Taking her anal cherry! [MF]

This evening will stick long in my memory for a few reasons.

At the time of this happening, we had been together around a year.

We were attending a party, at a friends house, she wearing a tiny little black dress, which showed her jaw dropping cleavage so much that there wasn’t much left in the top. It finished just below her ass, she wore some black hot pants underneath, as to not show her dignity to the world when ever she bent over. Me in my black jeans, white shirt combo.

We arrived, I went a dumped the beers in the fridge and make a bee line for my best mate. Who was hosting the party. I chat to my mate, for around half an hour, then head of to find my girl. I see her dancing and chatting with my mates girl. I gesture if she would like another drink, to which she holds up not 1 but 2 bottles of beer. That’s a no then I take it. She nods, as she chugs down 1 of the bottles, in fact while your going, grab me one please.

Of course.

[fMF] Wild Roses pt. 19: Wagon Camp [anal] [Msub]

The next morning, their tunics and hair cleaned and brushed, Autumn and Summer set off down the road, following their crude map. For lunch, Autumn downed a rabbit, which they cooked over a small campfire and shared, and by late afternoon, they had found the wagon track where the highway joined the road to the small village. A few miles along it, they came upon a wagon camp, consisting of an office and a small warehouse, a large gravel turning area, and six great stacks of lumber from the nearby forest ready to be shipped out along the road north, along with a pair of piles of large, freshly quarried rock.

No wagons were to be seen, but on a hunch the girls made their way up to the office and knocked, waiting for the proprietor to answer. The woman who swung the door open to them was a northerner, with fiery red hair and a muscular build, and her green eyes glittered in the fading sunlight as she greeted them at the door with a smile.

“Och, what’re’ye lookin’ for, lass?” she said with a broad smile, her large teeth shining like pearls between thick lips.

Me [M] fingering ex-girlfriend [F] to dangerous multiple orgasm while driving.

One thing you should know about my ex-girlfriend was that she was a whiny bitch. There were times when she would be shouting and screaming at me and I would genuinely have absolutely no idea what I had done to offend her. Which was the main reason we only lasted nine months.
However she was fucking dynamite in the sack and was so easy to make come it was almost ridiculous. I’ve never known a girl before or since who I could get off so easily. In our short time together we covered the whole board of sexual experience. Blowjobs, handjobs, titty-fucking, cumshots, squirting, pussy licking, fingering, anal, rimming. If only she hadn’t been such a colossal pain in the arse.
The main reason I was prepared to put up with her when she was moaning about my latest so called indiscretions was because I knew it would only be a matter of time before we would be having dirty sex again.
This story isn’t particularly dirty but was undoubtedly dangerous and highlights how much she loved getting off.
We were in the car one day and she was driving. I was sat alongside her in the passenger seat. I can’t remember what we were arguing about (this was nearly ten years ago now) but one thing I can remember is her shouting at me loudly.
I sat and looked out the window as her angry words washed over me. I looked down at my hands. My fists were clenched and I noticed were shaking silently in anger. Eventually it became too much for me.
“Will you just shut the fuck up?” I shouted.
She went silent, momentarily stunned at my outburst before she continued her diatribe.
“Don’t you fucking talk to me like that,” she shouted back.
“I’ll talk to you however I want you little bitch.”
Again she went silent. It was rare that I talked back to her. Most of the time I just couldn’t be bothered. She turned her eyes back to the road as the traffic light turned green.
“What is wrong with you?” she asked.
“What’s wrong with me?” I replied incredulous. “You’re what’s fucking wrong with me.”
“If you’re so unhappy why don’t you do something about?”
She would often do this. Dare me to break things off with her in impossible situations. Like I was just going to break up with her while we were driving along in the middle of a main road.
“I will fucking do something about it.”
“Go on then,” she taunted.
To this day I don’t know why I did it. She was driving along at 50mph with cars either side of us.
I leant across and ran my hand across her crotch.
“What the fuck are you doing? Get off me,” she responded.
“You love it you bitch. I can already tell you’re wet as fuck down there.”
I got no response and moved my right hand back across to her. I undid the top button of her jeans to make it easier to slide my hand down the front and ran my hands across the front of her thong. As I suspected she was already warm and moist.
She moaned quietly.
“Don’t make a fucking sound,” I said as I moved my hand inside her underwear and started playing with her clit.
She was really groaning now. She loved it when I played with her clit. I rubbed faster now as I could feel the juices leaking out of her pussy. Her head rocked back against her seat and she closed her eyes and let out a long groan.
“Keep your eyes on the fucking road,” I admonished.
“I’m going to come,” she said.
“Come for me you little slut.”
She obliged, bucking against the chair as she barely managed to keep her hands on the wheel and her foot on the accelerator. I could feel her wetness seeping all over my hand and the car smelt of her juices.
Her breathing was heavy and I stopped momentarily to give her a chance to get her breath back.
Then I started to tease her again.
“Please don’t…” she said quietly.
“Quiet,” I demanded. I was more aggressive this time. She could have multiple orgasms relatively easily and I knew I had her in the palm of my hand here. Literally.
She liked it when I was rough and she was crying out loudly now. How she was still managing to drive I had literally no idea. I felt her squirt in her knickers as she came for the second time. My hand was soaking.
As she pulled up at some traffic lights I noticed her jeans were now visibly soaking wet. I was rock hard and desperate to fuck her but still hadn’t forgiven her for her earlier outburst.
“Look how wet your jeans are you miserable little slut,” I taunted her.
“I’m sorry,” she whispered.
“You don’t get to be sorry,” I responded. “Your punishment isn’t over yet.”
And I went back to work. This time I went slower. I knew she was exhausted and I was now conscious that she could probably crash the car if she lost control. I worked my fingers around her pussy more slowly now, exploring every inch of her. My other hand started playing with my cock through my jeans.
She noticed this and moved her left hand off the gear stick and toward my cock.
“You don’t get to touch this, not yet,” I said.
She was groaning again, but this time more softly as I teased more gently and when she came for the third time in less than half an hour, I removed my hands from her now sopping jeans. She was so wet that the moisture had travelled all the way down her jeans to her knees. They were literally soacked through.
“Drive somewhere quiet,” I demanded.
She was quiet now. The last half an hour had left her unable to speak and she had certainly forgotten about the argument that had started all this off.
Eventually we pulled on to a quiet country road and I instructed her to pull over. My own boxers were now sticky with pre cum and I groaned with relief as I undid my belt and buttons on my jeans and released my hard dick.
She moved her hand down to it and started stroking me gently.
“No hands,” I instructed. “Just your mouth.”
She did as she was told and her tongue flickered gently across the head of my penis. I could feel the pre-cum practically leaking out of me now as she took my head in her mouth and sucked gently.
“You taste so good baby,” she said, before swallowing me to the back of her throat. She ignored my no hands rule and used her right hand to gently caress my balls. I decided to let this little indiscretion go.
Her head bobbed up and down on me more quickly now. The occasional car went by but nothing to worry me. She was moaning now as her head bounced up and down on me and it wasn’t long before I could feel my orgasm building.
Normally I would have given her some warning but she was being punished so I didn’t breathe a word. My breathing became heavier as wave after wave of pleasure coursed through my body. I felt the come shoot out of my penis and into her mouth. She hadn’t known it was coming but she carried on sucking greedily as I shot rope after rope of my hot sticky juice into the back of her throat.
She slowed down as my orgasm subsided, getting every last drop out of me.
She kissed me, her tongue darting into my mouth and giving me a taste of myself.
“Let’s go back to mine,” she said. “We need to fuck,”

