It was the summer after my 18th birthday when I first noticed him. He was a rugged looking guy with a mustache and cropped grey hair. His nose was a rugged roman style and he had blue blue eyes. He stood by the fence in what looked like silk dress pants and top, scanning the pool and observing the swimmers walk by. I'd never seen him around before but he was staring over in my direction. and so when I made eye contact I smiled nervously and he smiled a big wide smile back. Then he winked at me.
That really hit me funny. It was not like a hey nice to see you wink, it was a leering I see you and I know all about you kind of wink. I wondered if he was a cop who knew my friends and I had been dabbling in drugs. I also worried that if someone had been watching me, they might know my other secret.
I had been dabbling with crossdressing since I was probably 11. I snuck in sessions whenever I could get the house to myself. I always had a little stash of sexy panties and stockings and usually had a favorite dildo or buttplug stashed between my mattress. Most nights I slept in panties and pretty much rode a dildo off to sleep every night. That summer however, I'd been left to mind the house and work my summer job while my parents went up to the cottage.
Of course I took the opportunity to have my friends over to party. We usually just smoked pot but once in a while we took acid or even tried coke. When they'd all make their way home I was left with the house to myself to enjoy. Enjoy I had! I had a sexy little backless cocktail dress and high stiletto heels, a black satin garter belt and sexy stockings, I had even bought makeup and hair rollers. My hair was really long so by the time I was done, I looked like a little tart!
I fantasized about dating men, seducing them, sucking their cocks and being fucked by them. I wanted a strong daddy type. Someone who would take control and make me express it all for them. I sometimes spent nights watching porn videos and acting out the scenes with a dildo right on the entertainment room floor.
I didn't usually run around the main floor but if someone was watching me, they might see me or hear me. Can they tell what you are wearing with thermal imaging? They'd certainly be able to tell I was sucking on a big fake cock!
I realized I was being completely paranoid and dismissed it all. When I looked back at the fence I didn't see the man and I went and showered off, got dressed and went home.
That night after work I came home and no one came over to hang out. I still hadn't forgotten the man at the pool and I decided to lay low that night. I wanted to smoke a joint so I decided I'd go out for a stroll and no do it in the house. That way if the police did come, the house wouldn't smell. They'd have no excuse to come in. I decided to slip on a thong under my jeans just for kicks ( hope I don't get strip searched). I like walking around and feeling it stuck between my cheeks.
I headed along the trail beside the river and about half way down I ducked off the path and smoked a joint, looking out at the moon reflecting in the river. I heard a noise and realized someone was walking up the path. I doused the joint and held in the smoke watching. I was sure I wouldn't be seen. I saw a man walk up the path looking around. I couldn't make out his features because the moon was behind him. He seemed to be making sure no one was looking like he was about to do something illegal. Then he steeped out of his shorts and exposed an enormous semi hard cock perfectly silhouetted with the moon behind it. He spat in his hand and began working it in to a huge stiff gorgeous monster. He took his time and muttered and whispered as his breathing increased. I realized I was completely hard and turned on to near the point of cumming in my shorts.
I strained to hear what he was muttering, I think I heard him saying "don't be shy, come take that cock, yeah you sweet little pussy cum get it".
It was barely audible and my stoned mind could have been playing tricks on me. He groaned and ejaculated all over the path. Then he put his shorts on and and went strolling back the way he came. I kind of giggled to myself that he must be from one of the houses bordering the path out for a midnight wank. I wandered out from my hiding place to head back home in the opposite direction. I jumped out of my skin when I heard a deep voice from behind me.
"Off so soon? I hope next time you wont be so shy and bring that sweet little pussyboi ass out for daddy to play with."
I could hear him chuckle behind me as I ran as fast as I could. I knew he wasn't following. Had he known I was there the whole time? Had he watched me come in? Why did he call me a pussyboi? I figured it must be because I'm small (5'4") and have long hair. I also have really smooth skin so I don't look like a man's man. I did blow it off as coincidence and figured there was no way this man could know I was wearing a sexy little thong.
By the time I got home I had become very very turned on. A big part of me was wishing I had joined him. Actually I was beginning to wonder why I hadn't?
I spent that night furiously masturbating in the entertainment room. I pretended I had brought the man home and rode and sucked him all night. I didn't get to sleep until the sun was coming up!
The next day I woke up still horny. I had a big run in my stockings so I decided to hop on the bus and go out to the mall. The bus was really packed and I was shuffled to the back of the bus to look for a seat. The only available seat was next to the guy from the pool. He instantly recognized me to and shot me a big wide grin beckoning me to sit down. At the same time he was taking up too much room with his legs spread out a little too wide. There was no way I could sit next to him without our bare legs touching. I sat uncomfortably and he asked if I was off to the pool. I told him no I was out running errands no pool today.
