Husband Part 5

I was making progress as a slave but unkown to me, one of my stories helped Mistress Hannah see an opportunity for a particularly fun afternoon and a chance to help an old friend through a rough spot in her marriage. Several months of aerobic classes and feminization had increased my stamina and made me more comfortable when we spent our Sunday evenings out for dinner and as member/patrons at the theater club where I had been displayed on my coming-out evening. The pumping of my boobs and cock...

Crossdressing

Pure Innocence

It was an unseasonably warm Saturday and I decided to go out for a walk and clear my head. Instead of my normal guy garb, I decided to go out dressed as Aimee. But I was looking for a different look—totally cute and innocent which was not like me at all. I put on a little blue cotton dress, a pair of sandals, and donned a blond wig. The wig was long enough that I could put pigtails on either side. Even the light blue cotton panties I was wearing gave me the feeling of a young innocent female,...

Crossdressing

Two girlfriends have a couple over for a fun night

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, white top, and red high heels, and my cock was rock hard underneath my skirt, and my mouth was wide open at this...

Crossdressing

An Old Friend

Jerri is a close friend whom I have known for a long time. I was on an interview board for her when she joined the volunteer fire department. I was a little skeptical about her joining, especially since her husband seemed to be rather indifferent about it, but was overridden by the rest of the board. As time went on, she proved herself to be one of the top responders and an excellent Emergency Medical Technician. Eventually we became good friends and I even requested her as my lieutenant...

Crossdressing

A Nanny FEmtastic 9

A NANNY FEMTASTIC! Chapter 9 Thomas quickly pulled his hand from under my skirts, and stood up abruptly. “Fucking hell I don’t believe it!” he blurted out. Felicity was suddenly by my side. “What’s wrong?” she said. “forget it!” Thomas said, and stormed back inside, knocking over the table and drinks as he went. Bradley chased after him. I burst into tears and Felicity put her arm around me, and kissed me gently on the cheek saying, “Its ok Louise.” She handed me a tissue and I dabbed my eyes....

Crossdressing

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 go on like this, I had come very close to being beaten up when I was out and the chanting was just crazy. My...

Crossdressing

Felix becomes Felicity Chapter 4

FELIX becomes FELICITY Chapter 4 ..what a day I loved the tennis, Bradley was a pretty cool guy, but crikey what was happening! I only had something like 4 weeks left now so I was determined not to buckle under this, for my Mum and sisters sake. The next two weeks were quiet, I lounged around the house that suited me counting down the days. David continued to do our breakfast but work late. Mum pottered about. Jasmine continued meeting Thomas and kept coming back to say that Bradley had asked...

Crossdressing

Do it in Mexico

I live by the border to Mexico. I am a very low key cross-dresser . I moved out of my parents house at the age of 20 . Since I was financially O.k.. , like had a great job and was very independent. I was able to buy myself everything I wanted for cross dressing. When I turned 23 years old ,I decided that I wanted to go to Mexico and rent a house or apartment out there as a retreat or a getaway place if you will. This would be a great idea and an experience for me to dress up in public ,...

Crossdressing

Dressing at work

Having been crossdressing for sometime now I love the feeling of having fem things on when ever possible. I have started wearing things like garter belts, nylons and bras under my regular clothing. About a year ago I began to take some supplements to help grow breast and they are now a nice 36b and fill a bra nicely. As time has gone on I have even began to buy some clothes that even though they are womens they seem to go nicely with my regular clothes. As I have gotten braver I have also found...

She Males

Addiction to Dress

Addiction to Dress by Ellen (Revision 09/07/2000) Ed was on his way to an off campus books and school supply store to purchase some art supplies. The sun was out and the air really began to warm up. He took his usual route to the store today. The main reason was so that he could pass Marges' Bridal. As he approached the store front, Ed felt his heart rate go up. A twinge of excitement began to go through him. As he began to slowly pass the front window he saw a lovely white wedding...

The Making of Kairi Fox Part 2

For the next few days, it was safe to say my anxiety was through the roof. Every notification, email and slight noise from my laptop sent me into a frenzy of confusion and a little bit of horniness. Someone had been recording my dress-up sessions through my webcam. I had taped over it now and made sure that nothing could be seen. Everything I did online was careful, and I began using a VPN just for extra security. Sarina. Mistress, apparently. She already knew, though. Fuck.My days were wrought...

