SALLY'S RELUCTANT CROSSDRESSER free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)

CHAPTER ONE

       

       Sally and Dave had been dating since high school, it was a turbulent relationship, and at this moment in time they were having a few arguments, Sally called them dicusions. They were both nineteen and in love with each other, and both were jealous and possessive of each other. Sally was the one with the ideas, and Dave let things fall into place as he could never emulate her suggestions. They were sitting in the lounge of the flat they rented, they were not married but in a good relationship. They were both the same height at about five feet ten, both slim and Sally’s curves were something to behold, and very pleasant to the eyes. ?Don’t forget Sally, I have to go to my mother’s this afternoon, I cannot get in my clothes cupboard, the keys are in my other jacket, and that was left around there yesterday. Why did the builders put locks on wardrobes I have no idea, they must have had a warped sense of humour??

?We can go there after we have been to the shops, but I have to get some new shoes first.?

They had been walking around town for a while when one of Dave’s mates met them in the high street. They were chatting for a while leaving Sally out of the conversation, ?Come on Dave it looks like rain and we don’t want to get caught up in the downfall.?

       Dave’s friend looked at him and asked, ?Do you always do as she says??

       Dave went red in the face and answered ?No of course not, just wait for a moment Sally until I have finished talking.? These were the wrong words to say to her, and when Dave glanced at her out of the corner of his eye, her look said it all. His face went red once more, and he said quickly, ?Damn, I have just thought I have to collect a key, Sally is right and we must go.? He knew though that the damage had been done, and the last time he had upset her, it was as if, Pandora’s Box had been opened, and her face was looking like the Devil had possessed her. Dave was not frightened of Sally, but he was frightened of her temper, and she was very domineering when she wanted to be. He also knew that he would be held to ransom now, and there would be damn all he could do about it, he was also in no doubt that this time it was a big mistake, and his penance would be high.

       It could only get better or so he thought, and he went to put his arm around her back, but she pulled away, at the same time giving him a cold look. ?Don’t for one second think you can get round me like that, you humiliated me, treated me like a second class person. You big head, just like you, doing all that your mates tell you, what’s up did I eat into your ego? Well after I have finished with you, there will be no ego to damage, so you had better prepare for the worst because it is going to happen.?

Rather nervously Dave asked, ?What do you have in mind lover??

?Don’t you call me lover, you have just lost that right, and I am not sure what I will do to you, but it won’t be very nice I can assure you of that.?

They walked around to his mother’s house, but it was only to be told that she had gone away for the weekend, and there would be no one there until Monday. ?Now I will have to stay in these clothes all weekend, what a flipping mess.? It was just then that there was a crash of thunder and the sky’s opened up, within two minutes he was like a drowned rat, and so too was Sally.

?You see if you had walked on like I said big head, this would never have happened. Well it serves you right, and this is another thing that I will punish you for when we get home. I’m drowned, because you wanted to be the macho man, but I have just thought of something very funny that has cheered me up.?

?What’s cheered you up Sally, you’re drowned and so am I, so tell me and cheer me up??

?No, you’ll have to wait and find out.? She laughed as she walked just in front of him, and he followed behind with misgivings.

It had taken just over an hour to walk from the west end of London to the house, and they were both saturated. Sally ran to the bedroom and Dave walked to the toilet, five minutes later she was sitting in the lounge smiling. She watched as Dave walked out of the toilet and bathroom naked, and there was now a bigger smile across her face. She heard him shout out, ?Bloody hell, I’ve got no clothes to wear, now what the hell am I going to do??

Sally smiled once more and then shouted, ?What’s up Dave is there something wrong??

?What’s up Dave is there something wrong,? he mimicked ?Of course there is something wrong, I will have to walk around naked for the rest of the evening, because I can’t get into my wardrobe.?

Sally was sitting on the couch laughing and she said through her tears, ?Oh good.?

?What did you say, I couldn’t quite hear you??

Still laughing she answered ?I said oh dear what a pity.?

Dave walked out of the bedroom covering his genitals with both of his hands, ?What the hell is so funny, for god’s sake help me out.?

She stood up still laughing, ?You had better come into the bedroom and I will see what I can do.? Dave followed her, as there was nothing more that he could do. Once inside she went to her wardrobe, and pulled out a dress and walked over to him. His eyes now were like pigeon eggs, and he backed off, but she pressed it against his body saying, ?Yes flowers really suit you Dave.?

?I’m not putting that dress on, and that is all there is to it.?

?Shut up! You will do as I say you asshole, you humiliated me, and now it is my turn to do it to you. Put the dress on or you can kiss me goodbye, because you owe me big time.? She threw the dress at him and went back to her wardrobe, when she walked back she handed him a pair of yellow briefs. ?You had better put those on as well, because I don’t want to look at your prick all night.?

?Please Sally, haven’t you got any jeans??

?Yes but they won’t fit you, now get a move on I want to see how you look, I’ll bet you will look very sexy,? and she once again laughed. She watched as Dave reluctantly put the clothes on, and as he put the briefs on she could see the bulge in the front. Once he had completed the task, pure devilment made her walk over and put her arms around him, then pulling him tight she rubbed her body against his crutch. Sally could feel his hardness through her own clothes, and as she pushed him away, again she laughed. ?I think you like wearing my clothes Dave, because that is one hell of a reaction to wearing my knickers. Do you like wearing my knickers Dave,? and as she spoke softly to him she was giving him a little smile.

?No I don’t, how could you ask such a silly question, I’m a man and men don’t dress like this.? Sally could see that his face was now bright red, and she couldn’t help smiling more, well to be truthful it was a grin. My clothes will have to be washed and dried, I will have to use some of that money we won to buy new clothes, and it’s a damn good job I get an allowance from my father. I suppose the only lucky thing is, that tomorrow is Saturday and the shops will be still open.?

