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Crossdressing Charlie Episode 9 Everybody s Crazy

CROSSDRESSING CHARLIE Episode 9 EVERYBODY'S CRAZY "What are we going to do now?" Charlie yelled over the loud rush of passing cars. "I don't know!" cried Rachel, tears streaming down her face. "Well we can't just hang around the streets all night!" shouted Charlie. Rachel didn't say anything back. She continued to walk briskly ahead of Charlie as if she knew where she was going. Dusk was rapidly descending into night and the skyline of the distant city buildings was...

Crossdressing Charlie Episode 10 Prudence Svahnstrom

CROSSDRESSING CHARLIE Episode 10 PRUDENCE SVAHNSTROM The moment that Charlie was told that he would be moving out of his current home he could not help but feel a little sad at first. However, the more he thought about the prospect the more it made him feel hopeful for a brighter future. For so long he had been stuck in a never-ending chasm of darkness and now there was a light at the end of the tunnel. It was something to look forward to, something to root for and above all else a...

Crossdressing Charlie Episode 11 Under His Thumb

CROSSDRESSING CHARLIE Episode 11 UNDER HIS THUMB Prue watched him get into the car from the top of the steps. Dave, who was still standing outside of his car, stared at Prue maliciously. She returned the gesture, glaring intently with apprehension before watching him swing into the car. Dave was quieter than usual as he settled himself at the wheel. He looked unnerved, doubtful, and even a little irritated. He turned the key in the ignition and the engine revved up like a vicious...

Crossdressing Charlie Episode 12 Seventeen

CROSSDRESSING CHARLIE Episode 12 SEVENTEEN It is the 12th June, ten days after the shopping/cinema date and Charlie has not heard from Dave. He sits in the back garden on his deck chair, staring out into the dusk sky as the sun slowly sank down behind the distant housing estate. It is a warm mid-Junes evening and the sky is painted with pinks, reds and oranges across the dark blue canvas. Even the stars were beginning to protrude through the blackest parts of the sky. It is truly...

Crossdressing Charlie Episode 13 Hide and Seek

CROSSDRESSING CHARLIE Episode 13 HIDE AND SEEK TWO YEARS AGO... Dave watched the raindrops roll down the windowpane and morph into one another before they dripped away. Outside, it was pelting down so hard that it looked like the rain was coming up from beneath. He watched people scurry down the street with umbrellas, newspapers, and briefcases over their heads to protect their precious haircuts. It was dreadful weather. However, he was safely inside a nice warm caf? with a cup of t...

Crossdressing Charlie Vol 1 Episode 1 The School Uniform

CROSSDRESSING CHARLIE Volume One Episode 1 THE SCHOOL UNIFORM The thump of the car door made Charlie open his eyes. The sound of a second door slamming made him sit upright in the bed like a startled squirrel. He listened carefully. The ignition jerked several times before the engine started up. He was still as a statue as he listened to the low rumble of the car reversing out of the driveway. He scurried across the blankets, jumped off the side of the bed and stumbled over a pile...

Crossdressing Charlie Vol 1 Episode 15 Crime and Punishment

CROSSDRESSING CHARLIE Episode 15 CRIME AND PUNISHMENT Dave's long, golden hair hung gloriously down over his bosom, and down his back like an unrolled curtain of soft velvet. Covered with an explosive overdose of fake tan, his skin looked radiantly false yet hotly sensual. His face was painted like a dolls and his makeup was over the top and trampy. Like two fluttery butterfly wings, his lashes were thick, dark, and long. His lips appeared plumper as they were coated with neon-pink...

Crossdressing Charlie Vol 1 Episode 16 The Greatest Change

CROSSDRESSING CHARLIE Episode 16 THE GREATEST CHANGE Everything in Charlie's life became slow and dreary after a period of unexpected escalation. Yes, he returned home to his family after nearly being kidnapped by a psychotic blackmailer. However, that did not mean everything would immediately return to normal. There were still a lot of unanswered questions pressing on the minds of those who loved Charlie and he knew they would start asking sooner rather than later. He had prepared...

Crossdressing Vignettes 2 True Story

This is from the early 1990s, when I was in the occasional habit of crossdressing in lingerie and bottoming. I don't do that any more for several reasons, mainly because at my age I just don't have the body for it any more. About 20 miles from where my wife and I lived, on the outskirts of one of America's largest cities, there was an unofficial red light district. It was basically a very poor little village that had opened its boundaries to adult businesses in order to attract some kind of tax...

Crossdressing in Highschool but oddly enough my friends are alright with it

Never in your life, you thought you will be entering my school walk-in crossdressing as a girl. If you told yourself this two years ago you will be laughing at your face. But here you are swallowing your guts down into your stomach and pray to God that today is the day you die. Facing the high school doors that separate you from the inevitable humiliation. You close my eyes and push the doors open, immediately multiple eyes lock onto you. Freeze Frame Record Scratch. Let's go back all the way...

Transsexual

Crossdress Rendevous

I had to be out of town for a few of days for a demonstration an I knew there was a alternate lifestyle club located there and so I decided to take along with me a white silk dress, bra and panties and white hose and a pair of white stiletto heels. I didn't tell Carmen that I was hoping to connect with another man for sex, me dressed as a crossdresser in my outfit. I had finished early with the demonstration and went back to my motel and quietly changed into my white outfit. I left the motel...

