Telling Mom I'm A Crossdresser Part 8.5: Cops And Prostitutes free porn video

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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.

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Italy, september 2011. Sorry for bad english, I try to write correctly but don't know if I did. From tonight, I was a crossdresser. I'm been crossdresser from 12 to one day before my 27th birthday. Irony. I begin to have an answer to the question: "What feel girl?" Yes, a simple question. What feel girl when wear panty, tights, dress, skirt? What feel a woman in heels, purse, with her hair falling down the shoulder? What feel a teenage when begin to make up herself? When wear lipstick,...

2 years ago
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Chanda Ki Gandi Chudai 8211 Part 2

Hum dono abhi bhi nange hi thay. Chalte chalte usne paad maari. Uski gaand mein abhi bhi haddi akti hui thi. Nadi kinare, jhadiyon ke bich usko bithaya. “Hug le saali madarchod. Kab se paad rahi jai bhosdiki.” Woh hugne lagi. Uski gaand se haddi nikal gayi. Uski garam moot ki dhaar mere pairo pe giri. “Saali maderjaat! Mere pairon pe mootegi. Saali raand muh khol,” main uske muh mein mootne laga. Lavda uske gale mein ghus kar mootne laga. Maine apni tange faila di aur wahi khade khade hugne...

2 years ago
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Telling Mom Im A Crossdresser Part 4 Repeat Business and Roleplays

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...

4 years ago
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Telling Mom Im A Crossdresser Part 5 Movie Night and Gangbangs

I had decided to take a few days off from being Missy after Stan and Roger had left and my mom and I were finished with our little girl time. I spent the next few days just continuing with life as normal except for the throbbing pain in my asshole and my cock from the 3 days of constant sex. I couldn’t stop thinking about all the things I had done as Missy and all the kinky fetishes I had experienced since I came out to my mother, but I guess I have her to thank for all my new wonderful clothes...

1 year ago
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Alexander of SpartaChapter 2

Report to the King of Sparta. B.C 481 "We must conclude that there was more then one Persian ship in our waters. When one met with disaster in the storm, the other picked up survivors and as much wreckage as it could. The shield is the only piece of wreckage that signifies Persian identity. There can be no doubt that it was a spying mission or an attempt to land agents of Persia on our soil or the soil of a neighbouring state. We cannot ignore the possibility that a neighbour may actually...

2 years ago
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Telling Mom Im A Crossdresser part 135 Missy Brings Home A Stud

I told Thomas all the details of why I was out this night and he loved the idea. He took one of his Viagra and he led me out of the bar. I felt a little embarrassed at all the cum leaking down but some of the cross dressers were just smiling at me like they were saying “you go gurl!” which made me a little proud. Thomas followed me in his car until we got to my place and I took him by the hand until we got in the door. When I walked in I heard a thumping upstairs and asked Thomas if he would...

2 years ago
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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...

1 year 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

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