Tag: Anal

Free Weed! (F50s/F22/F21) [Mf, voyeur, age gap, transactional, embarrassment, professor/student, anal, reluct, drugs]

Free Weed! (F50s/F22/F21) [Mf, voyeur, age gap, transactional, embarrassment, professor/student, anal, reluct, drugs]

It must suck, attending a university in a state where pot is illegal. Well, at least Shelia (F22) has me.

I (M50) am a horny-ass old biology professor who grows marijuana just outside of town. I won’t sell it because I’d get busted and wouldn’t be able continue my oh-so-important research. But I’m willing to trade for certain goods and services, so to speak.

Shelia and her college pals know very well that the pretty girls go to the front of the line, but it’s not all puppy dogs and ponytails.

Among her group she’s the only one I’ll trade with. The rules are always the same. I get my 15 minutes of pleasure in her butthole, and she gets a Thursday-night’s worth of HQ weed for herself and her friends that would sell for $200.

Naturally, Shelia initially found this idea demeaning, but after her little clique tasted one of my varieties, they wanted more. So she said she’d do it _one last time_. And then again, and again. She insisted to her girls that she hated our backdoor transactions—and yet, each Wednesday night she couldn’t sleep, her mind returning to the thought of trading access to her most intimate and private place with a creep who holds all the power. Read more »

The most epic pegging fail… Shit happens [FM]

I’m always fascinated at how y’all respond when I write about pegging because they tend to be popular stories. My theory is that A LOT of y’all have pegging fantasies you’re reluctant to voice, so let me start by saying that pegging (any ass play generally) is fucking awesome. If you’re curious and with a consenting partner, try it. I truly feel bad at how many men are afraid to voice this because I think it’s wrapped up in unhealthy stigmas that shouldn’t exist.

I’ve been so reluctant to write this story out of fear it might dissuade some curious readers, but I also like to take moments to use this account to discuss some of the more “real” intimate parts of sex. It’s not always seamless.

Plus… This story is pretty fucking funny.

I’ve been lucky with ass play generally because I first experimented with a bisexual man. He was very into prep, communication, and general tenderness. The first time I pegged him I immediately understood the appeal. He came so hard his body started convulsing.

It prolongs ejaculation and stimulates a lot of nerve endings. It was super fun to give someone pleasure that way. Read more »

Coming Home From Work [mmf] [sharing] [anal] [oral] [cum]

I came home from work to find you on the bed with your legs in the air spread wide open. The man holding your legs up had his cock deep in your ass. You saw me and smiled. I sat down to watch from the couch.

He fucked you slowly and rhythmically and it made your breasts glide forwards and backwards. I could see from here how completely soaked your pussy was. I don’t know if it was from him fucking you before I got home or from the anticipation of me seeing your ass full of cock. Either way, no extra lube was needed.

I walked over to the bed. Your head was hanging slightly over the edge. I knelt down to whisper in your ear.

“My wife is an insatiable whore.” You moaned. “Good girl. Thank you for waiting to show me how your ass can take it.” You moaned again and squeezed your rock hard nipples. “I’m going to give you a little treat for being so thoughtful. Open wide.” Read more »

My hookup’s roommates wanted sloppy seconds. [FM]

I went clubbing last night for a friend’s birthday. Didn’t expect to leave with anyone but I really hit it off with a guy so at the end of the night, he took me over to his place.

He didn’t want to use a condom and honestly, I was just really drunk and horny, so after sucking his cock, I let him put it in raw. I’ve been tested recently anyway. The sex was good and I definitely felt satisfied. I was going to take a Plan B anyway so I let him cum wherever he wanted, so he came in my pussy once, then after a short break, we moved on to anal and finished with a facial.

I was pretty messy after to facial so I asked if I could take a quick shower. He gave me a towel and I walked to the bathroom with only it wrapped around my body. To my shock, his 3 housemates were all out in the living room area having a 3am meal. They all saw me wrapped in a towel that barely covered my ass, with cum on my face and dripping down my thighs! Read more »

Earliest friend turns into a FWB with a love of facials. [MF]

I grew up with Janine. She was one of the first girls I did anything sexually with. A rail thin blonde. Cute face. Tiny little tits. The perkiest nipples. Incredibly horny. This story is about an ‘arrangement’ we fell into one summer.

I was home from university. She’d never left home. We’d loosely stayed in touch but had a big circle of mutual friends. I encountered her in a nightclub one night. We flirted and made out but other than some brief gropes in the corner of the club, things didn’t go any further that night.

We started texting. One night she gets in touch. “I’m bored. Nobody’s home…”

I’m sure we all know what that message means. I hot foot it around there and we pick up where we left off years previously, namely her laying back and letting me do all the work. She had a tight pussy, waxed to perfection. Each time my length went all the way inside her she’d yelp, a red rash forming over her tight chest giving away home much she enjoyed it.

