Telling Mom I’m A Crossdresser Part 5: Movie Night And Gangbangs free porn video

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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 and experiences. After all, she is the one who sets everything up for Missy. I couldn’t wait to see what my next job as Missy would be like.

By the end of the week, my ass was feeling better and I know I had stretched my hole to the point where I don’t think I will be having any pain unless I get a client who was overly huge. I sat on the couch in a white bra and panties, nothing special, just something to dress in and feel comfortable yet girly while I watched a movie with my mom who was also in her underwear. My mother and I talked for a while and eventually I asked if Missy had another job for this weekend. She gazed at me with a smile and her eyes wide open as she laughed a little.

“Actually Missy does not have a job this weekend, but I do have something planned for us girls this Saturday night.”

I wanted to ask what it was but figured that it would be better left as a surprise.

Saturday came and I decided to get dressed. My mom came in and suggested I wore some more sexy lingerie and meet her in the basement. With that I got a little excited and quickly picked out a nice black see through slip with black lace around the bottom. I also put on a pair of pink panties and bra underneath so that it would be bright enough and visible through the black fabric. I finished with a pair of heels as I gave a look at myself in the mirror and thought I looked amazing.

When I felt I was ready I walked down the stairs to find a big screen and a couch set up for us to watch a movie together. Mom was wearing a full body fishnet suit with open areas around her pussy, ass and her nipples which I assume was for easy access and finished it with a pair of black heels similar to mine. I have to admit, she looked hot with her big breasts and ass filling out the body suit.

I sat down on the couch next to my mother and we started watching a porn movie about two women who are trying to raise money to bail a friend out of jail by becoming prostitutes. It got my mother and I a little horny but we continued to watch the video until the end.

Once it was over my mother and I both took a deep breath to relax seeing as though the video made us both awfully horny. I got up to go upstairs when my mother stopped me.

”Why don’t we go for a walk right now? It’s very nice out and it’s dark so no one will see either of us in the night.” She said with a loving smile towards me.

“Sure, a walk sounds nice right now and I am nowhere near tired enough to go to bed yet anyway.” I replied.

We went upstairs to a closet where we pulled out a couple of trench coats to cover the full lengths of our bodies as we headed out the door and began our walk. We continued on the sidewalk as cars flew by us, flashing their headlights and giving the occasional honk. We blushed and giggled a little as we continued on until we reached the nearby park that was usually empty at this time of night.

As we kept on walking we noticed a van parked out the front behind some trees. My mother took me by the hand and said we should check it out. I agreed and we walked closer to the van which seemed to have been moving the closer we got. We peaked in the window to find a very trashy looking woman being gangbanged by 9 different guys taking turns. I looked at my mother in disbelief but just as I did she started knocking on the van and getting the attention of everyone inside.

All the men got out of the van and stared at us like a dog who just had his food taken away mid-meal.

“What do you want?” one man asked.

My mother dropped her trench coat from her shoulders onto the ground revealing her amazing body and fishnet suit then grabbed mine and pulled it off.

“We thought you may want a few more holes to fill tonight. Besides, your friend there looks like she is worn out.”

She pointed toward the trashy looking woman who was collecting her money and getting dressed. Obviously she was a hooker and didn’t care if they were finished or not, she just wanted her money.

Mom rubbed her body up and down feeling all of her sexy curves as her pussy dripped down her thighs and the men looked at both of us up and down with rock hard cocks. They told us to get in but my mother stopped everything.

“If you want both of us you will each have to give us $400 for the night.” My mom said with a lustful grin and sparkle on her face.

I turned around and gave my ass a little wiggle and a spank.

“It’s still nice and tight boys and I promise we won’t disappoint.”

The men agreed but then said that they would ream out our holes to get their moneys worth. By now I was so horny I was going crazy as I’m sure my mom was as well as we hopped into the van and started playing and sucking with some of their cocks.

I dived right in like the little whore that I am taking a cock in each hand and stroking it while sucking on one deep in my mouth. I looked over at my mom and she was already on her back and stroking 2 of the cocks while one of the guys went down on her pussy and started eating her out. Then I started feeling a man run his hands along the crack of my ass.

Eventually I ended up on my back as well with my head next to moms. I went back and forth sucking on the cocks in each one of my hands. I looked over and saw one of the men were taking advantage of my moms big tits and was thrusting his cock between them while she stroked off the cocks in each of her hands. I could feel their hands all over my body which made me so hard and horny I just wanted to grab the biggest cock within reach and stick it deep in my ass. I got up onto my knees and pulled down my panties and spread my hole as wide as I could.

“Please fuck me with your cocks. I need something inside me.” I begged in my most girly voice.