[M]y kinky [F]un with a girl from Plenty of Fish

So this happened a couple of years ago and stuck in my mind as one of my hotter experiences with a cheeky girl from Plenty of Fish. A bit of backstory/buildup so if you want to get straight to the fucking, skip to the **sex** now. It’s a long story but with plenty of detail.

**If you like what you read…let me know.** I’ll share more experiences if this is popular.

I was 25, single and like most guys on POF, looking for an easy way to get a girl into bed. Preferably my bed. I think I did half decent job by being different to 99% of the other guys on there (i.e. by acting like a normal human being and not a total cringy twat) I’d had some success and gotten laid a few times.

This time around I’d gotten chatting to a cute looking Northern girl who was regularly down my end of the UK visiting family. I’m from the home counties (if you’re not from the UK, these are the areas surrounding London where all the middle class folk live) so I played the posh boy angle as much as possible with this girl, as she seemed to be lapping it up. For the sake of this story I’ll call her Rosie.

[FM] Angry sex is the best! [rough][anal] Part 2 of 2 Long

[Part 1 is found here](https://redd.it/5qzaz1)

There I am, bent over the edge of my bed, about to get probed rectally by Nik’s alien rod. Describing this exact moment is the sole reason I brought this account out of retirement. This agonizing moment of being more turned on by the thought of my man having his way with me and being terrified that it’s going to hurt and he will forever ruin this fantastic moment that had been building. I stared blankly at my wall while seconds ticked by as if hour hands on a clock.

Nik’s hands firmly rested on the top of my ass and I could feel his cock brushing up against my cheeks. I bit my lower lip as I could feel him spread my ample rear apart as my brown eye was fully exposed. He rested his tip at my exit and applied pressure. That instant full sensation sent waves around my lower half when my ring gave way. I muffled a yelp as the pain overtook everything else going on. I clenched up for just as moment as I exhaled through this temporary feeling. I had done this enough times to know what to expect but that first push was always the hardest. I exaggerated my breathing to get used to his girth.

