Sidedressing
- 4 years ago
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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...
My husband David and I have been talking about having an extra partner in our love life for a while. But we could never really decide on the place or time until about a week before my birthday. David came in from work one evening with a big naughty smile on his face. He started talking about my fantasy of having an extra male partner. There was a new guy who transferred from his companies home office. He said he was well built, but alittle bit smaller than him and that he thought I would like...
Previous stories: My Family Holiday With Boss: Mera naam raja hai main paiso k liye bahut poesssive hu.hamesha bivi kamaya ko job karne ke liye kahata hu par who nahi manti. Meri salary kam hai 6k/month isliye main condom bhi afford nahi kar pata. Waise kamala ke dad se paise lete rahata hu, thoda bahut aish karne ke liye main off main accountant hu aur sham ko ghar 8 tak aajata hu. Ek din mujhe pata chala ki off main mere boss ki personal secretary 6 month ka maternal leave par hai. Kisi kam...
“What do you think about Tech School,” asked Miss Ames, “it’s got a great computer department, one of the best in the area.” Britt Cain looked intently at the brochure her guidance counselor had placed in front of her, and replied, “I hadn’t even considered that but from the looks of it maybe I should!” It was a lot of work trying to pick the right college, and as counselor for two hundred seniors, Anna Ames had all she could handle scheduling...
Backwoods Bruises Chapter 1 The roadway off of the main street was bumpy and filled with muddy depressions, which left me with the impression that, at any time, my car might sink into the mire and leave me in an everlasting pit, from which I was doomed to never return to civilization. It went on that way for almost a quarter of a mile, before I finally saw the first and only house on the desolate forested expanse. The house itself had seen better days, totally lacking paint of any kind, with...
I was a younger man at the time around 45yo 6’2′ 210lbs and had been separated from my ex wife for several months. I was a frequent patron of a local bar after work, and stopped in for a few beers after work. The bar was pretty quiet except for the juke box playing country music, with only a few people sitting at a table at the back end of the bar. I noticed Judy sitting at the bar alone talking with her friend the owner. I had always been attracted to her so I sat down on the stool next to...
We were the last to leave the party. The band had already announced the last waltz, but we clung together for the final time. We were about to spend the rest of the night together in a hotel bedroom and we wanted to remember it as special.I'd just finished a run as the star of a West End musical show and I was sky high. I had a month off now and was looking forward to spending it with my lovely son who also acted as my manager.We were having the one night in this hotel and then we were jetting...
IncestAfter a long day of grading, Dr. Douglas Dyer was almost done. ‘Never again’, he vowed to himself, ‘will I give four essay finals on the last two days of finals week. It’s just too much.’ He could get one good night’s sleep, and double check his formulas, and file all his grades comfortably before tomorrow’s deadline of noon. He was very tired of grading. He checked his email. ‘Don’t forget that you still have an incomplete left over from last semester,’ read his latest. ‘Even if the grade...
Moving day. I wake up, shower, French braid my hair into pigtail braids, and get ready. I put on jean capris, a peach Juicy t-shirt, and my tennis shoes. On top of everything else that we have been doing lately, we have also been shopping, buying some new clothes that are popular here in the States. The good thing is that there are a lot of similar clothes all around the world. The house has been painted, the rugs put down, the kitchen redone, etc. So much has been done to that house that I...
Well I finally gave it a trial run guys, I took two of my favorite black dildos with us on a ‘Road Trip’ I guess you could call it. We got a babysitter and went out about 7:00 and headed east on I-80 from North Platte near where we live. Our blue Expedition washed and shiny, and the dusk setting in. We didn’t take my car because I knew I would need the room. We drove toward Lincoln, although I knew we wouldn’t go that far before we would turn around and head home again. Once it got dark I laid...
While we were dressing, Bobby called information, got the name of a shuttle company and ordered us a shuttle van to meet us here at 11:00 and take us to the border. We ate our breakfast at the cafeteria near the mall, then went back to wait for the shuttle to take us to the border. Juan Rodriguez was the driver and we found out he owned his own shuttle company, with three shuttles to shuttle tourists to and from the border. Bobby and Tia sat in the front seat with him and I heard them...
The next morning, Candice and I showered together again, which allowed us to rinse away that sex smell. Kelly joined us to wash and dry Candice's luxurious hair -- and to ask me to anally penetrate her. Not fuck her, not come -- just fill her back door and let her get used to the feeling. And what a feeling. I started tweaking her soapy nipples and she came anyway -- as always. The girls all ate breakfast topless or in their school bras, now, doing whatever was convenient. Mom, who had...
