Better with Age Ch. 03

It was the following Wednesday and I was in the office doing paperwork and various project follow up when my cell rang. The caller ID told me that the call was coming from Jean's office and my cock stirred thinking of the coming Friday appointment.

"Hello Mr. Dupree, this is Gretchen from Jean Merryweather's office. Can you hold for Ms. Merryweather?"

"Sure Gretchen, I'll hold."

"Mr. Dupree? Hi it's Jean. Listen something has come up and one of my clients is going to be here on Friday so I have to cancel our appointment." She was very professional in her delivery and you would think that our appointment was strictly business when it most certainly was anything but.

"But I want to make it up to you, are you available the following weekend? I have to travel to Pittsburgh next week for business and I see that the Mets are in to play the Pirates that weekend. I could fly you in on Saturday morning and we could go to the game together. Does that sound good to you? I've heard it's a great ballpark to see a game in."

Although I was disappointed that I wouldn't be getting laid this Friday I brightened at the prospect of having Jean to myself for a whole weekend. "I am up for it, I've got no plans. I could use a change of scenery also. Thank You."

"It will be my pleasure Mr. Dupree, I'll have Gretchen contact you with the travel arrangements. Don't worry about the cost, I can charge it off to my client as a consulting fee. If they only knew what kind of consult you provide me with." She laughed.

We rang off and immediately my mind started to dream up various scenarios for the weekend. After our last session in her office I knew that I could push the envelope with her and enter a whole new stratosphere of sexual experience that a month ago I would never imagine could happen to me. Just then my boss stopped by my office and pulled me back into reality and my lewd thoughts were put on hold for the time being.

The weekend came and went and I kept myself busy with work and a barbeque with some of my buddies. It was funny one of my friends wanted to hook me up with a chick in her 20s. I told him I would get back to him, knowing full well I couldn't go for the young ones anymore now that I've experienced the pleasures of an older woman.

On the Wednesday before the trip Gretchen called to get my email address so she could send me the flight confirmation and hotel booking. I wondered what she thought of me traveling out to meet her boss on a weekend. I suspected she knew something was going on in Jean's office that 2nd time I was there. If she hadn't left yet she most certainly would have heard us. Oh well I didn't care one way or the other. She told me that Jean would meet me at the airport Saturday morning and gave me her cell number if I needed it.

Thursday night I went out shopping for the weekend. I picked up some nice pants and a shirt for me to wear out after the game. Then I hit a woman's store and picked up a short skirt, a silky blouse that was about a size smaller than I imagined Jean wore and ever so slightly shear that would telegraph her wonderful breasts in the right light. A trip to a lingerie store for a matching pair of fire engine red panties and a push up bra (again a size smaller than I figured she was) and I had the slutty outfit I wanted her wear out to set the right tone for the night of debauchery I had planned for her.

Saturday morning I flew out for the short flight to Pittsburg. I managed to doze off a bit as visions of sex with Jean danced in my head. We landed and a short while later I was in the terminal picking up my luggage. Just as I got my bag I saw Jean come thru the revolving doors. She was dressed for the game already in her Mets home jersey and a pair of Khaki shorts. Her grey hair was pulled back in a short ponytail. She opened her arms and welcomed me with a kiss and pushed her breasts into my chest.

"I'm glad you came! It's a beautiful day out, great day for Baseball among other things." Jean said with a wink.

"I've been looking forward to it! Both the game and the other things." I chuckled.

We hopped into a taxi and headed off to the hotel to drop my luggage and get my game clothes on. She told me not to bother checking in; she already took care of cancelling my room so we would be together in her suite. She said she had to keep things above board so Gretchen wouldn't get the wrong idea. Once in the room she advanced on me, taking me in her arms for a much friendlier kiss than the one at the airport. Her hand roamed down to rub my cock thru my pants. "I'm so hot for you Mike; I've been thinking of fucking you since I woke up this morning."

"I'm hot for you too Jean, but I have big plans for you tonight. Let's hold off until then. I promise you it will be worth it." I pulled back and looked into her lusty eyes for acceptance. I saw it there, albeit a reluctant acceptance.

"You better make it worth it or you'll be on the first plane back to New York!" She chided me playfully.

