Crossdressing HD Porn Videos

Lunch Date With Clair

It was Tuesday morning and I had a rheumatology appointment in Maple Grove at 10:15 am. It was now about 7:30 and I thought I should start getting ready for my appointment and lunch date I had set up with Clair.When I talked with Clair on the phone last week, we decided an early lunch date would work for us. She told me to meet her at Biaggi's at 11:30 am and that she would be waiting.I jumped into the shower and shaved my body and legs. Making sure not to miss any hairs, I ran the razor over...

Night Trawling The Crossdresser

The streets of Pomona live two lives. Like maternal twins, they coexist in parallel, appearing as virtually identical to those merely passing through its old and storied neighborhoods. During the day, with the sun high overhead, myriads of people — whether they’re commuters traveling like drones or soccer moms distracted by their busy lives — they choke the streets in a constant pulse of life. Each person is absorbed by their own petty concerns, each oblivious to what is happening on the...

Second Encounter Ch 3

The sun is sinking low when I awake. You are already up sitting on the porch watching the waves roll onto the beach. "Jill is still asleep. Let's not wake her. It's a beautiful evening, Monique, let's go for a stroll," you suggest. "Great idea, I love long walks on the beach. It's so romantic," I respond."It's a full moon, as well," you say, "Perfect for a beach walk.""I'll change into my bathing suit," I say excitedly, eager for a chance to display my chest plate."Me, too," you reply. "I'd...

A Hotel With Candy

I got out of bed and looked at my sexy green camisole with bright pink fishnets, bra and panties that I liked to sleep in after I had just spent the night masturbating with my favorite dildo. I looked back at my nightstand to find it was still beside my pillow where I had left it the previous night and stilled wrapped in a condom all sticky with my favorite lube, strawberry flavored.I finally had gotten sick of fake cocks and wanted to try a real one. I went on to my favorite CD website and...

Missy Returns

It had been a long time from the seven days I spent with my studs, but sadly I went off to school and Missy had to go on an extended vacation. However, school did not work out as planned and I found myself in a new city and my own apartment with a small job. I had to help pay the bills. For a while I lived with a roommate who was a little homophobic and despised the ideas of trannies. He never found out that I was Missy but had come across the site once and never recognized me. Eventually, he...

My Sexual Odyssey Part III Becoming a Slut Continued

We got to Tom’s car, and he opened the door for me, then walked around and got in himself. The drive was short and uneventful, and we parked behind the club. There were some people arriving at the same time we were, and I noticed several who looked like they could be CD’s. We approached the club’s entrance, and I began to feel more relaxed. It is always uncertainty that is anxiety-producing, and once we arrived, the uncertainty diminished considerably; I now could see, not merely imagine, what...

Evie Becomes Tilley

A couple of weeks ago I’d sent a message to Mistress Jane saying that I’d managed to arrange a free weekend at the end of the month. Mistress Jane had promptly replied that she’d check her diary to make sure she was available. The next day I received a text from Jack saying that Mistress Jane had asked if he was free the same weekend and if so, would he like to pick me up from the train station.So here I was, walking outside the train station. Excited to be on my way to meet my Mistress again,...

Night Out

"Ladies hour, you get in for free." The bouncer nodded her in as she flashed her id. It was a spur of the moment that she decided to go to the club alone. As a Saturday night, it was ripe for excitement. Yet, none of her friends were up for it.She talked herself into going alone for once, the need to escape the monotony of the week and weak hookups were too strong. She yearned to feel the music, shake her body, and meld into the crowd of dancing bodies as alcohol flooded her veins. A little...

Lingerie and Domination

I had answered an ad on telephone dating service. She described herselfas a ‘bedroom dom’. I am not sure why I answered the ad and I didnot really expect a reply.She phoned when I least expected. I did not think she would beinterested but I had mentioned in my reply that I like to dress inlingerie — panties in particular.I met her for a drink. She was younger ( 38 ) than me and somewhatattractive but a bit on the heavy side. We had a nice chat and drink andwe went ours separate ways and I did...

Noodles Part 2

Mark and I were still smiling and reveling from our exciting private dance with Amber, as he pointed the car towards my neighborhood. Ever since Mark mentioned that Sunday nights are Ladies Night, I wanted to know more. I prodded him, "What's so crazy about it?""OK," Mark began. "For starters, 'ladies' don't pay cover. They get free champagne for the first hour. And their private shows are half-price. So when I say it's 'crazy', dude, it's packed. Mostly T-girls and crossdressers. They...

Lisa s Lessons

I used to spend a lot of time away from home for my job. It had its downsides, but it gave me a chance to do my favourite thing: show off. My toolbox had a locked compartment containing a small selection of cam-suitable wardrobe items: a single camisole, a few panties, and two pairs of nylons - one thigh-high and the other to the waist.I travelled a mostly predictable route, so I was a regular at several hotels around the region. Along with racking up enough points to take my wife on a nice...

Fear Part 2

Tyler sat there on the couch taking a long pull off his drink in an attempt to slow down his heart rate and calm the fear that had returned. He had just allowed his newfound friend Vince to kiss him and he kissed him back. What was puzzling to Tyler was that he enjoyed it and his raging hard-on hidden in his silk panties under his leather skirt were a testimony to that enjoyment."What's happening to me?" he silently asked himself.At first, they did nothing more than talk and Tyler began to...

