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Dressed to thrill

I had lost and now I had to pay the forfeit, the four of us never played for money nothing so boring for us. The one who lost his stake first had to carry out the order of the final winner. It was king who won this time,a devious man who played cards well, never yet had he lost first in two years but on the times he won his forfeit was always sexual in some way. This time was no exception but still it was a surprise when he spelled out to me what I had to do. King told me I had to go to his...

The Beauty And The King I

Carol King was the lesbian who used to pass as a man. Big Bro procured call girls for her every week. One night, however, he demanded a raise in his commission for obtaining the call girls as her sexual partners. Carol reluctantly made the deal with him before taking Dee as her girlfriend for 72. The prolonged GFE session turned out to be a momentous opportunity for both the girls to accept each other as life partners. Cast of Characters:Title Characters:Carol Maxine King AKA Carlos Maxwell...

A service recruit

What a wonderful weekend this was turning out to be, had she only met the divine Sammi just over twenty for hours before. Now she had set her up with Gordon and with her knees flexed back to her shoulders, Gordon was about to take his just deserts with the largest member she had ever seen. Thank goodness he had agreed to a sheath and allowed her to apply some lube. She had hardly recognized her own lacquered hands gently working Gordon into to the correct frame of mind. What a wonderful weekend...

The Beauty And The King II

Carol King was the lesbian who used to pass as a man. Big Bro procured call girls for her every week. One night, however, he demanded a raise in his commission for obtaining the call girls as her sexual partners. Carol reluctantly made the deal with him before taking Dee as her girlfriend for 72. The prolonged GFE session turned out to be a momentous opportunity for both the girls to accept each other as life partners. Cast of Characters:Title Characters:Carol Maxine King AKA Carlos Maxwell...

Turned out and on

After 20 years of marriage she caught me in her panties I have been a cross dresser since I was 15 years old. I have always kept it a secret until I was 40 yearsold and had been married for 20 years. Then one night it all changed.My wife and her best friend were headed out for a girls night out. I was excited because it meant I would have the house to myself and would be able to play around the house in my panties. She had barely pulled from the driveway and I was pulling out some of her...

The Prisoner Wore Panties Chapter 1

British prisoners during WW2 formed amateur dramatic societies in German POW camps to keep themselves occupied and men played female roles quite convincingly. Their German captors encouraged these activities to keep the prisoners active and their minds on things other than escape. But what if one of the prisoners disguised himself as a woman as a ruse to escape? Chapter One - Benny's Girls When the train slowed the young woman stood and took her small suitcase down from the overhead baggage...

My colleague

The story about an incident in a construction site. Ashish has a new project to renovate his farm house, the contract is given to Charlie. Things take a lot of turns after the work begins. [email protected]

Caught in Wife s Nylons

I love the feel of the stockings on my legs. The elegant theatre of rolling the nylon and placing over my toes and then slowly stretching and smoothing them up my legs. The detail of clipping over the suspenders and then slipping my feet into the high heels. I like to stand in front of the long mirror and let my eyes slowly rise from the black patent heels over the slight wrinkle of nylon on my instep, up my legs to the band of the stocking tops. And then my cock slowly dripping pre-cum,...

how it continues

Since I posted my How it started a few things have changed. I still borrow my wifes used panties to jerk off into and still really enjoy doing that. BUT I GOT CAUGHT AGAIN. This… Since I posted my How it started a few things have changed. I still borrow my wifes used panties to jerk off into and still really enjoy doing that. BUT I GOT CAUGHT AGAIN. This time by the daughter of a close friend. Last winter I spent a week at our cottage. The first few days our place was just to cold to stay...

Dave and I

This is a work of fiction. Any resemblance to any person living, or dead is purely coincidental.Later that day we sat at the table talking about the events of the past evening. The phone rang. It was Dave on the phone. He wanted me to go out with him on Friday and he wanted me to dress sexy.. I had been with Dave only one time; it was at my anniversary party. My wife arranged everything. She invited her friend Kim and her male friend, Dave. I did not know she'd invited anyone. I was dressed en...

The Wedding Proposal chapter III

I woke up and saw the bright, yellow orb of sun shining in through the broad windows. It was warm, and the thin linen was wrapped around my sweaty body. I was glad I remembered to remove the tight corset before going to sleep, and I was now wearing only the thigh-high stockings and garters. A pair of white panties lay on the floor where they had been hastily thrown. My fake breasts were still firmly attached, and I had already grown somewhat accustomed to the extra weight on my chest. Lying...

A Sissy s First Dildo Experience

Buying a dildo online was a bit nerve-wracking, honestly. Not for any huge reason or anything – I live alone, and the packaging is supposed to be discreet anyway, but there’s just something that made me nervous when I first put in the order.Sure enough, it wasn’t like it was a fat box labeled, “Tasty Black Dildos for Sissy Whores,” all around it; just a plain box, inside which was some bubble wrap and a plain, pink bag. But inside that bag was an unforgettable package.After carefully opening it...

Cross Dresser Loves being used

I have cross dressed for almost fifty years. It started in the UK when I was eighteen, I had often read the various catalogs for mail order purchases and used to look at the women's lingerie pages where the ladies were wearing garter belts, girdles, panties, stockings etc., and I used to get hard and play with myself and jack off to the pictures.I was always fascinated at my older sister who used to wear stockings, garter belt, etc. and it excited me. One day when nobody was home, I went to my...

