The Elusive Jenna

A story on SOL by JennaShoes inspired this, my first submission. I hope you enjoy it and please let me know your feelings, one way or the other.

I don't get the chance to get away from my consulting business very often but when the opportunity arises (literally) I take full advantage of it. My name is Mike Bradley and I retired from the military a number of years ago to pursue a career as a consultant in the security business. You can read what you will into that lifestyle and a lot of your assumptions will probably be correct. I may share some of my life-secrets with you in the future but, being a fairly closed mouth white Anglo-Saxon agnostic, I'll have to have a fairly good reason to.

I was in the middle of a three week spring break in a Dominican Island resort and had finally managed to reach an enjoyable level of relaxation while getting a pretty respectable tan over my 6' 2" frame. I tried to take these holidays at least twice a year to just relax, chill out and maintain my mental sanity. I'm not a bad looking guy for 43 and usually get lucky if put my mind to it. It's just that these vacations are for me and my well being, not about getting laid. However, if the opportunity arises, I have been known to take advantage of it. These vacations also allow me to spend significantly more time in the weight room than I was able to at home. I can tone up my 200 lb frame and I feel pretty good about myself as I hit the beach for my morning run after my workout. I had been doing this on a daily basis since my arrival, as much to avoid the intense heat of the day as to check out the female early risers and tease my other senses.

During these early morning jogs, I had noticed a thirty something, well endowed female who seemed to be busily laying out her chassis lounge and towel every time that I passed by. After the second day, I began to get the feeling that she was not only interested but was sending out signals. On that day as I passed by, she was bent over, her bikini panties pulled tightly across her ass. She seemed to spend an inordinate amount of time spreading out her towel as I jogged / tripped / stumbled by. She appeared to be amused by my antics as she turned her head and smiled as I went by.

This went on for a while, with both of us regularly exchanging smiles. On the fifth day of my routine, as I approached the area where she usually set herself up, I couldn't help but notice that she was already comfortably lying out on her lounger. What was different this morning was that the lounger was pointed down the beach, in my direction, rather than the other way to capture the sun's rays.

Even though she was wearing sun glasses in anticipation of the sun's eventual appearance, I could tell that she was watching my approach. A myriad of thoughts over this change in her routine and what it may mean were running through my head as I approached her. Uppermost in my mind was, "don't trip fool!"

I was probably about ten feet away when she spread her legs so that her feet rested on either side of the lounger rails. As I got closer to her, she slid a hand down between her legs and grasping the gusset of her bikini, pulled it aside as if to re-adjust an uncomfortable fit.

By this time I was directly in front of her and had a perfect view of her pussy. Even at this distance, the lips appeared to be pouty and slightly parted, framed by beautiful chestnut curls. In reality, it may not have been glistening with moisture but my imagination certainly painted it that way as I managed to stumble by.

By this time she was probably smiling or laughing at me but I didn't see anything but that perfectly pink pussy. As can be appreciated, that image caused a considerable tent in my cut-offs which stayed with me for the remainder of the day. (both the tent and my cut-offs)

That evening, after I had showered and changed into a light tropical shirt and beige slacks, I went to the resort restaurant and enjoyed another great meal by myself. While sitting there alone, I decided that I would break my routine. Instead of walking the beach as I usually did after supper, I would visit the lounge to see what was going on there.

Looking around as I entered the lounge, I spotted my "friendly" sunbather from the last couple of mornings. She was sitting at a table for two beside one of the floor to ceiling glass walls. One chair was empty and she appeared to be daydreaming with a half finished drink in front of her. Even if I hadn't of recognized her right away I was immediately drew to her form fitting pink floral sundress that accented her luscious curves. The pink silken belt securely tied beneath her large breasts only further enhanced the image as they just begged to be appreciated.

My mind went into overdrive as a million ideas ran through my mind about approaching her. As I stood there, for what seemed like hours but was probably only minutes, I couldn't help but ogle her gorgeous tanned legs accented with pink espadrille shoes. They had 5" wedge heels and fabric straps that wrapped around and up her ankles as they caressed her calves.

