Tag: High School

Tennis Lessons. Part 1. [MF] [MILF] [Younger man] [Older woman] [Masturbation]

*New writer here! Tips/advice appreciated. Part 2 coming tomorrow!*

TL;DR College tennis player picks up a job teaching moms at a country club. Fantasizes about pleasuring an unsatisfied MILF.

College is supposed to be the time of your life. You make friends for life and live on the wild side for a bit. Unfortunately for David Johnson, his junior year of college had been cut short by school closing because of COVID-19. He only got to play in one tennis match before the let out. Now, instead of going out every night, he’d be stuck with family movie nights and next to no friend time since they all lived far away. It looked like these next few summer months were going to be torture for David. No tennis, no parties, no friends. And to make things worse, his mom had the bright idea of him working all summer.

“You should be a tennis coach at the country club!” Eagerly suggested his mother. Read more »

I caught my husband watching a college video of mine and told him the story [Group]

I went to a small college without many folks and so on the weekends it totally cleared out aside from other out of towners and people on teams. Pretty early on in my freshman year I made friends with a bunch of guys on the lacrosse team. I ran track in high school and stayed as fit as possible and would work out a lot in the small school gym.

One night a few of the lacrosse guys were drinking and invited me to join in “as one of the guys.” I was stoked to get out of my room so I jumped at the chance. Our security guards are pretty oppressive so they told me they’d found a fun place to drink and after a few texts back and forth I found myself climbing up to the library roof with a handful of dudes to get wasted – which I was really excited about.

We’re two beers in and talking non stop about sex and to be honest, since I’d gotten to the school I’d been a bit intimidated and hadn’t found anyone to play with. So, I’m being honest and explaining how I feel and of course the guys are like, well shit, I’ll be that guy! And we’re joking about it. Read more »

[M]arried [M]an’s First Naughty Craigslist Encounter

# This will be the first installment of my confessions on my erotic deeds / misdeeds. I offer these not to brag, though there was often joy and exhilaration, or with a sense of conquest. And I offer them without moralizing, though there was also at times degradation. I tell them because we are all storytellers and where else but on an anonymous board like this one can I tell these stories? You can judge them and me if you want, but I can promise you that they are all true. So read on.

About me — I am now in my mid-to-late 60s, well liked and respected in my profession, a ‘success’ I suppose in that sense, and also have grown children and a few grandchildren who hold me in esteem. And I have been married to the same woman for several decades, the only woman I have ever been married to … unless you count that period of my great affair, when I loved and was loved by two women and somehow managed to get through it with everything more-less intact. But that is not the story for your ears, no offense, as I hold my experience with the other *her*, may she rest in peace, as sacred. But I digress. Read more »

[MFM]Life Lessons [Long]

A thing I have noticed on this board recently is that people are pretty much only talking about victories and successes. They are always about the hottest things that happen and never the fairly normal stuff that happens to. Maybe there’s a reason for it, but personally I miss the stories that were sweet, funny, or sometimes just outright embarrassing.

So for the sake of bringing some of those stories without pissing off too many of you, I’m going to warn you ahead of time: This story is about a crushing and embarrassing failure on my part that makes me laugh thinking about it now. Wasn’t so funny at the time. Unless I am told otherwise, future stories will not give this warning. They may be about success or failure… but considering my sex life they will probably still be hilariously awkward.

A long time ago I took a girl I was dating on summer vacation with me and some friends after we graduated high school. Near the end of the trip there were just three of us left in the cabin. Being a bunch of teenagers left alone in the woods obviously we got up to some stuff that will fit on this sub. Maybe I’ll go into those stories too later. Read more »

[MF] Our Last Day of Vacation Was an Interesting One.

My girlfriend and I have been together 3 years now. She 40 and got out of a 15yr marriage when I met her. The last 6 years or so of her marriage was nearly sexless. I’m 34 and can’t say I had much better luck with relationships. For most of the time we been together she did not want to talk about desire and sex, but would still want sex constantly. We have a great sex life, but there was always this communication block and it was a bit of enigma for me. After a time we explored, learned, and even started talking about sex. One of the things I learned, and a relevant tidbit for this story, is that she is really turned on by the idea of showing a 18yr guy how to eat pussy and showing him what a blowjob is like, especially if it’s before his first date. Another is being watched. She wants to see men’s erections caused by wanting her, but being unable to have her. I’m 100% on board with these fantasies. Partially, because I want her see her loose her damn mind living them out, but there is also this good house wife going naughty thing she has going on. Read more »

Erica, sister #2, part 1 [Str8][Mf](oral)

I tried to post this with a link to the first story, but it was removed. So if you want to read the first part, just check my profile, it’s easy to find.

