First Time With Crossdressers
- 4 years ago
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Im not an author in any way but I would like to tell you about my latest crossdressing adventures. I have been crossdressing for many years but maybe only twice in a year when the mood took my fancy and only ever indoors, the feel off nylon on my legs would get me very aroused and looking at my self in the mirror wearing high heels and a very short skirt had my cock pumping and I always had an intense orgasm, but over the last few years it has became more frequent and not confined to indoors...
hi, im new to this. this happened about 3 years ago now.I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from this simple thought I became massively aroused and started trying on her underwear, make up, and even a wig that was in the apartment. soon enough, I was looking like a slutty crossdresser.I thought enough...
When I was 27 years old and single, I really liked going to shows at night, to nightclubs, especially when it came to beautiful women. One day I went to a transvestite show and was fascinated.These men dressed as women groomed themselves more than any of the women he knew; her wardrobe, her makeup, even her movements, were more feminine than any woman's.I started visiting an exclusive nightclub, where every night there were transvestite performances imitating well-known artists and singers.I...
( . Y . )I just found out my Mom told a whole group of parents about an incident when she caught me in her cloths. Specifically, she caught me in her bra, panties, panty hose, and makeup. I am approaching thirty-five years old now and the individual that told me must have heard it from his mother, who was one of the other parents. We used to go camping every year and one night when the k**s were playing or sleeping the parents were talking. She let it slip that she caught me in her room with...
I had met Steve thru a gay dating site, we exchanged messages over a few weeks and then finally agreed to meet. I was very nervous on the way over to Steve's for two reasons. One was it was going to be my first gay encounter. The Second reason, and one i had only agreed to after Steve's insistence, was that i was going completely cross-dressed. I'd gotten dressed at home as Steve wanted. Putting on a satin and lace garter belt which i attached to lace top suspender stockings, then a lace bra...
had been a private cd for years and along with that secret I always wanted to give head .. but always to nervous . I used to be a long distance hgv driver and park up at night it what I call , naughty laybys . we all know the sort . did see quite a few things going on in them . especially single men turning up with hard cocks wanting some fun . most nights I would get dressed up and climb out and walk up and down and seeing if anyone saw me , then quickly run back to the lorry and hide . it was...
i first started to wear tights when i was 18,i was shocked when i first realised i loved tight panties and sheer tights. i was staying with my friends mother who was 65 at the time,she wore the sexiest lingerie i had ever seen,especially on a woman that age,but i felt drawn to the sheer stockings. the next day i was taking a bath when i noticed them on the wash basket,i had an urge to wear them,i was very shocked by this desire but had to!i slipped them on taking care not to rip them,they were...
My roommate and I were both bi and part-time cross-dressers. We were also familiar with consensual B & D and had already worked out several code words, then went a step further and wrote scenes for each other, so that when we’re in the mood, we could call up the scene rather than try to explain it or coach someone through it. Sometimes we did a scene to please each other sometimes we asked for a scene because we were in a specific mood. So it was that I got an e-mail at work, which would...
CHAPTER 1 Summer vacation was over already. And it was the start of my senior year. My alarm rang and I was filled with anxiousness. I don’t want to go. “John! Get up and get ready for school! Don’t want to be late on your first day.” My mom yells from downstairs. Fine. I get up and head over to the bathroom. My morning erection trying to poke out from my boxers. I say trying because it so small I couldn’t even grip it properly. I’m all washed and ready for the day. “John I really wish you...
Rick came into the apartment looking sexier than any woman I had ever seen.His long slim legs encased in silk stockings. He walked better in heels than my wife Caroline.My cock was hard just looking at himHe kissed me his tongue sliding in my mouth. I returned the kiss. My hands running down his back to his tight arse. I wanted him so badly.As we kissed the phone rang. It was Caroline and I knew I had to take the call we spoke at the same time every Sunday when I was working away. These rituals...
