I was between relationships at the time, about thirty-two years old, and had been sleeping with a twenty-one-year-old girl, but it was understood to be an officially open liaison (although I was the one sleeping with other people most often).

I think she was trying to turn it into a relationship, but I wasn’t in the headspace for it. We were sleeping together daily for a while, but I took a break, and apparently, she took advantage of that, as I went over to her place and was thinking we would have sex that night. We fooled around, but she stopped me before sex and said she didn’t feel right about it that night. I could tell she was a bit more sensitive than usual, and she finally came clean, telling me that she had sex with the guy she had been hanging out with.

Of course, I wanted to know more. She was a bit reluctant at first to give details, but she said that he was underwhelming and didn’t last long. She was a cute girl with large breasts, so I could kind of understand, as he was her age and apparently wasn’t very experienced. I told her I didn’t mind at all and was up for it if she was, but she declined, finally admitting she was a bit sore. It took me a bit to get it out of her, but apparently, he was really thick (which turned me on even more, as it is a turn-on for me to feel a woman who has been with a thicker guy recently. But she didn’t know that).

I guess it happened that afternoon, and when I asked how thick his cock was, she held up her arm and said, “About as thick as my wrist.” I was instantly hard, but she wasn’t in the mood to continue past just getting her off playing with her clitoris. She got off, and we cuddled up to sleep. At least she did. I was still massively turned on, and although we had sex without condoms, she said that they used one.

I was really curious, and couldn’t help myself. When she went to sleep, I looked in the trash can and found the used condom. She wasn’t lying, as I could tell it was quite stretched out, and I am happy to say he came quite a bit.

I was even more massively aroused by this, so I took it and went to the bathroom. I have rolled condoms on many times before, but never a used one. I had to be careful not to spill it as I slipped it on easily, with room to spare. I had to pinch the base of it as I masturbated with it on. I honestly didn’t last long, as I added my cum to it.

I wrapped it back up, put it back in the trash can, cleaned myself up, and went back to sleep next to her.

She never found out, and she admitted that she was surprised I was turned on by her sleeping with him. (I will admit I didn’t push to hear anything more about her and another guy, as that would have opened the door back up for her wanting a relationship. I know it’s complex, but she was into trying to please me, and I think her sleeping with someone else was her way of trying to get me to commit).