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Confessions of a Sex Crazy Cross Dresser Part 6

Here are the next two chapters of Sandy's adventures Chapter 11: Photo Shoot and the Elevator Ride I slept great on Monday night after my craziest night of cross dressing. My body felt great as I slept in late. However, I had to admit, I felt like my ass had been torn up from Stan’s incredible cock. I realized now that almost all men wanted to get their rocks off with strangers. Stan and Bob were perfect examples, they wanted to fuck a girl or at least get a blow job. They were so happy they...

Tea party for a cross dresser

I decided I'd walk over to her place. It wasn't far and it was a nice day. Once dressed I picked up the bag and headed out the door. I arrived just before 8. She answered the door in her dressing gown. "darling" she said and we kissed each other on both cheeks as I entered. I stood in the hall. The flat had high ceilings. We went to the kitchen. We discussed proceedings over tea and toast. Showers were a must. I had a lot of shaving to do. That would take some time. There was one...

My neighbor blackmailed and fucked me for Cross dressing

I had recently moved in a townhouse unit in Oklahoma. Still trying to adjust to the new neighborhood, I was also doing my best to keep my hobbies a secret. You see, I am a cross-dresser by passion. But my new neighborhood is strictly catholic and I can imagine the uproar my fantasies might stir. My next-door neighbor was an old man in his 60’s. He looked younger and stronger than his age. But, my secret unfolded and the neighbor fucked me for cross dressing. Within a couple of days of...

Dress Like a Boy for my Husband to Keep Sex Life Active Free Sex Stories and Adult Erotica Stories

When you are married for 10 years, your sex life tends to get a bit boring. It is the same old missionary followed by doggy or little suckity-suck here and there. Sometimes, even the thought of having fun with a new partner, runs through your mind. But, itâ€™s all the same. You will spend the initial years of your relationship, discovering the body of your new partner and then it all goes back to where you left from. So, the question is, does that make it a wise investment? Well, in my head, its...

How I became centre of attraction for rich gay men Free Sex Stories and Adult Erotica Stories

Hello friends, my name is Ricky and this is the story of how I became a paid cross dresser two years back. It was during the Christmas holidays when I was in need of some money. I called my friend Kris and asked for his help. Though he agreed, he asked a favour in return. When I met him, he told me that his job was in danger and that the only way to save is by pleasing my boss. He told that his boss was a bisexual who had a thing for cross dresser. I used to dress like a girl at times but never...

The Crossdresser s Quiz

The Crossdresser's Quiz By Ricky I have recently been educated. After all these years of simply wearing frilly clothes and thinking them feminine I have finally found out the secret of how to be a real woman. And all because my car is a clunker that just passed 100,000 miles... It happened this way. As soon as the odometer turned over, every time I got in the car something else major broke down. Within 3 weeks I replaced the rear main seal, the fuel injectors, water pump,...

Cock sucking Crossdresser

When I was out on my own I started to buy a few things' mostly panties and thigh high stockings then a skirt and a blouse things that where ease to get to fit me. From there I learned to find my size in dresses and shoes this started to put my wardrobe to gather, but I still needed a wig and makeup so it was back online for more shopping, With lots of practice I became pretty good at putting on my makeup, plus doing my wig hair and a waste cincher I looked pretty darn good if I say so my...

Telling Mom Im A Crossdresser part 13 5 Missy Brings Home A Stud

I told Thomas all the details of why I was out this night and he loved the idea. He took one of his Viagra and he led me out of the bar. I felt a little embarrassed at all the cum leaking down but some of the cross dressers were just smiling at me like they were saying “you go gurl!” which made me a little proud. Thomas followed me in his car until we got to my place and I took him by the hand until we got in the door. When I walked in I heard a thumping upstairs and asked Thomas if he would...

Telling Mom Im 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...

Party Surprise First sex as a Crossdresser

This is a work of Fantasy. I hope you enjoy.Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly she was jealous of my legs. She was a petite sexy woman and we were almost the same size but I still had my own stuff that I’d secretly obtained from eBay and op shops.I didn’t consider myself bisexual,...

Telling Mom I m A Crossdresser part 13 5 Missy Brings Home A Stud

I told Thomas all the details of why I was out this night and he loved the idea. He took one of his Viagra and he led me out of the bar. I felt a little embarrassed at all the cum leaking down but some of the cross dressers were just smiling at me like they were saying “you go gurl!” which made me a little proud.Thomas followed me in his car until we got to my place and I took him by the hand until we got in the door. When I walked in I heard a thumping upstairs and asked Thomas if he would...

