Jim's First Dress free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)

Jim's First Dress By Gigi For Jim It started as just another day. He worked downtown at the office, dressed as usual like any typical guy; tie, dark jeans and white shirt. At the end of the day, on his way to the bus stop, he just happened to walk through a big department store. Normally he'd quickly look at the men's wear but today the pastel-coloured summer dresses caught his attention. They were on sale: just $10 apiece. He immediately thought about what it would be like to wear one and suddenly felt a rush, his heart beat faster and he felt a little dizzy. This was puzzling to him. There was one in the XL rack that seemed to be about his size. He was tall but the dress looked like it would reach down to his knees. It was sleeveless, mostly light pink with a cute pattern of little yellow and blue flowers. It had a short V-neck with a pretty white lining. The hemline of the dress was wide and free-flowing. Overall it appeared very loose so he decided he wouldn't need to try it on. In fact he was too timid to even stand in front of a store mirror with it. He had never felt a stronger urge in his life than right now, to own this dress. He thought to myself, "If a store clerk asks, I'm buying it for my girlfriend." But the clerk said nothing as she rang through the purchase except for "Have a nice day." That done he went straight home. His girlfriend Tamara was away for the weekend. Jim wanted to try on the dress right away and then experiment with Tamara's makeup, try on a couple of her purses, shoes, etc. He took off his clothes and felt a rush as he slipped on his first dress, just like the feeling he had back in the store. He opened the closet to store his male clothes and there IT was. A summer dress similar to the one he was wearing, just a lot smaller. It was Tamara's. "That's interesting," was all that Jim thought. For the rest of that evening and weekend Jim lounged around in his first dress. He even watched football on Sunday afternoon wearing his pretty dress. He tried on every shade of lipstick, eye shadow, and blush owned by Tamara. But he was careful not to use too much of any one thing so that Tamara wouldn't notice... he hoped. Just a half hour before she arrived home, Jim had finished cleaning up the makeup and hiding the dress; running through his mind were ideas for the next time she was away!

0
0

21.01.2023
14
0

Same as Jim's First Dress Videos

jims wanking gets him in trouble part 7

a'so do i need to go and check the laundry basket or have you been behaving yourelf ?' amanda asks jim'please mom some of your knickers are covered in cum but its not mine mom''really so who's cum is it ?''uh its darryls cum mom''really and why would darryl feel the need to wank off onto my knickers ?''please mom i don't know mom but i'm telling you the truth mom its not my cum i didn't do it mom''well darrly was here to keep an eye on you and you were supposed to do as you were told so if its...

jims wanking gets him in trouble part 2

j'jim wake up' amanda says nudging jim'huh what whats happening what time is it ?''its 3am i bought your cup come on get up sit on the side of the bed and wank off for me' amanda hands him his cup'please mom no its really early you know i like my sleep please not now''you know my rules so come on stamd up get those pj's off wank into your cup don't keep mommy waiting' amanda smiles 'and in future i want you sleeping in the nude understood ?''yes mom' jim stands and takes off his pj's 'please...

Jims Discovery 1

Jim was halfway through his afternoon in the office. He hated his job. Well he didnt really hated it, it was just too boring. Especially on such a nice friday afternoon. He tried to concentrate but he couldnt, the job was just too boring, but then was saved by the bell. Or rather the ringing of his phone. He looked at the display and saw the number of his mother. "Hi mum, how are you?", Jim answered the phone. "Hi Jimmy, im fine, how are you?" "Great mum, but im at work, so i dont have too much...

jims wanking gets him in trouble part 3

'jens on the way round jim here take your cup start wanking i'm not sure if she's coming alone or bringing her sons with her but i want you in front of the door wanking off when she comes in ok''but mom please she may not be on her own i don't want to wank off in front of anyone else please mom''so you don't mind wanking off in front of your mom and your aunt but not anyone else ?''uh no mom i don't like wanking off in front of anyone mom''well if you don't like it why does your cock get hard...

