My Mature Fantasy Comes True

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He lost his virginity to an older woman.
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MrFalkirk
MrFalkirk
386 Followers

I don't know exactly when it was that I started having my recurring sexual fantasy. I guess it all goes back to puberty when I first discovered that something besides piss came out of the end of my cock. I also discovered that when that white fluid came out it felt a whole lot better than when I took a piss, that my entire body seemed to jerk and spasm in time with the discharge. Further, I found that I liked the feeling.

I had known that girls were different from boys for a long time, but being a bit slow on the uptake, I didn't put two and two together until that day that I came for the first time. I had noticed that rubbing my cock made it feel good and that the harder it got the better it felt. That day I was home alone after telling my mother that I wasn't feeling too well. Since I did well in school, I had no problem "sleeping in" for the morning. That morning, my cock rose to a semi-hard state and I started rubbing it in a fold in the covers over my naked body. It got harder and my breathing became faster and more panting. All of a sudden it felt like I had pissed in my bed, but it felt so much better than a normal piss. I rolled the cover off my body and discovered that, where I was looking for piss there was a white fluid all over the blanket. I touched it and it felt slippery. Being curious, I brought some of it to my mouth and tasted it. My first opinion was that it tasted pretty good. I still wondered just what it was, but I wanted to feel that feeling again and started rubbing my cock against the piled up covers until I spurted another load of white cream into them. Somehow, deep down, I knew that this was something I should keep to myself and I didn't say a word to anybody about it. Come to think about it, I still haven't said anything after all these years.

I finally figured out that the fluid that came out of my dick belonged inside a girl. Duh! A rocket scientist I've never been, but then I had never had the birds and the bees talk since my father had died when I was young and mother had never remarried. I was reasoning all of this out on my own without adult supervision or input and that did not make it any easier for me. Anyway, my life changed that day because on that day I became addicted to my own orgasms, my own cum and I decided I had to do something about making them a permanent part of my life.

Frustration reared its ugly head with a distinct lack of opportunity. I wasn't exactly a nerd when I was in high school, but I wasn't exactly chased by all the girls either. I started spending time in class imagining how it would feel for them to suck my cock or, even better, to fuck me. This caused a minor problem in that my dick hardly ever returned to a totally soft state though it wouldn't stand straight out either. But the fantasy didn't revolve around just one girl. Somehow I got the impression that you could tell how good you were by the number of girls you fucked and I wanted them all. Yep, every girl in my senior class was fair game to my vivid imagination. But, I really didn't want all one hundred or so senior class girls fucking me at one time. No, the fantasy was more like a production line type deal where as soon as I fucked one the next one would pop up and spread her legs wide.

Of course, the major problem was that none of these girls even knew I existed except as somebody they passed in the hall between classes and who sometimes got in their way. None of them would have even thought twice about saying no if I had been able to work up the courage to ask them out. Rejection had a way of turning me away from the girls at school and looking closer to home. But, the only females I had at home were my sister and my mother and I wasn't supposed to think about them in a sexual way. My sister didn't count simply because she was younger than I was and besides, we didn't like each other that much. My mother, who was still only in her mid-thirties--she'd had me when she was a mere fourteen--had given birth to me and I knew I wasn't supposed to return to the place from whence I had sprung on that momentous day.

If I had learned one thing from the girls at school it was that they were just as unsure as I was about sex. Now, I may have been somewhat slow, but I did realize that there was one group of women who knew much more about sex than I did, and that was the group of women who were old enough to have fucked. I began to fantasize about older women, women who knew their way around the male body and could actually teach me how to use mine to full advantage.

In my mind, I had a picture of the perfect woman. This perfect woman had my mother's gorgeously big 38DD tits, Mrs. Cole's lovely curved ass and long legs that stretched forever, and the angelic face of Mrs. Givens who lived behind us. All the neighborhood women contributed something to my fantasy woman which was the best parts of each of them all put together into one body. I honestly didn't know which one I wanted to fuck more. All of them had something I wanted to fuck.

