9 comments/ 87924 views/ 43 favorites My Babysitter Ch. 02 By: GreenGale There it was again. That hard, warm cock in my mouth. I loved it. I needed it. I knew it wouldn't last, though. I awoke from my dream with my hands on my dick as usual, but my mom was standing by my bed. I was so surprised to see her standing over the bed I almost forgot to conceal my erection. "Hey son we're home from our trip to Hawaii!" she beamed. "Oh great, hope you guys had fun" I groaned, secretly I knew quite well I had a lot more fun at home, with my babysitter. "That's not the attitude I like to hear, Mister! Does Annabelle need to come back, Sam?" she warned "Oh no, gosh, that was so embarrassing to have a babysitter!" I lied, hoping Annabelle would be forced back upon me. "We may have to give her another call if you give more trouble" my mom walked out of the room, I realized she was wearing nothing but a silky robe. I found it somewhat seductive. It made me think about all the crazy things my parents did in Hawaii. I wondered if they had awesome sex like I did, and if it was as kinky as mine. I went down to get breakfast when I found my mom bent over in her robe, looking under the kitchen sink for something. I stared at her ass for a couple of seconds before she noticed me. "Whatcha doin', son? You get breakfast yet?" she said. She was still bent over rummaging around. She had such an amazing ass it drove me wild. "N-no, not yet." I stammer, trying not to make it obvious her ass turned me on so badly. "Well get something! Oh yeah also, your dad's going to Seattle for another business trip, I'm not going on this one though. It's another week long trip. In about a month." My dad walked in, "yeah don't make us get Annabelle again to watch you" "But mom will be here this time!" I argued "We may need to get her for when your mom is at work!" he replied angrily "Okay, okay..." I tried to settle him down before it got worse. "Dont you give me that! We may have to get Annabelle if this attitude remains!" he said. That would be pretty great, though. If Annabelle came back. Oh how I longed for her already, and it hasn't even been a day yet. Days passed and I couldn't stop thinking of my week with Annabelle, my temptress of a babysitter. I liked everything about her: her freckles on her cheeks and nose, her long red hair, her slim body, and her sweet hanging breasts. I needed her so badly. So after a couple of weeks of waiting, I decided to give her a call. The phone rang for a couple seconds before she finally answered. "Hello, Annabelle Bunford speaking" "Hi, this is Sam." I muttered "SAM! Why has it taken so long to call me?!" she yelled, but with a excited tone "I'm sorry I've been so hesitant to call. I've been nervous, ya know?" I said, "but I think now it's time that we meet up again? Sound like fun?" "Of course dear? What do ya want to do?" she said "Well actually my dad is leaving in a couple of days and he might invite you to babysit again!" I said. "Oh that sounds good!" she responded. "One problem though, my mom will be there when she's not at work that week." I said wearily. "Thats fine, we'll have all day for me to do whatever you want to, to me" Annabelle whispered. After a couple days, my dad told me that I haven't shown enough responsibility to go a day without supervision, so he was going to call Annabelle. My dad left Monday morning and my mom left for work. The doorbell rang and I knew who was there. My sweet Annabelle. She was wearing a short, dark purple dress that barely covered her completely. The purple went well with her red hair. "So what do you want to do?" She asked when I let her in. "Oh, I dunno, had anything in mind?" I said "Actually yes." She responded, " I was thinking we'd watch porn together" I've never watched porn with any other person, but I was open to anything. "You choose the category!" She said and of course I chose the Transsexual section. From there we drifted to the crossdressing section and we watched a video of two crossdressers go at it. My cock started to get harder and harder and I noticed hers was as well under her dress and her slick lace panties. She started rubbing my throbbing dick through my pants and I reached into her panties and grabbed her hard, yet tiny little cock. It was so adorable yet so erotic I nearly came in my pants just by touching it. We started jerking each other off and after a while she said, "Wait I have a great idea. Your mom has a lot of kinky clothes, right? Why not wear some, if your into crossdressing so much!" "I-I-I dunno about that, Annabelle..." I said, completely saturated in fear. I've never worn my mother's clothes before. "Come on, it'll be fun!" Annabelle leaped up, her breasts jiggled. I followed her juicy ass upstairs to my parents bedroom and walked into my mother's closet. "Okay, lets see what she has here..." Annabelle started going through my mom's clothes. She finally picked out a pair of lace panties, lace bra, a short, red skirt and a white blouse. She stuffed the bra with tissues and snapped it on to me without delay. She slipped my mom's panties on over my precum-dripping penis and threw on the shirt as well. I slipped up the skirt and looked at myself in the mirror. It was so embarassing because I've seen my mother in this exact