jims wanking gets him in trouble cum uppance

jamanda kneels in front of her husband ben and starts sucking his cock'i know what you have been doing' ben says amanda lets bens hard cock fall out of her mouth 'um doing ? not sure i know what you mean''get your mouth back on my cock and keep sucking ' ben grabs her head and pushes his cock into her mouth 'i know what you have been doing to our son jim , and i don't mind that he's a lazy cunt and deserves everything that happens to him , eating his own cum and other peoples cum even some of...

jims wanking gets him in trouble part 8

a'everyone please lets sit around the table thankyou for coming to jim's birthday party ' ben saysaround the table are jim and his mother amanda ,bens sister jen her husband darryl and their 2 sons kev and martin 'i know all about the games you have been playing with my son jim and also your sons kev and martin and i don't care they are all lazy wankers and deserve all they get , however i want to make one thing understood , the only person who works and put roofs over all your heads is me as...

jims wanking gets him in trouble part 4

'jim come here' amanda called from the kitchen'yes mom' jim answered walking in from the sitting room where he was watching tv'i think in future if its just me and you at home you should be naked so i can keep a close eye on your cock''please mom no please don't make me do that mom''shutup i'm sure you will enjoy it now strip off come on'jim takes his clothes off and stands naked in front of his mother with his hands over his cock'you know better than that take your hands away let me see your...

Jims Mowing

My partner Krissy & I live a busy lifestyle so we often get additional help around the house when time is tight. You know, a person who comes to do the washing & ironing, home handy men etc.Once a month we get our lawns mowed by Jim's mowing, the guy is a rather nice, almost due to retire gentleman. It was an unusually warm Autumn day and Krissy answered the knock at the door expecting to find "Jim", she was rather gob-smacked to find a much younger man in a Jim's uniform smiling nicely...

The Dressmaker

THE DRESSMAKER By Lisa Lovelace I had utterly the most horrid crisis in my boudoir on Wednesday morning. Phineas and I had responded s'il vous pla?t to a Thursday night soiree at the Gardners' on Chestnut Street, on the coveted south slope of Beacon Hill. It was the grandest house to which we had yet been invited - and the gorgeous new gown that I planned to wear lay in ruins. It was two-layered floor-length tulle over light gold taffeta, embroidered with purple and plum flowers. The ...

First Time With Crossdressers

For once, I actually decided to look at some of the other categories on the streaming sites I'd visit. So many things came up under fetish. Some of it I don't get but to each their own. A BBW was mixed in with the fetish and as I had expected before hand, it wasn't my cup of tea. Several videos had girls dominating guys in leather or latex outfits. I liked how tight they were, showing off every curve of their body, leaving little to the imagination. Upon thought, I had never been...

The Scarlet Witch Versus The Hairdresser

Chapter 1. Recap and Introduction In her first encounter with the infamous follicle felon, the Hairdresser, the mutant heroine known as the Scarlet Witch, and commonly simply referred to as Scarlet though Wanda was her Christian name, had been lured into his diabolical styling salon under the premise of a beauty make over and hair coiffure. However, instead of a relaxing hair appointment to enhance her already natural beauty and provide a boost to her self-esteem, the Scarlet Witch had only...

firsts time Im seen as cd crossdresser

From a young age I liked dressing up in womens lingerie and clothing.... as I got older I grew up over weight a little and more so the older I got..... by the time I was I was in my late teens I had nice size breasts....nice enough to fill a bra. So worked up the courage to buy some lingerie online and when I received it in the mail I was so excited. I couldn't wait to try everything on.... I had brought a white lace bra, matching panties and white suspenders and stockings.....I tried them...

Chapter 5 Playing with a New Friend While Dresse

While my friend Jim was pretty much my best buddy, I never tried to involve him in my panty play. I didn’t believe he would go for it, and I was afraid to suggest it to him for fear I would lose his friendship and become the object of his ridicule.I did meet another boy my age, and I discovered he shared my passion for nylon. His name was Dale. He also had a mature woman fan the flames of his passion. It was his mother, but, as he told me, she merely facilitated his enjoyment of her...

