Tommy Boy

It was an unseasonably warm New Year's Eve for Chicago: 60 degrees, t-shirt weather for the natives. I had just left a dinner with my group of friends to head to a party in a neighboring suburb to which my friend James had invited me. Over the course of our winter break, sexual tension had been climbing between us but I still wasn't sure I wanted something to happen. He was staggeringly witty and had a chiseled jawbone but I found him just a tad too slick on occasion, and this put me on edge.

As a girl wholly disinterested in dressing up and playing nice, I was clad in my go-to outfit for most occasions barring weddings, funerals and job interviews: yoga pants, UGG boots and a shirt from Urban Outfitters that ran a thin line between beautifully fashion forward and merely questionable. I stood on the front porch enjoying the night, waiting for James to answer his phone. Mid-ring, the door opened and it wasn't James but his best friend Tommy.

Let me take a detour here and explain how I knew Tommy. At the first (and only) rager I ever threw at my house, James had come bringing several of his best friends. I was dating an enormous tan moron at the time but despite that my jaw had hit the floor the first time I saw Tommy. He was tall, 6 foot 2 and muscular in the best way possible: from years of working out and crew. He had a mouth normally set in a grim line and tawny eyes. When he laughed, his nose and eyes crinkled. He was perfectly masculine, devastatingly handsome and generally grumpy. While we didn't exchange more than a few words the night of my party, I had seen him once over winter break when we saw the latest installment of the Harry Potter movies with James. They had made fun of me for sobbing unrestrainedly when Dobby the house-elf died. I had no idea what he thought of me. He was the definition of stoic.

He ushered me into the house wordlessly and once inside we hugged awkwardly. The party was typical of college freshmen: lots of Natural Light beer and UV Blue drunk straight out of the bottle. At midnight we all gathered downstairs to watch the bottle drop. James and I had already joked that we would be each other's midnight kiss but secretly I was already wondering how angry he'd be if something happened between Tommy and myself. The ball dropped, Tommy popped the champagne and James and I kissed: closed mouth. He was well on his way to obliterated and I was quite sober so there was much attempt at Frenching on his part and hasty retreat on mine (insert disparaging remark about French here).

As Tommy passed me the bottle of cheap champagne, we heard that the host's aunt would be dropping by soon to check that all was in order. Naturally, this presented an issue for us so we gathered coats and shoes and met outside to game-plan.

Standing in a circle on the sidewalk, shivering slightly, we discussed what to do. There were parties all over the North Shore that we could go to, but none of us could drive by that point. Eventually we decided to walk and as we started to do so, Tommy reached down and firmly grabbed my ass. I looked up at him, honestly surprised and he grinned down at me. My heart flip flopped.

"Excuse you," I whispered (though everyone was far too drunk to notice) "That's my ass thank you very much."

"You're welcome." Tommy responded. "My hand is warm."

"You're a piece of shit," I reprimanded him, smiling inwardly. He withdrew his hand from my yoga pants and smacked my ass.

"Start walking, we're lagging behind" he commanded. My stomach fell out my butt. I love a man who orders me around.

Tommy, James, their best friend Henry and I began to walk towards a party we knew of. The night was fine when we were moving and we drank beers and smoked cigars as careless teenagers are wont to do. Cars honked at us and we yelled back a cacophony of happy new years' as we laughed and fell over ourselves. Tommy intermittently grabbed my ass and pulled me closer and I would scooch away, laughing. Henry and James were walking a few feet in front of us singing Irish drinking songs and making general asses of themselves. Tommy and I didn't speak much, just laughed and enjoyed the night and the moment.

Then we simultaneously looked at one another and he leaned down (I'm 5'4" on a good day) and kissed me while we walked. Yes it was as awkward as it sounds. And yes, sparks flew. We giggled to ourselves, enjoying the scandal of kissing while Henry and James walked just a few feet in front of us.

We hopped from party to party that night courtesy of a friend of James' who we happened upon (seriously) at a stop sign. I sat in between Henry and Tommy in the back seat and endured much fondling from both of the two drunkards.