The second night beyond the bookstore

I woke up Saturday morning still wearing my lace panties, bra, breast forms, and thigh high stockings from the night before. I had dried cum between my breast forms in my bra, my shoulders, face, and in the front of my panties. The crack of my ass was still a little wet with lubrication. I went into the bathroom and sat on the toilet feeling like a woman, still reveling in the orgy from last night. I turned on the shower before reluctantly stripping down. When I stepped into the shower, the...

Al

The sidewalk was lined with hogs, their front tires against the curb. Joe's Bar and Grill would be hopping tonight. I sauntered in and elbowed my way to the bar through the acrid smell of cigarettes, stale beer, and unwashed bodies.I perched myself on an empty stool and signaled Joe for a beer. He gave me a quizzical glance and pumped a stein of lager for me. As he set it down in front of me, he said, "Al, I don't need any trouble here tonight. Got it?"I parted my suit coat, smiled at him, and...

A Date For The Weekend Chapter 1

I've been crossdressing and living as a woman full time for years. I put a lot of time and work into transforming myself into an attractive woman that can accompany a man anywhere in public and never raise an eyebrow. I've long since moved on from having casual cheap hookups to expecting more elaborate playtimes, and generally only date men if we can plan a weekend or more together. I mean, if I spend all this time and effort I expect more payoff than ten minutes of action. I really provide a...

Jessie And Sue s Date Continues

Sue and I had a great time in the lingerie section of the department store. Getting caught by the sales clerk was definitely not something we planned on happening, but in some strange way it added a whole new dimension to what we had done. Both of us got out of the store as quickly as possible and headed into the mall. Sue suddenly turned to the right and stopped at a shoe store. This shoe store catered strictly for women, so part of me was uncomfortable, but another part of me was excited to...

First Encounter Ch 6

The elevator ride to our floor is thankfully uneventful. We manage to keep our hands off of each other until I unlock the door and we step in. As the door closes behind us, you grab me and we embrace tightly. Our lips lock and you rub my crotch through my pantyhose."Alone at last!" I breathe. "Let's get comfortable." "I'll take care of this," you exclaim as you drop to your knees and pull down my hose and panties.My balls and shaft spring from their confines and wave gloriously in your face. I...

Terry Gets It In The End

The converted attic was my room and it gave me loads of privacy. So as I grew up I could wear the clothes I liked, as long as I stayed in my room. By the time I was a senior in high school, I kept my toe nails painted all the time and I wore panties every day. At night I wore frilly little night gowns and more likely than not I would masturbate, always fantasizing that I was the girl and some faceless guy was fucking the shit out of me. I learned to dance and I loved the way my skirt flew up...

The Secretary Part 2

I arrived at Michael's office a few minutes before 9am. Being that he rented a small space with many other companies sharing his floor alone it was a a hive of activity. People arriving for work, bustling past each other, shouting greetings, enquiring into weekend activities. I received a few smiles and polite greetings as I walked through the corridors, as well as a few winks and impolite stares at my arse. I walked through the first door into the space Michael rented. A reasonably large area...

Dressing up

It was the summer of my sixteenth birthday. It was when I first thought of girls’ clothing as the clothes I would like to wear.My name is Matt and I live with my three sisters and mother. I am the youngest and as you may realize in this sort of set up, there is no shortage of girls’ clothing for me try on.I had just turned sixteen and it was summer. As usual, the four beautiful women in my life were sitting out in the garden sunbathing in their bikinis. Mom and of the girls were even topless,...

Anonymous Encounter

Well it was a boring day. It was fairly hot outside,somewhere around 93 degrees. The sun was shining, there were very few puffy clouds in the sky, and I was home alone. As usually happens when I am bored and home alone, I was horny as hell. I wanted to jerk myself off, but I wanted to do it to something different than the normal porn that I usually watch. I figured since no one would be back at the house until tomorrow, I would take the time and dress up and do my makeup and hair and really go...

Not Your Typical Traffic Stop

Hi my name is Stephanie and this is a fiction based on my dirty desires. I was making a risky trip to my local adult video store dressed as Stephanie. The sun was setting and the drive was only 10 minutes, tops. I figured with low light and close proximity of my playground of debauchery, I would be safe. I admit because of nerves I had my black 'fuck me' heels hard on the gas. My heart sunk as I heard the siren and saw the cop car behind me. I was fucked I thought as he would first notice I...

A Gift for Daddy

"I brought you a present, Daddy," Stephanie said, giggling, as we stood on the porch in the run-down neighborhood in the industrial part of town. The man standing inside was in the shade inside of the house and I squinted to get a look at him."Eyes down," Stephanie hissed, elbowing me. I did as she said and smiled inwardly. She was usually very submissive and proper when we were together and I felt the power balance shifting already. The door opened and I followed her in. Despite the disheveled...