It was another day in where i had to wait until very late for my wife to come home. We hadn't done it in many weeks, there was too much stress going on, and for her it's hurtful since her operation. We cuddle and share as many intimacies as possible, I cook and clean, so she doesn't need to do that when coming home. When I had a fulltime job, she did the same for me.My neighbor came with two friends. He has a houseboat of about thirty five feet, from which he fishes. Everything bigger then a...
I'm sitting in a crossdresser's sex bar – it’s dark. My companion Fifi is wearing only a pair of sheer silk panties in light blue, stocking and suspenders, and a pale blue matching corset that pinches his waist. His balls peak out of the tight panties. I’m wearing silk patterned stay-up stockings in black and a scarlet and black thong. The string of the thong rubs against my sensitive asshole and the soft skin of my ball sack: it’s a turn-on every time I move.A group of men and women approach...
I haven't mentioned this before but as a younger person I was bullied. Quite relentlessly at times by a couple of older k**s in the neighborhood, Gabriel and Tom. Tom went on to do something quite successful with his life but last I heard, Gabriel was on the unemployment benefit and selling weed. I'm OK now looking back they did have an effect on me. I'm pretty sure a lot of my social awkwardness came as a result of the months of concentrated attention by these 2 arseholes. Tim and I made a...
I was quite shocked with myself after mine and Tims extremely hot escalation the other night. (I had to finish up early due to becoming extremely horny remembering that tale. - Author) Let me finish the story.I sat up between Tims legs and released the grip of my lips. Just enough to let some of his cum gloss them. Tim watched my face closely as i sat there wondering what to do next. I'd already swallowed a portion, I'm sure. Tim giggled a bit at my facial expressions which made me grin and...
Well its our monthly party time again... we've been getting more and more adventurous over time and have built up a good roster of friends into the same lifestyle who are game for almost anything. Since my wife & I are hosting this one - we get to make the plan - explain it to everyone and also to have the most fun of anyone there... I have been getting more and more into wearing lingerie during our sexcapades - both together and more recently in groups... We made this party a "come in...
BisexualWant to get kinky at Fet Life? Never before have fetishes and kinks been as popular as they are today. I don’t know if it is because the invention of the internet has led to a greater level of transparency and communication when it comes to peoples’ deepest sexual desires or if it is because we are just becoming more open and accepting as a society. Or maybe it is something else altogether. Whatever the reason, more and more people are embracing their kinks, and it is a beautiful thing to...
Hookup SitesIt was a time of horrible raids by terrible marrauding hordes, which caused untold misery, fear and poverty in all of Pelopones. It was a time when Xena and Gabrielle were needed by all the towns, before it is too late, but she was nowhere to be found. The century before had been a good time for all, under the Cooperation Accord of Olympia, there was piece between all the polises, and Xena could concentrate on petty crime and feuding Gods. But now Xena had been on a mission in Asia for years,...
This is not the story of how my mother, my sister, and I escaped that catastrophe, of how the starliner Pegasus II tried to escape the disaster into FTL only to be destroyed by debris, of our flight to and rendezvous at the lifeboats, of the 24-person lifeboat jettisoning with just the three of us aboard. There are at least a dozen such accounts from the 87 survivors from the Peg, and most, to be honest, are more compelling. This is not the story of the first tumultuous hours after the...
Mom and Dad had been planning to renew their vows that very evening, and Mom had arrived at the lifeboat directly from the station where she had been shopping and getting made up for the ceremony. She was already in her white dress, tight around her torso to accentuate her remarkable figure but flowing in the skirt to give her an ethereal look. She wore white stockings underneath, the lacy tops barely visible where the skirt had ridden up. Like the rest of us, she was shoeless, probably...