Pumped While Wearing His Pumps

What a place to be stuck! Under a sign that says Coors Road and practically dying of thirst. I was now two-thirds of the way across the United States but perhaps the most difficult portion of my cross-country hitchhiking adventure lay ahead. It is all deserts from there on the outskirts of Albuquerque to the Pacific coast, my ultimate destination. I had left from Maine four days earlier and was starting to tire of the road. My most recent ride had been with a guy who picked me up in Denver. A...

Becky was born

Hello everybody, my name is Becky, this is the story of how I was born.I was 16 when I first started cross-dressing back in the seventies. I had been accosted by a man and masturbated him in the men’s washroom in the park. I still remember what he said about me. He said I looked so much like a girl even though I was a boy. After that happened, that statement stuck in my head. A little time after that, with that statement still floating around up in my head, I decided I would dress as a girl and...

Carolyn Makes Her Way part 2

After I left the office of my former employer I went immediately to see an attorney. There were two things I had to do: one see about suing the hell out of my former employer and two: I needed to get my name changed legally to Carolyn instead of Carl. I chose this attorney because I already knew him, very well in fact, right down to the birthmark above his nice cock. He wasn't surprised to see me in a dress nor was he surprised that I wanted to get my name changed. “Are you going all the way...

How my Best friend gave me what I always wanted

The day started from me being all alone in the house for a full day. My parents and sister were out and wouldn't be home until the next day. I decided that I would give my best friend a call and get her to come over to see me, we hadn't seen each other in quite some time. She was just as eager to see me as I was her and we were both very excited as we really enjoy each other's company.Now my best friend and I had a very normal friendship. Although I'd always had fantasies about her as she was...

Punished

I glanced around the second hand clothing shop to make sure that no one had seen me pick out the pink, pleated netball skirt from the rack. I hid it beneath a pair of long pants in my hand. I felt my heart start to beat furiously as I stood next to the change room and caught the attention of the shop assistant by waving the pair of pants I was carrying, and the hidden netball skirt in front of me. He nodded and with a smile on his face motioned me to enter the change room. I entered, and...

Losing at Strip Poker with Three Women

Well, last night was quite a night to say the least. Three girl/friends came by with wine coolers and tequila to do a little partying. The four of us have been very tight for over fifteen years. We are very special friends that can talk about anything to each other. I should have known they were up to something when they said the tequila was all mine and the coolers theirs. They know I love tequila a lot, and I can get really silly and easily manipulated, if you know what I mean. After a few...

Girls Night Out Part 2

Girls Night Out Part 2 Well everyone wants to hear about the second part of my night with Julie when I was in New Jersey. In case you didn’t read my first story, my name is Cassie, short for Cassandra (I also go by Sandy sometimes) and I am a cross dresser (CD). A while ago I was spending a hot summer night in New Jersey at a hotel with my friend Julie. We were attending a girl’s night out at a hotel bar with about 25 other t-girls and we had already made a scene with our attire and actions....

The Worm Turns Part 1

I must have read about a million of these stories and I have to confess that mine isn’t so unique--maybe only in the details, but not so much in how things started or how things ended. You can probably write the first lines yourself: “Things started out so innocently. We had a typical relationship that somewhere, some way, took a dramatic turn that I never saw coming. At first, I was all for the plan, but by the time I had become my wife’s feminized slut, I realized that things had gone too...

Vicky s First Time

I was very open about crossdressing when I met my wife when we were in our 20s. She has been very supportive and helpful. She helps me with my hair, makeup, and picking outfits. We started having sex with me dressed up as Vicky. This soon escalated to her taking me with a strap on. I loved the times she would fuck my ass with her cock. I had never considered myself gay or bisexual but the feeling of her cock inside me opened up the possibility for more.One Thursday she told me that we were...

The Feminisation of Michael Chapter 4

The Feminisation of Michael. Chapter 4 Sue had replenished my wardrobe again with new work clothes and had taken the secretary theme to heart! The skirt suits had been replaced with pencil skirts and pencil dresses. The blouses had been supplemented further with lace and ruffle fronted blouses. There were also several ribbed tight fitting cardigans in black, red and various pastel shades. I put on a black lace, slightly padded bra and matching panties along with suspender belt, as I now...

A weekend with Nancy

CHAPTER 1Upon arriving home from work one Friday afternoon my wife informed me that the kids would be staying the weekend at some friends house, and that she had made some special plans for us. She then went on to say that she would be gone for a couple of hours and that while she was gone I was to shower and to shave myself from head to toe. Then I was to get my "special clothing" from storage and neatly arrange them on the bed. You see, for years now I have enjoyed cross dressing and while...

My First Boyfriend Part One

Since my family had moved to our new house, Steve and I had become best friends. He lived next door and had moved in about a month before we did. With both of us being the new kids on the block we bonded quickly. He was two years older than me at eighteen and I had just turned sixteen a few months back. He was also taller and had more muscles than I did. He had tan skin and black hair where I was pale and had brown hair. He stood almost six feet tall and I was about five foot six. We played...

