[FM] An example of a typical frisky evening with friends!

I was asked a few times if I could post a story about how open I am with friends. I’m relatively active in other subreddits and it often comes up that I’m open about masturbation and general sexiness with almost everyone, especially my circle of friends.

For a bit of background, I’m a middle child (26F) with a 29F sister and 23M brother. I’m really skinny and have small boobs, japanese genes but otherwise american (southern californian in particular), and I’m married to a woman, we’re in love exclusively but she’s okay with me being frisky and sexual physically with my friends. I became sexually active at a very young age, although I don’t think that’s a cause of anything (it comes up a lot but I kind of resent it, it removes my own agency and responsibility for my sexuality).

I’ve had the same extremely close circle of friends since I was a kid, and we’re all open about sex and are casual about being with each other, with the exception of a few who have since become married. They’re still good friends, but they’re off-limits now :3

I wasn’t dreaming, 1st transexual experience (36y straight male) [MT]

[MT] I understand this may be off putting to some and others may be more accepting. Unfortunately I have no medium to discuss this, outside of anonymously online. As with most people in my situation, years ago I found transexual porn and was very drawn to it. I do not find myself attracted to men at all but there is something about a beautiful woman with a little something extra that is exotic and arousing. I recently found myself growing tired of just looking at porn and decided to see if there was anyone in my area that would be interested in meeting. I chose to use grindr simply due to ease of use and instant communication. I quickly became disappointed and discouraged because the majority of the women on the app require money to meet and I was not looking for that. The other women apparently did not find me attractive. I am a blue collar white male that has a few extra pounds but not heavy , just not like the super ripped pictures the other guys on the site are showing. About 10 days ago luck finally landed on my side and a beautiful ebony transexual replied to my text. I went to meet her and we hit it off very well. Then 20 minutes into our conversation she began to drop hints that she was actually a professional escort and my heart sank. However she interjected that she had no intention of wanting me to pay for anything. She said she really thought I was cute and her type, she likes corn fed country boys with a heart. We had a very honest discussion about her buisness and surprisingly I found myself ok with the situation. We spent some more time talking that night and parted ways. Two nights later she called and invited me over. I explained I was very eager to explore with her and also stated I have never done anything with a transexual. She was very understanding and we had a wonderful time exploring each others bodies. I was able to experience giving anal sex (protected of course) for the first time and when I left I felt liberated and not the least bit ashamed. Two nights later and she gently led me through my first experience with receiving anal sex(protected). It feels amazing that I found someone as wonderful as her to lead me through this journey. Then to my wild and gracious suprise, I was visiting with her at her friends house who also happens to be a beautiful ebony transexual. All of a sudden her friend came up to me, took my hand and said “now it’s my turn”. I looked at my friend and she winked and said have a good time. I then went to the bedroom and was met with the biggest **** I have ever seen. We spent two hours together pleasuring eachother with my friend coming in to check on us about an hour in. At the end of the night I was told by both ladies that I did such a good job that in a couple of days, since I proved myself capable I would get to enjoy them both at the same time. Now I cant stop thinking about what has happened in such a short period of time. I feel like this only happens in porn, how did things change so drastically.

[MFF] Just Fuck Her!

In the early days of my awakening, before I got married and so on, I had a couple of years of random sexual activities. I’m not the best looking of people nor the best endowed, and yet here we are. I’ve also been called “handsome” repeatedly, but being handsome is like the “nice guy” of lovers. I hate that label.

I’d been “dating” Marisa (not her real name), and I use dating in sarcastic air quotes because Marisa wasn’t into introducing me to her friends and/or family. I knew what was going on. I was 30 and she was 21. I want to stress that I’ve never been the kind of guy who sleeps with women specifically because they are younger. Until I met my wife I was all about picking spots and finding women who were into me. I’m 100% sure there was nothing wrong with my approach.

[MM] Bro helping a bro

So I went to a uni restroom today (26M) and was kind of horny as I still had blue balls from yesterday. There was nobody there and I had time so I went to a stall to rub one out. Like 10 minutes into it with porn on my phone, someone entered the restroom and ended up in the other stall. So I sat there for a bit, watching porn with a boner, thinking what’s the most curtious thing to do if the other guy really needs to shit, and was kind of quiet. After a bit I started feeling awkward that he cannot go with me there, so I started pretending to wipe and such, and suddenly I hear a silent slow fapping noise. I froze, listened for a bit to make sure I’m not hearing things, but it was kind of obvious by now. So I said fuck it, started the porn and jerking off again. It was obvious now that we’re both masturbating, I didn’t care that much, I’m straight but had a few jo buddies before (almost straight I guess?). A few minutes passed by and I got to my favorite passage of a hj/cumshot compilation with 2 girls jerking a guy at the same time (it was a really intense scene), so I was like wth and put my phone on the floor, slightly to the side, so he could watch if he wanted. He immediately said ‘nice’ and I asked if he was jerking off and he said yeah after a pause, so I asked why is not his gf helping out, he said he doesn’t have one. So I told him my story he said that sucks and then we just jerked off watching the video. We we’re interrupted a few times by people coming in, I always took the phone from the floor and then put it back when they left. My class was starting soon so I finished myself soon after the last interuption, came in my hand, and I heard a chuckle (I moan weirdly and much deeper than my voice I guess, even when I try not to), and he asked how are my blue balls now and I said quite empty and just put my hand with the pool of cum where the phone is to show it (I cum a lot) and he laughs again, says nice bro, and I started cleaning my dick. I left my phone down for him to watch while I clean myself from what’s mostly precum, and I hear him getting faster and then everything stopped. No sound at all for a few seconds, so I asked are you ok mate, when I hear he breathed out and said yeah, and he put his hand where I could see it the same way I did. His load seemed much thicker and all over his hand, I think it even dripped on a floor a bit. I told him good job, we laughed, and I went outside to clean my hand(s) in the sink. He was done cleaning fast, went to wash his hands next to me, I could still see he had cum on his hand. We chatted a bit and I found out he goes to the same gym as I do and in general he was such a normal average dude like me and there was no awkwardness or nothing sexual. I’m kind of new in the city and haven’t had a bro to hang out with or drink or talk about everything, and this was such a nice encounter even though we were basically total strangers jerking off next to each other showing each other loads. This never happened to me before, sometimes I read some random comments where some gay guys want to meet and understall suck or jerk off someone, and it always seemed kind of odd to me (no offense for people who like it, you be you). Shout out to all similar guys that just want a guy friend to talk about anything and are not embarrassed, no matter if lifting in a gym or watching porn together.

