I hooked up with a 53y.o ex-stripper/swinger for a few weeks when I was 21. Learned TONS. She was insatiable, we're talking like 4 hours of fucking. She could cum, and cum, and cum over and over. I'd cum and shed have me hard again in seconds/or minutes. One night I was so exhausted I made her a drink with tons of moonshine so shed get drunk and pass out so I'd get some sleep.

 

i was 17 and he was 55

 

I have to say he 60s. A few times with men 30+ years older than me and I'm 30 now.

 

I was 21 she was 49 and she taught me a lot and was very naughty lol

 

She was 26 and I was 18. Hot girl, covered in tats and pretty wild. That was a good weekend

 

It was with my mother's friend. I was 19. She was 51

 

My first husband was 11 years older than me. I was 16 when we got married. We divorced when I was in my early twenties.

 

Me 35, him 69. He knew EXACTLY what he was doing!

 

Oldest

I was 35she was the 60 year old hostess at a massage parlor which had closed for the evening.
She gave me a massage and I played with her ass. I felt her breasts and they were as firm as any I have ever touched.
She was the best fuck I had ever had.

 

I was 30 then and she was 54. it was funny caused her daughter was my age. Let just say it was a very good two months.

 

Older Woman My First

My father and I spent the summer between my 8th and 9th grade year living in a hotel in downtown Houston while waiting for our new home to be built on the north end of town. We stayed at a hotel where it was cheap to rent a room by the week. The hotel was popular with truckers and had a bar inside that was known to be a pick up spot for prostitutes and was known to be a wild place at night and on wknds. My father bought me a dirt bike to keep me occupied by day and then every night when he came in from work, we would head straight to the bar and stay til close at 2am. The bartendar was a 23 yr old woman who was a knockout and her mother and father owned the bar. I was 14 but could drink since Texas allows parents to serve their kids. The bartendar started flirting with me one night and mentioned to my dad that she was partying that night because her husband moved out and left town so it was going to be a night to remember and little did my young ass know how true she was. We ended up doing shots and drinking crown and seven and 7 & 7 all night long, one after the other and by the time that 2am rolled around, I was asked to bring my dad to an afterparty at the pool. My father was already hooking up with the bartendar's mother and making out with her in the bar with her husband watching the bar (i was clueless to swingers then but later found that the after parties at the hotel pool and in various rooms was a group of swingers that the bartendar's mom and dad started so my dad fit right in but I was a little worried and unsure about going to the party until the bartendar walked over to me as she closed the bar and was ready to lock up and head to the pool and walked right up and kissed me, running her hand down to my crotch and saying that she knew I was a virgin and wanted tonight to be all about me and she wanted me to let her be my first. She grabbed my hand and didn't wait for a response walking me to a hotel room right in front of the pool where I saw alot of ppl drinking making out and doing all kinds of drugs. The lights were out, blacklights on, music loud, strobe over the hotel bed which was round and large enough for 6-8 ppl. Anyway, she slipped me this pill and said take it with her, little did I know that would be the night that I would fall in love with X and in love with everyone in the room, in the world, trees, grass, air, myself, lmao...u get the point right...well when it hit me hard all i remember is my eyes rolling hard (which is awesome) and my teeth grinding back and forth but this feeling in my entire body was the most amazing thing in the world, she knew exactly when it hit and grabbed my hand walkiing me to the heated pool where now i found everyone in and naked, i saw 2 men and 1 lady, even saw a ladies two teen daughters who i met later and found they were 2 yrs older but they were naked in the pool and with an older man that her mother hooked them up with and she was with his son. So Kelly (I will call my