Unexpected Outing Part 1 free porn video

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"Unexpected Outing" Part 1. John returns home in female clothes following an accident. Fiction by Johnny Cumlately. John's earliest recollection of cross dressing when he was about 12. He would surreptitiously "borrow" his mother's underwear. She was even then years behind the times and wore pink satin knickers with elastic at waist and thighs. She also wore corsets with miles of lacing. John, now 35, had been happily married to Mary for about ten years. They lived in a pleasant suburban part of York, an old city in the North of England. John was an IT Consultant and mostly worked from home. Mary owned a lady's outfitters shop. Both regretted that they had been unable to start a family. His earlier wish to cross dress had persisted and he regularly "borrowed" his wife's clothes - panties, bras (which he stuffed with socks), tights and skirts - whenever she was out for a few hours, which was most days while she ran the shop. He also had a small collection of lingerie of his own. One of his hobbies was hill walking, a pursuit which Mary did not share but she happily agreed to him being away for an occasional weekend of healthy exercise. She would usually go to visit her sister. On this occasion in late autumn he arranged to drive to the foot of the moors, leave his car in the care of a local farmer and walk about 10 miles to a remote hamlet where there was a small "bed and breakfast" to which he had been recommended. It was run by a Mrs Appleby. As usual, John travelled light, carrying only a waterproof anorak and a toothbrush in his rucksack. Also as usual, he wore a pair of frilly panties under his jeans. The weather forecast had been good but by midday dark clouds appeared on the horizon and at two o'clock, the heavens opened and the rain fell in stair rods. John was accustomed to coping with wet conditions but found the short grass grazed by generations of sheep to be extremely slippery. The area was criss-crossed by several deep ravines and as he climbed down to cross a stream he missed his footing. He rolled down the hillside for about thirty feet until his fall was broken by some bushes which caught his clothing and tore his jeans. He nevertheless fell into the swollen stream and finished up to his chest in icy cold water. Although winded and shaken, he managed to climb out and survey the damage. He was bruised but did not seem to have broken any bones. One leg of his jeans had been torn almost from top to bottom, his boots had filled with water and all his clothes were wet through. He was cold and started to shiver. Fortunately, he was less than a mile from his destination and knew that he must press on as quickly as possible. His knock on the door of the B&B was quickly answered. "Oh my goodness! Whatever has happened to you? Come on in and get warm by the fire." Mrs Appleby did not wait for an explanation but showed him into the sitting room where a bright fire burned in the fireplace. She was a widow in her late fifties, amply proportioned but she had a shapely figure and an attractive face. She was dressed in a rather dowdy frock with a small floral pattern. "You stay there for a moment while I go and fill a bath for you. There's plenty of hot water." She went up stairs and returned a few moments later. "I'll show you your room. I've put out a couple of towels. Just strip off and I'll find you some dry clothes. Leave your wet ones on the floor." John enjoyed a good soak in the bath and got out feeling much happier. He wrapped one the towels around him and crossed the landing to his room. All his wet things had disappeared and on the bed was a neat pile of dry clothes. He was surprised to find that they consisted of a three-quarter length denim skirt, a pair of plain cotton white panties, and floral tee shirt, a blue cardigan and a pair of mule bedroom slippers with a pink bow. Having no choice, he put them on and sneaked a quick approving look in the mirror before going down to the sitting room. "Good! You'll be fine now. Sorry I haven't got any men's stuff. I got rid of all my husband's clothes after he died five years ago. The panties are a bit plain, but I guess that you'll be happy in view of what you had on." John blushed. He had forgotten that his frills were among the wet things he had taken off. "Your jeans are way beyond repair and I've put them out to burn with the rubbish." John sat down in an easy chair by the fire, smoothing the skirt over his knees. There was a knock on the door and Mrs Appleby hurried to answer it. He heard girl's voices and a moment later two girls were shown into the room. Both looked to be about thirty. Mrs Appleby introduced them. Wendy was slim with straight blond hair. John's interest in female clothing suggested about size 12. Her friend Angie was a brunette with a rather fuller figure, maybe size 16. They were obviously walkers dressed in sensible warm clothes - jeans, walking boots, and heavy anoraks. Before they had time to take in his appearance, Mrs Appleby managed to anticipate John's embarrassment. "John had a fall on the fells and finished up like a drowned rat so I've lent him some dry clothes. You two go and get your walking stuff off and come and join us. Then I'll make the tea." The tea was a typical Yorkshire High Tea - cold ham, pickles and salad with bread and butter, followed by trifle and cakes, all helped down with a large mug of hot tea. While they were eating, John learned that the girls also came from York where they shared a small rented house and both taught in the same primary school. They did a lot of walking and had visited Mrs Appleby