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These are the tales of my journey from an unhappily married man to a very sexually active single/divorced man. These stories are based on true events and relationships, although the quotes may not be verbatim, and all events are generally stated as best as I can recall, with some embellishment or artistic license as needed, especially considering I am writing this 20+ years after the events of the first story. But the substance of each story is true.
Everyone was over 18 and everything was consensual. Names and places have been changed or hidden to protect identities and privacy.
Chrissy
After about six months of separating, and soon after Debra and I split up, I moved out of my rental apartment and into a nice, big townhouse about ten blocks from Kim, my now soon to be ex-wife. Still in the same town and convenient to her house, the schools, parks etc.
We had an after school sitter quit on us in the middle of a school year, and had to scramble to replace her. We contacted Kelly, who had moved on after she got married, she didn’t need to babysit anymore.
We were in a jam. Then we got lucky with Chrissy.
Chrissy was the younger sister of Audrey, who was an occasional weekend and evening babysitter for us when the kids were babies. I remember Audrey telling us (about seven years prior) about her sister Chrissy who had just dropped out of college, moved back home, was basically a lost soul. Their father had left them when they were very young and was never around, Chrissy didn’t even remember him. Chrissy and Audrey had no father figure in their life, and Chrissy couldn’t ever deal with that. She was a hot mess.
Fast forward seven years later, and Chrissy had apparently turned her life around. Got her real estate license, and was selling homes in and around our region for a couple years. We had called Audrey to see if she knew of anyone that could help us, and she got us dikmen escort in touch with Chrissy, who agreed to help us out after school. She had a flexible schedule so she was available to accommodate us for those two or three after school hours each day.
Both kids were now in elementary school, so it was a matter of picking them up, getting them back to the appropriate parent’s house, and doing the usual after school things. We shared custody, so some days it was my house, other days Kim’s house.
Chrissy was young – only 25, and with me now almost 45, I was literally old enough to be her father. Chrissy had light brown hair, on the shorter side, maybe 5’4″, and a bit thicker. Not fat by any means, but a bit bigger of an ass, thicker thighs and some really big tits.
Around me, she was very formal and proper. “Yes sir,” “of course sir,” and addressed me as Mr. (Last Name). With my ex, she was much less formal, using Kim’s first name and generally being much bubblier. She treated the kids the same way at both houses.
One day I said, “Chrissy, please call me by my first name,” and I asked her to just be herself around me like she is with Kim.
She apologized and said that she’s not always comfortable around men, but she’d try.
Over time as I dug a bit deeper, she mentioned that her therapy had revealed that she wasn’t comfortable around men because she had no father, so she didn’t have much experience around grown men. That’s why she dropped out of college, too many male professors, one of whom she’d slept with.
I was shocked that she told me this, but once she did, a light bulb came on for me – she has daddy issues.
Now, I’ve heard that term before, but never really knew what it meant. But I was determined to find out. I wanted to fuck her, but I needed to be careful or I’d scare her away. She needed to really trust me first.
So, over the next dinar escort few months, I treated her more like family than an employee. I had her stay for dinner with us often, took her with us for ice cream after, bought her gifts, the whole nine yards.
This all paid off, because one day, out of the blue, she texted me a picture of herself in a bikini in front of a mirror. I thought maybe it was a mistake and meant for someone else, so I said nothing. The kids were with my ex that week and so I didn’t expect to see her.
A day later she texted, “Didn’t you like it?”
Playing dumb, I asked, “Like what?”
She said, “My picture. Am I fat?”
“No of course not, you’re beautiful,” I responded. “I just thought it was meant for someone else so I didn’t want to embarrass you.”
She said, “Do you really think I’m beautiful”
I replied, “Oh yes, you are stunning and quite sexy.”
“Do you want to see more?” she asked.
This girl was desperate for attention, so I said, “Yes, I want more. I want to see it all.”
She sent a pic of her bare tits, which were everything I had hoped and expected. I spent the next hour or so instructing her as to what pictures to take and send, and over the course of the rest of the evening, she sent me pix of her tits, her pussy, her asshole, with a dildo inside her, sucking the dildo, everything. I was blown away, sweet little Chrissy a naughty slut.
Toward the end of the night I said, “After you are done at Kim’s tomorrow, come to my
house. Be here by 6:30, not a minute sooner or later. Use the back patio entrance, the door will be unlocked.”
She replied, “Yes sir.”
When she walked in the door the next night at exactly 6:30, I called to her to come to my office. She found me sitting in my chair, naked, stroking my hard cock.
I said, “Come over here.”
She walked over to me and stood in front diyarbakır escort of me, still.
“On your knees, stroke my cock,” I commanded. She obeyed, never taking her eyes off of it.
“Look at me.” She did, while she stroked.
I said nothing, I wanted to see what she would do. Most women would eventually start sucking it, but she didn’t. She wanted to, but she was waiting for permission.
Finally she pleaded, “May I please suck your cock?”
I nodded, and she lowered her head and gave me some long slow licks and sucks. She was not very experienced, so I coached her.
“Lick me like this, suck like this, deeper, use your hands here etc.” She was a willing and eager student. She was getting me close to coming, so I did something I’ve always wanted to do but never had done.
I stood up, grabbed her head on both sides, and started fucking her mouth and throat. She didn’t know how to deep throat, but she was going to learn or die trying.
I said, “Look at me, and no crying.”
I shoved my cock down her throat and fucked her like it was her pussy (soon enough). She was gagging and drooling, thick ropes of saliva falling out of her mouth, but she never pulled away.
“Grab my balls”I ordered, then, “Stop, look at me.”
She looked up, my cock still buried in her throat, her eyes teary but looking happy.
“I’m going to come down your throat. Have you ever swallowed cum before?”
She nodded.
“I thought so, slut. Swallow it all, every drop. Don’t disappoint me.”
With that I resumed fucking her throat, harder, working to my orgasm. I hadn’t blown a load in over a week, so this was going to be a doozy.
Finally I thrusted all the way down, she gagged and coughed up some saliva, and I unloaded right down her throat. She was gasping for air, but never tried to get away. I could hear her gulping. When I was done, she held my softening cock in her mouth.
I said, “OK,” and she pulled back, her eyes teary, her mouth covered in cum and saliva, but an oddly satisfied look on her face. She had pleased me, and that pleased her.
“You can go,” I said. “I’ll be in touch.”
This was going to be fun.
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