High School Archives — Page 563 of 805 — NSFW story

Sisterly Support [FMF] [Oral] [Inc]

“How long is this going to take, Jan?” asked a restless Brittney Lawton.

“Why? Did you actually have plans for tonight?” replied her bemused older sister, Janet.

“Watching movies and eating leftover Thai food counts as plans.”

“In that case, this may take longer than I thought.”

Brittney groaned to herself as her older sister led her up the stairs of the quaint, suburban house she shared with her husband, Kyle. She wasn’t in the mood for another one of her half-hearted efforts to boost her spirits. She’d had enough of those over the past seven months. While her Janet’s heart was always in the right place, she had no idea what she was going through.

“Seriously, Jan,” she groaned, “I don’t have the energy for this tonight. I get that me living here is a pain in the ass, but let’s not make this harder than it already is.”

“I’ve been watching you loft about this place for months, looking miserable and depressed at every turn,” Janet said, stopping just at the top of the stairs. “Trust me. It can’t get much harder.”

“Famous last words,” Brittney muttered. Read more »

After Soccer Practice [M/F]

*Written by me; originally published to Literotica March ‘07* Hope you like it

Dan Wilson tossed his keys and wallet on his kitchen table. It was an unusually warm April afternoon, so Dan had used his boss’ absence as an excuse to skip out of work a few hours early. He loosened his tie and cracked open a cold beer from the fridge.

At 30 years old, Dan was rarity in his neighborhood- a single man in a community filled with families. But with his parents retiring and moving to Florida a few years earlier, Dan had taken the opportunity to move into his parents’ old home.

Sitting down to check out what was on TV, Dan heard the sound of a car door closing across the street and looked out the window to see his neighbor’s daughter, Emily White, getting dropped off from soccer practice. Dan had been eyeing Emily since he first moved in and since her recent 18th birthday he felt a lot less guilty about his increasingly frequent and wild fantasies about her. With a perfectly toned and tanned body, Emily was the object of desire of not only her fellow high school seniors but also her sex-starved neighbor. Read more »

My fiancee and I had a threesome with an escort [MFF].

***There was some interest in doing a write-up on this experience based on our recent post in r/sex, so here it is. Enjoy!

While I sat on the hotel bed, I rubbed my hands on the sheets. “Damn, they’re still clammy.”

This night had been nine months in the making. Tonight, my fiancee Jenny and I were going to have a threesome with another woman. Jenny and I had discussed everything about this night and had prepared things the best we could, but once you’re actually there it is a whole other story.

8:45 PM. It was fifteen minutes until Rosa was suppose to get here. We had found her through a high-end escort agency. The first thing Jenny said when she saw her picture was, “Damn she got some big ol titties!” But that confidence was now both gone from both of us as we nervously waited. Read more »

Cougar Co-Worker [MF]

She was 51, I was 27. It’s sometimes hard to believe that nearly six years has passed. I started my first job in “education” fresh out of college. At the time, I found myself lucky to be back at my high school. However, you find out quickly that nothing ever changes. The secretary who provided hundreds of boys with fantasies during my formative years was still working there and this time, freshly divorced. There she was, all five feet of her Italian-American olive-skinned curves. Brunette waves gently touching her shoulders and breasts that were balanced out well by her thick ass.

We developed a friendship easily and the office flirtation grew over time. Her sex appeal was evident as was her naivety. She confessed to me that she had never been with a man other than her ex-husband whom she had married at 19. I was in a serious relationship and didn’t want to fuck anything up, so I never stepped into my fantasies. Until I became unhappy – and she noticed. It only took about four and a half years, but we tiptoed into it. Read more »

Southern Hospitality [FM]

When I travelled for my first job, if I was going to be somewhere for consecutive weeks I’d usually just stay for the weekend instead of dealing with the flights back and forth. I worked with some cool people who would invite me over to eat so I wouldn’t be stuck with restaurant food for weeks at a time.

I got invited to a cookout with a friend from work one weekend and was the youngest non-child there by a few decades. As I’m meeting folks, making small talk, and getting to know my friend’s friends, one of the ladies started asking a lot of questions about how I spend my time travelling. “Call home? Call your girlfriend? Hang out with people down here?” So I explain I’m single, talk to my parents a few times a week, and usually sit at the bar and eat. “Well, let’s introduce you to some folks.”

