Two Cherries

by Typoman

Copyright© 1999 by Typoman

Erotica Sex Story: This story is about me and two lovers. One turned out bad, the other great. You might have to wade through a little bit to get to the sex parts, But they are in here.

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   Ma/ft   Consensual   First   Masturbation   .

I was a virgin when I got my first cherry. In a way, I was fooled into screwing my girlfriend. Later on I found out that she was one conniving little bitch. The world was a soap opera to her. Karen was her name. She lived just down the block from me. They had just moved to Arizona from New Joisey. I spied her while driving by her house. Our eyes met, and I was hooked. This was my first real girlfriend. We started seeing each other regularly after that. We would go over to my neighbor's house and make out in the basement. My older brother didn't like her. He told me that whatever I did, don't screw her. Well I took his advice at first. She had the kind of breasts that I learned to dislike. They were big floppy ones with an areola that just sorta blended into her tit. She was 16 at the time and I was just about ready to turn 18 and graduate high school. Even at that young age, her tits were starting to sag. She was maybe about 30 lbs. Overweight at the time. Soon after she turned into a real heifer (that's a type of cow if you don't know). Of course at the time, I was getting a great make out with her and she was really the first one that I got intimate with. I sucked and played with those titties till she was sore and we had to stop. I realize now that I could have fucked her at any time. One time we were swimming in my parents pool at night. I got her swimsuit off. She was sitting on the side of the pool by the steps with her legs in the water. The very first thing that I did was to eat her pussy. She started to quiver and shake about three seconds after I dived in to her box. Her pussy tasted a little like salmon and sulfur mixed together. I got past the taste pretty easily. After all, I was in front of a real live pussy. I hadn't seen one that close since I was about 7 years old. Back then, All I knew to do was to look at the girl standing there with her dress pulled up, panties off, legs spread wide and a stream of piss coming out of her. Eating Karen out made me realize just how it can affect a woman, I was hooked. Of course I had always wanted to try it. She didn't ask me to eat her and really wasn't expecting it either. She had a great orgasm. I showed her how to suck me off. That was pretty good, but not NEARLY as good as my second cherry, now my wife and lover of 23 years. That's the good part, so just hang in there till I get to her please.

Karen, Trish (my wife) and several others hung out together at school. At that time, I was not interested in Trish at all. She was a little smartass and always had a jibe ready to deliver to any unsuspecting person. Karen and I had a little bit of a stormy relationship. I got tired of her and she was seeing other people. Of course she told me all about the people she was going out with. It was just innocent friends from her old Catholic school. This dweeb (Miles) had some horses and Karen liked to ride. Anyway, my brother kept giving me hell about Karen. He called her "Karenal Kissy Face". What a fitting name it turned out to be!

One day after we broke up, she called me and sounded upset. She told me that she thought that she might be pregnant. Well, I knew that I wasn't the father, I never fucked her. I went over to her house and picked her up so we could talk. The story that she gave me was that she really didn't even know if Miles the dweeb had actually gotten his little prick inside her. He just made a few jabs at her pussy and came all over her.

I now realize that this was just one of her little ploys to get me to screw her. Well, I fell for it and before the night was out, We were no longer virgins. Now, Taking a girls virginity is supposed to be a real thriller. It ISN'T. When I broke the hymen of both girls in this story, it hurt them. There is also a responsibility that goes along with it. Karen told me later "You may not know it now Larry, but one of these days we are gonna be married!" Now that was a scary thought. I didn't want to marry her, I just wanted pussy! We had screwed the first time in the back of my car. I didn't blow a nut right away like my brother said I would do. But I couldn't get my prick all the way in her either. I'm not hung like a horse. Just normal sized, with a thick shaft. I remember that we went to her house afterwards and their little dog kept sniffing my hand, then her pussy, and my crotch. The little bastard was trying to squeal us out. The second time I screwed her I managed to get my prick all the way inside her. The third time I swear by all the gods her pussy was loose! It stayed loose too! Well I was young and stupid and horny so I didn't know the difference. We were soon screwing regularly, I was eating pussy and getting head too. Then Karen told me that sucking my cock made her sick to her stomach. She stopped giving me head. Of course I then stopped eating her pussy and just fucked her. The little bitch lied when she told me that she came when I just did the straight sex. She wasn't smart enough to even fake an orgasm. I never even asked her if she came because I knew she hadn't. after a while of no licking, she asked me why I stopped. I told her that "It made me sick!" she got the hint! Pretty soon she was back to polishing my knob like she used to.