             They were a very lucky couple, in the fact that neither had to work, Dave’s

Parents were middle class with money of their own, but they had split up when he was ten years old. His father gave him a large allowance every week, but his mother thought his father was a cheapskate and gave him more. Sally had been given an inheritance, and received dividends from shares that had come with the inheritance. Sally looked at Dave and said ?You had better go and dry your hair or you will catch your death from cold.? As Dave turned to walk back to the bathroom, Sally couldn’t help herself, she patted his buttocks and said, ?Mnnn, nice ass love,? and laughed when she saw his face go a scarlet in colour.

It was twenty minutes later when he walked back out, the hair dryer had fluffed up his hair as it always did. Dave’s hair was blonde, and when washed and shiny, it had that same sparkly tint; his hair was also long and come below his neckline. As he sat next to her on the couch, Sally looked at him and smiled. Dave felt her eyes, and turned to look at her, and in a questioning voice asked ?What??

?Nothing lover,? Sally answered.

?By calling me lover, does that mean you have forgiven me Sally??

?God forbid no, I said that because you are, but your punishment has not started yet, as I still have to find the correct solution.?

       ?Err umm, is this punishment going to be hard Sally??

       ?Of course it is silly, that is what punishment is all about, it might be hard or it might be difficult, but it will be humiliating. It has to be, to compensate me for your indiscretion, and insult to my femininity. Your disgusting behaviour this afternoon, where you publicly displayed your chauvinist ways has to be dealt with before we can move on.?

       ?Listen to you, you never by any chance swallowed a dictionary while in town today, you’re beginning to sound like my mother, and she’s a local councillor. What do you mean by humiliating, are we talking about public or private??

?We are not talking about anything, it is me that is talking about it, and you will know what it is all about when I am ready to tell you. I do think however, that there should be some sort of public humiliation, after all that big mouthed mate of yours will have spread it around, that you chastised me in public.?

?I never touched you Sally.?

?I’m talking about verbal chastisement, sometimes I wonder if you were in the same class as me at school. I was just wondering how you were going to walk down the chip shop like that?? She smiled as she watched his jaw drop, ?Well I suppose that is asking a lot, so I had better do it, but that is something else you will be punished for, not doing your weekly chores.?

?How can you punish me for that, I can’t go out dressed like this, and it is not my fault that I haven’t any clothes to wear.?

?You really are adding to your punishment by the minute, every time you open your mouth you drop yourself in it. Now you are lying to me. Of course it’s your fault, because if the keys to the wardrobe were in your pocket, and not around your mothers, then I am sure that you would be dressed differently. By the way that you have taken to dressing in my clothes like a duck to water, and no pun intended, I get the feeling that you are a secret cross dresser,? and once again she laughed at his red face. ?I think I am going to have so much fun with you from now on, and just to make sure you toe the line, I might even draw up a contract of do’s and don’ts.?

It was some hours later and they had both been watching a film on TV; Dave stood up and stretched himself after yawning. ?How come it took you so long to get the fish and chips??

?I was talking to the girl in the hardware store, I knew her from school.?

?What were you doing in there??

?Getting some shopping and it was things I might need later, I need things to experiment.?

?Well I’m going to bed are you coming Sally??

?Yes because we are going to play a little game, but I’m not sure that you are going to like it or not, but it doesn’t matter anyhow.?

Inside the bedroom Dave stripped off the dress and was just about to push the briefs to the floor. ?Stop, that’s far enough, I would like you to leave my knickers on, and lay on the bed Dave.?

?You’re joking right?? he asked her.

?Do I look as though I am joking, just do as I say, remember you owe me big time, you have a long way to go before you are forgiven.? She stepped back and watched as he did as she instructed, and he was now in the middle of the bed. ?Now put your arms out to the corner of the bed, and I dare you to move them until I say so.? Once again Dave did as instructed, he knew that to argue would be useless, and it would mean that he was in trouble for a lot longer. He watched as she walked to the edge of the bed, and she repeated what she had said about moving, and straddled his chest with her legs. Then without warning she leaned forward left and right, and slipped his wrists into cord with a slip knot attached, and removed her body from his chest. ?Can you move your hands Dave?? She watched as he tried to pull them down, and the immediate look of shock.

?I can’t move, what the hell are you playing at Sally??

?As you can see I’m not playing at anything, this is all very serious, and now I am going to lay out the rules. First though I have to check something out, I was wondering if I ought to bring Jill over here to have a look at the way you are dressed.? She looked at the shock on his face and then he started to wriggle, now stop doing that, it was a question and not a fact. But looking at the lump in my knickers, I think that you were relishing the thought of being seen in female attire. Now I am going to put some more clothes on you, but if you kick and struggle I will go and get Jill, she is in tonight and only two doors away.?

?Let me go Sally please, I will do all you ask without all this nonsense.?

?Now you know lover that I cannot do that, you have a penance to pay, and it starts right here tonight. Now lay back and relax, and I will dress you up as I see fit,? and he watched as she walked over to her wardrobe and opened the door. She picked up a few items and walked back to the bed, and looked down at Dave, ?You’re going to love this, and then again maybe not,? and she gave a little giggle. She opened a bag and took out a stocking, after slipping her arm inside she rolled it down to her wrist, and holding the ring with both hands she slipped it up his leg, and did the same with the other stocking. Sally put her arm across and felt his manhood, and it was rock hard. ?Wow, you really must like my clothes,? and then before he knew what was happening, she had slipped more bonds onto his ankles. Then Dave watched as Sally fitted a suspender belt, and attached the stockings, she made sure that the suspenders went under the knickers, there was plenty of time for a little fun later. ?I wonder if I ought to put a bra on you,? and she laughed and added, ?No, I think I will leave that until the next time.?

