A [F] shoves a big dildo up [M]y bisexual ass

I really love anal sex and I’ve given it and received it. (I’m a bisexual male). One past anal sex partner of mine we’ll call “Rosie.” Rosie was a short, white woman who wore think, but stylish, glasses and had brown, straight hair. Her body was average sized but she had a really thick ass that I noticed when I first met her through a mutual friend. What I learned being with Rosie from the time we spent together was that she was a very openminded woman, sexually speaking. Rosie once told me she wanted to anally penetrate a man, and I willingly volunteered to be her victim while we were hooking up. Rosie was delighted and pulled out a large, black and red dildo and a bottle of lube.

I got up on Rosie’s bed, undressed and faced her nightstand and a mirror that was hanging behind it so I had a full view of my face and Rosie as she crouched down on her knees behind me, putting lube onto the dildo as well as rubbing some on my butthole, which took me by surprise. Rosie applied a generous amount of lube on me and the dildo and then said “Are you ready?” I took a deep breath and said “Yes,” and the next noise I heard was the dildo turning on, vibrating as Rosie held it in her hand. The dildo was black and was large. I remember thinking to myself “I hope my butthole can handle it.”

Uber Driving Slut, Old Guy Gangbang [Group]

Hi Y’all,

From time to time I meet a guy that while I didn’t suck or fuck them initially, I stay in touch and eventually have fun with them. That’s exactly what happened with a guy I met named Tom. He is probably in his late 50s or early 60s but in great shape and very handsome, in a refined way. He told me he use to be in the Navy and flew F-14s and he looks exactly like that kinda guy. I met him while Ubering and didn’t admit any of my slutty ways to him until we started to exchange emails and chat online. Since then he’d been trying to set me up for a old guy gangbang that last night I finally took advantage of.

I met the guys at the Anchor Pub in Everett. The guys were all very eager to meet me.

There was Tom, Bill, Danny, and Jim.

In some ways there wasn’t much difference between them. If you had asked me I would have said the look like four older dudes except Tom looked like the handsome leader.

Tom was about 5’10” had greying hair but looked as handsome as I remembered him.

On the counter [MF]

I live in Florida right by the water and there’s this beach shack that serves great burgers and other tasty fast food right on the beach.

Well, as a seventeen year old at the time and of course being in high school the thing to do on the weekends back then was go drink some cheap alcohol and hang out down by the beach.

One of those weekends I had quite a night down at that beach with a guy who really made me work for it.

Now, Im sure you’re wondering where the counter comes in, and to that I say, patience.
All good things come in time ;).

So this guy I mentioned is someone that I had always been interested in, but never had much of a hard core crush on. Just someone that slipped into a naughty day dream from time to time. Well in the year this story takes place I had found out from a friend that he had started working at the shack as a waiter.

(Sorta) Got Caught Being a Slut [MF]

I was desperate. Desperate to get fucked. I hadn’t seen my boyfriend in a couple weeks and I really wanted his cock. So, to substitute, I texted my fuckbuddy, let’s call him Kane, instead. He blew off work yesterday to fuck me.

When I got in his car, I was in a tank top and short shorts, no panties, per his request. Soon after we started driving to his place, his cock was out and I was leaning over to suck it. Feeling him get hard in my mouth was interesting, considering of the times I’ve sucked anyone off before they were already hard. He would slip his hand in my shorts or spank me while I did so to make me moan on his cock, which just made him harder. There were a few instances where I had to stop so we wouldn’t get caught, which would’ve been easy since it was about noon at the time. However, I stopped right before he came when we saw the sheriff’s car in the next lane. We took that as a sign to wait until we got back to his place.

[M][F] drunk anal sex

Me and this woman I know once had anal sex when we were both drunk. We had known each other since college, and are good friends to this day. But this night, she and I got really drunk and spontaneously hooked up at my apartment. One of my biggest sexual desires is anal sex, and I asked this woman if she’d ever done it before. She said “No, but there’s always a first time for everything.” I said that I agreed, and she said if I had lube then she’d let me, as she put it, “stick it up her pooper” (I laughed a little when she said this). I grabbed my lube and she pulled down her panties and bent over my bed, with her feet still on my floor, arms on my bed. I positioned myself behind her and inserted my dick up her virgin butthole. She took it like a champ. I was so proud of her, and now I know what the inside of one of my friend’s butt’s feels like..AMAZING!

