Telling Mom I'm A Crossdresser Part 10: Another Day With Mom free porn video

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It was about 11am by the time I woke up and found myself still in bed with mom. I looked over to see she was still sleeping and still in her lingerie as was I. I got out of bed carefully and as soon as I did I felt how sore my ass really was. I decided to tighten up my stance a little by putting my legs together and squeezing the muscles in my ass tight as I walked. It was a lot like my sexy walk and to be honest it gave me my morning erection as I walked to my room.

Once I got there, I took off the lingerie and set it aside to be washed with my other clothes. As I bent over to pick up my panties, I could feel my worn out hole open and all those hot and sexy memories started flooding back with Lemar behind me and making me a real woman.

Once I removed the last piece of the lingerie I searched in my drawers for something else to put on. To my disappointment, I had worn all my sexy and slutty clothing and now only had my normal boring boy clothes. I searched through all my drawers and my closet for what seemed like forever before I finally found something to wear. It was a black thong and bra, it wasn’t much but I got out my black stockings and heels to go along with it. I quickly put on the clothing and started to think of what else I could put on. I finally decided on a nice black teddy that you could see through and my brunette wig. I gave a little turn and then bent over to pick up my clothing. As I did I looked at my sexy ass in the mirror and gave a little wiggle and a giggle to myself. I took all my dirty clothes to the laundry room and began washing them. I went into the living room nearby to wait for them to be finished. I soon grew board and was still horny from when I woke up so I thought why not have a little fun while I waited.

I went to my room to get a vibrator and looked through until I found a nice big black dildo and a normal plain looking vibrator. The dildo was about 7.5 to 8 inches long with big silicone balls at the base and a hole in the bottom for what I can only assume is for multiple uses, and I had one particular one in mind.

I grabbed my bottle of lube and a condom from my night stand and headed back to the living room. I put the vibrator in the dildo until the end with the dial for the vibration was inside the dildo as well. I got on my knees in front of the couch and placed the dildo on the couch and positioned it like there was someone sitting on the couch with their hard cock pointing right at my face. I started rubbing it and teasing the head a little so I could practice getting cocks as big as Lemars hard again.

After a few minutes I grab the condom I had brought and opened the package before putting it in my mouth. It was a flavored condom so it wasn’t as bad as a normal one would have been. I then grabbed the dildo again and I pressed my lips against the head. I opened my mouth and used only my tongue and teeth to roll the condom onto the big cock as far as I could go. With all the deep throat advice and practice I had gotten from mom, I was able to get just over 7 inches of the dildo into my throat and roll the condom far enough down so that it was in place. I rolled the last bit of the condom over the rest of the dildo and over the balls so I would not have to reposition it over and over again.

Once it was on, I rubbed it all over and felt the length and width in my hands and got myself horny enough to try and take the entire thing inside me. However, just as I was about to apply the lube the washer buzzed and I had to deal with the laundry again. Frustrated, I got up and went to the laundry room and got the washer and dryer going as quick as I could so I could return to my pretend lover.

When I returned to the living room, I looked for my dildo and could not find it anywhere. I started searching for it and lifting cushions then retracing my steps but still I could not find it. I stopped to think as I sat on the couch but then I heard mom’s voice from behind me.

“I see Missy wanted more and decided to get a little naughty as she was doing her chores.” She said with her famous smile.

I looked at her and saw she was still wearing her lingerie from last night but when I got to her waist and crotch area I saw she was wearing a strap on, and not just any strap on it had the dildo I was just using locked in the harness and looking ready to go.

“Mmm yes mam, I need more and I still feel so horny that I just needed relief as soon as possible.” I said as I got on my knees on the couch while facing her.

She walked up to the edge of the couch until she was right in front of my face. Then she grabbed my head and pushed her big dildo into my mouth.

“Then eat it you little whore, I’m going to satisfy you like no man can.” She spoke in a dominating voice.

I opened my mouth and let the massive black toy slide right inside as I started to moan and savor the flavor as my tongue swirled around the tip over and over again. I felt mom’s hand guide my head back and forth like a real telling me to go deeper onto his cock.

This continued for only 5 minutes, but I still loved every second of it. Then she pulled that massive silicone cock out of my mouth and slapped it around my dripping mouth. She called me a little whore, her hungry little plastic cock sucker and told me it was time I got filled.

I stuck out my ass and pulled down my thong like a good little slut as I moaned and watched as mom strutted around to my side and applied a generous amount of lube on her strap on. Mom rubbed the tip of her strap on to my hole and considering the intense fucking I had the night before, I had no worries that it would go in with any pain and I was right. The strap on went inside me and I could feel the slipperiness of every inch enter me and fill me.

Once the dildo was completely inside me, I pressed as deep as I could against mom’s body and grinded the dildo as deep and as hard as I could. The feeling of being full of cock again was great even if it wasn’t a real one, but it was still better then just masturbating.