?Err umm, what exactly do you mean by the next time, this will be the last time you can bet on that.?

?Oh dear Dave, there you go once again spouting off at the mouth, now for that remark you will have to wear high heels all day tomorrow. In fact just to show you that I mean what I say, I will put a pair on your feet now.? Once again she walked over to the wardrobe, and walked back with the said shoes in her hand. She pushed them on his feet and said, ?Same size as me, aren’t you lucky.?

?How? he asked in a squeaky voice and then cleared his throat. ?How do you mean that it is lucky??

?Well, think about it, the shoes could have been smaller and your little toes would be crushed,? and she gave another laugh. ?Now for the little bit of insurance,? and she walked to the chest of drawers and came back with a digital camera. Then for the next few minutes, Sally was taking photos from all angles, at one time she was up close and she said ?Smile,? and like a rabbit caught in the headlights of a car, he did just that. ?Damn, damn, damn, that was not called for,? he shouted, but she just pouted her lips in a kiss and then smiled. The session was over, and she walked across to the computer.

?Of all the people that I could have been in love with, I had to go and choose the twisted female version of David Bailey.? He tried to turn his head to see what she was doing, and in desperation asked her that very question?

?I’m just putting the photos in e mails to all your friends.?

?Do you hate me Sally??

She burst out laughing and answered, ?No, I am not sending them, but they can be sent any time I check into my mail box on my mobile, and then if you are naughty, zap, and your life as you know it will be over,? and once again she laughed.

?That lightning today Sally, it never struck you on the head did it, because there is still time to go to the hospital before the damage is permanent.?

Sally burst out laughing once more, and after a moment trying to control herself she replied, ?That’s right lover, keep your sense of humour.? Dave then watched as she walked across to the bed with a piece of A4 paper in her hand. ?Now listen in slave, and until you show me remorse that is exactly what you are, my slave. On this piece of paper are the rules that you will abide by, or I will send the e mails, do you understand slave??

?Err do I get the chance to appeal against your judgment??

?Let me think!? and she tapped her finger on the side of her face, ?In an answer of one syllable, no. Now, answer the question, are you going to abide by the rules??

?Yes,? he answered reluctantly, ?Do I get to see them??

?Of course you do,? and she turned the paper so that he could read what was written down. There was only one sentence saying; you will do all I say at all times, and punishment will be painful.

?Is that all, and what is the painful punishment, and after asking you I am not sure if I really want to know. I am getting feelings of misgivings and fear, but mostly fear.?

?Well I think we could start off with some gentle caning.?

?Gentle caning you crackpot, what planet did you come from, because it will sting like hell??

She was laughing at his outburst and then said, ?You now owe me three strokes for calling me a crackpot, and you know the saying slave, you have to be cruel to be kind.?

?Well if it’s all the same to you, I don’t want your kindness.?

?There are ways that you can reduce your strokes of the cane, and that is I will give you marks out of five for your love making. So you had better start improving, because you have been slacking of late, and if your points are above three you lose to strokes, and if your marks are below three, then you gain two. Wow, I’m beginning to like this game already, and I’ll bet you wish you had not humiliated me now slave??

?To be quite honest, I’m beginning to wish that I had not been born, anyway, where did you learn to use the cane??

?It just so happens I have been reading a training book of punishment, and it tells you the correct way to strike the buttocks with a cane.?

?I just know I am going to regret asking this question, but what is the book called.?

?The Marquis de Sade, and it was one hell of a good book, I’m still reading it and picking up points.?

?You are joking right Sally, and you’re not really reading it??

?Of course I’m joking you silly fool, I have already read it at school,? and she snatched the paper from him and laughed. ?One other thing, from now on you can call me Mistress.? Sally walked back over to the bed and said, ?Seeing as you have been a good slave and done all I asked, I will give you a treat.? She then pulled the two bows on either side of the yellow knickers, and they fell from his body. She saw his manhood standing proud, and said, ?Keep that thought.? Then she slowly began to strip off all of her clothes, and once she was naked she knelt down at the edge of the bed. Her hand slipped out to grasp Dave’s manhood, and at the moment she touched it, he gasped for air and held his breath. She was playing with it and gently masturbating him; and with her other hand she played with his glands watching him shut his eyes. Sally was doing this for some time, and then he started to buck his hips, in the hope of speeding up his climax, but she had better and far more rewarding ideas, but they were for her benefit. She was still masturbating him, and when he was ready to cum, she stopped, smiled and said, ?Damn my arm is tired and it needs a rest.? She heard him groan, and asked, ?Is something wrong slave??

?Nothing at all you bitch,? he murmured.

She smiled and asked, ?What did you say slave only I never heard??

?I just said that I had an itch Mistress,? but he was thinking, ‘steady Davey boy, you nearly got a few more strokes, and you don’t know what they feel like yet.’

She smiled at his answer, ?Well speak up in future, I don’t want to think that you are disrespecting me again.?

?God forbid I should ever do that Mistress,? and again thinking, ‘bloody hell I’ve started to creep to save my ass.’

While he was creeping to save pain, Sally was looking at his body, and the first thing she noticed was, that he had very little body hair if any, even the ones around his groin area and armpits were soft and few. She lifted herself up from the side of the bed, and then she looked down and smiled, she was going to get her own satisfaction first. She once again straddled his body, and his erect penis was just touching her buttocks, he was trying in vain to get relief, but she was not going to allow that. Sally moved her body forward so that her sex was almost touching his chin, ?Now slave, you have work to do before you get your satisfaction, and if you are not very good at the task, that I am about to set you, then your own satisfaction will not be forthcoming.? She moved closer, but not before looking down into his eyes, and then the final movement, and his mouth was clamped over her sex.