The blood was surging in my not so distant member as a number of erotic thoughts ran through my mind. Finally, raising my eyes to her face, I saw that same smile, albeit mocking, as she slowly ran her tongue over her lips, wetting the already bright red make-up. Was this a come-on?

I decided that I had had enough of the teasing! I confidently walked up to her, introduced myself and asked if she would mind sharing her table with a fellow vacationer. Ok, so it wasn't very original but then, after the past five days, my brain was close to being short-circuited anyway and, from the signals that she had been sending, I felt fairly confident. You can imagine the single vision that had been constantly in my mind.

Standing there with bated breath, waiting for her answer, I was confused by her attitude as she looked me over with a prudish air of intolerance and casually indicated the empty seat. She said, "My name is Jenna" while giving me the impression of being a queen holding court while I was but one of her very lowly subjects. Had I misread what I had thought were her intentions?

A cold feeling ran down my spine as I questioned whether I had a big mistake and was wasting a perfectly good evening just to get shot down. As my erection shriveled up inside me, my thoughts switched from being horny to wondering how I could cut this disaster short and retreat to the safety of anywhere else but here.

Things didn't appear to get any better as she appraised my over my six foot frame with an attitude of aloofness. As I sat down, the mild fragrance that she was wearing washed over me as I glanced at her luscious breasts while trying to maintain my gaze on her face. Poor attempt as her breasts were of above average proportions and it was obvious that, as she turned towards me, they were receiving no support. Nor did they need any! My erection again reared its head as the bulge in my pants started to increase. After all, attitude or not; I realized that I was extremely horny! Although I was receiving very conflicting signals from this woman, I couldn't help but notice that her attention had been drawn to the tent in my slacks. Her tongue again caressed her lips but this time I couldn't help but notice some degree of nervousness, as if driven by indecision. Had she misjudged her own desires? I intended on finding out.

After some minutes of idle conversation she raised her left hand to emphasize a point of conversation. I hadn't noticed it before but her body wasn't suntanned all over. Her ring finger stood out indicating an absence of wedding bands. The difference in skin tone was fairly obvious to the point that I instantly knew that this woman was married. She appeared to recognize the fact that she had made a faux pas as she quickly lowered her hand beneath the table.

I immediately assumed that I now knew why I was getting attitude. Her signals and desires on the beach over the previous mornings had been fairly strong and obvious. Her attitude this evening indicated that she may be having second thoughts now that we were face to face and regretted her rashness of this morning's encounter. I wasn't bothered by the same conflicting emotions. The fact that she had flashed me this morning was all of the incentive that I needed. Now all I had to do was to convince her of what she really wanted. Obviously, she already knew what she needed.

We attempted to avoid the elephant in the room as we enjoyed a couple of more drinks and quite a number of laughs, I could see that the woman of this morning was starting to slowly return to the table. The stories and jokes became a little more risque and titillating as the alcohol flowed and the evening moved on. I couldn't help but notice that her breathing was beginning to increase and, with that observation, the bulge in my slacks returned and increased to the point where it was gaining even more of her attention.

It was at about this time that she mentioned that she had to use the restroom. She had been sitting across from me and as she pushed her chair back, she rotated it so that she was directly facing me. Staring into my eyes, she slowly uncrossed her long legs, lifted the bottom of her sundress well over her knees which she tantalizingly separated so that I had a clear view of her thighs right up to her crotch. Her pale pink bikini cut panties barely concealed the indentation of her slit and the puffy lips that surrounded it. She passed her glass to me with a twinkle in her eye and a smile on her lips that lit up the lounge; and asked if I would be so kind as to refresh her drink. With that, she got up and headed for the restroom, all the time twitching her tight ass under the pale pink dress.

I had just been flashed for the second time in the same day! My erection threatened to burst right though my trousers. There was now no doubt in my mind that the lady had come to a decision and it was up to me to provide her with the joy that she had had so much indecision in deciding to enjoy. I ordered a couple of more drinks while I awaited Jenna's return. I glimpsed her coming towards me and her smile again made my heart sing in anticipation. I know knew that this was going to be a great night!

