Diane's Problem
Copyright© 2025 by A Vulgar Man
Chapter 1
Erotica Sex Story: Chapter 1 - Diane was gorgeous, she was hot to trot with yours truly, and she was eighteen, seventeen years younger than me. She and her parents were my next door neighbors and my friends. I have known Diane for her entire life and watched her grow up. All that changed when Diane decided that I was the perfect guy to be her first lover. This is the story of that and of the consequences of that decision.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Consensual Heterosexual Fiction First Facial Oral Sex
The lithe, long-legged beauty writhed over me, her thighs spread wide as her tight cunt resisted her efforts to get my meaty cock inside her. Diane gasped and moaned, her small hands clamped onto my forearms, her nails digging into my skin. Her eyes were squeezed shut, her teeth bared in an almost feral grimace as she worked at me, trying to sheath my eight inch rod in her belly. Her slim hips rolled around the pivot point of her virgin cunt, the outer lips splayed open around the plum sized head of my rampantly erect cock as she literally tried to screw herself slowly down onto my thick shaft.
I could see that she was going to need a touch of help, so I broke my own rule, opened the drawer of my nightstand and fished out a small bottle of lube. She whined when I slipped my hands under her perfect ass and lifted her off my cock. A moment later, the head of my cock was coated with the slickest shit known to man and I turned her loose to try again.
She centered my cock on her virgin cunt and started that amazing belly dance again, and almost immediately gasped, her sky blue eyes popping open as the head of my cock finally breached the portals of her tight little pussy, my cock head lodging just inside. She bent her head and stared at her wide spread cunt lips impaled on my spike, her long blond hair cascading past her shoulders and cloaking us in a shimmering, golden world all our own.
She smiled then, a small, private smile of victory and her hands loosened their grip. My hands slowly slid up from her narrow hips where they had been lightly holding her, past an impossibly tiny waist and onto her swollen softball sized breasts with their fat, puffy nipples, like ripened ruby red strawberries perched on mounds of vanilla ice cream. Her eyes drifted to my face and her breathing hitched as I gently pinched the turgidly erect buds.
The tireless engine of her hips started up again but slower this time, screwing herself inch by slow inch down my rigid shaft, her full lower lip caught in her teeth. It was quite possibly the most erotic thing I had ever seen anywhere in my thirty-five years. It just got better as she straightened up, gathered the thick mop of her hair in her hands and piled it on her head and held it there, her elbows out to the side and her back arched, her proud titties thrust out as her ass bobbed and weaved on my gradually disappearing cock.
My eyes raked over the ripe body on display for me, her creamy white breasts starkly outlined by her summer tan, the rest of her flawless skin a coffee-and-cream shade of tan except for the small, white triangle centered around her neatly trimmed pussy, now widely split by my steel hard cock half submerged in her hot, wet cunt.
I did nothing to help her, using all of my will power to just lay there, resisting the primal urge to thrust my hips upwards and take her. Her cherry was long gone, lost to gymnastics in the third grade and an overly confident attempt at a split on a slippery floor.
Finally, a few moments later she was sitting on my hips, my eight inches fully sheathed in her taut belly, a tiny, triumphant smile pulling at her full lips as her eyes sparkled down at me.
“See?” she said. “I told you it wasn’t too big.” I smiled back at her flushed face.
“You were right,” I admitted, looking again at her tight pussy, now with a full beard of my pubic hair. “I can’t believe you got the whole thing inside you.”
It was, I thought to myself, a rather remarkable feat. Diane was not a big girl, standing at around four feet and a half feet tall and weighing in at around one hundred pounds.
She was my next door neighbor’s daughter and I had known them for about eighteen years, ever since they moved in. It amazed me that she was making a play for me and I had foolishly decided to see how far she would go.
She was a remarkably beautiful girl with long, lean but well muscled and shapely legs, a delightfully round and firm ass, slim hips, a small waist and fat boobs about the size of softballs. Her neck was long and slender, her nose straight and small. She had big blue eyes, full lips and a brilliant smile all topped by a lush, thick mop of mid-back length blond hair.
She was a seductive little thing as well. Fucking her had not been on my agenda but apparently, it had been on hers. She had come over from next door to hang out with me in my swimming pool in my stockade-fenced backyard, just like she had done for the past thirteen years, ever since she was five. I had had a few beers between bouts of horseplay in the pool while she had lemonade. (She didn’t like beer.)
Two hours and five beers later, her tiny bikini and my swim trunks were floating in the pool, she had sucked my cock until it was hard and I had eaten her to what looked like a tremendous orgasm while she sat on the edge of the pool. And now, despite my misgivings concerning her diminutive size and my fat dick, she was mounted on me with my thick eight inch cock embedded in her formerly virginal snatch.
Earlier in the afternoon, after our horseplay was done and we were hanging on the side of the pool, she leaned forward and planted an unexpected kiss right on my lips. She pulled back and looked at me.
I cleared my suddenly tight throat and asked, “Diane, why did you do that?”
“I have these dreams,” she said quietly, “And you’re in all of them. So...”
“So...” I said, trying to encourage her.
“So,” she said, “I’ve picked you.”
“Picked me for what?”
She blushed and looked at my chest as she answered. “Umm ... I want you to ... Uhh ... I want you to...”
I reached out and tipped her face up to mine. “Come on sweetie, spit it out.”
She blushed again, then squared her shoulders and looked right at me. “I want you to be my first man!”
“You what?” I goggled at her, sure that I had not heard her right.
