My father and I had spent most of my summer vacation traveling around prowling the clubs. I was 16 and a junior in high school and he was a 31-year-old freelance programmer. Yup, that means he knocked up my mom (who I've never met) when he was younger than I was. I was raised mostly by his parents while he was in high school and college and then he took over as dad.
Even though for most of my childhood dad was constantly bringing home women for one-night stands, I was always his first priority. Throwing a traditional fatherly role to the wind, he always encouraged me to try to get laid and taught me the tricks of the trade of pleasing women. He rarely closed the door when he was jacking off to porn, so sometimes I would happen across his room and go see what he was watching.
We kept a folder on our computer desktop called "Hot Videos" where we would put our favorite videos so that the other one could watch them. Dad's idea of a hilarious joke would be coming into the bathroom while I was taking a hot bath and peeing into the water so that I would have to drain the whole tub and start over. When we decided we wanted to become worldlier in our woman-hunting ways, we started traveling around the States and staying in hotels in big cities. My fake-ID in hand, he and I would ask around for the best nightclubs and compete to see who could bring the hottest girl back to the hotel.
At first we would stay in separate hotel rooms, but after the first couple hotels we decided it wasn't worth the extra expense; plus, it was hard to tell who was doing a better job pleasuring their catch through a wall or across a hallway. We thought it would be difficult to convince ladies to have sex with another couple in the same room, (the men being father and son no less), but we found that usually they were too drunk to really care.
One night in Chicago I was having the worst of luck and somehow went the whole night without successfully baiting a sexy lady. My dad, however, was on his A-game and pulled me out of the club with his other arm around a perfect 10.
With an air of defeat, I dawdled behind them back to the hotel room, where I plopped myself down on my bed to watch my dad suavely undress her, push her backwards onto the bed, lower himself to her vagina and circle her clit with his tongue. I was becoming unbelievably horny and decided to masturbate, prompting the woman to gesture for me to join in the fun, pending approval from my father.
Dad didn't miss a beat and pointed at her inviting lips. I shuffled off my jeans and pulled off my shirt as I waddled over to their bed.
I then straddled the woman's chest and began fucking her mouth. As the rocking motions of our three-way configuration began to synchronize, dad stood up at the edge of the bed, spat on his hand and rubbed it on his dick, and began moving in and out of her pussy at the same tempo I was fucking her mouth.
When my dad reached down to fondle her breasts, he couldn't avoid touching my butt cheeks as well.
I was surprised at first but quickly became accustomed to my dad's hands on me. By the end of that night, it seemed silly that it felt weird, because dad and I had put our dicks in all the same places, kissed her after she had given the other one head, and even double-penetrated her such that our penises were in contact some of the time.
From that point on it didn't make a big difference if one of us didn't strike it rich one night, because we knew how to have fun either way.
When my dad and I arrived at our hotel room in Montreal we had to decide whether or not we were going to hit the town that night or if we were too exhausted from traveling.
My dad said he was tired, but I told him that all we'd been doing all day was sitting on a plane. "I require 'les pussois' tonight," I pleaded, anticipating having to fake some French for the locals as well. My dad rolled over and groaned. "I'll go…but you have to shave my ass. My back hurts from sitting on the plane." He thought this would deter me, but I was very eager to get laid that night.
I extracted his toiletries from the suitcase and told him to come into the bathroom. Dad was always sure to be very well shaven before prowling for pussy, as if women had some immense fear of male pubic hair.
Both dad and I would complain afterwards if one of our 'dates' didn't have a well-shaven vagina. As I lathered up some shaving cream in my hands and sat down on the floor, dad leaned over the sink and dropped his pants and underwear in one fell swoop.
He parted his legs so that from where I was sitting I could see his smooth asshole, his somewhat parted butt cheeks, his slightly hairy balls and his impressive cock hanging down several inches further.
Taking pride in the task as if it were my soul vocation, I spread the shaving cream evenly around all of the areas in question, including spreading it around his scrotum by cupping it in my hand and running my index finger along the sides of his butt crack.
