Friends With Benefits: A is for Anal [MF] (Part 1)

This happened to me when I was a sophomore in college.

I met Amy in my English Literature class. She was a cute girl, 5’6”, 135lbs, large brown doe eyes, a perky set of 36Cs, and a perfect round ass. Her short, bobbed haircut was dyed dark red which accentuated her slender neck. She’d often sit next to me in class, her ass occasionally brushing my arm as she maneuvered in between the desks to sit down next to me. She’d spent half the class leaning over to copy my notes, not that she could actually read my shitty handwriting.

Amy was from a small town in middle of nowhere North Carolina, a country girl that liked to ride horses. That explained her amazing ass and thighs. She’s way out my league, and I could never quite screw up the courage to ask her out. I was stuck in the “I’ll let you copy my notes in class friend zone” or so I thought…

Superbowl Party Turned Oral Orgy [MMMMMMF] [gangbang] [buk] [oral] [anal] [mast]

My buddy Chris has a Superbowl party every year. We order pizza and wings and everyone brings drinks and we’re set.

This year, a woman joined the mix, which wasn’t a big deal. But in an effort to set the tone early, she assured us we didn’t have to hold back any lewd comments about our girlfriends or wives.

We laughed it off and then one of the guys explained he was recently single. As we talked, we realized every single one of us, including the new girl, Margot.

“You French or something?” Mark asked Margot.

“I am not,” she said with a laugh.

“Too bad. I heard French girls like piss. That true?”

She laughed. “Well, I’m not French, so … I guess I wouldn’t know.”

“Do YOU like piss?” Margot asked.

“I … uh …” Mark stammered. “I don’t know. What? Why?”

“Well, you asked if I liked piss. I mean, if I’ve been out all day holding it in and I’ve really gotta pee, then, yeah, I love piss. But I assume you meant sexually. Like, do I like to be peed on. I’ve never thought about it. But you obviously have. Do you like to be peed on?”

Spying on the Girl Downstairs [M] [f] [voy] [mast] [oral] [anal] [pee] [squirt] [cum swallow]

A few nights a week, I’d dig out a cigar and go for a walk, always making sure to stop by the girl’s basement apartment. I could always see in and constantly prayed for a glimpse. I’d seen her on the street and she was a goddess — thick, muscular thighs, large breasts, great posture, blonde hair, ice blue eyes.

But I wanted to see more. I wanted to see her naked, walking around her apartment. After a few months, I got her schedule down. She’d come home around 730pm every night and would take a shower. I knew she was showering because she’d crack the window open and the steam would rush out. I’d linger, pretending to check my phone or re-light my cigar.

Eventually, she’d come out of the shower in a towel, but she’d step behind a closet door to change. She never closed the curtains, though, so I kept hoping that one day, I’d get a glimpse.

And one day, I did. I lingered around 7:55pm, waiting for her to come out of the shower. During that time, I did have to relight my cigar, which sent up a huge cloud of smoke.

[MF] Milfs ass popped out durring sex.

I’m working in a company for some years, almost from day1 a hot milf (12 yrs. older) draws my attention and she was drawn to me, at least I felt it. Could’nt really confirm it, since we only met at work and working in different departments.

[CD] to [cuck] Wife tells the story of how it started

My husband Ron and I have been going through some rougher than normal patches for the last few months or year. We have been married for 15 years and together for 17 years. We met early in life, actually while still in high school. Yes, we were high school sweet hearts but, neither of us were completely “unexperienced”. While I believe my past was a little wilder than his, he was handsome, sweet and made me want to be a good woman for him. Ron, was always a quite person and didn’t talk much about his past. That was good for me because I didn’t really want to talk about mine either. So, through the years we grow together. Yes, there were some fights but, nothing major.
One night a couple years back, Ron and I are talking like the best friends we are, while we are drifting off to sleep. He tells me that he used to dress in women’s clothing. This didn’t completely shock me, I’m aware a lot of boys crossdress at some point growing up. I console him, telling him that is no surprise and we fall asleep soon after.

Night long sex with the girl in the dress [MF]

I met this girl a little while ago back at a family gathering. It’s not incest shit lmfao…she’s my aunts niece, no relation. We hit it off right away but didn’t get together until a few nights ago. After a night out, skipping the boring details, she came back to my apartment and we went up to my room…

She unzipped my fly, pulled out my penis and put it in her mouth. She was still wearing her dress. I watched her long eyelashes and curled tips move as I grew bigger in her mouth. Her bracelets making a sound against each other. Wrapping around me with her long and soft tongue, I moaned I was about to cum.

As soon as I said that she stopped. She moved away and began to undress me. Taking off my shirt, pants, tie, underwear, everything. She made me lie down on the bed, her clothes still on. Sitting on the bed she took my hand and guided it to her vagina. She wasn’t wearing any panties. I felt the warmth of her vagina. As she shoved my fingers in, it was deep, warm and very wet.

[M][Anal] The Tale Of The Mentally Ill Man Who Has A Fetish For Tablespoon

Have you ever felt the sudden uncontrollable urge to stick something deep and far into your asshole? If not, consider yourself incredibly lucky. Everyday is a long lasting struggle of fighting the intense urge to stick tablespoons deep into my anal cavity. I’ve tried everything from butt plugs to XL dragon dildos, nothing satisfies my obscene craving for the small cold metallic rectangular handle of an everyday tablespoon. The cold that runs throughout my asshole brings me such an amount of pleasure I feel like my dick explodes every time.

