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Wayward Boy Ch. 05
After Diane there were several girls. I fucked Ellen Fran and Inez. Then my last assignment was Janice.
Janice was a big problem for me. Her father was the richest man in a very wealthy town. It was well known that messing with Janice would get a guy in very big trouble. However I got the word that I was to take Janice on a picnic. The word came from Janice grandmother. The old lady was in a wheelchair but she ran Janice house like a dictator. If grandma wanted it it would be OK.
Janice appeared for our tryst wearing a shirt and carrying the usual picnic basket. She skipped down the dock and jumped into my sail boat clearly ready to be taken out into Chesapeake Bay and fucked. She had the same in charge attitude she had always displayed back when we were in high school.
I set sail into Chesapeake Bay. Janice waited only until we could no longer see the dock in the dark and then she peeled off the shirt to reveal a sort of one-piece bathing suit. Only it was see-through mesh. It was as if Janice were nude only sexier.
As we sailed along Janice immediately began to tell me how things were.
She had remained a virgin all through high school because of the interference of her father and grandmother. She had finally talked to her grandmother and convinced the old lady that a girl needed to have some experience before her wedding night. However Janice did not need any publicity about the matter. Also I was tall and strong. Janice was tall and strong for a girl and she did not need a wimp.
Janice then confided in me that she had her cherry surgically removed by a doctor. If I made one joke about horseback riding I was in big trouble.
I told Janice that I would not make any jokes. I also asked Janice what would happen if I gave her the spanking she so obviously needed.
Janice was about to erupt when she suddenly realized that she was in the Read more…
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Back Seat Driver
I drove into Center Street Car Wash at 2:00 in the afternoon. Yes I was skipping out of work. There were just a couple guys there washing a big off-road truck. I pretended not to see them as I put my coins into the machine and then took off my suit-jacket. I knew the guys were still watching me no doubt hoping to see me get all soapy and wet as I washed down my car my tight black skirt riding up my thighs like something out of a music video. Whatever let them look. I wasn t in the mood for flirting. This was a very serious moment: possibly the last time I would ever wash Ginger. Someone had answered my ad.
I didn t exactly want to sell Ginger. But I had room for only one vehicle at my condo and I was beginning to realize that an early 70s muscle car wasn t the sort of vehicle that petroleum executives were expected to drive. Sure it consumed an obscene amount of gas but it didn t project the right aura. I had already gone down to the Mitsubishi dealership and picked out a shiny black SUV. I hated the conformity of that: an SUV. But it had to be done. Some guy was coming by at 7:00 to have a look.
My parents had bought ginger for me in 1990 when I turned 18 they got her from some estate sale for a fraction of what the car was worth. She s a 1970 Mercury Cougar a beautiful orange with a black stripe down the side rear spoiler and a 428 CID V8. I knew nothing about cars when I got her but I learned mostly because the car was a magnet for boys who knew about cars. They d ask me questions and I d blush in my bookish way and then the nice ones when they realized that I didn t know what they were talking about would explain things to me. Like how the 1970 was really the last year of the Cougar as a muscle-car. After that Mercury began to move it over into the luxury car market.
The guys watching me were car guys. Maybe they weren t watching me at all maybe they were watching Ginger. It was hard to tell Read more…
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The Awakening
Winter was almost upon them the evenings were coming earlier and with them they brought the cool South Westerly off the water. It was still early about five she guessed and it was already getting dark. Heavy grey clouds hung off to the west and the sound of distant thunder rumbled in the distance so deep that she felt it in her chest. Rain was on the way she could smell it rain together with newly opened roses drifted in from the garden below where she stood on the open porch.
The log cabin was built high up in the hills above Cape Town far from the hustle and bustle of city life and the stresses that it brings. A friend had insisted that she spend the weekend relaxing with him at his cabin he had long been trying to persuade her to come up to the hideaway but she had always made excuses why she could not. Now looking at the beautiful view she was sorry that she had not taken him up on the offer sooner. It was a strange relationship one that had developed over time without either of them giving it much thought. She was uncertain if he had intentions of taking their friendship further and she was afraid of how she would feel if he tried. Whatever his intentions she needed the break and was grateful for the opportunity to take advantage of this beautiful seclusion.
