Tag: High School

Chloe the Roommate 8 [TF/M]

Took longer than I was planning but I think I made it longer to make up for it. Enjoy!!

Chloe the Roommate Part 8

See. Chloe naked all day? Hell yeah, who wouldn’t want to see that. “What are the other rules?”

“If everything goes how I’m hoping, you will find out soon.”

“Fair enough. They take off those clothes.”

“You first”

I tried my best to put on a show but I felt like I wasn’t doing much. Chloe however thought differently as she was rubbing the outside of her shorts. I could see the bulge.

There I was standing in front of a girl, my roommate, my girlfriend, naked and at about half mast. She looked me up and down and then stood up and pushed me back down. Read more »

Step Sister Dilemma

I was taking an unexpected day off mid week. I had been in an electrician apprenticeship for nearly two years and finally, I was at a point that was really kicking it. I had been paying mom & dad rent for the last 6 months, and had just recently received my second bonus. The owner was also giving me a few days off as a way of saying thanks during this intense wave of heat.

I had been chilling in my room over the garage, binging on Netflix, when I saw an odd car pull into the drive. Out hopped a young man I had never seen before, but he walked up the drive like he’d been here before, and in he walked. I was more interested in the show than that guy, figuring it was someone from my step-step-sister’s classes. I was right, but not at all in the way I had pictured.

My step-step-sister is Arielle Wilder, and unlike myself, she had chosen to go to our local university and major in Art. When we would argue she would point out that she was engaged & her fiancé was quite well off, so it wasn’t like she would ever have a care, and to that point, Arielle was completely correct. Read more »

The time I [M26] played truth or dare with my high school crush [F25] and hooked up with her [MF]

So this story takes place back when I was 20 and she was 19. Me and my friend Lex (not real name) met when we were a junior a sophomore in high school. We hit it off pretty quickly and became really good friends. We had so many things in common and were so inseparable that half our highschool always assume we were dating. However this was not the case since we always had our own things going on. We almost never single when the other was, but when we were we would constantly flirt and banter back and forth or just lay on the couch cuddled up. We even made out a few times for fun but nothing even expanded out of that and I didn’t want to push it since I didn’t want to screw up what we had. I was young, sue me.

For context Lex was tall, had pale skin, bright blonde hair that went down to the middle of her back, a slender body with a nice perky b cup chest and some how a nice round butt with thicc thighs. That woman never lifted a weight but game my quads a run for their money. Not to mention she would always wear these tight fitting dresses that cling on to her in the best of ways. Read more »

