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Becoming an Escort

The nights second cock spurted hot sticky cum on my face and I greedily pushed into my mouth faking my enjoyment of that bitter taste. My “lover” dressed and left the room. I lay back on the bed where two men had fucked me that night and pondered how I had got into this position. Despite myself my cock was rock hard in its silk panties stained with my own cum. 3 weeks earlier I had told my wife we were broke and that my business was finished. She had been quite calm and had gone out of the...

A First Time For Everything

Matt looked exceptionally young for his age and blessed with a complexion that meant he wasn’t all that troubled by facial hair. Spots were non-existent, always had been, even in his teens. Yet at twenty-eight years old you could never classify him as normal. His slim body, born out of long legs and a standard-sized upper torso fulfilled all his needs. He couldn’t be described as ripped at all. In fact, with the right hair, makeup and clothes he would pass as a woman.It wasn’t that he hadn’t...

Friend s Treat

I had recently split with my wife and was feeling very down.I was invited to spend a few days with my old friend Dave and his wife Tracey.The first night I was there Tracey turned to Dave and said that we needed a boys' night out and why not go to his club. Dave agreed it was a good idea and within minutes Tracey was dropping us outside what appeared too be a Georgian townhouse.I hadn’t known that Dave was in a club and was surprised to find he was a member of one. He had refused to reveal what...

Felix becomes Felicity Chapter 7

FELIX becomes FELICITY Chapter 7 …We both fell asleep almost immediately. I got up whilst he was still asleep in the morning and put on his shirt loosely over my naked body. I woke him up with breakfast , we kissed and he left late morning. I had been lucky to escape him not discovering my penis! I had to think hard about what to do about this. I would just have to have to tell him my secret, that I was really a guy! Bradley was going to take me out to dinner that evening, and I thought it a...

Eat You re My Bitch Now

I was nervous as I waited patiently, watching the road. My hard cock was straining against the pink panties and the skimpy Victoria's Secret nightgown barely covered the bright red bra I wore. I stood by the window, looking in distance for my wife, Jenny's car.Jenny was just out on errands, one of which was dropping kids off at school. Officially, I was 'working from home', but in practice, I just had to check messages late in the afternoon. That meant, we had the house to ourselves with no one...

And It Begins

There seems to be a common belief, if you want to call it that, that there are basically three “levels” of Crossdressers or Crossdressing. The first of these is what is referred to as fetish dressing. These people have no intention of doing anything other than wearing items of feminine attire. They have no desire to even attempt to emulate the female persona. This is purely a very temporary thing for little more than the thrill of it. The next group that they describe are interested in...

Taking That First Step Part 2

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

In Wonderland Pt 1

When I was in high school I was always very camp, which was probably why almost all of my friends were girls. This was definitely why I first ended up crossdressing. I was sixteen and round one of my 'girlfriends' house for a few drinks on Halloween before we went to a house party nearby. I never much cared for Halloween, so just came as myself. When I came in they all sighed since I wasn't in a costume, but dropped it fairly quickly. We sat having a few glasses of wine and waiting for the last...

The Skimpy Red Dress

There is a very special sensuality in the image of a pretty blonde haired girl who is petite and shapely enough to be able to look great in a tight and skimpy dress. I confess to owning many of these types of sexy dresses. Because I am five foot five inches tall and slim, I am able to look rather alluring while dressed in one.I have many styles and colors and usually favor black. Once in a while however, I wear a skimpy, bright red dress that speaks volumes. I have to admit that on one special...

All by mistake

It all began by mistake. I had spent the morning at home, relaxing in one of my favourite outfits. I was starting to think that work beckoned, and had begun the transition back to drab. I took off my wig and make up, but decided to keep my panties, tights and bra on, as my clothes would hide what I was wearing. My attention was caught by a news item, and I sat watching the television for a few minutes. My viewing was disturbed by a ring on the door bell, and I went to see who was there. I...

Telling Mom I m A Crossdresser Part 8 5 Cops and Prostitutes

When morning came, I told mom what had happened the previous night. She had a surprised look on her face and I could tell she was feeling uneasy at the thought of me getting arrested while dressed as Missy as well. We talked for a while and she was glad as well that the police officer was a Missy fan.“We can definitely let him have a free night in exchange for not getting a criminal record.” Mom said as she gave a sigh of relief.We started to talk about the sybian that mom had bought and some...

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...

Phoenix Park Night

I am a 32 year old married guy who happens to like wearing ladies' lingerie. My fondness for wearing lingerie goes back to my late teen years when I would wear my mother's clothes and underwear. I went on to wear my sister's undies and this continued into adult life where I have worn the undies of many ladies (without them knowing it). Until the time of this story, I never ventured out wearing women's clothes but on this particular night, I put on a pair of my wife's tights and a pair of red...

