My Sexual Autobiography 8211 Part VIII 8211 With Teen Aged Boy
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My Really Wild Teen-Aged Sexual Adventures free porn video
I was working as a gopher for an auto-body shop to earn some extra spending money before starting college. I never worked so hard for so little, but really learned a lot about remaining employed. One day around noon, I asked the boss if he had anything for me to do; he told me to take the rest of the day off. I had some change in my pocket and walked across the street to get a milkshake.
As I entered the ice cream shop, I spied the sexiest woman I had ever seen in my short seventeen years. She was very curvy and very pretty, appearing to be about twenty-three years old. She gave me a big smile and took my order. As I attempted to pay, I dropped a handful of change on the floor. I was truly embarrassed.
She smiled at me and said, "Do you like what you see?"
I replied, "Best-looking milkshake I ever saw."
She then said that I was drooling all over the counter and obviously enamored with her barely covered tits and ass. As I turned to run out the door she said, "Come back at 6 pm and walk me home."
My older and wiser brother purchased an old beater of a Ford from the late 1930s that I could drive if I kept it repaired and filled with gas. This was a great deal for a broke seventeen-year-old.
When I arrived at the ice cream shop, I thought she was not going to get in the car. After a minute or two, the look of horror at seeing me in the battered old and smoking Ford turned into a smile and she entered the door I held open for her.
As I drove away she gave directions out of town. We soon came to a public park and she asked me to park in a shady spot at the rear of the park. After parking, she said, "I don't have a lot of time, as I still have a babysitter on the clock." She moved closer and again said, "Do you like what you see?"
I managed to tell her I really liked her very nice large and shapely, tits. I told her that her ass was spectacular but so was everything about her. I leaned towards her for a kiss as she wrapped her arms around me. I had never had such a passionate, sloppy, tonsil-tickling kiss
We started making out more passionately than I thought was possible. I reached up and fondled her tits, expecting to be slapped. It only made her response hotter. Feeling brave, I started to slip my hand under her skimpy T-shirt when she stopped me.
She then said, "If you play your cards right, you may be able to touch and suck these titties and play with my wonderful ass."
"Please tell me what I have to do," I pleaded.
She said, "Well, for picking me up from work, you will get to make out with me. If you pay my babysitter five dollars for keeping my babies, you can feel my pussy over my panties and fondle my tits over my bra. I have never been so turned on."
I told her I wanted to do more than that, and she told me that was a big step and would take a lot more to get there.
I begged for more info. She said, "I need for you to pretend you are my boyfriend and take me on a date Friday night. It will take another ten dollars for the babysitter and about six hours of your time as well as you being able to use your brother's car until after midnight."
I could see my college fund evaporating before my eyes. She advised I would be rewarded by being allowed to finger her pussy while we made out and kiss her wonderful titties. We had a deal. I would contact my boss and see about expanding my duties to make more money; obviously, I was going to need it.
For the next few days, I picked her up after work, drove to the park, and proceeded to passionately make out. Her kisses were really hot. After very passionate making out and rubbing her wonderfully juicy and wet pussy through her panties, I orgasmed in my pants every night. When I dropped her off at her home, I dutifully walked her to the door, where the babysitter was waiting for me to pay her five dollars. Arlys told me I could not go inside her residence as she did not want her children to see me. That also meant no goodbye kiss.
Friday night finally arrived and I picked her up at her home. She was dressed modestly, not at all like her show-all ice cream shop uniform. I dutifully paid the babysitter ten dollars and we left. Following her directions to a pizza parlor, I was instructed to purchase a large combination pizza and two six-packs of beer. The waitperson had to bring them out to the car as I obviously was not old enough to purchase alcohol.
As we drove away, she said she knew that was expensive but I would soon find out it was quite a bargain. While en route, she advised me to seriously pretend that I was her new boyfriend.
She directed me to a middle-class neighborhood and into the driveway of a very nice home. We were greeted by another beautiful lady that Arlys introduced as her sister Carol. We entered and I was introduced to Arlys' brother-in-law Mike. We were soon eating the pizza, but I declined a beer as I knew I would be in big trouble if a cop stopped me on the way home. We had a very relaxed visit and chatted about cars, sports and watched television.