The wind was picking up she stood with her legs pressed tightly together as the wind rippled her thin skirt around her thighs. Shivers ran down her back and the sensation caused the hair on the back of her neck to stand erect. She folded her arms tightly across her ample breasts and she felt her nipples harden as the thrill of the winds cool fingers caressed her dark skin. Her long jet-black hair which cascaded down over her shoulders and ended almost at the fold of her buttocks was teased gently by the pull of the breeze and she closed her eyes and drank in all the different sensations which assaulted her senses. Then suddenly much closer now the sound of Read more…
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From Girl To Womanhood
Laura was a beautiful 20 year old girl who was perfect in every sense. She was at University where she scored the highest mark in her first year and now she was taking the time off in the summer holidays to lie on the beach and work on her tan. She was very self-conscious about her body but she shouldn t be for she had a model body and a face that was both stunning and sweet. Laura was 5 ft 5 a blue eyed brunette with a very voluptuous figure with 34D breasts and long legs that were smooth and firm. She certainly emphasised her curvaceous body in the light blue bikini that she had on today which left little to the imagination. A lot of men had tried to woo Laura as you d might expect but she was not interested because she was so diligent and concentrated on her studies. Her mum had told her that men were to come later but now is the time to obtain your qualifications. Laura held that look of innocence about her and you could instantly tell that she was a virgin.
Laura was lying on her side with the sun beating down on her most gorgeous body inhaling the cool sea breeze and enjoying the feeling of the soft silky sand beneath her. She was reading this women s magazine and in it was this article on female masturbation. Laura was getting very aroused by this and without realising that she was in a crowded beach her fingers automatically reached down beneath her bikini and she started to slide two fingers in and out of her already moist opening.
Tom and Alex were both walking down to the beach hoping to have a good swim in the warm sea when they spotted Laura. They instantly felt their cocks move in their tight speedo swimming trunks. Tom and Alex were both firemen and they had the typical iron-man body with the six-pack and pecks broad shoulders and strong muscular legs. They had come to the beach for the weekend and had set up their own tent in a quiet area of the coast. The two stood over Laura for a minute and watched as she Read more…
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Algebra 101
It was my first year of college and my parents had saved for years to get me there. I was there although I was indeed broke. Being so far from home was the worst part of it I guess being that no one could actually be with me. I was truly on my own. For the first few months I made it it was tough and money was tight but I made it. Some of the classes were hard but I had some great teachers. Algebra was the hardest but it was also the class with the best teacher. Mr. Jemison was always willing to help and never minded taking extra time out of non class hours to work one on one with his students.
Once my money began to run low I knew I had to do something and of course the answer was to find a job. Experience was definitely something I was lacking so my options were limited. I spent the evenings going from one restaurant to the other many of which were hiring but none that could work with my school hours. I had not decided on a specific major or I could work on a pre-profession program. But considering it was already mid-term I was out of luck there. It seems like I had covered every coffee shop and every mini-mart in the area when I came across a tiny club called The Toy Box . It was pretty obvious that is was a strip club marked with all those XXX s on the door and sign. Believe it or not the place looked pretty cozy and I needed a drink BAD.
When I pulled in the thoughts of going to in to a female strip club for a drink crossed my mind as weird Okay really weird not that I thought for a moment I wouldn t fit in or have even a lack of self confidence. I had never actually been with another woman but I had kissed my best friend in high school while the locker room of basketball players watched of course I had never lived that one down. I didn t consider myself Bi but I did find the female body pretty in it s own way. If there was any thing that my parents and family had instilled in me it was self confidence. Read more…
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The Ranch
When I was 16 years old mom and dad went through a nasty divorce. I loved them both but stayed in New York when dad went out to Nevada to open his business. I was something of a nerd and wound up graduating form high school at the top of my class but still a virgin. A short while after graduation I reached my 18th birthday. Mom decided to marry a guy she had been dating a while. She asked my dad to have me live with him. I wasn’t too happy but my dad promised me a good time so I left home and joined dad in Nevada.
Dad met me at the airport and we started our drive to the ranch. I asked him weather he raised cattle or horses on the ranch. He said neither his ranch was like the chicken ranch. It was a large bordello and since I was going to be there all summer he would see that I had plenty of time in the “saddle.” He said by the time I got back to New York I would know so much about women and be so confident that women would fall all over me. It as important that I learn about women since this business would be mine. While I was there I would work as his assistant and sleep with a different woman every night. For tonight he would pick the woman since she would be my first after that the women would decide.
After arriving at the ranch dinner was served. Thick juicy steak and wonderful conversation with our companions. Both women were gorgeous and intelligent. I thought they must be managers or office staff. I did not think it was possible for women this intelligent and sophisticated to be prostitutes. But I was wrong. Allison the one who would take my virginity later that night had a master’s in psychology and was studying for her PhD. She was tall long legged and beautiful. Her auburn hair was long and hung to her shoulders. Her breasts were large and shapely. Her legs looked like they went down forever and were topped by a magnificent ass. But the most exquisite part of her was her face decorated by her large green eyes. Read more…
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A Seedy Halloween
Edited by La Pantera Bonita
Everybody remembers where and how they lost their virginity. However I doubt many of us have done so in a rite with an audience. I still have nightmares about the night I lost my virginity.
