Chapter 1: An On-Line Relationship With Charlene

Let me start by saying I think most people would say my sex life is not what you would call boring, to put it mildly. Like most of my close friends, I usually masturbate at least twice day, try to have sex at least daily, have fucked well over a hundred guys - including my dad and his brother although most were at parties, tried out the escort scene, entertained at bachelor parties, and in general just have had some fun times. The one thing, though, that I’ve never done is meet with anyone I’ve chatted with on-line, at least the ones I don’t know in “real” life. There are a number of reasons why, all of which I’ve tried to explain a thousand times but the basic reason is simple - why should I? When I chat I have absolutely no idea who is really out there talking to me and at the risk of sounding narcissistic, it’s not like I have any problems finding someone to fuck me or anything so why risk it? Indeed, I’ve had some incredible offers - trips, flights, vacations, you name it. There have been a few times when I was sorely tempted but the risks of getting on a plane to meet a total stranger ... just too high for me.

While I realize that this may be frustrating to the people I chat with, it’s been just fine for me. Then things changed a few weeks ago when I was chatting with a woman (at least “she” claimed to be a woman) on line who was telling me about her husband and kids. Charlene claimed to be 35 years old, married right out of high school when she was only eighteen to her high school sweetheart. As a result she had very little experience with men other than her husband. In fact, as hard as it was for someone like me who started when she was fourteen to believe, he was the only one she’d ever gone all the way with sexually. Charlene said she loved her husband dearly and during their seventeen years of marriage she’d always been faithful to him with no desire to ever be with another man. She claimed to have never kissed another girl, not even for fun at a party or anything, although sometimes she couldn’t help but wonder what it would be like to be intimate with another woman.

One evening Charlene asked me if I’d ever been with an older woman other than my mom and her sister, my Aunt Linda. Her question started me thinking because if you take away my mom and aunt, the only older woman I’ve ever been with was my mom’s best friend Tammy and that was only once, and years ago at that. Charlene and I chatted along those lines for a while and later that night as I masturbated I started to dream about what it would be like to be with someone like her, someone I didn’t have a close relationship with already, someone who had never had sex with a girl before. I’d been with a couple of girls my age and younger for their first times but never anyone even close to Charlene’s age.

The more I mulled about it over the next few days the more the idea turned me on. The only sticking point was the obvious question ... was Charlene really interested or was she just chatting to have some fun and appease her sexual curiosity through me on-line? Until recently I thought I had a pretty good idea of who she was. We’d been chatting off and on for months and traded photos of ourselves and our families. She had a sixteen year-old daughter and two sons at ages fifteen and six (yes, she admitted the six year old was a “surprise”). Two things came from our sharing. First she didn’t send me nudes. It’s funny (or not depending on how you look at it) how many so-called “real women” only have nudes to share. Sure I have some risqué photos of me, but it’s not like my photo albums are dominated by them. Whenever I run into these sort of people I know 100% that they’re fakes. Secondly, it was the quantity and diversity she shared. Vacation pics from different years, birthday parties, weddings, family outings, etc. Again, most fakers will quickly run out of photos to share which I find hilarious considering the thousands of pics I have for myself. Not to mention I really don’t care to see nudes in the first place. Like, I know what naked people look like. It’s how they dress, the things they do, that tell me about them and make me believe in them.