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Telling Mom I'm A Crossdresser Part 6: Missy and Mistress Keri

Missy has her first BDSM experience. Plz rate and comment
Up until now, I have enjoyed my time as Missy. My mom had kept me busy with clients and we pulled in a lot of extra income and I was able to experience a lot of different fantasies, However I had not had the chance to try anything involving BDSM, or not yet at least.

One day I came home from mowing the lawn for an elderly woman when I walked in the door to find my mother smiling deviously at the kitchen table. I instantly knew that Missy had been hired for another job.

I sat down next to my mother and she told me she had a new client lined up for me and this would be a little different then what I was used to. I asked her what she meant by this but as always she did not want to tell me anything and I had to find out on my own. The only thing she did tell me was some instructions as to what I needed to do to get in. It seemed strange but I agreed and she told me the instructions for the night ahead.

Friday came and as usual it was time for Missy to get to work. I went to the person’s home in my normal every day clothes as instructed and walked around to the back where there was a door that leads straight to the basement. I made sure to also bring the blonde wig as it was also asked of me. I knocked on the door three times and opened it.

“Hello, Missy is here to provide her services.” I said out loud as I entered the room and closed the door behind me.

There she was, A woman about 6 feet 5 inches tall in her thigh high leather boots with laces going all the way up the leg. Only the boots were leather where as the rest was a full PVC dominatrix suite that I had seen on my favorite tranny site to buy clothes. It was all one piece that went the full length of her arms all the way down her back to even around her busty ass and tits just to be completely zipped up the front from her neck to her pussy. She also held a paddle that said slut in big red letters across one side and punishment on the other side. Her nails were painted a bright red the same as her lips and her blonde hair flowed almost down to her ass. Oh my god, Her ass and breasts were amazing. Her bra size must have been the same size if not bigger then my mother’s and her ass looked so tight she could crack a walnut.

“Are you Keri?” I asked in a stuttering and almost fearful voice.

“That is Mistress Keri to you slut!” She said in a stern voice as she walked closer to me and grabbed me by my hair. She led me to the middle of the basement which was a fully equipped basement with everything you would see in a BDSM porn movie.

She threw me to the middle of the room and told me to strip. I did as told until I was completely naked.

“I hear you like to dress like a little tranny whore. Is that true whore?”

“Yes Mistress Keri.” I answered quickly and submissively.

“You are a boy, if you like to be a little girly whore then I guess I shall treat you like one.” She said as she smacked my ass with her paddle which made me flinch.

“Put on your wig and then put on the clothes I have in the corner.” She demanded.

In the corner I found a strict PVC crop top and sazzy PVC spank skirt with no panties, of course and only went far enough down to barley cover my hanging clitty cock. I quickly put on the clothes and my blonde wig as she watched. I could tell she was getting pleasure from watching me squirm and seeing my cock strain against the front of the skirt. She rubbed her pussy and walked over to me and gave my ass a hard spank as she spoke.

“So I hear Missy likes to get it in the ass. Is that true?” She asked sternly.

“Yes Mistress Keri, When I dress up as Missy I like to get fucked in the ass.” I replied sheepishly.

“Well tonight you are going to use your cock to please me and no excuses! I want you on the spanking horse now!” Mistress Keri demanded.

I got onto the horse with my legs spread apart. She clamped my ankles into the restraints near the floor and then used a type of wrist restraint that clamped my hands together about 2 feet away from my neck in front of me. She grabbed me by my hair and told me to lean forward as she started giving me a brutal spanking hard on my ass. It hurt at first but it gradually started to become erotic but still sting a little more each time she hit me hard on my ass. Then she went to her rack of BDSM equipment and got a riding crop and an inflatable penis gag.

“Little whore, you will learn the value of your voice and your body.” She slipped the penis gag into my mouth and smacked the rest of my body with the riding crop. She began with my chest smacking my nipples and my chest moving down to my thighs leaving red marks as she went. Finally she got to my genitals, She knew not to hit too hard but she decided to tease me instead while patting them.

“Such a naughty little tranny you are Missy, getting horny for men and woman and using your body in such dirty and slutty ways. Hmmm, I will make you a good boy tonight.”