[MF] fucked an old time friend

I hooked up with a girl that used to go to high school with me. We knew each other and had the same friends, but weren’t that close. Now, during my high school years, I had no sense of how to talk to girls, or how to flirt. I was your average short virgin-like Asian that lacked in social skills. As years went on, I wanted to change that, so I started working out, researching, reading, and practiced how to talk in general before I could talk to girls. After that, I started to get the hang of talking to girls, and later hooked up with a few girls a long the way.
Now after my transformation, one day, I get a message from her making a comment on one of my stories, which was of me working out. She said I changed a lot since high school, and look amazing because I had my shirt off in my story. I obviously thanked her, and flirted back saying, “that wasn’t the only thing that changed.” She laughed about it, and from there we messaged, sent pictures, and called for just 2 days.
The weekend was coming and I had nothing to do, so I messaged her and said if she wanted to chill and hang out. She accepted my invitation, and had dinner together, where I had a burger, and she had a steak. I won’t lie, during the entire dinner we flirted so much. When she got the steak, she ordered it medium rare, and when the waitress left, she looked at me and said, “that’s not the only thing I like rare.” When I was eating the burger, I was making a huge mess, and she was laughing at me, so I commented, “a preview of later tonight.” Once we finished our food and left the restaurant, the night was still young, and we were dying for some more of the fun we were having. I told her, “do you want to go back to our high school and skinny dip in the swimming pool?” She was a bit taken back, but she was down for a crazy and fun night.
We drive to our school, and park right outside the area leaving the doors unlock, just in case we need to make a quick get away. We jumped two fences, one for the school parking lot, and the other for the swimming pool. Right as we get in the swimming pool area, we had to make sure it was safe to move. Once we felt like there was no one around, we headed over to the mini water park our school had next to the main pool, and started getting undressed. We were a bit nervous for various reasons, but we just laughed and giggled at each other knowing that we’re about to see each other naked. Once I only had my briefs on, I looked up and saw her completely naked with her hands covering herself up. When I looked at her, her skin looked so soft and breasts look so plump, even though she was covering herself. I noticed her checking me out too, and she laughed a little seeing that I had a bulge trying to come out from my briefs. I told her why she was covering herself up, so she told me if I take off my briefs, she’ll uncover herself. Once I took off my briefs, she put down her hands, and there we are, standing there naked as we look at each other with laughter, and a bit sexually too.
A bit of awkwardness was there, but she laughs and runs to the water, and I chase afterwards. We splash water at each, I carry her on my shoulder, and hug each other we were kiss for the first time. Once we kissed, we just made out next and put all of those emotions held in into that make out session. During the make out, she grabs my dick and starts stroking it and then whispers to me that she wants to suck it. We get on dry land, where I lay down and had her suck me off. She was a nasty bitch, she deep throated, spitted, and slobbered on my dick. I told her that she never looked like she was the type during high school, and she laughed it off and kept sucking me till I came.
Once I came, we thought we heard someone around us, so we got our clothes and booked it back to the car. We put enough clothes back on, and drove off and parked somewhere. We laughed and stared at each other realizing what we did, and then made out again. She told me she wasn’t done with me, and I replied back saying the same thing, so we went back to her place to fuck. Once we got back to her place, we had to be a bit quiet because she had a roommate. Once we got into her room, we made out and fucked like our lives depended on it. We did so many things: fingered her till orgasm, fucked her missionary, doggystyle, carried her and fucked her against the wall, and fucked on the chair in her room. We did this for what felt like all night till morning came, but still knocked out and slept it off. Once I woke up, I put my close back on, went back home, and texted her once I got home and thanked her for the night.