One On The Way Part 2

On Saturday morning, Ryan was alone sitting at his kitchen table enjoying his morning coffee and cigarette. Normally, Belinda was with him but she got a call from her job offering her some overtime and she bolted. As he smoked, he thought about Belinda's newest request. It seems that dressing in lingerie wasn't enough for her, she wanted to see him in a wig and makeup.While dressing in lingerie was definitely out of his comfort zone, this newest suggestion went way beyond what he was prepared...

Gang banged at a private club

After yet another hot weekend at my friend Heberto’s house, I was packing up and getting ready to go home when he told me he had something “special" in mind for us next weekend. I begged him to tell me what he had in mind but he refused. So I left. My curiosity was peaked. The week dragged on thinking about all of the possibilities. The anticipation was killing me. Finally Friday arrived and that day at work could not have been any longer. I rushed home and followed my Friday routine of...

Date with my wife

It started with my love of sexy lingerie. I planned a date with my wife. She was to come home from work and go up stairs to clean up. Once all cleaned up she was to put on the outfit I laid out. She had lots of questions that I wasn't answering. She wasn't to come into the rest of the house until she was dressed. Well my day started by going to the store shopping for dinner and an outfit. After looking at lingerie picking out a pair of silky black panties, a satin black bra, a garter skirt and...

GAG A RIFIC BARRY

When I first met Barry, I immediately noticed that his smile was gorgeous. The second thing I noticed about him was how great his ass looked in tight jeans. He was flirtatious and playful. Barry and I had been dating just a month when we made a bet on a basketball game. I won the bet and jokingly said that I wanted Barry to wear a pair of my panties. Barry blushed but agreed. I did not think he would really go through with it but he went into the bathroom with a pair of my...

Miss Teresa s Beauty School

I wrote this story as a narrative and I made it into a 45 minute audio story. The Interview: Come in, I've been expecting you. I had a long talk with your boss the other day and it seems that you have a little fetish for women's underwear, isn't that right? In fact-you've been caught stealing things from the other girls lockers. Mostly their panties and pantyhose. Is it just too hard to be the only man at an all girl company? Do you want to be more like the other girls? Is that the problem...

Practice Pays Off

It was a beautiful Saturday late afternoon. I was done with all the things I had to do around the house. My wife was gone for the weekend and I was feeling a bit bored. I thought I would take a shower, shave and pull out the makeup and see if I could do myself any justice in looking passable. Many attempts before had failed, but I was getting a little better each time.I got out of the shower and was nice and clean, smooth from head to toe and went to the bedroom and pulled on a pair of my...

Wedding Night For Ken And Barbie Part One

When I went to my cousin's wedding in Monterey, California stag, at the reception dinner she had me seated next to the only other male stag invitee, the photographer. He was my age and tall and we hit it off, immediately. Ken was a sports car enthusiast and he told me about the thrilling rides he took along the Pacific Coast Highway. He talked about the beautiful views at scenic lookout points along the Big Sur where he he said you could park and watch the waves pound the coast. He said it was...

Mall Walking

I recently sighed a contract with an online Mistress. My main duty under the contract is to write or edit several publications I'm preparing for sale.If I displease her, she assigns me essays - writing of her choosing that doesn't contribute to my writing goals.I sent her a late response and she assigned me to write about a man following a woman in a mall because of her sexy pencil skirt. Here's the "essay:"What was that? Something attracted my left peripheral vision. I move that way, peering...

Mistress Sarah fucks Evie Chapter 4

I knelt by the door, anxious for the arrival of my Mistress. I could feel my arse pulsing around the butt plug in anticipation of what was to come. As I knelt and waited I could smell the pretty floral scent of the perfume that I had sprayed on my neck earlier. I felt soft and girly from all the day's events. I was in a prime mode to be fucked like a sissy. Even though I was not touching my cock, it was pulsing and hard with arousal. I was both excited and nervous about being fucked. I heard...

Night Out Ch 5 Shopping Spree

June's heart was racing; he visibly shook. Sweaty palms, nervous demeanor, he may as well be a dealer based on his level of suspicion–he'd just be noted as a bad one.The bag he carried felt heavy despite not holding anything of significant weight. Its contents may as well equate to a full ton due to the knowledge of what was inside.It was crazy to think a few moments ago this very man was imagining bending Evy over the next sturdy object he could see. Their games of teasing each other after...

From dream to reality

My name is William. I am the eldest of a family of four kids, two boys and two girls. At the time I was seventeen. We lived in a small town, and my parents were well respected. I did well at school, played and succeeded in sports. I was and still am living an intense inner life fantasising on my sporting exploits and sensual encounters. In those days, it was just as normal for teenage boys as well as girls to be baby-sitting at their parent’s friends and neighbours to make a few bucks. For...

The Arrival

It must be the hottest week of the year. I’ve tried to fix the air-conditioning the whole morning to no avail. Typical! My brain already works at about sixty-four per cent, and I find myself doing a three-person job. This is only my second year as the headmistress at this sixth-form girls' establishment.Of course, the superintendent is nowhere to be found, and the secretary decided to have a summer baby – without any notice! That lucky devil didn’t even look pregnant last year.Not that I’m not...

