2nd hookup turns into (m)y (f)irst time doing anal

I had seen this guy once before but we hadn’t met up in over a month. This is how our text conversation went.

Me “wanna fuck?” Him “when?” Me “now”

He says he needs an hour to get home from school but he’ll meet me then. Hearing that was exactly what I wanted. I went to the mall to kill some time and then texted him that I was on my way there. He says yeah come now. I drive to his place and park and he then tells me “PS I’m not perfectly groomed right now.” Like that matters at this point, I’m horny and really want to fuck him.

Some description of this guy, 26 years old, has scruffy facial hair, a very hairy chest which I love, he’s fit, cut, and the thickest person I have been with so far (my sample size is only 4 though lol). He is the hottest guy I have slept with and the one I have had the best sex with so far.

Probably some of you have read my stories before, but for those of you who haven’t.

My Airbnb guest (NSFW)

(This is kind of long and since it’s my first post, I wasn’t really sure what to include but I thought it was important to give the back story because that’s what made this such an amazing experience. Here goes…)

So it was late May of this year and my flatmate Alex was on this two week holiday mountain climbing in Switzerland. Before he left, he asked me if I would mind if he let out his room on Airbnb and I jokingly said no, as long as he found a hot girl to rent it to.

As of Saturday when he left, he still hadn’t had any luck. I don’t know if the price was too high or what, but he ended up leaving town without finding anybody.

We have a really sweet flat. It’s huge actually, and has this amazing view of the harbour and no matter what time of day, it’s really nice to sit out on our balcony, watching the people in sidewalk cafes or the gulls and swifts and cormorants. It faces south so we have both amazing sunrises and sunsets. A really prime location.

The Book Of David [mf][ff][inc][first][group]

She was gorgeous. Her black hair was straight and smooth and hung like a silk curtain over her shoulders. Her face was a work of art, with high cheekbones and luminous eyes. Her light skin was soft and unblemished. Even her name was uniquely gorgeous… “Cherys” (pronounced Sheh-REESE, her parents were hippies or something).

She was nineteen, in the full flower of youth with her best years still ahead of her. And despite her young age, I couldn’t help but think of her already as a woman. She had full curves perched around the tightness only a teenager possesses. Hers was a body that would be the envy of any model in the nude magazines my best friend swiped from his dad. I imagine that her body was the perfection that Adam first witnessed when God created Eve.

Her tits were so big, so round, and so indescribably magnetic. Her ass was buoyant and tight as a drum. Her irises flickered and changed color depending on the light, from green to blue to violet, each hue more beautiful than the last. Even her hands were delicate and utterly lovely. I was so in love.

Don’t Flash Your Tits At Strangers, Part 5 [MMMf] [blkmail] [huml] [reluc]

Aly had never been happier to be stressed out about exams. It meant she was finally getting back into the groove of being at school, and that her Spring Break drama was so far behind her that she actually had room in her thoughts to stress about things besides showing her tits to strangers and letting them cum all over her naked body.

“Aly, please. Let’s not pretend you didn’t ace that final,” teased Lena, Aly’s new friend from study group. To replace the sorority sisters who’d spurned her after her Spring Break sexcapade, Aly had returned to the type of people she was friends with in middle and high school – the smart kids who wore buttons downs, ballet flats and tight ponytails.

Even she had adopted the style this morning, donning a cute shift dress, cardigan and ballerina bun. Aly giggled.

“I mean, I think I did okay, but that doesn’t mean I’m not nervous still,” she said, sipping her iced latte. They were sitting at her favorite coffee shop just outside campus. They roasted the best espresso beans and, well, the barista/owner of the shop was absolutely gorgeous. His name was Ryan, and if Aly wasn’t mistaken, he gave her the eye every time she came in, but unfortunately, never spoke to her. *Just come and say hi already,* Aly groaned inwardly.

(M)y (FFF)riend lost his virginity.

I have been a long time reader and finally decided to attempt to put some of my own memories into words. Back story around 2008 when I was married to my ex wife, we were part of a car club which contained the majority of our friends. Our closest friends in the car club also were part of our little swinging circle. This circle mainly contained 3 different couples, AP and EW, AP was 29 years old, skinny but not too skinny, short hair. He is the rave party type with a military background (I know does not make since). EW is 20 years old around 5’3″ nice dark hair, great ass, smaller but nice tits she has some curves but not much. She is the down for anything party girl. Next we have HP and DJ. HP is 23 5’7″ long dark curly hair smaller but nice ass with C cup implants she is tall and slender. She is the more reserved, but when in the mood LOVES to party. DJ is your25 year old 6’0 high school football player. her is larger but not fat, and has the ex jock that parties hard attitude. Than there is AD and HD. we are the married couple and last of the circle of friends. HD is 22 5’3″ shorter dark hair with highlights, she has perky 34c’s with great ass and body. Her personality at the time (she is an ex wife for a reason) was the stereotypical preachers daughter. AKA seems very sweet and innocent, but behind closed doors is one hell of a closet freak. Than there is me. I’m the 24 5’8″ in shape but not built guy that gets along with everyone. I had the brown shaggy hair skater kinda pot head mentality (laid back and got along with everyone), people called me the hippy if that makes since. Last we have Squirt long story short he got his nick name from a party when some of the girls were grinding on him and he nutted himself with his pants on, squirt was the 18 year old senior that was not apart of our party group, but was in the car club so we knew him very well and hung out with him all the time. He was the kinda dorky not id say 5’11” not big not small. dark hair just all around innocent sheltered nice kid.

Revenge Is A (Naked Cumsoaked) B*tch, Part 3 [Mf] [blkmail] [huml] [reluc]

Despite saying she’d visit Bryce, Summer didn’t show up at the office the next day. Evan smirked at his desk, listening to all his coworkers lament the fact that they didn’t get to see their “lunchtime sunshine.” Ugh. Their worship of Summer made him kind of nauseous but at the same time, it gave him an odd sense of pleasure because the girl they bowed down to bowed down to him.