If you don’t like ass play, just don’t read this

You can tell it’s her by the way she walks, one heavy footfall followed by a lighter one remnants of an old high school wrestling injury.
You close your book as she unzips the entrance to the tent. A wave of moisture tickles your nose as fog rushes in from outside.
“How’d your hike go?” You ask as she sits down untying her shoes.
“Good super misty out there. Think it might rain later,” she said chucking one shoe off.
You pop your head outside the tent, your lips pass centimeters away from her arm letting you taste the perspiration from her hike on your lips.
“Looks like it,” you say trying to ignore the sudden hunger you feel.
“Yea looks like it will be power bars and chips for dinner,” she says retreating into the tent once she’s discarded her other shoe.
You zip up the opening keeping the moisture at bay, behind you hear her moving things around getting comfortable.
“How’s your book going?” She asks as her tank top crosses over her head managing to snag her hair tie along the way giving you a picturesque view of her long hair falling, draping her shoulders and kissing the tops of her breasts.
She acts nonchalantly examining her breasts like a doctor.
“How do they look? I kind just wish they’d sit a little higher like this,” she says cupping her breasts and pushing them up and together.
“Yea uh they look great,” you say finding it hard to think as blood rushes from one head to the other.
She cracks a smile still adjusting her bosom as she swipes her fingers under her breasts sweet glistening on the tips guiding them towards your face. Putting her wet fingers right below your nose, as you breath in gasping as your forced to adjust to sitting position, before letting them dance on your lips. You tremble at the smell. With great effort you play it cool closing your eyes and smiling with a quite mmhhm.
“You like that? How about this?” Your hear a soft slap as an elastic band snaps back into place against skin. Than she replaces one hand with the other pushing it past your lips and skimming it across your tongue.
The taste is a familiar combination of sweat, funk, her sex and something else you know but don’t have the brain power to recall. You suck on her finger a thirsty man in the desert as she hooks your teeth pulling you forward as she leans herself back.
“Take them off,” she says removing her fingers. You find your face close enough to her vulva that you can feel moist heat radiating from between her legs. You grab and pull as she twists and swings her hips helping you to quickly shed her shorts. You toss them in the corner, and are surprised to see her flip herself around, arching her back, and positioning one hand on her clit.
“You know I’m kinda mad at you, you let me go for a walk all by myself so you could read your book and now I’m all stinky and sweaty.”
You come closer putting one hand on each leg working your way from the knee up until you have one cheek firmly in each hand. You hear her purr and spread her lower lips trying to find that spot.
“Well that was mean of me. However shall I earn your forgiveness?”
“I’m sure you and that clever tongue of yours can think of something,” she replies moaning a little as she begins moving her fingers in a counter clockwise direction.
Needing no more prompting you spread her cheeks and begin rimming her asshole.
“Ah,” she says as your make smaller and faster circles working your way from the outside in than open your mouth wide like a snake encompassing her whole hole kissing it with the ferocity of a sailor just returned from sea. Than you plunge your tongue inside going as deep as you can burying your face between her derrière releasing her backside so her cheeks can slap against your face swallowing smooshing your face. Your know you have limited time before you have to come up for air, so you begin edging the inside of her asshole similar to the way you rimmed the outside but with more vigor.
“Oh fuck oh fuck!” She says pushing your face deeper a vice grip on your hair. You know there will be no breathing until she’s satisfied.
The blood is all gone from your head otherwise you might realize your running out of oxygen but instead you keep going, licking and rimming and edge and kisssing and rimming and edging and kissing, the smell of her suffocating you like a beautiful goddess of sin. Until her whole body trembles and shakes pushing you further in, your nose and tongue now firmly wedged in her asshole.
“Holy fuck!” She says letting out a breath as tremors from her orgasm subside.
You fall on your back taking in huge breathes, eyes closed as the world spins around. You hear her moving and are about to ask if she liked it when a drop lands on your nose. Curious you open your eyes to see her gorgeous rump hovering over you, her asshole clearly visible as she squats over you.
“You didn’t think I’d leave you all high and dry now did you?” You know she’s smiling even though you can’t see her.
Before you can answer she plants herself on top of you sliding up and down on your face using your nose as her personal buttplug. Your face little more than a seat to make her comfortable. While the gyrating continues on your face her hands slither across your torso one hand cupping you balls than gripping you shaft. You hear her spit as warm liquid drips down your cock. Than she begins to stroke you. The other hand goes lower finding your crack rimming the outside with two fingers just like you did with your tongue,you writhe and moan under her entranced in her spell until she is done with you. She stops gyrating as you plunge your tongue deep inside her asshole.
“That’s right baby just like that,” she says before licking her two rimming fingers. You feel a long drop of saliva hit your stomach as her finger move back to your asshole and plunge them inside. You moan gripping her legs unable to contain your ecstasy.
“That’s right baby,” she says inserting her fingers in and out in and out. Slower at first but building speed. You try to focus on using your tongue but it feels to good.
“Relax baby,” she says sliding up and down on your face her pungent crack filling your nose and mouth driving you closer and closer to the edge. Her fingers than stop plunging in and out instead making circular motions. It’s all too much and soon your muscles tighten up and you feel warm liquid shooting from your cock.
She dismounts your gathering all your cum in one hand licking it like an ice cream cone.
The two of you curl up underneath your blankets and realize it has started raining, the drops echoing as they splat against the tent. Both of you drift off the white noise of the rain lulling the both of you to sleep. Neither of you requiring dinner.

