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No Strings Attached The Reunion Chapter 25

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

My First Date

I had met Pete over an on-line dating site, and we had chatted for several weeks and developed a rapport when we decided to have our first real date. We agreed to meet at a local shopping mall parking lot and would do some shopping together. I spent the morning shaving my body smooth and getting ready. I went with a natural look for my make-up, and peachy pink lipstick. I slipped into a black shape-wear body suit to help with the curves and then slid on some sheer black nylons. I then slid on...

My Crossed Life Chapter 4 Inside Missy Literally

The hardest part of the school year and the winter was finding opportunities to explore my newfound feminine side. Often times I would sneak my bra and panties into the bathroom and masturbate while I replayed everything that happened in the back seat of Larry’s car in my mind. I would never forget touching his cock, feeling him get hard, the taste of his cum, and the satisfaction of knowing that I had the ability of making a man reach such sexual highs. I rarely took more than a few minutes...

Christine s Satin String Bikini Panties

I suppose to begin, my name is Ember, (at least for all intents and purposes here) and I have fancied silk and satin lingerie for as long as I can remember. I have been reading the stories and experiences of other authors for several years, I figured I would make an attempt to write about some of my experiences. The stories that I tell will be based on fact with a little fiction thrown in for the reader's enjoyment unless otherwise noted. Let’s begin, shall we…I was at my friend Mike’s house...

Caribbean Vacation part 1

Susan & I often traveled to the Caribbean for our vacations. We loved the laid back atmosphere and all the sun and gorgeous beaches. Last year though we arrived to find that the airline had lost my only bag containing all my clothing including my swim suit! Imagine arriving in the Caribbean without even having a swim suit to wear! I had just resigned myself to going down to the gift shop to purchase a pair of those crummy over priced swim trunks they sell when Sue spoke up. “You could always...

I was a wartime TV for the US Army

'I was a Wartime Transvestite for Uncle Sam! TJ Ryder Chapter 1 Reform School Romance! I couldn't believe that all I got from my uncle Bill when he died after all he said to me about my being hisfavorite grand nephew was an old diary from World War II. I mean I thought we got along pretty darn good, and its not like he had any money or anything, just another oldgeezer in an assisted care center who if he ever had anythinghad...

Dawn Visits Kansas Chapters Seven Eleven

Chapter Seven: WednesdayPart 1: Morning - Business UpdateI woke at sunrise, but Patti was still sound asleep, so I snuck out of bed, gathered lingerie, clothing, shoes, wig, and purse going into the bath to shower and shave. My dress for the day was a very simple, short-sleeve tie-waist shirtdress in tartan. After getting dressed and applying my makeup, I tiptoed out of the bedroom, closing the door behind me. Then I put on my two-inch black open-toe heels and went into the kitchen to make...

Free Clothes

I guess it is something that goes through the mind of every new or closeted crossdresser. Shopping for new clothes as a guy is awkward because it is difficult to do without making it obvious it is for you. Yeah you can go online, but it’s tough if you’re not used to the sizing and the clothes never seem to look the same as the picture. Thus, when searching for playmates on Craigslist, if you find someone purging some clothes, you have to check it out. And that’s exactly what happened. I was...

Crossdress boy s ultimate romp

He was in his late 20s.. I'm in my late teens. the thought of meeting him really didn’t come across my mind. however I was won over by his passion and sincerity and he doesn’t even mind if I didn’t shave my legs! wow! we arranged to meet at the car park near my place, he asked me to wait for him and he'll reach in about 45mins. I went straight to my aunts drawer, looking for my favourite pieces of lingerie.. I chose to wear a black lace t-back panty... a black padded bra.. and a pair of...

How to Treat a Lady

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

A Summer Night Cruise

I'm a thirty two year old slender, leggy, well-hung cross dresser. I've been wearing panties since my teens and probably always will. The feel of sheer nylon panties covering my cock and hugging my girly little ass makes my eight inches rock hard the minute I slip into them. The only thing better than jacking off while wearing them, is letting another guy do it for me while I'm pleasing his stiff cock that I've made hard for him. Going out in public while wearing girls clothes is a huge turn on...

Been A Long Time

Once I got married I pretty much gave up my crossdressing lifestyle to lead a more "normal" life.You know,settle down,have a couple of kids. I was a happily married man with two kids,what could be missing? Well one day while at work,I was on the internet and stumbled onto a crossdressing website,and all kinds of memories came rushing back to me. The feeling of sexy panties,bras and hose.The feel of a hard cock pushing it's way past my lips and down my throat.The taste of a hot load of cum. As...

The Wedding Proposal chapter VI

The dinner was wonderful. Tina was the sweetest sister-in-law I could ever wish for. We found that we had lots of things in common, and quickly bonded. She told me all sorts of stories about Tony, and I shared stories from my time as his friend. I had to concentrate to adapt the stories to the new ‘reality’, but as long as Tony played along it went great. He seemed a bit uncomfortable with us sharing so much of his earlier days, but had no choice but to laugh along with us. Besides, he was in...