I am now beginning to think that maybe fucking Karen was not one of my better choices in life but, as they say, life goes on and I don’t have any regrets about what I have done. All I need to do is work out how to make it happen. I spent a few days thinking about the best way to approach Susan on this. You just can’t come out and say “Susan, do you fancy a threesome with our daughter?” then one night while we were watching TV. I had an idea. Like every normal married couple Susan and I...
Marley loves her husband – they were childhood sweethearts and have endured everything together. Now they are married and they are best friends, and she can’t imagine her life without him. The only issue seems to be that she is more sexually adventurous than him, and feels she is missing out on something. After telling her husband she has another late night at the office, she continues an outrageous encounter with her boss. She doesn’t want her marriage to end, but what she is...
xmoviesforyouYou, Venus Xana, are ready for some fun. You sigh in petty annoyance though, because instead of going and doing as you're supposed to, you have been called back to hell to check on the humans you've captured, instead of finding another soul to steal. It has become so common, and you have lived so long, stealing the souls of men (and some women, when the times call for it) when they cannot control their desire for you. You've mastered your abilities to give them just what they want, and you are...
FantasyHi Any ladies who want friendship please mail to This is a true story about what happened to My aunt who was living my next door which she told me when we were enjoying. I am writing the story assuming that i am her husband.We have always had a great sex life and we had talked about our fantasies a lot to boost our sex life. One day we were talking in bed about what we would like to do and i said i would like to see her with another man, to my suprise she said she would like to have sex with a...
Once again they had argued before she went to work. The reason was also the usual one – sex. This particular morning Mark had woken unusually early, with his usual erection. Deciding to test Clare's mood, he had rolled over and nudged his naked penis against her, just after the alarm had gone. Letting his hand slide up her thigh, she had moaned gently and pushed back into him, letting his cock ease up against her warm full back panties. As his hand slid up and over her belly to aim for her...
CrossdressingWhat you are going to read is a true story, the names have been changed to protect the guilty…My wife and I have always played. Over time, it's gotten more adventurous and naughty over time, but this adventure was my favorite so far.We went to our local swinger pool to swim, talk, and fuck each other at least and who knows what else. Upon our arrival it was the usual crowd. Lots of couples, some singles. We both spotted a black guy sitting by himself. My wife turned to me and said “well...
Mornings on the island are so beautiful. The mornings were filled with the sounds of many birds since there were trees near the big house. The variety was amazing, as there were a couple of types of toucans, several long-billed birds, and some very noisy green macaws. Some of the birds almost were pets and often flew onto the porch to beg for treats. Mina shooed them off as fast as she could so that she didn't have to keep cleaning their droppings. She had a place out behind the kitchen...
Doston aasha Karti hoon ki meri yeh kahaani aapko pasand aayegi aapki bhabhi seema. Jab meri saadi hui toh main bahut dari hui thi. Sochti thi ki nayi jaghan par mann lagega ki nahin. Aur phir pariwar bhi itna bada tha. Par jald hi mujhe malum padd gaya ki humare liye ek naya flat kharid diya gaya hai aur hum wahin shift ho jaayenge. Jab main shift ho gayi toh mujhe bahut khusi hui. Inke office jane ke baad main aaram se Tv. Dekhti. Kabhi kabhi meri badi jethani mujhse milne aajati or unke...
Introduction: This is as close to reality as you would get – if you meet a young mother who has a fetish for kiddie porn.. Ever get the chance to help a mother educate her 2 young daughters in the art of love making? I did. I was 20, going on 17. A baby. And though I didnt know it at the time, I had all 3 girl age groups at my fingertips – 1. Girls under 12 (at summer camp for example) would get a crush so big they would swarm around me in groups, trying to impress. 2. Older teenage girls...
It had been a while since I was a center at one of Mark's parties. Due to work and well life I wasn't able to until recently. I got a phone call from Christie as I did just about once a week. She's always checking up on me and making sure I'm doing well. She's definitely a dear friend. Anyways, when she called me this time she asked if I were available for a party this coming Saturday. I checked my calendar and sure enough for the first time in ages, I didn't have to work. It had gotten to the...
