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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<a href="https://www.lushstories.com/stories/crossdressing/from-dream-to-reality-1.aspx">From dream to reality</a>