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My name is William. I am the eldest of a family of four kids, two boys and two girls. At the time I was seventeen. We lived in a small town, and my parents were well respected. I did well at school, played and succeeded in sports. I was and still am living an intense inner life fantasising on my sporting exploits and sensual encounters.

In those days, it was just as normal for teenage boys as well as girls to be baby-sitting at their parent’s friends and neighbours to make a few bucks.

For myself, I baby-sat at three houses. 

The D’s were friends of my parents. Mr D was a grumpy man, and Mrs. D a tall slim lady.

The O’s lived across the street, they were a happy spirited couple, Mr O took me out hunting small game and Mrs O was always busy in social organisations, their house was always in quite a state of disorder.

Then there was the G’s, our next-door neighbours. Mr G was a businessman, often away, never talking to anybody not even to his own family. Mrs G was a very nice looking woman, there were rumours in town she had a couple boyfriends. They had three kids, all monsters!

I was shy around girls and felt easier taking care of my sexual needs myself.

I preferred to fantasise about possible girlfriends and usually had crushes on older women like teachers, or Mrs D, O and G.

It all started at Mrs D’s. Checking on the sleeping girls, I noticed across the hall lying on their parent’s bed Mrs D’s clothes, either the one she’d worn before going out or one of the dresses she’d thought of wearing that night.

I entered the bedroom, looked at the dress, dreaming of watching Mrs D dressing and undressing. I then felt the material and put my hands under as if going up her legs and touching her breast. Naturally, I was getting excited and felt my hard on and lay on the dress as it was really her.

That night, I guess I just opened the drawers where she kept her panties and bras and felt with my hands getting hard then going on the couch to masturbate, dreaming about her. Later, I would feel, kiss and smell her lingerie and this brought me to the laundry bin where I could have her real smell and taste.

All week I would jerk off dreaming about them.

Mrs O was so disorganised that all of her clothes were stacked unfolded, I felt safer going through them without getting caught, so, at their place, I started to undress and put on some of her lingerie and walking about in their house. I fantasised of being a girl and having sex with Mr and Mrs O.

Mrs G had nighties like no other.

One day, I came back from school to find my mom and the three ladies sunbathing in our backyard. I was greeted with smiles, kisses and jokes about putting on a bathing suit and sunbathing with them. My mom was in her plain one piece, Mrs O in a small bikini showing off her small figure well and Mrs D had khaki shorts and a bikini top but to my surprise Mrs G was lying in a chaise-longue in panties and bra as if it were natural. For me it wasn’t, I’d put on those same panties and bra myself and knew the exciting feel of them.

Mrs, G asked me if I would check on her daughter sleeping while they enjoyed the sun, as the two boys had gone to their grandparents for the week.

As I went into the house, I only had in mind touching bra and panties as she was in, so after making sure Caroline was still asleep, I went to the bedroom, sure to be alone for some time. I pulled out one of Mrs G’s red silk nighties from her drawer, lay it on the bed and lay beside it running my hands over it, as if feeling her though the material and kissing her breast. I then undressed and put on one of her black corsage bras and assorted panties and lay back on the bed. I was in a world of my own, as I now regularly felt while babysitting.

I suddenly realized any of these ladies sunbathing next door could come back any time; I removed the lingerie, replaced it in the drawer, got dressed and walked back to our yard. Mrs G joked with me, asking if I’d fallen asleep in her house, I answered that I’d watched some TV. I walked into our house and went to my bedroom where I lay on my bed to masturbate once more, dreaming of my three ladies.

A couple of hours later, my mom shouted to me from downstairs that Mrs. G called to ask if I could go over to watch on her daughter because she had to go out urgently, so I went over.

As I got to her house, I heard Mrs G from her bedroom saying that she would be coming in a sec. Suddenly she appeared, wearing the same red nightie. I realized I had left it lying on her bed along with a white one, exactly the same as the one in her hands. I froze and my heart pounded, but at the same time, I was so excited seeing her this way. She came over to me, dropped the white nightie on my knees and said, “Will I had suspicions about you running though my drawers and putting some of my lingerie on, so now that I’m sure of it, you can do it with me. Put this on, now, get in the bedroom and put this on,” she repeated, pointing to her room.

As I walked into her bedroom I got the shock of seeing Mrs O sitting on the bed still in her bikini. She looked at me and said, “Will, I have noticed for a while that you play around with my panties and bras, now you will have to pay for the costume rental. Now show us what you do when you wear our lingerie.”

