re: Ever had a guilty crush? (Possibly NSFW)

1999-2000 timeframe Stephanie McMahon. Annoying voice and a not a great figure, but I always wanted to frick the bitch out of her.

Forgot to add earlier.....I'd move to S. Dakota for this

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Guilty crush would have to be someone you know in real life right? Like there has to be that element where your friends would shame you if you actually dated her.

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More along the lines of (now adult) daughters of beautiful women with whom you once had relationships, and still see often on a social basis. It is a bit disconcerting to sit between two gorgeous young ladies at a social event, knowing exactly what their mom was like in the sack. Remind yourself that you're a normal male and just have eyes that function and appreciate their attractiveness, but it can keep you awake staring at the ceiling at night.

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These aren't guilty crushes. Guilty crushes are like your sister in law or buddy's wife.

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Well, I picked a short haired, lesbian chic, so..........

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More along the lines of (now adult) daughters of beautiful women with whom you once had relationships, and still see often on a social basis. It is a bit disconcerting to sit between two gorgeous young ladies at a social event, knowing exactly what their mom was like in the sack. Remind yourself that you're a normal male and just have eyes that function and appreciate their attractiveness, but it can keep you awake staring at the ceiling at night

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Alright then this girl.

Some of y’all have interesting choices

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I love the OT. Shitting on women who aren’t fricking fat fricks

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Pretty sure Pink is transitioning to a man

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Disgusting creature with minimal femininity,

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What constitutes minimal femininity? She's got all the right parts??

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More along the lines of (now adult) daughters of beautiful women with whom you once had relationships, and still see often on a social basis. It is a bit disconcerting to sit between two gorgeous young ladies at a social event, knowing exactly what their mom was like in the sack. Remind yourself that you're a normal male and just have eyes that function and appreciate their attractiveness, but it can keep you awake staring at the ceiling at night.

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A friend of mine had a kid when we were 18.

We always screwed with him that one of us was going to marry her.

She's legal now, and anonymously I can say... Would smash.

Guilty crush??

I don’t have a photo but it would be my 1st girlfriends mother. They look very similar as mother daughters often do. (And no I did not bang her mother)

Backstory would help.

My first girlfriend would not “go all the way” for a long time but she was more than willing to give me head whenever I wanted. She had braces when we first started dating (we were both in the 10th grade). In braces, or out of braces - a beej is a wonderful thing for a 15 year older boy. (Or any age boy for that matter)

After her orthodontist removed my girlfriends braces, she had a beautiful smile. Her mother made comments about how much better her daughters smile looked and eventually her mom got braces.

Every time I looked at her mom with those braces, I got a woody. It was like one of those Pavlov’s dog situations where my wiener was trained to stand at attention for braces. Her mom would come up to me and smile and then try to hug me and I would have to pivot my body to the side to hide the wood in my pants.

Very guilty and very uncomfortable to endure.

That is a guilty crush.