Stacy s First Time

I have been cross-dressing for almost a year now. Ever since I can remember, I have had a fetish for high heels and finally was able to start buying my own secretively once I came to college. I have my own collection and wear feminine clothing mostly in my room, but one evening I was so horny from watching porn and wearing my dress and heels. I went on to an internet site to find someone in my area looking to get sucked. And lucky for me I did! I took a shower and shaved my ass and around my...

Evening In The Office

The normal workday had finished and I gladly filed away the tedious paperwork that I had been toiling with over the past few hours. Knowing that I wasn’t going to depart for a number of hours, I went to the common tea room and made myself a cup of coffee.Back in my office, I sat back, sipped my coffee and contemplated my plan for the next hour and a half before the evening students started to arrive. By now, the building had emptied of the usual complement of tutors and students, and so I knew...

The Pool Man

It was June and time for sunbathing by the pool in my backyard. To my pleasant surprise, I saw that the pool man the company sent this year was young and handsome with a muscular body and porn star mustache. I was instantly attracted to him the first time he came and we hit it off quickly.I was wearing a pair of cut-off shorts with a sexy black thong panty underneath. And I felt very sexy being near such a big, strong hunk. He had a way of looking at me like he could see through my nature and...

That First Halloween Part 2

They parted company long enough for Guy to reach his own car and pull up behind the SUV that was already on the street. As he followed it to the Carriage Hills condos, he was unsure how the evening would end. Carriage Hills was a gated community and the SUV stopped long enough for Zorro to address the guard on duty in the shack.They proceeded to an underground parking garage and parked their vehicles and boarded elevator. They rode the elevator attached to each other lips and their bodies...

Loverboy Ricky

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

Bobbie Breaks

Our routine continued for the rest of the time Amy was away on business. I would ask for money, and Joe would usually unbuckle his pants without a word. I’d give him a blowjob, and he’d give me some cash. I enjoyed it because it was the only time I was allowed to take my bra off.I channeled my frustration at having my girls locked away into being the biggest thot I could. He didn’t want to see my free swinging titties? Fine. He was gonna see every other inch of my body at every opportunity. And...

Simran A Crossdresser Part 1

Well I still remember the day back in the summer of 2010. I had just turned sixteen and was introduced to the world of cross dressing in the most fantastic way possible.I guess introductions are in order. I am Simar, an average guy from India, who goes to college, has a great family, great friends. Well something you gotta know first. My family follows sikhism so I have a beard, a mustache and body hair which I cannot remove because of religious reasons. But it is a blessing in disguise because...

Hitch hiking Baby Doll Part Three

When it comes to getting men to want to fuck her, a girl has to put her ass to good work. I discovered this when I was eighteen and first started being a tranny hooker around the adult book store. I was wearing my first miniskirt with a thong panty underneath, walking down the street. My ass cheeks were hanging out of the bottom of the miniskirt and men were slowing down to look at me, blow me kisses and talk to me. It wasn't long until I was in their cars and making money sucking them off or...

The Afterparty Part 2

As Summer lay in a pool of sperm soaken sheets, she dazed in and out from the hangover and the multiple orgasms she just had. She dazed in and out, coming into consciousness as she heard voices of two men down the hall. Neither one was the voice of Pete. The door was still open and the voices got closer. It took a lot of her strength just to try and pry her legs close as much as possible as she turned her head away. Her legs began to tremble as they approached the door. They did not enter,...

A Weekend away

Stevie had always wanted to have a weekend away with a load of like minded people, i.e. trannies and admirers. He decided to find a place where he could do this and be the real Stevie, or his girly name, Lucy Lou. He searched the net and found a place about two hours drive away. He booked it and counted down the days to be there.He had bought some new stuff and had practised his makeup. Then the time arrived. He decided not to stimulate himself for the whole week before so he would be feeling...

My date with Ben part 3

I was invited to Ben’s house for dinner Saturday evening and spent the day getting ready. His wife Susie was looking forward to meeting me again and getting to know me better. I was unsure how the evening was going to go, but I decided that I was going to try and enjoy it as much as possible. I spent the afternoon getting ready, and shaved smooth all over, hoping that Ben and I would get to be together again. I moisturized after my shower, and enjoyed the smooth feeling of my body. I had...

I Just Wanted a Kiss

Mike and I had been working together at Tony's Pizza for about a year. We were both twenty-two years old and we were both losers that didn't give a fuck. I lived at home in the room where my mom had changed me and tucked me in, I saw no need to move on. Mike lived in his sister's basement since his parents had kicked him out.We were both pot heads and we made enough at Tony's to buy some weed. We ate at Tony's and paid no rent. We both either walked, took the bus or road a bike. Picture a...