Dave was looking up at her body, and he could just see her breasts quivering like jelly, but it was only fleeting. His tongue was darting in and out of her sex, and he was now and again gently biting the soft folds that filled his mouth, but her hips were moving and pushing down. It was not a hard movement, and he could feel that she was using her legs to check her weight. There were times when she lifted up, and he lifted his head to lick the entrance to her sex. The pungent smell of sex and scent so close to his nose, was almost overpowering his breathing, but he knew now and just like the many other occasions her needs came first. There had never been a time that he had let her down, and failed in his quest to satisfy her craving for a powerful orgasm.

Sally was gently moving her body, now and again lifting it from his face and allowing him to breathe, there was no need to be cruel, and he was her lover as well as her slave. She had her hands on her breasts and playing with her nipples, tweaking and twisting pulling and making them rise tom the occasion. She was near to completion of her own sexual gratification, and she could feel the tremors running through her body, and exploding into the waiting orifice that was giving her so much pleasure. He had done well and it was only right that she should reward his efforts, but it was a foregone conclusion before the act that it would happen. Her body slipped down to his chest, and then down further so that their sexes were now touching, the fluids from the orgasm had lubricated her entrance, and she impaled herself on his manhood. She fell to his body pressing her breasts tight to his, and at the same time kissing him full on the mouth, and not for the first time tasting her own juices. It was giving her a feeling of immense pleasure just holding her lover so tight and close, but her lusts were on the boil once more, and she started her methodical movements of rising and falling.

As her sex enclosed his manhood, Dave closed his eyes and he never saw her mouth reaching out for him, but his response was instantaneous. The pleasure that this kiss was giving him was the compensation for the humiliation she was inflicting now, and he knew that there was more to come. But live for the moment he was thinking, there was nothing he would not do for the love of his woman, and now his Mistress. Her soft breasts were pressing against his, and her arms had slipped behind his back, and her strength was pulling him to her. In an instance Sally was again upright, he wanted to feel and play with her breasts, pull the nipples and torment them, but he could only pull on his bonds with frustration. Her body was lifting up and down, and he wanted her to go faster to quell the aching in his loins, but she only looked down and smiled.

Sally could see that his bonds were holding him fast, and she also knew what he wanted, and it was what she wanted also. Still keeping the rhythm, she lowered her body so that he could use his mouth on her breasts, and it was like a giant suction pipe, as he manipulated her nipples with his tongue. It was shortly after that when she pulled away and let him have his way, as she fell on his manhood, he was pushing hard to meet her, she saw his eyes turn upwards like many other occasions, and their orgasms met in the fires of ecstasy. Sally gently lay on Dave’s chest, her cheeks touching his, he had once again excelled in his love for her, and she appreciated his every effort. Without saying a word she slipped from the bed, and walked to the end, where she took the shoes off of Dave’s feet, and then after releasing his bonds she removed the stockings and belt. The last thing was to release his wrists before getting beside him and pulling the covers over them, ?Good night slave.?

?Good night Mistress,? Dave replied with his eyes closed, Sally smiled and closed hers.

Same as SALLY'S RELUCTANT CROSSDRESSER Videos

4 years ago
  • 0
  • 17
  • 0

Amazing Night With A Sexy Crossdresser

Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one. I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and...

2 years ago
  • 0
  • 26
  • 0

my life as a sissy crossdresser

it should be noted that i did not ask for this disposition to crossdress, rather it was presented to me quite by accident. circa 1958...grade school PTA fashion show. PTA fathers were asked to put on a fashion show dressed as their better halves. my dad was right in the mix. I remember he wore some mid calf, grey business suit w/jacket, tan stockings and black heels. i remember this because he practiced dressing days before the show. he wore some makeup and a wig. not very passable, but not...

1 year ago
  • 0
  • 16
  • 0

Sallys Holiday Part 5

Sally came into the lounge wearing a wrap over dress, stockings and high heels, the plunging neckline of the dress revealed a fair amount of cleavage and she looked drop-dead sexy. We headed out to a little restaurant not far from home, there were a few other early evening diners and Sally drew a few admiring glances as we went to our table. We took our seats and ordered drinks and the meal. I noticed a couple of guys glancing over and one of the staff had moved to a place where he was looking...

2 years ago
  • 0
  • 16
  • 0

Sallys Mum

My 22 year old daughter Clare had just got home from her new friend Sally. They had met at a local evening for young singles and got on well. Sally asked Clare to stay over for a couple of nights and she must have had such a good time she didn’t once phone home. She enthused about her new friend, and strangely enough also about her Mother. ‘Sally’s Mum is so cool.  She let’s Sally have all her friends around whenever they want and she makes sure everyone is enjoying themselves. She’s very...

3 years ago
  • 0
  • 17
  • 0

Sallys photo session

"Hello, come in, Sally isn't it. Can I take your coat? Could you just stand in the middle of the room and turn around slowly. That's it, you know your Polaroid's don't do you justice, you really are quite pretty. Now if we could just get the formalities out of the way first, you have brought your birth certificate haven't you. I'm sorry about this but you understand I can only employ people over 18. You know if I hadn't seen this I wouldn't have thought you were over 16. You're sure...

4 years ago
  • 0
  • 26
  • 0

Room 209 First Sex as a Crossdresser

crossdresser – trans – interracial – lgbt – first time – virgin – black cock – crossdressing – natural tits – braI've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a k** and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight...

4 years ago
  • 0
  • 16
  • 0

Sallys Holiday Part 6

The following morning I tried to draw Sally on what was in store for me, but she just smiled and said, ‘All in good time.’ We pottered about the house and garden for the morning, then, after lunch she led me to the bathroom. We showered and then she had me sit on the bed and watch while she put on a suspender belt, stockings, a pair of high heels and a flimsy shift dress which hugged her curves and left little to the imagination. While she dressed she set the scene… The events of the previous...