The Slut Within part 2

As I continued on my knees, I felt my little thong riding up my tight little butt. My skirt got in the way of spreading my legs and my tube top and my skin was all sticky with cum. Thankfully, I wouldn’t be wearing any of this much longer. Their watching eyes so aroused my slutty nature. I took off my tube top and skirt leaving my fishnets and six inch heels. I also wore a black thong and bra with the pink mesh that made me feel hot and sexy. I made a conscious effort to shake my hips and moan...

Jaime s Way part 2

I awoke to feel the dried cum on my face, ass and balls, and then remembering how I got that way made me smile. Crawling out of bed I made my way to the bathroom and took a hot shower and then easily shaved my already smooth legs. Out of the shower I brushed my hair and did what I could to make it appear more feminine. After I put on my make up I walked back to the bedroom and slipped into a pair of sheer blue panties. The cage Sherry had put on my dick prevented me from jacking off but since...

Confessions of a Sex Crazy Crossdresser Part 7

Chapter 13: One Hour Photo I checked in at the motel and went to my room. It was a standard motel near the freeway, two levels tall and I was on the lower level in the room farthest from the office and facing away from the freeway. I opened the door and turned on the air conditioner. It was still about 85 degrees and it was after 5:00. After a quick shower, I picked up my voice mails from home and returned a couple of calls for work and then got dressed into some nicer clothes. I knew there...

Truck Stop Tranny Sluts

My girlfriend and lover Candi and I were driving back to her place for some steamy tranny sex after a night of partying at a tranny/gay bar in town when we passed a truck stop on the highway. Buzzed and horny as we were, we laughed about stopping in the lot and doing so hookin’ as a means to get us some trucker cock. After a minute or two of silence, Candi said lets do it and before I could answer she was turning back for the truck stop! Candi and I are both bisexual crossdressers and we pass...

A Master For Julie Jizzbucket

I had spent the last couple months indulging in some mild cross dressing. After a few nights wearing clothes that made me feel so sexy and womanly. Until recently I had only worn panties, bras and a few sets of stockings and teddys that I had bought for an old girlfriend before she broke up with me to date a guy that had more money. I have also been going online to a site called Lush Stories to write some of my cross dressing fantasies. Once I had written a fair amount of stories, I found...

Summer dressing

It was the mid 1980s, I was 20 years old and it was the summer holidays. For the long break from college I'd managed to find a vacation job in Kent in the south of England. It wasn't brilliant but I was going to get some experience of working with computers, and earn a bit of money to keep me going during term time. The company was based in a small town where I had found a room in a house with a fairly old-fashioned landlady. The freedom of being fairly anonymous in this new job and town was...

Ever tried dogging

Nick steered his sleek silver turbo-charged coupe across the deserted Cambridgeshire by-roads towards Ely. The town was justly known as 'the ship of the Fens', as the tower of its majestic 16th century cathedral was like a navigational lode star. Ely's train station was only a few hundred yards from the cathedral and Cathy stood waiting in the shade of the station building's canopy. She wore the shortest of floral print dresses, with pink fishnet stockings and open-toed high heels, revealing...

Weekend Discovery 1

Friday had finally arrived. Andrew Lippincott glanced at the Rolex on his wrist and then began to pack his attaché case. It was only 4:00 pm but he was the office manager and one of the perks that came with this title was the ability to leave early. Winter had the city in its grasp and a travelers advisory had been posted.That meant there would be no unannounced guests to prevent him from enjoying the weekend the way he wanted. Simone Treco, his personal secretary issued her standard invite to...

Stranger Fuck

I noticed the time strike 10pm on my watch as I got out of the cab outside the Red Circle. Hopefully tonight I was going to get lucky. After paying the cabbie and stepping out of the cab, I fixed my tight pink and black striped dress as I stood outside the club. The Red Circle was the most notorious Sex Clubs in the city where couples and singles went to hook up. Tonight was their Gender Bender Fetish night, which is why I had got dressed up tonight.I have been crossdressing since I was quite...

Across The Street Part 3

Mike was leaning back in his desk chair enjoying the after-effects of his orgasm. He leaned forward and looked into his telescope to check on Leann. He saw that she was still in her chair with her eyes closed and her legs spread, floating down from her orgasmic high.As he flopped back in his chair, he still couldn't believe it. The girl he had been spying and masturbating to her dancing image was actually a male dressed as a female. What surprised Mike the most, was the fact that he was not...

Back At The Adult Bookstore For More

After several positive experiences with sucking dick, including swallowing, I started going to the adult bookstore once or twice a month. As always, I would stop at some obscure spot and change into my female clothes. Then, I would put on a coat to walk from my car in the parking lot into the bookstore where I would pay the clerk for entry into the darkened “theater”. It was really three small theaters connected by two hallways lined with viewing booths. There were usually several men leaning...

First Time Out

This is a true story about my first time I went out dressed at a club I had been in the closet for years and up until this point only a few people had ever seen me dressed my freind Bill and some guys I went to an adult book store. I had been dressing for Bill alot in mine and his apartment but I had this erge to go out clubbing dressed I had asked Bill several times but it seemed he enjoyed just what we were doing in our apartments but I needed more so I decided to do it without him, I made...

