by Matthew

Gender: Male
Age: 33
Race/ethnicity: White
Current location: Austin
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Radiologist
Relationship status: Divorced
Religious affiliation: Catholic
How religious are you? Somewhat
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Anything goes in the right circumstances
How many sexual partners have you had in your life (including oral sex)? 25
How many hookup stories have you here posted before? 1

Select Soccer & The Demanding Schedule

How long ago did this hookup happen? 18 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…)? A dirty secret

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? Mrs. B was the tall (6’2″) skinny mom of my best friend. She had the longest sexiest legs and always wore trendy short skirts and some type of leggings/hose with high heels. She is an avid runner and was very toned.  Her husband was some type of important man at IBM and was never around, that was true of most my friends on the team dads.  She lived two streets over from me since I was 6 years old and her son and I were inseperatable  from that day. Our travel soccer team was very elite and many have gone on to having careers in the pros.  But we all knew each other from 10 y.o. all the way to 18. This means our parents were also close and the moms especially being that they were always the ones traveling with us.  Mrs. B was the team parent and handled any problem involving the parents concerns or questions. She was very approachable as she was always loud and laughing and you couldn’t miss the long legs and short skirts…she was very eager to always talk with all the boys. All the 14 year old boys were always accepting of her hanging with us.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Our team traveled so often that we had a team tutor on our travels that helped every player pass, she would work with us in the hotels or on the buss or plane rides.  If the team took the buss then Mrs. B would drive her luxury travel van and follow, as well as some other moms did the same.  Well I was tired of all the noise on the buss and not being able to hear the movie and was getting very pissed at the situation and told Mrs. B that I had a headache and wanted to ride with her and go to sleep watching a movie. My mom had training at work that week and couldn’t make the game so Mrs. B was asked to look over me by my mom.  So mrs. B told me to hop in and throw on a movie.  Her friend (my other friends mom) was riding in the front with her, she was the one mom on the team that everyone agreed that she was the number 1 milf years running, her name was Tarah.  I felt lucky to be the only guy in that comfortable and quiet van with the two best looking moms on the team.  When we traveled the team all wore the same gear which was thin/short white shorts with 3 Adidas stripes on the sides with white socks and same black stripes and our travel jersey with just our names on it that was white with black stripes on the shoulders.  I never wore underwear and always joked if I got water spilled on me or sweat too much the moms would get a show, a lot of the boys did this as a game to excite the moms.
I jumped in the back of the van and leaned back the captains chair and propped my foot up on a igloo ice chest and laid back on my pillow to watch the movie on the back of the seat in front of me. I felt a breeze of air conditioner blow past my always sensitive 14 year old prick.  I was a good 8″ by age 14 and the boys called me tripod  or kickstand bc if I fell over my third leg would catch me, I didn’t mind bc these guys would tell all the girls the same…it was flattering.  When I felt this breeze I looked up to the rear view mirror and noticed the eyes of Mrs. B looking back at me. It was there I decided to adjust my thick and long cock to run down my leg where if you looked back at me you would see through my short leg that was propped up on the cooler.  My cock grew and soon I was pressing down on the base of my cock to make it not stick straight up and I made it run down my leg.  I pretended to be asleep and they turned off the movie. Tarah had to reach in the back to turn it off and when she did I heard a huge gasp for air and heard her say Mrs. B! Oh my god mrs. B look! My heart was racing and I tried to keep from smiling and just laid there pretending to sleep.  I heard Tarah giggling and saying you are not going to believe this. Then I heard the seat leather wrinkle and I knew she had turned back around.  I guess mrs. B couldn’t turn around bc she was driving so she was asking Tarah what was it? I couldn’t look.  Tarah just said I will hold the wheel, it’s something you’ll have to see to believe! So that’s what she did. I heard the seat wrinkle and I heard her voice say “oh! Well, oh my…that is so….ummm…just wow Tarah!” And Tarah said yeah I know babe!  They are both looking forward now and the topic has been all about my size and thickness and wishing they had a husband that was gifted like that.  They talked about adjusting their mirrors so they could see my cock at all times without having to look backwards and that’s what they did.  So I would act like I was stretching and I’d push down on the base hard and it would move my hard cock enough to make my shorts fall down more only now my young and big cock was sticking out all the way from my shorts and when I let go of it it laid back and pointed toward my stomach and stuck straight out for the whole world to see everything.  They both started squealing and frantically whispering oh my god, oh my god! And just laughing. When I would move they would look straight ahead and just stop talking then they were back at it again.  Tarah says “I just want to touch it one time, he won’t know, he is sleeping” !  Mrs. B didn’t say a word,  and about a minute later mrs. B tells Tarah to stop licking her lips and just don’t wake me… Tarah squealed, “really”!   And Tarah leaned back and I felt a warm soft hand firmly wrap around my shaft and slowly move up and down and my cock was starting to jump in synch with her strokes.  She stopped soon after and told mrs .b how hard and thick it is as we just pulled up to the hotel.  We parked and they called out my name and I woke up with my cock being soft and my shorts had fallen back over it.  I went in with the moms and I got my room key and they moms got theirs and their sons.  Everyone always slept in their parents room except me as I often had a room to myself…