As she sat down again, my eyes were instinctively drawn to her legs and I was not disappointed. I believe that my little Jenna is a bit of an exhibitionist! She again lifted her dress above her knees as she sat. As her ass hit the chair she again parted her legs more than normal affording me a look directly up her legs and past her thighs to her sweet pussy which was totally uncovered and bared before me.

I quickly looked back up at her face as she smiled brightly and pushed her dress over her knees to turn into the table. Reaching across with her closed left hand, she said "Mike, give me your hand".

I instinctively knew that she was offering me something as I stared at her closed hand on the table. Again, I couldn't help but notice the outline of her missing wedding bands. I moved my open hand across the table and Jenna placed hers in mine. She then placed her other hand on top, and continued to stare into my eyes.

Then, with the deepest, most sultry voice that I have ever heard she said, "I'm awfully sorry for my earlier attitude, Mike. Perhaps you would accept these as a token, as well as an indication of how much I would like to show you that I can be very, very nice."

As she drew the words, "very, very nice" out, I almost came in my pants. I will leave the vision resulting from those words up to your imagination as I still cannot put words to the sexual excitement that they caused.

Knowing what I held in my hand, I slowly raised it up to my face. I could feel the dampness of the panties as I brought them to my nose and inhaled deeply, savoring the fragrance of the pussy that I knew I would soon be worshiping in all its glory.

To say that Jenna had surprised me would be an understatement. The fragrance of her panties along with the glimpse of her pussy had the expected effect. I now had to decide how to deal with a stiffening cock in a public venue.

The problem was further compounded when Jenna pointed out that we hadn't received our drinks yet.

With a twinkle in her eye and that knowing smile upon her lips, she said, "Mike, why don't we have one more drink and then decide what to do next?"

I turned slightly so that I was directly in front of her as she had been with me. Leaning back and staring directly into her deep brown eyes, I slowly adjusted my cock so that it ran up the length of my stomach. I picked up our glasses and then stood up so that the bulge in my slacks was directly in front of her face. Her expression was worth the pain of my belt cutting into my cock as I stood up. Standing there in front of her, I watched as she licked her lips. I almost expected her to lean forward and swallow the front of my slacks.

Smiling to myself, I walked to the bar and ordered a couple of drinks. Waiting for the cocktails (don't you just love that word?) gave me the opportunity to calm down and allow my boner to return to its almost natural state. It was obvious to me that this woman with attitude was more than ready to play and I looked forward to the opportunity of getting her onto her back with her legs spread open before me.

After I returned to the table we continued our little game. The innuendos became more sexual in nature to the point that both of us became even more stimulated. We had a lot of fun discussing the funny way that I ran on the beach and her bikini "malfunctions."

As the evening progressed, I decided that it was time to move to the next level while we were both still very stimulated. I suggested a little game of "truth or dare". Turning towards Jenna, I leaned back for a second time, adjusted my stiffening cock and, looking her right in the eyes, and said "I have a little problem here that needs some immediate attention. I dare you to look after it?"

The look in her eyes was that of pure lust as she again ran her tongue over her lips. (Why is it that a woman can make that act look so erotic?) She hesitated for only a second before replying, "First, it looks like what you've got isn't a "little" problem. Secondly, I've never turned down a dare in my life and thirdly, do you want me to look after it here or would you like to go to your room?"

Nothing more need be said. With that, I helped her up and we quickly proceeded to the foyer. Watching her walk ahead of me was an experience in itself and a lesson for all less fortunate women in how to drive a man crazy. By firmly placing one foot in front of the other it accented the calves of her perfect legs while causing her tight ass to roll in ways that lesser women can only dream about.

The tall wedges with the sensual lacings only contributed to the entire effect. I'm sure that every man in the place was watching her ass as we walked by. You would think that she would be extremely sore from the visual fucking that she received as we walked the twenty yards to the elevator. Watching her destroy the lesser mortals, I thought to myself, 'Sex, your name is Jenna!"