She pushed me down on my back while still on the horse with my head hanging off the end. She unzipped her suit so that her pussy and ass were fully visible and her breasts were giving a tease of what they looked like with just her nipples giving an occasional hello. My cock throbbed as I looked at her beautiful body as she stood over my face and put her ass right over my nose with her pussy by my chin.

She started to inflate the penis gag which grew out of my mouth till it was seven inches out and went about 4-5 inches in my mouth. I swirl my tongue around it to get a feel of what it was like and noticed a little hole in the end where the tip was. The extension on the outside grew until it went inside her pussy. She moaned as it went deeper and deeper then she started to bounce on it, riding it like it was a mans cock deep in her pussy trying to make it shoot all its hot wonderful mess inside of her. I could tell she was enjoying it because her pussy juice started running from inside the penis gag and into my mouth like it was a funnel collecting her love juices and drooling it into my mouth. I swallowed again and again as I could feel her warm flood in my mouth.

“Mmm Missy they said you were good with your mouth but I didn’t know you were this good. Oh god yes that feels great, I’m going to take my time with you until I am satisfied.”

She rode my face until her orgasm squirted into my mouth making it shoot out of everywhere it could. I thought I was going to drown until she stopped and pulled me up to move the penis gag. She licked my face up of her cum and kissed me deeply swirling her tongue with mine as we made a deep passionate kiss. Then she broke the kiss and looked at my cock to see that I was rock hard and throbbing.

“I see my little slave has enjoyed himself a fair bit. You are a little masochist aren’t you?” she said to me playfully and rubbed my sore bottom as she teased her nipples. She grabbed me by my hair again and pushed me into a bondage chair with a dildo stuck to the seat. She forced me down onto it as it slid right inside my ass as she proceeded to bind my wrists and ankles to the chair.

“Since Missy enjoys cocks so much I thought my little slave would enjoy the pleasure of both worlds at once.” She smiled as she got onto her knees and started licking the tip of my cock.

I moaned as she slurped up the sides and lapped her tongue along my shaft and then moved down to my balls. The dildo in my ass was ecstatic as her sucking made my hips move making the dildo grind inside me. Then I heard a click and the dildo started vibrating making me moan louder and my mistress take my cock deeper into her throat until she had completely swallowed my cock. She started to bob her head up and down on it while we looked at each other straight in the eyes. Suddenly, my eyes became wide and my jaw dropped as I seen Mistress Keri hold up a pump that had a hose that connected to somewhere in the chair. She started pumping it and the vibrating cock in my ass got bigger and bigger with every pump.

After about 10 minutes of this treatment I couldn’t last anymore as I warned my mistress of my impending orgasm.

“Mistress Keri if you keep going I’m going to cum!” This was apparently what she wanted because she sucked incredibly hard now until I came filling her mouth with my cum.

She got up and straddled me with her mouth full of my jizz as she held my mouth open and drooled my own cum into my mouth. She looked me in the eyes and told me to give it back and I did as told kissing her and swapping my cum back and forth until I was hard again.

With the dildo still in my ass and my cock hard again my mistress took my cock and stuffed it into her pussy and started to ride me.

“Now slave you will make your Mistress cum with your huge cock!”

“Yes Mistress Keri.” I said with excitement.

Her pussy was so warm and wet, I could feel every part of her warm canal squeeze me so tight and it swallowed up and pulled my cock over and over again inside her. Every so often she would grind her hips onto me before riding me even harder almost pulling my cock completely out of her and slamming back down making a slapping noise with each thrust.

This continued for 30 minutes and now her legs were up on my shoulders. I was at my very limit as I could tell she was as well and this time both of us were going to cum like a flood. I leaned forward and sucked on her nipples and gently nibbled them. This sent her over the edge and made her clamp down hard around my cock hard which in turn sent me over the edge as well. We Screamed as our orgasms collided into each other inside Mistress Keri as she fell into me and panted.

She untied me and unattached the dildo while it was till inside me with the straps and then tied it around my thighs to keep it in place. My cock needed more time to rest but she didn’t plan on letting me use it again quite yet anyway. She attached a leash around my neck and pulled on it as she gave my ass a little slap with the riding crop.

