This one may be longer than my last! I have started recounting some stories of my favorite hookups (you can see my first lesbian experience [here](https://www.reddit.com/r/gonewildstories/comments/btq4jy/my_first_lesbian_experience_ff/)). This one is the first time I did anal on a first date! I’m no stranger to anal. Its one of my favorite activities, and I find it mind-numbingly pleasurable. But there’s something intimate about anal to me. You have to be really comfortable with a person to be able to take on that level of potential nastiness on a first date!
Tag: Anal
I [F] went on vacation with a man I met online while my husband was out of town and he made me his slut
A little backstory of myself (f24)- I’ve been married to my husband for 5 years now and we have a 4 year old together. Before this weekend I’ve only ever been with 4 guys and the past 7 years I’ve only been with my husband. I was 20 when our daughter was born so I’ve been fortunate to regain my pre-pregnancy body. Now- I’m 5ft1, 105 lbs with petite tits and frame but a nice ass. Long brown hair, big brown eyes and a young looking baby face (I’m great at flashing puppy dog eyes one second, and fuck me eyes the next ;). I lost my virginity at 16 and was a bit of a wild child with the guy that took my virginity but once I started dating my husband I settled down a bit sexually, he is about average in size (just under 6 in.) but fucks like a rabbit when he’s in the mood.
From Friends to Friends with Benefits [mf][friends][fingering][blowjob][creampie]
I can’t believe what I’m hearing or seeing.
Amanda. The millennial. Mandy. She wants to fuck me? Right here and now?
Obviously I’ve often fantasized about having sex with her, or even just seeing her naked body. She’s 24 and skinny with small tits and a nice smile. What’s not to like or be curious about?
But now here we sit, alone at her place uptown and she’s actually interested in making it happen? To what do I owe this extreme good fortune?
A couple of hours earlier, I was sitting at the restaurant texting with her and our other friend Matt. I was on time, they were late. What else was new?
Amanda was in an Uber a few minutes away and Matt was MIA as usual.
“Prolly gonna no show on us,” I texted her. “He’s the worst!”
Secretly, I had hoped he wouldn’t show up and then it would just be me and her. Two’s company, three’s a crowd, after all.
I’d known Amanda for a few years from work and after she quit to go work somewhere else, we all kept in touch. Mostly it was bitching about our jobs and in the case of Matt and me, our wives.
Sharing the Love at the pool party, Part 3 [MF]
Hey all, thanks for [the good feedback and upvotes on my last piece.](https://www.reddit.com/r/eroticliterature/comments/btnhxk/sharing_the_love_at_the_pool_party_part_1_2_mf/) Here’s part 3 of the story. And if you’re wanting a full on-version, let me know, and I can edit this or re-post it all in one shot!
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The group walked through John’s massive house and went upstairs to his bedroom. It was a bit weird for Alfred seeing his girl walk through his best friend’s house like this, in a one-piece bikini of all things. Still, he was slightly turned on. While Kim looked like your typical innocent 22-year-old Asian girl, she had a sexual mind of her own. She always found a way to make the sex fun, and here she was doing it again.
They were now sitting in John’s room. Naked pictures of models were all up against the wall. John never matured, he always was a horndog, and he always told Alfred about how her got off watching Japanese porno movies. But tonight was different, he finally was going to fuck a girl.
“So, how should we get started?” Alfred asked Kim, curious to see if she will take the lead. “This threesome was your idea.” “I might be older than you at 26, but you’re the one with all the sexual experience.”
She had the best ass I had ever seen and I took her anal virginity. [MF] (WARNING: Drug use).
This happened around the end of 2017/ beginning of 2018. I have always been an ass man and I think other ass obsessed perverts will appreciate it.
I met this girl in inpatient drug rehabilitation. I was 30 and in there for alcoholism, she was 27 and in there for meth. After we left treatment we started dating but relapsed after a couple of months.
Her face was really cute. Unique but still very pretty. Cute angular upturned nose, somewhat prominent but still very feminine chin, almond hazel eyes.
She had a very cute smile with a little gap between her front teeth. Full lips. Shoulder length light brown hair parted down the middle. There was an innocence to her despite her extensive drug use. You would never guess she had been a meth user for 6 years.
She was classy cute and always dressed well. She described herself as a spoiled rich kid. She started out doing rave drugs but meth grabbed ahold of her and consumed her. Despite being somewhat modest and averse to sex talk, she always wore leggings that hugged her perfect ass.
Her First Butt Plug (M/F, anal, butt plug, 1st time)
“I have something for you.” he said after dinner while finishing the last of the dishes.
“Oh yeah?” I raised an eyebrow.
“Give me one sec.” he replied as he dried off a glass.
