What is the largest age difference that you had sex with?

Flaguy Xper 6

What is the largest age difference that you have had sex with? How old were you and how old was your partner?

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Most Helpful Girls

Megalyssa Xper 6
+1 y
14 years difference. I was 46 he was 32. We lived together for 5 years. Overall that's 7 years together. My last one was 20, he claimed to be older but could not go to a club with me. That was for a few months
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- Flaguy
  +1 y
  You were with a 20 year old? How old were you, you Cougar You!
- Megalyssa
  +1 y
  Hm hmm 52... fun fun
DizzyDesii Editor
+1 y
Zero. I was 15 and so was he. #NoRegerts #OnlyRegrets lol
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Most Helpful Guys

martyfellow Editor
+1 y
7 years,, but she lied to me and said it was only 2 years. An obvious lie given the age of her children...
0 2 0 0
- Flaguy
  +1 y
  How old were you and her?
TaureanBull81 Guru
+1 y
18 years. When I was 19 i lost my virginity to a 37 year old woman 😉
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- Flaguy
  +1 y
  Did she know you were a virgin? How did you 2 meet?
- TaureanBull81
  +1 y
  I told her when we got to the bedroom at her place. It turned her on more that she was taking my virginity haha 😂 We met each other while out on the town.
- Flaguy
  +1 y
  Was she married?
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- TaureanBull81
  +1 y
  I don't believe so lol.
- Flaguy
  +1 y
  Did you go bareback or did you use a condom?
- TaureanBull81
  +1 y
  We fucked bareback and I've been a bareback lover ever since 😉 🍌
- Flaguy
  +1 y
  Same here! Did she tell you if she was on birth control, or did she not mention it so you just went for it!
- TaureanBull81
  +1 y
  She didn't say anything about birth control that night but I didn't pullout either!

