Tag: High School

Coerced by my stepdad into having sex…not regretting it (m/f)

This happened just over three years ago when I was a senior in high school.

 

My mom had been dating a rich guy named Steven for six months and we just moved into his house before Christmas when they got engaged. I don't really like him, but my mom LOVES him and he basically took us from a small apartment in a bad area to a huge house in a good neighborhood. He is handsome and has money so I'm happy for her, but he was saying sexual things to me which creeped me out and kinda turned me on at the same time. In front of her, he would call us his "beautiful girls" and make comments about what I was wearing and what about me I got from my mom. He said stuff like "I'm glad she has a boyfriend so there aren't all these strange boys knocking on my door…"

When she wasn't around, Steven complimented me more sexually and one time he hugged me and his hand went down my lower back to my ass. The most obvious sexual thing, and the catalyst for our sexual encounter, was he walked in the kitchen in just his boxer briefs when I was eating breakfast and my mom was in the shower. Read more »

Freshman Adventures: Spring Break, Part 3

I rested my head on Anjali's chest for a few moments thinking of what I'd do to get her screaming. As I pondered, she sat up and shifted forward and next thing I knew her mouth was around my cock, furiously sucking it while grabbing me by the waist as if I might escape. I nutted in her mouth in about three minutes and she tilted her head back, again, as if having done more coke, and swallowed three times. I stepped back and almost fell against her window. I felt so fucking good in that moment and shut my eyes. The next room over, I heard the door shut and Dirk and Anjali talking in whispers.

I began laughing. I heard her chuckle. I opened my eyes and burst out laughing and she burst out laughing also. Her cheeks were red and it looked almost as if she’d been crying. She sat up and looked down at her stomach, quickly, with an embarrassed grin, and back up at me with a grin that could not believed I had persuaded her in to this situation. Read more »

The Night I Played a Game Called Cluster(f)uck

Here’s a story that happened a few years ago when I was single and child free. It happened one weekend when I was visiting my friend at college in New York. I had been friends with Jessica since high school and I hadn’t seen her in the six months since she had swapped cities. She was living in a dorm and had a new boyfriend that she met there. At the time we were all 19 or 20, Jessica is around 5’5 with blonde hair and blue eyes but her greatest asset had always been her large tits that measured in at 32DD. Her boyfriend was called Marcus, I had never met him before but found him to be very attractive and charming. He was a native New Yorker, around 6’2 with dark hair and a well-developed body due to his weightlifting regime.

I arrived on Saturday morning at JFK and got the train to Jamaica Station where Jess and Marcus were waiting to meet me. I was immediately attracted to Marcus and it was great to see my friend again after so long. We got the train to Manhattan and spent the day being tourists and catching up. We had our dinner downtown before it was time to head home, Jessica told me that we were going to get drunk that evening and have some fun. Little did I know! Read more »

My First Time Having Sex in Public. (m/f)

I've never considered myself much of a writer, but I figured I should contribute to this sub since I visit it so often. My sex life has been waning in recent years, but it was pretty exciting for the majority of my adult life. Maybe I'll post more if this goes well. Feel free to comment, I'm genuinely interested in what people think.

Background: All through high school, and Bailey and I were close friends. She was about 5'5”, pale as can be, and though I dont know the specific size, she had the largest breasts I have ever had the pleasure of pleasuring. Her face always reminded me of Kate Winslet, but with a deep purple bob cut. She definitely played to the 20's flapper girl type of fashion, which I loved. All of that being said, my intense attraction to her was by far more mental. We were both huge geeks, and aside from obvious nerdy fair, we would spend hours and hours talking about religions, politics, philosophy. It was clear that there was a mutual attraction from day one, but being young in high school, we never pursued it beyond friendship. Read more »

(M)y second time with a (T)rans girl

This is a follow-up to my first story. Still a true story, so I apologize in advance if something is less than sensational. This one is a bit longer though.

I left my friend's birthday party in a fog. I had just had the most amazing sexual experience with a trans girl I had met at the party. It was something so unexpected, both for the fact that it happened and because I had never thought of doing anything like that before. Don't get me wrong…I had no hangups about it. No regrets or anything like that. I was just in this stupor from how awesome it was.