Crossdress swaps clothes and gets assfucked in pub

A few years ago I was on a weekend trip to Brussels and Amsterdam with some friends, and found out a girl I knew from Ukraine was now living in Lille, not so far away, so I decided to make a quick trip to see her the evening before we were due to fly home. I caught the train from Brussels to Lille and she and her boyfriend picked me up at the station. She was a short, curvy blonde, with equally large breasts and ass. She loved wearing sexy outfits which showed them off. This evening she was...

Crossdress Sex With My Driver

Hi my name is Sunil(although I preferred to be called as Sunita). I 29 and I am a beautiful cross dresser with very nice body. I own three beauty parlor in Delhi, and most of the times I am dressed as a girl. I go out wearing woman clothing and no one can say that I am a boy. Now coming to the story, one day my old driver called me saying he is sick and so he is sending his son to do the duty for a couple of days. That day I was dressed in a pink tight salwar kamiz, when the door bell rang. I...

Gay Male

Crossdress fuck

One day while at university I went to the toilet. There was some one in the next cubicle. I could see a shadow under the partition. It was moving back and fort very fast. Was he wanking? I started to feel horny thinking about it. As a cross-dresser i was wearing a satin night-dress under my clothes. I decided to get brave. I stood on the toilet and looked over the thin wall. Oh god ya, he was masturbating hard. I pleasured my self as I witness something new & exiting. Then I let out an...

Crossdress

Things had changed greatly since the children had grown. She had become more accustomed to his peculiarities and understood him better. Things which formerly disturbed her she now accepted. He too was more understanding and patient. Thus, when she returned from shopping he did not begin by asking how much she had spent. Instead he asked what she bought and listened with genuine interest when she told him of the dress and shoes which she got and how she decided to get a hand bag to...

Crossdress Fun

We have all had those experiences of meeting someone on-line and chatting and things really get hot and exciting and then the huge let down when the person leaves you hanging with a hard-on or even worse when the time comes to meet they don’t show.Well this story is one with a happy ending.I met Paul (not his real name), on line and we chatted for ages. He was from a town about an hour away so on-line chatting was really our only safe way of communicating. When he found out I was into...

cross dressing fun turned sour

A few nights ago, one of my pals whom I have some great fun with, said he had tickets for a great Hypnotist would I like to go? Of course, I agreed and off we went. Shit, the show was awful. He picked on me as one of the last clients, should I say. He dragged me on stage (no pun intended) and tried to put me under. I knew he didn't succeed, or so I thought, Tom, my mate, waited until I returned to my seat. “Load of crap” I told him. “Ah” said Tom “You did not see what we, the audience...

Cross dressed fucked and loving it

I opened the door to see two really attractive women, a blonde and a brunette, definitely C cups, and dressed to show them off. They must have been wearing four inch plus leather heels that went up to the knee, tight short skirts, and tops that didn’t leave much to the imagination. I was rock hard and they hadn’t even said anything yet. Both of them were carrying two huge suitcases, and when the blonde saw me look down at them she said, “Oh, were going to have so much fun tonight!” The brunette...

cross country run

PART THREE This was such an unexpected adventure. We were out for a run , not a marathon sex session. As we held her lovely body horizontal and Tom had just slowly penetrated her ass, our hands were everywhere and Rachel was wriggling madly. We just couldn’t hold her and we lowered her to the floor, all three of us sitting back breathless for a moment. Rachel stood up. I personally am in awe of the magnificent beauty of a woman, I pay full respect to whatever god or gods sculpted such beauty. I...

cross dressing fantasy i didnt know that i had

went on a stag holiday to ibiza with about 20 of my mates a couple of years ago.the holiday mostly consisted d**g taking copius amounts of drink and sl**ping with llots of women. the main stag night was fancy dress,and id already planned before i came away id already decided that i was gonna wear i toga and my girlfriends flat gladiator sandals and go as troy.a few of us got quite pally with the girls in the appartment opposite and the daytime before the main nite out one of them commented that...

Cross country run

We watched as Tom continued to caress her. She moaned loudly as his fingers pressed against her crotch. We could see her panties dark with moisture around her most intimate part. Tom rubbed the silky material: ‘ Rachel, your knickers are just as wet as we were when we came in. I think I should take them off and dry them by the fire. Stop me if you wish.’ He began to tug them down. She wriggled a little, saying no, but her body movements were saying yes and they were soon down to her knees....

Cross country run

Final part The lady had a fantasy of her own, and now that she had three eager men beside her she decided to go for it. She was a runner herself, and she now told us she often fantasised about being overtaken in the woods, and being overpowered and thoroughly and comprehensively shagged while pretending to put up a struggle. While we donned our running gear again she put on some of her own and left quickly. We gave her five minutes start and set out after her. When we came in sight of her she...

Cross

Darren closed his eyes and rested his head in his hands for the umpteenth time that day. How could he have been so stupid? He’d always been the careful one out of every crowd he’d been involved with. Coming from a dirt poor background, he knew the smallest thing would mar his reputation and he would be screwed for the rest of his life. His whole life, he had been a straight A student. Before graduating high school a month ago, his scholarship at Princeton had already been confirmed. One night...

