Anal Archives — Page 738 of 957 — NSFW story

The woman they call babe [MF]

At the beautiful age of 18 I was fresh on the scene at my new home in beautiful shilo. Cold as fuck but I can finally drink , 18 for drinking in manitoba. Anyways we go to this real gem of a place called cecils out side the base. This place has since burned to the ground.

The night. I’ve been on the base for 2 weeks, it’s January and cold as hell. Like -47c cold. Yeah, perfect. We make our way to the cecils and proceed to get fucking wasted. Then she came out of the washroom . Not sure if she had been there all night (the bar). I make my way over and I’m rico fucking suave in my mind. We talk and next thing I know she’s honestly giving the shocks a workout in my friends car as we drive back to the base. Read more »

HATE FUCK WITH THE EX [mf] [oral] [anal] [mast]

John was single and loving it. He fucked more women in the six months since his breakup than he’d fucked in his entire life. The guy was making his way through the never ending supply of women. He fucked BBWs, asian women, MILFs, early 20s college students. You name it, he did it. He fucked a woman’s throat while she masturbated. He fucked a woman in the ass on their first date. He fucked a 24 year old who insisted she was swallow his load every time he came (three times that evening).

On one particular date with a very curvy woman, things didn’t go well. There was no click, no passion. No interest. Sure, she was pretty. But she wasn’t very interested or interesting. They wrapped up the date, parted ways, and then around 11pm that evening, she called to say she wasn’t really into him, but was horny, so … Well, he jumped in his car, went upstairs, fucked her brains out for an hour, came on her face, kissed her goodnight and parted ways again.

He never saw her again.

Just World Theory Part 1

“Which one of you boys could handle a top secret special assignment?”

Harper Grais crossed her legs on Cavaggio’s desk and made eye contact with the new junior engineer, Chang.

“Boyos, give us a minute” Frankie Cavaggio barked over his shoulder, still staring at Harper from the corner of his eye.

The other IT guys fled the basement server room as Cavaggio, flustered, gathered himself.

“Ms Grais anything. Miss. Ma’am”

Chang’s face turned bright red as Harper adjusted her skirt and puckered her red lips.

“Wonderful. Here’s the super secret assignment. Head down to P. S. Harrington’s…”

“The bank?”

“Yes Frankie, the bank. Well, technically, private equity firm.”

“Ok”

“And find out whose security badge this is.”

Harper placed a black plastic fob on the desk that had “P. S. Harrington” impressed on the face of it.

Frankie Cavaggio had a background in computer hacking and social engineering. He was never caught so he “went legit” and made his way into a relatively comfortable information security post at the United States Attorney’s office. Read more »

First anal for my young lover [MF]

Being in an open relationship with my girlfriend definitely has its perks, like being able to sleep with a much younger girl that works in the same building I do.

Cassie looks like a typical office/front desk employee. But under the prim and proper work exterior a hard-partying, tattooed rocker girl (with one or two daddy issues) is hidden.

When I hooked up with her for the first time Cassie summarily denied anal. With a little bit of convincing every now and then however I convinced her to work up to it however.

It took some doing getting her ready. Playing with her lovely, perky bottom is definitely something I looked forward to. So after a period of careful preparation the day had come.

We met for dinner after work. And while Cassie normally is a hard drinker too, I could tell by the way she nursing her drink and looking uncharacteristically insecure, that she was nervous.

So when we were back at my and my girlfriend’s place, (She was out of town for work) I decided to be more gentle with Cassie. Normally she likes it at least a little rough, but I think the prospect of taking it up her other hole had nerves in disarray enough. Read more »

My afternoon yesterday: plugged, waiting for him to come home and [F]uck me

“I want to tie you up tonight” he texted me, around noon. Five fuckless hours to go.

“So, I should be waiting in bed for you?”

“Yes, put a plug in and don’t touch yourself ?”

Fuck. I couldn’t concentrate on work anymore. My stuffy, windowless office pressed in on me. Middle aged women in the hall erupted in laughter. Fuck me.

I left at 3:30, couldn’t take it anymore. The holidays are so close, there’s nothing to do, and I’m aching for him. If I weren’t so turned on, I’d be uncomfortable.

I start straightening up the bedroom, neatening the sheets, putting away junk on the nightstand, turning on some mood lighting, just in case he felt like filming it this time. I eye the drawer with my vibrator in it… Release is so close. But no. I can’t. I need him.

I opt for some personal grooming instead. Frankly, it’s been awhile. It’s cold out, and sitting naked and spread legged for 20 minutes, meticulously shaving delicate skin, hasn’t seemed appealing. But warmth is radiating off my skin and flushing my cheeks, so now seems like a good time. I leave one patch–I never cared for the bald look–and focus my attention on getting my skin as smooth as possible. Read more »

How it started…. Part 7 [Anal] [MF] [cheating]

We spent the evening at a gig watching a band with B’s wife and some other friends. We really didn’t get up to much mischief at all as my abdominal muscles and lady parts were on absolute fire, just a few moments of making out snuck in here and there and a sneaky ass grope or two.

