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I’d known Debbie for about four or five years and our relationship had grown, over that time into one of a very close sexual and emotional one, in fact id go as much as to say I was madly in love with her. I was also, during this period, also having an ‘affair’ with a divorced woman I worked with called Sandra who knew of my crossdressing desires and also my meets with Debbie. It was a bit different with Sandra insomuch as that I was very fond of her but it was definitely more of sexual ‘arrangement’. She just couldn’t get enough sex and I was happy to oblige! On one of my visits to Amy Jane’… Read more

I love a nice dick! It's beautiful, it's perfect, it's delicious! Your skin is soft, divine, delicious, wonderful!! And when the balls explode that delicious treasure that is cum, it drives me crazy to savor every last drop!!! It's so good!!!... I love a nice ass! Full, perfect, beautiful and tight!!! I love drowning my mouth in the beautiful and soft buttocks!!!.... And then feeling my very tight, in a wonderful and divine fuck!!!! I love bodies, I love sex, I love touching my nipples!!!.... But then I like being used, eating me... all of it! I like to give myself!!! I like to feel the vigor… Read more

“My Bra and Panties are Missing!” I’m Jan, and my favorite low cut sexy bra, and sexy panties both were missing. I wondered if my mom found them and chucked them out? I told my boyfriend Trav of the mystery. He checked his car and….nothing. It nagged at me how could this be? That night we were watching porn in my room and he was flipping around porn pictures and stopped at a site to view some. It was young guys cross dressing. We giggled at some of the guys wearing women’s clothes. We clicked around and that’s when I saw them. The same bra and panties I couldn’t find. I stopped and carefu… Read more

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"Now girls, if you want to open your desks, choose a dildo, and we will have some cocksucking practice." I looked around and saw everyone else opening their desks, so I opened mine, and what I saw was a collection of any sex toy you could think of, and many I had probably never heard of (yet!). There were dildos, vibrators, butt plugs, nipple clamps, and various whips and restraints. I quickly glanced at Frankie, and saw she had chosen a medium sized dildo, realistic looking, but pliable. Then I glanced around and saw some had chosen massive black cocks, but some were more modest sizes. "Now… Read more

When Miss Thorne came into the room, she looked at me with a mischievous grin on her face, making me realise she knew exactly what had just gone on in the office, I even looked round the room to see if I could see any cameras. "Follow me, Samantha" she said, and for the second time I was following her sexy body. Fortunately it was not far, because I hardly felt capable to go far, and she went into a room, and I followed. The room was almost like a shop, there were racks of schoolgirl uniforms, as you might expect, but also cheerleader outfits, ball gowns and what even looked like maids dress… Read more

As I followed Miss Thorne out of the room, I was amazed at how quickly she was walking. I remembered when I had tried to walk in heels that high, and I just fell over, yet she did not appear to be rushing, and I felt I almost had to run to keep up with her. The view I has was magnificent, her pony tail swinging from side to side,  her arse wriggling in the tight skirt, in fact it was so tight I am sure I could see the tell tale ridges showing that she was wearing a suspender belt. As I struggled to keep up with her I was aware that everything I was wearing was reminding me of the feminine… Read more

I can think of worst ways to wake up. Frankie's body was spooned against mine, my cock nestling in the cleft of her bum, my arm over her body and my hand on the curve of her tit. I gently moved my hand across her skin until I feel her nipple. I could feel her nipple harden, and my cock was doing the same, pushing even further into the cleft of her bum. She gave a soft mmmmm of pleasure and wriggled her body, showing she was more than happy with what was happening. Then...... In the distance we could hear , bang, bang, bang "time to get up ladies." The reaction was immediate, Frankie jumped out… Read more

How I first met Frankie was bizarre, but nowhere near as bizarre as the events that followed. Firstly to introduce myself, I am Sam Holder, I am 18 years old and was enjoying having a beer in the pub, thinking that I would finish this, then go home have a few goes on the PlayStation then probably watch some porn and have a wank. Maybe not the most exciting thing, but I would have been happy with that. Then I heard a voice say "There you are sweetie." As I looked up, the first thing I noticed was a perfect pair of legs, with a skirt that came to mid thigh. My eyes travelled up, taking in the s… Read more

When I was a boy I loved going to the cinema. I lived in London not far from Dalston. There were several cinemas on the main road there in those days, maybe 4 or 5. I would often spend my pocket money going from one cinema to the other. Firstly for the Saturday morning club and after the clubs finished I would re-enter to see the main weekly programme. One Saturday morning I was sitting a bit apart from the main group in the cinema (everyone always wanted to be near the big screen!) when a man came and sat two seats away from me. I didn't take much notice of him and continued watching… Read more