Cross Breed

You wake up in a daze, a blinding bright light shines right into your eyes. Struggling to adapt to the light, you try to shield your eyes from the light, but notice your hands are restrained. Instinct and panic make you try and jerk free, but your legs are restrained. You are trapped in a strange place. You are completely nude, with your head restrained so you can barely move it. You start to hyperventilate, and as your eyes adapt to the light, your fear deepens. Looking around, you are in a...

Fantasy

Cross dressing first time out

Now I had been seeing mike for a few months now and the relationship was going well. He had introduced me to paul he work friend for a three some which was amazing and the dressing up was getting more and more kinky!!! He hadn't never pushed the boundaries with me kept it simple and sweet, until now!! I always did as as he asked to a point, never anything abusive or nasty he knew what I was into. So when he asked me to dress up and go to a night club i was shaken and a bit scared!! I had never...

cross friends trick 4

I came down from my orgasm to see Jenna and Katey French kissing and licking my cum from each others faces, whilst still holding my cock in their hands.“My god, I never knew it would taste that good” said Katey. “Believe me” said Jenna,” it doesn’t always.”“You've done this before?” said Katey surprised, and Jenna blushed as she sheepishly looked at me, “Oh yes, and you and your girlfriends would be surprised who with” Jenna said bashfully. “Lots of those high school jocks you hang around with...

cross friends trick 2

It was probably a fortnight before the call arrived. Jimmy and I had just gone back to being the best of mates, and nothing had been mentioned about what we had done that night. The phone rang in the hall and I went to answer. Jimmy had never needed to call me before, if we weren’t already together somewhere, we would have already planned what we were going to do so it was a shock when the call came.“Hello, two one, double five,” I said, and the voice at the other end whispered to me, “Would...

cross friends trick

We’d been friends for pretty much all of our young lives and did everything together. I never expected to be sharing this though.From being k**s ‘playing out’ together, to first stolen drinks, cigarettes, and spliffs, we had shared everything. Basically Jimmy’s dad was rich and they had a huge 5 bed roomed house with double garages, and outbuildings and quite a bit of land with a small wood and fields.Jimmy’s bedroom was above the garages, and when I say bedroom I mean fully fitted flat. He had...

Cross County With My Aunt Jo

Summer is finally upon us as I have finally finished up with school and graduated. My aunt has been wanting to take me on the road with her. She is a trucker and takes long trips across the entire country. As I was afresh new 18 year old lad I was excited to see the world. Or at least the little bit we call home. I get dropped off at my aunts house with my bag in tow. I walk up to her big truck and can see the door is open. I peek in and see her putting away a few things under the bed. She is...

Cross dressing self bondage in an empty apartment

Tonight is the night that I am going to try a daring crossdressing self bondage experience that I have been planning for some time.First of all I start with my complete feminisation. As I am going to be a total slut tonight I apply my make-up accordingly. Once I have applied foundation and powder, I use a dark eye shadow to give me a smokey eye look. Then black eye-liner under the eye and I apply long false eye-lashes. I paint my lips a deep red and then lip gloss on top, making them full and...

Cross dressing sissy transgender car shopping

Car Shopping I could never repay mom for what she has done for me in the way she accepted and encouraged who and what I am. Being successful in my career has allowed me to come from a small mobile home in a rundown trailer park to my current life style and affords me to do things for he. So, two Years ago on Mother’s day I wanted to do something special. I got her a brand new car. Not knowing anything at all about cars (know lots about dolls and fashion) I asked a friend (Gary) to go with me...

Cross dressing with my sister

I turned up at my s.....s flat, ready for a Friday night out. We got the drink flowing and started to get dressed up for the night. Pru said that she was going to wear knee high leather boots, a short skirt that will show off her ass and a top to die for. I said " what the heck do I wear that will make me stand out".pru stood there in her robe and said " let's dress you as a girl, that'll make you stand out!I jumped at the chance to get dressed as a woman,.She looked into her draw and came...

Cross Dressing for Ann Again

About a week after my first amazing session with Ann, the neighbour from downstairs who blackmailed me into modelling her lingerie, I was again accosted by her on the stairs.“Hi,” she said, coming out of her front door as I was passing. “I’m glad I bumped into you” (I knew she was lying in wait behind the door watching out through the spyhole) “are you doing anything on Wednesday night?”I said I wasn’t and she said that as John and Ian (her husband and son) were going to Aberdeen to watch the...

Cross Country Cocksucking

The bus driver came into the restroom and stood right next to me at the long urinal trough. As he unzipped and reached in to fish out his dick, he leaned over uncomfortably close to me, staring down at my exposed dick, and whispered in a husky, emotion-filled voice, "Boy, that's some great looking piece of meat you got, there." And with that, he hauled out a man-sized, already partially erect, perfect penis, sort of hefting it for my inspection. He turned slightly towards me as if offering the...

cross dressed cocks

I was looking forward to the fun I could have in my own place. I spent some time on the male chat line looking for someone to play with. he to liked to dress but like me was not at all passable . when he showed up at my place he hade on black thigh highs open toe heels and a corset ,he was taller then me and of average build . it was the bulge in his panties i was interested in. I was dressed in pink thigh highs red strappy heels pink panties and a light purple chemise with a pink bra under...

