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That's My Babysitter In That Porn Video!

I notice my substitute babysitter on a free porn site and fall in love.
Following my divorce, my company transferred me across the country and the custody agreement with the ex allowed me to have my daughter for six months then she would go back to her mother’s place on the West Coast for another six. I had a deadline rapidly approaching and desperately needed some uninterrupted time in my home office to complete my reports. I called my usual babysitter and she apologized but had accepted another job for the evening. I explained my situation and asked if she had any friends she might recommend.

She said, “I’ll call my friend Jo to see if she’s free. She doesn’t sit very often any more but she’s filled in for me a couple times when I ended up double-booked. I’ll have her give you a call if she’s willing.”

I thanked her and went to check on my daughter who was doing homework at the dining room table. I spent a minute helping her with her math assignment when the phone rang.

“Hello?”

“Hi, Mr. Craig? My name is Jo, I just got a call from Taylor who told me you need a sitter this evening.”

I said, “Hi, Jo. I have a huge amount of paperwork I need to finish before work in the morning and I just need someone to keep an eye on my daughter Sami. She’s 11 years old, goes to bed at 9pm and won’t be any trouble. I just need some uninterrupted time at my desk and Sami won’t give me that time unless someone else helps keep her time occupied. I’ll probably need you for no more than four to five hours.”

She said, “That’s fine, I don’t really sit much any more except as favors to friends. How does 50 for the evening sound?”

I said, “If I can get my report done without interruption, it would be worth twice that to me.”

We agreed on a starting time and wage for the evening and told me a family member would be dropping her off a few minutes before starting time. Sami and I had just finished dinner when the doorbell sounded. I answered the door and an absolutely gorgeous young lady with blonde hair in pigtails wearing a short denim skirt and a midriff baring tee shirt.

She said, “Hi, I’m Jo.”

I shook her hand and said, “It’s nice to meet you. Come meet Sami.”

She said, “OK.”

We walked into the dining room and I said, “Sami, this is Jo. She’s going to hang out with you while Daddy works in his office, OK?”

Sami said, “Sure Daddy. Hi, Jo.”

Jo said, “Hi, Sami. What are you doing there?”

Sami said, “Math. I hate it.” She said, “I did pretty well in Math before I graduated, would you like me to see if I can help?”

Sami said, “Yes, please.”

I excused myself, went down the hallway to my office, and shut the door.

I spent around an hour organizing the data for my report and needed a short break. I headed out to the kitchen, got myself a cup of coffee, checked in on Sami and Jo who were finished with Sami’s school work and were now playing a video game in the living room. Watching Jo was generating a bit of lust in me. Since Sami arrived, I had only gone out maybe two or three times and hadn’t had sex for several months.

I sat down with my coffee, looked at the stack of documents, the half-completed report and decided the diversion I needed to restore my ambition and get my thoughts off the hot babysitter in the living room was a bit of adult entertainment. With Jo fueling my lust, I went to my favorite free porn website and typed the words pigtail and babysitter into the search box. I scanned through the first three or four pages and saw a thumbnail shot from a video I decided to check out with the title ‘sexy babysitter in pigtails seduced by her boss’.

I clicked on the image and the first scene was the ‘boss’ answering the doorbell when the babysitter arrived. I did a double take when the girl came inside.

“Shit,” I said. “That looks just like Jo.”

I watched in earnest as the plot rapidly advanced to wear the man was putting his moves on the young girl. Soon her shirt was up, revealing her boobs and she was half-heartedly trying to resist his advances. The clip was short, only about six minutes long, so it wasn’t long before they were fucking like crazy and I was stroking my rock-hard erection as I watched the guy pull out of her pussy, take it in the mouth and then let him come all over her tits. I shot stream after stream of cum into the air, most of which ended up on my thighs and belly.

I closed the video window after book marking the clip and went into the bathroom to clean and straighten myself up. I poured the rest of my coffee down the sink, giving me an excuse to go back to the kitchen.

I found Jo and Sami still playing the video game and I said, “It’s getting close to bedtime, sweetie. You can play another 15 minutes then it’s time to brush your teeth and change into your jammies. I’ll come tuck you in when you’re ready.”

She said, “OK, Daddy.” I said, “Jo, I’d appreciate it if you hang around until she’s sound asleep, OK?” She said, “Sure, Mr. Craig.”

I went back to work on the report and a few minutes later, there was a knock on my office door. Sami’s voice called to me, “Daddy?”

I went to the door and saw Sami standing there in her pajamas holding Jo’s hand. “I’m ready for bed, Daddy,” she said, “Jo helped me.”

I said, “That was very nice of her.” Jo said, “I didn’t mind at all, Sami and I are getting along great.”

The three of us walked to Sami’s bedroom where Sami asked if Jo could tuck her in tonight. That was a first; I had never seen her become so comfortable with a stranger this quickly. She never let Taylor tuck her in if I was home. Once Jo tucked her in, I leaned over and gave her a kiss good night then we turned out the light.

