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Diane a new Beginning

Diane, A new beginning Janet L. Stickney [email protected] Somehow the dress just felt right. I had dreamed of this moment for a long time, yet I had always been too scared to even try it! That was the first time I have ever worn women's clothing, and now I know for sure that it was exactly what was missing in my life. I don't know why I had dreamed about it, but quite often over the years, in my dreams, I drew a mental picture of myself as a girl, one that I was sure I...

Living the Dream

I would like to thank Cassandra Morgan's 'A Few More Favourite Themes' for putting me on to the stories by Mrs Anyonamrs and Miss Anyonamiss : Careful and Careful 2. They were basically one story from two perspectives, but provided the inspiration for my short and comparatively dim shadow of an offering here. The original stories seemed to hang in the air, have the author(s) thought of giving them both a definite finish? They were too good to be just left with unanswered...

A College Education

He was rubbing my silk-covered ass, slowly, sensually, both hands, one on each cheek. Gently squeezing, running his fingers down to my inner thighs then back up again, down my crack, pushing, probing. I had my legs spread apart shoulder-width, my hands flat on the wall, pushing myself up with my back slightly arched. He was silent, just rubbing and squeezing and teasing me. I was moaning softly, hard in my panties, naked aside from the flimsy underwear. His hands were large but...

Elliana

ELLIANA! By Olivia Evans Our story begins, oddly enough, at the end of the story. The opening scene is in a large theater filled with "A" list actors and actress. Also, in the theater are family members of the stars, and in some cases, the star's entourage of "beautiful" people. Most of the Awards have already been given out. Only three remain, the Best Actress in a Leading Role, Best Actor in a Leading Role and the award that is most eagerly awaited, the Best Picture. ...

Revival of the Fittest

Five years of my life, up in smoke. I'd been suspicious of Claire for a while. Nothing major, just the odd thing. How she was more careful of her appearance. She was staying at work a lot later. She'd started being more cruel towards me, taking potshots that I wasn't the most masculine of guys. Making cracks like I wasn't a real man because I liked watching Strictly, how I'd probably prefer to wear the dresses (I didn't. Well, not then at any rate) or be held by the big muscular men, how...

Beginnings A Winnisimmet Tales story

This story was made possible with the help of Josette Du Pres, Ib12us, Nuuan, Sammi, Portia Bennett, Erin G, and Dawnfyre. All of you helped out in multiple ways with personal stories and recollections and pointed me in the right direction. It was a dreary day in mid-June as John Finn and his two elder sisters, Leslie Sylvester and Karen Smith, stood over an old, weathered grave marked only with a number in Forest Hills Cemetery in Roslindale, Massachusetts. They were alongside...

Diane a New Beginning

Diane, A new beginning Janet L. Stickney [email protected] Somehow the dress just felt right. I had dreamed of this moment for a long time, yet I had always been too scared to even try it! That was the first time I have ever worn women's clothing, and now I know for sure that it was exactly what was missing in my life. I don't know why I had dreamed about it, but quite often over the years, in my dreams, I drew a mental picture of myself as a girl, one that I was sure I could...

One Her Own Part 1

There is a funny paradox that goes on in Hollywood. Fame isn't all it's cracked up to be. Fame is more of a curse than a blessing, especially when you are the less-than-famous relative of celebrities. For 99.9999% of the time, you live in a bubble. Your entire life is scripted. Nothing happens without a reason and it is often for the benefit of others that it happens, not yourself. Being a child in Hollywood is even worse, especially if you aren't the, "Chosen" one among your family....

On Her Own Part 2

In the morning, Anita felt refreshed for the first time in a long time. Looking around, she remembered that she was in the Finn home and was their guest until her situation was settled. She tried hard to think of a reason why they would want her there, but remembering Cat and Ella and their brothers' reactions to her eased her anxiety as none of them seemed to be offended by her presence there. Ella entered to check on her and gave her an outfit to wear. Anita felt weird accepting the...

Francis to Frances

It was never my intention to go to live with Aunt Matilda and Aunt May, in New York state five hundred miles east of Arlsberg but when I was offered a place at Uni a short bus ride from their place that Dad suggested I should see if I could stay with them.Dad always referred to them as Aunt Matilda and Aunt May but actually Matilda is my dad's aunt and May is just her special friend, and they are at least fifty years old and dedicated to each other and dedicated to their local church and it's...

Creating A Hellion

Creating A Hellion Elizabeth Parris Lonnie wasn't going to allow herself to go down the hopeless dead-end path that her mother and aunt had been forced to follow. They weren't forced she thought to herself. They were both smart, but they just couldn't imagine another life. Well, once every now and again Aunt Chloe talked about getting' out of here, but Ma always told her to shush up less she wanted trouble. That ain't going to happen to me. Gonna go down to the recruiter in the...

Sissy Maid

SISMAID.TXT by Cindy V. femdom, TV, humiliation This is the fourth fantasy story in a series of five written at the command of my creative mistress, inspired by page 46 of the January, 1995 issue of Cosmopolitan magazine, a pictorial entitled "In Search of the Perfect Bra." This story involves the model in the bottom photo - Padded. My mistress has a date tonight. First I am to dress as her "personal" maid. She took great care to emphasize the word "personal." Then I am to help her get...

