A few years back, someone finally bought the house across the street that had been empty after a divorce case. I was anxious to see who might move in.
The day the woman moved in looked, From across the street, llooked like she was in her mid 20's, slim, blonde, short hair (which I like) and very sexy.
A few weeks later I met her. Actually, I wasn't sure it was her because she was somewhere between 50 and 60, not mid-20's, but the body and hair where the same. I thought that maybe she was the mother of the woman who had moved in. As it turned out, she was a real estate agent, and they usually wear lots of make-up.
Her name was Jackie. She worked hard. She had to. At heart, she was really too nice to be a Real Estate Agent. I could tell Jackie had lots of nervous sexual energy. She had two adult sons, but no husband, or man (or woman).
Once, I told her the foibles of my marriage, and she remarked how she was glad that she didn't have a boyfriend, as it was too much work. I thought, she really needs to release some of that sexual energy. She never even takes a vacation. If she did, she could get secretly fucked by some black stud with a big cock at some vacation spot, and get some release.
I got to know her even better I found her increasingly attractive. She had a cute way about her, was very sweet, and had a great ass. She was very old-fashioned in attitude, or at least pretended to be. I knew that it would be very hard for her to admit that she had needs, and much much harder for her to let go of her perceived morals and do what should come naturally to an uninhibited human. I made it my goal over the next few years to stuff my cock into all 3 of her holes. Little did I expect what happened.
I started my quest subtly. One Day she asked about a gardening book with the word complete in it. I found a Complete Guide to Sex book, and gave it to her, saying gardening does involve a lot of sex. She took it.
Whenever I was home, off-work, I would make an excuse to see her. I asked how she enjoyed the book. She said that it didn't have much to do with gardening.
One evening, when my family was out, I managed to find her working in her yard. She had obviously had a few glasses of wine (which seemed to be her only outlet). I helped her move some heavy bags of mulch to the back of her yard. After, I was hot and bothered, and sweaty, and accepted her offer of a beer, on the condition that she join me with another glass of wine.
As we sat in the backyard I turned the subject to the book, and her lack of a man. She did admit that she liked sex, and was getting bored with masturbating. She told me she masturbated each morning and night. After some prompting She admitted that she had at least 10 orgasms in the morning, so that she could start her day, and 15 at night so that she could sleep. Wow, I thought, my type of woman. I told her that when I was 21 my record was 11 orgasms in 24 hours (that made my girlfriend at the time sore, but, after a while she said that it got used to it) with the usual being 4-5. Today, at 45, it is maybe 3 or 4 on a good day, but mostly 1-2 times. I sat there imagining tasting that cute ass, and with all the juices running down from her dripping wet labia. I nearly came in my pants right there
I told her that I found her irresistibly cute (I have always liked older women) and I would be happy to be her "special friend". She was horrified, as I expected she would be. Calmly I suggested that it would help us both. My wife likes sex every 12 weeks, if she isn't sick/tired or stressed. I love her and our kids, but have no intention of leaving them, but I really need more sex. With me Jackie could get some of the advantages of a man, without the issues of a relationship.
Anyway I said that she should consider my offer. I suggested that we could follow the Bill Clinton definition of sex, no vaginal intercourse, to keep the guilt quotient down.
A couple of weeks later I met Jackie on the street. She Said, "Well there is one thing that I would like to try. I read in your book about rimming. It sounds very pleasurable. Would do that for me?" Yippee, the activity I most want to do with her.
"I would be happy to do that for you," I said trying hard to hide my glee and erection.
Jackie told me she noticed how hard my cock got when I suggested being a "special friend". "I didn't think that at my age any man would be turned on by me." She confessed. I found out that she was 59.
We arranged to meet at her house on night of soccer practice. Her ass was every bit as delicious as I expected. I spent over an hour trying to get my tongue ever deeper into her brown eye. It went further and further in as she relaxed. She started rubbing her clit and the juices flowed to my mouth. Yummy. After a while I started caressing her dripping wet labia lips, then as she moaned more and more she took her hand off her clit and I took over. Before long I was slurping up her juices and flicking her clit with tongue.