PART 1 Them fuckin’ Armed Services get all the credit, but who gets their asses blown out of the water to get them their crap, for chrissake? Us fuckers in the Merchant Marine, that’s who. Goddamn sub-bait. And then they don’t send nobody to fish us out. Goddamn Krauts. Goddamn war! Cookie bobbed in his lifejacket and watched his ship disappear, a sorry excuse for a vessel, to be sure, but nonetheless, his ship. Sailors deep-six all the time, the risk they signed on for, perhaps. Bad luck,...
So, after I blew the guy downstairs and told him to come and knock on my door and pay me to blow him again anytime, I went up and took a long hot shower and put on a nighty and went to sleep. I slept surprisingly well considering I had just spent a long night out selling my ass. I thought about how much it scared me and aroused me as I drifted off to sleep. The next day I called Jesse and talked about what happened. We talked about how turned on I was by the whole thing she told me I was nuts....
Tracey the LifeguardBy: Jake OliveNote: As always, feedback is greatly appreciated. [email protected] had finally come to England and Tracey was very happy to be working as a pool lifeguard. At 22 Tracey was probably a bit too old to still be holding temporary summer employment but she had spent the last four summers working as a lifeguard and she couldn’t think of any reason to stop now! Tracey’s wasn‘t always the brightest or most mature girl in the world and unfortunately she had...
“So, how should we do these Stone’s songs?” Phil asked at our rehearsal session. “I think we all know the music, we just need to come up with a pretty awesome arrangement; we don’t want to sound like yet another cheap cover band.” “I had some ideas, if it’s okay for me to make some suggestions,” Allison said. “Of course it is,” Phil said. “Everyone can have a say, there’s no rule that says you can’t participate in the discussion.” “Thanks, Phil, I guess being the newest here, I’m a bit...
“That’s one pound fifty change, and your band. Pool closes in twenty-five minutes.” “Do I need to wear this?” The receptionist had given me a blue band such as one would receive at a gig. “Yes, the lifeguard will need to see it,” she replied. The receptionist was a petite girl, blonde hair sitting on her shoulders, wearing the supplied blue polo shirt all the staff wore. For a petite girl she had an impressive cleavage, pushing at the buttons on her shirt. I thought I’ll just show it to the...
FetishLast night I went to the pool late and ended up having a threesome in the showers.Usually, I go to the pool during the day. It feels warmer, I get some work on my speedo tan, and in the middle of the day, the pool is generally quiet. Yesterday (Friday) I was busy with work all day and time just got away from me. The pool closes at nine pm and just before eight pm, I decided to go for a late-night swim. I really wanted to get out of the house and had nothing else planned.The pool was quiet...
Gay MaleEric was in town for business. He hated having to take trips for business, but always made sure to book a room at an upscale hotel with fitness facilities, a hot tub, sauna and a pool. It was late when he arrived and got settled in his room. Figuring that he had just enough time to swim a few quick laps before the pool closed, and maybe take a short soak in a hot tub, he stripped off his street clothes and slipped into a black lycra speedo with a colorful print pattern on the front, one of his...
Después de lo que había pasado en el hotel aquel, no podía quitarme de la cabeza lo ocurrido.Antes de salir de la habitación me había dado un pequeño papel con la dirección de su trabajo y el número de teléfono.Había pasado ya casi un mes cuando encontré esa nota guardada en mi cajón entre mi ropa anterior, la saque y no pude evitar sentir que mi respiración se agito recordando de nuevo aquella verga en mis labios entrando y saliendo, sus venas marcadas.Cargue la nota entre mis libros unos días...
Ships, particularly warships, have watertight compartments to stop internal flooding from torpedoes, bombs, or other hull damage to the ship. Sailors slam the heavy steel doors (hatches) shut and seal them tight, also known as dogging the hatches. This keeps the ship afloat during times of crisis.Military people, particularly those who have seen combat, also have compartments. When you’re flying off of your leader’s wing (who is also your best friend) and he gets blown out of the sky and you...