My First Time Final Chapter

The Friday that Lydia told me about had finally arrived and she would be bringing some of her friends over for drinks after work, and I was to serve them as Melissa. Lydia had also advised me that unlike the dominatrix persona I used during my first outing on Halloween, Melissa the maid, was totally subservient. That morning after my usual visit to the gym I cleaned the house and set up the bar. I had become a combination of nervous, excited, and scared while preforming these tasks as the hours...

My Neighbor s Wife

Carol, my neighbor's wife, had been suspecting for some time it seems, and when her husband had to go away for several days she took it upon herself to confirm her suspicions. That was the beginning. It was early morning when there was a knock at the door. I thought 'What the fuck? No one comes to my door!'I was surprised to find Carol at the door. Although Carol was smokin' hot. She had long wavy blond hair, ample breasts, a nice ass, and long slender legs. I think it is mutual when I say we...

Blueberry Fields Forever

I have been cross-dressing in secret since I was in my late teens. Over the years, I have accumulated quite a wardrobe and whenever I get a chance I like to get dressed. When there is little time, I just throw on a sexy bra, panties, and genderless outer clothes like a sweat suit and sneak off to the local adult bookstore in a totally non-passable condition. There I can usually find some dick to suck or someone to fuck my ass. Sometimes when the family is away, I get fully dressed in clearly...

An Uneven Romance Part Two

“Hey, Sam.” I jumped and spun around, startled. One of my housemates, Mark, had walked into the kitchen where I was preparing breakfast for Sarah, the incredible girl I’d brought home the night before. Sarah was a pretty special girl; after a night spent with my head between her legs she had eventually let me cum this morning. She’d somehow coaxed me into wearing her wet panties from the night before though, and when I came she fed it to me, rubbing what was left all over my cock and her...

Attractive To A Fault

Events in our lives can often change us in ways we never expect. In my case I certainly felt different as a young boy. I possessed very real, mysterious, unexplainable, emotions that I can describe only as feminine needs, in spite of being athletic and quite normal in appearance. These internal feline longings and desires were intense and drew me to all kinds of feminine things.I knew that I loved to feel like and even look like a girl. In my youth I would secretly dress up like one though my...

A Nanny Femtastic 7

A NANNY FEMTASTIC! Chapter 7 After that first dinner Bradley and Felicity retired to their bedroom. And even though they were in a separate wing of the sprawling villa I could hear them making love! I thought of what Felicity felt as a transsexual woman having had a vagina created out of what was her penis. To feel Bradley rigid penis inside her. I wondered how nice it would be to put on a skimpy pair of knickers or a g-string and feel it flat against your own vagina. The thoughts turned me on...

Hard 2

Well, that didn't work out well. I mean, we're fine at work, but once again, you're all proven right. I accept what's been said and that I deserve anything else you have to say about me. Well, maybe not anything, Azalea. Remember to keep some thoughts to yourself, my love.In unrelated news, I've been wearing pants the last few days. It's weird, but ultimately okay. I get that trousers are not strictly menswear, but after wearing skirts and dresses for so long, I find myself feeling...

Two girlfriends stay in for the night

The other day I came home from work and was looking forward to spending the evening with my wife. We had the next day off, and it was going to be great to just get some time with her. After I was home and settled my wife Dawn came and found me and told me she wanted to spend the evening with a girlfriend and have some fun. I was a little disappointed, but a few seconds later, she told me that she had some plans for her and her girlfriend Ashlynn, which is the other name I go by, and suddenly I...

A Tale of Two Clitties

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

The Engineering Costume Party Part 2

After realizing I might be the only guy dressed as a skank for the Skanks and Robots Party I timidly waited in the dorm room and “pre-gamed” with Anthony and Jillian for the upcoming festivities. I drank vodka and cranberry with Jillian while Anthony had beer. I hoped some “liquid courage” would help me to feel more comfortable going to the party dressed in such a slutty outfit. Now, I had tried on some of my sister’s more scandalous clothes before, but I had never been out in public en femme...

Derek and Amy Derek s Turn

As I walked into the hotel room hours in advance, my cock was rock hard with anticipation. The last time me, my lover Amy, and her husband Matt were all together, it was my dear love Amy's turn to be in charge. Amy had Matt and I dress like two Fifties sluts. The kind of girls uptight parents used to believe would cause the downfall of society. It was both Matt and I's first times with other males though not my first time dressed up. He is still fairly new to this as his wife just discovered...

My New BFF Part Two

It was midnight by the time I got home from Tiffany's. I took off my shirt and pants and put on the silk nightie she gave me over the bra and panties I wore home. The feeling was exquisite. It felt so comfortable when I got in bed that I fell asleep within minutes.When I woke up the next morning, I reluctantly took my lingerie off so I could take my morning shower before starting my workday. I work at home on my computer taking and entering sales orders and customer assistance for an office...

felix becomes felicity

FELIX becomes FELICITY Chapter 1 “Gynecomastia is the abnormally large development of mammary glands in males, resulting in breast enlargement……… In teenage boys this does not have to be linked to obesity……… The word Gynecomastia derives from the Greek for woman and breast” I logged off from my regular searches on the internet and felt sick as usual. I am 16 and a normal schoolboy, except I have this condition of Gynecomastia, the “woman” and “breast” bit ringing in my ears! Basically I...

