i was 18, just got into pubs legally and was met a girl and her boyfriend, got chatting and her mum who was drinking with them came over. Her husband had split with her a year before and it was her 50th birthday and she was looking for a good time
Ended up drinking lots, dancing into the night and then screwing in the back of a taxi

 

19. I'm only 20 though, so it's not much of a stretch for me.

 

my oldest

I used to be a bartender in college. Have a lot of stories from those days. The single oldest was when I was 22 and she was 48. It happened a couple times. She was recently divorced and loving life.

The biggest combined age gap happened at 22 as well. They were 74. One at 36 who was a faculty member of my college and her friend that 38. Orginally it was just suppose to be me and the friend, but it turned into a 3sum. I am not complaining though!

 

Fucking stupid question.

 

I was 18, when I worked at a high rise apartment complex as the night time concierge, while in college. On a regular basis I was servicing 35, 40, and 55 yr old women. I had 60 yr old married man who liked to suck my dick before he went to bed 1-2 a week.

 

My Ex husband who is 9 years older than I

 

Neighbor down the street

She was 44 I was 17 at the time. This took place in March of 1988. I moved away when I was 15 and came back a couple years later, and moved into a new place. I went over to the neighborhood that I grew up in over a few days and talked to my old neighbors. It was fun catching up with all of my old neighbors.
Then I went to my old buddies house and his mom pulled up as I knocked on the door. I walked over to her car, she got out and squealed my name. Who knew a woman at 44 could squeal like that? At that time not me. I got a big, long hug from her. I didn't mind since she was a total hottie. Kathy had dark shoulderblade length hair, a dark tan, dark eyes and was slim and muscular. Not WWE muscular, but fit muscular, the woman played tennis and golf quite often and lifted weights to stay in shape, and did the yoga thing. She looked damn good in a leotard.
But as I was saying she gave me a big hug and pressed her beautiful body against mine. I returned the favor and she grabbed my ass. I thought, " holy shit, this cant be happening", but it was. The fox of a neighbor was hitting on me, as if I would've said no. I pulled up her tennis skirt and grabbed her tight, wonderful ass. Yes, I said tennis skirt. The place that she played at had inside and outside courts.
She said lets go inside and talk, and we talked for a while. She asked me if I wanted a drink, I said sure and followed her into the kitchen. As she was bent over in the fridge I reacted quickly, got behind her, grabbed her hips and ground my cock into her ass. Kathy looked at me and grinned.
She told me that she needed to shower and I said I'll join you. She grinned larger, took my hand and I followed her upstairs to the room she shared with her husband. I stared at her ass and damn near blew my load in my pants as she led the way. I'm sure I was grinning from ear to ear like a moron.
We got to her bathroom and I started taking off my shirt. She stopped me and said let me do it. She slowly stipped me and kissed me all over. I was in heaven. At this point I had, had a crush on her since I was 11 and would masturbate thinking about her quite often when I was growing up. She got me naked and liked my cock, which i blushed about when she told me that.
She stripped and I went slack jawed. This woman had an incredible body. Firm high turned natural tits, a bit on the small side, but I knew that I would enjoy them. She took everything off, dropped to her knees and took my cock all the way in her mouth. After a few minutes I came in her mouth and blushed. I was so embarrassed.
She turned on the shower and we stepped in where we made out for a while. Her lips felt great and her tongue and mine wrestled quite frequently. She got back to her knees and started pumping her head up and down on my cock, in and out it went. She would run her tongue all over my cock as it was in her mouth. She took my cock out, put her hand on it gripped it and started stroking it. She lowered her mouth and licked and gently sucked on my balls. She would move her tongue between my balls and my shaft. Damn it felt good.
After a few minutes of this wonderful torture she stood up and said fuck me. I told her I didn't have a condom. She said I don't care, I want your cum in me. I grinned like a fool again. She laughed and put her hands against the shower wall and said fuck me Tim.
I grabbed my cock, put it against her pussylips, i searched for her hole and finally found it. She looked back at me and accused me of teasing her. I just went along and said yep, cause you've been teasing me with this beautiful body for years.
Anyway I found her pussyhole and slid all the way in. I slowly pumped in and out. She moaned and said, "Harder Tim fuck me harder. I want your cum in my cunt." I never knew that she had such a dirty mouth. So I obliged her and picked up the pace. We fucked each other faster, faster. My hips hitting her ass as we fucked.
She told me, "Grab my hair and yank. Call me slut, call whore, talk dirty to me, Tim" So I did. I wrapped her hair around my hand and yanked back her head by the hair. I called her all sorts of dirty names and kept saying fuck me you cunt. Take my cock whore. I reached around with my other hand and twisted her nipples. She gasped as I did. And told me to yank on them. I yanked and pulled and twisted them. I sucked on her ear and bit down on it. I told her, " I'm going to cum in you slut."
"Yes, yes, fill my twat, lover. Fill me with your seed, Master."
I yanked her head back further and came in her. That day started what would be over 2 years of sex between us and my dominating her.

 

i was 18, she was my 49 year old mother of two who lived next door.

her hubby had walked out a few years earlier for a younger woman (IIRC it was for a 17 yr old goth). she did the usual things after that, changed her style.... started chasing younger guys (and i found out tried women as well)....

my turn was a rather cliche'd affair..... was asked to take a look at her daughters computer that was playing up with a virus.... the payment was to fuck the mother....

I have to admit i very nearly said no..... quite glad i didn't... she was kinky as anything

 

I was 14 she was 46 she babysitted me and took my virginity pm for the whole story

 

When i was 20 i had sex with a woman that was 47

 

Amazing

Me 32 her 36, first girl I ever fell in love with, God, i wish i was still with her!!

 

She would be 84 now!

 

i was 37 she was 89 yo

 

She was maybe 15 years older than me, definetly in her late 50's,she had a great set of titties, and a real sweetheart!

 

Oldest

 

Yesterday afternoon we finally found time for each other after over a week and really went for it. No slow foreplay. By the time I'd delighted in feeling her clit become really firm, briefly denied her demands to make her cum, felt her writhe to my touch and felt her cum twice, I was soo ready to cum myself. Just managed to hold off long enough so we could cum together. Then a daughter 'phoned ! Abrupt exit from bedroom! Oh, and our ages - 66/74! So all you young folk have got plenty of lifetime to find great sex.

 

i was 18

and had sex with a man 57 years old

 

oldest person i had sex with was my mom. she was 38 and i was...well,i was a few years shy from legal

 

My girlfriend, shes 21.

 

That is fucking hot, and I think it's my hottest fantasy to pleasure a mom and daughter. It's probably every guy's fantasy.