A Walk at the Beach, A Morality Tale with a Tail "Thirty bucks for this piece of shit? What a joke!" The man was clearly used to speaking his mind and getting his way. He loomed over the tired looking woman next to him. "Oh Larry," said the tired looking woman, "you don't have to buy me anything." She said it in the resigned voice of someone who knew that it made no difference. He turned toward the far end of the cluttered little shop where a frizzy- haired woman in a tie-dyed...
Another Piece of Paradise By JJ This is a work of fiction (unfortunately). It may also contain adult themes and opinions that some may find objectionable. If you are not of the age to be able to view such things, then stop now. I'm writing in the universe of Patricia's "Changes in Paradise," If you have not read her magnum opus, and are interested in mermaids, then you should go right over to Fictionmania.tv and read them post haste. This story assumes that you have some...
I've always enjoyed a wide variety of sexual adventures, although when I was married, my wife wasn't quite as adventurous and broad minded as me. In her eyes, the most daring thing she'd ever done was to go out with no knickers one summers afternoon, and watch me have a wank in the woods.However, when we divorced, my sexual world opened up an endless amount of adventure. Once I'd found a flat, my first thoughts turned to cross dressing, and I went to a local supermarket, and added a few Paris...
"This exercise is called trust." I have my charges lined up on the practice field. Alys, Nev, Brin, even Godiva has decided to join in. I want to help them regain some of the trust in themselves and in their fellow man. I remember this game from one of the thousand classes I took when I as trying to find my place as a teenager. I was pretty sure it was a stupid game at the time. As it will serve a purpose today, so I no longer think it so. "That's a stupid name," Brin whines agreeing...
The day of the party arrived. I awoke, after hardly sleeping, and headed to the gym. When I arrived back at the house, Nancy was up at the counter. She was drinking coffee and looking at her Facebook account. My wife was right, she was very stunning. She wore a half cropped shirt, which showed the bottoms of her large breasts. Her hair was pulled back in a pony tail and she wore the tightest boy short panties which hugged her ass perfectly. She was totally focused on her phone and must not have...
As I walk up to the coffee shop, he chose for us to meet at, my heart was racing. I had met men from the internet before, but never this soon. I hardly knew him, but it seemed that things went faster with him than usual. I agreed to meet him wondering what exactly I was getting myself into. I had put an ad on the internet hoping to find an older married black man that would want to have sex with me for a little while. I wasn't after just sex; any woman can go to a bar and find that. I was...
Hello, sex story readers. It was my first day at college. Fresh out of the school. I still looked as if I should be in school. I looked like I was 15. Short height very slender body, breasts just starting to grow and short hair – almost a boy cut. Don’t get me wrong. I wasn’t ugly. I have great looks, I have perfect girl abs that let me pull off crop tops almost perfectly and I have a pair of properly toned legs. I also have a very good fashion sense that makes me quite popular among the guys...
Gasping, you pulled the old drunken hobo off of the tracks. He must have fallen on while drinking - it's a shame he didn't have pants. You have seen sights nobody should have to see. The hobo blearily blinked at me, pointing some kind of remote at you. "...John Doe, huh?" The hobo shook his head and sighed. "Well, fine. Might as well pass it on, not like I'm using it." He tossed the remote at you and nodded. "Thanks for saving my life. Use that to have fun, just don't focus on it too much or...
Mind ControlOver the next 2 weeks, our relationship became worse. What little communication we had left, was now gone. Our sex life, well it was suffering also. Brian would no longer fuck my pussy, he started me out on a butt plug until I stretched enough to accommodate his dick. A lot of our fucking involved him sitting on the couch. He loved leaning back on the couch, and me lowering my ass to his cock. The first couple of times we tried that position, I thought I was going to die. But he started...
George Simpson received the package just this morning. He now sat behind his desk as he stared at it. His daughter Elise has sent him the package. And he wondered why. His birthday is some months away and he couldn’t think of any other occasion that would merit a gift.With eager fingers, he quickly opened the brown envelope. Slightly surprised when he unwrapped a videotape.Wondering what this is all about, he slipped it on the VCR and sat back to watch the curious tape.After a few seconds, his...
The others showed up one day around noon, after we had been on the island about a month. Oueenie, her two brothers, and a black stud named Art. They came marching down the beach, carrying a white flag, wearing very brief bathing suits. We scrambled into our clothes, which we hadn't had on for the whole month, then met them at the surf line. They were all gorgeous, with the same sensuality we had acquired. They seemed a little nervous, and Mom said "Hi. I'm, um, Madge, and these are my...
