My Cougar - Finally!

(Names and occasionally some details have been changed in this story.)

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I knew it all along that I had an attraction to older women. First it was my ninth grade world history teacher, Mrs. Patterson, whose usual attire included a striped blouse that barely contained her D cup breasts, and who would tell us the lurid sexual secrets of Europe's most famous despots. She had fire engine red lip gloss and wore tons of makeup to conceal her age, but I believe she was about fifty at the time. I am sure she noticed my eyes playing over her chest during every class, and raised my final grade out of compassion for yet another victim of teenage hormones (and problems with attention span). Then it was my calculus teacher, Miss Rose Dewitt, a true blonde with a classic hourglass figure who was just approaching thirty.

Of course my favorite was a teacher who didn't even teach a single class I was in - Miss Dupree. Rumors tended to circle about her possible lesbianism, although in the same breath the students would say that several guys in her class had been treated to some personal extracurricular activities. Of all the teachers at my school she was hit on the most, and she seemed to quietly embrace her reputation. After high school I met her in a store and struck up a conversation that turned a little flirty. Unfortunately, when I mentioned the job I had taken over the summer, she became confused by my pronunciation of the word "cement" - and my attempt to clarify myself, by saying, "you know, like a sack of cement?" only made her think I was being perverted. Either she came from another part of the country, or perhaps, she just had a really dirty mind!

College brought a torrent of young ladies wearing skimpy summer outfits, but I still remember being attracted to a couple of my professors, and even to an ex-girlfriend's mom - who I thought was even more attractive than her offspring. The girl I dated after her, though, was like a dream come true for me. She was a Japanese national and naughty as a 21 year old virgin could ever be. We told each other all of our fantasies. One that I told her about was of a woman who was older or who had some authority, like a teacher. So she got a nice outfit and pretended to be my ninth grade history teacher, occasionally undressing when I answered a question right and smacking me with a ruler when I didn't. She really seemed to enjoy that part. As tiny as she was she was quite dominant.

Losing my virginity with her the same night, however, was not enjoyable. Not only did it hurt her a lot, but she felt so insecure that after a couple of minutes she told me to stop - and I did, immediately, but not without asking her what went wrong. She turned away and wouldn't look at me or even talk to me. I felt horrible, and even now, knowing that it wasn't my fault (she was worried I was imagining she was one of my exes) it still bothers me to think about that night. To this day, I have not dated another virgin.

When I looked for jobs after graduating, I discovered the reason why people always ask liberal arts majors what they plan to do with their lives. It took me a full three months to find a job in customer service. I was placed in an office with three older women, but the one I was attracted to the most was Liz, a 44 year old grandmother of three. I knew - thought - nothing would ever happen between her and myself because her chain smoking was a major turn off to me, but that did not stop me from crushing on her. Over time that became more apparent and we would occasionally cross lines.

Liz admitted to me that she had dated younger men, for one. I would walk over to her side of the office and gently massage her temples and neck while brushing my hand over her shoulder length blond hair. Sometimes I would make it a point to think sexy thoughts right before I came into the office from some errand - to get myself semi-hard in front of her so she could play her eyes over my bulge. I stared at her juicy red lips, imagining what it would be like to french kiss her. She would tease me with playful banter and tested my knowledge of French by asking me to sleep with her. Of course, I said yes. I was always thinking of the next clever way to get her to bend over and reveal her lower back tattoo. I'm sure she did so quite willingly.

When the management hired a new employee, a girl a year younger than me called Ashleigh, my flirting with Liz suddenly became the topic of office gossip. Suddenly two other older women seemed fixated on me - and Pam, in her mid-50s, even gave me her telephone number. Ashleigh was exceedingly jealous of the fact that I had so many admirers, even though she claimed that she wasn't interested in me. The sexual tension was palpable, and the only way I could safely get it off my chest in words was during my daily lunches with the technicians, who were all men, and who seemed quite understanding of my predicament. After a few months of this, the economy tanked, and I was let go. Liz suggested we should go get coffee together, but I turned her down, because at the time I was living with my parents, who would not approve.

When I finally moved out, I had freedom for the first time. Within three days of the beginning of my first semester at my new college, I had a 19-year-old girl from India naked in my bed. She had a perfect swimmer's body with nice, firm C-cup breasts and even sported some feminine abs. Her pussy was too irresistible not to lick (for hours at a time), but I noticed after several weeks that I was pleasing her with nothing in return. Disappointed, I broke things off with her. My sexual frustration had reached new heights, and was only cured when a nice married women and I began a series of chats leading up to a friends with benefits relationship. She was my age; her dilemma was that her husband was sexually attracted only to men. She too had been dealing with frustration.

When I showed her my cock she responded immediately that she wanted to suck it and told me it was one of the largest she had ever seen. She confirmed this when she settled herself over me and guided me into her smooth pussy. After a few ups and downs she threw her hips into a quick, rhythmic rocking motion that seemed impossible given her size. She was a big girl but she could really move her body! My first enjoyable intercourse was more or less the result of a forced, but exceedingly powerful orgasm. When she finally found a permanent boyfriend, I was left wishing I had snagged her while I had the chance.

After screwing two other women who had very little self respect, I found an old ex. She turned out to be obsessed with me still, and within two weeks she took to wearing a ring that she called our engagement ring. I admit I loved being in her tight pussy, and she was very sweet to me when I was in love with her, but when she attempted to trap me into a quick marriage, I broke things off with her. She and the next girl I was with had the strange belief that if they didn't get married and have children by the age of 30 they would promptly develop wrinkles and age spots - that, or turn into a pumpkin.

