Checking Out 1

I met this girl in a library of all places. To begin with, I'm not that good looking a guy, so randomly picking up women isn't something I do very much. I'm fairly tall, and have hazel eyes, so there are a few things going for me. That said, I'm a bit chunky and tend to be kind of geeky. I had split with my previous girlfriend several months ago. It was getting to be depressing, especially since I was 30.

Anyway, a striking girl with long brown hair nudged past me with a faint "excuse me." I looked over at her. She was short, only coming up to my shoulders, and a little chubby in that good way that some girls have. It was impossible not to notice her enormous breasts, straining against a purple tank top. She also had her legs on display in a pair of very short shorts. It was the beginning of summer, though, so a lot of girls were dressed that way. She looked at me and brushed a lock of hair back from her face.

"Find anything good to read?" she said.

"Not yet, I don't think. What are you looking for?"

She got a sparkle in her blue eyes and smiled shyly. "Something dirty."

"Really."

"Yeah. I guess I'm in that kind of mood. I'm Jessica." She held out her hand.

I gave her my name and shook.

"Don't worry, I'm eighteen," she said.

"Why should I be worried?"

The sparkle in her eyes returned. "We'll see."

We went on flirting for a while there in amongst the shelves, walking around, looking through books and occasionally stealing glances at one another. Jessica came up beside me, standing hip to hip, and softly told me that she lived a few blocks away.

"Are you inviting me over?" I said.

She nodded. We left the library without checking anything out and walked out into the early summer heat. It wasn't a long walk to her apartment. She lived in an aging building, and I quickly found out that her place was very small.

"I have to tell you something," said Jessica as we walked up the stairs.

"Go ahead."

"I haven't really had sex very many times. It's been like after parties, and..." She trailed off. "I just don't want you to expect something and not get it.'

I nodded. "You don't remember much about it, and you're not sure how far you want to go with me right now."

"Right."

"Don't worry about it. I'm having the best day I've had in a long time."

Jessica turned around and kissed me, a lingering embrace that left just the faint impression of her tongue behind my lips.

"Thank you," she said as she unlocked the door.

It was a tiny one bedroom apartment with hardwood floors, and had a futon in the living room. Another girl was there, blonde, slim, a bit taller than Jessica, and only slightly less busty. She waved as we walked in.

"Who's this?" she asked.

Jessica gave her my name, and told her how we met. The other girl held out her hand.

"I'm Madison, the roommate. Actually, we trade off getting the bedroom and sleeping on this thing," she said, indicating the futon.

"Nice to meet you."

"I'm going to get something to drink," Jessica said, putting her hand on my arm. "You want anything?"

"Just some water," I said.

"So," said Madison. "What do you do?"

I sat on the opposite end of the futon from her. "I work at a company that designs standardized tests."

"So I ought to punch you after having to take the SAT and ACT?"

"Probably not. I don't have anything to do with either of those. But you might have plenty of other reasons to hit me once you get to know me."

Madison laughed softly, and Jessica sat down between us, handing me a glass of water.

"Keep an eye on your new boyfriend, Jess. I'm starting to like him," said Madison.

That wicked sparkle I'd come to enjoy so much popped up again in Jessica's eyes. "I don't see why we couldn't share."

Jessica leaned in close to me. I put my arm around her and pressed my lips to hers. She instantly responded, wrapping her arms around my neck and gently probing into my mouth with her tongue. When we broke the kiss, she lifted her top, exposing her huge breasts, and tossed it aside. She stood up and pulled down her shorts, revealing a pair of white panties with a little bow at the top. Madison moved down the futon next to me. Jessica was now naked, having quickly stripped her panties off, giving me a full view of her gorgeous body. Aside from her breasts, she had a soft but flat belly, nice legs, and a smooth pussy. I guess she noticed me looking at it.

"I wax," she said. "So does Madison."

Madison was looking in my eyes with some hesitation. I began kissing her, and she was no less enthusiastic than Jessica had been. I felt Jessica's hand on my crotch, rubbing my erection through my jeans.

"Oh wow," she breathed.

"What?" I said.

"It feels like you have a huge cock."

Huge wasn't a word I'd heard used about my member before, though I knew I wasn't small. I let her go on rubbing me and took off Madison's t-shirt. Like Jessica, she wasn't wearing a bra. She was wearing a small green jewel in her pierced navel. I squeezed her breasts and she began moaning softly.