The occasion of my tenth birthday was a special memory. My birthday fell on a Monday, with all the usual fanfare and fuss made when reaching double digits. I got some great presents and had a nice family dinner, but what I was really looking forward to was staying over at Danny’s house that coming weekend. Not just for one night, but two! I was to head home after school on Friday, grab my bag and stay at Danny’s Friday and Saturday nights. By this time, I had stayed at Danny’s numerous times and his house was easily my favorite place on Earth. His Mom was a big part of that, of course. Just t… Read more

I watched Mrs. Gordon exit the room, marveling at the way her nightgown swayed with the movement of her hips and ass as she walked. I turned, thinking I would say as much to Danny, and found his head still resting beside me on my pillow. He smiled a smile that said he knew exactly how incredible his mother was. “Your Mom is amazing!” I said. “I know” he replied smiling. He shuffled a little on his side, and brought his knees up to rest against my right leg. “I’m really glad you came, this is my first sleepover.” “Mine too” I replied. He asked if I had had fun and I replied that I had.… Read more

I saw Danny again at school on Monday. We didn’t directly talk about what happened at his house on the weekend, but the dynamic between us had changed. We spent more time together in breaks, usually sitting under a tree chatting or in the library mulling over a book. He would always sit very close so our legs touched and, a couple of times in the library, his fingers would sometimes brush against my leg under the desk. He was always very careful to make sure no one was watching though . By Tuesday, Danny had asked if I wanted to come over again after school, but I wasn’t allowed. The next day,… Read more

A few days had passed since my last visit to Mr. J’s house with nothing much to do. I hadn’t bothered canvasing the neighborhood for work, I was making good money at Mr. J’s, and I much preferred the work at his place to what I’d have to do elsewhere. So, telling my mother I was off to look for work, instead I would just go to various locations and masturbate. Sometimes it would just be the Junior High across the street from home, sometimes further afield. A nice woody park was a favorite, and, if I was on my bike, there were a few bays around where I could play. Sometimes there would be sunb… Read more

The next morning I rose a little late, around 9am. I had spent quite a few hours the night before engaged in vigorous and repeated masturbation reliving the events of the day before. Half an hour later I was excitedly riding to Mr. J’s house. Arriving at his house, I was suddenly nervous. I definitely wanted more, a repeat of yesterday’s activities, and maybe more. I had been thinking of his cock all night, and I was pretty sure I wanted to do more than just touch it. I wanted to taste it. To lick it and take him in my mouth. I wanted to taste his cum, like he had tasted mine, but most of all… Read more

In the summer of 1980-1981 I was ************. In the southern hemisphere, summer starts on December 1st and ends at the end of February. For much of that time is the summer school holidays. School ends two weeks before Christmas and starts up again at the end of January. That’s six weeks off – a fantastically long time when you’re 11. Between hanging out with some friends and biking around and masturbating in secluded spots I had quite a lot of free time and my parents sat me down one day and suggested I could maybe look at getting some kind of summer job. I had never had a job, so I wasn’t… Read more

First things first – you should read “A Surprise at Danny’s House” before reading this. In fact, you should read the other Danny stories as well before reading this. All my writings are true, they all happened. My 10th Birthday. The week of my 10th birthday dragged. After the events of the previous weekend, I couldn’t wait for the week to end. I had a two-day sleepover at Danny’s organized for the coming weekend and I had a feeling it was going to be epic. I wasn’t wrong! At school on Friday, Danny was so excited. He had been excited all week, as had I, and the anticipation was almost over… Read more

So I log on to the site I use for meeting my subs. It's mid afternoon and work is boring. So why not have a browse? I am busy looking at the usual emails from hairy panty wearing old men and jokers the 'lets fuck' brigade that have not even read my profile. As if I would waste my seed in some t**t that isn't deserving of Masters breeding juice. The notification goes and I open the mail 'wannabe sissy girl' is the profile name and there is a message.... 'Hi Sir, total femboi degradee, I will do any thing you say Sir, are you free?' So, let's put this to the test bitch, I think. 'Ok I am free no… Read more

So, this bitches' ass cheeks are reddening nicely. The femmeboi is struggling to breath and cope with the enslaught my meat is carrying out on her throat. Her pink nakedness is such a contrast to the dark greenery and the woods that surround us. Her pert tight sissy body is there on display, on all fours. The bitch was there naked and just waiting for me to do as I please! An opportunity I did not intend to waste. The woods remained silent apart from the immediate grunt and slurp of this bitch, as I raid her mouth and throat. The odd whimper spurs me in to greater thrusts, expertly angling my… Read more

When you see a condom on your top, what do you do? a) I close my eyes and go through it despite the uncomfortable feeling b) I tell him that I‘d prefer it raw c) I walk away d) I do it like a pro and show him what I want. I pull the rubber off his cock and throw it in the trash bin.… Read more

i was reminded of a big man that i invited over from an ad. He was older and i felt his manliness and desire as soon as he entered the room. He held me in his arms and gave a gentle tweak to my nipple making me feel submissive and girlie. He stripped of me of my clothes and brought me to bed to lay next to him. Soon he guided me towards his cock to feel my wet mouth sucking his manhood to attention. He had mentioned he did not enjoy wearing a condom but know he whispered that he was going to take me bareback and fill my ass wit… Read more

