Storytime - Lisa

(EDITED)

Maribeth and I were snuggled against one another's naked bodies in the St. Anthony Hotel in San Antonio.

Earlier in the day we had participated in our first attempt at role playing, which consisted of her pretending to be a mysterious woman from Eastern Europe who I spied at the hotel bar. My role was to 'seduce' this woman, as Maribeth was curious to experience my 'technique' which I had described to her on several occasions.

The fact that I had been successful was now more than apparent since we were naked in bed. We were, or more correctly, she was, recovering from a prolonged bout of oral sex. I had tongued her pussy and clit for over an hour which had brought her to several mini and one grand mal orgasm. After this last, Maribeth was too sensitive to continue, so at her request, I related a "story" of one other time I had seduced a woman.

I had just finished telling her about Lisa, who I had met in a bar in Louisville, Kentucky when I hosted a Kentucky Derby party there in 1980. Lisa was typical of a few women I had picked up over the years, in that she exhibited both reluctance and encouragement in equal measures as I attempted to persuade her to share my bed.

Maribeth's soft voice opined that she found the prospect that any woman would be so reluctant as to be not believable. I kissed the top of her head, which was the only part of her that my lips could easily reach and thanked her for that great endorsement.

"Tell me what happened the next day?" She asked.

Well, as I said, after my most enjoyable night with Lisa in my hotel, I had invited her and her co-worker Ellen, to my Derby Party where I was hosting a few of my largest clients and some of their guests.

I arose early on Saturday morning and dressed in a pressed gray suit and red tie. I was personally picking up one client at the airport, and had arranged limos for the rest. Racing started at noon, but I expected most people would arrive between then and 2 pm. The Derby itself wasn't scheduled to be run until after 6 pm.

I had arranged two venues. One was a 30' x 18' tent which had bars located at each end, a huge buffet table in the center and various tables and chairs scatted around. To actually watch the races, I had rented a box in the grandstand. There were no seats in the box, so it would be standing room only.

A few invitees had hotel reservations, but most were just flying or driving in for the day. I was spending a small king's ransom for the venues and I wasn't inclined to pay for lodging on top of that.

As I expected, most people had arrived by 2 pm and the party was well underway when a few minutes later I noticed that Lisa and another woman, who I assumed would be Ellen, arrived. Lisa looked wonderful in a black dress that complimented her figure. Ellen was dressed in a similar fashion, but her dress was gray and green. Her figure carried a few more pounds than Lisa's, but it was still attractive. Somehow, both women had found those outlandish hats that seemed to be de rigor for the Derby. I was with a major client and couldn't pull away but Lisa caught my eye and gave me a wink.

Maribeth seemed to perk up at the mention of ladies hats, and I had to attempt to describe these in as much detail as I could remember. I had to admit that these creations gave the event a certain eclectic charm, but in my opinion, a hat should have at least a modicum of functionality. Then I returned to the gist of the story.

It wasn't until sometime later that our paths crossed. I was returning from the grandstand box when I met Lisa and Ellen coming the other way. Lisa gave me a quick hug and introduced her friend. Ellen was probably in her late 40's, a little taller and a few pounds heavier than Lisa. She was from Dothan, Alabama and still had a sweet southern accent. She thanked me for the invitation and I wondered to myself how much Lisa had told her of how it came about.

I explained that I was on a tight schedule, but that I hoped to get a chance to talk to them a little later. As I walked away, I thought I saw Lisa give me a knowing smile.

As the big race approached, most of my guests were discussing how they were planning to bet. A horse named Rockhill Native was the 2-to-1 favorite, and Plugged Nickel, at 5-to-2 was the second choice. I heard almost none of the other horses mentioned. Soon the tent began to empty as everyone headed to the box.

When I arrived, I found myself standing next to Lisa and I casually asked her how she bet. "I have a hundred on Genuine Risk to win," she answered. I vaguely recalled that Genuine Risk was a filly that had been entered and a quick glance at the tote board revealed that she was probably going to go off at about 32-1. "Like longshots much?" I asked, and Lisa smiled and nodded. Just as I turned back to view the race, I heard her say, "I like to bet on the girls."