My birthday treat

My next door neighbour had begun helping me with my crossdressing by buying me my own clothes, and despite her initial stipulation that I continue to dress in secret, we had experienced a moment where that had all changed. Once that day had passed, Ellie and I became almost inseparable. If we weren't together, we were texting or talking on the phone. We would do everything an ordinary pair of best friends would, with the exception, of course, that Ellie would help me with my little secret....

First Time First Fuck New Porn Star

I am just a normal guy however I have what some would call an abnormal fetish. I am a 23 year old guy and I like to wear and dress up as womanly as possible. I am 5’9, a little chubby but can still pass as a woman, with brown hair, brown eyes and a 5 inch cock. One night I had gone out with one of my friends and had gone drinking to a few bars. As we went from place to place we started to get more and more people with us until we had a fairly large group. At about 2am, the friend I had...

Surrendering to Temptation

Sixteen-year-old Grant waited until he was sure that the house was empty before heading to the laundry room in the basement to recover his basket of clean clothes. He needed to be alone because of what happens when he went down there and today would be no exception. However, today was the day he decided to do something about it. As he switched on the lights and slowly descended the stairs his heart began to beat a little faster with anticipation. Once in the laundry room portion of the...

Nice Encounter

We walked into his apartment and he said we can be comfortable here in the living room. He started to remove his pants, so I did also. He was down to his bikini panties and after he took off his shirt, he pulled his panties down and off. He was now nude and I got my first look at his cock. He looked large, long that is, and he was cut. I finished removing my shirt and stood there in my garter belt, black stockings, and black bikini panties.He said, “Nice.” I had told him over the phone what I...

A Nanny Femtastic Chapter 1

A NANNY FEMTASTIC! Chapter 1 My story starts during a very bleak time in my life where I was unable to find continuous work of any meaningful type. I had, I suppose, looking back now, rather stupidly pursued Child and Nursery Care as a further education route. Much to my parents consternation! Yes I was the only guy in the college but I thought I would soon move into management positions and my career path would take off! It was actually cool to have so many women around me, and I did have...

Chris s First Anal Experience

A few days after my first oral experience with a man, I decided I needed tits like a real woman. I went online to a few cross-dresser sites looking at their breast forms. There was quite a large variety. I looked through the few bras I had to see which size fit and looked best.The 32B was cute and seemed proportional to my small frame. I ordered a pair of symmetrical forms and a pair of asymmetrical forms in a 32B size along with the medical adhesive to attach them. The confirmation noted it...

Accepting an invitation

On the third day of house sitting, I awoke to a nice surprise. After my neighbour, Daniel, had unexpectedly visited, I had decided to work on my make up and mannerisms. After a day of walking in heels, I had perfected my sexy walk as well as getting my make up just right. I was feeling in the mood to show off my new found skills so was excited to see a note waiting by the front door. It was from Daniel. It said that his wife and daughter would be out all day and he would like me to come over...

GurlsOut

Having been into womens clothing since an early age,as I got older I often wondered about going out dressed up and hitting a local bar as a girl. Well I finally got my chance back in 1984. I was in the Air Force stationed in North Carolina and had already made a connection with a local man down there and we had sex on a pretty regular basis. He knew of my desire and one night we decided to go for it. I am pretty small body wise and kept my whole body shaved and I could pass as a woman when...

My First Time

This a fantasy of mine and my first story that I am submiting. For a long time I had thought about oral sex with another man. I was married a few times and it never really satisfied me completely, I loved sex with them but I longed for sex with a man. I had wondered what it would be like to find a man looking like a woman, I talked to female friend and she helped me to dress up like a sexy hot woman. She helped me to shave my legs and she picked out some hot looking clothes. As I put on the...

Very Good Friends Continued

JimTurning around, Gerry came back and kissed me while cupping my groin and giving it a squeeze. He led me through the back door and around toward my car. After one more kiss, he suggested, "How about I meet you at Fratellis in about an hour. I need to rinse off the sawdust and change into something a little sexier.""Okay, but you better not stand me up, or I'll come looking for you.""No chance of that!" he grinned before imparting one last kiss.GerryYou slide into your car and drive off.I go...

Soldier Standing to Attention

I had been flirting with a soldier that I had met online for a while. He was a lot younger than the guys I normally go for, but surprisingly open minded for his age. He was also really hot and had a nice body, so I agreed to meet. We toyed with the idea of some roleplay during our online chats. My favorite was the wounded soldier and the slutty nurse; it made me very hot. I got myself a nurses outfit for the date. It was PVC and very short. I also got some new, white stockings with bows on them...

