I [M] roleplayed with a Milf as her Stepson.

So like many, I use a lot of the apps to date/meet up etc. one day I matched with a woman in her early 40’s and she immediately messaged me saying “Omg you look just like my step son.” I was kind of taken back it was a little strange to hear that on a dating/hook up app but whatever. I message back saying something just kinda funny like, “haha oh yeah? Is that a good thing?” We start chatting back and forth and get more familiar. She divulges to me that she’s always thought her stepson was very attractive and she’d thought of him in a sexual manner but never actually acted on it.

For our first meet we just wanted to chat see how our chemistry was nothing sexual. We met at a bar and hit it off really well. Have a few drinks and great conversation. Say we will see each other again soon and leave. She texts me later that night and asks me, “We got on great, and I don’t wanna scare or freak you out but.. could you roleplay as my stepson next date?” I gave it some thought before answering, it was a bit odd, but I wasn’t opposed to it. She shared with me some personal details about him and how he typically acts.

Next time we met up I roleplayed as her stepson. We met at a different bar, again great conversation. This time she kept referring to me as her son and how big I’d gotten. The bartender occasionally gave us looks but it didn’t feel too strange. After a few drinks she got more handsy putting her hands on my thighs, whispering naughty things in my ear. Even going so far as saying to the bartender “can you believe how hot my son is?” He gave me a look like wtf dude? I just laughed and shrugged. She asked me to come back to her place with her.

She said everyone was gone for the weekend. She wanted me to go into her step sons room, undress and lay in his bed and wait for her. I got to his room, undressed and laid in bed naked. She came in some time later wearing only a robe and said “oh sweetie, can momma cuddle with you?” I nodded and she removed her robe, completely naked underneath and got into bed next to me. She immediately started rubbing my cock, and whispering to me, “oh I’ve wanted this for so long Sean (her stepsons name).” We then ended up having sex in his bed, with her climaxing while I came inside her. That was the first time we met up, it was not our last…

Source: reddit.com/r/gonewildstories/comments/qg6psi/i_m_roleplayed_with_a_milf_as_her_stepson