The two favorites were the clear leaders until the top of the final stretch when a smallish bay colored horse slipped between them and into the lead. It was Genuine Risk. The little filly pulled ahead and held off two late chargers to win by a length. The crowd went crazy. I glanced over my shoulder to find Lisa with exactly that knowing smile I had seen a few minutes earlier. She caught my look and just gave me a silent thumbs up. Pretty classy I thought for someone who was about to pocket around $3,200!

Maribeth inquired about which horse I had bet on. I replied that I hadn't bet at all. I just wasn't very lucky. A small voice from around my shoulder said something about nothing could be further from the truth.

The rest of the party was pretty anti-climatic. People began to seek me out to say their good-bye's and I was relatively sure that I wouldn't be fielding any last minute dinner invitations. As the crowd thinned, I noticed that Lisa and Ellen had two full glasses of wine at one of the tables. I got one of what I thought they were drinking and joined them.

Once again, Ellen took the lead to thank me again for such an enjoyable day. Then, nodding in Lisa's direction, she asked if I was aware that she had bet on the winner. I said that indeed I did. I turned to Lisa and asked her what she planned to do with her bounty. She smiled and said, "I'm taking you both to dinner, if you're free of course." I quickly looked around to confirm, then I smiled in Lisa's direction and said, "it appears I'm all yours." Ellen smiled too, but I'm sure she was unaware of the double entendre contained within my answer.

I signed a couple of checks for the caterer and used cash to tip the servers and the three of us headed toward the parking lots. Since we had driven separately, we parted to find our respective cars, but arranged to meet at the same restaurant where I had met Lisa the night before.

Conscious of Jen's Rule #1, I drove to the inn, jumped in the shower, shaved and dressed in casual beige slacks, a blue dress shirt and the brown jacket I'd worn the previous evening. I assumed that the ladies had probably gone to their hotel and were going through a similar ritual.

The restaurant was much more crowded than was the case yesterday. I suspected that it was going to be a good payday for almost every restaurant in town as 131,000 people want to be fed. Fortunately, we didn't have to wait long, and soon we were seated at a table next to the big stone fireplace.

It turned out that Ellen was quite the talker and more than once, I caught Lisa's eye when Ellen was telling some story about what seemed to be a very extensive and dis-functional family. I don't remember what we ordered or much else about dinner, but thankfully when it was over, Ellen declined our invitation to join us for a nightcap in the lower bar. I assured her that I would make sure that Lisa was delivered back to her hotel safely, and with a last thank you, Ellen departed and Lisa and I were finally alone.

I looked at Lisa and Lisa looked at me and we both broke into laughter as we fell into each other's arms. I'm sure the bar patrons wondered about the two crazies by the stairs who were laughing and kissing, but I don't think either one of us noticed nor cared.

I took Lisa's hand and led her to a small table in the corner of the bar. A small lamp provided a modicum of illumination but it made Lisa's skin positively glow. I had pretty much had it with wine and beer wasn't very appealing either. I asked Lisa if she'd ever had a B-52, and she shook her head. I told her she had to try, so I ordered two.

A B-52 is a layered cordial, which means the bartender gently pours the liquors so that they form three distinct layers. In the case of a B-52, gran Marnier is poured first, then Bailey's Irish Cream and finally Kahula. It's very pretty in it's layered appearance, but of course you don't actually drink it that way. You need to mix it up. Lisa took a sip, and I could tell just by looking at her reaction that she really liked the taste.

She leaned across the table and I had the pleasure of tasting the mixture on Lisa's lips. "You really are full of surprises, aren't you," she said. "I think I need to surprise you too."

Lisa had changed into a nice kelly green skirt that hugged her hips with a hemline that ended four inches above her knees. This was topped with a white blouse that looked exactly like the one she had worn the previous night, except this one had elastic cuffs instead of buttoned ones. Noting this, I pouted that my opportunity to bind her hands was much diminished. Lisa laughed and said something like, "we'll see."

The walk back to my room at the inn was nothing like the same journey the night before. Where that walk was headed to an unknowable outcome, this time we both knew what we wanted and we were impatient to arrive.

