Girls who broke your heart thread

To be fair during the times I was single and desperate, I might have thought "ah fuck... a hole is a hole" and gone for it.

Hell, during those times I was (luckily) always too poor to just pay someone for sex... and too poor to drive halfway across the country to find a swinger club.

Antarius said:

Met a cross dresser off craigslist. I got a blowjob, and then fucked him. I used protection. He looked like a woman, was "passable". It was disconcerting and disturbing to me, however, that I felt his dick swinging back and forth when I started to fuck him. It is not something I am interested in ever doing again.

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The single and desperate thing doesn"t apply considering he paid this guy. I highly doubt Boy George was the only person available on Craigslist that day.

Antarius said:

Met a cross dresser off craigslist. I got a blowjob, and then fucked him. I used protection. He looked like a woman, was "passable". It was disconcerting and disturbing to me, however, that I felt his dick swinging back and forth when I started to fuck him. It is not something I am interested in ever doing again.

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For realz though, as far as paying for sex goes, that"s a line I"m not comfortable in crossing. Or at least I haven"t as of yet. I don"t judge people who do though. I just personally have never gotten to the point where paying for sex is something that"s seemed a viable option, and it seems like something that could be a very slippery slope as well.

Who knows what the future holds though!

And no, I"m not looking to start that idiotic "you pay for it no matter what" discussion.

As far as my personal number goes, I think it"s around 20 or so. I"d have to give it some real thought.

Antarius said:

Met a cross dresser off craigslist. I got a blowjob, and then fucked him. I used protection. He looked like a woman, was "passable". It was disconcerting and disturbing to me, however, that I felt his dick swinging back and forth when I started to fuck him. It is not something I am interested in ever doing again.

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Calling this for my sig

Antarius said:

webcam girl - mfc.com 2010

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Explain.

That site is fucking awesome btw. Regular porn is obsolete now.

Antarius said:

Met a cross dresser off craigslist. I got a blowjob, and then fucked him. I used protection. He looked like a woman, was "passable". It was disconcerting and disturbing to me, however, that I felt his dick swinging back and forth when I started to fuck him. It is not something I am interested in ever doing again.

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Obligatory:

Grumpus said:

Explain.

That site is fucking awesome btw. Regular porn is obsolete now.

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20 year old chick that lives about 4 hours away (west of toledo). She used to watch my cam, while I would watch her, she is overweight, but still decent looking, I"d guess 190lbs at 5"4?.


We talked for about a month. Her room is usually slow, maybe 30 people at peak, and often just 4-5 when it was slow. I suggested we meet, she agreed. We met in a hotel and fucked (twice). Nothing really came out of it.

Antarius said:

20 year old chick that lives about 4 hours away (west of toledo). She used to watch my cam, while I would watch her, she is overweight, but still decent looking, I"d guess 190lbs at 5"4?.


We talked for about a month. Her room is usually slow, maybe 30 people at peak, and often just 4-5 when it was slow. I suggested we meet, she agreed. We met in a hotel and fucked (twice). Nothing really came out of it.

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So what you are saying is, there is an inkling of a chance that I will get to fuck LexxiStar. Today is a good day.

(there really is no chance)

Antarius said:

Met a cross dresser off craigslist. I got a blowjob, and then fucked him. I used protection. He looked like a woman, was "passable". It was disconcerting and disturbing to me, however, that I felt his dick swinging back and forth when I started to fuck him. It is not something I am interested in ever doing again.

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....

Jesus that is some shit you take to the grave. It was posted so nonchalantly like it"s nothing. You went this far, might as well post the whole story. Let"s all agree to +net him for the story.

I"m not against paying for sex, but the thought of it makes me hugely uncomfortable. It would just be so awkward. One guy I met traveling though would have hookers approach him at bars in SE Asia and they"d be flirting and dancing all night, then he paid them. I understood that a bit more. You already have some rapport with the girl. But to just arrange it like a business deal is weird. I"m not criticizing it, just something I couldn"t see myself doing ever.

Antarius said:

Met a cross dresser off craigslist. I got a blowjob, and then fucked him. I used protection. He looked like a woman, was "passable". It was disconcerting and disturbing to me, however, that I felt his dick swinging back and forth when I started to fuck him. It is not something I am interested in ever doing again.

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So hold on. You got a blow job and he didn"t finish you off that way, or you got a full blow job, laid around talking and cuddling andthenfucked him?

Fammaden said:

So hold on. You got a blow job and he didn"t finish you off that way, or you got a full blow job, laid around talking and cuddling andthenfucked him?

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I actually wondered this as well

Fammaden said:

So hold on. You got a blow job and he didn"t finish you off that way, or you got a full blow job, laid around talking and cuddling andthenfucked him?

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The former.

He spent about 20 minutes working on it, I was hard, but yea, it wasn"t working.

So then he suggested I try fucking him. That was even worse. I started to go soft after about 7-8 minutes of that.

He seemed to feel pretty bad about it, not just because I was taking a long time, but he seemed genuinely upset that I wasn"t cumming. He ended up going back to blowing me. I closed my eyes and imagined I was with the last girl I"d fucked, and then I finished.

Total elapsed time, start to finish, 45 minutes. It was awkward and shitty and not really that enjoyable.


On the complete opposite end of the spectrum, I just spent about 3 hours screwing my current girlfriend in the bathroom of her house, (she has kids so it was the only place we"d be guaranteed privacy), one extended break in the middle. It was fucking awesome the entire time, hot, slippery, cramped. She ended up finishing me off with one of the best and hottest blowjobs I"ve ever gotten (she told me not to cum in her mouth at the start, I warned her right before I came, I was holding her head, but she didn"t even try to pull away successkid.jpg).

So yea, this girl is pretty cool. 2 years older than me... but she had her first kid when she was 15... I mean wtf, I was literally still a virgin when her oldest kid turned 13, which kind of blows my mind.

Anyway, I"d really love to have a family of my own one day. Like it"s probably the biggest motivating factor in my entire life right now. She introduced me to her kids 2 weeks ago, I"ve hung out at her house a couple more times since then, I"ve been helping her youngest with homework and stuff while she"ll cook dinner....

Anyways, the downside is, her tubes are tied, she can"t have more kids. I can"t possibly see this ending well. I really like her, I like her kids, but I want children of my own one day, Not just magically seeing kids at 10+

She seemed to just want a FWB situation when we first started (her words, not mine), but it seems like we"re hanging out more and actually having a relationship... Do I continue seeing her, having amazing sex and getting attached to her kids, do I cut ties now and be miserable and lonely for a few months or go back to prostitutes (which honestly make me feel even worse afterward).

And how much did you pay for this....experience? Were you drunk? Lol.