Emily Ch. 01

There was a knock at the door.

I chose to ignore it. It was probably just the delivery guy with some package my girlfriend had ordered. He could just leave it in the hall. I was, shall we say, indisposed at the moment: in bed, pants off, headphones on... you get the picture. My girlfriend was at work and I had chosen to spend my evening with a little stress relief. We have a healthy and active sex life, don't get me wrong. But there's something different about doing it yourself every now and then.

"Ben, open up!"

Goddamnit. I recognized that voice. Although, I had never heard it here before. That was my girlfriend's coworker, Emily. They were waitresses together at the place a couple buildings over. The nice thing about living downtown is that everywhere we needed to go, including work, was walking distance. I had met Emily on several occasions when I'd come by the restaurant. We had even gone out for drinks as a group after my girlfriend got off work.

I always liked hanging out with Emily. She was genuinely sweet, funny, and enjoyable company. She was also, coincidentally, stacked. I can only guess of course, but I'd estimate she's 5'6", 110 pounds (10 of which were boobs), and maybe a 34E. She looked like a brunette Kate Upton. And clearly, I wasn't the only one who thought so. My girlfriend had raved about how nice Emily's boobs were, and would affectionately laugh at how her friend always seemed to show up to work sans bra when rent was due. One night after drinks, I was feeling particularly brash, and on the walk home I confessed to my girlfriend that I found her friend difficult to look in the face. She playfully slapped my arm, but then conceded that she too struggled to make eye contact after a couple beers. That wasn't the only allusion my girlfriend made to her bicuriousity, but that's a story for another time.

"Ben, hurry, I know you're in there! I only have a few minutes!"

Whoops. How long had I left Emily knocking at the door? I guess my reminiscing had melded into my fantasizing. Goddamnit, "Coming!" I yelled to her. I thought I heard a small giggle from the hallway. I opened the door from my apartment only wide enough to stick my head out. I didn't necessarily want her to see the rest of me like this. "Hey, Emily, what's up?"

"Finally!" Emily said. "Your girlfriend told me you'd be home to let me in. Look, while we were doing our sidework, I accidentally spilled marinara sauce all over my shirt. I don't have time to run all the way home to change, and your place is so close to work, and your girlfriend said I could borrow a shirt."

"Oh, um, sure. Of course. Um, come in..." I hoped my extra long t-shirt would hide my dwindling erection. I wasn't sure how my girlfriend expected one of her shirts to fit Emily - my girlfriend is the hottest girl I know, but she's not as well-endowed as Emily; no one I'd ever met is as well-endowed as Emily.

Emily pushed past me into the apartment. She gave me a quick look up and down, smirked, and said, "Cute outfit. Where's your girlfriend's dresser?"

"In the bedroom, to the left there," I informed her. I was so pleased to be of assistance to this wildly attractive, platonic friend that I briefly forgot the state of the bedroom. A little too late, I clamored to follow Emily in, hoping to subtly straighten up.

Emily saw the sheets thrown back, the open laptop, the headphones. She looked back at me, starting with my boxers, and then flicking her eyes up to meet mine. She smirked, and said, "Don't worry. Your girlfriend warned me what I'd be interrupting."

Great, I thought. I know girls talk, but I'd prefer these sorts of habits were more of a private matter between me and my girlfriend.

"And don't be embarrassed," Emily continued. "I spend my days off the same way."

That shocked me. While my sex life had been pretty active since getting to college, and I had learned a lot about the world from the internet and my girlfriend, I had grown up in a very conservative household - the type where it was assumed girls didn't enjoy sex and that masturbation was an exclusively male past time. I was relieved to learn over the past couple years that those were all inaccurate assumptions.

While I was reeling from Emily's brazen confession (and trying not to picture her in action until after she'd left), she had apparently chosen a shirt: one my girlfriend would probably consider over-sized and comfy, but might look tight and sexy on Emily's frame. Emily had exited to the living room, and I distractedly followed. "Well, I'm glad I was able to help. Are you gonna make it back to the restaurant in time for-"

I froze mid-sentence. Emily had stripped off her t-shirt right there in my living room - right there in front of me! Lucky for me, it was the end of the month... Her boobs were as perfect as I had imagined. They didn't sag or droop an inch when released from her tight shirt. Her nipples were tight and erect, right at the center of two perfect pink, quarter-sized areola.

"Ben? Ben. Ben!" Emily giggled and I became aware I'd missed the last several seconds of whatever she'd been saying. "Are you alright, Ben?" I nodded. "They're just tits, Ben. Although, I'm happy you like them." I nodded again. "Why don't you have a seat, Ben? You look like you're gonna fall over." Emily giggled again. I loved that giggle.

