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My favorite sitter part 2

If you read the first one, we can pick right up where we left off.
Having had hot sex with my sitter, I began to feel all grown up. I walked around my house with a swagger in my step. I was now the Man of the house. When Mom suggested I go with her to the store, I quickly grabbed her car keys and went to the drivers side of the car, because the man always drives, right? Mom quickly squashed that, laughing as she stopped me from taking her spot in the drivers seat.
The next time I saw Heather, she wasn’t sitting that night. She just came by to pick up money my mom owed her from the last time she sat for me. I peeked around my mom at the doorway to wave hi, and I saw she had some asshole guy with her. As I got red with rage, she glanced at me and gave me a quick wink while continuing the conversation with my mother. I was really upset but since we weren’t supposed to be doing what we had done anyway, I couldn’t let my feelings show. I ran to my room and pouted, but I guess if I was now a grown up, I had to leave that kind of behavior in the past.
I was really angry and disappointed, since I was supposed to be her little boyfriend. I thought maybe I could see if there were any other girls, women really, that would be willing to play those adult games, but I had to know what Heather was thinking. Why that jerk? He had his stupid backwards hat, and his stupid thin, fake looking mustache and his stupid tattoo “tribal” armband. If she was going to be with a guy her own age, at least it shouldn’t be an asshole like that.
I fumed for a week or so, wondering when I would see her again, so I could tell her what I thought of the whole thing. Finally one night, my mom was getting ready to go out and she told me Heather was on her way over. She wondered at my cold response and when she asked me what was wrong, I told her I thought the guy she was with last time we saw her was a big fat stupid jerk. My mom said it was cute that I was jealous, but she thought it was good Heather was seeing a handsome young man, because she was afraid Heather might’ve liked girls. I sorta glossed over that because I didn’t really understand but my moms comment about a handsome young man infuriated me even further. I believe the term is; petulant.
Anyway, Heather finally showed up, and I didn’t give her the customary hug, and tried to act indifferent about her arrival. When she got the preliminaries out of the way, and my mom left, she plopped on the couch next to me so I moved away. She asked me what was wrong and I told her she knew what was wrong. If I was supposed to be her little boyfriend than what was she doing with that stupid reject the other day? She laughed at me, and told me she was sorry I got so jealous, but that guy Keith wasn’t anything to her but a friend. She told me he would never get in her pants and she would never spend time with him the way her and I did. I still didn’t understand why she was with him then. She told me he was there because she was giving him some money so she could score some weed. I asked her what that was and she told me we would get into it later.
Anyway now that our little spat was straightened out, we cuddled on the couch, and she asked me if I wanted to play more adult games. I said sure and then she asked me if I ever smoked before. I said no, and she told me to come with her out to the back porch. She lit a joint and passed it to me. Obviously I didn’t know what to do so I kinda sucked in and accidently tried to swallow. I coughed and gagged for a full minute while she laughed her ass off. When I finally got the hang of it, we both took 4 or 5 hits, and I started to feel really weird. She put it out and we ran back inside. She asked me how I felt, and I told her it was weird. She said she liked it because it made her really horny. She reached for my dick, and it was so hard and pointy, and I didn’t even realize until she touched me. She said she guessed it did the same thing to me. Without any warning, she pushed me back on the couch, pulled my dick out of my pants, and started slurping on it. It felt great. I was still pretty woozy so I just laid there and let her continue. She stopped, took her pants and shirt off and asked me to lick her pussy. I jumped at the chance, grinding my penis against her legs while I eagerly lapped at the entire length of her slit. She lifted her legs up out of my way to let me put my tongue in her butthole. My nose was just poking into her pussy while I greedily licked her butt. I kept doing it as long as I could, and then with a few quick moans, she came and had to push me away because I wouldn’t stop.
We were catching our breath when she asked me if I wanted to really do it like grown ups. I said yeah even though I wasn’t really sure what she meant. She pushed me back on the couch, sat on top of me, and guided my hard little tool into her hole. I thought my little dicklet wouldn’t make a dent in her pussy but honestly, it was tight as hell, and warm, and wet. She whispered that she was glad her first time with a man was with me, her little man. I didn’t grasp the implications of that, I was just along for the ride. And ride she did! She humped up and down on me furiously while I groped her swinging breasts. It felt so good when her slick wet pussy slid up and down my dick. I started feeling like I would have another one of those heart attack feeling orgasms, but before I could, she came and rolled off of me. She asked me if I liked it, and I said sure. She told me that I was no longer a virgin, and now neither was she.
