Sidedressing
- 4 years ago
- 27
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This is a series of stories rather than one story. It talks of my experiences as a crossdresser.
My first experience as a crossdresser came as a teenager when I tried out some of the clothes belonging to a woman who was staying at our home. She was a gorgeous French woman with very pretty clothes and I did enjoy trying them on, but primarily as it got me closer to this woman who was way out of my league.
When away from home the first time I bought a few clothes through a mail order catalogue – a dress, one-piece swimsuit, skirt, nightwear and lingerie. I tried them on and slept in the nightwear but I thought that I looked foolish when I saw myself in the mirror and soon discarded the clothes.
Hi back again… This is my friend new story. I met him in London last week .his name was mike. So let start… It all started a few weekends ago when I (mike) had been incredibly horny and my girlfriend was out of town. She wasn’t expected to be back for another two days and I needed some relief. She always wore really sexy panties and I loved the way they felt when she would grind up against my bare cock during foreplay. Being as horny as I was I went to the dirty clothes hamper and found the...
Gay MaleYou walk into the lobby head held high, back straight. Confidences oozes off you in such a way heads turns to watch you walk by. Your not the most beautifulest thing in the world, your not rich, when you make plans it doesn't shake the world. But it doesn't stop you from getting shit done. When you want something you get it every damn time. You make things happen with your will alone. You are fucking fierce. You have had ppl try to tear you down, break you, remake you into their idea of beauty,...
I could never pass as a woman. I am clearly a sissy put into woman’s close. Love being sent out like that. Exposed. Knowing whoever sees me knows just what I am. I have only done that at adult bookstores and at adult theaters. When openly dressed there, either in nothing but lingerie and stockings and panties, or if I go in a skirt, stockings, blouse, bra and breast forms, it is not only clear what I am, but most men who enjoy sissies see it as an open invitation to use me. When dressed like...
I could never pass as a woman. I am clearly a sissy put into woman’s close. Love being sent out like that. Exposed. Knowing whoever sees me knows just what I am. I have only done that at adult bookstores and at adult theaters. When openly dressed there, either in nothing but lingerie and stockings and panties, or if I go in a skirt, stockings, blouse, bra and breast forms, it is not only clear what I am, but most men who enjoy sissies see it as an open invitation to use me. When dressed like...
Dresses: This young blonde woman started working across the street from me last week. She wore skirts that were so short they barely covered her ass. In fact she was forever pulling her skirt down to make sure it covered her ass whenever I walked past her. I felt she was a bit of a bimbo. The girls who worked for me wore longer skirts. She had a team of boys working for her, all just out of college like the girls who worked for me. I had been married before and as I just said...
This is my first story; I hope you like reading it as much as I enjoyed writing it. Please feel free to comment, and please give constructive criticism. Thank you. Jane is a 16-year-old girl who is very confident with her body and knows how to mess with boys' heads at school. She’s about 5'2" tall and has well-shaped legs to complement her sexy, curvy body even at her age, a set of C cup tits and a nice round ass. Not bad for white girl! She has beautiful dark long hair that falls just past her...
MasturbationIt’s spa day for nubile brunette Matty and she goes to Thomas Stone for a massage. What the young cutie doesn’t know is that he has a foot fetish and a humongous cock. The stud masseur gets turned on by the sight of her pretty pedicured toes and is soon sucking on them and unleashing his big dick to rub them with it. The lithe sex kitten then gives him a blowjob and a footjob before getting her tight shaved pussy fucked until he cums all over her delectable feet in this kinky...
xmoviesforyouArriving early, I walk into the room and immediately look for the mini-bar. Finding the tiny fridge with several small bottles of cheap zinfandel, I twist the cap off one and take a long much needed sip before kicking my heels off next to the bedside table. A king sized bed lay draped in plush white linens which is fastened against a painted on headboard happens to be the focal point of the room aside from the over-sized tub in the corner. Twisting the cap back on the mini-bottle, I fall back...
It happen when I was 18 years old. I was working for a clothing company at the time and it was a slow Tuesday morning. As I was folding clothes, a tall (I’m 5’5 he was 6’2) light skinned black man approached me. He introduced himself as Sam. He looked like he was well into his forties but was really fit. He inquire about several clothing articles in our store and slowly the conversation became more about me. How old was I? Did I like working there. Innocent questions that raised no alarms in my...
