Way outside my comfort zone.

[EStaccato]

Been talking to a special friend here on Lit that convinced me to lift my dress and pee in my backyard, behind a cypress tree, about 20’ from two guys fishing.

There was a lot more to it than that, but it was about the furthest out of my comfort zone I’ve been in a very long time. It was also insanely hot. Don’t ask me how he got me to do it - I hardly even remember - I just know he’s a fucking sexual genius.

 

[manofewords]

having sex with a woman who has cerebral palsy. no use of her legs. i've known her for over 30 years and whenever i'm in her town we fuck like rabbits. phone sex is great with her as well. i will say, and she agrees, that she is a slut. i've thought about writing of our escapades but i'm not sure if anyone will get offended by it.

I'm slightly offended that people would be offended, I mean, are people with disabilities not allowed to have sex?! Of course they fuck, and some are probably just as kinky as anyone else! Write the stories, if people are offended, it shows their own prejudices.

 

[Erosfan]

Many years ago my first wife and lived in a mid size Pennsylvania town. She insisted we go for nude walks late at night. We never went far , just a few blocks from our house . At first it was way outside my comfort zone , but I gradually got used to it and started enjoying those walks. I actually kind of miss them , my first wife , not so much.

Many years ago, my first wife and I had an almost sexless life. Late at night I would leave the house naked and go for walks in our neighborhood. I would jack off and cum somewhere along the way. At that time in my life, I became very nervous and shy after my orgasm. At first it was almost unbearable. Something about that fear led me to keep doing it, two or three times a week. After a while it became fun and I really enjoyed it.

 

[Iwant2havefun]

Giving this a bump. After reading through this thread, there were some very interesting experiences described. Would love to hear some more! What things have you done to take you out of your "comfort zone"? Have you ever found yourself in a situation where you said "I CAN'T BELIEVE I'M DOING THIS?"

 

[drobert44]

Well, there was the time I sucked a gay man off on first date............duh.

 

[SmokingFap]

Not really sure how I would get out of my comfort zone. I'm pretty comfortable with anything. I guess maybe pulling out my cock in this bar and jerking off before they bring out my wings would qualify as outside my comfort zone...

 

[Goldenfinger]

The comfort zone changes quickly especially if the experience is enjoyable.

 

[Goldenfinger]

My wife has pushed me outside my comfort zone. But when I really think about it, I did it to her first Now the roles are just reversed.

 

[CuttingEdge]

I am a guy, but believe it or not, it was in having a one-night stand.

While that may be some guy's greatest aspirations, that is just not me. So, the first time I am at this lady's house, and for whatever reason I am fully naked first, and I am thinking, "if this ever went bad, I could be in a world of hurt here". The whole time I am thinking, "what the hell am I doing here completely naked", but managed to continue. As imagined, she did not work out too well as a long term girlfriend, so I continued to date other lady's afterwards.

Two weeks later though, I am in the same situation. At a strange lady's house, for whatever reason, naked first, and thinking the same thing again, that any wrong move or statement and I'll be accused of rape or any other imagined bad things", but this time... it worked out. In fact, it was the best sex I had in my life, and she says the same thing.

Now my fiancé and I laugh about it, because for whatever reason, I am always naked first. I am not an exhibitionist, nor aggressive for sex, or any of that, but it seems I am forever naked for her, and naked first. Either way, I am glad that horrific period of dating is over. That is just not for me.

 

[el_uno77]

Taking pics of myself could fall in this category. I'm very skinny, and sometimes and don't feel as comfortable with my body as I wish. I make an effort to workout regularly and change my physical appearance.

I joined Lit to work on that, sharing with some other people and feel more confident with my body. Even when sometimes it's a little difficult, many people here have blessed genes

beauty is in the eye of the beholder. i've dated women who can hide behind a sawing needle and those who were 200+ pounds. it never bothered me in the least. work on yourself image and be dammed what everyone else thinks.

 

[AppleCucumber]

My first anal and any other time a cock is introduced to my ass lol