I asked her about that, and she told me that, yes she was a virgin, at least that she had never had a real dick inside her until she had mine. I asked her how she knew so much about sex if she’d never done it before, and she told me she’d had lots of sex, but not with boys. Aha! So she did like girls like my mom said. I still didn’t really understand what they did or what that meant, especially for me, but I thought the world of her so I didn’t really care.
She could sense my confusion about the subject so she tried to explain. Finally she asked me if I remembered the last time we played how I liked how it felt with my finger in my butt and how when she sucked on me and fingered me, how much I liked that. I remembered that so she explained that her pussy was the same way, and that it didn’t matter if it was a girls finger or a boys. Since guys her age were such jerks she didn’t really see what difference it made. I asked her how girls played together and she got a mischievous grin on her face and told me she’d show me.
She pulled a weird looking pointy plastic thing out of her purse, twisted the other end, and held it out to me while it started to vibrate. I asked her what it was and she had me lay down while she demonstrated.
She slowly stroked my dick and rubbed my butthole with her fingertip. As I started to warm up, she rubbed the outer part of my butthole with the pointy plastic thing. She then turned on the vibration and my head quickly exploded. It felt so amazing and when she slipped the end into my butt, I went crazy. She stroked me faster and started to push her vibrator in and out of my rectum. It felt great, and I started pushing back into it. She smiled and said she thought I might like that. I started to get that heart attack feeling again and just when I thought I was going to die, she let go of my cock and pulled the vibrator out. I was laying there panting and wondering why she stopped when I was so close.
She explained to me that that wasn’t all that girls could do for each other, and reached into her bag again. She took out something that looked a lot like the vibrator but it had a backing and a bunch of straps on it. I was confused, but she spread out the straps, stepped into them and pulled it up to her waist. While she adjusted it, I finally got what it was. It stuck out from her front just.like a dick so she could fuck like a man! I didn’t know things like that existed.
She had me lay back again, and she carefully put the end into my now eager butt. When I relaxed and got used to it being up there, she started rocking back and forth, shoving the strapon deeper and deeper while I moaned out in my ecstasy. I grabbed onto her tittys and began to suckle on the tips while she fucked me. I couldn’t believe how good it felt and pretty soon she was fucking me pretty hard. When I couldn’t take it anymore, I lunged down against her fake dick and pulled her down on top of me, so her belly squished my dick. That was the only contact she had with my dick while she had the strapon in me, but that was all it took to make me have a real, squirting, orgasm. My first real cum went all over my belly and some oozed down to my ass, where it coated her fake dick, encouraging her to pick up the pace and continue to fuck my ass. She moaned out, oh fuck yeah, and thrashed around, presumably having a big orgasm herself. In the process, she had pushed that thing as far as it would go up inside me, and I started getting into it. I wanted to keep going by then, but she pulled it out and collapsed next to me.
I asked her if she was ok, and she told me she felt great but she had to rest a little. I was getting horny looking at her, so I straddled on top of her and played with her fake dick, rubbing it on my dick and around my butthole. She was still breathing hard but looked up at me and smiled. I couldn’t quite get the fake dick back inside me. I guess it dried out while we sat there, so I dropped down and put it in my mouth to wet it. She called me an amazing little pervert. It tasted poopy but I guess I was too far gone to care. I crawled up and sat on her fake dick and started riding up and down the way she did to me when she put my dick inside her earlier. I sat all the way down until that thing was all the way in, and she grabbed me by the waist and rocked me back and forth. She humped me back and soon I came. It wasn’t a big squirt like before but it was still amazing. Before I could dismount on my own, she pushed me off, bent me over, and did it to me dog style. It was funny how my moans were broken up by the impact of her slamming into my butt. She finally screamed oh yeah, you’re my little bitch, and collapsed in orgasm.
I was amazed that we did it so many ways in one night. It was a lot of firsts for me to absorb at once. I didn’t know anything about what we were doing. I just knew I liked it. She did patiently explain to me that what we did wasn’t necessarily what all people did for sex. She also reminded me that if I wanted to remain her little boyfriend I’d have to keep it all secret.
I promised I would do what she asked, because she would always be my favorite sitter.

Updated: October 21, 2016 — 1:30 pm

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