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ITT: Inappropriate relationships
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ITT: Inappropriate relationships

Have you anons ever gone into something with somebody you really shouldn't to? Friend's wives, sisters, bosses, employees, teachers, students...

Not quite a wincest thread, but if it is the only thing you got, feel free to share...
I am currently deeply in love with the girlfriend of my best friend, who is also a very good friend.
It fucking drives me insane.
I've banged my best friend's mom for over a year until he found out and beat the shit out of me... Got into a one week coma for this.
But does she knows about it or is something hidden?!
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>Meet lesbian
>She's getting over her ex girlfriend
>I fall in love with her
>She sort of falls in love with me
>But I'm a guy
>We date for a bit
>Ends really badly
>Go back to being really good friends after a while
>Still in love with her
>She's falling for me again
>We hook up occasionally
>Sort of hell for both of us
>But the sex rocks
And that's where it's at right now. Tears me apart really. I get involved with different girls here and there but nothing compares to her.
Don't go that way dude... It will bring you pain... Trust me!
Why is it a hell? Date her again in a "open relationship" deal!
I was a janitor with this chick for a while and we would make out fingerbang in the janitor closets and shit. I never went dick in cunt with her though because it's to take your hands out of someone's pants than it is to pull your pants up if your supervisor comes in.
Nope, they doesn't know about it.
No one knows about it.
I know it's a line that shouldn't be crossed, so I wont tell anybody, but I can't refrain the feeling.
I really love her.
Dude, u r a real lousy friend!
Never thought about only opening the zipper?!
Also ruined lesbian porn for me. We do really cool shit like hike together and hang out at the top for hours smoking and drinking together. We talk a lot and usually talk through the night until one of us falls asleep but we try to stay awake for each other. We check out sunsets and stuff.
I'm not solely focused on her, I work and go to school and we both give each other space. If a new girl came into my life I would go with it, same with her. She did date a girl and we still stayed really good friends, we just don't talk about our relationships with other people. If we do, we stay really vague out of respect.
It's incredibly painful but really exciting in a weird way. We're both growing a lot through.
I've never really been able to talk about it so this kind of helps.
I'm a jealous person so an open relationship wouldn't work. Plus she's lesbian, nothing can change that so we can't force it. We both wish it was different but it is what it is.
Getting your dick caught in a zipper
I understand you! It must be really complicated... But I've seen things like these with a friend of mine. She has a bf and a gf and both of them knows about it. All of them hang out together.

Never, really never... Very cautious with that!

Do not supress your feelings too much. It will be bad for you!
Four married women.
Two 17 year olds when I was 34.

carried on a year long affair with friends fiance.
turns out she had 2 affairs going, haha

they got married but it didnt last as they both were cheating. ...and i stupidly went back out with her after it all. just fizzled out and we are still friends.
Soul of a woman was created below
I actually thought about what that would be like. If I wasn't a jealous person that would rock haha. How do they do dates, are they all on the same work or school schedule or what?
Also getting your dick caught in a zipper is incredibly painful. 0/10 would not reccomend
your mom
you pussy.
Im fucking my bosses wife. He has no idea he just thinks its nice that hes wife has a close female friend.
I banged my dad's 42 year old secretary for a year and a half. We have matching tattoos and I even got her pregnant. My mom found out and freaked.
Still some of the best see I've ever had.

and I had this odd thing with my boss when i was a lifeguard at a private poolclub.
I knew her as she was a substitute teacher at my school. But she was married and had a kid2 years younger than me. She was the pool director for that summer and I was playtoy. I would let her watch me shower and jerk off. And she would let me put sunblock all over... while i jerk off on her. Never went further then 2nd base stuff and no kissing. But jesus fn christ was it hotttt.
My entire relationship history is inappropriate

>4 coworkers (some with boyfriends) extended affairs
>3 women with boyfriends (one night cheats)
> 1 girl while her fiancé was in jail
> one night stands with a few friends girlfriends
>roommates sister while she was visiting
> second cousin when she visits
> recently began hooking up a bit with my sister even though she is married .

Yep I'm a home wrecker luckily most of these have never been found out .

And this is why I no trust the womenz either.

