Way outside my comfort zone.

[Iwant2havefun]

What things have you done to take you out of your comfort zone? Have you found yourself in a situation where you're saying "i can't believe I'm doing this? It happened to me today. This is a true story, from just a few hours ago.

i'm in a new city today, staying in a hotel. i decided to put a plug in, a silicone cock ring over my cock and balls, and slip on a black lace thong. i do that often to masturbate, and i really like it, so that's not a big deal. i like to wear panties when i'm alone, love older women who are nurturing and encouraging, and it really gets me excited to chat or talk to women when i've got my panties on. Only today, i decided to go out with the plug in and the thong on, which i've only ever done on a very limited basis. i wore just a t-shirt and gym shorts over them.

i drove to Walmart, got a cart, and started "shopping." i didn't really need anything, but just being out knowing i was wearing panties and so FULL with the plug was intoxicating. i walked up and down aisles, and passed a lot of woman shopping. i kept thinking of Lit, and all the women here on the threads. Those women shop...could a woman from Lit be here in the store? My imagination ran wild.

Then i pulled the lace waistband of the thong up, and lowered the waistband of my shorts just a little. The t-shirt fell about 2" below the waistband of the shorts, so nobody could see anything, but running my fingers over the lace while people were walking past me in the store was erotic.

i saw a woman with a shopping cart by herself. She was probably about 60, but she was wearing shorts and a halter top, with wedge-heels. She had a "sexy" look to her, if that makes sense, and i talked myself into the fact that she might actually enjoy seeing panties.

i positioned my cart next to hers while she was looking on a shelf, and i bent down to a squatting position to look on the lowest shelf, making sure my t-shirt lifted up a bit to my hips. it was obvious what i had on, and i was able to get a quick glance to see if she saw, but she just pushed her cart and left the aisle. i think she saw, but noting came of that. Except i was saying to myself "what are you doing? Are you crazy?!" i guess being in a different city took away all inhibitions.

i decided i would buy some new panties while i was in the store. i went over to the women's section and found the proper aisle and picked up a pink pair and a white pair, lace and silk. The woman who runs the dressing rooms was literally 10 feet from me, and again i was so excited that i was wearing panties and plugged, and she had no idea. i did bend down to the lower shelf to look at panties, but she was doing something else and i don't think she saw anything.

As i was heading the the register, i cut down one of the grocery aisles. There was a woman in the aisle standing and looking at the shelves. Her cart was blocking me, and i asked "hi...do you mind if i slide by you?" She smiled and said "well, i'll let you if you'll help me get that bottle of juice off the top shelf." OMG. i couldn't have written it any better, because i knew if i reached up to the top shelf, my t-shirt would rise up and she'd clearly see my panties. My heart started racing 100 mph.

i turned to the shelf, and asked her "this one?".

"no," she said...."the one further back."

so i reached up and back to grab the juice bottle for her. She HAD to have seen the panties. i know my shirt lifted, and the panties also had a big long tag on them. When i turned to give her the juice, she smiled and said thank you. i said "i'm very happy to help you," hoping for some reaction, but nothing. Her smile of apparent acknowledgement was enough, though.

i went to the self-check out to purchase the panties and a couple of other small items in my cart. On the way, i casually lifted my t-shirt a couple of times to expose the waistband, but i didn't see if anyone saw.

So.....exciting and erotic, right? But it wasn't over yet.

i went to my car and started driving back to the hotel. It was about a 10 minute drive. A couple of minutes into the drive, a car pulled up next to mine, on the driver's side. The driver was a guy about 22, thick brown hair, muscular. He looked over at me, which i noticed, and i looked back. My windows are tinted, so i know he could see me.

He reached across his passenger seat and pushed the sun visor so it was parallel with the passenger window. i thought that was odd. Maybe he thought i was staring at him, and he was trying to block my view? i realized he was staying completely aligned with me, and when i looked back again he had his cock out and was stroking it.

His cock was big and thick, probably 7' or 8", and he was looking right into my window. Now i slowed down to stay lined up with him. i like women, but the rush i got was incredible. It stood up almost straight against his stomach, and it was rock hard. he was stroking it with both hands at one point, using his thighs to hold the wheel straight. We drove like this for about a mile, and i was incredibly turned on.

He appeared to motion to me, but it wasn't clear what he wanted. He turned on his left blinker and turned into a shopping center. i immediately made a left at the next corner, and also entered the same shopping center. i really was hoping he was going to stop and let me see him finish. i looked up and down a few parking aisles, unsuccessfully. i parked in the corner of the lot too, hoping he had turned in expecting me to, but he never came back.

i've never seen anyone jerk off before "in person" and it was fucking HOT. As i drove the rest of the way back to the hotel, i thought "nobody would believe this happened to me today." First, i wore panties and a plug out of the house, then exposed the fact i was wearing panties to two women, then had a guy pull up to my car and start jerking his giant cock.

And only as i was writing this, just now, did i think "wait, maybe he saw me in the store wearing panties, and followed me out of the parking lot?" and that's when i really got excited. i'm going to edge for a few hours, fantasizing that one of the ladies or the guy are on LIT and will see this. Then i'll blow an incredible load. The toy is still inside me, and it feels amazing BTW.

 

[writerzblok92]

Great story. Wonder if that lady really did enjoy your show.

 

[drobert44]

I loved taking my sissy shopping in NYC. I made sure the salesgirls knew she was my sissy, so fun! They smiled and snickered.

 

[water_moutina]

What things have you done to take you out of your comfort zone? Have you found yourself in a situation where you're saying "i can't believe I'm doing this?