Surprise

Aubrey swallowed the lump in his throat as his wrists grew sore from his restraints-being handcuffed to the headboard of the bed, naturally he grew stiff. Speaking of stiff... he peered down, under the frilly black miniskirt of his maid outfit was a visible bump, straining against the panties that constricted it, said lingerie was clinging to his soft pale skin. He bit a plump bottom lip and sighed, blowing a scarlet lock of hair away from his face. If only his bastard of a boyfriend would get...

Surprise Delight

It was a beautiful day outside and it had been a long hard week at work. I decided to pamper myself by taking a nice long bath and just soak my sore muscles. After my bath and weekly grooming I decide it was time to slip into something a bit more slutty to wear around the house (I don't go out dressed up, not quite passable for that step). I walked into my room and looked in my closet, where I kept my sluttiest outfits. I picked out my bright pink and purple trimmed corset with matching garter...

Tina and me

"Dang, I don't have any clean underwear!" I said out loud."Want to wear mine?" Tina asked.I didn't know what to say. Tina and I had been together for only a few months, but things were going well; she had just moved some of her belongings into my house and was staying over almost every night. Did she know more than I thought? How could she?Maybe she'd gone through my dresser drawers and found the girly clothes I kept there or looked way in the back of the closet where my three dresses hung.I...

A Nanny Femtatastic 4

NANNY FEMTASTIC! Chapter 4 ….I was aware I may be called upon by one of the girls in the night so would have to stay in bra and panties. I also had to ensure I shaved thoroughly early in the morning and hid away my razor and foam! I woke very early the next morning, thankfully no calls in the night! I shaved everywhere and slipped into a fresh bra and knickers, ensuring my special strapping for my penis was re-fitted. I dressed in a white blouse and put on a pale blue pinafore dress, tights...

I Dressed Charlie Like A Girl And She Never Went Back

Today is our long awaited graduation exercises. I am just waking up from last night's party, Charlene is already up and in the shower. Not surprising, because she always loves to look her best in the morning. This morning was going to be very special in honor of graduation and celebration of our almost four-year love affair. Well, at least that's what she promised.I kicked off the sheets and admired my morning wood. I could hear Charlene humming so I knew she was done showering and was now...

The Feminisation of Michael Chapter 6

The Feminisation of Michael. Chapter 6 The taxi dropped me off at a top hotel in London. I checked in as Miss Michaela Wilson. My new name! I had credit cards and bank account details sorted out when I was in hospital so had a purse full of plastic! A bit like I now had a bra full as well! After the porter had left me alone in my suite of rooms I just collapsed onto my bed. What an amazing few months I thought. This is now the start of a new life as a totally new person, in every way! ...

Late Night Bus

It's a beautiful, foggy English night. Panting, my lungs aching from the cold, I reach the bus stop at a dead run skidding to a halt on the loose crumbling tarmac. The salty taste of Steve's cum still fresh on my tongue and my anger unabashed. Catching a breath, I realise just how much I love nights like these. The ubiquitous street lights struggle to penetrate the gloom of their individual kingdoms, the trees and shrubs of this quiet suburban avenue glistening darkly in the moist chilled air,...

In Her Shoes Part 3

I guided Peter into the main shopping mall in town leading him straight into a shoe shop. The girl in the shop fetched a few pairs for me to try on and I relished asking Peters opinion. He tried not to look too obvious that he was hooked on my shoes and feet. I 'hummed' and 'ahmmed' a short while, telling the girl I was undecided and may well be back later.Grabbing his arm once more we walked around the mall going into various shoe shops. In the ones without sales staff I would make him fetch...

The start of my life as a submissive crossdresser

I am a bisexual cross-dresser/sissy and have been enjoying my life as such for many years. It all began for me when a friend asked me to look at some of his 'girlie' magazines.We went up to his bedroom and looking through the magazine got Chris really excited and he got his cock out and started to masturbate. I couldn't take my eyes off his cock and I slowly reached out and touched it and when he removed his hand I curled my fingers around his erect shaft and began to slowly wank him.I just...

Mia s Story

Before I start, a little about myself: I am Korean but born in the U.S. in Jonesboro, Georgia. Jonesboro is about twenty miles south of Atlanta. I am a third-generation Korean American so no I don't speak Korean and the only accent I have is a southern accent, not a Korean one. I was born a male and two months premature. While I was not born with any birth defects, as I got older, I never fully developed as other boys my age did. At the age of sixteen, I was much shorter, thinner, and had a...

Seduction of Piper

I want to thank Farmgal who's sexiness inspired this erotic and steamy tale. Thank you Farmgal, I enjoyed writing my sexy fantasy of seducing you.Stephanie was attending the check out register at Victoria’s Secrete when an extremely sexy woman strolled into the store. Stephanie’s heart beat faster and her eyes locked on this sexy woman as she sauntered towards the display of the new line of sexy panties and bras. The woman’s eyes locked with Stephanie’s for more than a few seconds. Stephanie’s...