Anyone for tennis part 2

After she had gone I looked in the bag. There were three nighties with matching knickers (including the set I had worn last night). There was some make-up and a booklet explaining make-up techniques, and also a pack of wipes for make-up removal. There was something that looked a bit like an electric razor but was, I discovered, something called an epilator. The instructions told me to use it every day, as it would remove hairs from my legs even before I could really see them and keep my...

Rachel s Tale

"Oh come on, honey, please, no." Will knew that pleading with his wife never got results, and Penny knew that if she gave into pleadIng even once it would set a dangerous precedent. "It is completely within the agreed process," she told Will. He pouted and sighed theatrically but could not deny that she was correct. He had been a tranny since his teens and when he told Penny, her response was that she would tolerate a reasonable level of activity, but added the acid clause that once...

Almost Damsel Almost in Distress 2

ALMOST DAMSEL IN ALMOST DISTRESS 2 By: Shawna Summers [email protected] I woke up sweaty and a bit confused. I was also having a bit of trouble breathing. I realized I was still wearing my heavy duty corset. I also realized there was someone snuggled up against me! Suddenly visions of last night's self-bondage session came back to me and I remembered Alex, my neighbor, had spent the night. I had a momentary surge of excitement at remembering him finding me in bondage and...

Femail order part 7

Over the following days and weeks I settled more and more into my new lifestyle. I bought more clothes and shoes so that I had more outfits suitable for my job in the office. I couldn't keep wearing the same things all the time, could I? Julie helped me make more space in my wardrobes by taking away the rest of my male clothes. And she taught me how to use more makeup and to look after my skin with moisturiser and so on. She was also helping me in the evenings, making me practise...

The Story of Prissy

DISCLAIMER This story is originally written by Linda Lafrance. It is her hard work, and dedication. It was one of the original pieces that drew me to TG fictions, but has become increasingly difficult to find on the internet. I have posted this in its entirety unedited and unaltered. I hope people find it as fun as I did the first time I read it. I take no credit in writing or editing this piece. If Linda Lafrance has an account on this site I wish for the piece to be moved. If she...

A Tale of Two Clitties

A Tale of Two ClittiesOne day I was checking out the bulletin board in a local adult bookstore. My eyes danced across the listings. Dungeon masters, couples looking for a third, but then I stopped, there it was, "Lonely virgin crossdresser seeks same". My heart jumped in my chest, and my cock twitched in anticipation. I tore off a tab with her number and promised my feminine side I'd call.A few days later I finally worked up the nerve to call her. I had battled all the familiar fears; would I...

Crossdressing

Finally a Princess Pt 02

Part two of a crossdresser who loves Disney who has come out to his wife while on a Disney Cruise. New experiences and adventures are ahead. Finally a Princess (Part Two) I woke the next morning around six thirty which was a little late for me. I laid in bed and thought about what had happened yesterday. I had actually spent time in front of my wife Sarah in women's clothing. My lost luggage had been the excuse for me to be able to live a part of my dream. I actually spent a...

Finally a Princess Pt 03

Finally a Princess (Part 3) Part three of a crossdresser who loves Disney who has come out to his wife while on a Disney Cruise. The experiences and adventures begin to heat up. I woke up early but could see that the sun was coming up as a trickle of light could be seen through the blinds. I laid in bed and started the morning off on reflecting just how fast things had moved yesterday. I had gone from being forced to wear some of my wife's things because of missing luggage, to...

The inheritance part 2

I woke next day wondering where I was. And why did I have large falsies attached to my chest. Then I remembered. My hand reached for my cock. And it was ready for my hand. Hard, but encased in soft knickers. I sat on the edge of the bed. One hand holding my cock through my knickers. the other hand cupping my breast through my nightie. I made it to the bathroom before gushing into my knickers. The cum soaked through onto my hand. I licked it. A curious taste. But I wanted more. I...

My Downward Spiral

My Downward Spiral Author's note. Each chapter is told from the point of view of the character listed. I am a newish writer of fiction and am struggling with wanting to convey the feelings and perspective of my different characters. I hope it is not too confusing. Also, I have tried to use a few Japanese terms to add color to my writing. I believe Kasuga Senmu would, in English, be Senior Managing Director Kasuga. 1 - Shiori Tsukada, OL "Shiori, if I could interrupt your...

Legacies Part 2

Things settled into a groove and saw Stan starting to work with the boys about defending themselves so they could stand by Jeff if someone tried another go at him. The boys' fathers were a bit put-off about it but it was clear why: they were jealous of Stan and what he could do that they couldn't do. All four of the boys did well, so well that Stan thought that they could make a go if they ever wanted to go pro. The intense training saw the boys putting on muscles which caught the eyes...

Legacies Part 4 Finale

The kids enjoyed a relaxing day in Winnisimmet, MA playing video games in the Finn's basement, out in the yard running around, and just walking around their neighborhood. They were greeted warmly by many of the residents, with the kids telling the Coles that those were their relatives and were keeping an eye on them to ensure that the Coles didn't go off into the city without permission. Jennifer was the unofficial leader of the group, but happily deferred to the younger girls among them...