Two girlfriends have a couple over for a fun night

My wife Dawn had surprised me by saying we were spending the night in as two girlfriends, laying out my clothes so we matched. Then after having amazing sex, Dawn surprised me by telling me that she had invited her friend, Maria, and Maria’s husband, Mark, over for some fun with the two of us and to fulfill the fantasies of all of us.So I was standing there with my red plaid skirt, white top, and red high heels, and my cock was rock hard underneath my skirt, and my mouth was wide open at this...

Telling Mom I m A Crossdresser Part 6 Missy and Mistress Keri

Up until now, I have enjoyed my time as Missy. My mom had kept me busy with clients and we pulled in a lot of extra income and I was able to experience a lot of different fantasies, However I had not had the chance to try anything involving BDSM, or not yet at least.One day I came home from mowing the lawn for an elderly woman when I walked in the door to find my mother smiling deviously at the kitchen table. I instantly knew that Missy had been hired for another job.I sat down next to my...

Jaq Invites Crossdresser Over

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

Dad Pimps Me Out

I think once dad caught Jack fucking me,he wasn't upset,but more so he thought of a way to use this to his advantage. After that it was nothing for me to walk around the house in womens clothing,for my dad and I had a talk and I told him that it felt right. One night when he brought home a sexy outfit for me,I knew he was up to something. He handed me a bag and said "here,go put this on". He tells me to get my make up on and meet him back in the living room in 20 minutes. I go into my room and...

Lovers in the Afternoon

Through the scrim curtains, the soft afternoon sun lights the room with a pastel glow. I sit at the chair in front of the dressing table, quietly smiling to myself. I finish putting on my make-up; a light touch of lip gloss. I look at myself in the mirror. Quite good I think. I am getting better all the time. I can feel the tension and excitement in my body. My perfume fills my head. My skin tingles, only partially from the hot shower of 30 minutes ago. I brush my hair into place. A movement...

Doing the landlord Do It In Mexico 2

...........I got home from my first day gone public fully dressed as a lady. It was late in the afternoon, I filled my bathtub with warm water , put in scented bathoil in it , laid in there for an hour and 20 min. Thinking of that day in town , when I was getting fucked by FRANKLIN . Just thinking of that whole scenerio made me horny . I started slightly fingering my asshole, but that could not compare to the hard cock FRANKLIN drove inside me with such TLC. My cock was so...

No Strings Attached Sweetness and Lace Chapter 20

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

The lady in 237 Conclusion

As his orgasm ebbed Nick pushed himself off the wall and headed to the bathroom to clean off. Once complete he wrapped a large bath towel around himself instead of finding the clothes he arrived in and returned to the bar where he found Candice waiting for him. He took a seat on the stool next to her and she slid a fresh drink toward him and they once again clinked glasses.As he watched her drink he still could not see any trace of a male in the female next to him. As they drank in silence Nick...

Taking Control

this is a story of how my wife busted me doing some of my favorite things and then took control of the situation with some role reversal to satisfy both her and my hidden desires - enjoy! It was one of those rare days when I was working from home and my wife had plans to be out running around with a couple of girlfriends for most of the day. Work had been dragging me down and I was in serious need of some personal time. As soon as I kissed my wife goodbye, I scurried into the bedroom to raid...

Jessie s Fantasy Chapter 7 The Tables Got Turned

Here I was, getting my boy pussy plowed by my good friend Scott, when Mark decides that he needs to call Jesse, the male me. As he was starting to dial my phone number I realized that I never turned the ringer to vibrate after we left the night club. I was panic stricken as they all knew the distinct ringtone that I used. I couldn’t let my phone blow my cover. I had to think fast, but what to do? Suddenly, Scott moaned that he was getting ready to cum. This was my chance. I now had a plan. The...

My New BFF Part Five

Wednesday morning I woke up and took a shower before going back to my bedroom to pick out some clothes to wear. Although I was starting to accumulate a small wardrobe, I still had a long way to go and found myself with little choice for the day. Also, most of my clothes were now in need of being washed. I put on a pair of lacy pink panties, a matching padded bra, and the only clean pair of shorts and blouse remaining. It had been five days since I wore any male clothes. I thought about...

My First Sissygasm

This is a true story about the first time I felt the sensation of cumming like a girl. I don’t mean a prostate orgasm, where you ejaculate through anal penetration, but my first time feeling what I can only describe as a full body sissygasm. It was another night alone, dressing up in my apartment. I was feeling really girly and really horny. I took my time getting myself dressed up. After a nice long shower, I shaved my legs and any other annoying body hair. I got out, dried myself off,...

