Tag: BJ

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

[Repost from my previous account. I’m going to put up a few of my previous posts to fill in my history–leading into posts about other experiences I’ve had, too. For the impatient I’ve placed an **action starts here** below, as I realize this is long.]

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. Read more »

I finally [f]ooled around with my handso[m]e older friend/former boss.

I first met Chet 5 years ago at a work related event at a bar. I was a cute little 24 year old in ripped tights and a short dress, and he was a very handsome 40 year old man, well dressed in a casual suit. We chatted for a bit while I smoked a cigarette, thinking I was being so charming and adult, and we’ve been friends ever since.

Im tall, long legs, a bit of a belly but nothing crazy, perky smallish boobs, long dark hair and a pretty face. With these features I’m certainly not everyone’s type, but the guys who are into it think I’m hot haha. I’m in a creative field and am used to hooking up with guys who are like me, grungy and disheveled, which I love! But Chet is different, an executive at a financial company, he wears suits and nice clothes, combs his full head of thick gray hair back and parted, and he looks a lot like a less-heavy Alec Baldwin in 30 rock. It drives me crazy. The first few years I knew him it was as a casual friend. He’s interested in my creative field and would show up to lots of my work related events to drink with me and my friends in the same field. Read more »

I (23/F) Cheated with my Snowboard Instructor [MF]

This was just last week. I’ve been thinking about it every since, and obviously can’t talk to anyone about it so I figured this would be a good way to share since it was one of the most amazing experiences of my life!

We were on a ski/snowboarding trip in the mountains in BC (that’s about as specific as I will get to protect his identity). It was my fiance and I, as well as a few of his friends and one of their girlfriends. We rented a condo right on the hill, so it was 5 days of skiing, hot tubbing and drinks. My fiance both skis and snowboards, where as I am an experienced skier that just this year is attempting to learn to snowboard. I skied for the first 2 days, then on the 3rd day, my fiance agreed to hang back from the rest of the group and try teach me to board. That’s where thing started to go wrong! It’d be an understatement to say it didn’t come natural to me, and I could tell he was getting frustrated, then I was getting frustrated at his frustration and my inability to catch on. By the end of the day, I had enough and I’m pretty sure he was regretting getting me the snowboard for Christmas. We were barely talking to each other. Read more »

[MF] Department Store Dressing Room Fucking

One more story (for now) involving my cougar girlfriend “Jessica”. For those of you who don’t know, she’s 47 and I’m 21. She is a total hottie who has a 27 year old body complete with 10/10 ass and legs. Her tits are normal sized but nice. She’s Latina with perfect skin and a beautiful face especially when she smiles. About a month after we started dating, she wanted me to go shopping with her. I said to myself, “Shit. This is going to be a waste of a perfectly good Saturday.” But I was still trying to impress her so off to the fucking mall we went.

So we got there and went into one of the higher end stores. The sales lady was this old no nonsense bitch who reminded me of my third grade teacher. Jessica picked out some outfits, mini skirts, jeans, stuff like that and took them into the dressing room with her. I sat in one of those chairs they have for the guys to sit in while their SO tries on clothes for hours on end. Read more »

Just another first ti[m]e cock sucking story

In the last year and a bit, I (27 y/o male) have been considering the possibility of being sexually attracted to men. Kinda crept up on me out of nowhere, never had any urges like that earlier but I’m a naturally curious person and started considering that cocks aren’t a turn-off.

Anyhow, I’ve been growing to be closer friends with my friend circle’s resident slutty man, since he and I have many overlapping interests and get along well. He is very open about his polyamorous and bi status, so it has been fun flirting with him.

My fiancée is herself delightfully dirty and we started dirty talking about me sucking cock while we would be having sex to our mutual titilation. Finally though, we invited our friend over to play card games on a weekend. Part of the delay had to do with our apartment finally becoming clean enough to invite people over.

My fiancée isn’t a big fan of wearing clothes in our apartment and we knew that our friend would be ok with that, and since we’d discussed the possibility of naked card games before, our friend joined in on the nudity. Read more »

[MF] Fucked my boss and enjoyed every second of it

Towards the tail end of graduate school, while I was finishing my thesis and job hunting, I started working full time at a regional bank as a teller. They placed me in one of those branch units in a grocery store and although it paid okay for the difficulty of the job, I never felt it paid enough for the customer service aggravation it entailed. People understandably get really irksome when it comes to their money, and have a tendency to take it out on the messenger when they discover they can’t manage their business very well.

