A Sissy Nappy Boy's Dream Comes True free porn video

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Pure fantasy with only the first and fifth paragraphs being true….

My wife is away for a month, overseas with her sisters and friends. Being a crossdressing sissy nappy boy, I’ve been running amok. I’ve been wearing nappies almost 24/7 and 99% of my time is spent dressed only in women’s underwear and usually with a wet nappy underneath. I have a fetish for the old lady style of granny panties, full slips, DD bras, girdles, shapewear (full body suits and high waisted control panties) full slips and full length nylon panties.
Sue has been gone for nearly three weeks and I have become somewhat complacent. I often have the front and back doors open to keep fresh air coming in. I try and keep an ear out for any visitors but sometimes when I’m watching x rated videos, I forget to turn down the sound. And this is what led to my fantasies coming true…

I was sitting at the computer, my back to the front door, watching a video on Xhamster of two young crossdressing twinks in panties and lingerie fuck each other senseless. I was completely engrossed in it. Their young toned hairless bodies with enormous cocks, ramming each other in the bottom. It was enthralling. I was wearing a women’s full length white cotton leotard. Under that I had on my DD cup bra, with the cups filled with white nylon full slips to give me huge breasts. I was also wearing a very, very wet nappy under the leotard which was full of skin cream. I use that partly to stop nappy rash but mainly because it makes the nappy so, so squishy. I had wet it numerous times over the last 4 hours and it had leaked a lot, making the upper parts of the leotard legs soaking wet. A nappy is no fun unless it leaks. And over all of that, I had on my very frilly, very lacy, bright pink adult baby dress which came down to the tops of my legs.

Without any warning I hear a voice behind me….”Well, Hi Dave…” Oh fuck me. My heart stops. I spin around in my chair from the computer and see Jill standing at the front door. Thanks to the way the house is lit up in the late morning, there is absolutely no doubt she can see me in all my full glory. I am royally screwed and I freeze like a deer in the headlights….

Jill is an old, old friend Sue and I have known for years. We have knocked around with her through thick and thin. Her husband, who used to be my best mate, turned out to be a d**g fucked asshole who treated her badly. We were so happy when he finally left. After he did, Jill would visit us often and share a joint with us. When we were renting a place that had a pool, we would often swim naked and then lounge around the pool with no clothes on. I always had trouble trying not to get an erection. Jill was no raving beauty but she was one of those women who just oozed sexuality. Her eyes, her voice, the way she moved…she was very, very attractive in an a****l way. Because Sue and her were so close, Jill knew that I wore panties. And she had caught me a couple of times when we stayed with her while we were building our first house, outside the shed we were staying in, wearing only a short white t-shirt and pink nylon frilly panties. She never made a fuss, she just knew that was who I was. I loved her for it. (This paragraph is entirely true)

So here I am. Dressed as a complete sissy boy, frilly pink dress and all. I had been hard as a rock in my nappy, watching that video. Now I could feel my cock shrink back to almost nothing as Jill just stares at me, open mouthed.

“Oh shit, Jill. I’m so sorry! I…I didn’t hear you coming. I…oh fuck. Oh please Jill, you can’t tell Sue about this! She’ll…"

“Ssshhh…” she said quietly and put a finger to her lips as she walked towards me. “It’s ok. This is your own house after all. You can do whatever you like” I stood up as she approached and she came right up to me, staring into my eyes. Oh, that look! She can stop a bull elephant in its tracks with that sultry gaze. I found myself speechless.

“I knew you were into panties, but wow! I never knew you were this kinky!” she said. “Look at you! You are a very, very kinky little boy, aren’t you?” I went to answer her but she stopped me by putting a finger to my lips this time. “Just be quiet while I look you over” she said.

She took a step back and ran her eyes over me from head to toe. “Turn around for me” she said.

“Jill, I…” I said but she silenced me with that look again. “Just be quiet and do what I ask” she said. “I want to have a real good look at you”

I turned slowly around, full circle, and stopped when I was facing her again. She came closer and reached for the hem of my dress. I went to stop her but she brushed my hand away and kept going. She lifted the front of my dress, all the way up to my huge fake boobs. She touched one, and then let her hand lightly trail down the front of my body, stopping when she got to the enormous bulge from my wet nappy.

“Now, I know that bulge cannot be your tiny cock, can it” she said. “I’ve seen your cock lots of times and it’s just not that big. So what’s making that huge mound between your legs, hmm?”

“I…I’m…wearing a nappy” I said quietly.

“I thought so. Sue told me you had…expanded…your fetishes. She wasn’t very happy about it, was she?” she said.