We ended up at the house of a kid that everyone but me knew. In his expansive basement we cracked beers and sat around shooting the shit. James was extremely drunk, Henry and Tommy less so and I was sober. Henry had been noticing the sparks flying all night and was taking full advantage of giving us shit. James was oblivious, more intent on feeding Heineken to our host's mastiff.

Eventually I got up to go to the bathroom and as I walked around the corner, Tommy grabbed me and pulled me into the basement bedroom.

He slammed the door closed behind him and growled in my ear, "This ends here." I swooned.

I grasped his face with two hands and we kissed, really kissed. Our lips pressed together and something even better than fireworks exploded behind my closed eyes. Our tongues grappled with one another and he bit my bottom lip, less than gently.

He picked me up and threw me onto the unmade king sized bed and that's when I realized we were in the host's bedroom. Given the moment, I threw caution to the winds.

We rolled around the bed kissing furiously. Tommy unzipped my shirt and threw it across the room. His lips found my neck and my earlobe and he kissed me furiously, his stubble scratching across the sensitive skin.

"You're so sexy, you're so sexy" he kept whispering into my ear. His hands were large and calloused and he had me tightly ensnared in his grip. That being said, I had no intention of leaving. I could feel him pressing through his corduroys and I shifted my shoulders to place one hand gently on the bulge. He stiffened and looked at me through the gloom.

"Is this what you want?" I whispered.

"Yes." He half growled, half groaned.

"Tell me what you want," I bit his earlobe.

"I want to be inside of you."

That was all I had to hear. My yoga pants and one sock were flying across the room not even a second later and a condom was coming out of his wallet. He threw me back against the pillows and rolled the condom onto his impressive length.

"Go slowly," I warned him (A side note: I have reason to believe that am the tightest non-virgin alive. It doesn't matter if I had sex five minutes ago or five weeks ago, it's a fortress. And I haven't met a man yet that doesn't love it. Tommy was no exception).

Our skin on our chests met and burned as he slowly pushed into me. I wrapped my legs around his broad back and gasped as I felt the head of his cock move into my pussy. Though I was dripping wet by that point, he moved inch by inch until I was full and there was still more of him left. He looked down at me.

"There we go," he groaned. "There we fucking go."

I grabbed the back of his head as he began to punish me and kissed him with all my might while hanging on for dear life. I pushed my hips back against his and we settled into a perfect furious rhythm, my lips at his neck and his enormous hands around my hips. His panting in my ear only served to excite me more but I didn't want to cum just yet.

"Hold on," I gasped, putting my hand on his burning chest. "Let's switch it up a little bit. Tell me what you like."

He blinked at me, obviously struggling to pull a lucid thought together out of the fog of testosterone and alcohol. "I don't know," he murmured. "I guess..." He pulled out of me with a loud slurp and flipped me over, pushing me up against the headboard. I lifted my hips and let him in from behind. He groaned audibly and bent over my back whispering in my ear how tight I was. I laughed and pushed back against his hips even harder.

He began to fuck me from behind and I could feel myself getting close. His enormous hand closed around one of my breasts and began to knead it hungrily. I reached back between our legs and got hold of his balls, which were tightening with every second. He groaned and slammed into me harder until I was also moaning audibly as he stretched my pussy more and more with every passing second.

All of a sudden he stopped. "I want to eat you out." He pulled out again and threw me on my back and just as his tongue touched my clit a thunderous hammering on the door began. I was livid. And I was so close another two seconds would have had me cumming harder than I had in two months. We could hear James slurring outside the door to come out. We both groaned and Tommy gently kissed my now red and sopping pussy. I almost grabbed his head and pushed him back down there but we were guests, and I was sober enough to know better.

We rolled off the bed and began searching for our clothes. Tommy's massive erection was still very much there and I looked at it and then looked at him. "Suck my dick," he growled, peeling off the condom. I knelt down and as my tongue touched the tip the hammering on the door began again.

"Jess, Tommy get outta there!" James slurred. "You needa come outta there!" he reiterated.

A frantic search for clothes ensued and we slunk out of the room minutes later, stinking of sex, our cheeks glowing.

To be continued...