My Sexual Odyssey Part VII Turning Tricks

The next day I went to work as usual, but skipped my noon time ‘date’ with Brad. When I got home, I called Candy and confirmed the party invitation. Then I called Trixie and asked if she could use me at the club. “Of course! Are you kidding? Anytime!” “Well great, what time should I come by?” “How early can you make it? We open at nine, as you know, but although nothing much happens until close to midnight, there is always a lot of action for the girls.” “Well, I could be there by ten or...

Jenny Learns Her Place Part 2

“Thank you, Master,” I said as I slowly brought myself to my feet, tears of pain rolling down my cheeks. I couldn't see my ass but it was probably purple with bruising and I was happy with that. Bobby would now know that I could withstand a hard spanking with the paddle without falling back on the safe word. “And for good measure,” Bobby said and put the clips back on my nipples. Wincing with the incredible pain, I managed to stand straight. The nipple clips hurt much more this time than the...

Discovery

How did I end up in this position? This was the thought running through my head as I lay face down across the bed. My mind flashed back to the moment it all began. It was a beautiful Sunday morning with a cool springtime breeze blowing through the open window. I was cleaning the house. I hated cleaning, mostly because it is never fully done. No matter how much cleaning you do, there will always be more. I'd have much rather been out enjoying the nice spring day, but it had to be done. Then it...

Call Me Julie Part 4

Scott coaxed me out of the car and we walked the ten feet to the front door, he was practically dragging me while reassuring me that everything would be alright. "Kelly is expecting us, don't you worry about a thing." "She is expecting me? Dressed up like this? Somehow I don't think you are telling me everything Scott, if this ends badly I will be kicking your sweet ass," I told him. He chuckled as he opened the door and announced, "Kelly, we are here." Kelly replied from the kitchen, "Okay...

The Brother Bride

My twin sister Julie and I had always been close. Growing up, we shared each other’s deepest secrets. I had always told her I would do anything for her.Julie was a girly-girl, and loved being female. She had said she would be happy if she could wear dresses and heels all the time. Her wardrobe reflected that. She had also known about my urge to wear female clothes since we were young, and being my dear sister, never told anyone else. She told me she could never mock me or embarrass me in front...

First Time Bareback

I have written an earlier story about the first time my boyfriend Mike and I fucked. After our first encounter, I couldn't get enough of Mike and his cock. We went from meeting every other week to him spending some weekends at my house with me dressed the entire time. As we got to know each other better, we started to discuss our sexual histories and some of our fantasies. I could tell Mike was a little jealous of a former lover of mine, Steve, and his seven and a half inch cock. I assured Mike...

The Dress

“Mmm. I missed you, Rick.” Julie moaned as she lay in bed with Rick spooning her. Biting her lip in a smile, she moved her hips to make her backside tease Rick’s semi-erection.Rick chuckled in Julie’s ear, whispering, “Are you wanting a third time tonight, Babydoll?” He traced her arm as she increased the pressure against him. “I think there’s my answer.” He moved his hand to grab her jaw, pulling her head around to meet his lips. After he kissed her, Rick looked into her eyes and whispered,...

An Introduction To Crossdressing The Finale

Reliving our evening’s events had Jackie and Chandra pretty worked up. “You girls seem to be getting a little excited," I stated. "Are you ready for some more fun?” Simultaneously they both grunted, “Yes we are!” I leaned across the table to find them both holding the others cock and slowly working each other into a frenzy. “You should probably save some of that for back at the hotel, before you run dry,” I said. But that didn’t seem to deter their enthusiasm, until Susan walked up. “I’m done...

What I Do When I m Alone

With the wife off to work today, I decide to indulge in my fetish. I wait a little bit till I know she is at work and it's upstairs I go. I take my computer with me to chat with friends and others I happen to meet in chat rooms. I lie down on my bed and start chatting with people and seeing which friends are on. It takes about an hour before I finally find someone to chat with. What follows is what I usually do when I find someone to chat with, this is no direct account of what happens, its...

Mom s Old Boyfriend Part One

It happened quite by chance and we managed to keep it a secret, ever since. I was home alone on a Friday evening wearing my mom's favorite black lace lingerie and her old boyfriend, Ron, came by to see her. He still had a key from when he was seeing my mom and he walked in without knocking on the door, startling me. And he caught me playing with myself through the sexy little black lace panties on the living room couch. My little six inch clitty dick was rock hard and leaking juices into the...

Who Would Have Known

Dave never realized how much he would like it. He didn't have a complete understanding of who he was and how he felt. Dave is a dockworker, a motorcycle rider, a beer drinker, an average Joe, and likes his women as fast as his bikes. How was he to know that one day his life would change in a way he could not fathom? Dave works as a longshoreman at the Port of Oakland. He works the docks by day, lives in a four-story apartment complex by night. Working at the port is physically demanding, so...