I went home that night and couldn't keep the night from replaying over and over in my head. And yeah, I rubbed one out thinking about it. I was still so hot over the situation.

Before we left the party, I got Claudia's number. I definitely wanted to see her again, but also was trying to play it a little cool by giving it a day or two before calling her. The party was on a Saturday and by Tuesday, I couldn't wait any longer and gave her a call. It was a bit awkward because I was thinking the whole time "hey, you remember Saturday when we banged like there was no tomorrow? Yeah, I want to do that again." To her credit, she was really easy to talk to and seemed eager to meet up again. Read more »

(F)alling towards the dark side (m/f/f)

Before I go into my life, a little about my life. You can call my Alyssa, I'm currently 23, I am part Norwegian and part Italian, with Texas in my blood. I'm 5'3, have lush black hair that I keep at shoulder length, I'm 109 lbs, I have 34b cup breasts, and small but perky booty that I try to work on day to day to keep in shape from my high school lacrosse days. Back in high school I was a prude. I didn't have an interest in sex and hardly had many boyfriends. My senior year I had boyfriend that I finally let take my virginity, and although it was not the most pleasant experience it exposed me to my first orgasm. After he and I started dating more sex followed as well as the acceptance of masturbation, and how much of a loser I was for not realizing how amazing that was before either. Anyways the high school boyfriend and I broke up and I moved to Florida to go to college and further expand my experiences. College was an eye opener. I was exposed to so many new things sexually that I started to really realize how much I enjoyed having sex. My first major eye opener was when I had my first threesome. One of my friends Meg who I remain friends with today had a boyfriend at the time named Alex. Alex and Meg were always together during our freshman year, and even more so when Meg and I moved into a house together our sophomore year. The two of them were constantly having sex in the house and I ran into both of them on occasions strolling down to the kitchen fully naked after sex. Meg and I were also attached at the hip so we would talk about guys and sex a lot with each other. One night we discussed the topic of threesomes and she asked if I had ever had one. I explained that I hadn't but came close to having one freshman year in college. She explained that she had had a few with Alex and that it was fun. We talked about the idea but never acted on it until a few months later. Alex, Meg, and I were all out partying with some friends one night when I became the designated driver and drove Meg's car back with Alex and Meg fooling around in the back seat the whole time. When we finally got back to the house they made a few drinks in the kitchen and I joined them. Meg came up to me at one point and whispered in my ear that she was horny and wanted me to join her and Alex. At first I was embarrassed at the proposal but after a few drinks and seeing them grope each other in the kitchen I made my way over and started making out with Meg. Meg kissed me back sliding her tongue into my mouth while she reached her hands around my hips and pulled me in closely. Alex jus stood there and whispered "fuck" to himself while Meg and I continued to embrace each other. Meg slowly stopped kissing me and guided me towards Alex. I tiptoed up to Alex so that I could reach his lips and kissed him slowly. By now I had been with my fair share of guys and although Alex wasn't the best kisser he knew how to turn me on. Alex lightly bot my bottom lip while her grabbed my ass as Meg stood behind me and undid the back of my dress. Alex and I broke our kiss as Meg tugged my dress down to the ground as I stepped out of my heels around the dress leaving me in just my bra and panties. Alex lifted up Megs skirt and began rubbing her pussy through her underwear. Meg moaned into my ear as Alex playfully bit her neck. From there Alex undid his pants and pulled out his dick. It was average length and thickness but got skinny towards the tip. Meg knelt to the ground and told me to join her. She lick the tip a few times before smiling at me and telling me to try. my introduction to blowjobs my freshman year had me hooked and Meg knew how much I loved it. She guided my head towards her boyfriends dick before my lips were brushing the tip. I ran my tongue around the tip a few times before I licked down his shaft and sucked on his balls. While I was licking his balls Meg returned to sucking the tip of his dick while she stroked him back and forth. We switched positions after a little while before he explained he was going to cum. Meg and I straightened back up kneeling in front of his dick while he pumped his fist back and forth on his cock. He shot his first spurt of cum onto Meg's face before pointing at me and pumping a few more spurts onto my face and tongue. He went back to Meg to finish up before falling to his knees and kissing Meg on the forehead. Meg looked at me and kissed me with her cum covered lips as mine hit hers. We kissed some more before getting up and cleaning ourselves up. We went upstairs after we got cleaned up and climbed into Meg's bed to continue the fun.