You men out there that don't eat pussy are really missing out. A pussy eating induced orgasm is about the most powerful orgasm that a woman can have. If she has never had her pussy licked before, she's yours for life. How can a man have a good time screwing a woman if she hasn't already had her pussy licked till she came her brains out then tried to buck you out of the saddle! Once she's had her first good orgasm, the second or the third or fourth etc. are really easy for her. The greatest feeling of power and control is when a woman is in the throws of orgasm. Especially while your prick is buried deep inside her. Nowadays, getting a woman off is what really drives me to orgasm.

Well. Sorry about that lecture, back to the story.

One morning Karen snuck through my bedroom window and we fucked in my bed. Later on I came back homed to find my bed all made up and the covers turned down to expose a big pussy juice stain! I was busted! My mother never said a word about it, but she definitely knew!

One time at an all night party at the river, Karen was stoned along with most everyone else. We were in a double sleeping bag together right at the fire and everyone else. She got horny and ducked inside the sleeping bag and started to blow me. Everyone could tell what was happening because of her head bobbing up and down under the bag. Naturally, I was a little embarrassed but hey! I was getting a blow job so I didn't even want to stop her. Someone yelled out, "Hey Karen! What the hell are you doing under there?" She flopped the top of the bag back and yelled out "SHADDAP!" in that New Joisey accent that was more than just a little irritating.

Later on, we moved our bag away from the crowd and she asked me to fuck her up the ass. Naturally, I went for it. I didn't know about how to properly prepare a butt for anal sex, also we had no lube. Of course that stopped my only chance to ever have anal sex so far. She stopped the action right quick after! I got about half way up her rectum.

One time while we were broke up, she came over to my house and told me that her father had choked her and kicked her out of the house. Later she amended the story. She fled the house in fear of her life. She was still underage. Like a real dumass, I fell for it and we got back together. I called my sister Nancy and she said that Karen could stay with her until she worked something out. Nancy lived about 50 miles away. I took Karen there and we spent the night together. I went over to her parent's house that same day so they wouldn't suspect that I had the little conniving bitch with me. Naturally, her father and mother were worried sick about her and hadn't the faintest idea why she had run away. Wouldn't you know it, as a result of that night she turned up pregnant! I told her that I would marry her. (Sounds like deja vu?) Well, later on everyone convinced her that an abortion was the smartest thing to do. I was off the hook! We broke up again.

By then I was sharing an apartment with a couple of friends. She wanted to move in with us really badly, although she never asked. She was still only 17 and still in school. She would call me up and ask if she could come over. I would tell her that I couldn't pick her up. She got desperate enough that she would ride her bike the 6 miles to my place. By then I was getting pretty tired of her, especially after she cooked me a meal!

Occasionally I would get desperate from lack of pussy and seek her out. She tried to play the "Look here! I have two men after me and I just don't know what to do!" game. I refused to play, and would leave. The competition was little Miles that couldn't break a cherry. He was not what I considered fair competition. We were broke up for good it seemed.

A few years and a couple of one nighters with different women would pass before I encountered the girl that turned out to be the love of my life once again.

Enter Trish

Now comes the good part. Thanks for being patient with my ramblings so far. As I have said before, I met Trish through Karen. I remember one night, the Gang was spending the night partying at the river.

Randy, one of my friends, took an interest in Trish. He was pretty slick and usually had no problem getting into a woman's pants. He told me that night that he thought Trish had a really nice pair of titties and was gonna make a try for her. He spent all that night making out with Trish and hardly got her halter top off. He gave up after that.

Trish was great at defending her virginity. Not that she was a prude. She just wanted to wait till the right person came along. Her parents were very happily married and Trish knew what a great relationship could be like.

One night my brother and I were cruising Main Street with this big old school bus that were going to convert into a recreational vehicle. We had parked that big old monster right on the main drag and were sitting up on the roof watching the cruisers. I heard someone call my name. It was Trish. She was cruising with Darlene, her sister in law. I waved to them and invited them up on the roof with us. Boy had she changed. She was a different girl when apart from her closest friend at the time (My future sister in law Christine). I felt an immediate attraction to her. She was also interested in me. We chatted for a short while then she had to leave. She gave me her number when I asker for it. I told her that I would call her. It took about two weeks until I finally got a hold of her. Either she was out when I called, or I was out when she returned my call. Well, we finally talked and she invited me over to another friend's house for a party. She asked me to bring a friend so the boy/girl numbers would be even. I brought Randy with me. Randy had told me to forget about Trish cause he couldn't get very far with her. He never would tell me just how far he got but he sorta intimated that he got her top off and that was about it.

 
There is more of this story...

To read this story you need a Registration + Premier Membership
If you have an account, then please Log In or Register (Why register?)

Close
 

WARNING! ADULT CONTENT...

Storiesonline is for adult entertainment only. By accessing this site you declare that you are of legal age and that you agree with our Terms of Service and Privacy Policy.