Cross Dresser And Escort Bhabhi

Hello reader! I’m NaughtGuy 21 years from Mumbai and any Girls, Bhabhi, Aunty, Mom, Milf, BBW wants to have some good time for free, email me at This is my real sex story. This is my first sex story, and my best sexual experience, Crossdressers name is Pinky. Escort’s name is Reema (Names Changed) One day, I happened to watch porn in which a guy has fun with crossdressers and a female, it was a group fun which made me really horny, So I decided to jerk off but it didn’t satisfy me, then I...

Cross dressed slavery

Oh just try it on, don’t act so…stereotypical.”I started to protest again, I mean I was not trying to be a jerk, but I did not feel like serving as Leena’s dress dummy all afternoon. I felt uncomfortable enough around her and her clothes. The way she dressed made me crazy and I knew she would tease me all afternoon if I let her. It was my own fault really, I approached her at her last ‘fashion show’ and offered to take some pictures. I really did like her designs, but mostly because of my...

Cross Dressed In Kerala 8211 Part 1

First of all its a fictional story ..This is one of my desires ..Hi guys myself Karthik and I like to be karthika this feeling started during my 10th std and coming to my stats I am 5ft 6 inch height and weighs about 80 resembles similar to nithya menon .. This incident happened to me when I was a fresher working in a company in kerala where I met my man who later fulfilled my dream and became my husband till my marriage . I was very fat and after my puberty only my man-boobs and ass grew big...

Gay Male

Cross Country Fantasy

A good friend of mine was moving to the west coast. Being in the moving business I offered to do their move at cost. We loaded their belongings Sunday and I would be leaving Monday, meeting them in BC the following weekend. Ralph and the family were planning to fly out on Saturday. His daughter Kim asked if she could go with me and see the sights along the way. We all agreed that would be fine and we left early Monday morning. Having known the entire family for a very long time I knew Kim would...

Cross Dressing In Goa 8211 Part 1

I am Sumit, a regular reader and fan of ISS. This is my first time so kindly ignore spelling mistakes. I am a19 year old chubby boy. I am fair and 5 feet 4 inches tall. This incident happened when I went to Goa with my friends. After semester exam, my classmates decided to visit Goa to relax. We reached Goa early in morning. Everybody was tired because of 8 hr train journey in general compartment. We all had breakfast and decided to take rest. After a while we went on beach. We played football,...

Gay Male

Cross Dressing Bus Journey Fun

Hi All, This is Vinnie Cd here. 26. I love wearing short skirts panties and thongs a lot. I wear nice laced panties to work many Times too. Had a nice time even with couple of cab guys thanks to my cute girly ass in frilly Panties. I love sucking and getting fucked outside. It really makes me horny n slutty. Last year, I was travelling to pune in a bus and was wearing thongs sports bra a loose Tee-shirt and jacket tracks outside. I also wear a nice girly deo. It was sleeper and I got in And got...

cross dressing fantasy i didnt know that i had

went on a stag holiday to ibiza with about 20 of my mates a couple of years ago.the holiday mostly consisted d**g taking copius amounts of drink and sleeping with llots of women. the main stag night was fancy dress,and id already planned before i came away id already decided that i was gonna wear i toga and my girlfriends flat gladiator sandals and go as troy.a few of us got quite pally with the girls in the appartment opposite and the daytime before the main nite out one of them commented that...

Cross Dresser Become Whore 8211 Part II

I am a Anis a crossdresser and I had got a female persona Sonal and I use to crossdress in secrecy at my home. One day my friend Rajesh caught me while crossdressing buthe like my female persona.That day we make love as lovers. Then whenever we get chance I use to dress up as a girl for Rajesh and he use to make love to me. I had almost become his wife but mean while Rajesh got bad habit of drinking and betting gambling etc.He use to spend lot of money on gambling sometime he even take money...

Cross Country Vayage For Sex 8211 Part I

Hello everybody, I am Sojol, a resident of Western Eurpoe. I am 28 yrs old, six ft tall, medium built physical structure. I work for an investment bank in a junior management position. I had a relation with a girl through ISS and Orkut, who lived in Savona, Northern Italy. Her name was NILA,22 yrs old, a graduate student in nearby University. We used to chat and talk very dirty. We then decided to meet each other. Hers being a conservative family, she told her parents that she was going to...

Cross Dress in College

This is a fantasy story: This happened in my college days. I was sharing my room with Rahul. He was the average Indian guy with a good body. I was of small built (5ft 4inches tall and 50 Kgs) and and had a petite body. Rahul used to ask me to grow my hair long (he used to tell me it is the fashion) and until later I did not realise why he wanted me to do that. We were quite good friends (just like all hostel room mates are) and used to be very comfortable changing arnd each other. One day, I...

Gay Male

Cross country run

Final part The lady had a fantasy of her own, and now that she had three eager men beside her she decided to go for it. She was a runner herself, and she now told us she often fantasised about being overtaken in the woods, and being overpowered and thoroughly and comprehensively shagged while pretending to put up a struggle. While we donned our running gear again she put on some of her own and left quickly. We gave her five minutes start and set out after her. When we came in sight of her she...