Night of Many Firsts Part 3

Night of Many Firsts 3Don Abdul ©Eddie is still caressing her tits, and rubbing his way up and down her torso when he feels her gentle movement, as she sways her hips opening up her ass to take in more of his cock. When he reaches in between her legs and rubs her clit, her rhythm changes and he begins to fuck her ass more actively. They continue to move together in blissful harmony and in enjoyment of their shared anal dance. The thought, and the pleasure of his cock live and breathing deep...

Sex Survey Females Firsts 3

I invite all my fine female dear readers to respond to this sweet sexy survey of their number #1 erotic experience. I invite you to write me the best possible sex you dream to have in the future, or maybe it better stays only fantasy?I invite you to tell us as much as you like about the ideal circumstances needed and the sexy scenario you long for.I invite you to share your feelings about your favourite fantasy. Why is it so special? A secret? A taboo? A fetish?I invite you all to check as well...

Night of Many Firsts Part 3

Night of Many Firsts 3Don Abdul ©Eddie is still caressing her tits, and rubbing his way up and down her torso when he feels her gentle movement, as she sways her hips opening up her ass to take in more of his cock. When he reaches in between her legs and rubs her clit, her rhythm changes and he begins to fuck her ass more actively. They continue to move together in blissful harmony and in enjoyment of their shared anal dance. The thought, and the pleasure of his cock live and breathing deep...

Chronicles With Sexy Crossdressers

My email id is Do not forget to let me know how this sex story was. Who knows, we might get even lucky if everything goes well ;) Clean shaved men inside female clothes (or people who are known by the name crossdressers) are my new found favorites. Believe me, I always make it a point to taste every bit of them with passion and fire. My hands and tongue never leave an inch of their body. Hairless, like women and the ‘EXTRA’ jackpot called ‘COCK’, is simply divine. This is a story of how a...

Playing Dressup

My parents have a library. I was a very lucky girl growing up, not because of the collection of classics that they had in leather bound editions, or even the enormous number of new books that they seemed to add constantly from visits to the book store or from various book clubs that they belonged to. I liked a lot of those, but my favorite books in their collection weren’t actually on the shelves in the spare room that we used as a library, they were in dusty boxes stacked in the garage and...

In her Dressingroom

With a make-up wipe I took the orange glaze, the white glitter and the sweat of my face. It was always such a satisfying moment. After the show was done, my muscles sore, I would take off the sweaty costume of the Sugarplum fairy, but before I jumped into the shower of my private dressing room I first took the make-up off my face. Seeing the Sugarplum fairy disappear and my own face reappear. A moment of self care. A moment off calm, no sounds, no music, just the soft rumbling of the...

Cuckoldress

The Jamaican culture is rife with cuckold stories, white women bored with their husbands taking advantage of numerous available lovers to satisfy their needs. I went to school with the product of many such unions. Later as I matured sexually, I listened as the old bulls told of interesting liaisons, with the tourist women, who frequented our idyllic island looking for the same. So it was one night a bunch of us young ‘Turks’ were hanging out scoping the women hoping to get lucky before the...

Babs dresss

My father used to look after and maintain the garden of a local business man who had a large mansion, and at times I would go with him to cut some flowers for the lady of the house to decorate the lounge and other rooms . She would show me how to do flower arranging using the flowers and ferns, she was always very nice and pleasant with me because they had no c***dren of their own, and would at times she would ask me to tea after school. I always agreed because my parents were always arguing,...

Filipa becomes a cuckoldress

Filipa had been annoyed by her boyfriend Mark for sometime now about getting into cuckolding . She had resisted the idea of dating and sleeping with other men because of her religious upbringing but recently she had become more comfortable with the idea.She had been chatting with several guys online and was starting to feel a connection with one in particular "Derek" .He had been trying to persuade her to meet him for a drink. he was tall 6,2 to be exact with a muscular ripped body and a great...