Almost Damsel Almost in Distress 3

Almost Damsel, Almost in Distress 3 Shawna Summers [email protected] I felt Alex moving around the bed, I figured he was going to pee, and sure enough, he came back a few moments later and snuggled back into me. I did really want to ask him about last night's adventure and if he was my mystery lover or not. Though I was pretty sure it was him, the thrill of not knowing, made me wonder who else it might have been. The thought it was one of the guys from work did give me a...

Harold ella and Betty

I won't soon forget the night with my lover Ella, no longer my granny but a mature woman in her early seventies who knows exactly what is going on in life and loved life itself. Ella knew what was going through my mind or what was left of it as I lay in her bed wearing her skirt;blouse; black patent hiheels as I romanced her gold half-round reading glasses with the small pearls beaded neck chain wrapped around my cock, she knew that symbolicly I wanted her as I romanced her half-glasses and...

Wife s Erotic Peccadilloes

Pamela was my wife at the time and is prominently featured in "Ooh Good Boy". This tome will be the concluding act (or sex acts if you prefer) about her. By the time our life together vaporized... Pam was very much INTO dildos and vibrators IN to HER! Please excuse the use of caps here. They are essential in that they convey the message of her masturbation be'coming' obsessively compulsive! My older mentor Tina had unwrapped her angel wings from around me and bid me to fly on my own....

Being Pretty For Princess

Oh no, I thought, my Princess will be arriving shortly and I still haven't even shaved my legs yet. In a panic, I went to the bathroom and ran a very hot bath. As soon as I stepped in, it was almost as if I was in another world. My name, Stephanie, echoed through my head as I reached for the razor and shaving creme. Being generous, I lathed on the creme and started to shave quickly lest my Princess arrived early. I don't know what I had been thinking, but I had been distracted for quite a...

Why Didn t I Just Chapter 4

I slept until dinner time. At the dinner table, all of us were talking about our upcoming trip out to California. My father planned on driving out along the Southern route, stopping off in Texas and Las Vegas to see friends of his. My mother wanted to drive up North, through Minnesota, so that she could see her sister who lived on a farm near Marshall. I wasn't looking forward to being stuck in a car with my parents for a week, and I didn't have anyone that I wanted to visit. My father got...

Caught Chapter 3

I won't soon forget the night with my lover Ella, no longer my granny but a mature woman in her early seventies who knows exactly what is going on in life and loved life itself. Ella knew what was going through my mind or what was left of it as I lay in her bed wearing her skirt;blouse; black patent hiheels as I romanced her gold half-round reading glasses with the small pearls beaded neck chain wrapped around my cock, she knew that symbolicly I wanted her as I romanced her half-glasses and...

No Contest Book 3 Tallying the Score 2001 2003Chapter 24

Cheryl met Joe at LAX, giving him an intense hug and kiss. As soon as his luggage arrived, she pulled him away from the others and into her rental car. Rachel had a limo waiting, but Cheryl wanted Joe. Taking him to her hotel room, she ravaged him before he ravaged her. Despite depleted energy, he managed to be as relentless as she needed. Her frequent, ramping orgasms definitely helped keep his energy up. They said little on the way there. Cheryl about the kids. Joe about Hong Kong and...

Out and about part 3

I went back down to the living room and looked in the bag Audrey had given. There were two packages in it, both covered in gift wrap. One was a box shape, the other could be some sort of garment. I took hold of the box-shaped item and ripped off the wrapping paper. There was indeed a box inside. When I opened it I saw it contained a cock dildo. A more or less normal sized erect penis with a shiny pink knob end and balls. Rather like what I would have had if my own cock wasn't locked...

The New Student

There is a theory that girls make better students than boys do. This the story of what happened to me when I started at college (OK - some details have been embellished here and there)... When I gained a place at University, my mother was worried about where I would live, and within a few weeks announced that she had arranged with a family friend for me to have a bed-sit. "Apparently there are a few other students in the house, so you won't be lonely," she explained. The weeks passed...

Little Miss Sissy Whore

Chapter 1 -- The Pick-up Every year I waited eagerly for the three days when PC-Expo was back in town. In the past, I was always able to find some willing and naive out-of-town female to pick up, "do the nasty," and say my hasty good-byes. Most of them were from some small hick town and were entranced with the Big Apple. In fact, that was both the nickname for the city, and for me. Most women just couldn't wait to sink their teeth into me. So there I was, looking for some love, on the last day...

Little MIss Sissywhore

Little Miss Sissy Whore Chapter 1 -- The Pick-up Every year I waited eagerly for the three days when PC-Expo was back in town. In the past, I was always able to find some willing and naive out-of-town female to pick up, "do the nasty," and say my hasty good-byes. Most of them were from some small hick town and were entranced with the Big Apple. In fact, that was both the nickname for the city, and for me. Most women just couldn't wait to sink their teeth into me. So there I was, looking for...

The Office Girl

This story is incomplete. I wrote the first part and then thought it could be just a beginning of a longer tale. I would love to collaborate with someone on turning it into a finished product. Being a businessman, I particularly enjoy this theme. Contact me via the hyperboard or via Mindy on fictionmania who can contact me reagrding working with me to finish this story. The Office Girl by Charlene This is the story as I began it about a year ago. Here's the fantasy as it...

