Crossdressing with Walt
- 2 years ago
- 38
- 0
I had been sitting reading when the phone rang and answering it, Walt was calling and telling me to put on a short blouse and skirt with my stocking and heels and to come down to his basement. I knew he had set up a small office with a sofa and a couple of tables and chairs so I figured he would want sex on the sofa and so I got dressed as ordered and off I went. As I entered the basement Walt was sitting behind his desk and drinking from a large wine glass. He motioned me over to the table to...
There was going to be a charity dance that I desperately wanted to attend, but found out that Joe wouldn't be home that weekend so I stopped by Walt's and Ruth's place and sat down to express my disappointment. After a couple of minutes Walt patted his leg and told me to come and sit on his lap. I moved over and sat down and as he put his arm around me I felt a slight tingle. We talked a bit more and he looked at me, "How can I make you feel better?" he asked. I looked at him, "A kiss would...
My name is Larry and I earn a living as a computer consultant. Most of my work consists of contracts with technology companies that last anywhere from three months to a year. Once in a while I'll do a favor for a friend and fix their home computer. One night while I was between contracts my phone rang and it was an old school buddy asking if I would help out some friends of his whose computer was completely hosed. The local computer shops were asking anywhere from one hundred to two hundred...
I had stopped by to drop off some papers to Walt when I found him sitting in the large lounge chair and Ruth over by the fireplace in her rocking chair. I climbed onto the arm rest of the chair next to Walt, put my arm around the back of his shoulders, gave him the papers which he briefly looked at, them and then tossed them onto the coffee table. It was a rather warm day and I had on a top with no bra underneath and a pair of shorts, no panties under them as well. I could see Walt was more...
I had stopped by and picked up Ron on my way over to Walt's and Ruth's place and as we drove over, Ron started getting a little frisky with me. He calmly reached over and cupped my one tit and started to squeeze it until I batted it away "What do you think you're doing?" I asked him. He looked at me and smiled, "I just wanna feel those gorgeous tits of yours" he replied "Not while I'm driving you won't" I answered back and he behaved himself until we got to Walt's place. Upon entering I saw...
PRELUDE It was 1961 and it was my second year stationed in Naples, Italy. My best friend Tom had also been there a year. He was my main stay as he had convinced me to spend my time and money touring the country and enjoying the culture. That was a far cry from so many other servicemen who spent all their time drinking and sleeping with working girls. Tom and I would also spend the night with a working girl when we were in the mood. We always went to this one bar where we had our favorites,...
During the summer months Tom and I liked to go to Capri on weekends. If we weren’t on leave or visiting other places like Pompeii, the Amalfi Coast and other point of interest, we would go to Capri. It was incredibly reasonable as long as you knew where to stay and where to eat. As soon as we had liberty call on Friday afternoon, we took a city bus downtown and then the ferry to Marina Grande. Once we arrived we took the incline up to Anacapri and made our way to the Hotel Roberts. It was a...
AUTHORS NOTE: Just a heads up that this chapter contains a bi-sex/gay sex encounter. Summer was coming to a close so Tom and I spent another weekend in Capri. We brought two of the working girls with us Pia and Petula. We stayed at the same hotel and the girls registered in one room and Tom and I in the other. Of course at night Tom went to be with Petula and Pia came to my room. We had a great time and great sex that weekend even though we spent more money than usual. Tom and I paid for...
After a long weekend of guard duty Tom and I had liberty on Monday and Wednesday nights but we opted to stay at the barracks to work out and then work on our gear. We had guard duty on Tuesday and Thursday but then the long weekend beginning Friday. Tom informed me that he was meeting Gianna on the Isle of Ischia and that she was already there. Ischia is the sister Isle to Capri although not as famous it is a fun place to visit. Gianna was trying to keep a low profile by going there instead of...
The college visit with not my niece. Pt2 I hope that you are reading this because you enjoyed part 1 of the story. Ellie and I met a few weeks ago and have shared a few fantasies. I decided to write them down and share them as stories. I do not have permission from her to share her identity, but trust me, she is real and damn.. she is hot! +++++++++ We went back to the hotel by 9:00, washed and changed into jeans and shirts and then hit a club near the hotel I enjoyed the sights of all of...
The headmaster pt2I am the Gardner/caretaker it may help to understand if you have read pt1.Victoria, the Head Girl is due any second at the Pavilion. I can see her crossing the rugby pitch in the moonless night. She has her short skirt swaying as she purposely strides my way. Her boobs bounce behind her crisp white shirt as she comes up the steps.We kiss and in doing so my hands grab her bum. Before our kiss parts I have manoeuvred her skirt up so that my palms cup her beautiful bum. The fact...