Did she ever need this release; she must have come 25 or 30 times. Afterward she looked so much more relaxed. I cuddled up to her and caressed her beautiful face.
She looked at me and said, "yes you can be my special friend, but we must stick to the Clinton definition of sex." Fine by me. It was a start. I could score two of her three apertures by that definition.
I had to have a shower. There was no way it could go home reeking of her female juices to my wife. I wanted her to join me, but she looked afraid. "Is it because you are afraid that your make-up will wash off and I won't want to be you special friend anymore?" I asked? She nodded. "Don't worry; the person behind that make-up is so beautiful, that I will want you even more, I promise."
We stepped into the shower together. Of course one thing lead to another and we stared lathering each other. I massaged her head to ass. She started to get hot again, we kissed and she started rubbing my dick. Her bony hands were perfect little dick massagers. I came in no time. Soon the hot water ran out, and we toweled each other off slowly sensually, and lovingly, being fully relaxed.
She looked at me and said, you are the first person to see me without make-up for over 20 years. I smiled and kissed her soft mouth gently.
"Don't my saggy tits bother you?" She asked me.
"No, I love saggy tits, small saggy ones the best. I could worship yours all day."
"Next time," she cooed.
We continued to meet (she needed lots of help with snow blower, and her lawnmower). She became more and more relaxed and we got more and more adventurous. After enjoying more rimming she asked me about anal sex (heaven I thought). I told her how many people enjoyed it, but it had to be done slowly, and right. Starting with rimming was good.
So she had after glasses of wine and I started. Rimming, then lubing, then one finger, then two. At this point she started bucking. "I think that I am one of those people who would like anal sex," she said. I started to ease my slender 7.5 incher into her beautiful brown eye. She jerked at first, but then the rubbing sensations took over, and she was really moaning. We started doggie style, and then went on to other positions as her ass loosened up. Finally we got so that she was riding my cock, rocking back and forth on it as she sat on me while I was lying down. She told me that she had had at least three orgasms without even touching herself while I was pounding her ass. Then, she said I am going get you off with my ass. And she worked my cock with her ass until I had no choice but to explode. I spewed a huge wad into her spacing ass, probably the biggest of my life, and then she smiled the cutest little smile. It was made even more beautiful because now, when we got together, she always took off her make-up.
Your balls are kind of in the way. I explained to her about cock and ball straps, and she got excited. She was too embaressed to go buy one herself so she gave me some money. There was enough left over for me to buy her some real classy silk stockings, I detest the feel of nylons, and a garter belt. I also got her some vibrators as a special present. Including a vibrating egg where the battery was inside, so there no wires, and a labia clip to keep her lips closed so she could hold the egg inside while walking about.
As we lay together after a particularly hot session she asked me if I liked eating her, or if I just did it to please her. I would do all day if I could I told her.
Later that week, while wearing the egg, she showed a man a house, that he didn't seem very interested in. On a whim she dropped to her knees and gave him a blowjob. He bought the house, full price. Men are easy to please she agreed. I could foresee her sales rate going up. I popped a boner, and asked if she had any houses that could go to fuck in right now.
Jackie stared at me; "you really are Horny all the time, aren't you." I nodded.
"There is a boy in my office who does the gopher work who confided in me that he is a virgin.He confided in me because he thought that I was sexless old biddy. He is skinny, about 19, and I have seen the huge bulge in his pants. He looks quite pent-up, like I used to feel before I met you. Maybe we should invite him over." giggled Jackie.
We all got together soon after. We sat and discussed how nervous he was. He asked if could smoke a joint to calm his nerves.
Great for me, I thought, THC makes me even hornier. "OK," I agreed "but Jackie has to try some too."
.... There is more of this story ...