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What Girls & Guys Said

5 17

MadeInAmerica Guru
+1 y
5 years. My wife.
0 2 0 0
- Flaguy
  +1 y
  Is she older or younger than you?
- MadeInAmerica
  +1 y
  Younger
ClothingOptional Xper 5
+1 y
21 years 😳
0 2 0 0
- Flaguy
  +1 y
  How old were you and how old was your partner?
- ClothingOptional
  +1 y
  I am 40 and he was 19
- Flaguy
  +1 y
  how did you 2 meet?
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- ClothingOptional
  +1 y
  Online
- Flaguy
  +1 y
  Were you looking for young guys?
- ClothingOptional
  +1 y
  No. He found me. I usually go for older.
- Flaguy
  +1 y
  Did you have sex with him on the first date?
- ClothingOptional
  +1 y
  It was only a hook up so yes.
- Flaguy
  +1 y
  Did you let him go bareback or did he use a condom?
- ClothingOptional
  +1 y
  Condom because I didn't know anything about him really.
Lolita911 Xper 6
+1 y
I was 21 and he was 18
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truthbeknown Master
+1 y
My wife is 5.5 years younger.
0 2 0 0
fauchelevent Master
+1 y
5 days older than me.
0 1 0 0
rubyrose83 Yoda
+1 y
I was 18, he was 31
0 3 1 1
- Flaguy
  +1 y
  Did he know how young you were?
- rubyrose83
  +1 y
  Yep, I was legal lol
CapnHawk Guru
+1 y
10.5 years older than me.
0 1 1 0
- Flaguy
  +1 y
  How old were you when it happened?
- CapnHawk
  +1 y
  Eleven years ago. She was 34 and I was 24. She was my oldest virgin.
- Flaguy
  +1 y
  Sweet. Was she any good?
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- CapnHawk
  +1 y
  She had a lot to learn. She was an ex-nun and had just left the convent.
- Flaguy
  +1 y
  WOW! Did you see her just that one time?
- CapnHawk
  +1 y
  Oh, no, we dated for about four months. An LDR that didn't work out, as to be expected.
- Flaguy
  +1 y
  any time you can take a cherry is special
- CapnHawk
  +1 y
  I've popped my fair share.
- Flaguy
  +1 y
  So you popped a 34 year old cherry. What is the youngest cherry?
- CapnHawk
  +1 y
  17 years old - when I was 17.
JustinTheGreat Editor
+1 y
I was 16, they were 20
0 1 1 0
dolemite68 Guru
+1 y
I was 20 and she was 36, she was so much fun
0 2 1 0
- Flaguy
  +1 y
  Was it a one night stand or did you see her for a while?
- dolemite68
  +1 y
  saw her for a few months, met her at the gym she had just gotten divorced
- Flaguy
  +1 y
  So did you ask her out or did she ask you?
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- dolemite68
  +1 y
  she asked me to hang out but I would definitely have asked her I just wasn't sure if a woman that age would be interested in me
- Flaguy
  +1 y
  Was she married?
- dolemite68
  +1 y
  recently divorced
- Flaguy
  +1 y
  Did she let you go bareback or did you use a condom?
- dolemite68
  +1 y
  bareback : )
- Flaguy
  +1 y
  Awesome! Did she say if she was on birth control or not? Or did she not mention anything about birth control or condoms so you just went for it?
- dolemite68
  +1 y
  she actually had her tubes tied, she had two kids and was adamant about not having any more
- Flaguy
  +1 y
  That is cool! Why did you stop seeing her?
- dolemite68
  +1 y
  I was out of state for college so we kind of just ended it on good terms when I went home for the summer. Could definitely tell she wanted to be in a relationship with someone closer to her age I was just a bootycall which I totally get I mean that was a pretty big age difference
OlderGuy965 Yoda
+1 y
At 51, fucked a 22 year old a few times. Just in November I did it the first time
0 1 0 0
NightOwl8801 Guru
+1 y
I was 27 and she was 42
0 2 1 0
- Flaguy
  +1 y
  Was it a one night stand or did you see her for a while?
- NightOwl8801
  +1 y
  My current work schedule keeps me from seeing her , not enough time unfortunately.
- Flaguy
  +1 y
  Is she married?
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- NightOwl8801
  +1 y
  Never married and no kids. I like her , its just I never have the time to see her due to work constraints.
- Flaguy
  +1 y
  Does she let you go bareback or do you use a condom
Marinepilot Guru
+1 y
I slept with a woman 12 years older than me. I was 23 and she was 35.
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- Flaguy
  +1 y
  did she cum on to you or did you cum on to her? How did you 2 meet?
- Marinepilot
  +1 y
  We lived in the same apartment complex. We just hit it off.
- Flaguy
  +1 y
  Was she married?
- Show All Show Less
- Marinepilot
  +1 y
  Divorced. No kids and could fuck like a Mink in heat !
- Flaguy
  +1 y
  Awesome! Did she let you go bareback or did you use a condom?
- Marinepilot
  +1 y
