Between best friends...ever crossed the line?

[archetypal_mystic]

This is a question for all guys, gay, straight and in between. Have you ever crossed the sexual line with a best friend or buddy...from any stage of your life. I know several people who have...both guy-girl and guy-guy combos. I am speaking of anything, from kissing, watching each other self pleasre, mutual masturbation, oral, full on sex. I think that sometimes when that bond is very strong, there is a natural feeling to "go further". Has happened to me...and it made us closer.

 

[MisterVIP]

I had a female friend when I was 20, we hung out a lot (she dated one of my friends briefly). She asked me if I ever thought of us becoming more than friends, I said no, because I didn't want to risk the friendship. This was on the way to pick up dinner to take back to my place; she was driving. When we got back, she said she felt ill and needed to go home. She ended the friendship not long after that...like the next day or so. I was not expecting that.

 

[Hatt_101]

In high school my best female friend and I were so close but she and I never did any thing because we both valued our friendship more. Ironically I did sort of date her younger sister when she came to the school.

 

[twoton]

I've had a few very close female friends but never crossed the line. One definitely wanted to, but I kinda hedged on it and nothing happened. I was never the kind of guy who could fool around with a woman unless it was a one-night thing or we were moving toward an intimate relationship. I was never comfortable enough to do it with "friends." Never had a FWB.

 

[DickFiend]

I did as a teen. My best friend was years older than me and naturally, boys are horny and they experiment.
I told him I was gay and he told me he was straight but during a game of truth or dare, he dared me to suck him and I did.
This went on for a year and a half with us sneaking out at night, sucking each other in various public places.
Laundromats, the elevator of our apartment complex, in between cars, the staircases, etc...

I of course, began to develop feelings but it all ended when he moved to another state. I was devastated.
Never saw him again but we did connect on Facebook.

 

[keenobserver]

I did it with two best female friends. It was really strange how it worked out as I am 100% gay. The first friend was a friend from school. During school she dated an older guy. He was her first serious boy friend. After he graduated the stayed together long distance. When we were freshmen in college she asked me to have sex with her because she wanted to do it with someone before she did it with him. They had planned a big weekend together to do "it" and she was a virgin. She had told him she was experienced when they started dating, so he assumed a past that did not exist. We did the deed . It went okay, and her weekend went well too. They have been married for almost 40 years now.

The second was similar - a girl in college was dating a guy and they were unable to have penetration. He could not get in. She was upset - thinking it was her fault. The first girl had told her about us so she asked me to do the same. For a guy who was not attracted to girls I was tripping over pussy. We tried and I too failed to achieve entry. She went to the doctor and he told her that her hymen was extremely thick and he actually had to do a procedure to open it.

It did not change the relationship too much - it probably make us closer. Later we all transferred to different
schools and over time drifted apart.

I never tried anything with my best guy friends - although a longed to do so. I was really closeted and feared that I would loose the friendship.

 

[328982]

I had a female friend when I was 20, we hung out a lot (she dated one of my friends briefly). She asked me if I ever thought of us becoming more than friends, I said no, because I didn't want to risk the friendship. This was on the way to pick up dinner to take back to my place; she was driving. When we got back, she said she felt ill and needed to go home. She ended the friendship not long after that...like the next day or so. I was not expecting that.

That's sad, guess she had strong feelings for you. Were you upset that she ended the friendship?

 

[MisterVIP]

That's sad, guess she had strong feelings for you. Were you upset that she ended the friendship?

Yeah, I didn't expect that. When I gave her my answer, she said she agreed (but sounded a bit flustered) and said that if we each found someone to date, that we would remain close friends no matter what.

Next time I called her to see how she was feeling, she said she needed to take a break from talking to me, and that was it.

The friend of mine she dated, she met through me, and when they broke up we hung out more, up until that day.

 

[alcor972]

I did it with two best female friends. It was really strange how it worked out as I am 100% gay. The first friend was a friend from school. During school she dated an older guy. He was her first serious boy friend. After he graduated the stayed together long distance. When we were freshmen in college she asked me to have sex with her because she wanted to do it with someone before she did it with him. They had planned a big weekend together to do "it" and she was a virgin. She had told him she was experienced when they started dating, so he assumed a past that did not exist. We did the deed . It went okay, and her weekend went well too. They have been married for almost 40 years now.

The second was similar - a girl in college was dating a guy and they were unable to have penetration. He could not get in. She was upset - thinking it was her fault. The first girl had told her about us so she asked me to do the same. For a guy who was not attracted to girls I was tripping over pussy. We tried and I too failed to achieve entry. She went to the doctor and he told her that her hymen was extremely thick and he actually had to do a procedure to open it.