“On your knees bitch beside you mistress we are going to a special room of mine.”

She leads me through a door near by and opens it to reveal a bed with a fucking machine that had two working dildos near the foot of it. She tells me to get up on the bed and spread my legs wide open. I do as told but as I get up on the bed she rips the dildo from my ass and starts smacking me on both cheeks.

“Whose the little slut here?! Who is it?!” She yells sternly waiting for my response.

“I said who slave!” She shoves 3 fingers in my gaping hole to keep me wide open.

“Ahh, I am Mistress! I am a little slut and I am the biggest slut here!” I yelled and moaned in pleasure and excitement.

I got to lay on the bed on my back and spread my ass wide keeping my hole open as Mistress Keri positioned the dildo to my hole and turned it on so it started to slowly go in and out of my ass as I moaned.

“Such a good little whore, your pimp wasn’t lying when she said Missy will do anything.” She said with a devious grin and a giggle.

Then she positions herself on top of me with her breasts in my face as she got the other dildo positioned against her asshole. She turns on hers to about the same rate as mine and tells me to suck on her tits. I do as told and lick and suck on them hungrily, gently nibbling on them again as I sucked them into my mouth as deep and as hard as I could while the dildo plunged the full 7.5 inches into my ass. I’m sure my mistress also was feeling very good with her anal dildo as well because she was moaning wildly as she rubbed her pussy and stroked my cock hard. Eventually she pulled my mouth off her tits and attached nipple clamps with chains to our nipples, but not from one nipple to the other. She attached the nipple clamps to each other, her right nipple to mine and my right nipple to hers and every time one of us moved it would pull the chains on the other.

We moaned like whores and took the dildos hard for what seemed like 45 minutes or an hour, who would be counting when the waves of pleasure were this intense. We could feel ourselves building to an amazing orgasm as I wrapped my legs around my mistress then she came close and pressed her tits against my body and our chains rubbed together. We kissed deeply swirling our tongues together with deep passion as we came all over ourselves, the dildos and the bed. We turned off the machines and panted as we fell asleep for the night.

Morning came and Keri was gone but left an envelop with a lipstick mark on the front that read “To Missy”. I opened it to find $1000 dollars and a picture of her naked body spread eagle. I turned it over to find writing on the back that said to come back anytime and that she loved her time with Missy.

I went upstairs and found her half naked with only a full body fishnet on similar to what my mother had worn so many nights before. She saw me and instantly pounced and started grinding my crotch.

“I want more, not as your mistress or you as Missy but just a good fuck. Can you handle it big boy?” She said confidently.

“Yes Keri.” I moaned.

We spent that morning having sex in every position we could think of. I bent her over the kitchen table and smacked her ass, she sat me down on her couch and rode my cock forwards and back giving me a good view of both and even pile driving her pussy and ass until we were sweating and our cum oozed from both her holes.

I got my normal clothes back on and started to leave when she stopped me.

“Here you can keep the clothes you used, think of it as a memento and for future fun with me and here is some extra money for the wonderful morning.” She said with giggles and a devious smile on her face as she handed me another $1000 and tapped the paddle on her hand.

I smiled and said thank you but she stopped me again with another present. I opened it to find that it was 2 little collars. Both were black and one had big shiny letters that said on one SLUT and the other said Slave.

“I felt that Missy really earned these and I hope the next time I want her services she will be wearing one of those for me.” She winked and padded my butt to send me on my way.

I got home and told my mom everything and handed her the money as usual.

“I see Missy was a good little slave because this is more then what I had asked.” She smirked and gave me a little wink to say I had done a good job.

I went upstairs to add my new clothes to my collection when I found that my drawer was empty. I looked around and then to my closet to find my clothes had been neatly hung up and perfectly divided next to my normal boy clothes. I thought to myself I guess mom decided that I needed more room for the clothes I was getting, and she was right.

That night I laid in bed to rest and listen to a new Ipod and music I had gotten with my money. I was really enjoying my time as Missy and hoped it would not end as well as hoping I would have another new sexual experience soon.

To be continued. J

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.

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