On a passage on my Love Boat with two uninhibited whores.
3. Figuring It Out
Two blowjobs and a makeout session, all before noon. Not bad for an old salt whose draw is nothing more than a sailboat. This passage to the Keys, quite boring when done solo, was showing promise.
We sailed throughout the day, making small talk. Pam, it turns out, was a renegade hippie. In her teens she had run away from a dysfunctional household, especially an abusive dad. He started molesting her when she started grade school. Her uncle had joined in a couple of years later. The men would send the mom out shopping, then take Pam to the basement and have their way with her, passing her back and forth, sometimes doubling up on her.
In high school she quickly became known as the football teams private property. After daily practice, three or four players would gangbang her. Then home for more sex with dad or dad and uncle. After the Friday night football games, she would have to service the whole team. The team would chip in for a motel room and bring the cheerleaders along. To make matters worse, her grades suffered and she had to have tutoring. Of course, the teachers, both male and female, knew of Pam's situation and reputation. They all took advantage, too. She was everyone's darling.
These football team orgies, the daily dad sex and the weekly romps with her tutors went on until Pam escaped. In her junior year of high school she ran away, ending up in a commune out west. Because everyone viewed her as a "free use", no holds barred sex goddess, she ended up in a commune based on "free love." The concept intrigued and attracted her. Little did she know that the charismatic leader of this commune viewed free love as free sex. He was no different from any of the others who had used her so freely for so many years.
Pam was eagerly accepted into the commune community. She quickly became the darling of the entire population there, sharing her body with anyone and everyone. Inevitably, she got pregnant and Christy appeared. Shortly afterwards, Pam got notice that her dad had died. Seeing an opportunity to escape her commune prison and secure a more normal life for Christy, they moved in with Pam's mom.
Pam got a minimum wage job while grandma babysat Christy. In order to make ends meet, Pam would occasionally turn tricks for money in the same basement where she had learned those tricks years earlier. So when
Christy came of age, Pam took it upon herself to educate her regarding sex. She would allow Christy to watch as she pleasured her clients. The men would invariably demand that Christy join in but Pam was adamant. She denied every request.
As for Christy, her upbringing was was much more traditional in most ways. She had been taught from a young age that only the doctor could touch her private parts. When she had her first period, she and Pam had a long talk. Her mom had eased her into the concept of sex by having her watch as Pam turned tricks for extra money. Christy explained "I learned that most men are selfish, pretty brutal and are only interested in satisfying themselves, with no regard for their partner. They're pretty mean, slapping, spanking and spitting on their partner. I had a few boyfriends in high school and I always made them respect me. No respect, no pussy.
"Don't get me wrong, Sailor - there are times when I love rough sex. Having a hard cock just pound the shit out of me. Grab my head and just have your way with my mouth, ram it in deep. And I adore having both my pussy and my ass in play at the same time. Sometimes I'll have a dildo up my ass while some guy is fucking my pussy. I've learned that there's a time and place for all variations.
"Then, when I needed extra money for something special I wanted, I finally convinced my mom to let me entertain a few of her clients. She hand picked them for me so I didn't get the lowlifes. To be honest, I actually prefer older men, like you. Sure the young studly guys are cute and they can fuck for hours. But that doesn't compare to the touch, the finesse, the experience of older guys.
"What about you, Sailor? What's your story? How'd you end up here?" "Well, ladies, it's a long story and we're close to our first anchorage. Maybe I'll regale you with my tale during sundowner time. Now, one of you go forward and prepare the anchor." They looked at each other with a vacant stare. Finally, Pam blurted out "We're not sure what that entails, Sailor. Maybe you could show me what's involved while Christy drives the boat." After her rookie mistake with the mooring lines, I was hesitant to put my six figure boat in her hands. But there was no other choice.
Once safely hooked to the ground, I asked if either of them knew how to mix drinks. Pam volunteered. "What’s your drink of choice, Sailor?" "I'll have 4 fingers of scotch on the rocks, please." Pam scurried below to bartend leaving me alone with Christy in the cockpit. As soon as Pam was out of sight, Christy scooched over next to me, legs touching. She looked enticing, she smelled delicious and she seemed more than willing.
I put one arm around her shoulder and leaned it to kiss her. She responded appropriately and we were soon liplocked. I slid my free hand under her shirt and cupped her bare breast in my hand. It was young and firm and her nipple was fully erect. We kissed as I fondled her chest, her free hand exploring my junk through my boxers. Suddenly, Pam reappeared "Uh, excuse me. Hope I'm not interrupting anything important."
We enjoyed our drinks and some stimulating, raunchy conversation for an hour or so, admiring the sunset. Pam related some of the more extreme sexual situations she had experienced. "For some reason, men seem to like to fuck assholes. Mine got so used it seemed to loosen up, losing that tight hole guys crave. It got to where even two dicks at once hardly even registered.
Initially, I loved the feeling of having my asshole stretched, but after years of use I guess I got complacent. That is, until I got to the commune. There were a few perverts there who introduced me to fisting. The first time I had my asshole fisted, that feeling of pleasure returned. Oh, my God! Then when I got my pussy fisted, it was similar. I can't really describe how much pleasure that gave me. It still elicits very intense orgasms."
All I could do was smile, nod approvingly and request another drink. This time Christy clamored below, returning with a fresh round. She could barely contain herself. "Oh, my God, yes! I didn't know anything about fisting until recently. I may have mentioned that I enjoy having both my lower holes in play at the same time. Knowing this, my mom suggested fisting. She's been slowly introducing me to it over the past year or so. At first it was a bit much for my tight holes, but I'm growing to like it more and more. I'm excited to try having both holes fisted at the same time but I'm still working up to that."
"Wow! You two have some interesting history. Mine is not nearly so avant guarde. In fact, it's quite the opposite. That is, until my wife passed away some years ago. Before that we lived the classic American dream. Then the boys came along. After that sex vanished from our life. We tried everything but the spark was just gone.
"After my wife passed, I met my "any" girl. Bipolar, heavily medicated, I call her my any girl because she would do anything, with anybody, anywhere. Just ask and she'd provide. That lasted about 10 years until I retired and moved aboard my Love Boat. Since then it's been sort of catch as catch can. Different ports, different girls. Some willing and raunchy, others not so much. Looks like I've won the lottery with you two.
"I'm feeling a good buzz on and all this sex talk has got me going. It occurs to me that you two have been doing all the work so far. I've had two blowjobs and I haven't gotten either of you off yet. How about we go below and see what comes up?"