Anal Archives — Page 32 of 957 — NSFW story

Tale of Two Friends: Part 5 [ff] [college] [work] [ffm] [anal] [creampie]

Sarah and I (Olivia) showed up to our first day of work training excited. We looked into it and discovered that the owner of the concession stand, Mr. Wickson, rarely worked anymore but that instead his two sons Josh and Tim worked as the managers. We’d been in the same grade as Tim and while we didn’t really know him Sarah had had a class with him so was at least friendly with him.

So we showed up to training on a Monday, when the stand is usually closed, and were greeted by both Tim and Josh. Tim had changed from a skinny and average teen to look quiet a bit like his older brother. As the day came to a close they said we could come in for opening day of the season on Wednesday as scheduled or if we were available we could come in for a half day the next day, Tuesday, and Tim would run a mock opening for us; Sarah and I agreed. Read more »

I simply love pegging [26F] [OC]

I remember I first saw the term “femdom” or “pegging” while randomly watching porn, and I was intrigued by the idea of flipping the script and being the one in charge.

One night, after we had been dating for a few months, I finally worked up the courage to talk to him about pegging. To my surprise, he was open to the idea and excited to try it out. We’ve decided to take things slow and start with some gentle anal play to make sure they were both comfortable.

Over the next few weeks, we explored different toys and positions, gradually working our way up to using a strap-on. At first, I felt a bit awkward and unsure of myself, but he was patient and supportive, giving me lots of positive feedback and encouragement. As we became more experienced, I began to love the feeling of power and control that came with pegging.

I enjoyed being the one to set the pace and decide what they would do next. He, meanwhile, was thrilled to be able to explore his submissive side with someone he trusted. Eventually, we got to a point where we were having regular pegging sessions, sometimes multiple times a week. Read more »

[F] I wingwoman’d for my colleague [M] and hooked him up with a friend [F] after his drought. He did anal for the first time and now jokes that he owes me forever

My poor friend. I work with him and he went through a rough breakup. Anyway, after a few months, I told him he has to get back out there. I could see his confidence had seen better days. I had to do something productive.

In steps my friend, Erin. She met after work one day and said he was rather handsome. He had zero idea. So, I made she sure DM’d him, and before I knew it, they’re talking loads.

I joked I would stay out of it but secretly hoped they’d have fun. They both seemed a little shy and maybe it’d cancel things out.

After two weeks of talking, one day, he says he and Erin spent the night together. I felt like such a good wingwoman. I didn’t ask specific details, until he randomly came out with, “I did anal for the first time.”

I nearly spat my drink out. Erin was NOT the friend who I’d imagine doing anal. It came out of nowhere. We’ve spoken everything sexual and I knew she’d never had a dick between her cheeks.

The brief silence and random facial expressions from me resulted in a, “I owe you until the end of time.” Read more »

Choking on Incubus Cock for Valentine’s Day [MFM] [Reverse Harem Vibes] [Reader-Insert] [Female POV] [Flash Fiction] [Dirty Talk] [“Good girl”] [Choose Your Own Ending] [Anal] [Creampie]

You lean over in front of the mirror, admiring at the way your skimpy, red thong bikini bottom highlights your ass cheeks. It’s your first time wearing something so daring in public, and you can’t wait for everyone at the hot tub party to see your big ass on full display.

Satisfied that you look hot as hell, you pull on a thin, white T-shirt and cut-off denim shorts that show off the bottoms of your cheeks.

You don’t know the party hosts very well, but you know it’s going to be a *hot* hot tub party, that’s for sure.

But to your surprise, when you arrive at the party house, there’s only one other car there.

Who invited you, again? It’s oddly fuzzy, now that you try to remember.

But the front door is already opening, and a shockingly handsome man stands in the frame, complete with toned arms and chiseled abs.

He leers at you as you walk inside, and a slow, evil smirk spreads across his face as he shuts the door behind you.

“You picked a good one,” he says to a second man, leaning in the shadows. Read more »

[F] My pegging experience

I Have Peggedd 7 guys now and it’s the best thing ever I can’t explain how much I love watching a guy bend over and lemme take him from behind the words are just unexplainable

And I am good. I mean really good. All of them give some silly ultimatum like “oh ok but if you get to peg me then I get to do anal too!” Guess what, nobody has ever wanted to do the anal afterwards. They just get the best orgasm of their life and can barely walk and then they can’t think about anything else and they come right back for more. I’m happy to give it to them too, any time and any place.

I’d say I have 3 regulars who ask for it about once a week. I do extra special stuff for those boys because they at least admit they love it. Then there’s 1 that will never ask for it but asks to hang out and then spends the whole time talking about what we did last time until I go get the strap then he becomes a nice obedient little boy and bends over for me. Then of course there’s the other 2. Reluctant to admit how amazing I am but they’ve both had it more than twice now and every time they say “ok cool I’m only doing it cause you’re hot though, I wouldn’t normally do this” but weirdly they just keep coming back. Silly guys. Read more »

First Public sex & first public anal at the same time at a Spa [MF]

So me F(22) and my BF(M27) live a horrible 8h train ride apart..
since I’m starting a new job soon I won’t be able to do the trip down to see him that often anymore, so I decided to visit him for a complete week rather then the normal weekend stay.

