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Telling Mom I'm A Crossdresser Part 2: The Adult Store

Missy goes out and meets her first gloryhole. Please comment and rate all of my stories. :)
I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived.
 
It was just past 9am when I heard a fumbling at the door, my mother had walked in with her heels in her hands and her clothes hanging loose a little from her body.

"Seems as though im not the only one who was having fun last night." I smiled and thought to myself.

As she made her way to the kitchen, she started taking off her clothes leaving on only her panties and bra. She looked me up and down and smiled.

"I see you opened your presents, what did you think of them?" As she rubbed her body up and down feeling more confortable in her underwear.

Smiling I replied, "It was fun and he said he was gonna come back next week."

Putting her hands on her hips she said, "Oh? Did he leave any money with you?"

I pulled the money out of my basque as my mother walked up and snatched it from my hand, counting it to make sure it was all there.

"You naughty girl, he must have liked you because he left you some extra in here."

I blushed as she put the money in her bra and looked at me up and down again and told me to go change because she had more plans for Missy tonight. I just looked at her and wondered what those plans could have been as I started walking to the stairs. She stopped me and told me to drop all my clothes except for my thong. I did as told leaving it on the floor in front of her as she smacked my ass and pointed upstairs.

It was after supper time when my mom called me Missy again. I came into her room and she told me to sit down in the bathroom because she was gonna do my makeup after she laid out my outfit for the night. 

"Yes, Mistress Mommy," I replied and obeyed as I went to the bathroom to wait for her.

A few minutes later she walked in and sat down beside me. She started with my eyes applying shadow and mascara then working down my cheeks and onto my lips. All together, she laid the makeup on a little heavy but I didn't mind because I had become instantly hard. Then she proceeded to do the same with her and placed the blonde wig back on my head. She just looked at my erection and giggled as she handed me the cum stopper and lube and told me to put it on since I was ready so soon.

I slipped on the cum stopper and she finished with my makeup.

"Well now don't you look pretty Missy, All the boys will want in your pants in no time," she teased as my face burned hot. 

Then my mother took my hand and led me back into her room. There on her bed were two outfits that were almost identical but I could tell the smaller size was for me. Mine had a pink g-string and bra with some PVC hotpants and a tank top that showed off my tummy and shoulders. Her clothing was similar however her underwear was black as well as the tank top. Her hotpants were the same as mine, however when she slipped it on she had alot more to show as it just barely fit over her hips while mine clenched my ass tight. We pulled our thongs up over our hips then put on our tank tops for the night.

"Wait a minute." She suddenly stopped us as she looked over at me and realized she forgot something.

"Bend over and pull your pants and thong down a bit I need to insert your toy for the night."

She winked and went to her drawer as she pulled out a butt plug slightly larger then what I had worn last night as well as some breastforms to put in my bra to give me tits almost as big as hers. She put the breasts forms in my bra and handed me the lube and plug as she sat down on her bed.

"Put it in slow and don't hurt yourself."

Blushing, I slowly pushed the toy in moving it back and forth making it slide into my ass till it was solid in place. Then I pulled up my pants and we finished our outfits with our heels. She put on some pink, open toed 5 inch heels and I put on the same shoes but in black.

By this time it was now 8pm and getting dark out. She told me to practice walking in the heels a little to get used to them. I started giving sexy poses as my mom had grabbed her digital camera and we took pictures of eachother being two slutty girls.
 
"Oh sweetie look how sexy you are! Missy is going to get alot of attention when we go out tonight."

 I stopped in my tracks and shuddered for a second before remembering that it was dark and I was an open crossdresser anyway and continued modeling like a porn star for the camera as my mom did the same.

An hour had went by and it was time to leave. My mother had put the digital camera in her purse and took my hand as we walked out the door and down the street. We walked a few blocks and listened to the clicking of our heels until we had gotten to an Adult store. She caught me looking at it and decided to walk towards it.

"Hey I have an idea, let's go in and look at a few things maybe get you a new toy," she said with a grin on her face.

We walked into the store as the cashier looked us up and down and whistled at us. I blushed but my mom giggled as we walked around and looked at the merchandise that was available. I looked at a few of the dildos as I saw my mom get a key from the cashier. She said nothing but motioned for me to come with her as she led me to a room that was just barely big enough for both of us and a hole about crotch high in the wall. I instantly knew what it was.