In Her Shoes

I opened my online mail box as usual, looking down the list in case any new spam was in amongst the thirty-seven mails I had received. As I scrolled down the page I noticed a new mail from one of the sites I used to find new partners for sex. I clicked it open straight away not wanting to waste any time, hoping that this mail for once was from someone more sane and rational than the usual, and hopefully close to where I lived. Hello Kylie, My name is Peter I’m a 31 year old straight male and...

Jaq enjoys both of us

We had known Dave and Maria for a while through our various clubs, unfortunately we had not played as a foursome. It was a Friday night at one of our swingers parties, Dave, Maria, Jaq and myself found ourselves chatting together. The wine had been flowing freely and the conversation was very much revolving around sexual desires.Dave went off for a round of drinks, this is when Maria confided that Dave loved to dress as a slut with Maria but was a little shy to take it any further. We explained...

Tennis

Sandra and I had been going out together for about six months. She was the perfect looking girl for me, with her beautiful freckled face, slim turned-up nose, pouty red lips, light green eyes, long blonde hair that she usually kept in a ponytail or braids, a great body topped with perky B-cup tits, and a cute firm ass that just screamed to be pumped. She was only 23, but Sandra already knew what she wanted out of life, and wasn’t afraid to go for it. She had met her latest acquaintance at the...

Caught and the Consequences Part 2

Part 2 While sitting there I went through the usual stages, despair that I had been caught, fright as to what would happen next, would she still want me as her husband or was this going to be a third divorce, and that made me feel very sad as it suddenly dawned on me how much I loved her and I quietly resolved to do anything I could to save my marriage. It also made me realise that our relationship was already a sub/Domme one, in subtle ways I had not...

Total Sub CD Slut

I could not wait to get home from work on Friday. My routine was the same. It was total preperation for the weekend.I was a highly placed executive with the company I worked for at the time. Nobody knew that I lived as a total sissy slut cock worshipping whore on the weekends.I was seeing a guy who was very dominate. I met him online. The first night he took me home he dressed me before having sex with me. He made it clear that I was to not only always be a "girl" around him but I was to come...

My Boyfriend s Blue Silk Panties

My boyfriend, Allen, is a man's man. Let's get that straight from the start. He rides a Harley and he scoops me up in his big strong arms like I'm light as a feather (which I'm not...let's get that straight from the start, too).So it was a big stretch for me to ask my masculine lover to slip into a pair of silk panties just for me. It was a secret fantasy I'd harbored for years but had never found the courage to ask a man to do. Allen was special, though, and I wanted him to be the one to...

Made Maryanne

It was 3 am. I was busy whacking myself off in the bathroom when Beatrice caught me. She and I had only been together for a few weeks when I started taking a special interest in her underwear. I loved the smell of her wet pussy, combined with the cozy softness of the cotton panty gusset pressed against my nose. Wearing one pair, feeling the delicate material clinging tightly to my ass, I held up the other and inhaled deeply. My cock was throbbing steadily, enjoying the attention afforded by the...

Adventures in a Woman s Body Chapter 3 Used by Strangers

I put his softening cock back into his pants as he parked the car. He got out and I crawled up after him. Having been on my knees for so long, my knees were aching and my legs were sore, but at least my feet got a rest from walking in my seven inch black stilettos. “What’s your name, by the way?” I asked him, since I don’t know what to call him by. “Just call me your Daddy, sugarslut.” He chuckled, putting his arm around my ass again and leading me to walk. I was feeling so anxious, scared, and...

Park n Play

Being the social butterfly that I can be at times, I was checking a website that listed my area to see of there were any 'cruising' areas I could check out in hopes to share my fetish for crossdressing and pleasure. There were several areas, too many to choose from, so I opted for a forested state park. Since much of the funding for the parks in Ohio have been suspended or cut, the chances of being targeted by a park ranger or law enforcement for public indecency can be pretty low. I've heard...

From the Bookstore to the Bedroom

Some of my stories are true, or at least, based on actual experiences. Others are complete fantasy. This one starts with an actual experience and turns into a fantasy of how I wish it would end. I never get as much “gurl time” as I would like. It seems when I dress, the time flies by too fast. So, when I get the rare opportunity to get away from my captive male life for more than the usual few hours, I make the best of it. In this case, taking the hours required for a complete transition...

Girlyboy Gone Wild Part Four

Being a slutty sorority girl having sex with my professor was really fun. I was sitting in his lap with my back to him with his big 11 inch cock between my freshly-shaved legs and rubbing it against my hard clitty dick. My little white cotton panties were soaking wet in front with pre-cum. My teacher was playing with my titties while I stroked his big one."I'm going to take your bra off, okay, Courtney?""Please do," I said. "I want you to feel my hard nipples without my bra on."I held my arms...

Jamie s gradual grooming

"Jamie? Is that you?" A voice shouted out from across the road. Jamie lived in a relatively small town or village so it must be someone he knew. "Jamie, it's Mike from three doors down, Phillippa's dad?". With that Jamie stopped, he walked over to the very fast and expensive looking BMW. "Hi Mike, sorry I didn't recognise the voice at first are you okay?" Mike explained, he has seen my Mum the day before, who had aired my dirty laundry with him, charming! "Do you want to go and get some food...