It did not change the relationship too much - it probably make us closer. Later we all transferred to different
schools and over time drifted apart.

I never tried anything with my best guy friends - although a longed to do so. I was really closeted and feared that I would loose the friendship.

... Did the girls know you were gay?...
... Was it one of the reasons for they chose you?...
Thank you, keenobserver.

 

[keenobserver]

... Did the girls know you were gay?...
... Was it one of the reasons for they chose you?...
Thank you, keenobserver.

No, they did not know I was gay. I was very closeted for a few more years. They chose me because I had told them I was sexually experienced - which was true. We all three went to the same high school together and then we went to the same college together for a year before we went in different directions. The second girl wanted me because the first girl told her I was large. Her boyfriend, who I knew personally, had been unable to penetrate her and she thought it was a size issue on his part. It really wasn't - he was a solid average.

 

[lapdog2001]

In my adult life I seem to have had a serial string of good female friends, and all but one case, no lines were ever crossed. The common denominator for my good female friends is that I was attracted to, and interested in dating, all but one of them, but I ended up being 'just friends' with them at their request.

The one exception for crossing the line, was a friend of about a year that I ended up seducing one evening after we had spent the day together. I had expressed interest in her in the past, but she always politely declined. She was crashing on my couch that night and a goodnight hug (we always hugged), turned into a kiss on the neck, a caress, more caresses, all the way to '3rd base' The next morning, things quickly escalated into oral sex and intercourse.

The relationship got really messy for about a year or so, as I had fallen in love, and she hadn't. We were were extremely sexually compatible, so even when she just wanted to return to just being friends, our sexual chemistry won out 99% of the time. Eventually after I was able to deal with my emotions, and accept that we wouldn't be a romantic couple, we settled into a FWB relationship, which continued on for many years. We joked with each other that we'd still be fucking each other when we were senior citizens!

As for guy friends? ... Uhm, no, those thoughts never crossed my mind.

 

[killerb]

years ago I was horsing around with a buddy of mine & then out of nowhere, he kissed me right in the mouth....a few horny minutes later he ended up blowing me...that was kind of a shocker.

 

[archetypal_mystic]

hey, could you add to that story...its just the kind of spontaneous moment that I had in mind when I asked the question. How were you guys about it afterwards? Did it ever happen again, and did it alter the relationship in any way?

 

[halcyondays]

Never with a best. Danced around the issue with a really good friend long ago when we were housemates without doing anything about it.

 

[933295]

Yep, my best buddy and I were jerking off together one time, and for some reason we started kissing each other. I kept kissing him until he came. He said that it was the intimacy of kissing that made him shoot. Cool experience.

 

[baffledking]

I have had such a naturally evolving friendship with two of my friends (guys). One was when I was in 11th and 12th grade. The other was in college. With both situations, we became so closely bonded that it naturally progressed. We had an amazing bond and were inseparable. It was awkward with this one friend the morning after and a few other times when it came up in a negative way. But otherwise, it did strengthen our bond more. It continued on for a few years.

The bond that we share is special even to this day. Both of them are 100% straight, married with children.

 

[french_lp]

My best friend and I were often spending the week end together, mostly to hang out, but also at some point when we were both single to try and meet women.
We were quite horny but also quite unable to hit up on girls...
It often ended up in back-from-bar-drunken-masturbation-watching-porn, without touching each other, but one crazy night I went down on him and just sucked his cock.. he didn't seem to bother at all, I quite enjoyed doing it, but at some point that night I let him know I'd like him to go down on me and he refused.
So we stopped, went back to other stuff, and never mentionned it again.

 

[igotthebigone]

This is a question for all guys, gay, straight and in between. Have you ever crossed the sexual line with a best friend or buddy...from any stage of your life. I know several people who have...both guy-girl and guy-guy combos. I am speaking of anything, from kissing, watching each other self pleasre, mutual masturbation, oral, full on sex. I think that sometimes when that bond is very strong, there is a natural feeling to "go further". Has happened to me...and it made us closer.

No I haven't tried that yet

 

[nnjjock24]

I have with both a female friend and a male friend. Both happened after drinking. Things with the female didn't turn out so well. Things with the male are fine to this day. We no longer hook up but are still great friends.

 

[TexanStar]

Every time

Every relationship I had started as a friendship that grew into something more romantic and/or torrid, so in every case there was a moment where that line got crossed.

If you're asking about the case where the line was crossed and then went back to just being friends, only with one woman (one of my best friends & first love back in my younger days). I don't think we were really compatible as lovers, but she's one of the most interesting women I've ever met and a role model of sorts and it was certainly fun trying to make it work even if it didn't.