Telling Mom I’m A Crossdresser Part 4: Repeat Business And Roleplays free porn video

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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.

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Telling Mom Im A Crossdresser Part 7 The Spa

I could barely sit for days after Mistress Keri thoroughly tanned my hide and I had to take almost a week off so that I could heal. My mom knew this to and said we should go on a “girls” weekend to a spa for cross dressers and women, she also said that since it was for others like me then I could spend the entire trip as Missy. I loved that idea and hurried upstairs to pack Missy’s bag. I packed the essentials including a mini dress, a few different pairs of bras and panties, a very sexy and...

3 years ago
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Telling Mom Im A Crossdresser Part 75 Amateur Pole Dancers

After our time at the spa, I spent a lot of time in my room trying out all the new sex toys we got from Richard and Monica. They were all exciting in their own ways and I came so much with each one. Some vibrated, some went deep and some felt good stretching my ass wide. The feeling of all the sensations I could get from my new plastic and electric friends were amazing and found myself spending long hours with them. Once I was finished, I had to stop to rest as they had left me completely...

3 years ago
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Telling Mom Im A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

Crossdressing
2 years ago
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Chanda Ki Gandi Chudai 8211 Part 1

Mera naam Rudra hai. Ek number ka harami aur besharam. Mera dimaag mere lavde mein hai, jo saala har waqt chudai ke liye uchalte rehta hai. Kasarati badan jo ghanto tak lavde ka saath deta hai. Waise toh bachpan se hi kaafi chudai ki hai. Lekin yeh wali sabse achi wali, ya yeh kahu ki sab se gandi wali hai. Main tab 30 saal ka tha. Shaadi hui nahi thi. Ghar mein rehta hi nahi tha. Naukri hi aisi thi ke sheher-sheher gaon-gaon bhatakna padta tha. Peshe se ek civil engineer, jiski degree paiso se...

2 years ago
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Andrea On Her Own Part 3 of Andreas Stand

Andrea On Her Own (Part 3 of Andrea's Stand) A Note Before: If you have not read parts 1 and 2, please go back and do so. I have spent some time trying to develop the characters involved and a brief description of the plot so far will not help you much. Chapter 1: Needing More I leaned back in my chair and stretched. It had been a long hour and a half finishing the homework from my calc. class. As I stretched I felt the sweater pressing against the breast forms and glanced...

4 years ago
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Andrew Running Part 1 of Andreas Stand

Andrew Running (part 1 of Andrea's Stand) Chapter 1: Running I called my Aunt Clara from the bus station. She didn't seem that surprised to hear from me and when I explained why I was there she told me to walk a couple of blocks to the local diner and get myself a cup of coffee. She'd pick me up in about half an hour. I sat and sipped chocolate milk and tried to eat a pastry while I glanced nervously out of the window waiting for my father to show up and force me into his...

2 years ago
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Telling Mom Im A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5’10’ in height. She is also a fairly busty woman with a 30DD chest with about 35′ hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

2 years ago
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Crossdresser porn story 1

Ray Hirsch sat at a desk filling out form after form. It was amazing, the information that an employer required before you could start working at a new job: health insurance forms, Social Security, etc., and etc. He was now filling out a questionnaire on his background which would be used to conduct a security investigation, since his work might involve working on classified government projects. He stopped for a minute at the question: List any aliases you have used. “I wonder if I should...

2 years ago
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Sandy and RandyChapter 8 Mom

Sandy left to see her father with Randy stuck behind due to an illness that his mom determined was just a stomach bug. He’d be ok in a few days but would have to stay at home as it could be the Norovirus, very contagious, but usually not serious unless you were the one that had it. Then you felt like it’s the worst thing ever. But a couple days in, Randy was settled enough that he could sleep. His mom stayed close, taking care of him. Since she had no job at the moment and they had the...

2 years ago
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Telling Mom Im A Crossdresser Part 12 Tow Truck Drivers Big Score

Sorry it has been so long since my last story. I have been busy with alot of things and I thank you for your patience. Lately, I’ve been working part time at a restaurant to make a little extra cash on the side along with my nights as Missy. I was saving up for a cruise I wanted to go on that I heard was for like minded people such as Missy. When people ask me about what I want to do with the money I am saving I just tell them I am thinking of getting a new car or something, but that’s not the...

2 years ago
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Nandini Deshpande 8211 Part 1Introduction

This introduction story is based on true events. All the characters mentioned are above the age of 18. For personal reasons, the names of the characters have been changed. Any resemblance to any person, living or dead, is purely coincidental. The writer does not believe in any kind of discrimination or disrespect towards women. The story has been written for sexual satisfaction and should be held in the same regard. “Aah!” Nandini moaned as my thick member entered her...