While we sat chatting in earnest and watching the porn film Brenda was rubbing my balls. The film finished and Chris said “Do you mind if I choose the next one?” “You carry on Chris” I replied, to busy enjoying the attention my balls and cock was getting from Brenda, my cock was beginning to rise again. Chris changed the film on the DVD, as I watched the titles roll up the screen Brenda lowered her head and began to suck on my penis. ...
BisexualIt was a beautiful, sunny Friday evening after a long, hard, rainy work week. My mind was burnt out from dealing with coworkers' mistakes, irate clients, and a husband at home that wasn't paying very much attention to me when I came home from my long days working hard to pay the bills. When I clocked out of work at 5:30pm, I left excitedly for a massage appointment I had set for 6:15pm. There was no way I was going to be late- I'd been looking to my Swedish massage appointment for days, needing...
Straight SexI finally made the decision to join a gym and try to get into shape. I’m not obese but over the years I have definitely put on a little fat. I stand 5’6 and weigh almost 210, according to my latest weigh in, with black hair, blue eyes and a well-trimmed beard. I have never been the most confident person in the world but since hitting 200 pounds I have found a new low. The first couple weeks were pretty rough since I hadn’t done much physical activity in the last few years. I decided to go to...
Quickie SexFunny how clouded your judgement gets at times. What seems irresistible and so right can seem so wrong after a few days. Or hours. Or in this case, about ten minutes. Liz has been cutting my hair for a least five years. She runs a women’s salon out of her home and my girlfriend pulled me in last year to start getting her to cut and colour my hair. Liz is in her late 30s or early 40s and I’ve always found her attractive. She has one of those bubbly personalities and she is cute as hell to boot....
New Dice Dare - Extreme Rules At the request of many cucks who does not want public exposure but like to have exteme exsposure to Dom, Here is an extreme variation to the original dice-dare rules, that doesn't involve the exposure of information online. Dom agrees to not expose any details online.You must be willing to give it all up to play this version; there are more questions and pics and more info options for the Dom to collect of your wife for his private collection, including all her...
Hi friends, my name is Fzee (pet name) I am a regular ISS reader and most stories read on this site have helped me in flirting and gave me new sex positions. Today I am writing you a true incident of my life. It is how I lost my virginity. First let me tell you something about myself. I am 18 years of age, tall handsome and well built body. I am currently doing my engineering in Pune. Pune is not my hometown. I stay alone in a rented flat and have joint Tiffin service for lunch and dinner. My...
Hello everyone, I am Riya, back with the next story in the series. Request all of you to read the previous parts first, as this will be a direct continuation. The next day, I went to my college as usual. But all day, the thoughts of foursome sex were running in my mind. Then when it was 2 pm, I saw Rahul at the college gate. I got on his bike, did not say anything, and he started driving. I just asked him where he is taking me. He said that Pratham’s parents are out of town, and we are going...
In the morning, we rose, cleaned up, and went into the dining room for breakfast. Marianne had a happy look on her face. My parents joined us moments later. I smiled as we were all served. "Marianne, what are you so happy about?" "Tom's going to take me to the prom. He's such a nice guy. We sat in the den and talked for a long time." My father looked at her for a moment and then smiled. "Perhaps we need to meet and talk to this young man more and soon." Marianne said, "Dad, he...
I woke up to the most beautiful feeling. Glancing down, I saw Glen kneeling between my legs. He was bent over and gently licking my pussy. Reaching down, I ran my fingers through his hair."Mmmm, what a nice way to wake up," I said.Keeping his mouth glued to my pussy, Glen glanced up. He flicked his tongue over my clit and then buzzed his lips. My brother continued to lick me and nibble my clit. I dropped my head back on the pillow. He moved his hands up to my breasts and started toying...
IncestMy first time was when I was 15 with one of my brothers friends named Guy. It was after a drunken party at our house when I woke up with my head resting on his arm and his other hand stroking my hips enroute to my increasingly erect penis. He was close and whispering in my ear how much he liked me while kissing my neck intensly. It felt wonderful!, even though I tried to convince my self it didn't. This wasn't the first time he had made advances as the drunken parties had become a weekly...
“Please let me go”, she said shaking with fear. “I have money, and you can have it all, just don’t hurt me please”. “Shhs” , I cooed her trying to calm her down. “I’m not going to hurt you Roz, and thanks, but I don’t want your money, I only want to please you…and myself of course”. I said in a calm and non-threatening voice. “If you only cooperate and not try to alarm anyone I’ll be done within an hour or two, and you may even experience pleasure in this”. “So you just want to use me like...
