First Time Cheating On My Girlfriend

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sexy-massageI don’t like to brag but I was quite handsome as a teenager. And every time I had a girlfriend it seemed like more girls wanted me. I guess girls want what they can’t have.

When I was fifteen I happened to be a single man for the summer. Most of my friends had girlfriends and most of their girlfriends gave me plenty of signs that they like me.

It was a strange time, because I felt really full of myself on one side and on the other side I felt deceitful; even though I haven’t done anything wrong….yet!

Strange as it sounds I used to tell girls that I just met that I love them; in a funny and playful way. Sort of like this: Let’s say that I met Judy at the park and we started chatting, she’d say something cute and I’d reply “I love you for that Judy”. Each girl that I entangled into this web became instantly more attracted to me.

Before long, I had a list of girls who outwardly or secretly loved me. I even had girls call me up after they got through with their dates and some of those dates were with my friends.

 At the time I was loving the attention. I am a Leo and when girls give me attention like that,  I tend to become an attention whore, LOL!

I set one of my cuties up with a friend of mine. They went out for a while, but every now and then Jen would call me up to tease me. She would ask me to come over at 11pm at night.

I used to go over Jen’s house at night to hangout and fool around a little while her parents were asleep. Jen’s parents were strict and they didn’t allow her to have boys over. So Jen would open her window for me and I’d have to climb in to her room through it.

I lived close to Jen, it was only a 10 minute walk down the street.

One day I started to date this girl Mary and the word got out soon through the teenage girl hotline. Soon my beeper was being filled with reminders of all the girls who seemed to want me even more. Jen stepped up her game to.

I had a thing for Jen because she had a real cute body and she tended to wear practically nothing when I came over. She would always ask for massages, while she was just in her bra and panties. I had no complaints of course.

I remember sitting on her soft butt while needing her shoulders and just visualizing pulling her panties off and having sex. Jen moaned and groaned when I gave her back rubs and that drove me crazy.

So when Jen heard the news about Mary she upped her ante. She would call me late at night as usual and beg me to come over. I told her that I shouldn’t because I just started dating someone. She begged and begged and finally said “if you come over I’ll be naked for you”.

What am I made of stone? Of course I made a trip over to Jens house only to find her in some sexy underwear and a skin tight tee shirt that made her breast and nipples pop out of it like crazy.

As she opened her window her nipples practically made me drool all over myself as I looked at her smiling at me.

What is going to happen to today am I going to cheat on my girlfriend? I thought to myself. I climbed into Jen’s room and the sexual tension in the air was thicker than gravy.

I walked over to her and gave her a hug gripping her Jlo ass in my hands. I gave it a little squeeze and a gasp escaped her lips. I began to smell her hair and then began sucking on her neck, because I couldn’t control myself anymore. I wanted Jen more than I wanted my girlfriend.

Jen began moaning quietly and my hand slipped inside her panties onto her naked butt. The feel of her bare ass in my hands made me hard instantly and my hardon began pressing against her stomach.

She couldn’t take the teasing anymore and moved in for a kiss, then began passionately making out with me. In the process I pulled her panties to her knees and began playing with her as she kept kissing and moaning .

We moved over to her bed and she slid down to my jeans and unbuckled my belt. She unzipped my jeans and pulled them down slowly to expose my boxers completely. Then she rubbed her face against my boxers until there was no more blood left in the remaining parts of my body.

She took out my member and sucked on me so well that I completely forgot where I was for a moment. Just looking at her face with it in her mouth made me drool on myself. She looked adorable to me (Am I crazy for thinking that’s adorable?).

She slowly pulled me out of her mouth and her saliva had covered my shaft completely. She then slid up my body and began making out with me as my wet member slipped into her tight wet hole.

We had sex for at least an hour and it felt like the best massage I ever had. Her wet warmness gripped me with the perfect tightness and slid on me with such grace that I thought I’d forget to pull out before it’s too late.

Jen came twice during our affair and the second time she came, I pulled out because the sound of her orgasm put me over the edge. I laid my member against her butt and came all over it as she began to relax from her climax.

We both lay in that position for a few minutes before reality set in and I just realized that I cheated on my girlfriend.

At first I tried to comfort myself by telling myself that I only been dating Mary for a few dates so technically its not really cheating, or its not that bad. But the truth is the truth. Mary was at home while I’m at Jen’s with my member glued to her Jlo butt.

Love and sex are strange things. I didn’t intend to have sex with Jen but the moment I climbed through that window we both knew that we’d be devouring each other soon. The moment took us over, I guess that’s why people say “it just happened”.

That’s what happened to me the first time that I cheated on a girl.

( 21 Votes )
Author Profile: VinceM

This author has published 26 articles so far. More info about the author is coming soon.


-2 #2 RE: First Time Cheating On My Girlfriendkobra000 2010-06-02 20:32
did the other chick ever find out? are you proud of yourself for this?
0 #1 NiceJames G 2010-05-19 02:09
Thats a really good story very emoitional and it was just narly.