431 After the passing pt2He stared hard at the images, flipping the pages, checking each image carefully Ann of Hull, Sarah of Liverpool, and Tina of kings-Lynn all leered at him as he turned the readers wives pages. That took about two minutes as laughing he picked her easily, her face more youthful and smiling but recognisably her, he then looked at the clothed body, now beside him, markedly more robust, but to him still most attractive. She was flattered that he recognised her so easily. “Do...
416 A SUNDAY SHOP GIRL REMEMBERS (PT2)(See 196 Sunday shop girl 1)Sadly, this is a very true story. It was sent to me by a lass that is now, a nurse in north America, where she moved to too escape these folk as soon as she was able Anne-Marrie (as we know from part 1) had been coached from an innocent young virgin to a used young lady, still a virgin technically but no longer the innocent, unable though because of the trap she had fallen into to tell anyone and wrapped in the shame of the web...
410 Dave`s reassuring hand holding pt2They sat at the table she naked, he in PJ`s, coffee and a chip and egg meal, filling empty stomach`s, it was the Sunday evening and she had been sleeping all day after her overnight ordeal. He too had slept after masturbating a number of times watching the video and marvelling at her absorption of the pain she had endured. They were both wondering how to break the massive silence between them. In the end it was Gaye who spoke, “Well? Am I the biggest whore...
MUM 1 PT2Well it has been 4 week sence life changed with my mum Jean on her birthday when we first moved into an i****tual relationship and most evening mum and I would email or skype each other the on skpe it would normally be with mum and I naked watching each other get off she would always know just when to talk filthy at me telling to shot my load in her slutty whore cunt or start pissing for me to watch and telling me she can't wait till I visit again so she can suck my cock or have me...
Caught by Mom PT2Following on from Caught by Mom- Just Fucked the Most Popular Girl in SchoolSuzy wasn’t in school today. The day after we lost out virginities and being caught by Mom. Although Mom enjoyed having me as a ‘companion’ in her bed last night and despite receiving a very nice blowjob, I’m desperate to get my hands on Suzy again. No Suzy at School! After a very long day at school I reluctantly wander home. Could I have misread Suzy’s intensions? Has she lost interest in me? Dragging...
274 Visiting a Yorkshire lady. Pt2 They sat talking most of the afternoon, filling in the inevitable gaps while they had the time together reinforced by sandwiches and her home-made cake. She pealed spuds, and prepared vegetables, for the main meal of the day, as they sat surrounded by the smell of a steak and k**ney pudding in the oven. He fetched a bottle of wine from the car, a present for Sharon, and some beer for Mark and himself, while he was away Mary slipped away and returned in a...
But I'm married. PT2 I felt great on my walk home. It wasn't until I got to the front door of my house when I felt guilty.What have I done? I just fucked the masseuse and let a lady eat me out.Hi honey I'm home.Mmm that's nice.What an ass I thought.My massage went well.Mmm that's nice.With that all the guilt I felt quickly disappeared. When should I make my next appointment? Two weeks I thought. I too want my pussy to be on fire like the petite girl who bit me on my tit. I was sitting on the...
But I'm married. PT2 I felt great on my walk home. It wasn't until I got to the front door of my house when I felt guilty.What have I done? I just fucked the masseuse and let a lady eat me out.Hi honey I'm home.Mmm that's nice.What an ass I thought.My massage went well.Mmm that's nice.With that all the guilt I felt quickly disappeared. When should I make my next appointment? Two weeks I thought. I too want my pussy to be on fire like the petite girl who bit me on my tit. I was sitting on the...
.Rachel pt2Just after the summer of fun with Liz and Mark my father got transferred to the other side of the country which really pissed me off . So with heavy heart we packed up and left within a week. I was so depressed I really loved Mark and Liz and was going to miss them so much, for awhile I thought I might never have such fantastic sex again I will always remember Mark hammering my pussy from behind as I would eat out Liz's cunt it was perfect. It took almost three days to get to our new...
The boys in the group Pt2: The meeting...My first time was with my best friend, later known as my boyfriend named Mark. It happened by chance one day after scuool, back at his parents house and he told me to keep it a secret afterwards. Mark even made me promise not to tell any of the other boys in the group, afraid that they might over react so I didn't.We all started hanging out together as a group again during my last year in highh scuool. After a long while of Mark and me doing things in...
173 Visiting aunt Fiona. pt2We left Fiona bound of tits, and cuffed of wrist, laid on the carpet of the living room, Amy beside her had just returned from a multi climax induced faint and the two men were sat naked waiting Amy`s full return Phil just having had a BJ from the cuckolded Rob. The three were glad of the respite, Fiona though found the tender tits a trial, purple like balloons tied and bound, as they had been for near 30 long minutes now, they were causing her some discomforts, the...