Wife s Crossdressing Fantasy

This is a work of fiction. Any resemblance to persons or incidents is coincidental. My adventure began while I was a senior in high school. My mother took me to the dentist. It was late afternoon and shortly after I was called into the examination room the receptionist and assistant went home. The dentist then closed the door of the room we were in. He walked over to me and started making small talk... I guess to make me feel at ease. We talked about many things. He told me I was cute and that...

My Foggy Late Night Story

It was a cold, wet December night. Here I was in my room, feeling exhausted, and laying on my bed doing the whole Netflix and chill thing. I had just pulled a long afternoon and evening event with my college study group. We spent the day as total masochists painfully cramming whatever we could into our tired brains for our finals. It had worn me out so much that I didn’t want to do anything, including exercising, which was another problem I had to deal with since I hadn't exercised in nearly a...

CD Domina training two slaves

Just five days had passed since my last session with my slave Candy and already I was yearning for his sexy body again. I was in need of another meeting and had something special planned for it. I called Candy's phone and just like previously he answered before it could ring twice and greeted me anxiously."Hello Mistress Cheyenne," Candy said as he answered his phone."Hello slave Candy," I replied. "I want you to be at my house tonight at 8 PM and this time I want you wearing nothing but the...

Vicky s Education

My wife was very pleased with how I had performed as Vicky. My cross-dressing had progressed from a sexual role play with my wife to her setting me up for my first sexual experience with a man. At the same time, she had picked up her own guy and had taken him back to our bedroom. She cuckolded me and had me clean up her pussy after I got home. From that time on, the only time I was not dressed up as Vicky was when I went to work or we had a family function. This was at my wife’s insistence. A...

Sex With Wife Who Doesn t Know

A little about myself. I have been married for 40 years. I work in a professional career and I secretly like to cross dress. My wife does not know, or, I suspect she might, but prefers to not acknowledge it.I started dressing about twenty years ago when our two daughters were off to college and we were empty nesters. Out of curiosity I tried my wife’s panties on one day while she was gone. It really felt good – different. I was not sure this was right and afraid of getting caught so I did not...

Getting Caught By A Friend and First Blow Job

After my first time dressing in my sisters clothes and imagining being with a man, I dressed every chance I got when my family wasn’t home. It had been four years since I started and now when I dressed it always included fantasy about being with a man and masturbation. I had grown up into a proper slut that craved cock and needed to be deflowered of her virginity. Only anal I ever had was a small brush handle up my ass, but I wanted so bad for a real cock. I have experienced all my sisters...

Rite Of Passage John Or Jennifer

John turned eighteen that day. His father was at work. His mother and sister Lisa were spending the day shopping, saying they wouldn't get back until very late in the afternoon. He decided he wanted to pamper himself, celebrating in the best way possible. That way was by dressing up as a female. John had been a crossdresser since he was sixteen. He believed he had managed to keep that part of himself hidden from the rest of the family.After taking a luxurious bubble bath, he carefully made up...

My First Boyfriend Part Two

NOTE- this story will make more sense if you read part one,it can be accessed through my profile page. The week leading up to today had been one of the longest of my life. I was very excited that today had finally arrived. My boyfriend Steve’s parents left early that morning and would not be back for three days. My parents had agreed to let me stay over while they were gone. Steve and I were going to experience our first time living like a real couple in a real house and not in our fort as...

The Clothes Make the Sissy

I don’t know what happened to my clothes. It seemed like they just kept disappearing. Amy’s solution was always for me to wear her clothes, and I must admit that they made me feel really sexy. I’d worn women’s clothes before here and there, but it was always for a party or some special function where it was expected or at least accepted.My feminine build always gets lots of attention from guys, and it’s not hard to understand why. I’m a petite boy with a big ass, lips, and chest, and a small...

Milked On The Train

I was still a virgin, at my advanced age (17), but aroused a lot, loved reading sex scenes in books, imagining it, touching myself. I traveled every day on a crowded train, on the way to my classes. One day I was standing, as usual, holding on to the pole while the train rocked and slowly made its way.An older man, maybe forties, was holding on to the pole across from me. He was taller, holding on lower on the pole, and as the train rocked at one point my groin hit the back of his hand. I...

crossdresser confession part 1

I really loved my wife; she was the most beautiful creature I have ever known. Tall, brunette and the longest legs you have ever seen. Myrtle's beautiful face is framed by her gorgeous brown hair. She was about 5'8" and had a great ass. Her curves were soft and very feminine, not a big chest but nice and perky tits I loved to play with.She would drive me crazy when she donned a pair of pantyhose and heels with a short skirt. She didn't know it, but she would not have been able to keep my hands...

An Old Friend Comes to Visit

Five o’clock finally arrived and it was all I could do to stop myself from doing handsprings out to my car. I’d really done nothing but fidget in my chair all day anyway. The only thing on my mind from the moment I woke that morning was my plans for the following week. An old friend would be arriving to stay with me and I’d taken the following week off so we’d have nine lust filled days together. Actually, Rob was more than a friend, he not only, had the biggest cock I’d ever taken, at nine...