At 9 pm, Arlys' sister announced that she had to go to work at a hospital, where she was employed as a nurse from 10 pm until 6 am, but we were welcome to stay and finish watching the ball game.
As soon as we heard her car drive away Arlys asked me to follow her to the bathroom. She said to get to the next big step, I would have to stay in the bathroom until she came back for me. There was a box of books to read, a cooler with soft drinks, and the rest of the pizza in the bathroom. The bathroom was large, but there was only one place to sit. She asked me if I understood that short of the house burning down, I was not to come out.
Almost immediately, I could hear bed springs squeaking, a headboard banging and the now-familiar sound of Arlys loudly moaning coming through the walls of the bathroom from the bedroom. I can honestly say that I have never been so embarrassed or felt so stupid. I thought the time would never pass. It was the same for the next three hours: Arlys loudly moaning, bed springs squeaking, and the headboard banging on the wall.
Finally, Arlys came to the bathroom and opened the door, saying it was time to leave. I could hear Mike snoring as we walked past the bedroom and out the front door.
The ride home was totally silent. When we arrived at her residence, she asked if I was going to pick her up after work tomorrow, to which I said no. She knew that I was disappointed with her and very angry. She reminded me that I had earned considerably more in the sexual favors department and it would be a shame to let that go to waste.
I replied that the only way I would pick her up tomorrow would be a blow job now and one tomorrow after work.
She said, "I can take care of the first one now."
She started massaging my cock through my pants and soon unzipped me and slipped my cock into her mouth. The results were instantaneous; I started cumming before her lips reached my pubic hair. She continued to stroke and suck my cock until all the cum was swallowed. She continued to suck and very soon it was starting to feel very good again. The second orgasm took about fifteen minutes. She continued sucking until it was drained and swallowed. She said that I should walk her to the door and that she expected to see me after work tomorrow.
I was on cloud nine as I drove to the apartment, which I shared with my older brother. We were under the close surveillance of our landlady, who lived next door. Needless to say, no monkey business such as wild parties or bringing young ladies home would be tolerated. Due to the surveillance, my brother now stayed with his girlfriend most of the time and only came home to do laundry and check the mail.
After a quick shower, I was hanging up my clothing when I noticed a folded piece of paper in my right rear pants pocket. I opened the paper and it was a note addressed to me.
Dear Richard, this note is for your eyes only. Please do not tell Arlys I contacted you. I knew what they had planned last night and I would like to talk to you about it. Please call me at work. You can usually get me after midnight until 6 am.
My curiosity got the best of me and I dialed her immediately. She answered and thanked me for calling her. She asked me to come by the hospital cafeteria at 6 am and she would meet me there, have breakfast, and discuss what had occurred. She would not elaborate further, stating that she did not want to be overheard.
I arrived at about 6 am, found a vacant table, and started on a cup of coffee. Ten minutes later, Carol arrived and we went through the serving line, getting two huge breakfasts at a very reasonable price. I had just found my new favorite place to eat.
Once breakfast was completed, Carol took my arm and led me to an outside patio eating area that was rarely used.
Carol told me that she was quite aware that her sister and husband were having an affair and she hoped that I would help her correct her current situation. I asked her what I could possibly do to help her.
"You and my husband look very similar. I would like for you to impregnate me and give me a baby. Hopefully, we will be able to pull this off twice. He is drunk most of the time he screws me and will think he forgot the condom or it leaked."
I had read of ladies secretly keeping, the used condoms, extracting the sperm, and injecting it into their vaginas with a turkey baster. When I asked her if that was what she wanted to do, she laughed and said, "No, big boy, you get to fuck my brains out. It will be a big win for both of us." She said she would like to maybe pull this off twice then divorce him. "He is an engineer making big bucks, so he will be able to support the children."
As I was thinking to myself, it will serve the bastard right, Carol then told me she was housesitting for a lady intern for the next two weeks and we could use her unoccupied home while she was gone on vacation.
On the way to the home, Carol told me that the best time to get pregnant was the week around the thirteen days before her next menstrual cycle and today would be a perfect day to start. When we arrived, we took a shower together. Wow, her body was even nicer than Arlys' with no stretch marks as Carol never had a child.