Crossdresser to Fuckable Mannequin

I have been contacted to join the cross dressers pop mannequin society. Ok I have dressed for years but never been involved I such a thing. The day arrived and I was apprehensive but awoke with an unusual great hard on. After coffee I shave all over and greased my pussy. A 9 inch dildo opened me up. Slipping into my silk G-string, and matching bra I felt good. Applying glue to my chest I quickly poisoned my size D breasts in place and pulled my lovely Victoria's secret bra over them to...

The hottest crossdresser

I was drinking with my friend Curtis one night as his girlfriend Jane was out with her friends having some drinks. The topic turned to cross dressers, as I had had let it slip, that one time I mentioned to him, I had dressed as a girl a few times when I younger in my moms clothes, and it felt great. He asked if I had any girl’s clothes at home that I wear from time to time, which I reluctantly said yes. With that Curtis asked if I would wear some of Jane’s clothes to see how I looked. “Sure,...

Picking up a Crossdresser in a Bar

This happened about 20 years ago. The basic events are completely true, but in those days I drank a lot, so I don't remember many of the details. For the purposes of a good story, I made up a few things to fill in the blanks in my memory.It was a weekend, and my wife had taken the k**s to visit her father 400 miles away. I was alone at the house, and I knew an opportunity when I saw it. At the time we lived in a small city, and there was a gay bar in town that advertised a weekly drag show on...

crossdressers first time with a guy

hi, im new to this. this happened about 3 years ago now.I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from this simple thought I became massively aroused and started trying on her underwear, make up, and even a wig that was in the apartment. soon enough, I was looking like a slutty crossdresser.I thought enough...

My first Crossdresser Part One

When she walked in to the restaurant I knew I was in trouble. It was the end of three long days at the convention and I was tired. I had come down to the NASCAR Cafe for a sandwich, mainly because it was the only bar in the Sahara that didn't have video poker...I lose a lot of money playing video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's strutting toward a table.Convincing she was not, a crossdresser without question. But pretty, really...

My hottie night with two crossdressers

When I was 27 years old and single, I really liked going to shows at night, to nightclubs, especially when it came to beautiful women. One day I went to a transvestite show and was fascinated.These men dressed as women groomed themselves more than any of the women he knew; her wardrobe, her makeup, even her movements, were more feminine than any woman's.I started visiting an exclusive nightclub, where every night there were transvestite performances imitating well-known artists and singers.I...

Confessions of a Sex Crazy Cross Dresser Part 11

Hi All, it required a couple of re-writes to make it better. The final chapter of Sandy’s adventures in book 1. Please let me know if I should publish book 2 Chapter 21: Nikki’s Night and Sandy ’s Night to Remember I finished shaving Nikki spending a lot of time shaving her pubic hair. I made a small heart shape right above her clit and took off all the rest of her hair. When I finished shaving my new love muffin, I took a shower. When I was dry we got dressed together after a couple more...

Bi Cross dresser that s me part 2

A week later Chris and I met to go cloths shopping. We met at a coffee shop in a town a hour drive from me. She greeted me with a warm hug followed by a deep kiss. Our obvious age difference drew some judgmental stares from a lot of the other patrons. Chris sensed the fact that I was uncomfortable. She whispered in my ear "If only they knew all of the cum I licked from your ass". We grabbed two coffees to go and headed out."So Eric said I needed to get something kinky to wear the...

Fun with a cross dresser

I had a really good experience with a cross dresser yesterday. A mutual friend had recommended him after enjoying his services so I got in touch and he immediately responded by inviting me to go and meet him. It was most enjoyable. I have never been with a CD before but he seemed okay. He is late 50s and very slim. It was really quite strange. He came to the door in a dressing gown and invited me into the lounge where he explained how he had got involved in all of this by dressing up in his...

Telling Mom I m A Cross Dresser Part 19 Christmas Special

Christmas Special It was now around Christmas time and I couldn’t have been happier. Any other year we would have had family over which meant I had to dress normal because the other members of our family still had no idea or at least weren’t talking. However this year we had no plans at all, our cousins were off on vacation to Mexico until new years, my grandparents were not in a visiting mood because of some family matters that keep us from talking to each other at the moment and others we...

Me Mom and the Hair Dresser

Growing up as a only c***d I was smothered by my Mother, I don't know if it was normal ,but at 14 she was still breast feeding me,bathing me, and sharing one bed . I was a very shy boy, we moved every year so I was always getting beat up at the new school. I had no thoughts until my 14th birthday. It's funny how these things change so fast,I had received my first computer, I was looking up and typed in the words "Mother and Son" I was directed to a porn site one of the pictures was of a mature...

Step Mother s Sex Slave Cross dresser blackma

My heart pounds as I tip-toe across the soft, pink carpet in my parents' room. I'm home alone. My stepmother's lingerie collection awaits.A floorboard creaks as I make my way to the dresser. I'm facing my worst nightmare--getting caught playing with Ann's lacy undies. But I'm totally hooked on wrapping myself in her silk and lace. I decide to move forward. The risk adds to the adrenaline rush.I stretch out my fingers to grab the drawer's brass knobs. The sensual pleasures of cross-dressing are...