We continued some more kissing and a bit of petting before we had to get ready for the ball game. I put on my own Mets away jersey and cap and we were off to the game. We arrived early enough to catch batting practice and explore the park before the first pitch. We grabbed a couple of the local beers that were sold in the concessions and took our seats. They were along the 3rd base line about 10 rows up from the field. Jean told me she got them from her client who had season tickets.

The sun beat down on us as we thoroughly enjoyed watching the Mets beat up on the home town Pirates. We continued to down cold beers and I was surprised to see her keep up with me. We easily put down 6 each by the time the game ended with the Mets on top 7-2. Afterwards we hit a local pub for some burgers and a few more beers. By the time we made it back to the hotel we were both pretty tipsy and somewhat tired from being in the sun all day.

When we got into the room Jean began to get frisky again, and I had to use all my self control not to give in and let her have her way with me. We playfully stroked and kissed each other on the bed but eventually the alcohol and sun caught up to us and we were both drifted off to sleep for a much needed nap.

I awoke with a start an hour later a bit groggy and not sure where I was. I turned and saw Jean resting next to me and my fog cleared and I remembered where I was. I lay back in bed and recalled the day at the ballpark. We had a lot of fun and I think Jean and I were becoming close spiritually in addition to sexually. But the lecher that I am I started to think about the night ahead and I started to get aroused. I mentally shook the images out of my head and ambled off to the shower to wake myself up. I had just put shampoo in my hair when I heard the bathroom door open. A minute later a naked Jean slipped into the shower with me and I felt her breasts against my back. Her hands went to my head and she massaged the shampoo into my hair in a seductive way I didn't think was possible.

She bent my head into the spray to rinse off and began to slowly hump my ass as she continued to massage my head. When my hair was cleansed of soap I turned and took her in my arms and our mouths joined each other in a tender kiss that quickly changed into a tongue fight, each of us trying to suck the others tongue into the others mouth. I reached for the soap and began to rub it all over her body. We each spent a generous amount of time soaping up each other's asses, and slippery hands spent ample time on my cock and her tits. Tempting as it was to take things further I kept with my charge and we rinsed and toweled off to get ready for the night ahead.

I told Jean I had picked out an outfit for her to wear for the evening and she raised an eyebrow and said "Really Mr. Dupree? I didn't think you woodworkers had that in you."

We laughed and I went to my bag and extracted the items I had bought and had wrapped. I gave her the undergarments first and she oohed and aahhed before seductively putting them on for me. I never knew a reverse strip tease could be so sexy. I reached into my bag again and brought out my own silk boxer shorts and emulated her actions to a T and got a rousing ovation for my efforts. Next I pulled out the shirt and skirt that were packaged together and presented them to her. Again she expressed her pleasure with my selections and made a show of putting them on. I followed her lead and soon was decked out in my new duds, looking very upscale yet relaxed at the same time.

Jean was a vision of sex before my eyes. The skirt was a bit tight and came up to her mid thigh, hugging them and showing off her long sexy legs. The blouse was buttoned up to just above the swell of her large breasts and showed a generous crack of cleavage. The red pushup was doing its job well and the color was evident thru the fabric of the blouse. What really sold it was her very erect nipples were on display and her excitement evident.

We went down to the street and hailed a cab to the restaurant. We put on a show for the cabbie as we French kissed in the back seat like school kids. I pinched and pulled on her nipples and they stood out even more through the sheer fabric. I also made a show of caressing her thighs and running my hand up to the crotch of her red panties. She spread her legs wider and gave the driver a view up her skirt in the rear view mirror. By the time we got to the restaurant Jean looked like a bitch in heat and I like the sly fox ready to mount her.

We strode into the bar area after checking in with the maitre d and many pairs of eyes were on Jean, some leering on the part of the men and some disapproving looks from the women. One woman actually looked Jean up and down and licked her lips. Jean ate all the attention up and I think her already protruding nipples got even harder if that was at all possible. We found 2 open seats at the bar and ordered drinks from the bartender who had a hard time keeping his eyes off of Jean's deep cleavage. She whispered in my ear. "People are looking at me like I'm some kind of slut." After a brief pause she added "It's getting me hot!"