several times before. They addressed her by her Christian name, Betty. It was soon arranged that the girls would walk with John to his car the next day and he would then give them a lift home. Tea had been cleared away and the girls had helped wash the dishes. They were all back in the sitting room when Betty looked at John "You know, many guys would be embarrassed to be dressed in those clothes sitting here with three girls." Turning to Wendy she said "He seems very comfortable with them, doesn't he?" "From what I've heard, a lot of blokes like to dress up sometimes. It releases their softer side." "My late husband did and I used to encourage him. We had lovely girlie evenings here by the fireside." Angie had been looking closely at John. "Pity he has such a flat chest. He'd look much better with boobs and more hair." "Actually, although I threw out all my hubby's male clothes, I couldn't resist keeping some of his dressing up kit. I'll go and get it." John really was getting embarrassed by now as he started to guess what might follow. Betty returned with a bag full of stuff. "Come on John, I know you'd love to look convincingly female and we would love to help you." Betty pulled a bra and a pair of very realistic breast forms from the bag. "Just take that cardigan and tee shirt off for a moment." Reluctantly, John stood up and Betty helped him take them off. She manoeuvred his arms into the bra and did up the hooks at the back, then put the forms into the cups. She spent a few moments adjusting the straps. "Those are size 42C. Now put the tee shirt on again and go and look in the mirror in the hall." He had worn one of Mary's bras stuffed with socks but this as so much better. It just felt absolutely right and he returned to the sitting room to note Angie and Wendy's obvious approval and saw Betty pulling a wig from the bag. It had fair wavy shoulder length hair and was soon being attached to his real hair with a couple of hairpins. "Angie, it's your turn. You use your makeup on him and he'll soon be one of us!" She used plenty of foundation to cover the 5 o'clock shadow but was very sparing with the rest of the make up. John was amazed how little lip stick was needed. And so it was that John was fully "dressed" for the very first time. "All he needs now is a girl's name - how about Gillian?" The four girls spent the rest of the evening enjoying girlie small talk in which Gillian became a happy participant. Eventually, the girls said it was time for bed. Wendy said "We're looking forward to our walk tomorrow. We want to go with Gillian, not some odd guy in a skirt. You'll be safe with us. If we meet anyone, they won't look twice at three girls together. And we won't be dressed for a fashion parade with hiking boots! Good Night!" After they had gone up, John turned to Betty and said, simply, "Thank you". "When I saw those nice panties of yours, I guessed you might enjoy wearing some of my old things. And I really didn't have any jeans to lend you. I was surprised how quickly the girls took the hint and joined in the fun. You're welcome to keep those clothes. Sleep well!" "Thank you very much indeed. My little collection is only panties. It will be nice to own some real clothes. Good Night, Betty." Up in his room, John took off the skirt and tee shirt but decided to leave the pants and bra on. He kept feeling his new bust and soon succumbed to the temptation to masturbate. He then slept fitfully. In the morning he washed and dressed again in the skirt. His wig was a bit tousled and when he got down to breakfast, the girls insisted on redoing his makeup and tidying his hair. He thanked Betty again and the three girls had an uneventful walk back. to his car. He really enjoyed their company and his first day out en femme. He took them to their home in York. When he arrived home, he was surprised to see Mary's car in the drive. He had assumed that she would not yet have got back from seeing her sister. However, he had no choice but to go in, hoping that Mary might be busy in the kitchen and that he could go upstairs unobserved. It was not to be and she met him at the door. She took one look at him. "Who are you pretending to be? What have you been doing while you were away? So you've decided to come out of the closet. Go and take those clothes off, have a shower and come down dressed as my husband. You can tell me all about it then." John realised that he had finally got to come clean. But his unexpected outing as a cross dresser had not been remotely the way he had imagined. John did as he was told and came down to the lounge to find Mary sitting waiting with a tray of tea and cakes. She waited until she had poured two cups and cut him a piece off a sponge cake before either of them spoke. "Now, tell me exactly what you've been up to." He gave her a full account of his fall and how Mrs Appleby had provided the clothes. And how she and the girls had decided to dress him up completely and called him Gillian. The only thing he left out was that he had been wearing his own panties. Mary listened without interruption. "Well, I suppose that's your story. I'm not sure I really believe it but I'm not really surprised. I've known about your dressing up for years. You thought you had been very careful to put my things back as you found them, but once I had my suspicions, I could tell every time. I even found your small cache of lingerie. And I know you have been masturbating frequently - there have been tell tale marks on your clothing. Anyway, at last its out in the open and I can decide what we will do about it!" To be continued..................... Fiction by Johnny Cumlately [email protected] August 2008.

