My (F)irst Orgasm with Dad’s Best Friend on High School Graduation Night

Long time lurker… I’ve shared this story with a few DPPers and decided it was finally time to give back and share my corruption with my first, jill-off sub-reddit.

My need to be a slut for married men all started the night of my high school graduation. He was my dad’s best friend. And I was best friends with his daughter, naturally. We went out celebrating that night. She was a year younger than me and had to be home at curfew. But my parents thought I was at a sleepover with girls from my class. I’d just planned to stay out all night. I got drunk and the parties started to dwindle. And I didn’t have anywhere to go. So, I went to her place and tapped on her window, but I couldn’t wake her up without waking up the whole house.

I slipped through their back gate and decided it would be fun to get in the pool. The pool was slightly downhill from the house and there was a kitchen/grill area and storage for towels and bathing suits. I stripped down and put on a little bikini. I opened up the minifridge and took out a bottle of beer and slipped into the water. I was starting to pass out on a float, when the sound of the back door opening startled me and I fell into the water.

It turns out I’d set off a silent alarm and Mr. Hayes had gotten a call on his cell phone from the alarm company. He looked at the security cameras and saw me digging through the swimsuit drawer. He told them everything was fine and continued to watch me – rubbing his dick as he spied on me slipping off my dress, then bra and panties. My naked little body first pulling on the tiny bikini bottoms and then adjusting my tits in to the string top. (I took that red bikini – his wife’s – later that summer and still have it :P) I, of course didn’t know about all that in the moment I’d been caught, and I just thought I was in big trouble.

Hoping to scramble out and hide, I’d only made it to the shallow end stairs as he appeared in his boxers and an open robe.

You’re stealing my beer huh? he asked me as I came out of the pool, water dripping from my body. I’m soooo sorry Mr. Hayes, I said terrified of the consequences of him telling on me. My dad would know about all of it; the sneaking out, the drinking, the breaking and entering. But he just smiled at me and told me to be quiet or we’d wake the house up.

It’s ok. You look like you’ve had fun tonight. I felt like his eyes were dancing over my body and I was incredibly aware of my nipples hardening under his gaze as my wet body was freezing. I wasn’t very experienced at all at the time. But I was so relieved that it didn’t look like I was going to get in trouble.

“I don’t think you’re in any state to be out here alone. I don’t want you drowning,” he said as he grabbed a towel for me. He opened it wide and I stepped in. He wrapped it around my body and hugged me in to his warm body drying me off as he ran his hands up and down my arms over the towel. He let his hands rub the sides of my tits as he did, but I still couldn’t be sure if it was an accident or not. I had goosebumps, but not from the chill, it was from the feeling I was getting from him.

He pointed me towards the outdoor couch and ended up opening another couple of beers of us. He asked me again if I’d had a good time tonight and how I’d ended up at his house. When I told him the parties had ended and I didn’t have anywhere else to go, he said he found that hard to believe. “You didn’t have anyone to go home with?” he asked, with a raised eyebrow.

I blushed furiously. I was drying off except for the trail down my back from my wet hair. I started to let the towel wrapped around me loosen up and fall. I was loving the way he was looking at me, and I wanted him to see my tits again.

I shrugged and told him the boys at school were never really interested in me, “Maybe I’ll have more luck at college.” He told me he found that hard to believe as he’d watched me “blossom” – that word still makes me instantly wet – into a beautiful young woman. I loved hearing him call me a woman. He put his hand on my knee and as we continued talking, he slowly started stroking my thighs. It was like nothing I’d ever felt before. He knew what he was doing and he wasn’t rushing like the couple of boys I’d fooled around with until then.

He went so slowly starting at my knee and working his way up as we chatted. Intermixed in our small talk were his stories of noticing me becoming mature. How beautiful I’d looked at prom that year. I felt so comfortable with him and partially because I was beyond tipsy I began confessing my insecurities. He assured me that guys my age were too immature to appreciate my beauty. That he had no doubt that I would could have any man -“man!” he’d said- at college. All the time he was making his way up my thigh. As his hand creeped higher my legs instinctively fell apart. just enough for him to touch me but not so much that I couldn’t lie to myself that I wasn’t inviting his touch.