MILF

cross country run

PART THREE This was such an unexpected adventure. We were out for a run , not a marathon sex session. As we held her lovely body horizontal and Tom had just slowly penetrated her ass, our hands were everywhere and Rachel was wriggling madly. We just couldn't hold her and we lowered her to the floor, all three of us sitting back breathless for a moment. Rachel stood up. I personally am in awe of the magnificent beauty of a woman; I pay full respect to whatever god or gods sculpted such beauty. I...

MILF

Cross country run

We watched as Tom continued to caress her. She moaned loudly as his fingers pressed against her crotch. We could see her panties dark with moisture around her most intimate part. Tom rubbed the silky material: " Rachel, your knickers are just as wet as we were when we came in. I think I should take them off and dry them by the fire. Stop me if you wish." He began to tug them down. She wriggled a little, saying no, but her body movements were saying yes and they were soon down to her knees. Tom...

MILF

Cross dressing

Hello is my story. This happened. It was the mid 80’s and I just turned 17 so I thought I would go to the mall near my home town on Long Island and go shopping with my birthday money. I was looking for clothes with and I need to use the rest room. I walked into the bathroom, and the floors were wet so when I made a turn, I slipped. I put my hand against the door of a stall that was closed as not to fall, and the door it flung open because it was not locked properly. I looked inside and a man...

Cross Country Trip

It was damn hot on this, the second day of our trip, and I don't think that any of us were enjoying the travel. Dad, Mom and I were going almost right across the country so as Dad could take up a relieving managers position brought about by illness. Initially the plan was for him to fly and live in hotel accommodation but as it would probably last for almost 6 months we decided to go as a family, enabling Mom and I to experience of quite different culture and living style. We had departed...

Crossing the fence

My body shuddered as I collapsed back into the water,...My legs were tired from holding position, beads of sweat drip from my blonde locks,... my heart rate slows,...as I gather my breath. My legs fall to the sides as my ravished pussy once again is submerged,... reddened by pleasure. My once tight grip weakens from the rails I held so tightly. A displacement wave cascades over the edge of the tub,... as the roar of the water jet,... forges on, like an unrelenting monster of pleasure....

Crossing Training

Cross Training By Karen Elizabeth L. Copyright 1997 Mom and dad broke up a few years ago and even with child support my family doesn't have much money. That all changed recently when mom won the lottery. We now had more money than we ever dreamt of and our lives were about to change! I was just a normal boy doing what boys do, not paying attention to my mom or teachers, and being a pain in the butt to my older sister Barbara and her friends. One of my favorite thing s to do...

Crossing Worlds Part Three

The magic portal cracked and within a moment of walking all three had arrived in the majestic bedroom of the Creneth mansion in all its ivory and harwood and silk splendor. "Welcome, Jaina, to the 21th century on earth." Markus leaped on his bed with a big smile as he could once again enjoy the oh so soft feeling of his own bed with a proper support system. The best beds of Jaina's world couldn't compare. With a big smile on her face Andrea followed behind Markus, crawling over the bed...

Crossdressers Spanking Scene

My roommate and I were both bi and part-time cross-dressers. We were also familiar with consensual B & D and had already worked out several code words, then went a step further and wrote scenes for each other, so that when we’re in the mood, we could call up the scene rather than try to explain it or coach someone through it. Sometimes we did a scene to please each other sometimes we asked for a scene because we were in a specific mood. So it was that I got an e-mail at work, which would...

Crossdressers Bully

CHAPTER 1 Summer vacation was over already. And it was the start of my senior year. My alarm rang and I was filled with anxiousness. I don’t want to go. “John! Get up and get ready for school! Don’t want to be late on your first day.” My mom yells from downstairs. Fine. I get up and head over to the bathroom. My morning erection trying to poke out from my boxers. I say trying because it so small I couldn’t even grip it properly. I’m all washed and ready for the day. “John I really wish you...

Crossdressers first gay encounters

I had met Steve thru a gay dating site, we exchanged messages over a few weeks and then finally agreed to meet. I was very nervous on the way over to Steve's for two reasons. One was it was going to be my first gay encounter. The Second reason, and one i had only agreed to after Steve's insistence, was that i was going completely cross-dressed. I'd gotten dressed at home as Steve wanted. Putting on a satin and lace garter belt which i attached to lace top suspender stockings, then a lace bra...

crossdressers first blowjob

had been a private cd for years and along with that secret I always wanted to give head .. but always to nervous . I used to be a long distance hgv driver and park up at night it what I call , naughty laybys . we all know the sort . did see quite a few things going on in them . especially single men turning up with hard cocks wanting some fun . most nights I would get dressed up and climb out and walk up and down and seeing if anyone saw me , then quickly run back to the lorry and hide . it was...