Love Stories(C) Mojavejoe420 2020 Ships, particularly warships, have watertight compartments to stop internal flooding from torpedoes, bombs, or other hull damage to the ship. Sailors slam the heavy steel doors (hatches) shut and seal them tight, also known as dogging the hatches. This keeps the ship afloat during times of crisis. Military people, particularly those who have seen combat, also have compartments. When you’re flying off of your leader’s wing (who is also your best friend) and he gets...
I am the mighty Cernunnos, nature god of the old world. I am the lord of all male animals, fertility, and procreation. There was a time when you humans revered me. Then, you decided to worship false gods that you invented. You worship material possessions and worse more, you worship gods like the Christian one. Your kind has forgotten me, but I will be ignored no longer! I have taken one of your most desirable women, now I shall take another. I used a minor version of my spell for the first...
JOANNE SLAM - A LIFETIME OF CROSSDRESSING…..Almost!!!I have been doing this for a long time, cross dressing and my wanton ways with my transvestite fetish, my feelings of bi-sexuality and the thoughts of being “The Nasty Looking Slut” when I would look at porn magazines. This was in the late 60s and early 70’s mind you so I was seeing very cool, I thought anyway, looking back now it was that vintage lingerie and under-garments style and as a teenager it was most likely finding these kinds of...
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...
“Tim, we have got to talk!” Leslie said in a strange tone the moment I showed up for work the next day. I assumed I was either in trouble or getting fired or both.“What’s up Les,” I asked nervously.“The ladies don’t want Ellen back as their lifeguard. They want you,” she said. “You made such a nice impression on them that they want you to be their regular lifeguard. And obviously naked, of course,” she grinned. “Did you ever think that you would be paid for walking around nude?”“I don’t...
MILFI just turned 16 and my parents strongly encouraged me to find a job. I say “strongly encouraged” because they were cutting off my allowance now that I was old enough to work. Fair enough.I checked the want ads in the local paper and didn’t see anything that sounded remotely interesting. This was going to be harder than I thought. But then on Monday, I went to PE class and saw a help wanted ad on the locker room bulletin board. A new local health club was opening and needed a lifeguard for...
MILFLifeguard At A Nudist Camp I could not believe it when I got hired as a lifeguard at a nudist camp. Interestingly I had to wear trunks that identified me as the lifeguard, while everyone else was naked. The job came with food and lodging. I saw women from babies through teenagers, adults, and old ladies. I saw breasts from nonexistent to drooping to their waists. I saw guys too but tried not to look at their cocks, even so I saw some real monsters. I saw all sorts of scars from...
In the swimming pool, fixed and fucked. I am a 22 year young girl, was with friends at the pool, and looked where to swim. When I was suddenly thrown another into the pool. There was a problem, I could not swim. I tried again to get out of the pool but could not. Eventually, 2 lifeguards jumped into the water and rescued me. But I was not responsive. The lifeguard took me out of the water, put me on the stretcher and took me in a locked room. Civil servants me until I was again accessible....
In the swimming pool, fixed and fucked. I am a 22 year young girl, was with friends at the pool, and looked where to swim. When I was suddenly thrown another into the pool. There was a problem, I could not swim. I tried again to get out of the pool but could not. Eventually, 2 lifeguards jumped into the water and rescued me. But I was not responsive. The lifeguard took me out of the water, put me on the stretcher and took me in a locked room. Civil servants me until I was again accessible....
In the swimming pool, fixed and fucked. I am a 22 year young girl, was with friends at the pool, and looked where to swim. When I was suddenly thrown another into the pool. There was a problem, I could not swim. I tried again to get out of the pool but could not. Eventually, 2 lifeguards jumped into the water and rescued me. But I was not responsive. The lifeguard took me out of the water, put me on the stretcher and took me in a locked room. Civil servants me until I was again accessible. They...