It was a weird job and I met a lot of kooky people during my tenure there. And a lot of strippers. So many strippers. “Oh, Von Scriptenstein, that’s so cool, you partied down with strippers?” I hear you asking me, and the answer is no. I took the previous evening’s earnings from strippers to deposit. Often. And if you think that’s super rad, you’ve never held a black light up to cash. There’s a reason you see so much hand sanitizer when you go to the bank. Read more »

First time I [M] fucked a girl [F] from the anonymous app Whisper

So over the summer i downloaded the app whisper. I forgot how I came across it. At first my intentions weren’t to hook up with people. I figured people weren’t on there for that reason so why even bother. If I wanted to meet up with someone from the internet I would use Tinder or an app like that. The app is amusing though. About one month into the app I still hadn’t met up with anyone. Wasn’t really trying like I said. Then my luck changed. I started talking to someone and we met up and made out. Didn’t have sex though. About a couple of days later on a saturday night i posted a Whisper asking women how long did they take before they decided to sleep with a guy. I got a couple of replies and one or two dms. One of the replies was sent by a girl who lived not too far away. We start talking and got along pretty well. We talk again the next morning and i ask her if she wants to hang out. To my surprise she said yes. She takes an uber to the train station where i meet up with her. We head back to my place. During the walk we were both a little nervous. I hadn’t gotten laid since June so I was a bit sexually frustrated. We get to my place and we sit on the couch. No time was wasted. I touch her leg and tell her to get on top of me. We make out for a bit. I then pick her up and carry her to my room. I place her down on my bed and get in the bed with her. We’re making out. I then take off her shorts and panties and her shirt as well. I spread her legs and start fingering her. She was dripping wet. I then eat her out. I eat and finger her for a bit. Afterwards i place her legs over my shoulder and drill her. We then went at it for the next 4 or 5 hours. Breaks were taken but for the most part we fucked nonstop. We fucked on my bed, the couch, the floor, against the wall, in the shower, standing up. We even did anal which was my first time doing it. I got rough with her at times. I spanked her, pulled her hair, choked her a little. Threw her around the bed. Not once did she resist. She gave in completely and let me manhandle her and enjoy her body. By the end of it my cock was sore. I walked her back to the train station and said goodbye to her. We met up one more time after that. Did much of the same. I started hooking up with other people and well she started seeing someone. We still keep in touch. I’d be lying to you if i said i don’t think about fucking her again. She was some of the best sex I’v ever had. Since then I’ve met up with 19 more girls off the app. I’ve fucked 11 of them total. One gave me a bj and with a couple I’ve made out. I want to stop but I can’t. The app is addictive. AMA you may want to know

[MF] Losing My Virginity On a Post-Graduation Vacation

It was a sunny day in late November. I’d not long since graduated high school, and full of youthful energy, and a naivety and enthusiasm that only a lack of exposure to the real world can bring, I embarked on a week long holiday with four of my closest friends at the time to a sleepy little town in coastal Australia to celebrate our achievements by abusing substances, and attempting to sleep with complete strangers. I wasn’t much of a “party hard” kind of guy in high school. I’m still not, but I wasn’t then either. With a little bit of soul searching and pressure from my friends, two guys (Declan and Lewis), and two girls (Jess and Sasha), I realised this was a literal once in a lifetime opportunity, and I should seize it with both hands. Read more »

[MF] The night I fucked a girl in front of my best friend (exhibition)

The second night with Amy was out of the blue. Being from California, my best friends live there. My best friend came and picked me up, we went tried going to Russian river for Pliny the Younger, but the line as around the block, and our motel was only walking distance from Lagunitas, so we went there. They introduces us to liquid heaven, the San Francisco Fusion, a triple IPA to compete with Pliny the younger. We talked for a while, catching up, I told him about Amy and he said to invite her over, so I did and she told me she would get ready and head over. A couple beers later(when I drink I don’t count time I count drinks) she texted me that she was there. Like stated in my previous post, and I actually asked, she is a 5’1″ brunette with a hourglass body, nice tight firm ass, and beautiful fake breasts. She was wearing a super tight white and blue striped dress. The first thing she said might be one of the sexiest thing she has said to me, and yes she talks dirty, she simply said, “I’ll buy the next round!” I gave her a kiss hello and she ordered the next beers. My friend, her, and myself all drank, told stories, and listened to the music. We all walked to the smoking area, and I couldn’t help myself from looking at her body barely concealed by her dress. I looked at her, smiled and winked, looked at my buddy and told him to drink our beers. I grabbed her hand and started to bring her back to the motel. We couldn’t keep our hands off of each other and I ended up pushing her up against a sign on our way there, she pulled out my cock and started to stroke it. Not wanting to get arrested I put it back in my pants and we made our way to the motel. We fucked like rabbits but thats not the sex part of this story. Read more »

[MF] The creepy roommate of my FWB Part 2: Return of the Creeper

**[Link to Part 1](https://www.reddit.com/r/gonewildstories/comments/5woprb/mf_exhibition_the_creepy_roommate_of_my_fwb/)**

*Fair warning that this is long, and that it does not represent my proudest moments. As I was writing I kept going back and adding little details as I remembered them. Do you ever conjure up an embarrassing memory and your brain can’t stop building on it, making you remember more and more little things until that shame bomb is primed to detonate? This whole story represents that process, I think.*

True to my word, I had Tink over to my tiny little apartment the following day, despite the fact that I was really crunched for time at that point (I’d been working on three separate papers for grad school and needed to finish my research). As exciting as Creeper’s voyeuristic interlude had been the night before, it didn’t do much to alleviate the guilt I felt over staring at her while I fucked Tink. Not telling Tink about it felt more than a bit like lying, but I was also afraid to just come right out and say what had happened as Tink always struck me as a bit vindictive and I wasn’t exactly keen to incur that wrath. Read more »