Various Stories of Single Life [mf] [oral] [anal] [mast] [swallow] [facial]

My ex and I were together for six years. Initially, I was lured in with the promise of wild sex with a sexy woman. On a road trip, she asked if I’d ever gotten road head. When I said no, she leaned over and put her head in my lap and sucked until I came in her mouth. She swallowed and then we went back to listening to some podcast as if nothing had happened. In a hotel room in Miami, she told me to cum on her face. Gradually, though, things settled down and we ended up, as most people in long term relationships, having pretty boring sex. Missionary. Doggy. Missionary. Doggy. No more blowjobs. More more swallowing cum. No more facials.

She admitted one evening that she never really *liked* doing those things. She just tolerated them because she was trying to win me over. Huh. I settled on the fact that this is just how it was. Women didn’t like swallowing. They didn’t like facials. They didn’t like rimjobs or anal or getting face fucked.

And then, for various reasons, we broke up.

Owned by the Maid Ch. 2 [F/m] [F/f] [domination] [mental control]

*This wealthy family has a new live-in maid and her presence has them all in hot water… This story is fiction.*

JERRY – The new maid was really testing my limits. In the last couple of years, I had finally gotten better at controlling myself… or maybe I was just getting old. Either way, I hadn’t cheated on my wife in a few years. I was content to jerk off to porn instead.

But Natalie woke something up in me that would not be put back to rest. Her tits and her ass and her mouth. So tender and graceful. I was obsessed. I couldn’t think about anything else but getting my dick inside her.  

At first, I tried to avoid her as much as I could and I managed to steer clear while she did the laundry or scrubbed the floors. But when she served us dinner every night, I always had to eat with a raging boner. After a few weeks, I had still somehow managed to not cross any lines but my desperation grew to a fever pitch, and my boner completely took over my life. I was literally sick with lust – sleep deprived from staying up late jerking off, nauseous with shame, exhausted from constantly controlling my urges. I thought I was stuck in this hell forever.

I[F] met a guy off tinder and he brought a bag of toys

I work in retail and often have a lot of free time. I came across a handsome professional man with an adorable face and perfect ass.

We chatted while I was working and I decided to add him on snap chat.

We ended up getting a little cheeky while chatting and he ended up sending me a picture of his dick.
However, it was an unsolicited dick pic – while I was at work.
Luckily for him, my boss was being a total ass hole so I was ready for something fast and hard after my shift was over.

While I was working, I would run to the washroom to send him pictures of my breast and of course, watch the videos of him jerking off and shoving a glass dildo up his butt. He came within 2 times within the 2 hours we were talking.

I was soaked and so ready for some good fun.

He said he’d pick me up after work and head to my place to fuck me real good.

Aunties Panties[inc][F][m][oral]

It was early afternoon on a wednesday and it felt as though there was nothing on earth that could have distracted me from my task. I had a pair of red satin panties wrapped around my throbbing cock and a black lace bra draped over my face. Both belonged to my aunt, a thick, beautiful woman who I had always secretly wanted. I inhaled her scent and felt the moisture she had left behind in her panties on my shaft as I pumped. My cock was out as I laid in her bed and I was nearing orgasm, ready to cum into the soft fabric, when the bedroom door opened.

I jumped in surprise as my Aunt Cindy walked through the door, catching me in my perverted act. I tried to cover myself with a pillow and attempted to explain myself but there were no words to save me from the situation and I gotten myself into.

“Shit! Aunt Cindy, I wasn’t doing anything, I swear!” I lied, my erection stiff and rubbing against the cotton pillow case as I tried to hide my shame.

I Regularly Teach Virgin Women How to Suck Cock [MF]

Admittedly this will be a bit different than my other posts in that it is an amalgamation of experiences, as opposed to one particular one.

I wanted to write about it because several people were surprised that I do this, and expressed interest in learning more. If there is a better subreddit for this, please let me know!

So over the last year or so, I have been on dating apps and Reddit regularly. Once in a while I meet women, who for whatever reason (religion, fear, life constraints) are still virgins.

People looking mostly for casual sex like myself would often stop the conversation there. Instead of that, I ask them about why, and how that has affected their dating life. These women often communicate how they are scared of any sexual situation, because they don’t trust themselves to be able to say no without bothering their partner.

I actually care a lot about women being able to safely explore sex, so sometimes I will offer to teach these virgin women. I believe that the safest way for a woman who doesn’t feel super comfortable saying no to avoid having sex with a dominant partner is to get him off in a different way. So that ends up being the focus.