“Hold on slut, Momma is going to ruin the little boy pussy of yours.” She said as she started to spank my ass hard and grind the dildo deep into me.

I moaned as I felt the lube get warmer and warmer inside me and she churned my insides before pulling out and slamming back in again as I just held on helplessly as my ass was pounded. It wasn’t long before I was panting, moaning and sweating hard as slapping noises could be heard from behind me each time she thrust deep into my ass. All of a sudden I felt a sudden surge of pleasure wash over me and my body shivered then relaxed. I looked down but my cock was still rock hard and throbbing even though I had felt an orgasm. I rolled over on my back as mom pulled the dildo out.

“I see Missy just had an orgasm from her ass without shooting her sticky load at all. You are very lucky, that means you can fuck without waiting this time.” She giggled as she removed the strapon. Then she turned around and bent over just enough to let me watch as she slowly pushed it deep inside her ass as much as I had taken it. When she had it in all the way, I reached over and turned on the vibrator inside to max then gave her ass a couple good slaps like she did me.

Mom turned around quick and moaned as she bit her lip as if she was telling me not to stop and to keep going. Then I quickly got down onto my knees right in front of her and started to eat her pussy. I started by kissing all the way up her inner thighs then gently blew some air onto her glistening wet lips. My mouth went straight to her clit and I started licking it and flicking my tongue on it over and over again as I squeezed her ass and massaged it like it was a couple of big chunks of bread dough. I moved down till I was against her wet juicy lips and slowly stuck my tongue out and licked all around the outside not missing a single spot. As I continued, I could hear her moans get louder and more intense as I got deeper and deeper into her nether regions.

Now it was time for the best part. I pushed out my tongue and wiggled my way deep inside her pussy. I could feel her wet juicy lips squeeze my tongue tight as I moved it in and out then went as deep as I could as I swirled around and even rubbed her g-spot as hard and as fast as I could. It wasn’t long before she started to shake then explode in squirt after squirt onto my face and down my body. The feel of her warm wet liquids oozed down my body and coated my bra and teddy in what felt like a warm shower with the most erotic scent ever.

“That was very good Missy, but I think it’s time your little friend got some attention as well.” She pointed down to my throbbing hard cock then pushed me onto my back and told me to lay flat on my back.

I did as I was told and laid down on my back with my cock twitching and pointing straight up in the air. She sat down on my body with my cock between her legs then she started to rub the length of my cock along her pussy lips. It felt so good I almost started moaning just from that experience alone. Then she raised her body high enough so that my cock could stand straight up once again as she lowered herself back down again, inserting the full length of my cock into her pussy.

Without saying a word, she started to ride me. She started slow by grinding her hips as my cock was buried deep inside her warm wet dripping pussy. I could feel every squeeze and twist her pussy made as it clenched my cock hard, trying to make it shoot its juices inside her. I could tell mom was starting to feel good as well because she started to moan like I was and even began to bounce her hips and ride my cock up and down. Now it was becoming very intense and gave me a feeling I had almost completely forgotten about.

I grabbed mom’s hips and started thrusting up into her, she obviously loved how it felt because her jaw dropped and she grabbed her tits. I saw this as an opportunity for Missy to have some control for once, and control she got.

I sat up and pushed mom onto her back and I got up onto my knees and began to thrust into her mercilessly. Each time my balls slapped against her pussy, she squeezed me tighter and tighter and I started to call her all the slutty names she had called me in the past.

“Take it! Take it you dirty little slut! Squeeze my cock hard with your worn out whore holes that Lemar ruined for all other men last night.” I demanded of her as I reached up and pinched both her nipples hard making her not only squirm, but also give her just enough of a sensation to send her over the edge and cum all over my cock.

As I felt her juices flow over my cock, I knew this was the perfect opportunity to become the pimp rather then the hoe and I think mom wanted that as well.

“Get on your knees slut, all fours now! I want to see that fucking ass in the air so I can fuck you like a dog.“

“Yes mam.” She purred.

Mom was on all fours and grinding against my cock in no time. I gave her ass 4 hard slaps on each cheek as I made her scream and beg for my cock. Then I plunged my finger in her ass and made her quiver for only a second before I shoved my cock into her pussy, surprising her and making her extremely horny. Then I grabbed the dildo we were playing with and shoved it deep into her ass and turned on the vibe. I pressed the base with the balls up against my body as I moved both my cock and the dildo in and out of her at the same time like she was being fucked by a man with 2 cocks.

It didn’t take long for my need to cum to bubble up since it had been a while since I had used my cock and fucked a pussy but I didn’t want to show that I was trying to keep from cumming so instead I went with it. I left the dildo in her ass and vibrating as I pulled out my cock then went around to my moms face. I stroked my cock a few times then blew my load all over her face and told her to clean me up.

