My best friend from college after college, a mutual friend of myself and my brother at a house party, and a girl from craigslist who actually showed up and was attractive.

 

Never thoguht

It was a former student. She was back for Homecoming after being out of school for about 3 years. We met at a tailgate and she was a little drunk. We hugged at meeting each other and she whispered into my ear that she always wanted to fuck me. Well that night in her hotel room she got the chance! She did a great job!

 

A Best Friend's Mother

Then Him!

 

My girlfriend. She 21 years younger than me and is simply the best.

 

Last year at 10yr HS reunion hooked up with our class valedictorian. She was by far the last person i'd ever have imagined hooking up with.

In highschool she was a year younger but bumped ahead a year, she was hot then but a massive prude who was rather stuck up and looked down on most people, the type who wouldn't even think of associating with my group of gearheads and jocks. After highschool i'd heard she had an affair with her manager at mcdonalds, got knocked up, got married then popped out two more.

We had a sort of last minute get together at the main pub in our hometown, decent turn out of 50 or so people. She was dressed up more than most and did not look at all like she had 3 kids, still very skinny, tall and incredibly fit, after dinner most people broke off into their old cliques and started drinking, oddly she came and sat with me and a few buddies at our table, she was some new age independent business women with her own company [honestly couldnt say what it was, i really didnt care], we all drank and caught up, we were all getting pretty drunk, i'd lost track of how many i'd had and she'd put back at least a bottle and a of wine, buddies head outside for a smoke and she starts inquiring about whether or not im in a relationship [i wasnt], just keeping things going i ask if she is and she starts telling me bout her family, i play along as if i know nothing, ask why her husband didn't come out and she tells me hes watching the kids and he likely wouldnt have had much fun, i asked why not and she says cause hes a bit older and getting drunk wasn't his thing anymore, i asked how much older and she says hes 49, i was a little surprised to be honest, i asked how that was working out and she starts telling me how they'd had a few rough patches but after some counseling and shit they'd realized that source of problems was their very opposite sex drives so they'd decided to have an open marriage where she could sleep with other guys[ she just had to use a condom] and things had been great ever since, i wasn't really sure what to say, then she asked if i still lived nearby [i did], she leans in and says "If you want to we could head back to your place" , the look on her face said it all so we left, she was rubbing my cock the second we got in the cab, when we got to my place i couldn't believe this was the same chick from highschool, she was wild and we went about 4 rounds followed by a quickie before she left in the morning, she left her business card and said she wanted to hook up again, unfortunately the last two times she's been in town ive been out of town.

 

This girl that was a senior when I was a junior.....I lusted after her (as did damn near every other guy in school)....about a month after I graduated, I ran into her at a bonfire where there was plenty to drink, plenty to smoke, plenty to snort, & the music was loud....I haven't thought of that night in years but there's a big-ass smile on my face and a bigger boner reminiscing......

 

yes... my older sisters best friend growing up and throughout higshcool and college

 

My sister's friend, Sonya. She was staying the night at our house. She was BBW and very nice too. she married young and was recently divorced 6 months later. she lived far away and occasionally stayed at our house. We got naked one late night and I fucked her brains out all night and when my sister went to work the next day...the whole day...was intense.

 

Yes, a young neighbor who watched after my place when I was away. He asked me to pretend to be his girlfriend so he could impress (not that I'm impressive) his friends. I ended up taking him home and to bed with me.

 

An ex next door neighbour - she had lived next door for over six years and in all that time the only words we had exchanged where neighbourly pleasantries, never had any conversations. If she'd been a bit more friendly I would have 'made a try' because she was very attractive.
One day I was sunbathing, nude as always and as always for some reason when sunbathing nude I got a full hard-on and started stroking myself.
After about 5 minutes I heard a voice say "You're not going to waste that are you, I've been watching and I've got very horny, if you want I'll come round".
Looking up I saw her leaning out of her bedroom window and all I could do was vigorously nod (both my heads) in acceptance.
She came round dressed in a kaftan type dress which she immediately stripped off to revel she was also totally naked.
No foreplay, nothing said she just 'mounted me' and rode us both to orgasm ..... Then she told me that her husband had been working away for three months and she had been 'in need'. We went inside and spent the rest of the afternoon trying our best to destroy my bed and carried on doing so every day until her husband returned ..... after that it was back to just neighbourly pleasantries.

 

I would have to say my sister, a woman that was in her 70’s and I was 22 doing some work at her house and a gf’s sister

 

My best friends ex wife with him watching

 

a guy i was dating. His daughter was 19. she confided in me that she liked girls and was afraid to say something to her dad. Many of the guys i date I dont mention that I am bisexual, however I told her. We spend the next few nights at my house in a 69

 

A woman that lives in the neighborhood. We met at the park, talked as we would jog nothing sexual at all. She just bought a house around the corner from me, divorce finalized. Well winter came and we didn’t see each other. When warner weather hit we saw each other in the park. She invited me back to her place and we spent the morning fucking.

 

I answered back in 2010 as well. For guys, we rarely know when we are getting laid so every time is a surprise. Ha.

Anyway, I was at a wedding in 20o9. The host was tha mother of a famous major league baseball player. She was 51 at the time. I was 42. I stuck around and helped clean up her home after the party. Eventually it was just the two of us. She walked over, thanked me, and started kissing me.

Next thing I know she's sucking my dick, I am eating her pussy, and then we are fucking. I never saw her again. We fucked twice that night and again in the morning. We did anal the second time. She swallowed twice.

Mature women are absolutely the best in bed.

 

Yeah, my wife's girlfriend. Well, she was really her best friend and bridesmaid. I thought she was only going to blow me. But one thing led to another and you know how shit happens? And once that shit happens it's a continuous flow.

 

Nearly a decade after he was my third-grade teacher - I fucked my third-grade teacher.