outfit, but I'll admit I looked pretty cute. "Ooh, you'd make a cute girl" Annabelle said as she kissed me. I looked at her kissing me partially in the mirror and it was weird to see two girls kissing eachother in the mirror while in actuality our dicks were rubbing against one another under our skirts. She started kissing me on the neck as we moved to my parents bed and that got me incredibly aroused. I was so scared but so turned on. Annabelle pulled out her dick and started jerking it off right in my face. I felt so dirty. She started calling me her bitch and slapped me around a bit before I took her cock in my mouth. "Mmmmm yeah. Take it all the way in, bitch" Annabelle said lustily. I could feel my cock about to burst out of my mother's panties when Annabelle forced me to deepthroat her penis all the way in. It was the moment after that changed my life, though. It was when the doorknob turning and I looked out of the corner of my eye, while I was still sucking my transsexual babysitter's cock, when I saw my mom walk in the room and see me wearing her clothes and having sex with the baby sitter. At that moment I thought my life was over. I dreaded what came next. But actually, it did not go as expected. "Oh Sam, you dirty, dirty boy. You need a good spanking." My mom said. She walked right over to me, while I was still sucking on Annabelle's cute little cock, and spanked my ass. It hurt, but it felt so good. What made it better was that my mom kind of squeezed my ass too while she did it. "Damn, you look good in my skirt, son." She said. "Nice of you to make it, Mrs. Woods!" Annabelle said, with a huge smile stretching over her face. I was trying to pull her cock out of my mouth to try to piece together that Annabelle invited my mom to have sex with us, but she just forced me down harder. "It's been quite a while, Annie." My mom said as she walked into the bathroom. "I'll be right back." Annabelle winked at me as she pulled her dick out of my mouth. "So, that was a surprise, wasn't it? You naughty cocksucker!" "Yeah, what the hell, Annabelle! What is my mom doing home earlier than usual, and why are you okay with her around seeing you get your dick sucked by her son?!" I said. "We used to do the kinkiest things all the time when you were younger!" Annabelle said, "its kind of how they repaid me for having to deal with you, mister pain-in-the-butt (now literally and metaphorically)!" She smiled. "Also, I think your mom was turned on seeing you wear her clothes. She'll be out in a second for your second round, mister. You're getting a poundin' from your mother." Ohhhh boy, I thought. My mom doesn't have a dick, does she. That would ruin me. All of a sudden my mom came out of her bathroom in a black leather dominatrix outfit. It drove me wild but I tried not to show it. While climbing to a safer spot on the bed, I noticed my mom was wearing a strap-on. I knew I was in for it at that point. My mom walked over to Annabelle and kissed her right on the mouth. It wasn't just a kiss, though. There was tongue and I saw her stroke Annabelle's saliva-covered cock with her leather gloves. It was an amazing and erotic sight to see. Not many guys get to see their mothers make out with a transsexual, and boy, it is amazing. My mother moved from Annabelle to me, her blue, clear, 6 inch long, stap-on swinging between her legs. I didn't know what exactly I had in store, but I was scared. My mom moved in to kiss me, it was fantastic. She slid her hand up my leg while we kissed and fondled my balls in my (her) panties. It was so erotic and fantastic I could hardly react to anything. My penis has never been as hard my entire life. We parted lips and she whispered into my ear "bend over, son, your ass is about to be ravaged." I got into doggystyle position and my mom slid my panties aside and pressed the dildo into my asshole. I looked back at her and told her I've never had my ass penetrated before and she said "Well you're in for some fun then!" and pressed in harder. The rubber dildo at this point was in about two inches and it felt like nothing before. Annabelle gazed at my mother in her dominatrix outfit sliding an artificial dick into her son's ass. She looked at my cute little outfit, so innocent and virgin-like minutes ago, but now, things were kinky. It was fair to say I was a full-on slut from that moment on. My mom slapped my ass and started pumping harder on my ass. It felt amazing. Annabelle walked over and wagged her dick in my face. "Its not gonna suck itself, silly!" she tempted me with her 4-inch cock. I slipped the little guy into my mouth and I took both dicks at once. Slurping down on Annabelle's dick, I could feel it throbbing down in my mouth while at the same time, I felt the pumping motion of my mom in my asshole, now going about 5 inches deep into my ass, pumping away. "Oooh I wish I knew my son was such a slut, we would've been doing this for ages!" my mom joked with Annabelle. "Yeah he looks so cute in your clothes, he should wear them more often!" Annabelle said back to my mom. I could feel Annabelle's dick about to climax in my mouth and finally she came in my mouth. I swallowed her sweet, juicy cum. It tasted a little salty, but delicious. My mom went over to my mouth and made me suck off