Crossdressing

Pleasures at Dressing Manor

Pleasures at Dressing Manor - part 1 of 7 Chapter 1: Who can help poor Lyndon Blonding? Dear Mr Johnson, I am writing this letter to tell you about my stepmother, Vera, and how she has kept me away from school for the past two weeks. I am not allowed out of the house; in fact I am imprisoned in my bedroom with the door and windows locked. Not only that, sir, but my stepmother has taken away all my clothes. I have to wear a little short sleeved white shirt and pale green...

The Party I Fucked

Phebe stepped out of the bathroom and pulled on my panties. Bill had been fun but she needed to get home and change into men's clothes to go to work. The wig, frilly skirt, stockings, blouse and wig would stay at home."Bye Bill, need to get home." With a peck on his cheek, Phebe rushed out the door to her car. Her ass was a little sore from Bill trying to fuck the shit out of her. Phebe had loved every stroke.My phone rang just as Phebe started driving home."Hey George, what's up?" "Hey...

Crossdressing

Pleasing Bill A Crossdressing Story 3

[/b]I woke up early the morning after my first day of being Bill’s live in slut. I got up to listen and hear my dad and siblings leaving for work around 7. I was going to wait for all of them to leave before I dress and go back to Bill’s at 12. I went to lie back down but before I could, I heard my mom call me. “James, honey. Can you come down here?” I didn’t know what to say a first. She probably wants to talk about how she saw me last night. I guess there was nothing else I could do but go...

Pleasing Bill A Crossdressing Story 1

One very long boring day in the middle of summer, i was home all alone, my parents were at work and my siblings out somewhere. I decided it would be a good day to dress up and have fun while i was home alone. I went to my secret stash of clothes i keep in my closet and picked out my purple lingerie. It consisted of a purple and black lace bra with matching thong and garter belt with black stockings. I put it on then went to get my cute blonde shoulder length wig, it fitted nicely as i applied...

Stage nine of my journey to becoming Joann

It was almost midnight when I got home from my foursome. When I walked into the house Mandy was sitting on the couch watching the television wearing a shear teddy with nothing underneath. She looked at me and said, “Where have you been all night young lady?” I answered, “Out with the boys, Sis.” “I hope you don’t mean what that sounds like.” I responded, “If it sounds like I had sex with multiple men at the same time, then that’s what it means. I didn’t realize Joann was such a slut.” Sis...

Crossdressing

Car Park

I finally got the nerve to go out in public dressed. I've been dressing in private for years. It started with panties, Some of my wife's, some of in-laws that have stayed with us from time to time.I finally got the nerve to buy some at a store. So exciting, looking at panties wondering how they will look on you. Took a while to find my correct size; I like them tight not no so tight I fall out of them. Some were so big they looked my something my grandma would wear. I now have collected a nice...

Crossdressing

Car Park

I finally got the nerve to go out in public dressed. I've been dressing in private for years. It started with panties, Some of my wife's, some of in-laws that have stayed with us from time to time.I finally got the nerve to buy some at a store. So exciting, looking at panties wondering how they will look on you. Took a while to find my correct size; I like them tight not no so tight I fall out of them. Some were so big they looked my something my grandma would wear. I now have collected a nice...

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

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 really big, thick cock, and the more I watched the more I found myself attracted to the guy in the scene and his...

Crossdressing

Taking That First Step Part 2

Lance's family was surprised to hear him up and moving at 6:00 AM. Saturday was his day to sleep in now that school was out for the summer and he didn't work on the weekends. They didn't question it and soon fell back to sleep as Lance headed to the master bathroom. He showered and then toweled off before heading back to his room.Once in his room with the door locked behind him, he removed the sexy lingerie that the stunning Cassandra have given him from its hiding place. Lance recalled how he...

Crossdressing

Curious No More

I began dressing in my sister's clothes. I would get so hard and excited when I felt the soft panties against my cock and the bra wrapped tightly around me. But my dress up time was always short. Now that I live on my own I have my own femme wardrobe and plenty of time to dress and perfect my makeup and appearance. The more I dressed and the longer I stayed dressed, the more I wondered what it would be like to be held closely by a man and feel his warm embrace. Soon I began to wonder what it...

Crossdressing

First Time With A Crossdresser Part 1 of 2

I’m Scott, 36 years old and recently divorced from my wife of 12 years. It was an amicable split with no kids to complicate matters. We sold up, divided everything two ways and went on our merry way. Our sex life was good and regular but a little boring. We stuck to the same three positions – missionary, her on top and spooning. I’d give her oral but she wasn’t that keen on going down on me and her facial expression when she was blowing me put me off asking for it! I’ve never needed more than...