Alone in the elevator, she turned into me before the doors had finished closing. Turning towards her, our lips came together with a fiery intensity. As our tongues starting dueling, she thrust her pelvis against my stiffening rod which caused it to further rise to the occasion. Reaching down, she grasped my cock and breathed into my mouth, "Jesus Christ, I really need this. It feels huge!"

Always ready with a quip, I replied, "Actually; my name is Mike and we're at my floor."

A giggle escaped her lips as she squeezed me one last time and proceeded out of the elevator for the short walk down the corridor. I loved the feeling of her tight body closely held against mine as I stiffly tried to walk beside her.

Entering the room, her actions left little room for discussion. Her pink sun dress took on the essence of a sail as she launched it over her head. It floated across the room to land in a chair. In seconds she stood before me wearing only those delectable wedges.

Standing naked, perched upon the 5" heels with the straps interwoven up her calves, in all of her feminine glory, she appeared as a roman goddess, exuding the sexuality of all of the ages. How could any man have let this beauty out alone?

Extending her arms while turning slowly towards me, in that low, sultry voice she asked, "You like?"

I removed my shirt and unbuttoned my slacks in what must have appeared as one quick motion. Actually, I think that I tore them off! I stood before her with my now engorged cock licking at my belly button.

Just as my slacks hit the floor I couldn't help but notice a look of concern cross Jenna's face. She moaned, "Fuuuck Mike, it's too big. I'll never fit."

This wasn't the first time that I had heard this lament and I was ready for it. "Don't worry Jenna honey, it's gone into a lot of other women before and all of them have loved it. I'll be gentle as you cum like you've never cum before."

This seemed to settle her down as her hands slowly rose up her side in a caress that came to a stop as she cupped both breasts squeezing the nipples between her fingers.

This vision of beauty stood before me as I drank in a female of lustful proportions. Directly in front of me her breasts stood upright and proud. Moving forward, I filled my hands, allowing the firm nipples to sit comfortably between my fingers and thumb as I rolled and teased them to their fullest extension.

Large, with a hint of maturity, they begged to be caressed. They were capped with brownish aureoles whose bumps were very visible as a result of her excitement. The nipples protruded a good half inch or better and I couldn't resist sucking the erect nipple into my mouth. I squeezed the two of them together until I had both nipples clenched between my teeth. Biting down gently I beat a tune upon the nipples with my tongue while Jenna moaned and grasped my cock with both hands in her excitement.

I released one breast and reached down over her mons to run my fingers through her brown bush. Pushing further I slipped a finger into her slit to find it already sopping wet with lubrication and her lips swollen in arousal.

As her pussy continued to lubricate Jenna separated her beautiful legs even further to allow me access as her moans became louder and more intense. Breathing into my ear she hissed, "Oh fuck that feels sooo fucking good, Mike".

I moved her backwards toward the bed until Jenna had no where else to go. Pushing forward, we fell onto the bed. I was still grasping Jenna's nipple with my mouth while my two fingers were buried deep in here sodden pussy. She was jacking my cock up and down and I could feel her rubbing the cream leaking from my cock over the head. While lying on top of her I added a third finger to her hole in order to feverishly finger-fuck her while running my thumb over her engorged, very erect clit.

Jenna's encouraging, "Yes, yes... please fuck me now. I need you to fuck me. Put that big cock into me!" caused an increase in my efforts until Jenna came with a loud scream and even more lubrication was released from her pussy over my fingers as she hit her first orgasm.

I released her nipple which by now was red and swollen from my efforts. I rolled Jenna over and pulled her ass up on the bed so that her feet were on the floor while her face and chest rested on the bed. Her ass and pussy were predominantly in my face with the pouty wet lips begging for attention.

I grabbed her ass cheeks in both hands and spread them wide apart as my tongue bathed a path from her clit up to her ass. Gathering lubrication on the way, it was easy for me to drive my tongue into her little starburst with no effort. This was met with a loud gasp as she pushed her ass back towards my face. I continued my efforts until her slit was totally soaked with her moisture.