It wasn't long before we saw two fingers poke through the hole as I got down on my knees to look. My mom knocked on the wall a couple times and stuck her hand by the hole demanding that we should get the money first. I felt like such a dirty little whore with my mom there and her using me to make money, but I have to admit it was alot of fun.

Suddenly, out popped $200 with a voice.

"That's two hundred for a blow job with no condom right?"

"That's right." My mom moaned while squeezing her tits and staring at the hole.

Then his cock poked through the hole, it was about 7.5 inches with thick veins running along the sides of it. He had a strong smell, like he needed to shoot a huge load of cum but hadn't gotten the chance to in a long time. I grabbed his cock and started stroking it up and down as my mom just watched and took out her digital cam. She looked at me and winked as I started sucking on the cock while taking pictures through the entire session.

I started to lick up his shaft and around the head as I gently kissed the tip leaving a few good lipstick marks all over his cock. I felt him get harder like a rock as I pressed my lips to his head and slowly lowered my head down his shaft, swirling my tounge all around the head and pressing my tounge hard down his shaft as I went up and down Then everytime I came up, I would swirl my tongue around his head again and every so often kissing and sucking on his balls while I stroked him just to give him something new.

I started to hear moaning as I sucked harder, faster and deeper. I deep throated his cock again and again going right down to his thick bush he had. I heard my mom snap picture after picture of me with the big cock in my mouth. Losing myself in my lust I couldn't help but stick my tongue out and lick his head like a lollipop and popping his cock out of my mouth from the side of my cheek just to pose for the camera.

Suddenly he started to shoot as I pulled my head back and opened my mouth for him to let load after load onto my face and tongue. The smell was intense and my mother took several different pictures of my face covered in cum as she smiled with a devious grin. Then she got down on her knees and took his cock in her mouth as well, licking him clean and stroking out a few more shots. I just watched as he got hard again from my mom sucking his cock. She told him to wait and started to fiddle around in her purse.

She pulls out her 6 inch dildo that she had caught me with a few days before, and stuck it to the opposite wall directly across and same height as the man's cock. She gave my ass a hard slap and looked me in the eye.

"You know what to do Missy," she said with a sexy wink and slowly stroking the man's cock to keep him hard.

Getting back onto my knees, I pulled down my hot pants leaving my thong on as I moved it to the side and removed the butt plug. Then with my ass already lubed and wet, I inserted the dildo into my ass and moaned as I took the man's cock back in my throat once again. I rocked my body back and forth being penetrated by the dildo then pulling off it as I took the juicy real cock down my throat but never at the same time. By this time, my mom had started using the recording function on the camera and was taking a video as she watched her little whore at work and earn her living. 

I started to rock faster and faster, gagging on the cock as I felt him twtich in my throat as I moaned making him throb more and more. I moan as well as I feel the dildo go in and out of my ass sending waves of pleasure one after the other every time it went down and making the cock taste so much better.

"I'm cumming!" The man yelled from the other side of the wall.

I leaned back, stroking his cock as I moaned loudly with the dildo going deep into my ass, making me feel an orgasm as well but it couldn't escape through the cum stopper. The man came a few more good shots onto my face as I screamed in pleasure before sitting up to rest with the dildo still in my ass. I felt my hole throbbing as I watched the man's cock disappear through the hole. Mistress Mommy told me to keep the dildo in my ass as deep as it would go and pulled up my pants and kept it there till we got home. She lubed up the butt plug and put it in her ass and pulled up her pants as well.

We walked out of the small room to find the man waiting for us. He wanted to see us one more time and meet the hot little slut that was sucking his cock so good. My mom pointed to me and I blushed as he handed me another $100 down my shirt, spun both my mom and I around and squeezed our asses hard, rubbing our toys and making us moan. My mom wrote our numbers on a piece of paper and we both left a lipstick stain on it before he walked out of the store. Before we left, my mom went to the dildo section once again and picked out 2 nice looking 7.5 inch jelly anal dildos, one with a suction cup and one without. She grabbed the money from my shirt.

"With your hard earned money I think you deserve a reward Missy, and of course your pimp gets something as well along with the money," she said with a horny grin and rubbed along the box of her new dildo before we walked out of the store holding hands to go home.

Later that night, I found my my mother at her computer.

"Hey mom what are you doing?"

She turned to me and grinned as I found the pictures and video she had taken on an escort site she had made for Missy's services, with spaces for clients to put in details of their fantasies for her to comply with. 

To be continued?

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

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