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Gary's Golf Outing -- Chapter 16 The Morning After I woke up the next morning in a cold sweat, a hot, cramped hand, a warm sticky substance in my mouth and a pole gagging me. I was afraid to open my eyes, but an expert cock sucker was sucking my cock and I had to see what was happening. The cold sweat turned out to be a pool of warm semen that had drooled from my mouth during the night and turned cold. The warm sticky substance was fresh cum from the pole that was trying to enter...

2 years ago
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Garys Golf Outing Chapter 18 Home Cumming

Gary's Golf "Outing" Chapter 18- Home Cumming "Shhhh," Kay said to Penny as she unlocked the door to her condo. "We don't want to wake Gary. He'll want to join us in bed. I want you all to myself tonight. Gary can wait until tomorrow night." She locked the door behind them and lit a night light in the living room. They tip-toed past the guest bedroom to the master bedroom. "Shhh," Kay whispered again and carefully peeked in. The room was empty. "He's not here," she whispered again....

4 years ago
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Garys Golf Outing Chapter 19 Shoppinh Shenanigans

Gary's Golf Outing Chapter 19 Kay Cums Home, Shopping Shenanigans Kay's home-cumming was a great start to a great week. Every evening was a variation on the theme that began early Saturday morning, and ended Saturday evening, with Kay sandwiched between me and Penny with me in front with my prick in Kay's pussy and Penny behind with her six inch clitoris in Kay's rosebud. Sunday's bedtime arrangement had Penny sandwiched between Kay, with Penny's clit in Kay's pussy and my 6...

4 years ago
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Garys Golf Outing Chapter 20 House Guest

Gary's Golf Outing Chapter 20 - House Guest "Are you ready for your ass-fucking, my love?" Kay asked when I opened my eyes. "Just as soon as I use the facilities," I responded. "Let me join you," she said. "I want to give myself an enema and I'll give you one, too." I wasn't keen on enemas but, at this point, I was ready to do anything Kay wanted me to do. I never thought I'd say it, but the enema was extremely erotic. Maybe it was because it preceded my first morning...

3 years ago
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Garys Golf Outing Chapter 21 A Good Time Was Had By All

Gary's Golf Outing Chapter 21 - A Good Time Was Had By All I poked Kay's pretty pussy with my prick to wake her up. "What." She said groggily. I said, "I'm ready for my morning fuck." "What time is it?" she asked. "It's 7:15. What difference does it make?" "You have to be at the golf course by 8:30. We won't have time for your morning fuck." "Oh shit. I forgot all about golf. With my prick in your ass all night I couldn't think of anything else except getting your big...