"As I was saying," Emily continued, "I actually don't have to be back at work for a little while. It turns out they overscheduled us tonight. I just want to be back for the dinner rush. Seeing as we've got some time to kill, I thought maybe I'd hang out here for a little bit?"

I finally found my voice. "That sounds great!" Too eager. "That sounds great," I repeated more measuredly. I'm not sure when Emily had put on my girlfriend's shirt, but I was finding it easier to think now - even despite her nipples poking so prominently through the thin cotton. "What do you want to do?"

"Well..." Emily stretched out the word as she stretched her arms up to the ceiling, bringing the shirt up to expose her midriff temporarily. She giggled again as she couldn't help but notice me noticing her body. "Maybe we could finish what you started?"

"What?"

"You know. You could go get your laptop and we could finish whatever you were watching. I'm always curious what other people are into."

"I don't know..."

"Come on, Ben, it'll be fun!" She bounced in her chair as she said so. I was still hesitating, so Emily got up and went back to the bedroom herself. She talked as she walked, "Look, it'll be harmless. You touch yourself; I'll touch myself. No harm, no foul."

I finally gave up. This was too good an opportunity to miss. And she was right, if we both kept to ourselves, then we weren't doing anything too illicit, right? But then I remembered what I had been watching when Emily knocked.

"Ohhhh," I heard from the doorway. "Busty college slut titty-fucks lucky guy," Emily read the title as she carried my laptop back to the living room. "I should have guessed. And she's a brunette too. Fantasizing about anyone in particular?" she teased me.

I was so embarrassed. I don't always masturbate thinking about Emily... but I'd be lying if I didn't say she's a lead actress in my mental entourage. I didn't know how this was supposed to proceed (my girlfriend knew I watched porn, but we had never watched together), so I was glad Emily was taking the lead. She set my laptop on the coffee table, sat down next to me, unzipped her pants, and cuddled up next to me. Already, we were touching, but I guess it wasn't sexual touching.

"I usually watch girl on girl," Emily casually informed me. "I just find the female form more sensual. But I can get off to this too."

I was watching, but I couldn't pay attention. I was too nervous about what I was expected to do next, and I kept stealing glances at Emily's unzipped jeans. Emily kept looking from the porn to me, back to the porn, and back to me. "Go ahead," she encouraged. "Finish what you started." When I hesitated, Emily stood up, unceremoniously shoved her pants and underwear to the floor in one motion, and sat back down. That was enough for me. One glance at Emily's tight ass, and my dick popped through the flap of my boxers all by itself. "Finally!" Emily said. "That's what I've been waiting for."

The porn was long-forgotten. I was too busy admiring Emily's fit body, the curve of her thighs, and the trimmed brunette triangle of hair just above her pussy lips. Likewise, Emily was too busy admiring my penis. It stood proudly erect, 8" long and 4" around. "You've got some good equipment," she complimented me as casually as if we were comparing kitchenaid mixers. And with that, she got to work: she stuck three fingers of her right hand in her mouth, sucked them gratuitously, lowered them to her pussy, and began fingering her clit. I was awestruck and frozen in place. Rolling her eyes, Emily grabbed my right hand, licked my palm up to my fingertips, sucked three of my fingers into her mouth, and then placed my hand on my dick. I got the message and started stroking.

We watched each other play for what felt like a lifetime. Every fidget of her fingers, every twitch of her thighs, every flutter of her eyelashes, and every gasp from her lips was burned into my memory forever. She knew exactly how to touch herself to get herself off, and I knew she was telling the truth when she said she spent her days off the same way I do. All too soon, her body tensed up and I knew she was on the verge of orgasm. Still, she surprised me one last time.

"Choke me," she demanded softly.

"What?"

She looked me right in the eye, and said, "Choke me."

I was too far gone to remember our "hands to ourselves" rule, so ever the accommodating host, I wrapped my left hand around her neck and squeezed. That pushed Emily over the edge and her whole body convulsed and shook with orgasm. Her fingers were a blur on her clit. Her face turned red and her lips clamped tightly shut. I almost came just at the sight of this powerful orgasm.

When she finally opened her eyes and gasped for breath, I released my grip on her throat. She came down slowly and her breathing evened out. She looked me in the eyes again. "Thank you."

"No, honestly, thank you! That was the sexiest thing I've ever seen."

"Did you get off too?" Emily asked, while looking around for some evidence of my cum.

"No, not yet."

"Is that due to performance anxiety, or wishful thinking?" Emily asked coyly.

"I was a bit distracted," I teased back.

