when i was about 21 i was living in St Paul, grew up in Chicago, and had to go back home for a family event. At the event i ran into my aunts bff who i had a crush on since i got my first hard on. I dont recall the exact circumstances but she told me she wanted to get "coffee" next time i came home. Now, i am no casanova, but i am fully functioning so i noticed that something about the way she said coffee, didnt mean coffee.
Now, i knew something was going on but i really did not know what. All i was sure of was that i had to get back to Chicago and get some gd coffee with, lets call her Cougarmilf. As a back story i was in the middle of a 3 year relationship with the 3rd woman that let me inside her
and i am a faithful partner.
Again, i dont recall why i was in Chicago, but i was there and obv hit up the CM and inquired as to the details of our coffee date. She didn't respond until 10pm saturday night. Her response was something like "i am at my friends, her son is having a HS grad party and you should com". My fam is on the north side and she was in a south suburb (min hour drive) so i did what any young man would do, i asked my uncle (CM's now semi-brother in law by bff) to borrow his car to go see a friend. The only inquiry I got from Unc was after he knew it was to see a girl he dgaf.
Hahaha, the details coming in are great.
For the cherry on top, when i got back to St Paul, my roommate picked me up in his car and when i scooped me i immediately jumped in the car with the biggest **** eating grinn ever and when he asked "how was it" i couldn't wait to belt out "you won't believe what happened", bc i just bagged a gd cougar i had jerked off to literally hundreds of times, and i was met with my current GF leaning forward from the back seat asking "what happened!??!?!" FMFL
So i get to the house, and its a condo in a large planned development, and there are a lot of wasted HS kids. The CM sees me, makes a B-Line for me, grabs me by the collar and jams her tongue in my mouth. That happens, i come up for air and all i here is "let's go upstairs". Now my lizard brain was taking over and i wanted to be a "good guy" but all i could muster up was "The brakes don't work so good". That fell on deaf ears and next thing i know i am upstairs with no clothes on.
So i am upstairs and all my clothes are off and i am inside her mouth but she still has her underwear on so i naturally tell her to take it off and find my way in the promised land. Now idk what i have but anytime i hear a girl go "its so big" i tend to just think its lip service, but this braid carried on about it the whole time. And not just in passing, like making strange comments like "you are so bigger than my husband", etc. Now, in retrospect i would write it off to dirty talk, but i was 21 and way out of my depth. So eventually i had her legs around my kneck and was giving it all i had (SSRI's can really make climaxing difficult) and she was carrying on about a lot of **** and eventually i hear "what did your mother feed you". At this point in my life i was not preparred to handle this lievel of kink/dirty talk/****ed up partner to really run with it so i just stopped, clothed up and left. The mommy talk killed the hard on.
The real ****ty part was on the ride home the car ran out of gas on the highway entrance, at ~3am on the south side of Chicago and i had to get a tow in my uncles car, hwich invlolved a lot of calls to him and the dealer and the warranty service for the tow (warranty was free tows under 50 miles and i was 49 miles away at 3am, fmfl). As soon as i got back to his place around 6am he asked me what happened. I told him i went to meet the cougarmilf for coffee. He has never said another word to me about it
Last edited by thabighurt35; 01-11-2018 at 12:40 AM.