Becoming Mary Part II

When Lucy had told me about Amanda liking men wearing panties I thought she was talking about a fetish thing. I didn’t realize there was more to it than that. About a week later I had just arrived home from work when I met Amanda in our apartment hallway. She had been to see Lucy and was on her way out. “Hi Amanda,” I said as she stepped into to the elevator, “How are you?” “I’m fine,” She answered rather abruptly, “But Lucy isn’t at all happy.” Before I could react, she had pressed the door...

The Slut Within

I was 22 years old at the time, and I had been crossdressing for a few years. For some reason I could never control my desire to put on women's clothes and prance around my apartment looking all sexy and slutty. Normally I can never decide what specifically to wear as I like to change it up all the time, from wearing latex lingerie to sexy roleplay outfits and beyond. I am 5'9 with a slim build, shaved body and long brown hair and eyes, with a 5 inch clitty cock. I had never had sex with a man...

Telling Mom I m A Crossdresser Part 15 2 Kinky Girls

It had been a week since Mom and I spent the 4 days at the spa and hung out with my old babysitter Laci and for a while it was back into our old routine of working and coming home. Day after day I kept thinking about how her warm wet pussy felt wrapped around my cock while the feel of a sexy thong rubbed against my asshole.I came home one day to find my mom was packing a bag. I asked her what she was doing and she told me that she was going out for the weekend to visit an old friend from high...

Completing My Visit To Joann s Club Paradise

It was the second day at Joann’s Club Paradise. We finished our breakfast and decided to lay by the pool since we were all up late the night before. After a few hours, I told Gail I wanted to go to the salon to have my wig and breast forms checked. She told Tom and Vince we needed to fetch some “lady things” and we would return in an hour. Amanda was at the salon counter when we went in. She smiled and asked how we were doing. I told her my wig was looking messy and asked her how long I could...

Second Encounter Ch 4

I awaken at the first rays of light streaming through the curtains. I slip out of bed, freshen up in the bathroom, and make my way to the kitchen. I start the coffee pot, and soon the rich aroma fills the cottage. I hear you in the bathroom, and soon you make an entrance into the kitchen. "Good morning, Sunshine," I quip, " How did you sleep?""Solid as a rock," you say as you rub your eyes."Coffee?" I ask."Absolutely!" you say with gusto."What would you like in it?" I ask."Cream, and lots of...

Early one morning

I work 12 hour shifts, days or nights, so I'm up at all hours. One morning, I was up at 4am to start at 6.30, so I had a quick cuppa then took the dog down to the park. It being September, it was very dark and very quiet. As I walked round the path, letting the dog do her business, I noticed a woman sitting on a bench under a street light. As I approached her, she said good morning, I replied in kind and we started to chat. 'She' was actually a CD, and she asked me if I minded her being dressed...

Making friends with my housemates

People always react in different ways when they find out about my cross dressing. Girls are usually more accepting than guys but everyone is different. I was twenty-two when I went to university and decided I would be completely open about it with everyone I met there. I found that most people were pretty cool with it, although some took some time to get used to it. I spent the first year living in halls with three girls and two boys, and thanks to the first night together where we all had a...

My Crossed Life Chapter 5 A Very Happy Halloween

The days couldn’t go by fast enough as I patiently waited for the last weekend of October. While crossdressing on Halloween seemed all too cliché, Missy and I had collaborated on quite an outfit that undoubtedly would be my most outlandish and revealing look yet. Missy and her friend Laura had decided that a trio of slutty pirates would be the perfect opportunity for Jenni to make her college campus debut. Missy said she was up for the challenge to make me undeniably passable as long as I was...

Do you want to wear my skirt

As I sat in the meeting I couldn't take my eyes off her. She was young and so cute and she was wearing a short pleated wool skirt. The skirt was a pink and light blue plaid color. She would cross her legs and pull the skirt down being sure not to show too much. When we went on a break many of us went outside. It was a nice comfortable fall day. I watched as she came out and stood by herself. She took out a cigarette, lit it and started to smoke, just enjoying her break. I was surprised she was...

Girlyboy Gone Wild Part Seven

After getting Rich big and hard with my sexy outfit, I was now ready to put on a show for himWhenever men see me in my panties, they want me like a girl. It follows that whoever wears sexy little panties also likes big hard cocks to suck on and play with. My sexy French maid outfit was especially good at making me feel like a slut for a man. Since so many men had fantasized about being with a French maid, wearing the outfit makes a girl feel extra seductive and slutty.With his big hard boner...

Wedding Night Part One

As a tranny callboy/escort, I was always fulfilling the fantasies of lots of gay and bisexual men. But there was a fantasy of my own I had had for awhile that I wanted to fulfill with a handsome bisexual escort myself. I wanted to hire a handsome stud escort to pretend he was my hubby and have honeymoon sex with me like I was a bride on her wedding night.Every single girl fantasizes about having a big handsome man to please every night, to sleep with her and spoon together after sex, feeling...

