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Telling Mom I’m A Crossdresser: Part 2.5 My New Toy

This is a simple intermediate story i wrote between part 2 and part 3. Plz rate and comment :)
It was a few days later after my night with mom at the adult shop, and my ass was still sore and I could still remember the taste of the cum in my mouth from that man. I could also still feel the pain in my ass from having to walk all the way home with my mom’s dildo in my ass.

My mind wandered as I thought about how my mom reacted to getting her dildo and how horny she got just by looking at it and me during that night. After we got home, my mom told me to have a bath and go to bed because it was late. Then she just disappeared into her room with her toy and left mine with me. I could tell from the moaning I heard while laying in bed that she was trying it out, which to be honest made me want to try my new dildo even more.

I was sitting on the couch as I thought about that night and decided to go up to my drawer and look at all my outfits I had accumulated since coming out to my mother. I laid the outfits on my bed in their proper organization starting with the latex one I had worn during my first time with the outfit I wore to the adult store next to it. Next I went into my drawer again to get out my other clothing that my mom had given me and put them in a big pile by my pillow. I set my sex toys next to them including the butt plug, the cum stopper, my new jelly 7.5 inch dildo and the breast forms all on one of my pillows to prop them up as if they were on show at an art gallery. I especially took pride in my new dildo. It was soft yet very flexible, with a long smooth shaft that was only about 1 ½ inches in diameter but reached a good solid length and a tapered end for smooth anal penetration. Looking at it I had to smile and was glad that my mom had taken the one without the suction cup because I loved the idea of sticking this thing all over the house for different sex positions.

Since my mother was out I decided to have a little fun while she was gone and got out some of the tranny porn she had given me but first I decided to get dressed in something sexy. After searching through some of my clothes I had decided on a nice pair of lingerie. It had a nice black bra and panties with pink mesh with some black fishnets and a cute leather twinkle collar that had bells on it and was pink colored. It matched nicely with my bra and panties. I finished with some lipstick and mascara, a pair of 5 inch platform heels just like what strippers wear and my blonde wig. Then I grabbed my new dildo, the small bottle of baby oil I had and a porn video. I stopped and thought it would be easier to clean this thing if I got a condom to put over it. I went to my mother’s room and got one, then I headed to the living room so my fun could begin.

I put the dvd in the player and sat down on the couch as it started. As I continued to watch the video I started to become horny as my cock got hard in the panties. I rubbed my cock and laid on my side with my panties off so that I could rub my hole and lube my ass.

It felt so slippery as I dipped my finger in and out feeling my ass enclose around my finger and try to pull it in as I took out my finger just to welcome it back again. I stuck in another finger to accommodate the width of the dildo and started to move back and forth and spreading my fingers till I was loose enough to for it to enter. I moaned as I looked up and saw an incredibly sexy shemale on the screen sucking a man’s cock.

I decided to do the same and put the dildo in my mouth as I fingered my hole deeper and deeper making myself moan even louder. I went on like this for about 10 minutes before applying the condom and have some fun.

While still laying on my side, I put the dildo up to my ass and started to push. I moaned as the dildo passed my opening and made its way into me. I could feel my ass suck in the dildo as it slides through my fingers and into my ass till it was 6 inches in. I moaned as I started to move it back and forth stroking my cock as I did.

I continued for about 15 minutes before that position had gotten boring. I went to the kitchen to retrieve a chair and put it in the middle of the floor so I could continue and still watch my movie. I stuck it hard to the chair straight up so that I could ride the dildo in the chair like the shemale in the video who was taking the man’s cock inside her so hard. I leaned forward and rubbed it along my cock pouring lube all over it while it was still in the crack of my ass. Then I went up and sat down on it, making it slip inside me up to the 6 inches I made it to before. I decided to go deeper as I spread my legs wide and slide down until my cheeks touched the chair.

I took a few deep breathes as I got used to it being inside me. I quivered as I could feel my ass throb around it all the way down. I started to pump up and down on the shaft as I stood on my heels using my smooth shaven thighs and legs to let my pretend stud go in and out of my ass, grinding on it deep and hard then pulling it out up to the head then thrusting all the way back down making myself moan and scream as I almost reach orgasm.

Then I hear a door click, frozen I don’t move as my mother walks in and catches me masturbating with a dildo again. She just smiles at me and says she had been watching me for a while. I look down at her pants which are soaking wet and her nipples that are hard as rocks sticking through her shirt.

I don’t move from my spot as she goes upstairs to take off her clothes and retrieve her toys as well to join me. She comes down in a pair of white stockings, garter belt and panties with a white basque that did nothing to cover her big beautiful tits. She held up her Jelly dildo and sucked on the end while she rubbed her pussy.

She sat down on the chair beside me with her legs up in the air spread eagle and running her dildo along her pussy lips and onto her hole then back up to her clit. She pulled off her panties and started running her toy in and out of her pussy as I watched, I got hard instantly. As I felt my cock grow hard again I started to feel the dildo in my ass feel even better. I started to ride the dildo like I was before when my mom got up in front of me. She buried my face into her pussy as I started licking her, sucking her clit and burying my tongue deep into her dripping lips as she moaned.

I got up because my legs were getting tired and started sucking on her nipples while she stroked my cock. I ran my hands up and down her body feeling her sexy lingerie as she felt all along mine. She went around and grabbed my ass putting her fingers in me as I put fingers into her pussy then glided around to her ass. She moaned loudly as she stretched my hole open making me so horny I just buried 2 fingers into her ass and 3 fingers into her dripping pussy.