Auto Ride Made Me A Cross Dresser Whore 8211 Part 1

I’m a male, and cross-dresses occasionally in private. After cross dressing I get hard and then get off rubbing my dick against bed. Sometimes I post my cross-dressing photos online and get excited by comments and chats. I fantasizes about being seduced/forced to cross-dress and made to serve like a whore by dominant stranger(s). I’m darkish brown, lean. Has little hair on my upper body. Thin. Have slender arms. Soft face. And thick lips. And finger thick but long. My butt is rather fine and...

Confessions of a Sex Crazy Cross Dresser Part 11

Hi All, it required a couple of re-writes to make it better. The final chapter of Sandy's adventures in book 1. Please let me know if I should publish book 2 Chapter 21: Nikki’s Night and Sandy ’s Night to Remember I finished shaving Nikki spending a lot of time shaving her pubic hair. I made a small heart shape right above her clit and took off all the rest of her hair. When I finished shaving my new love muffin, I took a shower. When I was dry we got dressed together after a couple more...

Confessions of a Sex Crazy Cross Dresser Part 3

Part 3 of Book #1. Chapters 5 and 6. Please review and let me know if you want moreChapter 5: Da’ Place Adventures Sunday that week was definitely going to be a day of rest. After all my adventures on Saturday including a coast to coast airplane flight, I was exhausted. Collette called me and asked me if I wanted to get together tonight and I asked her for a rain check. I ran some errands during the day and late afternoon I spent watching a football game on my television and around 6 PM when...

Auto Ride Made Me A Cross Dresser Whore 8211 Part 4

Thanks for the nice feedback I received for this series about a cross dresser. If not for them, I might have discontinued this as I was making progress at an agonizingly slow pace. Apologies for the delay in the update. I am sending the next part, so for the first time, I sending two parts together. I also have some plans for another 2-3 parts of Rakhi’s journey and her slow conversion into a whore. I will start right from where we left off. Please read part three and parts before that to find...

Cross Dresser Fuels Feminine Passion In Sai Now Sindhu

Hi, My name is Sindhu (using a female name). Here, I am going to write about how I am smitten by my girlfriend’s brother and turned from a straight guy to a dick-loving cross-dresser. My girlfriend and I started living together after both of us got a job in the same city. Both our families knew about this, and they were cool with us. We were happy together; we were enjoying our life to the fullest until her elder brother came to stay with us and took me to a fantasy world which showed me how...

Cross Dresser Fuels Feminine Passion In Sai Now Sindhu

Hi, My name is Sindhu (using a female name). Here, I am going to write about how I am smitten by my girlfriend’s brother and turned from a straight guy to a dick-loving cross-dresser. My girlfriend and I started living together after both of us got a job in the same city. Both our families knew about this, and they were cool with us. We were happy together; we were enjoying our life to the fullest until her elder brother came to stay with us and took me to a fantasy world which showed me how...

Crossdressers in a bisexual sex bar gang bang

I'm sitting in a crossdresser's sex bar – it’s dark. My companion Fifi is wearing only a pair of sheer silk panties in light blue, stocking and suspenders, and a pale blue matching corset that pinches his waist. His balls peak out of the tight panties. I’m wearing silk patterned stay-up stockings in black and a scarlet and black thong. The string of the thong rubs against my sensitive asshole and the soft skin of my ball sack: it’s a turn-on every time I move.A group of men and women approach...

A crossdressers first time fantasy

Im not an author in any way but I would like to tell you about my latest crossdressing adventures. I have been crossdressing for many years but maybe only twice in a year when the mood took my fancy and only ever indoors, the feel off nylon on my legs would get me very aroused and looking at my self in the mirror wearing high heels and a very short skirt had my cock pumping and I always had an intense orgasm, but over the last few years it has became more frequent and not confined to indoors...

Craigslist crossdresser

It finally happened. I got a response! I’d been corresponding with him on Craigslist, but then suddenly Craigslist personals were banned. I tried to reply to the Craigslist generated email that I thought was his, but I’d deleted all of his email’s in a moment of weakness. Now I had no way to get in touch with him. He’d posted about hosting crossdressers and providing a safe, relaxed place for us to fulfill our fantasies. He said he would be gentle. I’d told him who I was, that I liked to wear...