This takes place at the beginning of my senior year in high school, about a year after I dated Connie. During that year, I had become a lot more experienced with girls and confident. I lost my virginity, but it’s not really worth a whole story, since it only lasted the typical 30 seconds. This story is worth sharing for several reasons.

I played soccer in high school, and while I was not good, it did come with some great perks, which is why I played all the way through my senior year. Due to the limited school funding, my school didn’t have enough room for the girls and guys to practice completely separately. The teams shared a field, and a lot of the time during conditioning, we ended up all running together. Since it was so hot outside, most of the time the guys went shirtless, and the girls usually only wore shorts and sports bras. At the beginning of senior year, all of the guy players were eagerly looking forward to see the group of younger girls moving up to varsity that would start practicing with us. Read more »

New Beginnings: Chapter Two [Alien Encounter] [Sci-fi] [Interracial] [Straight Sex]

“B,” Bill said as they sat in the utility vehicle. They were parked just outside the food court of the mall.

​

Things had gotten back to normal. Well, as usual as they could be with a giant alien spacecraft sitting in their backyard. The mall was busier than it had ever been. Chuck, the realtor, had told them that he had rented out or sold more houses and apartments in these few days than in his whole career, seeing as he took over his family business straight out of high school that was saying something.

​

“Nah, A tops,” Adrian replied.

​

The two of them were playing their favorite game, guessing the cup sizes of the women that walked out of the exit. There wasn’t much to do for security around here now that the military had set up small substations all over town. Crime had dropped to an all-time low. Everyone liked their presence except for a few individuals.

​

“So, you are coming tonight, right?” Bill looked over at Adrian.

​ Read more »

Celebrating the Uniqueness of Mature Women – A [M]an’s Testimony

I posted this on r/cougarsandcubs to celebrate the uniqueness and differences between the women us younger men love and enjoy while also sharing my own unique taste and appreciation for the women I have had the pleasure of getting to know. This is the uncensored version. The first time meeting a woman is exciting. The smell and touch of a woman is just magical. For some reason, meeting a woman older than myself for the first time is an even more surreal and almost out-of-body experience. The nerves of anticipation, the first eye contact and then touch, the path of the conversation, the initial physical intimacy, the exploration, the syncing of body and mind, and on and on.

Background: A long-term relationship I was in with a woman my age ended mutually last spring. After some self-reflection, I decided I would fully pursue my long-time attraction to women older than myself. I had briefly attempted it as a 20 year old with no luck. I was now in my late 20s and had filled out physically. My personality had also matured with life experience leading to a boost in confidence and intuition to carry on a conversation with most any sane human. It took a month or so to figure out my approach, but I was ready. Read more »

Summer Interns In Heat [MFF] [BDSM] [Ddlg/Roleplay]

While balls deep, in her shouldn’t be so tight MILF pussy, I thought I felt a fly land on my leg. I tried to focus, but it was too late. Mel, my cube neighbor and former D1 athlete, hit me square in the face with a balled-up piece of paper. The daydream was over. She looked down, as if she knew I was almost fully erect, underneath my desk.

“Now what were you dreaming about, Drew?” She knew full well that it was about her, and her still perfectly toned 45-year-old ass. I’d never been so attracted to someone more than older than me before. I usually prefer women of the younger persuasion, my ex wife was a decade younger. I mean, I’m 40, so i guess things are finally changing. It also didn’t hurt that our personalities meshed so well.

“Dammit Mel, I was almost most there. And whaddya mean, didn’t you see Katie and Rachel setting up that massive new whiteboard earlier?!” Read more »

Honeymoon With Mom – an 80s porn tribute – Chapter One [FMM, INCEST]

**CHAPTER ONE**

***Today…***

“Hurry up, Mom!

Brandon Crane sprawled on the bed in the master suite of the Aruban resort hotel, anything but relaxed.

His mother stood at the foot of the bed, clad in pink slippers and a short transparent nightgown that only accentuated the lush curves of her body. A ravishing, ivory-skinned redhead, at thirty-eight years of age Nicole Andrews, nee Crane, still had what it took to harden any man’s cock – especially her nineteen-year-old son’s.

“Patience is a virtue,” she teased, turning slowly so as to make sure that Brandon got a long look from every angle. Thanks to years of dedicated exercise she was fully aware that her lush, peach-shaped ass was still as high and round as a girl’s. Her slim thighs betrayed not a trace of middle-aged jiggle. Long hours at the gym had paid off in more than one way.

She had to admit that her most striking feature, her tits, were mostly a gift of heredity. She was delicately built, with a slender bone structure, yet her breasts were large and round and still firm with only the beginning traces of a little sag. Read more »