This story comes in multiple parts (the reason I’m posting this first one is because of what just happened recently).
It starts during the early days of the 2008 Financial crisis. Understand, the feeling of uncertainty, not knowing if we will have a job the next day, co-workers getting pink slips in mass waves, we were all on edge during the early days. My company was in transition and consolidating multiple branches into a new location. Most of the staff/processors who didn’t get let go were temporarily moved to our Headquarters across the county while our new location was in the final stages of being renovated. Our branch was now a skeleton crew of essential only personal. In fact, the first time I even met Avery was at the town hall meeting after the 2nd wave of layoffs. Upon recollection, she was not one that left any impression with me other than she was rather plain-Jane looking. She did have an attractive hourglass figure going for her but rather shy with new people. Avery lost most of her friends in the layoffs and employee move the previous months. Again, that was just my first impression of her. That all changed one fateful evening when I volunteered to drive her home because she had continuous car problems and her friend bailed on her. During the ride to her place, I found out we had quite a bit in common. TV shows, foodie stops, even hobbies we shared (obscure animation, not just Disney).
From that day forward, going into work was just a little bit better knowing we both became friends. We both found excuses to visit each other at our cubicles throughout the day, even started taking lunches together. Neither of us were dating at the time and given the atmosphere, neither of us were really looking. At that time, I considered Avery just-a-friend because “Don’t shit where you eat” was a saying engrained in me from my childhood.
Tag: Anal
NYC 27[M] I was deepthroated by 21[F] and came in her ass [Video/Pic included]
I was out pretty late for a Tuesday and was about to head back home to Brooklyn when an old fwb shot me a text that’s hard to turn down: “want to fuck?”
She lives in a different part of Brooklyn than me so I headed over to her place. From previous encounters I know she absolutely loves being submissive. She has roommates but it was late so the second I walked through the door I told her to drop to her knees and start sucking me off.
“But we’re in the living room…my roommates might see?”
“Then let them see what a good slut you are.”
From that point, I could tell how much this turned her on given how quickly she attacked swallowing my dick. She gagged on me a few times [I think I am pretty normally endowed but you be the judge] before we moved into her bedroom.
[FFM] SEX, DRUGS & A DRUG INDUCED FFM THREESOME (TRUE STORY)
## Backstory…
A few years ago, I was dating a lovely young woman; for the sake of this story, we will call her Carolyn. She was my ex’s best friend, and we always knew we had chemistry. Needless to say, when things ended with my ex, Carolyn swooped in and claimed me for her own. I definitely wasn’t complaining. Carolyn was definitely petite, coming in at five-foot-two-inches, ninety-five pounds. The thing that got me was her 28H breasts and the tightest, tiniest pussy I’ve ever experienced. She was a goddess, and little did I know she was a freak too.
Once during the time with my ex, she told me a story about her and Carolyn getting drunk together in the hot tub. According to my ex, Carolyn started asking ‘weird questions’.
> “Don’t you think girls’ bodies are so sexy?”
Followed shortly after by…
> “Have you ever considered being with a girl?”
After more of these questions, my ex got a little nervous. She then felt a hand on her inner thigh. She didn’t know what to do, so she tried talking about something trivial. As she talked, the hand moved up her thigh and under her swimsuit and began rubbing her clit. My ex-girlfriend freaked out, got up, and left, and she and Carolyn never spoke of it again.
My manager walked in on me [MF]
LONG READ!!
So some backstory, about two months ago I started this new job as a waiter at a small family owned Italian restaurant. I mainly took the second job to pay for college but would soon realize it was a much better decision. My manager, we’ll call her Kate, is the definition of a hot MILF. She’s in her mid 30’s about 5’6 with an athletic build, skinny hips but a big juicy ass and perky d tits. As for me I’m white and tall but built with about an 8” cock.
So about two weeks ago I got to work on a Wednesday it wasn’t too busy yet and it seemed like a pretty normal day. About halfway through my shift I had to go to the bathroom so I went in the back and did my business. Right as I’m finishing up I hear someone coming and then the door opens. It’s my manager. Kate looks at me, eyes wide as she realizes what just happened and then looks down at my dick, which I hurriedly tried to pull my boxers up. She steps in the bathroom and closes the door and walks toward me. She grabs my crotch and tells me that I need to stay after close to have a chat with her, and then she left. The rest of my shift I was losing my mind about what was going to happen and she was constantly starring at me.
So about last night [MF][Crossdressing][Pegging]
There is a weird and somewhat surreal thought exercise I like to engage in while sitting here in front of my company issued perfectly adequate yet utterly uninteresting laptop, over-hearing our office manager complaining again about people not refilling what I consider the world’s most inoffensively generic pot of mediocre coffee. I wonder ‘Am I the only kinky bastard in this room right now?’.
The high strung office manager with her ‘I want to talk to your manager’ haircut, has she ever been on the business end of a flogger? Jim in accounting, does he have some kind of smoking hot wife at home whom he just utterly dominates when he gets home, swapping his blue short sleeve button up shirt for a supple leather vest and single tail whip? My boss Kathy, with her exhausted eyes and comfortable but cheap shoes, does she have some titillating memories of the heady days of carefree left coast college explorative sex adventures?