3 years ago
  • 0
  • 36
  • 0

Night Trawling The Crossdresser

The streets of Pomona live two lives. Like maternal twins, they coexist in parallel, appearing as virtually identical to those merely passing through its old and storied neighborhoods. During the day, with the sun high overhead, myriads of people — whether they’re commuters traveling like drones or soccer moms distracted by their busy lives — they choke the streets in a constant pulse of life. Each person is absorbed by their own petty concerns, each oblivious to what is happening on the...

Crossdressing
4 years ago
  • 0
  • 19
  • 0

Sallys Holiday Part 4

Later that morning, Sally said she wanted to go shopping, I groaned, saying that I would rather not. She sidled up to me saying that we could have a little fun while we were out. I looked inquisitively and she said that she would wear something sexy and we could do a bit of flashing. Now she had my attention, we had done this a few times before and I just loved the reaction it got from other guys. I had readily agreed, so she went and changed and we headed out. She had put on some seamed...

1 year ago
  • 0
  • 17
  • 0

Sallys Holiday Part 1

Some time ago my wife, Sally, took up the offer of a couple of girlfriends to join them on a short holiday to Ibiza. The weekend before she went, we were shopping for bits for her to take when she asked my opinion on a skimpy bikini set, consisting of a thong, plunge type cleavage enhancing top and a little matching skirt. I love her showing her gorgeous body off, for a woman in her late forties she is firm and shapely, with gorgeous round tits – all natural, so encouraged her to get it. I...

1 year ago
  • 0
  • 30
  • 0

Hitchhiking teen crossdresser

It was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter, I had my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to...

1 year ago
  • 0
  • 17
  • 0

My first time with another crossdresser

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my brother and sister. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer...

3 years ago
  • 0
  • 40
  • 0

My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or...

2 years ago
  • 0
  • 18
  • 0

Sallys Fantasy

Momentarily, I am disconcerted. My habit of letting my mind drift away to sex is not usually a problem, usually I can absorb what’s being said at the same time. It’s a useful trick because I think about sex a lot. If it becomes too intense, i make an excuse, slip away to the ladies room, lock myself in a cubicle and deal with it. If I’m that aroused, it doesn’t take long. This time, though, I have to ask Ty to repeat the question.Paul, my husband, says the infamous statistic about how often men...

2 years ago
  • 0
  • 20
  • 0

Sallys Holiday Part 2

I had lain on the floor of the living room, thinking about all my wife had just confessed, trying to collect my thoughts. She had owned up to fucking another guy and while it had always been a fantasy of mine, I never thought she would ever give me such a graphic account. I replayed it in my head seeing her with this well hung guy, sucking and fucking him in such a wanton way. I suddenly realised that I was holding my cock, which was already getting hard again at the thought of what else she...

3 years ago
  • 0
  • 19
  • 0

Sallys Holiday Part 3

The following morning, I had been enjoying my Saturday lie in and awoke with a raging erection, but something was different, it was in Sally’s mouth, she was doing exactly as she had to Roy. She removed me from her mouth long enough to say ‘Good morning my horny cuckold, fancy another episode of my holiday tales?’ I told her that I was as she returned to sucking my cock. She sucked me for a while then moved up the bed. Straddling me, she began to massage my cock with her pussy lips, lowering...

4 years ago
  • 0
  • 16
  • 0

First Time With Crossdressers

For once, I actually decided to look at some of the other categories on the streaming sites I'd visit. So many things came up under fetish. Some of it I don't get but to each their own. A BBW was mixed in with the fetish and as I had expected before hand, it wasn't my cup of tea. Several videos had girls dominating guys in leather or latex outfits. I liked how tight they were, showing off every curve of their body, leaving little to the imagination. Upon thought, I had never been...

2 years ago
  • 0
  • 27
  • 0

Chronicles With Sexy Crossdressers

My email id is Do not forget to let me know how this sex story was. Who knows, we might get even lucky if everything goes well ;) Clean shaved men inside female clothes (or people who are known by the name crossdressers) are my new found favorites. Believe me, I always make it a point to taste every bit of them with passion and fire. My hands and tongue never leave an inch of their body. Hairless, like women and the ‘EXTRA’ jackpot called ‘COCK’, is simply divine. This is a story of how a...

Gay Male
2 years ago
  • 0
  • 34
  • 0

Experiences Of A Crossdresser

This is an introduction to my crossdressing experiences – touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever.I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like slips and sheer blouses. I would typically be drawn to anything black, but did have a fondness for nude tights and white slips, also. I usually...

3 years ago
  • 0
  • 18
  • 0

First Time With A Hot Crossdresser

My email id is Please contact me for any queries, doubts or proposals. I usually work late nights, and leave home by 1 am. I take a rickshaw for home, which happens to cross this one spot where post-midnight you usually find young crossdressers here on business at the side of the road. They are dressed mostly in skimpy western outfits, some of them are really attractive. That’s saying a lot coming from me, for a 26-year-old straight guy. I’ve never been bi-curious either. It’s been months I’ve...

Gay Male
2 years ago
  • 0
  • 44
  • 0

firsts time Im seen as cd crossdresser

From a young age I liked dressing up in womens lingerie and clothing.... as I got older I grew up over weight a little and more so the older I got..... by the time I was I was in my late teens I had nice size breasts....nice enough to fill a bra. So worked up the courage to buy some lingerie online and when I received it in the mail I was so excited. I couldn't wait to try everything on.... I had brought a white lace bra, matching panties and white suspenders and stockings.....I tried them...

