[MF] Three Month Long Unique Roleplay I found myself in with younger woman

This might be written not as “sexy” as some of the other entries on here, but that might be because my story actually really happened, and some of these seem totally made up. Anyway:

I am fairly boring and average man in my mid-forties who sort of has always focused on my career more than settling down, etc. I’ve had girlfriends over the years and some one night stands, but never really wanted to get married or anything. I’m also fairly vanilla when it comes to sex, never did anything too crazy or out there.

Until I met Hannah (not her real name). She was just out of college, 22 years old but looked 18 or 19, a redhead with brown eyes and super perky on every level, she was like five feet tall and one hundred pounds. She had just started working at a sister company of ours, the type where we did a lot of of business together and overlapped, so we’d see each other a couple times a month but didn’t work together directly, especially since I was in a different department and way above her in terms of job titles.

She was always very pleasant but I didn’t know she was “into me” until we were in a group of six or seven people traveling across country for a conference, and we found ourselves together one night at the hotel bar. We both had quite a few drinks, and as she got more and more and more drunk and flirtatious, she revealed to me (after I had to keep telling her I wouldn’t judge her) that she had a very specific fetish that she felt like I would be the perfect man to act out with.

Basically, she had never met her own father but she seemingly had a true crush and intense on her stepfather her whole life. She said she would obviously never act on it with her real stepfather, but no matter what she did she always had to think of him while she was either masturbating or having sex in order to orgasm. I was sort of shocked, as I said I am usually very boring sexually, but she asked if I would “act” as him in a sexual roleplay that night, and promised I wouldn’t judge her or tell anyone. We talked it out for awhile more, I wanted to make sure I wasn’t taking advantage of her or anything as an older guy, and then, both super drunk, went upstairs to her hotel room and had the best sex of (at least my) life.

I want to reiterate I am not bragging; women this age or of this attractiveness never look twice at me, but I sort of fell into this incredible sexual roleplay that lasted about three months. Apparently she chose me because of my graying hair, my look (which was similar to his) and that I was “safe”. aka boring.

Back in our city, we’d meet at each other’s apartments (usually mine since she had a roommate) and she’d call me by her Stepfather’s name, or “Daddy” and we’d act out sexual roleplays she had with him throughout her whole life, and she’d sometimes even bring me his shirts to wear, etc. We’d always talk to make sure this was something I was comfortable with and vice versa, since it took me awhile to really get into the role, but I accepted or at least convinced myself that this was something she needed in a “healthy” way, whether that is the case or not I don’t know. I mean, clearly she had “daddy issues” but she was also in light therapy at the time for those same specific issues. Still, our arrangement was always respectful and we both sort of enjoyed what the other was providing.

All I know is that it was the best few months of my life in terms of sexual activity, and after awhile she started dating a guy from her office (her age) and it sort of fizzled out. She is now at another company and last I heard seems to be doing well. I wish her the best and even though I’d never do something like that again, it was fun while it lasted. I later found out these types of roleplay things are super common on like Pornhub and stuff, but at the time it was super taboo to me. Anyway, thanks for reading. If you have any questions, I will try to answer them in the comments.

Source: reddit.com/r/gonewildstories/comments/e762pq/mf_three_month_long_unique_roleplay_i_found