Late 40’s [F] and the college boy [M]: A first for both of us

Just discovered this subreddit recently and I’m a total nube to writing about my experiences–so hopefully these won’t be a waste of your time. Please be gentle!

Should probably start with a little explanation. As I was growing up I was tall, gawky, had glasses and an overbite. Then I was a wrestler throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles), but I still have the perception of myself as a gawky kid with glasses and can still be somewhat shy until engaged and alternate between overconfidence and no confidence.

I remember hearing my dad and his buddies laugh about how ridiculous and unrealistic “I can’t believe it happened to me” letters that were in Penthouse (or Playboy? Both?) and that’s kind of how I feel about the experiences I’ve been fortunate enough to have–I don’t consider myself overly sexual or deviant, but I’ve somehow managed to have a lot of encounters that, upon reflection, are large in volume (everything from college girls to probably an unusually high amount of milfs/cougars) and kind of unusual (in semi-public rooms, fingering under the covers in front of the girl’s family, threesomes, with food, tying up, and so on) and seem like bs.

[oral] [mWM] [disguise]

“Mrs. Fuller, I didn’t expect to see you!” Adam stood, in khakis and a shirt and sweater, at the doorway of the Fuller house, expecting to see Sarah, his girlfriend. She lived with her parents, Mr. and Mrs. Fuller, while she waited to hear back from various jobs she’d applied to since graduating from college.

“Hello Adam! Come in, come in,” Mrs. Fuller said. She wore a cornflower blue blouse and white pants, and althought her blonde hair was beginning to go grey, Adam found her a very attractive woman. Most of Sarah’s beauty came from her mother.

Adam entered and followed Mrs. Fuller to the living room. “I suppose you’re looking for Sarah, of course. She should be back soon, she’s out somewhere. Can I offer you a tea in the meantime?”

“Yes, please,” Adam said, “that would be lovely. Thank you.”

As Mrs. Fuller went to the kitchen, Adam surveyed the photographs on the mantle above the fireplace. He saw pictures of Fuller family trips, Sarah growing from a child to her age. In many of them Adam saw the stern, mustachioed face of Mr. Fuller, a serious man whom Adam had only met a few times. Adam wasn’t too sure Mr. Fuller liked him.

22/F, the results of my “30 guys in 30 days” experiment. [F] [FM] [FFM] [FMM]

This summer I came up with the idea to do a 30 guys in 30 days experiment. I’m not sure what I set out to prove, other than collect interesting information, and force me to break out of my shell of regulars and see what else is out there. The rules were pretty simple: Fuck a new guy every day, for 30 days, and record the results. Had to be somebody I had never fucked before, and will never go back and fuck again. Here’s how it went:

9/21/16 – Met a guy on Tinder, black hair, black beard, and chubby. We fucked in the back of his car parked in a quiet parking lot. He wore a condom, and finished in my mouth. I did not cum.

9/22/16 – Another guy from Tinder, also black hair and chubby, but surprisingly handsome and had a lot of tattoos. Fucked on my bed while my roommate did the dishes. He lasted a long time and we did a lot of positions, he came twice, both times into condoms inside my pussy. I came a bunch of times.

[MF] I Love Maths

This is my first time writing so please excuse the bad quality. This happened about 6-7 months ago.

Ashleigh (21): White (slightly tanned skin), light brown/blonde hair, light brown eyes, amazing body figure, nice handful tits, and a decent ass (could be amazing if she works on it a bit more!), 5ft 2in

Me (22): Athletic body type (go to the gym often), light brown skin, black hair, brown eyes, 5ft 8in

Getting some relief from the new girl at work. [MF]

So this has all unfolded pretty recently. I’m making myself write it up now because I know what I’m like, and I just won’t get round to it otherwise! I’m a big-time lurker on Gonewildstories, and am pretty excited to be sharing! Hope it’s still okay to post with a throwaway – none of this is illegal, but I would get into some seriously deep shite if it ever came out. Oh – skip ahead to the bit in bold if you’re impatient!