Second Place Winner

I’ve been dressing up as a girl in dresses and going out in public for the past two years since entering college. My goal has always been to be as pretty and as believably female as possible, when I choose to dress up as a female. I am blessed with being short and slim with facial features that can make me very realistic in make-up. Blonde hair extensions, false eyelashes, and glue on nails complete a look that can be credibly convincing according to friends!I have always tried to work my...

Femme Boy Gets Cock Drunk

I’m not a very masculine guy. In fact, I’m downright girly. I blame my body. I’m 5’3” and weigh 110lbs, but the first thing people notice is my fat ass. It’s fat, tight, and juicy. It’s the kind of ass that women these days pay a queen’s ransom for. It flares out with my wide hips from a narrow waist and flat stomach and is complemented by proportionally thick thighs. My calves are well-defined, my ankles thin and delicate, as is my upper body. Other than my ass and thighs, the only fat on me...

The Opportunity

THE OPPORTUNITY PART ONE I suppose looking back, that my childhood was to blame, that is if there was any real blame to be attached. It could have just been my inherited genes so I can happily blame my mother and father for being the smallest in the class, but I somehow also got left out when the popularity genes were issued, I became a loner and spent far too much time in my own company for any real good to come of it. I loved the movies, the actresses were goddesses...

Discovery

Discovery, one of the greatest fears he has. All others take a backseat to his fear of being discovered indulging in his passion. You see Kyle is a cross dresser.Like so may others he doesn't know where this desire to dress up came from, but soon it was too strong to ignore. He started out with pilfering a few items from his sister's room and wearing them behind closed doors when the house was empty. But it wasn't enough.To his delight he discovered that there were literally hundreds of sites...

Meeting One of the Neighbors

Tom was almost seventy. We lived on adjacent streets and his property backed on mine. I had moved in only a couple of weeks earlier. I was renting the place. I was so excited to be on my own at last, especially because I loved to crossdress. My new freedom was exhilarating. One day I’d been in my back yard in the late evening, dressed in a cute white bikini. I was lying face down on a lounger, my bikini briefs down low enough to free my cock and ass. There had been a full moon that evening...

My First Cock

I am now Staying with my cousin after my previous story so I can dress up as much as I like. my Birthday was coming up soon and my cousin said she would have a celebration all weekend for me as it was during the week she said this would be my entrance into womanhood. It finally arrived this weekend I thought would be the best I just showered shaved what body hair I had off then left the bathroom into my room where I found a naughty school girl outfit with a note from my cousin saying put...

Warehouse slut

There I sat at my computer, ready for another morning of chatting with my new online lover, much like all other mornings for the last two weeks. It had become quite routine for us to chat for about an hour in the mornings, then off to our lives. I was, quite honestly, starting to lose interest, figuring he was just another of the "Internet fakes". We have all run into them, the guys who are all talk and no action. This morning, however, would turn out much different and I was in for a quite...

Taking That First Step A New Chapter Begins

The Summer was drawing to a close, and Lance would soon return to school for his senior year. As excited as he was about his final year, he was saddened that meant no more early morning rendezvous with the stunning Cassandra.It had been a great Summer. Thanks to her assistance Lance had taken his desire to crossdress to a whole new level and he became Lana. In order to complete his stunning transformation he spent many hours in his room at night working on his skill at makeup. Over...

48 Hours Chapter 3

Chris spent a couple of hours mowing the lawn, cleaning the car, and all the other normal weekend jobs that need getting out of the way, the only difference from normal being that he was still wearing the panties and camisole under his jeans and tee-shirt. From time to time he practiced speaking in his feminine voice, working on making it more consistent.Lynn had gone out again, and when she returned, she asked Chris if he had anything in mind for the evening, but he said he was easy."In that...

Happy To Be Used Pt 7

Bachelor party Friday was finally here. I would have woken up early, but I had partied really hard the night before and so I woke up with a crazy hangover. Good thing I had until that night to recover and get ready for my performance.Being hungover turned out to be a blessing in disguise because rather than doing anything all day and using up my energy, I essentially sat around the house, smoked a ton of dope and relaxed. By the time 5:00 p.m. arrived, I had slept for at least five hours and I...

Three nights in London Night 1 Irene s transformation

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

Caught

It seemed to Ken that time had slowed down to a snails pace as he watched the events unfold before him. The door to his sister's bedroom seemed to take forever to open and for Connie to step inside. Connie's head was down as she placed something in her purse before it rose up. That act also seemed to take forever as did her eyes growing wide as she took in the scene in front of her.Ken could blame no one but himself as had been pushing his luck as of late, but never imagined that he would...

Caught and the Consequences Part 3

Part 3 I signed the contract and handed it back to my wife, well my Mistress now I guess. She took it from me and said ‘Good girl’ ‘As you will have seen you are now Philippa, now go and get all your male clothes.’ ‘Can I get dressed’ I said. She slapped me hard across the cheek. ‘When you speak it will be respectfully and always address me as Mistress or I will make you remember’ ‘Sorry Mistress, may...