They have different schedules, but all of them live near each other. The only thing is that my friend usually "gets physical" with only one of them per time (but some sources said that she had a threesome with both some times). Her BF doesn't date her GF by her back, they only get some action with my friend involved.

If your boss discovers this, will he ask for a threesome?

I fucked a girl who worked for me for about a year and a half. Her b/f that she lived with las vegas had no idea. I was in vegas about a year ago and hooked up with her again. she said she recently got married.
You could become a woman.
I have one that inappropriate, borderline incest but never crosses the border so I think it fits this thread. it's copypasta but it's mine.

>be 12-13
>single mom 35ish
>mom dates occasionally, has sex in her bedroom when she thinks I am asleep. Listen and very horny but no jacking off yet.
> Then lrn2bate and much cum spilled everywhere
> start videotaping my bates and cum. no idea why but watch them and bate over them
>start trying on my mom's lingerie
>bate while wearing it, super cum
>cum all over lingerie, hide it in my room, ashamed
>mom finds her stuff crusty, confronts me
>she went looking for it because she'd found my bate tape too, Going to die from embarrassment
>mom is chill, just tells me it's ok, and that I need wash her stuff after I am done (i already wash my own clothes)
>Not long after, mom buys new lingerie she shows it to me when she gets home, not trying it on or anything. Just showing me what she got
>asks me if I want "first crack at it", playing vidya and ignore her, super embarrassed, say nothing
>go to room later on and the new lingerie is on my bed, cum buckets on it and in it
>She opened the floodgates so I start wearing her panties all the time, under my clothes.
>They are slightly too big, but not very, mom is not fat.
>mom has the talk with me, "are you gay" etc. Don't answer, embarrassed. Mom assumes I am, but is ok with it.

to be cont.

>Mom buys me panties in my size. Nice silky shit. Be about 15 now.
>Mom starts trying on lingerie in front of me after she buys it. Much fapping after.
>Then mom asks if I am still recording myself. “Nah”. She keeps asking, worried I was putting it on the internet or something. It’s an old tape video camera. “Nah, mom. “
>Mom asks “will you?”
>confused, embarrassed, fucking horrified, turned on. Mom says it’s ok if I don’t want to but she would like to see it. She thinks it’s cute and sexy and she likes seeing me “hot and bothered”.
>Jerk on cam. Leave tape on mom’s bed.
>Mom gives me a big kiss on the cheek the next day. “I loved your tape.” Tells me she wants me to wear a specific outfit. Garters and shit. Do it. Cum buckets.
>Goes on till I am about 17. Start saying “Mom” sometimes when I cum.
>No reaction from her later though. Never caught her bating or watching the tape. She still asks me if I “recorded anything” every once in a while. Usually that means she wants the tape or wants me to record something new. Still buys me panties.
>Start using hand lotion sometimes. Find lube on my bed soon after. That tells me mom is still watching.
>Use her vibrator in my ass on camera. Had used it a few times before off camera. Cum super buckets.
>Mom asks me not to use it. “We shouldn’t share things like that. Germs and stuff.” Buys me a vibe of my own. Love my mom. Humped that thing a lot.

to be concluded
Not all are like my luckily for you lads.
I sure hope he does

ugh...i did this...no one ever knew but makes me cringe when the memories cross my mind...my fucking mom though...god damn
In 7th grade, I dated a 4th grader...but in all fairness, she got held back and should have been a 5th grader. Everyone gave me shit for it until I dumped her a month later


>Start moaning more on camera, talking dirty. Strange that I can say ‘fuck’ for her on cam but not in conversation. I got really kinky as time went on. Started jerking all over the house, once in the backyard, frequently on my mom’s bed. I would cum in my hand and eat it. Came on my face a couple of times. Since I knew someone was watching, I felt the need to perform.
>Mom really didn’t react to any of this later. She would occasionally grab the back of my pants and look down them to see if I was wearing panties. “Just checking” or she would just smile.
>End of story. Nothing ever happened between us. Still wear panties.
Other than the stuff above our relationship was completely normal. Love her for encouraging me but she had to be a perv too. Don’t really want to fuck her at all now, but there was a time where I know I would have if it had been presented to me. We don’t talk about it at all really. I know now that she was getting off on it but I wasn’t sure at the time. I still get hard thinking about it.
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