Next thing I know, her phone is out and she’s talking to someone. “Come over to the Jones’ house. I have someone I’d like you to meet.” Read more »

[MF] College bday weekend with H

It was my last birthday during my college year.
Having a January Birthday means it falls during winter break 70% of the time. So this year was no different except for the fact that I decided not to go back home this year. I wanted to spend my bday on campus with my friends.

Well just my luck my bestfriend went home because his brother was having a kid so I decided to send out a few texts to friends I knew at other schools to see if anyone wanted to come up for a few days. One response popped up. H was a good friend I knew from high school. I found out she recently broke up with her dude and just wanted to party. H ended up driving the hour to my apartment where we spent most of the time just hanging out and drinking until it was dark out.

So a few beers and about half a bottle later we decided to head out to the local bars to have some fun. With it being my birthday I had one objective… get absolutely trashed. From what I can remember of the drunken time traveling experience through the night, H and I relieved a lot of sexual tension while dancing. My tongue down her throat as I gripped her ass. Her grabbing my increasingly large bulge in the middle of the floor and asking me to leave. Read more »

The [F] awakening

The summer between junior and senior year I had blossomed into womanhood with a vengeance. My mom had always said I was a late bloomer. All of the women in the family were. My body decided to make up for it in those few months. I got taller, thinner, and filled out in all the right places. When I returned to start my senior year there were rumors I had plastic surgery over the summer because of the dramatic changes. Because of the newly acquired boobs and butt, I had been getting attention from boys who had previously ignored me. Here I am 18 years old, not much over 5 foot tall, around 100 pounds and DD tits. I looked like my mom and her side of the family. Her best advice was that with great breasts come great responsibility.

We were preparing to have a final party before high school graduation. I was at my friend’s house helping get things ready. Really just drunk proofing the house. The handfull of people lending a hand had gone outside to smoke. I have asthma and smoke allergies so I stayed inside. Read more »

[MF] 18 Misty Part One – Church parking lot

When I was a senior in high school, I starting dating Misty. She was short 5’3 with decently heavy C cups and a tight 18yo ass. We had been dating for several months and even though this was not the first sex we have had it certainly was the most exhilarating and my first foray into the world of less than vanilla sex. I had picked her up from her parent’s house and the intention was to attend her church together. While driving there I was starting to get handsy and my fingers began wandering up and down her thigh. “You’re starting to make me wet,” she said as I continued to rub her leg. Misty let out a little moan as I moved my hand down between her thighs and began rubbing her crotch. I kept teasing her all the way into the parking lot. Because we were running late we had to park at the back. Misty attended one of the mega churches in the city so there were already a few hundred cars there. Once we parked Misty reached out and grabbed the bulge in my pants and started stroking my cock through my pants. “Fuck, I’m so horny. I don’t think I wait till after church,” she said while rubbing my cock. She undid my belt and zipper then pulled my cock free. I then reclined my seat so she could blow me. Leaning over her seat, Misty then started licking up and down my shaft. Slowly teasing me, she started blowing me right in the church parking lot. After a minute I couldn’t take being teased anymore and told Misty I needed to fuck her. She then undid her shoes and pants and slid them onto the floorboard of my passenger seat. I reclined my seat back farther and she climbed ontop of me. She slid my cock into her soaking wet pussy and started to rock back and forth on my lap. Moving up and down, she started pumping my cock as we made out in my car. After only a few minutes I couldn’t last any longer and shot my cum deep into her welcoming pussy. She milked my cock for a few more good thrusts then slid off me and back into her seat. We skipped church and went back to my parent’s house to have more sex.

[MF] Business Travel Fun

So this happened about 3 months ago. I was traveling for work and after a long flight I finally arrived at my hotel ready to check-in and go up to my room. I get to the lobby and it’s packed. Apparently there was some high school drama competition or something for the state and they were all staying at the same hotel.

After waiting a long time to finally check-in, I head up to my room and do some work for a few hours. At about 10/10:30 I decided to go to the hotel bar and have a drink or two to unwind.

I go up to the bar and order a drink; that’s when I see her. 5’2”, dark hair, Latina, thick with a big round ass and big, fake DD tits. She’s wearing a blue dress that has a white collar. She looks young (not like high school young, like early/mid 20s young). Read more »