Hooking up in college, with the help of a Milf. [MF]

Okay hopefully I will keep this short. Freshman year of college I became friends with a cute girl (Jess) who I just happened to hold an umbrella for her b/c she forgot to bring one. (IK romantic) It quickly became more than friends as we began hooking up 1-2 times a week. Everything is going smooth until the beginning of December when she starts pushing hard for us to become a couple. I was fine with it, she was cute, friendly, smart, the whole works.

Over X-mas break I get invited over her house, we lived only a half hour apart. As soon as we walk through the door, the mom (Let’s call her Katie) almost runs me over, gives me a huge hug (an extremely intimate hug considering we just met). And to put the cherry on top of the awkwardness sundae she feels up my bicep as she is pulling away.

Some background on Katie, divorced from a super-rich, attorney. Total blonde trophy wife, that works hard to stay in shape and young. (Later found out she dated some guy that no homo was sexy and was still in his late 20’s) Dinner was fine except that Katie kept sliding in comments about how attractive I was and how cute we were. Those comments said once are harmless but repeated five times each is creepy. But I shrugged it off at the time.

So summer time came around, still dating. One day my car broke down, I knew Katie worked nearby and she was glad to pick me up and drive me. So were about 10 mins out from the house, when all of a sudden Katie drops this bomb. “So when was the last time you and Jess had sex?” Completely blindsided I mumble out a reply, “uhhh, uhh idk 2 weeks ago.” (The truth, we were just busy lately) Are you not attracted to her anymore? She asks. Trust me I am very much attracted to your daughter. I reply. Okay well Jess does not need a boyfriend who is some god-damn wimp! Listen I’m not going to be coming home for a while, when I drop you off, you better grow a fucking pair, be a man, and fuck her. I stayed silent, But instead of thinking with my head and telling her she is out of her mind, I thought with my penis instead.

I was a weird combination of horny and angry, I walk in the door, Jess is making PB and J sandwiches happy to see me. “Hey what’s up, I’m glad—-” no words, I pick her up, carry her up the stairs and fuck the shit out of her. No emotion whatsoever, just pure animalistic sex. When I finished, I heard her sniffling and wiping away tears. Still no words, I just didn’t know what to say, we waited in separate rooms until my parents picked me up. I called her the next day, and balled by eyes out and told her I was sorry b/c I really was, If I was thinking clearly I would have never done that. I could not however, come to tell her the reason behind why I did that.

Just as things were getting back to normal, Katie sits Jess and I down and. essentially says I know you guys are having sex and that is normal and healthy and a bunch of other BS, safe sex, etc. She then says I want to ensure we continue to have fun and that she is ordering gifts for us. I get a text from Jess the following week to come over immediately. I ring the door bell, and Jess answers wearing some expensive looking black lingerie set. She tells me to come to her room, and I could not believe my eyes. Boxes and Boxes of Victoria Secret Lingerie, literally it was if there was one of everything from the store. Next week, a shit ton of sex toys arrive. Jess literally has so much crap, she has a sex closet which just stores the sex stuff and lingerie. I asked Katie the reason behind this and how much money it cost, to which she replied to not worry about it and to just enjoy. wtf does that even mean.

But nevertheless, the rest of my summer was filled with amazing sex, with a girl I loved, especially as we got more and more experience with each other, and learned to maximize the pleasure for each other. The summer came to a great end with a vacation to the Caribbean, just for the two of us, funded by Katie’s seemingly endless divorce money. I think the week can be summarized by saying that Jess had to get off the horse early during horseback riding because her vagina was sore.

In conclusion, we are just starting our Senior year of college and nothing has really changed. The same hot sex, and the mom still acting weird as hell. However, even though I love Jess, there is no way in hell, I can have Katie as a mother-in law, but I am afraid of the repercussions of breaking up with her. Pain to her, (I’m her first and only love) and of course who knows wtf to expect with Katie, if I break up.

Phew, that’s it. I’ll be happy to answer any questions.

Pics: https://imgur.com/a/Lx3hXQ3

Source: reddit.com/r/gonewildstories/comments/9lk42b/hooking_up_in_college_with_the_help_of_a_milf_mf