Both ladies sat at the top of the bed and repeated, “C’mon Will or....”

Still I couldn’t move, so Mrs O stood up and pulled my t-shirt off while Mrs G unbuttoned my pants and pulled them down.

“Now Will, you change into this nightie or we’ll get angry and call your mom in.”

So, I turned around, finished getting undressed and put the panties and top on, I turned back towards them, looking down at the floor, naturally I had a super hard on just by the feel of the silk on my skin. The two women were lying side-by-side facing each other looking at me, I didn’t know if their faces were angry or smiling.

“Ok Will, now show us and tell us what you do when you dress like this.”

Not realizing what I was saying or doing I answered honestly.

“I’d put another set on the bed and act as if I was a girl having sex with you.”

Mrs O stood up, took my hand leading me to the bed and said, “Okay, now show us with a real woman in the lingerie.”

Mrs G lay on her back and removed her bikini, I shivered at the sight of her small breasts and shaved pussy, whilst Mrs O backed up and sat in a lazyboy chair in the corner. Now Mrs G said, “Show me!”

Nervously, I placed one hand on her thigh and put my lips close to her breast, again without realizing I said, “Ohhh! I’d love to have breasts like yours.”

I put my other hand on my right nipple, rolling and pinching it. Then as I lowered my hand to grab my cock, she said, “No, no you don’t, Olive will teach you to make yourself cum like a woman.”

As I lay on my back she knelt over me, one hand going under her silky top and the other feeling her pussy. Mrs G then took my both hands to her lips taking my middle fingers into her mouth, sucking and licking with her tongue. She then took my right hand to my left nipple and my left hand, again holding my middle finger, to the tip of my cock at the point where foreskin edges the gland and lowered her lips to that exact same spot. I exploded immediately sending cum all over her lips and face and dripping back onto my belly.

“Will, you’re being very naughty, this is not the way a lady pleases herself and lover.”

By this time I’d noticed that Mrs O had joined us on the bed and it seemed to me that she now had a cock instead of a shaved pussy.

“Charlie will have to punish you for being dirty,” said Mrs G, Mrs O’s name was Charlotte but her friends called her Charlie.

Mrs O gently kissed Mrs G, licking her face and lips clean. At the same time she held the long slim dick that she’d strapped to her lap then rubbed my belly where some more of my cum had ran.

“Dirty little girls like cock in their mouth, clean Charlie’s cock with your lips Willy,” said Mrs G as Mrs O moved closer to my face taking my head and thrusting her long apparatus deep in my mouth almost suffocating me. Mrs G. had, by then, pulled her legs under mine, holding tight to my ass cheeks I could feel her fingers running up and down my crack and circling at my hole. I moved my ass as if wanting her fingers inside me.

“Willy girl is ready,” said Mrs G as she moved from under me to almost sit on my face, holding my legs up as Mrs O now knelt with both her cock and mine in her hands.

“Take her Charlie,” said Mrs G as she lowered herself onto my face rubbing her pussy and ass all over it.

Mrs O applied lube to the cock and my hole, sliding first one finger inside and then a second. I moaned, remembering the candle that I sometimes used on myself at home. The sensation now was so much better because this was really happening, just like I'd dreamt. She placed the cock at the entrance and pushed slightly, my ass clenched, this thing was so much bigger than that candle.

"Relax baby, you're going to love it." Mrs O cooed.

I let my body go limp and the cock entered my ass. I was shocked at how easily it went in and how little pain there was. She pushed the cock right in and I felt her legs on the back of my thighs. She began pulling out and pushing in, each stroke hitting my prostate and making me moan like a girl. She increased the speed of her strokes and my cock started jumping. This was better than any dream I'd had, I was being used like a little girl and loving every minute.

Soon I felt the familiar build up in my balls, I knew I was going to cum and I hadn't even touched my cock. My head lifted and I started licking franticly at Mrs G's pussy as I shot stream after stream of cum over my chest. It was by far the biggest and the best orgasm I'd had in my young life.

Mrs G laughed and said, "Well Charlie it looks like our girly boy enjoyed that, he'll be wanting a lot more of it. We might just let our husbands play next time, I'm sure she'd like that."

And I did but that's for another time.

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Welcome to Reality

I stare at my own reflection, still not convinced that that is really me. It’s not how I would usually picture myself; not how I usually saw myself. My eyes seem duller than usual. The hair on my head not quite so lush and verdant, but more hair than I’m used to everywhere else. My chest somehow thinner and not as toned. And, as my eyes roam down the reflection, I don’t quite recognise my cock, which is very strange given how often I look at it and think about it.The mirror is spotless, but all...