The Wedding Present

Chardonnay had been Phil’s live in sissy lover and constant companion for just coming up to two years. She wanted to do something very special for him and had saved enough money at last. She phoned an exclusive hotel, giving great detail into what she required. She made a few more calls that afternoon while Phil was working. As she finished the last call, she gave a huge grin to herself in the hallway mirror.Phil had given her an engagement ring the previous year, which she found such a delight...

Mistress Hannah s Pathetic Husband Part 8

As we tried to sleep one Friday night after Mistress Hannah had used my ass with unusual vigor, she was tossing and turning and keeping me awake. I got the impression that she was struggling with some personal demon that was becoming an urgent threat. Something had changed around the time two months earlier when I had first achieved the goal of putting my puny pud up her ass. I don't think my attitude toward her had changed, but I think maybe her attitude toward me had. I was still her weekend...

A Nanny Femtastic 6

A Nanny Femtastic Chapter 6 ......... felt incredibly empowered, with women and Men coming onto me! I was loving being between the two sexes but presenting as a glamorous female. Alex was very dominant and bought me drinks and acted in the male role very much that night. Lou and her slept together generally, but there was no issue with Alex coming onto me. Later in the evening we found a private booth and kissed passionately. She fondled my breasts through my lace bra, and put her hand up my...

A weekend with Nancy part 2

Nancy informed Alice that she would be using the bedroom to dress me, and that she should pick out an outfit consisting of no fewer than seven articles, gather her make-up and whatever else she required and then use another room to get dressed. Furthermore, Nancy informed Alice if she didn't like what she was wearing when she returned that she would be punished, and to not waste any time dressing as she would require her help in transforming me. I had the feeling that no matter what she came...

Confessions of a Ladyboy Part 1

I was eighteen and new in the boy's hostel. No one had wanted me at home. I had never known my father. I saw my mother go out with a different man almost every night ever since I was old enough to remember such things. She taught me some valuable lessons - how to be attractive, how to carry myself, how to be seductive, how to do my makeup.She always said, "You are such a cute boy, you were meant to be a girl."She caught me one day, dressing as a girl in front of the mirror when I was very young...

my first time

I’m 28 now. I have been interested in women’s clothing as long as I can remember. I can remember when I was around 7 my sister caught me trying on a pair of her panties that I stole out of her room, I don’t think she ever told on me about that. As I grew I was always stealing pantyhose, dresses, skirts and etc from mostly my family and my friends sisters. I wasn’t really turned on by guys, but when I would slide those sexy pantyhose over my legs, I would find myself fantasizing a friend...

Vanessa and Ken s Second Date

It had been a couple of weeks since Ellie and had our little trysts with Derek and Ken, and I couldn't stop thinking about it. As much as I loved being with Ellie, there was something magical about that night with Ken. We had talked about it, and I downplayed how wonderful it was to make love to Ken. She told me that she enjoyed her night with Derek too, but she didn't really seem to make a big deal about it. I wondered if she was downplaying it too, but part of me didn't even care. Maybe...

Mistress Hannah s Pathetic Husband Part 3

The first week of having a useful cock went well. For the first time since we got married, we had sex every night. After strapping my extension on, I would lick Hannah's pussy enough to get her turned on and then she'd choose a position. If I got physically worn out, she would choose another position. Because I was having sex so often and doing some research on the Internet, I was able to develop some control over how soon I came. I was easily lasting over two minutes, partly because there...

Adventures in a Woman s Body Chapter 5 Secretarial Duties

John waited for me to finish eating my cum burger, and then he told me to get up because we were leaving. I stood back up onto my six inch stilettos and walked with his arm around me, which firmly grabbed my ass. We exited the food court and made our way to his office building. The mall had a vast underground network so we were able to walk to his workplace without going outdoors. Along the way though, he never turned down the vibrating dildo in my sissyhole so I was on the verge of climaxing...

Uncharted Territory

Of all the activities that Cal Markus imagined he'd be doing on his summer vacation, this was not one of them. Here he was in his longtime friend John's attic wearing an almost sheer pair of black silk panties over a pair of black crotchless pantyhose and seated in front of a large lit makeup table as his friend was busily bustling around the room depositing items of makeup on the table.The sensation of the silky panties against his skin was unbelievable as was the sight of his cock pushing...

Oh Daddy

It all started with an online ad. I had always known I was different. I tried to pretend I liked girls, but I really wanted to be one. Let me describe myself. My name is Tony. I am 17. I'm 5' 10", 125 pounds. I have long blonde hair that girls are always jealous of, but it's always my blue eyes that draw everyone's attention. I was pretty shy and mostly kept to myself. I had a few friends, but I didn't spend much time outside school with them, as I was trying to keep my feelings secret. As I...

My first Cross Dresser and me

I laid down beside her and gave her the soda. We sipped slowly and talked about what had just happened. I sat the sodas on the night stand and moved up closer to Toni (a name we will use for this article) crossing my leg over hers so that my clitty rested on her nylons. We kissed for several minutes as I played with her nipples thru the silky bra. Toni looked up with lust in her eyes and said she wanted me to fuck her.I started kissing her neck and started down her soft body, I raised her bra...