My Sexual Odyssey Part VI A Working Girl

I decided to go to the club again that night, and talk to some of the people there. As nothing much happens until fairly late, I waited until an hour before midnight, then drove downtown. I entered the club and was greeted by the people who tended the entrance, to whom I was becoming a familiar sight. I looked for a table off to the side and searched for someone with whom I could converse. In no time I spied Trixie and waved for her to come over. “Hi Tracy, what have you been doing?” “Oh, all...

A Dirty Fantasy

TuesdayI’m looking at the parcel on the table right now. It seems a big box for what’s inside but that’s packaging for you. I offer my thumb up to my mouth and bite on it; nibbling at the skin before my hands come down on the packaging. I pick up the knife and rip open the seams; spilling out the contents on the table.I feel excited. Like this is something I have always wanted to do, to feel.I swallow hard as I pick up the inner parcel.I’m a little disappointed. It looks smaller than I imagined...

The Next Night Crossdresser Part 2 of 2

I woke up early from the sunlight shining through the windows. We’d forgotten to close the curtains when we collapsed into bed last night. Jenny was already awake and watching me. ‘I was just about to wake you up with a blow job,’ she smiled.‘Funny, I was thinking of doing the same to you!’ I laughed.Jenny kissed me then turned around in the bed to lay on her side so our cocks were facing each other. We both had erections already. I shuffled close and took her long cock in my mouth, closing my...

The Meeting

I initially met Richard through a TG Community site and we seemed to hit it off from the very start. He was very open about his likes and dislikes, about him being a TG admirer, about having had a fair number of encounters and dates, but he never pressured to know anything about me. Drawn by his gentleness and gentleman ways though I found myself sharing my deepest dreams and wildest fantasies with him through regular emails over the following several months. Richard had this way of...

Noodles Part 7

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

Prom Date Part 1

Jody was pretty much a typical 18 year old boy. He liked sports, hanging out with his friends, and playing video games. However, Jody had one deep, dark secret. He was addicted to wearing his sister's clothes. Every time the house was empty and he had the chance, he would sneak into her room and try on something pretty. Jody was always mortified of getting caught so he was very careful. He would only try on clothing and shoes. In other words, he wouldn't risk putting on any makeup or nail...

Aunt and Uncle Sex Slave

It was the summer of '82 and mom and dad were going through an awful divorce. They decided that it would be best that I stay with some good friends of theirs, Charles and Betty, while they got through this difficult time. They were an older couple, both were around sixty at the time.By this time I was a fully fledged cross dresser and no one knew of my secret except a neighbor. I had all of my own lingerie, heels, wigs, panties and hose, including breast forms to stuff my bras with. This was...

Across The Street The Conclusion

Mike left his telescope at the window even though it wasn't used any longer; his laptop was the new tool of choice. Every night around midnight he would receive a chat request and a second later Leann's beautiful face would fill his screen. There was the usual small talk about their day as Mike stared at her pretty face.They didn't have to talk about sex. Between her looks, dress and voice Mike always got hard. Leann seemed to be able to sense when he was ready and would start her music and...

What Happened After Police Arrest

Hi.I am now a mature gay crossdresser.A bit of history of my life as a crossdresser.I have been gay for as long as I can remember. I have always lusted after men. As with most crossdressers, I have tried to be (normal) but have always returned.I even got married and still am officially. Very rarely did I get hard for sex and was often punished for my failure, ordered to lick her out. I only enjoyed the punishment and luckily, she found sex elsewhere.Many encounters leading to my first anal and...

Porn Star Babe Part One

As a hot, 20 year-old girly boy, I was invited by another girly boy to star in a porn movie with her. It sounded fun and I was adventurous sexually, anyway. So, becoming an actress getting lots of big loads of cum from her handsome co-stars was very exciting to me.The movie was shot in a private house where I drove to with my girlfriend, Chrissie Licks, a pretty, 21 year-old, aspiring porn star. Chris was a cute blonde when dressed as a boy. He was also a call boy who was popular with older gay...

Returning To Old Habits

Like many cross dressers, I found my habit has a certain ebb and flow. I would bury myself into my kinky hobby for several weeks, only to hide everything away again. I used to have purges too from time to time, where I'd convince myself it was wrong and throw my clothes away, swearing I'd never do it again. The last time I purged was in my mid twenties. I'd been with my then girlfriend for around a year and we had decided to live together, so, in order to keep things secret, I threw all my...