A Night at the Ambassador

While on business in Colorado Springs, I had the opportunity to visit one of the adult theaters that I had visited previously. Although the booth area was in full swing, the booths had no doors and there was no privacy what so ever. One could still have a good time if they were so inclined. The attendants were cool and they did not mind the actions of others as long as there were no complaints. On this late afternoon, I kept with my usual habit of dressing up in lingerie under my clothing and...

My Crossed Life Chapter 1 This is Jenni

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

Felix becomes Felicity Chapter 2

FELIX becomes FELICITY Chapter 2 My Mum and Sister went downstairs and I had a moment to myself looking in the mirror. I didn’t recognise me in the reflection I saw a teenage girl, a very attractive teenage girl! I joined my Mum and sister downstairs. I was becoming better on the heels “Mum I have to reiterate that this all ends in 6 weeks time right?”, “Of course sweet that’s what Dave said and I’m so sorry but very proud of how you’ve dealt with this.” She touched my hand. “And we can...

Work Hard Play Hard

After a long hard day of work, everyone decided to go to the bar after work. It was a busy day and everyone was stressed out; a beer amongst friends was just what the doctor ordered. The whole gang met at a Gino's, a local bar in a small Illinois town. The bosses were buying round after round, till everyone was all nice and liquored up. There was quite the crowd; about 15 in all. Dirty jokes, loud music, and smoke filled the air in the bar. We walked around like we owned the place, of course we...

Double dildo Please

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

My Dream story Part 2

"So you like this huh?" All I could do was stare.. "Y...yes Sarah" She walked over to me and slapped my ass hard. "Don't you dare call me that. From now on you will call me Mistress and you will be my little sissy slut. Got it?" "Yes Mistress. Sorry Mistress." I said. The feeling of my ass being slapped had instantly made me hers. I could feel my clitty strain against the soft fabric of my thong and I couldn't help but stare again at the big black cock and her massive plump breasts. ...

All The Way Part 3

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

Jenny Learns Her Place

His hands held my hips tightly and his very large hard cock slammed into my asshole again and again, as if he were was going to ram it all the way out my mouth. I whimpered with each long stroke while my own small dick dripped the remains of my orgasm. It was amazing that he was hard so quickly after pumping my mouth full of sweet jism, some of it even spraying onto my face. “Oh! Oh! Oh! Ooohhh fuck me good, baby,” I moaned over and over. I'd known Bobby since grade school and had even enjoyed...

The Best of Both Worlds

Daniel had known from the start, what he was risking when he entered into a relationship with Arya. There was a reason the woman had never settled down with any one person. Always open and honest about her sexuality, Arya was bi with an equal level of attraction to both sexes. She was also very sexually active, always telling her friends that she would never settle down with anyone, as the loyalty required for a serious relationship would mean giving up physical intimacy with at least one...

Being a Bride

The alarm went off and I turned over in bed, I could not believe the day had finally come. I slipped out of bed and adjusted my satin night dress, fixed one of the spaghetti straps on my shoulder and covered one of my breasts that was exposed.In the kitchen I got myself a juice and croissant and sat at the table.My thoughts went back several months to my first meeting with Steve, I had signed up to a website that helped crossdressers like me hook up with men who wanted to be with people like...

How Andrew became Andrea Part 2

"Did you cum?" Lacy asked."Yeah," he answered trying not to look at her."No need to feel embarrassed. It's all right.""I think I better go," he said and stood to leave."Can you come over tomorrow?""Yes, if you want me to.""Yes, I want you to. I will have a proposition for you," she said as she escorted him to the door."A proposition? What kind?""Tomorrow," she said giving him another long lingering kiss.Later that night in his room Andy jacked off as he replayed the events at Lacy's house. This...

Halloween Fun

My friend talked me into dressing up as a female this Halloween. It wasn't much of talking into; I was a closet cross dresser for sometime. The only person who ever knew was an old girlfriend, Mel, a few years back. It was a good thing she was bisexual because she was really into me wearing her clothes. She even mentioned that I looked better in her clothes than she did. So, I started wearing her panties to work, painted my toenails, and she even did my make up. We did break up, but I still...

Six Months

After all those years of longing to be free, stuck in relationships with women that frowned upon my cross dressing, I was still very much relishing my freedom. I was dressing every moment I could, the minute I got home from work every single day; a mini dress, heels and stockings were what I craved so desperately. I had been living alone now for a couple of years and would have thought he urge would have sated by now but I still hungered to be feminine at every moment. I am five foot six, small...