As we climbed into the bed, Carol wanted to make out for a while to warm up. I was all for that. I massaged her beautiful breasts while kissing her sweet lips. I then sucked and kissed those tits until I was hard as a rock. Carol warned me against having a premature climax as she wanted to fill my balls with cum before fucking to increase her chances of getting pregnant.
I told Carol that I would love to kiss and lick her pussy. She placed her hands on my head and gently directed me between her now widely spread legs. What a beautiful sight: her swollen pink lips raised out of her shiny blond pussy hairs. The aroma was divine. The taste was really wonderful.
I licked her pussy lips from her ass to her clit, creating a flood of pussy juice. She was pushing my face into her pussy and squeezing my head with her thighs. Her very loud moaning was music to my ears. Her body stiffened and convulsed a couple of times before she pulled my pussy-drenched face to her face, and I kissed her longer and harder than I ever kissed anyone.
She was breathing very hard as she asked me not to cum too soon. "I need a big load in my pussy," she said. Her body was still trembling as I kissed my way down to her wonderful tits. The more that I licked and kissed her tits, the more she trembled.
Her body started to stiffen again as I kissed my way down to her pussy. She was well into an orgasm as I clamped my pursed lips around her love button and started massaging it with my tongue. She was bucking like a wild horse, loudly moaning as I held her tightly with my arms around her thighs.
Her moaning got really loud, turning into screams and then totally quiet. Her body went limp. Her only movement was the rapid rising and falling of her chest as she breathed deeply. It appeared that she had fainted.
I rolled off and lay beside her as her breathing normalized. We lay there for a few minutes, both covered with perspiration. She asked me to turn on the overhead fan to cool us down. She looked at me and asked if I had cum yet.
I put her hand on my still hard cock and said that I was saving it for her pussy. She smiled and placed a pillow under her beautiful ass, then pulled me over on top. Her legs were spread wide as we started having loving and sensual sex. As we slowly fucked, my cock continued to get harder. As I got closer to cumming, she told me to push deeper into her pussy and not to pull back when I started cumming.
She wanted to seal the massive load of sperm deep in her vagina, forcing live sperm into her Fallopian tubes searching for the elusive egg to fertilize. She gently moved her vagina and flexed her vagina walls to maintain my pleasure to keep my erection from decreasing in rigidity too soon.
As we lay there, she said that she wanted to continue to lie with her hips elevated to keep a large amount of sperm deep in her vagina to increase the chances of conception.
Carol said she needed to have a fresh, large insertion of sperm daily for the next ten days to maximize the chances of getting pregnant. I told her I would be at the hospital cafeteria daily for the next ten days or however long it would take to get the job done. Just to show my good intentions, I got back in bed with her and she pulled me back on top. Within half an hour I left her a second large sperm infusion, which we both thoroughly enjoyed.
I left Carol sleeping; she planned to get up around noon and go home. I went to Wally's Garage to talk about more hours. He was quite receptive and offered me a great incentive: more pay, more hours, and other benefits. He had been in the same all-steel, ten thousand square foot metal building for more than twenty years.
Recently he was paid a surprise visit from the City Zoning inspector and the Fire Marshal. It seems he had collected thousands of gallons of used oil, paint, and other chemicals. He had tons of tires and car parts, including many used automobiles. He had one year to clean up the mess and make the business legal or start paying monthly fines until in compliance.
Part of the compensation would be full use of the company truck, which was actually quite nice for a fifteen-year-old vehicle. I worked very hard cleaning up the illegal materials at Wally's Garage. I drove home, took a long, hot shower then drove to pick up Arlys at work.
She was waiting outside when I arrived and quickly hopped into the truck. As we drove away, she said, "Now what happens?"
"It depends on you," I told her.
"My babysitter can stay until 10 pm tonight for an extra five dollars."
"What do I get to do until 10 pm?" I replied.
"Anything you desire. I owe you a big time for last night. I know that you have not asked, but I need to tell you. No one ever fucked and satisfies me like Mike. My sister stole him from me and I never got over him."
