Today, I met up with my first guy named John. Because I only spoke briefly with him and he told me he wasn’t into anything kinky, just wanted to be with a beautiful woman, I started to get paranoid two minutes before he arrived, wondering if he might be a cop. Then again, he pestered the hell out of me via email to arrange this, and I doubted a cop would put so much energy into one woman. He showed up and was young and thin and good looking, which made me nervous.
But it turns out he was just as nervous and new at this. My ad had finally prompted him to pursue an experience like this. I kept asking him what he liked, and he kept deferring to me, so I finally decided he had no idea what to do and probably wasn’t used to being with a sexually open woman, so I just took the lead.
I asked him if he liked kissing, his balls licked, etc. I undressed slowly in front of him and undressed him as well. I asked him if he wanted to touch my breasts. He loved that. I asked if he wanted to see my pussy, if he wanted to touch it, if he wanted to watch me touch it. I played with myself and asked him to suck my tits as I did it. It was so hot, I felt like we were kids in high school experimenting, or that I was the older woman showing a guy what to do. He freaked out over the blowjob I gave him and made me stop so he wouldn’t cum.
After I came (he suckled my breasts as I masturbated), we fucked. I told him exactly what I wanted, and he followed my requests beautifully. I told him I wanted to fuck doggy style, but I wanted him to tease me first, just rub his head up and down my cunt. Then I wanted him to push the head in, just a bit, give me only half of it at first, pull it out, keep teasing me, until finally he could push it slowly all the way in. And I wanted him to fuck me and grab on to my hips. He came silently. I’m sure he was nervous about the whole thing, wasn’t sure what to expect, and it made me happy that it turned out to be a very positive experience for him. He could have gotten one of those other women who didn’t get it.
¤ ¤ ¤ ¤ ¤ ¤
I met a 53-year-old high school biology teacher for drinks. It was a meet-n-greet before we had a real session. I wish I had time to do this with each of my clients.
I sat in the parking lot of the restaurant and read as I waited for him to show up. I had no idea what he looked like. But as soon as the guy pulled up next to me in the red sports car convertible with a spoiler, I thought, Yep, that’s him. I turned and gave him The Look—the one exuding confidence, knowing, sexuality. Later he told me he drove that car just to impress me. Awww—little does he know that I don’t give a shit about cars, especially ones with spoilers.
He was perfectly cute and academic, glasses, total high-energy type-A personality, did most of the talking. We talked about general things like cable TV and his classes, but within the hour he was pouring out his life story to me, telling me about how angry he was for years and how he went to therapy to get over it. He was angry at his alcoholic parents, the fact that his neighbors raised him, putting himself through school, his painful divorce. I asked him how he got over it, and he told me men’s group therapy sessions helped a lot.
The conversation ended with him talking about his best friend who died a few years ago in a sudden freak motorcycle accident. A truck trailer came unhinged and slammed into him. His friend always kept a silver dollar in his pocket, the same silver dollar his dad carried with him for over 50 years. And now he has it. He pulled it out of his pocket and showed it to me. The date was 1922, and both sides were worn shiny from constant rubbing.
My client’s voice dropped as he said, “Whenever I have a bad day, a hard time at school, or things seem rough, I always pull this out of my pocket and look at it. It reminds me of how fortunate I am—that I get a tomorrow. I get to have another day.”
But it turns out he was just as nervous and new at this. My ad had finally prompted him to pursue an experience like this. I kept asking him what he liked, and he kept deferring to me, so I finally decided he had no idea what to do and probably wasn’t used to being with a sexually open woman, so I just took the lead.
I asked him if he liked kissing, his balls licked, etc. I undressed slowly in front of him and undressed him as well. I asked him if he wanted to touch my breasts. He loved that. I asked if he wanted to see my pussy, if he wanted to touch it, if he wanted to watch me touch it. I played with myself and asked him to suck my tits as I did it. It was so hot, I felt like we were kids in high school experimenting, or that I was the older woman showing a guy what to do. He freaked out over the blowjob I gave him and made me stop so he wouldn’t cum.
After I came (he suckled my breasts as I masturbated), we fucked. I told him exactly what I wanted, and he followed my requests beautifully. I told him I wanted to fuck doggy style, but I wanted him to tease me first, just rub his head up and down my cunt. Then I wanted him to push the head in, just a bit, give me only half of it at first, pull it out, keep teasing me, until finally he could push it slowly all the way in. And I wanted him to fuck me and grab on to my hips. He came silently. I’m sure he was nervous about the whole thing, wasn’t sure what to expect, and it made me happy that it turned out to be a very positive experience for him. He could have gotten one of those other women who didn’t get it.
¤ ¤ ¤ ¤ ¤ ¤
I met a 53-year-old high school biology teacher for drinks. It was a meet-n-greet before we had a real session. I wish I had time to do this with each of my clients.
I sat in the parking lot of the restaurant and read as I waited for him to show up. I had no idea what he looked like. But as soon as the guy pulled up next to me in the red sports car convertible with a spoiler, I thought, Yep, that’s him. I turned and gave him The Look—the one exuding confidence, knowing, sexuality. Later he told me he drove that car just to impress me. Awww—little does he know that I don’t give a shit about cars, especially ones with spoilers.
He was perfectly cute and academic, glasses, total high-energy type-A personality, did most of the talking. We talked about general things like cable TV and his classes, but within the hour he was pouring out his life story to me, telling me about how angry he was for years and how he went to therapy to get over it. He was angry at his alcoholic parents, the fact that his neighbors raised him, putting himself through school, his painful divorce. I asked him how he got over it, and he told me men’s group therapy sessions helped a lot.
The conversation ended with him talking about his best friend who died a few years ago in a sudden freak motorcycle accident. A truck trailer came unhinged and slammed into him. His friend always kept a silver dollar in his pocket, the same silver dollar his dad carried with him for over 50 years. And now he has it. He pulled it out of his pocket and showed it to me. The date was 1922, and both sides were worn shiny from constant rubbing.
My client’s voice dropped as he said, “Whenever I have a bad day, a hard time at school, or things seem rough, I always pull this out of my pocket and look at it. It reminds me of how fortunate I am—that I get a tomorrow. I get to have another day.”
Beautiful. I've read all the posts so far - I can't stop! - but the end of this one really is a beautiful detail to include.