High School Archives — Page 251 of 805 — NSFW story

The Boss’s Wife: Part Two [MF] [Busty] [Interracial] [Huge Boobs] [Straight Sex] [Cheating]

After the events of last night, I didn’t want to look Tammy in the eyes. I couldn’t believe how many times I masturbated to her videos. I think she would see my need to see more of her if she looked into my eyes. The moment I woke up I gathered my clothes and called a taxi.

I didn’t wait for the taxi to get to the gate. I met the driver halfway down the street. I paid him in advance if he took the fastest route. Once I got back to my apartment, I fell back onto my bed.

“Damn,” I said as I paused the video on my phone. Tammy was on all fours on the floor of her dance room. Her big tits hung low, nearly touching the floor. Her ass was high in the air, and she was seductively looking at the screen.

Instantly my hand started reaching for my hardening dick. Just as my hand wrapped around it, my phone scared me as it began to ring. It was Tammy.

“Fuck!” I said aloud. I didn’t want her to think I was ignoring her, so I answered. Read more »

A Family Affair (No Incest) [MM] Part One

This happened when I was 19. I had been fooling around with a good male friend since high school. I would hang out at his house and we would do all sorts of things NSFW and SFW. LOL But this story is about something that happened one night when I was there visiting.

My friend’s father who had a job that took him out of state was home at the time. I volunteered to help with the dishes, he washed and I dried. My friend was waiting for me upstairs, so I was kind of thinking about that while we stood there. I had a pretty prominent tent going in my basketball shorts.

I realized that the father was staring at me. You know that feeling that you get when someone is looking but you can see them. I looked up an smirked at him, “Sorry” I said. He smiled back and we went back to the dishes. His hand a couple times brushed up against my hard-on, “by accident” I’m sure. We finished the dishes and he turned to me and I couldn’t help but notice his own erection. Read more »

Miss Personality: Final Chapter

Diane recrossed her toned legs for the tenth time under the glass table at the upscale bistro then wrapped a foot around the back of her calf to caress the lean muscle with the painted toenails peeking out her Givenchy stiletto. The distinct sound of her silky flesh, slithering back and forth, rang in every man’s head within earshot of the teenaged girl in her slinky cocktail dress. One man, unfortunately seated nearby, was pleading with his wife to not submarine the evening after she noticed him repeatedly glancing underneath Diane’s table. It was not the young girl’s intention to be provocative; she had simply never worn a cocktail dress before. When she purchased the garment at Nordstrom a week prior, she loved the way it fell so perfectly on her fit, youthful figure, dropping a few inches above her shapely knees. However, she had not accounted for the ensemble retreating up her thighs when seated. The hem was no longer alluringly floating mid-thigh, but encroaching on the lacy but minimalistic black thong that was the only other thing the girl was wearing. The tight-fitting dress formed a passable shelf for Diane’s massive but perky breasts. She had attempted to find a suitable backless bra but the only options she could find possessed neither the structural integrity to be useful nor achieved the intended aesthetic. Read more »

18 [F] Pantiless at the family and friends BBQ

I recently completed high school, so my parents decided to throw a backyard BBQ to celebrate my achievement. They invited all family and large swaths of friends and members of our church community (Evangelicals), since I didnt really have any friends of my own to invite.

Now, I’d be lying to say I don’t have at least some negative feelings towards most of the people in attendance since they are all close minded, religious fanatics, with strict and well defined gender roles I do not align with. So I decided to take action to make the most of it and enjoy myself!

And enjoy I did…

Before the BBQ, I asked around on what outfits to wear and even polled you, my online friends, whether I should be wearing any panties underneath my sundress.

It was so incredibly refreshing and empowering to walk around with just a flimsy piece of fabric covering my womanly body (I am thin but curvy), and talk to these people I had no sympathies for in most cases. I am normally very shy and socially awkward, but I just had such exciting news to share-with me moving away to attend UCLA at the end of summer- that I couldn’t stop going around to ensure I shared it with everyone before they left. Read more »

[M]y first [F]WB Made Me Cum in My Boxers, Pt. 3: How Many Pairs of Boxers Can She Ruin in One Day?

