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.

Our First Date [MF]

C and I met 2 months ago. She’s 19 and I just turned 21. Since we started dating, we’ve been fucking nonstop. Before we met, she was a very VERY horny virgin who wanted to be treated like a slut but also wanted something serious. I was all too happy to oblige. And as I’m writing this, she’s beneath the sheets sucking my dick.

So onto our first date.

She and I met outside a restaurant at a local outdoor mall. Dinner was going well and I felt things were going great. All of a sudden, she starts talking about how she gets turned on by outdoor sex and would love to fuck outdoors one day. Immediately the whole atmosphere of the date changed and I knew we were gonna mess around.

We quickly get our check, and walk out to my car. We get in the back seat and start making out while I grab her pierced nipples and suck on her neck.

I’ll let her take a break from sucking me to tell you how the rest went down:
He asked me “have you ever sucked dick before?” I answered no having had no prior sexual encounters before this. He said “do you want to try” and I was all too happy to oblige.

[MF] Getting the nerdy dancer

In my 20s, I worked full-time, went to grad school at night, and had picked up a part-time job with a local minor league team in my city.

One perk of working with the team was interacting with the dancers. They were a mix of “older” women in their mid-20s to mid-30s that had reached the term limit of the local NFL team, and then the aspiring 18-20 year olds, just out of high school.

During an official post-game after party, I flirted a bit with one of the dancers, Ali, after the other girls teased her for liking Lord of the Rings. Apparently her father had read it to her as a kid, and they saw all the movies together, and it was a big thing. I jumped into the conversation, telling her I loved LotR. The other dancers laughed at us and left.

I geeked out a bit with her, discussion the books and films, and we made plans for her to come over for dinner and start watching the trilogy.

She was supposed to show up at 8, but knocked on my door around 7. She was coming from dance team practice, and figured it would be easier to just shower and change at my place.

A Helping Hand: My Best Friend’s Mom [Fm] [str8] [handjob]

The sky was unusually cloudless that morning and the slight breeze the wind was casting felt more refreshing than chilling on their salt covered bodies. Bodie and Ziggy were on their way back from a morning swim off the coast of Boca Raton, their bodies aching slightly from the rough waves they had attempted to bodysurf. Bodie lived about three blocks up from the beach in a cozy little house with his mother. Summer break had started roughly three weeks ago and the last day of school was the same day as ZIggy’s 16h birthday. There was an extra reason to celebrate that year.

“Thank God the ocean floor is all sand, otherwise I think I would have bashed my head on some coral on that last one.”, Bodie said massaging his neck.

“Maybe if you were a better bodysurfer you wouldn’t have that problem.”, Ziggy quipped back. Bodie gave him a friendly jab with his fist.

“Well, you saw those girls that were watching, I had to do something impressive.”, laughed Bodie.

Roommate [F] caught me [M] masturbating [college] [inexperienced] – Part 2

Link to Original Post here: https://www.reddit.com/r/gonewildstories/comments/59t4ga/roommate_f_caught_me_m_masturbating_college/

Holy crap Reddit. Sorry for not posting for so long – some big things happened in my life just a week after my original post, and I completely slipped on updating this story. Things are still settling, so I’m not sure when I can post again, but I had a free night and wanted to post part 2 of my previous account of my sophomore year of college.

Once again, same warning: not the kinkiest story around, just the classic story of a boy jerking it to a girl. And be prepared for a lot of jerking (seriously, a ton). Also, Part 2 is LONG AS HELL. A lot of setup took place before the next big thing happened between us.

At the end of my last post, I said the embarrassment was gone once I had caught Vanessa masturbating after she caught ME dick-handed in the bathroom. Well, I was wrong. By morning, I was so completely ashamed and embarrassed that I didn’t even come out of my room. I had absolutely no idea what to say, and even less idea of what to do. But all I know is that I was completely blindsided – Vanessa was SMOKING HOT and I couldn’t believe that I hadn’t seen it before. My Sunday morning was filled with two cycles of embarrassment followed by replaying the events of the previous night followed by jacking off followed by deep shame. Rinse, repeat.