Our drinks came, wine for Jean, scotch for me, and we clinked our glasses and toasted the Mets. I took a long pull and felt the heat from the scotch radiate within. I leaned in to whisper in Jean's ear and put my hand on her thigh. "I want you to go to the ladies room and take off your panties and bring them to me."

Jean looked at me with a combination of surprise and excitement. "And go another button down on the blouse." I added as she jumped off the bar stool and headed off towards the ladies room. 5 minutes later Jean returned to the bar. I thought her tits were going to pop out of her blouse with the next button undone as she bent slightly to hand me her panties. She made a show of opening up her thighs as she mounted the bar stool and the patrons in the booths across from the bar got quite a view of her now naked pussy before she turned back towards the bar and me.

I took her bright red panties and stuck them in my back pocket with about 2" hanging out for all to see. I leaned in to whisper in her ear "I could fuck you right here and now you look so god damned hot". I put my hand on her knee and slowly rubbed it back and forth. I was inching my way towards her skirt when the Maitre D came to tell us that our table was ready. Jean turned around on the stool and I took her hand as she slid off and her skirt slid up her thighs giving the man a quick beaver shot that left him stammering as he led us to our table.

We were fortunate to get a booth table all the way in the back of the restaurant. It was one of those places with dark mahogany wood and solid color paints that gave it a feeling of intimacy. There were only 2 tables that had a viewing vantage of our table and the couples at those tables were thoroughly engaged in their own conversations to notice us as we took our seats, me facing the restaurant and Jean facing me. Jean leaned forward and rested her great tits on the table top and took my hands in hers.

"I'm having a great time Mike, but I can't wait to get out of here and start fucking."

Just then the waiter appeared. He must have been briefed by the Maitre D about Jean's little show so he was prepared and acted professionally when he asked for our drink order and gave us our menus. Not once did his eyes wander to her bountiful cleavage, which was no small effort for any man I can say from experience. Jean ordered another glass of wine and I got a seltzer water (I had enough booze for one day and wanted to keep up my stamina, I was going to need it). When the waiter had disappeared I slid my hand across the table and began playing with Jean's left nipple thru her blouse. I kept an eye on the couples nearest us but they had no interest in us, not that I would have cared either way.

"I want to get that waiter to notice you when he comes back, the nerve of him not checking out your beautiful tits."

I slid my hand inside her blouse and squeezed her tit, feeling the hard nub of her nipple in my palm.

"I want to taste you, stick your finger in your wet pussy and feed me your juice."

I gazed into her lusty eyes. Jean moaned slightly as she slid her hand under the table and followed my instructions. She finger fucked herself for a few seconds before bringing her moist fingers up for me to lick. I had just finished cleaning her juices off when the waiter returned with our drinks. I think he could smell Jean's sex and this time he tried to steal glances at her hard nipples poking through her blouse. I upped the ante by "accidentally" knocking my fork off the table. The waiter bent to pick it up and Jean taking my cue spread her legs wide and gave him a close up view of her hot cunt. When he stood back up we could see that he was starting to get wood and rushed to take our order and go before he got in trouble.

Jean and I continued our sex play while we waited for our orders to come. She would finger herself and I would suck her dry. She occasionally would bring her foot up to rub my boner thru my pants. I played with her tits whenever the opportunity presented itself (which was often surprisingly enough). By the time the food came we were practically ready to fuck on the table. In fact if we weren't so ravenous for food I think we would have left long ago. So after another tease with the waiter we tucked into our meals and ate like hungry animals as we both knew that desert that night was what we really wanted to get to.

I paid the bill, under protest from Jean of course, and we headed for the exit. We were all over each other in the cab back to the hotel and I thought the cabbie was going to crash his taxi because his eyes were open wide and in the rearview mirror every time I looked up at him. But we made it back in one piece and I threw some money to the cabbie while we put our clothing back in somewhat presentable shape before rushing into the hotel lobby towards the elevators.