“Take as long as you like. I’m enjoying the view.” I smiled staring at his ass. I was perched on a stool at our kitchen island as we finished up our Sunday routine. I cooked, we ate, he cleaned.
He smirked over his shoulder, wiped his hands on his jeans and kissed my forehead before walking out of the kitchen.
I wondered what he had come up with. The last surprise was a bunch of beautiful bras and underwear after I had mentioned needing to toss some old ones. I set my wine down when he returned. He sat next to me, handing over a small box, his eyes sparkling.
I pulled the lid off and opened the thick layer of red tissue paper to find a bottle of lube and a steel butt plug with a giant purple rhinestone on the end of it.
“What the fuck?” I took it out, examining it.
Uber Anal [FM]
Hi Y’all,
It’s been a very bad week for me. I won’t go into it but you can check out my posting history to understand what happened on Friday.
I decided last night, since the kids were all staying over at friends and my husband was up in Alaska for his Air Force Reserve duty, I’d do what I knew best and find a horny guy in my Uber to fuck me. I needed that thrill and the intense passion I get from the excitement of fucking a complete strange I just met.
I struck gold on my third ride as I was picking up a rider in Columbia City in Seattle after just dropping off a rider I’d taken from SeaTac. The guy was middle aged, slightly overweight but had a good blonde head of hair and very nice smile. He looked like the kind of guy who probably fucked plenty of girls in high school and college but was likely now married and not staying in top form. I thought he was very cute and fuckable!
Spreading her wings (and legs!)
continued from “What More Could a Man Want?”
One of the things I began to notice was that Chastity liked strangers more than she liked them after the second or third time she fucked them. During one of our infrequent conversations about her having sex with complete strangers she revealed the attraction for her – she liked to make strangers cum in her pussy. She felt some amount of control over the situation, and of them. However, she was still extremely shy so when we would go out with the intention of finding someone to fuck her I had to do all the talking, which didn’t take long. All I had to do is tell some guy that my wife thought he was cute. He would look at her, always wearing something short and sexy, coupled with a top that revealed those beautiful tits, and would say, “Well I think she is absolutely beautiful!” I would then proceed to tell him that she likes to make strangers cum in her pussy and that I liked to fuck her while she still had cum dripping out of her pussy from the last guy(s) she fucked. I would then ask, “Would you like to be that guy?” No one ever refused. It didn’t matter if they were single or married, they never passed up the chance to have sex with an incredibly beautiful woman.
Cougar gangbang [Group][F43]
Posting this on an alternate acct. I might share my main through pm if you really wanna know.
Roughly 8 years ago, I was having some fun on an adult hookup site. I was (and still am) in an open marriage and I’d met a few guys but I’m picky (and worth it) so I hadn’t found exactly what I was looking for. At the time, I did not consider myself a cougar.
Then, he arrived in my inbox. We’ll just call him D. D was 18, curly blonde hair, fit as fuck and hung like a horse. He was also uncut, which would quickly become my preference. I had some misgivings about his age at first but got over them pretty quickly.
D and I met and sparks flew. Our first meeting, he brought a friend who just wanted to watch so he watched me deep throat D’s huge cock like it was my fucking job. Our second meeting was just me and D and I got to feel that cock hit all the right spots. I like it hard and rough and D could give it to me just the way I wanted it.
Jennifer [Commission] [MF] [FDom] [Panty Fetish] [Kink] [Surprise partner] [Teasing] [Bondage] [Precum] [Anal]
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**Jennifer**
*An Erotic Story by Katherine Summers*
—
It always felt good.
But tonight, it felt especially sweet.
Daniel had made an effort this time. He had showered as soon as he got home from college and dimmed the lights in his room. Propping himself up on his bed, naked and feeling fresh, he threaded his feet through the leg-holes and slid them up his thighs. These were a pair of soft, cotton panties, red and black stripes with a thin line of black lace around the hem that tickled the sensitive skin of inner thighs as he pulled them up until they were holding his balls just so. He stretched out his legs, his face breaking out into a smile.
Closing his eyes, he let himself feel the softness of the fabric, the tightness pressing against his balls, riding up between his buttocks in a way that wasn’t at all unpleasant. He ran his fingertips over the bulge formed by his cock, enjoying the unique, ticklish sensation that only came from being touched over cotton panties. Inhaling deeply, he let out a sigh. The sun was just setting outside his windows and a little of the light spilled in through the chink in the curtains, casting a bar of gold cross his legs. He could hear his roommate and her friends chattering in the kitchen, preparing to watch a horror film. Their pleasant feminine voices soothed him. He imagined it was one of them, Jennifer, that was stroking his cock, long and slow, base to tip…