I know Linda reads this site. I hope she gets off knowing people read her story. DT
I recently started dating a woman, Linda, I met by using the e-Harmony system. She is 12 years older than me, petite, and in very good shape for a lady of her age.
She was married for many years to a man she lost her virginity to when she was 18, married at 22 and had 2 kids with by the time she was 25. She left him after 20+ years when he became a born-again and devoted all his spare time to a church she did not believe in. He also had a small cock and pre-ejaculation issues.
After her divorce Linda had a one night stand with a stranger when a bit drunk. Other than her husband this was the only sexual experience she ever had before me. She was very sexually repressed; never masturbating when she was a teen. Linda only began to masturbate and explore her own sexuality until after she had been separated for some time.
Unlike her ex; I have a rather large penis and can keep it up for a long time. I masturbate almost every day, and have done so since I began many years ago. I keep a bottle of Astroglide in my bedside table and another in my shaving kit for when I travel for work. I have learned many techniques that work for me and often experiment with different ways to stimulate my penis. As I get older, it now takes longer to reach orgasm, now at least 20 minutes of consent stroking, sometimes more. I still enjoy the sensations, but often worry about loss of sensitivity due to masturbating every day.
My job requires travel and I spend over 100 nights a year in hotels. I make a point of coming in every hotel I stay in and like to write my initials in semen on the wall over the bed. (I am just being honest about what I do)
My first date with Linda was just dinner, drinks and a quick kiss in the parking lot. I was a bit embarrassed as when I went to kiss her I realized I had an erection and hoped she did not notice. The second date was a movie, but this time when I dropped her off at her apartment, I made a point of pressing my hard cock against her belly when we kissed goodnight. She later told me this got her very aroused and masturbated several times that night, thinking of my cock inside her. She called me the next evening to thank me for the date. As we spoke, I began to masturbate and brought myself to a powerful orgasm while we spoke.
We had our third date two weeks later. I had been away on a business trip for a week and wanted to make her wait to see me again. This time she invited me into her apartment for a cocktail before going to the movies again. As we sat on the sofa I could see her nipples sticking out through her sweater. Without saying a word I put down my drink, took her in my arms and ran my hand up between her legs, under her skirt. I could feel the warm moistness of her sex as I slipped my fingers inside her panties and into her vagina. With the tips of my fingers hooked into her vagina I gently and rhythmically pressed the palm of my hand against her clit. She spread her legs and just melted into my arms while I kissed her with an open mouth.
Her orgasm came on quickly. Linda arched her back and bucked her hips against me hand and as I felt her vagina clamp down on my fingers, I slid them into her as deep as I could, pressing hard against her G spot. With a high-pitched squeal that could have broken glass she squirted onto my hand, shoved me away, rolled slowly off the sofa and ended up on the floor, gasping for breath, pressing her hands tightly between her legs.
After a moment she managed to stand up and looking horrified, saw a large wet spot on the sofa. Clearly humiliated she thought she had pissed herself. I stood up from the sofa, gave her a big hug and she broke down into tears and cried for a while.
Later I took her into the bedroom and we talked for a long time about her life, mainly from a sexual perspective. This made me very horny and I wanted to make love to her in the worst possible way. Linda said she would not have sex without a condom and I did not have any with me. I said that was OK, but we could still fool around and masturbate together, touch each other without penetration.
We started kissing again and undressed each other. I had a huge erection by this time. Linda had never seen a penis that big before, but was somewhat reluctant to touch me. I did not know it at the time but, she had never really touched a penis before, never given her husband a hand-job, never watched a man masturbate.
At this point I needed to get off and could not wait any longer. I need to use a lube when I masturbate and after frantically looking through the bathroom medicine cabinet I found some baby oil. Normally, I don't use baby oil as it is too thin and does not give me the right friction, but this was an emergency. I lay on my back in the middle of the bed and lubed myself up and started to slowly stroke my cock while Linda watched. I got her to sit beside me with her legs open so I could see her vagina. It took me a long time to reach orgasm. I had to pull the skin tight with one hand while stimulating the head with very light pressure. It was an intense, almost painful climax as I shot semen high enough into the air some landed on Linda's leg, several feet away.
Afterwards I told her it was her turn. Although uncomfortable with me watching, Linda piled some pillows up and lay back with her legs raised. She slowly rubbed her clit up and down, but after a few minutes stopped, saying she could not concentrate.
Pushing the pillows aside I buried my face between her legs and ate her out until she came. (Another first for her)
Linda and I are now having regular intercourse at least twice a week, but we like to start with a mutual masturbation session, often flipping a coin to see who does who. I have learned that I can get her to squirt by rubbing her G spot. She will lie on her back blindfolded, legs spread, her hips and knees raised on pillows. I then kneel in front of her and with a well lubed hand get two or three fingers inside her and rub on the upper, front side of her vagina while putting pressure on her clit with my other hand if I am not jerking-off at the same time. Our game is that she can't move. If she does then I stop whatever it was I am doing, count to 10 then begin again. I do not bring myself to orgasm very often, but if I do, I will ejaculate onto Linda's vagina.