Black BBW Cuckoldress

I meant Janine on live links. Actually I was drunk when I called the line. Just hoping to talk a woman while I jacked my little pink dicklet. In my introduction I mentioned that I was into cuckolding, and SPH, and that I had preference for BBW's. This was in the Detroit area so most of the ladies on the line were African-American. Her ad stated that she liked to have her asshole licked, and was looking for a long term relationship where she could really control the person she was with. At the...

The Irish Cuckoldress

"I finally got a date with her!", I shout loudly as I walk home. Of course the people around me have no idea who or what I am talking about, nor do they care. Her name is Claire and is an absolute Goddess. https://es.xhamster.com/photos/gallery/4582166/104421822She is 6 feet tall, blonde, big titts, long legs, and a body that a porn star only has. She is beyond beautiful and pretty. I have tried for months to get a date with this amazing wonder like woman but have always been rejected due to...

Marrying a cuckodress

So it's my wedding day, i look at my future husband as i walk down the aisle and see his smile, then i look at his best man and wonder if i'm rally doing the right thing getting married. It wasn't that Alex wasn't a nice guy, he totally was and he was the sweetest guy i'd ever met, but i was just used to being with dickheads, a lot of dickheads , and didn't know if someone like Alex could handle a woman like me. I knew he was very inexperienced, although we hadn't actually done anything much...

cuckoldress

Today my very lucky & equally pathetic cuck bitch hand delivered me a £500.00 cash tribute along with a bottle of champagne, some vodka, flowers & cocktail shaker..he thought he was just dropping them off & meeting my bf in preparation for our big joint session in a couple of weeks..nothing could of prepared slut for what I had in store for him....Here in his words is part one..After a near sleepless night thinking about the day to come it was with eagerness and trepidation I set...

Black Cuckoldress

I met Shanice at work three years ago. We worked for a manufacturing company, I worked in the plant and she worked in the lab. It was at the company Christmas party that we really had a chance to talk. I had such a great time with her at the party that I decided to ask her out. Things progressed from there and soon we were dating on a regular basis. I can still remember the first time we had sex. Shanice is a beautiful, athletic black woman. I had never seen a naked black woman up close before...

Babs dresss

My father used to look after and maintain the garden of a local business man who had a large mansion, and at times I would go with him to cut some flowers for the lady of the house to decorate the lounge and other rooms . She would show me how to do flower arranging using the flowers and ferns, she was always very nice and pleasant with me because they had no c***dren of their own, and would at times she would ask me to tea after school. I always agreed because my parents were always arguing,...

Military School Crosdresser

MILITARY SCHOOL CROSSDRESSER By Kresha Matay PART 1 Tim was a sensitive young boy, bright and intelligent, but lacking many of the physical characteristics of Joe, his father. The father had wanted a son who was interested in sports, hunting and fishing just like himself. Unfortunately, through no fault of his own, young Tim couldn't measure up to the desired image. Joe had expected his son to grow up to "be a chip off the old block" and when he didn't, his father felt...

Mommys Darling 2 Playing Dressup

Mommy's Darling 2: Playing Dress Up - By Billie Lovelace At twelve, I was deeply conflicted. On the one hand, I was a normal boy. At school I liked sports, roughhousing, and teasing girls. On the other hand, mother hated masculine aggressiveness. So at home I was more girlish. I played the piano, did housework, and spent hours with mother -- brushing her hair, polishing her nails, and helping her in and out of her high heels. It was so confusing. I wanted to be like other boys....

1900DRESSUP

1-900-DRESSUP By Ricky I'm sure that you have seen an ad or two (or twenty) for one of those 900 phone services. They usually have neat names like 1-900-HOT-HOTT, which is a real number that a teenage neighbor called twice on my garage phone before I caught him. If I ever could understand why someone would pay $25 for the first four minutes of talk when for a smaller monetary investment you could go to a bar somewhere and buy some floozy a few drinks and get the talk live, or...