Crossdressers in a bisexual sex bar gang bang

I'm sitting in a crossdresser's sex bar – it’s dark. My companion Fifi is wearing only a pair of sheer silk panties in light blue, stocking and suspenders, and a pale blue matching corset that pinches his waist. His balls peak out of the tight panties. I’m wearing silk patterned stay-up stockings in black and a scarlet and black thong. The string of the thong rubs against my sensitive asshole and the soft skin of my ball sack: it’s a turn-on every time I move.A group of men and women approach...

crossdressers first time with a guy

hi, im new to this. this happened about 3 years ago now.I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from this simple thought I became massively aroused and started trying on her underwear, make up, and even a wig that was in the apartment. soon enough, I was looking like a slutty crossdresser.I thought enough...

crossdressers first time

i first started to wear tights when i was 18,i was shocked when i first realised i loved tight panties and sheer tights. i was staying with my friends mother who was 65 at the time,she wore the sexiest lingerie i had ever seen,especially on a woman that age,but i felt drawn to the sheer stockings. the next day i was taking a bath when i noticed them on the wash basket,i had an urge to wear them,i was very shocked by this desire but had to!i slipped them on taking care not to rip them,they were...

Crossdressers On Third Base

I haven't mentioned this before but as a younger person I was bullied. Quite relentlessly at times by a couple of older k**s in the neighborhood, Gabriel and Tom. Tom went on to do something quite successful with his life but last I heard, Gabriel was on the unemployment benefit and selling weed. I'm OK now looking back they did have an effect on me. I'm pretty sure a lot of my social awkwardness came as a result of the months of concentrated attention by these 2 arseholes. Tim and I made a...

Crossdressers On Third Base 2

I was quite shocked with myself after mine and Tims extremely hot escalation the other night. (I had to finish up early due to becoming extremely horny remembering that tale. - Author) Let me finish the story.I sat up between Tims legs and released the grip of my lips. Just enough to let some of his cum gloss them. Tim watched my face closely as i sat there wondering what to do next. I'd already swallowed a portion, I'm sure. Tim giggled a bit at my facial expressions which made me grin and...

Crossing the Forest

This place is familiar, so I know where to go. But I continue to lay on my belly with my hands behind my back. I have sense a nice wind goes from my legs to my shoulders. It`s so nice that I even feels like wind touches insides of my pussy. Sensation of been like this in night forest driving me on. I have a lot of fillings about it. Oh, looks like some insect goes up on inner side of my leg. This thing has lot of legs it tickling a little. Interesting, where do this thing goes then come to my...

Crossroads Ch 3

A tale of pure fiction and fantasy. I was actually considering going all the way. Going all the way in becoming female. I had been living as a female in all phases of my life for some time. I continued on the hormones and all my desires said I should do this. I had called the plastic surgeon who had done my breasts and explained what I wanted. She suggested going to see a doctor in Vancouver who was an expert in SRS. I called his office and made an appointment. Luckily he could see me on a...

Crossroads Ch 5

A pure fantasy about a young man changing his life by becoming a woman. I pulled up to the valet parking of the hotel. As I got out I saw the young attendant look down my dress and then look at my legs as I swung them out to stand up. I smiled to myself. I was really going to do this. I was going into the bar in this hotel and pick up a nice guy. If I liked him enough I was going to have sex with him as a woman. My new equipment was ready and I had to try it out.

Crossroads

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

Crossroads Ch 02

The second chapter in this crazy little tale. I really loved my little adventure out as a woman. I liked the power I had over men. I was seriously thinking that I would like to live as a woman full time. That would be quite a commitment and one that would change my life forever. As I said before I worked for a really liberal company and one day I got up some courage and went to my boss. I explained to her my desire to live in public as a woman. She smiled and was very understanding and said...

Crossroads Ch 4

I am on an airplane flying to Vancouver. I have an appointment with a doctor to have sexual reassignment surgery. I am so excited I can’t stand it. I know this is what I want. My recent encounter with a woman convinced me. I have no doubt about it now and won’t look back. We land and as we deplane I notice, as always, the admiring looks I am getting from men, including the pilots. I am wearing some chic pants that show off my ass and a camisole top under my jacket. It is low cut and shows...

Crossroads Part 3 fiction

Something clicked into place in my mind as I looked at the reflection of myself and the approaching Rachel and Alice. I felt their warmth as their arms embraced me. We looked at each other in the mirror and knew this was just the beginning, there was no going back for me now, Pandora's box had been opened. I was steered towards the bed and as I walked I could feel the tightness in my calf muscles caused by wearing the high heels. I was certainly steadier on them than I thought I would be. I...

Crossroads Ch 5

A pure fantasy about a young man changing his life by becoming a woman. I pulled up to the valet parking of the hotel. As I got out I saw the young attendant look down my dress and then look at my legs as I swung them out to stand up. I smiled to myself. I was really going to do this. I was going into the bar in this hotel and pick up a nice guy. If I liked him enough I was going to have sex with him as a woman. My new equipment was ready and I had to try it out. I felt very sexy in my...

Trans

Crossroads Ch 4

I am on an airplane flying to Vancouver. I have an appointment with a doctor to have sexual reassignment surgery. I am so excited I can't stand it. I know this is what I want. My recent encounter with a woman convinced me. I have no doubt about it now and won't look back. We land and as we deplane I notice, as always, the admiring looks I am getting from men, including the pilots. I am wearing some chic pants that show off my ass and a camisole top under my jacket. It is low cut and shows...

