Unexpected Outing Part 2 free porn video

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"Unexpected Outing" Part 2. Fiction by Johnny Cumlately John returns home dressed as a woman and tries to explain to his wife, Mary. "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! "I have researched your problem fairly fully. There are a lot of internet sites about cross dressing and several articles written from the woman's point of view. I've also learned a bit about masturbation and we'll deal with that problem first." Mary reached behind her chair and produced a small box. "This is a chastity device called a CB3000. I bought it some time ago in anticipation of this moment. It's not the very latest model but it will do for now. Go upstairs and put it on. There's a leaflet with some instructions. Then present yourself for inspection." John was somewhat taken aback at this turn of events. He had vaguely heard of such things but had never actually seen one before. It consisted of a sort of plastic cage for his penis held in place by a ring which went around the back of his scrotum, trapping his balls. He had some difficulty putting it on and needed to experiment with several rings and spacers until he found one that was only just big enough. He eventually succeeded. It felt very constricting. The leaflet had an illustration which showed a small padlock but the lock was not in the box. Back in the lounge, Mary told him to drop his pants. She examined the CB very carefully and tugged it to make sure it was secure. She then put the padlock into the ring and clicked it to. "Right. That should stop you playing with yourself and stop you getting fully erect so you won't be able to cum. I guess you'll find it frustrating but you'll soon get used to it. I want you to sleep in the spare room tonight so you won't be tossing and turning next to me. Oh, and by the way, I imagine you'll find peeing rather messy, so please get used to sitting like I do. Use plenty of paper and put a sanitary pad in your panties. "I'm going to do some more research on the computer and then think out our next move. I suggest you sit and read the Sunday papers. I'll see you at breakfast." John was left wondering what would be in store for him. "How long do I have to wear this thing?" "I will unlock you once a week for exactly half an hour so that you can keep it clean and relieve yourself if you need to. Then you will be locked up again." Mary went off to the computer and John tried to concentrate on the papers. He had always known that he would be caught out sooner or later but never imagined that it would happen like this. Nor the predicament in which he found himself, locked into a chastity device. Mary had not only found him out but had been fully prepared for this day.. He gave up trying to read and went up to the spare room bed. Whereas sleep had come very slowly the previous night due to his excitement at being dressed, tonight he was already frustrated at not being able to touch himself, let alone get an erection. He eventually dozed off but was woken by his usual nocturnal erection being stopped by the infernal CB. How would he cope if Mary kept him locked in it for weeks, maybe months on end? At breakfast next morning Mary asked him, "Did you sleep well?" "No. This thing you've locked on me is uncomfortable as well as frustrating." "Poor darling! I understand they take a bit of getting used to. After a month or so, it will have just become part of you." A month or so! John shuddered. When the coffee cups had been cleared away, Mary said, "We need to decide what we are going to do about you. First of all, I want to know what you get out of wearing women's clothes. Is it just a fetish to help you masturbate? Or does wearing them make you want to masturbate? Do you get a thrill just wearing them? Do you want to wear them permanently, become a "woman" and even have surgery?" "Wow! Those are leading questions. This weekend was the very first time that I have been fully dressed and the first time I have ever talked about it with sympathetic strangers, or been dressed while in their company. I just found the whole experience very liberating and enjoyable. I can't imagine being dressed permanently. And it is not just a fetish but I don't deny that it leads to wanting to masturbate occasionally. I would love to be able to dress for a day or so from time to time." "I guessed that would be your answer so I know what we are going to do. Most of what I have read leads me to believe that your urge to dress up in women's clothes is something that you are always likely to have and that it will resurface eventually even if we manage to suppress it for years. I also suspect, and you have just confirmed, that for you it is linked to the urge to masturbate. The CB will stop that. But I am going to allow you to dress up once a month. For two days, you will leave this house as a woman. You will not take a shred of male clothing and your CB will remain locked on. You will not contact me during that time. What you do and where you go will be up to you. I don't want to know. "I will help you collect a selection of suitable clothes. I may have a few at the shop, together will some foundation garments which should give you a more feminine figure and ensure there are no unsightly bulges. There are lots of other items you will need such as cosmetics. You will find it expensive and you have a lot of hard learning to do. "You will need tuition which I will arrange. I also want you to contact the girls you met at Mrs Appleby's. From what you've told me, I suspect they will be happy to assist. Do you have their phone number? If not, I'm sure Mrs Appleby will have it. You probably want to speak to her anyway to tell her how you've got on now you're home. "I must be off to the shop now. Please meet me there at 5 o'clock this afternoon when we close. We will have it to ourselves then. Bring all the clothes you wore yesterday and have a bath before you come so that you will be nice and clean to try things on.." Mary picked up her handbag and some things she needed for the day and left John somewhat bemused. He had a lot to think about but his main feeling was relief that his wife was being so co-operative. He phoned Betty. They had a good chat and she gave him the girls' number. Betty