While the passionate kiss just inside my door was reminiscent of a similar kiss yesterday, though it contained none of the reluctance that Lisa had exhibited. Indeed, if anything, the pursuer was starting to feel very much like the pursued.

Lisa pushed my jacket off my shoulders and went to work on the buttons of my shirt. Likewise I did the same with her. Unlike the last time I unclipped her bra about the same time she relieved me of the shirt. We were both now naked from the waist up and we took a moment to press our bodies together. I was happy that my torso had retained most of my masculine musculature and I noticed that Lisa seemed to be enjoying pressing her breasts against it.

"Ready for your surprise?" was whispered in my ear. I assumed the answer was "yes," so that's what I said. Lisa kissed her way down my chest until she arrived at my beltline. I watched as she unzipped my pants and pulled them down my legs. The removing my shoes and socks, she pulled the slacks completely off. Only my briefs remained.

Lisa got on her knees and began kissing my stomach with featherlike pressure. Her hands slipped behind my butt and she filled them with my cheeks. I sensed her lips navigating through the sparse hair on my stomach when one of her hands quit squeezing my ass and slipped over my still covered cock. She traced the outline of me and squeezed the shaft. Then looking up into my eyes, she began to lower my briefs.

"I've never done this before," were her exact words, "you'll be my first. I need you to teach me."

I kicked the briefs aside when they reached my ankles, and I watched with anticipation as Lisa's eyes and fingers began to explore. At first her touch was tentative, almost like she was afraid to hurt me. She looked on with some amazement as she witnessed my penis in the act of firming.

I was pretty sure where this was heading, but I wanted Lisa to take whatever time she thought she needed. She placed my testicles in the palm of one of her small hands and seemed to gauge their weight. Then taking a quick look up at my face, she leaned forward and kissed the flesh of my inner thigh at the very junction where it joins my sac.

I know from Maribeth that this very spot is the apparent source of the masculine pheromones that she says drives her crazy. It must be so, because Lisa spent some time there inhaling my musky scent, kissing the ball sac and rubbing her face against me. In the process she had used one hand and grasped my still growing shaft and held it out of the way. I was finding her attention to be quite pleasurable, but I knew my own body and it was definitely beginning to respond.

It was at this point that Lisa stopped and pushed me to a sitting position in the lounge chair in the corner of the bed room. Then she quickly doffed her skirt and panties. The skirt simply fell to the floor and Lisa was preparing to toss her panties on top when I grabbed them from her. They were positively soaked. I held them up as if questioning their condition and pulled Lisa closer. I extended my hand and felt the space between her legs. Also a sopping mess.

"It's been like that all day," Lisa confessed. "That's my third pair, I've been thinking of you all day. I don't know what's happening to me." She was almost crying.

I lowered her to her knees so that we could embrace. I had no words, so I didn't try to invent some. I just took her in my arms and held her. After a few minutes, she leaned back and wiped her eyes with the backs of her hands. "You must think I'm a total mess."

"Yep," I agreed, "and a beautiful and sexy one at that."

Lisa laughed at this, and it seemed to break the tension I suspect she was feeling. She pressed me back into the chair and graped me again with her right hand, then looking down she said, "my hand almost doesn't go around it." She leaned closer. I could feel her warm breath, her lips were mere inches away.

"Did I tell you that I've never done this?" I simply nodded, and with that she took half my length into her warm mouth. My cock gave an involuntary jerk when it sensed it had been enveloped, and Lisa quickly removed it and looked up, seeking some assurance.

I smiled and said, "it does that when the sensation is especially pleasurable." Lisa smiled back and returned me to her mouth. I assume that Lisa had heard something about blow jobs because she started moving her head up and down my shaft. I told her to try to run her tongue around the underside of my glans and she immediately tried to comply. A few more directions from me and she had it down.

For a first timer she was very good and I told her so with every opportunity. Several times her eyes raised seeking my approval and I met each glance with a smile and a nod. However the night was proceeding too fast and I wanted to savor the time I had left, so it was with some reluctance that I pulled Lisa to me. When she lost contact with my penis, she looked at me in alarm, as if she had done something wrong. I was quick to assure her that such was not the case.