My plea’s were answered as a cock was thrust deep into me. I just moaned as the cock went deep inside me with ease as the man started pumping his cock into me. I grabbed 2 more cocks and stroked them in my hands again as a 4 th man got in front of me and put his cock in my mouth. I looked over at my mom who was stilling giving hand jobs and a titty fuck to guys but now had 2 guys fucking her ass and her pussy at the same time. The cocks were slamming into us harder and harder as their balls slapped us and would have made us scream in pleasure if it weren’t for being fucked in our cock hungry mouths.

This continued for 15-20 minutes before the men came filling our holes. They pulled out of us before the next round of men took their places. Now we were on our sides, I watched as my mother took a big cock in her ass and in her mouth while her sexy tits bounced back and forth while she moaned like a slut. While watching this I couldn’t help but take my attention to my ass getting its own hard pounding with my hands being held together and my mouthing being fucked.

“Oh yea fuck me boys, fuck this little whore in all of her holes and make her scream like a little cunt.” I heard my mom yell in pleasure.

Eventually my mouth was free for a second as well because the man fucking my mouth had came and pulled out.

“Oh god this feels so good. Ahh yes please keep fucking me, make me your little cum dump slut whore. Oh please I think I’m going to cum.” I moaned ecstatically.

Eventually these men came as well and allowing for another round of guys to take their places once again. This time it was a gangbang 69 with my mother and I. I laid on my back while my mother got overtop of me with her pussy and ass just above my face and my clitty cock just below hers. Two men took my mother in both of her holes just above my face as I watched in lust as got completely filled by cock. I felt the same as well as a man penetrated me and started ramming me as hard as the other 2 men were ramming her. I wrapped my legs around my mothers shoulders just as I feel her wrap her lips around my cock and start going back and forth between bobbing on my cock and the cock of the man who wanted to fuck her mouth.

Once we were in this position, it continued for what seemed like 2 hours before all the men were now spent and could not continue. We got out of the vehicle all sticky with cum and completely encased by the scent of fresh semen that started to dry and crust on our clothes and bodies.

“That was a lot of fun boys, we will have to do this again sometime.” I said playfully and my mom agreed.

The men gave us the money and drove away in the van, leaving us to walk home without our trench coats and sticky with cum. My mother and I just held hands as we walked home, scraping the cum off our bodies and sharing it with each other all the way home.

“Mom, did you plan this?” I asked her as we walked in the door.

“No sweetie but I am sure glad we did tonight.” She smiled savoring the last of the cum on her face.

I licked the last bit from off my thighs as I looked back at her and smiled.

“I am glad we did this to. We really should do this again and next time maybe we can do our own little role play. Maybe we could pretend to be slutty hookers or something?” I said jokingly and giggled.

“Missy my dear, we are already slutty hookers and we are definitely going to do this again.” She laughed and wiggled her bum to her room.

I did the same and as I drifted off to sleep all I could think of was what tomorrow had in store for Missy.

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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...

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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A Crossdressers Night in the Park

Last night I was on line in a crossdresser chat room where I was talking with Master Brian about me being a pain loving, submissive, bisexual crossdresser who was looking a master to use and abuse me. As we talked Master Brian asked me if I was dressed as a woman while I was on line with him. I told him that I was and then he asked me what I was wearing. I told him that I was all dressed up wearing a black silk mini skirtwith a black stretchy lace blouse. Master Brian then asked me what I had...

4 years ago
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Amazing Night With A Sexy Crossdresser

Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one. I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and...

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...

3 years ago
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Late night movie and my mom

Hi! I have seen several stories over here from mother’s perspective! How about a son’s perspective? So I am writing my experience. You can call me Ajith and I have no guilt in saying I am a motherfucker. In fact I enjoy being a mother fucker. In my opinion there is no other cunt in this world better than mother’s cunt for fulfilling our carnal desires. For me, my mom’s heavily fucked baby-making pussy is tastier than an eighteen year old girl pussy. Growing up as a son in India, I was always...

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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...

2 years ago
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Candice and Tony Movie Night

Candice is a 43 year old 5’3” brunette with hazel eyes, 115 lbs. 42c chest. A single mother for the past 2 years. Has been that way since her husband of 21 years left her for a younger woman. Her son, Tony, will graduate high school shortly after his 19th birthday in a few weeks. Tony is 5’ 9” tall, 175 lbs, brown hair and piercing green eyes, a shy man and a bit of a geek. He has had a couple girlfriends but none have ever given him the love he wanted. It was a month ago that Tony and...

3 years ago
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Night Trawling The Crossdresser

The streets of Pomona live two lives. Like maternal twins, they coexist in parallel, appearing as virtually identical to those merely passing through its old and storied neighborhoods. During the day, with the sun high overhead, myriads of people — whether they’re commuters traveling like drones or soccer moms distracted by their busy lives — they choke the streets in a constant pulse of life. Each person is absorbed by their own petty concerns, each oblivious to what is happening on the...

Crossdressing
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...

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