That awkward moment when you find out something crazy about a good friend.

[kane]

Today I was at lunch with a buddy of mine. I have known this guy since the 5th grade. We start talking about high school reunions (our 20th was in 2009) and he ends up telling me that the summer after we graduated high school he banged a mutal friend of our's mom. That friend had gone into the military and his mom was selling the house and moving into a smaller place. He went to help her move some stuff and she basically came right out and told him that she wanted him to bang her.

She was decent looking, but not hot. She was always a little crazy though. He said she rocked his 18 year-old world!

[troncarver]

cool story bro

[jimmy-3-way]

Originally Posted by kane

Today I was at lunch with a buddy of mine. I have known this guy since the 5th grade. We start talking about high school reunions (our 20th was in 2009) and he ends up telling me that the summer after we graduated high school he banged a mutal friend of our's mom. That friend had gone into the military and his mom was selling the house and moving into a smaller place. He went to help her move some stuff and she basically came right out and told him that she wanted him to bang her.

She was decent looking, but not hot. She was always a little crazy though. He said she rocked his 18 year-old world!

In this particular case you buy a round...

[porno jew]

that is literally a my friends hot mom episode. smells like bullshit.

[BlackCrayon]

who didn't do that at one point or another?

[L-Pink]

He banged Stifler's mom?

.

[AsianDivaGirlsWebDude]

ADG

[Spunky]

Lol @the summer of 42,reminded me of the same thing

[smutnut]

Look, when you find out your girlfriend has a penis (or your boyfriend doesn't), that's an awkward moment. Everything else is easy to deal with.

[_Richard_]

hippies; at least it wasn't in a dead horse

[kane]

Originally Posted by smutnut

Look, when you find out your girlfriend has a penis (or your boyfriend doesn't), that's an awkward moment. Everything else is easy to deal with.

On the grand scale of things girlfriend having a penis would be far more awkward than finding out a friend banged another friends mom. LOL

[smutnut]

Originally Posted by kane

On the grand scale of things girlfriend having a penis would be far more awkward than finding out a friend banged another friends mom. LOL

I'm not sure everyone would agree with that, but - Okay.

[kane]

Originally Posted by L-Pink

He banged Stifler's mom?

.

Sadly no. the funny thing is our conversation was about Stifler's mom because we were talking about the new American Pie Reunion movie. I mentioned that our group of friends never had a Stifler's mom kind of mom. My buddy says, "Mikes mom was kind of like that." I said, "She was a little flirty, but not hot or aggressive." He then tells me that he once saw her naked and she had a huge, massive 70's bush. I ask when this was and he then explains that it was when he helped her move. That house had a pool so she suggested they go for a swim after loading up the truck. She got naked and jumped in.

[u-Bob]

That awkward moment when you find out something crazy about a good friend.

... like when people ask you to fix their computers because "you work with computers"... and you find their home videos?

[DWB]

You think that is awkward, I literally walked in on my friend getting fucked in the ass doggie style by a shemale. Not kidding.

He was up in 2nd floor loft and I walked in the room and yelled for him. He pops up from the bed as does the shemale behind him who was screwing his ass. So I asked what I needed to ask, we talked for a minute, and then I left.

These days it would be pretty normal to walk in on something like that, but back when this happened it was really awkward. I kept thinking, I just walked in on dude getting fucked in the ass and carried on a conversation with him like nothing was happening.

[kane]

Originally Posted by DWB

You think that is awkward, I literally walked in on my friend getting fucked in the ass doggie style by a shemale. Not kidding.

He was up in 2nd floor loft and I walked in the room and yelled for him. He pops up from the bed as does the shemale behind him who was screwing his ass. So I asked what I needed to ask, we talked for a minute, and then I left.

These days it would be pretty normal to walk in on something like that, but back when this happened it was really awkward. I kept thinking, I just walked in on dude getting fucked in the ass and carried on a conversation with him like nothing was happening.

LOL that would be awkward for sure. Long ago at this place I worked one of the women I worked with invited a bunch of us over to her new place for a housewarming party. she is a very quiet, conservative girl who was nice, but shy. Her house was one of those houses where all the bedrooms are upstairs. I need to use the bathroom an someone is in the one that is downstairs so she tells me to use the one upstairs. I go up the stairs and open the first door I come to which was an empty room. The second door in the master bedroom. On the unmade bed is a giant black dildo that is around 15 inches long. I laughed and shut the door, found the bathroom, did my business and went back downstairs. I found another woman I worked with, told her what I found so she could warn the homeowner that she might want to cover that up with people running around the house. She has the news whispered to her, turns bright red and runs upstairs. Every day after that when I would see her come in I would wonder if last night she punished her pussy with that black thunder of a dildo.