My wife said to prepare for my new position, that I will have to spend as much time 'en femme' as possible. That meant that all day I would be wearing high heels, as well as my lingerie, as she quite rightly said, the last thing I would want to happen is stumble, fall and reveal my secret. Also I had to practice my female voice and she told me to record myself reading out loud from her 'Cosmopolitan' magazine. Let me tell you some of the articles in there were as raunchy as any men's mags, there were articles like 'Good vibrations: which is the best vibrator for you?' and 'Oral sex, spit or… Read more

Friday At last my wife has relented, and released my cock. I can feel it throbbing, enjoying it’s new found liberty. It is tenting my knickers, at the moment of release when it snakes past the waistband of my knickers. The feeling of the elastic of my knickers, as it rubs against the underside of my cock is fantastic, this kind if restraint I don’t mind at all. I am not sure when she had removed my cage, it must have been while I was asleep. I look over to her, and see her breathing slowly and deeply, showing she is still asleep. I almost feel like kissing her feet in gratitude, and the thoug… Read more

I felt the blood drain from my face and I waited for her to start shouting and screaming and probably talking about divorce, but what what she said shocked me even more. "You are right Mum, he does look pretty as a sissy." I turned back to face Joan and she said "could you get him ready to be my sissy." My wife took me by the hand and led me to the bed. I followed meekly, almost in a daze, not knowing what was happening. My wife got me to kneel down in front of the bed, with my arms stretched across the bed, I had the unusual sensation of my boobs pressing against my chest, making me think th… Read more

The weeks that followed Christmas were hectic with preparing for Joan to move into her new house. It seemed an endless round of measuring rooms, going to shops and ordering furniture and fittings. Then when she moved into her house, it was waiting for deliveries and moving things around to her satisfaction. On the first weekend after she had moved in, I was relaxing on the sofa, just wanting to relax and do nothing, then the phone rang. Lesley answered it and it was obviously her mum on the phone and as she was chatting I heard the ominous words of "I'm sure he won't mind", and I knew my pl… Read more

Nothing else happened until Christmas day. We had decided to open our presents together in the living room, but there was one present that I had got for my wife that I didn't think was for public unwrapping and on Christmas morning when we woke up I handed it to Lesley. With a smile she said " I thought we were opening the presents together ". My cock was already throbbing with the thought of her seeing the present "I don't think you would want your mum seeing this." She opened the present and pulled out a red lacy suspender belt, with matching bra, and crotchless knickers. "Hmm I see what y… Read more

I woke in the next morning, and I was aware my wife's body was spooning mine, and her hand was stroking my nipple. I know my nipple was getting hard, and so was my cock. I reached my hand to stroke her body, expecting to feel the silky feel of her nightie, but all I felt was bare skin. As I moved my hand further down her body I felt that she was wearing stockings and suspenders, but no knickers. By now my cock was rock hard. She pulled my shoulder so that I was laying on my back and said "I was hoping you would be awake when I came in last night, as I had something to celebrate........I got a… Read more

We woke up about an hour afterwards, and the tea was totally cold, so we got up. After having a shower and getting dressed, I went downstairs and Joan was already in the living room, this time fully dressed. I was expecting a knowing smile, or wink or even a suggestive comment, but all she said was "Good morning sleepy head." It was such a 'normal' thing to say, I began to think it had been a 'wardrobe malfunction' that she flashed her nightie, or had I imagined it! For the next two weeks nothing unusual happened, and I began to wonder if the events had happened, or was it my imagination. Th… Read more

I lay on the bed, stunned by what had happened. Joan's reaction to seeing me on the bed, dressed in her lingerie was almost as though it is the most normal thing to see. There was no screaming, no abuse, and she did not get my wife, to show her what a pervert she is married to. After about 10 minutes, I could feel the cum soaked lingerie was getting cold, which made me spring into action. I took all the clothes off, and put them in a pile, tidied up all the other lingerie and put them in the drawer, along with the dildos. I knew I didn't have to try to put them back as they were, as my Moth… Read more

To know how I became my Mother in law's sissy, I will give you some background first. My name is Mike and my wife, Lesley, is about 10 years younger than me, and her mum, Joan, gave birth to her when she was just 16. I believe it was a consequence of a 'fumble behind the bike sheds' which went too far after the school disco. But it does mean that I am closer in age to her mum, than I am to my wife. She bought her up as a single mum, and it was only when Lesley was 18 and had her own flat and was independent that she met someone who she married, and he had a property in Spain, so she went there… Read more