Darren s Dilemma Chapter One

Darren's Dilemma Chapter One Crimes And Chastisements By Suzie Q Haff I reached into my pocket, pulled my door key out and unlocked the front door of our two story house. As I entered I closed the door behind me and dropped my book-bag next to the coat rack. I walked down the hall towards the kitchen trying to be as stealthy as a fourteen year old boy knew how. It was Friday and I was trying to figure a way to get out of bring grounded. Slowly I pushed open the swinging door to the...

Dolly part 2

My heart was pounding as I walked to her front door. I rang the doorbell. The door opened. She looked at me questioningly. I handed her the pack of depilatory cream. She weighed it in her hand. She didn't need to look at the tube inside. It was obviously much lighter than when she had given it to me. A big smile lit up her face. "Come into the doll's house," she giggled. I stepped into the hallway and she closed the front door. "Let's go upstairs," she said. Once in the bedroom she...

Stage Three Of My Journey To Becoming Joann

As we drove home from the Halloween party Sis asked me if I enjoyed my first time out as Joann. I replied, “It was great. How did you come up with the name Joann?”“Well, I really didn’t think about it until I introduced you to Michelle. I actually started to say Joseph when I realized I needed to correct myself. I guess Joann was the only logical name at that point. Do you like it?”“Yeah, it’s nice,” I replied. “Thank you for dressing me up and taking me out. I hate to say it, but I really...

Incest

Aunties Niece

Auntie's Niece By Carol Francine Saunders Many years ago, when I was age 15 and visiting my Aunt Jean, I had worked up the nerve to ask her to dress me in my cousin Sally's clothes. I had always been especially fond of Aunt Jean. I enjoyed spending two weeks with her each summer. She seemed so easy to talk with, much easier than her sister, my mother. Aunt Jean was divorced from her husband. She and Sally had lived together until last year when Sally moved away...

sold

sold By stephanie winner as he opened his eyes he couldn't see anything. total darkness around him. he tried to move but realized that he couldn't move his hands either his feet. he was tied! he moved his head around and saw that he was caught in a trunk. he felt the trunk moving. 'must be a car-trunk,' stephan thought. then he felt the car stopping, moving backwards. he tried to say something but his tongue was like a big woollen scarf in his mouth. he must have been...

Two Way Stretch

This is a work of FICTION for ADULTS only. Do NOT read this if you are under 18 or if you are not an adult according to the laws of your state or country. Do NOT read this if you are offended by fantasies involving sexually explicit material. Written by Bethany Jacques. Comments welcome to [email protected] Two Way Stretch 1 By Bethany Jacques It started out as a chance to make some money, in a rather forced situation, thank you dear Aunt Daphne. It ended up as a whole...

Madhouse 2

Author's Note: I have no idea where this story is headed. I know I started this because there were, at the time, a lot of well, not very excellent stories being posted (that has certainly changed). So being sleepy, I figured I'd try to push the envelope a bit. I wanted to go to far, when love and kinks go astray and make the reading painful. And then just let it go from there. So I typed. Here's my own review for it: Good writing, bad story. (But who knows, maybe it can be...

Both Ways

BOTH WAYS by Barbara (My fifth story) This story is in two parts. There is very little CD/TV in part I. Even if you want to skip to Part II, you should skim Part I. It is a setup to Part II and explains how the characters got where they are in the story. PART I My name is Edward, Edward Wister. My friends call my Eddy. I was 18 the summer I graduated from high school. Neither me nor my best friend, Sparky, were totally...

The Yellow Sundress Ch 04 Observation

The Yellow Sundress © Titania Midsummer - 2016 Chapter 4 - Observation Adam did not return the next day, though he did drop a note into her letter-box saying he would be a few days. He had to give notice to his landlady and to the restaurant manager. He wrote that as casual staff are easily found he would be under no further obligation after three days. Judy was a little disappointed, but at least he was doing the right thing which boded well for their future...

Sissy Outed part 3 Audrey finds out

As I walked the fairly short distance between the supermarket and Helen's flat, I was aware of an increasing sense of trepidation. Although by this time I was reasonably confident when being seen on the street in girls' clothes, I was more aware than usual of being a boy who had been forced to wear feminine attire. OK, "forced" is perhaps too strong a word. I had liked dressing in girly things while in the privacy of my own home. But since my little secret had been discovered, I knew that...

Bra and Knickers part 2

The following morning she told me to get up, to take off my sleep bra and knickers, put my knickers in the laundry basket, and then come to the bathroom. "I'm going to put some depilatory cream on you," she explained. "It smells a bit weird, but you'll be lovely and smooth afterwards." She applied the cream to everywhere that was hairy below my neck line. I wasn't a very hairy person, but that still meant that most of my body was covered. While I was standing there waiting for the cream...

Femail order part 4

I woke up early the next morning. It took me a few moments to get used to the new sensations round my body. I fondled my tits. A wonderful sensation. My cock wanted to grow but seemed to be pushing against a locked door. This made me feel more girly. Not only did I have tits, but I couldn't get an erection any more. I didn't need the glass by my bedside. Conscious that I needed to look my best in the office, I shaved my face twice and used the depilatory cream on my legs. I had decided...

The Phone Call

This story is not erotic and there is minimal sex, if you can call it that. I hope it is romantic, in its own way. It is more a study where the feeling and symptoms are taken from actual case studies about this problem and are all put into one story. Since I have been there and done that, I knew what I was looking for. So there is no one person named Kara -- she is a compilation of hundreds of case studies I read about on sites for this type of problem as background for the story. If I did not...