A Satin Dream Comes True

I’d explored my fantasies with a transsexual escort several times and after my last encounter, which was the basic girlfriend experience, though she did wear a corset and stockings with satin panties as I asked. She was very open to fantasy play I have long had a scene I’d wanted to play out and she seemed to be the perfect gentle dominant.Now my thing is dress up. My iconic Mistress isn’t the hard core type. She’s actually quite playful and gentle but she is definitely in charge. My vision is...

My Crossed Life Chapter 6 Valleys Peaks The Professor

The sexual high of Halloween weekend came crashing down three weeks later when Missy stopped by my house unexpectedly. She was in tears. I assumed the worst, thinking something had happened at school. It was far worse. Missy’s brother and I had grown apart. I was a jock by day, diva by night kind of guy. He was kind of a stoner who had abandoned our friend group. So while it wasn’t surprising he wasn’t the one delivering the news, having a tearful Missy show up at my front door was.“My family...

The Change Up Part 4 Tower Chair

Looking through the sheer curtains of the cabana, I see about a dozen people looking at both of us. Some I just met tonight and others that I don't recognize. Then Emily says to me, "Since you been a naughty cum slut again, I will have you service some of the VIP members tonight! Remember don't talk to anyone and only whisper into my ear." Cuddling next to Emily, I think back to the start of the day, being caught by Emily dressed as Deedra. What a glorious day, having sex with my special...

Confessions of a Sex Crazy Cross Dresser Part 2

Chapter 3: New York with Linda I didn’t really get a lot of time to think about what I had just done with Carlos. I fell asleep shortly after he left due to all the drinks I put away during the night. I actually fell asleep on my couch, still full dressed except for my jacket and shoes. When I woke up, I had a headache and was starving; I never even had a piece of the pizza Carlos brought. It was 2:00 in the morning and I was scared to look in the mirror.I took a shower to clean off the make up...

The postman

Lucy was in her man mode at home when she heard a knock at the door. She answered it and it was the postman delivering a couple of packages for her. They were full of sexy lingerie and three sexy dresses. The postman came inside her hall to talk. The postman had obviously found out what was inside the bag.“I’m sorry, but one of the bags broke so we had to repack it for you.”“Thanks. Everything Okay, nothing damaged?”“Well, if you like you can open it up and check.”Lucy did and saw the guy...

Webmeets Diary Ch 04

Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible.As I neared the end of my university course I had less and less time for playing around on adult personals sites, and spent most of my free time planning my...

Being Christy Part 3

My experiences with Jenny and James had been amazing, but summer drew to an end and it was time for me to take up my place at university. I didn’t need much and only took a couple of bags with me, but the move did mean saying goodbye to my sister’s wardrobe. My parents gave me a lift to my student digs and after some typically over the top parental farewells, I was left alone three hundred miles from home.Settling in to student life was simple. There was an immediate social network in my fellow...

Confessions of a Sex Crazy Cross Dresser Part 5

I hope you enjoy Sandy's continuing adventures. Please comment and let me know if I should include the next two chapters. Chapter 9: Joe’s Pizza Sunday morning I got up pretty early. I decided to call a cab and go over and pick up my van from Glenn and John’s. After I got back I decided to do some sit ups, as I had not been exercising as much lately. A quick shower after my exercises and then I decided to get ready for my trip. I spent a couple of hours packing as I was going to be gone for...

Where do I begin Chapter 1

Where do I begin? I’m normally not very open about my private life, seeing as I grew up under the pretense that secrets are meant to be secrets. However it seems I have come to a point where I am comfortable with who I am and where I have been. Comfortable enough to bare to you all my deepest secrets. Deep breath in, slowly let it out. My name is Alicia, well that's my new name, my old name is Michael. If that confuses you then I should explain that I am a cross dresser, been so for about a few...

Fulfilling A Girl s Male Fantasy Part 1

"Get undressed," the pretty brunette told me, and I obeyed. She was called Jennifer, we'd met the night before at the rock nightclub, and I'd thought that she looked gorgeous in her goth make up so she invited me back to her place. It turned out that she was eighteen and still living at home, so we locked her door and did our best to keep quiet as we fucked the night away. Now it was noon, her parents were at work, she was on half-term break from sixth form college, I had the day off uni and we...

Three nights in London night 3 Irene rocks

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

An Afternoon with Suzie C cksucker

One of the strangest relationships I've had over the years was with awoman named Laura. She saw my profile on Yahoo and dropped me a note. It was like manna from heaven. She was very into the idea of fucking a man in the ass with a strap-on dildo. She'd not done it before but had fantasized about it for years. Would I be willing to help? You bet! We chatted for a long time before we finally agreed to meet. Her trailer park wasn't too far from where I was staying at the time and I went to see...

Office Caught 2

I couldn't focus, my head was racing with all kind of thoughts. I had no idea what this would result in. My manager and teammate noticed something was wrong. I just told them I was coming down with something and felt ill. As there was only about an hour before closing time, my boss told be to finish early and get myself home, dosed up and to recuperate over the weekend. I didn't need to be told twice, this meant I could escape before bumping into Helen and being confronted about wearing...