4 years ago
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Garys Golf Outing Chapter 23 Party PreparationsGarys

Gary's Golf Outing - Chapter 23 - Party Preparations Somehow, Kay and Gabrielle left Betty's Boutique unobserved, Gabrielle in her red French maid uniform, red stockings and strappy red high heeled sandals, and Kay in the sexy black bra with her bright red lipstick painted nipples protruding through holes, a black garter belt and panties and black four inch high patent leather pumps. When Kay and Gabrielle got into the car, Kay said, "Can you drive with those shoes on or do you...

3 years ago
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Garys Golf Outing Chapter 24 Brads Big Birthday Bash

Gary's Golf Outing Chapter 24 - Brad's Big Birthday Bash Gabrielle woke up early Saturday morning with morning wood, even though she had spilled a copious amount of cum the night before when Kay fucked her with her squirting dildo. I guess sleeping between two gorgeous girls all night could contribute to that condition. Kay had fucked Heather the night before, too, but, of course, Heather had no visible signs of arousal. "Would you like me to take care of that for you, Honey?" Kay...

3 years ago
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Before Outing Smooth And Rough Sex

Hi All, this will be my first post however not the last depending on the responses I receive from you the readers of our favorite site :). Call me Sandy, physical look wise not a six pack carved body but having a little bulge in the middle with a frame of 5 feet 9.5 inches. Typical Mumbaite with easy going nature working in a MNC as a manager. The incident am gonna narrate took place when I was in Chennai. I was posted there to help set up the new location and new process. Was sent there for...

3 years ago
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A Difficult Outing

A DIFFICULT OUTING By, Salty Lady I was walking down the road in a black, flower print dress. My heals clicked on the pavement. The street lights showing my destroyed makeup. To myself I say. "But I do know what I need to do." THREE DAYS BEFORE Not a good sign when you are talking to yourself, but I was as I walked back to my dorm. "Twenty-four years old and I'm living in a fucking dorm full of eighteen-year-olds. I'm an average guy. I'm average height and average build, with...

3 years ago
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The AtonementChapter 4 The Outing

Barbara stood staring at the outfit she had purchased for today's shopping trip with Cheryl. The black leather mini-skirt looked like it belonged on a 12 year-old, not a woman her age who was the mother of two. When she tried it on at the store, she had to buy a smaller size just to get the effect of 'barely covering your ass' that Cheryl had directed her to buy. It did barely cover her ass. If she were to bend over or reach for anything, the skirt rode up and exposed everything worth...

3 years ago
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Unexpected Restroom Lust 8211 Part 2 8211 The Fuck Part

Hi this is Arjun again for ISS. This is my second story for ISS. To get to know a little about myself and to know what happened before this story PLS check out the previous story “Unexpected Restroom lust”. The previous story had a few spelling mistakes and I think this will too :P. Pls bear with me. This story is a continuation of my first sexperience with my college mate JananiPriya, that too in our college restroom. Weird place to have sex isn’t it. So, with no time to waste; ill start the...

4 years ago
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Unexpected Fun After A Ball Party

Hi, this is my first story at ISS. I have been a regular reader of sex stories over here and at last thought to pen down my real experiences. This is my first experience which I am writing here. I am not a descriptive writer so Please forgive me for my mistakes. Fair comments will encourage me to further share my other experiences in a better way. You can send your feedback on my mail address at I m raj at present 32 years of age, highly educated,well mannered, suave and articulate . I stand...

4 years ago
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Unexpected Sexperience With Unexpected Woman

Hello dear readers… Hope you are ready to be aroused by my new unexpected yet wonderful experience. Not delaying any more… here I start my experience :) I am a male bdw ;) and I am staying with my friends in a house. As many guys have that anxiety about woman and their hidden treasures, I was also curious about them and always wanted to have some fun with woman but never got a chance. So… why am I writing this post? It’s because every one is given a fair chance, I also got mine and that too in...

