I am a 38 year-old man. I have been married for 11 years and I was with my wife for a few years before that. Over that time I have cheated on her with numerous women. Each year, I usually have affairs with one or two other women along with a few one-night stands. The longest I've gone without cheating is about 9 months after we first got married.
I was a cheater long before I got married. Outside of my high school girlfriend, I think I have cheated on every serious girlfriend I have had. It's never been my significant other's fault. There have been times when my significant other and I have had sex almost daily, and I still cheated. I get off on being bad and being with new women.
This is the story of how I first found out I loved to cheat.
I was a late bloomer in high school. At the start of my sophomore year, I was 6' tall and weighted about 140 lb. I was a dork and not well respected by the popular kids. I did join the football team to bolster my college applications and get in better shape. It was a non-cut sport so I was guaranteed a spot on the team. In my sophomore and junior years I never sniffed the field, but I practiced hard. Between mid-sophomore year and the beginning of my senior year I grew about 3 inches and added 30+ pounds of mostly muscle. In my head, I was still a dork even though my body was a jock's body. I actually became a starter on the football team and was named all-conference in my senior year (due mostly to my conference being pretty weak overall and very weak at tight end).
I started dating a dorky girl at the beginning of my junior year. I lost my virginity to her. She had lost hers the summer before. She was very open sexually and was always willing to tell me what she liked and didn't like and was good at constructive, ego-building coaching. She even researched techniques and positions in her older sister's Cosmo's and her older brother's Penthouses. By the end of high school, she had trained me to give her orgasms at a pretty consistent rate. We broke up when we went to college.
When I went to college, I still had the self-image of a dork, but girls clearly didn't see me that way. My first week there, the most beautiful girl I'd ever seen asked me out (looking back at pictures she was maybe an 8, but that was easily 2 points higher than any girl in high school who paid attention to me). I'll call her Mary. She was a sophomore. She was the cliché queen bee, sorority girl. She was very charming and complimentary when we first met and for the first few weeks of dating.
Over time she became less and less nice. It is a pattern I saw with most of her relationships both romantic ones and friends. She starts off very friendly and sweet. Then she starts talking shit behind their backs. Then she slowly gets more and more passive aggressive to their face. By a few months in, she was treating me pretty badly, but I stayed because I didn't think I could do better plus having regular sex was pretty good.
She also had the bad habit of bragging and exaggerating. I witnessed on many occasions her embellishing or outright lying to seem more impressive. She had bragged about how rich her parents were and how her house was practically a mansion. I later found out her parents were just upper middle class with a nice house but definitely not a mansion.
While I was willing to suffer her abuse, a lot of her friends and sorority sisters were getting fed up. As I found out later, she had also been bragging about my prowess in bed. While I was totally competent, I wasn't a giant dick'd porn star that stayed rock hard for hours on end like she described me.
Early in December, Mary and I had just had a fight. I left because I needed to get to a study group. The group was 4 people including myself: a couple guys who were pretty cool and one of Mary's sorority sisters, Lisa. We studied for a few hours. We had a big exam coming up. The two guys left after we wrapped up. I asked Lisa if she needed a walk home. There had been some campus sexual assaults so everyone was on edge. She said yes.
While we were walking she asked why I seemed so agitated when I arrived. I told her about the fight with Mary. She rolled her eyes and said something about "classic Mary." I asked her what she meant. She had known Mary for a year more than me and gave me her take on her: the slow flip from sweet heart to bitch, the small slights that became bigger slights. It was music to my ears to hear it wasn't just me. When we got to Lisa's apartment, she asked if I wanted to keep talking upstairs. I said, "I know Mary wouldn't like it. She could get jealous... so yes."
Lisa laughed, and we went upstairs. Her roommates were out. We sat on the sofa. She gave me a beer. We chatted for a while. We gradually got closer and closer until she was curled up right next to me. I apologized for hijacking her night to bitch about my girlfriend. She said, "That's alright. But if you want to make if up to me..."
She leaned in and kissed me. I was stunned. She was every bit as attractive as Mary. I thought I had struck the jackpot with Mary. Now Lisa was into me.
Lisa was 5'9'' and had the body of a volleyball player: lean, thin, with a perky toned ass. She was probably a d-cup. She was a redhead with freckles all over. Personality-wise, she is what I would call a charming bitch (and I mean that as a compliment). She would talk trash with a great deal of charisma. She would give people guff to their faces. Behind their back, she was more likely to give people shit for being catty than to cut that target down. I had a bit of a crush on her.
I said, "I don't" - kiss - "know if" - kiss - "I" - kiss - "should." - kiss - "what about Mary?" - kiss
"Fuck Mary. If she didn't want me to hook up with you, she shouldn't have told me how good you are at it." It was a convincing point.
She crawled on top me and straddled my lap. We had moved from kissing to making out. I was running my hands up her legs to the edge of her skirt and holding her waist but not venturing up or down.
She broke our kiss. She slid one hand up her skirt to her ass and the other up from her waist to her breast. "Quit fucking around with this innocent bullshit."
With that, it just dawned on me that we might end up having sex. Call me naive. I was unleashed.
I flipped her onto her back on the sofa with me on top of her. I kissed her neck and nibbled her ear while squeezing her breasts. She pulled off my shirt. She pushed me away to check out my body, which at the time was very well defined. She bit her lip while she slowly ran her hands from my thick neck to my broad shoulders to my wide chest to my ripped abs. She looked up to me with smiling eyes.
I started unbuttoning her blouse. I ended up ripping off almost half the buttons because of my clumsy eagerness. My eyes almost came out of their sockets when I saw her chest. I knew Lisa was buxom but she was a full two cup sizes bigger than Mary on the same sized frame. Mary was a petite b-cup. My high school girl friend was a chubby d-cup. I had missed big boobs and seeing them on such a fit girl was incredible.
I started to go for her bra and she stopped me and said, "Let me."
I guess my shirt performance had made her wary. I sucked and bit her nipples. She moaned and grabbed two handfuls of my hair. She moved me from one breast to the other. Then she started pushing me down. Her skirt was bunched around her waist. I got between her legs and grabbed her panties. I looked up at her. She was flushed, biting her lip. She vigorously nodded her head up and down to tell me "Yeah dummy, that's what you're down there for."
I pulled off her panties. I dove straight in. I licked up and down her pussy. "God you taste so much better."
She got a big smile and pulled my face into her pussy by my hair. I used every bit of my training. With Mary, I just try to make her cum as quickly as I can so we can get to fucking. With Lisa, I felt I owed her more. I listened to her moans to draw it out and maximize her pleasure as best I could.
After I teased her by licking up and down her slit, I spread her labia with my fingers and unleashed my full tongue. Both Mary and my high school girlfriend loved my Gene Simmons-style tongue. I went in deep. Lisa squealed, threw her head back then looked down at me with disbelief.
While I probed with my tongue, I rubbed her clit with my thumb. I used my other hand on her ass to keep her close and maximize how deep I was getting.
After about 10 minutes, she came hard on my face. She pulled me up by my hair and we kissed some more. "That lived up to the legend."
I didn't know what she meant. Didn't care. We started to hear the front door open. She told me to get up and pointed to her bedroom. We grabbed most of our clothes, but I left my shirt and she left her bra. We closed her bedroom door as her roommate came in. We heard her chuckle and say, "Lisa, you slut."
We laughed and started back up. She pushed me onto the bed. She took off my jeans and boxers. She held my cock and looked it over. She looked at me, smiled and said, "Not bad." Guess my 6.5'' didn't live up to the hype.
