Crossdressing With My Mami
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I went through a period in the '80s and '90s when I was very much into crossdressing and being a bottom. I didn't write these events down at the time, but I wish I had. As the events come to memory, I'll write and post them. Here's one such story:In the '90s, I was married, and my wife didn't (as far as I knew, anyway) know about my bi or crossdressing interests. I loved her very much, but I had these other desires I never shared with her. I kept a small bag of lingerie, condoms, and lube...
Let me know if you enjoy this story. Email me at Arian (at) rocketmail.com It was my first visit to Zanzibar an exotic island in Africa. Most people know Zanzibar as the place where Freddy Mercury was born. I was working for a telecom company in South Africa and as one of the project managers I was sent to Zanzibar to install computers for one of the hotels in Stone town. I am in my mid thirties and traveling around the country and Africa was part of my job. After nearly three days of hard work...
Sally moaned as Brad’s body moved within her spread legs. Connected by only the thin, but now very hard, muscle that was his cock, they were so intent upon consummating their passion that they did not even notice me taking pictures.As I watched and photographed my slut wife being fucked by a man she hardly knew, I thought back to the chain of events that had brought us to this place. Both of us enjoy travel and, not long after we were married ten years ago, we had talked about places we wanted...
“I know this is a strange town but I’m sure you’ll be safe,” I told Sally, “I’ll be with you.” We were on vacation and I was trying to persuade her to go with me to an adult video shop I’d seen a few miles from our motel. “We can look for a new vibrator for you,” I continued. “Well, okay, it might be interesting,” Sally finally replied. I then told her about some of the women I had seen in other shops. I remember one foxy...
I've always had a feminine body, slim but some female curves so I've been able to pull of being woman in public a few times already. I started by placing an ad in the local erotic escort guide with some of my best pictures and immediately got replies from interested men. I decided to call one of them who wanted to bring a buddy and we set a date at a local hotel for 8 pm. I wanted to look amazing for the first time so I started by shaving and making sure I had no body hair...
Hello indian sex stories dot net friends , my name is preeti(fake name) age 20. Ye baat kafi purani hai lagbhag 3 saal pehle ki . Mai ek part time crossdresser tha aur mujhe meri chachi bahut pasand thi aur hain . To mai jab vo aur ya koi b ghar pe nahi hota tha to mai unke room mai jake unke innerwear pehnta tha . Aur jaise ki mujhe bondage bahut pasand hai to chachi ke kapde pehnke self bondage karta tha jab ghar pe koi ni hota tha . Isi tarah ek din ghar pe koi ni tha aur mai chachi k room...
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...
I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained. I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels. The first time I saw him I had brief fantasies of my hands and mouth exploring every inch of his petite and...
The act of crossdressing for sex is incredibly arousing. It gets me in the mood for the debauchery to come and allows me to come Brooke the cock loving whore. Even having been dressing for over twenty years, I still look forward to it. Adding to the experience I like to dress while my lover waits in another room. I want them to sit there thinking about what I am doing, what I’m putting on, what I will look like when I enter the room. I want their imagination to flow, and I want their cock...
Hello this is my first story I really hope you enjoy it I am a crossdressing truck driver and with my job I have a lot of time to enjoy dressing up in my truck. One night I was all dressed up in one of my sexy outfits watching some porn and thinking about trying to find a nice hard cock to suck. So I put an ad on Craigslist and got a few but none of them wanted to come to me then I got a message from a guy, he said that he was a driver and was at the truck stop. I ask him what he wanted to do...
I placed an advert on Craigslist as I fancied something new. I'd been crossdressing for a while and had met a few people for fun but wanted to try something a bit more exciting. My advert was looking for someone to meet in public for sex with me dressed in lingerie. A few replies came but the one that caught my eye wanted to meet in an adult cinema in London near city road. I heard of this place and fancied trying it out. We agreed to meet at 11am in a coffee shop nearby and go to the cinema...
I have been crossdressing for several years mostly at home going to the theaters some and to local bars. I was on my way to the Theater one night and stop at a service station and was being hit on by a couple different guys. I flirted back a little then one guy came up to me at the gas pump and said I would love to eat that pussy. I smiled and said maybe next time. When I got home it got me thinking that maybe I should go on a CD date. I looked on a couple dating and personal sites and one...
