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I have a secret Lolita fantasy - I imagine being younger (I'm currently 22) and seducing an older man. I don't know why. I think it's because I was really mature at a young age and I would fantasize that an older, sexier, experienced man would recognize that. I also just love the thought of being the untouchable object of someones lust. Of driving someone nuts because it's taboo.

Needless to say I never got a chance to live this fantasy when I was younger, which was probably for the best. But I still get a thrill out of sex with large age gaps. The oldest I've been with is 38, and I get a thrill knowing that I'm the largest age gap he's ever had too.

So what is the largest age gap between you and a sexual partner? Has anyone got to act out a Lolita-like fantasy, even through role play? Share your stories wink
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shepm00n Amateur Jackinchatter

123 posts since 2010-08-08
72 year old bisexual from Minnesota
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I wouldn't call it a lolita fantasy, just a relationship, but my largest age gap was about 20 years. She was in her 30s, I in my 50s. Aside from energy levels (!), one thing I found was that we didn't always share cultural references, like music or tv shows. Think of that Steely Dan song, Hey 19. "Hey 19, that's Aretha Franklin..." Like that. (And if you don't know who Steely Dan is...well there ya go!)
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Backhand Novice Jackinchatter

8 posts since 2010-05-26
43 year old
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This really turns me on as well. I like the porn series Teens for Cash just for that reason. I am sure many are familiar but for the others it is hot 18-19 yr olds fucking guys in their 50-60's. For me it is super hot to see that scenario.
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j_bryon Amateur Jackinchatter

456 posts since 2005-08-12
50 year old heterosexual male from Southern Wisconsin
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I once had a one nighter with a woman who was 48 or 49 when I was 26. She had an awesome body and was so into me it was unbelievable! The best thing about this was my aunt, who is only 4 1/2 years older than me, was at the bar with me the night I picked this woman up. She was so against me being with her it was almost hilarious. Better yet was my mom is closer in age to me than this woman was.
Jacking when it's necessary and it's necessary often.
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aquist Amateur Jackinchatter

192 posts since 2010-04-09
84 year old bisexual from arkansas
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I am 70 and just this week I was having sex with a 27 yo. let me see. thats 43 years age difference. we frotted we masturbated,and we sucked. We both enjoyed it.
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i jerked and sucked off a 44 year old when i was 22
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gondo Professional Jackinchatter

1117 posts since 2008-02-09
70 year old curious male from Toronto, Canada
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When I was in my mid-late 30's I went back to college. One of my classmates was an absolutely lovely 18 year old raven haired beauty, who made it clear she was interested in me. I resisted briefly - very briefly. We ended up dating - well fucking mostly - for a few months. She was great: besides having an incredible body, she was intelligent, funny and mature. Eventually she found someone a little closer to her own age. But we had such hot times and she left me with a lifetime of stroking memories!
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I was around 18-19 and I worked with a woman who was married at the time, she was around her early thirties, and had a son almost my age! I flirted on and off with her for quite some time and eventually ended up sneaking over to their house once night he was out of town, and got the blow of my life from her! I came quick, she was impressed with my size and I gave her a huge load ... which she promptly ran off to spit frown
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pantyshots3 Novice Jackinchatter

77 posts since 2009-04-15
54 year old curious from Virginia
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This turns me on a LOT. I am 40 now, and when I was 35, I was with a 19 year old for a weekend of naked fun! Awesome small titties, beautiful pussy and she really knew how to give a great blowjob. I would have hung out with her longer, but my ex wife was due back home Monday, lol.
When I was 23 I was with a 51 year old, petite attractive woman! Great body. The only way you could tell she had some age to her, was by looking at her hands. She also had a son older than me, lol.
A friends daughter (18 now) and I played a little bit when I was 37 1/2. (you do the math)
And I have totally fantasized about my girlfriends younger step sister. She is 18 now and I have been checking her out for quite some time.
More stories, but probably not for here.
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