My first threesome [MFM]

Let me preface this by saying that I'm a virgin and have very little sexual experience besides porn, which I've been watching since I was about 12. Yes, even after this happened I'm still a virgin at 19.

Alright a little set up. My best friend of nearly my entire life and his girlfriend, my best friend of a few years had recently got an apartment and I had been spending a lot of time over there. We all became very close, forming a trust circle where we all felt comfortable telling each other anything. We do the average adolescent stuff. Talk about sex, life, and our secrets. Well, little did I know that something that I'd wanted for a long long time and had jokingly suggested between the three of us would come true on one of our drunken nights.

I've always been self conscious about my penis but James and I were pretty drunk, and I guess alcohol gives me a bit of a confidence boost so I was very open. I'm circumcised and he's not. We got to talking and thought it was odd that despite the fact that we've lived in the same house together at times, we still haven't seen each other's penis.

I’m back: Sex with the girl from my apartment building [m/f]

Some of you might remember me. I posted under a different ironman name up until recently. I deleted my account, because it got hacked. Some of the stories I posted over the last couple of years are gone forever from reddit, so I figured I would come back and start posting some old ones to make sure they aren't lost. I will post new stories as well when I have a chance. (New Stories Will Come I Promise). Here is an old one. Hope you enjoy:

Like I've said in previous posts. I figured it would be fun to go back to my promiscuous (man-whore) days and recall some of the stories from back then. I'm generally considered a really good-looking guy (used to model, 6’3”, dark hair, blue eyes, swimmers build, workout regularly), so that enabled me to have quite a fun sex life. These stories are 100% true and not embellished in any way. I think that a straight honest story even if not as exciting at times is a bigger turn on, so that is what I will continue to try to give.

A bunny girl’s midnight rendezvous (F/M)

I don't know what it is, but I've found myself being exceedingly horny most of the time lately in spite of some recent encounters, and this horniness coupled with a boring wet and windy Friday led to me posting a Craigslist ad offering myself up in my trust bunny girl outfit (which I haven't worn in some time) to see what sort of responses I would get.

Needless to say I was flooded with replies, most of which were trash, but I received a few interesting responses and ended up focusing on one in particular from a guy who was articulate and had more to offer in his replies than just "I wanna fuck you". We kept on mailing back and forth and got on pretty well, and eventually I was feeling really turned on as our ideas manifested into a plan. There was one problem however – figuring out where and when to get together, as our schedules never seemed to match. As we both got more excited at the idea we were keen to meet as soon as possible, but as he had band practice with some friends he wouldn't be free until midnight – throwing caution to the wind, we ultimately agreed to meet then.

[M/F] I had my first time in a Laundromat, and it was amazing.

I shared a short version of this story before on /r/offmychest because as hard as it may be to believe. I felt burdened by what happened.

Anyways, I was 19 and pretty down on my luck. I had dropped out of college and things weren't looking great, I was unemployed and suffering from real depression. I missed my friends from Highschool who had all gone off to great colleges out of state. On top of that I was feeling pretty restless about being a virgin. I had no real reason to be a virgin, as a tall tan and muscular Hispanic dude. I used to have no shortage of opportunities in terms of girls that I could experience sex with. But my self confidence was shot after my recent college mishap.

Since I was basically either at the gym or at home playing video games I was in charge of doing the laundry which I had no issues with, it was only fair. So I started to frequent the local Laundromat as the machines made the job way quicker than doing it at home.

One of my bartending adventures [M/F/M]

I'm new here, my friend said I should post some of my stories. Some set-up first, I am a 37 year old divorced woman, no kids, and a couple of years ago I bought a bar. It's a great job and I love it, plus it affords me the opportunity for some flirting and sometimes more every night!

This first one I wanted to share was shortly after I took over the bar. It was a pretty busy night and I talked to a lot of people but one guy in particular caught my attention. We flirted back and forth for a while but he was there with a friend and eventually went back to drink with him, but we flirted more whenever he came up for more drinks. Toward closing time the two of them were still there and they moved up to the bar and all three of us got to talking and flirting. We started showing off our tattoos to each other, which involved the first guy, Joel, opening his shirt to show me some on his chest. By then I decided to make a move and so I asked them if they would stick around after closing, and they agreed. I called for last call, and people started filing out.

Reconnected With an Ex & Had Amazing Sex

This is the final story of my Ex. Since this story, we haven't communicated as she needed to get away from me completely. To update you guys on timeline from the last story, we broke up and never spoke for roughly 2 years out of High School.

