tagAnalA New Experience for Ann

A New Experience for Ann

byfuninthesun56©

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?"

"Completely," I replied, although I suspect I wasn't being completely honest with myself on that one.

"In about an hour, five other men are going to walk through that door. Your job will be to please every one of us over the course of the evening, in whatever way we so choose. No one will hurt you, and I can guarantee you will enjoy yourself, if you allow yourself to let loose. I've watched you for a long time, and I'm confident enough in my ability to judge a person to know that you will enjoy this, even if you don't believe it right now."

"Uh oh," I thought to myself, "this is so NOT what I signed on for." I couldn't believe he would think I wanted to do this! But even as the thought entered my head, I felt a strange sensation course through me and my skimpy thongs suddenly became very, very wet.

I decided then and there that it was definitely in my best interests to leave, but Tom reached out and lightly encircled my arm with his large hand, pulling me close to him. His other hand brushed over the curve of my breast, and naturally my nipples couldn't have cared less what I was thinking as they became hard and strained against the flimsy material covering them. Pulling down the straps of my sundress, one at a time, he tugged the garment down over my shoulders, then freeing my breasts he leaned over and began suckling on first one, then the other. As his tongue circled round an erect nipple, he gently bit down, sending a fiery surge coursing through my body. I could hear myself moaning as I let my head fall back, shamelessly pressing my breasts up towards him, silently begging for more, all thoughts of leaving gone for the moment.

Pulling his head back, Tom smiled as he pulled my dress the rest of the way down, allowing it to fall around my ankles. As his fingers dipped underneath the thong, he felt the smoothness of my pussy.

"Nice" he murmured, pulling them down farther. "Let me see all of you."

He took a step back as I carefully removed my thong and stepped out of the pile of clothing. I was a little embarrassed to be completely naked, except for my high-heeled sandals, but not ashamed of my body. Tom stood in silent admiration, but he didn't touch me again, even though I knew he could see me pleading with my eyes for him to finish what he had just started. He had played me perfectly, I thought, just enough to make sure I was desperate for more.

"Come on, let me give you a tour of the place."

I reached down to pick up my clothes, but stopped when he said,

"Just leave those there,."

I looked at him in disbelief.

"Are you crazy? Tom I'm naked."

"And your point would be? Believe me, Ann, you won't be needing them the rest of the night, so you might as well get comfortable now. Come on, I want to show you everything." He ignored my dismay and grabbing my hand, pulled me along with him.

Like a little kid showing off his newest toys, Tom led me into the guest room where his computer equipment was set up, to the master bedroom with the plasma TV hanging on the wall opposite his bed, and all the different remotes that worked too many things for me to ever figure out, to the shower with heads sticking out from different sides and heights, and to the tub with too many jets to count in his master bath.

"Believe me, you're going to love those jets someday." He smirked as if he knew something I didn't.

I refused to answer, so he moved back to the bedroom and the sliding doors that opened onto the lanai. He walked outside, clearly expecting me to follow, but there was no way I was stepping outside without a stitch of clothes on.

"Tom, we can get arrested if I walk out there."

"There's no one out there to see you! Look." With a sharp tug, he pulled me out the door into the relentless sunshine. I felt its warmth immediately soaking into my skin, especially those parts that don't normally see the sun. If I was sure no one was watching I would have stretched like a cat, but I wasn't convinced.

"Look around, do you see anyone?"

I had to admit, I couldn't see anything or anyone on either side, mainly because of the thick ficus hedge which ran the length of the property on both sides, and the beach was empty as far as I could see.

"Don't be so nervous."

"That's really easy for you to say, Tom. You're not the one standing here with nothing on. Can I please go put some clothes back on?"

"Absolutely not." He reached out and grabbed one of my breasts in his hand, leaning over he began to tease and nibble, sending a shiver up my back. His tongue licked repeatedly until the soft skin was wetly glistening, and of course I stood there unable to move. "Why would you ever want to cover up this body? If you lived with me, you would never wear clothes from the moment you walked in that front door until the moment you left."

"Thank God I don't, then." I replied.

He smacked me on the bottom, enough that it stung and I was sure left a handprint.

"Ouch!"

"You deserved that." With a grin, he relented and drew me back inside.

"Come over here." We moved into the kitchen, which was shaped like a galley, long and narrow, with one side open to the living room, the other with a large window overlooking the side yard. Granite countertops ran each length, white cabinets with glass fronts up above, truly a cook's dream kitchen. I looked around in appreciation, more at home here than with the electronic equipment.

He asked once again, "Ann, do you trust me?"

Knowing I probably wasn't going to like what came next, I replied a little hesitantly, "Yes."

"Okay, I want you to bend over the counter for me." He pressed on my back, urging me down.

