I was looking forward to leaving the cold of the Midwest for the warmer temperatures in Texas. Our Company had decided to hold its winter conference in Southwestern Texas at a posh golf resort. And as in the past, the meeting would bring in members of our sales team from across the country.
After the first day of meetings we headed off to a private part of the resort for a reception and dinner. As often is the case, there was drinking and socializing going on and laughter could be heard at every corner of the room. The food was of southwestern Tex-Mex variety and the beer and mixed drinks flowed freely.
I had been hanging around some of our reps from our western region and they had decided to move to the back part of the restaurant where there were a couple of pool tables. Our group had been playing pool for about 30 minutes when I found myself getting teamed up with Mary. Mary was an average looking lady with large breasts, a slender figure and long flowing brown hair. I had worked with Mary throughout the year and found her to be a nice lady who had recently gotten a divorce. The pool game was a lot of fun with everyone talking smack and drinking beer. Mary and I won our game and prepared to take on the next team. “Well, that was easy” she said. Answering back, “Yep, you played well”.
As we began winning each team we played we began to get comfortable with each other and became a couple of smartasses. The smack talk flowed freely, as did the booze. And before long we had beaten anyone who dared to team up against us. Mary wanted to keep playing pool, and asked, “You wanna keep playing?” “Sure” I said, “what do you want to play for?” Mary looked at me for a moment and then smiling said “Oh, I dunno, how ‘bout the winner get’s the looser to do anything they ask for the rest of the night.” For the first time I began to look at Mary in a different way. What did she mean by that comment? I wondered… “Anything?” I asked. Setting up the balls again Mary answered, “Well, within reason, of course.” “You’re on” was my response.
Now I’m not the best pool player, but neither was Mary. Our earlier winning streak had been heavily influenced by good luck Either that, or our opponents were drunk. Still, we played a good, close game. Throughout the game we gave each other some smack talk, each poking jabs at the other’s ability, or lack thereof. At this point we were alone in the pool table area, as everyone had returned to the bar for more drinking. And when a waitress came in to ask if everything was OK, Mary said “Perfect. Things are perfect.” “I think I’ll switch to a 7 and 7”. Looking at me the waitress asked “how about you sir?” “Ah, I’ll just have a bottle of water, thanks” Upon hearing my request for water Mary stopped eyeing up her shot and looking over her shoulder said “so you think switching to water will give you advantage?” “Nah” I said. “I’m just pacing myself.” Mary looked back at her shot and said “Not me. I’m just getting started”.
I won the first game and began asking, “So, I wonder what I should have you do for me?” when Mary shot back “Best 2 out of 3”. Mary began to rack them up again and handed me the pool cue. This time I noticed her hold the stick a little longer. Stilling holding on the cue she slammed back the last of her drink and asked for another. I had lost count of just how many drinks Mary had downed, but I was pretty sure she wasn’t feeling any pain. This was confirmed when I began to size up my break shot and I looked over across the table and Mary turned sideways to me and was undoing the top button of her top. She then turned and leaned forward in my direction. Smiling, Mary said, “Now concentrate. We want a clean break.”
From where we were to the rest of our group, no one could see us. So no one but me could see the ample cleavage Mary had just opened up for me. Staring back I responded with “Mary, I’m afraid you’ll have to do more than that to get me to mess this game up.” I made my breaking shot and sank four balls. Mary was giggling a little bit as she stood up. I noticed that she didn’t button her blouse back up. “Hmmm,” I began to wonder. Could this evening get even more interesting? Time would tell.
We traded turns and when it was my turn again Mary sat on the corner of the table and leaned back in a very seductive pose. As she did this I was certain that yet another button had been unfastened. Taking a sip of her drink, Mary smiled and said, “Is this having any affect on your shooting yet?” Swallowing hard I said, “Well, it might if I thought you were being serious”. I took my shot and sank a ball. When I stood straight and walked around the table to size up my next shot Mary walked by me and slid her hand across my hip and ass. Then right before she lifted her hand off my ass she gave my ass check a little squeeze. “Hmmm” I said, “you must be getting nervous that I might win.” Taking another drink Mary winked at me.
