This was my only experience with a significantly older woman. Unless a few rounds with a thirty-six year old when I was twenty-nine counts.
Her name was Charlotte and she was about 45 at the time. It was the summer between my second and third years of university, I turned twenty that August. It started the 4th of July weekend of 1993. She was a neighbor and friend of my mother. She was the very well cared for ex-wife of a CNN corespondent and originally from South Africa. She was a tall, skinny, fit and intelligent but plain brunette. She was also completely neurotic and adrift. Lydia from Breaking Bad reminds me of her. At the time she pounced on me her life was a train wreck. She was recently divorced, her runaway daughter had just been thrown in prison and she had just been denied a visa to live in the UK.
I kept feeling bad about the whole thing, like I was taking advantage of her. I had to keep reminding myself that this had never crossed my mind and she came to me. I was also terrified that my mother would find out or a busybody would say something after seeing me come and go from the divorced woman's house. But at the end of the day nobody knew anything and she gave the most sensual and paralyzing head. The girls my own age I had been with up to that point were just robotic, sucking till something came out and being done with it.
I had just showered and she was sitting on my bed. She was topless and had come over while my parents were away for a day trip under the auspices of using our darkroom. I just stared awkwardly. Partially freaked out, partially worried my parents would find out, partially mesmerized by her firm little breasts and slightly concerned she was just fucking crazy.
She walked me back to the bed, tossed a pillow on the floor, kneeled in front of me and pulled my shorts down. Holding my dick as I was getting hard she told me emphasizing her sharp accent that if I held her head down she would leave, I could cum in her mouth but nowhere else and if I got any in her hair she would never do this again. She then set to work slowly putting it in her mouth and sucking hard as she pulled it out as slowly as possible while her tongue shot around like a pinball. She did that for about two minutes before stopping to let me collect myself. She starts again at a higher tempo before settling into a head bobbing, tongue flicking rhythm, stopping several times to stop me from losing it immediately. Eventually I was sweating, trembling and gasping. She kept eye contact as she finished the job. When I couldn't possibly hold back another second she squeezed the base of my dick really hard and sucked my head as hard as possible. When she released her thumb the sensation of suction as I shot the load she had held back just floored me. She swallowed and went right back to the long slow sucks she started with but I was done. I just collapsed into bed gasping. She stood over me as she put her bra and blouse back on. She only said she wanted to see me again and I knew where to find her.
Three days later I worked up the courage to approach her in her yard as she was gardening, she smiled and asked me if I had recovered. She then led me to the backyard, I was expecting another blowjob but instead she took off her gloves and touched my lips with two of her fingers and made a circling motion for a number of seconds as she stared intensely. This was more than a little creepy. She then rubbed the back of my hand under her skirt. I felt nothing but her moist labia, no hair, no stubble. She then ran her hand over my two or three days of beard, told me to shave and come back in an hour. After an abridged version of the previous blowjob I was facedown in her pussy in her bedroom, there was no warming her up, after giving head she was always fully aroused. I had done it before but her pussy was magnificent. The other girls had all shaved, but had stubble and pimples for their effort. She had electrolysis and I was in heaven. Her clitoris was a little larger than usual and protruded from the hood, when I saw it all I thought was "cheat code activated". I took the the top of her pussy in my mouth and sucked while I flicked her clit with my tongue. I had trouble keeping this going because she wouldn't stay still enough. She started just running her fingers through my hair but soon she was holding my head down as she tried to keep me on the spot as she spasmed. I found this more than a little ironic, but I didn't go anywhere.
In a way she ruined blowjobs for me as a young man, I was almost thirty before I was with another woman who even came close and I have never been with another woman who just plain loved oral sex way she did. She also made me appreciate small firm breasts as a good long-term investment. And she was the first woman I had sex without a condom with (tubes tied), the sensation was nice but she just flopped on her back. Roll her over and she would just sort of rock back and forth. I couldn't comprehend how a woman who gave such an aggressive blowjob and would fuck your face while you were eating her out could be so passive for intercourse. I thought she would fuck me senseless. She told me that coming of age in a small town in South Africa in the early 60's birth control and condoms just weren't available to anyone, ever, but she always had a very high sex drive so she adapted. When she got to the UK for university she didn't just see didn't see what the appeal was for a man or woman over receiving oral sex unless you were trying for a baby. She said most of the British men she was with in that time were if not experienced at least willing and before her husband left her for his younger assistant had been perfectly willing to defer to her oral inclinations for twenty years.
Come the end of the summer we had hooked up dozen times and twice more at Christmas. When I came home the following summer, balls blue as a smurf my mother mentioned in the car driving me home from the airport that she was so relieved to see Charlotte in a relationship again after two years. That was a long dry summer. I had a brief romance with a former girlfriend from high school but I could barely stay hard when she gave me head. My last time with Charlotte was the following thanksgiving, she went home to South Africa for Christmas and come Spring I was graduating and moving to the east coast for a job. She is around 65 now, never remarried and still lives in the same house in San Diego and from the pictures on my mothers Facebook other than going gray she looks the same and she is still thin and firm. I would go for it in a second if the opportunity presented itself.
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