Peggy

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After finals, drinks lead to a friend with new benefits.
2.4k words
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I stepped out of the hall, free at last. No more class, no more finals, and a summer ahead of me before I started working at PWC in the fall. Making bank there, too. Without even meaning to, I broke into a wide grin.

Back at my apartment, just off campus, I did what any self respecting graduatee would do: two shots of Fireball. Then I headed next door to see what was happening, with a bottle of cheap wine in hand.

Our friend group had split two apartments next to each other - the guys lived in one, the girls in another. It worked out well. We'd rotate who would host pregames. Everyone got a bit of privacy otherwise, though of course we'd usually be in one apartment or the other just hanging out most nights. And while I'm pretty sure a few people have hooked up over the years, no relationships have complicated anything.

"Hi," I said, knocking on the door as I swung it open. "Anyone home?"

"Hey Winston!" Peggy called.

I entered the living room to find her sitting on the couch, glass in hand of something dark, watching a rerun of How I Met Your Mother.

"Hey!" I said. "All done with finals, so I brought some wine!" I lifted the bottle to show her.

"Yes!" she cried. "I'm all done with finals too. But Yvonne and Joanna still have a couple. I thought I was going to be solo." She smiled. "Glad you showed up."

"Happy to help."

I uncorked the bottle and poured two glasses, then settled in next to Peggy on the couch. She held the wine glass up to mine. "Cheers!" she said with a smile.

"Did you want to keep watching this?" she asked, "Or rather watch something else?"

I was taking a drink of wine. "This is fine."

She took a gulp to finish off her other drink, then sighed and leaned her head on my shoulder. I put my head on hers for a second of intimacy, then sat back up. That is, until my eyes were drawn to the collar of her shirt... and then lower. At the angle I had, it was a clear shot straight into the crevice between her breasts. I realized what I was doing and my head snapped forwards towards the TV.

We talked about post-graduation plans, and when the episode ended I helped myself to a second glass of wine, Peggy reluctantly sliding back up to a seated position.

"Hey, um, Winson...," she said, softly.

"Yeah?" I asked.

"Do you want to maybe do something besides TV?"

"Like what?"

"Maybe... I dunno... we could play a game or something?" She bit her lip uncertainly.

"Sure," I said, without thinking about it too much. "I'm down to play a game. What did you have in mind?"

"What about truth... or strip?"

I choked on the wine. "What?" I asked.

Peggy smirked a little. "So you've played truth or dare, right? Well, instead of daring... it's always truth. And if you refuse to answer, you have to take a piece of clothing off instead."

My mind flashed back to my peek of Peggy's cleavage and my dick jumped a bit at the idea of seeing her boobs completely.

"Uh, sure. I guess I can play that," I said, my mind racing at the possibility. I just needed to figure out what I could ask that she wouldn't answer.

"Okay, then," she said. "I'll start. When did you lose your virginity?"

"Freshman year of college."

"With who?" she asked.

"Nope, that's a second question," I told her. I decided to go straight for a hard question... with a game called truth or strip, I had little doubt where these were going to end up anyways. "Who was the most scandalous person you masturbated to?"

Peggy's jaw dropped slightly, then she smirked. "My cousin Raymond. He used to be on the swim team and would show up jacked as hell in a speedo to family gatherings."

My eyebrow lifted, and she stood up.

"I'm going to get a drink," she said. She came back with her wine glass nearly full to the brim, and sat down right next to me, our legs touching.

"My next question: what's your kinkiest fetish?"

"Nope," I said quickly. "Not happening."

"Oh, really?" she said. "That kinky? Such a shame." She put her finger on my chest and ran it down to my navel. "I guess something here is coming off. So what'll it be?"

I took a quick inventory: shirt, shorts, and briefs. I had walked over here in sandals, which were at the door. This would be a short one if I wasn't willing to bare the truth.

"Fine," I said. I set my drink on the coffee table and took my shirt and pulled it up over my head, then tossed it on the ground. "Happy?" I asked.