I had just finished up Navy boot camp in Orlando Florida. Like so many in my family before have done when the nation calls we serve. And we always serve in the Navy to avoid getting shot. Vietnam was winding down. No new troops were being sent over and intelligent geeks who volunteered for submarines would never get to see a rubber tree except maybe in a picture. For some reason all my family and friends assumed I was going to serve on a gunboat in the Mekong Delta. Perhaps they got the idea from me. I neglected to mention the submarine stuff.
My cute girlfriend was waiting on me. Our relationship was at a point where we would engage in mutual masturbation at the end of a date. Okay the last week I was getting some blowjobs but we never had sex as defined in the Funk and Clinton Dictionary.
Terry had a nice build with shapely muscular legs and ass. Her pussy was tight with slightly darker hair. Her breasts varied between 34B and 36C cup sizes depending on maker of the bra and time of the month. She would let me play with her breasts while she would jerk me off.
Terry was at the house while we were carving our pumpkins. My older sister Sarah (named for Mom) and family were down in South Carolina visiting us at the time. Her two children Todd age 7 and Tony age 5 were of course with her and were all agog about carving out pumpkins. There were four of us carving at the table with newspapers spread out to prevent any sticky mess on the floor and table. Todd had his own pumpkin with only minor adult supervision I was helping Terry carve some face Felicia my baby sister and about 12 years of age (see MIKE RETURNS HOME when she becomes of age) had one corner. Read more…
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A Cheerleader s Cherry
Melissa Haley walked across the 5th wing hallway and felt eyes piercing through her green blouse and tight jeans. A group of geeks drooled as their heads moved with her hypnotizing walk while a group of skateboarders watched her in disgust. She turned her head only to greet few of other cheerleaders and football players but ignored the rest. Melissa pulled up her purse to her shoulder and winked at a guy that was staring at her wide hips and he swooned to the ground. This was the life of a cheerleader.
Since Melissa became a cheerleader popularity was no problem for her social life. If she thought someone was worthy of being even looking at it was so but if she chose to ignore them then that was the way it was. She had all the friends she needed in her cheerleading squad and her best friend was the cheerleading captain Andrea Swanks. Every day every week every month she would have guys drooling over her or girls staring jealously at her strawberry blonde hair hazel eyes curving figure and perfect hips that were as if God Himself specially took His time to craft her body. Her only problem was her small chest which were approximately 32B which was probably the smallest section of boobs in the whole cheerleading squad. However she did not take this as a hindrance at all since nobody argued Melissa had small boobs.
There she is whispered a boy with curly hair and thick glasses. Man she s a spotlight!
You ll never get her George joked his friend Tommy. The only girls you get is probably online.
As Melissa got closed to the exit of the 5th wing Andrea and her fleet of boys and girls came into view.
Hey Melissa called out Andrea.
Hi Andrea.
Remember what I told you last week? asked Andrea excitedly as her friends suddenly began to cheer loudly.
You mean about the party at the Leaf House? I thought you said there was Read more…
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Delia Remembers
It was whilst reading the Notices in the local paper that Delia saw that her old friend and one-time Mayor of the town had died from a heart attack leaving a wife and two married children. Sitting in her chair glass of wine at her side Delia s mind recalled the events of very many years previously. Society rules were very different then.
After leaving the local Art College Delia worked in the studio of a small textile design firm. She overcame the tedium of the repetitive work over her light-box with fantasies of the promised joy of copulation or if she wasn t feeling particularly randy of stunning dramatic performances in the great plays of Shakespeare at the Old Vic Theatre. She loved to imagine the sound of tumultuous applause ringing in her ears as an alternative to the imaginary feeling of a man thrusting his large cock up and down inside her aching body.
She wouldn t let Johnnie her boyfriend have intercourse with her yet of course even though they were now engaged. She had hoped to be still a virgin on their wedding night. That was expected of her. Anyway providing Johnnie really thought she was she would be to him. Besides she was afraid that her mother might just be right in her warning that Johnnie may lose interest in her if she gave way to his sexual lust before marrying him.
But alas she no longer was a virgin. At their joint eighteenth birthday party given by Roly and their friends at Roly s home. Drinks starting with punch were flowing. Neither Delia nor Johnnie were used to much alcohol and both got a bit unsteady fairly quickly. Silly games were played and there was much kissing all round in Postman s Knock and similar games most of which required the lights to be turned out. Breasts were eagerly fondled by sweaty hands and erections groped for the thrill of feeling a cock.
Before turning to the food Roly decided to play the game of Murder. It was a quiet and lengthier Read more…