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My Career
                                                                                                                                                                                                                                                                                                                                                                                                                                                                                   To understand where this story is going to go let me say it’s inspired by the character played by Richard Gere in the film “American Gigolo†and my thought’s when I watched this movie about how do you get into this line of work.
My name is Barry and it’s my 30th birthday tomorrow and as I sit and reflect it seems to me as if all the things that shaped my life happened around my birth date especially the past 18 years. My mom and I share the same birthday, I was her 18th birthday present, and my Dad is twelve years older than Mom.
Dad was always moaning about how getting married and having a child had spoiled all the things he planned to do. Two weeks after my 15th birthday Mom and I came home to find he had left to “discover†himself. The house was paid for and he'd left us enough money to get by for a while and occasionally sent money from places around the world. This was the catalyst for my decision to opt out of the high school, college, career then family trip and I decided that I needed enough money up front to enjoy my life at the pace I wanted.
I live in an enclosed estate and there are not many kids here. I joined up with Mr Tink, the estate handyman, and I started working the neighbourhood doing odd jobs. All the land around here belonged to Mr Tink when he was a a famer. He sold the land to housing developers but stayed on to do odd jobs having given the money to his children and grand children. Most of the people who bought places here were middle management or IT specialists and while the husbands earnt good money they were away most of the time, commuting to the city, leaving the women home and alone.
I soon had a selection of regular jobs from ladies who kept me busy. Because I was a kid they felt safer than having some burly tradesman around and were a bit more open and friendly. Nothing of a direct sexual nature happened for several months but the women did dress up or down and flirt with me occasionally flashing some cleavage or arse and making suggestive comments or telling “rude “jokes.
A few weeks short of my 16th birthday that changed. I was at Mrs Finch’s doing a full day of lawns, pool and car. Mr Finch travels a lot in his job and is often away for weeks at a time. I had noticed Mrs Finch, Val, dressing differently and generally watching me while I worked. All the work and fresh air had filled out my frame and browned my skin and as I regularly worked in shorts and T-shirts the women would check me out. When I arrived Val was wearing cargo shorts and a blouse. Later she had changed into short cut-off jeans that revealed long tanned legs and the blouse was now tied up under her boobs exposing her midriff. By the end of the day she was wearing an almost see through sun dress. My only access to sex was some magazines I’d found in a garage clear out so I had an idea of what things looked like and how they went together but I still hadn’t done it yet.
Val kept bringing me drinks, mostly orange juice, and by days end I was feeling a little worse for wear. I didn’t think it was the work or the sun so maybe Val spiked my drinks. I was sitting on the lounge waiting be paid and Mr Tink to come and collect me when Val came in to say she had to go to the bank to get some cash. I told her she could pay me later. Just then a beep sounded from the laundry and Val asked could I do one last job while she was gone and fold the underwear that was in the drier.
It seemed a lot of underwear for a lady living by herself but maybe she just let it build up till she had a full load. I began by selecting matching socks and balling them up. Then I selected underwear by colour and folded it into various piles. I started to look at the different styles, materials and colours and thinking of how they looked on Val and it was then that I felt my dick begin to swell. I picked up a pair of briefs made from a sheer material and on the front panel was am image of a finger pointing down to where her clit would be. On the back were two hands that appeared to be gripping her arse. My dick was throbbing to my heart beat and was as stiff as I can remember it being. Then I pushed my hand into the pile and grabbed a pair at random hitting the jack pot. These were a black stretchy lace pair of crotch-less briefs. Before I’d just had an image of Val in my mind wearing the briefs and showing me her arse and how they shaped to her curves but these were different because you would only wear crotch-less briefs if you were having sex.
My mind drew up images from the magazines with Val’s face and these briefs. I closed my eyes and brought them up to my face. It was then that Val asked did I like ladies underwear.
“I know what you charge for outside work but do you have a special rate for indoor work?†Val asked in a whisper in my ear.
She pushed me back onto the lounge and kneeling over me began to kiss me all over my face. Then she stood and pulling up the sundress revealed a pair of briefs with the words “Fuck here†written on the front. She grabbed my head and pushed it into her crotch humping it across my face. Unsure of what to do I just kissed her upper legs or panties or whatever was in front of my face. This seemed to please her as she kept repeating the word “yes†over and over.
Next she stopped and began removing her clothes and told me to get naked as well. Still not sure what was happening I undressed and as my dick sprang from my shorts Val gave a gasp and dropped to her knees and taking it in one hand slowly fed it into her mouth. Her tongue swirled around the head as inch by inch it disappeared down her throat. She took all seven inches and had her nose in my pubic hair. She let it slide from her lips and gripping it began to seriously work the head. My knees were getting weak from a combination of the work on my dick and the effect of the alcohol on my brain. Val stopped sucking my dick and placed a cushion on the floor telling me to lay over it.
I lay with the cushion under my arse which pushed my dick higher. Val stood over me and I could see her pussy as she squatted over my dick. She gripped my dick to keep it steady as she guided it to her cunt. My fuzzy brain began to think of two spacecraft docking and I still didn’t think this was happening to me. Then my dick made contact with her pussy lips and an electric tingle ran through my body. A little more movement and I was in and a feeling of warm dampness engulfed my dick.
Val, sank my dick in to the balls, leant forward to feed me one of her breasts. I hadn’t even noticed them but they were large and firm, the nipples round and brown and standing stiff. I sucked and bit at her breast as she moved her arse up and down on my cock. I locked my arms around her back pulling her tightly to me. Her movements were becoming faster as she rose up and slammed down on my dick. Val was nearly bouncing off the floor as she ground her clit against me with each downward slam. Her breathing was becoming ragged and she started yelling for me to fuck her and to fill her with cum. Finally the sensations became too much for me and arching my back off the cushion I shot my first ever load of cum deep into a woman’s cunt. Val cried in delight while I just made a deep grunting sound as another spurt left my dick.
We lay together for a few minutes just listening to each other breath. I don’t know how long it would have gone on or what may have happen next because Mr Tink tooted the horn to announce he was here to pick me up.
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