I rose and pulled Lisa to her feet. My lips found hers and I savored the taste of her. Then, guiding her to the bed, I pushed the sheets aside and we both slipped under. I laid her on her side and placed her head on my shoulder. It was the exact same position that I had Mariberh in, years later as I related this story.

Lisa wanted to talk about what had just happened. "I thought it would be different," she said. "What would be different?" I asked as if I didn't know the subject of her comment.

"Your....thing in my mouth."

"I liked it. I thought it would be something I'd have to get used to, but it seemed...so, so....natural"

"Lisa, you were perfect," I said truthfully. Well, maybe "perfect" Isn't the best word, but she was pretty damn good.

She smiled at my humble attempt to compliment her effort and it melted my heart. Resting in my arms she seemed so vulnerable at that point. I turned my body slightly so that I could encircle her body with my free arm. My fingers caressed her bare skin and my lips reached for hers. The kiss lasted a long time and I sensed that not only was Lisa comforted, but she was becoming more aroused.

My fingers, which had been innocently caressing her back were put to use on her tits and between her legs. She still felt wet even though we had taken a short hiatus, and my own arousal was building as well. All doubt was erased when Lisa whispered, "please....fuck me."

I turned completely which positioned her directly below me. I didn't wait for Lisa. I grasped myself and slid the tip of my cock up and down Lisa's slit, liberally coating it with her own moisture. As I brought it to the opening of her vagina, I sensed her push forward. It wasn't enough to impale her, but it sufficed to lodge me firmly at her entrance. It only then required a small effort on my part to complete our union.

Lisa's "noooo's" of yesterday vanished in her "yessssss's" of today.

We made love gently and passionately. We would climb mountains and sail placid seas. As we moved together, we felt more than a physical union and neither of us wanted it to end.

I was pleased when Lisa's body began to push hard against me and her ragged words implored me to "take her." Her legs would alternately grab me and then splay apart in total surrender. I knew Lisa was getting close when her hand slipped between our sweating bodies and her fingers found her clit. A few seconds later she came beneath me, her fingernails clawing my back and her teeth biting my shoulder.

Her back arched as the waves of pleasure washed over her. I continued to thrust into her and she kept calling my name, over and over.

Secure in the knowledge that I had pushed Lisa over the edge, I redoubled my own efforts and fucked her almost savagely. Lisa became aware of what was happening and as before, implored me to avoid spending inside of her. For the second time in two days, I erupted on her stomach and I could see Lisa watching.

After the last pulsation, I fell to the bed beside her gasping for breath. Sweat poured from my face and it burned my eyes. I was completely spent. In the distance I thought I heard Lisa's voice but I was too weak to answer.

I had collapsed on my side and I became aware that my ragged gasps were starting to recede Soon I felt a cool cloth pressed against my face, and I saw Lisa looking down at me. She was calling my name and when I opened my eyes, she threw her arms around me and kissed me all over my face.

Several times I heard her start a sentence, only to falter after a few words. "That was.... It was,,," were the starters, but she just couldn't complete the thought. I reached out and pulled her into the bed, then found the covers and snuggled beneath their weight. I wiggled into position behind Lisa and wrapped an arm over her breasts. I nibbled at her ear and thanked her for the pleasure she'd given me.

It was after midnight when we awoke. I never remember falling asleep, nor did Lisa when I asked, but apparently we had.

Nature was calling both of us and we took turns in the bathroom. My flight wasn't until late afternoon and I gave Lisa the choice of whether to spend the night or go back to her hotel. She looked sad when she told me that it was probably best that she leave. She said that she would have liked nothing better than to come back to bed, but she couldn't miss work. I knew the feeling, but when duty calls...

The last time I kissed Lisa was just before I let her off at her hotel, but we never saw or spoke to one another again after that night. Six months later, I received a card in the mail at the office. It was a wedding announcement. I wrote a brief message on the back of the card and sent it back. I wrote Lisa that I wished her well and the groom was one lucky guy.

I will always remember Lisa, and of course Genuine Risk.

For the last five minutes of this story, Maribeth had been stroking my cock beneath the sheets and had succeeded in bringing me to a full erection. I chose not to tell her that the mental images that I was recounting had also contributed to that outcome.