My boyfriend broke up with me several months ago. At first, I was heartbroken because I thought he was the one I was supposed to be with for the rest of my life. As time went on, I realized that I was better without him. He only called me when he needed something; he rarely checked on me when I was sick. And the worst part was that he was abysmal at sex. He fucked me like a jackhammer, which never brought me to orgasm. He never went down on me.
I dated a few guys after he dumped me, but we didn't have sex. I wanted to wait until I was part of an official couple before I went that far with a man. The whole "don't give away the milk for free" thing, you know. My vibrator and I became frequent friends during my long dry spell. I would gasp with orgasm by using my fingers and vibrator, enjoying the pleasurable release before I fell asleep. But I missed the feel of a living, breathing man with a warm dick and someone that could hold me afterward.
I usually cruised the dating websites like Match.com and eHarmony.com to look for a compatible man. One night, though, I realized how much I wanted a man next to me. I wanted to be fucked and pleased. I wanted to be eaten out, something my ex-boyfriend refused to do. It had been five years since I had been eaten out. When I was with him, I could pretend that it didn't matter because I did have his body next to me. Now, though, I realized how much an orgasm with a man meant to me.
That lonely Friday afternoon I decided to abandon my usual dating websites, where everyone claimed to enjoy long walks on the beach and leisurely gourmet dinners. I wanted something different. I wanted to meet a man for some good old-fashioned intimacy with someone who knew how to please a woman. I signed up at CasualEncounters.com and started to sift through the men's ads.
I gravitated toward the older men's section. Maybe I knew that these men had the experience to know how to please a woman. Maybe I knew that being 25 years old and reasonably attractive meant that I would have more men vying for my attention. I searched through the profiles and was figuring out which man I would choose to contact.
One gentleman interested me in particular. His ad got me wet:
Fit 60-year old wants to pleasure you with his tongue, fingers, and more... I haven't been with a woman in a long time, and I have a lot of unreleased passion that's waiting to fill you. This is my first ad, and I hope it's my last. I'm not looking for a one-night stand. I'm not necessarily looking for a long-term relationship either. I'm looking for someone like me, someone who lives a solitary life and would like to occasionally explore her passion with a clean, attractive man who will leave her satisfied. Please write me a line and let's see where this goes.
I wrote him that night. I told him my first name, my age, that I hadn't had an orgasm with a man since my first boyfriend seven years ago. I told him that I wasted way too much time in my second relationship, especially since it wasn't sexually pleasurable for me. I also explained that this was my first time looking on a website like this. I wanted something clean, safe, and discreet. I took a quick headshot with my webcam and sent the picture file.
He wrote back within an hour. His name was Kevin, and he told me that his wife died a year ago after a long battle with cancer. Kevin wasn't interested in anything serious, but like me he wanted to explore his physicality with someone. He wanted to meet for dinner tonight and possibly more afterward.
When I opened the attached file, I was happy to see that Kevin's picture looked almost exactly like I pictured him. He had a head of silver hair, a well-maintained mustache, and a rugged look about him. In the picture he was wearing jeans and a flannel shirt. I couldn't see much in the way of his chest, but he didn't look like he had a pot belly like most other guys his age did. I found myself drawn to that telltale bulge in his jeans. I wanted this man.
If I had more time to really think about what was going to happen, I would have likely backed out of the impromptu date. After all, meeting a strange guy that was more than twice my age for sex wasn't a typical night for me. But it happened so fast. One minute I was lounging around in my pajamas getting wet reading internet personals, and the next minute I was getting a shower and putting on a sexy dress. I hadn't put on a sexy dress in years.
I took great care in getting ready with a steamy shower. I shaved every hair that wasn't on my head off my body. I hadn't had a shaved pussy in years, and I couldn't get over how thrilling it was to feel the air against me. Even casually bumping up against the footboard of the bed was a titillating experience. I decided to wear a thong with a lacy garter belt. I slid my turquoise dress over my curvy body. I loved how it hugged my generous, full breasts, tiny waist, and gently-curved hips. I expertly applied a minimal amount of makeup, spritzed my favorite perfume on my wrists and behind my ears, and looked at myself in the full-length mirror, applying final touches until I was 100% pleased with the end result.
Kevin and I were to meet at a fancy steakhouse in downtown. I got there about five minutes early, and I nervously waited in the reception area. Every time the front door opened, I held my breath, anticipating the living version of the picture I saw. Each time I became more disappointed when it wasn't him. Finally, Kevin arrived. He looked even yummier in person. He was wearing a suit with a green tie, which matched his emerald eyes.
He strode right over to me. "Tabitha, you look gorgeous." He leaned over and gave me a peck on the cheek. The mustache gently tickled my cheek. "You look better in person than I ever anticipated."
I smiled teasingly, "It was a bad picture, wasn't it?"
"I couldn't see your body. Why were you hiding it?" Kevin asked gruffly as we approached the hostess.
"I didn't want you to come just based on my hot body," I murmured in his ear.