After a break from their first round of sex, she made them drinks and they refreshed their minds and bodies. She stood there smiling at him, as her pussy still throbbed from his mouth and tongue. He told her: “I have to have you. I have to have you now.” Her lover held her against the wall in the living room as he dry humped her body. His cock was like a rock and his need was so great. She bit and sucked on his tongue deep in her mouth feeling his cock rubbing against her!“Oh fuck I feel like...
Hi ISS Readers! This is Jack from Vijaywada for the first time to post. I being new 4 this writing community need your valuable outputs and feed backs so plz don’t stop after reading but send me your input thru mail. Straightaway let me come to the incident that took place with me during my graduation to employee age with my sisters. Even I too feel shame but erotic by those. We are a middle class family; I am staying with my 2 elder brothers, mother and father in Visakhapatnam. At that time I...
IncestPART 2 The next morning I woke with my aunt impaled on my once again rock hard cock and my face buried in her huge tits. Unfortunately it didn’t take long for my balls to throb as I pumped load after load of hot cum into her tight cunt. She bounced and bounced on me until I slipped out of her then she took me in her mouth and sucked the last drops of cum from me. I was in heaven. We showered and I dressed in a matching black bra, panties and suspender belt with black stockings. Put ...
I sucked it , it was hard oh so hard and hot while throbbing like nothing i had ever felt before .... michael got closer to me and then started to feel my body with his hands before going to my penis which went hard , i reached round with my hand and started to play with michael .............after a while barry said hes going to make it up to me now but he made me promise not to tell anyone , i promised . He said lay down on my back , i did , he parted my legs and then started to feel my...
Coach had barely turned around and the couples were all going at it. Chris and Jamar were aggressive, Devon and D.J. were deliberate, and Lee and Trey were subtle and romantic.Mark had his head on a swivel as he was soaking up everything going on around him. There was the interaction of the couples and the individuals who were slowly peeling off their clothes and getting ready for their moment to pounce. Mark quickly took off his clothes and stripped down to just his jockstrap.Chris and Jamar...
Gay MaleIn this story I have changed some information for privacy reasons: Address: 12 Brick Road Name: Brian - 15 Neighbors: Jack – Father 44 Kate – Mother 43 Drew – Son 12 Kelly – Daughter 11 Jenna - Daughter 9 Grace - Daughter 8 Amanda – Full Time Babysitter 22 My name is Brian and I live at 12 Brick Road and next to me are my neighbors at 15 Brick road. They have 4 kids named Drew, Kelly, Jenna, and Grace. They also have a super sexy babysitter named Amanda. We are close...
The next few weeks I walked around in a daze. Danny was always by my side making sure I would get through everything. Soon we were back in school. Years passed and this new routine became normal. Then Mom started dating. Some of the guys seemed nice but none of them lasted. Then she met Bob. I hated him from the moment I set eyes on him. I always felt his eyes on me, watching as I walked around the house. Then came the news: Mom and Bob were getting married. I couldn’t believe it. The night...
Karl 5 pm, Tuesday, November 1st, 2006 I closed my geology textbook as the mantle clock chimed five o'clock. It was time. They say we nerds are clever plotters. Tonight I was going to prove them right. If what I'm thinking works out, let's just say that I'll be very happy. I went upstairs to take a quick shower. Afterwards I looked through clothes for something that would not provoke Julia. I was going to take a big risk tonight. Selecting clothes that would not upset her was the...
One pulls out of my face and climbs off. The other pulls out of my arse. They untie my legs, I can see they have used lifting straps to tie me up, what an ingenious use of gym equipment. One picks me up and carries me over to the one who called. He is standing in the squat rack. “Thanks guys, that was my best gym session ever.” I say to my new gym buddies, as I mop up the cum and sweat from my crotch. A late finish meant my gym time was delayed by a few hours. It was populated by...
GroupIt was still dark outside when Whitaker’s cell phone rang. Taylor, who was usually the first of the pair to wake up thanks to being a light sleeper since his first deployment, found he couldn’t get his arm around to pick it up. Whitaker was all but lying on top of him, her head nestled on his chest almost up to his chin. After several tugs, he finally got one arm free and grabbed the phone. “Agent Whitaker’s phone.” “Taylor,” Crawford’s voice said through the line. “A plane is standing by...