Discovery Part 2

It had been an amazing year for Kyle. At eighteen he attended his first get together for those that cross dressed and their supporters. It the first time since the urge to dress up came upon him he finally felt safe and accepted.Over the following months, he perfected his skills at makeup along with dressing, walking and talking like a female. Soon he was one hundred percent passable in any light and he couldn't have been happier. It happened one afternoon that Kyle's secret had been discovered...

The Night Of A Thousand Dreams

There was a few odd looking drugs laying on the side from a party. Being bored I decided to see what they were all about, I had dabbled before but had no idea what they all were. I had seen someone use a bottle with an inhaler on it, one good slug later I felt good.I looked through my wardrobe and decided that all guys seem to go for the more cute look in a girl. As I was feeling daring I thought what the hell, lets try something outrageous. I wanted to make sure that as many men would want me....

The Making Of Tara

I grew up in a small town where nothing really happened. It was a nice upbringing far away from the inner cities and their problems. My school was safe and since I was very young, I would walk to school by myself. My parents seldom locked the doors and on the weekends there were neighbourhood BBQ’s. My friends and I would play street hockey outside our houses or football in a nearby park.As far as girls went there were a few but since it was such a small town everyone was concerned about their...

Jessie s Fantasy Chapter 5 Afterthoughts

After Tracy mouthed, “I love you” to me, I knew right then and there that Tracy not only loved me as a male but also me as Jessie. I could feel my cheeks get warm and flushed from her comment and my thoughts. This was turning out to be the best day of my life. My thoughts were interrupted when Mark’s cock softened to the point that he slid out of my backside. Now my thoughts were replaced by something totally different.It was the thought of sudden emptiness. Something that truly belonged, but...

Carolyn Makes Her Way

After tucking my penis and balls away, I started dressing with the basics, panties first, a sheer yellow thing, and then my bra with the silicon helpers we girls so love, and then a pair of black stay up stockings. Next, I stepped into a short green miniskirt which I loved primarily because of house it would reveal my bottom when I bent over and shot pool. After that came my blouse, a long sleeve silky cream colored number that I left the top two buttons open. Dressed now, I went to the vanity...

Becoming C Her

I remember when I first felt it - silk. It was the most luxurious fabric my hands had ever touched. My fingers handled it with care in the department store. I was a teenager shopping when I noticed the silk nightgowns donned by the mannequins, draped so elegantly over their bodies. My body responded immediately and I had to buy some. That day, I bought a long nightgown and three pairs of panties - my first purchases in ladies' apparel.In the privacy of my bedroom, I slipped the panties on and...

Under His Thumb

I was sitting at my desk in a t-shirt and running shorts when my roommate Dave came in. He saw the towel I’d dropped on the floor, and immediately his nostrils flared.“How many times have I told you to hang up your towel?” he said as he bent over to pick it up. He hung it on a hook on my closet door. I looked back at him and rolled my eyes.“You’re so anal,” I said, turning back to my computer screen.Just then, I felt his strong hand grab my skinny biceps and yank me out of my chair.“Unnh!!” I...

Chris s First Oral Experience

My name is Christopher, I’m twenty-eight years old, and have my own apartment. I work for a company which furnishes custom programs for businesses. We build the programs in our office, then some of us have to go to the customer to implement it, train their employees, then monitor it for a few weeks to assure it operates properly.While we’re at the customers, we look for improvements that can be made so we can expand the program, increasing our charges to them. This starts a cycle of going back...

film fun

I met Lucy on the net, she was a married BBW with massive breasts (46g) and ass to match and loved to dress how I like my ladies to. That means mini skirt, high heels, stockings and suspenders and a low cut top. We had met a couple of times before I got to meet her husband Ray. Lucy and Ray had arranged to come to my house one Saturday night for some food , drink and fun, but I had no idea what sort of fun they had in mind. After a couple of drinks we went upstairs to the bedroom and Ray...

Andrew Andrea

My mum and I lived on the outskirts of a small Scottish village. John and his mother Beth were our neighbors, and he and I were best friends from an early age, sharing everything as we grew up. At Primary School and then Senior Secondary School, we were an inseparable pair, supporting each other through the good and bad times. This idyll came to an end when we had just turned sixteen. He and his mom moved away from the area to go look after a sick relative.The house was quickly re-occupied and...

He s So Pretty In Pink

He is sixteen years my junior, six feet tall, blond haired and blue eyed, with an insatiable desire to be my submissive sissy slut. I never could figure out what drives his desire for an older woman, such as myself, but he can never keep his eyes off my long legs or my round, voluptuous ass. He pestered me to no end to dress him as a proper sissy and take his hungry ass with my strap on and was quite relentless about it.Finally he wore me down, so I invited him over one afternoon to give him...

Girlyboy Gone Wild Part Six

With both of my hands wrapped around Dan's big 11 inch cock, I felt just like a little girl in his classroom. I jerked him off with both hands while I sucked on the head of his cock, getting it ready for him to put in my tight little girly ass.I licked around the big head of his cock, smelling my sticky-wet, cum-soaked white cotton panties he was wearing. Oh, it was all so kinky and fun and made me feel like a slutty sorority girl getting it on after class with her big handsome professor. He...

Porn Trends