First time cumming in my GF [MF] [21/20] [Anal] [Long]

Juliet and I have been dating for almost six months now, and the sex we have is definitely the best of my life. I’ve thought of submitting some of our sexual stories in the past, maybe if this gets enough attention I’ll write a few more. She is 20, about 5’6, 125 pounds, and wears a 32D. She takes excellent care of herself, and we go to the gym 3 or 4 times a week (her ab workout alone is more than most can handle). She has curly blonde hair that’s just past her shoulders, and bright blue eyes. I am 21, 6’3, and 195 pounds with wavy auburn hair and hazel eyes. We started out as roommates in the same university apartment with two other male roommates, and we began dating almost immediately.

I have had anal sex in the past with a couple previous partners, but it was something Juliet has been reluctant to attempt for reasons I consider perfectly reasonable. I’ve made it clear that it’s not something I need by any means, just something I like fantasizing about sometimes, and something I would happily do again. She once tried with a previous partner but says he never even got inside, and the furthest anything has been in her ass have been my fingers on occasion while we’re having sex.

[FM] Angry sex is the best! [rough][anal] Part 1 of 2 Long

Bit of a backstory. I’m 32, on the curvier side, currently shoulder length auburn hair with blond highlights and proud of my accomplishments in life. I normally would have posted this on my /r/EroticLiterature handle but because the subject of this gonewild adventure is one previously talked about in a story, I thought I’d reuse this throwaway.

My casual fling (Nik) and I had been going well for a while and for some unknown reason, he became distant with me at the start of last year. Not gonna lie, I was hurt, angry and ticked off at him for the snub. I rebounded in the best way I knew how, by dated a few other guys. I even had a good time with a few of them but none were my type. I really liked Nik so the lack of answers and communication ran deep.

Eventually Nik finally got over his moody tantrum that actually didn’t have anything to do with me at all. When began talking to me again, I told him that I dated a few guys during his absence. Knowing full well what that implied, he got pissed at me for being with someone else even though he was the one that left things hanging with the communication blackout. I couldn’t handle Nik’s constant drama so I left. For 5 months I had a cursed dry spell (story of my life) and for a kinky gal like me, it’s not healthy.

[M]assaging a [F]riend Leads to More

This is my first story here and I’m pretty bad at writing so I hope that doesn’t detract from the story.

BACKSTORY:
Over the course of the past few years after meeting my friend Angelica we slowly built up a casual relationship that’s had some bad spots but then some amazing spots as well. This is about the first couple times we did more than just hang out.
I first met Angelica at my friends house who was having a gaming night back in early 2014. Ill be honest I was immediately awestruck. Angelica is simply put beautiful. She is a petite Latina around 5 foot and was 20 or 21 years old at the time, me being 19 or 20 I don’t recall. At the time she would change her hair color regularly which I find extremely hot. She had multiple piercings as well not as many now but still sexy. All her piercings at the time are as follows, septum, tongue, snake bites, ears, belly button and clit piercings. She also had a couple tattoos at the time, now she has more. I cant recall what ones she had then. All of this combined makes easily her one of the sexiest women I know.

[MM] Craigslist hookup with older anal virgin.

The other day I meet him at a Walgreens parking lot so I can follow him to his dad’s house. His dad is still awake so we’re all watching Jimmy Kimmel and it’s 11 p.m. his dad goes to bed and he starts to rub my crotch and I get erect immediately I pull down my pants and my hard dick is in his mouth giving me fantastic head. We go into the bedroom and we get naked and he gets onto the bed doggystyle I put lube on my fingers and start fingering his tight virgin ass he’s moaning, I’m really horny so I lube up my dick and try to insert myself but he is too damn tight so I tell him to lay on his side I get into the bed too and I slide into him the third try he moans in pleasure I fuck him for a few minutes and tell him to lay on his back and lift his legs up he does and I enter his right ass again and pound him as hard as I could and I cum inside him in a couple of minutes.

[MF] s[ex]y time with an old fling [kink][anal]

Still reeling from what just happened last night. I’m not all that GoneWild as of late but this one goes down as one of my favorites for sure.

Ok, so a bit of a backstory. My ex [Page] and I were together for over a year and a half. The sex was fairly good and frequent which we both enjoyed. She had a fairly kinky mindset which rivaled mine so when we weren’t fucking like rabbits like most nights, we collected and used bondage stuff often in our sessions. She sports a Betty Page look with jet black hair down to her mid back but she’s more on the curvy side than thin. Perfect!

Sadly, we broke up over some major life choices that had us both going in different direction. Financially I’m good, while she spends money faster than she can make. I have to be near my elderly retired parents to take care of them now and then. Page however, wants us to move 2 hours away near her family and teenage kids (long story with her rich ex). The separation was mutual but bitter for the first few months. Eventually its water under the bridge