The following story is true.
About 13 years ago I was married to a woman that wasn't quite my perfect match. Sufficeth to say that we were having problems. Not in the bedroom, as you might suspect, but we didn't mesh spiritually. She carried an air of superiority that hung over me like a dark rain cloud. I felt that I was never enough for her and the stress was unwelcome, to say the least.
To cope with the stress, I sought relief through porn. I had refrained from porn for almsot 2 years now. It wasn't difficult with our daily sexual escapades, but nonetheless I returned to that seductive black hole that sucked me in further than ever before.
I began with normal porn: lesbian, doggy style, Bbw, cunnilingus, and fisting. Fisting was for sure the most extreme, but then I found anal. I had never been attracted to anal before, but the women in the videos seemed to love it. I became obsessed and would watch it in secret when my wife was away.
One day, I learned about pegging. It was new and intoxicating. Watching the men take a dildo up the ass from a sexy, huge breasted, fatty, got me hard. I found that thin, muscular, or average men ruined the experience. my cock would spring alive for a nice, chubby man. A nice fat ass; large, round belly; and man tits: these were a few of my new favorite things.
Little did I know what it would lead me to.
One day, as I was searching for something on craigslist, I stumbled on the Personals. Having no clue what this was, I clicked on it and was introduced to a whole new world. Boy was I naive. I had found the naughty underbelly of the internet. A place where depraved and lonely sought to satisfy their desires and stave off their loneliness for a time only to be met with regret and shame.
I was enamored and searched. Over several weeks, I perused the ads, one after another seeking to slake my lust vicariously through their confessions of desire. As I grew more brazen, I felt a desire well up inside of me to experience anal sex for myself. I didn't want to fuck a sexy, Bbw in the ass. No, I wanted to experience a dick sliding into my ass.
I was so wrapped up in my lust. It drove me. I would stay up nights texting with other men about what we would do. I always flaked and was too scared to meet up in person until I read one posting stating how annoying flakes were. I could understand this sentiment. Therefore, I resolved to not be a flake.
This world had successfully drawn me in. I was quickly pulled in with a need to satisfy a desire that wasn't supposed to be. Yet here I was. Texting with another man interested in seeing me naked and talking of sexual experimentation. Like me, he was inexperienced.
One night, he and I were taken with lust and decided to meet in person. He didn't have a vehicle so I would pick him up and we would find a discreet place to park and... well we hadn't planned that far.
I quickly got ready, hoping that it wouldn't hurt when he slid his cock inside me. I prepared myself in the restroom, showered, and got dressed. I contemplated what I might have to do. Was I willing to suck his cock if he asked? All I wanted was to be taken from behind, have my ass spread and my hole violated. I hoped he wouldn't ask.
All dressed up and ready, I hopped into my truck and headed his way. My truck was a simple, single cab with a 6 foot bed. It wasn't particularly roomy, but we'd cross that bridge when we got there. As I drove, it dawned on me that I didn't even know what this guy looked like. I knew he was in his early 20s, mexican, and horny. I realized that if he turned out to be muscular, or skinny, this might not go the way I want. Will I be turned on? I had discovered my desire to get penetrated while envisioning a man with a portly stomach and generous hips.
As I drove up, I looked for the man in yellow, but this one had a different monkey.
Anyway, I saw him standing there in all his chubby glory. He had a belly that put santa to shame. He couldnt have been much taller than 5'7". His ass was ample, too. Through his jacket I could make out two round man tits. His nipples were hard, making them easy to spot through his dull yellow shirt. I quickly conjured up an idea of an appropriate first greeting. I parked, got out of the car and met him with a hug.
He wasn't quite expecting a hug, and therefore gave me an awkward side hug as I went for a full frontal assault. I realized he wasn't quite sure what to do in this situation, putting us on the same page. Trying to recover some dignity, I opened the car door and let him climb in and returned to the drivers seat.
"Where should we go," I asked.
"There is a place not too far from here where we can hide in some trees." he replied.