"Well, I think I need to thank you for letting me in to borrow a shirt," she suggested. My heart leapt as Emily slid to the floor in front of me. She grabbed my dick with her right hand, which was still wet from playing with her pussy. She started to jack me off, slowly but firmly. As I sunk into my seat on the couch, she leaned forward and licked all the way up my shaft, before sucking the head into her mouth. She rolled the head around and flicked her tongue on the underside. Then, she steadily and deliberately pushed my dick deeper and deeper into her throat until her nose was in my pubic hair. I twitched in her mouth, but held on for dear life. I didn't want this to end just yet. She pulled her head back off my penis and breathed in deeply, a trail of spit leading from my tip to her lips.

"Have you ever actually titty-fucked a busty college slut?" she asked me. I shook my head violently and Emily giggled. "Well, what are you waiting for?" She got up on her knees in front of me, bunched up my girlfriend's shirt until it covered her boobs but exposed her midriff again, and pulled me by my knees toward the front of the couch. She spit into her own cleavage and then rubbed it in. Seemingly frustrated by the lack of lubrication, her eyebrows furrowed briefly. Then, her eyes brightened as she reached down to her still dripping pussy, inserted one finger at a time between her lips, and then brought her now re-wetted hand to rub into her cleavage. Satisfied, she turned her attention back on me and thrust my penis between her luscious boobs. As she bounced her tits on my cock, I thought nothing could ever top this experience.

I was glad I had already cum this afternoon and had been on round two when Emily knocked, or I never would've lasted as long as I did. The feeling of her big boobs squeezing my cock, the knowledge that her pussy juice was providing the lube, the sight of my dick peeking out of her cleavage, and the taboo of Emily wearing my girlfriend's shirt were leading me to orgasm quickly. Emily looked up at me with her big beautiful doe eyes and asked if I wanted to try one more thing with my little college slut. Of course I did.

Emily extracted my cock from her tits, stood up, and walked around the coffee table. I watched her ass sway and wondered what she had in store for me next. Emily laid on her back on the coffee table with her head towards me, poked her chin toward the ceiling, looked me in the eye, and winked. That was all the invitation I needed. I got on my knees and roughly shoved my cock down her throat again. I fucked her face like I longed to fuck her pussy. Emily fondled my balls while I drove my dick in and out of her mouth recklessly. This final position was too much and I quickly told her, "I'm gonna cum!" I pulled out and reached to start jerking myself off, but Emily slapped my hand out of the way and took over finishing the job.

"Cum!" she ordered. "Cum all over my pretty little face. Cum all over my slutty little lips. Cum all over my tits in your girlfriend's tiny little shirt!" Who was I to refuse her request? After so much buildup, I came everywhere. I came on her pretty little face. I came on her slutty little lips. I came on her tits in my girlfriend's tiny little shirt.

Emily smiled and giggled. "Yummmm, that was so much fun!" she exclaimed. She sat upright and turned to look at me. Her mascara was running down her cheeks, there was spit all over her face, cum was dangling off her nose and her chin, there were puddles of cum on her clavicle running down into her cleavage, and there were wet spots of cum on her shirt.

In my post-cum clarity, I began to feel an inkling of guilt, but Emily promptly squashed that. "Your girlfriend was in on this by the way."

"What!?"

"Your girlfriend was in on this. She spilled the marinara on me on purpose. She told me you'd be here masturbating. She told me you fantasized about my tits. She told me to get a little crazy with you. If you don't believe me, check your phone."

My phone? Where was my phone? I ran to the bedroom to retrieve it, and there was a text from my girlfriend from half an hour ago. "Send me a photo of that little cumslut!" I chuckled at how I'd been set up, and in admiration for my wonderful girlfriend. We'd talked about opening our relationship but only as a fantasy while we were fucking. I never thought she'd actually condone it.

"She wants a photo," I informed Emily. Emily smiled at me with cum still dripping off her face, with her nipples poking through my girlfriend's shirt, and with her neatly trimmed bush on display. She gave a peace sign as she posed for the photo.

"Send that to me too," Emily requested. I offered her a tissue, but she only cleaned up the mascara and then threw the tissue away. "I think I'll leave the cum there. At least until I get back to work. I heard it's good for the skin." Emily winked at me as she pulled on her jeans. "Hey, you should meet us for drinks after work. And no more jacking off between now and then! I don't think we're done with you just yet."

Emily headed out the door, and I collapsed onto the couch. As I looked to my right, I saw Emily's black thong on the floor under the coffee table. My phone chimed, and I saw a new message had arrived. Emily had sent me a photo. She was back at work and she had taken a selfie in the bathroom mirror. My girlfriend was with her and was licking a glob of my cum off Emily's face. The message read, "I got some help cleaning up before I clocked in." Despite all it had been through today, my cock rallied to attention. It was going to be tough not masturbating again until I met up with these girls for drinks.