We drove to a small town about twenty miles away and checked into a very small mom-and-pop motel. It was very clean, private, and very affordable.
We quickly undressed and climbed into bed. She said, "What is your pleasure?"
"Everything you have is my pleasure, but I have a question. How much longer are you going to fuck me?"
She inquired why I asked and I answered that I would slowly like to explore her whole body starting with her pussy. If today was the last time, I would start with eating pussy, followed by a pussy fuck, a sixty-nine. I would then finish with a rip-roaring ass fuck.
"There is no rush for me," she said, "you will tire of me after the newness wears off. Most men do not stay long with a divorcee with two children. You may stay with me a little longer as you are young and inexperienced. You have a lot to learn and I would love to be the one to teach you."
In my mind, I knew this was an offer too good to pass up.
I started slowly licking her wonderful pussy. Her pussy juices had lubricated her well, allowing my tongue to slide effortlessly up and down her slit, starting with her clit and traveling to her wonderful vaginal opening, into which I pushed my tongue, and down to her ass. I repeated this many times as she was having serious orgasms as long as I savored her wonderful pussy.
After an hour or so, my cock was so hard that it began to hurt. I climbed on and gently rubbed my cock up and down her very wet pussy. My cock was tender from the workout with Carol this morning. Still, the feeling was sublime. Arlys was the mother of two and had a rigorous fucking the night before with Mike. I assumed her pussy would be large and loose, which was absolutely not the case. Her cunt had a velvet-like feeling which gently accepted my cock with just the right amount of pressure in all the right places.
We started slowly, enjoying the wonderful feeling. My cock slowly continued to harden and the pleasure increased. When I was approaching a climax, I slid down her legs and slowly began to lick her very juicy pussy.
She soon realized the great opportunity at hand and placed her hands on the back of my head and was able to position my tongue over her magnificent and hard clit. She would begin a gentle and rolling climax which was almost continuous. When the pleasure became too intense, she would gently slide my tongue away from her clit and to my favorite place, inside her pussy tunnel, where the tasty fresh pussy juice was flowing.
Little did I know that over the next year she would highly refine this technique to allow us to enjoy the wonderful feeling for hours, usually finishing with a mutual phenomenal sixty-nine orgasm with her sucking my cock dry.
We arrived at her home at 10 pm. Before walking to her door, she asked if I would pick her up at work tomorrow. I assured her I would be there.
When we got to the door, the babysitter came out and accepted the ten dollars. She asked if I could give her a ride home as it was starting to rain. I agreed and we left for her apartment about a mile away. On arrival, she invited me in for a cup of coffee.
She introduced herself as Jan and thanked me for the babysitting payments and said it was time we met and talked. She said she was staying here with her sister. Babysitting would never pay the rent on this nice of an apartment.
Jan was tall, about five feet nine inches tall and slender. She was what you would describe as a plain jane, but should clean up nicely. She had a great smile and a nice personality.
I asked her what we needed to talk about. She said she knew I was fucking Arlys and Carol. I was surprised at her bluntness and asked why she would care. She told me that those affairs would not last long and she asked if she could be next on my list when they moved on. She further stated that she was about the same age as they were, with a lot fewer miles and not nearly so promiscuous. I told her I might be interested if she would give me a few more reasons.
She said that I could have an exclusive as long as I wanted it. Her pussy would be mine and mine alone, available anytime I wanted it. She told me that she was just above a virgin in the actual sexual experience. She said that she was a fast learner, clean, eager to learn, and was sure I would not be disappointed. She gave me a big smile and told me that she hoped that I would teach her to be the best sexual partner in my life.
For the next few months, I kept very busy. I worked for Wally's Garage nine to five and was making a lot of progress cleaning up the mess. I usually picked up Arlys around 6 pm and was having sex with her several times a week. I would meet Carol for breakfast several times a week and was often having delicious unprotected sex.
I was still taking Jan home most nights. I was becoming very fond of Jan. We would make out and she would let me lick and play with her slender body. We often had very hot foreplay sessions with no penetration. She insisted on waiting for penetration until she would be the only one. I was still fucking Arlys and Carol very frequently, so this was fine with me.