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? I told mrs. B that since she is supposed to watch over me while I’m here then I should give her a spare key to my hotel room, and I said goodnight to the moms and they both said “oh it was”! And started laughing, then said goodnight Matt.
I went to my room and made sure not to lock the chain so if mrs b needed to see me she could get in;) it was about 10 and I took a shower and ordered a movie on the Telly and I actually fell asleep with the tv on.  It was about 230 am and i felt a hand massaging my chest.  I was in shock at first, I didn’t know who was in my bed and I kinda jumped and then looked at my right and saw mrs b laying there in a babydoll see through nightgown and a black thong.  She quickly put her fingers over my lips and shushed me and calmed me…when I saw it was her, my dick got so hard,so fast! I was wearing a towel but it had found its way off and I was laying there naked with my friends mom!  I had seen some porn and knew the basics I guess. And I knew what was about to happen!  She slid her leg over mine and rubbed my balls with her knees and gripped my hard cock in her long skinny hands and then sucked my lips and stuck her tongue in my mouth! I couldn’t do anything but lay there and exhale deeply.  She told me, “while you slept in my van today, I saw your huge cock sticking out the leg of your shorts and I couldn’t let on how much I wanted it in my mouth or in every hole in my body.  Even Tarah wanted your hard dick and she couldn’t stop herself and felt it in the van, I didn’t want her knowing how interested I was so that I could keep this between us possibly…
I told her of course we can, your son would hate me and the team would hate me bc they might think I’d do the same to their moms, so it’s not a problem at all.  I wasn’t going to have her undermine my capabilities as a fuck buddy. So I was very rough and demanding of what I wanted from her.  I stood up on the floor and I brought her long legs up over my shoulders and grabbed her thighs and scooted her ass and wet shaved pussy toward the edge of the bed.  I wiped my cock head on her wet slippery slit and slid it over her swollen clit and down into her contracting hole.  I then just rammed it in balls deep and leaned forward pressing her legs against her tits and I put my hands around her neck and I squeezed as I thrust into her deep and hard! I squeezed hard and pumped harder as she gasped for air and rubbed her pussy so rough,even spanking it a few times in between rubs.  She started shaking and her body tightened up and squeezed my cock and I pumped my cock in tip to balls and let out a huge gallon of cum all over her pussy and asshole. It was fast an over soon but it was intense and I couldn’t go long as she just took my virginity and it was my friends mom! It was kinky enough so I came really fast.

Did you have an orgasm? Did your partner(s)? Yes we both came hard and laid in sweat after.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None, I was a kid and she was married . Thought it was safe enough.

What were your REASONS for having this hookup? I fantasized about this and wanted to lose my virginity. She was so sexy

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? We hooked up for years after. Many more experiences. It was all fun and wonderful for both of us

To whom did you talk about the hookup? How did they react? She told Tarah and I told my uncle years later

Was this a consensual and/or wanted experience for you? For your partner? It was consensual and wanted by both.  She said she couldn’t resist

Do you regret this hookup? If so, why? No

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? I have a fetish for hot Milford now! And tall women

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup or anything else? My friend found out eventually

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