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Telling Mom I'm A Crossdresser Part 8.5: Cops and Prostitutes

What Missy needs to do instead of going to jail for prostitution. (continue of part 8)

When morning came, I told mom what had happened the previous night. She had a surprised look on her face and I could tell she was feeling uneasy at the thought of me getting arrested while dressed as Missy as well. We talked for a while and she was glad as well that the police officer was a Missy fan.

“We can definitely let him have a free night in exchange for not getting a criminal record.” Mom said as she gave a sigh of relief.

We started to talk about the sybian that mom had bought and some plans for it and the website when the phone rang. The first to answer the phone was mom and she talked to the caller for a few minutes before hanging up.

“Who was that mom?” I asked.

“It was the police officer you were just telling me about. He said he would like to call in his favor for Friday night.” Mom replied.

She continued and told me the details for Friday night, and I have to say it was a little different then what my other clients have asked.

I found out that the officer’s name was Greg and I was to meet him at his place. I arrived there by taking the bus around 9pm and wore my normal clothes like I would any other day. I found it to be a new experience seeing as though I was to start off as my self and not as Missy but I figured that was because he didn’t want his neighbors seeing a cross dresser enter his house at night. I wasn’t completely without any of my Missy stuff, I brought along a small back pack with my wig and some make-up as well as some money and a change of clothes in case I ended up spending the night there. I knocked and he opened the door.

“Missy is at your service.” I said to him to show that I was who he thought I was.

“Come on in and make that hot ass of yours comfortable.” He said seductively and with a wink.

I sat down on his couch with my bag on my lap as he excused himself and said he would be back soon. Greg came back a short time later with a bunch of clothes in his arms. He gave them to me and said I could get changed in the upstairs bathroom.

When I got to the bathroom I laid out the clothes to see what I had to wear. It was a sexy woman’s police uniform like what you would see some women wear at Halloween to dress up and still be sexy. It had tight fitting skirt and top with long black stockings. It even had a baton that had the head of cock on the tip instead of a smooth surface. Finally there was a pair of black 6 inch platform heels and a hat to match the outfit. I put everything on and when I was done with my makeup and the hat I looked in the mirror and thought that I looked like real slutty cop and I loved it.

I grabbed the dildo baton and made my way down stairs. When I got down stairs, I saw Greg walking around dressed in his police uniform like he was going to work. He smiled at me and and pointed his fingers at me like a gun.

“Hands up!” He shouted.

I put my hands up and smiled as he walked closer to me. He took the dildo baton from my hand and cuffed my hands behind my back. I giggled as I rubbed my ass against his growing cock. Greg gave my ass a little squeeze as he walked me around his house a little and pretended to read my rights.

“You have the right to remain a slut. Anything you have can and will be inserted into you tight little fuck hole.” He said as with both gave little giggles to his creativity.

Once he walked me through the entire house he brought me to the kitchen and started to frisk me. He felt his way from each of my ankles and worked his way up. He felt up my legs and all around my thighs as he felt and squeezed my inner thighs then rubbed around to my ass which he spent extra time on, squeezing, slapping and rubbing all over. This was making me extremely horny as he worked his way around the front. Greg then went up to my head as he felt around and put his finger into my mouth. I gave a little moan as he slipped it in and I began to suck it while I bent over slightly to rub his cock with my hands and my ass. Then he pulled his finger from my mouth and felt down my body. Greg gave my fake tits a little squeeze as he felt around for my hardening nipples to press them and pinch them through the shirt.

I gave a little groan and asked for more but he just ignored it and continued to frisk me. Greg was now back to my ass but instead of massaging it more he went to my front and felt my hard cock poking straight out.

“I see your carrying a concealed weapon.” Greg said in a devious and sensual tone.

“Tee hee, you got me officer.” I replied in a girly voice.

He pushed me so I was bent over a kitchen island he had and spread my legs wide.

“It’s time for a cavity search.” He said as he took my dildo baton away from me and pulled my skirt up.

He poured some lube onto it and spread it around on the baton and my ass. Then he glided it up and down my crack teasing me.

By this time I really wanted something in me and I wanted to scream for him to push that toy into my ass deep and fuck me with it but instead I kept to the role.

“Make sure to check deep inside partner, I might have some contraband inside there. I’ve been a naughty officer and you should put me under your parole.” I said with a giggle as I grinded my ass against the dildo baton and rubbed my hand along his crotch.

He seemed to have liked that because he pushed the tip to my ass and plunged it in as deep as it could go. At first I thought it was too big and I grabbed the kitchen island as it went in. I could feel it stretching me from the width and the length was going deeper then I ever think I have had before.

He started to fuck me with it, going in and out a little faster each time but also careful to go the same length each time. It felt so incredible and smooth and slick I finally broke, I started moaning and panting deeply and loudly giving loud wheezes with each breath as I felt the baton go in and out of me and almost reaming me inside out.

Greg fucked me like that for 5 minutes until I was loosened up and all soft and warm on the inside then he pulled out and made my asshole gape for him. As he held my ass open I held it open for him as long as he could as he poured lube straight into me. Once he had some in I closed it and made it wink as he poured more on the opening. The lube felt so good as it squished around inside me and making my insides all slippery, I felt as if I could take a cock long enough to go the entire length of my insides.