Dawn Visits Kansas Chapters One Six

Prologue:In an earlier story, Dan Becomes Dawn, Dan had stopped in Denver, coming out as Dawn, a crossdresser, to former neighbors. At a swinging party the next night, Dawn had met, and connected with, Patti. She accompanied Dawn to Steamboat Springs on a business trip for two nights. Dawn worked three more days, then returned to the former neighbors’ home for a second weekend before returning to Florida. Meanwhile, Patti visited her daughter in Aspen, then returned to her parents’ farm in...

Fucked in the Fitting Room Part Two The Explosive Conclusion

I took Allen's hard cock in my mouth and began to suck it slowly. "Oh, God," said Allen. I rolled my tongue around the tip of his cock and then ran it up and down the sides."Suck it faster, babe," said Allen. I happily complied, bobbing my head up and down on his cock as fast as I could.I grabbed his balls in my hand and stroked them gently with my fingers."Oh, baby, that feels soooo good," said Allen."Take your clothes off," said Allen. I stopped sucking that beautiful penis. My pussy was...

A Great Date

I was so excited to sign online and see a message from my sexy college boy. We hadn't spoken in a while and I guessed that we would never get the chance to finally meet. Many a night had I masturbated thinking about his lovely cock, though I had only pictures to please me. It turned out that he had been thinking about me too. "I can't get you out of my mind," he said. "I need to meet you. Let's go on a date sometime." He knew that I wanted so badly to have a sweet man take me out on a real...

First Time With A Crossdresser Part 1 of 2

I’m Scott, 36 years old and recently divorced from my wife of 12 years. It was an amicable split with no kids to complicate matters. We sold up, divided everything two ways and went on our merry way. Our sex life was good and regular but a little boring. We stuck to the same three positions – missionary, her on top and spooning. I’d give her oral but she wasn’t that keen on going down on me and her facial expression when she was blowing me put me off asking for it! I’ve never needed more than...

Dan into Dani Part 2 Getting used to girlhood lingerie shopping

OK, Dani, take off my knickers, choose a fresh pair from the drawer, and let’s get you dressed,” said Lucy.Dan sat up in bed. He was wearing a tight-fitting white bra and Lucy’s knickers - the ones he had pulled down Lucy’s legs before he had plunged his throbbing cock into her wet and inviting cunt. The night before. When he had been a boy.Now everything had changed. He had been tricked into putting on a bra that had magically and instantly turned him into a girl.He had been a six-foot shy...

Kaitlyn

(Saturday, Dec. 14, 2013)Mitch was expecting someone. He paced his living room floor nervously, anticipating the person’s arrival. As he took another step, he wobbled and nearly turned an ankle. “Stupid heels,” he muttered. He was still getting used to walking in high heels. He’d just put them on about fifteen minutes ago. He glanced down at the high heeled sandals, his exposed feet and his red, painted toenails. Is this for real? He asked himself. He heard the sound of a car door slam. His...

Workouts with My P E Coach

My P.E.coach, Coach Cocker, was a tall, handsome man. More than once when I saw him blow into his whistle, I wished he was blowing me. I was a seventeen-year-old tranny-in-training and I loved having a big handsome man sucking my dickie for me. So, it was only natural that I would want Coach Cocker sexually. I already liked flirting with him like the girls did. And I thought he liked me, too. Then, one day, I was walking in from the sports field toward the gym. I was wearing my sexy little gym...

Jessie s Fantasy Chapter 1 Losing a Bet

Nearly everyone has a sexual fantasy that they would love to act on sometime in their life. Unfortunately for some, it never becomes reality. There are many different reasons, ranging from having fear or hesitation, to fantasizing about someone they can’t have, or the situation just never presents itself. This is a story of one such fantasy. Hope you enjoy! It was a Friday evening and I was on my way to meet my usual group of friends. The eight of us had been friends since high school, and we...

Becoming Sarah

I was driving home from a work trip. That is how it started. There was roughly 85 miles to home. I had been driving for about an hour when my mind began wandering the way it always does when I'm not preoccupied. It always goes to the same place. For the better part of five years, I have been cross-dressing in secret whenever I have the house to myself. Sometimes I do it because it excites me sexually, and sometimes I do it just because it feels right. The way silky panties slide around on...

Stage Ten Of My Journey To Becoming Joann

I was excited about the next soccer practice. There were no guys at the last practice due to Gurls Night. I was hoping Donny would be there this week. I stopped working at 4:00 so I would have enough to time to get ready. I went into the bathroom and filled my douche bag with a little over two quarts of warm water and special soap. I took off my shorts and panties before pushing the enema nozzle into my ass. I still get a hard-on as the warm liquid fills my bowels. I cleaned my face as I held...

Christmas At The Salon

Back in October I introduced my friend Susan to boys that wanted to be girls for her beauty school.They would come in for help with their hair and makeup and her students could practice on them.Everyone had a ball and it worked out very well. Soon the girls realized that this was a dream come true for the boys and became more demanding of them.Keeping the place clean was just one of their many new tasks.They had to speak in a feminine voice when they were there and address each girl as...

Maid to be Submissive part 1

As I stared up at the ceiling, contemplating my own existence, I couldn't help but retrace the last few weeks in my mind. My girlfriend had just broken up with me, apparently, she had met someone else and had been cheating on me for months.The same week, I found out that my company was laying people off and I was about to lose my job too. This is how I ended up at age twenty-five, living with my mom again.It wasn't all bad, I thought, trying to convince myself. My mom owned a long-stay motel,...