Unexpected Birthday Presents (Public Finger Fuck) (Forced Orgasm) (Light mDom/fSub)
It’s your birthday today and I promised to take you downtown where we would search the stores for the perfect gift for you. The weather was warm as we popped into shop after shop. You tried on jewelry, scarves – even hats, but nothing really jumped out at you as being right. We continued walking down a side street when we came across a “sex toy store.” And not one of those gross, seedy places you see in the darker corners of town. This was a real “boutique.” Very upscale. We both looked at each other with curious smiles before I took you by the hand and pulled you in. The shelves and displays were packed with every type of device that could go in, on, or around one’s body. To be honest, some of the devices looked quite intimidating, but we roamed the store, hand-in-hand, picking up various toys and exploring them with our hands.
I watched you run your slender fingers over a large, realistic, 12 inch dildo. Your fingertips stroking the bulbous head and tracing down the thick, veiny shaft. I had a moment of insecurity and wondered for a moment if you would prefer a man with a monster cock like that to fuck you. I was so relieved when you put it back on the shelf with a laugh, saying that you thought it was “fucking scary.”
[MF] Came inside the cutest girl I’ve ever gone out with on the first date part 2 – second date, came in her ass and kept going
You can find the first post [here](https://www.reddit.com/r/gonewildstories/comments/ayw946/mf_came_inside_the_cutest_girl_ive_ever_gone_out/).
Our second date was at a bookstore. I showed up and at this point realized Elizabeth was naturally shy, which I found amusing considering what had transpired a few days ago, but she loosened up quickly a few minutes into the date. I kissed her intermittently whenever we were alone in the shelves, and I could tell it was getting her turned on the more I did it, with her pouting every time I pulled away.
By the time we got outside, she was aggressively making out with me, which was surprising for such a shy and timid girl. I suggested we go back to my place and watch TV, both of us knowing full well we were just going to fuck.
We get to mine, I make myself some tea, and we ended up on the couch making out. I picked her up and took her to my room, where I threw her on my bed. She instantly gets up and starts kissing me under my shirt. The next thing I know, my pants were undone and my cock was in her hands. She looked up at me and started making out with my cock and lathering it with spit, straight out of a porn scene. After a couple of minutes I decide to get rough, grabbed her by her hair, and slowly fucked her mouth.
The things that I want [F][anal][bd][bdsm][blkmail][bst][buk][cuck][drugs][exh][Fdom][fist][Fsub][huml][mast][nc][oral][prost][reluc][voy][sm][public][freeuse]
I want to be fucked on a park bench.
I want to feel two fists inside me.
I want to be on a leash. I want the leash to clip to my clit piercing.
I want to get choked while I’m being fucked in the ass.
I want to be fucked to an emotional wreck.
I want to be made so wet it drips down my thighs walking around.
I want to feel cum drip down my thighs.
I want to be a 24/7 live-in sub.
I want to know how big of a buttplug I can take.
I want to have all 3 holes abused at the same time.
I want to feel your cum pumping down my throat.
I want to cum so hard it makes me pass out. Every day.
I want to be passed around so many guys I lose count.
I want to my ass gaped.
I want to be a sex-doll.
I want to blow you at the movies.
I want to masturbate over and over again until my body is limp.
She flew in for a sex holiday [MF] [long]
This needs some introduction. Bear with me.
I met Anna in the same class I met Jane. ([Story here](https://www.reddit.com/r/gonewildstories/comments/asfw0m/three_in_the_bed_mff_long/)). Anna didn’t much like Jane so we had a very separate friendship. Anna had just got married that summer prior to the class and used to bring wedding photos to school. Turns out it was quite an unhappy marriage. One night We three are driving and they get in a big fight, he storms off and I drive her home. As we talked, she opens up about the unhappy marriage and I have this odd, powerful lustful attraction. It didn’t happen and she moved across the country.
Years later, I’m with Tina. ([Here’s a bit of fun with Tina](https://www.reddit.com/r/gonewildstories/comments/aysgc9/low_tide_at_sunset_turned_into_sexy_times_mf/)). Tina and I had numerous talks about how if we ever had reason to cheat, we would both be open to discuss it. She was a virgin when I met her, and had only kissed one boy in high school. I gave her a free pass if she ever wanted more experiences.
Need to get over a heartbreak? Double anal fuck a girl with your friend! [MFM]
**New friends**
I’m Domenico. 25 years old. Good looking guy. Athletic body. Build like a rugby player, people tell me. Tall, dark and handsome. I’m Italian and live somewhere in Europe. Recently I was in love with a girl but she chose to be with another guy. What are you gonna do, huh? I need to move on.
On Monday I will be starting my new job. I will be working for that girl’s dad, actually. In their house. So this man has private security guards (don’t ask). I will be doing business, but I also will be in charge of security. He tells me *”Get to know the guys before you start, you need their trust and respect”*.
Sure. So I talk to these security guys, two of them come with me to a nightclub last night. Tough guys, early twenties. My best friend and cousin Gennaro comes with us. VIP booth (or whatever it’s called in English), one of the hottest night clubs in the city. We have lots of fun.