Crossdressing with my Girlfriend and Boyfriend By Cindybelle Part 3 At the rehearsal on Friday night Mrs Cartwright asked me how my mother was getting on with the dresses for the show. "She has just about finished two dresses for me, including the wedding dress," I said. "I'm sure they will be very pretty, she did so well with your costume for Dorothy last time I can't wait to see them," replied Mrs Cartwright. I...
Crossdressing with my Girlfriend and Boyfriend By Cindybelle Part 4 Oh no, I thought, I sensed that dizzy feeling coming over me again, there was so much going on in my life I didn't understand, with my mom, with Jason and with Aubrey as well and now Janette was going to tell me about mom and dad and being brave. I sat with my own thoughts for a while and then I noticed we were not driving home. "Where are we...
CROSSDRESSING CHARLIE Episode 2 HIGH WAISTED SKIRT "Oh Charlie, you're burning up!" said Mom. She took her hand off of his forehead and read the thermometer. She then left the room to get some medicine. Charlie took the thermometer out of his mouth, held it up against the lamp on the bedside locker, grabbed his hot water bottle and placed it on his face. He left it there for a few seconds before he heard approaching footsteps echoing from the hallway. He slipped the hot water...
CROSSDRESSING CHARLIE Episode 3 RELINQUISHMENT Charlie stared at the door as if it were a wave of fire rapidly heading toward him. His eyes watered and his hands trembled with shock. His could hear his mother's heels clicking against the shiny wooden floor getting louder and louder as she approached her bedroom door. Then, something electric shocked Charlie's brain which broke him free from his frozen state as adrenaline pumped through his body. He jumped to his feet and turned for...
CROSSDRESSING CHARLIE Episode 4 Lust The sky was blue. Yes, just blue, not a cloud to be seen. Every so often a light sliver jet could be seen, trailing white smoke behind it. The sun hung over the city like a warm light bulb, belting its warm rays unto the necks of people within the hustle and bustle of the packed streets. People wore shorts, t-shirts, sunglasses and sun cream, making the most of the rarely seen good weather. The sounds of construction workers banging and drilling...
CROSSDRESSING CHARLIE Episode 5 RACHEL'S DATE Rachel sat in front of her makeup station brushing her hair whilst humming a soft happy tune. She had just dried her hair after getting out of the shower. She was dressed only her in bathrobe as she wasn't in the least bit cold because outside the sun was splitting the rocks and melting the tar on the roads. As soon as she was done brushing her hair into a silky shiny doo she walked over to her chest of drawers and began to put on her...
CROSSDRESSING CHARLIE Episode 6 THE TENNIS UNIFORM Since Charlie and Rachel's day of sorrow three weeks ago, much has been altered in their lives. For a brief time they became closer than ever as they shared their feelings with each other. Emotions of pain, jealousy, hurt; anger and betrayal were common occurrences of feeling in their deep immersive conversations. Despite the fact that their mother felt alienated and that she was alone in the universe she still felt a glimmer...
CROSSDRESSING CHARLIE Episode 8 FAMILY AND NIGHTMARES His eyes opened quickly. The first thing that came into view was his bedroom door. His heart slowed down as he exhaled into his pillow. It was just a dream. He thought. Well of course it was! His eye's swirled about in their sockets like a startled animals as he rolled over onto his back and licked the inside of his mouth. That usual morning taste was in his mouth and he couldn't wait to get his hands on his toothbrush. He...
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 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 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 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 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 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 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...
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...
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...
Transsexual100% fiction! My brother & i boarded the train bound for grandma's. During the 3 hour journey we had plenty of time to talk about the good old days when we would get into trouble chasing her chickens & how she would bake for us. She was very lonley these days & had asked for us to pay her a visit. After getting off the train we made the short walk to her house. Grandma was delighted to see us & as usual had baked plenty for us. She was very elegantly dressed in blue satin blouse,black skirt &...