I Was Wearing Panties When I Met Her

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

A Night of Firsts pt 3

We all took a sip of our drink. Catherine, Anna and myself, presided over by Lauren. I felt like a new gurl at this party. I bit my lower lip, I wriggled in my seat for my dress giving an accidental glimpse of way too much upper pantyhosed thigh.I blushed so deeply. Lauren must have sensed it as she leaned in closer and told me that I was a flirty gurl and those legs of mine might get me in trouble. I lowered my eyes and she giggled when I didn't meet her gaze. I fumbled for conversation until...

having some in panties with friend

First time ever sucking cock in panties: This is the first encounter Taylor had with another man. Taylor had just started wearing his mothers panties after taking interest in a mesh thong he found in the laundry. After a few weeks of wearing them he wanted to share his passion with someone else but never thought of who it could be with. All he knew is that it had to happen soon. That when Donnie came into the picture... literally.. It all started innocently enough...

The Wedding Proposal chapter I

I slowly let the sheer, white stockings slide up along my closely shaven legs. They were smooth as silk, and no hint of coarseness caught the fabric as I stepped into them. The broad bands of elaborate lace hugged my thighs and made me feel great. Four straps, each decorated with a small silk ribbon, held the stockings attached to the garter belt I wore around my waist. The coarse lace felt tight around my body, but I loved the feeling of the feminine garment. It filled me with joy and arousal....

For Mistress Sarafina Part One

Alice was clad in a tight pair of black lace silken panties that felt so smooth upon her caged genitals. This pair of panties, more so than any other pair Alice owned sent aroused shivers up and down her whole body whenever she was made to wear them by her Mistress. Mistress Sarafina had left Alice a detailed text message earlier in the day explaining what Mistress Sarafina expected from Alice when Mistress Sarafina returned home later in the day at 4pm. It was now 3:55pm and Alice was making...

House Sitting For The Holidays part three

We had been texting for a few days following our date, even spending a few late nights sending erotic messages to each other. Jackson seemed desperate for another date and I couldn't stop thinking about his cock.I lay sprawled across the suede sofa in the front room playing with my hair, wearing a bra and thong, some shape pantyhose and a pair of six-inch black high heels. I'd become accustomed to wearing ladies' clothes at all times and felt so natural in them now.My phone flashed as a...

Under The Table

The Bear on the Hill is one of my regular drinking establishments on a Friday evening. I seemed to have reserved this place in the corner consisting of a couple of chairs, a table that’s just high enough to sit under and a wonderful view of the bar. It’s slightly set down by a small step, and it’s where I go to be me.My name’s Carol. My other name is Carl, but when I go out to The Bear, I always dress as Carol. The clientele has only ever known me as Carol and I’m more than happy with that. I’m...

Dear Cum Captain Quentin Stocking

This morning I popped down to Pret a Manger to meet up with my good friend Albert Einstein for a slice of red velvet cake with a vanilla butter-icing topping and a medium cappuccino on the side. "Albert Einstein," I hear you say in a somewhat incredulous tone. Yes, Albert Einstein! THE Albert Einstein. I gave you all a perfect opportunity to invite me out for a yummy little Pret-fest back in Dr Flappyduck, but did any of you offer? Did you fuck, so it's just me and Albie yet again for our...

My wife catches me cheating then takes a year long revenge

Where to start? This is my favorite fantasy. I just got married two years ago, and my wife caught me cheating with her best friend. At first she was enraged and didn't speak to me for three weeks except to insult me, with constant references to my very little dick and what did Carol see in me but to hurt her? If I had understood how women feel, then this would never had happened! Then like a light switch she became sweet as ever. Waiting on me hand and foot, and the sex was like our honeymoon...

Meeting Clair

I was on my way home from the Minneapolis metro area. I was going right past the outlet mall and need to pick up some pantyhose to replenish my supply. I wear pantyhose everyday since I had my varicose vein surgery. The doctor suggested that I wear support hose to keep the problem from coming back. The nurse at the vascular surgeons office suggested that I wear Hanes Alive pantyhose as they were the right compression and that they would stay up better than thigh highs. She knows I work...

What s In The Name Shazstoned

It was a Saturday night some years ago, I was home alone, it was time to dress fully for the first time. I showered and had a good shave.I started with my false eyelashes on the top and bottom of my eyes, next the foundation and powder, eye shadow, a glittery green, dark red blusher to highlight my cheeks, black eye liner and masscarra followed. I added bright red lippy, all was applied quite heavy, how I like it.I got myself dressed, basque, seemed stockings and thong all in black, a very...

Husband Caught Cheating Punished

This is what happens when you get caught cheating on your wife. I love my wife dearly and never set out to hurt her. I was working away from home several years ago, and while I was away I became chatty with a lady at a nearby bar. Her name was Helen; she was very well spoken and was gorgeous. I had been visiting the bar for a drink most days after work, and Helen always seemed to be there. I was due to travel home on Saturday, and this was Thursday evening. While chatting, Helen asked if I...