“I want you,” she pointed at me, “ ... to be my first man. I want you to take my cherry!”
“Oh sweetie,” I said, almost strangling while trying to talk through the lump in my throat. “I’m flattered honey, but sweetie, I can’t! Your parents would kill me!”
Her face clouded up and she looked at me sadly. “I’m of age,” she said softly, “They have no say in who I decide to take to bed. And you know that I’d never tell them anyway.”
“Sweetie...”
“I wouldn’t,” she said sadly. “If I’m going to lose my virginity, shouldn’t it be with someone who knows me and loves me, someone who would think of me rather than just himself and would make my first time good for me?”
I stared at her with my mouth hanging open as we clung to the side of my pool and that’s when she made her second move, swooping in for the kill, glomming onto my mouth with hers and trying to lick my tonsils. I unthinkingly kissed her back and by the time my brain kicked into gear, she had both of her hands down the front of my bathing suit, playing with my rapidly hardening cock.
And somehow I found my hands mauling her proud tits under the tiny top of her bikini. She took her hands out of my suit long enough to pull the string that held her top in place, broke the mind-bending kiss she had started and lunged out of the water, climbing up me like I was a ladder and cramming a fat, erect nipple between my lips.
The little head took over and my hands slipped down to her tight, world class ass, holding her in place as I sucked about half of her plump tit into my mouth, sucking and chewing her rapidly hardening nipple as we submerged into the water. My feet hit bottom and I walked towards the shallow end until her ass was level with the side of the pool and sat her there on the edge. Her arms went around my head, holding my mouth on her breast while she used her feet to push my bathing suit down to my knees.
I sucked her nipples until they were hard enough to scratch glass. Her hands left my head long enough to pull the strings tied at her hips and there was a tiny splash as her bottoms hit the water behind me. Then her hands were back on my head and she was pushing me down, my lips and tongue caressing her flat, muscular belly and then her hot, virgin cunt.
I ate her out with all the skill I could muster, (the little head at work again!) as I wanted her to come back for more and I was afraid that she wouldn’t. She bucked and writhed her way through what seemed like a huge orgasm and then pushed me away, saying she was too sensitive for more. Then she slithered off the lip of the pool and submerged right in front of me.
I damn near jumped out of my skin when her hot mouth plunged down over my half hard cock, sucking it deep inside and working it over like a woman twice her age. She stayed down there for over a minute, blowing me until I reached down and pulled her up. She wrapped her long, lithe legs around my waist, trapping my by now steel hard cock between our bellies and kissed me again, grinding her steaming hot cunt against the underside of my cock.
My hands went to her taut, round ass, cupping a cheek in each hand. She moaned her approval in my mouth as my two index fingers found her drooling little cunt and slid inside. She was furnace hot in there and very, very tight. She moaned into my mouth again and her hips started moving, bobbing up and down on the two fingers that were embedded in her pussy.
I turned and found my way blindly out of the pool and sat naked on a big, thickly padded chaise lounge, kissing my hot lover-to-be all the while. Uncounted minutes later, she stopped kissing me as I finally drew a small orgasm out of her with my fingers.
She tucked her face into the corner of my jaw as she gasped and moaned through her orgasm, her hard nippled tits drilling into my chest as she rode it out. I laid back with her sprawled on top of me, her narrow hips still grinding against my turgidly erect cock.
Her hot breath huffed against my neck as she laid on me, recovering from her cum. Then she put her hands on my chest and levered herself upright, still sitting on my cock. She looked at me gravely for a moment, then pulled off her bathing cap and shook out her long hair, combing it with her fingers, arms up, elbows out, ripe breasts thrust out and on display in the timeless manner of women everywhere. Neither one of us said a word.
She lowered her arms and leaned on my chest again, giving me a lust-filled, smokey look. She got to her knees and my cock, drenched in her fluids came up with her. She took it in her hand, crouched over me and aimed my rigid cock at her wet cunt.
“No,” I croaked.
“Why?”
“You’re too small, I’m too big.”
I was surprised that my cock didn’t turn around and clout me in the mouth. I wanted this young woman. I wanted her to sit on my cock. I wanted to fuck her. I wanted her more than I’ve ever wanted any woman in my life. And that’s why I said no. Because no matter what the little head said and despite what I’d already done with her, she was not just an easy lay. She was a breath-taking, beautiful eighteen-year-old woman and the daughter of two of my closest friends. I was unwilling to chance hurting her. My cock was too thick. Something would tear.
“I’m on the pill.”
“I’m too big,” I said again as I gawked at her.
“Bullshit!” she cried. “You don’t have to do anything, ok? I’m not gonna do it if it hurts! Let me try! Please!”
“I don’t know...” I said reluctantly.
“This...” she said, putting her hand on her pussy, “was designed to widen enough to give birth!” She grabbed my cock, “This is big, but it ain’t that big! Please, let me try. Please!”
I wanted her. I really, really wanted to be the guy who taught her how to make love. “Ok,” I said. “If you can get it in, we’ll make love, all right? But if you can’t, or if it hurts you, I’ll know and we stop. Agreed?” She leaned over, gave me a kiss that scorched my tonsils and got back up on her knees.
“I’ll take that as a yes.” I croaked.
“Thank you,” she said, a serious look on her face.
“All right. Go ahead. But I’m not going to help. You’re on your own.” I gave her my patented ‘I Know All’ look. “Just remember, I’ll know if it hurts,” I warned her.
“Don’t worry,” she replied. “It won’t.” And she started.