New Neighbor Makes Me her Bitch Pt2 That was Saturday. Then came Sunday. Being dominated completely and being helpless for a 6’3” bull that has been a strength coach is a dream come true. If it is yours as well, Please read. I knocked on the door and she stood there looking at me with a mix of happiness and condescension on her face. She had on black yoga pants that hugged her muscular lower body. Her tanned abs were obvious below the sport bra that fought to control her large breasts. ...
Taking an XHamster Lover and Teaching Her Pt2 In part 1, I took my sexy nymph from the fancy restaurant where we met to the hotel where we enjoyed a very hot evening of sex!!! When I left off the story, we were just getting ready to shower and sit in the in room hot tub. This story picks up just a little while after the tub. I am relaxing she is drying her hair. Can you hear the hair dryer? [/Image]~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Sitting in my chair I smiled as I swirled the...
Charlie had positioned himself behind me and was rubbing his huge penis glans over my bung hole. I whimpered as his huge member probed my outer anal muscle ring till it parted and admitted his head to enter my neither region. I begged 'please, don't do me like this, please don't,' Charlie growled 'bitch, you just swallowed my cousins seed, I'm gonna breed this ass pussy, you ain't sucking me dry till I seed your ass.' Charlie pulled his penis back and slid more into me, I gripped the mattress...
The roommates pt2When we arrived every light in the house was out. We figured that 2am was a little late for poor Mark and Josh. Mark snoring like a lumberjack and Josh playing soft music and burning inscents burning.Smiling we entered our bedroom and closed the door. The next morning Dash and I had ALOT to tell Mark and Josh, but wehesitated to tell them until we got a feel for what our to new roommates were into, we decided to start doing little things to gauge how comfortable they were with...
I looked at Claude's crotch and saw that he was stroking a monster of a penis, Joseph grabbed my feet and Brad held my hands. Claude crawled over my butt and bust my sloppy bung hole wide open with his enormous penis. I cried out all to no avail, Claude grunted and slammed his penis up in my butt without mercy for all of 20 minutes. With a growl deep from with in, Claude erupted a flood of semen that flushed out from around the massive shaft that filled my anus. With each throb of his penis...
After Bra had left, I filled the tub with warm water and slid down into it. My butt hole was swollen and painful to the touch, the tissue had traces of blood. After I had bath, I dried off and went into my folks room to find something to soothe my aching bung hole. I found some petroleum jelly and smeared a generous amount in and around my tender puckering bung hole. A glance in the mirror told me that it was a bright reddish color and hurt like hell. It was late Wednesday as my folks and I...
For a ... For a recap of the story so far read Curious pt1, and yes I know I have bad punctuation and grammar CURIOUS PT2 By Dake9872 8:05! The clock radio read. There we go! After pinching myself and slapping myself for five minutes it looked like I wasn't dreaming. I really was Brooke Morgan; I felt exactly what beautiful women felt like to touch, from the long hair and killer figure, to the boobs and clit. Hopefully Brooke wasn't me. I mean going to bed Esmeralda and waking...
Trying to Scratch that Itch PT2 Thanks for all the reviews and some of the ideas! Please read the first installment because this is an ongoing story. Please enjoy Tabitha's adventures. "Don't take any longer than an hour you slut!" as she pokes her head out of the shower and gives me a wink. I blow her a kiss and close the door. I grab my purse and I wiggle out that door. I put my purse in the crook of my arm and have my elbow down and my wrist up and bent forward and my other...
Hii, mere naam ankit hai. Main mumbai ka rahnewala hoo. Yeh kahani meri or meri mami ki hai jab hum sath me crossdressing kiya karte hai. Meri mami ma naam sabita hai. Unki lambai 5ft or woh thodi moti type ki hai. Unka koi baby nhi. Lekin fashion ke mamlo me save age rahti hai. Jab mai 10std me padta tha tab meri mami or mama culcutta se mumbai aaye. Yaha aane ki unki ek hee wajah thi paisa. Mujhe pahle se hee porn video dekhna achcha lagta tha. Mujhe femdom, bdsm, bondage jaisi porn bahut...
The next morning after the poker game Walt reminded me that I was to visit all three of his poker pals this day and make sure that I did whatever they wanted. I agreed and he had me pack two separate bags with the other outfits I would be wearing along with what I had on at that time. My first visit was to be with Jeff, the one that I thought would be the nicest to me. I drove to his house and went up to his door when I got there, rang the bell and Jeff opened up. "I'm here to be yours for this...
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...
CrossdressingI 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...
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...
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 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...
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...
TranssexualI 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 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...