Once again, thank you all for your response to the previous stories of my quick, fun times with Haley. I’ve really enjoyed all of your comments, DMs/chats, and even awards (!!!). Sorry for the delay in posting these, I want to take my time writing them up! For those who have missed previous ones, you can find [Part One here](https://www.reddit.com/r/gonewildstories/comments/nh63ic/my_first_fwb_made_me_cum_in_my_boxers_which_led/) and [Part Two here](http://reddit.com/r/gonewildstories/comments/njidm7/my_first_fwb_made_me_cum_in_my_boxers_pt_2_video/).

Just to recap who I and Haley are, I’m Tyler. Currently 31, but an 18yo high school senior at this point. I was a late bloomer; a bit chubby until I grew into my height (6’2), and then became pretty tall and lanky. My cock is slightly above average size-wise (6.5 to 7″ if I’m really feeling it!), though I had no idea at the time that I was above average. I played baseball and was in decent shape, though the years of social awkwardness and not seeing myself as attractive had left me pretty unexperienced; I had kissed a girl, but never gotten past first base at this point. Until I started talking to Haley. Read more »

[MF] The college boy and the mature mom (very long)

[Repost from my previous account. I’m going to put up a few of my previous posts to give context to some recent experiences.]

Should probably start with a little explanation. As I was growing up I was tall and gawky with glasses and an overbite. Then I was an athlete 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 still understand the perception of not being considered attractive.

This isn’t the first experience I had or necessarily the hottest (though I think it’s pretty hot), but the easiest to write–my first experience with an older woman, which really got me into enjoying older women. I really am into the build-up and noticing details and emotions and hope you are too.

I was a junior in college, fall semester, still living on campus. On Tuesdays my best friend and I had a large open swath of time just after 11am, so we’d usually do something together–go shoot ball, grab lunch, go to a bookstore, lift, etc. For some reason on this cloudy, early October blah Tuesday we decided to go off campus and treat ourselves to that fine restaurant chain known as Chilis. We’re seated at a table next to three women in their late 40’s, early 50’s. My friend and I order our drinks and start looking through the menu. Read more »

Dorm Room Surprises Roomate[18][f]

I hated the start of my Freshmen year with a passion. Our dorms sucked. No privacy at all. They consisted of two, two person rooms with a shared bathroom. No control over who your room mate or suite mates were was also a sore spot with me. I did not go to college with any of my high school friends. So, I was stuck with who ever they assigned me with. The floors were supposed to be segregated by gender. However, our RA didn’t give two shits if we had girls in our rooms at all hours.

On the first day, my room mate and our suite mates got together and talked. It turned out that my room mate, Jeff, had a long term girlfriend, Christy, and both of my suite mates also had girlfriends. I liked my room mate. He was very considerate of our shared space. He would always ask if his girlfriend could spend the night with him in our room. However, the douche bag suitemates never asked us once. Even though we all shared the bathroom that their girlfriends would be using. Read more »

[F] Relationship with my boss to pay for my son’s education

Hello to all,

I’m not proud of it. But the last two years my boss and I have had a secret relationship. I have a 18 year old son who just graduated high school. I’m a business professional and work in the medical field. I do outside marketing. Essentially, this started happening two years ago when I told my boss I was thinking about leaving for more money because I was dealing with financial issues. We discussed my future with the company. He offered to be my mentor and invest more time into me. Things weren’t sexual at first. But it developed into that. I doubled my commission because he gave me more territory to work with. I have no regrets and it’s still ongoing.

The MILF Chronicles – Prologue

This is a first draft. Comments and constructive criticism always welcomed
The MILF Chronicles

Part One: Prologue

Everyone has a story to tell I guess. Some are more interesting than others, so I will let you be the judge of mine. My story is one of change. Perhaps change is a bit understated. Radical transformation might be a better way to describe it. I want to relate to you my tale of how I evolved from simple, middle-class housewife to a voracious sex crazed Cougar. It all began with a divorce.

I know that most of these stories begin the same. We married young, right out of college. Had our son less than a year later. He went to work climbing the corporate ladder and I stayed at home being the mom.

Our sex life was average. Nothing out of the ordinary. He was an attentive lover, always making sure that I had at least one orgasm, but doggy style was considered adventurous for us. As the years passed and our son grew, sex became less frequent, less passionate, more like going through the motions. Read more »