A Night of Firsts pt 2

I opened the door to the club and walked inside. From the outside, the older brick building looked sort of run down, but once inside I found myself in a club with large bar on one side, polished brass railings, mirrors, subdued lighting, tasteful seats at the bar, hardwood floors, tables, a few booths further away and at the very end of the club a large stage with karaoke being sung. This was no seedy dive bar, thank goodness.The lights, the music (karaoke music is always so loud as if...

Mistress Sarah makes Evie a Sissy 2

"Look at you Evie. You're so slutty in your teddy and stockings,” said Mistress Sarah. Then she looked down at my hard cock and said, "....and your clitty is so big. Excited are, you?" Mistress Sarah reached out and firmly squeezed my cock a few times. It was a welcome sensation that reverberated though my entire body. Before I could respond, she ordered, "Turn around slut. Let me see that arse of yours." Ever since I had met Mistress Sarah online, I had dreamed of her fucking me in the arse....

The Rendevous

The Rendezvous He called Saturday night just after ten. His wife was being admitted and they may induce her labor. He told me how much he missed me and how needy he was for my warm, wet mouth. I told him to be patient. His responsibility was to take good care of business. He told me that his wife was fine and that he hoped to see me on Sunday. We hung up. I hadn't meant for it to happen, but it did. I'd been drunk and tired and that night at the party when the hot stud...

Chrissy Gets Bolder Meeting Todd Again

I really hadn't expected Todd to call me after that night. I know how guys are when the night is getting short and you need someone to satisfy your needs. I did think about him a few times and wanted to see him again.I had enjoyed my first experience with a man so much it seemed that's all I could think about was my next cock. When I went to class I would catch myself looking at guys as much as I was girls. I made it a point when I got home from class to work on my make-up and doing my hair. I...

The Wedding Proposal Wedding Night Intermission

I could feel his hot breath on my face as my red lips slowly retreated. He drew air in through his nose, savouring my perfume and smiling back at me. My hands left his crotch and gently moved up along his tight torso. The slightly contoured muscles felt warm through the stiff cotton shirt. My long fingernails complicated the unbuttoning of his shirt, but I approached my goal one button at a time, all the while saturated with tension and expectation. At the same time, he began pulling his pants...

slut on the town

I got put in a full nelson the other night by a naked black guy. It happened in a video preview booth at Corey's Adult Video store in Oakland. I had been hanging out in the arcade, wearing just a black two-piece string bikini, and a pair of fire engine red high heels.I had been there for about a half hour, but I hadn't seen anyone. But it was early, only 3.30 p.m. Then I heard the buzzer go off and I knew someone had entered the arcade. I stood near a corner, waiting. It was pretty dark in the...

Have A Good Feel She Loves It Part One

I initially came across David like so many other people I know on the scene whilst fishing around on the internet. Unlike many though, he was 100% genuine, he’d read my profile on the transvestite contact site with interest and taken the time to write to me. It was a well thought out message that consisted of real words, put together in sentences with no text speak. I liked him for that from the start. We arranged to chat online one night, he wanted to see if I was the kind of chick he was...

Extended Vacation

Hi Everyone...this is the first chapter of my second book. I will publish more chapters if you like this one. Extended Vacation Chapter 1 Hello my name is Cassandra. You can call me Cassie (or Sandy, but recently, I like Cassie). I have been cross dressing for many years. However, the last year, since I turned 40, I have been dressing more than I ever have in my entire life. I made a very smart decision two years ago in regards to my cross dressing. I spent almost a year preparing to be...

It s Just Dinner At The Lakehouse My Sissy Transformation Part 2

The week flew by and before I could blink it was Friday. The blur of a week was mostly spent getting everything I needed to make sure the weekend at the lake house would be a success. I got new clothes, invested in more high-end crossdressing products, and went down a research rabbit hole of sexuality. One dinner party sent me on a downward spiral.Does this make me gay? Is it fucked up that I kind of liked it? What the fucks wrong with me? Unfortunately, the Internet could only help so much so...

Early Morning Run Turns Into Mid Morning Fun

I walk my dogs every morning, usually between 6:30 and 7:30. The road is remote and in most cases, the only people and cars on the road are neighbors and the occasional contractor. The walks are a great way to start the day. Between morning thickness, the warm sun, and gentle breeze, more times than not I am extremely horny when I get home. Cumming while taking a shower and watching various styles of porn is a great way to start any day. At least a couple of times a week I see Paula walking...

Another Road Trip Story

With trembling fingers, he began to pack his large suitcase. First, he started with some of the silkiest and sexiest lingerie in his extensive collection. At least a half dozen silk and lace bikini panties along with tiny silky thongs were placed inside first along with their matching bras.Garter belts made of satin and silk came next. A half a dozen pairs of black nylons that were either seamed or patterned shared a spot along with crotchless pantyhose. Four long silky full slips each boasting...