"Very," she said with a smile.

"My turn then: which of my roommates have you slept with?"

Peggy weighed her options, then frowned. "Fine," she said, "Hold my drink." She teasingly grabbed the hem, rolled it in her hands a bit, then slowly brought it up, higher and higher, revealing her stomach, then a baby blue bra pushing her breasts together, and finally off her head.

"Happy?" she asked, adjusting her bra. She glanced down at my crotch, a noticeable bulge starting to rise. "Never mind."

"For your question," she said slowly, pondering, "have you fooled around with a guy?"

I shook my head. "Nope."

"Really?" she said. "Curious."

"Okay, then. Spit or swallow?"

"Easy, swallow. Ever played with your ass or had it played with?"

My eyes widened. "Fuck. Yes."

"Did you enjoy it?"

"My turn now, nice try. What was the kinkiest thing you've ever actually done?"

Peggy smiled and stood up. "Not happening," she said as she slowly inched her shorts down over her ass and stepped out of them. She wore matching baby blue panties, nothing too scandalous but a bit revealing. "Chill out," she said, as my eyes drifted lower. "My turn now. Ever eaten your own cum?"

I grimaced and stood up. Peggy laughed. "You totally have!" she said.

"Fuck you," I said as I pulled my shorts off, any chance of hiding my now erect cock completely off the table. My briefs were not exactly full coverage to begin with (I like to feel sexy!), but with my dick straining at the fabric, there was no doubt at the details of it. Peggy whistled.

"When was the last time you masturbated?" I asked.

"Yesterday after my final. That's all you got? Okay, my next question. Have you ever masturbated to me?"

I wasn't giving her the satisfaction, but I had no choice. I wasn't going to lose the game before I got to see at least some boobs. "Yes," I said finally. "Have you ever masturbated to me?"

"Not fair! You can't ask the question I just asked," Peggy complained.

"That was never a rule," I said, "So answer the question."

Peggy let out a sigh, then wordlessly stood up and reached behind her back to let open the clasp to her bra. She held the cups up as the straps fell, pausing for a moment for dramatic effect to watch me on the edge of my seat, cock straining, before letting them fall to the ground. Her tits were fantastic. Round, plump, with rock hard nipples splayed out.

"Happy?" she asked. But she had a grin on her face. She had known since this started where it would end up going. "Clearly," she said. She reached her hand out and patted the tip of my cock, tenting my briefs.

"Want to take this to my room?" Peggy asked as her hand slowly wrapped around my dick.

"Yes," I choked out.

We collected our clothes and carried them. I'd been in Peggy's room before, but being practically naked with her was a different environment entirely. She had some pink curtains over the windows, with a big Bikini Kill poster (sans any bikinis) hung over her bed.

Peggy closed the door softly behind me, then tossed her clothes on the floor near her closet. "Bed," she ordered.

I dropped my clothes onto the floor where I stood and sat down on the edge of the bed. Peggy climbed onto my lap, her body crushing my dick into my thigh. Then she kissed me. I lifted my hands up to hold her head as she assaulted my mouth. Her hand snaked down my chest to the edge of my waistband, then her fingers snuck in to wrap around the base of my cock, which throbbed.

I tried to stand up to pull my underwear off but couldn't with her solidly on top of me. So instead I rolled her to the side and continued to kiss her with one hand under her head, while my other hand pulled off my briefs as fast as I could.

Peggy shifted from under me and climbed up further onto the bed, laying on her back and looking at me expectedly. I tried to climb up to kiss her some more, but her hand pushed my head down onto her breast. I took the hint and slowly sucked on her nipple. My right thumb started to slowly caress her other nipple, then I grabbed it between my index finger and thumb and started to roll it. Meanwhile I ran my tongue around in circles on her nipple.

She let out a moan of satisfaction. Then she put some more pressure on my head, pushing me further south. I had never eaten a girl out before, but I was so turned on that I didn't care about my inexperience. I inched south, kissing softly on her stomach along the way. My fingers found the waistband of her blue panties, and I pulled them down. Peggy lifted her hips a bit to help. Then I tossed them to the side, not caring where they landed.