[MF] Caught in a Duck Blind

This is the story of how Lisa “RosieGunner813” and I met. It happened a couple years ago but we both still bring it up and laugh about it.

Lisa and I matched on a dating site and we went through the set of motions one would while meeting someone online. We chatted for a while and moved to texting, talked about ourselves and interest. Things were going well but really took off when we started to talk about our past sexual experience and the kinks we were into.

We kept chatting and decided we had to meet. I throw out the idea of going for a hike, sure fire way to see if someone can keep up with me and is a good way to meet someone in public but also have some more private conversations. We meet up at the trail head and she’s even more stunning in person than her pics. We started to hike on the main path around a reservoir which was pretty packed with other people. We decided we wanted to increase the difficulty and head off the main gravel path which also happens to be more secluded. After walking around aimlessly for about ten minutes and not seeing anyone else on the trail and a ton of flirting back and forth, I lock eyes with her.

[Mf] the unknown virgin.

This is a story about a girl I was with a good long while ago. It was when I was a cook at a restaurant and as most hookups at that time go- she was a waitress.

I found this girl to be so hot. Tight nice body, round ass, perky tits. She was 22 and in college. She loved to party and drink and have fun. A very sweet and genuine girl which made her more attractive.

After a month and a half trying to charm her and half just being me with no apologies because I didn’t think I had a shot, she gave me one.

She invited me over her place while her parents and brother were out. They were supposed to be out most the evening. On my ride over I was so nervous because she was a hot college chick who partied and I was a weirdo with long hair and piercings who never went to college. I figured she was well versed in seriously getting fucked.

[M] [F] [M] My gf gave my dad a lap dance and more while I watched

Heads up, this is a long story, and I’m a bit of a writer so it’s set up like a story instead of idle convo. Hope everyone likes this, felt the need to talk about it.

This happened about 10 years ago. I was in my late 20s and she was 22. She was 5’7, shoulder length brown hair, 36b tits and sometimes shaved pussy or a landing strip.

My parents were splitting up at the time and my dad was turning 50. My gf had an idea to invite him over for a bday dinner and celebrate 50. I called him up and set it all up.

A few days before his bday, my gf said out of the blue, “I wanna give him a lap dance!” Now I knew she was openminded and willing to try things, hence why I fell in love with her. So I said “ok, like just a dance or you gonna show him a good time?”

Her eyes perked and she smiled, “oh I’m gonna give him a good time.”

I left it at that with a laugh and a smile.

[MF] Fucked my wife with a dildo while she sucked my cock

I got to have a simulated threesome with my wife using a dildo.

So my wife has a dildo but she doesn’t really ever like to use it…. like ever. I’ll sometimes ask and she’ll say no almost always.

This morning things got frisky and as things were heating up this morning We starting 69ing and I went from just licking to use a bullet vibe on her clit while I licked her labia. I could tell she was really enjoying it so I popped the question “can I fuck you with the dildo”. And her reply was “mhmmmhm” as her mouth was stuffed with my cock. I quickly lubed it up and started fucking her with it while using the vibrator in my other hand. She started making noises I’d never heard before and loudly too (she’s usually quiet) She even stopped sucking my cock she was moaning so much.

Hopefully she’ll start wanting to incorporate the dildo more because I love fucking her with it

[FF] My First Time With A Girl Was With My Best Friend’s Older Sister (PART TWO)

[PART ONE](https://www.reddit.com/r/gonewildstories/comments/bi2oox/ff_my_first_time_with_a_girl_was_with_my_best/)

The day after Katie became the first person (outside of myself) to make me cum, I stayed inside my room most of the day. I was still in shock. I wasn’t raised in some crazy religious household where being gay was worse than murder. It’s not like I was afraid or embarrassed. I was just confused. On top of being confused, I was extremely horny. I would try to distract myself by watching a movie on my laptop, but I took at least three breaks to rub my clit while thinking about Katie’s head between my legs.

I heard Katie leave at around four or five in the afternoon, so I escaped from my room and made myself something to eat inside the kitchen. After eating and doing the dishes, I took a shower and then went back to my bedroom. I didn’t bother to put on anything more than a bra and panties because I didn’t expect to leave the room again.