the dildo she just used on me. It tasted strange, and it was so erotic to me to suck on my mom's "dick." My mom put me down on my back and started pushing the dildo into my ass again. This time she stroked my cock while plowing away at my ass. I came in the matter of seconds after she started stroking my dick and she got the cum all over her face and her milky tits. Her cum-soaked tits we now hanging in my face and she forced me to lick the cum off of them. My own cum tasted delicious on my mom's breasts. "Come like it off my face too" she said. I started licked my cum off of my mom's face and she started moaning. Annabelle, my mother, and I all kissed and stroked each other's bodies until morning came. While Annabelle started to go downstairs that morning she looked at my mom and I and said "please promise me that every night this week will be like last night." It was a promise I planned on keeping. My Babysitter Ch. 03 Getting forced down, a big, fat cock shoved down my throat. I was choking on it, I couldn't breathe. Oh, and another one, ramming my ass. It felt so powerful, and I felt powerless. These things never last though, and before I knew it, I was awake. I opened my eyes and there was the most beautiful woman to me, Annabelle. Well, that is if you consider her a woman. It doesn't matter to me, though, she's so perfect. From her juicy, pale ass to her soft, red lips. Then I felt a touch that was so familiar but strangely different. The warm, friendly touch of my mother. "How'd you sleep last night, my little guy?" My mom beamed. "Mmmm good, still a little sore" I respond. I turned to Annabelle and she opened her eyes and fixated them on me. She then gave me a sweet morning kiss. "Good morning, you little slut." She said "Ya know you still have your mother's clothes on? You're so hot in those." I blushed. "Oh gosh I forgot about these" The pink lace bra and the black lace panties were still on, my morning wood now poking out of them and out of my red pleated skirt, pressed against my white blouse. "I see that cute little fella right there" Annabelle grinned, and rubbed her fingers across my dick. After laying around in the bed a little, mom had to get up to go to work. Annabelle and I only had 5 more days to fool around, cause we cant do this kind of stuff when he gets back from Seattle on Sunday. I was downstairs when Annabelle comes downstairs wearing a white tanktop and a red pair of shorts, her bulge prominent. She walked straight over to me and kissed me. Her lips were like soft and alluring. It turned me right the fuck on. Annabelle stopped kissing me. "I got an idea actually. Lets look up a random porno and reenact it." She said with a smile. "I dunno, what if they do something weird I'm not comfortable with?" I said "Sam. What the hell are you not comfortable with?" She said, questioning me. "I guess, lets do it." I say, unsure. She opens up a porn site and searches "tranny + male" and clicks the random button. The video comes up and we both are watching intently. The video starts with the boy tied up to a bed. At this point I know its gonna be bad. Annabelle ties me down with some rope to my bed. I feel so restricted and vulnerable, my cock so exposed. The video continued, the tranny walks up and shes wearing fishnet stockings, leather highheel boots, a yellow dress. Annabelle found a set of these clothes or the closest thing she could find in my mom's closet. The tranny in the video begins to do some spanking, and I shook in my bed to try to get it. But I was secured too well. She slapped my legs and squeezed my balls tightly. They were so sensitive. I felt so susceptible and afraid. The video then showed the tranny hop onto the man and rub him all over, Annabelle emulated this. She ran her tongue along his entire body and finally ended on his dick. I felt so connected to the man in the video. It was like we were the same person. Annabelle and the tranny begin to suck on mine and the man's dick, slow and really showy. The video skipped to a scene where the guy is tied by his neck to the bed like a collar with the rope tying his hands behind his back too. I was so horrified at this sight, even though I've taken it in the ass before. She tied me up and my ass just stuck in the air like a lone hill on the plains. The video tranny started rubbing her fingers over the guy's ass and circled her fingers around his asshole. Annabelle repeated this and it turned me on like crazy. It kind of tickled. I tried to squirm but my hands were immobilized. Annabelle and the video girl started slipping her dick into mine and the man's ass. I felt her little cock push into my ass. She started fucking me harder, and I realize I've never had cum in my ass. I tried not to worry about it and just enjoyed the ride. She kept pounding relentlessly and finally she screamed "ooh baby I'm cumming!" and I felt the warm cum ooze into my ass. It felt amazing. I felt like a little slut. She leaned in and started licking the cum up out of my ass. It tickled and felt so wet. We cleaned up and just enjoyed the rest of the evening together kissing and watching movies. Tuesday was almost over and the countdown to my dad being home was looming over our heads. We went to sleep that night with cum still dripping out of my ass.