Becoming Mary Part I

Lucy and I had been living together for a couple of months when it all started. She was in her early twenties, and I was a couple of years younger. Up until I moved in with her, I’d lived my parents. My stay-at-home mother had taken care of all the household chores while my father went out to work. It was the typical old-fashioned family structure. From day one, living with Lucy was proving to be a bit of a challenge. For one, she had a full-time job and therefore not much time for housework,...

An Introduction to Crossdressing Pt 5

As Jackie and I pulled up to the club my mind was racing. My main concern is whether we look passable, and that if we don’t, that we might be laughed at and teased. As I expressed my concerns to Jackie, he said, "Remember that we are at a place for people like us who are a little different." As his statement sinks into my thick skull, all my anxiety starts to slip away. For the first time in a long time, I start to feel fearless. Being fearless is one thing, but making sure we look hot is...

Office Caught

My name is Peter. I'm twenty three and I'm a member of the small internal IT team at a large corporation. It's a typical office setup and our small team of three were kept busy with the day to day tasks; failures, PCs and printers and general support. I'm generally pretty quiet and unassuming and, whilst polite and good at small talk, I'm pretty shy, so just keep my head down and do my job. I joined as a junior aged twenty one straight from University. The office was full of people of all ages...

Ashley s BBC Therapy

I couldn't breathe, my whole midsection was tensing up as he deepened inside me. I moaned and expelled all the air from my lungs and took a deep breath. I already knew that this would be a challenge but I had no idea that it would be so enormous. He was an alpha, by all means, he shoved it inside and split me open like I was disposable, which I was to him most likely.But why do I care?I'm a brainless fuck doll and a sorry excuse of a man, I should bite the sheets, remain silent and be thankful....

Panty Slut

You little bitch! I can’t believe you're wearing my panties again. Do you want to be a girl? Do you? Well that bulge in your panties tells me you're lying. Come on in here Jennifer. That’s right, I told Jennifer all about you jerking off in my lingerie. I don’t think she believed me. Stay right there so Jenn can see what a little sissy you are. Isn’t he cute Jenn? Go ahead take some pictures. Don’t move bitch! I want you to pose for a few pictures for us. ...

Bookstore Bunny Gang Bang

Dressing as a sexy girl is my favorite way to meet men and have fun. There are so many different sexy outfits a girl can wear to attract men and turn them on, they ensure it never gets boring for a man. Every girl wants to be her sexiest when wearing lingerie and I am no different. Recently, I was on a business trip which included spending the night in a motel located across the street from an adult bookstore. Immediately upon checking into the motel, I got the urge to dress up in sexy...

Caught Used and Loving it Part 2

It had been two weeks since I had been caught and used by the mystery woman and her boyfriend. They had left as quietly as they came, and I was left kneeling on the floor dressed in all my best female clothing, cum dripping off my face, and my own cock dribbling cum on the floor. Since then, I had had only two emails. One was sent immediately after they had left and contained ten pictures of me, starting with me kneeling down, all dressed up and tongue out, ready to lick the mystery woman’s...

Getting A Grip On The Situation Part 2

Ken felt himself being shaken and heard a voice urging him to wake up. When he opened his eyes he didn't know where he was for a second until he turned his head and saw Vanessa next to him."Hey babe, you've got to get up and moving. It's getting late and my parents will be home," she said softly.Ken was out of bed like a shot and quickly redressed. He must have been so deeply asleep that he was unaware of Vanessa leaving the bed. She was now dressed in a short terrycloth robe and he still...

Friday Night Maid Part 2

Friday Night Maid Part II - by Diane Leonard As I finished folding his socks, he stood up and looked down on me. "Diane, remove my pants now, but do not get up after you do, just fold them and lay them on the edge of the bed." I reached up, removed his belt, and lay it on the bed. I opened his trousers and as they slid down his legs, I notice that he was wearing boxer shorts and that his manhood was semi erect and poking through the slit in the front. Embarrassed, I looked down and folded his...

Mistress Hannah s Pathetic Husband Part 9

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

Jessie s Fantasy Chapter 8 A New Beginning

I sat in stunned silence after the love of my life gave up my little secret to all of my friends. After losing a bet with John, I had to dress up as a woman and try to hook up with a guy as payment. Tracy and her friends did such a good job making me look like a woman, that I was able to fool all of my friends into having unplanned, but very much enjoyed, sex with me. It wasn’t until Ross and Steve had their turn with me that Tracy decided to announce to my friends who Jessie really was.Tracy...

My 2 AM Phone Call Part Four

They let me finish my cigarette and glass of wine which I appreciated very much. I sat very still on the bed smoking and sipping the wine while they watched me intently. A few minutes earlier when he locked the motel room door and I heard the lock click, I felt just a little fear, but that now gave way to excitement. The guys remaining in the room of this cheap, motel had seen me perform for about an hour. They saw what I could do, what I could take and what I had to offer. So, I did not think...

