There Might Be a Connection Here

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Sometimes age really doesn't matter.
7.5k words
4.62
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Part 1 of the 3 part series

Updated 06/07/2023
Created 01/01/2016
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Well, if you plan on having sex with a woman, it's always a good idea to meet one first as they say.

Being in my early 50's, I still prefer to meet someone in person rather than on the internet just because I still believe in it being more fun if two people have some level of chemistry between them. There's nothing more enjoyable than watching a woman's hips while she walks, or checking out the bounce in her breasts, or her smile and especially how she smells to build the interest level in her. A woman with the right perfume can totally distract me from any conversation I might be having with her and in the most pleasant way. I can't get that kind of thrill from an internet profile, no matter how hard I try.

Unfortunately the social dry spell has been a long one, more than three years and my confidence with the fairer sex is not what it used to be. I won't go into the history but suffice it to say I am well on the way to getting much healthier, which hopefully will make me more desirable as well. When I can walk around the house and get the occasional random erection in my pants thinking about an old flame, I know my comeback is headed in the right direction.

So today I found myself in the wine aisle at the grocery store. I know nothing about wine but figured I should have a bottle of some kind of white and some kind of red in the house just in case some female company stopped in. Otherwise their only choices would be whiskey or milk, neither of which the women in my past have gravitated to.

As my confusion started to build with all the choices and prices, I decided to do what I always do----ask any friendly woman within proximity what her choice would be. I quickly spotted a friendly looking but slightly overweight woman dressed in her nursing outfit and decided she would be as good as anyone to help.

"Excuse me, I could use a little help picking out a bottle of wine. Do you have a favorite you serve when entertaining guests?"

"Oh," she said. "Sure. Is it for dinner or no particular occasion?"

She had friendly eyes which I enjoy looking into. She had very feminine features and little makeup, letting her natural beauty show. Unfortunately the scrubs hid any indication of her figure. Better that way, I guess. No sense in getting caught checking out her cleavage when I was just trying to get some friendly help.

"Nothing in particular. I just want to have something on hand for guests. I'm not really a wine drinker so have no idea which type or label is a good quality for the price and what a lot of people might like."

"In that case, I would suggest you get a bottle of white zinfandel and a bottle of merlot. A&C Vinters is a good brand, any guest should be happy with one of those."

"Thanks I appreciate the suggestions." I grabbed a bottle of each and put them in my cart. As I was doing so, she said, "No problem" and headed off with her cart to finish her own shopping. I couldn't help but wonder what kind of panties nurses wore under their scrubs. Figured they would be granny panties as they would go for comfort and not sexiness while on the job. She was a little heavy in the hips but I always liked a girl with a bit more padding. More to squeeze and hang on to when doing her doggy style.

Whoa! Time to put the imagination in check unless I wanted a reputation for being the dirty old man who hits on women at the market. Flirting is not what it used to be, everyone seems to be on edge all the time nowadays. You can divulge your most personal history and language on the internet with no consequences yet smile at a woman the wrong way in public and they are ready to swear out a warrant for your arrest as a pervert. Oh well, adapt.

I paid for my wine and was walking out to my car when the imagination kicked in again. Now I was wondering how she shaved her pussy. I really did not like the bare look, just occasionally for variety on my women. I still enjoyed rubbing my nose through a women's pubic hair while eating her. It just activates one more sense.

I could still remember the first girl I went down on in college. It was so erotic to pull off her jeans and then her mid-rise panties (that was the sexiest style worn in those days) to unveil her gorgeous brunette bush. The sensation of kissing my way up each of her thighs before burying my nose in her bush and my tongue in her pussy sticks in my memory to this day. I'm sure I was really lousy at giving her head but when you are only 19, youth and hormones can make up pretty good for a lack of skill. I smiled at the memory.

I took the wine home and put it away. Looking at the clock I noticed it was 7 pm and I still hadn't had dinner. Not wanting to cook or get fast food, I decided I still had time to run down to the Mexican restaurant down the street and grab a bite before turning in.

The bar had several openings so I grabbed a stool. Julie gave me a big smile and handed me an ice cold bottle of Budweiser, my usual. After placing my order, I turned my focus to the ball game on the television behind the bar.