I pushed the call button and we waited impatiently for the elevator to arrive. When it finally arrived we got on and I pushed the door closed button. Just then another couple came and the guy stuck his foot out to stop the doors from closing. The couple got on and smiled at us and thanked us for holding the car for them. I wasn't that happy because I was planning on starting to fuck Jean in the elevator on the way up but what could I do. We were on the 20th floor and the couple pushed for the 19th floor so my plan was pretty much shot.

The cab was kind of small so I backed into the corner and Jean was just to my left slightly in front of me. The couple was an attractive elderly gentleman and slightly younger woman and they started up some elevator small talk with Jean (must have been the grey hair I thought). While they chatted enthusiastically about the weather etcetera I slid my left hand under Jean's skirt and between her legs. I deliberately slid a finger into her pussy and started to slowly fuck her with it. Her voice faltered slightly while she tried to keep up her end of the conversation with the elderly couple, but she managed to keep them from knowing what I was doing.

Soon enough the elevator arrived at the 19th floor and the couple wished us a good night and exited the cab. As soon as the doors closed Jean wheeled on me.

"You fucking bastard!"

She pushed me against the wall and threw her arms around me and kissed me hard on the mouth. She just started grinding her crotch into my hardness when the indicator dinged and the doors opened onto our floor. Not wanting to waste another minute I grabbed Jean by the hand and we practically ran out of the cab and down the hall to our room. Jean fumbled thru her purse for the key card and finally got it out and put it in the slot. The light turned green and we pushed the door open and entered the room.

The door closed and Jean was on me like a lioness on her prey. She threw me up against the wall in the entry foyer and began kissing me so hard I thought she would draw blood. Simultaneously my hands were on her tits as hers grabbed my cock thru my pants. I grabbed the insides of her blouse and pulled outward, buttons popping every which way. I pulled the blouse down and off her then grabbed her pushup bra and pulled it down so her huge tits spilled out into my hands. I grabbed her breasts roughly and squeezed while we continued to kiss hungrily. By this point my pants were undone and Jean had my hard cock in one hand while the other pushed my pants and underwear down my legs. I kicked off my shoes and my pants when they got down to my ankles. I broke our kiss long enough to say "bed!" in as demanding a manner as I could muster and pushed Jean in the direction of the king sized bed.

I quickly removed my shirt as Jean dove backwards on the bed. She hiked her skirt up and spread her legs wide. I jumped on the bed and pushed my head down between her legs and my mouth slammed into her pussy with an audible smack. I began feasting on her hot wet pussy, not with any finesse, just plain hunger. My mouth and tongue were everywhere, on her lips, between them, on her clit, over it. She was moaning her pleasure and her much needed release was fast approaching. I took her clit between my teeth and pulled slightly outward. I let it spring back and attacked it with my tongue. Round and round, back and forth. Licking it, lashing it.

I pulled my head back and looked up at Jean, gyrating on the bed. "Your cunt tastes so fucking good!" I exclaimed. My words were quickly muffled because she just grabbed my head and pushed it back into her juicy gash.

"Fuck, Fuck, Fuuuuuuuckkkkk, Eat me, Eat me, Ohhh, Ohhhhhhh!!"

Jean yelled out as her first orgasmic wave of the evening crashed on shore. I obliged and continued my frantic licking and sucking of her spasming cunt while she pushed it into my mouth and pushed harder on my head, almost trying to impale herself on my head. She continued to cry out as her orgasm continued in waves as the pent up lust from the day poured out. I stuck my tongue out and fucked her open pussy as fast as I could. I did this for about half a minute and then took her hard clit back in my mouth again and sucked hard. Jean came again, hard, and almost bucked me off the bed. I never had a lover get this fucking hot before and it drove me wild with lust.

As Jean started to come down I pulled her skirt completely off and I crawled up her body and shoved my rock hard 8 inches deep into her pussy, my balls slapping against her ass.

"Ooof, oh yeah baby Fuck me with your big dick, give it to me, fuck me hard!"

I didn't need any further incentive and did just as she asked. I pulled almost all the way out and shoved it right back in. Over and over again I assaulted her hot fuck tunnel with my fuck stick. The bed rocked and the room filled with the sounds of hot fucking. Jean oohed and aahed and I moaned and groaned as I pounded her relentlessly. Her tits were bouncing all over the place as she took my cock over and over again.