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The First Time I Stepped Outthis story is part of the FanClub (fm:adultery, 1788 words)

Author: artsoccerdude
Added: Mar 30 2026Views / Reads: 2931 / 2412 [82%]Story vote: 9.30 (12 votes)
This is an account of the first time I ever cheated on anyone.
 


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In some of my other stories, I have mentioned Amy ("My First Time", "Meeting Her Mom", and several others). I lost my virginity to her on our first date. She was my first love; my college sweetheart. But it didn't last. We were together nearly 2.5 years and had a very, very brief engagement. But this isn't about the end of that relationship. Rather, it is about the time I first ever cheated.

We had been together a year and a half. Things had been amazing. That first year, we both lived in the dorms and since she was an RA I spent most nights with her in her bed. The second year, I had an apartment and she spent most nights with me. She had an insatiable sex drive, much like me. My roommates (Drew from several other stories and Dave) were almost certainly annoyed that at almost any moment Amy and I could be fucking. And while she wasn't exactly loud, she wasn't silent. We would fuck in the shower and sensuously wash one another. We would fuck hard and passionate in my room. We would tease one another in the living room regardless of who was there with us.

But as the year progressed, sex decreased. Maybe our relationship was maturing. But it went form multiple times a day to a few times a week to by the end of the school year oral sex once or so a month. That was a huge change for a guy who had been getting laid daily. So naturally, I began looking at porn much more often to relieve my frustration.

As summer approached, Amy had a summer trip to Canada with her family. ...

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