Jamie and Donna s Girls Night Out

Girls’ Night Out Tonight: Getting ready Donna was looking in the mirror, sponge in hand, ready to blend the foundation that dotted her face. She had shaved and moisturized her face; she didn’t need Jamie's help for that. Fortunately, Don’s facial hair was fine and light-colored, so Donna didn't need to cake on too much concealer. Don had tried to use stubble as an excuse to cut these nights short but Jamie wouldn't have it. She knew her husband's face would still be smooth when they went to...

Love Stories

Growing up chapter 6

Ashley my lab partner was a sorority girl with long straight blonde hair and hazel eyes. She said she was a cheerleader in High School and she still had the tight gymnast body and a cute ass. I can imagine her in a pleated skirt and cheer pants. I think navy blue would be her best color. I wondered what she was like in bed and what the look on her face would be as my dick slid into her. Fun to think about. But innapropriate! After Cindy’s second weekend visit when we’d been seen in the...

Pornstar Ch 04

Pornstar Ch 04: Being an Item We walked up the hill through the wood. Nancy wanted to hold my hand, which was cool with me. For a long while we didn’t talk, and that was OK too. At one point I slipped on a tree-root and caught my ribs, and just doubled up, gasping. Nancy knelt down and held me. After a couple of moments it was a bit better and I straightened up and leant on a tree trunk and apologised for being a wimp, and Nancy just came up and put her hands on my shoulders. She had her head...

Jaclyn part one

Not too long after that I discovered transvestite website’s, I was stunned how these men would dress up, and pass as women, it went from transvestite to she males, even the sissy hypnotic videos, I watched them all, for a long time, the desire to dress up and wanting become a girl grew inside of me I wanted nothing more than to do those things I saw on line. I learned some basic’s from them how to dress, do make-up, everything that a girlie boy would want to learn. My friend George would...

The Bradford Family Saga Part 1

Through her wide open legs she watched the last drops of her morning piss cling to her silky blonde pussy-hair, then drop into the bowl. She stretched and yawned, willing her reluctant body awake. "Mike?" she called. "Yeah?" her husband answered, pushing the bathroom door open. "Well, aren't you a pretty sight?" he said. "Look, who's talking. You look as bad as I feel," she said with a smile. Her husband was naked except for a towel around his mid-section, his flaccid...

Beginnings at the Adult Book Store

There are two types of cross-dressers. The first are those who dress all the time. They are usually quite passable since they spend a great deal of time and effort. The second are wannabe women who live in a world where there are circumstances that prevent them from being full-time out of the closet cross-dressers. They are usually not passable since they cannot shave their entire bodies, grow and style their hair, purchase and maintain a female wardrobe, and/or learn and understand make-up. I...

Crossdressing

Slaved

Slaved. The fan above the bed creaked and groaned ineffectively in the suffocating heat, barely cooling the legion of flies that crawled exhaustedly over it, the clock said three a.m which meant I had been watching the fan for two solid hours as I desperately tried to get some sleep. The images from the day kept scudding through my mind, the old walled city the Mosques with their Minarets, the myriad places for a sniper to hide up, and the old slave market, especially the old slave...

Never too late part 2

PART 2 The next morning I woke with my aunt impaled on my once again rock hard cock and my face buried in her huge tits. Unfortunately it didn’t take long for my balls to throb as I pumped load after load of hot cum into her tight cunt. She bounced and bounced on me until I slipped out of her then she took me in her mouth and sucked the last drops of cum from me. I was in heaven. We showered and I dressed in a matching black bra, panties and suspender belt with black stockings. Put ...

My Neighbor s Wife Pt 2

Suddenly, I was awake. Or was I just dreaming? It was hard to tell. Then I tried to move but couldn't. I could feel that what I was wearing when I last conscious, had been removed. I was naked, except... The last thing I remember was being face down and Carol on top of me steadily fucking my ass, somewhere in all that pleasure and pain, I must have either past out or have withdrawn inward. But now. What was going on? I began to realize Carol had found the bottom drawer of the dresser. The...

Crossdressing

The Injustice of the World

“There they go,“ I muttered to no one in particular, “baggy fucking t-shirts, formless trackies and bloody horrible dirty trainers. It’s disgusting.”I could almost cry.The school run and its procession of drab figures slouch pass my ground floor window twice a day, each time it's like a stab to the heart. The little ones are running and laughing, playing tag, shouting to unseen friends or generally enthralled at another bright sunny day.Their parents? Slagging off such-and-such to another...

Trans

My sisters their friends and me their sissy Part 2

Part Four Jolt after jolt of electricity passed through my body. Each longer and worse than the one before it. I held my number two hole shut because I believed what Joy had said about losing any of the water. But the pain was becoming almost too much. I knew that in another jolt or two my control would be completely gone and even with the help of the big thing back there plugging me I was certain to lose that water. And there were two gallons in me making me look really pregnant....

My sisters their friends and me their sissy

Part One My oldest sister Vickie, was 18 when my mom died. My middle sister Michelle, was 14 and my youngest sister Joy, was 11. I, Mark was the baby of the family at 7 and had been the only male in the house since father had passed away when I was 2. He left us well off and with his money well invested we lived very nicely indeed. We had a private tutor/governess, Ms Wells, a young lady of some thirty or so I suppose. A live-in housekeeper Ms Dee Dee, a French exchange student...