IncestRight, Chris, Sarah’s new boyfriend, you know what an exhibitionist she is? Well, has she told you about the time she did a strip for 10 men, and what they did to her? Surely she will have told you about that. No, well, I had better then, hadn’t I?She had asked me a month previously about if I minded if she let men finger her pussy, as long as they didn’t fuck her. I’d told her I didn’t mind much. Actually, I’d quite enjoyed seeing men feeling her tits, even that tramp in the last story about...
It was a beautiful setting for a wedding. The bride, Kate, and her husband had chosen to have a small ceremony, set on the beach, with just their closest friends and relatives in attendance. Everyone was in the festive mood that comes with a wedding. The husband could hardly take his eyes off his lovely wife. The ceremony was short, the guests gathered on a secluded spot on the beach near the hotel where the bride and groom where staying. Pictures were taken, vows were made, everyone...
So we're lying in bed watching TV when out of the blue my wife Ellen says, "Honey, I've been a naughty girl..." Our car had been smashed up in an accident, so we had been relying on my company car to get around whilst it was in the repair shop. With me being away on the road a lot, this mean't Ellen had to ride public transport to get around. Her story was about her trip home from work a few days earlier. She said she was waiting for the train in the subway station when she needed to go to the...
Cheating WifesMy wife, Cynthia, and I are in our early thirties and living on a small farm outside the small town of Waycross, Georgia. I have an insurance agency in town, and Cynthia stays busy on the farm and raising our two kids. I’ve recently been thinking about the amazing experiences I had growing up with my parents in Waycross, where they still live, and even continuing, recent experiences. My name is Kevin, and this story will start with some recollections from my childhood.I suppose that most people...
IncestHi, I am Ashley and this is one of my Dirty Senior High School Chapter :PAshley, Ash as people would generally call me in School, I was tall, slim build.I was 5'7, Long brown hair, Fair skin tone, Pink high-cheek boned cheeks, Light brown eyes, Perfect lips, Long toned legs, Curved body, Always a waxed body, A bald tight pussy, Yummy 36C boobs with pink nipples, A round tempting ass which made guys just want to muff drive me, Suck my boobs, and fuck and eat my pussy.I was not very good at 1...
Hi Y’all,Well, I guess you can only go so long without being recognized as the Uber driving slut mom. I live outside of Joint Base Lewis McChord in Washington state. Just yesterday, after dropping the kids off at school, I decided to turn on my Uber app and see if I could make some money before needing to complete some errands and clean the house some. Within seconds of turning on the app, there was a request just down the street. It was a young guy who turned out to be late for high school and...
Group SexA Strangers Cum Part OneMy thrusts increased in both tempo and depth as I neared my release, I could feel Kathy getting more insistent as she was obviously getting nearer herself and it looked good for a simultaneous orgasm if I could just hang on a little bit longer, but suddenly Kathy stopped moving and urged me to stop as she felt her orgasm start and she became too sensitive for me too move, I had no choice but to wait until her sensitive phase was over then finally it was my turn and I...
Hi Y’all,Well I guess you can only go so long without being recognized as the Uber driving slut mom. I live outside of Joint Base Lewis McChord in Washington state. Just yesterday when after dropping the k**s off at school I decided to turn on my Uber app and see if I could make some money before needing to complete some errands and clean the house some. Within seconds of turning on the app there was a request just down the street. It was a young guy who turned out to be late for high school...
0700hrs??Master makes contact on my phone with the message 0700hrs??Master makes contact on my phone with the message. ?Meet you at our special place, Fri, 8 O?clock sharp. Usual items required, usual rules apply.? I catch my breath and close my eyes. Friday night is only 2 nights away and he wants to use me again. I so look forward to his contact, usually once a week at my place we fuck and play, he teases and tortures me and he leaves next morning. Recently, he has been booking a room...
Hi Everyone….This is Silver back with a new experience…My last experience I had written was Sales women in Sept 2009, and thank you to those who mailed me back, some with comments and some for experience….and also thanks to all readers of ISS. This is not an incest story, but still i think this section is the most read. thats y I’m writing it here. I would like to apologize to one of the readers who had mailed to me, for my inability to relate to her situation coz of my lack of understanding,...