CrossdressingMy name is Aswin, working in Bangalore in IT Company. This is the continuation of the second part; guys, who have not read, read the first part and second part from the couple’s category. In first part, I told about how I got used by my best friend’s ex- gf without allowing me to insert into her. In second part, I told how I satisfied her using my tongue. In this part, I will tell how I fucked her even though she got engaged to someone. Before starting the final part, let me tell about me and...
I’m the Man of the House 2Following Mom’s bare butt to the bathroom, she got the shower started and adjusted the water temp, as I stopped at the toilet and peed, to relieve myself, and then Maryann stepped into the shower, and when I finished peeing, I flushed, then stepped over to the shower, and pulled back the curtain, and stepped in behind Maryann, then closed the curtain behind me, “You never take a shower this early of a morning babe.”Yes I know, but watching your little round sexy ass...
My affair with Judy lasted almost a full five years. We were never caught and no one ever suspected anything about us. The only two people that knew were my wife, who Judy confessed to last summer, and Judy's friend Jennifer, who Judy told a long time ago and who I hooked up with separately (a mother in law referral).Had we wanted to, we could have kept going. Even today, we could still be hooking up once a week and having an amazing affair but it got to the point where neither of us really...
MatureI was just leaving work at when I noticed my boss's wife in the car park looking very distressed and upset. At first, I was wary of approaching her because the other workers had told me she was a bit of a dragon, but she looked almost ready to cry so I just said, "Excuse me ma'am is there anything I can do?"She looked as if she was about to chew me out, but she shook her head and said softly. "No but thank you for offering, I'm supposed to be flying over to Ireland on the 14:50 flight from the...
AnalIn the bedroom Leanne and Ben lay on the bed for some minutes slowly recovering from the excitement of the game. Ben spoke first “Won’t Dean be upset with this?” Leanne replied “What Dean and I have is something really special, we have come through stuff that would have destroyed other couples. We love each other with a passion that is unshakable. This is pure sex and enjoyment and loads of fun with no emotional strings so don’t worry on that score.”“What do you want me to do now?” asked...
She wants to go to Urasawa in Beverly Hills, then that is where we are going. “I would like to make a reservation for two this evening,” I said to whoever answered the phone at Urasawa. “Could you be so kind as to ask Urasawa-Sama if he could squeeze in David Jones and a guest this evening? I’m sure he won’t have a problem with making room for us.” “Yeah, sure. I need a laugh,” the woman on the phone said. A man came to the phone in a few minutes and said, “Jones-San, It would be my...
Janice Stover drove her old Jeep Wrangler into the parking lot of her software company. She felt a surge of pride when she saw all the other cars there. It had been a struggle from her first day of operation, but the hard work and long hours were now beginning to pay off. They now had 23 employees and were recruiting more. She slowly drove to her assigned spot beside the employee entrance and parked her old Jeep. She was dressed in her usual clothes, faded jeans, T-shirt, and broken down...
At Christmas, inspired, I remembered a Christmas fifteen years ago with my grandparents and I went to the storeroom in the back of the house and brought up an old Christmas tree that we had first used when I came on vacation from High School. It was an old artificial tree, in a place full of live pines, which had grown old with. Mom; it was still packed full of old ornaments and lights. We, Natasha and me, spent that evening putting it up and we thoroughly enjoyed decorating the tree as we...
Here's another true story from my wife and I in college...So, you already know that my wife came from a strict Asian background. During college summers, when we weren't living in the dorms, we went from non-stop sex to nothing (because she was living back at home). The funny thing was, sometimes her parents would let me spend the night at their house. I lived about an hour away and they didn't want me to stay for dinner and then have to drive back too late. I would crash on their basement couch...
It was summer, school was out, and my stepmother's younger sister, Susan, was visiting us for a few weeks, so I was sitting in the family room playing a computer game when she came out to see why her little boy, Nathan, two years old, was crying in his daybed across the room. I was trying to ignore the crying as I really didn't feel comfortable around babies, well, most thirteen-year old boys probably are the same way, and was relieved when I heard her come in. "What's wrong, Nathan,...