Then I felt Greg press his cock against my hole as we rocked back and forth with him pressing his cock inside me more and more until his head popped inside. It felt so good as I felt his cock head more around just past my opening like a little plug, but before long he shoved his cock the full length inside me with one thrust. Greg held his cock there for only a few seconds before he started fucking me really hard and deep. It felt amazing and I was already starting to sweat and precum all over.

After a while, he pulled out of my ass and turned me around so that now I was laying on my back while still on the kitchen island with the soles of my feet on each corner of the kitchen island. He took the baton and gave it to me which I happily accepted and started sucking on it like I was giving it a blowjob as he watched. Greg loved it, as did I to show him. As I did, he pulled my hips closer to him and held my legs by my ankles. Then he pushed my legs as far back as he could get them and plunged his cock back deep into my ass and continued to fuck me.

The pounding became so intense as his cock reached deep inside me. I started to moan louder and louder each time his balls slapped against my ass I even let go of the baton and it dropped rolled to the edge of the kitchen island top before Greg caught it. He stopped and slapped the dildo to my lips and told me to open wide. I could feel his throbbing cock deep in my ass as I could only moan in agreement and opened my mouth and stuck out my tongue. Greg took the baton and slide it down my throat making me gag as he rapidly and shallowly fucked my mouth with it.

Eventually Greg got up onto the kitchen island as well and continued to fuck me. His cock got hotter and hotter as we were now making very sloppy and slutty noises as his cock went in and out of my ass. I opened my mouth as wide as I could and Greg slid the baton all the way down my throat. It stayed in my throat and he fucked me over and over for what seemed like hours, however it wasn’t long and we both needed to cum. Greg shot his first 2 loads into my ass as he pulled the baton out of my mouth leaving my face sopping wet along with the baton. Then he pulled out and shot the rest onto the baton as best as he could to cover it but missed a couple times as they shot onto my body and my uniform. When this happened it sent me over the edge as well, making my cum shoot straight up and all over myself. God it felt so hot as it fell from the sky and onto my sweat covered body with the uniform chafing tight to my body.

We sat down and panted for a few minutes as he told me that he needed some recovery time and needed to clean up as did I. Once we caught our breath, Greg went up stairs and I got out of my clothes. As I did, Greg came back down and gave me a bra and some panties and told me to come upstairs with him. I folded the clothes and put them next to my bag with the dildo baton on top. I slipped on the panties and walked with Greg up the stairs as I put on the bra. I walked ahead of him and he gave my ass a little smack and I turned to him with a smile and giggle as I continued up stairs. I walked ahead of Greg a few extra steps as I pulled my panties up into my crack like a thong. Then I gave my ass a little slap and wiggled my ass in my slut strut until I got up the stairs and into his room.

When we got there, he told me I could sleep in his bed tonight. I just smiled and crawled into his bed as he got in with me. Then he grabbed a pair of hand cuffs and cuffed my hands together and put the chain behind the bed post so now I was restrained with my hands unable to move away from the headboard of the bed. He started to rub up and down my body. He then reached over and grabbed some lube he had in his night stand and started rubbing it all over his cock just inches from my face. I was able to reach over and lick his head a little as I tasted his cock. Greg loved to watch this and started to stroke his cock as he sat on my chest and slapped his cock on my face and made me lick the head and suck on it while he stroked. I could only watch as he stroked his big, hard, throbbing and dripping cock just inches from my hungry lips as my ass tingled for more. He must have saw I was ready because he got off of my chest and lifted my legs up enough to place a pillow under my hips to raise my ass up a little. Then he pulled my panties to around my knees and rested my legs on his shoulders. Then he took out a pair of scissors and cut holes big enough for just my hard nipples to pop through.

Then he moved to his night stand again and pulled out 2 clothes pins which he used to clip right onto my nipples. I could feel my nipples become more and more sensitive as he gently tugged on each one then shoved his cock back into my ass. He fucked me like that for about an hour as he came in me over and over and filled my ass with his cum. It felt so gooey and warm and his constant thrusting with my ass on the pillow made him hit my P-spot and made me cum just as much as Greg did.

Once we were finished again, Greg took off the cuffs and clothes pins and we went right to sleep.

The next morning I woke up fairly early and saw Greg was still sleeping naked beside me with the blanket barely covering his soft cock and dried cum all along my ass crack. Thinking of last night and feeling the cum in my crack made me horny and I moved over to Greg’s cock and started licking it to make it hard. Needless to say it got hard as a rock and I woke him up with a great blowjob. I sucked him deep and hard as my tongue glided over every part of his cock until he came one more time, however we weren’t done yet. I giggled as he looked at me then spoke.

“How about another fuck before you go home?” Greg asked with a lustful look on his face.

I smiled and nodded my head as I put the uniform back on and fucked the rest of the morning away. When we were finally finished, I packed my bag up and took a quick shower before putting my normal clothes back on and heading home.

Once I was home, I looked in my bag and found the uniform and dildo baton I wore the previous night and that morning with a note.

“To Missy,

“I really enjoyed Missy’s services and I hope I can arrest you again sometime.” He said with a little smiley wink that he drew at the end.

He continued to say.

“P.S. Since Missy enjoyed the uniform she wore so much I figured she could keep it as a memento of the night and maybe use it in an erotic video on her website that she could dedicate to me. Hope to fuck you soon.”

I turned around to find mom walking in and I let her read the note as I hung the uniform and baton in my closet next to my other clothes as mom spoke.

“Why don’t we give him what he wants Missy?” She laughed.

I was hoping she would say that.

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 9: A New First for Missy

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