Fantasy & Sci-Fi
4 years ago
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Ring of Reality

Simon found the ring in a storm drain, half buried under decomposing leaves, discolored cigarette butts, and disintegrating paper bags and cups and other trash. He was waiting for the train to take him home after a long afternoon of accomplishing very little and the ring's glint caught his eye as he disinterestedly surveyed the gutters. He picked it out of the foul, rotten mess without a thought and slipped it into his pants pocket. The light winter rain washed the brown filth away...

2 years ago
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VR Sex Becomes Reality

I continue my yard work and think of my stepdaughter naked and in the shower and how daddy would love to be in there to start fucking her there. I go inside to get the key to her car and of course, it’s not where we hang all the car keys. She’s done in the shower and must be in her room, I go to the top of the stairs and yell to her to give me her keys. She doesn’t answer after I yell a couple of times. I curse to myself as I go down to her room to get the keys and to give her hell for not...

1 year ago
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Daydreams to Reality

A hectic week at university is over and done with so I thought I’d travel to Nathan’s house. A long-time friend of mine. We’d been meaning to have a catch-up but we had both been so busy for the last couple of months. We’d finally found a weekend where we’re both free and decided to have a sleepover.I pull up to his house and stare out my window. I bite my lip and sigh. If only he knew how he made me feel... Every time he smirks at me with those dimples of his, I get all hot and flustered. I...

Quickie Sex
4 years ago
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Dreams Become Reality

It’s a warm summer night and I have left the windows of my room wide open to allow the gentle breeze to cool the room. The soft light of the full moon shining through the sheer curtains faintly illuminates the room. I lay naked in my huge bed my body tangled in the thinnest of sheets after having tossed the blankets to the side during the night. You slip quietly through the window glancing briefly at the large dog lying on the floor at the foot of the bed. The dog looks up at you for a moment...

2 years ago
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Virtual Reality

“Walls have ears.” You may have heard someone say that; allow me to let you in on the secret – they have eyes and ears and can sometimes see into the minds of the people and creatures who live within those walls. Not every mind, not every wall: just special ones that are open enough, working on the right wavelengths, and so manage to connect. I can’t generalise, I’m a building, I can’t go around doing surveys and interviewing other buildings to aggregate their experience. I can read, I can...

Voyeur
1 year ago
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RealityPornKing

It is exciting to watch a slut getting plowed and see her vigorously bounce on a cock. Only a few things in life are as pleaurable as wanking to bitches getting fucked.I have to say that reviewing porn sites and forums is one of the best jobs ever. I get to watch tons of videos and view endless about of pictures of sluts masturbating and getting fucked hard.Even those who constantly try to demonize porn cannot deny that watching porn is one of the most pleasurable experiences. There is no...

Twitter Porn Accounts
2 years ago
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A Dream Witch Became Reality

"I can't belive this...morning...","Tudy!" , "Ahhh...crap..Yea mom i'm awake!".This is how each and every one of my mornings start...i'm Tudy by the way a 16 year old guy which just started the 9th grade.Where was i ....ah yes... I entered the bathroom washed my teeth, my face, and got ready 4 school. "Tudy, u already miss the school bus, here take some money and call a cab" , "Yea mom , sorry mom", after my dad died a year before she was quite overprotective when it came...

2 years ago
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Dream Reality

Cassie laid upon her bed in her dorm room cramming for her last exam of the semester. Economics was not her strong suit and she was getting quite tired of staring at the book laying in front of her. She would have enjoyed studying biology more, but that was a subject she had yet to take. Her dormmate was out studying with her boyfriend for her last exam, so that gave Cassie the room to herself. The quiet of the room was beginning to close in on her, causing her attention to fade, so she got up...

1 year ago
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Dream or reality

[This is the first story which I created for CHYOA, so please be indulgent. I translated it, I also made some changes (like the appearance of characters and rewriting some chapters so that it is more arousing). I have want it to be more like my own fantasy. I adapt the story (create chyoa chapters, review the formatting and maybe in time some alternative choices.) I also adapt it to the norm of age that is used here since the French law is not the same about age. The story was originally...

Incest
1 year ago
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A Dream Fantasy Hoping To Turn Into Reality

My name is Anand (name changed). I am 21 years old and live in Bangalore and desperate to lose my virginity. So as you can expect this is a fantasy story. I hope some horny girl or aunty might get lucky taking my virginity. You won’t believe that I did not even kiss a girl until now. So I am a desperate youngster. So coming to my story. I had recently attended the DJ snake concert where I went stoned with my college friends. Then I was lost in the crowd alone and totally high. I did not know...