Desire repressed and fulfilled ( womens bisexual desire filled.) it

It was an August day hot and humid. I had just finished with my last client for the day and decided I would head to the liquor store to buy some wine for my husband and myself for dinner. As I stood there looking at the wine I heard a familiar voice from behind me.
“Mrs James? Is that you?” I spun around see the familiar face that was connected to that Smoky, sultry voice. It was Sarah , my oldest son’s girlfriend during his Junior and senior years of high school. She was older now the last time I had seen her was at their graduation when I was 39 and she was 18. My world had been opened up to bisexuality and the wonders of a woman’s body when I was 32 years old and Sarah who was cute as a button and was also a little flirt. She had this cute round face with a perky little nose adorable blue eyes coupled with a cute little upturned smile and had the cutest dimples. She and my son would lay out and tan in the backyard and quite often I would peek out at her lovely young body as they laid there in their swimsuits. Of course it was hands off, she was underage and between the ages of 16, 17 and 18.
However I won’t lie sometimes our hello and goodbye hugs and kisses were a little bit more intense than pleasant greetings.
I smiled and held my arms out holding a bottle of wine in one hand.
“Saraaaahhhh, how are you I haven’t seen you in such a long time. Come here.!!”
Even though it was almost two decades later she still had that same adorable smile.
She put out her arms and stepped forward into mine. We embraced warmly and I saw the heads of a few other shoppers turn. Releasing our embrace I reached over and sat down the bottle of wine and put my hands on either side of her face cupping her cheeks and smiling into her eyes. As I held her it was no longer that firm young body of a girl but the full soft femininity of a woman.
” So tell me how are you? I haven’t seen you in such a long time.”I said to her.
” Oh it’s been good, I attended college for 2 years got an associate’s degree and a job at a lawyer’s office. Met a boyfriend moved to California with the him he wanted to pursue acting. I grew up a lot during those years and we wound up breaking up and I came back home, got married that lasted one year and now I’m single.”
My hands slipped down from her face over her shoulders and down the length of her arms. I held onto her hands and looked at her with concern.
I asked her.” Are you busy tonight? I mean what are you going to do when you leave the store? ” Would you like to come over and have some wine? We can catch up”
She smiled again then squeezed my hands back tightly.
“I have absolutely no plans and I would love that.”
We shopped together and picked out some wine then headed over to my house. My husband wouldn’t be home for another 3 hours and that would give us plenty of time to catch up.
We pulled into the driveway. And I got out of the car she stepped up behind me and we walked up towards the house entering through the garage door. She peeked out the back door.
“Yep it’s just how I remember it. I remember skinny dipping with your son in that pool. ” She giggled.
In all actuality I knew all about the skinny dipping but I acted surprised.
We walked into the house poured some wine and talked about how hot it was. I asked her if she was interested in going for a swim and she said yes indeed. I offered her one of my swimsuits but it didn’t fit very well our yard was secluded and I stated.
“Well since you skinny dipped in this pool before perhaps we should just do it again you wouldn’t mind would you?”
She let me see the biggest smile then immediately began removing her suit. Her short compact body was as beautiful as it was when she was younger her nipples were pink and stiff perfectly poised on her c cup breasts which gracefully spilled down her chest only to swoop up much like a ski jump. My eyes drifted down to her stomach and below where she had a full blonde bush neatly trimmed, the split in her vagina leaking substantially up high not showing any traces of labia.
I unbuttoned my blouse and unhooked my bra removing it, my breasts fell from the D cups.unzipping my skirt I wiggled out of it standing there in panties and heels. I saw her bite her lip as she watched me. Leaning against the wall I lifted one foot and pulled off my heel then the other and wiggled out of my panties.
She looked down at my cleanly shaven pelvic mound. My husband always said it amazed him at how pronounce it was…..
Again she bit her lip.
“I always wondered what you looked like all those years when I would see you come out in your swimming suit or shorts. My gosh you’re beautiful Mrs James.”
I could feel myself beginning to moist en and those familiar butterflies in my stomach, my nipples had already stiffened, I usually wide dark areolas where now pulled tight, tugging at the skin of my breasts with want.
How I wanted to take her right there !
Her gaze from me never veered away there was no attempt to hide that she was absorbing every part of me into her memory.
But I didn’t, I smiled and told her she was sweet for saying that. Walking past her with my clothes in my hands I brushed against her and felt such excitement. I set the clothing down on the bed then turned around to see her standing immediately behind me I almost bumped into her. We stood there naked looking into one another’s eyes for what seemed to be an hour although it was mere seconds. I reached my hands back up to cup her face and she put her hands on my hips. I leaned forward and we kissed.