  Bareback. We had a pregnancy scare. That would not have been good. But she wasn't pregnant.
- Flaguy
  +1 y
  That is good that it was just a scare. Was she on birth control? or did she not mention it and did not stop you when you did not have a condom on and so you just went for it?
- Marinepilot
  +1 y
  We got hot and bothered and carried away. We fucked about 10 times that night. After the first time I asked if she was on bc. She said no. I thought to myself, "Oh shit ! I just knocked up a much older woman ! " I figure either she was or wasn't knocked up at that point, se we might as well enjoy it. We lasted for awhile, then she got back with her ex husband. Damn she was some GREAT pussy !
AmericanDude Xper 5
+1 y
I fucked a 52 year old woman before.
0 2 1 0
- Flaguy
  +1 y
  How old were you? how did you 2 meet?
- AmericanDude
  +1 y
  I was 19 and she was my professor
- Flaguy
  +1 y
  Was she married?
- Show All Show Less
- AmericanDude
  +1 y
  She was getting a divorce at the time. Now I'm dating a 45 year old woman.
- Flaguy
  +1 y
  Did she let you go bareback or did you use a condom?
- AmericanDude
  +1 y
  A condom
Tim-loves-it Guru
+1 y
17-20 years.. a supervisor at work!
0 2 0 0
- Flaguy
  +1 y
  was it a guy or girl supervisor?
- Tim-loves-it
  +1 y
  It was a hot chick!
- Flaguy
  +1 y
  Was she married?
- Show All Show Less
- Tim-loves-it
  +1 y
  Yes she was. Her husband was military and on temporary duty for 2 years in korea
Randy_Grant Xper 3
+1 y
I was 24 and she was 47
0 1 1 0
Anonymous
+1 y
5 years older
0 1 0 0
Anonymous
+1 y
A 12 year difference
0 1 1 0
- Flaguy
  +1 y
  how old were you and her?
- Opinion Owner
  +1 y
  Me=27... Her=15... I know, I know, I was an idiot
- Flaguy
  +1 y
  I am not going to judge you. If she was ready then it is ok. Did you date her or was it just a hook up?
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- Opinion Owner
  +1 y
  She was the cousin of a girl that one of my roomates knew, and introduced me to. I guess you could call it a "hook up" although I got together with those 2 girls, and another guy, at least a few times
- Flaguy
  +1 y
  So you are still hooking up with her?
- Flaguy
  +1 y
  Did you go bareback or did you use a condom?
- Opinion Owner
  +1 y
  No, that was a LONG time ago
- Opinion Owner
  +1 y
  No condom. by the way, she sorta instigated it and we'd both been drinking...
- Flaguy
  +1 y
  That is cool. Did she say she was on birth control, or did she not mention it and she did not say anything when you did not have a condom on so you just went for it
- Opinion Owner
  +1 y
  She never said anything about birth control, and I didn't ask. But she seemed to know what she was doing. What was funny is that when she un-did my belt buckle, she literally pulled the entire belt out of my pants and tossed it across the room... my roomate's room
Anonymous
+1 y
I was early 20s she was late 40s
0 2 1 0
- Flaguy
  +1 y
  Was it a one night stand?
- Opinion Owner
  +1 y
  yeah
- Flaguy
  +1 y
  Did she let you go bareback or did you use a condom
- Show All Show Less
- Opinion Owner
  +1 y
  I met her on an online dating site. she was a married woman and she and he husband were swingers. He slept on the couch while I nailed her in the bedroom and yeah I did, she had a latex allergy and insisted on it.
- Flaguy
  +1 y
  That is sweet. Did it bother you that her husband was there?
- Opinion Owner
  +1 y
  he was outside and nah. he was chill
- Flaguy
  +1 y
  Is she the only married woman you have been with?
Anonymous
+1 y
I am 52 she is 20
0 2 1 1
- Flaguy
  +1 y
  Nice! how did you 2 first meet?
- Opinion Owner
  +1 y
  On line. She answered my personal
- Flaguy
  +1 y
  awesome... did you know how young she was?
Anonymous
+1 y
28 years
0 1 0 0
- Opinion Owner
  +1 y
  I was 17 and she was 45
- Flaguy
  +1 y
  Was it a 1 night stand or did you see her for a while? How did you 2 meet?
- Opinion Owner
  +1 y
  Not a one night stand. This lady used to be my neighbor and it was my first time. Then it went on for quite some time.
- Show All Show Less
- Flaguy
  +1 y
  Was she married?
- Opinion Owner
  +1 y
  Yes, he elder son was a year older than me.
- Flaguy
  +1 y
  Did her son ever find out you were doing his mom?
- Opinion Owner
  +1 y
  Never.
- Flaguy
  +1 y
  Did she invite you over, or did you cum on to her?
- Opinion Owner
  +1 y
  She seduced me. I was too young then I guess.
- Flaguy
  +1 y
  Did she take your virginity?
- Opinion Owner
  +1 y
  Yes, she did
- Flaguy
  +1 y
  Did she let you go bareback or did you use a condom?
- Opinion Owner
  +1 y
  Bare back it was
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