[smutnut]

Originally Posted by kane

LOL that would be awkward for sure. Long ago at this place I worked one of the women I worked with invited a bunch of us over to her new place for a housewarming party. she is a very quiet, conservative girl who was nice, but shy. Her house was one of those houses where all the bedrooms are upstairs. I need to use the bathroom an someone is in the one that is downstairs so she tells me to use the one upstairs. I go up the stairs and open the first door I come to which was an empty room. The second door in the master bedroom. On the unmade bed is a giant black dildo that is around 15 inches long. I laughed and shut the door, found the bathroom, did my business and went back downstairs. I found another woman I worked with, told her what I found so she could warn the homeowner that she might want to cover that up with people running around the house. She has the news whispered to her, turns bright red and runs upstairs. Every day after that when I would see her come in I would wonder if last night she punished her pussy with that black thunder of a dildo.

Remember those little PENTHOUSE FORUM Things back in the day?

[kane]

Originally Posted by u-Bob

... like when people ask you to fix their computers because "you work with computers"... and you find their home videos?

LOL that would be troubling.

[kane]

Originally Posted by smutnut

Remember those little PENTHOUSE FORUM Things back in the day?

Vaguely. When I was about 13 or 14 a couple friends of mine and I found and old trash bag with about a dozen pentyhouse and playboy magazines in it. Sadly, they were so water damaged you couldn't really read the words, but some of the pictures were okay. By the time I was old enough to buy it I lived a few blocks from a porn store and ended up moving right on to movies.

So I know what you are talking about, but I never really read them.

[Nikki_Licks]

I just experienced what I would call the most unusual awkward moment I have ever encountered.

We just got some shocking news from a friend the other day, who we met via the adult industry.

I was chatting away on ICQ with this guy and he told me he had re invented himself and asked if were sitting down, (he made sure to ask me about five times), then told me that he had been on hormones for about two years and was going to do the full sex change. He basically told me his titties were looking good and perky and he was going to have his dick turned inside out.

I have to admit, I was totally speechless and truthfully did not know how to react, never the less give some sort of response that could be somewhat supportive. I have known this guy for years, he has a beautiful wife and not once did I ever see a sign that he may be on the feminine side or something different about him.....seemed like a normal guy.

Now that I think about it, he did come over for one of our BBQ pool party's and we did give him crap about having big puffy nipples......

Maybe he thinks life will be better as a woman, who knows

[kane]

Originally Posted by Nikki_Licks

I just experienced what I would call the most unusual awkward moment I have ever encountered.

We just got some shocking news from a friend the other day, who we met via the adult industry.

I was chatting away on ICQ with this guy and he told me he had re invented himself and asked if were sitting down, (he made sure to ask me about five times), then told me that he had been on hormones for about two years and was going to do the full sex change. He basically told me his titties were looking good and perky and he was going to have his dick turned inside out.

I have to admit, I was totally speechless and truthfully did not know how to react, never the less give some sort of response that could be somewhat supportive. I have known this guy for years, he has a beautiful wife and not once did I ever see a sign that he may be on the feminine side or something different about him.....seemed like a normal guy.

Now that I think about it, he did come over for one of our BBQ pool party and we did give him crap about having big puffy nipples......

Maybe he thinks life will be better as a woman, who knows

Damn, that would be a shock! Is his wife going to stay with him? I saw a documentary several years ago that followed three guys who were all in the process of becoming women. All three were married and all three had wives who said they would stick with them. In the end within a year of them getting the last surgery the wives were long gone. I can't say as I blame them.

[Nikki_Licks]

Originally Posted by kane

Damn, that would be a shock! Is his wife going to stay with him? I saw a documentary several years ago that followed three guys who were all in the process of becoming women. All three were married and all three had wives who said they would stick with them. In the end within a year of them getting the last surgery the wives were long gone. I can't say as I blame them.

To tell you the truth, I did not ask as I was totally taken off guard. My wife asked me the same question. I am going to contact him to ask some questions now that I have had time to think about this. I don't think his wife is bi, but who knows.....hell I totally missed any signs from him.

[EddyTheDog]

Originally Posted by DWB

You think that is awkward, I literally walked in on my friend getting fucked in the ass doggie style by a shemale. Not kidding.

He was up in 2nd floor loft and I walked in the room and yelled for him. He pops up from the bed as does the shemale behind him who was screwing his ass. So I asked what I needed to ask, we talked for a minute, and then I left.

These days it would be pretty normal to walk in on something like that, but back when this happened it was really awkward. I kept thinking, I just walked in on dude getting fucked in the ass and carried on a conversation with him like nothing was happening.

"These days it would be pretty normal to walk in on something like that".

Pretty sure that would still be pretty awkward...

[MattPIVO]

Bump for more stories like this

[candyflip]

I fucked a friend's mom in High School.

[kane]

Originally Posted by candyflip

I fucked a friend's mom in High School.

Did your friend ever find out about it?

[Phoenix]

i banged my moms friend after first year in university.
she had been coming onto me for years, but i was clueless to it.
she was hot

[bean-aid]

milfs are hot...