By the time I was done working my magic, his rear, were it not toned and a bit larger, could easily have been mistaken for a pre-adolescent boy's.
"Now do me!" I demanded, impressed with my tonsorial skills and feeling that I deserved some pampering. Despite the fact that I had just made a masterpiece out of his ass, he was reluctant to agree. I disrobed and bent over such that my asshole was staring directly at his face. I could sense that he was overcome with the same sense of duty that I was, and he became fairly involved in shaving my balls, butt, and pubic region. We then stepped into the shower to wash up before going out, where we each did one final inspection to check for missed patches, spreading each other's butt cheeks and nearly penetrating one another with our noses.
This ordeal quickly became a pre-clubbing ritual, and we became the most cleanly shaven straight men in North America. In Seattle we were returning to a hotel one night, but this time I had found a blonde girl who was about 19 years old and my dad hadn't found anyone.
Though while we were walking I had slid my hand underneath her miniskirt and was cupping her firm ass, she didn't seem to mind the additional attention of my dad's hand as it slid around her shoulder down into her top. She had seemed pretty timid at the club, but once we got her naked we found that she was very domineering. She had my dad lay down on his back while she stood over his face facing his feet and lowered her pussy onto his face prompting him to start lapping up the copious juices that were flowing.
She looked at my dad's cock standing at full attention out of her arm's reach, and then she looked at me. "A little help?" she asked. This girl was so hot I would have done anything she said. I leaned over the bed and took just the tip of my dad's cock in my mouth, unintentionally smearing his pre-cum all over my lips. I had seen my dad been blown enough times to know how this was done.
I took as much of his penis as possible into my mouth and used a twisting motion as I bobbed up and down. I could tell I was doing a good job, because as I sped up, my dad started thrashing his tongue around faster in the girl's vagina and she started moaning.
She watched me for a few more moments before she stood up, jumped off the bed, and said "let my show you how this is done." I watched as the girl took my dad's entire cock into her mouth and down her throat. As she moved her head up and down, I could see the head of my dad's cock creating a lump on her neck like an Adam's Apple which moved up and down. Dad and I had never found a lady who would deep-throat us before, so in his intrigue, my dad brought his head off the pillow to watch her impressive display.
She gestured towards dad's head and muttered for an instant when her mouth wasn't full of my dad's cock, "Hold him down. Sit on his face." I crawled up on the bed, pushed my dad's head back down onto the pillow and straddled his face just as she had done earlier. To my surprise, my dad opened his mouth and took both my whole scrotum into his mouth, running his tongue between and around my balls. At that point the girl crawled up onto my dad's cock so that she was facing me and started bouncing up and down, causing my dad to moan into my balls.
The girl reached forward and started to stroke my cock as well as sticking her tongue into her mouth and kissing me. I could taste more of my dad's pre-cum in her mouth. I moved forward just an inch or so to facilitate the kissing, and now my dad's tongue was directly in line with my butt hole. When he began moving his tongue in circles around my butt hole, I lost it and moaned loudly as I came in four hearty spurts against the girl's stomach.
She then used her hands to spread my cum all around her stomach and tits. Once I had caught my breath, I moved out of the way and she leaned over my dad so he could suck my cum off of her tits.
At a loss for what to do, I went around to the foot of the bed and watched my dad's penis moving in and out of her vagina. I got down on my knees and started licking my dad's hairless balls to return the favor while also fingering the girl's ass.
Every few licks I would throw in one where I started on my dad's balls and then licked all the way up the underside of his shaft and into the rear crest of her vagina.
After just a few minutes, my dad blew his stack into her vagina, and a stream of his spunk flowed down out of her vagina down to his balls, which I proceeded to lick clean. Once we had both cum, the three of us crawled into bed together, sandwiching the girl into the middle.
She, however, said she had to get home. Once she hopped out of bed, got dressed, and darted out of the hotel room, my dad and I moved in closer to fill the gap so that his flaccid penis was pressed up against my ass crack and his arm was around me and his hand on my stomach.