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Telling Mom I’m A Crossdresser Part 4: Repeat Business and Roleplays

4th installment of Missy :) please rate and comment :)

When my mom and I had gotten home, I immediately ran into the house to take a shower and change as quick as I could. I re-shaved my entire body and removed my makeup so that I could start from scratch and apply it again.

Once I was finished with my makeup, I see a new outfit laid out on my bed. This was a cute nurse outfit with a short tight skirt that barely covered my ass. It was also pink with white stockings and long lace gloves that went up to my shoulders. Finally the top was like satin just like the skirt but had a little hospital symbol on the chest over each nipple. Then I completed the outfit with a cute little nurse hat that you can only see in porn now these days. I looked at the outfit and noticed something, there was no underwear but there was a garter belt to hold up the stockings. I didn’t mind that there was no underwear but I guess that just meant that I didn’t need to take off the outfit anyway.

Just then my mom came in and started to tell me the details of the night. I was to be in that nurse uniform and it was to be a role play with Stan being my patient and I was to “treat” him as best as I could.

I love the idea of role plays, they have always been my favorite kink in the bedroom and I have always loved all the naughty clothes to wear.

Then my mother smiled and told me that the plan had changed somewhat from the time she went to pick me up until now. I asked her what that was but she said it would be a surprise and I was to continue to role play no matter what happens. I just smiled and blushed as I put the finishing touches on the outfit. The only thing I did not like about the outfit was that if I spread my legs a little my clitty cock would fall out the bottom and you could see the tip, but this didn’t matter to much to me.

Once I was finished I walked down stairs to meet my mother who was already talking to Stan. He still looked as sexy as my last night with him but tonight he looked a lot hornier to see me. I escorted him up to my room and my mother followed with the digital camera. She set it up in perfect view of the entire room. She said she would be filming the entire session and putting it up on the website for sale and to advertise some of Missy’s services, then we began our fun.

I walked into the room with a clip board and asked how he was doing today.

“I’m alright but I have this pain and a little swelling in my groin area.”

I walked closer to him and asked where the pain was.

“On my cock, it feels sore and its been having this tight hard feeling since you walked in the room.”

“Oh that’s no good.” I replied sweetly as I pulled off the blanket to reveal his fully aroused 7 inch cock that I had missed since his last visit.

“well well this is a problem we have here. I will have to apply some “ointment” to this and rub it all over where you feel the pain.” I said as I grabbed a bottle of lube and started rubbing it all over his cock.

“Oh nurse the pain is starting to go away; it’s feeling a little better already.” He started to moan while he spoke.

I got up onto the bed and stuck out my ass making my skirt ride up and show off my crease of my ass and my clitty cock hanging loose.

“I will now administer a procedure that has been proven to relieve pain and swelling in the penis area.” I said looking him in the eyes and licking my lips.

I then took him into my mouth and started sucking his cock, licking up his shaft and dancing my tongue around his head before kissing down his shaft and taking each one of his balls in my mouth while stroking his big cock.

“Oh nurse, I think your procedure is working. My penis feels incredible, please don’t stop.” He moaned as I sucked his cock for another 10 minutes.

“Now I must administer the last portion of the procedure. However I must apply more “ointment” in order for this procedure to be effective.”

I grabbed the bottle of lube and applied a large amount to his cock before getting on top of him and inserting his big hard cock into my ass. I rode his cock for 20 minutes and tried everything from on my feet and thrusting up and down to leaning forward and smacking my ass and guiding his cock to show off for the camera. By this time my mom had already gotten closer and taken all kinds of different perspectives and angles so she could make this as much of a real porn movie as she could.

Just then the door opened and the man from the adult shop entered in a doctor’s uniform and his big 7.5 inch rock hard cock hanging out, this was obviously the change in plans she told me about earlier. I found out later that his name was Roger and he had called with a similar fantasy and my mom had thought she could “kill three birds with one stone”. I just played along and acted like I knew this was going to happen.

“Oh doctor I was just treating the patient, he complained of a soreness and swelling between his legs.”

“Well done nurse but there seems to be an epidemic of that condition because I have come down with the disease as well.” He told me as he thrust his big meaty shaft in the air toward me.

