[First Time] 28M. Receiving anal [m/m]

I am now a 28M and this happened when I was a bit younger. Sorry for the wall of text.

I was staying at my friends house and we had had laid down on the floor getting ready for bed. After laying there for about a half hour in the dark I felt my friends hand come to rest on my waist. It slowly made its way down to my dick. He started rubbing it which made me really hard. He must have taken this as a sign to continue on. His hand made its way back up to my waist band. He started to pull my shorts down until they were around my knees.

He then reached around and started jacking my dick which felt great. I could then feel the hard and warmness of his dick working it's way between my ass cheeks looking for the right spot. Once he found it he started to push a little harder and I relaxed and he slid in. Not sure what was used for lube but it worked.

Oral sex in the camp office [m/f]

Emily was my first college fling. She was a gorgeous brunette, with green eyes, handful sized tits and what an ass. We "dated" through Spring semester. We had a lot of firsts together, and did pretty much everything but PIV or anal sex. We mutually agreed to cut things off at the end of the school year.

I was working at a summer camp in the mountains that summer, as a photographer. There was no cell reception or WiFi at camp, so communication with the outside world was limited.

Even though we did have Internet, Emily would write me letters. She loved having an excuse to use paper mail. I wrote her back and so we stayed in touch. A few weeks into the summer Emily told me she would come up to visit. She had a few other friends on staff.

On the day Emily was supposed to arrive I was crazy busy and lost track of time. When I saw her I was caught completely off guard. She was wearing a white t-shirt and running shorts. To lost people, it didn't show off her toned swimmers body. But I knew exactly what was under the thin layers of fabric and I knew I wanted her badly.

MM the first and only time I took a guys bi virginity.

I had a really bad introduction to guy on guy sex. Mostly selfish guys who are just looking out to shoot their load into someone rather than having a good experience. So when I was asked by a swinging friend to be his first anal experience I was determined to make it count.

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Peter came over straight after work at my request and I told him that I wanted to get him comfortable with us being together from the start. The second the door was closed I turned to him, put my arms around him and we snogged as we had in swinging sessions in the past (originally to satisfy a fantasy of a female friend). I told him we weren't starting anything yet and to relax. We cracked open some beers and got the xbox on.

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After a few hours of banter, gaming and snogging stops we were completely chilled out. Both of us only in boxer shorts and curled up on the sofa playing a co-op game. I made my move and started kissing his neck and shoulders and said "let's go to bed".

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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.

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.

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.

So Wrong to Want What I Want [BDSM][interracial]

This is so wrong… I kept telling myself. For several years however my fetish just grew and grew. After my last boyfriend left me I decided to finally take the plunge and tell my 'bff' what I wanted. I thought she would be shocked! Instead she told me about how she indulges in her fetish life with her boyfriend all the time and even go to fetish events. But she had never heard of someone with my particular fetish before.

You see, I am an African American woman, my great-great-grandparents were slaves. And I, more than anything, wanted to be sold as a sex slave. It is hard to even quantify the cultural significance of what I wanted. I knew it was wrong. Slavery was ingrained in me as the worst injustice ever perpetrated. That I actually wanted a white master and mistress to own me, even to rape me, was against everything I believed in. Yet it was what I wanted.

After a few weeks of discussion she gave me a suggestion that would change my life. She suggested that I pretend to be her (and her boyfriends) slave for a month.

[M/F] Honeymoon anal. With long back story.

Long time lurker, first time poster. Skip to the honeymoon part for the point of the story and the more detail.

We have been together for six and a half years now, and just recently married. She is 5'4", brunette, lusciously curvy with an ass to die for. I am 5'10" average build, broad shoulders, nothing too wild. We began our relationship her as a virgin with very little experience, and myself who had sex about three times with a past girlfriend.

Throughout the start of our relationship, we began to slowly explore our sexual boundaries. It started as usual with groping, teasing, leading to oral and eventually we did the dirty. This opened up a whole new side of both of us as we were constantly horny and in need of each other. Three, four and five times a day and we had to stop just because we were so sore. We talked about each others fantasies, and mine being the standard for a guy – anal, facial, swallow, etc.; and hers being on the conservative side – back seat of the car, different places in the house, the most elaborate of wanting to be in a tent outside. We started to slowly satisfy each others desires albeit, rather clumsy.

skype sex -> first foursome! [mffm][18/17/18/18] – warning: really long

note: you can skip down to where the foursome starts – keep scrolling until you see the bolded note

backstory: this was the summer before we all went to our respective universities. I (f/17) was with my boyfriend (John), my friend (Dean), and his girlfriend (Katie). We all went to the same high school and were pretty good friends. I'm 5'5, asian, and curvy. Definitely not thin, but I have a nice hourglass with nice boobs (36dd) and hips/ass. Katie is around my height, blonde, and a smoking hot 10/10. She's thin, but goddamn she has such a nice ass. She had cute perky boobs, a nice thin waist that flowed ever so beautifully into her hips and amazing ass. John is 6', blonde, lanky, with slightly above average length dick. Dean is a bit shorter than John, had that ex water polo player build (not rock hard anymore but fit and had a nice ass), and his dick was just slightly shorter than John's but was also slightly thicker.