2 years ago
  • 0
  • 21
  • 0

Telling Mom Im A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

Crossdressing
1 year ago
  • 0
  • 14
  • 0

Telling Mom Im A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5’10’ in height. She is also a fairly busty woman with a 30DD chest with about 35′ hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

1 year ago
  • 0
  • 24
  • 0

The start of my life as a submissive crossdresser

I am a bisexual cross-dresser/sissy and have been enjoying my life as such for many years. It all began for me when a friend asked me to look at some of his 'girlie' magazines.We went up to his bedroom and looking through the magazine got Chris really excited and he got his cock out and started to masturbate. I couldn't take my eyes off his cock and I slowly reached out and touched it and when he removed his hand I curled my fingers around his erect shaft and began to slowly wank him.I just...

Crossdressing
4 years ago
  • 0
  • 26
  • 0

Craigslist crossdresser

It finally happened. I got a response! I’d been corresponding with him on Craigslist, but then suddenly Craigslist personals were banned. I tried to reply to the Craigslist generated email that I thought was his, but I’d deleted all of his email’s in a moment of weakness. Now I had no way to get in touch with him. He’d posted about hosting crossdressers and providing a safe, relaxed place for us to fulfill our fantasies. He said he would be gentle. I’d told him who I was, that I liked to wear...

2 years ago
  • 0
  • 24
  • 0

Motel Fun for College Crossdresser

Before I start the story I want to describe the setting so you get a better idea: it's a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a family sleep that's for sure. The layout of the motel is a rectangle. The rooms surround the rectangle's perimeter, in the center there is a pool, a park area, and a parking lot. There is a walkway around the entire inside perimeter of the rectangle and every room has two doors, one facing the exit and...

Crossdressing
2 years ago
  • 0
  • 21
  • 0

A Tale Of Crossdresser

Hey, this is my first story that I am writing but not definite new to the glorious crossdressing field, Kindly forgive me if there are any mistakes, suggestions are welcomed people who are moving to Bangalore or in Bangalore if they want to my friends or a hook up we a cross dresser can contact me at m First, I don’t have a perfect girl figure but I wanted to be dressed as a girl, do a girl activity from a long time but it didn’t come true. I always used to wear my mom’s clothes like bra &...

Gay Male
3 years ago
  • 0
  • 12
  • 0

indian crossdresser

hiiiiiiiiii every one here's kiran from india ,punjab first of all its not a fictitous story ,it is  a real part of my life my actual name is rahul and me a guy now of 20 yrs old. so lets start frm my age of 12 yrs............................... me frm starting was very likely to kiddish me always remain at home .not to go any where else than in my street. in mid of june when our holidays were going on my parents were with at home ,i asked them about there relationship .they bit were not happy...

Crossdressing
4 years ago
  • 0
  • 13
  • 0

A great experience as a crossdresser

I was born and grew up for the first 27 years in England. Ever since I was 16 years old I have always had an infatuation with sexy ladies lingerie.I used to dress up in my mothers and older sisters lingerie and get very turned on and wank myself off while dressed up. I am now 53 years old and still tremendously enjoy the thrills of dressing up and wearing sexy lingerie.One of my early experiences was when I was 18 going on 19. I had been to a thrift store and purchased several items of ladies...

Crossdressing
3 years ago
  • 0
  • 18
  • 0

The Reluctant Maid

THE RELUCTANT MAID Patricia Goodwin was in a foul mood. In spite of not being quite thirty, she owned and ran several very successful businesses including real estate rented out, that she had inherited from her father, and she was on top of her game except for that fateful afternoon. First her husband of seven years Len , had phoned her at noon to say that the company he worked for had been put into administration. It was going bust. Then her car had started to play up as she was...

2 years ago
  • 0
  • 17
  • 0

Reluctant Rebecca

This story was inspired by two of the web’s best authors on the topic of reluctant lesbians – LCDRJMC and Jenna Tarp, although neither seems to be writing these days much to my dismay. Many of the themes contained within can be found in their works, although probably better written then my attempt here. My hope is you’ll enjoy the story and that either the two authors will love it and be inspired to write more, or hate it and be inspired to write more – either way it’s a win for me. You should...

3 years ago
  • 0
  • 19
  • 0

Cock sucking Crossdresser

When I was out on my own I started to buy a few things' mostly panties and thigh high stockings then a skirt and a blouse things that where ease to get to fit me. From there I learned to find my size in dresses and shoes this started to put my wardrobe to gather, but I still needed a wig and makeup so it was back online for more shopping, With lots of practice I became pretty good at putting on my makeup, plus doing my wig hair and a waste cincher I looked pretty darn good if I say so my...

2 years ago
  • 0
  • 15
  • 0

The feminine crossdresser

Chucky open’s his eyes as he awakes, looking around at his familiar surroundings in his bedroom. Band posters, comic books and video games all over the floor. His parents always gave him crap about the things he liked and tell him the typical “you’re too old to be into thoses kinda things!” He didn’t care though. He stepped out of his bed in his black t-shirt and grey track pant’s that he wear’s to bed and walks over to the window to look out as he...

4 years ago
  • 0
  • 12
  • 0

Made My Friend A Crossdresser

I am having a tsunami of mixed feeling about this friend of mine who’s name shall remain anonymous but for now lets call him Anshul. He’s a good guy and a hot one. He got flawlessly creamy skin with awesome bubbly butts. This started a few years ago when we met for the first time in India. We worked in same company and he was a friend of a friend. At that time I was crazy about my physique and was well built up and he got motivated and asked about my workout routine and slowly he started...