“No” I replied quietly. “She went ballistic”

“Yes she did. She told me all about it. And now here you are, doing it again. She wouldn’t be thrilled to know that, would she? And she would be very, very upset to know you’d been caught like this, wouldn’t she?”

“Jill, please…” I began but again, she silenced me with a finger to my mouth.

“Oh, don’t worry. I’m just playing with you. I would never, ever tell anyone. And besides, if I did, that would probably ruin my plans….” she said, with a mischievous grin.

“Your plans?” I replied. “What plans?”

“Ok, I’ll be straight up front with you” she said. “I remember being very turned on when I first saw you wearing panties. You probably hadn’t thought about this but I am just as kinky, if not more so, than you are. I have a very strong sex drive and vanilla sex just bores me stupid. I want to try everything! I tried to get Kevin to wear panties and lingerie, or fuck him with a strapon, or piss on me or just anything out of the ordinary. But he wouldn’t even consider it. He was the most boring man when it came to sex. I used to get so horny all the time but I had no release. I would masturbate several times a day, every day, trying to scratch that itch”

“But just playing with myself never really fulfilled me. And then that day, the first time I caught you wearing panties outside your shed….oh, wow! I hadn’t been so turned on for years. I could feel my cunt get instantly wet. It was kinky of you and I loved that! I noticed your dick starting to rise, you didn’t hide it very well. After I left you, I went back inside and rubbed myself through my soaking wet panties. I squirted so hard when I came, I had to change the sheets! And remember the next time I caught you? How I talked and talked just to keep you from going back inside? I’m surprised you didn’t notice the wet patch between my legs. I was dripping so much juice from my cunt! Fuck, I loved it! And yes, I did see a little wet spot on your panties as well. You were just as turned on as I was, weren’t you?”

“Well…yeah…I was” I replied “Really turned on. I tried and tried to think of something else so my dick would stop growing but it was no use. I just loved the fact that you were seeing me wear women’s underwear. It’s a huge fetish for me, as you well know. I felt guilty though. It was sort of like cheating on Sue. That’s why I stopped going outside in panties unless I knew for certain you weren’t home”

Jill laughed. Or more accurately, she smirked. “You think just because I wasn’t home, I couldn’t see you?” she said. “Have you never heard of….home surveillance cameras?”

My heart suddenly sank. I was starting to get hard in my nappy again, from the way Jill was talking. But now, the penny dropped. And it dropped hard. I’m pretty sure my penis simply disappeared up into my body. Because I now had flashbacks. Long buried memories of all the things I did at that time, thinking no-one would ever see or know just how kinky and perverted I was.

Whenever Sue went to work and I had seen Jill leave in her car, so I knew I was alone, my dick got instantly hard. Because I could then dress up and play outside to my heart’s content. I would get my stash of panties and lingerie and sex toys, dress myself to the nines and go outside. I would try on all sorts of combinations. Panties, bras, slips, teddies, girdles…everything. I would often piss in whatever I was wearing because I loved doing that. Feeling the hot piss run down my legs always made me feel so good. And sometimes, I would raid Jill’s laundry basket for her dirty panties. I would piss and masturbate in them, then rinse them out and dry them before Jill got back. I did so many kinky perverted things in hers and my panties and lingerie. I shot load after load of cum in them while outside. And I used to fuck myself silly with dildos and butt plugs. And many, many other filthy, perverted things.

And now, the realisation dawned on me. Jill had seen it all.

Jill was just staring into my eyes. She was pretty much reading my mind. I think she could actually see and hear my thoughts. She was smiling in that so, so seductive way that only she can. Her eyes were literally smouldering, her gaze boring into me.

“Yes, Dave” she said. “Yes, I saw it all. I was amazed at your…creativity… at times. I never thought a man could be so….perverted. Kinky. Filthy…”

I was now close to tears. My life was crashing down around me and I began to sob.

“Oh, no!” she said, walking towards me, and embracing me now. “You’ve got it all wrong! You don’t understand! I fucking loved it! I would replay the tapes over and over and I would masturbate over and over, squirting all over my bed as I watched you. I would fuck myself silly with my dildos, just like you did. Don’t you get it yet? I am just as kinky and perverted as you are. And to be honest, I haven’t caught you entirely by accident today. I planned this. I parked the car up the road and walked quietly up the drive and as quietly as I could to the front door. I’ve been watching you for a while you know”

Suddenly, this day has gone from the worst of my life, to being one full of potential. Jill was rubbing my back as she consoled me and now, I noticed her hand going down towards my puffy nappied bottom. I just stood there while Jill continued to massage my bottom through my wet nappy. She started to get right into it, and then she brought her other hand around to the front, cupping and rubbing the bulge there. I was getting hard again, and more than a bit turned on.

