My One & Only Cougar... Part I

Before the term “cougar” became synonymous with Ashton Kutcher and Demi Moore, I was fortunate enough to experience my own experiences with an older woman. Not once, but many many times.

I re-wound the memory bank back twenty years ago to when I was a student at Richland College in Dallas. I was taking a government class at night, which mostly consisted of older students. I was in my early twenties but felt very young when compared to the men and women who were in their 30s and 40s. I had always had a fetish for older women, probably the first memory I had was baby-sitting a divorcee’s kids on New Year’s Eve when I was thirteen. After getting the kids to bed, I rummaged through her dresser looking for the treasure chest of gold – her panties. I mostly fondled all of her silk and cotton panties and marveled at them especially since she had a big ***. Being a thirteen year old pubescent boy with a hard-on that could shatter glass, I wound up jacking off and uncontrollably spewing my *** all over and into a pair of her panties within minutes. I digress.

The government instructor assigned a class project the first week of class. As a social retard, I loathed the thought of having to pair up with another class mate to work on a project; especially the project I was assigned – “Arguing the Pros and Cons of Abortion.” What the hell did I know about abortion? I didn’t even have a steady girlfriend and spent most of my time jacking off to HBO! Nonetheless, I met with my partner at the end of class. I didn’t have a clue how old she was; I thought maybe 40ish? We agreed to meet after class and discuss our projects. Man I thought, she’s kinda like my mom! We grabbed a bench outside of the classroom and introduced ourselves. Her name was Judy Phillips and she was taking night course and working towards a degree. She was a secretary at a telecommunications company in Richardson, TX.

It was January and cold for even Dallas weather. Judy wore a very long plaid skirt and a white turtle neck sweater. Her **** were very small but the curve of her cleavage was evident in the tightly fitted sweater. She had long black boots that disappeared into her skirt. Her hair was light brown that could have been mistaken for a 1960s Doris Day hairstyle with perfecting matching brown eyes. She oozed sweetness and was also a social retard, blushing on several occasions as I asked more about her. As we talked we became quite comfortable with each other. We parted campus on that cold January night agreeing to talk later in the week to decide how we would approach the government project. I hurried home thinking about her and wondering why I was feeling giddy about an older woman. I rushed through the back door, bolted past my parents who were sitting half a-sleep in their recliners, and headed for my bedroom in the back of the house. I quickly checked the HBO and Cinemax guide to see what ***** flicks were on as I ******** down to my underwear.

As I proceeded with my nightly ************ session with my cable TV, my thoughts weren’t on the blonde bombshells with big **** on the flickering screen, but were on this woman I just met and quite frankly was probably old enough to be my mom. Rather than stroke myself to an immediate ******, I held back and milked my **** slowly as I started to get close to an explosion. A combination of pre-*** and my creamy ***** would ooze out the tip of my **** as I would stop suddenly not wanting to shoot my load and waste an incredible feeling. All I could think about was lifting that plaid skirt up and spreading her thighs which surely would be wet awaiting my mouth. I knew then I wanted to eat Judy’s ***** which caused an enormous explosion of *** to shoot all over my chest, face, and hair.

We didn’t make the phone connection we had promised each other. This was pre-mobile phones so if you weren’t tethered to your “land-line,” then you played the answering machine game. In between the next class I was to see her, I jacked off every night, sometimes even in the morning. My **** was starting to become raw with all the strokes but it was a good sore feeling. We met over the next couple of weeks after class and started to formulate our project. I was to take the pro-abortion stance and she was the anti. I didn’t have a clue about abortion so I needed to brush up on some background. I wound up going to the Routh Street Woman’s Clinic in Dallas and met with some very vocal and somewhat feminist woman who were beyond passionate about abortions. To say I was intimidated by the woman at the clinic would be an understatement. Either way, I garnered loads of pamphlets, information, and notes with my interviews to take back to Judy to start presenting my arguments for the project.

Judy had also been conducting her research. As I later found out, she underwent an abortion when she was younger because her first husband didn’t want any more children. This gave her an extremely personal and somewhat passionate view on abortions; as well as an opportunity for her to open up more about herself. We decided that meeting after class at 10 p.m. to discuss our project wasn’t feasible. She asked if I would be interested in coming over to her house to work on the project. I calmly accepted and I was hopeful that she didn’t see the immediate rise in my pants at the incredible dirty thoughts that polluted my mind. We decided on Saturday morning.