As I sized up my next shot I saw Mary look around the room as if to see if the coast was clear. Then she lifted her blouse from her pants letting it hang natural. Next she quickly unbuttoned the last of her buttons and leaned over the opposite side of the table to look at me. When she did this her entire chest was exposed and her ample breasts were barely concealed by a red lace bra. “How about now?” she asked. “Well, I must admit it’s getting a little harder for me to focus on the game.” Grinning, she reached inside her blouse and unfastened the front of her bra and pulled the cups back to totally expose her beautiful breasts. Her tits had to be D-cups, for sure. Their pale white color was in sharp contrast to her brown nipples and open burgundy blouse. I stood frozen. “What’s the matter?” she asked. All I could say was “Wow!” Laughing, Mary said, “Go ahead, make your shot. Or are you conceding the game?” I was on to her little game now. She was determined to win at all costs. So I thought “Two can play at that game.” I leaned in and took my shot. Mary’s breasts were having an affect on my aim and my penis. I missed the shot, as my penis begin to harden.
Laughing, Mary sarcastically said, “I guess you can’t concentrate, can you?” and re-fastened two buttons on her blouse. This would hide her breasts just in case someone returned to the room, but left me to think wild thoughts about what I had just seen. Trying to figure out what I could do to get Mary’s concentration messed up, I positioned myself behind her for her next shot. As she was bent over in preparation of her shot I said, “Mary, you sure have a nice ass.” Mary let her head fall towards the table and laughed. “That’s not going to work on me, Jeff” “Really?” I questioned. “OK, then I’ll shut up”. And just before Mary was to shoot I again spoke up and said “Really, Mary. Your ass looks very inviting in those tight pants.” Mary responded by shifting the weight of her legs to make her ass stick out further, and then took her shot. She missed.
“Oh, I’m so sorry” I said sarcastically. “My turn now”.
Mary quickly went over to the other side of the table and opened up her blouse to expose her full breasts again. This time she cupped each breast in her hands and pinched her nipples between her fingers and thumbs. I responded with “You’ll have to do better than that”. But actually, her display was indeed having an affect on me. I was bent over aiming for my next shot while my penis was pointing towards my belly. I wasn’t sure if Mary could see the obvious lump in my Dockers or not, until she said, “Well, I think you are lying. That lump in your pants tells me that you are very distracted.”
Smiling and clearing my throat, I took my shot. I missed. “Hot damn! My turn” Mary said in relief. As she leaned in to take her shot Mary decided to leave her breasts fully exposed. Feeling brave, I walked up behind her and slide the thick end of my pool cue along the crack of her ass. Mary let out a startled scream from the sudden feeling at her crotch. She spun around and said “Hey, that’s not fair.” “Why not” I said. “You touched my ass earlier, I figured this was allowed.” Still smiling Mary turned back around and assumed her position at the table. I once again slide the pool stick along her ass crack and this time Mary opened her stance a little so that the pool cue went up between her legs. When I reached her pussy she clamped her legs together and moaned, “Hmmm, I wish that was something else” and took her shot. When it was clear that she missed I asked Mary, “So, what would you like it to be?” “Well, you’ll have to see after I beat you at this game” she said with a sexy grin.
This game had gotten real interesting indeed. Remembering back to what she set up for the wager, it became clear that no matter if I won or lost, it was looking like I was going to win that night, in more ways than one. Up until our games I hadn’t considered Mary to be very sexy. Yet as the night wore on, with the possibilities for seeing much more of her, I began to look at her in a whole new way.
It was my turn now. And as she had done before Mary stood there cupping her breasts and pinching her nipples. Sensing that she needed to do something even bolder, Mary stood back from the table, undid her belt and unbuttoned her pants. I froze. Was she serious? The answer came quickly. Mary smiled and looked into my eyes and slowly lowered her zipper. I could clearly see that she was wearing a matching set of red lace panties. Very sexy, indeed. “Go ahead and take your shot Jeff.” Mary was holding her pants by the tops of her belt loops. So I leaned in to make my shot and Mary pushed her pants down to reveal her hips and the tops of her thighs. My pool cue glanced off the white ball and I scratched. “Ah Shit!” was all I could say. Mary re-buttoned the top of her pants and walked around the table for her next shot.
When she had found her shot she leaned in to take aim. I was busy in my pants playing a little pocket pool of my own when a wicked idea raced into my head. I quickly walked up behind her and pressed my pants-covered erect penis into the crack of her ass. Mary didn’t miss a beat. She kept sliding the pool cue in her hand taking aim at the 6 ball, corner pocket. And just as she made her shot I pushed into her ass firmly planting my dick right where it would love to be. Mary missed her shot, but didn’t move. She seemed to like the feeling of my hard dick on her ass. She laid her head down on the pool table and pushed back against my dick. I felt it throb, and so did Mary. She let out a gasp when it twitched in her crack. I pulled away and began walking around the table for my next shot.
