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 15 years. My mom and I share the same birthday, I was her 18th birthday present, and my Dad is twelve years older than Mom. He was a 70’s rock star but as his career faded he became a music teacher which was how he met 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 neighborhood doing odd jobs. All the land around here belonged to Mr Tink when he was 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. As a fifteen year old and not to wise in the ways of sexual relations I just grinned or laughed and sometimes went home and jacked off.
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. I headed towards the laundry as Val left the house which is why I didn’t hear the car leave. I collected the underwear in the basket and as I passed through the kitchen I saw an open vodka bottle on the bench top.
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. Surprised I dropped the briefs and stood up but they caught on my erection that was tenting my shorts. Val walked over and as she took the briefs off my shorts gave my dick a squeeze.
“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. I felt a third and a forth spurt as my dick throbbed with a life of its own. At last Val collapsed on to me and we both lay on the floor my dick still in her cunt but losing its size.
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.
When I got home Mom asked me why I was smiling and happy and I just said that I’d finally completed a job that I’d been dreaming about. I went to my room to clean up before dinner and while having a nice soak in the bath thought about losing my virginity to a married women no less. Boy did I feel cool.
Over the next week I began to notice my lady customers dressing a bit more revealing. As Spring rolled into Summer swimsuits made an appearance and while none tried anything of a direct sexual nature they did begin to show more of themselves. In the past when they would have stayed indoors while I did the yard or pool now they lay on their sun lounges and hidden under hats and behind sunglasses I could feel their eyes on me while I worked. Again I felt so cool that these married women thought I was worth checking out.
It had been a week since I’d last been to Val’s and I was feeling a bit worried as Mr Tink dropped me off.
“I’ve got three jobs down on Valley today” he said “are you OK to get home by your self when you’re finished here?”
“I’ll be fine, just in and do the yard and the pool and I’ll be gone by lunch.” I told him.
“Just watch these women. The heat makes ’em act funny. So I’ll see you tomorrow.” he spoke as the truck drove off.
I was about to knock on the door when Mr Finch opened it as he was leaving for work. He pulled me aside and asked me to do him a favor.
“My boy, my wife is acting a little strange this week. I think there may be another man in her life.” he said
My heart skipped a beat and then he said to me “keep an eye out for any men showing up while I’m away and there’s an extra $20 for you when I get back in a few days time.” he gave me a wink and a nudge and the walked to his car.
I went inside and closed the door behind me. I couldn’t hear anything so I called out an hello. Val answered from upstairs calling me up. When I entered her bedroom she was dressed in a toweling robe and looking out the window through a telescope.
Without turning from the telescope she said “You can see all the way to the security gate with this. Ah there he goes on his way to work and that secretary with the blonde hair and fake boobs”
“Well what did my husband say to you before he left?” she asked
“He thinks you have another man and he wants me to keep a look out for strangers coming to visit.”
She laughed as she turned towards me. I could see her legs encased by black stockings disappearing under the robe.
“I know you are learning all this maintenance stuff with Mr Tink but I’d would like to be your teacher in another field. Are you interested?” she said as she smiled.
“What do you want to teach me?” I stammered.
“No need to be afraid, I’m going to teach you how to make love to a woman.” Val dropped the robe as she walked towards me revealing her tanned body. She was wearing a black satin bra the pushed her breasts together making them appear larger and firm. I also saw the stockings coming to the tops of her shapely thighs. In between she had on the black crotchless panties she had caught me with last week.
Val walked right up to me and placing her hand behind my head pulled my face to hers giving me a strong, long passionate kiss.
When Val released me she asked if she had been my first. I told her she was the one to take my virginity and with that she grabbed me and kissed me again and again. Her hands were rubbing my head and back and I responded by rubbing her back as well. My hands were working their way to her lace covered arse. We stopped for a breath and Val told me to undress. I quickly removed my shorts and t-shirt.
“Lesson one” she breathed in my ear “where to kiss a women.”
Val turned her back to me and told me to kiss her neck and nibble her ears. I began doing as I was told while my arms wrapped around her waist holding her arse close to my cock so it sat erect in her crack. Val was humming and moaning from my kisses and her hands grasped mine and brought them to her breasts.
“Lesson two, how a women feels.” she said softly as my hands massaged her breasts through the satin material of her bra.
She reached for the clip at the front of the bra and undoing it released her round but firm breasts. While I continued to kiss her neck I was also noticing how heavy and firm her breasts were. The nipples had gone from flat to stiff points of brown flesh topping these tanned mounds. Val turned and fed a nipple into my mouth and I latched on like a newborn sucking deeply and flicking the nipple with my tongue. Val was moaning louder and her hand briefly squeezed my cock before making its way to her pussy.