The first Saturday meeting was the most memorable day with Judy. We laid out our project and actually we were pretty close to completing it even though we weren’t even half way into the semester. She made some sandwiches and we ate and continued to exchange conversation. She was somewhat flighty but very enjoyable. In fact, she was down-right babbly once she got going. I just sat on the couch and tuned out her words and started fantasizing once again about eating her *****. It was early afternoon and I thought I should be going when she asked me if I was interested in art. Honestly, I wasn’t interested in art but I figured what the hell and said yes. She pulled herself off the couch and went over to her bookcase thumbing through the many shelves of books. I watched lazily from the couch sizing up her *** in the faded pink sweat pants that hung off her hips. She then turned on a dime and said “I know where it is, hang on, I’ll be right back.” I couldn’t have been anymore puzzled.

She returned within the minute carrying a very large and oversized white book. She raved about the art in the book and basically gave me a world art history lesson against my will. The good part was she nuzzled up very close to me and laid the gargantuan book across both of our laps. Occasionally I would feign an interested look on the opposite page thus giving me an opportunity to lean into her shoulder. After several attempts of rubbing up against her, I bravely shot the moon. I put my arm around her waist to take a deeper lean across her, nudging any part of her body I could. She had a deep, scented soapy perfume lighting off of her body which instantly aroused me beyond control. If I didn’t know any better, my side of the book was no doubt tilting upwards! I decided to steal another base and cupped my hand on the right side of her hip slightly sliding my fingers under her thigh and ***. She was so busy providing me explanations of each picture and its historical perspective she either didn’t notice my cheap move, or, she wasn’t slighted by it.

The droning of art history dragged on. I didn’t have any more moves in my repertoire when she turned to a section on nude art. Now we’re talking. Looking at art from hundreds of years ago and the different periods of art history can be somewhat boring if that isn’t your forte. Whether out of purpose or just a genuine love for art, she continued turning the pages. On some pages, she said nothing. What is there to say about renaissance painting of a plump man with a small **** suckling an even plumper woman with a big *** and tiny ****? After a few dozen pages of nude art, I noticed her breathing had increased. She was less talkative as I nudged up against her with my false interest in art. I was flush and I’m sure my face was speckled with redness; not looking at the nude art, but being next to her body. She finally closed up the book and set it on the floor. I quickly leaned back away from her as if I had been caught stealing pie from the neighbor’s window sill but quickly returned to my position. I put my hand on her leg and started rubbing her legs down to her knees. I parted her legs with a little force and started rubbing the inside of her thighs. She just stared at me with those big brown eyes expressionless.

Earlier in the day, she told me she was married. It was her third marriage. Her husband lived in California and she lived in Texas. She tried living in California but didn’t like it. Her kids and grandkids were in the Dallas area and she wanted to be close to them. She was 51 years old and just hadn’t gotten around to divorcing her third husband. I continued to explore the inside of her thighs through her worn pink sweat pants. She was very warm to the touch even through the cotton. Her face was flush with pure heat and she was enjoying the physical yet innocent pleasures. My **** was throbbing so hard it was starting to hurt. I leaned into her and softly kissed her lips intending on pulling away. She opened her mouth and led me to her warm and wet tongue which caused my tongue to attack her mouth. I moved my hand closer to her ***** while trying to concentrate on the incredibly hot kiss I was now engaged in. I didn’t have to look down to know that I had a very large wet spot where my **** was gasping to get out.

As fast as our passionate touches started, they ended. She pulled away and revealed tear filled eyes. “I’m sorry” she said. “I think you need to leave.” Stunned, I stammered out several questions asking what I had done wrong. My questioning only caused the tears to increase. “I’m married” she said. “I can’t do this.” I apologized profusely, got up off the couch with my throbbing **** that was in plain sight and walked to the front door. She followed with a silent walk only with the occasional sniffle coming from behind me. She apologized again and let me out the door. I drove my blue balls home confused as to what had happened finishing off with what must have been a twenty second jack off session before blowing the load I had hoped to have dumped in her *****. She called me that night…


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26-30
May 24, 2012