With his footage of her dirty bachelorette night fling, Evan had Summer literally on her knees. He could tell her to do anything — maybe kneel under his desk and deep-throat his cock while he pretended to work. Or maybe sit on his lap and let him play with her pussy while he continued his online search of where to go on vacation.

Evan could do whatever the fuck he wanted to Summer.

But before that, he needed her to at least show up to the fucking office.

“Wait a goddamned second,” Evan muttered to himself, realizing his own sheer idiocy.

He had just blackmailed his boss into keeping him on the payroll. He had just blackmailed Summer yesterday into jerking him off topless. Why the fuck did he still think he needed to play by any sort of rules?

The Abducted Librarian is Entertainment for the Sadistic Bikers [Str8][Reluc][sadism][BDSM][Mdom][Fsub][MF][deep throat][oral sex][machine sex]

“I’m going to take you home soon, but know that we own you now. You’ll be coming back, Jane. And do not even think about trying to hide from us,” he explained softly. As he spoke, I felt his lips moving against my ear and his breath against it which pitifully turned me on. “I own you, Jane. Tell me how I own you,” he said, his arm around my waist giving me a squeeze.

I hesitated because I felt like it would be signing a contract. “Jake, I don’t want to tell…” I paused when his grip on my waist tightened, clueing me in that I was giving the wrong answer. I didn’t care at all…until he caught my chin and directed my gaze toward the wall of whips on display. “Yeah. You own me, Jake,” I corrected immediately.

His hand clasped on my shoulder and he turned me to face him, then pushed me down to my knees. That quickly gave me the picture of what he wanted, and I unzipped his pants and took out his thick cock because his perfect cock in my mouth seemed like a much more agreeable activity than anything involving the horrible whips displayed on the wall.

Fun in the Sand [Str8] [Oral] [Voy]

So this is another story of Lily and I, about two years after Bracelet BJ. We hit a beach town in Delaware, complete with boardwalk and everything. We were wandering around, me in swimsuit and trunks, she wearing a bikini underneath a flowery light blue summer dress and her hair in a ponytail. Big sunglasses, and a beach bag over her shoulder. We found a place to camp out; relatively secluded. We were sitting on a beach towel in the shade of a sand dune, and she had this wild idea. She took her sun dress off, leaving her in this dark blue string bikini. Her tits were fighting the top because it was an old bikini from when she was younger, so her tits were bulging out. She was sitting next to me, putting sun tan lotion on. She looked over at me asked asked if I needed a hand, and I said yeah. Before I knew it, her optioned hand was in my swim trunks and around my cock. She starts jacking me off, and I’m leaning back moaning. The she moves between my legs and does another favorite of mine. My cock out of my swim trunks, she pops her tits out of her top, leans over, and begins to titfuck me. Her tits are so soft and supple, I just love when she does it! And we’re on a public beach on our honeymoon…the danger was there. But she was a little tipsy already, enough to release her inhibitions of doing anything in public. God the sight; her ponytail bobbing; her making eye contact with me, then focusing on my cock; the way her ass looked with her legs tucked underneath. It was phenomenal. I rubbed her back and kept an eye out; we found a secluded spot, but didn’t know how long we had it for before someone discovered us. But Lily didn’t care at the time. So she kept rocking faster, and looking up at me, smiling. Just another honeymoon adventure. I stayed quiet, and before I could tell her I was coming, well, I came. All over her tits and chest, thick white globs in strings. One jet hit her on the chin. She is a reluctant cummer; meaning, she normally doesn’t like getting cummed on. In the heat of the moment she’s ok with it. And if she’s drunk. She giggled, put her top on, and ran into the ocean to wash off with no one the wiser.

Fun in the Sand [Oral] [MF][Voy]

This is another story of Lily and I…so this story is from our honeymoon. We hit a beach town in Delaware, complete with boardwalk and everything. We were wandering around, me in swimsuit and trunks, she wearing a bikini underneath a flowery light blue summer dress and her hair in a ponytail. Big sunglasses, and a beach bag over her shoulder. We found a place to camp out; relatively secluded. We were sitting on a beach towel in the shade of a sand dune, and she had this wild idea. She took her sun dress off, leaving her in this dark blue string bikini. Her tits were fighting the top because it was an old bikini from when she was younger, so her tits were bulging out. She was sitting next to me, putting sun tan lotion on. She looked over at me asked asked if I needed a hand, and I said yeah. Before I knew it, her optioned hand was in my swim trunks and around my cock. She starts jacking me off, and I’m leaning back moaning. The she moves between my legs and does another favorite of mine. My cock out of my swim trunks, she pops her tits out of her top, leans over, and begins to titfuck me. Her tits are so soft and supple, I just love when she does it! And we’re on a public beach on our honeymoon…the danger was there. But she was a little tipsy already, enough to release her inhibitions of doing anything in public. God the sight; her ponytail bobbing; her making eye contact with me, then focusing on my cock; the way her ass looked with her legs tucked underneath. It was phenomenal. I rubbed her back and kept an eye out; we found a secluded spot, but didn’t know how long we had it for before someone discovered us. But Lily didn’t care at the time. So she kept rocking faster, and looking up at me, smiling. Just another honeymoon adventure. I stayed quiet, and before I could tell her I was coming, well, I came. All over her tits and chest, thick white globs in strings. One jet hit her on the chin. She is a reluctant cummer; meaning, she normally doesn’t like getting cummed on. In the heat of the moment she’s ok with it. And if she’s drunk. She giggled, put her top on, and ran into the ocean to wash off with no one the wiser.