Turning into a Middle Age Slut Part 1

I have had the crossdressing bug for many years and have collected some items to fully dress with, such as a wig, makeup, fake boobs and all that makes me look as fem looking as possible. Being in my mid fifties however, there was really no way that I was going to be truly passable or that hot, so I thought Over the years, I collected my lingerie, heels, wigs and experimented with makeup. I mostly took it with me on travel to experiment with in the hotel rooms. I bought most of the stuff off...

A Whole New Me Part 1

“Honey! Are you around?” I shouted from my room, rummaging through my drawers and naked from the shower. “What’s up, sweetie?” My girlfriend, Lisa, popped her head around the bedroom door. Her eyes taking in my body and a cheeky smile forming on her pretty face “Oh, looking good.” I wasn’t the most muscular guy but I wasn’t fat at all and Lisa always claimed she liked my body not being so hard and rough. She even convinced me to shave it more or less hairless; saying she preferred it that...

The Afterparty

Steve awoke dizzy and confused. His head was spinning from all the alcohol he consumed from the party last night. As he tried to focus his eyes in the pitch black bedroom he realized he was bound to each corner of the bed. He struggled to free himself but the straps were to tight. It wasn't his bedroom; the sheets didn't feel the same and the bed was much bigger than his. Perhaps someone at the party was playing a joke on him. As Steve struggled he noticed the clothes he was wearing were not...

Meeting Mistress Sarah

My heart pounded fiercely as I stood at the door to Mistress's house. I did not expect to be so nervous at meeting her again. After all I had known her for quite a while now. Mistress Sarah had been gracious enough to allow me back into her world. I was fortunate to fall under the control of such a dominant woman. She had moulded me into an obedient and submissive slave through the use of e-mail, texts, and online chat sessions. At the insistence of Mistress Sarah, the time had finally come to...

My 2 AM Phone Call Part Five

Bondage means different things to different people. To some, it just means being tied up, but I always felt that true bondage means a lot more. It can mean total surrender to the situation I find myself in and total embracing of the situation, knowing I can't do anything about it.When I looked more carefully at the machine that was in front of me, I realized that this was to be a special challenge. It was pretty clear I was going to be positioned on the machine in such a way that I could not...

All Tamara s Panties

Jimmy Swann liked to believe he was the consummate businessman; suave, sophisticated and with an eye for the ladies. He saw himself as an international dealer in supply and demand but In reality, he was barely one step above the small-time drug dealing bottom feeders. He tried not to draw too much attention to himself and thought that as long as he kept his nose clean and paid off the cops who mattered, he would be allowed to work his patch without too much harassment. He did, however, enjoy...

Night Out Ch 3 Talk to me

I wonder if it’s too late? I mean...it has been three days."Jamie, we have a meeting coming up around 2:15 pm. Did you get the email?"He looked up ungluing his zoned eyes that were unfocused on the screen of his work computer. Again, he was lost in his thoughts as he feigned being busy due to the inability to focus. Evy was heavily on his mind; invading his workday. He almost didn't recognize his name, which highlighted another obstacle of hesitance with reaching out to her."Uh yeah. It was...

Caught

I stood in front of my full length mirror wearing my new black heels. Not just the heels of course! I had a sexy, short black dress to go with them. Underneath, I had some incredible purple and black underwear; all silk and lace. I twisted on my heels and pulled my dress up a little, wiggling my thong covered ass at the mirror pretending somebody could see... ...And that’s when he knocked! My flatmate Derek knocked on my bedroom door and shouted me. I had thought he was out for the night so...

Neena Wanted To See My Panties

I've always fantasized about it, Neena wrote. Meeting a man in a bar. Going back to my place. And discovering that he's wearing panties. It’s so taboo.We were texting one another. A few days earlier, she'd responded to a simple ad that I'd placed online. There wasn't much text--just a picture of my hard bulge barely contained in panties. She was the only woman to reply.Have you ever been with a man in panties? I asked.No, she responded. I've posted a few ads myself looking for it. ...

My Lesbian Lover

My wife was trying to come to grips with the realization that I cross dressed, with marginal success. Part of her plan was for me to meet in the Twin Cities with other CDs so I could have a ‘safe’ place to dress up, away from our small town. To be safe, I was to drive up, change clothes there, meet with my friends and then change again for the drive home. A good plan … a safe plan … but not one I particularly liked (so I changed it a bit!) Kim was a mutual friend who lived in town. Although she...

What Do You Do When

The weekend arrives and mom and dad are going out and I assume they are going to one of their swinger parties and won't be home until early the next morning. So I do my normal thing when they are gone and play dress up and go out and hunt for dick. But this time I knew they would be gone and had already planned an evening of fun with a couple of guys I had met at the adult bookstore my parents owned. Once they left I called the two guys on the phone and told them to come over,that it was safe....

Porn Star Babe Part Two

Being a sexy girly boy about to make her debut as a porn actress with two handsome, well-hung studs was so exciting to me. And having my friend, Chrissie Licks, along to show me how it is done was especially re-assuring.Chrissie and I were naked and about to get into our sexy lingerie for the shoot when Summer Cox, another hot tranny porn star, came to help us with our hair and make-up. Summer was a beautiful, lively blonde and alot of fun to be with. She and Chrissie explained to me that...

No Strings Attached The Reunion Chapter 25

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

My First Date

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

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