When you're single & alone, you wonder what ever happened to your past girlfriends… Thats how I felt the day I emailed her. She was shocked to hear from me, but at the same time was interested in catching up. Our break-up was rough and she rebounded on two guys she regretted… I couldn't say I didn't as a week later I dated another girl in High School. We talked, texted, we were hitting it off again. It was apparent that our chemistry was sparking and things turned sexual quickly. It wasn't long until we were reliving previous sexual encounters sharing eachothers favorite details. Then came sexting. A lot of sexting to the point where we stayed up all night completing eachothers stories. She was phenomenal at it – vivid imagery, and stories in great length – we were making eachother lust for one another. So the day came where we grew tired of story telling, and wanted to relive it. A bit of rearranging schedules and her getting her story straight where she was going, we planned to go out during the evening. It was fall, the sun set quicker during the day and I picked her up as the night sky shine.

[M]y best conference experience yet [M/F]!

Just this summer, I was sent to toronto for a week long training conference. I usually don't mind this except for the fact that I have to pay for everything up front and get reimbursed after. So 7 days of eating out and entertainment is gonna rack up fast. My hotel was situated on the popular main street that is known for it's extensive night life. Heck, even a connecting flight had a group of ladies sitting next to me on the plane talked about hidden gems similar to that of las vagas. I figured I scored big time!

I touch in on sunday and get situated at the hotel. It is around 10pm so I figure I unwind and get ready for the grueling 8am-5pm training day. I get to know the guys at the course, all of them men, considering I work for the tech industry. We all decide to go into town one evening and check out the night life after dinner. We hit a few bars and have few drinks and laughs. Nothing expectantly happens.

If you have anal sex, are you still a virgin? [m/f]

Following up my last story https://redd.it/3row3b with my anal experience with my second GF.

We met through a friend of a friend and were set up on a blind date. She was 27 (I was 25), Asian and average looking, not the clubbing type, think more librarian. She was 5'1, around 125lbs, and had a pretty nice set of C cup breasts that I could see through her black sweater. Dinner went well and we had a few more dates after that.

After a few weeks of seeing each other, she confessed to me that she was a virgin. That was a little surprising given her age but I didn't mind because I had only lost my virginity a few years before. One night after a nice dinner, we went back to my apartment to watch a movie. I lived with two other guys so we went straight to my bedroom. As soon as I closed the door, she started taking her clothes off! She was wearing another tight black sweater and a pencil skirt with what I assumed was pantyhose. The sweater was off and I could see her nice full breasts in her bra. Underneath her skirt was a garter belt connected to thigh high stockings. Needless to say, she came prepared and was ready to lose her virginity that night.

Falling asleep with my cock in her ass M20s/F20s

I've written about this with a different throwaway account, but it feels so awesome I wanted to share it again. Mods, feel free to trash this if that breaks the rules.
We've been married a couple of decades (the M20s/F20s tag is for when we started doing this). So this isn't a new story, but it's one that gets repeated frequently.
She's a super sound sleeper and gets a little annoyed if I wake her up for morning sex. But she does enjoy anal (it was actually the first type of sex we ever had) so with a little coaxing I can usually wake her up around 4-5AM and get her to go prep herself. A couple of minutes later, she'll groggily stumble back into bed and hand me the bottle of lube.
A little foreplay with fingers and such, and she'll give "the moan" that's her signal for "put it inside me, now!" I'll scoot myself forward a bit, put the head of my cock up against her hole, and apply pressure until the ring of muscle opens and engulfs me.
At this point, I'll usually be too horny to resist fucking her ass. But I've never been able to last very long with morningwood, so it'll only be a few minutes before I unload inside her.
Like most guys, the end of the orgasm is when I stop being horny. Dunno why this happens, but it does. But she HATES it when I pull out right after fucking, anal or otherwise. So the only thing to do is grit my teeth and push in a little deeper. Eventually, the post-cum sensitivity goes away and it's sheer bliss just resting there with her ass gripping my deflating cock.
With regular vaginal sex, I'll eventually just slip out when I go limp. But with anal, there's the tight sphincter muscle holding me in.
And at this point, she'll sigh, press her ass back up against me, and wrap her legs around my top leg to hold me in place. And then seconds later, she'll be in a deep sleep. Being a dude, and having just filled my favorite oriface with cum, I'll slide down into a post orgasmic coma.
I can't stay asleep in that position, though. I'll wake every fifteen minutes or so, realize that her ass is snugly gripping my cock, think about how awesome that feels, and then drift away again. Sometimes, her ass does this involuntary "grip-and-release" thing where it tightens up almost to the point of painful compression and then completely relaxes again. This can be repeated dozens of times either slowly or sometimes in rapid succession about the same speed as a nurse inflating a BP cuff. She has no idea she does it because it only happens when she's deeply asleep.
Eventually, the alarm clock will interrupt our bliss. Time to wake up. But sometimes you just gatta hit snooze and fuck that ass one more time before getting ready for work.

CL bj – First Time Swallowing

I've gotten a few requests to write about more experiences I've had, and specifically more about the hookups I've had with the Craigslist guy. This story is about the last time I hooked up with him and the first time that I swallowed (and tasted) cum.