He began making small talk and regularly touching my leg. It made me really uncomfortable but mostly because I was worried it was going to make me horny. I felt very feminine in the presence of this man and just the size of his rough hand on my little smooth thigh was making me feel really turned on.
I was just about to make a dash for the next stop when he once again squeezed my thigh with his hand and said "nice chatting the next stop is mind if you'd please excuse me".
I said sure and have a good day and I'll see you around. He looked back at me with that leer again(I'm blushing this is weird ) and then a voice I recognized said "Don't be shy now"
I was floored. Was that the guy who was jerking off on the path? Did this guy have a thing for me? Is this my fantasy coming true? Do I want it? I was dizzy and becoming hornier by the second. My heart was racing and I decided that the perfect thing to calm me would be something new and sexy. Something I always wanted but haven't had the courage to buy. I decided to buy my first merry widow. I'd always loved them in my dad's Playboys and have always wanted my own.
I went to the lingerie shop and confidently walked in and began browsing. Soon an older sales lady came to help me. I told her what I wanted and pulled a crumpled piece of paper out of my pocket pretending to read measurements (mine memorized) off of it. The transaction went smoothly and soon I was on my way out with my merrywidow, and 3 pairs of lace top stockings.
I decided that since I was pretty sure that guy was a perv and not a cop, I could treat myself to a little acid trip that night. I love doing acid and just playing, I get so into my fantasies and I was excited to reflect on this man's seeming desire to make them come true. A while after I peaked I decided I needed some fresh air and to go out for a walk.
It wasn't my conscious decision but soon I found myself of in the direction of the river path. I decided I needed to investigate and see if that guy was actually looking for me down there. I wandered down the path and went past where I had hid to smoke. Just beyond there was a bench and there he sat.
"Well well" He chuckled " I didn't expect to see you here tonight after the big shopping day!"
"Oh I needed to walk off some energy."
"I can think of a way to help you burn some of that" He laughed.
"What do you mean?" I said my voice quivering. I knew what he meant.
"I know who you are Kori, I've taken quite an interest in you these past few months"
My jaw dropped and I was quite surprised to hear him say my name.
"Don't be afraid, I like you very much and I wouldn't do anything to hurt you"
"I think I should get going" I stammered.
"This time I'm not letting you run away! You watched me, I saw you, I know you liked it!"
"I never...."
"I could hear you breathing I bet you almost came in your panties!"
I was living my biggest fear and my biggest fantasy at the same time!
"You know you liked it and you know it's what you've always wanted it!"
I stammered again " You don't know me you can't.."
"What you don't know is that I've been making little videos of you playing around in your rec room!"
I practically fainted.
"This is for your own good. Tonight you are going to go and pack up that sexy little outfit and other necessaries to make yourself look sweet for daddy. Be back at my place at 45 parkway crescent or that movie goes on the internet. I'm going to help you grow up tonight."
I was near tears I went to stammer something.
"You'd better hurry up and get there with a smile on your face and a positive attitude. We both know this is what you need tonight. You better get running!"
I was tripping right out and running. My mind was replaying what he'd just told me over and over. I thought about the footage he must have. My heart was in my throat and I ran.
At home I was panicking. I had only 35 minutes and he lived 30 away! I packed up my stuff in my backpack, my stilettos, makeup. earrings, hair styling stuff and of course the merry widow. I wore my strippers thong that tears off at the sides. By the time I was done I knew I wouldn't make it if I walked or ran. I grabbed my bike and raced his house.
I got there with 5 minutes to spare and took the time to take a deep breath. My head was swimming and I was so tripped out too! I realized that my little cock was so hard it was exploding. I decided a smile was in order and walked up and rang the doorbell.
He answered the door with a grin and said " Come on in don't be shy"
His hand was already on my ass and he was pushing me along into his TV room.
There paused on the screen was me in a garterbelt sucking my dildo.
"Just wanted to make sure you knew that I'm being and will be honest with you" He said in a very serious tone.
"Now go up to the bedroom and and get dressed up nice and pretty for Daddy. When I get done with you tonight you're not going to want that piece of rubber anymore!"
"Yes Daddy" I said meekly and started for the stairs.
As I passed him he grabbed hold of me and pulled me tight to him. Than he began kissing me hard as he ran his hands over my body. I resisted at first but soon had given in and was getting lost in the passion. He broke the kiss and was needing my
bum cheeks.
"mmmm this is going to be very nice" he purred.