It was about a year ago that I finally got it into my mind that I wanted to date an older woman, if nothing else, just to see what it was like. The women who responded to me on the dating website was a lovely brunette of 40 years who drove a white sports car and shared my interest in running. We had a very enjoyable date that included a nice meal and which I concluded with a kiss. I thought I had sealed the deal when I got with her for a second date, but during that date she brought up her age and the fact that she could no longer have children. I told her it didn't matter to me, but she was unconvinced. After that day, I never saw or heard from her again. All I have of her are photos and a faint memory of what she looked like.

It was only a month ago that I got a hit on another website, this one specifically geared toward pairings of older women with younger men. I found that Jane and I had a lot of the same interests, including women. Jane is a curvy brunette with light brown eyes that sparkle in just the right light and breasts that are still quite firm. She invited me to a burlesque show in her town, where we necked and groped each other in the middle of the establishment. That weekend she came over to my place for a movie. I greeted her outside with a big hug and a kiss. The movie I put on, of course, did not last long. She went from feeling my cock over my shorts to reaching in, to practically tugging me into my own bedroom.

I laid her down and got beside her. After snuggling a bit, our hands playing all over each others' bodies, my cock responded by standing at full attention. She smiled and I pulled out one of my extra large condoms, kept in a convenient box on my night stand, fitted it gingerly over my thick erection and pulled the covers over both of us. I felt in heaven as soon as I got into her, her hips grinding eagerly against mine, moving me in and out of her. I felt myself building toward an orgasm, but I waited for her to come before I unleashed myself. After I was done, I pulled off the condom and tossed it to the floor.

"I've always used condoms," I told her. "I don't trust young women who just say they're on the pill." Having been with two women whose only ambition was to get married and pregnant before turning 30, you can probably understand why. Jane responded, saying that she couldn't have children anymore and that she was totally clean (having been tested recently), so really, there was no need. I told her I was nervous - I would feel naked without a condom. She laughed and told me the feeling would be incredible. I told her I needed to think about it first. I got her off a dozen times more that night before she finally had to leave. Her kids would be waiting for her in the morning, after all.

A week later she visited me again. I was ready, and swept her into the bedroom. I took full advantage of her submissiveness, much to her delight. I pulled out a pair of cuffs I had bought online and latched her to the bed while I went to work pleasing her. As soon as she was wet enough, I guided my unsheathed cock into her soft, wet pussy. A warm sensation rushed over me in my most sensitive places, coming and going as I began to thrust gently. I let her use her fingers to play with her clit while I moved back and forth inside her, and within minutes she was cumming violently, gripping the bed rails for dear life. I continued ravaging her, taking her hand away from her clit and pushing her down on the bed. She opened her eyes at that point, those big beautiful brown eyes, and I knew I had made a real impression on her.

"This is just beginning," I told her, as I undid the cuffs and guided myself into a sideways position - her left leg lifted to allow access, my left leg extended underneath her left leg, my right leg bracing against her left to add momentum to my thrusts, my hands enjoying her curves and playing with her perky sensitive nipples. A minute later she was in ecstasy, her orgasms converging into a series of gasps and brief screams, her pussy alternatively tensing and relaxing around my hard young cock.

I smiled at her and she replied by flashing her pretty eyes at me - more, please. I lifted her legs high and knelt between her legs, thrusting up against her g-spot as she went into another momentous orgasm. "Had enough?" I asked. She still wanted more! (Of course. What girl wouldn't?) So I got beside her and entered her from behind, eventually rolling her body on top of mine so I could thrust from underneath. She turned her head and offered me the sweetest kisses I have ever known. She melted in my arms as I made love to her body with my hands. If she had any apprehension that I would not find her attractive, that dissolved at that point! I let her know that I desired her fully. And then, I flipped her over and again, entered her from behind. She buried her face into the pillow, occasionally matching my thrusts with her own thrusting back at me. I embraced her, my torso melting into her from behind, my hand fondling her ample breasts. Finally, she couldn't take it any more.

"I want your cum in me!" she demanded. I turned her over and took full control. Her legs split wide open and my hands gripped her arms as she looked helplessly into my deep blue eyes, searching, waiting for the moment to come. I knew she was holding back her best orgasm for last. I fucked her harder and harder, straining my abdominal muscles against her tummy, my motions now causing the bed to solidly contact the wall with every thrust. "Cum for me!" she pleaded, and dug her sharp fingernails into my butt, holding me into her. I pulled back, feeling my orgasm start to build momentum. Sweat dripping onto her from my drenched hair, panting desperately, I could do little more than hold my mouth wide open as the sensations began to envelop my body. Nothing came out, not a sound, until the first orgasmic pulse hit me like a ton of bricks. I felt my insides contract and a wave of ecstasy shot through my body. The second wave brought with it a rush of fluid that went into the deepest parts of her vagina. She was now moving into a powerful orgasm as well. I moaned in pleasurable agony as one shot after another of my hot seed went out of me into her grateful body. As mine began to lose its momentum, hers had its strongest pulse. Her legs shook violently, her contractions almost pushing me out of her body, but I held on for dear life. Fifteen seconds later, I settled on top of her, nearly comatose. Neither she nor I made a sound for the next few minutes. She gently rubbed my back as she bathed in the pleasure that had been ours for the last few minutes.

I was the first to say anything: "Wow."

I love my cougar!