Every guys dream 1

My wife and I eventually divorced and I moved out. It was not easy being on my own again especially being in my 30's but I was able to rediscover my fetish with the help of internet shopping. I could buy all of the women's panties and bras I wanted and they would arrive at my door without anyone knowing my kinky little secret. I collected all kinds of sexy panties, garter belts and thigh high stockings. I even started to buy dresses and perfume and would spend my day taking a long hot bath,...

Every guys dream 0

My wife and I eventually divorced and I moved out. It was not easy being on my own again especially being in my 30's but I was able to rediscover my fetish with the help of internet shopping. I could buy all of the women's panties and bras I wanted and they would arrive at my door without anyone knowing my kinky little secret. I collected all kinds of sexy panties, garter belts and thigh high stockings. I even started to buy dresses and perfume and would spend my day taking a long hot bath,...

A boy s femininity awakened Part two early girlhood

Sissy boy John was petticoated at Secondary School after falling foul of Jenny Tough, a school bully. During his week of penance, John found that he was more at ease and happier amongst girls than with boys. John decided, therefore, to explore his feminine side by trying to live as a girl. John’s Mum was shocked when he first arrived at home wearing a schoolgirl’s uniform but calmly listened to his story.“Well, sweetie, this is a bombshell. You’ve always been a sensitive boy, but I never...

Crossdressing

Miss Tiffany Fulfilling Her Dream

Ever since I was a little boy, I had always thought my neighbor Steven was extremely handsome and sexy. At 6 feet 3 inches, Steven is exactly what described as tall, dark, hard tone and muscular. Tonight, I would finally have my chance to fulfill a fantasy to show him just how much I wanted him. When I was growing up, I always heard he was ladies man with many women lusting and chasing after him. So I always lusted every time I seen him with a women or in passing but not as boy but...

Nudists have sex part 3

Once again Ron awoke with a feeling of excitement. It was another beautiful day outside, and Julie had bought Ken home Friday evening, planning to take him to “Bare River Bend” nudist resort for a week of vacation before school started. Ron’s weekend job had ended, so he too was preparing for another year of school. Life would be better now that he was going into his junior year of high school. No longer was he going to be a kid, but one of the more esteemed class. In addition, he knew...

Discovering Faith Pt 02

This is a story continued from ‘DISCOVERING FAITH Ch. 1-12: Pt. 01. Please read that to understand the context and characters involved in this second installment. CHAPTER 13 – THE MOVIE BEGINS The following Monday, we all met at Gene’s to go over the production schedule. Glenn had arranged all of the locations and we would be shooting the offsite scenes first. Faith, being used to stage plays, was fascinated with the idea of filming out of sequence for later editing. The first week was used...

My story is about the start of my transition to a woman and finding the perfect guy

This story started a couple of years ago, or should I say it all started 40 years ago when I was young. It seems I have always enjoyed dressing in women’s clothes. I have been a closet cross dresser for most of my life, starting with dressing in my mother’s, sister’s, aunts, friends, etc. underwear then my wife’s and at any opportunity pinching other women’s underwear when the opportunity arose, then wearing them under my regular clothes. Recently I bought a video...

A story about a Bi Transvestite who meets up with some guys

The cooling effect of autumn made it’s presence known to me as I leant back against the tiles of the toilet with my shoulders and slowly wanked my rigid cock ‘ my lightweight raincoat hanging loosely at my sides. Having been a confirmed tranny for the last fifteen years or so, I was in one of my favourite haunts ‘ the public toilets in the park as I looked for anyone that wanted some adult fun with me. I particularly liked using these toilets at this time of the year because...

Caught and the Consequences

‘What the hell do you think you are’ I just lay there not knowing what to say and I am sure going very red under my make up. ……….. I will go back many years and start at an earlier age. For as long as I can remember I have cross dressed, always in private, without my partners or girlfriends knowing, totally in the closet, and when dressed I often practised self bondage, used dildos on myself, especially before wanking. I enjoyed shaving when I could, had the usual purges, it has...

Kiss me

Hi my name is Opal Hydrangea Ho. Are you done smirking? My friends call me H2O. Come on get it over with. My friends say that I have a personality like a Chameleon, fitting to my namesake opals which display different colors when viewed from different directions. Anyway my Dad is a Gemologist, and my Mom is a Horticulturist they are Americanized Chinese. My grandparents came to America when they were 12. My grandpa was 25 and grandma was 22 when they got married, my Dad was 21 and my Mom...

Playtime Stories Ch 11 Carla the Theater Whore a

11. After I was done stage fucking the nice-tiitted dirty-blonde school girl in her thirties, Carla had lined up some more meat for us. She’d been “working” the crowd while I had the blonde bent over on her knees. Carla and I sucked off about three more cocks each before the crowd waned. It was late. Carla offered to take me to her place and although I really wanted to go, I had to make sure I made it to my meeting on time in the morning. I knew it was past three o’clock in the morning. We...