2 years ago
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A jolly girls outing

I get a call from Lisa“What have you got planned this Saturday”“Nothing really, was going to my mums, but apart from that nothing special…Why?” I asked“I have an idea, I think you will like….are you up for it then”Thinking about our previous encounters I was getting slightly damp in the crotch as she spoke“Yes…Alright then…what time” Lisa paused while she sounded like she was looking through something“About 8am…Is that good”I thought about what she might have planned“Yes…that’s great…are you...

2 years ago
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I am Me an Outing

"I am Me!" "A Night Out" By Anna Feie What can I say, I am Me! That's right, I am an older gal of indeterminate age. I have always felt that I am special - not better than someone else, but special in self. I had a normal childhood, grew up running wild. I spent the school years being a invisible student and the summers working outdoors for my parents or playing in the hundreds of acres of forest, waters, hills and dales surrounding my home. Events took a hand in my rearing. ...

2 years ago
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Unexpected Visitor3

Chapter 1 It was after ten o'clock on a gloomy January night. There was a cold rain falling, and it was being driven by a stiff wind. It was a good night to stay in. I was sitting in front of my computer about to finish my data entry assignments for the night. I thought I would read a porn story or two after that. The only light I had on in the house was the one on my desk. Suddenly, I was startled by a knock on my door. Being naturally suspicious of such unexpected visitors at...

3 years ago
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Unexpected Kinky Birthday Party

Hello readers. Handshake to boys and boobs shake to girls. The story is a half-fiction and half-real, written for kinky and hardcore sex lovers. Relax and hands inside underwear now! I’m a 25 year old Software professional leading a healthy (I mean boring) life. I never had a girlfriend and led a lonely life nearly entire life. Although family life was nice, that desire to have a girlfriend was always there. Many might disagree but I feel a guy needs a girlfriend or at least a close friend who...

1 year ago
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Unexpected Titty

Reddit Unexpected Titty, aka r/UnexpectedTitty! Sometimes, we are lucky enough to be present during something unexpectedly hot, and that is basically what r/unexpectedtitty/ is all about. I think the name of the subreddit pretty much says it all, and you can expect a lot of unexpected titties or so to speak. With just a bit browsing, I am sure that you will get the gist of what r/unexpectedtitty/ is all about.Now, keep in mind that Reddit.com is a free website, and there are loads of NSFW...

Reddit NSFW List
2 years ago
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Unexpected Desire

To understand how totally unexpected the event of several months ago was, knowing my history, well my sexual history, is helpful. I am a twenty-four year old lesbian. Well, at least I was a lesbian, but now I'm probably bi. The change in sexual orientation is what this story is about. I learned I was attracted to girls when I first turned sixteen and began exploring the secret world of sex in high school. Earlier, I didn't think much about the subject, and it wasn't a topic at home. Some of...

Lesbian
3 years ago
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Unexpected Night With My Best Friend

Hey this is Dhruv. This is my first sex experience which I want to share with u guys. This experience and situation was completely unexpected. Its with my best friend Tina. Tina and me are best friends from childhood.. but one unexpected night got us together physically too.. Coming to info about me I am a boy age 21, and I am studying.. and good looking. My best friend Tina is my childhood friend. Both of us played together, shared everything..but never had such feelings of getting physical....

4 years ago
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Unexpected Sex Experience With Lustful Neighbor

Hi friends… Gary from Calcutta. Thanks to ISS for publishing all my previous stories and the wonderful responses from the readers. I have been blessed amazingly in matters of love and sex, especially in last 3 years after coming to Calcutta. For those who are reading my escapade for the first time, I am a 34 year old guy with lots of sex drive. I love to keep myself fit by regularly gymming, and various sports. And being a part of a high end residential society, get many chances to interact...

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