My “addiction” as my 13 therapists and 18 mental counselors call it, consists of sitting with my ass open aimed towards the sky, what follow is me sticking the coldest tablespoon I can find’s small handle deep into my rectum. I’ve never been able to push down the entire shaft of the tablespoon, most of my “sessions” nowadays just involve me getting it hardly a quarter of an inch in before my dick shoots out semen like a fire hose.

[M]y [F]irst story. Broke the only two rules with my GF.

LONG STORY

So my girlfriend, let’s call her Sarah, I have known each other for 7 years but only have been dating for 2. During that 7 years we had an ongoing FWB relationship and often would bring in other women for threesomes. She also likes watching women suck me off or ride me while she just masturbated. We had an amazing sex life.

I finally asked her to be my girlfriend and she said yes, and that I could continue to fuck other women, with only two exceptions. The first girl I wasn’t allowed to fuck was her best friend, who we’re going to call Brittany, a 5’5″ 130 lb mixed race knockout with a big ass and DD tits. She’s a kinky and flirty girl but I never had trouble swerving that shit. The second was my longtime best friend who’s 6’3″ 180ish, massive tits and a pretty nice ass, and for the sake of confusion I’m gonna call her Jennifer. I’ve never had a shot with my best friend because she likes men taller than her and I’m 5’9″. My girlfriend felt insecure about these two women because of how close we all were.

[FM] My first anal orgasm

I’m back with another part of my experience yesterday! (Referencing previous post about the fwb and I and our 3 weeks of pent up sexual frustration being let loose) So, one of the things that I credit my fwb for getting me into is anal. Before meeting him, anal was something that I never thought I would enjoy. I was too scared of it being painful, etc. Since we started hooking up in August I went from being completely against it to absolutely LOVING it. It started out with a finger in my ass while riding him in reverse cowgirl, and progressed to me using my dildo for practice when alone. We’d only recently attempted anal with him penetrating me about a month ago, and it was great! I didn’t cum from it, but it definitely felt amazing, aside from a little bit of pain upon initial penetration and thrusting. I knew I wanted to keep at it though, and I really wanted to be able to cum with his cock filling my ass.

[MF][anal] having my asshole fucked and filled with cum for the first time

hey everyone!
This story is about the first time I, obviously, had cum on my face.
For backstory, I was 16 (he was 18) when this happened. we were in a car after a movie. we had been rubbing each other a little during the movie, but not much. He basically asked if I would give him a bj, and he would eat my pussy in return.
keep in mind that i’d never had real sex or anything before this point. so, we drove over to his house. it was a 7-9 movie, and his parents were gone. we immediately went to the bedroom. he said “do you want to do something really naughty?”, or some word of that nature. being the 16 y/o girl I was, very wet and ready at the time, I was pretty much up for anything. he told me that he wanted to do anal.
so you can imagine what it was like, here are a couple details.
I’d never showed anybody my vagina before. he wanted to see my butthole? it was embarrassing. I was super insecure about that part of my body for obvious reasons.
My butthole was SUPER tight. I knew because I had tried to finger myself a couple times before, but it was hard and pretty painful so I gave up. I also knew the feeling – it felt like I had to shit the entire time. so I wasn’t a fan of the feeling, but it sounded naughty so I said “fuck yeah”, albeit nervously.
I ran to the bathroom, emptied my bowels, cleaned my hole up a bit, and went back in. he was playing some sort of catchy rap music. he told me to get naked and bend over. I took off my leggings and my panties, nervously bending over and exposing my asshole. he admired it for a minute. then, he spat on it a few times, getting it nice and wet.
this was my first time, but not his. i’d played with my pussy/ass before, but this was on a whole new level. he started by licking it. the perfect combination of rimming and eating the inside made it feel incredible. he then started fingering it, middle finger first, slowly in and out. I was a bit more relaxed, so it went in and out easier.
“ready?” he said. “no”, I replied, smiling a little. he knew what I meant. He grabbed a little lotion, applying it to my butthole, and began rubbing the hole with the tip. he slowly moved in, making gradual progress. he seemed to hit a “wall” a couple inches in. he stayed at that depth for a few minutes. as he would take his cock out, a couple farts would occasionally leave, which were super embarrassing, but neither of us minded that much.
we were eventually to the point that it was mostly in (about 5″). it felt incredible. it still felt like I had to shit, but I kinda liked that sensation, and I could tell it was mutual. he fucked straight for about five minutes, really managing to open my ass up. by this point, I got used to the queefing that was occurring (still embarrassing!).
he informed me, on taking it out, that it was “wide open for me”. I could feel air flowing in and out, my ass exposed to the outside air, which felt kinda good.
he told me that he was gonna cum as we relaxed for a minute, my ass still in the air, him rimming it a bit, fondling with his fingers, etc. I told him he could, but I didn’t say where, so he assumed I was okay with it. he stuck the cock back in my ass, rubbing my pussy, and came. that went on for about fifteen seconds. I could feel it sliding down the inner edges of my ass. it felt very good, and it seemed to fill me up.
he then told me to “fart it out”. I went into the bathroom and sat on the toilet, and he followed me, which was embarrassing again but I didn’t protest. he also requested that I turn around, so he could see it come out of my ass. for a good five minutes, I farted the cum out.
honestly, it was one of the most shameful and embarrassing experiences I’ve ever had. but that was the fun part. i, the shy seeming yet slutty girl i was, loved the feeling of being shamed and embarrassed like that.
thanks for reading! xoxo if you have any questions, comments, or wanna talk/rp, pm me!