If you’ve never seen Liya Silver before then welcome to witnessing pure perfection in action. This college girl is an absolute stunner with perhaps the greatest rack and ass you might ever lay your eyes upon. Liya is ready to report for duty in her cheeky military uniform with a skirt so short that her cheeks are literally hanging out. And by duty we mean performing dirty sexual deeds on her Sergeant Vince Carter who walks in on her cleaning and can’t help himself from wanting to...
xmoviesforyouMy live-in relationship with Shekhar at Kolkata was quite memorable and there was not a single day when we did not experience sex in all the ways possible. At the age of 55 years, Shekhar’s vigor and vitality was commendable. He possessed the stamina to satisfy me four to five times in a day. One fine Sunday, we had completed a sexual bout of around 1 hour in the morning, had our breakfast, went to the market and then had lunch. It was hot a humid in Kolkata and we both retired to the bedroom,...
"Cherry-Pie; with extra napkins." I breathed luridly into the receiver of my wireless phone as I paced back and forth through my lonely, sparse, and untidy apartment. That was the code word for two prostitutes. I had to have an extra one this time. As long as you were content to never, ever be in the limelight, there were certain perks that came with working for an agency that didn't exist with billion- dollar budgets. The number that I dialed, the extension that I used, and a series of...
Hello everyone…This is the second part of my story “Horny Me”. I hope all of u liked the first part….i’ve got many e mails regarding the story and i really wanna thank all of you for liking it. As you all know my name is Ruchika, 26 yrs old and i am a housewife..my stats are 32 28 34 and married 6 months ago. I live in Delhi. In my first story i described how i seduced a delivery guy and how he quenched my thirst. Now continuing….. Main Pramod(main bata na hi bhul gai thi uska naam) ka intezaar...
Two years later... Time: Friday, June 2, 2006, 8:12 PM I look out of my window at Baker House a few minutes before sunset, and I can't help but feel a wave of nostalgia. I have gotten so familiar with my room's view of the river and the majestic Boston skyline. But after four tough and magical years at M.I.T., I am one week away from Commencement and receiving my Bachelors degree. And Melanie and I will marry a day later. My time and identity as single and an M.I.T. undergrad are drawing...
I had come home off of leave to see my family and my old friend Jim. We had known each other since c***dhood but became close running partners at the age of 21 when we both returned home. For two years we hung out getting high, going out drinking and having a good time just partying.Jim was a red head with long red hair a thick well trimmed red beard and a lightly freckled skin tone . Same medium height and build as I, we met up again at my old girlfriend’s house. We were both driving the same...
Billy's Many Adventures I Billy is an average young man at the age of 21 has had his share of women that he has met at the clubs. Billy has one secret is that he is a crossdresser. Billy has been one since before he can remember. He enjoyed wearing women's clothing, starting with going through his mother's drawers and finding her panties, and finding enjoyment in wearing them for brief periods of time. As a child Billy did like most young cross dressers wore his mother's underwear...
Alex drove Vicki and me home, since the girls had already made arrangements to stay with us ... or, rather, with Zoe ... following the homecoming dance. No one talked in the car, although I could tell it was more Vicki giving me space to think, rather than her being mad at me too. When we got home, mom pointed me at a chair at the kitchen table. "Vicki, the girls are already upstairs. You head on up and let me talk to Cas for a minute." Vicki patted me on the back once then headed up to...
On Saturday morning, I took a cab to a car rental agency and picked up the Mercedes that I had arranged for. I had cancelled my regular shopping trip in favor of going to Greenwich. I had rented a Mercedes so that we would blend in with the regular resident of that area. Carol was unaware of our destination until we entered Greenwich and she saw the sign at the exit ramp. Then she started to shake more than I had ever seen anybody shake before. I had purposely not told her where we were...
Michael was at work and as was his habit several times a week, he checked the MW4M section of the Craigslist Casual Encounters Personals section. Ever since his wife had died, he never had the desire to even attempt another love connection. He was always on the lookout for couples seeking a BBC to make a connection with. This satisfied his sexual needs with no strings, no romance, just pure primal lust. Since Claire was gone he continued enjoying white women, especially married white women, and...