Sidedressing

Sidedressing By Tyrone Slothrop Older sisters can be a boy's good friend and most effective torturer. Bernadette, charged with watching her little brother, was getting bored and decided to see how far she could manipulate him. Nothing nasty just keeping her hand in. Practice makes perfect. "Ralphie, come here, I want to try a new game." Ralph heard his sister and put down his videogame. He wandered into her room. At thirteen he was fairly average in height, about five feet...

Babs dresss

My father used to look after and maintain the garden of a local business man who had a large mansion, and at times I would go with him to cut some flowers for the lady of the house to decorate the lounge and other rooms . She would show me how to do flower arranging using the flowers and ferns, she was always very nice and pleasant with me because they had no c***dren of their own, and would at times she would ask me to tea after school. I always agreed because my parents were always arguing,...

Playing Dressup

My parents have a library. I was a very lucky girl growing up, not because of the collection of classics that they had in leather bound editions, or even the enormous number of new books that they seemed to add constantly from visits to the book store or from various book clubs that they belonged to. I liked a lot of those, but my favorite books in their collection weren't actually on the shelves in the spare room that we used as a library, they were in dusty boxes stacked in the garage and...

Confessions of a Cuckoldress

Confessions of a CuckoldressHi! I’m Melissa. I’m just a regular gal that has a very active sex drive. I found a great solution to the age old problem white women have had since the beginning of time and this is my story about how I found this solution.We white gals love our white boys. They are great for cuddling, doing housework, showering us with affection and of course worshipping us. The problem with white boys is their little dicks! What is a girl to do when she is in love with a white boy...

Cuckoldress

The Jamaican culture is rife with cuckold stories; white women bored with their husbands taking advantage of numerous available lovers to satisfy their needs. I went to school with the product of many such unions.Later as I matured sexually, I listened as the old bulls told of interesting liaisons, with the tourist women, who frequented our idyllic island looking for the same.So it was one night a bunch of us young "Turks" were hanging out scoping the women hoping to get lucky before the night...

Custom Cuckoldress

Tonight's the night. My boyfriend has been insistent that I try to fuck another man. I've been hesitant because it seems so bizarre, but, ultimately if we do it safely, I guess once can't hurt, right? We've had a few group dates with an African American man named Markus, and decided he'll be the one. I'm fairly anxious, I've never been with anyone other than my boyfriend. I've been trying to keep my head on my shoulders. We arrive to the hotel. Underneath my clothes I'm wearing some dangerous...

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,...

A Night of Firsts

I have been crossdressing in private since I was young. Now in my late forties and after three failed marriages, I had decided to step outside as Jessica.So after a lot of planning over several months, the day had finally come.I stepped in the bath as JD and shaved any hairs on my body that should not be there. It did not take long as I had been preparing my body for weeks to be smooth. I stepped out of the bath as Jessica and dried myself off. I wrapped the towel around myself just like any...

A Day of Firsts

A Day of Firsts by Kathy Nelson [email protected] (c):Kathryn Nelson, 1998 It was one of those hectic work periods where I was putting in 70 to 80 hours a week. You know, when there's no time for anything else in your life except the job. But, thank god the rush was over and it looked like things were going to calm down. Friday night had come around and I was going home at a decent hour. I even had the whole weekend off and I was ready to celebrate. Well, more like...

An Afternoon of Firsts

The bar was crowded for the big football game. Standing room only. I was alone but hoped to find another regular to watch the game with. I ordered a beer and resigned myself to a disappointing spectacle. A good game was much more enhanced when watching with a familiar face or two. Halfway through my beer, I see Jim walk in. Jim was a guy a frequently chatted with and we really hit it off. He was the perfect guy to watch the game with. I flagged him over, shook hands and told him "Looks like...