In the swimming pool, fixed and fucked. I am a 22 year young girl, was with friends at the pool, and looked where to swim. When I was suddenly thrown another into the pool. There was a problem, I could not swim. I tried again to get out of the pool but could not. Eventually, 2 lifeguards jumped into the water and rescued me. But I was not responsive. The lifeguard took me out of the water, put me on the stretcher and took me in a locked room. Civil servants me until I was again accessible. They...
It is now almost a year later and I am a year older, my hormone treatment has been going on for some time. The short version of the past few months seems some of the most poignant in my life but not conducive to this readership. My skin was getting softer, my body hair lighter and most important to me, I started to grow breasts. Sam was watching the whole process and thought that I would, some day, have nicer breasts than her. My oversized penis was still that but at this point I didn't mind....
Introduction: First, let me introduce myself…the author. I am a 37 year old divorced career woman, no kids. I am in a serious hetero relationship with an interesting sex life…pretty creative, with role playing and outdoor encounters being the most exciting. I have been lurking here for a few weeks, reading all the hot, sexy stories members have posted. I thought Id try my hand at writing and keep it busy and away from my coochie for a change. Im going to try telling this story as a male, to...
James Thurbers 1939 classic "The Secret Life of Walter Mitty" was about an elderly inefficient husband having heroic daydreams. In 2002, Pretzelgirl published a wonderful pastiche, "The Secret Life of Willie Malter", about an elderly inefficient husband daydreaming of womanhood. But times keep changing - so I hope there is still room for another story about a quite young and efficient husband who has, nonetheless, problems which set him daydreaming in a third way... (Since here the...
When he raped me he thought I was 16 or so – it wasn’t until after the gang rape I told him I was only 13 – I told him so he would let me go but instead all he saw were dollar signs; lots of perverts want to fuck kids and they will pay heaps to do it. The type of men Jack whored me to liked little girls who cried and got frightened so I was perfect. He dressed me in clothes a 5 year old would wear and since every customer acted out raping me – the clothes were only ever worn once. I had...
I woke up late missed breakfast on my second day, I made my way to the shower cleaned Jake's smell off my body, I dried myself off put on my new Blue Bikini and headed out for a different pool than yesterday. Not sure if I just wanted to stay away from Jake and his buddies or just wanted new adventure! Once I arrived I found a chair took my cover off and lay down. It was another glorious day the weather was sunny and hot. The woman next to me started a conversation with me asking if I was here...
Introduction: Best read the stories in sequence! Lifes Strange Turns, Part 3 Monday and Tuesday came and went, with nothing exciting happening, except that Sandy called to say that she had gotten a nice offer on the house from a couple about 30. Her kids were back from their Dads, so she couldnt come over, but wanted to. Id gone to the gym after work Monday, Tuesday and Wednesday, and chatted with a pretty woman in the my age bracket that was interesting and had no rings or other evidence of...
Theron won the great sparta and Queen of Sparta. By doing sexual war with Queen Gorgo. [email protected]
FantasyFrom the Lifeguard 1 Story:I woke up sometime later with my spent mother on my chest snoring peacefully, my now soft penis still in her anus. My mother was smaller than me, so her weight wasn’t an issue, it’s just that I really needed to pee. So I started trying to wriggle out from her embrace. When I did she stirred. She said, “Don’t move.”She slowly pulled herself off of my penis, did a quick spin where her asshole was in front of my face, and said, “Eat it out.” Before I could even form a...
IncestThis sex story involves my favorite and the greatest and most beautiful pornstar in the entire world, Madison Ivy. Okay. Now, in this sex story. Madison Ivy looks and sounds exactly the same. The only difference is that she has a huge, long, veiny, and hairless cock. I am in this sex story, as usual. In this sex story, I am medium built muscular. I have a pretty great size for a cock, and the most sexiest, hairless, cutest ass that nobody can resist. And, as usual. I love and crave getting...