Crossdressers first gay encounters

I had met Steve thru a gay dating site, we exchanged messages over a few weeks and then finally agreed to meet. I was very nervous on the way over to Steve's for two reasons. One was it was going to be my first gay encounter. The Second reason, and one i had only agreed to after Steve's insistence, was that i was going completely cross-dressed. I'd gotten dressed at home as Steve wanted. Putting on a satin and lace garter belt which i attached to lace top suspender stockings, then a lace bra...

crossdressers first blowjob

had been a private cd for years and along with that secret I always wanted to give head .. but always to nervous . I used to be a long distance hgv driver and park up at night it what I call , naughty laybys . we all know the sort . did see quite a few things going on in them . especially single men turning up with hard cocks wanting some fun . most nights I would get dressed up and climb out and walk up and down and seeing if anyone saw me , then quickly run back to the lorry and hide . it was...

Xdresser Housewife Roxys daily chores while wife i

Well i must be the luckiest guy in the world ,my wife earns all the money so I stay at home to do all the house work and cooking .Now I've always wondered what it would be like to be a girl because women to me are so powerful when they are hot and sexy ,a women can get what she wants when she wants without even speaking as long as she has a sexy pair of platform heels on with a tight micro mini and a great set of tits that's enough to get anything from anyone ,if that isn't power what is ?So...

You Always Sleep With Your Hairdresser Don t You

I sleep with my gardener as well. I hadn’t really thought about it much until we moved locally about a mile to our present area. The new garden needed a lot of work and effort put into it to change it from wilderness to respectable. Me, I just like pottering, my wife likes ‘gardening’ as she puts it. The family joke started when, early that spring, I was doing some of the heavy work Jan couldn't manage. It was early evening and I was on my own out the front of our plot. It’s a reasonable size...

Sherry got fucked by the Shemale hairdresser Shemale Sex Stories

Living in the poshest parts of New York, Sherry was perfectly happy with every aspect of her life. She was ambitious and had a great job. She earned enough to lead a luxurious life in this part of the city. The only trouble was her hectic lifestyle and how it left her with no time to date. Her last breakup was rather messy. It has been three months since she broke up with her boyfriend. The only thing she misses now is the sex. She was not much into flings and one-night-stands so finding a...

You Always Sleep with Your Hairdresser Don t You

I sleep with my gardener as well. I hadn't really thought about it much until we moved locally about a mile to our present area. The new garden needed a lot of work and effort put into it to change it from wilderness to respectable. Me - I just like pottering - my wife likes 'gardening' as she puts it. The family joke started when, early that spring, I was doing some of the heavy work Jan can't manage. It was early evening and I was on my own out the front of our plot. It's a reasonable...

The United Kingdom of Zoo A fake BBC documentary series s3e10 Stacy 44 hairdresser from London

Series 3, Episode 10: Stacy On one side of the street a row of pre-War three-story buildings – shopfront downstairs, residential apartment/flats above. On the other side of the street, modern four/five level office buildings, and an old train station with a sign outside that reads, “Welcome to Enfield Chase”. We’re in North London to meet our next subject, and she’s a subject who’s worth meeting. Back to those shopfronts – one in particular – Hair By Hottinger. A modest hair and beauty...

Confession and testament of a crossdresser

Italy, september 2011. Sorry for bad english, I try to write correctly but don't know if I did. From tonight, I was a crossdresser. I'm been crossdresser from 12 to one day before my 27th birthday. Irony. I begin to have an answer to the question: "What feel girl?" Yes, a simple question. What feel girl when wear panty, tights, dress, skirt? What feel a woman in heels, purse, with her hair falling down the shoulder? What feel a teenage when begin to make up herself? When wear lipstick,...

Me and my milf hairdresser Sophia

My name is Jake, I’m 19 years old and this is a story about me and my hairdresser Sophia. Sophia is a 38 year old brunette, she’s married to Ryan and they have an 8 year old son. She has been my hairdresser for a few years now and I’ve always had a thing for her. She is a self-employed hairdresser with her own hair salon at home. This story took place last week. On Tuesday I called Sophia to make an appointment to cut my hair. She told me that I could come around 7 PM on Thursday.

The hairdresser shop opens for us

On Saturday evening, we had been invited to a party by some old friends.My sexy wife Ana wanted to be sexier than ever, so she arranged with her hairdresser to open the shop late, so my wife could have her hair done that same evening.Anita had been going to the same hairdresser for over many, many years. She was a young nice girl, in her late twenties; she had recently married.Her name was Carla and I had always had the hots for her; but she was too young for me; so I just dreamed about one day...

Me and my milf hairdresser Sophia

My name is Jake, I'm 19 years old and this is a story about me and my hairdresser Sophia. Sophia is a 38 year old brunette, she's married to Ryan and they have an 8 year old son. She has been my hairdresser for a few years now and I've always had a thing for her. She is a self-employed hairdresser with her own hair salon at home. This story took place last week. On Tuesday I called Sophia to make an appointment to cut my hair. She told me that I could come around 7 PM on Thursday. It was 6.35...

xdresser roxxi s mistress is my wifes sister

For a long time now i have wanted to see a mistress but as i am married its hard to get the money to pay for the services of a professional so i have not been able to fullfill my fantasy that was until last week. The adult store i go to to get all my sex toys has a billboard and people put up a picture and what they are into sexually .Its basically so like minded people can meet to explore there sexuallity . I went home took some sexy...