I’m 28, and I work for a small/medium non-profit organisation, in a brand & marketing role. Pretty interesting, if ordinary, job. Being a non-profit we often get volunteers in to help out – good for the sector and good for those looking to get into it. My little team hadn’t really had any volunteers before but seeing as we had an influx of work coming our way, my friend/colleague Harry and I decided we’d give it a go.

We got sign-off from our manager and put the advert out, looking for someone with a creative streak to put in a couple of days a week. Our replies were quite disappointing to be honest. A few people who were clearly fumbling in the dark with no understanding of the organisation, and a few who were only looking to make a very short-term commitment.

[MF] a week of spanking and sex: Friday (pics)

Angela: five-six, about 150 pounds, around 30 years old. Long brown hair, dark brown eyes. Soft all over. Her breasts are probably a C or D cup, but I don’t remember exactly. She has children, and when she’s naked she’s completely unselfconscious about the changes that having children made to her body. I think she’s gorgeous and sexy. Oh, and she’s a squirter, too. Every single time.

Me: Six feet tall, about 290 when this occurred, mid-30s, brown hair, blue eyes. My hands are pretty large. That’s about all you need to know.

[Tuesday](https://www.reddit.com/r/gonewildstories/comments/58jemg/mf_a_week_of_spanking_and_sex_tuesday_pic/) | [Wednesday and Thursday] (https://www.reddit.com/r/gonewildstories/comments/58ptvi/mf_a_week_of_spanking_and_sex_wednesday_and/)

The weather was finally good, so I went into the office while Angela did some sightseeing. We went home, she talked to her kids, and then we had dinner.

I do, however, want to show you [this photo](https://eroshare.com/i/0rovkyye), which I took around 6:50pm. I had only given her a few fun swats here and there in the morning and when we got home, but her backside was still very pink — even after she’d been on her feet all day, being a tourist. I’m rather proud of that.

A good date can lead to a great orgy [m][f][m][f][m][f][f][f] [group] (pics included)

A good date can lead to a great orgy.

A couple weeks ago we went on a date with a couple, Steve and Jess, who seemed promising; though the logistics in setting up the date were tangled, we eventually got together, had a drink or two, and thought about going home with them that night, the main problem being that we had to get some sleep and wake up the next morning to “work” so we could have “money” to “pay rent” and do those other horrible tasks that stand between humans and pleasure.

Rain check. Eventually all four of us set something up for Saturday night. They know a lot of people and we [met some at the last sex party](http://seattle255.tumblr.com/post/150780477759/about-killing-kittens-sex-parties), so the date night grew in number from four to six to eight to a couple of single girls thrown in. It grew in scope from a drink to night of total debauched group sex.

The day of, one couple has one member who’s sick and another has plans that they decide they can’t alter. So it’s six couples and two single girls: one is Alicia, a woman we know from that sex party (her significant other is tragically out of town), and the other comes via Steve and Jess.