Janine wasn’t a skilled lay but she was fun to fuck. She’d try a few new things but had some hard limits (no anal – I asked more than once). Read more »

[M41/F39] how my wife transformed from a low libido stay-at-home mom into a submissive cum slut and I from a passive nerdy dad into an assertive dom. (Part 2 of 2) [Romance] [True]

Link to [Part 1](https://www.reddit.com/r/eroticliterature/comments/11a25tr/m41f39_how_my_wife_transformed_from_a_low_libido/?utm_source=share&utm_medium=android_app&utm_name=androidcss&utm_term=1&utm_content=share_button)

The next several days were like a symphony. Each melody, each note, each piece of our relationship and newly adventurous sex life, weaved themselves together into a swelling composition; beautiful, emotional, and building to crescendo. Nerd that I am, I spent chunks of my work days researching my wife’s newly discovered kinks. Reading about dominance and submission, bondage and praise, and brushing up on my boy scout skills – which now had a much more practical purpose – by practicing tying knots. She continued chatting with various redditors, both men and women. Her bicuriosity had manifested itself long before the evolution of our bedroom; in fact, it had become apparent even before we took the initial baby steps in repairing our sexual relationship. With her confidence on the rise and my support and encouragement, she had found a means to begin exploring it – and after several extremely fulfilling chats, we laughed together that perhaps she had graduated past mere curiosity. I watched her and held her at every opportunity, full with contentment and pride as she explored and bolstered her rediscovered confidence and reclaimed her sexual empowerment. Read more »

[MF] How my wife transformed from a low libido stay-at-home mom into a submissive cum slut and I from a passive nerdy dad into an assertive dom. [Part 3 of 3]

Link to [Part 1](https://www.reddit.com/r/gonewildstories/comments/119hka9/mf_how_my_wife_transformed_from_a_low_libido/?utm_source=share&utm_medium=android_app&utm_name=androidcss&utm_term=1&utm_content=share_button)

Link to [Part 2](https://www.reddit.com/r/gonewildstories/comments/11a1ola/mf_how_my_wife_transformed_from_a_low_libido/?utm_source=share&utm_medium=android_app&utm_name=androidcss&utm_term=1&utm_content=share_button)

The next several days were like a symphony. Each melody, each note, each piece of our relationship and newly adventurous sex life, weaved themselves together into a swelling composition; beautiful, emotional, and building to crescendo. Nerd that I am, I spent chunks of my work days researching my wife’s newly discovered kinks. Reading about dominance and submission, bondage and praise, and brushing up on my boy scout skills – which now had a much more practical purpose – by practicing tying knots. She continued chatting with various redditors, both men and women. Her bicuriosity had manifested itself long before the evolution of our bedroom; in fact, it had become apparent even before we took the initial baby steps in repairing our sexual relationship. With her confidence on the rise and my support and encouragement, she had found a means to begin exploring it – and after several extremely fulfilling chats, we laughed together that perhaps she had graduated past mere curiosity. I watched her and held her at every opportunity, full with contentment and pride as she explored and bolstered her rediscovered confidence and reclaimed her sexual empowerment. Read more »

[MF] Breaking the rules and fucking the ass of my favourite hotwife [hotwife] [cheating] [anal] [cheating]

There were two rules. The first was that he got to see.

She was bent over in front of me, gripping the rails of the bed harder and harder. Her wedding ring was glinting in the light against the metal bars.

My right hand was in her dark hair. I had a tight fistful, pulling her into me and arching her back. My left hand was holding her phone, pointing down to capture her gorgeous, round ass bouncing off my cock as I pounded her tight, wet pussy from behind. Each video was sent straight to her husband.

I felt her start to cum, her beautiful, wet, married pussy tightening round my cock as I fucked her harder and harder. “Good girl,” I growled. “Cum for me baby, nice and hard.” I kept stroking, fast and deep, to hold her there until she was shaking and breathless.

I slid out of her dripping, quivering pussy and dropped the phone. I gently moved my cock upwards and started to tease her tight, round ass with the tip.

The second rule.

My other hand moved to her throat and I pulled her in tighter. Read more »

[FM] 19F Anal beginnings

I had my first real anal experience with my now ex bf from my college. We started as just sex friends, then began dating more. We had sex often, even in public.

One night I gave him a bj in the parking garage before our classes started. I can be pretty kinky lol. Swallowed his cum then we walked to class holding hands.

Then Monday we both had off.

I’ve tried anal twice before that, but the guy never finished in me as I had him stop because it hurt and I wasn’t big into anal then. Well that all changed Monday.

Monday I slept at his place. So we decided to have sex all day. As he was fucking me, he asked if I had ever done anal. I guess in the heat of the moment I said yes but I didn’t explain that I’ve only tried it. Then I asked him if he had lube. He didn’t, so I had him spit in my asshole to lube it up, and stick a few fingers in to losen it up for his thick cock. Read more »

The final fuck with my ex [MF] Part 2 of 3

If you missed Part 1 where my ex tried seducing me with lingerie to rekindle our relationship, here it is [https://www.reddit.com/r/gonewildstories/comments/11a8sop/the_last_fuck_with_my_slightly_crazy_ex_mf_part_1/?utm_source=share&utm_medium=web2x&context=3](https://www.reddit.com/r/gonewildstories/comments/11a8sop/the_last_fuck_with_my_slightly_crazy_ex_mf_part_1/?utm_source=share&utm_medium=web2x&context=3).

As we stood in Elle’s bedroom, her ass pressed against my waist, my hands on her hips and our lips locked, I thought of the things I wanted to do to her.

My first thought was that I wanted to fuck her in the ass, but anal had been off the table our entire relationship and while she definitely wanted me back, I don’t think she was willing to go down that road tonight.

The lingerie was something new, though, and I knew I’d be keeping it on her.

I ran my hands from her hips up her body, enjoying the lace beneath my fingers and Elle’s soft skin. Gently, I wrapped a hand around her throat and spun her around so she was facing me.

“On the bed,” I instructed. She laid back with her knees in the air and feet on the edge of the bed. I got down on my knees and began to kiss down her thighs, causing Elle to moan. When I reached her pussy, I kissed and nibbled the thin fabric covering it. My hands moved to her ass, kneading and squeezing her firm cheeks. Read more »