Xdresser Housewife Roxys daily chores while wife i

Well the best fuck I've ever had and continue to have all started when we intalled a pool in our back yard .Once the pool was in the pool shop sent over a young guy to set up the pump and show us how to use it ,as it was a Saturday my wife was home and she was in a bikini looking very hot. Well in walks this 6"5 very toned very sexy black guy ,when I say sexy he is the sexiest guy I've laid my eyes on and the body his arms were huge ,not one ounce of fat ,man the thoughts going through my head...

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...

outside the hairdressers

My wife had gone to the hairdressers, I was sat round the corner in the car waiting for her, it was opposite the employment office, where all the screbs go to get money off the state, it was a run down area but I never felt unsafe, as I was sat there I reached for a cigarette, as I opened the packet a girl was next to the car, she said "Do you have a spare cigaretts", I said "Maybe".She was around 20, long brown hair, slightly chubby, wearing a trakkie bottom and a white top. She said "I really...

Private Ariana Van X Paola Hard Horny Hairdressers Enjoy Interracial Threesome

Ariana Van X and Paola Hard have both come to Private Specials, Happy Ending Hairdressers for their www.private.com debuts and after a rough patch with her man Jesús Reyes, Ariana is happy to spice things up as she calls in co-worker Paola for a helping hand. These two babes are the definition of sexy, one blonde, one brunette, a dream duo, and today the lucky Jesús will find out first hand as they treat him to some incredible deepthroat, tit fucking and pussy pounding action that has them both...

The hairdresser

The place I used to work at last yr had a hairdresser that came in on a regular basis to do the older ladies hair , I noticed her from the word go as she was such a sexy little thing, about 5” 1 and blonde with a sweet little figure and a lovely set off boobs, a little older than I was but at the time I didn’t know by how much, over a few weeks and a little small talk I asked her if she would like to have dinner, and with a little persuasion from a colleague she agreed, I made dinner and we had...

Lockdown Hairdresser

Like most self-employed people Becky was struggling as a hairdresser during lockdown. No clients meant no money, but the bills didn’t seem to stop. She’d already resorted to cancelling every subscription she had and had even sold her TV on eBay. But she was still short of cash. At twenty-six years old and living the single life she had no one to help with the bills.Out of desperation she’d texted one of her clients to see if he needed a haircut and didn’t mind breaking the lockdown rules to...

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...

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...

Jaq Invites Crossdresser Over

Anyone who follows our adventures will know what type of lifestyle we lead.A short while ago Jaq got chatting to a crossdresser online. It turned out that he only lived a short drive from where we live. Kieran was twenty-two, his pictures looked amazing. Jaq asked me if she could invite Kieran to visit, an offer that I could not refuse.All was set for the Friday evening. To say we were excited would be an understatement. Jaq and I showered and dressed. Jaq looked amazing as always in a very...

Milwaukee Cuckold rsquo s Wife and the Crossdresser

Judy used several sites over the years to find her friends with benefits. She never tells me until afterwards what she has done. It’s rare she tells me anything in advance. One day she advised me the k**s were at my parents and she was entertaining that night and I would have to stay in the family room. My curiosity was getting the better of me.She went and took a shower and asked me to come in and shave her pussy. She had me paint her fingernails and toenails. Once she was ready she put on her...

Crossdresser for mature couple

I am a bi crossdresser....love some pussy or cock. I registered on an fabswingers looking for a meeting with similar people.I was actively looking for an older couple to have some fun with. To cut a long story short, I finally got talking to a guy called Bill. He and his wife could entertain a gurl like me for a fun filled evening, if I was game. We both had a list of dos and donts for the night and we went over a few ground rules etc.I was to be their maid and waitress for the evening. They...

A Crossdresser s Night in the Park

Last night I was on line in a crossdresser chat room where I was talking with Master Brian about me being a pain loving, submissive, bisexual crossdresser who was looking a master to use and abuse me. As we talked Master Brian asked me if I was dressed as a woman while I was on line with him. I told him that I was and then he asked me what I was wearing. I told him that I was all dressed up wearing a black silk mini skirtwith a black stretchy lace blouse. Master Brian then asked me what I had...