InterracialKat had been taken from the shuttle and straight to the ship's brig. Her cell, a four by six meter rectangle, was brutally simple and very effective. There was an extruded plastic platform, about the size of a coffin, glued to the floor and intended as a bed. There was a plastic toilet, also glued to the floor and to the bulkhead. One wall of the cell was floor to ceiling metal bars, spaced too closely for even her smaller arm to squeeze through, and broken only by a door with an...
After our afternoon at the beach, Megan and I head back to my place to freshen up before the cncert this evening. Megan gets an unwanted surprise and questions what she is doing this weekend.Megan was sitting on the back porch as I returned home from walking the dogs. Her hair was still wet and she looked a bit distraught. “What’s wrong?” I said sitting next to her.She held up her phone and showed me the text string.“So, he knows what is going on?” I asked.“Yes, he watched us at the beach...
CheatingI must have been 16 back in the day, but I always looked older so it didn't really affect anyone's judgement in the sex world that I had loved since I can remember jerking off for the first time.I was walking the streets of Amsterdam that day, the Red light Disctrict looked like paradise on earth, all those hot hot girls smiling and telling you to come in...I don't even know how much they wanted, I didn't care, just walking in those tiny streets and seeing those creatures was more than...
The Question He woke up with a hard-on. The question was what to do with it.He thought of Janey, whom he'd been with last night; they'd had a fine evening, dinner and a show, and back to her place for a nightcap.Janey was a touch over five feet tall, and by this man's standards, she was wonderfully proportioned. She'd attained an extra layer or two of fat, and the man appreciated it, knowing it would serve her well if she ever went on that North Pole excursion, or was suddenly transferred to...
She glared at him, willing him to notice her. Shifting position, she edged closer, nudging his arm as he scooped up the pile of meeting minutes stacked precariously on the edge of his desk. She gasped when he wavered and struggled to stop his load from toppling.Looking up, he frowned at her."Sorry," she said, fluttering her lashes.She smiled, anxiously hoping he'd smile back.He didn't. Hugging the folders to his chest, he pushed in his chair with a flick of his hip."Do you want...
Office SexIve caught her a couple times when i was young. one time one i was six i went to sleep in her room with my dad cuz i heard thunder and saw lightening. i ended up crashing on the end of the bed but an hour into sleep i heard heavy breathing then i turned over to see my mom naked riding my dad for about 3 min or so ha. she was in better shape then and it was a site to look at..im guess small C cups but she has a big round butt! my dad was naked too but i didnt pay too much attention to his...
As I stood there joking with these black boys I kept thinking about my wife. Thinking how hard she made the young man earlier today and how that turned her on. I was wondering if she was enjoying the IR movie that was playing in our room. Was she touching herself? I knew she wouldn't finger herself to orgasm but I bet she was going to the edge and stopping. I imagine she was wondering what was taking me so long. I wanted these boys to see my wife's tits. I started to devise a plan. It was a...
Hi ISS readers. I am going to write down a life-changing story of mine. I came to know that my real sex satisfaction can be achieved only through one person, that’s my mother. My name is Raja Ranjith. I am working in the IT sector. I am always horny. I have a 5.5″ inch tool, which became bigger and better after having sex with my mother. My family consists of 3 people. My father passed away during the final year of my college days because of chain-smoking. He never satisfied my mother in...
Incest“It’s not fair,” Nova mumbles into the lip of the whiskey bottle as her tongue seduces out the last drop, wanting more of that burn. Her eyes are hazy from a blend of the liquor and grass she's been consuming from sunrise to sunset for the last four days. Her chest is tightening, making it hard to breathe like she's drowning in a sea of barbed wire. That's the only way she knows how to explain it. Every breath constricting the wire, stabbing the tiny razor blades into her heart. “It’s not...
Love StoriesEllen awoke, in her warm bed, the sun pouring in the farmhouse window. She was lying on her side in her evening attire of lacy bra, stockings and garter, with no panties. I had awoken her, as my hard cock had separated her pussy lips, and buried itself deep within her. I had touched her clit and pussy from the front until she was soaking wet. Then I slid my manhood deep within her, slowly pumping her till her wetness covered my cock and I was able to pump harder. She awoke slowly, moaning, as...