3 years ago
  • 0
  • 10
  • 0

indian crossdresser

hiiiiiiiiii every one here’s kiran from india ,punjab first of all its not a fictitous story ,it is  a real part of my life my actual name is rahul and me a guy now of 20 yrs old. so lets start frm my age of 12 yrs…………………………. me frm starting was very likely to kiddish me always remain at home .not to go any where else than in my street. in mid of june when our holidays were going on my parents were with at home ,i asked them about there relationship .they bit were not happy with each other...

2 years ago
  • 0
  • 14
  • 0

Motel Fun for College Crossdresser

Before I start the story I want to describe the setting so you get a better idea: it’s a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a family sleep that’s for sure. The layout of the motel is a rectangle. The rooms surround the rectangle’s perimeter, in the center there is a pool, a park area, and a parking lot. There is a walkway around the entire inside perimeter of the rectangle and every room has two doors, one facing the exit and...

4 years ago
  • 0
  • 35
  • 0

My Night with a Crossdresser

I am not a good writer but this was the hottest night of my life.I was out of town on a Business trip, staying alone at a nice hotel. After a long day of meetings, I was sitting at the Hotel bar drinking a glass of Scotch.The bar wasn’t crowded but wasn’t empty either. The seat next to me was open. Wasn’t long before what I initially thought was a woman came in and sat next to me. She said hello and ordered a glass of white wine. I realized then that she was a Cross Dresser. she looked to be...

3 years ago
  • 0
  • 31
  • 0

Halloween cd crossdresser

TinkerbelleMy sister , Candy, and I were fraternal twins, but looked nearlyidentical. Pretty much the same height weight and build. In high school,she was always teased about having small tits and I was always teasedbecause I was small, thin and had a big ass for a guy. Because of this wewere extremely close. Best friends really. We spent nearly all our timetogether.After college she became a consultant and I became a math teacher. Becausewe were so close, I spent lots of time at her house...

3 years ago
  • 0
  • 23
  • 0

Uber driver fuckes teen Crossdresser

Hi guys im a cd from Orange County and i had the sex ever last night with someone I never expected. So it was around 1 and i had just soent the night with my “friend” well I had just blew him and watched a movie and he got me an uber so i kissed him and left when tge uber came and I went on my night. He told me it was a white truck and espanic i went in and told me my “friends” name and we drove off. It wasnt even 10 seconds and he said what was my name i told him i was “. “ and he said nice to...

3 years ago
  • 0
  • 17
  • 0

My first time as a Crossdresser

Its 18 months ago. I had now become comfortable wearing womens clothes. I had been experimenting for around 3 months. I gradually started to get more confident in both my clothes ......and without. I started to dress more like a slut. Short skits. Suspenders. Corsets. I had also become more comfortable with my body as well. My hole was tight as could be. Like everyone, i started with fingers, one, two .....before moving on to small toys. After a few months, i had graduated to a 9 inch...

2 years ago
  • 0
  • 25
  • 0

First taste of cum for a Crossdresser

I had never really been with another man before and I had always thought about it as I dressed up as a slutty girl and played with my little toys to orgasm. I'm a little tall at 5, 9 and with heels a monster! I have an average body, nothing feminine, but not out of shape and a nice big bubble ass.Until that night. I had been sent to Dallas for a business trip and was super excited to dress up in my hotel room and play around! I played around a couple days in my room and just got dressed did...

2 years ago
  • 0
  • 25
  • 0

My First Crossdresser

Only a few years back in my young 20's i discovered Craigslist. I had no idea something like that existed and was immediately drawn to it. After building up the courage to meet up with a few guys a couple times i found an add in the T4M section. I got instantly hard when i seen this girls pictures. A slim sexy girl with an ass to die for and a desire for Cock. After some back and forth emailing for a few days we agreed to meet in her place.I went around to her place late that night when the...

1 year ago
  • 0
  • 29
  • 0

Made My Friend A Crossdresser

I am having a tsunami of mixed feeling about this friend of mine who’s name shall remain anonymous but for now lets call him Anshul. He’s a good guy and a hot one. He got flawlessly creamy skin with awesome bubbly butts.This started a few years ago when we met for the first time in India. We worked in same company and he was a friend of a friend. At that time I was crazy about my physique and was well built up and he got motivated and asked about my workout routine and slowly he started joining...

2 years ago
  • 0
  • 19
  • 0

How I became Jayne The Crossdresser

It started in 1976,around August,I had just met John a guy my around my age,who lived alone near me. He wasn't shy to admit he was gay,and I was curious,and I told him one Friday after we got back from the pub about my interest. Before I knew it John & I had undressed & I had Johns cock in my mouth,sucking him off,& he soon quaked into an orgasm,cumming in my mouth so fast I gagged slightly before I managed to swallow most of it.John was keen to make it a pleasure for me &...

4 years ago
  • 0
  • 21
  • 0

Natural Ingredients for a crossdresser

It was still snowing outside and I wasn't going to be recieving any visitors today so I decided to treat myself and while the day dressed how I wanted.... I had set the heating up high at my place, so I could wear one of my sexy side tie bikinis which show off my sweet little ass so well. Having enjoyed the view in a full length mirror and got some self shot snaps, I found myself sitting at my dressing table wondering how to amuse myself next.... Looking at my face in the mirror I noted a...

2 years ago
  • 0
  • 26
  • 0

Patni Patni A Crossdresser

“Oh Ramesh! I am so happy that you came today.”, I pressed my boobs against his chest and wrapped my arms around him, as soon as Ramesh entered in my flat. And he grabbed be in his arms too like a real man. He began to touch my body and moved his hands all over my back and lower waist. I was titillated by his sensual touch. “Where else I could be, my darling.”, he said and slowly slipped one of his fingers from the back of my saree blouse. He was feeling my bra strap with his finger. We two...