We were both lost and rapture. The moment we both had longed for long ago was now happening and our kisses were filled with torrod passion. Immediately I was transported back almost two decades to when she was in high school and we would give each other a little longer than a peck for goodbye hello. I slipped my hands back off of her and wrap my arms around her pulling her body to me and feeling her skin against mine. A whimper escaped her lips. I took charge immediately becoming dominant. My hand slipped up from her back under her hair and I grasped the handful pulling her head back gently. My lips move down from hers as I kissed around the bottom of her chin and neck. I moved my other hand over the front of her body grasping her breasts pinching and pulling her nipples. She emitted a number of different sounds cries and whimpers and moans.
I turned her around towards the bed leaning into her until she finally had no choice but to fall onto it. She laid there looking up at me. I leaned forward placing one hand gently around her throat my other hand on her shoulder ever so slowly and gently I raked my fingernails down over her breasts and ribs and stomach. She bit her lip and I could tell by the look in her eyes that she was loving it. I pressed her legs apart with my knees.
Slipping a hand down onto her lower stomach. I let my fingers move slowly down through the curly pubic hair. It was light and fluffy and soft. I played there for a while as I leaned my mouth forward and began to kiss her breast. I sucked and teased her nipple with my tongue and lips. Nibbling on it until I would feel wiggle under me. My hand moved down and I felt her wet lips. My forefinger and index finger riding down the outside of her labia and dragging the moisture up and pressing firmly on her clitoris and circling firmly as I continued to work her nipples and made my way up to her neck kissing and chewing on her ear lobes and neck moving over to her mouth we kissed and then she moaned in my mouth.
She laid there like a puppy enjoying the petting it wasn’t but 3 minutes before I felt her pelvis begin to rise and fall erupting into a joyous orgasm, she was loud and expressive clawing at the bedspread.. I kissed all the way down because I wanted to taste her wrapping my hands around the backs of her knees I yanked her forward then drop to my knees and put her in the legs over my shoulders. It was delicious wet and sticky. I eagerly lapped up all of the juices that leaked out of her as she erupted one more time in orgasm in response to my licking. Her opening pulsated against my tongue and I thrust the tip in between lips until she stopped.
Standing up I held my fingers to my mouth licking them clean and then slipping them back down and inside her. I began to fuck her with my fingers her eyes were glazed her pupils dilated. I slipped one hand up over her throat as I continued to thrust my fingers in and out circling my thumb over her clitoris at the same time. I loved her cute little face I always did and I loved seeing it in this manner. Her mouth opened wide and her eyes rolled back she moaned and groaned and began to spasm. This time her orgasm lasted for a longer period of time. As it subsided I laid my body down on top of hers and began to grind my pelvis into hers. We began a sort of wrestling match and she rolled me over into my back rising up in between my legs she began to grind her pussy down on mine. The two of us were worked up into a frenzy she leaned forward placing a hand on each one of my breasts and squeezing. The pain I felt was delightful. We ground ourselves into each other until we both erupted in orgasm together dropping down on top of me. We kissed and fondled and caressed. Finally relenting to the fact that we have both come to the point of what we both wanted for so long.
After laying there for a while together we got up grabbed our wine and headed out to the pool. We talked for an hour or more we kissed we caressed and we made an agreement that this would become regular. She climbed out onto the edge of the pool and I moved myself in between her legs licking her once more to orgasm.
Sliding her body back down we embraced in the water. I had been with women but this was one of the best moments with a woman I had ever had. After a while we climbed out dried off and got dressed. Walking to the door I kissed her and we made out for another good 15 or 20 minutes our clothes opening and starting to come back off. She lowered herself to her knees and I spread my legs as I moved myself over her. She ran her tongue up and down my cleanly shaven pussy. I looked down at her adoringly, all I could see was the top of her head her eyes looking at me over my mound she appeared as if she was still that teenager who was dating my son. My eruption was loud and strong I fell forward my hands bracing myself from falling forward against the wall. I slid down to my knees in front of her and we kissed more.
Finally we stood up I walked her out to the car and we made a date for the following week.
I have relived that day in my personal playtimes over and over since.
We went on to meet on a regular basis for the next year where she moved out of town with another job.