“Come here then doctor and I will treat you as well.” I said in a sexy voice and motioned with my finger for him to come closer.”

Roger came up beside me and stuck his cock right into my mouth which I sucked on greedily while still riding Stan’s cock hard and deep, grinding my hips like a whore who was starved for cock. Then I turned around so my back was facing Stan with his cock still inside me as Roger got up onto the bed. I got onto my feet and started grinding my ass onto Stan’s cock while leaning back and just overtop of him. Then Roger go closer to my face and started fucking my mouth deep with his cock. This would have made me gag however by now I had gotten used to the feeling of huge cocks down my throat so it was able to slide down easy. This continued for a few minutes before I continued but leaning forward for another 10 minutes then my legs got tired.

I got off of the bed and bent over at my waist and took Stan’s cock in my mouth so that now Roger could fuck me. I completely swallowed Stan as Roger got behind me and shoved his full hard length deep into my hungry hole.

“Nurse I believe you need an injection of 50cc’s of my cum in your ass so that you don’t get pregnant.” He said while pumping into my ass with his balls slapping against mine.

“Oh nurse, the pain is almost gone I think I’m about to be cured.” Stan said moaning as I felt his balls tighten.

Stan let loose a load of cum into my mouth, and then he pulled out and shot another 2 good ropes onto my face. Seeing this, Roger came as well and filled my ass. We all panted for a sec but then I looked over at their cocks and seen that they were both still hard as rocks.

“The procedure was not as successful as I had hoped. However it is common that a condition such as the ones both of you have require the same treatment multiple times.” I said with a giggle and a smile while wiping the cum from my face and into my mouth.

I laid on the bed sideways with my legs in the air as Stan (who was still playing the patient) got behind me and pushed his cock into my hole that was still sticky from Roger’s cum.

“You are the best and sluttiest nurse I have ever got treatment from. Please nurse, cure me and my aching cock.”

“God yes, Fuck ya mmmm. Oh yes I love treating my patients I will do anything to make them and their wonderful cocks feel better.” I yelled and screamed in pleasure.

Just then Roger (still playing the doctor) got in front to my mouth and stuck his cock in my throat and started thrusting it in and out as I gave a muffled moan.

“You are a very dedicated nurse and I am glad that you and your tight little fuck holes work for this establishment.”

I felt Stan’s cock throb in my hole and make squishing noises from the cum as I licked and sucked all around Roger’s cock up and down his shaft and gently nibbled his balls when I could but mostly deep throated him. They continued to fuck me like that for another 15 minutes before they needed to cum again.

I got down on my knees and stroked and sucked both of their cocks giving them kisses and slurping up every inch of them till they were just about to blow.

“Yes, Yes, Release your liquid and give me your samples so that I may cure those huge throbbing cocks of yours. Oh god yes!” I screamed as they shot their loads onto my face as my mom got in real close and made sure she got a perfect close up of me “collecting the samples”.

When Roger and Stan were finished I licked the cocks clean and blew a kiss to the camera and decided to give a slutty advertisment for the end. I turned around and spread my cheeks wide, showing off my gaping asshole as my cock shot its load on the floor.

“Please give me your load to. If you want me and my holes, ask for Missy and she will take your sample as well.” I waved goodbye and my mother shut off the camera.

After it was over, the boys each left $800 dollars and said it was nice to fuck me again. They gave me each a kiss and a slap on my ass as they left, leaving me to get cleaned up and changed for the night.

When I got out of the shower, I found a beautiful lingerie outfit sitting on my bed with my mom sitting next to it in her bathrobe. She gave me a big hug and told me she was proud of her little slut and thought she may like a little reward after working so hard tonight.

The lingerie was a sexy green camisole with tie ups in the back with a pair of matching green panties and bra with black stockings that went up to my thighs. My mother pulled off her rope to reveal she was wearing similar clothing however hers was all black with her breasts making the front ride up a lot because they were so big. She started licking her dildo and rubbing her pussy as she looked at me.

“I think it’s time Missy got to cum with her clitty and her ass at the same time, But don’t worry I will be having fun tonight as well.” She said with a moan and rubbing my cock.

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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