In the hallway on the way back to the living room, I gathered my courage and said, “Jo, I’m not sure what you know about my situation. My wife and I divorced after 10 years of marriage. She remained out west and I was transferred here. We share custody of Sami – 6 months each. Anyhow, the divorce really devastated me, I rarely go out on dates anymore and it’s been ages since I spent the night with a woman, consequently I turn to self-satisfaction for relief, mainly while watching porn on the computer.”

She said, “Why are you telling me all this, Mr. Craig?”

I said, “Well, I found myself taking a break a bit earlier and tried to get primed up a bit for later when I go to bed and I found your twin on a porn video I watched – or was it you? The resemblance was unmistakable.”

Jo’s face reddened and said, “I was worried this might happen someday. I just knew that someone would end up recognizing me eventually. I’m so ashamed.”

I said, “You have nothing to be ashamed about, Jo.” I thought you looked beautiful and it was so incredibly hot. It really made me wish I was the lucky guy who had the privilege of being with you.”

She said, “Those videos were taken by my jerk of an ex-boyfriend. He was a real smooth talker and managed to talk me into doing them a few times – he let his best friend do the camera work, it made me feel like a whore… being filmed by a third guy while having sex with my boyfriend. Not the sex and role playing itself, that was actually kinda fun.”

I said, “So you’re not doing that anymore?”

She said, “The videos or the sex? I don’t let myself be filmed or photographed anymore and as much as I love sex, I really don’t get as much of that as I like, either.”

I said, “You’re a beautiful, sexy girl. I can’t imagine not having a swarm of guys who want to be with you – you certainly turned me on. By the way, as much enjoyment as I got watching you and wishing I could see more videos of you, I’m glad you no longer do them.”

She turned to me and said, “It really turned you on, huh?” She glanced down and noticed the obvious bulge in my trousers.

I said, “Very much, you’re an incredibly sexy girl, Jo.”

She rubbed the bulge in my pants and said, “Thank you, Mr. Craig.”

I said, “As long as you’re touching me that way, I think you should call me Steven.”

She said, “So which video did you see, Steven?”

I said, “One called ‘sexy babysitter in pigtails seduced by boss’, how many did you do?”

She said, “Four altogether, and that was probably the worst of the batch. I think the one called ‘teen in pigtails gets plowed’ was the hottest.”

I said, “I didn’t see that one listed.”

She said, “Where’s your computer, I’ll show you.”

I couldn’t believe it. I discovered one porn video out of a bunch made by my babysitter and now she actually wants to show me the one she thought was the best! I led her into my office and let her sit in my desk chair while I moved another chair next to hers. She deftly used the mouse and keyboard and found the video she was looking for and clicked ‘play’.

As the video played, I couldn’t help but rub myself and attempted to do so as discreetly as possible, but it wasn’t long before Jo noticed and said, “A handsome man like you shouldn’t have to resort to pleasuring himself when there is someone already here willing to do it for him.” I just stammered a bit in response. She clicked on the stop button, rotated the chair toward me and stood up. She pulled the tee shirt over her head, exposing her perfect braless chest then pulled me up to my feet and kissed me passionately. She said, “So do you want to take this to your room or do it here?”

I said, “I should make sure Sami is asleep first but I’d much rather do it in my room.”

We walked into Sami’s room and found her sound asleep, which was good because I didn’t know how I’d explain why her babysitter was now half-naked if she happened to see her.

Jo said, “You’ve got such a precious little girl, Steven. Lying there sleeping, she looks like an angel.”

She took my hand and said, “So, where is your room?”

I led her to my room and as soon as the door was closed, she kissed me again and started undressing me. She dropped my pants to the floor then worked my boxers down over my erection. She kissed me one last time before dropping to her knees and sucking my cock into her mouth. When she had it well coated with saliva, she deep-throated it – the first time anyone has done that since before I was married, since my ex-wife was unable (or perhaps unwilling?) to attempt the maneuver on me.

My cock isn’t much longer than most, but a lot of girls I’ve been with comment that they’ve never had one with more girth, so being deep-throated was a rare occurrence for me. Not only was Jo very proficient at it, she seemed to enjoy it very much.

I led her to the bed and talked her into lying on our sides so we could eat each other at the same time. I put my tongue in the pussy I had seen on a porn site just minutes earlier and marveled at her really tiny labia. I always thought large labia were unappealing and loved the appearance of a tiny vagina. I liked the way hers enveloped my tongue as I pushed it into her wetness and how her clit grew to an amazing size as I licked it.

She let my cock out of her mouth following her first orgasm to ask me if I wanted to finish in her mouth or pussy. I told her it had been so long, I’d love the chance to come in her pussy. We switched positions and I got between her legs where I slowly worked my cock into her amazingly tight pussy. She moaned continually and after changing positions several times, I reached the point of no return while I was on top again, her ankles resting on my shoulders as we fucked as hard and fast as we could. When she felt the first stream of cum deep inside her, she had a strong, gushing orgasm.

As we lay there cuddling in our post coital bliss, she told me how great she felt. I asked her what the chances were she’d be willing to pursue a continuing relationship with me. We gave it a try, are now living together and planning to marry. Of course, my ex isn’t very happy that I’m with a beautiful, sexy girl closer to Sami’s age than my own, but we’re happy, Sami and Jo love each other dearly and we feel we have an exciting life ahead of us.

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