Mrs. Cole's ass led to a pair of fantastic legs that I dreamed would wrap themselves around me just as I spurted my hot seed deep inside her body. And those legs were connected to two of the holes that I wanted to explore the most. Mrs. Givens had a mouth that looked as if it belonged wrapped around my hard dick, sucking the living juice right out of me. And I wanted nothing more than to replace my blankets with my own mother's magnificent tits and spurt my hot cream inside the valley they formed on her chest. I even went so far as to write all of these things down and hide it in my room, though the hiding place wasn't the best place in the world. I had a tear in my mattress and stuffed my fantasy "diary" inside the hole where I was sure nobody would ever look.

Then this new widow moved into the neighborhood. Her name was Gloria St. James, she was forty years old that year, and she had all the attributes or more that I could ever ask for in my fantasies. She fulfilled all of my specifications from my mother's 38DD tits to Mrs. Cole's lovely curved ass and long legs that stretched forever, to Mrs. Givens' angelic mouth. And it was all wrapped up in one person! The only problem was that, despite being a friend of my mother's, she hardly knew I was around.

I was eighteen just a month before she moved into the house next door. Her bedroom was on the ground floor and just opposite my upstairs window. Gloria St. James also sometimes forgot to close her curtains all the way, thus allowing me little peeks of her gorgeously firm body from time to time. I soon discovered that this show only happened after I had turned my lights out and sat in the shadows beside the open window. She never undressed while my lights were on. I know that she saw me looking down into her bedroom on at least two occasions and I feared that she would tell my mother, who would have had me change rooms with my sister and put me on the other side of the house. But she never did tell my mother and she did continue to "forget" to close her curtains at least two or three times a week though for some reason there was one week every month when her curtains were never opened at night. This went on from early March when she moved in until the early part of June. I was in heaven and beating my meat on a daily basis with enough jerk-off material to keep a young stud like me in cum for a long time.

My bedroom also overlooked her backyard with its swimming pool surrounded by deck chairs. Her yard had a seven foot high privacy fence around it, but my room looked right over that fence and gave a clear view of her entire backyard. Starting the month after she arrived just as soon as the sun was warm enough, she started taking sunbaths in her back yard. She dressed in the skimpiest of bikinis and always undid the top. The days that were a special treat were the days that she laid on her back letting the sun turn her two lovely breasts golden brown in the sun.

Her red hair hung as far as her shoulders and she normally tied it up in a ponytail. Oh, how I wanted to know if she were a "true" redhead or not. I accidentally found out about a week before my high school graduation when I was once again at home and just chanced to look into Gloria's backyard just after lunch. She was sunning herself totally naked and, even from as far away as I was, I could see that her pubic hair was just as flaming red and natural as the hair on her head. Just the sight of her laying there naked caused my cock to shoot a load of cum inside my shorts without me even touching it.

Then, for some reason--maybe I moved and she saw the movement-- she looked up at my window and her eyes locked with mine. Busted! Was I in for it now! How could I explain looking at her from my window while she was naked in her own yard behind a seven foot high privacy fence? My mother would kill me when she got home from her secretarial job. Gloria, she was Mrs. St. James whenever my mother was around, slowly got up and, still without a stitch of clothing on, unhurriedly entered her house through the back door. I watched as her ass swung seductively with each step she took.

Not two minutes after she entered the house the phone rang. I debated not answering it, but figured she already knew I was home so, with a very dry mouth, I picked up the receiver and croaked "Hello."

"Kevin, this is Gloria St. James from next door."

"Y-y-yes ma'am?"

"I couldn't help but notice that you were home and was wondering if you would please be so kind as to come over to my house and do me a favor?"

"Y-y-yes ma'am."

"Good. I'll see you in a couple of minutes then. Why don't you wear your swimsuit and have a dip in my pool when you get done with what I need you to do."

"O-o-ok."

"Kevin, is something wrong?" Now how do you answer that question when you know you've been caught dead to rights staring at your neighbor's naked body with it's lovely tits, gorgeous ass, and flaming red pussy hair?

"N-n-no."

"OK, I'll see you in a couple of minutes." I looked at the phone after it had gone dead and wondered why she wasn't angry with me. I'd invaded her privacy by looking over her fence and into her yard and, in return, she'd actually asked me to have a swim in her back yard pool.