[MM] My first and only gay experience

One night I was looking to get with this girl who I’d been wanting for so long. We were both pretty drunk and when the club closed, we went to her gay friend’s house with some other people. She and I were cuddling and all of a sudden she just started crying in my arms. Her girl friend called her a taxi and they got out of there. I was bummed, but plenty of people were still hanging around so I thought I might as well stay. I got talking to the gay guy that was renting out the place and we ended up talking for a good hour. When we paused for a moment, I realised everyone had left. We started asking each other sexual questions and I was beginning to get turned on. I had never been with a guy, but I had jerked off to gay porn. He was a twink with bleach blonde hair. It must have been obvious that I was checking him out. All of a sudden I said “I’ve only ever thought about kissing a guy once before, but I can honestly say that I could probably kiss you right now”. I had never been so forward in my life, I rarely ever made the first move. He smiled and asked “Well why don’t you kiss me?” I started shaking, I was so nervous and turned on. I came closer to him and his lips met mine, first softly, then we had our tongues intertwining. He asked if he could give me a blowjob. I became nervous once again, I had never shown another guy my cock. He didn’t wait for me to answer and unzipped my jeans and pulled out my penis. Before I could drunkenly object, his mouth was around me. It was pure bliss. I’d been blown by plenty of girls who thought they were good, and I thought they were good, but this guy was an expert. After a while, we got up and went to his bedroom. “Oh my god” I thought to myself “Am I going to fuck him?” We laid on the bed and kissed passionately again, he played with my cock. I thought I should stop being greedy, and I unbuttoned his jeans, and pulled out his penis. It was about the same size as my own, an average size, but I remember feeling it, thinking to myself that it felt silky. It felt good. He pulled away from me and brought his mouth to my cock once more. Again, I began to feel greedy and so I pulled his mouth off of me. I didn’t fuck around, I wasn’t nervous any more. I popped his cock in my mouth and tried my best to imitate his earlier performance. I swirled my tongue around his head and went up and down on his shaft without trying to use too much teeth. I felt him moving around and thought he was going to cum soon. To my surprise, he was merely adjusting himself so as he could suck my cock while I was sucking his. We 69’d for a while, both enjoying each other, both in drunken bliss. Eventually we stopped. I was so horny, but I was really tired and drunk. We kissed a bit more and touched each other’s penises. He wanted more but I was becoming really disoriented. He put his back to me and we cuddled for some time, my cock resting just near his ass. He grinned against me, wanting me to fuck him, but I was exhausted. Eventually he relaxed, sensing that I was done. We fell asleep with my arms around him. I woke up around 5:00 am. Not much of a sleep. I had sobered up a lot however, and I realised how much I smelled of rum and horny sweat. Feeling of embarrassment started creeping into my psyche. I got up and began to get dressed. He woke up and asked if I was going. “Yes, I should go home. I have to work soon” I lied, “thanks for letting me sleep here, and thanks for everything else. I had a good time.” I hugged him and left. I called a taxi and went home. I felt so confused. Was I supposed to be ashamed? I thought I was straight. Yet, I had kissed and sucked a guy and enjoyed it immensely. I got home and slept.

[MFF] – Met up with a couple, took the girl home with us

Hi GWS. I wanted to share another story the sexual adventures that my girlfriend and I have recently started embarking on. Forgive me, for I am not a writer and have an affinity for using long sentences and passive voice. All the name of sexy time. Long read, but I hope worth it. Enjoy!

My girlfriend and I have been together for over 5 years. When we started dating, the whole internet dating scene was still very young, with only notables like OkCupid and Match.com being around. We always felt like we missed out on the proliferation of dating apps, mostly notably Tinder.

A couple years ago, we decided to try our hand at finding either another female or another couple to expand our sexual horizons and quickly found 3nder. Basically, Tinder for couples looking for threesomes, foursomes, and moresomes. The app has since renamed itself due to a lawsuit from Tinder, but it will always be 3nder to us.

babygirl and Daddy get an afternoon off together [BDSM] [D/s] [M/F]

It was one of those rare days that they never got. Daddy and babygirl never had days off together due to the distance between them and the busy-ness of their lives. The days that they woke up with babygirl in Daddy’s arms were few and far between already but the fact that she woke up in his arms with nothing to do all day? It felt like her birthday had come months early.

Daddy had no plans of letting this day go to waste though. After a brunch out and general laziness on the couch, he patted babygirl’s hip to get her attention off the TV. “babygirl, go use the restroom and then grab the lube.”
babygirl looked up at her Sir. He caught the excitement in her eyes, and knew she was already set to go. She launched herself off the couch and scurried to the restroom.

By the time she returned, Daddy had thrown their cuffs and two pieces of rope on to the bed and was standing next to it. Without a word, babygirl walked to stand next to him, and then kneeled on the bed, her back towards Daddy. With his left hand, he pushed her forward and her ass popped up in the air. Daddy leaned over her and took the lube in hand and, after opening the top, squirted a dollop on her asshole.