Anal Archives — Page 525 of 957 — NSFW story

[MF] My college girlfriend and I open new horizons from facesitting to mutually first anal

Signing back up for Reddit combined with quarantine time to get nostalgic has me fondly recalling memories of nights (and mornings) past. Let’s be honest too, we’re all fucking horny right now.

As a creative outlet and a meager attempt to contribute to Sexy Reddit of which I’m so fond, going to post some formative stories along my personal sexual journey starting from the start – as explained below. Hope at least a few of you enjoy!!

I start the tales at the opening of my eyes to all that sexuality would one day mean to me.

I led a happy and sexual adolescence but it wasn’t until 21 years old that things got interesting. In art school and loving life, I had been dating Emmy (also 21 years old) for a few months.

She was beautiful – Lebanese, average height, long curly hair, perky C cups, a firm but large handful of a butt, and a deep and thoughtful smile that combined with piercings eyes to melt any heart. Emmy had a tough and wise exterior – as friends before we dated she was quick to talk about a previous relationship with a professor – but beneath the protective shell, she was a sensitive, deeply curious girl whose experience with sex was limited to a few flings with older men and little in the way of making love or any sort of relationship with real trust and connection. Read more »

Boots & Beauties[FF][celebrity][oral][boots][boot fetish]

The party was in full swing, and the gathering of celebrities was intimidating to the new-to-the-scene Hailee Steinfeld. The most starstruck she had ever been, however, was when she finally got the courage to approach her secret celebrity crush, Ariana Grande. The rest of the party seemed to fade away into the background, and all Halie could focus on was Ariana’s big doe eyes and full pouty glossed lips. She was wearing a skin tight, navy sequin dress with a low neckline and a high hem. Her hair was in her signature tight ponytail, and she wore black, thigh high suede boots with a techno blade stiletto heel.

The moment Ariana made eye contact with the young actress, Hailee began to blush.

“Hey girl, how you doing tonight? I hope you’re having a good time so far.” Ariana smiled and enthusiastically addressed the shy Hailee.

“Oh, yeah, it’s great!” Hailee stuttered nervously. “I, um, I really love your boots!” Hailee giggled, gesturing to her own identical pair of boots. Hailee was dressed slightly more modestly in a burgundy, halter short leg jumpsuit that tied behind the neck. Her boots matched the ones that Ariana was wearing, and they giggled over the coincidence. Read more »

Her Bargain Ch1 Part 2 of 2 M/F BDSM

Part 2.

“I do believe we need to discuss your dress code. We can’t have you running around naked like the wanton slut you are now. So I stopped on the way home and picked up some new clothes for you to wear around the house.”
I grabbed the bag from the pile of items on the bed. I picked out one item. Held it up to her. It was an extremely girly pink pair of panties with a ribbon on front that had a little princess stitched across the crotch and frilly lace on all of the edges. I set the panties to the side and picked up the top. It was another extremely girly pink shirt. With frilly lace and princess also printed across the front.
“Look! A matching set!” I chuckled
She didn’t seem to find that very amusing. I smirked.
I grabbed the next item off the bed. A pink leather collar. She seemed disappointed. She really loved her collar I’d given her when we first started this relationship dynamic.
“I know you love your forever collar but you need a full transformation.” I said dismissively
I reached down and took her sleek platinum collar off and replaced it with the pink collar
Last but not least. I picked up a big pink strand of ribbon. “You’ll need to wear this in your hair. Really brings the outfit together” i smirked again.
“Stand up”
She took my now fully erect cock out of her mouth and stood up.
“Try it on” Read more »

First time anal [mm]

A few years ago I was living in Brooklyn and while I was mostly dating women, occasionally I met up with guys on dating apps. The first few times didn’t really go very far – at most a bj, but I never let anyone cum in my mouth. That all changed one weekend afternoon in early summer. I met a guy online in Brooklyn Heights. He was an older guy – maybe about 60 – and I was about 35. (Older guys are my fav when it comes to getting with other men).

I got to his place which was in a nice doorman building and he let me up to his apartment which was on a high floor. The place was really big – probably 3 bedrooms. I got up there and we had a seat on the couch. I was super nervous but he opened a bottle of wine and we got to chatting. Before long we kissed and I reached between his legs and felt his big bulge.