Teenage crossdresser

Here are the usual disclaimers this story is for adults only if you are viewing this andare not 18 years of age or older please close this page immediatly.There is no cross dressing in the story but this is how I began my transformation fromregular boy into cock suckking teenage crossdresser.We were having a really hot heat wave. i meat with my older brother (wear red shorts, and a black T-shirt) wanted me to get out of the house and off the computer so she suggested a movie. I felt wierd going...

crossdresser s 1st time

hi, im new to this. this happened about 3 years ago now.I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from this simple thought I became massively aroused and started trying on her underwear, make up, and even a wig that was in the apartment. soon enough, I was looking like a slutty crossdresser.I thought enough...

mature crossdresser 18 year old PART 1

Myself being a fulltime crossdresser and wear mini skirt and dresses all the time an high heels. A few weeks ago some new people move in across the street from me to be extact it was a woman and her 18 yr son.I talked to her few times and she was very nice and in our talks asked her if it bother her that i was a cd/tv she said nope. Well after couple weeks we became good friends and found out her son was shy and kind of a nerd. One day she came over to me and was little upset over something she...

Crossdresser Got Caught By The Neighbor

Hello readers, my name is Rajesh, a 24-year-old guy who likes to dress like a girl. I am in Australia now. This story will tell you how a crossdresser got caught by a neighbor and had to do whatever the neighbor ordered. His name is Roy (name changed), he is 6’1 height with a well-built body, and he is in his late 50’s. I recently had to move to another unit as my old unit’s lease got finished. On a Friday morning, I was leaving for my office. I saw an old man (who lives in the next door unit)...

The hairdresser

This happened in 2010Donna used the same hairdresser for over ten years. She was an Indian girl, really pretty and only recently married. She's called Gina, 30 years old, 5'5", thin with dark hair and extremely pretty. As Donna wanted her hair doing for a party we were going to Gina offered to open her shop late so she could have her hair done the same evening.Friday came round quickly, as I dropped Donna off at 6pm, the town was quiet and there was no-one in the salon, I told her I'd be back...

Girlfriend s Hairdresser

“Look, honey,” proclaimed Kamron as he held a mirror in front of his client.“I like it,” she declared with a smile. “How much,” she asked.“Fifty-five,” the five-foot-nine-inch big booty effeminate hairdresser replied.“Alright,” she said digging through her purse. “Oh damn. I left my billfold in my other purse. Do you mind if I get Tavares to drop it off when he gets off work,” she inquired referring to her live-in boyfriend that worked at the auto parts factory in town.“Yeah, chile. That’s...

Hairdresser Lesbian Experience

After a short summer vacation with too much to do, I thought I'd get my hair done before the school doors open for the year. One thing, one project, one crisis lead to another and I just couldn't get to my usual hair stylist in time. I called three days before school started and she was booked solid, right through the following week. So out of desperation, and with my eyes closed tight, I prayed that things would work out as I, with great hesitation, opened the heavy metal door of this new...

Hairdresser g f

One of my girlfriends after my divorce was a hairdresser, very useful in more than one way ! Been going out for a couple months , fucked a few times, all going well when I asked her if she cut cut my hair , “no probs hun” was her reply . So next evening after work I had been invited over for tea and to stay , all or offspring were staying at with partners so a free night . On arrival at hers , the house smelt lovely of a full roast dinner , her kitchen table laid with cutlery and her barbers...

Private Vasilisa Lisa Teen Hairdresser Addicted To Anal

Today on www.private.com, we introduce you to Vasilisa Lisa, a sexy teen hairdresser with a beautiful tattooed body who has come to Private Specials, Anal Chicks ready to go the extra mile to satisfy her customers. Getting the Vasilisa treatment today is the lucky Andrew Fire, and he soon finds out that this sexy new girl is just as skilled with her tongue as she is with scissors. Then enjoy this young debutant’s incredible figure in action as she goes on to take a hard and deep anal pounding...

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when she stood up. A box fell from her hands and onto the floor. Being the nice guy that I am, I picked it up...

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...

my life as a sissy crossdresser

it should be noted that i did not ask for this disposition to crossdress, rather it was presented to me quite by accident. circa 1958...grade school PTA fashion show. PTA fathers were asked to put on a fashion show dressed as their better halves. my dad was right in the mix. I remember he wore some mid calf, grey business suit w/jacket, tan stockings and black heels. i remember this because he practiced dressing days before the show. he wore some makeup and a wig. not very passable, but not...

CD crossdresser daughter rsquo s bitch

Note : This story is completely fictional!How did I end up like this? On my hands and knees dressed in just sexy stockings and suspenders and a lacy corset, my face in slutty make up, my lips wrapped around my daughter's boyfriend's cock while my daughter herself rammed an eight inch strapon up my arse. The worst of it was, humiliated though I felt, this was really turning me on. This is the story of how I became my daughter's bitch and how I came to love it.I suppose I shouldn't have let...