Hi peter was my best mate we lived a very small town in Australia .we done every thing from watching our sisters get mood that was grate .until the day o DG a school swimming day we were the last in the showers but every one had gone so I took off my swimmers nude we never seen eacher nude I was just turned 15 peter was 14 . as I hard looked at cock he was watching me soap up and he was pulling his dick his dick was small but hard my cock was getting hard also I dropped the so as on...
Ok, This is how I ended up with a married couple. Let me describe everyone in this story. First the old man. Actually, he is a man who can not satisfy his own wife I think. He was in his 50s and a wealthy man. Then me I am 18 and don't have a job yet. I was after an exam for a job. Best for the last, the wife. She was in her 40s. Actually, she was 40. Has a great body with perfect bombs and ass. Had a great face like a model. Everyone who sees her thinks she is very young. Like she is 28 or...
Palace of the Queen, Merka Planet Remza Universe Recta 9: Conference Room 4.6 Preliminary Strategy Discussion Attendees: Gen. Nastovor Sarajengus — Head of the Armed forces for the Azayal; Chairman. Adm. Maron Mergazengis — Chief admiral of the Azayal Fleet. Adm. Pawela Hage — Intelligence Chief combined forces. Jacob Peck — President of the Flock of the Una. Grefel Magoo — Director of Intelligence of the Una. Queen Mergal Ravengus — Queen of the Azayal. Lisirra Chamadar — Crown...
Note : This story is completely fictional! Never try to do it in real live - it BAD! My mother and father started fighting when I was young and it was something I got used to. I don’t know exactly what they were arguing about but they always did. It was late that night, it had already passed midnight and I could hear them shouting in the other room. The door slammed and my father came storming out of the room. I hid under my covers as I heard his footsteps come by my door. My door pushed open...
IncestHi All. This is Nitya from Hyderabad. I get excited when i share my experiences with strangers. So i want to post my experience and your comment will excite me. Coming to myself, I am 23 old fair normal sized girl with 34 -28-34 figure. Before I meet Jay [My boy friend] i was traditional and shy girl. The relationship with Jay really changed my behavior and dressing style. Coming to story, When i am in my B Tech 2nd yr Jay proposed me. I can’t say no him because he is so handsome and rich. He...
Jeff smiled as he walked toward his neighbor's house. He loved when they went out of town and he watched their dog. This meant he had to go there at lest three or four times a day. This gave him plenty of time to explore.Jeff loved to see women's panties and his neighbor presented two opportunities. First there was Nancy who was 45 but who looked 30. She was a sexy in a MILF way. She was about 5' 7" and was in excellent shape. Jeff had always wanted to fuck her but that was unlikely to happen...
Thank you for ParadiseThis hot shemale story was sent to me by our forum member Leeya and i'm anxious to share it here with everybody. It's a classy story about a guy who went to an Asian country on a business trip and met a very beautiful womain in a very romantic atmosphere... Little did he know that this young voluptuous lady was a ladyboy.Thanks for this story Leeya. As a reminder to all others, if you have a story suitable for this section, by all means post it either here as a comment or...
Unsurprisingly I woke very early the following morning, well before I heard Ron drive off to his fishing. Again I'd been contemplating going across to Jacqui as soon as Ron had left. This time I'd convinced myself that I should. I gave the Rover ten minutes, just in case he'd left something behind before I pulled on my shorts and left the tent. My heart was pounding and my stomach churning like never before. I wondered whether to knock or just go in but decided I'd better knock. My trepid...
Georgina, twenty-one-years-old, looked at herself in the mirror. She wore a short-sleeved white blouse and a dark blue pencil skirt with a hem just above her knee. It was summer so she had bare legs and wore high-heeled dark blue shoes. She looked every bit the strict school teacher; in fact much the way Miss Watson used to dress for class. She had met up with Miss Watson a few times since they first met back at the school and Georgina had spanked and caned her ex-teacher in the Punishment...
SpankingWe must have slept because an hour had passed. We all got up and went to the kitchen, naked, to get some water and lunch. Funny I was drinking water. This is new to me as I prefer coffee or coke-cola. I asked the girls to sit at the table and I would make lunch for them. Collecting 6 eggs, 3 pieces of bacon, 3 spring onions, 3 radishes, 6 mushrooms, 3 garlic bulbs, and two tins of chopped tomatoes. I cooked the bacon, garlic and mushroom in some olive oil in the large frying pan. Beat the...
