Doggy Style
'Put it in all the way. Do it now!' She whispered in my ear.
I was totally surprised, it just didn't make sense.
'But ... but ... I ...'
'Just do it. All the way in ... all the way in ... now!'
I placed my hands on her firm cheeks and thrust forward not knowing why I was complying.
'Yes, oh God yes.' She whispered.
***
I love taking my dog on a walk around this wonderful area. We had just started a daily regimen of walking. Tippy liked it. Lots of trees to sniff, two park areas to add to the bountiful sniffing areas. We were always armed with plastic bags.
This way cool neighborhood was an amalgamation of million dollar condominiums and upscale retail stores anchored by names like Apple, Tommy John, Starbucks, Nike, Barnes and Noble, Victoria Secrets and even a Tesla store. Add in a variety of restaurants with menus of high end steakhouses, fish, tex-mex, burgers, smoothies, and a good old Cheesecake Factory. A big hotel had a lot of business due to the relative proximity to the airport.
At the center of the town, there stood the building that reminded one of a small town courthouse. This all in one facility housed city administration and judicial courthouse. It was fronted by one of the park areas.
Every street in the area was nicely landscaped and maintained every day. If a leaf fell from a tree, it was blown into a pile by a worker, bagged up and removed.
When we divorced, I rescued Tippy from the city animal shelter. It was love at first sight. If I had any doubts about adopting a dog going into the shelter they dissolved when I saw her. So glad she liked me too.
We (Tippy and I) were creatures of habit for our morning walk. After a short drive from home, we always parked by the Starbucks to start the route. Our only abort was heavy rain. Other than that, we were clockwork. Very predictable.
I ordered ahead for my favorite -- Grande Pike. Starbucks by policy doesn't allow dogs in their 'food' establishment. I cheated a little on that, walking in with Tippy (a rare canine mute) to grab my pre-order stacked next to a dozen others. My eyesight had gone downhill, one reason for my forced retirement. I had to look at most of the tiny, printed labels. Luck of the draw, it was usually the last cup. Others with better sight behind me were usually and justifiably impatient. Sorry!
Of on the walk, we varied the route a little depending on our needed stop time.
One day, we headed down the main street. Typically, the only people we encountered were businesspeople coming from the hotel heading to Starbucks.
Today, on the opposite side of the street about a block away, I spotted a dog walker. Couldn't tell much about either the walker or the dog. I kept walking. At first, I guessed female walker. Closer ... closer ... closer -- yes female with a labradoodle -- so cute -- both of them. As we closed the distance between us, I just kept my eyes forward watching Tippy sniff another tree.
'Hi!' She enthusiastically called out to me from across the street.
'Hi' I meekly responded and weakly waved.
'Have a good day!' She was so energetic.
'Thanks.' I said almost inaudibly.
I don't know why I gave such perfunctory responses. I turned to watch her walk away. She was wearing tight, white jeans that fit her body like a glove. I could see the separation of her cheeks, the jeans were that tight. Her top was sleeveless. Her hair in a blond ponytail poking out from the back of her baseball cap. I love that look.
She swayed confidently as she walked away. She effused sexiness even in that ordinary outfit. What an idiot I am! Being single at the moment I was looking for friendship and more. You never know when it will present. If I run into to her again, I need to have a plan for that encounter.
***
We headed back to the house. I couldn't stop thinking about her. A wave and a good day and I can't stop thinking about her? I am really hard up, I guess. I need to get focused and get back to my writing. After semi-retiring and divorce I had to fill a gap. A gap created by living to work versus working to live. Now, I turned down contract work unless it fit my criteria -- minimal travel, no more than a year and a rate that was outrageous. Amazing how many companies met all that. I had a lot of bills to pay though.
I thought about finding out more about her, but I really didn't have nothing to go on. I needed more. I thought through a plan if I saw her again. I put those thoughts aside.
I focused and continued my writing. I had never written or published anything before except for business, but I was inspired to put my thoughts into words. I wrote for me hoping others would enjoy the pieces. I found out most do, but some don't.
My ex called.
'Tom, can you take the kids to school tomorrow?'
'Absolutely I can do that. Pick them up at 7?'
'Yes, that would be great. Please bring Tippy? They love her!'
'Of course. She loves them too.'
My ex had full custody of the kids. I was that bad. I just couldn't keep it in my pants. She is an attorney. She and her divorce attorney nailed me to a cross during the hearings. I didn't have a chance. She asked for full custody and built the case to get it. I swore my next wife would not be an attorney. Plan ahead.
