by Justin

Gender: Male
Age: 28
Current location: California
Highest education received: Some college (not currently in college)
Occupation: Self-employed
Relationship status: With somebody
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 10+
How many hookup stories have you here posted before? 0

Fucked My Friends’ Mom While They Slept Next Door

How long ago did this hookup happen? 4 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Secret love affair

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Kate (this is the name I’m using for her) was the 40 year old mother of a friend that I knew, she was pretty, had a really great and loving personality and always treated me well and called me son.  Kate had a flair about her, the way she carried herself as a confident and I would even describe her as a desirably cocky person, this was the sexiest part about her.  I didn’t know her too well but she was just that type of person to always welcome you with open arms.    I have to say I had a crush on her but this was before I ever imagined realistically being involved with an older woman.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? When I was still in college, she would invite me over to hang out with her and her daughter and just be around and sleep over and be apart of the family (no father around so I kind of took over as the man of the house).

The house was full of people so I would spend nights in her room, sleeping on the couch but one night I was feeling bad about a personal matter.

As far as what she told me later on, it was one time we went to travel a couple months prior to the hookup where I kissed her on the cheek in a playful manner when she started developing feelings for me.  We did not plan to have sex and in terms of actual sex, I think the instigating leaned more to her side.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? She asked me into her bed and we talked for a little, then in a vulnerable moment she kissed my face all over leading to my mouth and we just made out passionately.  (Believe me when I say I was completely shocked this had occured).  I quickly became horny as fuck and threw her on top of me continuing to kiss and I literally just couldn’t take it anymore and had to get inside her so I took my penis out of my boxer hole and slid her panties to the side and we had crazy but quiet sex.  We did it in every position constantly changing.  She was loving every second of it and so was I.   Kate had a “move” where she would squat on my cock and just use her vagina to fuck the head of my dick over and over again, sometimes she would come down but take it up right before her ass hit my pelvis.  Then when I’d least expect it, she would slam her ass all the way down and it was the most fuck-tacular thing I’ve ever experienced. (one time she slammed it down right as I came, most memorable fuck ever)  I honestly don’t remember how that night ended but I’m pretty sure I woke up on the couch.

Did you have an orgasm? Did your partner(s)? I did not cum and I’m not sure if she did because we kept it so quiet because every room in the house was filled with people and the kids were right next door.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No precautions, I gave we just assumed each others’ history was all good.

What were your REASONS for having this hookup? We were just attracted to each other but we never ever had a really good opportunity to get it on until now.

Were alcohol or drugs involved? If so, how much? None

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? The second we stopped having sex the day after our hookup was one of the most, if not, THE MOST insanely emotional day of my life.  I was already so ingrained to the family that having crazy sex with Kate was just unimaginable from my standpoint. We both tried to go back to normal the next day because we didn’t know what to do at all, with anything.  It was somewhat awkward but we talked a little and she was telling me how we would get used to what just happened and how we need time to get back to normal.  Eventually we hugged and talked about how we shouldn’t let that happen again.  We pretty much kept up our secret love affair for about half a year and fucked whenever we had the chance.  Eventually I had to go back to reality and work and school but it was very fun, while it all lasted.

To whom did you talk about the hookup? How did they react? I told a good friend that something like that happened with a woman that age but I never got into details and who and when and what.  I personally don’t like to talk about my sex life to others.

Was this a consensual and/or wanted experience for you? For your partner? Consensual and amazing.

Do you regret this hookup? If so, why? Not at all.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Best thing was I finally was able to indulge in an older and EXPERIENCED woman.  Worst thing was we could not publically show our affection because everybody that knew us saw us as informal son and mother.  It was crazy.  This experience definitely got me more experienced, she was the best sex I’ve ever had, ever.  “Kate’s Move” was so brilliant that it left me wanting it after we had drifted apart.  To this day, I wish my sex partners would do this move.  Maybe one day we will reuinte again.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup or anything else? I think about her every now and then and I’m sure she does too.  If I ever had the chance to have sex with her again, I might do it but I also might not as I’m already in a relationship right now.  We have lost contact with each other and haven’t talked for four years although I do have her phone number, I’m not sure if I want to call her.  I still communicate with her kids though and we both thought they suspected us of our fling.

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