Crossdresser to Trans Escort Part 3

This is a continuation of my Crossdresser to Trans Escort series.After my first fuck for money with the restaurant owner, things escalated. I arrived at work the next morning wearing a pair of black trousers, black blouse and flat ballet shoes. The owner called me into the back office before we opened up for the customers. He was sitting behind his desk wearing a tight black t-shirt which showed off his tanned skin and bulging muscles. 'I really enjoyed our transaction last night' he grinned,...

Crossdresser in Love

I woke up with my hands bound, my mouth gagged, and my ass plugged. The bed I was on was comfortable enough. This was just a reminder that these parts of my body were no longer mine to do with as I pleased. For tonight would be my wedding night. For months we had planned things out. Picking out a dress, a place for the ceremony, all the things that brides do with their future husbands. But for me, it also included a regimen of hormones to complete my becoming as feminine as can be for my man. I...

Hitchhiking teen crossdresser

It was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter, I had my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to...

Room 209 First Sex as a Crossdresser

crossdresser – trans – interracial – lgbt – first time – virgin – black cock – crossdressing – natural tits – braI've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a k** and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight...

My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or...

Crossdresser Turns Gay To Seduce His Tailor

Hi all! I am a family man with a loving wife, but she doesn’t know about my crossdressing. It just so happened that she had gone to her mother’s place during her pregnancy, and I got ample time for my crossdressing. I did all of my shopping on Myntra and bought myself some nice soft satin sarees, dresses, gowns, tops, high-heel shoes, a makeup kit, perfumes, and loads of bras. I was waiting for the delivery like a curious kid waits for their birthday gifts. Finally, the day arrived and the...

olderman and mature crossdresser part 1

It was just a normal friday day so I went to the store to buy some food for the week.I wore a jean mini skirt and pink t-shirt and tan pantyhose with my 3"heels and make up and all. As I made my way down thru the ailse I notice a older tall gray haired slim man following me.Well I gave him a couple bending over shots and eye contact.I made my way to the check out an seen him in other line.I finshed checking out when I got outside to load my bags in my car he was parked next to me.He spoke to me...

My first time with another crossdresser

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my brother and sister. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer...

Crossdresser wanting some dick on the road

I`ve been crossdressing since I was 20 years old.One of my favorite things to do is get all dressed up in womens clothes and drive around on the open road.Several years ago I was mad at my ex wife for doing some stupid shit with our checking account and we were split up for some well needed cooling off time.The more I got to thinking about her stupidity the more I got to smoking some pot and drinking a few mixed drinks to get the crap off my mind.I got pretty stoned and decided to get dolled...

A Crossdresser 8217 s Life

Hi! This is my first story on ISS so don’t be harsh on me. This isn’t a real story, but a fantasy which i am going to share with you,though the characters are real. I am a boy(21)(crossdresser) doing my engineering in Bangalore in a reputed college. I stay at one of my fathers friends house, his name is Rajesh. His first wife died due to cancer so he married again. His new wifes name is Rajni. Rajni, in her 30s, is a damn hot woman with a plus size figure. Now lets move on to story… Initially i...

Telling Mom I m A Crossdresser Part 2 The Adult Store

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived. It was just past 9am when I heard a fumbling at the door, my mother had walked in with her heels in her hands and her clothes hanging loose...

Danni The Crossdresser First Time Sissy

by - sissy debbie This is a true story about what happened to me after graduating high school and how I became a sissy for woman who was nearly twice as old as me. --------------------- The summer after my senior year of high school a neighbor asked me to look after her house and her cat for a week while she took a trip with some friends. Her name was Heidi and she was an attractive woman about 38 years old. She just wanted me to stop in and check on everything a few times. I...

Nenu Crossdresser Nunchi Gay

Hi, na peru ajay. nenu tenth class ki vachinappatiki naku crossdressing alavatu ayyindi. enduko emo telidu, kani adavalla laga chira, jackettu vesukovatam istham. mukhamga Bra and Panty. ma inti venaka oka portion lo vunde oka ammayyi thana battalu vutiki bayata aresedi. ala aresina vatilo thana Bra lu kuda vundevi. mamuluga avi sayantram avi tisesedi. kani oko sari marichipoyo emo battalu tisedi kadu. ala tiyanappudo leka oko sari Valla bathroom lone vadilesina battallono (valla bathroom...

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when she stood up. A box fell from her hands and onto the floor. Being the nice guy that I am, I picked it up...

Crossdresser ke saath maza

Hello frnds.How is everybody.I recently got another hot encounter in July 2008.It happend at my sis home.Both my sis and her husband work for an MNC.They had recently employed a new maid.They were supposed to go to Pune for some seminar from their company.Since this new maid is new in town and has nowhere to go so my sis said me to stay at her at home so that maid will not face any difficulty.i said ok.I understood the problem and said ok for the proposal.So i reached her home on the day on the...