I sized up the table and leaned into my next shot. Mary had come up behind me and as I was sizing up my shot she cupped both of my ass cheeks and leaned into my back. I could clearly feel her ample breasts mush up against my back. I was sure that I felt her rock-hard nipples on my back. And then when I slid the cue back to shoot, Mary shocked me by reaching around and took a firm hold of my hard penis. I could have cum right there. Obviously, I completely missed my shot. However, I didn’t care. Like Mary had done with her shot, I didn’t move. I was enjoying Mary’s caressing of my penis and the feeling of her hard nipples on my back. I reached back to try to fondle her tits and ass but Mary stood up and walked around the table to look for her next shot. This game had taken a really sudden change in direction and I was “up” for the challenge.
When Mary had found her shot I walked up behind her and when she bent over to shoot I leaned in again. With my dick firmed lodged in the crack of her pants, I reached around and cupped both tits. Mary let out a heavy sigh and stood very still. Rather than take her shot Mary was enjoying my caressing of her tits. I began caressing her breasts in a less-playful way and began to massage them in the most sensuous way possible. I then slid my right hand down her breast, down over her stomach and onto the button of her pants. In a quick twist, the button was loose and her pants were free. Still kneading her breasts with my left hand I slid my right hand down into her pants onto the front of her red lace panties. My middle finger easily found the center of her pussy fold and I gently pressed onto what I hoped was her clit. I figured I had hit jackpot when Mary’s breathing stopped for a second and she twitched.
“Aren’t you going to take your shot?” I asked. “Who cares, you win,” she said breathlessly.
I slid my left hand off her breasts and down the front of her until I came to her left hip. I slid my right hand up to match it’s left brother and grabbed Mary’s pants in my hands and tugged them down. They easily fell to the floor. And there under my erect penis was Mary’s naked legs and panty-covered ass. At this moment Mary dropped the pool cue on the table and slid her hands across the table to clear the balls that were under her. She then laid her head on the pool table and brought her hands around to the front of my pants. What happened next amazed me. In what seemed like one quick motion Mary had unfastened my Dockers, pulled my zipper down and grabbed the top of my underwear releasing my erect penis. The next thing I knew, Mary is guiding my erect penis into something very wet and warm. Using her right hand she had pulled her panties to one side and with her left she had guided me into her luscious pussy.
I couldn’t believe what had happened. It seemed that one second Mary was about to shoot the 4 ball in the corner pocket and now my own hard pool cue was going in and out of her corner pocket. Then it hit me. “Shit Mary! We’re still at the restaurant!” “Someone could come in right now and we’d be history!” Mary stood up quickly, coming back to her senses too. I tried to stuff my very wet and hard penis back into my pants, and Mary was bent over at the waist grabbing her pants. Mary and I frantically were tucking our shirts back into our pants when we heard some laughter and voices headed our way. We were no sooner fully covered when several members of our Ohio sales office came in. With my dick making a hell of a tent in my Docker pants, Mary grabbed me told me “Stay close to me and walk directly in back of me. Let’s get the hell out of here.”
We paused for a moment in the hallway, making sure that the Ohio folks hadn’t seen anything. Laughing, and half embarrassed, we smiled at each other. “That was incredible, Mary.” “Yeah, I don’t know what came over me” she said. Smirking I said, “Well, actually nothing came over you… yet. I do believe I won the game and for my win I think I want to finish what we started on the pool table back in your room.” Mary reached over and gave my crotch a squeeze and said, “I’ll get my coat.”
With my hard-on still sticking out noticeably, I stuck my hands in my pockets and quickly retrieved my jacket from the poolroom. I met Mary by the door and we left the restaurant. We kept our distance from each other, as we didn’t want to raise any suspicion from any of the people from the Company. It was about 10pm when we left, so there were still many people around the resort. Despite this, when we had made it far enough from the restaurant Mary leaned in and put her arm around mine and leaned her head on my shoulder. As we walked Mary whispered, “that was incredible what you did back there.” “What I did?! You started it with your sexy breast display.” “What else could I do?” Mary then said “you had me so turned on that I had to feel your dick in me.” “So how’d you get my pants undone so fast?” I asked. Mary only laughed.
We walked in silence the rest of the way to the cabanas. When we had reached the elevator I pressed the button, which opened the elevator doors. As soon as the doors closed Mary spun around and began French-kissing me passionately. It was then that I realized that while Mary had buttoned up her blouse, her breasts were still loose. She hadn’t had time to refasten her bra. So I reached up and began fondling her breasts. It didn’t take long to feel her nipples get hard again under my touch. Just then, the elevator came to a stop, and the doors opened. Composing ourselves, we got off on her floor. We made our way to her room and just as soon as the door closed behind us Mary had placed her hands on my face and resumed her passionate French kiss. So, I resumed my breast exploration.