Her tongue felt amazing as it slid all around my head then once up my shaft. Mom’s saliva was very warm and wet that I knew if I was to just let her continue she would have been able to get me hard again in seconds, however I had much bigger plans in stored for her holes. As she licked off the last few drops from my cock head, I removed the dildo/vibrator from her ass and pulled the vibrator from out of the dildo. The cock hungry look in her eyes told me she wanted it back in as soon as possible and not being one to disappoint, I created the perfect way for a CD like me to fuck.

Since I had already removed the vibrator, I put the dildo back into its strap-on harness andTo continue reading this story you must be a member. Join for FREE here.

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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
1 year 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...

1 year 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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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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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...

3 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....

3 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,...

2 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...

Gay Male
2 years ago
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My first Crossdresser Part One

When she walked in to the restaurant I knew I was in trouble. It was the end of three long days at the convention and I was tired. I had come down to the NASCAR Cafe for a sandwich, mainly because it was the only bar in the Sahara that didn't have video poker...I lose a lot of money playing video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's strutting toward a table.Convincing she was not, a crossdresser without question. But pretty, really...

3 years ago
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Jaq Invites Crossdresser Over

Anyone who follows our adventures will know what type of lifestyle we lead.A short while ago Jaq got chatting to a crossdresser online. It turned out that he only lived a short drive from where we live. Kieran was twenty-two, his pictures looked amazing. Jaq asked me if she could invite Kieran to visit, an offer that I could not refuse.All was set for the Friday evening. To say we were excited would be an understatement. Jaq and I showered and dressed. Jaq looked amazing as always in a very...

Crossdressing
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...

1 year ago
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My first time with another crossdresser

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my brother and sister. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer...

2 years ago
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Milwaukee Cuckoldrsquos Wife and the Crossdresser

Judy used several sites over the years to find her friends with benefits. She never tells me until afterwards what she has done. It’s rare she tells me anything in advance. One day she advised me the k**s were at my parents and she was entertaining that night and I would have to stay in the family room. My curiosity was getting the better of me.She went and took a shower and asked me to come in and shave her pussy. She had me paint her fingernails and toenails. Once she was ready she put on her...

2 years ago
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Crossdresser for mature couple

I am a bi crossdresser....love some pussy or cock. I registered on an fabswingers looking for a meeting with similar people.I was actively looking for an older couple to have some fun with. To cut a long story short, I finally got talking to a guy called Bill. He and his wife could entertain a gurl like me for a fun filled evening, if I was game. We both had a list of dos and donts for the night and we went over a few ground rules etc.I was to be their maid and waitress for the evening. They...

1 year 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...

3 years ago
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Teenage crossdresser

Here are the usual disclaimers this story is for adults only if you are viewing this andare not 18 years of age or older please close this page immediatly.There is no cross dressing in the story but this is how I began my transformation fromregular boy into cock suckking teenage crossdresser.We were having a really hot heat wave. i meat with my older brother (wear red shorts, and a black T-shirt) wanted me to get out of the house and off the computer so she suggested a movie. I felt wierd going...

4 years ago
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crossdressers 1st time

hi, im new to this. this happened about 3 years ago now.I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from this simple thought I became massively aroused and started trying on her underwear, make up, and even a wig that was in the apartment. soon enough, I was looking like a slutty crossdresser.I thought enough...

3 years ago
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Crossdresser Got Caught By The Neighbor

Hello readers, my name is Rajesh, a 24-year-old guy who likes to dress like a girl. I am in Australia now.  This story will tell you how a crossdresser got caught by a neighbor and had to do whatever the neighbor ordered. His name is Roy (name changed), he is 6’1 height with a well-built body, and he is in his late 50’s. I recently had to move to another unit as my old unit’s lease got finished. On a Friday morning, I was leaving for my office. I saw an old man (who lives in the next door unit)...

Gay Male
4 years ago
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Crossdresser to Trans Escort Part 3

This is a continuation of my Crossdresser to Trans Escort series.After my first fuck for money with the restaurant owner, things escalated. I arrived at work the next morning wearing a pair of black trousers, black blouse and flat ballet shoes. The owner called me into the back office before we opened up for the customers. He was sitting behind his desk wearing a tight black t-shirt which showed off his tanned skin and bulging muscles. 'I really enjoyed our transaction last night' he grinned,...

3 years ago
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Cd crossdresser sissy caught by mom and dad pt5

Sorry I haven’t made any posts. Have been very busy with school and work. I started to write a story, would get about halfway through It then quit and not safe any of what I wrote. Last story was a few months ago when my parents and I went to the Bahamas on our boat. It was really fun. I’ve been taking hormones for a few months now and have little 36B boobs. My nipples are crazy sensitive now too! I haven’t really been wearing a chastity belt very much recently. Weirdly find It pleasing to wear...

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