Tag: Anal

Low SMV old lady tries to get lucky on craigslist: The first buddy – part two.

The First Fuck Buddy: part one https://www.reddit.com/r/gonewildstories/comments/40r7fj/low_smv_old_lady_tries_to_get_lucky_on_craigslist/

The Second Fuck Buddy https://www.reddit.com/r/gonewildstories/comments/40rbku/low_smv_old_lady_tries_to_get_lucky_on_craigslist/

Two weeks after dumping me and literally the day after I had gone off and fucked and got dumped by another guy, my first craigslist fuck buddy calls me. I'm pleased. We meet up and fuck. He does his disappearing act. By now, I know that's just the way it's gonna be with him. I wait for him to summon me.

Two weeks later, he does. We get into some nasty texting. he tells me he has a party to go to but then he'll do me. I wait all night for him to call me but he never does. A week later, the same thing happens. A week after that, it happens again. This guy keeps spinning me up and then standing me up.

I start to feel like, this fucker must be married or something. I tell him I think he must be married. He says, "LOL! You're the biggest idiot! Come fuck me!" I say, well okay. He stands me up. This went on for about a month and I finally say, to hell with this. I email him and tell him he needs to go find someone he's actually attracted to. He tries to talk me out of it. I ignore him. He stops trying to contact me for a little while. Read more »

Coming home from a business trip

Little bit about us first. I am M25 5’8 average build she is 24 a sexy 5’9 slender 34 D and a nice ass (ex Playboy model). Been together for nearly 7 years and living at her parents house due to a recent move back home

I was out of town on a business trip and was very much missing her, I decided to stop by our favorite sex store to pick up a few goodies for tonight, butt plug, lube and some pleasure tape. Now anal is something we never do unless she is really drunk and its something I have been trying to ease her into. Always trying to get a finger near her cute butt hole.

The whole drive home (3 hrs) I was thinking about what I would do to her. I already had this whole Dom/Sub situation playing in my head. At one point I was asking her to send me some nudes but she refused. I got home and decided we should go have a dinner and movie date. I showed her the goodies I got and tried to talk her into wearing the butt plug all night but she was worried about wearing it all night since we are knew to anal and promised to wear it tonight once we got home. Read more »

[F] Dildo training advice

So I started dating this guy recently that has a really big dick that is way too big for my pussy. So he actually bought me a really big dildo so I could practice and loosen myself up with it so it wouldn't hurt so much when we have sex but today I tried getting the dildo inside me and I could barely get in a couple inches in before it started to hurt too bad and I stopped. In a weird way I like the challenge of being able to take his cock inside me without a problem but I realized how much practice I need and I'm afraid of the pain :( I guess I just was hoping to get some advice or encouragement on how to stretch myself out for him in the least painful way possible. He also knows I've done anal with other guys and wants me to do it with him but I don't think there's any way I could prepare my ass for what would happen if he put his dick inside me :/

The (F)irst of Many Do(m)/Sub Nights

We were on the way home from a night of hookah and mint tea, a favorite Friday night activity. I’m a blonde 20-something, slender build, just-a-handful breasts and shapely hips—think Kristen Bell with a more unique nose. He is around 6 feet, tan and dark hair with an equally aggravating and cute smile. Oh right, and a very pretty 7” dick. Relaxed and buzzed from the hookah, the conversation turned to his upcoming dinner plans with an old friend. “You know, I think she could seriously be a candidate,” he said, referencing our current search for a threesome partner. My ears pricked, and I got this feeling—“Wait a second, how are you so sure? Did you hook up with her in school?” He grinned, knowing how much I salivate over hearing about his past sexcapades. He is far more experienced—and I get smug (and turned on) from knowing that he’s been with all these different women, but has stuck with me for the longest. After a few minutes of cajoling, he admitted that she was actually pretty wild: over-the-top vocal and a bit domineering. ‘Oh shit,’ I thought, ‘that might actually work for us.’ Describing what we would each do to her (and vice versa), not surprising that we were both super turned on by the end of the car ride. Read more »

[23m] [23f] The night I realised how amazing it is to be filled up.

First time posting here. (A little long)

This is a night me and my fiancé talk about quite regularly, I also think about it quite often as well. I've never had a guy cum in me before and have always wanted to know what the feeling is like ( we tend to play it safe).

On this particular evening him and myself felt sexually frustrated, work and life in general getting in the way of some action.

It was late, we were high and decided a shower and then bed was a good idea. We began getting undressed and from there we begun the usual shower routine.