“I’d like to see you in just your nappy and bra” she said. “That would be so erotic!” Her eyes gleamed as I took my dress off and started to remove the leotard. Shortly I stood before her, wearing only a very wet nappy and my nightie stuffed bra. While I was undressing, Jill did the same and was shortly completely naked in front of me.

She came towards me again and this time, she put her legs either side of one of mine and started to rub her wet cunt up and down my leg. At the same time, she put one hand down the rear of my nappy and went straight to my anus. Because of all the skin cream, her finger slipped straight into me. I moaned a little with pleasure. With her other hand she was rubbing the front of my nappy, harder and harder. This had the effect of moving my rigid penis around in the warm squishy creamy confines of my soaked nappy.

I finally took the initiative and reached down to her cunt with one hand. She was soaking wet. I put two fingers inside her and started finger fucking her vigorously. She moaned loudly and thrust herself hard and down on my fingers. I put my other hand on her ass cheeks, cupping her bottom and pushing her onto my other hand. She then turned around and spread her legs and bent forward at the waist.

“Play with my bottom Dave” she said huskily. “Do whatever you want to with it”

I got down on my knees and parted her cheeks with my hands. I leaned into her and started to lick her anus. She cooed with delight “Oh yes! Yes! Lick my bottom you kinky pervert. Put your tongue inside me!” I curled my tongue and went in as hard as I can. I managed to penetrate her only a little bit but it drove her wild. She was panting and moaning. At the same time, I was fingering her cunt, her juices dripping down my arm.

She pulled away suddenly and turned around. “Pull out the front of your nappy, I need to pee” she said. I did as I was told and she came close, thrusting her cunt out and bending at the knees. She stood like that quietly for just a moment and then, she started to piss down my nappy. It was a dribble at first but then turned into a gushing stream. I managed to catch almost all of it in my nappy with only a few drops hitting the floor. The feeling of her hot piss running down over my hard cock and then pooling in my nappy between my legs was euphoric. There was so much of it, my nappy started to leak a little around the legs. This was my major fantasy coming true, having someone piss in my nappy.
When she finished pissing, she straightened up and then pushed her hairless cunt into my face.

“Lick me clean, sissy boy” she commanded. I licked and sucked at her cunt for all I was worth. She put her hands on the back of my head and pulled me harder into her. I was putting my tongue completely inside of her cunt and I could feel her start to shake and quiver. Without warning she came, her juices blasting from her cunt in a powerful jet of clear liquid. I swallowed some before she pulled away, raining her cum all over the front of me, soaking my bra and nighties, and topping up my nappy even more.

As her orgasm subsided, she sank to the floor and lay on her back, legs spread, her pussy glistening with juices, as she fought to regain her breath. I was still on my knees, trying to process what had just happened. From the time she first started fondling my bottom until she came had only been less than 5 minutes. She must have been well and truly on heat well before she even got here.

“Ooohhh fuck me!” she said. “That was so fucking spectacularly brilliant! Finally, I got to act out my fantasy. Or at least, part of it”

“Part of it?” I asked.

“Yes, only part of it. The best is yet to come. I’ve always wanted to have my way with you while you’re dressed as a sissy. I want to experiment on you. Find new and different ways to make you feel more like the sissy slut you really are. And that is what you are, isn’t it Dave”

I hesitated for a second but she nailed me again with her eyes. I was powerless under that sultry, sex filled, lustful, perverted gaze.

“Yes! Yes, I am a sissy slut and I fucking love it!!” I yelled. We both fell about laughing then, giggling like schoolgirls.

“Oh boy, you are everything I hoped you would be Dave. A first class, world beating, filthy perverted sissy slut. I’m going to have a lot of fun with you! But first, I think we need to clean you up a bit” she said, her gaze moving to the bulging piss and cum filled nappy hanging low between my legs. A puddle of juices was growing on the floor.

“We’ll use the kitchen table as a changing table” she said. “Grab some towels and lay them on it, then get your soggy ass up there. Where are all your sex toys?”

“In the bedroom in the box next to the bed” I answered over my shoulder as I waddled off to get the towels. By the time I got back to the table and laid out the white fluffy cotton towels, and got up on the table and lay down on them, she had brought the box out and was looking through it.

“Goodness me, some of these are huge! Do you use them all?” she asked.

“Mostly. I still can’t get the bigger ones all the way in but I’ve been practising” I replied

“Well, we’ll see about that” she said as she started to untape my nappy. As she pulled the front of my nappy down and laid it between my legs, my cream, piss and girl cum covered cock sprang to attention. She licked her lips and grabbed it with one hand and started to masturbate me.