I reached up and began to unbutton her blouse. I struggled with the second button a little bit and before I could do anything Mary stepped back and in a quick tear she had ripped open her blouse tearing off all of the buttons. Now her blouse was totally open and her beautiful breasts in plain view. The light in her room was brighter than the restaurant so I was more easily able to see just how beautiful her breasts were. I stepped back and admired how perfect they were. While big, they didn’t sag one bit. They were definitely Playboy-perfect! I leaned in and took her right nipple into my mouth and swirled my tongue around her rock-hard nipple. Reaching up and cupping each breast I moved back and forth from left to right and right to left sucking on her large and very erect nipples.
While I was working on her tits Mary had shed her jacket and let her blouse fall to the floor behind her. Mary was now standing before me totally naked from the waste up. I began to kiss her softly in between her breasts and moved my head up into the “V” in her beast bone, and then moved my mouth along her neckline to just under her right ear. I was giving her soft sensual kisses on her neck and Mary seemed to be trying to catch her breath. Obviously turned on, she aggressively grabbed my head and forcefully began French kissing me again.
I reached up behind her and began slowing massaging her back with my hands. Mary moaned into my open mouth as we kissed. Mary then pulled back and began to remove my coat and shirt. Once I lifted my shirt off and over my head Mary began caressing my chest. She began to slide down my chest and down onto her knees. In a slower motion than she did at the restaurant, Mary unfastened my pants. She slid my pants and underwear down my legs past my knees and immediately took my erect penis into her mouth.
Mary was a pro, let me tell you. She made love to my dick like no other women I knew. She proceeded to deep throat me, fucking my penis down to the base and then back up to the tip. She was skillfully bringing me close to orgasm, but stopped short each time. Mary seemed to know when I was getting close to cumming and would slow her pace or lessen the tension. My knees were getting weak from all the pleasure, so I leaned back against the wall. This was when Mary began using her hand in unison with her mouth. The feeling was incredible and she had me close to cumming in no time at all. I told Mary “You have me so close to cumming”. This seemed to excite her even more as her pace quickened and her enthusiasm increased on my dick. In a matter of seconds I began to feel that familiar feeling and then it hit. “I’m cumming, I’m cumming!” Mary kept her pace as I filled her mouth up with my cum. Mary kept her mouth over my penis as it spasmed. Holding me tight with her hands on my hips, I fully enjoyed the sensation of her hat mouth on my penis.
Once my orgasm had somewhat subsided she opened her mouth a little bit and kept the head of my penis on her tongue. This caused my cum to rush out of her mouth and pour out all over her beautiful breasts. I had seen some sexy cum shots in porn movies before, but what Mary had just done was the most awesome sight I had ever seen. She kept licking my still-erect penis and my cum continued to drip out of her mouth and off her tongue, down her chin and neck, and down onto breasts. Absolutely beautiful!
I lifted Mary back to her feet and we began kissing passionately again. The slight taste of my own semen was kind of erotic and dirty all at the same time. We kissed for what seemed like forever, with me working my semen into the flesh of her breasts. Mary seemed to enjoy this very much and left out little moans when I circled my cum-covered fingers on her erect nipples.
I broke away from our kiss and told Mary “now its your turn”. I kicked off my pants and led her by the hand to the bed. Kissing her again I laid her back onto the bedspread. With my wet cum still glistening on her breasts and chin, I began to remove her pants. After sliding her pants off I leaned up and began to kiss her belly button. Lying between her open legs I began to massage her thighs and hips with my hands, all the while I kept kissing her belly. Mary let out another moan of approval. In this position I could clearly make out that unmistakable smell of a women’s sex. I leaned back to have a close look and I was greeted with an obvious dark mound under her panties with an equally obvious wet spot forming in her crotch.
After some more kissing on her thighs and belly I reached up and grabbed her red panties and slid them down her hips and thighs, past her claves and off her feet. And there she was, totally naked for my personal viewing. To be honest, Mary was a very attractive and sexy lady. I never asked her how old she was but I had assumed that she was in her early 40’s. And as I thought about that it occurred to me just how sexy her body was. She had taken good care of herself.
I leaned back down onto the bed and between her legs. Using my hands I lifted her legs up and apart to give me full access to her wet pussy. Mary’s pussy was full and somewhat hairy. She had kept her pubic hair trimmed, but obviously didn’t believe in shaving. This natural look was a turn on. Despite her full mound of hair, her pussy lips protruded nicely and her clit was standing out from between her lips. When I lifted her legs up and outward, I could clearly see her moisture dripping out from between her pussy lips and down around her asshole and cheeks. She was very turned on.