"Looks like you are eating alone. Mind if I join you?" And then I sensed a body filling the chair next to me. It was Tracy from the Ace Hardware store.

"No, not at all," I said and smiled. "Just get off work?"

Tracy was in her early 30's I guessed but other than that I really knew nothing about her. She was about 5'2", cute face, great smile, brown eyes, mostly straight brown hair held back in a pony tail tonight and a great personality. He body was average but cute, nice 34B breasts I guessed, just a little cushion around a mostly trim waist and then nice rounded hips. I often asked myself while checking out if I would fuck her given the chance and decided I would. Being 20 years older than her, I didn't worry about it ever happening however.

"I actually was off an hour ago. I had time to run home and get cleaned up. Then decided I was not cooking so ended up here. It's so close to home I'm surprised I have never been here before. It's good to run into a familiar face."

"Well," I told her, "the food is good and it's not too loud, even in the bar. First drink is on me---what would you like?"

"Rum and coke please," she said. I passed that along to Julie who delivered it quickly, gave me a friendly smirk then headed off to the other end of the bar.

Tracy and I began talking about nothing in particular. It was easy to talk to her and several times she flashed me a warm smile, telling me she was enjoying herself. She was just wearing jeans and a black button up blouse but it was open enough for me to sneak a peak at her breasts and the white lace bra holding them in. She would put a little cleavage on display at the hardware store, which I am sure was good for business, but always maintained a business presence.

"Can you watch my purse for a minute? I need to run to the ladies room."

"Sure," I said. She hopped off the stool and headed out to the restrooms. I enjoyed the site of her ass in the tight jeans walking away from me. Womanly curves, I thought to myself. I wondered if she liked to be spanked.....

I focused on my food and the ball game on TV when I felt a hand on my shoulder and a breast on my arm. Tracy was back and using me to steady herself as she got back into her chair. Seems the space between the chairs had tightened up over the last half hour as more of the dinner crowd arrived. She smiled and briefly faced me before turning back to her food at the bar. I could have sworn that two more buttons on her blouse were now undone, giving me a much better view of her breasts. Or was it wishful thinking?

"Did you miss me? Did I miss anything exciting in the game?" she asked as she looked and grinned at me.

"Yes and no," I replied.

I made it a point to check out her blouse again, hoping I wasn't being obvious. She knew I was looking but just grinned and let me. I was visualizing how hot she would look in just a black lace bra and boy shorts against her white skin. It was enough to get half hard at just the thought.

Grinning, she put her hand on my thigh and whispered in my ear, "Your food is getting cold." But she did not remove her hand.

After about 10 seconds, she turned back and looked at me and then down at her hand and asked, "Is that OK?"

I put my hand on hers and moved it almost to my crotch and whispered in her ear, "I'll shoot you if you move it.," to which she lightly chuckled. I don't know why but it was almost electric to just be flirting with a woman who was enjoying it as much as me. Flirting is almost a lost art.

Just as we finished eating, Tracy looked at her watch and said we needed to go to one of her favorite bars down the street for one more drink as it was happy hour there. I quickly agreed and we settled our tab and headed out. It was so busy now, Julie did not even notice I was leaving with someone. Good thing, I don't need to be the subject of any gossip at this point in my life.

Ever the gentleman, I told her I would walk her to her car and then follow her to the next bar in mine. Once at her car she opened the door, through her purse in the driver's seat, then turned to me, and put her arms around my neck.

"So what's the deal?" she asked. "I was doing my best to flirt with you in there and you barely tried to touch me. You don't think I'm attractive?"

"Actually just the opposite, I think you are very attractive but I am a bit older than you." I put my arms around her waist and held her but kept my hands at belt level, still not sure how far this was going.

"Yes you are," she said. "But it doesn't bother me if it doesn't bother you. We're just two friends having a nice evening. Does that work for you?"

"Works for me," I said.

Tracy pulled me closer so she could whisper in my ear. "Ok then, relax and follow me to my place." She then gave me several light kisses along my ear and down my neck and moved her hips against my crotch. It would be impossible for her not to know she had my cock hard by now.

