Ex Hookup's Relative

HungBtmVegas

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Would you hook up with the sibling of an old fling who you have no contact with anymore?

The brother of a guy who I casually saw and almost seriously dated about 2 years ago started messaging me on Facebook a few days ago and we went from cautiously talking to him sending me pictures of his cock and wanting to meet up since he's here in town this weekend. Granted it's a little weird bc he knows his brother and I used to have sex and almost dated, but am I myself crossing a line?
 

halcyondays

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I have. She was the younger sister of a college gf to whom I was engaged. A few years after the breakup her younger sister contacted me asking for help with her hot water heater. I fixed it. Then she led me into her bedroom and took off all her clothes. We had an intense private affair for several months until she acquired a new boyfriend.

So far as I know her sister (my ex) never found out. We kept it secret. I told nobody.

We both felt we had crossed a line. The only remedy was to keep it super secret.
 

marriedasian

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it all depends on how it ended with your ex because you don't want to rehash all those bad memories being that you're now gonna smash a person who is so close to your ex. also, you don't know how your ex will react and since your ex knows all the finer details about you (both good and bad), they can have a strong influence on your new relationship.

my advice, don't do it.

i have personally fucked two sisters with them both knowing and it was all fine since they were both okay with it being that the younger sister brought the older sister to me but outside of this, i won't cross that line.
 
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sudcalifornio

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Would you hook up with the sibling of an old fling who you have no contact with anymore?

The brother of a guy who I casually saw and almost seriously dated about 2 years ago started messaging me on Facebook a few days ago and we went from cautiously talking to him sending me pictures of his cock and wanting to meet up since he's here in town this weekend. Granted it's a little weird bc he knows his brother and I used to have sex and almost dated, but am I myself crossing a line?
This question should be ask by the sibling, what has to do with you?
 

Poivre89

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So... I accidentally made my way through three members of the same family. When I was 18 I hooked up with this one dude and it was great. Then in my early 20s I hooked up with a waiter that I had given my number to. After the fact I found out that it was the aforementioned guy's brother. A few months after that I started seriously dating a different guy who happened to be the other two guys' cousin.
We all went to the same small town highschool but they were all older than me so I didn't KNOW them in highschool.
 

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My first boyfriend's (now ex) brother was hot! One year, I bought the ex a new video camera for Christmas. When we were at his brother's house that day, most of the video I filmed was of his brother. My ex knew I had the hots for his brother and made fun of me for filming his brother so much.

One day the ex and I were at the adult bookstore that I worked at. We were in the back talking when in the video camera monitor, I saw ex's brother getting quarters and going back to the booth area. I looked at my ex (we were still boyfriends at the time) and ex told me to go ahead, he knew how much I wanted to do it. So I went into the booth next to his brother, put some quarters in the slot and turned it to a straight porn movie. He dropped a few quarters and I kept looking through the gloryhole. I could see him from the waist down. He grabbed his crotch a few times but he never did anything. When his time ran out, he left the bookstore. I had never seen him there before that or after that.

His brother recently divorced his wife, so he is single. I don't talk to my ex, but I am still friends with other members of the family. I don't think it would surprise my ex if I were to do something with his brother.
 

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My wife's started seeing her very well hung ex-boyfriend regularly years after we were married. About 2 years after she started seeing him again he moved for a job transfer. 6 weeks after he moved we were at a fund raiser and ran into his younger brother. He wasn't as big, but still very well hung. For 4 months the little brother fucked my wife until her ex-boyfriend for a new job and moved back.
 
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SlipShop

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The brother of a guy who I casually saw and almost seriously dated about 2 years ago started messaging me on Facebook a few days ago and we went from cautiously talking to him sending me pictures of his cock and wanting to meet up since he's here in town this weekend. Granted it's a little weird bc he knows his brother and I used to have sex and almost dated, but am I myself crossing a line?

Any more news about that situation, Hung?
 
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startrek1

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Would you hook up with the sibling of an old fling who you have no contact with anymore?

The brother of a guy who I casually saw and almost seriously dated about 2 years ago started messaging me on Facebook a few days ago and we went from cautiously talking to him sending me pictures of his cock and wanting to meet up since he's here in town this weekend. Granted it's a little weird bc he knows his brother and I used to have sex and almost dated, but am I myself crossing a line?

When I was about 25 I was regularly banging a girl and her brother (the girl didn't know). It all adds to the rich tapestry of life!
 

lapdog2001

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I have an ex in mind who has a sister that I definitely would fuck, consequences be damned.
An old girlfriend of mine had a very hot sister, I found her extremely attractive as she closely resembled my girl, but she had DDs vs my girlfriend's nice full C cups. There was never any chance of us ever getting together and I only saw her a few times over the years I was with my girlfriend. Would I have hooked up with her after my relationship with her sister ended if the opportunity arose? Fuck yeah! My girlfriend was head-turning hot, and her sister was even hotter!
 
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steveh9

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I dated a girl for over a year, had great sex with her. She had a younger sister, too young at the time. We broke up, a few years go by and i ran into the sister. She told me she could hear us fucking at times and had seen us once fucking on the sofa in the living room. Ended up fucking her too
 

brownthickone

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Would you hook up with the sibling of an old fling who you have no contact with anymore?

The brother of a guy who I casually saw and almost seriously dated about 2 years ago started messaging me on Facebook a few days ago and we went from cautiously talking to him sending me pictures of his cock and wanting to meet up since he's here in town this weekend. Granted it's a little weird bc he knows his brother and I used to have sex and almost dated, but am I myself crossing a line?
So what happened?
 

brownthickone

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My first boyfriend's (now ex) brother was hot! One year, I bought the ex a new video camera for Christmas. When we were at his brother's house that day, most of the video I filmed was of his brother. My ex knew I had the hots for his brother and made fun of me for filming his brother so much.

One day the ex and I were at the adult bookstore that I worked at. We were in the back talking when in the video camera monitor, I saw ex's brother getting quarters and going back to the booth area. I looked at my ex (we were still boyfriends at the time) and ex told me to go ahead, he knew how much I wanted to do it. So I went into the booth next to his brother, put some quarters in the slot and turned it to a straight porn movie. He dropped a few quarters and I kept looking through the gloryhole. I could see him from the waist down. He grabbed his crotch a few times but he never did anything. When his time ran out, he left the bookstore. I had never seen him there before that or after that.

His brother recently divorced his wife, so he is single. I don't talk to my ex, but I am still friends with other members of the family. I don't think it would surprise my ex if I were to do something with his brother.
Especially, since you were already given the green light! Good luck!