3 years ago
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HH7 Appearance and Reality

HH7: Appearance versus Reality, part of the HH series TG adult fiction by talltglover. If you are offended by men or women having sex with transgenders or hermaphrodites, or live in an area where such activity is illegal, or are too young to be reading adult erotica, please do not continue. This story is unlike most of my other fiction, which concerns men turning into women (conceptually) or hermaphrodites and having sex with other men. This story was written as a special request,...

2 years ago
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Fantasy turned into reality

Fantasy turned into reality “Hey cuckold, did you enjoy fucking Ann last night, would you like to fuck her again?” my wife shouted across the room. “Oh yes, it was fucking great and please can I fuck her again,” I pleaded. “If you are a good boy, I will arrange another meet but I have another surprise for you this Wednesday,” she said. This had become our sex party night and I could not wait. A full six days to go. Was it a different woman, I wondered. I begged her to tell me more but she...

Wife Lovers
3 years ago
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Virtual Reality Reality

Like so many people in this year of 2023, we had all hoped the worst was behind us. The vaccine programs were only partially effective and the virus kept mutating putting more and more people at risk. The changes in society were almost unbelievable. I know no one would have predicted a several year lock-down, but it is proving effective. You could literally go days without seeing anyone, except your immediate family.Shopping was all done online and delivered with drones. Groceries were packed...

Medical
1 year ago
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Fantasy Reality

- 1 - Steve was used to the drive down through Wales. He lived in Lancashire, his parents in Carmarthenshire; it was not only the obvious route down in terms of speed and cost, but was much more interesting than sticking to motorways. And it avoided the toll on the Severn Bridge. This was a quick, practical trip down over the weekend; his wife was still at home, getting up to who-knows-what, but probably just watching telly. Lovely as she was, she was also trustable. Safe. It was times like...

Bisexual
1 year ago
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David Dreamscape Ch 01

His name was David, and David was ugly. I knew David in ‘real life’, he was the brother of a girl I went to high school with, and he really was so very unattractive. He certainly wasn’t my type of guy, I hardly ever spoke to him let alone look at him. Poor David, poor ugly David. For obvious reasons, I hadn’t thought of David, or his sister, for a very long time, and was therefore a bit surprised to find myself waking up after having dreamt about him. And it wasn’t just any old dream, it was...

2 years ago
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Beyond Dreamscape Part 3 Best Served Cold

Beyond Dreamscape Part 3: Best Served Cold By Diana Kimberly Heche Janet took him to be a little less than twice her age, thirty-five, perhaps. Simply saying he was handsome and obviously in great shape. Looking him over, his clothes, especially his shoes, screamed "money". He watched Janet, as all men do, however he did it with a calm confidence which neither spoke of cockiness or lechery. He didn't seem to be in a hurry to approach her, perhaps he was married or thought he...

1 year ago
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Saintly Dream Comes True

Stella Saint had an erotic dream, which disturbed her every night. She discussed the odd situation with Denise Moore, who persuaded her to enact the dream. Stella agreed to do so at a hotel. Little did she know that someone else had planned to make out with her. Cast of Characters: Major Characters: Stella Saint: Protagonist. Denise Moore: Stella’s friend and an intelligent psychology major. Leona: A lesbian felina. Minor Characters: Jonathan Wood: A businessman and Stella’s...

Lesbian
4 years ago
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The Dream Reaper

Chapter 1I awoke feeling the sperm running down my thigh. It had happened again, a wet dream that I’dbeen having three times a night. It always started the same way, I would be in a bar getting adrink, and once I sat down in an alcove that was situated at the back of the bar, someone wouldget under the table and start to give me the best damn blowjob ever. However, I couldn’t see whoit was, and when they’d taken me to the very edge, I would cum for real, and wake up. I cleanedup the mess, and...

1 year ago
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Virtually Reality

Shelly wasn't so sure she agreed. Her life was connected enough, without spending extra time playing with weird electronics. The evening could have been spent on a date, or studying, or just relaxing. Instead, she'd spent it listening about Ximena's new obsession, and now it was turning into some lame geekfest. "Aren't these 3-D glasses like they used to use with old TVs?" Shelly asked, watching her friend tease out the cords and plug them into the surprisingly large box. "Do you...

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