Playtime Stories Ch 13 Unbelievable Motel Reward

Ok, so this one is hot, but is mostly fantasy…I have ‘earned’ a few nights kinda like this though… 13. I also fuck the hotel managers of another city. To be able to come and go all dressed up without anyone noticing is usually very important. Sometimes my company will have me stay at a premium ‘nice’ hotel. So I’ll get a slightly less nice motel on the side so I can do what I want without having it get back to my boss. A little caution and a few extra expenses go a long way. One of the...

Audrey

The people involved in tonight’s tale are, Anne, her god-parent Audrey, and myself. A few weeks ago, Anne told me about her god-parent Audrey getting ripped off by the guy that was living with her. Apparently he’s been seeing someone else after moving in with Audrey for a year or so. During that time he’s persuaded her to buy a bigger house and get a mortgage to do so. Then things started going wrong and he’s claiming half of the house and other bits and pieces. It’s usually the woman that...

My First Trip Out of the Closet

I have wanted to write this story for many years but I hesitated to do so out of my fear of the unknown. Since moving to Florida , I have pretty much been on my own for the first time in a long time. Let’s just say that now that I am older, I’m bolder! I no longer care who knows my sexual interests. It’s funny, because everyone I currently see understands my desires and approves of my different fetishes. Foremost of these, is my predilection to live my non-professional life as a...

Have A Good Feel She Loves It Part Three

After half an hour I was ready to go again. I looked back to the days before I got onto the scene whilst I prepared to rejoin the party. I would watch the likes of Bukkake porn and say to myself “I’d love to do that” thinking that in reality I would never even get the opportunity to try it. And there I was washing my cum covered face after having two guys wank over it in the middle of a hotel bar with people watching, and boy, did it feel good. I felt like one of those porn stars that I used to...

How My Life Changed

How My Life Changed Chapter 1 My wife Mary and I had been married for over eight years and I thought our life was very good. She was an attorney for an important law firm and rapidly rising towards a partnership. She made a lot more money than I did in my job as a fast food worker. That didn’t bother me as much as it might have many men. We had a nice house and lived well. Mary is 28, 5’6′, 120 pounds and had 38D breasts. She is a beautiful brunette with brown eyes. I am 5’8′, 140 pounds and...

Miss Tiffany Fulfilling Her Dream

Miss Tiffany Fulfilling Her Dream Finally, I had everything I needed to dress up for a little fantasy today. Ever since I was a little boy, I had always thought my neighbor Steven was extremely handsome and sexy. At 6 feet 3 inches, Steven is exactly what described as tall, dark, hard tone and muscular. Tonight, I would finally have my chance to fulfill a fantasy to show him just how much I wanted him. When I was growing up, I always heard he was ladies man with many women lusting and...

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...

The very first time with lots more to come

I guess we all remember our “first time”, and in my case the first time I was with a man while dressed was a awesome experience that I still remember vividly, and it happened by accident. I started crossdressing when I was about 14 due to my fascination with sexy women. The first time I slipped into a bra and panties and put on mascara and lipstick I knew I was hooked. I felt all tingly and excited like never before and after that I dressed up as often as I could. My single mom worked...

How My Life Changed

My wife Mary and I had been married for over eight years and I thought our life was very good. She was an attorney for an important law firm and rapidly rising towards a partnership. She made a lot more money than I did in my job as a fast food worker. That didn’t bother me as much as it might have many men. We had a nice house and lived well. Mary is 28, 5’6′, 120 pounds and had 38D breasts. She is a beautiful brunette with brown eyes. I am 5’8′, 140 pounds and used to taking orders from the...

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

Changing My Luck And Other Things

“Hey there, hard-on,” a melodious contralto voice asked, “you got a light?”I looked over at the tall black girl next to me and saw she held a cigarette between two long-nailed fingers, angling it in my direction. As I fished the lighter out of my shirt pocket, she stepped closer. I flicked the Zippo's friction wheel and she moved even closer as she bent over to touch the cigarette tip to the flame and suck it alight.She was taller than me in her high heels, but she was right about one thing: I...

Trans

Key West Nudist Queen For 2018

Cindy Weston was a properly behaved UK girl touring the Florida beach scene and enjoying every minute of it.Her best friend Josie from Bath was her semi-attached shadow and constantly reassured her that she was the most beautiful girl to be found in any direction as far as the eye could see. The serious-minded Josie was ever present at Cindy’s side to lather her up with the sun screen block at appropriate intervals. Both of the girls were a mature eighteen with the unfortunate circumstance that...

Voyeur

My magical birthday Girls Night Out True story

Names have been changed to protect the guilty... LolPhotos are a mix from that night and other nights... I simply couldn't concentrate on taking photos all night long with sooooooo many beautiful distractions ?One of the greatest nights of my life started with a simple request for my birthday. When my wife/Mistress, Madison, asked me what I wanted to do, I told her that I wanted to go out with her and have a night of dancing and chatting as “Chelsea”, my girly-side. I had been cross-dressing...

Dear Diary ndash He was so cute

Hot summer day I was planning on taking a walk thought the woods to the lake to see if the local boys were hanging out like the normally did. I dressed in a cute white sundress with butterflies and bumble bees on it, black lace pushup bra, and black lace panties (visible from under my sheer dress). Did my makeup put a cute pink bow in my hair and set off. About 20 yards down the trail I heard “Hi Michelle” turning to look seeing one of the younger neighborhood boys emerge from the woods. I was...

