High School Archives — Page 50 of 805 — NSFW story

I [F22] had sex with another guy and he came inside me hours before seeing my boyfriend (boyfriend didn’t know) then my boyfriend wanted to have sex with me and started eating me out… [F]

This is back when my boyfriend and I were both 20, we were high school sweethearts and I feel really bad about it. We’ve been broken up for years but I just wanted to tell my story.

My boyfriend and I dated all throughout high school. We were deeply in love with each other. He was the nicest guy ever and I still regret it. So I have always had a thing for this guy that was 2 grade levels ahead of us. Let’s call him J. He was cocky, douchey, arrogant, and a running back on the football team. His physique was amazing, and he was so hot. All the girls wanted him. We’ve always followed each other on social media and I wanted to keep in touch with him. Read more »

Dishevelled [F], [M], [writer], [professor]

I walk into his office. His desk covered in books, disorganized and bookmarked in seemingly random ways. Papers waiting to be reviewed and read. Plants, half dead that have been forgotten to be watered. Sunlight peaks through the window behind him as he sits in his chair. I met him at a reading which we both were asked to attend and share our writing at. Both of our pieces filled with both sadness and a redefining of ourselves. He came to me afterwards, sharing his appreciation for what I had shared with the small crowd at the bookstore cafe.

“I think you’re writing is impressive. There is so much emotion and rawness that is balanced with insight and reflectiveness. It makes your writing extremely engaging, despite it being in essay form”. He says to me, as he takes a sip of his coffee. I have a few suggestions for edits, however, nothing major. The bones of the work is there. You are a very talented writer. Did you ever take any classes? Major in writing or literature?” Read more »

[MF] halloween taught me (26M) a valuable lesson! Always sexy maids (24F) over drugs!

A few halloweens ago. I started hanging out with this super cute girl. We had known each other for a while but she was definitely pointing me more in the direction of friendzone. So I invited her to see a movie. Maybe sneak some booze in the theatre. Something we’ve done a few times in high school. Things have changed a lot since then. We don’t really drink much anymore. She got into heroine and I got into crack. So our addictive lifestyles don’t really match up well.

Anyway…. I get to her place. And she’s waring this super slutty Maid costume. Fishnets and super short skirt. I’m waiting for her to get her makeup done and then we’ll head to see a movie. But in the middle of her doing that, her roommate who sells her dope busts in and accuses her of stealing his dope while he was passed out. He says she ain’t leaving anywhere until they find that dope…. So movie night is off. So I say fuck it plan B. I’ll go grab a bottle n we’ll just drink Here in this drug den haha. A few drinks in and I’m grabbing handfuls of that fat ass. She starts straddling me and I lean in to initiate a kiss. She started kissing me back. And then my phone fucking rings and it’s my dealer outside. So I get up and tell her don’t worry. Take it slow n we’ll get there haha. Read more »

Some short, embarrassing, and very true stories about how [m]y high school GF’s [f]amily would talk about my big dick

If you’re a reader who tends to dislike/doubt when a writer talks about having a sizeable penis, this will not be the read for you and I politely ask you to please ignore and move on. I understand where the doubt comes from, but these stories are as true as they come, and I included some non-nude evidential pictures to try to help clarify my story points.

This is a series of short stories that happened over the course of a few years, some years ago, and are organized from earliest to latest moment. Pretty much none of these are sexual but definitely as real as they come regarding big dick experiences. About me, I’m 23, 6’4”, Latino with green eyes and curly hair, lanky but fit skater boy, with 8”x 7” (girth is cone shaped, 6” at the head, 6.7 in the middle, and 7.2 at the base) below the belt.

1. Read more »

[M] The time I cheated with my best [F]riend from college

This happened a couple years ago. I think the backstory adds to this, but those that want to skip it can scroll down to the “- – -“

I met Annie during a chemistry lab our freshman year of college and we kept up over our time at school. We flirted on and off over that first year, but eventually she started dating someone else. It hurt, but I put a relationship with her our out of mind and focused on being friends. Some of my best memories of college were with her, lounging and watching Netflix in my apartment or playing horror games. Inevitably, we would end up leaning against each other during a movie or jumping, screaming, and laughing onto each other. Nothing sexual, but there was always a certain tension I couldn’t help but hope would snap. But she would always leave once we were through for the night, and nothing came of it. Read more »

I got gangbanged at a party by my drug dealer and his friends. It turned into a freeuse weekend. [FM]

