Walking up and down the aisles of the grocery store, I hoped I wasn't forgetting everything on the list I'd left hanging on the refrigerator door, like an idiot. I figured I could be forgiven, though, because I couldn't keep my mind off the evening ahead. Tom had promised it would be a night I wouldn't forget for a long, long time, if ever. When he had said this, the look he leveled on me had been blatantly sexual, shocking me because of its unexpectedness. The rest of the night at work had passed in a blur.
Tom was a bartender at the same sports bar where I worked in this small, southern town on the Gulf of Mexico. I was in my fifth year of college and figured at the rate I was going, I had about three more to go before I finished. I liked my job, the people I came in contact with every night, and the people I worked with. A degree in business didn't appeal that much to me, but I felt the need to finish, figuring it would come in handy someday when I bought my own restaurant/bar. How that dream would ever come true was beyond me, but I had my goals and wasn't about to give them up.
When Tom invited me to come to his house for a small get-together with some friends, as I said, I had been a little surprised, to say the least. We'd been carrying on a flirtation with each other for quite awhile, but it had never progressed beyond the workplace. I had been eyeing Tom for a long time, but didn't want to make the first move. How humiliating would that be if he turned me down and I had to keep working with him? The fact that he had asked me over, and made it so clear that more would be involved than just dinner, had made me a mindless idiot all day long.
Over time, I'd picked up on snippets of conversations from a few regulars at the bar that made me believe there was quite a bit of sex involved at Tom's get-togethers. Well, I could sure use some of that, it had been a long time since I'd been with another person, in fact, it had been well over a year. Between work and school, the hours I kept made it hard to meet new people or develop any sort of relationship, so I'd almost given up hope of ever finding that perfect man.
As I wandered through the produce section, the few men who were shopping paused to take a second look at me. I was almost 5'5" and knew my lean body didn't have an ounce of fat on it, thanks to the hard work I did. I'm proud of my tight ass, and while my breasts aren't that large, they definitely will fill a man's hands. I've been told I'm good looking, and am used to being looked at, and in a town of this size, I know most of those men doing the looking. I like to go bra-less, but usually remember to wear one when going to the grocery store. Those frozen food aisles make it a necessity. Well, being distracted as I was on this particular day, I hadn't worn one. So of course my nipples were hard and showing through my t-shirt. I'm not an exhibitionist, and was embarrassed enough to try to cover them by pulling my hair over my shoulders. They rubbed against the cotton fabric, already sensitive from the thoughts running through my head.
Finishing up quickly, I smiled at the clerk as she rang up my purchases, thanked the bagger, and headed out the double doors into the oppressive heat of the early August afternoon. Within moments, sweat replaced the goose-bumps. Thankfully, the air conditioning in my ten-year old car still blasted out cold air. Unfortunately, by the time I reached home, it was just beginning to cool, and I knew I was more than ready for a nice, cool shower.
Walking in the door of my small apartment, I dropped my keys and purse on the table, the perishables in the refrigerator and everything else on the counter, then headed straight to the bathroom and the shower.
Turning the water on cool, I let it cool down my overheated body before finally picking up the soap to lather myself. As I washed, my hands lingered on my breasts, squeezing and kneading them enough to send a sharp ache down through my body. I imagined Tom's hands on me as I rubbed my nipples hard a few times before moving lower. Spreading my labia with one hand, I used the soap to wash carefully in every crack and crevice. My hands explored, one finger finding its way inside while with the other hand, I found my nub and squeezed and rubbed and manipulated until I was ready to cum. Hovering on the brink, I forced myself to stop, saving that particular reward until later that evening.
One night at work, I had overheard Tom talking to another bartender about a woman he obviously knew well. He didn't realize I was listening as he described her clean-shaven pussy and how that was such a huge turn-on to him. Replaying that conversation in my mind, I spent extra time doing the same to myself. I was a little embarrassed by the way I looked when I was done, but hopefully Tom would be turned on when he saw it, as I was convinced he would at some point tonight.
Shower finished, clean-shaven, makeup on, and horny as all get out, I threw on a sundress with no bra, a skimpy thong underneath, and my newest pair of high-heeled sandals, better known as Fuck Me sandals. I grabbed up keys and purse and headed out the door before I could change my mind. I could feel the thong rub against my hairless skin in a way I wasn't used to, heightening my sensitivity. Nervousness coursed through me at what I was about to do, but I was determined to let my hair down and have some fun. The thought of getting down and dirty with Tom was enough to keep me from running back inside.
Believe me, I am not normally over-sexed. But this man was drop dead gorgeous, he had a fantastic body, and I've worked in close quarters with him for the last few years, and to top that all off, I haven't had any real relief for way too long. I don't consider getting myself off as "real relief". And there is definitely a sexual chemistry between the two of us. We have just never explored it.
Tom's house was just a short distance away and overlooked the beach. It only took me a few minutes to drive there, and as I pulled in, I realized no other cars had arrived yet, even though I was sure I wasn't early. Shrugging my shoulders, I hopped out of the car and made my way up the flagstone walk to the front door. I had never been here before and was pleasantly surprised by the charm of the cottage. Before I had time to look around, though, Tom opened the door, a drink held in one hand, the other ushering me inside. He leaned over and placed a light peck on my cheek.
I glanced around, expecting to see a typical guy's place. Surprisingly, it was nothing of the sort. The look was definitely tropical, and when I thought about it, it suited Tom perfectly. He was definitely an island type of guy with his sun-bleached hair, deep tan, khaki shorts, white polo shirt and bare feet. I'm sure he got a lot of that tan sitting outside on his lanai, or down on the beach just a stone's throw away. I had to wonder if he had tan lines...
"Come on in, we have a lot to do to get you ready for tonight. Pam was supposed to come, too, but just called and said she's been sick in bed for the last two days. So you're it, darling...the sole entertainment for the evening!" Tom grinned at me, placing a hand on my back and steering me forward through the house.
I was too stunned by this announcement to utter a word. I was the sole entertainment for the evening? What was Tom talking about? I hesitated, but a drink appeared in my one hand, and grabbing the other, he led me into the center of the living room. He stopped and touched me lightly on the chin, turning my face to look directly into his. His eyes were a deep blue, and seemed to look deep down into my soul, reading my uncertainty.
"How long have you known me, Ann?"
"I don't know, three years?"
"At least, and in that time, have I ever done anything that would make you think you can't trust me?"
I thought back over the time I'd known him and had to admit that Tom was the type of person you could trust implicitly, at work and beyond. I shook my head.
"So, you know you can trust me, right?"
This time I nodded my head in agreement.
"Some things are going to happen tonight" he continued, "that I'm sure you've never taken part in before. But I want you to keep an open mind, explore your sexuality, and most importantly, trust me.
"I'm pretty sure this is going to be your first time with more than one man, but I can assure you, you will love it and by night's end, will want to do it again." Tom looked at me confidently, much more sure of me than I was myself.
"What exactly are you asking of me, Tom?" I was ready to bolt for the door, beginning to see that this might not be about just the two of us.
"Do you want me to be completely honest and upfront?"