Even though he was older, he was fit (he actually made one of his bedrooms into a gym) and he was hung, I’d guess about 8 inches and thick. He was really the ideal guy for me – hung and older! Read more »

Rimming, anal, and cum play with drunk wife [MF]

As she laid down on the edge of the bed with her legs in the air and her freshly waxed pussy and ass exposed, I knew this night was going to be different.

We’ve been married for 6 years, but started dating when we were 19. Our sex life through our mid 20s was amazing. It slowed down in recent years, but with the stress of work and kids that’s to be expected.

We’re both 32 and have great careers. Both definitely above average in the looks department. I’m 6’1, 185, and in pretty good shape (pics in profile). My wife is 5’8, 130, perky b cups, and a perfectly round ass.

Since moving to the suburbs, we really haven’t made friends. Everywhere we go, we are on the lookout for couples who look like they’d be cool.

My wife chatted up a few other couples at the bar. It was innocent but kind of sexy. With each conversation, all I could think about was watching my wife going down on the other woman but that’s a story for another time. At dinner, she mentioned it felt like we were trying to date other couples and she kind of loved the chase. Read more »

39[F]irst trip in public with my anal plug in was SO hot!

Recent love of wearing my anal plug in public

This is my first post. I’m recently single and love being with both men and women. I’ve had more experience with men, but there is nothing quite like hearing the moan when you lick a sexy pussy right.

I’ve recently discovered how delicious anal can be and how amazing it can feel. I had one of the strongest orgasms of my life the first time a tinder hook up filled both holes and worked them like he meant it. I’d been reading some of the naughty stories on Reddit and decided I wanted to try wearing an anal plug out in public. The stories I heard of how fucking hot it was to know you secretly had a plug in and how wet the ladies would get with the plug in turned me on so very much. So, I stopped at the sex store and purchase several different sizes of anal plugs, so I’d have an option. I bought the plugs on Wednesday and planned to go grocery shopping with the plug in on Saturday. Sometime before Saturday, I also decided to get my hood pierced and was super excited. Read more »

Myself 24 [F] and my bf [M] had sex on mushrooms for hours

Had an awesome experience and eager to share!

My boyfriend, 25, and I, 24, decided to take a mushroom trip together for the first time. We have both done shrooms on our own but never together. It’s important to know that everything we did was consensual and we are both into sub/dom, roleplay and BDSM. I enjoy pain in the bedroom and we do have a safe word I have yet to use.

After tripping for a few hours, we went upstairs to our room. I was laying there and he told me to take my bra off. I did and he lifted my shirt to expose my large breasts. He put his hands around one of them and started sucking on it with his eyes closed. I felt a rush come over me and my pussy was gushing. He started biting my nipple and I felt like I was going to cum. I buried my fingers in his hair and started convulsing and moaning.

I took one of his hands off my breast and put it on my pussy. Between whimpering I whispered to him “I have never been this wet in my life” Read more »

Sophie Trades Her Body For A Mansion (mf | oral | anal | atm | bribe | celebrity)

Today I have a young woman coming to look at potentially buying my mansion that I recently put on the market. I do not know much about this woman, but she must have a decent amount of money. This large Hollywood mansion was listed at a high price. From the application I know that she is a young woman that lives alone and makes a large amount of money. She is on her way over to meet me now to view the house. On the phone she sounded ready to negotiate the terms of purchase of the house. I see her car pull into the drive way, it is a very nice sports car and I watch as the door opens. Her long white legs exit the vehicle as she stands up out of the car and I can not help but notice how sexy this woman is. She has long natural red hair, long white legs, and she is wearing a very sexy outfit for our meeting. She had on a short black skirt, that showed offer her long toned legs. Keeping the look professional, she had on a white dress shirt with short sleeves that barely covered her shoulders. The top was buttoned almost all the way up, but I could see the sexy nape of her neck. Her long red hair was up in a ponytail to match the business attire style. She had on a large pair of black sunglasses that covered most of her face. She walked towards the house carrying a small folder and her purse. I opened the door just as she was walking onto the front porch. Read more »