"My boobs are really sensitive," she said as I kissed her neck. I bent down and took a nipple into my mouth. Her skin smelled faintly of strawberries, from what I learned later was a body wash she liked. I worked her shorts down. Madison wasn't wearing panties, and as promised, had a smooth, waxed pussy. I started fingering her, and her moans got louder.

Jessica had loosened my belt, and was working on getting my zipper down. I raised my hips to help her a bit. I continued to finger Madison and kiss her mouth, neck, and breasts in turns. I felt Jessica's hand go into my boxer briefs and start stroking my cock.

"Ooh, you are a big boy," she said.

"Why don't you pull his shorts off so I can see?" said Madison.

I stopped fingering her to get my jeans and underwear off. My cock sprang out, to girlish squeals of delight from both Jessica and Madison.

"You've already felt it," Madison said. "Come up here and get fingered while I give him a blowjob."

Jessica crawled up onto the futon beside me, and I finally got to put my hands on those glorious breasts. As Madison's mouth enveloped my cock in a warm, wet embrace, I squeezed and sucked on Jessica's boobs while I slipped a finger into her. She held me close and gasped. I worked my fingers in and out of her pussy in the same rhythm that Madison used to bob her mouth up and down on my cock.

After a few minutes, they switched places, Jessica taking my cock into her mouth and Madison coming up for more fingering. She first licked Jessica's juices from my fingers.

"You taste nice, Jess," she said. Jessica didn't respond, but kept sucking my dick intently, and hard.

Finally, I decided that I needed more than blowjobs. "Lay on your back, Jessica," I said. She did, wordlessly, intuitively spreading her legs wide.

I slowly entered her. Jessica was extremely tight, as I knew from fingering her. That might have been why she'd wanted to reassure me of her age. I wasn't ready for what she told me when I was inside her.

"About what I said before, only having sex a few times?" she whispered, giving my earlobe a bite. "I can't really be sure how far it went. This is the first I'll really remember. You're definitely the first guy I've sucked."

"Does Madison know you're so inexperienced?" I asked, softly. Madison was watching us, masturbating openly as I thrust into Jessica.

"No."

I started going at Jessica harder, making her moan loudly and her enormous breasts bounce. Madison had three fingers inside herself, and was moaning almost as loudly as her roommate. Jessica pulled me close and shuddered as I thrust myself completely into her pussy. She kissed me.

"I just came," she said.

"Good."

"Do you want Madison now?"

"Yes."

I pulled out of Jessica, my cock feeling cold now that I wasn't inside her anymore. Madison laid down for me, legs spread as Jessica had done. I slid myself into her, giving her a deep kiss as I did.

She wasn't quite as tight as Jessica, but then Madison was, I'd learn, rather more experienced She was eighteen, though, so I could feel her pussy working my cock as I thrust in and out of her. Madison was loud, moaning and screaming as I pounded her. Jessica had adopted Madison's practice of masturbating as she watched. She was fingering herself slowly, already having come.

Madison wrapped her legs around my back. "Harder!" she cried.

I started pounding her, ramming my cock into her soaking pussy. She arched her back and screamed. I felt her pussy contract and juices flood out of it. Madison was panting when her orgasm subsided. She pulled me down to kiss me.

"Well, that just happened," she whispered, grinding her hips slowly. "That dick of yours really split me open. Are you close to cumming?" she said.

"Pretty close."

"Who do you want to get you off?"

There wasn't really a choice. "Jessica," I said.

She laid down again, and I slipped my cock into her. She was just as tight and wet as before. I didn't take long before I was about to explode.

"Where do you want it?" I asked.

"All over me," said Jessica. "I want to watch it squirt out."

I pulled out of her, so close that I didn't have to stroke myself to start shooting on her. The first couple of spurts landed on her breasts. Both Jessica and Madison were letting out the squeals I'd found so endearing when they first saw my cock. I kept shooting on Jessica's naked body again and again and again, covering her belly in semen.

"Wow," said Madison. "Do you always shoot like that?" She bent down and started licking the semen off of Jessica.

The last of my cum oozed out onto Jessica's pussy mound. "Usually," I said.

"Save some for me," said Jessica. Madison licked up a mouthful of cum and kissed Jessica, giving her my cum.

"Good, isn't it?" said Madison. Jessica just smiled and brought some more cum up to her mouth on her fingers and licked it off.

Ultimately, there wasn't a future for us. We went on for a few months hanging out occasionally and having sex a few times a week, all three of us. But they were too young for me, and we all had our lives to live. It was a hard goodbye to Jessica, though. In the end, we found that we really had shared something special, and neither of us will ever forget that.