He always drives about 1h to get me from the train station so I don’t have to wait for the next train to his town there all alone at night.. but this time he supprised me with tickets to an indoor paradise pool SPA.

For people who don’t know what I mean: it’s basically an indoor vacation spot. Hottub, salt baths, sauna and a full on palm tree surrounded pool with a bar inside of it where you could get drinks all while swimming around.

Normally we would come here with some friends and have a few drinks, but this time we were alone and wanted to have some quality time.
After enjoying the salt baths and the occasional grabs we went to the outside pool area to chill in one of the hottubs. Read more »

Professional Backdoor Man (M30/F31)[anal, size]

I have a great job. I (M30) fuck women up the ass. You schedule an appointment on my app and I arrive at your home or hotel room—any private space where you’re comfortable—with a goodie bag. The best part for you is that I have a foot-long cock and I know how to use it!

I’d be very gentle with you (F37) at first, caressing and kissing you, letting you decide how much foreplay and what kind. Maybe, to delay taking my cock in your rear, you would want to give me head—you could do that for a few minutes but it couldn’t go on forever. I’d gently but firmly move you toward anal play, eventually rimming you while I massage your pretty pussy lips.

Eventually, you would be on your hands and knees, back arched in anticipation, excitement, and nervousness. With a few fingers, a dildo, and lots of KY (both from the goodie bag), I’d have you lubricated, stretched and relaxed before you know it. Read more »

Lost my anal VIRGINITY by a guy over twice my age in my parents hot tub! [F]

I just had the wildest experience while my parents were gone! I met a cute older guy on tinder and he asked if i ever did anal before. I never really thought about doing it before and i just turned 18 so i was already craving an older guy inside of me. Anyways, when my parents left I invited him over. We decided to skinny dip in the hot tub. We started making out and i started sucking his dick. He fingered my tight asshole before sticking his hard big dick in me. I thought it would hurt but i guess the warm water made me feel really relaxed! I told him to go as hard as he wanted to and trust me he did lol. I let him cum inside me and that really turned me on. I could just feel my asshole gaping when he pulled out. Best experience ever so far!

[F] First Date Anal with Tinder Hookup

I met a guy from Tinder a few years ago. We were smoking and chilling and just having a good time. He offered to give me a massage, and of course I said yes. He was rubbing my back, shoulders and arms for a while. It felt amazing but it was making me so horny. He would get so close to my boobs and then pull away. I was crawling out of my skin from the tease. I finally begged him to please just touch my boobs and he kind of laughed and kept doing what he was doing.

Finally he touched my tits and my ass but was teasing my legs and not touching my pussy. I was literally trying to angle my body in a way that he would touch, but he didn’t. He was making me beg for it and he was getting so hard watching me squirm.

We were fooling around and I sucked his dick, when I asked him to fuck me, we both realized we didn’t have condoms. He came in my mouth instead. By this point it was almost 3 AM and I ended up sleeping over. In the morning I was pushing my ass on his dick. We ended up being so horny that he fucked my ass without a condom. Read more »

[MFF 20’s] Threesome at the outdoor pool in the moonlight (Part 3/4) [Bi] [Outdoor] [Anal] [Fingering] [Cunnilingus]

*Part 3/4 of a long, fictional story*
[Part 1](https://reddit.com/r/eroticliterature/comments/110gnx0/mff_20s_threesome_at_the_outdoor_pool_in_the/)
[Part 2](https://reddit.com/r/eroticliterature/comments/110gzeb/mff_20s_threesome_at_the_outdoor_pool_in_the/)

“So, do you like how your idea of sneaking into the pool is turning out so far?” Cathy asked me smilingly after we had settled down a bit. “I didn’t expect you to make it that crazy but I’m not going to complain” I responded. “Where does your fascination for bisexual women come from?” Megan wanted to know. “Wait, what are you talking about? I never said anything like that.” I replied. “Oh yeah, you never told us, how could we possibly know?” Megan seemed to make fun of me now. “As soon as we were talking about that topic earlier today, the cool and tough man you pretended to be transformed into a teenager that had just reached legal age” she laughed. I was glad about the darkness covering my face which was turning red. Those girls knew exactly what they were doing, I thought to myself. In fact, they were basically toying with me. I felt a little embarrassed but at the same time something about that thought seemed to turn me on even more. “Megan, I’m pretty sure that just about legal teenager you were referring to could never have fucked you the way I just did” was my rather desperate attempt to restore my male honor. “You did a good job there, I’ll let you have that. But remember, it wasn’t you that made me cum, it was Cathy” she replied with a smile. “Well two versus one, that’s just not fair” was my weak excuse. “I would have easily lasted long enough to make you cum if it wasn’t for Cathy. Her orgasm just drove me insane.” “Well, that’s part of the challenge if you want to get involved with women like us” Cathy said. Despite clearly coming off worst I really enjoyed the teasing nature of this conversation as none of us was taking it all too seriously. But soon enough my female companions in this adventure became more and more active in caressing each other again. I realized that talking would not keep them satisfied for much longer. Read more »