Incest
3 years ago
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Nandini Deshpande 8211 Part 1Introduction

This introduction story is based on true events. All the characters mentioned are above the age of 18. For personal reasons, the names of the characters have been changed. Any resemblance to any person, living or dead, is purely coincidental. The writer does not believe in any kind of discrimination or disrespect towards women. The story has been written for sexual satisfaction and should be held in the same regard. “Aah!” Nandini moaned as my thick member entered her...

Incest
3 years ago
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mature crossdresser 18 year old PART 1

Myself being a fulltime crossdresser and wear mini skirt and dresses all the time an high heels. A few weeks ago some new people move in across the street from me to be extact it was a woman and her 18 yr son.I talked to her few times and she was very nice and in our talks asked her if it bother her that i was a cd/tv she said nope. Well after couple weeks we became good friends and found out her son was shy and kind of a nerd. One day she came over to me and was little upset over something she...

4 years ago
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The Crossdresser Body Swap Part 1

The Crossdresser Body Swap Chapter 1 Ashleigh finished polishing her toenails with a final dab of red nail paint. She rolled onto her belly whilst letting her feet dangle off the bed to dry. She noticed the time on her phone and let out a sigh of annoyance, her neighbours would be coming around for another dinner night soon. Ashleigh always thought they were a weird bunch, always practicing meditation in their garden, plus their house was littered with all this voodoo and spiritual...

4 years ago
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Portrait of a Crossdresser as a Young Man

Portrait of a crossdresser as a young man By Sara Keltaine I didn't write this for others but instead as an outlet to release the demons that have haunted me since I was a child. Some might think this story funny, others might think it sad, and the people that think they know me the best would be shocked. I'm writing under a pseudonym that has become my alter ego but I will get into why's of that later. I've been told I was a happy infant and my memories of that time...

4 years ago
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Telling Mom Im A Crossdresser Part 3 Missys Weekend

One day while watching T.V, my mother had come in and told me Missy’s services had been requested for the entire weekend and we needed to go shopping. I smiled as we got into the car and went to the store to buy lots more sexy clothing for me to play in. After we had bought all the clothes and makeup needed for the weekend, my mother and I went home so that she could give me the details of what was to happen. She told me that I was to live with a couple this weekend and do everything they say....

4 years ago
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Telling Mom Im A Crossdresser Part 2 The Adult Store

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...

4 years ago
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CD crossdresser sissy caught by mom and dad pt3

Please go back and read part 1 and 2 before reading this or nothing will make any sense. I ended part two after going to the pool with my mom and dad, having sex then coming home and showing together. That was a few days ago. Not much happened between now and yesterday but I've been wearing girls clothes when at home, basically a bra and thong, heels, and normally a dress. My mom ordered me a romper and some skirts and blouses to wear too. I've also been wearing the chastity belt all the time...

2 years ago
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Cd crossdresser sissy caught by mom and dad pt4

Sorry to all those waiting on another post - been busy and haven't gotten to it.So my mom, dad and I just returned from a wonderful trip to the Bahamas on our boat and we had some wonderful sex.I had totally forgotten about this trip until the day before we left when my dad brought our boat home from the place we keep it about 20 minutes from our house. My mom had rented a house on one of the islands in the bahamas with a small private beach and a place to put our boat. Well I started packing,...

3 years ago
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CD crossdresser sissy caught by mom and dad pt2

So I left off my true story last right when I woke up the morning after getting caught by my mom and her and my father having sex with me, go read that before you read this otherwise it wont make since.That was about a week ago now. Well that next morning I woke up naked in my parents bed at about 9:30 naked from the sex the night before, walked into my kitchen and saw my mom sitting at the table in lingerie with a coverup just wrapped around her but not hiding anything with my one of my dress...

2 years ago
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A Crossdresser Gets Caught

Johnny was gentle and had slightly feminine mannerisms for a guy. He had had quite a few escapades with women, a couple of failed marriages and a dozen or so relationships but all had fizzled out. He had never thought about the fact that maybe he was gay or bisexual and although he was not homophobic he thought the idea was not for him. He found women attractive and loved them wearing sexy lingerie and became almost obsessed with lingerie and all its variations, sometimes even more than the...

Crossdressing
3 years ago
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AutoRide Made Me A Crossdresser Whore 8211 Part 5

Except for some dirty and humiliating ones, most of Raghav’s dialogue will be in English in this part about the crossdresser whore. I thought that it is easier for me than translating each of the dialogues. The ride home was uneventful. I just sat dumbfounded in the back seat while Ragahv just fled the auto fast. In a short time, we reached my place. I picked my bags and climbed the stairs. Raghav followed me, carrying another small bag. Where did he get it from? I am sure he was spotting a...

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