She pushed me off and told me to get on the floor on all fours. I did as told and watched as she took our 2 jelly dildos and stuck the suction cup end of mine onto the base of hers making a double jelly dildo. I watched as she got down onto her knees as well and inserted one end into her ass as deep as it would go and pressed the other end to mine. I couldn’t last anymore as I backed into it hard just as she put the end to my hole and went right back to the suction cup, pressing into her more as well.

“You naughty little slut Missy, are you that impatient for a cock in you?” She says pushing back into me making me moan loudly and her quiver. We started to push our sexy asses back into each other making the dildo thrust into the other moaning loudly with me stroking my cock and her rubbing her pussy as we both squirted onto the floor.

I turned around and smacked her ass then held onto the dildo as I thrust back deeper into her until she was at the suction cup to. She screamed as that put her over the edge and her pussy squirted all over the floor and onto my balls. I could smell and feel her juice and the scent of her wet pussy which made me crazy. I fell to the floor pumping the dildo into her more as it mixed with her juices. Then my mom pulled the dildo out of her and grabbed me by my choker as she pulled me back smacking my ass hard.

 "Bad girl Missy, You made your mistress cum before you. Such a naughty slut you are!"

She laid on her back and put her legs wide open in the air as she told me to do the same. I felt as she inserted the dildo back into my ass and hers as well. We both sat up at the same time and thrusted our hips into eachother watching eachothers genitals leak our juices like two girls sharing a dildo in one of those lesbian movies I watch when im not Missy. We stared at eachother with lustful eyes before I grabbed my mothers ankles in my hands with the dildo still inside me and got on top of her. I started riding the dildo Like I was in the chair, but this time it was plunging into my mother's asshole. We both moaned like little sluts as the dildo went in and out of us with furious motion making both of us want to cum buckets of pussy juice and cum.

Finally we were just about to cum when the dildo slipped out of our asses and fell to the floor. My mother grabbed me and stuck my cock deep into her pussy, making me fuck her wildly like an animal as we kissed with deep emotion until she let out another orgasm as did I deep in her pussy.

She pushed me on my back and laid me down as she straddled my face and pumping the dildo in and out of my ass. I spread my legs wide as she fucked me harder calling me a slut.

 "Eat my pussy you dirty girl. If you enjoy making my pussy cum so much you can eat up my juices afterward."

I lapped up her pussy as she sucked my cock making me hard and moan while still pushing the dildo in deep until I needed to shoot my load of cum into her mouth. She held her mouth there until I was done and cleaned me up. Each shot hitting the back of her throat while she licked all around my head. Then my mother turned around and kissed me deep making me taste my own cum and swirling our tongues together before she took the cum back and swallowed it all.

"Get on the couch and wait for me you slut. I will be right back with a friend." She said with a grin savouring the flavour in her mouth.

I watched as she walked away and her juices flowed down her thighs. I licked all around the inside of my mouth tasting all the delicious flavours.

It wasn’t long before she came back wearing only her white stockings heels and a big strap-on with one of the jelly dildos secured in it. She picked me up by my hair and smacked my ass all the way to her bedroom. She threw me down next to a little box that felt cold. She picked it up and opened it to reveal 6 condoms full of cum. Then she went over to her dresser and started record on the camera she used on the adult store again. This time I knew what it was for.

“Suck on my cock you little whore.” She said in a demanding voice.

I started licking the dildo sucking it just like it was a mans cock as I started up at my mother’s face. I reached under and started rubbing her pussy as she rubbed her big breasts together making her even more horny and wet then I could already feel between her legs. As I sucked the strap-on hard and deep, She took out the condoms full of cum and one by one started dripping them onto the tip of her cock with my mouth open catching what ran off.

Once the last one had been emptied onto my face I was all messy and sticky and my fingers had plunged deep into her pussy and my throat had completely swallowed her strap-on cock. After about 5 minutes of sucking her cock, She pushed me back on the bed, put her fingers in my mouth and fucked me in my ass balls deep while in the doggy position.

“You like that you little bitch? You like my hot, plastic, cum covered cock fucking you deep in your gaping ass?” She said in a dominating voice, pumping and spanking my ass while I moaned like a slut.

“Yes! Oh god yes Mistress Mommy! I love your big plastic cock deep in my ass. I love how you fuck me so hard and deep in my gaping ass like a little bitch. I love you, and I love that you are my pimp and I’m Missy, your dirty little cock sucking whore.”

With that she got up onto her heels and opened her legs while still fucking me in the doggy position. She got overtop of me and got balls deep as she fucked me with my ass in the air and the strap-on rubbing her clit madly making her close to orgasm the same as me. As we both neared orgasm, she smacked my ass a couple more times and asked if I wanted her cum.

“Yes Mistress, I want you to cum inside me. Make me your slut.”

She smiled as I heard a click and felt an instant rush of warm liquid filling my ass which I later found out was her pussy juice mixed with lotion. Her strap-on fell from my ass as I laid on my back and panted heavily along with her.

She stared into my eyes with a satisfied look on her face as I did the same but with a smile on my face. She then got up and sat on my face.

“Lick my pussy and clean me up bitch.” She moaned and fell forward cleaning my hole and my cock clean.

I proceeded to clean her up licking her clean as she did the same. I licked both her holes clean up her lips and inside her ass then back down into her pussy which I reamed out thoroughly. We cleaned each other for 20 minutes before rolling over and going to sleep in each others arms.

To be continued.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

Continue reading Telling Mom I'm A Crossdresser Part 3: Missy's Weekend

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Posted 07 Mar 2014 16:36
you are great and reading your stories are helping me in learning to be a women
Posted 04 Jan 2013 16:43
what a great writer you are
Posted 22 Feb 2012 12:03
this I just how I would love to interact with a woman. just great

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