was fascinated to hear what was happening to him and he promised to keep in touch. At 5 prompt, John arrived at Mary's shop. He knew exactly what it sold as he had helped with stocktaking. Mary locked the door and put the "closed" sign in the window. "Now the first thing we need to do is to find some foundation garments to give you a more female figure. Then we can measure you for the right size clothes. I've picked out a couple of panty girdles and some bras. Come into the back room and strip off." The first was a white brief leg girdle with a fairly high waist. John pulled it on and was surprised how it held him in all the right places. It felt quite comfortable but the waist tended to roll down and there was a noticeable bulge over his CB. Mary explained that the other girdle was "extra control" and was usually sold to mature ladies trying to keep their figure. It was a white long leg, high waisted panty girdle with some discreet built in stays and a zip up one side from hip to top. John stepped into it cautiously. Mary told him to breath in while she did the zip up. It was very, very tight and held his CB closely to his crotch, although there was still a slight bulge. Mary got the tape and confirmed that it reduced his waist measurement by two inches. She told him to keep it on while she tried several bras using the breast forms which Betty Appleby had given him. Eventually she selected one and set about taking a full set of measurements. "Pity your hips aren't a bit wider. We should use some pads really. But that is not bad for a start. About a size 18 - we get lots worse in the shop! I'll go through finding some dresses and skirts some other time. For now, we'll keep the girdle and bra you have on. You can wear them home under your own clothes. You must get used to having your waist pulled in. I'll open an account for you because I'm not paying for your foibles. "I've also been looking at other sorts of chastity belts. I think we should order you a Neosteel SheMale belt. It will be expensive but it will hold your waist in with a nice flat front and, incidentally, it's virtually escape proof - not that you would try, would you?" Back home, John called the girls. "Hi! this is Gillian. Hope you enjoyed our walk as much as I did. I'm ringing because I need some help and my wife Mary wants to meet you. Could you both come over for coffee tomorrow night? You can! We'll look forward to seeing you." He went on to give the address and directions. Then they went on the internet and ordered a Neosteel measuring kit, more breast forms and some hip padding - all part of Mary's insistence on getting the profile correct. John had only vaguely heard about chastity belts before and had never seen pictures of the Neosteel which appeared awesome. The possibility of being locked in one for weeks or even months on end filled him with apprehension. However, at least the web site indicated a long wait for delivery - maybe Mary might had softened her plans by then? Mary told John that she had booked him a full day session the following week at a place in Manchester which offered services to transvestites and transgendered customers. Their staff would dress him from foundations to make up. It would be a chance to experiment and enjoy relaxing as a complete female. She intended to come with him so that she could also learn what he would need and see just how he could look if professionally dressed. That night Mary told John he could return to the marital bed. She refused to unlock his CB and produced a strap on dildo which she told him to put on - what else had she bought in anticipation of his eventual d?nouement? She snuggled up close to him and moved his hands between her legs while she teased his nipples. "Just because your cock is locked away, it doesn't mean I'm going to miss out. I want to feel that big new cock inside me." John climbed onto her in the missionary position they usually used and eased it into her. She was soon moaning loudly with pleasure, but, of course, John felt nothing but frustration as she turned over and was soon fast asleep. Next evening, he introduced Mary to the Girls and told them briefly what had happened when he got home - omitting the CB! Mary thanked them for their part in the events over the weekend. She said she wanted John to be happy and that she recognised that his kink about dressing would not go way. Perhaps they could give John - or perhaps she should call him Gillian to them - some useful tips on make up. Angie explained that, when she left school, she spent four years working in a beauty salon before deciding to go college and become a teacher. Later, over coffee, the three girls sat on the settee turning the pages of some clothes catalogues and trying to decide what would suit him. Mary asked them to come over again when Gillian had some clothes to try on. She said she was not going to let Gillian loose without very thorough preparation and training. After they had gone, Mary said, "I've a feeling those girls are lesbians. After all, they seem a very close couple and live together in the same house. Maybe that's why they were so keen to help at Mrs Appleby's? If I'm right, you'll be perfectly safe with them, CB or no CB!" By now, John began to realise just how much there really was to buy, to learn and practice, and that Mary had been right to call it hard work. To be continued..................... Fiction by Johnny Cumlately [email protected]

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Gary's Golf "Outing" Chapter 14 - Ladies' Favorite Activity I finished all of my work assignments and my home chores by Thursday. I had chatted with Kay a few times and was surprised when the phone rang on Thursday evening. "Hi Gabrielle, this is Kimberly. Are you all set for Saturday?" "Hi Kimberly, what's happening Saturday?" "Don't bull-shit me, you bastard. You know what's happening as well as I do and I'll bet you've been thinking about it all week." "I have...

3 years ago
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Garys Golf Outing Chapter 16 The Morning After

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...

3 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
2 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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