Confessions of a Slut Ch. 01

I am a white woman and my stories from West Palm Beach occurred from the age of 24-34 years old. (I'm now 41 years old, married, and living back in Virginia now). At the age of 24 I broke up with my boyfriend of four years and moved from Virginia to Florida; West Palm Beach to be exact. I moved in with a friend of mine who I had met in college prior to both of us dropping out. I was hired as a waitress at a bar/restaurant I will not name. My stories pick up from there. The names have been changed for anonymity.

Upon moving to West Palm Beach from Virginia, I was able to secure a job as a waitress with no experience. Needless to say it took some adjusting. To be honest I had never held a job other than being a swim instructor growing up. Waitressing was a fun job but very stressful at first - especially for someone who has bouts of anxiety such as myself. Top it off with having to make new friends and living away from my family and I was a certifiable mess.

One of the things that I found solace in was sports - especially my Washington Redskins. West Palm is a very transient city so there were a lot of football fans from all over the United States. I worked all the Sunday's I could as the tips were good. Banter amongst the staff was common and playful. One particular Sunday a bartender, we'll call him Jimmy for the sake of this story, had a friend at the bar watching football who had just moved to WPB from California. He was short, about 5'8", but not shorter than me. I was 5'6" and weighed about 135 pounds give or take. I had blond hair, not yet bleached, brown eyes and had West Palm boobs (36c) but not a West Palm body. That is to say I wasn't fit but I wasn't exactly what most areas of the United States would call fat. I just wasn't toned.

Anyways, Jimmy's Philadelphia Eagles were playing my Redskins so the trash talk was flowing. Prior to the game Jimmy offered a me a bet - if the Redskins won he would put in a word with his friend about getting me training and a bartending job at a different bar/restaurant. If I lost I had to go on a date with his friend who was sitting at the bar - who we will call Shane. It was a close game but to get to the point, the Redskins lost by two. I didn't particularly want to go on a date with his friend - he was cute enough but fairly unremarkable. He was white and his short, dark brown hair was thinning young (he was 28). He was slightly overweight but by no means fat. He did have these great blue eyes though.

I gave Shane my number and agreed we could go out for drinks sometime when I was off the next two days. Shane called me on Monday and asked me to meet him for happy hour drinks downtown. We agreed on a taco place that had decent happy hours. I threw on some jeans, a cute black tank, and I met him around 5pm.

The talk was stale at first - he was a golf instructor, moved here for a new start, had big family - and I sought solace in my margaritas to ease the awkwardness. I'm not sure whether it was the margaritas, his genuine interest in me, or the fact I didn't eat many tacos to soak up the margs - but I was finding myself more and more interested in Shane. So much so I agreed to grab more drinks down the street.

We arrived at a tiki bar where I switched from margaritas to a Red Bull vodka (bad idea) and we exchanged a kiss at the bar. It was a good kiss. Nice soft lips but the kiss was still firm. His hand on my cheeks pushing my mouth onto his. In short, I liked it. He asked me if I wanted to go back to his apartment for more drinks and I agreed.

We got to his place around 11pm. His roommate was already asleep so he made me a vodka cran and he grabbed a beer. We sat on the living room couch and had a few sips of our drinks before the make out session continued on his couch. His kisses were much more aggressive this time (which I liked) and so were his hands (which I also liked). I'm self conscious about making out when sober but it's something I genuinely enjoy when drunk. His hands pulled down the straps of my shirt but he had trouble unclasping my bra. It wasn't really a turn off but I was annoyed the kissing had to stop while I reached back and unclapsed it myself. I would say I was topless but my tank was down around my stomach - which I sorta liked since I was somewhat self conscious of my stomach back then.

Sadly, we didn't resume kissing as his mouth found his way to my left breast and then right, alternating while I sat there somewhat awkwardly, not sure whether to simply enjoy it, kiss more, or call it a night and try to get some sleep. I wasn't really tired but I was drunk enough that I could've slept immediately if needed.

At that point we heard the toilet flush and I quickly pulled up my tank to cover myself. Luckily his roommate never came out to the living room but we decided it was best to move to Shane's bedroom regardless. We grabbed our drinks and went to his room and he shut the door behind me.

He began kissing me firmly as he pulled my breasts out of my tank. That's not exactly the most comfortable feeling so I did us both a favor and just took my tank off. I felt awkward standing so I asked if we could move to the bed. He concurred and after taking my shoes off I hoped into his bed.

His pillow had a typical man smell - a bit of natural odor mixed in with Old Spice and Aqua de Gio. He climbed into bed fully clothed and immediately returned his oral attention to my breasts. Now it's not that I don't like my breasts involved in foreplay but they aren't big pleasure zones for me. I gently moved his head away, took a drink of my vodka cran and decided this needed to go in a different direction.

I walked over to his side of the bed and pulled off the black v neck he was wearing over his head. He had they type of chest and stomach that showed he probably belonged to a gym at one time but mostly just drank beers nowadays. A hint of former muscle tone was evident but mostly it was just your average male torso. As I stood at the edge of his bed, he sat there shirtless, leaning in to kiss my breasts again. I grabbed his thinning hair and told him we've done enough of that.

I pushed him back so that he was laying on his back, his torso on the bed, his legs hanging off. I bent over and unbuttoned his jeans. He lifted his ass so that I could wiggle them off and I saw he was already hard. It was a pleasant surprise - not huge, maybe 6 inches, but his dick had good thickness.

I told him to spin around so that his whole body was on the bed the proper way. Shane was clearly either not very experienced or just clueless in bed. I crawled onto the bed and grabbed his penis in my right hand, noticing he already had some precum. I took the tip of his dick in my mouth, a nice thick purple-ish head. I then pulled it out and licked down his shaft, stopping at the balls to give them a few licks before coming back up and giving him a proper blow job. I could easily take the length of him in my mouth but his thickness stretched my lips slightly. Surprisingly, he sat up abruptly and asked me to stop.

He rolled me over onto my back and unbuttoned my jeans, pulling them off me awkwardly and aggressively. He then began going down on me, except my panties were still on so he was licking me through the fabric. At this point I was about to call it a night when he slid my panties off.

Finally. I thought he was going to go back down on me but instead he knelt there and slid one, then two fingers inside of me. It felt good and my hips arched up to meet his fingers. He then slid a third finger in my pussy while his left hand found my clitoris - something my ex boyfriend of four years often failed to do. What a turn this had taken!

His fingers were well trained at finding just the right spots with just the right amount of pressure and speed. I came and came hard, pushing his hands away due to the sensitivity. I rolled over onto my side to gather myself. My chest flushed red, my breath heavy, and my pussy now wetter than it had been in years.

As I lay there gathering myself I felt his hand on my left ass cheek, squeezing it, spreading it, and pushing me onto my stomach. Without any warning I felt his thick dick part my lips and slide fully into my pussy. I laid there surprised how quick this had progressed. Hours ago I didn't even want to be on a date with this guy and now I'm laying in his bed, one pillow muffling my moans while he slid another under my pelvis.

Long slow strokes of his dick inside me developed into harder, faster strokes. He reached his hand around and expertly found my clitoris again - rubbing it more furiously than he had before. He then grabbed my hips and pulled me up on all fours. My breasts swaying uncontrollably as he thrusted harder and harder. His hands now alternated from grabbing my breasts to rubbing my clit to grabbing and spreading my ass. Me caught somewhere between self consciousness and eroticism.

With a thrust and a minor grunt of his, the session ended - his cum uncomfortably leaking out of my pussy confirmed it. I cleaned up and took a taxi home, the first of what would be many WPB sexcapades.