One day Carol met me for breakfast and told me her pregnancy test was positive. She was very happy and in a funny sort of way I was happy also. She asked me if it would alright to limit our morning sex to about once a month until she was ready to get pregnant again. I agreed, thinking it was a great deal as she was a terrific and enthusiastic sex partner, particularly with no condom.
I still gave Arlys a ride home daily and could have sex with her anytime I wanted, which was often, particularly with Carol pregnant and unable to have rigorous sex. Her ex-husband was showing a lot more interest in their children and spending more time there. Arlys was fucking her brother-in-law much less frequently now and I was spending much less time in their bathroom.
Now that he was going to be a father, Mike cut back on his drinking and was treating Carol much better. She was still angry at the infidelity and poor treatment but was beginning to think her marriage could be salvaged. She still kept our once-or-twice-a-month morning fucks and blow jobs as she feared her husband could revert back to his old ways.
Jan and I both enrolled in two evening classes at City College. The City College classes, although a long way from going to college full-time, made my parents exceedingly happy.
They purchased me a very nice used car for my eighteenth birthday, which ensured that I would continue the evening classes. I ignored the fact I would be thirty-nine years old when I graduated taking two night classes a semester.
Jan got a very nice part-time job with a legal office, having flexible hours, doing mostly filing and typing of non-urgent documents.
One night after class, Jan and I were making out very hot and heavy. I was getting a lot more rest and a lot less pussy due to much less contact with Arlys and Carol. We were in my much larger and nicer car. I had her blouse and bra removed and her skirt above her hips and her panties around her knees. She allowed a lot of foreplay as long as no penetration was attempted.
In the truck, limited space kept her legs bent enough that my cock never got close to her pussy. This bigger car allowed her to lie back. In a lust-driven mood, I climbed on top and entered her before she could protest. She started to cry, saying that I should stop as it really hurt. I immediately pulled out. She said she was sorry, but the pain was too much. We got dressed and made out a while and went into the house.
I often spent the night there but never had sex inside when her sister was there. I lay awake all night feeling horrible. I had really begun to love Jan and was afraid that I may have really made a big mistake. She woke up in the morning and snuggled up very close and kissed me.
She apologized again, saying that she should have admitted to being a virgin. I apologized and asked if she hated me. She said absolutely not and would love to try again for penetration in a few days when her pussy was not still sore, and a lot more gently this time. No more uncontrolled deep thrusts until she was ready. I hoped that would be very soon.
Jan and I continued to attend City College and graduated in three years rather than the usual two. Jan was offered a very nice full-time great paying position with her company. This allowed her to afford a much nicer apartment for us. Jan decided not to transfer to the university, saying she already had a great job. She said that we would probably get married and start having children when I graduated from the university and got a better job.
After I transferred to the university, I continued the part-time employment with Wally, who was quite happy with my progress in getting his business cleaned up, legal, and very professional looking.
Surprisingly, Arlys, Carol, Jan, and I all remained friends. I still could get an occasional very hot and sexy fuck from Arlys and Carol. It really did not feel like cheating, but I never told Jan. A year and a half later, Carol asked to resume the morning fucks without a condom, to which I readily agreed. Jan was getting a lot of overtime and never noticed. About six weeks later, Carol showed up for breakfast literally glowing. She was pregnant again. She said we could go her home for a really hot fuck as her husband was working out of town.
I called Wally and requested to come in at noon, which he approved.
I often dreamed of the good old days with Carol. She was the best sex partner I ever had, before or since. We started off with me eating her pussy through a half dozen orgasms. I then took her doggy style through several more pussy juice-producing orgasms, which I sucked and licked clean when I would get too close to cumming. We joined for an unbelievable satisfying sixty-nine that lasted for an hour. We orgasmed together with her sucking every drop of my cum and swallowing.
As we were cleaning up and getting dressed, Carol said for me to never change my phone number, as she would still like to have a mind-blowing fuck like we just did at least once a month. She further said that she may also need more of the ten-day-in-a-row fucks if she decided on a third and maybe a fourth child. I assured her that I would always be in touch and ready to be of service.
Life is very very good, even going to college nights for the rest of my life.
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