Hirst Hall (German)Anmerkung des Autors: Dies ist die deutsche Fassung des englischen Originals von Hirst Hall. Hirst Hall hat mich von Anfang an so in seinen Bann gezogen, dass ich Surtea einfach um die Erlaubnis bitten musste, dieses meiner Meinung nach meisterlichen Werkes, in die deutsche Sprache ?bersetzen zu d?rfen. Leider sind meine Englischkenntnisse sehr bescheiden, so dass dies keine 100% ?bersetzung wird. Aber ich denke, zu 90% werde ich es hinbekommen, zumal Surtea die ?bersetzung v...
Sabina und ihr neues Leben (german)Kapitel 1: WutSabina ist eine gelangweilte Ehefrau, die seit sieben Jahren mit Sven verheiratet ist. Da ihr Mann als selbstst?ndiger Anlageberater sehr gut verdient, musste sie seit der Heirat nicht mehr arbeiten.Mit ihren 31 Jahren k?nnte Sie sehr gut aussehen, doch da Sie merkte, dass ihr Mann Wachs in ihren H?nden war, gab Sie sich keine M?he mehr. Ihr rotblondes Haar hatte sie sich aus Bequemlichkeit ziemlich kurz schneiden lassen, w?hrend ihre Fotze, die fr?he...
Horror-Urlaub im S?djemen (German)Sehr harte S&M- Short story: Tags: FemDev., slavery, non-consent, abuse, debauchery, pet-play, slaughtering, interracial breeding, canibalVon: ?2011 masostud, die Rechte verbleiben beim Autor.Vorwort: Der S?djemen, der sich vor seiner Wiedervereinigung mit dem eher westlich orientierten Nordjemen (gegen?ber von ?thiopien am Roten Meer gelegen) nach dem Abzug der ungeliebten Briten hochtrabend als ?Demokratische VOLKSrepublik Jemen? (gegen?ber von Somalia am Golf ...
Hi, I am back with another story about my ex-girlfriend being used by strangers blindfolded. The incident includes a beggar, rickshaw-puller, and a fruit hawker. As you have read before, we used to love kinky sex. Anything goes except a few things. We often speak about sex with strangers – someone we would meet just once, have fun and then leave without ever meeting them again. Once we were watching porn and there was a scene of a blindfolded wife used by 3 old men while the husband watched....
(An Incestuous Harem Story) Chapter Twelve: Daughter's Slutty Fun By mypenname3000 Copyright 2017 Note: Thanks to wrc264 for beta reading this! Leyla Umayyah Kimmy's braces flashed as she beamed at me. She lay atop her father, the nineteen-year-old girl practically glowing after having her virginity popped. My own pussy was so juicy from watching. I had such a delicious orgasm capturing the entire event on my camera phone. I set that on the nightstand as I headed to the bed, my...
Introduction: Meth + Wife + Friend = A Real Live Fuckfest CHAPTER 1 A little more than a week had passed since Id watched my wife Sara getting fucked to death by JRock, one of our tweaker friends, it was her first time fucking a black man, & my first time wife sharing – and we both loved it. J-Rock brought Mike to the apartment to introduce us, Mike was an MMA fighter, occasional enforcer/protection for higher ranking local Blood members, and, perhaps most importantly, he had been released...
Saturday, December 23rd. Lunchtime. It was lunchtime by the time Dave and Olivia left the bedroom, having completed the first half of their impromptu testing of whether a woman who had been dosed with SLuT9 would secrete Serotoxin, one of the two active ingredients of all the SLuT formulas, and, if so, would it cause a reaction in her partner. Both Dave and Olivia were relaxed, smiling, and freshly showered. They had already planned to do the second part of their testing where Dave would...
Introduction: a woman cant help her Orgasms when she feels a strangers cum A Strangers Cum 4 When we arrived home I headed for the shower intending to get rid of a load as Sues story had me erect all afternoon but before I even had a chance to soap it up Kathy joined me, I soon had her pinned to the wall as I fucked her hard and fast from behind and luckily she was as horny as me and we both came within minutes. Satisfied I dried off and headed out the back in the nude to do some yard work...