Crossdressing

Jessie and the Office Girls

I spent the weekend trying to recover from the pounding that I received from Dan, Aaron, and Zach. I was their slave, and I had enjoyed it immensely. What I didn’t plan on was having all of my moans, groans, and enjoyment being filmed from twelve different angles, along with Dan telling me that he was going to share this video with our office mates. I was worried, yet anticipating what Monday would bring to me in the office. Come Monday, my ass was still sore from what Dan, Aaron, and Zach did...

Crossdressing

A Lifelong Love Of Lingerie

At the time I was sixteen, my mother was divorced and living with me, and she still worked and was gone until late in the afternoon on some days, so I would have the house to myself. I did not have access to porn until later, but there was Cosmopolitan magazine and other magazines which had the sorts of ads and stories that intrigued me, underwear ads, tampon ads - they all did the trick. I am still very turned on by the picture from the little pamphlet that came inside a box of tampons showing...

Crossdressing

Call Me Julie Part 4

Scott coaxed me out of the car and we walked the ten feet to the front door, he was practically dragging me while reassuring me that everything would be alright. "Kelly is expecting us, don't you worry about a thing." "She is expecting me? Dressed up like this? Somehow I don't think you are telling me everything Scott, if this ends badly I will be kicking your sweet ass," I told him. He chuckled as he opened the door and announced, "Kelly, we are here." Kelly replied from the kitchen, "Okay...

Crossdressing

Christina and Cheryl Part 3

I woke up naked being spooned by Christina. Her smooth arms held me tight against her. I turned around and woke her up with a kiss. She opened her eyes and kissed back before pushing my head down. I kiss down her body and slipped her pink panties off. I kissed up her thigh and edged closer towards her clitoris, this is how we spent most mornings. "No, my ass." I lifted her legs allowing me to lick her ass. Christina knew how turned on I got doing this, the humiliation of it. She pushed my...

Crossdressing

Hitch hiking Baby Doll Part One

I hadn't been in his cab for more than a half hour when the driver who picked me up, brought up the subject of sex to me."Last week, I had a guy and girl riding with me and they both liked giving me blow jobs. And, you know, if I closed my eyes, I couldn't tell the difference of which one was sucking me off. They were both excellent at sucking cock.""That sounds like you had a fun ride," I replied.The fact that I was a cute cross-dressing boy made the solution simple to me. My trucker was about...

Crossdressing

My Early Crossdressing

I started cross dressing around 12. At first it was knickers or tights. As I got older I started to get more serious with it. Just after I turned 16, I'd often go out round the streets round town dressed in full girls clothes. I'd always prefer going out late in the evening in winter, as I'd not pass many people and id normally only pass a few cars, some would slow down as I walked along the side of the road.One day I was home alone, my parents were away for the week and my sister was staying...

Telling Mom I m A Crossdresser Part 14 Back to the spa and a familiar face

Part 14: Back to the spaI'm sorry this story is a fair bit longer then my usual ones however I didnt want to separate thes and have another story with almost no sex in the first one so soon. Having said that I hope you enjoy my story and please read the whole thing. I promise you will not be dissappointed. I woke up the next morning lying next to mom in her bed. I was wearing a pair of white stockings and a corset and mom had her bra on. After Thomas had left Mom and I spent the night licking...

Crossdressing

I am Suzie

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 the work. Feeling the weight of it in my crack. I was thinking about nothing other then being the best whore...

Crossdressing

Satin lingerie

My sexy pink satin panties felt so good against my skin and looked great with black stockings and garter belt, my matching satin camisole top was so soft and I was gently creasing my pert nipples through the fabric. It was around 10pm and I was feeling a little bit tipsy after my bottle of wine The DVD was playing Cock in Frock and had some sexy clad shemales in compromising positions, god I love my nights in. I have always loved dressing like a slut and have now shaved all my...

Crossdressing

Is crossdressing addictive

By: AnonymousYes, it can be very addictive.Right around 2008, in the middle of the Financial Crises, I was going to school part-time, and working as a bartender in North Atlanta. I lost my job. The only place that I could find that was hiring was this Drag club in Buckhead. I didn't really want to work there, but I needed a job, and the manager offered me a great salary.I found out later that she assumed I was a cross dresser. This never came up in our interview, but it WAS a Drag club, and I...

Double dildo Please

In my mind, there are two types of closeted cross-dressers. One dresses strictly for themselves in the confines of their home or other completely private area. The second, ventures out into public or semi-public for the thrill of being dressed as a woman in front of others, but still keep their cross-dressing a secret from those who know them. Many in the second category, also engage in sexual activity. I fall in the enhanced second category. However, due to limited time and resources, my...

Crossdressing

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