Every time I got involved in pee play lol
I'm not into it, but I like that the guy was into it, so it made me even more horny

 

[peekingone]

Every time I got involved in pee play lol
I'm not into it, but I like that the guy was into it, so it made me even more horny

Sure sounds fun!!!

 

[NC_Coastal]

Every time I got involved in pee play lol
I'm not into it, but I like that the guy was into it, so it made me even more horny

I had a girlfriend who had to pee really bad one night while we were walking in her neighborhood. Her house was a half-mile away, and she really didn't have a choice. And with houses all around, she couldn't take her jeans off. So she sat on the curb and peed in her pants. I don't why, but it turned us both on. We repeated it several more times in risky places. So bad, but so fucking hot.

 

[falkor207]

Playing with the girlfriend, recently gave her control of when I cum. Looking possibly into a cage, but she's in the dark on that.

 

[peterheer51]

Anal with a not passable sissy.

 

[gin53man]

Having my first threesome was way outside my comfort zone.

another woman? another man?

 

[uncle easy]

how do you feel about it now ?

 

[aaa666]

As a male I had tried on skirts in private, but have recently gone out shopping etc wearing them. Wasnt sure how I'd feel with being seen and still not sure about being seen by friends/family but in areas where I'm unknown I like the look and feel of them

 

[StrongMaster7]

Two things pop to mind.

Years ago, when sexy chat with women was plentiful, I was chatting with a very hot woman. She was snapping pix of herself in real time and sharing them with me as we both chatted and masturbated, what used to be called cybersex. She was my dreamgirl. Long hair, huge tits, shapely body, great legs and she was super fun and sexy to chat with. Once she had me hooked, she said she wanted me to chat about having gay sex or no more pics. I immediately began to make up a story about having gay sex and she send another pic of her using a toy. I felt so weird having never thought much about gay sex, but it got me what I wanted.

And also long ago, I met a woman for a one-nighter and she asked me to strip for her to get things started. I was happy to oblige. Then she asked me to turn around facing away from her. Then she asked me to bend over. I felt a finger apply some lube and then a small dildo pushed up my ass. She worked it in and out for a little while and then removed it. The deepthroat and anal sex I got from her was more than worth it.

 

[el_uno77]

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.

 

[oneblueye]

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.

with the eclectic group that we have here I GUARANTEE you someone will get offended...so go on and do it.

 

[NewOldGuy77]

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, for one, would love to read it.

 

[UtilityCurve]

my BF and his friend

See, now that's troubling. When I hear "outside my comfort zone," that's it. Full stop. What goes outside the zone is assault, no?

Now, maybe we need a new expression (I would borrow "termination shock" from the astrophysicists--I believe it refers to the edge of the heliosphere beyond which things are different.)

I hope when the lights came on, it was a good memory; obviously it sure was different!

 

[Islander55]

See, now that's troubling. When I hear "outside my comfort zone," that's it. Full stop. What goes outside the zone is assault, no?

Now, maybe we need a new expression (I would borrow "termination shock" from the astrophysicists--I believe it refers to the edge of the heliosphere beyond which things are different.)

I hope when the lights came on, it was a good memory; obviously it sure was different!

Being outside your comfort zone could simple mean that it was new and you were unsure about it. I think we do need to get out of out comfort zone now and then and experiment to find things we might like. If you are talking about forcing someone, that is totally different. With my first DP, I was not sure I would like it but I was agreeable to trying it and I fully trusted the two guys involved to stop if I said so. Perhaps a different term would work better but I am not sure what that would be.

 

[UtilityCurve]

Since you quoted me, I'll answer this. As someone who had been a one-man girl, doing a threesome wasn't something I had ever considered doing. I didn't think I would be comfortable having someone else there while I was making love with my boyfriend. Believe me, we talked ALOT about it for months before, both between me and my boyfriend and with his friend there as well. When I did agree to do it, I was nervous as hell, which is not comfortable to me at all. I was a bit anxious but my BF had convinced me it would be ok, and so when we went through with it, I loved it.

The original questions are "What things have you done to take you out of your comfort zone? Have you found yourself in a situation where you're saying "i can't believe I'm doing this?" and that was what I answered. The experience took me out of my comfort zone, and, I couldn't believe I was doing this.

If that doesn't fall within someone's parameters of what being taken out of their comfort zone is, then that is their problem, not mine. ¯\_(ツ)_/¯

I guess it comes down to what "comfort zone" means to the individual.

Is it something familiar--or something that produces a bit of apprehension or anxiety?

I agree that novelty often correlates with apprehension/anxiety.  Duh, in fact. But I guess I was looking into the afterglow and sometimes in retrospect "I am neither glad nor even comfortable remembering that experience" is the feeling. Accidents happen, no doubt (a GF frankly got jealous when she learned--hey,  she asked!!!--that other females had let me penetrate them anally and she hurried, terribly unsuccessfully [it hurt her too much to go on] to "catch up" to my past), but in the main, my ideal of sex is both partners sharing a curiosity about how the two of them would do/enjoy something. No one should regret trying something new out of curiosity; just out of jealousy or obligation.

 

[stiv837]

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.

 

[Baldo_bearded]

I've enjoyed pushing my boundaries with a willing partner. Found out I am into having my ass played with and definitely enjoy being a sub to the right Dom ladies.

 

[crazy4myhusband]

I've found that with the right motivation scissoring can be quite enjoyable. Way out of my comfort zone but oh well...

 

[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?"