Then he slapped me in the ass and said "Well you better get moving and get dressed so we can get that little bod to work!"
I was turned on a ready to go. I had decided that this was an opportunity I had always hoped for. Tonight years of fantasizing would become reality!
It took me 45 minutes to get ready. Makeup and hair took most of the time but now I had a good little slutty look going with little curly rings framing my face. The merrywidow hugged my body tight and made my ass look even bigger and rounder.
When I walked out to him I strutted. I felt sexy and he looked floored! I smiled and stared him in the eye seductively as I made a little show swiveling my hips as I walked. He grinned like a wolf his big (nine inches I'm guessing) cock out and hard and being stroked.
"Come on now, don't be shy honey, bring that hot little bod to daddy" He almost sneered out lustily.
I obeyed and soon was stander before him, he running his hands gently up and down my stockinged legs. He grabbed me by the hips and guided me around so I was facing away and began licking up the backs of my legs. I began moaning aloud as he started gently kissing my bum.
"Mmmm yeah you like that huh" he purred at me in a deep voice
"oh yes daddy your making me feel so sexy" I whined
"alright pup let's see what kind of a blowjob you can give"
"With pleasure daddy! Let me just get one thing from my bag"
He looked flustered but I promised to be quick. I grabbed my edible lube and headed back looking at him seductively. Just an aside if your giving a blowjob edible lube makes so many great things possible;-)
I stared into his eyes as I knelt before him and began gently stroking his cock against his stomach. I smiled and grabbed it and began gently licking from base to head. I licked up the shaft as he began to relax and moan with pleasure.
"Oh yeah you are such a sweet little thing. Lick that cock baby , say hello to your new best friend!"
I was really getting into it now. Licking up the shaft and swirling around the head. Teasing the slit and sucking hard on the head till it pops free. He was clearly enjoying this. I decided to move to the balls gently sucking each. Then I lifted his sack and tickled his asshole with my tongue. He was full out moaning and huffing like a bull now. I went back to work on his cock, covering it in lube and working it with my hand while I talked dirty to him.
"You like that daddy? I can be a good girl see? I got it all slippery and now I have to clean it off?"
"mmm well you better get too it my sweet little pussy ass"
I worked up to a full out deep throat and soon his balls tightened and he was shooting wad after wad down my throat. I swallowed hungrily but let a little drip off my chin for a visual for him.
He looked at me wild eyed.
"Get up and kneel on that couch" he ordered
I didn't hesitate for a second. Before long he had his tongue buried in my ass and I was squealing with delight! He spanked me, pinched my nipples, nibbled my ear and was soon removing my panties releasing the side clasps.
With my bum exposed he had me kneel in front of him resting on my elbows. He rubbed his now hard cock (again!!!) up and down in the crack of my ass, spanking me and telling me what a beautiful tight little ass I have. Soon he took some more lube and stuck his finger in my ass. Before long his dick followed.
He started slow and really it was me trying to pick up the pace. He just held my hips tightly and kept the same steady pace. I would try to push back to go faster, he'd hold my hips and slow it down. I'd try to pull forward when he went in so deep and I felt like I would explode. But he held me tightly and dictated the pace. I gave in and fell into his rhythm.
I was squealing and moaning and saying begging for more. He did pick up the pace but it never got to jack rabbit pace. Soon he picked me up and placed me kneeling on a footstool with my hands on the ground. Then he straddled behind me and began really driving me steady.
I could feel an incredible orgasm building and building. It was coming from so deep and radiating out towards every part of my body. I had never felt like this. It was so powerful it was almost scaring me.
"Oh my god it's never....Oh god Oh god...I can't....Oh Bill I've never oooooo it's never felt like this!! Oh god Oh god I'm...."
It kept building, he didn't slow and he had a good hold on me as my body went into spasms of ecstasy. He coaxed me along.
"Yeah that's it girlie, take it all, that's it take it all, oh yeah let it go don't be shy COME ON COME ON!"
He slapped me in the ass just as I began to climax and then grabbed my hips and held me tight against his crotch while I shrieked incoherently under the incredible power of this stud. He caught my cum in his hand and put his hand out for me to lick it off. Before I could finish he pushed his hand to my mouth and rubbed it around my face and into my lips.
As my orgasm subsided he began sawing away again and soon grabbed me by the hair and shot a big load all over my smiling face. Then I licked him clean.
We cuddled as he played our session back to me (he video tapes our sessions). He gave me pointers and I eagerly learned. He's really helped me blossom!
I moved in to the spare room the next fall. He's kept my secret but I've always behaved myself and lived up to my end too.
Merry Christmas everyone! Luv Kori:-)