I slowly brought my mouth up to her pussy lips and blew softly into her mound. This caused Mary to let out a soft moan and arch her back in anticipation. Next I gently slid my tongue up her snatch and across her clit, stopping on top of her clit to swirl my tongue around the bulb. I then took her clit into my lips and gently sucked on it. This took Mary’s breath away. “Ummm, Jeff that feels incredible. Please don’t stop!”
I kept repeating a sequence of licking around her opening, then up her slit, around her clit, and then sucking her clit into my mouth. I did this for a few minutes and noticed that her pussy had become completely drenched. She was so wet that her moisture was now leaking onto the bedspread and was beginning to leave a circle of wetness. Sensing that she needed more I brought my right hand around and inserted my middle finger into her pussy. Forming a slight hook shape upward I found Mary’s g-spot. With my finger swirling around her g-spot I returned to licking and sucking on her clitoris. Mary’s breathing became more labored and her hips began to gyrate. “That’s it. That’s it. Like that, Oh yes, like that!” she panted. Soon, she began to shout “Oh, I’m cumming!” and practically broke my jaw with the thrusting of her hips.
Mary came very hard, and for what seemed like forever. I kept my g-spot movement and sucking going, but eased up a bit. This allowed her to enjoy the waves of orgasm without being overwhelmed with too much intensity. Then it happened again. “Oh God, I’m cumming again! Yes, Yes, Yeesssss!” she screamed. Finally spent, I let Mary regain her breath and enjoy the post-orgasm twitches. As I moved up her soft body I licked her tits a little more, and then moved onto the sides of her neck just below her ears. Cooing she turned and gently kissed my lips. Savoring her taste on my lips, she sucked on my lips and face to take in all of her sex juice. Never before had I been with a woman so appreciative of her orgasm.
At this point I was positioned between her legs and my hard penis was a few inches away from her honey pot. I moved up and my dick easily entered her succulent pussy. The feeling was awesome – smooth, silky and warm. Wanting to savor the moment I moved slowly in and out of her pussy. Mary had begun to move her hips in rhythm to my thrusting and was doing what she could to get me insider her as deeply as possible. I then placed my arms up under her legs so that my forearms and biceps were holding up the backs of her knees. This allowed me to penetrate her as deeply as possible. She was moaning and taking deep breaths with every thrust.
Wanting to enjoy this time with Mary to the fullest, I withdrew my dick and spun her over onto her knees. Then I knelt behind her and using my right hand to move the tip of my penis up and down her very wet crack, I found her pussy and eased it in. “Oh God I love this position” she said. Mary then took her hands and pulled her ass cheeks apart to give me the very best access to her sensational pussy. I leaned back to check out the view and saw her little brown eye winking at me as we thrust back and forth. I could clearly see my sopping wet dick moving in and out of her glistening pussy. Her pussy lips seemed to be sucking my penis in with each thrust. This view was just about all I could take. I soon began to get that familiar feeling of my impending orgasm. Sensing this, Mary picked up the pace and began panting “Cum for me baby. Cum in my wet pussy!” A few more thrusts and I began to feel my orgasm building deep within my body and then, with a force I can’t ever remember feeling before, I shot one, two and three jets of cum into Mary’s wet box. I held my dick in her pussy as deep as I could get it while wave after wave of orgasmic bliss flowed over me. As my orgasm began to subside, I moved my penis in and out feeling how different her pussy felt with my cum mixed in with her pussy juice.
When I pulled out and sat back on my heels Mary stayed on her elbows and knees trying to catch her breath. And while doing this I could see my cum mixed in with her juice drip out of her pussy and onto the bed. Mary then took her right hand and began massaging her clit and pussy, mixing up my cum and her juice and rubbing it all over her pussy. What an awesome sight!
Sighing, Mary rolled over onto her back and then she did something that was truly amazing. Mary took the fingers of her right hand and held them at the opening of her pussy. Looking directly into my eyes, Mary managed to push some of my cum out of her pussy and onto her waiting fingers. And then to my amazement, she lifted her hand to her mouth and held her fingers up over her open mouth. I watched in awe as she let my cum drip into her mouth and then licked her fingers clean. Then she swallowed it all with a smile. This lady was truly amazing and in credibly sexy. I loved it!
It had been quite a night, and we both knew that we needed to separate for the night. The next day we’d have to act like nothing happened, so that no one would ever suspect anything had happened between us. She walked me to the door, kissed me softly, and thanked me for “a fabulous screw.” I gave her a soft kiss and turned and left. That would be the only time Mary and I would connect like this and we’ve managed to keep our relationship strictly professional, every since.