Crossdressing

Crossroads Ch 3

A tale of pure fiction and fantasy. I was actually considering going all the way. Going all the way in becoming female. I had been living as a female in all phases of my life for some time. I continued on the hormones and all my desires said I should do this. I had called the plastic surgeon who had done my breasts and explained what I wanted. She suggested going to see a doctor in Vancouver who was an expert in SRS. I called his office and made an appointment. Luckily he could see me on...

Crossdressing

Crossroads Ch 02

The second chapter in this crazy little tale. I really loved my little adventure out as a woman. I liked the power I had over men. I was seriously thinking that I would like to live as a woman full time. That would be quite a commitment and one that would change my life forever. As I said before I worked for a really liberal company and one day I got up some courage and went to my boss. I explained to her my desire to live in public as a woman. She smiled and was very understanding and said...

Crossdressing

Crossroads

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

Crossdressing

Crossroads

Chapter 1 "She'd never been what anyone would consider an 'ideal' daughter, for any parent. Holly could easily be described as being a bit of a brat. She was 17 years old, with beautiful green eyes, and dark brown hair. She had a body that most men would die to get their hands on, and she knew it. Often in high school, Holly would use her charms on any guy she wanted, and never seemed to have a problem getting whoever she targeted. Sadly, Holly hardly ever found a guy worth being...

Crossroads RulesChapter 3

The main street of the town was a mess. Rain had turned it into a strip of mud that sucked at his feet and threatened to pull his boots off with each step. Although he had expected to see wood planks laid out to make crossing the street less messy, there were none. It wasn’t even clean mud, but had manure from a variety of animals mixed in with it. The air was ripe with the odor of shit, spoiled food, and human activities. In the middle of the town, a two wheeled cart pulled by an ox had...

Crossing the Line 1

As we grew older, we would share our problems with one another, our successes, our failures, and we would share our sexual experiences. Suffice it to say, we were closer than the average cousins. As we entered our 30's, life dealt us both a hard hand. She was living with a guy named Mike, who wasn't exactly loving to her, and I myself was going through a period of sexual frustration with my girlfriend. During a conversation, I spilled the beans about desiring more oral sex. I love...

Crossing The Line

My sister’s boyfriend Luke Weston was possibly the sexiest dude I’d ever laid eyes on. I rarely found myself hung up on a dude but I’d been hung up on Luke since the day he and my sister met. After a year of dating my sister, he moved into our house and it made the sexual tension I’d been experiencing a million times worse. I didn’t want to continue being a third wheel so I began to look for a new place to live. Immediately after I told them I was looking for my own place, Luke’s attitude...

Crossing A Different Line

In my personal journey from straight, married heterosexual to bi male, I discovered, along the way, that I was aroused by women’s lingerie. It started with trying on a pair of my wife’s nylon panties. The feel of the silky material, and the sight of how it fit, quickly brought on an erection. I used another silky pair in my hand to jack myself off, being careful not to get any cum on the panties. The orgasm was unusually powerful. In the weeks following, I pursued my new found curiosity,...

Crossdressing

Crossing Lines The Beginning

I watch from the doorway, trying to gauge her mood. She is milling about the kitchen, seemingly happy, softly humming.I approach her with optimism, drawing her towards me. "You're so beautiful." "You have to say that. You're my husband," she says, wriggling away."No, I mean it. I would love to show you what you mean to me," I continue, trying to kiss her."Hun, I have things I need to do," she replies, turning her cheek to my lips.I move in again, coaxing, "But, the kids are gone for the...

Cheating

Crossing the Line

I crossed the line about sixteen years ago.Larry had said one of his fantasies was to watch me with another man. At first I thought it was just one of his fantasies. Then I thought it was an excuse to get to lay other women because he was tired of me. I guess I went through all the suspicions. One time we were out camping for a few days with a friend. Larry had gone to the station wagon to sleep while Terry and I stayed up sitting at one of those cement picnic tables. He started out just...

Cheating

Crossing The Street 2

"Took you long enough!" I blinked away the sleepiness that last night’s fitful slumber hadn't resolved. "I said to be at the phone at ten. Where were you?" Dana accused. "I...I was just here... I..." My words trailed off, remembering last night's dinner, the distracted conversation, the DVR shows Mitch and I had watched that I couldn't recall, my brain occupied by yesterday's events. Tossing and turning all night as Mitch snored, blissfully unaware of what his proper wife had been up to that...

Reluctance

CROSSING THE LINE

It was late on a Saturday morning and I was feeling restless. I had just come back from a five mile run. At 41 I took pride in keeping myself in shape. I was in my bathroom and was about to get in the shower. I had dropped the robe I was wearing and looked myself over in the mirror. My legs were toned and long. My ass too was high and tight from years of running. Even my stomach was flat even though I had two k**s. The only thing that was a little out of place were my boobs, they were a little...

Crossing the Divide Part One

London, and indeed the whole of the UK is in Lockdown.Everyone is required to remain indoors. It is now illegal for us to leave our homes without a valid reason. We are caged, held captive, with no end in sight.It is hardly surprising then that two young women seek ways to reach out in their lust for lesbian love.Suzy writes:You and I have not yet met, but we both live in a modern apartment building near a beautiful park. The building is arranged in a horseshoe shape so that some apartments...