Just to make sure we were both on the same page, I put one hand on each of her butt checks and pulled her in to me. We ground our hips lightly together.

"Hmmmm, that's much better but we need to get out of this parking lot," she said. Pulling away from my grasp, she got in her car. "I want a little privacy tonight. Follow me."

As we arrived at her place, I parked on the street and followed her through the garage door into the kitchen of her house.

"I need to go to the ladies room real quick. The booze is in that cabinet by the refrigerator. Can you make me a rum and coke and whatever you want and I'll be right back." With that she gave me a peck on the lips, a quick smile and headed down the hallway.

Tracy returned just as I finished mixing the drinks. Now her blouse was being held closed by just the bottom two buttons and she was barefoot.

"Thanks. Which one is mine?"

I pointed to the glass on the left. She looked straight at me while she took a sip.

"Hmm, not too strong. Still the gentleman huh?"

"Just trying to behave myself a bit. Don't want you to think I was trying to get you drunk and take advantage of you. I'm enjoying myself too much to have this evening end now."

Tracy set her glass down on the counter, put her arms around my neck, pulled me close, looked into my eyes and said, "And what will it take to get you beyond that gentleman phase?"

"Well it's been a while, if you get my drift, so I am just taking things slow," I said.

She kissed me lightly on the lips a couple of times, and then gently stuck her tongue in my mouth. As we French kissed, I put my hands on her ass again and we ground our hips together. She pulled away and whispered in my ear again.

"We're not in the parking lot anymore so you can do a lot more if you want to," she said and then starting kissing me again.

"I definitely want to," I whispered.

With that, I moved my right hand off her ass cheek and up to her left breast. I hadn't noticed but she had removed her bra when she went to the restroom. I slipped my hand under her blouse so I could cup her breast and gently massage her nipple.

"The other one too," she whispered. So I moved my left hand off her ass and up to her right breast and began massaging it too.

"Oh god," she said in between kisses.

"Uh huh......geez you smell so good! Were you wearing that perfume at dinner? It is so nice....."

"I just freshened up," she said. "It's Jimmy Choo. Do you really like it?"

"I love it!" I told her. "It makes me want to nibble on your neck and ears."

"Well don't do that," she said. "No marks please. But I will tell you I splashed a little on a few other parts of my body too, but you will need to find out for yourself where those places are."

She was really starting to tease me now and we were both enjoying it.

After another minute of this, she pulled away.

"Hmmm. Let's grab our drinks and go sit on the couch for a minute and talk."

We each grabbed our drinks and she grabbed my hand and led me to the couch. I sat a one end of the couch and she settled in right next to me, her left arm around my neck and her right hand holding her drink.

We each sipped on our drinks for a few minutes and she busied herself with her left hand running her fingers through my hair. Then she spoke.

"Since you said it had been a while, I thought we should take a short break and make sure you were doing OK," she said.

"I'm doing fine. I'm still just a little surprised you are interested in me."

"Still hung up on the age thing, huh? Well I'm not, so no more talk about that OK?"

"Works for me," I said. I took my right hand and started running it up and down her left thigh, all the way to her crotch and back. Tracy just looked at me and smiled.

"By the way," I said, "I want you to know how much I am enjoying being here with you. You are a very special person and not just because you are half naked right now."

"Well, complement accepted and I am very much enjoying your company too."

I set my drink down on the end table, moved my hands higher the next time and proceeded to undo the last two remaining buttons on her blouse. I gently opened it up and proceed to gently massage her breasts again.

Her breasts were small but all natural, soft to the touch and crowned with pencil eraser shaped nipples, just meant for sucking. Periodically I would tweak each nipple by gently rubbing each one between my thumb and index finger.

Tracy just closed her eyes for a moment to enjoy the sensations on her breasts and nipples. She took another sip of her rum and coke, set the glass down and came in for another wet French kiss.

She backed away from me but kept her gaze on my eyes. She put her right hand on my right thigh, gently squeezed it, then moved it slowly up until it was in my crotch. When she found my stiff cock, she grinned and started to gently massage it.

"Very nice." Every man likes to be complemented on his cock, especially when most of us are just average in size. She won a lot of points with those two little words.