Eileen Learns What A Furry Is/Happy Hour; [FMTT][furry][gang][anal][drugs][exh][huml][fantasy]

Does this make me a bad person? Maybe… Do I plan on stopping soon? Hell no. You’re gonna take this disgusting filth, and you’re going to like it ;)

~~~~~

There’s a lot of blame to go around for what happened this time, and I’ll admit, some of that blame belongs to me. Before I get into that, I’ve got to ask, do **you** know what a furry is? I mean really. I thought I knew. I mean, I’ve seen some of their artwork on the internet. I’ve even seen clips of conventions, with adults going around in suits, to drunken orgies.

When you’re a sex offender, your social circle has a way of shrinking. If you’re a known horse fucker, even your family will abandon you. I found myself sitting alone at a bar on the wrong side of the wrong town, just to be in a place where no one knew my name. I was in a stupor by 3pm, head down on the bar, with peanut shells in my dirty blonde loose ends. I was at rock bottom.

Daddy Took My Virginity On My 18th Birthday[Str8][fM][inc][oral]

My name is Felicity, I am 18 years old and I have just become a woman. This is the story of that moment and of the realization of my most shameful and glorious fantasy.

When I hit puberty I never really was very interested in boys, I didn’t date, I didn’t even begin touching myself until i was 16. I just had no interest, i had seen sex scenes in movies, some friends in high school used to giggle while watching porn videos at sleep overs, i dont know, it never really seemed exciting to me. I tried, of course, i participated in the normal slumber party experimentation, but even as i had a cute 17 year old red head buried in my pussy, i just felt bored and underwhelmed by it all. The very first time i felt that sexual tingle was when, at 16, my father walked into the bathroom as i was showering. Something to note, i look very similar to my step mother. We are the same build and height, we both have fairly small, perky breasts and pale white skin. I have lighter and shorter blonde hair than she does, down past my shoulders, but when wet it looks a lot darker. At this moment i wonder, well, i secretly hope, that my father married her because she looks like me.

[MF] Losing my virginity to a complete stranger

Ok, this is the night of the first because this is my first post in GWS and IDK how to format the story. This literally happened an hour ago and I just got home still baffled and I’m kinda paranoid because I lost my V card but it was with some random ass stranger I don’t even know and I really hope I don’t get a disease for this.

I think you start with some background about yourself? I don’t really know but anyhow I’m a 5’4 black male college student in my second year ( if this turns you off you can leave). I’m not sure if I’m attractive or not because most of my friends are not so attractive nerds but sometimes I get the look from women (maybe it’s cause I look like a freaking 12-year-old IDK). I weight 140lbs with a 8% BMI and I am a do wrestling on my free time( I guess this helps with sex)

Starla’s Sex Journal 1/3/17 [Ff][Fdom][Fsub][breastfeeding][trib][oral][non-fic]

Kiera and I had a deep, productive heart to heart over cider last night. I figured it would be best to come clean about the story that I posted about us, but to do so when she was slightly buzzed. I wish I could say that she was thrilled about it, and we immediately banged each other on the couch, but that’s not what happened at all.

She was very creeped out by it at first. She told me to delete it; I said I would, but I wanted to explain myself. I told her that when we did what we did, it was such an amazing, unique experience, but I didn’t have anyone to share that with. Not talking about it with anyone was pure torment, and I couldn’t handle it. So, I told a bunch of strangers online, who will never know our identities. She asked if she could read what I said.

There was a sliver of cider left in the bottom of her glass by the time she read through it. I waited, two couch cushions over, for her verdict. She didn’t turn her head to me, but she leaned away from the screen, and set her glass down, to speak. “You made me sound like a cow…”

[MF] Breaking out of the friend zone and popping my cherry all in one night

This true story takes place in the mid 1980’s in a northern English market town. It is my first post so please let me know what your thoughts are.

First off about me, average geeky 19 yr old teenager tall with average looks and an average sized packet; Mr average all round. Her, tall brunette, same age, on the chubby side but sexy as hell with big tits, we’ll call her Jen.

We met at college and had known one another for 3 or 4 months. Because we lived in the same suburb we would often catch the same bus together. I would always make sure that i walked her home before heading to my house.

As I say I was a typical geeky teen and more than a little nervous, shy and socially awkward around girls. As much as I wanted to, I couldn’t bring myself to try it on with her, fear of being rejected was probably high on the list.

Thursday, Friday and Saturday nights were always huge party nights and going downtown to get hammered was the normal routine for most college students.