Call Me Julie part 3

I stretched and reached out like a cat waking from a nap. Scott was resting on his side with his elbow down and his head resting on his hand looking down at me. "Enjoy your nap?" he asked as he stroked my shoulder. "How long was I out, how long have you been watching me?" I replied. "Not too long on either of your questions," he replied. I glanced at the clock and it read 8:00, I stretched again and reached for his face to pull him towards me for a kiss. My tongue entered his mouth and we...

Keeping A Secret

The drive home from the Cities was always long. After work I had stopped at Kim’s to change and emerged as Samantha. I drove to the meeting and then went out for a drink (or maybe two) with some of the other ‘girls’. By the time I was half way home my eyes just wouldn't stay open any longer. I decided to pull over in a secluded wayside rest area. If I could just catch a little catnap I knew I could drive the rest of the way. I wanted to be back at Kim’s to change before it got light so her...

Girlyboy Gone Wild Part One

Wearing sexy lingerie for a man is my favorite way to feel like a girl. I've been doing it since I was 16 and have never been shy about it. Every few months, I get the urge to do it. So, this month I did it again.To find men to turn on with my sexy lingerie, I placed an ad on the local dating line:"Hi. I'm a hot girlyboy who likes older men. I'm having a party in my panties this weekend and I want you to come. It will just be the two of us. All you have to bring for me is your big one. I like...

My Crossed Life Chapter 3 Practice Makes Perfect Jenni s First Blowjob

Who was this girl? Just minutes ago, Missy was giving me an incredible blowjob. Now she was casually reminding me to make sure I turned over to balance out my tan lines as she sipped from her glass of water like nothing had happened. I was looking straight up at a nearly perfect sky for a September weekend day, feeling the warmth from the sun beating down on me. Three months ago, I was playing dress-up with this girl as a dare and somehow it had progressed to being her little sex project. Part...

The Adventures of Patty

“You're wearing my things again!” Brenda screamed when she came home early from community college and found me prancing around the house in one of her short skirts. “Take them off, you little pervert!” It wouldn't be nearly as bad if I were her little sister and trying on her clothes but I was her brother. But it wasn't as bad as it could be. I mean, if she knew what Tommy and I had been doing just two short hours ago, she'd really be pissed. Truthfully, Tommy and I had never really done...

My First Time

I met Lydia while living in Florida. I had recently won a law suit and didn’t need to find employment for a while, so I spent the first three months partying. A good friend had sponsored my membership at a well known and popular yacht club. They had a public side and a members-only side; the members-only side had better bands and more folks.If you parked your yacht and paid the docking fees, admission to the members' side was free. Otherwise, admission was for members, or in the company of one,...

Nice surprise for the delivery man

I'm a crossdresser in my early 20's and still live at home unfortunately. The day started as it usually does when I'm home alone, dressing up. On this day I had gone for a pink G-string with a matching bra, my breast forms, and some tight leggings which showed off my pert bum very nicely. A black lace top and of course my light brown shoulder-length wig and my make-up. I was in a bit of a horny mood so I went for the red lipstick and lip gloss to give them a sparkle, red nail varnish with...

Stage Two Of My Journey To Becoming Joann

Life was becoming a little confusing. I was out of high school and attending the local community college part-time at night while I worked at the machine shop during the day. I played soccer on the college team in the inter-county conference. Mom helped me buy a nice used car. Still, I wore panties, a bra, and nightshirt to bed every night. Sis was working part-time at a hairdresser while taking cosmetology courses in the evening. We still sat together in our panties and nightshirts...

Sissy Slut Gets All His Holes Filled

He was waiting for me as instructed, dressed in the bag of clothes I had left for him earlier in the week. I entered the motel room to find him sitting on the bed in the mini skirt, sheer blouse, lace topped thigh high stockings and stiletto heels from his goodie bag. With his legs crossed, he appeared to be quite demure but I knew the desperate, horny slut that was raging beneath the surface of his sissy attire. He knew I was the only person on the planet that could satisfy all his perverted...

My first time in a bar

For a while now I had been chatting with a sweet guy named Allen, who was bisexual and was eager to meet a crossdresser. He was very muscular and handsome, a hard body but with friendly eyes. He seemed to really like my pictures and said he had cum, stroking himself, while looking at them several times, and was eager to meet me in person. He wanted to meet in a bar which is something I had never done before. I have had sex outdoors before but in a secluded spot, I had only toyed with the idea...

Crossroads

A crazy little story where a young man finds out if his hidden desires are what he really wants. This all started with my desire to see what it felt like to have big breasts. That's a little odd for a guy. I was a normal heterosexual guy who dated some in high school and now that I was in my mid 20's I found myself at a crossroad. A couple of years ago I had decided to start taking some female hormones. This would help me fulfill my desire to grow boobs. All my life people would tell me...