"No way!"

"Come on, you're going to like it." He was pretty convincing, but then again, he sort of had the upper hand here.

"Tom, I really am beginning to feel like a slut. This is just not me. I don't strip for guys I've dated for awhile, much less a co-worker who I've never gone out with."

"Did you ever think that might be your problem? You're a little too uptight. I hardly think you're a slut, either. Do I want to get in your pants? Absolutely. And since you don't have any pants on, I don't think it's going to be too hard." His smug grin only proved how confident he was in convincing me to go along with his plan. "And I promise to respect you in the morning."

I just looked at him and shook my head.

"Darling, not a single person will ever know what went on between these walls. Not a one of us ever kisses and tells. What we do, stays here. We all let go and allow our more basic instincts to rule for awhile. And yours are telling you that you like this."

I resisted at first, then decided what the hell. What was the worst that could happen? Tom had promised I wouldn't be hurt, and had even said I would want more of whatever it was I was going to get tonight. "Well, let's find out," I thought to myself. I had come this far, hadn't I? In the back of my mind it shocked me to realize I wanted this, too. I was beginning to discover something about myself that I wasn't sure was a good thing. Wouldn't any normal female be running for the hills by now?

"Let me finish my drink first, okay?" I downed my rum & coke in one gulp, set the glass down and then bent completely over, my breasts smashed against the cool countertop, my ass sticking up in the air for the entire world to see, if indeed the entire world wanted to look. As it was, knowing that it was just Tom made me almost cum with no help at all.

"Ahhh, I knew your ass looked good in shorts, but this is absolutely beautiful."

I felt his hands moving over me, lightly edging down my thighs and back up again. He squeezed both cheeks in his hands, massaging them gently, then harder as he pulled them apart and exposed my hole to his view. I whimpered, but didn't move. Warmth from his breath brushed across me and I felt his wet tongue rim me. It moved in slow circles around the outer edge, dipping in and out just enough to tease. This time when I groaned, I did try to move, but he held me tight as his tongue suddenly pushed harder at the entrance to my ass. I tried to push back, suddenly wanting it more than I thought possible. I felt the wetness of his saliva mixing with my own juices to begin trickling down my inner thighs. He continued to fuck my ass with his tongue, until to my dismay, he retreated, but then made up for it by licking his way down to my pussy. His tongue played games with my clit, sucking on it, flicking it back and forth before nipping at it with his teeth. I felt an orgasm building to an intensity I'd never felt before, and when I felt a finger gently pushing its was into my ass, I fell over the edge, shaking and trembling with the effects of the most incredible orgasm I had ever experienced in my entire life. I could barely stand, my legs were shaking so much.

"Okay, I'll do anything." I whispered, "As long as you promise more of those."

I heard his laughter as I started to rise, but his hand held me firmly in place.

"Not so fast, we're not done here." He pinched my clit one more time, sending aftershocks rippling through me. Then as he moved away, I heard a drawer being opened and the sound of running water from the sink.

"Remember when I said I needed to get you ready for tonight?" Without waiting for a response, he continued on, "here's where we start."

After what seemed a long time, I felt the tip of his finger against the entrance to my asshole again. I could feel him rubbing a lubricant into and around it, his finger sliding gently in and out. My muscles grabbed at his finger, tightening around it. I heard his soft laughter as he removed the finger and replaced it with something harder and larger. I was confused, I knew it wasn't his cock, he was still fully clothed. Which I might say is pretty humiliating when you picture the two of us and what we were doing.

Whatever it was, I felt it pushing further into me. It slipped past my sphincter muscle with little difficulty, I was well-lubed and it wasn't that large. I suddenly felt a peculiar warmth spreading through my bowels, filling me. I tried to jerk away from it, but Tom's large hand on my back held me firmly in place. Try as I might, I couldn't get away from the strange sensation flooding through me.

"What are you doing?" I demanded.

"You're getting an enema, and believe me, you will appreciate it before the night's over. You need to be clean inside and out. A lot of fluids will be in here before the end of the night, and you really don't want anything else coming back out along with them."

I suddenly felt more humiliated than I had ever felt before in my entire life. Here I was, ass sticking up high in the air, in the kitchen of a man I had foolishly hoped to build some sort of relationship with, and he was giving me an enema in preparation for what was obviously going to be a very long night.

"I need another drink." I begged. "And I lied about doing anything. I don't want to do this."

"Relax, you'll be fine." He soothingly stroked his hand along my back as he continued slowly filling my rectum with the warm liquid. One of his legs pushed between mine, spreading them farther apart. I heard the sound of his zipper being lowered and soon felt the head of his cock pushing against my pussy, sliding in almost too easily through the wetness I was generating.

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