Friday, October 11, 2013It was a Friday night and I was sitting in my outdoor hot tub, naked and alone. On the edge of the hot tub was my scotch. It wasn't the cheap stuff; I drink Glen Morangie or Glenfiddich. When I was younger and didn't have much money, I drank the cheap stuff; now that I have some money, I prefer single malt scotch.It really didn't matter how good the scotch was, or how nice and warm the hot tub was, or how much privacy I had with a solid eight foot masonry fence around my...
Hi friends, this is Vishal again. I had posted before a sex story about my fun with my previous girlfriend. After our breakup I was just alone and searching for sex like a mad dog and finally I got my heroine. But it did not last long as she was shifted to her home town. So I thought to explore some new fun and finally I got that. If someone wants to spent a nice time with me then mail me on As stated in the previous story, when I was transferred to patna (bihar), I had rented a room in a...
The New Slave The New Slave Putting down my paintbrush, I looked at the clock and saw I had only ten minutes until Master William would arrive.? I covered up the painting and put the brushes away, thinking all the time about the strange direction my life had taken over the last two years.? By the time I had put away my paints and put on the handcuffs Master William insisted I wear each time he visited, it was almost time. I felt the rush of fear I always felt before he arrived and worst...
Als die achtzehnjährige, blondlockige Melanie den Partykeller betritt, dauert es einige Sekunden lang, bis ihre Augen sich nach dem hellen Sommerlicht an das Halbdunkel des Raumes gewöhnt haben. Rechts neben dem Eingang ist eine kleine Bar mit diversen Flaschen Alkoholika aufgebaut, links von ihr stehen diverse HiFi-Geräte auf einem Tisch. In der Mitte des Raumes tanzen mehrere Pärchen engumschlungen im langsamen Rhythmus eines Schmuse-Songs. An den übrigen Wänden des Raumes stehen diverse...
This is a totally true story of what happened this time last year. My name is Sophie and I’m 47 years old, five feet two inches tall with short black hair, and 34a chest and I am married to Rob. We have often spoke about having some kind of swinging fun but never really had the nerve to try, especially as Rob was more keen than me and I just never felt it was the right thing for us. Anyway last year we were going to my Rob’s workplace Christmas dinner with his best mate Gary and his wife...
Hi friends, I am Gopika, 28 years old with a decent structure 34-36-32. I got married very recently. My hubby is working in Gurugram as a teacher. He visits home only on weekends. I started missing him a lot. My hubby always encourages me to be active on social media. I too slowly started to use WhatsApp and had a habit of keeping the WhatsApp status regularly. I started posting my selfies. My hubby also encouraged me by giving good comments about that. My school friend Ganesh started to like...
Author's note: You don't have to have read the other stories to enjoy this one. Sit back, relax, and enjoy! - Vivica“What can I get you?” the acne-riddled teenager behind the counter asked. Aubrey looked at me, waiting for my response.“Whatever you want, go nuts,” I smiled.“We want a giant bucket of popcorn, a bag of Sour Patch k**s, a small diet Coke for me and whatever he wants to drink,” she said.“I’ll also do a small diet, please.”“So that’s one big bucket, one Sour Patch and two small...
This is just a small first story to see what people think of my style. Behind-the-story stuff in comments. But warning, it’s kind of a dream-esque style. she doesn’t really have an age, but I’m judging from my random images of her she’s 18 too. ——————————- I’m already naked as she pushes me down onto the bed. I can’t see her face, as always. It’s in shadows. All I see is her pale skin and red lips. She smiles behind pressed lips as she lightly drags her nails up my chest. She is also naked as...
Wow it must have been more than a decade ago when I first discovered Looking Glass Magazine. I was living in Manhattan. Whenever there was a dry spell with the ladies I would visit one of the many random adult book and video stores. Usually I went right for the booths or the live shows but on one ocassion after perusing the current VHS films out I decided to check out the magazines. Juggs, Gent, Over 40, Over 50 all the usual titles were there. Then lo and behold I saw something I had never...