I went to my room and quickly got my bathing suit on. I glanced out of the window, but Gloria was nowhere to be seen. Then I grabbed a towel from the laundry room on my way out the back door. As I crossed the grass to her back door all kinds of things were going through my mind, but none of them were very positive other than I knew positively that I was positively dead meat five minutes after my mother got home that night. How wrong I was!

I rang the doorbell and waited with disaster raging in my heart. I knew that I was in big trouble, really big trouble and I could see no way to get out of it. I danced from foot to foot as all sorts of punishments rolled through my mind one after the other. Then the door opened. Whatever I expected, it was not what met my eyes when that door opened.

Gloria St. James was standing in front of me literally wearing nothing more than a smile. My eyes popped out of my head and I stopped breathing as I stared at her beautiful body exposed to my gaze. She didn't move and I didn't dare move for fear of waking up and finding that all this was nothing more than an elaborate dream.

"Kevin. Please come in. Don't stand there like you've never seen my naked body before. I've surely given you enough chances, haven't I?"

My jaw dropped. Had I heard right? Had she said that she had given me chances to see her naked body? I couldn't quite believe what I was hearing, but I did enter her house. As soon as the door closed behind me, she took my hand and led me through the den out to the patio where she pulled my swimsuit down around my knees and let it drop around my ankles.

"We can't have you overdressed, now can we, Kevin? If I'm going to be on display, I think I should get to see what I am going to get, don't you? Quit gawking boy! You've seen me through my windows at night and today you saw me totally naked in my back yard, so I know you've seen a naked woman before. What's the matter, cat got your tongue?"

I couldn't speak. My eyes traveled from her pussy to her tits over and over again like a yo-yo on a string. Then she did the most amazing thing. She took my right hand and placed it on her breast. "Go ahead and touch it. I won't break."

I couldn't believe how soft her pear shaped tits were and yet how firm with such little sag to them despite her age. Somewhere I had heard that the older a woman got, the more her tits sagged until they reached the area around her knees. Suddenly, I knew that was wrong. Gloria was standing there letting me feel her tit with one hand and then she took my left hand and placed it between her legs, letting it come in contact with the moist lips of her adult pussy. I thought I had died and gone to heaven. From never having seen a girl naked to feeling what was between Gloria's legs was almost overload and my cock was as stiff as a piece of tempered steel within seconds.

"Well, I see you like what you see and feel. May I?" She reached for my cock and all I could do was slowly nod my head as if I were in a daze, which I guess I really was. It all seemed so unreal, like my mind had gone into a meltdown and started to refuse to process feelings and emotions. As her hand came in contact with my dick, I was sure I was going to blow my load on the spot, but she pinched the base of the urethra and stopped my cum before it had a chance to escape.

Then she did an amazing thing. She dropped to her knees in front of me and took my cock into her mouth. The warmth and the moistness had me once again on the verge of an explosion, but she once again pinched off the urethra and I got my body back under control. I warned her that her sucking was going to cause me to let lose before too long and she just increased the suction. This time she didn't stop the semen from gushing out of the slit at the end of my prick and I splattered hot sperm all over the inside of her mouth. She sucked, she swallowed, and she finally let some drip from her mouth only to have it fall on the top slopes of her breasts and drip down to the erect nipples. My spasms stopped and my cock started getting soft. Gloria gave me a couple of more gentle sucks and lifted her mouth from the head of my cock. She scooped up my sperm from her breasts and brought it to my mouth for me to taste.

She looked surprised when I sucked her fingers clean and then bent my head to her nipples and sucked the spunk from them drawing a low moan from her lips that told me I was doing something. I looked up afraid I was hurting her, but she pushed my mouth back down to her tits and held it there while my tongue went back to work.

"Oh, Kevin! I was hoping you were going to be good to me. I am going to teach you all kinds of things about fucking a woman and loving her, but right now I just want your hard cock stuffed up my hot, horny cunt. Fuck me hard boy!"

"Mrs. St...."

"If you can fuck me, you can call me Gloria."

"Gloria, I've never made love to a woman before. I-I-I'm a virgin."

"A virgin! God, Kevin, it's time somebody took your cherry and I guess that somebody's going to be me. I don't think I've ever had a virgin before."

