*The basis of this story is true, while the acts are fantasy. Names have been changed to protect the deviant.
*
Kimberly and I were always close growing up, only being a few years apart. Despite our families only getting together for weddings, funerals and Bar/Bat Mitzvahs (like any good semi-religious half-Jewish extended family does) we maintained some semblance of contact via phone or email before the days of social media. However, since moving overseas for work brought me out of touch with most of my extended family, it wasn't until the past 2 years that I started contacting her again. Recently, while I was going through my own divorce, she'd separated from her husband and was looking to me for emotional support and advice on how to proceed.
Let's just say that Kim and I are cut from the same cloth. Hell, we share some chromosomes, it's only natural. We are both foul-mouthed chuckleheads, always trying to one-up each other on something nasty or perverted trying to get the other one to get grossed out. My job has prepared me for the worst, so 90% of the time ends in a stalemate. We love talking dirty, and with no one to talk dirty to, we usually go at each other in jest.
I'll have to admit, I've been attracted to Kim for years. She always did look beautiful in a dress, seeing that's how I usually saw her when family met. Chatting this way was stirring up some old memories, and I wanted to test the waters on how far I could go with this. Recently, during one of our particularly dirty conversations, she mentions that she's a squirter. Seeing an opportunity to worm in some more direct line of questioning, I ask if she does it herself or does she need someone else to do it.
"I need someone else," she replies.
In my normal fashion I say, "Come here and I could help with that. My cock is built perfect for that, it curves upward, rubs the G-spot perfectly!" This point is where she would usually go TMI and laugh it off. Not this time.
"Yay! I just might, Mike!" she exclaims. Hmmm, hurdle one jumped. Let's see if I can go for number two.
"Here's a thought, want to learn how to make yourself squirt?"
Kim says ok, thinking I'm still playing around. I tell her that as soon as I got home from work, I'll give her a call and walk her through pleasuring herself to an amazing squirting orgasm.
When it dawned on her that I wasn't kidding, she replied, "Ohhh gawd! My cousin is going to teach me how to make myself squirt! Ha!" Laughter—hurdle two jumped! Let's try three for three!
I say, "Just think of it this way, we are both adults, and this is for science!"
"Haha, there's something not right about you!"
"Hey, we share the same DNA, same goes for you!" I retort. Two can fence this game. Her going on the defensive means that I'm right about something, so the time is right for me to go into the home stretch and bring this plan into motion.
"And think, because you are agreeing to this experiment, means you don't give a rat's ass to modern conventional moral thinking." Check.
"I married Jon, I have no morals!" Kim moves her queen to block, and now to go in for the kill!
"But that's why honestly you think that me talking you through fingering yourself to orgasm makes you wet, and don't deny it!" Bishop takes queen, check. A minute or two passes by with no response, so I goad her into admitting it. "Silence is the same as admission, you know?"
"Shush, you! So?" Mate! I have her.
"See? You would totally have me! Honestly, I see nothing wrong with it." Now is where the long game comes into play.