(M)ore o(f) my misspent youth.

This story follows up a story I wrote a few months ago.

I’d been in a relationship with Sara for a year before we split up. Sara was fun in bed but public sex was her thing. It turned her on to think we might be caught in the act. She loved fucking in her little red Toyota MR2. I’m six-one so her petite body was the only thing that made it possible. She had places to park all over the DC metro area, but we had car sex mostly in Northern Virginia where we worked.

I remember spending the night at her parents house. I slept in the guest room but in the morning I went to her room, she insisted we leave the door open which was one of her parents rules. She said, “Keep your clothes on then lay behind me on your side and we’ll spoon. I’ll slide my pajamas down and you pull your pants down.” It wasn’t great sex, I’d have liked to tear off her clothes and had her bounce on my cock. Later we went for a bike ride and fucked in a field just out of sight from the bike path, it was fun but really not very comfortable. Read more »

Taking /u/highavailability’s anal virginity. Lots of pictures. [f/m] xposted from /r/hastories

It’s no secret that I’m kindof obsessed with HA’s ass. It truly is a thing of beauty. I’ve never been particularly interested in exploring the male-gspot with anybody else, but HA’s ass is just begging to be played with. I initially approached that line awhile back when we were both pretty heavily under the influence. There was only light external massage on that occasion (mostly bc I have long fingernails), but I couldn’t stop thinking about it thereafter. HA was, understandably, apprehensive about the possibility, but somewhere along the way his curiosity got the best of him and he gave me carte blanche to do whatever I wanted…with the stipulation that anything I did to him, he could also do to me. Well, seeing as how he has fucked me in the ass on multiple occasions, this fine print didn’t dissuade me in the least.

At the time, I didn’t think I’d be seeing HA until mid-January, so I leisurely started reading up on prostate massage, watching tutorial videos, and consulting with my gay bestie. I ordered some things online and continued with my “education” because I approach sex like I do everything else….all or nothing, and if I’m going to do it, I’m going to do it right. Read more »

Cheating on my boyfriend by sucking 2 guys [FMM]

So I've always been a horny person but never considered myself super slutty. I had my share of hookups and I'd done some kinky stuff but I wasn't nearly as slutty as some of the girls I'd seen at parties and stuff. About me – 5"10', tanned, D cups, long brown hair, athletic body. I've always got attention from boys and I admit I'm a huge flirt and a tease most of the time, but if never cheated before. I started dating a guy named Ben the summer after high school. He was the 5th guy is ever been with and I figured it'd just be a summer fling hook up type of thing but we got really close and started dating towards the end of summer. Our colleges were a few hours apart which made it hard and left me really horny no matter how much I masturbated haha, it just wasn't the same. We tried to see each other every other weekend but as Christmas break of freshman year guy closer we saw each other less and less with bad weather and conflicting finals schedules. Read more »

Lost my virginity to my best friend (mf) (Cheating)

So to start this off, I'm here to turn people on, not start a moral debate, if you don't like what I've done, don't read it.

In my last year in high school I was a bit of a late bloomer. I had a handful of girlfriends but nothing past second base. I started getting close to Erika and Anna both at the end of the year. Anna was in a long term relationship, but we had grown extremely close to the point that I considered her my closest friend. Anna was about 5'2'', blonde, blue eyes, with curvy hips and D cups. Erika, while on the less attractive end of the scale, had a great personality, with red hair and freckles. She never wore makeup and was a tom-boy.

Erika and I entered a highschool type, hands holding, light peck kisses only type of relationship a couple months before prom. We never had sex, she'd barely touch me for the most part. We had next to zero chemistry, but I wanted to give it a go anyways, since I had gotten desperate. As the partying picked up, Anna and I would flirt more and more. Grinding, arm on the leg when laughing ect. The sexual tension between us became palpable when we were alone. Read more »