He ran his fingers across the damp bikini bottoms just above where my slit began and then his fingers traced down my left thigh and back up across and down. He probably did this for 10 minutes. All the while, chatting and making me feel so desirable, and so horny, my legs fell open. I wanted his touch so much.

Soon enough he ran his hands up and down the fabric covering my wet slit while his family slept inside. He leaned in to my ear and asked if I was still wet from the pool. I shook my head no as he pressed harder into my folds – my wetness leaked out of the lycra crotch on to his fingers. His fingers ran over my cunt lips first over the fabric and then just to the side of it. I could feel him spreading my wetness on to the bare skin where my thighs met my lips. His fingers slipped beneath the tight fabric. He felt my bare pussy lips and groaned lightly: you shaved…. before running his finger up and down my wet slit.

I moaned out and he reminded me to be quiet. ‘Does this feel good?’ I shook my head yes, furiously, and he wrapped his other arm around me and pulled my back against his chest. My left leg remained propped up on the couch and my right foot fell to the ground. He continued to play with my pussy now circling his wet fingers around clit.

His left hand brushed up my stomach and over my breast. He massaged my globe and flicked his finger over my nipple until it was so hard and throbbing. I shuddered as the fabric scraped against it as he pulled the tiny triangle covering my tits to the side. He brushed his hand across my chest revealing my other globe. My tits were just big Bs/small Cs at the time but they were being pushed up and together framed by the red fabric.

I turned my head to look at him and he was staring down a my body. I must have looked like such a complete fuck toy. My creamy tits out, hard pink pebble nipples, a flat white tummy and his hand inside the red string bikini bottoms. My hips grinding against his fingers on my clit.

You look so fucking hot he whispered into my ear as he moved his fingers down and slipped one into my sopping wet pussy. I yelped and he brought his hand up and over my mouth. Shhhhhhhh, or we’ll have to stop the fun. The feeling of the shhh and his breath hot breath against the wet skin around my ears and neck sent shivers through my body. No one had ever paid attention to me like this. I had never felt this good.

He brought his hand down around my throat holding me against his chest and keeping me from making any loud noises. He continued to murmur in my ear. ‘Just like that baby girl, just like that..’ as my hips thrust in a circular pattern. I was instinctively trying to grind my clit into the palm of his hand as he moved his finger in and out of me.

My breath was becoming short, my legs started to shake. ‘That’s it cum for me. You are so fucking sex,’ He murmured in my ear. I nearly choked on his hand around my throat as my back seized up. My sharp shoulder blades cutting into his chest, my tits arched out, as my body began to roll against his hand. He was wiggling his finger back and forth inside me and had the heel of his hand pressed firmly against my engorged clit. ‘Cum for me,’ he said one last time – like I had any say in the matter. My legs slammed together tightly trapping his hand in my cunt as my knees flew up to my chest. I was a tight ball against him and I whimpered as my body had its first orgasm.

As I came down from a high that I still chase. I relaxed. He took his hand from my throat, but was still cupping my dripping pussy in thw other. ‘I’m sorry,’ I said, dazed and unsure of what had just happened. He chuckled. You have nothing to be sorry for. You are perfect. So sexy, he said nuzzling into my neck.

My chest continued to heave as I struggled to regain my breath. And I felt his head turn to watch the show. As I began to fully relax, he pulled his hand out from crotch. He chuckled and said you nearly broke my finger off.

‘I’m so sorry,’ I apologized again. ‘Never apologize for pleasure,’ he scolded me. ‘You’re a woman now.’ The hand that had been around my throat was now leisurely drifting up and down the side of my torso. It tickled and it was making me horny – again. He would continue by hefting my breasts, massaging them, and teasing my nipples. This all happening in the background of our next exchange, but it kept me so warmed up.