Being Naughty with 2 strangersBy Dina PetroThe resort was very huge, spread over a wide area with many activities and fields, I was all alone spending a couple of days, it was mid-afternoon of a hot summer day when I took my dress off, stayed with a two piece bikini, sun tanning next to a playground in the middle of a green area surrounded by many trees.Two men walked into that field, a black guy and a white guy, both in their early thirties, real good looking men, and seemed to be flirty, they...
I adore my wife, Sofia. She is a true British hot girl. Tall, long, fit legs, Has a round, firm arse made for slapping and squeezing and firm, natural breasts. She is pretty in a hot, sexy way. I see how other guys look at her and I know what they’re thinking. (I bet she’s a good fuck!) She oozes sex appeal. She is one hot girl but is modest with it. She doesn’t know it (or so I thought). We have a great sex life and we like to keep it fresh. Sexy lingerie, toys, porn and filthy talk. We share...
I adore my wife, Sofia. She is a true British hot girl. Tall, long, fit legs, Has a round, firm arse made for slapping and squeezing and firm, natural breasts. She is pretty in a hot, sexy way. I see how other guys look at her and I know what they’re thinking. (I bet she’s a good fuck!) She oozes sex appeal. She is one hot girl but is modest with it. She doesn’t know it (or so I thought). We have a great sex life and we like to keep it fresh. Sexy lingerie, toys, porn and filthy talk. We share...
Hi, this is part 2 from where I left before. That night after my top was removed, I was kissing my boyfriend like there is no tomorrow. Sitting on his lap, my legs were crossed around his hip. I myself decided that I should go with the flow, and have a group sex with the other 3 roommates. I was sitting topless, and they have seen me near naked. I want to know if my boyfriend can digest this. I slowly stood up and moved towards the room. I removed my shorts and I was full nude before them for...
After my last conquest, (see Flirting with Strangers (cuckold) ) My husband and I have now decided that it is far better, and kinkier, to find impromptu meets with strangers. Instead of knowing when, where, and with whom I am going to have kinky cuckold sex with via arranged meets. The excitement of not knowing, for both my husband and I of when it's going to happen is wonderful, each day I get braver and more comfortable in my new flirting hobby. Although suggesting sex with perfect strangers...
After my last conquest, (see Flirting with Strangers (cuckold) ) My husband and I have now decided that it is far better, and kinkier, to find impromptu meets with strangers. Instead of knowing when, where, and with whom I am going to have kinky cuckold sex with via arranged meets. The excitement of not knowing, for both my husband and I, of when it's going to happen is wonderful, each day I get braver and more comfortable in my new flirting hobby. Although suggesting sex with perfect strangers...
I forgot about my dvd and took the picture. It was inspiration for several orgasms. A long black haired wig hung down to his shoulders and a black leather corset was squeezing his body tightly. I only wished that the picture went down further so I could see his cock. Part of me wanted to tell him that I knew. At least then, we would both have someone to share this interest with. I figured I’d talk to him about sexual interests and fetishes, see where it led. “So…Joe. What kind...
I have enjoyed reading the stories written by men to get a better understanding of what it is like to crossdress. As a woman, I find that I really enjoy and am very aroused with a feminized man. I guess I have always been a bit of a tomboy and enjoy doing athletic things, so being with a man that is the opposite seems natural to me. I used to play gender swap cross dress role play with my ex boyfriend. It started one afternoon when he came back from playing basketball. I had just finished...
Walt and I headed out to the living room and as i sat down, Walt went into the kitchen and came back with two beers. As he sat down next to me he handed me a beer and for the next several minutes we sat there quietly drinking our beers. Walt finished his first and after he put his empty can aside he looked over at me. "You were fuckin' great" he said as he moved his hand over and laid it on my crotch. We were both still had on our outfits and as he now started to caress my crotch, I looked at...
Jack let himself in the front door. It had been a long day at the store. He’d noticed Ray’s Porsche in the garage. “Honey, I’m home.” From the kitchen came a sweet “Hi Janice how was your day.” “Pretty rough.” “Well just sit down on the couch and relax. I’ll have dinner ready in jiff.” They had divided up the house chores and Jack was glad that Ray had taken over the cooking. The meals were always delicious. Ray walked in...