CL Memories 1 Crossdresser True Story

I used to get a lot of fun out of CL. I'll post some short stories about some of my experiences there. I sure do miss it. This happened about 10 years ago. I was divorced and living alone, and playing whenever I got the hots and had a good opportunity.I checked CL one weekend night to see if there was any fun to be had, and found a post from a crossdresser visiting a nearby city and looking for company. She (I'll use that pronoun here) had a room in a local motel for the night. I responded to...

Auto Ride Made Me A Crossdresser Whore 8211 Part 5

Except for some dirty and humiliating ones, most of Raghav’s dialogue will be in English in this part about the crossdresser whore. I thought that it is easier for me than translating each of the dialogues. The ride home was uneventful. I just sat dumbfounded in the back seat while Ragahv just fled the auto fast. In a short time, we reached my place. I picked my bags and climbed the stairs. Raghav followed me, carrying another small bag. Where did he get it from? I am sure he was spotting a...

The Avon Lady

The Avon Lady by Sheila Anne Morgan The layoff of six hundred workers was devastating in this small Southeastern town. The plant was the largest employer in the area where jobs were already scarce and now it was closed. David and Lori had bought their house a year earlier when everything was going good, before the company sold out to the big conglomerate that announced they would be closing the plant and shifting the...

Programming Conflict

Programming Conflict by Trish "So what you're saying is I'm dammed if I do, or we're dammed poor if don't!" "Er, yeah," Sue said, trying not to press me. Sue knew that I was just as aware as she was that if I played along with the plan, we three, or rather our 'hobby' cum burgeoning computer games company would be very handsomely rewarded. We were talking real money as well, not the couple of hundred pounds or so we had occasionally made selling our games at computer fairs in...

Jacqueline s interview

Jacqueline's interview by mya fantasy story description in this story a 21 year old proud and confident crossdresser named jacqueline agrees to be part of a research study being carried out by a psychology professor named chris. This is a complete transcript of the interview consisting of over 30 questions. Note: the interview questions are in upper case text and were written by a human (me) using the pen name mya fantasy. The answers are those provided by chatgpt without any...

Whores And Pimps Part 1

Whores and Pimps – Part I By Michele Nylons Malcolm was a middle manager with a small business in a large city. Malcolm led a pretty boring life, he was in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm had a few girlfriends over the years but never anything serious, he kept himself to himself and rarely socialised outside of a small circle of...

Whores And Pimps

Whores and Pimps - Part I By Michele Nylons Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm had a few girlfriends over the years but never anything serious; he kept himself to himself and rarely socialised outside of a small circle of...

Kate Part 2

Kate, Part 2 By Ricky Having made the decision to live as Kate over the summer, I spent even more time on the net, reading and learning. What did men with a need to crossdress do before the Internet? It must have been incredibly lonely. The evening we agreed to make Kate a real person, I ordered a voice training CD and subsequently spent a lot of time talking to a tape recorder. For that matter I spent a lot of time looking for a tape recorder; they're going the way of the...

WoMen In Red

WoMen in red Writen by: Julian069 1. Part. Julian is caught by 4 women in his penchant for women's clothing and forced to become a Dolly. 2. Part. Julian's wife gambles Julian's self-determination, both of them get into slave service. 3. Part. Julian takes on his role as a woman, experiences erotic adventures, but also finds an explanation for his passion. Part 1: I am male, my name is Julian, live in Berlin Germany, I am 44 years old, 178 tall, weigh 70 kg, happily married,...

Barford File 2 The Betancourts Chapters IX and X Final Chapters

IX: Training Daze Harvey Betancourt kept his eyes closed, his mind in an almost Zen-like state, as his wife continued to run the buzz of her old-school clippers over areas of his head. Glenda was almost done shaping his hair to resemble the look of the eager new recruit that was a day shy of being shipped out to Europe. Only back then, he wasn't as pleasantly well-built, nor as tanned, as he was now. The radio played a Benny Goodman swing tune as Glenda worked. He remembered...

David s Story

David's Story Chapter 1. How it all started. I lay there with my eyes closed just enjoying David's touches and kisses. They were so soft and sensual. He's always been a great lover and able to excite me, but tonight it was special. Very special. David and I had met in high school during our freshman year. And, when most of the other girls were chasing the jocks, I saw something in David that really attracted me to him. ...

Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

Flat Mates Part 3 Chapter 13 A Parting of the Ways

FLAT MATES - Part 3 Chapter 13 - "A Parting of the Ways" The first few days after Gavin flew to America I mopped about the house, listless and without any energy to do anything. I couldn't even be bothered to dress properly and wandered about in a pair of women's satin pyjamas and a towelling dressing gown. I didn't bother to shave and my long hair soon became a tangled mess. I looked frightful! Deep inside I knew I would have to snap out of this lethargy; Gloria would not have...

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