4th bi experiencemany firststrue story

My 4th Bi experience happened that night of my 3rd experience. I'll never forget it was on a Saturday,Sept 24 1983. I was 16. It was 7:16 pm when I looked at the clock for what seemed like the millionth time. My parents were down the street at another neighbors house. I was sitting in my bedroom wondering what time I should go over to Charles house the anticipation was killing me. Earlier that day he asked if I wanted to come over tonight but what time should I go? I had occasionally looked out...

A Vacation of Firsts The Conclusion

Eric watched with unblinking eyes as the tiny panties revealed a small but erect cock hidden underneath, and that was another first for him. The stunning woman before him had just pulled her panties down and revealed a cock and he was not repulsed. Tonya's head was bowed in shame with this act. To her, it was like showing off a birth defect. Eric responded by placing his fist under her chin and gently raised it up and looked her in the eyes. He gave her a warm smile and then removed his boxer...

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 First Dress

My First Dress by Sissy Susie It all started the day mum had to take my sister Sandra to London for the day. My sister's school orchestra were playing in the regional finals of a competition. As there would be a lot of waiting around mum had decided that I would spend the day with my aunt Caroline and my twin cousins Becky and Kirsty. I did not mind because although the twins were fourteen, two years older than me, they enjoyed things like football and we even played it together,...

My Qualifications to Write About Crossdressing

My Qualifications to Write About Crossdressing By Ricky How ironic! While looking for something in my files the other day I found I have been writing about crossdressing more than 10 years now. The problem is, I now realize I am completely unqualified to be a crossdresser, let alone a writer on the subject. Think about it, just what are the qualifications for a crossdresser? Surely you've read a multitude of "true life stories" in the crossdressing magazines. Perhaps if we...

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...

His First Time In A Dress

The next morning, Andrew woke up to find a text from Emily on his phone.“Come over at 11,” it read. “Gr8 idea 4 2nite.”That sounded intriguing, he thought. He showered, made himself some breakfast, then ambled over to Cavendish Hall. When he got to Emily’s room, Calum was already there, sitting with his feet on the table and nursing a cup of coffee.“Hey, Andy,” he said with a wave. “Last night, eh? Wow. My arse is still sore from the banging you gave it.”“That’s cool,” said Andrew, trying to...

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...

Fantasy I have with my hairdresser

My name is Gary and I’m married and I’ve had this thing about a hair dresser I use to visit. Her name is Deena and she’s twenty years younger than me. I haven’t had Deena cut my hair in a couple of years and missed her. So I called her for an appointment as I was thinking about her recently. “Hi Gary, it’s been a while,” she said answering the call. “I know. I’ve been extremely busy with work.” “What can I do for you?” All...

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...

First Swing Party in a Prom Dress

Cindy and Dennis stand outside the large mansion that has a swinger's party tonight. Dennis had called yesterday and got an enthusiastic invitation. Cindy was a cute blonde 18 year old recent high school grad. She is wearing her beautiful pink prom gown that barely holds in her full breasts and shows off her slim figure and firm small ass. Dennis told her to dress very nicely and Cindy had learned the hard way not to say no to Dennis. He had spanked her sweet ass until it was beet red when she...

My first Dress

My first dress By Dedra Post This is one of my short stories about my life as a cross dresser. The beginning I had just turned 8 when Linda came to work for us as a live-in sitter/housekeeper, mom had put a advertisement in the help wanted section, Linda was the only one that would work for the salary mom could afford. She had just moved away from home in Washington state. She had lived with her father and four brothers and had the home maker for them since her mother died...

Milwaukee Cuckoldrsquos 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...

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...

Amazing Night With A Sexy Crossdresser

Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one. I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and...

A Confession A Night of Firsts

I hope you enjoy it. Please PM me or comment below and let me know what you thought. Of course I also encourage voting. If you go into the Forum section of the site you will see the Sex Stories Section. The CAW10 entries are there... I strongly suggest reading them as they are wonderful and written by very talented people. Enjoy! A Confession – A Night of Firsts I am a bit worried as I write this. Mostly because of what I have done and what I know, with absolute certainty, I...

Porn Trends