Overtime she allowed me to have time with kids. Plus, I was now her go to when she had a conflict and needed to get one of the kids somewhere.
The timing of picking up and dropping off the kids would disrupt our daily walk schedule, but that's OK. I love my kids and would do anything for them. Plus, Tippy can't tell time. Uh -- maybe not totally true, she is my morning alarm clock. How do dogs tell time?
I was hoping I would see the woman in white jeans with a dog -- a working name. If she was a stickler for schedule like me, I would miss her today. Not the end of the world, I need to curb a growing obsession. I have been there before. Sad to say with my ex-wife's sister Grace that led to the divorce. They made up and are back to talking to each other Grace told me. We stay in touch. Her husband forgave her, not sure I could do something like that.
I dropped the kids off and headed to Starbucks. We were 20 minutes off schedule. Tippy and I did our Starbucks stop and started our walk hoping that today she was off schedule. No lady in white jeans. Oh well. Maybe she sticks to the same schedule.
***
The next day, Tippy and I were right on schedule. In the car, as we turned onto the street to head to Starbucks, I saw her down the block on the street we just turned off of. White jeans again with her dog. We scored a Starbuck's parking spot. I debated to wait or start the walk. I decided to start the walk but cross to the streetside she would probably walk. A gamble. I grabbed my Pike -- it was the first cup -- a good omen. I was so excited to execute my engagement plan. We walked toward her. She had crossed the street! Damn it.
She stopped.
'Hi! I can't believe we are meeting like this again!'
I was not prepped for this! Shit! Once again, another stupid response.
'Yes!' I tried to sound excited but failed.
'Have a great day!' She replied.
She started walking the last block to Starbucks. Should I do a 180 and follow her? No! Live to fight another day. Our schedule is her schedule, it just depended on path.
I had a closer view of her today. Her breasts bulged out from her sleeveless workout top. Man, I was even more turned on. I got to get some balls to engage. Maybe she was interested, maybe not, but I had to try.
***
Dawn broke, Tippy hadn't woke me up yet.
My thoughts drifted to the shapely cheeks in the white jeans and the breasts pushing out against the sleeveless workout top. Just a hint of the side of her workout bra visible in the sleeveless top. I moved my hand down between my legs, playing with my sleeping cock, massaging it as I thought about her. Caressing my ball sack, pulling on my shaft, playing with the sensitive spot on the head. With my other hand tweaking my nipples till the buds were hard. Soon I was a hard and upright. I stroked it while visualizing undoing her belt and then the top button. I pulled down her zipper and her jeans seeking the sight of her pussy.
I fantasized her begging me to pull off her panties so that she could mount me. I pulled them down for her. She moved in to position herself on top of me.
I picked up the stroking pace.
She guided my cock into her pussy.
Faster stroking.
I imagined penetrating her soft, wet pussy pushing aside the outer lips, moving in deeper.
Harder stroking. Harder, harder, harder ... I was going to cum.
She was begging for more, go deeper, go harder, Give it to me now she said.
Tippy started barking at me. She jumped up on the bed. She started licking my face.
'OK baby, time to get up.'
She jumped off the bed. I laid there for a moment admiring the tent I made. I could see a wet spot on the sheet. I have got to connect with her.
We followed our normal route that morning, but no sight of her. Sigh, I was ready to make a pitch.
Three more days, no white jeans and dog. Maybe she was not a regular. Oh well, it was fun while it lasted. I could still fantasize about her.
***
I had to put her out of mind. I let Tippy lead the way on today's walk. We were heading back to the car, turned the corner and there she was. I was stunned, not just the surprise of seeing her, but seeing her in a different outfit. The top was a v cut putting on display her bountiful breasts. Short, shorts barely covering the rounded, firm cheeks. She was looking down at her dog sniffing a tree and didn't see me. Time to be charming,
'Hi!' I said in my mostly fake, exuberant voice.
She looked up from her dog, 'Well hello to you. Didn't I see you a week ago across the street?'
I can't believe she remembered.
'Yes, that was me.' I froze. I couldn't think of my next line.
'What is your dogs name?'
Brilliant! Why didn't I think of asking that?
'Tippy. She is my best friend, my alarm clock and work out buddy.'
That, sounded so, so lame, I am hopeless. I will be stuck with my right hand as my partner forever.
'So is Lizzy for me!'
Thank God! Something in common.
She suggested, 'Could Tippy have a playdate with Lizzy? Maybe tomorrow afternoon? She could come to my place. You could come too. If that works for you and Tippy.'