Putting one hand on my head she pushed me into a kneeling position in front of her crotch. Val put one leg up on the bed and pulled the panties aside giving me a close up look at her pussy. Her pubic hair was trimmed into a thin strip leading straight to the goal.
“Lesson three, eating a women.” said Val her voice now deep and husky.
She thrust her pussy into my face grinding her lips against mine. I did what I’d seen in magazines and poked my tongue deep into her slit and licked the length from clit to arse hole. This was really firing her up and she then told me to put a finger in her hole. My finger slipped all the way into this warm, wet hole. I began to pump my finger as well as kissing, licking and biting her pussy.
“Give me another” she moaned and I obliged by pushing a second finger alongside the first. I was really pumping her now and my hand was slick with her juice. My tongue was working overtime licking and flicking her clit.
“Stick one in my arse” she said and with one finger in her pussy I slid my other well greased finger up her butt.
Val was nearly jumping off the floor and looking up I could see her squeezing her breasts and licking her own nipples. I took my finger from her pussy and like I’d done before slid it into her arse hole along side the other. Her hand on my head continued to push my face deep into her pussy while my fingers fucked her arse.
Breaking away Val collapsed on the bed and screamed at me to fuck her. I climbed on top and lining my cock up with her hole slid gently forward. Once again I felt the electric tingle as my cock entered her pussy. Being as slick as it was my seven inches slipped right on in. Val raised her arse off the bed to force me deeper and I responded by pulling almost all the way out before slamming home.
Again and again and again I repeated this performance. My body was drenched in sweat and I had almost stopped breathing. The two of us were nearly bouncing off the bed as I continued to pound away the pent up feelings of a teenage boy. Val was now incoherent her ragged voice switched between moans and screams. I told her I could not hang on much longer and I was about to cum. Val told me not to shoot my load into her cunt. Being a dumb teenage boy I thought she didn’t want to get pregnant so I slid my cock from her cunt and stood beside the bed. Val grabbed my cock tightly in one hand and from beside the bed she produced a wine glass. Val pumped my cock until I shot my load into the glass and continued to milk it of every last drop of cum.
Val used her finger to stir the white goo with some powder already in the glass and then upending the glass swallowed the whole mixture in one gulp.
“A wise old women told me that if I drink the cum of one who fucks me for their first time we will be lovers for ever.” she said as she moved across the bed giving me room to lay beside her.
“So was your first lesson enough to bring you back.” she spoke as her finger traced a circle around my lips.
Breathlessly I said I would like to continue and she rolled on top of me and gave me a deep tongue kiss.
We lay together for several minutes just kissing and feeling not speaking a word. Then the phone rang and Val rolled away to answer it. As she talked on the phone she picked up her bra and put it back on then took off the panties and got another pair from he draw. I just lay on the bed listening to her conversation and was stunned when she told whoever was on the line that she was still dressing because her lover had just given her a good fucking. Looking at me she laughed and said goodbye to the phone call and hung up.
“You better get dressed and out in the yard before my friends arrive.” she said tossing me my shorts and walking towards her wardrobe.
“I’ll be going out with my SLUT friends.” Val giggled.”SLUTS stand for Summer Land Unique Tea Service and its a group of women from the estate who get together for morning or afternoon tea and maybe a movie.” Val turned her back to me and motioned for me to zip her up.
I was in the yard when I heard her leave and once I’d finished I went inside to get a drink and to lock up. I’d never seen much of this house from the inside and it was larger than my house so I decided to have a look around. I wasn’t going to take anything just a browse at how others on the estate lived. Having a wicked thought I went back to Val’s bedroom and poked about in her dressing table. Tucked away at the back I found a vibrator and apart from some other sexy underwear there was nothing of interest here.
I wandered from room to room, they had a pool table in one room and a home theatre in another. The system was run from a computer which I thought was off but the screen popped up when I touched it. I began to scroll through the movies on file and it was a mixed collection. Then towards the end I came across a folder that had several unnamed files attached. I clicked one with the mouse and and a window asked if I wished to see this film. Tapping yes the lights dimmed and the movie was projected onto the wall at the front of the room. Staring at the screen I was seeing Val and Bev, another of my regulars, having sex on the pool table I’d passed on the way in.
I reached for the mouse and clicked on the next file and this was of another client, Maggie, getting fucked by an unknown guy. In quick succession I went through each film and they were all of women I deal with having sex in a variety of position with different men and women. I shut everything down and left wondering what I was in for.