This happened around 4 years ago when I was 21 and living in a different state than now.
So I was a huge pothead in my early 20s and always used the same dealer. We will call him Kavion. I had known Kavion since my freshman year of high school and would call us friends. I was pretty shy and reserved and he was always nice and easy to talk too. Mainly, I bought weed from him and hung out to sometimes to smoke but that’s pretty much it. Kavion knew EVERYBODY and was generally popular, we also were from a relatively small suburban town. Anyways, after high school I started hooking up with one of Kavions friends. Honestly, I have always thought he was hot but we were always just friends. I was in a long time relationship in high school and we broke up after we graduated and I entered what you would call my slut phase. One of my regular fwbs was one of Kavion friends. We ended up falling out but I guess to told Kavion about our hookups.
Fast forward to this night. I go over to Kavions to buy weed like normal, it’s after work maybe like 11 pm. I show up and there’s way more people there than normal. I walk in and there’s people I don’t know at all smoking and drinking and listening to music. Clearly he’s having a party but I don’t see Kavion. After a second he comes down the stairs, sees me and waves me up. Nothing too abnormal, he almost always has people over but I’ve never been there while there was a party. I go up stairs to his room and it’s him and 5 of his friends. I knew maybe 2 of them tangentially from high school. I get my weed, he asks me if I want to smoke. I am a little hesitant but I say yes. We spark up and at some point someone hands me a drink. I drink it not having work in the morning. After a while of smoking and drinking I am pretty fucked up, any more and I definitely wouldn’t be driving home I get and start to head out. I get down the stairs and everyone is gone, I look at my phone and it’s way later than I though like 2:30-3:00 am. Before I get to the door I hear Kavion call my name.
I turn around and he comes down the stairs and comes up to me. He says “I forgot to ask you something, is this you?” He shows me a video of my, my old fwb and one of his friends spit roasting me. I knew he took the video and I trusted him not to send it to anyone but whatever. Pretty much everyone knew I was easy now. Anyways I blush and don’t say anything and he leans in and asks me “are you sure you need to go now?” I don’t say anything so he grabs my ass and pulls me closer. I can feel him already bulging. I don’t push away so he unbuttons my shorts and pushes them down. I haven’t exactly decided if I wanted to fuck and especially right now thinking about his friends up stairs hearing us but I am definitely wet. He pulls down his gym shorts and his cock practically bounces out. It’s was almost comical how big it was, it had to be 10-11” and 4.5-6” girth. I am clearly staring and he smiles “So…?” I start to lead him to the bathroom thinking maybe we could do a quickie in there and his friends won’t hear.
Passing the living room I feel my hair get yanked, hard, and I squeak with pain and I fall backwards into his lap the couch. Without saying anything he shoved my face onto his cock. I wasn’t really expecting it but I was soaking wet now so I went with it. I did so much suck his cock as he fucked my throat. Basically him holding my head down as far as possible and me gagging a lot, him occasionally pulling my head off so I can breathe. His dick is so big I can barely fit it in my mouth and it’s really hot but I am definitely making a lot of noise. Next time he lets me breathe I ask if we can go to the bathroom so it’s quieter. My shirt is off at this point so it’s just my bra and thong. Instead of answering pulls me in and kisses me hard, my saliva all of my face and makeup running. I fell his hand reach between my legs, grab my thong and yank it forward so hard it rips off my ass. I squeak with pain again and he shoves me over onto the couch and hiked my ass up. Without any teasing he shoves his cock into my pussy and pushes my head into the couch. I definitely have not fucked someone as big as him before but it feels so good and I am moaning. At this point I didn’t care about how much noise I was making and I guessed his friends probably didn’t care about people fucking downstairs.
He’s railing into my pussy and smacking my ass when I feel someone grab my bra strap and hair and yank both, breaking my bra clasps. Confused, my head yanked up I see 4 of 5 of his friends down stairs and I am face to face with the cock of one of the guys I kind of knew from high school. Up until now I hadn’t even considered that this could turn into a gangbang and Kavion had not asked about it. Before I can think or say anything his friend grabs my chin, opens his mouth and shoves his cock in. He’s not nearly as big but has a nice cock probably 7”. Now normally, I probably wouldn’t even have fucked Kavion but I was drunk and high and I had been really horny because I didn’t have a fwb anymore. I had been fucked by 2 guys a few times and 3 once but this was definitely the most at one time.
I am getting my face and pussy railed and it is really really hot. I feel Kavion grab my ass and push as far as he could into me and empty his load in my pussy. It was so deep I was pretty much seeing stars and when I felt him pulsing I started to squirt. (I am definitely a squirted. He pulls out and before cum really has a chance to leak out another cock gets shoved into my pussy. He’s the smallest so far probably like 5 inches. He thrusts once or twice then pulls out and pushes his cock, covered in cum and my pussy juices, into my ass. This is the first time someone is fucking my ass tonight and I love anal. I push my mouth further on the guys cock and lick with my tongue around his head. He pulls out, jacks off a few times and comes all of my face.
They turn me over so my ass is on top of the guy fucking my ass and my legs off the couch. Two of the three guys left get in front of me and one of them shoves their dick in into me. I have the last guys dick in my mouth but when someone starts fuckig my pussy again he pulls it out, covered in saliva, and comes around me next to the guy fucking me and shoves his cock into my pussy. One of them is probably like 5″-6″ but the other is the second biggest at like 9″. I gasp scream and squirt immediately. Right after that the guy fucking my ass thrusts and cums in my ass, spillout out around his dick. He pulls out and I expect the last guy who I havent done anything with to start on my ass. To my surprise I feel Kavions huge cock shove into my ass. With cum as lube now it goes in, but barely. I am pretty much just screaming now non stop when the last guy stands on the couch, straddling my face and shoves his cock into my throat. They all continue to fuck me cumming in my pussy, ass, throat and all of my for a good 15-25 minutes more.
When they are all finished I am laying on the couch, leaking and gasping and barely able to comprehend what just happened. I feel Kavion throw a towel on me. “Damn Martha, I didnt know you had it like that” he said. I sit up and smile and wipe off and start to look for my shirt and shorts so I can get myself together enough to head home. However, and this is the hottest part, I couldnt find them. My keys are in my shorts pocket.
“Hey where is my stuff?” I ask. He smiles “You think youre going home? We are all free all weekend.” I also didnt have to work that weekend and I thought about it and decided to play along. “Ok…but what if we go somewhere?” I ask. “I’ll let you know if we let you wear clothes or not when we go out.” This turned into proabaly the hottest experience of my life. I was a a freeuse whore for them the whole weekend. Like I said this was four years ago, I live in a different state and have a boyfriend now. This could have probably three more parts with the hottest things we did so let me know if you liked it :)