It was on my way home when I decided not to tell Tim about Sin. This was very private and it was already bad enough that I knew, also, I had no idea what Tim might say or do. I did want to stay friends with her, now more than ever.It was friday morning, the day after Sin was ****d and I was eager to get to school and talk to her, but she didn't show up, even after lunch I still could not find her. I asked our teacher if he knew but he just shook his head. I offered to take her homework and he...
You feel your body jolt forward and suddenly stop. You stumble around for a few steps as your head shakes and nausea sinks in. You bend over with your hands on your knees as you try to stabilize yourself while also not throwing up. After taking a few deep breaths your head starts to feel fine and the nausea goes away until you can finally stand upright again. As you do you look around and notice you’re surrounded by nothingness except whiteness. “Where the hell am I?” you openly ask even though...
FantasyYou wake up, or at least the closest thing to waking up. All around you is a bright, searing light. It has no source yet it burns with a raging heat, as if sentient, that you want desperately to avoid but you cannot close your eyes. You reach to cover your face but you find you have no arms, nor even a face. You can feel your body, every nerve ending shattering like glass and limbs flailing, but it is not visible or present. The broken remains of your consciousness tumble through the emptiness...
FetishIntroduction: Youll want to read Part 1 first! Lifes Strange Turns, Part 2 The phone rang, waking both Karen and myself with a start. Wed slept for only about 15 minutes. Well, it would have been bad to sleep longer, but it would have been almost tragic if the phone had rung while we were writhing around having such marvelous sex. Especially if shed had my cock in her mouth I thought! To give Karen some phone privacy and to take care of some personal hygiene issues, I ran into the shower and...
This is Lifes a bitch and now so am I!!! This is a fiction story!! The people in the story are not real!Please exsuse the puntuation and spelling I'm just a blond sissy!I start of my story with my wife leaving to go bingo with her mum, as soon as the car pulls away I'm up to my secret girl cloth's and sex toys.I am a sissy cross dresser, I can't help it i love the feel and how girlie it makes me look. I have...
We stayed in a three-story townhouse in a neighborhood called Carriage Mill. When you came in the front door, you were immediately greeted by two staircases, one leading down to a restroom, the laundry room, my office and the garage, and the other leading up to the dining room, restroom, living room, kitchen, den and patio. But at the top of those stairs, another set of stairs awaited, leading to the three bedrooms and two baths. It was a small, quaint home that I’d grown accustomed to, but I...
In this story, many will find what happened to me socially unacceptable. But since this has happened to me, I get to tell it and if you like, listen.I was very young when I found myself on the streets and it seems long ago that some things I do not remember but its the important stuff that I do. And yes, like so many other stories start, here is how I looked. 4 foot nothing, skinny, long blond hair and even then had more angelic features then not. I do believe that now, that I was a woman even...
Many things happened over the next few months, for one, I healed maybe better than I ever was, I discovered that there was another side to me and most important I met Tim. He was the one that found me and maybe even saved me. A middle aged man who once had a daughter, I know that because I am now living in her bedroom, sleeping in her bed and wearing her clothes.But lets rewind for a moment, the first thing I remember waking up is seeing Tim. He asked me my name, "Danny" I said, he introduced...
Hi! This is my first story on ISS so don’t be harsh on me. This isn’t a real story, but a fantasy which i am going to share with you,though the characters are real. I am a boy(21)(crossdresser) doing my engineering in Bangalore in a reputed college. I stay at one of my fathers friends house, his name is Rajesh. His first wife died due to cancer so he married again. His new wifes name is Rajni. Rajni, in her 30s, is a damn hot woman with a plus size figure. Now lets move on to story… Initially i...
Gay MaleIt was the night before my first day of school, I was excited. Sam was over and we were chatting away, she was really becoming a good friend. I told her about what had happened with Mike the week before and she listened to the whole story. She asked me how I had felt about it and I kind of laughed, "It left me with a good memory even though I am sorry it won't happen again, I don't think he will want me anymore but you warned me about it". Then I grinned, "I did have a really sore butt for a...