[FF] 18 long and slow build up to my best ever orgasm

I’m F 18 with long red hair a nice smile and a cross country runners body. I’m pretty femme and like wearing cute sundresses and a bow in my hair.

My freind is F 20. She is a brunette with very long straight hair with a round face, perfect eyebrows and a great smile. She has a skinny volleyball players body. She is also femme but likes to be more dominant.

When we started having six last month it was my first everything. I never came out in high school, never dated or even kissed a girl, and really didn’t even know how to finger myself.

We started having sex a lot, like all the time. Even though she is pretty experienced (and phenomenal in bed) it takes me a while to cum. The first time took almost 3 hours. Since then I’ve cum quicker but it still takes a while.

The Friday before labor day we had been flirting and sexting all day during class. We were both really horny and she mentioned that she wanted to eat me out all night. Read more »

First time in the backseat…in broad daylight [MF]

There are those that might have some crazy stories for when they first had sex but I think I (M) can say that my first time was a little unconventional as well. I was with my girlfriend at the time and after school we would meet up, drive around and head back to my parents place. We were both in our teens. We would make out for long times on end. We would reach into each other’s pants, take off each other’s clothes, and then we would give each other head. She would give me a blowjob and at first she wasn’t sure how to do it so her teeth did grind a bit so it hurt but she got better. I would lick her pussy but could not say what made her feel great vs. good. We never had actual sex yet where I stuck my dick in her pussy. Read more »

I fucked my High School Teacher (Part 3: The Finale) [M] 23

Part 1:

I fucked my high school teacher [M] 23 [F] 35 from gonewildstories

Part 2:

I Fucked my High School Teacher (Part 2). [M] 23 from gonewildstories

I slam my former teacher on the bed and kiss her soft lips.

I spread her legs and rub the head of my cock on her pussy and clit. I tease her tight hole and slide the head of my cock inside her.

She grabbed my shaft, looked me in the eyes and told me to go slow. She said she had never had a cock this big inside her before.

I begin to slide my cock inside her, inch, after inch, until she is taking my entire cock!

I start off very slow, in and out, in and out, at a very slow passionate pace. She started thrusting her hips forward after a few minutes so I start to go a little faster.

After I notice her really getting into it I bend her over and start fucking her from behind. Watching her tight little ass ram against me is a great sight to see. Read more »

the unsatisfied wife part 1 [milf, teens]

I got married two years ago. It was my second marriage, but I had no children from the first one – which only lasted a few years. I was busy with my career and he was busy with his. You know, the usual story about not really having enough time to invest in a marriage.

When I married John, his stepson, Matt, came along with package. Matt was eighteen at the time and in no mood to have a “new mom.” I dealt with the usual stuff that happens in situations like this. He either ignored me or was just plain rude and never really paid me much attention – let alone listen to me when I would ask why he was late coming home or trying to get him up on time for school. His dad kept telling me to give him time. John is wonderful. He is caring and compassionate and gives me access to his bank account to buy stuff for the house or for myself. What else could a girl want? Read more »