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.

[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)

[M]y [f]avorite summer with the college girl next door

This story took place around five years ago, but I still remember it quite well…

I had graduated college, and got a job in a small town. Finding nothing but overpriced rentals in trashy neighborhoods, I decided to buy a house of my own. I finally found a fixer upper right on a quiet street that was surrounded by mainly older families from what I could tell. Between a cold winter, work, and remodeling, I didn’t meet any of the neighbors other than a passing wave. Not much changed until spring had passed, and a warm summer was arriving.

I was outside doing some landscaping one day when I noticed a car pull into the house directly across the street. I could see the back seat was packed full of bags and boxes. I put two and two together and realized it was a college student returning home for the summer. My full attention was focused that way when I first saw the long blond hair come out of the car. I watched as a beautiful tall, fit, tan body emerged from the car, as I tried to not stare. Fortunately she was busy gathering bags and boxes to carry inside and didn’t notice me across the street. Since she was only wearing a tank top and shorts, I could see her toned arms, shoulders and legs, and knew she was obviously an athlete. The basketball hoop in the driveway that I hadn’t really noticed before suddenly became obvious. She carried her things inside and I did not see her again that day.

[MF] Fiona, Part One [exhibition]

So, sequel to my last story. After my relationship with Chelsea finally, definitively brokeup, I had a one night stand with my friend, Alexis, who was married to my friend Brian. Then I went on a hardcore celibacy phase just to focus on myself. It was paying off in that I was working out more, getting ahead in my career, and building confidence. I was sharing an apartment with a roommate at the time. His name was Derek, and we got along fine, but sometimes I just needed to get out and have my own space, especially when his girlfriend, Elise was over. There was this local bar in my neighborhood, the Blue Star, that had good beer, chill clientele, and no TVs. It was a great place to kill an afternoon with just reading.

The Time With the Theater Girl From the UK [MF]

My economics class my sophomore year was brutal. Like, impossibly hard. Not because the subject was one I didn’t grasp, but because the professor was the most inept college professor ever. She was this little, mousy lady who had chicken scratch for handwriting. Anytime she would write on the board, it was impossible to read. And she never taught what was on the exams. This was one of those classes that you had to teach yourself and hope for the best.

From the beginning of the semester, I usually sat in the same seat each class (I’m just weird like that), and for the most part the same people sat around me, but everyone tended to keep to themselves. There was one girl in particular that always sat on my left with a seat between us. She wasn’t drop dead gorgeous, but her face was striking. Very symmetrical and intense. And for that reason, she was attractive. She had shoulder length auburn hair, dark brown eyes, and wore a bit too much eye makeup in my opinion with the winged eyeliner, but it fit her I guess. Her body was nothing to brag about other than she was tall and slim. She could definitely be a model, but had no real curves. The only other thing I knew about her was that her name was Leonie, which I thought was interesting.

Splitting [MF] [oral] [bd] [Mdom] [long]

Splitting

“I’m sorry sir! I won’t do it again! Please! Please!”

“No. You won’t”. I bent over the bed to kiss her one last time, placed a hand on her throat, lightly squeezing. “I’m going to leave this cabin and you’re going to lay there and think about how close you came to disobeying me. When I’m done out there I’m going to come back in here and fuck you senseless. Once you’ve swallowed every drop of my cum, it might be your turn. Do you understand?”

Her body writhed against the restraints, pulling at the cords. Her breath came staccato as she continued to subdue her arousal.

“Yes sir. I understand” I moved my face close to her, one hand over her throat.

“What is going to happen?” I whispered into her ear.

“I’m going to lay here” she recited, “and think about how close I got to cumming. When you’re finished, you’re going to come back here and fuck me senseless. Then I’m going to swallow your cum. And then you’ll let me come.”

I pulled back and gazed into her eyes: “Maybe.”

My first time with a girl. [FF]

You guys seemed to like my last story so here’s another.

I always knew I was gay. My family is super religious so I did my best to stay in the closet (dad’s a minister). Finally when I got serious with a man, I knew I couldn’t take it anymore. I came out, but I had no idea how to talk to women as I’d only kissed them, so I hit up Tinder.

I was too nervous to talk to girls on Tinder, until I met this sexy tomboyish blonde, S. We talked for a couple months, I repeatedly blew her off due to nervousness, and we finally met up at a coffee shop.

I was early and my phone was dead. I pretended it wasn’t, because I was so uncomfortable. As soon as she walked in, my jaw dropped. She was tomboyish, yes, but she was fucking gorgeous also. Imagine Jodie Foster with a side shave. We talked for hours. I left, and then hit her up a couple hours later saying I didn’t actually have to leave, I was just nervous.

[FM] Fun on the beach during a short vacation

My previous story is [here](https://www.reddit.com/r/gonewildstories/comments/5jr9ly/fm_quiet_guy_at_the_bar/).

I tried writing in a bit of a different style than the last one, still trying to find what works. Hope you enjoy!

My parents have a timeshare that they generously allow me to use. You can get lavish hotel nearly anywhere in the world. Sometimes I travel with them, or with friends, and sometimes I go alone (I also get discounts on flights). You might think it’s scary for a woman to travel alone (I was at first, and sometimes it is), but generally people are very nice and friendly, especially if you speak a bit of the local language. The timeshare works on a points system: you get an allotment of points per year, and different hotels cost a different amount of points per night. One summer, they offered me their remaining points for the year. They had already booked a few vacations for themselves, so there was not much left over for me. The points-cost of a night’s stay followed supply and demand, so hotter and more tropical places are much cheaper in the summer than in the winter, since everyone wants to go to warmer places in January. So what could I afford with my small amount of points in the middle of summer? A modest three weeknight stay at a remote tropical beach resort in another country! Luckily I don’t mind the heat.

First time with my hotwife in person [MFM] (X-post r/hotwife)

Had a really fun night so need to share! Also looking for some thoughts/feedback at the end (EDIT: And naked pics!).

Wife and I have been non-monogamous for a long time, both occasionally taking advantage of it. Last night we went to a swingers club (not for the first time) but I had the first experience where I was just watching instead of participating.

When the play area opened I spent a little while eating her out and having a good time, after she came we got up and went for a bit of a walk. This club has a sex swing that she’s always wanted to use, but I wasn’t really feeling it tonight, so I slapped her on the ass and said “go up to someone and say ‘I’ve always wanted to try the sex swing, want to come join?'”

She wanders away, and as she’s walking back into the room someone taps her on the shoulder and whispers something into here ear. I see her nod, and the guy reaches around her and grasps both of her breasts massaging them and kissing the back of her neck, which is one of her favorite things. She smiled at me as he pinched one of her nipples, then she gasped kissed him, and they separated.