At one stage B wants me to dance with him and I decline, I’m feeling shy and very aware that his wife and friends are here with us and I don’t want to look too intimate in front of them, I worry I’ll get carried away on the dance floor. He keeps pestering me about it and I keep refusing until he leans forward and whispers in my ear ‘You can’t be shy with me, I licked your asshole this afternoon’

With that my mouth drops open and I KNOW my face has flushed red. I can feel the heat in my cheeks. I stare at him looking for something clever to say as a come back but I’ve got nothing. While I’m in my dumbfounded stupor he takes the opportunity to grab my hand and drag me onto the dance floor. Read more »

Daddy Kole

It all started with a wink. A wink from Ethan he was sat with Sergio in the morning before class, conversing about whatever guy they found cute this week, and a wink from me, Kole Hollington , the well-known fuck boy of the school. Girls drooled over me and guys wished they were me. I have a new girl under my wing each day, but they weren’t up for sex- hence why there was a new one each day. I thrive for sex. I dreamed of a submissive sweetheart, maybe two, ideally one with an irish accent or an alcoholic who was rumoured to be in a relationship with their cat. Now, i’m not gay, but i’m open and recently boys have been the ones who hubba my bubba. Sergio was who I dreamed of, and recently Ethan. “Hey baby.” I lowly growled with a prominent smirk as I pushed Sergio into the corner of the hallway, instantly making Ethan beyond jealous. Sergio gulped, his whole body tingling as he felt my warm breath on his tender, untouched skin. I snaked my hands up Sergio’s shirt, my hands gripping his bare waist as I pulled his body close to mine. I could feel his small package against mine. Looking up at me, Sergio bit his lip. I leant down slightly, giving the Irish boy a hard, rough kiss. “Teachers’ lounge, lunch time. On the fucking dot. Don’t be naughty, babyboy. Be there on time, or you’ll be punished!” I ordered, tracing his jawline with my finger, whispering: “And I know you love being punished.” I smirked, placing a hand on his ass as I spin him around and sent him off to class, a deep blush on his face. Lunch time rolled around, and Sergio was ten minutes late to the teachers’ lounge. The 15-year-old tugged at his jumper sleeves, which revealed his prominent collarbones. His tight jeans showed off his ass which I admired ever so dearly. With a smirk, I slammed the door shut and locked it. “Well, look who’s late!” I tutted, grabbing him and pushing him on the couch. “You’re such a bitch, you know who wasn’t late? Ethan.” Read more »

MY OLD HIGH SCHOOL TUTOR [mF] [oral] [anal] [gape] [spit] [piss] [swallow] [facial] [mast] [rimjob] [prostate]

In high school math wasn’t my strong suit. At one point, I had a tutor who was an elderly British woman, but she retired to Florida to live out her years and recommended a woman named Nicole.

“You’ll just love Nicole,” she said with a wink.

I knew what she meant the moment Nicole walked in. She had curly blonde hair, large breasts, a tight stomach, toned legs, a firm ass. She looked like Julie Bowen from Modern Family. But even the best tutors, like Nicole, had trouble reaching me. I just wasn’t interested in math. One afternoon, Nicole had one of those “lightbulb moments” when she caught me staring down her blouse. She was wearing a lace bra—black—her cleavage was hard to ignore.

“Oh,” she said, a hush falling over the room. I was 100% certain that would be the end of that. I blushed, stammered, struggled to come up with a lie, but instead Nicole just winked at me and said, “I think I know how to motivate you.”

MOVIE MATINEE [Anal Play]

Years ago. Summertime. The weekend. My wife and I decided, last minute, to go see a movie matinee – one of those big blockbuster superhero movies at the megaplex.

We were running late. The parking lot at the theater was packed. I parked way at the far end of the lot which my wife wasn’t happy about, but that’s where there were open spaces.

We were hustling towards the theater entrance, or I was … my wife was sorta ambling. She was wearing one of those long maxi dresses that feels like a t-shirt, flip-flops, and sunglasses. She was high and had said she wanted popcorn, Twizzlers and a Diet Coke.

Thinking about the line at concessions I was getting impatient. “Come on,” I urged. “We’re gonna miss the beginning.”

My wife huffed in annoyance but did pick up her pace.

We were halfway there when she abruptly veered right, stepping between two parked cars. She hauled the hem of her dress up to her waist and squatted. She wasn’t wearing underwear.

Thinking she was about to take a piss I said, “You couldn’t wait until we were inside?” Read more »

Partner Swap, a Bet and BBC/Cuckolding [MF]

A warning for starters. This is not going to go as you might expect from the title.

For a while now my girlfriend, Ivy, and I have been in an open relationship. We have experimented with threesomes before and in our MFM threesome I found I am not into watching her fuck other guys. It made me want to punch the other guy in the face, but I went through with it anyway, as Ivy had arranged a MFF threesome for me before.

I was ok with her sleeping with other guys, I just don’t want to watch. Ivy mostly has one-night stands while on business trips and I am mostly seeing a younger woman, Cassie, that works in the same building I do, aside from some few meaningless one-night stands.

However a while back Ivy wanted to try a partner swap. So while I don’t relish seeing her with another guy, Ivy is a big enough woman to tolerate me essentially dating a younger woman on the side. So with a healthy amount of reservedness I agreed and let Ivy set things up. Read more »