High-Strung, Preppy Girl Giving Me a Helping Hand [MF] [public]

I was saving this story until after I told my bit about [Courtney](https://www.reddit.com/r/gonewildstories/comments/6ncbpr/my_childhood_friend_forcing_me_to_fuck_her/). I’m not exactly building a Marvel Universe, but context, I think, is what makes these stories, to me. I tried to retell the conversations as accurately I could remember. This may not be the dirtiest story ever, but I love thinking about it. Plus, it’s the introduction of dirtier stories with her.

—
The embodiment of prep with a pinch of hipster, Isobel was always busy with school functions, charities, and extra-curricular activities. She had a rotating clique and was intimidating to befriend. She barely broke 5″5 in her tan cardigan that draped over a white tank top. Her breasts weren’t perky, instead, they hung so perfectly, so maturely, they reminded me of lavish raindrops – pert enough for her cleavage to swallow some of her necklaces.
She had a feathery black pixie cut that cruved to each side of her lips. When she wore fashionably torn shorts, you could see the results of her gymnastics in the toned lines of her legs. She rarely dressed to her body’s strengths, though, so guys called her “beautiful” instead of “hot.” She was hot. High-class, sometimes snoody, and hot.

We didn’t talk much (I barely talked at all) in the classes we shared, but we exchanged smiles whenever we made eye contact. She was a few tiers above me in social hierarchy, so it seemed almost like a favor she did for me. She seemed pretty out of place walking into the post-grad party thrown by my sociable flirty friend, Courtney. Her white dress bloomed out just over her knees and her hazel eyes shone through her eyeliner.

I eventually found myself in a beer pong match alongside her. You could tell she was forcing herself to let loose.
“No fair! My partner is handicapped!” Isobel joked, referring to the cast on my right arm. Oh, yeah, by the way, I broke my arm prior to this. I pretended to be offended and offered to drink all the penalty beers since my tolerance was very high. I ended up drinking a lottt of penalty beer, but it was worth actually talking to her like a real person for once.

A bulk of the party relocated to the basement to play video games on a giant horseshoe couch. It was Isobel’s turn at Smash Bros. against Courtney, Courtney’s boyfriend, and some random dude. After a few rounds of unfair slaughter, Courtney proposed evening out the battles with teams and wagered, “If we, the girls, win, you two have to duet a love song at karaoke. If you guys win… Isobel and I will make out.” This wasn’t out of the ordinary for Courtney, but Isobel blushed with hesitance before settling on the bet.

It came down to the very last kill, and, probably to satisfy her guests, I suspected that Courtney took a dive. To a roar of excitement, the two girls stood up and faced each other before slowly locking tongues for a solid 30 seconds. Isobel stayed reserved, but Courtney grabbed her waist and traced her lips with her thumb, making Isobel giggle a bit out of embarrassment. Both girls were relatively short-haired, neither flowed past their shoulder, which gave perfect view of their breasts peaking out of their tops, now hugging against each other. I think she liked being a bit ‘slutty,’ though, because she rode this confidence throughout the night. Also I wanted to include this part because it was super hot.

—
“I’m trying to make as many memories as I can while I’m still in town. This one guy was supposed to be just a fun little fling, but … he’s already giving hints that I’m not enough. Like, constantly bringing up threesomes. We’re not exclusive, but still… Not flattering.” She was drinking wine now and occasionally putting her head on my shoulder. *Hm.*

“So, wait,” Courtney leaned over while looking at my cast, hanging her own tits in my face, “How do you masturbate?” She was such a diva and acted overly concerned, but I got a kick out of her shtick.

“…With a lot of motivation?” I joked. They both laughed and I sat feeling pretty good.
“Oh, can I borrow your phone?” Isobel brushed my arm. “I’ll need to find a ride later.” Damnit, I’ve been drinking whiskey all night, otherwise I’d drive her. Deflated, I handed it over. She came back later and thanked me.

“Can you take a picture of us!?” She nestled up with Courtney and posed. I turned my phone and saw something unmistakable in the bottom right “last photo taken” display. It was a bathroom mirror selfie of Isobel with the top of her dress pulled down, exposing her hot pink bra. *Holy fuck*, I thought while looking at them through my phone. My entire body blushed.

The party was winding down when a group of us walked to the park down the block. It was an expansive field with a playground partially encased by a school. The playground and road were separated by a small hill, so at night it felt secluded. I ended up having a lot of fun memories here… The girls ran over to the swings in drunken excitement and the dudes went to push them.

Isobel broke off and jogged to the monkey bars, springing up on the nearest one. Only I followed her. Oh, yeah, she’s a gymnast.
“Ah, I do that upside down, usually,” I joked.
“Umm, like…this?” She threw her legs straight up and curled them on a single bar, flattening her dress so it doesn’t fall down her upside down body.
“No, I meant with no arms,” I obviously pushed. She laughed and looked at me. Then, she relaxed her arms to give me what I wanted. Her dress fell down revealing her pink panties. “Like this?”
“Gold medal,” I cornballed. “I would join you up there, but…” I lifted up my cast.
“Do it with one arm!” I honestly didn’t want to embarrass myself in case I couldn’t, but I jumped up and hung on with my left arm.
“Now kick your legs up!”
“You’re just trying to see my panties,” I joked.

