Tag: Anal

So I just bought (m)y first dildo…

And it feels huge! But amazing. The following story is basically how I truly came to understand what virgins feel when being penetrated for the first time.

As a straight guy, I've been interested in anal play for a long time and have progressed through (what I consider) the basic phases of exploration. i.e. fingers, small objects, larger objects. I even made a wooden dildo out of a dowel that I would cover with a condom and use if I knew I'd be home alone for long enough. That is, until last week. The online store that I had bought a cock ring from for my girlfriend and I to play with sent me an email with blowout sale deals.

Being a curious (and slightly horny) cat, I clicked the link and began scrolling down the page littered with cheap sex outfits and flavored lubes no one wanted to buy. Then, a dildo crests the bottom of my browser with a price tag that piqued my interest. Adam's PleasureSkin Natural Dildo. $15? hmm.. I could buy that and some lube for less than $30 including shipping! I was sold. A week later, it shows up in the mail and I break it open as quickly as I can. Read more »

Modeled for a massage demo. Reposting. 20F [M/F], Anal.

Since there seems to be a bit of an outcry over assholes calling stories fake, I figured I'll try to post my story one more time. Hopefully this time it won't get pulled because of stupid idiots.

I have written before about how my friend Todd, a masseur, used me as a model for a massage demonstration for couples. Todd knows I have a bit of an exhibionist streak and used that opportunity to expose me in front of everyone. I wrote about it here: http://www.reddit.com/r/gonewildstories/comments/2l4uj8/massage_demonstration/

Since then, Todd has kept bugging me that we do another demo. A few weeks I finally relented and told Todd to set it up. It took him less than a week to call me back and tell me he managed to get a bunch of couples who wanted to come see a demonstration of proper massage techniques for couples. They were even willing to pay and I would get a cut. Read more »

How we became swingers [MFM].

My wife Liz has always been a bit wild. She has periods of mild manic episodes that always urge her to do something risque. First it was nipple piercings. Next it was risky sex in public places. Then it was the clit piercing, and after that it was open sex in an adult theater with strangers watching us. On this occasion it became much much more. Read more »

Threesome in Paris with a French couple.

This is rather long and I have to break it up a bit. This is the first part and if anyone is interested, let me know and I'll add more.

This happened last Thursday, and I’m still having trouble believing it. My motto in life is that I’m willing to try anything at least three times before saying I don’t like it and swearing off to it. Back in freshman year, my best friend and I had a threesome with one of our guy friends, which is a story on its own. I didn’t fully enjoy it so I’ve been hesitant to try again. Anyways, it’s been on my mind lately, and not knowing anyone in this town (studying abroad), I decided to hit up craigslist. I replied to three ads, and only one of them messaged me back. Her name was Lola and she was this hot blonde from Greece and her boyfriend, Guy, was French. Lola spoke Greek, English, and French. Guy only spoke French but understood some English. After sending a few emails back and forth, we decided to meet up. She told me that this was gonna be a surprise for Guy and he didn’t know what was going to happen yet, only that I was a friend coming over for drinks. They had talked about threesomes, but had not met someone yet. Read more »

Update: My (f)irst wild fuck with a coworker..with pictures [M/F]

This is a follow up to my first wild encounter with my coworker that I posted last weekend:

http://www.reddit.com/r/gonewildstories/comments/3378b3/my_first_wild_fuck_with_a_coworkerwith_pictures_mf/

After that encounter, we sexted, texted and fooled around a few times. We did not do it again until I met him on the last Friday of March for happy hours. He broke me the news that he was leaving. He went on a vacation in February to meet his daughter who stays with his wife. Apparently he wanted to be more closer to her. So, he took a job in the nearby city so that he can meet his daughter more often. I told him that he made the right decision.

Then he asked me if I want to do it again. I said yes. He told that he wanted to do anal and like he said during our first fuck, he would regret if he didn't do that. I told him that I have never done it and I am not sure if it is right or wrong. Actually, I never had to even think about it before as none of my previous boyfriends wanted it. He said that it might be something I should thin as my next boyfriend might ask for it. He suggested that it might be a good idea to try with him and come to an opinion. I suggested jokingly that we should do it in the trial room. We both laughed and had drinks and chatted with our colleague. Read more »

Stealthy anal with my girlfriend at her sister’s place [m/f]

I had only known Norah for a couple of weeks and our relationship was brand new. Which is to say we had fucked for the first time the night before. And after we managed to get over the first initial awkward sex session, we were both really eager to do it again.

The night after our first fuck, her older sister was throwing a party at her place. We were twenty-one, she was twenty-three, so not much older. Likewise, her friends were all about our age. She had a ton of friends so the place was packed.

We were drinking and dancing and just generally having a good time. We kissed and made out lots. It was late summer and the weather was beginning to get cooler but Norah was still wearing short summer dresses. My hands kept going up her thighs to her ass whenever we were making out.

Her sister shared an apartment with a roommate. The place was big but it still felt cramped and finding some privacy was difficult. The bedrooms were officially off limit but we got so horny we didn't care. We slipped in Norah's sister's room when she wasn't looking. Read more »

I [f]ound a fun use for my new toy.

I just typed this up for one of my friends, and thought you guys might also enjoy it.

A bit of back-story: I'm a super high libido woman who hasn't had sex for ages. I was getting crazy tight, so for the past few months have been purchasing and playing with a lot of sex toys. It's been… a fun ride.

Okay, so here we go.

I was really horny and struggling to focus, so got in the shower and put my new suction-cap dildo on the wall. I reversed onto it and started trying to figure out what worked. It's quite a small dildo, about 4.5" insertable, and I think 1.25" in diameter? Not sure, I think that's 4" around or less. So yes, much narrower and shorter than the average guy.

Anyway, I discovered fairly quickly that it probably wasn't going to do it for me – it wasn't long enough for me to use on the wall properly, I couldn't get the angle/depth right. Not that I didn't play for a long time, grinding myself back onto it, pushing myself up and down. It felt pretty good, but even playing with my clit, I wasn't going to get there. Read more »

A recent online dating Experience [M][F] first ever story, reposting because I forgot gender tags… These take a while to write, who knew?!

I commented in a thread about sexual achievements and thought this sub might like my story:

So recently I started using online dating…

Me: 6-2, 215 pounds, very fit, big arms, big chest, good abs. Think a slightly fluffy steve reeves but without the large thighs…

I started seeing this one girl, cute, smart but not terribly experienced though very willing to try new things. Our ages are both between 25-35, she is about 5-8, slight runner build, asian with a small pert chest. Our first night together we had anal sex for her first time, went very well too. This isn't about the first time…

About a week after we had started having sex I started asking her to send me nudes. Nothing gets my creative juices flowing like a nice booty shot. She sent me a few the day before so when she was due to come over, I was ready for action. I knew what I wanted to do. Read more »

My [29F] (f)irst wild fuck with a coworker [37M]

This happened last month. It was the first time I fucked some one without dating. It was also my wildest fuck.

I am 29 and I work in the marketing department of an IT company in the mid west. I broke up last December and I am in my current job for three years. Last June a guy joined the company as Test Lead. He is a single dad, divorced and has a daughter. Our company organizes lot of happy hours and we get to meet every one there. My colleague who is a technical writer introduced me to this guy. They were both working on the same module. The guy was testing the module and my colleague writes training manuals and helps marketing write descriptions. Read more »