Simran A Crossdresser Part 3

After that rather eventful evening with Ram, I opened up to my fears and inhibitions. Now performing on cam or coming out dressed in front of an online crowd was something I could do easily. I still covered my face, since I wasn't yet ready to reveal my identity. As far as I remember, it was a couple of weeks after my interaction with Ram that I heard a commotion outside the house. I went downstairs and looked through the window, and what I saw was astonishing. People were running, screaming...

My Night at the XXX Video Theatre Part One

It was almost 2 AM when I pulled into the Big Town XXX video theatre in the southeast part of where I live. It was a Saturday and the parking lot was full. I had never been to this particular theatre but it was in the adult theatre chain that I had been visiting for the past two years. Each theatre is different depending usually on the part of town where it is located. Southest part of my city is rough. It is predominately African American. This theatre is in a small run-down strip shopping...

The Panty Princess

Jane and I had only been living together for three weeks when I was caught red-handed. I was mortified when I saw her in the mirror, standing behind me with her mouth wide open. She had managed to come through the front door, up the stairs and into the bedroom without making any noise. I tried to explain that it was the first time I’d ever done such a thing, but she was having none of it. For the next hour we sat on the edge of the bed while she bombarded me with questions about my sexuality,...

My Parents Friend

The year was 1987 and I was home on leave from the military. One particular Saturday night my parents were haveing a get together with some friends so I decided to go out and try and find someone to have fun with. I couldn't decide what to wear until I just decided on what I thought would make me look sexy. I grab my things and head into the bathroom and put on my sexiest black satin panties,black bra,a black skirt type garter belt and black hose and a mini one peice tight fitting black skirt....

Finding Tammy

John knocked on the door to his friend’s house and it swung gently open. The latest chart music boomed from inside. He called out, “Hi its John?”No answer; so he went further in the house the music was coming from upstairs so John went to investigate. He needed to find someone so he could pick up the money. The music was louder upstairs and though he called out again no one answered.Then he saw his friend’s thirty year old son Tim. He was dancing around in a red lace thong to the music. Tim saw...

The Path to Satin Liv and James Meet Again

LivI walk down the hallway, spotting you at the party. I haven't seen you in so long. I swing my long hair over my shoulder, sliding up behind you as my hand slips across your ass. I pretend to act innocent while reaching for a cup of punch. Leaning in to whisper, I say, "It's been so long. I took a walk down memory lane and missed so much." My hand trails up your back then away as a guest walks by. I lean in again. "Meet me upstairs. I have a surprise in my purse." I set the punch down,...

A Close Encounter Part 3

Homeward Bound "Well, how was it for you?" My question was directed at my wife's reflection in the rearview mirror. She looked quite fresh considering that she'd just been fucked. "Yeh, it was good! Pass me a tissue, babe." Sam stretched an arm between the front seats. "It was certainly different!" Paul's assessment of the last hour's shenanigans raised a chortle. "Not 'aff!" I concurred in a deep baritone totally alien to my look. While Samantha wiped some of Ross's cum from her...

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...

Allen s Sweet Surprise Part One

My pussy was dripping as I zipped my car into the parking spot in front of the mall.I was having another secret meeting with my boyfriend, Allen. Only, this time we'd arranged a little twist to our usual tryst.After years of Allen and I seeing each other, I'd finally worked up the nerve to share my fantasy of him dressing up like a woman for me.It wasn't easy for me to do. I'm a shy, reserved girl and Allen was about as masculine a guy as you'd ever find. I was afraid he'd break up with me when...

The Wedding Proposal chapter V

I turned the key in my apartment door. As I heard the lock click, and the door swinging open, I suddenly felt a strong sense of abandonment. The sensation was so strong that I had to close my eyes and draw a deep, long breath. I was surprised, but instantly knew what it signified. Stepping through that door would be the final return to myself. To who I really was. The magic would be broken and the fairytale become a dream of times past. Life on the yacht with my husband and friend had been a...

My best friends dick

I was a closet crossdresser with a crush on my best friend and finally, after we had both graduated I worked up the courage to show him how I felt. I invited him only and met him at the door dressed in my sexiest/sluttiest outfit. I fell to know knees and gave him his first bj. It was also the first j I had ever given. It was wonderful for the both of us. It was something I had wanted to do for a long time and he had no idea that I was into cross dressing or wanting to be with a guy. After...

My first boy experience

It was my friend, Karly's birthday. Her choice for going out to celebrate was a drag night at a club. It wasn't so much fixed on drag as it was on gender parodies and cross-dressing for fun. I had been a closet cross-dresser for a long time, although I had told a couple of girls I knew. Everyone was going to cross-dress and have fun, but I was going to revel in it. I had never been with a boy before, not even kissed one, but every time I was in women's clothing I wanted cock. During the...

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