Her pussy was shaved, with just a hint of stubble showing. It tickled a little bit as I kissed below her panty line and found her opening. Experimentally I licked along the slit.

"That's it," she said, "Right here." Her hand guided my head up a bit. I dabbed my tongue out and slowly ran it along her clit. "Ahhhh," Peggy sighed.

I kept going with my tongue, and moved my finger up to run up and down her pussy while I did. Then I slid it inside. "More," Peggy breathed. I slid another finger inside, then started moving them in and out. She moved a hand to her nipple and started to play with it, and her breath increased, quicker and quicker.

"Don't stop," Peggy warned. I had no intention of stopping, not until she had come. Her sighs continued to rise in pitch, sexy as fuck, making me as hard as I'd ever been. But my focus was all on Peggy. Her hand grabbed the back of my head and held it down against her clit as her hips started to buck up and down. "I'm gonna come," she breathed. "I'm gonna... don't stop, I'm gonna come. Fuck!"

With a final gasp, her legs started to shake and she let out a scream, "Yes! Oh god!"

I stopped my licking and fingers and look up at her smiling face, practically out of this world. "Good?" I asked.

"Fuck... yes," she breathed.

"That was... I hadn't ever done that before," I admitted.

"Well, you're a natural," Peggy said. She sat up and reached out to grab my dick. "Your turn now. Lay down."

I was on my back faster than she could blink. Peggy reached a hand out and slowly wrapped it around the base of my cock. Tantalizingly, she stroked up and down, barely an inch. My hips thrust anxiously, to no avail.

"Slowly, now. Enjoy this," she said, "And no touching!"

Reluctantly, I put my hands behind my head to prop it up so I could better watch, because if they were anywhere else they'd be wrapped around my dick.

Her hand picked up speed, going faster now. With her other hand, she brushed the head of my cock with the palm of her hand. I let out a groan.

"You like that?" Peggy asked, "Then you'll love this." Her head dipped down, the tip of her tongue stretching out to lick the underside of my cock like a lollipop. My eyes rolled in pleasure. Then her mouth engulfed the tip with hot fire, while her hand kept moving ever so slightly up and down on the base of my dick. I moaned, resisting the urge to grab her head and shove it down all the way to the base. I could feel myself getting close. This wouldn't be long.

She paused to lick a finger, her hand and mouth speeding up a bit. I felt it press against my asshole, and my hips jumped away from it in surprise.

"Trust me," she said, "I know what I'm doing."

So I tried to relax as her finger slipped into my ass, only to moan with pleasure as she found what must have been my prostate and pressed against it. I was moaning constantly now, as my balls tensed.

"I'm going to come," I warned Peggy.

She didn't slow down at all, just sped up. Her hand pumped the base of my cock like a piston, while her mouth sucked and rolled the head. Meanwhile, her finger was massaging my prostate. I felt immense pressure from both ends, the electric rising along my cock until finally, with a loud cry, I exploded into Peggy's mouth.

She kept going on my cock and prostate as my eyes closed from the pleasure. I kept firing shot after shot into her hot mouth until finally I ran out. She slowly removed her mouth from my cock, swallowed, then opened her mouth to show me.

"How was that?" she asked with a smile.

I just let out a contented sigh. Peggy crawled up my body next to me and kissed me. The taste of cum was still heavy in her mouth, but I didn't care. Then she laid on my chest, a finger idly drawing circles on my stomach.

I closed my eyes and took a nap with Peggy besides me.

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AnonymousAnonymousover 4 years ago
Short and sweet!

A very nice first story! I found myself wishing I was Winston. It was sweet of his friend, Peggy-with-the-fantastic-tits, to suck him off and swallow him. More from these two would be wonderful. Thanks for writing!

AnonymousAnonymousover 4 years ago
Yet another Story only half finished

Why not finish what you started

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