tagTranssexuals & CrossdressersMy Babysitter Ch. 02

My Babysitter Ch. 02


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.

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