Exhibitionism

Crossing the Divide Part 6

Suzy writes:"It must be fully charged by now!""Not until the red light goes out," Amanda replies.Amanda is reading from the instruction leaflet and sitting cross-legged on the bed. I am lying beside her, biting my bottom lip in anticipation."It says here that it combines sweet suction with soft pressure waves." Amanda continues her perusal of the leaflet. "Six intensity settings.... " My body is quivering with its own intensity settings. With my back against a mound of pillows and my legs...

Lesbian

Crossing Boundaries Part One

Kael fidgeted, anxious to see just what would come of the meeting, a young man with neatly trimmed hair. His father stood before him, taking the lead in the meeting, though it was the first time he had ever been allowed to stand so close to the anthro ambassador of their closest neighbours, a chameleon with a particularly noble look about his strangely rounded face. Long robes fell to the floor around his ankles and he tried not to make it too obvious just how uncomfortable he was in them, for...

Fetish

Crossing the Horizon Part 3

Rachel felt the long, damp grass tickle against the back of her legs. Ever part of her body was on alert now as she made her way through the wild field. Dressed in her own homemade outfit of a brown half-poncho and double-sided loincloth, she could certainly feel the cold breeze. She also had on some coverings for her lower legs that went right up to her knees and were strung up at the back and a pair of moccasins on her feet. Rachel had spent all the past week getting the outfit ready and she...

Crossing the Horizon Part 1

Rachel was nervous as she approached the steel blue door on this unmarked building. Her friend Sarah had given her the contact number at her recent birthday party saying it would help cheer her up after the split from her boyfriend. She had been pretty melancholic for the past month as she was 32 now and the latest split was another instance of a pattern she had fallen into – meet a guy, date a guy, get too close to the guy and realize that you are actually bored of the guy so quietly drift...

Crossing the Horizon Part 4

Rachel was waiting outside the warehouse in her jacket and jeans. She had her weekend bag with her, packed full of the usual essentials, as well as a few face paints and things like that just in case. It hadn't been a hard to decision to do this in the end. Work was its usual droning self and the only thing really occupying her mind was Max and that magical day in the woods. The film had been sent around to the club and the feedback had been so incredible. Rachel didn't know what to do or...

Crossing the Border

A light orange hue was inching across top floors of a building opposite our house while the chirping of birds hiding somewhere in an oak tree in the backyard was drowning out traffic noise. I knew she would be back any minute from her run, so turning away from window and taking my hands out of pockets went into kitchen to make coffee. Putting the cups on a round bare wooden table in the lounge, sat down and began thinking about the past month. While life hadn't been easy for us, especially...

Crossing the Line

Book One - Author, Author "This meeting is never going to end." Cathy Donohue thought to herself as she looked up on the wall of the makeshift conference room and saw that it was already twenty to eleven. The regular PTA meeting had broken up over an hour ago and this little gathering of the executive committee was supposed to be brief. Just a quick chance for the committee to settle a few outstanding problems before adjourning for the summer. That was, however, before Dolores Azucena took...

Crossing the LineChapter 3 Winterhaven

Winterhaven Silence reigned inside the Jeep as Mike and Sam neared the finish of their 5 hour drive back home from the camp site. Things had changed drastically the second morning of the groups planned 3-day camping excursion, having been abandoned by her boyfriend during what should have been the most erotic and sensational experience of their young lives up to that point. With all 4 of their group high on Ecstasy and marijuana, their shared tent had quickly evolved into a temple of the...

Crossing the LineChapter 4 Santa s little helper

Winterhaven was the night before last, its Christmas Eve now and the Konders family was in full Christmas time mode. Sam’s mom Brittany was at the mall picking up a few last-minute stocking stuffers to add to all of the little kids stockings and Dad was at work driving his oil tanker hoping to be home in plenty of time for the evenings festivities. Alex was at work with Brian, both of whom worked at a local car dealership as ‘lot attendants’, washing cars, putting up sales prices on the...

Crossing the LineChapter 5 Nicole

It’s mid-January and High-school seniors across the country are stressing out about making their final decisions for which colleges they want to apply to, having only a few weeks left to get their applications sent out, that way the colleges can make their decisions and send out responses by April. The last couple of years, Sam had been just assuming she would go to NorthWestern State University in Louisiana. That is where both of her parents had attended and both sets of her grandparents...

Crossed Lines

Everything was perfect and exactly as the book had detailed, the chalked lines the definition of precision on the designated aspen wood floor, stones and gems of varying origin expertly carved with runes long extinct from the world placed around the central circle, candles dotting each of many points, the wax of the candles infused with his own blood, the fire burning with a slightly greenish tinge, a sign things were as they should be. Now all he had to do to take his rightful place in...

Crossdresser Stories 8211 Assfucking in panties

I have been ‘mildly’ crossdressing for over a year now. I say ‘mildly’ because I am not into full feminization, I just love the feel and look of lace panties when they are hugging a good looking cock, not to mention the taboo. I have taken to wearing stockings too which feel amazing, it’s like having your whole lower half caressed persistently. I have thought of wearing a bra but, although I can almost imagine how amazing it would feel, I don’t think men look...

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...

Crossdressing

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