She pulled my face back to her tits and pressed my mouth to a nipple as she massaged my back and ran her hands down to my ass feeling down the crack. Her finger found my asshole and rubbed it gently before insinuating itself inside my back passage. I moaned as first one knuckle then two found their way into my body massaging my prostate from the inside. My cock grew harder and she pushed me backwards into a chair releasing her fingers from my ass as I sat down. Gloria then straddled my legs lowering her body on my rigid shaft. I felt the head slip between her moist cunt lips and moaned. I groaned as I felt her flaming red pussy hair massage my balls and mix with my own blond pubic hair. She sat still for a moment savoring the feel of my cock inside her pussy.

I had never felt so warm and protected before in my eighteen years of life. It felt as if a warm velvet glove had wrapped itself around my dick and was slowly milking it from the bottom to the top. I had jerked my cock raw with my fantasies, but never had I dreamed that a pussy would feel as good as Gloria's did right then. Then she started slowly moving her pussy up and down and giving it a twist on every second or third downstroke. My cock stiffened even more and I heard Gloria say "Fill my cunt with your hot seed. Spray my womb with your cum. Come on, Kev, make me feel good. "

Just as she said that, Gloria went into spasms and I was afraid I had hurt her, but one look at her face told me that I had not hurt her, that I was giving her intense pleasure with my cock. I felt the pressure building up in my balls and knew that I was going to blow my load pretty quickly. I started humping up to meet Gloria's thrusts and my movements started getting frantic and jerky. Then I came, and came, and came, and came. I don't think I have ever sprayed as much cum from my balls as I did into Gloria's cunt that first time. It felt as if it must have been at least a gallon or more of scalding hot man cream jetting from the slit on my cock head. There was so much that I felt it scald my nuts as it dripped from Gloria's sopping pussy.

Gloria collapsed against me as I sat there in the chair and I waited for her breathing to near normal. She opened her eyes and smiled at me.

"Hello, lover. You are my lover now, you know."

"I know."

"You can't tell anybody about this, right?"

"Right."

"Well, that's not really true, Kevin. There are a couple of people who already know."

"I know and you know."

"Yes, but there are others."

"Others?"

"Oh,, yes. You don't think I did this all alone did you?"

"UH?" I was totally confused.

"Hello, Kevin."

"Mom! Mrs. Givens. Mrs. Cole. What are you guys doing here?" I noticed that not a single one of them had a stitch of clothing between them. Mom's tits sagged just a bit more than Gloria's, but they were still more than nice, they were great! Donna Cole's ass looked just as yummy without clothes as it did with clothes. Marcie Givens was licking her pouting red lips as she smiled at my half-erect cock dangling between my legs. She reached over and took it gently in her hand jerking it up and down causing the blood to flow back in and stiffen it once again.

"Watching you lose your cherry. Watching you get fucked for the first time."

"But-but-but..."

"Relax, Kevin. We all read your diary. We all know what you have been fantasizing about for the last three or four years. You want Donna Cole's ass. She's going to give it to you. You want Marcie Givens' mouth. She's going to suck you. You want to fuck my tits. They're all yours for the taking."

"Mom..."

"Kevin, none of us have men who will fuck us like we want to be fucked. You have said you wanted the job. We're here to interview you for that job and see if you meet our expectations. If you pass our test, you will get to fuck anyone of us whenever you want as long as people don't find out, including Donna and Marcie's husbands and kids. As for fucking me, as long as your sister is none the wiser, you are welcome to come to my bed any night starting tonight."

"Then, this was all planned?"

"Yes. We just had to wait until you decided you wanted to stay home and peep on Gloria again. When you told me you wanted to stay home today. I left as if I were going to work but went over to Donna's and called in sick. Then we called Gloria and Marcie and told them that today was the day. Well, Gloria, is he any good?"

"Well, Nancy, he's a bit raw around the edges, but I think he'll train up really nicely. Of course, Marcie may have to work on him a bit to get his cock hard again, but I think his staying power is going to let us all have a lot of good, hot cum all day long."

MrFalkirk
MrFalkirk
386 Followers
12