Back from Boston

Tuesday, April 28, 2009

Sorry not to post for a while... had a lovely weekend away in Boston visiting my college friend Grace. Grace is fantastic, she always lifts my spirits and we have a shit ton of fun together. I got in late Friday night and we stayed up until dawn, drinking and catching up. We spent the day Saturday wandering around the city, eating crappy (yet delicious!) hot dogs in the gardens and shopping at H&M on Newbury Street. I bought a super hot dress, and Grace got a low cut top that makes the most of her stunning tits.

We had planned to go out from there, but decided to run to her place to get all tarted up in our new outfits. Boston nightlife is a bit different from NYC nightlife. Sure, you'll see girls dressed to the nines downtown, but for the most part folks are more low-key than in New York. I like that. Sometimes going out in NY surrounded by statuesque stunners, I feel like the frumpy country cousin. I mean, seriously, is everyone in New York a model? Because sometimes it feels that way. Everyone wears the latest fashions and looks so put-together, even when they're rocking the 'I just threw on whatever I found on my floor' look. But in Boston, the vibe is much more relaxed.

Still, on a hot night, a sex kitten dress and killer heels don't look out of place in any city...

After getting all dolled up, Grace and I headed out to one of my two favorite bars in Boston, Bukowski Tavern. It's a fun place to go on a weekend night. Not a great place to talk and catch up, because it's super loud, but a good time nonetheless. I tend not to like too many bars in Boston, and certainly not downtown... If given a choice, I'd go out in Cambridge, but since Grace lives in Boston now, going out in the South End requires less drunken walking/cabbing at the end of the night. That's one thing I hate about Boston - the lack of public transportation late at night. If you stay until closing time, you're pretty much shit of luck for transport options unless you take a cab. I often take cabs when I'm at home, but Cambridge to Boston can be an expensive ride.

We stayed at Bukowski for a bit and decided to walk to my other favorite spot, Delux Cafe... Much as I love Bukowski, there's only so much yell-talking I can do before my throat starts to hurt. Plus, it was such a nice night out we wanted to take a drunk stroll.

Delux is one of those quirky little bars with a strange assortment of crap on the walls - Elvis memorabilia, Christmas lights, the works... cheap drinks, fun atmosphere. It's kinda teeny tiny, so it can be hard to get a seat, but it doesn't really matter.

When we got there, it was packed, so Grace and I wormed our way towards the bar to order drinks. She managed to get up front, so I waited behind her to grab our drinks. I was sorta standing there, spacing out a little when the guy in front of me turned around with two beers in his hand. I tried to back up a little to let him past, and looked up at him briefly. We locked eyes and he gave me such a big, genuine, amazing smile that I couldn't help but smile back. I'm normally so shy and awkward that when a hot guy smiles at me, I look away... But this smile was so infectious, so warm, I smiled back without even thinking. Just then Grace turned around with our drinks, so I followed her towards the back. Amazingly, a table emptied just as soon as we headed back, and we made a beeline for it. As we sat down, I whispered to Grace 'the hottest guy just smiled at me'... 'You mean the guy over there that keeps staring at you?' she hissed back... I stole a quick glance in the direction she indicated and saw the guy looking right at me. Thankfully, the darkness of the bar covered the bright red spreading across my chest. But still, I averted my eyes, totally embarrassed. If it weren't for Grace, I probably wouldn't have ever talked to the guy, but totally uninhibited woman that she is, waved him over.

He and his friend made his way back to our table and I realized he was even hotter than I'd first thought. I sipped my drink and tried to think of something witty to say, but was completely tongue-tied. Thank god for Grace... she started talking, the guys bought us more drinks, and soon I was drunk enough to chatter away and overcome my shyness...

The night wore on and I got steadily drunker. At one point I decided to duck outside for a smoke - I don't generally smoke anymore, but when I drink I like to have the occasional cigarette. As I tried to push my way through the crowd, I felt someone's hand grab mine. I looked back to see Caleb following me, a mischievous glint in his blue eyes. I smiled back at him and kept my hand clasped in his as we snaked out through the bar...

Once outside, we stood around chatting awkwardly amongst the other smokers. I nervously toyed with my lighter, not yet taking out a cigarette. I desperately wanted to kiss him, run my hands underneath his shirt, feel the warmth of his stomach under my fingertips. I was so mesmerized by his lips, imagining what he'd taste like, that it was all I could do to focus on what he was saying. Without stopping to think and before I could lose my nerve, I grabbed his hand and dragged him around the corner of the bar. As soon as we were away from the crowds, I pushed him back against the wall of a building and kissed him. God, he smelled amazing, warm and spicy and sunny...

I pulled back for a second, suddenly worried that I'd been too forward. Caleb took the opportunity to pull me further into the darkness, this time pressing me against the rough brick wall... I spent a semester abroad in Dublin my junior year, and it's the site of one of my favorite fantasies... In it, I'm in Ireland, drinking in a pub and meet this sexy stranger with an accent that melts me like butter, and before I know it we're fucking wildly outside against the wall of the pub, my skirt hiked above my waist, his strong fingers cupping my ass. Sadly, this did not happen during my time there, although I kept hoping! However, the fantasy did keep me entertained on many a lonely drunken night. Tonight, with Caleb, my back pressed against the wall, his hands on my tits, my fingers curled into the waistband of his jeans, stroking that tantalizing bit of flesh just above his cock, was the closest I'd come to my fantasy Irish fuck (minus the accent) and it was driving me wild...

The layers of clothes between us were too much, even my thin dress and his lightweight t-shirt were too much fabric, too much of a barrier between us. I pushed him away from me and, while keeping my eyes fixed upon his gaze, hitched up my dress and showed him a glimpse of my panties. I hadn't dressed with the intention of them being seen but did make sure to wear something sexy, just in case. His eyes darted down and took in my white lace boyshorts, quickly returning to my face with a beam. Apparently Caleb approved.

He unbuckled his belt, popping the top couple of buttons of his jeans. Lifting his t-shirt a little I could make out his wonderfully chiseled hips and toned stomach. While certainly not a muscled being, he was in terrific shape. I pulled him close to me once more, pressing my mouth against his. Passion spread throughout our bodies like wildfire. I reached down, now able to ease my hands into the opening at the top of his jeans and was able to clasp his cock in between my fingers. Gently I squeezed the head, pulling what appeared from touch at least to be his uncut foreskin back and forth along his thick shaft. He shifted his position, letting my hand drop further into his pants. My hand felt its way along his entire length, his cock throbbing as I touched. Slowly I made my way towards his balls, and cupped them gently as I stroked him.

Caleb made sure I didn't miss out. As I toyed with him he grabbed my thigh and made his way towards my soaked panties. My knees trembled as he traveled towards my pussy, while still he forcefully and wonderfully darted his tongue into my mouth. I felt two of his fingers pull the fabric to one side before two more pressed against the walls of my pussy. They didn't exactly meet much resistance. He plunged them into me; deep, fast and hard. Caleb finger fucked me so wildly that I knew sex with him would be even more amazing.
'Condom?' I asked between pants.
'Don't have one' he said, still fingering me furiously.

To cut a long story short (though I've just re-read what I've written so far and this is certainly not short!) I will have to wait until I can feel Caleb's cock inside me. He didn't have a condom and neither did I, and not wanting to take a stranger back to Grace's (not that she'd mind, I'm sure but I hate to impose!) we ended up swapping numbers and terribly guilty and disgusting looks when we eventually straightened ourselves up and went back inside. Fear not; I will get my man!