A Nanny FEmtastic 9

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

Caught and punished by my manager part 1

My job as a sales rep meant I had to work away a lot, traveling around the country to various events and conferences. It suited my lifestyle as it meant I was able to indulge in my secret obsession of crossdressing. Every week I'd pack my suitcase with a new outfit of sexy lingerie, heels, wigs, makeup, a vibrating cock; all the things I’d need to satisfy my sexual urges each night when I’d finished work. The hotels were great as the rooms always had a shower, a large bed and lots of mirrors to...

Double header on the beach

My favorite beach is less than an hour from where I live on the Mid-Atlantic coast. It is actually more on the bay than the ocean with the upper portion of it being an unofficial nude beach. Due to its limited access and lengthy walk, the upper beach has become a haven for gay and bisexual activity. At its peak season, it is still sparsely occupied with fewer than two or three people per hundred yards. The beach is only twenty or so feet wide, at high tide, with heavy vegetation behind it...

Adventures in a Woman s Body Chapter 1 Plugging Up

After two years of hard work, I've finally come as close to being a woman as possible. The hormones and drugs that I've been taking for the past five years have made my body and voice quite feminine. With the help of toning exercises, I now have long slender legs, a soft and juicy ass, very feminine hips and a thin waist. My skin is very soft, smooth, and white thanks to the skin care products that I've been using every day. Also, with the help of makeup, I look totally passable as a hot and...

My Sexual Odyssey Part 1 How I Got Started

I was always extremely sensuous, expressed in the love of the feel of satin and silk, as well as the feel of going barefoot, which was nearly impossible in the city, even indoors, not part of the culture. Where I live now it is, and so I go not only barefoot but also nude when at home. I don’t know if this is significant or not. However, the first time I noticed anything unusual was probably when I saw a film on TV in which a boy masqueraded as a girl for some reason or other. I recall how...

Motel Fun for College Crossdresser

Before I start the story I want to describe the setting so you get a better idea: it's a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a family sleep that's for sure. The layout of the motel is a rectangle. The rooms surround the rectangle's perimeter, in the center there is a pool, a park area, and a parking lot. There is a walkway around the entire inside perimeter of the rectangle and every room has two doors, one facing the exit and...

Unexpected Turn of Events

I sat in my favourite bar sipping at my glass of Chardonnay; I had been coming to ‘The R Lounge’ for a couple of years. I watched the guy talking to his friends across the room. They were all dressed with a bit if style but he had caught my attention. He was wearing trousers with a casual blue and black stripped shirt. He was probably five feet nine inches tall. He had an average build; not to slim but trim enough to know that he tried to stay fit. I guessed he was around forty years old. But...

A Crossdresser Gets Caught

Johnny was gentle and had slightly feminine mannerisms for a guy. He had had quite a few escapades with women, a couple of failed marriages and a dozen or so relationships but all had fizzled out. He had never thought about the fact that maybe he was gay or bisexual and although he was not homophobic he thought the idea was not for him. He found women attractive and loved them wearing sexy lingerie and became almost obsessed with lingerie and all its variations, sometimes even more than the...

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

When my mom and I had gotten home, I immediately ran into the house to take a shower and change as quick as I could. I re-shaved my entire body and removed my makeup so that I could start from scratch and apply it again.Once I was finished with my makeup, I see a new outfit laid out on my bed. This was a cute nurse outfit with a short tight skirt that barely covered my ass. It was also pink with white stockings and long lace gloves that went up to my shoulders. Finally the top was like satin...

Becoming John Collins Mistress Part Two

The next day, everyone was a bit hung over. I needed to pick up my car, which I’d left at the bar the night before. Joe said it was on his way and he’d be glad to take me. I borrowed a raincoat from John to wear over my skimpy outfit, then Joe and I headed out. Joe was making eyes at me during the drive, and I decided it would be best to come clean. “Joe, there’s something you should know about me,” I started. Joe quickly said, “Hey, baby, there’s a lot I’d like to know about you.” “Yeah,...

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...

A Close Encounter Part 2

The dim ambient lighting inside the Coach House Inn gave the lounge a golden hue that was ideally suited for a guy masquerading as a gal. I couldn't have wished for a better location for Judy to come out to play. My wish list, however, would not have included the guy breathing into my left ear."Perfume?" I croaked, continuing with the 'sore throat' ruse.I began to feign a cough in order to turn away from Ross's advances. Paul had just retrieved his tongue from inside my wife's mouth and...

Uncharted Territory The Conclusion

Cal was up earlier than normal for a vacation day and was in and out of the shower long before his parents woke. As he waited for the coffee to finish brewing, he wondered what the day would bring. He also thought about the dreams he had last night and hoped it was a premonition of things to come.In his dream, he was clad in the softest and silkiest lingerie imaginable. Cal saw himself in a black bra trimmed with delicate black lace and a garter belt that matched. The garter belt held up a pair...