2 years ago
  • 0
  • 21
  • 0

transforming into ashley crossdresser

durring the day,i'm working i'm dressed in my work clothes,but when I come home I take a hot bath washing all over my body,then shave my legs,arms chest,and face.I even add babyoil in the water so that my skin becomes soft.then I will clean myself ass inside/out.then as i'm drying off i'll start ptting on my makeup,this takes me about an hour,I like taking my time so that my makeup looks perfect,so that when I put my wig on I'll have that female look.then go in the bedroom pick out something to...

2 years ago
  • 0
  • 19
  • 0

Party Surprise First sex as a Crossdresser

This is a work of Fantasy. I hope you enjoy.Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly she was jealous of my legs. She was a petite sexy woman and we were almost the same size but I still had my own stuff that I’d secretly obtained from eBay and op shops.I didn’t consider myself bisexual,...

2 years ago
  • 0
  • 16
  • 0

Made My Friend A Crossdresser

I am having a tsunami of mixed feeling about this friend of mine who’s name shall remain anonymous but for now lets call him Anshul. He’s a good guy and a hot one. He got flawlessly creamy skin with awesome bubbly butts. This started a few years ago when we met for the first time in India. We worked in same company and he was a friend of a friend. At that time I was crazy about my physique and was well built up and he got motivated and asked about my workout routine and slowly he started...

Gay Male
2 years ago
  • 0
  • 11
  • 0

A great experience as a crossdresser

Note: ——I am NOT the author!so plz Don't ask me about part two,am simply sharing this lovely story with all of you because I have not seen it on hereI was born and grew up for the first 27 years in England. Ever since I was 16 years old I have always had an infatuation with sexy ladies lingerie.I used to dress up in my mothers and older sisters lingerie and get very turned on and wank myself off while dressed up. I am now 53 years old and still tremendously enjoy the thrills of dressing up and...

2 years ago
  • 0
  • 11
  • 0

A great experience as a crossdresser

I was born and grew up for the first 27 years in England. Ever since I was 16 years old I have always had an infatuation with sexy ladies lingerie.I used to dress up in my mothers and older sisters lingerie and get very turned on and wank myself off while dressed up. I am now 53 years old and still tremendously enjoy the thrills of dressing up and wearing sexy lingerie.One of my early experiences was when I was 18 going on 19. I had been to a thrift store and purchased several items of ladies...

1 year ago
  • 0
  • 16
  • 0

Beauty And A Crossdresser

Hi this is hotslutaddy back with my friend ishika’s story. Hi this is ishika. Those who have read my first story “lost virginity from behind” in virgin archive should know that I am a cross-dressing bottom gay.It had been 8 months till that incident and I had completed my schooling. Kartik had become my boyfriend and I love him more than my life. Now I was in a college in a nearby town and I lived at a house on rent. I lived alone there so I had an almira full of female clothes and make up.Most...

Lesbian
1 year ago
  • 0
  • 27
  • 0

The 2nd Halloween for a Boy Dressed as a GirlPart 1 A Blissful Young Crossdresser

5th Grade. 11 years old. Dressed as a girl again on Halloween. As a cheerleader. My next old sister's cheer uniform. Her idea. Her bra and panty too. My special "Boob" socks to give the appearance of breast. A discussion I had with my next 2 older sisters. How ample were my false breast to be? Normal size for girls my age? Bigger for my ego as a girl, for all the times I have dressed up with them through the years? Dolly Parton size? Because my 2nd oldest sis Joan, made...

1 year ago
  • 0
  • 14
  • 0

The hottest crossdresser

I was drinking with my friend Curtis one night as his girlfriend Jane was out with her friends having some drinks. The topic turned to cross dressers, as I had had let it slip, that one time I mentioned to him, I had dressed as a girl a few times when I younger in my moms clothes, and it felt great. He asked if I had any girl’s clothes at home that I wear from time to time, which I reluctantly said yes. With that Curtis asked if I would wear some of Jane’s clothes to see how I looked. “Sure,...

Bisexual
3 years ago
  • 0
  • 17
  • 0

The Reluctant Performer

This story contains sexual material and transgender themes. If you're not 18 or over, or are offended by such material then don't read it! This story can be posted on Fictionmania or any other free sites however, I do ask that you notify me first before doing so. The Reluctant Performer By Kelly Davidson December 2000 Mrs. Applegate walked into the office to gather some papers. So many things to do before tonight's play, she didn't know how anyone could keep track of it...

2 years ago
  • 0
  • 15
  • 0

A Story about Black Cock and a Wifes reluctants

I'm always amused when I read stories that involve black men, and how all of them are so well endowed. I think that the writers of these stories have not seen very many black men naked, or they have a very vivid imagination.Having been in college athletics for four years, I have seen a large number of both white and black men naked, and in my opinion there is essentially no difference in penis size between white and black men.However, there are some rare notable exceptions in both white and...

1 year ago
  • 0
  • 31
  • 0

Valeries Reluctant Evening

Valerie Marie Stephenson was scared shitless. She was scared, but it was in a tingly way; paralyzed with fear, but also feeling tingles of curiosity. She was sitting next to her husband, but she was too nervous to really have his words register. "It's a nice place. I think you will like it. Remember; you don't have to do anything you don't want to. We are just going to go in and see what this place is like. If you don't like it, we can leave." He didn't really have the courage to look...

1 year ago
  • 0
  • 24
  • 0

Reluctant Invite

A few years ago he had met Erin. The opposite of his wife; Erin was a brunette with curves in just the right places, and craved sex all the time. She was insatiable. Erin had seen pictures of his wife and drooled over her constantly. Feeling sorry for Tripp, she wanted to turn his wife to the dark side. If nothing else, she would see that the Bitch paid for her cold ways. Erin knew just the push. A few days later, the weekend had come around. Tripp found himself driving his wife up to a...

Porn Trends