bartendar) was all over me in the pool and I was not concerned about anythhing but the fact that I am about to get my first sexual experience by a 23 yr old hot ass woman so yes I was hard as a rock and we made out and all we did in the pool was touch, and kiss and grind...lol...then she grabbed my hand after about 20-30 minutes of that and said it's time to do this, are you ready. Nervous as a goose in a hail storm I was able to answer yes but that was about all I could say due to cotton mouth and shaking inside like Ray Charles... anyway, we get inside and she crawls on this round bed asking if it would be ok with me to do it there in front of everyone in the room and anyone walking in from the pool as the doors always stayed open. I asked her to follow me in the restroom first so I could ask her a few things, she did and as I started to show how nervous I was about being out in that room having sex, she just said hold on, you are only unsure because you don't know what you are doing which every person out there has experienced and understands as well. She continued saying noone out there is here to make fun or criticize, they like wathching it and it turns them on so you would be appreciated. I started getting a little less nervous and then she said, look let's you and I do it right now, right here to warm up and once we finish in here, i know you'll go out there so she took out two more tabs and we took them. She went don on me, and we ended up in the floor of this bathroom on a huge rug. As I went down on her, she coached me and told me everything that women love to have a man dfo to them, she was a good coach because I was able to make her cum and I had no clue, lmao. She looked at me and told me to get between her legs and put my cock in her hands so she could put me inside her, of course the end of this story is near because the moment I entered her and followed her instruction to slowly thrust all the way until I can go no further, I blew a load that felt like A MAJOR FIREWORKS SHOW ON NEW YEARS EVE SHOOTING OUT OF MY ASS, MY COCK, MY EYEBALLS, MY EARS AND ALMOST OUT MY NAVAL, BRINGING ME TO MY KNEES AND THINKING THAT I WAS SO THANKFUL I TOOK THAT 2ND TAB CAUSE NOW I WANTED TO HAVE SEX WITH HER IN THE ROOM IN FRONT OF EVERYONE, IN THE POOL, AND ANYWHERE ELSE WE COULD DO IT IN THE NEXT 16 HRS...LOL...THE GRAND FINALE FOR MY FIRST NIGHT WAS THAT WHEN WE STARTED MAKING OUT AGAIN ON THAT ROUND BED IN FRONT OF ABOUT 20 CPLS WHO WERE ALL NAKED AND EITHER DOING THE SAME OR MORE, I SUDDENLY FELT HER PULL ME CLOSE TO HER FACE AND SHE SAID, LOOK INTO MY EYES AND DONT WORRY ABOUT ANYTHING, EVERYTHING IS OK AND YOU JUST NEED TO ALLOW EVERYTHING TO HAPPEN NATURALLY AND YOU'LL HAVE THE BEST NIGHT EVER, WELL WHILE SHE WAS SAYING THIS, HER MOTHER APPEARED ON THE BED NEXT TO US, MY DAD WAS WITH HER AND HER OTHER DAUGHTER, HER HUSBAND WAS ALSO ON THE BED WITH A FRIEND OF THEIRS AND THEN I REALIZED THAT WE HAD ABOUT 8 CPLS THAT WERE THEIR CLOSE FRIENDS ON THE BED WITH US AND THE WOMEN WERE ALL KISSING EACH OTHER AND TOUCHING ALL THE MEN, INCLUDING ME AND ALL I CAN SAY IS THAT MY FIRST WAS AWESOME BUT MY FIRST NIGHT INCLUDED ABOUT 15-20 TIMES WITH 8-10 DIFFERENT WOMEN AND EVEN WITH KELLY AND HER MOM IN A 3SOME TO END THE NIGHT WHICH WAS ACTUALLY THE NEXT AFTERNOON...LOL..KELLY WAS 23, HER MOM WAS HOT TOO AND IN HER MID 50'S, ONCE AGAIN, I WAS A VERY HAPPY 14 YR OLD. ANYWAY, SORRY FOR THE RAMBLING AND LONG FREAKING TOUR I TOOK YOU ON TO ANSWER YOUR QUESTION. TBO

 

I was 29, She was 50.....Her hub was 51 and my wife was 30..... swinging is fun lol

 

I was around 16 and he was in his 40s a friend of my father

 

The wife. She's forty . . . um . . . er . . . something.

 

Just had amazing sex with my 50 year old step-mother. I'm 19 btw

 

i was 19 she was 44 n after we fucked n car she was like boy u fuck like ur daddy i was like huh ,omg i didnt know she used fuck my dad back when they went high school lol, all my daddy could do was laugh years later when told him

 

Me 25, her 34

 

55

 

Me 38, her 41
I've also had phone sex several times over the last 2 years or so with a married woman in her early 50s. Her husband hasn't touched her in years, she's always horny

 

I was 16 legal here in UK and he was about late 50's early 60's