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.

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.

I was the first pussy he’d had in 2 years [MF]

Very long time lurker and first time poster. And I’m not too great at writing out stories but I thought I’d share with you guys here.

So to get things started here I’m 21. I have dark brown hair, 38C, pretty fat ass and curvy since having a baby a few mornings ago. He’s 31 short black hair and a little scruffy mustache and beard. Has a bit of a beer gut but overall dad bod (which is funny cause he also has a kid).

We met on Craigslist. Strictly Platonic page. It was his ad looking for someone to talk to? I can’t really recall because we started talking in mid August. He has his child and is a single dad. The mom isn’t in the picture. And same for me as well. He has a very busy schedule and lives about 50 minutes north from me so meeting has been very trying.

A ridiculous sequence of events – Casual sex [m/f], casual sex [m/f] that lead to a threesome [mff] – Long!

My third story is a very random series of events, I’ll try not to waffle too much.

Me and my best friend used to work in the city, so naturally it became our regular place to have a night out. I was in my lower 20s at the time, young, dumb… you know the rest. We were out most Friday and/or Saturday nights, drinking the night away and looking for skirt. This one particular night I was particularly hammered and started pulling about a blonde girl who was a bit older than me, just groping on the dance floor nothing major happened that night. I woke up the next day and genuinely could not picture her face and remember much about her, but a bit later that Sunday I received a text from her, so we must of at least swapped numbers at some point. What followed were a pretty normal few weeks of occasional texts being exchanged. I had no burning desire to see this girl again as I couldn’t remember anything about her and the texts never got steamy or anything like that. One day at work I receive a text just straight up asking if I wanted to meet up for some fun, which is when my curiosity got the better of me. After all, I’d finally get to see what she looked like. The first meeting came around and it was typically awkward for two people that hardly knew each other. She was below average build, with some nice boobs. She was quite sweet, not the most intelligent lass but we had a giggle and it was all quite innocent. Eventually we hopped in the back seat and got down to business. Her boobs turned out to be less perkier than I was hoping and it was the first and only time that a girl has ever sucked my cock while I had a condom on. Those things can’t taste good.

We Promised to Be Quiet. I Broke Our Promise.

It’s not strange to hear my dorm room shower running at 3 AM on any given evening. Saturday’s less so; four girls sharing two rooms, we’ve learned to ignore the footfalls in that tiled hall, the rattling click of a lock just outside of our dreams. We only ever barely wake up to the sounds of drunken giggles in the commons, or the fridge’s hermetic gush when we try to sneak our midnight snacks. Three AM is the safest hour to interrupt wetdreams. Mine were brought to a blind reality with that perfect, pushing hand.

Tonight, you and I are still very much in the waking world, even if we’re palming our way through the total darkness of this dorm. The first creak of my bed wouldn’t wake Vanessa up. The second creak of springs when I exit these innocent blankets and pillows could stir her – but it’s nothing more than her roommate going to the restroom, right? That other lump she saw when she walked in earlier, the other shape beneath the sheets was just a guest – surely, she thinks, they’re left behind in bed. The darkness hides even her own hand before her face, and sleep takes it to guide her away from our plans. We are safe to lace each other’s fingers, to open the door and push naked heels from carpet to cold floors. One finger is pressed to your lips until you wrap your tongue and suck it soft. Bad. I’d slap you how you like it, if I knew it wouldn’t echo through the hall.

How a MILF at a softball game wanting cock saved my marriage (LONG – x-post from r/truebigdickstories) [MF] [Cheating] [Group] [Swinging]

I’ve been posting on r/truebigdickstories and it was suggested I post here.

Long story short, I’m 47, a widower, and fighting cancer these days, and I’m recalling my previous experiences, focusing on the big dick centric stuff b/c of that sub. But I was kind of a slut in my younger years, having slept with 100-ish women, and being endowed (9 inches or so) played a role in some of that. Most of it had nothing to do with that, but whatever. Anyway if you want to see more, see my post history.

And I know I’m wordy — I’ve tried to go out of my way to make it short. It’s still long though — I tried.

Before I get to it, I need to explain how my wife and I got together.

When I was younger (high school and mainly college), I slept with way too many women. Over 30 or so… I can’t really keep track. I had lots of girlfriends (call me a romantic, but most of the girls I slept with were girlfriends). I tried not to sleep with random girls who weren’t girlfriends though it did happen 10 or 15 times, sometimes on accident and sometimes for sport. But I did go through girlfriends like water, I’ll admit.

Friday Night Drinks [MF]

My fiancé and I met when we were 15, kissed, and thought that would be the end of it. We would never come across each other again. Turns out that we met again when we were both 18, and stayed together from that day onwards.

For the next seven years we were soulmates. We became so engrossed in each other’s lives that her nieces and nephews were mine as well. So much so that we were chosen to be one of her nephew’s god parents (despite being not even remotely religious).

I loved her family as well. Except one of her sisters. She was a pain in the ass. There was a time that we lived with her, and she was THE WORST. As in, the kind of housemate that you would just want to kick the ass of. Never did her own dishes, never cleaned when it was her turn, and never even tidied the goddamn bathroom. The worst.

After all that, we moved into our own place and looked forward to the future. That is, until we found out we were living with a brain tumour.
In the end, it was over pretty quickly. I never, ever, thought I would bury the love of my life. But that is exactly what I ended up doing.

In The Laundry Rm. [FM][inc][voy][mast]

It was a quiet Sunday morning when my horny landlady, Mrs. Sinclair left for her weekly trip to Thunder Bird casino fifty miles away. If she stays true to her schedule, she won’t be home until dinner time. With her gone, I feel free to use the house, hang out by the pool and do some laundry in peace. Shasta, her twenty one year old daughter was in her room as usual. Connor, her nineteen year old son was gaming in the family room. They stuck to themselves while I hung out by the pool drinking a beer and doing laundry.

The night my (M40) wife (F34) gave a stranger an orgasm – LONG – (FF)

Just a little back story, Julia and I have been married almost 11 years. We have been around the “lifestyle” for most of those but have typically been a – watch and be watched – kind of thing. The last several months have been a little stressed. She is a wedding planner, and I’m in sports marketing (football mainly), so we have both been very busy with our careers. It’s definitely taken a toll on our sexual life. Don’t get me wrong, we have a GREAT sex life, but sometimes the ‘life’ part gets in the way.

We live in Nashville and there’s an amazing lifestyle club here called Ménages. We have been many times and had a lot of fun but haven’t been in a while. We had decided to have a nice date night this past Saturday so we got a hotel and planned on a trip to the swingers club. As I mentioned earlier, she is a wedding planner so Saturday morning/afternoon, she was working a rehearsal for the following day. When she finished, she met me at the hotel. I suggested that she go pick out a new dress for the night; something to make her feel sexy and more of her exhibitionist side. She is about 5’2”, small perky B cup breasts, an ass to die for and one of THE most beautiful faces I’ve ever seen.

Impromptu Wife Swap: A Lake Trip Gone Awry

—If you want to get right to the action, skip to just after the — break

Sarah, her husband Dan, and I have been friends for 15 years dating back to high school. My wife, Lauren, became part of our regular hangouts a few years back. Every year we all watch football on Saturdays and Sunday’s together and swap who makes meals each week. So when Sarah asked if we would want to take a trip to her parent’s new lake house for the first weekend of the NFL season, we jumped at it.

As soon as work ended on Friday we all jumped in Dan’s SUV and headed towards Lake Norris in Tennessee. We all chatted about the previous week’s work, the upcoming election, and the upcoming NFL season, making sure to get our jabs in at each other’s respective teams.