“Poor, hurt boy,” she started teasing sympathy, “so crippled!”
“Well, that’s not…”
She dropped down onto her feet and sat on a raised platform with her legs hanging over. “I’ll have to help you with everyday tasks so you don’t die,” she slightly slurred as I dropped down, too.

“I’m not useless,” I laughed. In reality, I was arguing I’m not hurt enough not to fuck. I walked up to her and touched her bare leg. “Mmmmmm I think you look pretty useless. I’ll have to help you eat. Annnnd change shirts…”

“I’m capable,” I attempted to play hard to get. I was an on/off switch, anyway.
She was pretty physical for a small girl, I thought when she turned me around by my shoulders. Her hips pressed against the small of my back and her legs hooked my thighs. “See? You can’t even fight off a small girl,” she asserted from behind.

She was way better at flirting than I’d thought. She always seemed so serious-minded, but I never knew her outside of class. I missed out on a lot. “Well, at least my killer left damning evidence on my phone.”
“Diiiid you like it?”
“I’ll probably like it pretty often.”

Her hands slipped from the seam of my pants pocket down the inside of my leg. I was already hard, she found out, and she started tracing my bulge. “I can help motivate you even further,” she slurred slightly into my ear.

Isobel’s soft hands snaked down my pants before realizing it was a tight fit and began unbuttoning. She looked around to make sure the others were still silhouettes by the swings before freeing my package from my jeans. I melted as she tugged on my shaft, which felt great in the breeze. It’s been awhile since I was even interested in sex. I was still in a shell of distance and cynicism from my break-up.

“Do you want my help?” she asked brightly. “Yeah,” I breathed. I felt her shoulders shrug in and her tits press against my back. She rubbed me faster, every now and then stopping at my tip to polish it. I couldn’t believe the girl who basically fit in with the school staff members, who never swore or broke her prestigious demeanor, was carressing my cock on the playground.
Her other hand cupped my balls.
“Were you going to jerk off to my picture tonight?”
“Mhm..”
“And imagine yourself cumming on me?” she wanted details as she jerked me off harder. “Yeah,” I moaned.
“On… my boobs?”
“….Yeah….” I gripped her leg as my head fell back against her breasts. She was still playing lookout.
“…Or on my lips?” I still kept from losing all self-control, but with that question, I was done. I didn’t want to cum yet, this was too hot. I wanted to savor this.
“In your mouth…” I closed my eyes.
“Hm, yeah?” She sounded like she challenged it.

She started to kiss my neck when we heard footsteps in the pebbles and 2 silhouettes coming closer. Fuuuuck. Isobel slowed down as we stared at the two shadows, but they ran over to the field across the way from us. Years later, Courtney said she did see us and left us alone to finish. This was awesome of her, and a bit weird since she also claims to have “loved” me during this period. I don’t know. That complex girl is beyond me.

We were alone again, but felt so self-aware. She had my cock in her still hand, laughing devilishly. “We can go against the school wall,” I implied while trying to make my hand reach her pussy. It was a tough angle.

“Or, we can have that to look forward to.” I wondered when she meant, if not tonight, but her palm molded my dick keeping it erect. She sped up and I felt her tits jiggling along on my back. “I wanna help you cum right now.” Her free hand grabbed around to my chest. I leaned back enough so I could kiss her, sucking on her tongue as it poked its way through my mouth. Luckily, she was short enough and sitting at the perfect height for this not to be uncomfortable.
She wrapped her legs even tighter around me and whispered into my mouth, “Don’t hold back… You’re so hard… Show me how much you want my mouth around your cock. Cum all over my hands.”

“I’m about to…” I fucking love girls’ voices when they talk dirty.

I held her head to lock our lips while I erupted warm cum all over her hand and some on my stomach. I drifted in exhaustion onto her pillowy breasts as she chuckled, pleased with herself. “You can text me whenever you need me.”

She was my first ever “fuckbuddy” that summer (Courtney tried, but she was always in a relationship). She would text me all hours of the day and request shower pictures, dirty talk, mutual masturbation via Skype, sometimes an outright proposal to meet up: “bj?” We were using each other to release pent up sexual urges at the perfect intersections of our lives. There’s something about knowing you’ll never see a person again that brings out the primal slut (goes for me too).

—-
What made it significantly better was that she was basically the love of one of my best friends’ life – the one I recently found out was hooking up with my long-term ex. That may have played a factor in how sexually aggressive I became with her. I didn’t seek her out, she literally fell into my lap. I ended up using Isobel to get a bit of “revenge” (she was onboard), but that’s a story for another time. She was the 2nd most fun I’ve ever had.

Source: reddit.com/r/gonewildstories/comments/6psy7v/highstrung_preppy_girl_giving_me_a_helping_hand