“You know, Kevin’s cock was massive but on the rare occasions I could get him to use it on me, he always went so hard and fast it was more pain than pleasure. I tried anal with him only the once. It hurt so badly. But this sissy little cocklett, this I can see fitting my bottom rather nicely” she said as she continued to wank me. “But first, let’s see what fit’s in your bottom, my little sissy boy”

She rummaged through the box and came out with a small butt plug and the bottle of lube. She squirted lube on to her fingers and started massaging my anus. She then inserted a finger into me and slowly moved it in and out. I lifted my legs higher and spread them further, exposing myself fully to her. She took the hint and removed her finger and put the butt plug in. It was the smallest one I had and it slipped in easily.

“Seems like you have been practising, haven’t you?” she said “Your sissy boy cunt is loose like a well-used vagina” She took the small one out and grabbed a medium sized one. It went in reasonably easy and I couldn’t help moaning as she moved it in and out of my hole. With her other hand, she continued to rub my swollen cock. I started thrusting into her hand.

“Don’t you cum yet, sissy boy!” she barked. “I want your boy juices inside of me, not wasted anywhere else, do you hear me?”

“Oooohhh yes, yes” I moaned “But I can’t hold off much longer! This is so fucking hot!”

“Ok, well we better get thing moving along then” With that, she took out the plug and grabbed a large, realistic looking heavily veined dildo. She brought it to my ass and started to work it inside of me. She added more lube and twisted and turned it as she worked it into me. I lifted my legs up over my head, fully opening my ass to her. It finally popped all the way in and I nearly screamed in pleasure. I was bucking my hips against the dildo, forcing it as deep as I could. She pulled my legs back down and brought them together, holding the dildo tight inside me. She then climbed up and straddled me, her dripping cunt only inches above my cock.

“I would let you fuck my cunt but I think you’ll cum too soon. I want the first of your sissy spurts to go up my bottom” she said

She lowered herself down and grabbed my cock. She guided it to the entrance of her anus and pushed down slightly. With all the cream and cum and piss coating both her and me, my cock slipped inside of her easily. She didn’t come all the way down, rather hovering just high enough for my engorged penis to not fall out. I started to involuntarily thrust myself up and into her. She started fingering herself again, her fingers moving rapidly over her cunt lips, making a wet slapping sound as she rained cunt juice down onto my belly.

I was now pistoning into her as hard as I could, our bodies slapping together and making all sorts of sucking, squishing, wet sounds. I was in seventh heaven and was now on auto-pilot, just thrusting blindly into her. Nothing could have stopped me at that point. Jill was breathing very hard and moaning constantly, making little mewling sounds of pleasure and ecstasy.

Then I felt the first twitches and that deep, deep down feeling somewhere behind my cock. It was unstoppable. After just a few more thrusts, I came deep inside of her. I thrust up and stayed buried in her as my cock blasted cum deep into her bottom. I have never had a cum like it. I lost count but I think I ejaculated about 10 or 12 times. Jill orgasmed again at the same time, showering me again with her hot, slippery cunt juices. She fell forward on to my chest and my cock slipped out of her. I could then feel all my cum pouring out of her bottom and running down between my legs and into the nappy.

We lay there for some time, trying to catch our breath. Our bodies were slippery from all the piss and cum and the cream from my nappy and we just squirmed quietly together in little movements, making the most of the afterglow. Eventually, we had to get up.

We stood next to the table, looking at the wreckage of our uncontrollable lusting. A wet nappy, sex toys and drenched towels. Without thinking I put my hand on Jill’s bottom and cupped her cheeks and she did the same to me. We then both had the same thought and slipped a finger inside of each other.

And staying like that, we walked towards the bathroom……

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Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

4 years ago
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Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

2 years ago
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Sissy Rules Reads like a proper job description

(Found this on the internet... #65 seems especially made for me) Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows...

1 year ago
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Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

2 years ago
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Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl outfits, super swishy behavior and a little sex, not to mention dominant women, are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fictional fantasy work. No references...

1 year ago
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Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

3 years ago
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Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

4 years ago
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Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

3 years ago
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Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

2 years ago
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Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA....

4 years ago
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Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

2 years ago
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Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

2 years ago
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Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

1 year ago
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Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

3 years ago
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Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

1 year ago
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sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
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Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

3 years ago
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Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

3 years ago
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Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - By: Beverly Taff List of Characters. Me, Michelle: A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Doctor Shirley Williams: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine, AKA. Uncle Penny: My transvestite uncle. (Aunty...

3 years ago
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Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
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Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
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Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

2 years ago
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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

1 year ago
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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

3 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

1 year ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

1 year ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

2 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

1 year ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie Jamie, ...

1 year ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
1 year ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

3 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

3 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

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