"So," she said, "since we are both adults here, how about we just share with each other what we like to do in the bedroom and then head in there for more fun?"

"I like that idea. Ladies first," I said.

Tracy giggled. "Somehow I knew you would say that. OK here goes. I'll share some and then you have to share some. But you have to quit playing with my boobs for a few minutes because you are really distracting me"

"Perfect," I said. "But you'll have to quit playing with my cock, too, unless you want a big fat wet spot in there."

"Deal," she said as she moved her hand back to my thigh and I pulled my hands back from her breasts, putting one of them on top of hers on my thigh.

Tracy then moved in close to my right ear and I knew she was going to start whispering to me again. Instead, she gave my ear several wet licks and kisses first, then began sharing her desires.

"I like my nipples sucked, gently at first, then a little harder but no teeth," she said. "I prefer to give head rather than receive it but we can 69 if you like. Now it's your turn."

"I like 69 too. I like to have my cock sucked...."

"Big surprise there!" she chuckled.

"And I like my partner to swallow my cum but you don't have to if you don't want to. I also like to have my balls licked and ass played with."

"I like my ass played with too, but don't plan on sticking anything up there besides the occasional finger," she said. "My favorite position is doggy style and you can spank me lightly if you want to."

"Hmmm, I like doggy style, too. But I do enjoy a finger put in my ass once in a while so, if you are willing, I would enjoy that," I said. "Where do you like your partner to cum?"

Tracy gave me a soft kiss and then said, "Baby, you can cum wherever you want tonight. What's your favorite? You want to cum in my pussy or my mouth?"

"Oh my......"

"Somebody likes dirty talk don't they?" she said. I just grinned back at her. "Well so do I so I think we'll do more of that tonight, too."

She sat up a bit, grabbed her blouse and opened it wide up, showing off both breasts and her hard nipples. She gentle massaged each nipple with her index fingers.

Grinning at me she said, "Or maybe you would like to shoot your cum on my tits?"

With that move, I grabbed her and pulled her down on top of me. After a very sloppy kiss, I said, "Let's head into the bedroom so I can get you naked and we can fuck."

"Best idea I've heard all night," she said.

Tracy stood up and grabbed her drink so she could take one more sip.

"Wait," I said. "First we need to get you out of these. I want you in just your panties right now."

With that I turned Tracy to face me, undid her belt and unzipped her pants. I was so glad she wasn't wearing skinny jeans; I did not need that challenge tonight. I ran my hands around to her ass cheeks and found them largely bare. As I moved her jeans off her hips her g-string came into view. As I continued to move the jeans down her legs, I placed my face in her crotch so I could smell her pussy.

Putting my left hand back on her ass, I moved my right hand up to her pussy so I could massage it. She was both hot and getting wetter.

"Hmmm.....baby......oooh..." she said.

I could sense her knees were starting to bend with this attention.

"Baby, stop.....I need to get out of these pants or I'll fall over...C'mon taken them off and lets go to the bedroom. You can play more with my pussy there."

I looked up her and she was smiling back at me. She knew the dirty talk was making my cock harder.

I finished removing her feet from the jeans we just left them on the floor. Tracy looked at me, gave me a slow French kiss and started to massage my cock through my jeans with both hands.

"I can't wait to get my mouth on that and suck it," she said.

"Walk in front of me," I said. "I want to watch that gorgeous ass in just your panties walking in front of me."

Tracy grinned, turned and starting walking to the bedroom with me right behind her. Her ass was firm but had the nicest wiggle to it as she walked. It was naturally firm, not workout firm. Youth does have its advantages.

As she walked across the bedroom to close the drapes, she took off her blouse dropping it on the floor and said to me, "Strip down to you underwear, baby but stop there. I want to take those off myself."

I quickly removed my shirt, pants and shoes, leaving me in just my briefs.

Tracy lit a couple of candles in the room and then turned to look at me, and then my hard cock in my briefs. She moved to the side of the bed and sat, motioning me over in between her spread legs. She slid both of her hands around to my back, into the waist band of my briefs, and pulled them below my ass cheeks but not moving her hands from my ass cheeks.

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