It soon became part of my shower routine to slide the soap gloriously over my hole before sawing a couple of fingers in and out of my ass while jerking off to the memory of being rabbit fucked. But afterwards, these sessions only seemed to leave me feeling empty and unsatisfied. I needed more than a finger up there. It wasn’t long before I graduated to a long thin dildo, then a vibrator until I finally graduated to fucking myself with a thrusting vibrator.
My taste in porn selections when I was playing with my ass also evolved along with my toys. I had started out with my usual straight porn, but then I started viewing pegging videos where a hot babe would ream out some straight guy’s ass with a strap on! The trouble was that the gals all were either too gentle or bored when they were fucking the guys and the guys seemed like they were faking their enthusiasm at having a plastic cock up their butt. So of course, I eventually caved and started searching for gay butt porn. Wow! While there were still a lot of scenes with bored actors faking it, there were also a LOT of scenes of built guys enthusiastically ramming some poor moaning slim dude’s ass HARD! I could truly identify with the bottoms who looked like they were loving and hating it at the same time.
Something that bothered me, but also helped me get into this kind of porn, was that a lot of the bottom guys kind of looked like me. Apparently, there was a term for guys like me in our twenties with guy next door looks, scruffy brown hair, a lightly hairy athletic body and a cute butt. I guess I was an OTTER. Although if I shaved my body smooth, I could almost be a TWINK…
OK, I was 27 and 5′-10″, so I was a little too tall and long in the tooth to be called a twink, but I still had a trim 30-inch waist from my college soccer days and my shaggy hair gave me a boyish look. That I physically resembled the guys getting plowed made it easy to imagine myself as being in their place and that my toy thrusting tirelessly into my butt belonged to one of those big studs.
After a couple of months playing with toys that never seemed to be able to recreate the actual experience of being mounted by another man, I hesitantly decided to finally try the real thing. I know it sounds lame, but I thought that if I sampled the real thing just once that I could get this out of my system and move on with my straight life. The next thing I knew, I was searching hookup apps for someone to fuck me. There was no shortage of big guys with big dicks willing to take my virginity – for real this time! Concerned that the experience could put me on a slippery slope into a gay relationship, I decided to look for an older guy who was just looking for a good time. Eventually I found a 40-year-old married man who was willing to be gentle for my first time and was also willing to engage in just a one-night stand. Just a quick cum and go! Perfect!
At lunch time on Tuesday, I got a message from him that he could hook up after work. I eagerly agreed and hit send. It didn’t take long for the import of what I had done to hit me. SHIT! Was I really ready for this? Since I had agreed to host, he had my address and would be eagerly knocking on my door in a few hours! Having been ghosted myself, I hated to wimp out on him at the last minute and decided to see this through. I was a nervous wreck the rest of the day.
I raced home after work to get ready. I gave myself an enema so I was clean up there, took a shower and used the syringe from my vibrator to pre-lube my butthole. I closed the blinds, tidied up and laid out some condoms and lube in my bedroom. With one eye on the clock, I struggled with what to wear. I could just throw on some sweats and a tee shirt, but that seemed kind of tawdry. I wanted to make a good impression and also wanted to wear something that would accentuate my butt, but not make me look slutty. My khaki shorts! They were casual and fit my butt perfectly. The buzzer rang. SHIT! He was here. I buzzed him in and quickly slipped into my white CK briefs, khaki shorts and a red polo shirt that accentuated my pecs. The doorbell rang just as I stepped into my boat shoes. OMG! This is it!!!
I felt like I was playing a real-life version of mystery date as I turned the doorknob and swung it open. GULP! We both raked our eyes over each other appraisingly. Suddenly I felt like one of those little twinks. My “date” finished raking his eyes over me and smiled like a hungry bear. The term “bear” fit him perfectly! He was at least four inches taller than me and fifty pounds heavier. He had a full close-cropped salt and pepper beard that matched his crew cut.
“H-Hi,” I stammered, offering my hand. “C-C’mon in…” Shit! Did my voice just crack?
“Thanks” his voice was deep like a bear too. My hand felt small and soft in his big paw. He looked like he had just come off a construction site. His jeans were well worn and his sweatshirt had a company logo on the left pec of his barrel chest.
“C-Can I get you a beer or water?”
His blue eyes twinkled as he smiled at my nervousness. “Water sounds great.”
I went to get us a couple of bottles out of the frig. “Did you have any trouble finding the place?”
“Piece of cake.” He replied as I bent to fish the waters out of the frig. “Speaking of cake, nice butt!”
I must have been redder than my shirt as I nervously handed him a bottle. He took a swig. “You really are new at this, huh?” he smiled.
I smiled back. “Is it that obvious?”
He chucked me under the chin. “Don’t worry. I’ll go easy.” His thumb stroked my cheek as he started to lean in. Alarm bells went off in my head as we looked into each other’s eyes. Is he going to kiss me? I didn’t sign up for this! Instead of pulling away, my eyes closed in submission. Contact! I felt his lips press against mine and his beard scratched my smooth cheeks. He put his water down on the counter and I gasped as his tongue slid between my lips. His free hand wrapped around my lower back and pulled me into an embrace as his tongue dove deeper. I put my bottle down too and I had one hand against his chest as he pulled me into him until our bodies were pressed together.
I found myself melting into his embrace even though I was well aware that I was assuming the classic female pose for a first kiss. His tongue was fully exploring my mouth and I moaned submissively as I returned his kiss. Part of me was screaming to pull away but when his big strong hand slid down to cup and knead my ass, I completely surrendered myself to this powerful man.
He finally broke the kiss and reached down to peel my shirt off. He growled hungrily at my chest and bent down to suck on my left nipple. I groaned at the sensation while he grabbed my butt and roughly kneaded my cheeks like he owned them. He came up for air and pulled off his sweatshirt, revealing his hairy barrel chest. He pulled my head toward his right pec and I sucked and teased his nipple with my tongue and teeth like he had done to me. It felt so weird to worship a hair covered chest. A few minutes later he grabbed my butt and sat me on the counter so we were at eye level and breathing heavily in lust.