Confessions of a transvestite hooker or whore

Confessions of a transvestite hooker or whore – you cannot be serious I hear you cry – well I am as I reflect on my life in dresses to date and some of my experiences which I am about to write about here as a memoirs of a life in dresses.So why use the term ‘hooker’ or ‘whore’ – well what I am about to relate from my current stage of life the memories are that upon reflection the meets I am about to relate felt more like me being a provider of sexual services and pleasure to people desperate...

Teen Twink Sells Himself to Mature Men

My childhood was a little traumatic, growing up in a working-class family in South Boston in the 1990s. My mother and father are both pure-blooded, Irish Catholics, and I inherited their pale skin, freckles, and bright red hair. I was teased mercilessly and picked on by many of the other kids. They derisively called me a ‘ginger’, and some of the boys even bullied and beat me up. I couldn't defend myself very well either. I'm short, slimly built, effeminate looking, and even considered to be...

Crossdressing

CD Rebeca Vegas Play Pt 4 Binge Pt 2

These Vegas Play stories are about my time in Las Vegas between age about 19 1/2 to 25. I encourage you to read all of my stories, but these Vegas Play stories are really hot and present a younger portion of my experiences. Message me if you want, and always comment- Thanks!!Vegas Sex Binge Pt 2The guy who had enjoyed my anonymous half'n half with the guy and my anal orgasm shot his load just a moment after thanking me for the show. About ten seats away, he stroked and then cum spewed out and...

Stewardess And Her Daughter

The Stewardess And Her Daughter: A Bangkok Slaver StoryBy Marlissa [email protected] as crowded as ever at five minutes of eleven -- the hottest go-go bar in Joytown, which was Bangkok's most depraved sex-bar complex. Vopat, the proprietor, gave me that fat, oily grin of his as he raced backstage to prepare for the next act. A minute later, a gorgeous s*******n year old Thai bargirl appeared. I thought her name was Chani, but wasn't sure. Not that it mattered. Her marvelously...

Three nights in London night 3 Irene rocks

I woke up looking into the smiling face of a pretty redhead. Sunlight was streaming through the curtains of her bedroom. "Good morning, Irene," she said, and she kissed me on my nose. I smiled back and slowly remembered my adventures of yesterday. When I moved my legs it dawned on me that I was still fully dressed. I even had my high heeled boots on. My skimpy black dress was pulled up and revealed the tops of nude holdup stockings. The front zipper of Gabrielle's leather dress was open and...

Crossdressing

Three nights in London night 2 Irene is going out

"Irene,wake up sweetie." Slowly the mist from my dream started to lift. Irene, who's that? I slowly became aware that I was holding something soft and cuddly in my arms. A Teddy bear? I moved and felt something tugging at my chest. Breasts? I opened my eyes slowly and saw the broad smile of a pretty redhead just in front of my face. "Wake up, pretty girl." In a flash everything from last night came back. Oh, my god, so it wasn't a dream! I sat up and looked down at myself. Through strands of...

Crossdressing

Ready Waiting In my wife s lingerie

“Billy, can I see you in the bedroom?” I walked down the hall and into the bedroom, surprised to see lingerie laid out on the bed.I asked, “What’s this?”“We’re going to play a little game today. I need to de-stress, and you’re going to help me.”“Help you how?”“Take off your clothes and go shower.”After my shower, I returned to the bedroom completely naked. And erect. I kissed Betty. She pushed me away.“Not yet. I’m going for a massage. When I come home, I'll have my way with you. And you’re...

Crossdressing

Halloween Hostess

This story is one of my fondest memories where it let me be the girl i always wanted to be. I was in my mid twenties and had a girl friend who i will call Kathy. Now Kathy was a real demanding bitch if there ever was one. Kathy would say jump and i would say how high why i chose to be with her is any ones guess. There were plenty of nice girls that i could have been with but i wanted to be with Kathy. Maybe i needed that dominant person in my life Kathy was sure that Kathy was very good looking...

HOW ROBERT BECAME SISSY ROBERTA hottest Crossdre

Long before Robert L. even reached puberty, the seeds of his impending Sexuality were deeply implanted with strong personality molding roots. This by his single parent mother Bee, whose only real wish in life had been to give birth to and to raise a cute little cuddily sweet girl. So while all of the other boys in his small rural country town grew up playing army, sports or flirting with many of the interested and suddenly budding young girls, a poor and very sheltered Robert was made to spend...

Jaime s Way Part 1

I'd only been married a very short time when my wife came home and caught me masturbating while wearing a pair of panties and a bra. This in itself was bad enough but then she caught me again, and then again. The first time she caught me she was shocked and appalled but the twentieth time or so that she found me wearing panties and bra and with a dildo in my ass she really lowered the boom on me. “Are you a fucking fagot? Is that why you wear women's undies while you jack off? Do you try and...

Crossdressing

beta boi story

I couldn't believe it. My wife, Tarla, had been bringing me along gradually for the past year. First she had gotten me to confess my cuckold fantasies. Over two months she went from flirting with guys to petting and then letting them take her to bed. Sometimes I had to be where she went to get picked up -- usually some downtown club -- and see her leave with someone. Other times I was told to stay home and she would send me photos as the night progressed. I would lie in bed, naked at her...

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