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

After our time at the spa, I spent a lot of time in my room trying out all the new sex toys we got from Richard and Monica. They were all exciting in their own ways and I came so much with each one. Some vibrated, some went deep and some felt good stretching my ass wide. The feeling of all the sensations I could get from my new plastic and electric friends were amazing and found myself spending long hours with them. Once I was finished, I had to stop to rest as they had left me completely...

Son s Bikini

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

A Nanny Femtastic 2

A NANNY FEMTASTIC! Chapter 2 …I just couldn’t work out what was happening. I loved dressing in girl clothes, I felt relaxed and unstressed. But where was this leading! How could this work? I had never seen my parents that regularly maybe twice a year and they had mentioned on the telephone about meeting a few times. I put it off due mainly to my eyebrows! But I couldn’t put them off indefinitely. I had also stopped seeing my mates who I used to hang around with at the rock clubs. Alex came...

The Early Steps of an Odd Couple

Louisa and I were of the same age, lived with our mothers only a few streets from each other, and attended the same Secondary school. Yet, we had never met. In the 1950s, the belief that boys and girls should be kept apart and raised separately still held sway and was strictly enforced. Incredible as it may seem today, a boy or girl observed so much as talking to each other would certainly be punished for wanton behaviour. Believe me, there were plenty of busybodies and miseries around only too...

Surviving The Covid 19 Lockdown

Tristan or Tris as he preferred to be addressed had everything he needed to survive the mandatory lockdown. His larder was so well stocked that it would be about six months before he would need to worry. He was ahead on his bills and mortgage payments and he had money in the bank so that was not a worry.He had purchased one of the top-of-the-line gyms on the market today not too long ago cause he found one at a decent price. Now he could continue with his fitness regime without interruption of...

Vanessa Spends a Night Semi alone

One night I was laying around bored, so I decided to get all sexied up for no one but me. I got out one of my favorite outfits, which you can see in my picture. I was so excited as I undressed, and laid everything out that I was about to slip on.First I put on my sexy Victoria's Secret thong. It was white with black lace, and it felt so hot as it slid on. Then, I put on the matching bra. It had a lot of padding, so even though I have a little bit of a chest, it really helped to give me that...

Two Girls Are Better Than One

My girlfriend, Sherry, had nice, big C-cup titties and a face like a young Marilyn Monroe. Needless to say, she got hit on by lots of men wherever she went. She was also a nyphomaniac who liked to be fucked ten times a day, so we had a great sex life. She found out I enjoyed wearing lingerie, so, as part of our sex play, she would dress me up in her panties and bras and stockings and put lipstick and makeup and eye shadow on me. This kept me hard for her for hours and she really enjoyed all the...

The Awakening of Susi

Ever since I can remember I have loved being feminized and being made to wear very slutty clothing. This is a true story of my first experience at a glory hole and a coming of age for my sissy self. I had many female friends who loved to dress me up in their sexy clothes and strut me around in front of their boyfriends. They thought it was cute to see me in full makeup and a wig wearing a sexy nighty or a micro mini with fishnets and heels. I loved every minute of it and learned a lot about how...

Sissy Blane s Liquid Assets

I became familiar with the Plumrose Dossier one cool February morning when it was read to me in the private rooms of Madame H at the Clinic.***I'd arrived that morning for my weekly 'therapy' and had only enough time to hang up my outer clothes in the Sissies' cloakroom and don my Eva Gabor wig before a facilitator poked her head in and told me I was wanted in Madame H’s office immediately. Even at that point I knew this couldn't be good so I shrugged into a nylon dressing gown and followed her...

Simran A crossdresser part 2

Well after my little adventure in the bathroom with my mom's panties, I went out for a couple of drinks with my friends. But, in spite of having company, the only thing that kept playing in my mind was the feel of those satin panties and how horny I had felt in them. All I could imagine was getting back to the house as soon as possible, before my parents returned, and having one more go at it. I returned around seven in the evening. Since my parents had a convenience store, I knew they wouldn't...

An Uneven Christmas

By Christmas, Sarah and I had been ‘dating’ for a few weeks. If you could call it that. I had been spending a lot of my time with her, but I often felt more like a servant than her boyfriend. Most couples might curl up together to watch a film, I was more used to curling up at her feet. Worse, I was sure my friends realised there was something odd going on. Mark, who had the room next to mine often smirked knowingly at me. The others were always a little cold around Sarah and had started...

An Introduction to Crossdressing Pt 3

As I was following Jackie to the hotel I couldn’t stop looking in the rear view mirror at what was a complete transformation in my mind. I kept doing that thing where you look away and then back hoping to catch your reflection not keeping up with you because you are sure it is not you. It is probably a good thing that there were not very many cars on the road since I wasn’t paying any attention to it while I was admiring myself. I did see Jackie’s turn signal and brake lights just in time to...

It s A Family Affair

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

576 Shadow Oak Drive Part 1

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

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