After almost being done, I asked my fiancé if he could wash my back and give me a massage. He obliged. That's where things started to heat up.

He started rubbing my lower back just above my ass, slowly moving his hands lower and lower until he was cupping my ass. He ran his hands up the side of my body until he reached my chest, from there he begun playing with my tits and nipples. He knows this gets me in the mood. Read more »

That time I tried anal (m/f)

Hi everyone! I'm back after a few months of being a total whore. A LOT has happened since my last post, so I thought I would pop back in now and then and share some of the happenings. (:

I'd been sleeping with this guy I met on RAOM (Random Acts of Muff Dive). He posted an ad, I responded, and within a few days of talking he was in my bed and between my legs. The voracity in which he ate my pussy was unparalleled by anyone I'd met before. We began fucking a few nights after that, and it has been some of the most fulfilling sexual experiences I've had. We are strictly platonic, and we are very well aware of each other's situations and there is a true level of mutual trust and respect there.

After playing around for a few weeks, he told me he was going to be out of town for an extended business trip. I thought this was a great opportunity to ask for what I've been wanting: anal. He had fingered my ass before, and had rimmed me, too. But neither of us ever really pushed the issue. I texted him and said "so maybe you could fuck me up the ass before you leave? It might be a nice send off, you cumming up my ass and then heading out ;)" he responded with a resounding "fuck yes" and we began talking about how he would go about shoving his cock up my ass. Read more »

Fucking the cute nerdy christian girl PART 2

Hey everyone, since you guys liked my earlier post I decided to post some more nasty sex stories for you. If you havent read the first post. Its right here Its not necessary but it might help with the immersion! This is prolly gonna be long too so buckle in haha

Alright so basically after I fucked Allie that morning we ended up seeing each other a lot. I kinda started to like her but she was still with her boyfriend, she felt reaaaally guilty about having sex and acting so slutty around me while being with him. I was fine with it. Eventually I sat her down and said that if she wasn't happy with him she would be better off with me! Sounds good right? Wrong…Allie basically told me that she was not looking for anything serious at all. After her first shit bf and all she wasn't gonna jump for another. Shit man I actually was growing to like her. She told me that she liked having sex with me and doesnt want that to change. Uhh okay, this made me feel a little confused at first but I found it really hot immediately after. My personal fuck buddy. A girl who had no idea what sex would be a week ago and now wants my cock all the time. Sexy as fuck. Read more »

Anal [f]un with [m]y girlfriend

First time poster, long time lurker. Apologies in advance for typos as I'm typing on my phone at work. Apologies if this is long.

Anyway, a little background. I've been with my gf for almost 4 years now and we have a great sex life. She's about 5'2" with a gymnast build, has amazing D cups and an ass you could stare at for days. I'm a 5'9" with a muscular build, 6.5 inches cut with good girth. We have done anal a few times before and she loves to be fingered while I go down on her but this is the kinkiest anal experience we've had to date.

We've been going through a bit of a dry spell lately. We went from having sex 4-5 times a week to maybe 1 time every 2 weeks. Until one night last week.

It was a normal Thursday night and we had just finished cleaning the kitchen after dinner. I had been lurking on Reddit all week and was pretty horny from not indulging myself. She had worked out right before dinner so she stepped into the shower after we were done with the dishes. I'm sitting on the couch which looks right toward the bathroom mirror in our small downtown apartment. Read more »

Taking /u/highavailability’s anal virginity. Lots of pictures. [f/m] xposted from /r/hastories

It’s no secret that I’m kindof obsessed with HA’s ass. It truly is a thing of beauty. I’ve never been particularly interested in exploring the male-gspot with anybody else, but HA’s ass is just begging to be played with. I initially approached that line awhile back when we were both pretty heavily under the influence. There was only light external massage on that occasion (mostly bc I have long fingernails), but I couldn’t stop thinking about it thereafter. HA was, understandably, apprehensive about the possibility, but somewhere along the way his curiosity got the best of him and he gave me carte blanche to do whatever I wanted…with the stipulation that anything I did to him, he could also do to me. Well, seeing as how he has fucked me in the ass on multiple occasions, this fine print didn’t dissuade me in the least.

At the time, I didn’t think I’d be seeing HA until mid-January, so I leisurely started reading up on prostate massage, watching tutorial videos, and consulting with my gay bestie. I ordered some things online and continued with my “education” because I approach sex like I do everything else….all or nothing, and if I’m going to do it, I’m going to do it right. Read more »