[FM] I had sex with my best friends dad

I had sex with my best friends dad

My best friend has no idea that I fucked her dad. I don’t know if I’ll ever be able to tell her , but i want to get it off my chest . Her dad is divorced and he is very attractive . He is a pe teacher at a high school and he’s very well built . He had always turned me on since I first met him .

Friday after work I decided to stop by my friends house and surprise her with some food so we could hang out but turns out she took a shift at work and wasn’t home. Her dad was very friendly and told me that he loves Chinese so I decided to ask if he would like to eat it with me. He invited me in and we ate .

We had a very good conversation. I eventually shot my shot and told him I couldn’t believe he was single since he’s so handsome. He then told me how Im one of those most attractive friends his daughter has . He reached out and touched my arm across the table. Read more »

The Tutor [F20/F18] [Domme/sub] [Role reversal]

**Author’s Note:** While this is technically a Patreon story of mine, I’m also gradually releasing parts for free on my website. Mods, let me know if that’s too much of a gray area and I’ll refrain from posts like this in the future. Just wanted to share another story on here, with some fair advance warning.

–Lady Lucia

**PART ONE**

First day on the job.

I was still a little hesitant about committing myself to this; the only reason I said ‘yes’ in the first place was because the money was just too good to pass up.

Back in high school, I would have answered the call to tutor without any hesitation. A chance to make a little bit of extra cash, by only giving up a small fraction of my free time? Sign me up. It would have been a far better alternative than the soul-sucking retail job I ended up dealing with for the sake of saving some money away for university. Read more »

New Years Eve at my gf Amy’s house. Part 1. My gf Amy tells me a story about her hot past. (MMMMFF 19)

I called my gf, Amy after my interesting threesome with Mary and Josie and told Amy all about it. Amy said, “Do you want me to dress like a kitty?”

I said, “um…holy shit…maybe…yes..”

Amy laughed and said, “I can’t wait to see you on Friday at my New Year’s Eve party. What time are you guys driving up?”

I said, “I think Mary and Josie said we could leave early. They want to get up to your house and claim a good bedroom.”

Amy said, “There’s enough bedrooms for everyone. It’s not going to be that many people.”

I said, “Who is coming?”

Amy said, “It’s just you, me, Mary, Josie, Sarah, Hyun and a friend of mine from high school.”

I said, “Am I the only guy at this party?”

Amy chuckled and said, “You are indeed. I thought it would be weird bringing in other people when all of us have sex together.”

I said, “But, what about your high school friend?”

Amy nervously said, “Well, she kind of invited herself. Don’t get me wrong she is a good friend. I just don’t know what she will think of all of us girls fooling around and I don’t know there’s some other things.” Read more »