Telling Mom I’m A Crossdresser: Part 2.5 My New Toy free porn video

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It was a few days later after my night with mom at the adult shop, and my ass was still sore and I could still remember the taste of the cum in my mouth from that man. I could also still feel the pain in my ass from having to walk all the way home with my mom’s dildo in my ass.

My mind wandered as I thought about how my mom reacted to getting her dildo and how horny she got just by looking at it and me during that night. After we got home, my mom told me to have a bath and go to bed because it was late. Then she just disappeared into her room with her toy and left mine with me. I could tell from the moaning I heard while laying in bed that she was trying it out, which to be honest made me want to try my new dildo even more.

I was sitting on the couch as I thought about that night and decided to go up to my drawer and look at all my outfits I had accumulated since coming out to my mother. I laid the outfits on my bed in their proper organization starting with the latex one I had worn during my first time with the outfit I wore to the adult store next to it. Next I went into my drawer again to get out my other clothing that my mom had given me and put them in a big pile by my pillow. I set my sex toys next to them including the butt plug, the cum stopper, my new jelly 7.5 inch dildo and the breast forms all on one of my pillows to prop them up as if they were on show at an art gallery. I especially took pride in my new dildo. It was soft yet very flexible, with a long smooth shaft that was only about 1 ½ inches in diameter but reached a good solid length and a tapered end for smooth anal penetration. Looking at it I had to smile and was glad that my mom had taken the one without the suction cup because I loved the idea of sticking this thing all over the house for different sex positions.

Since my mother was out I decided to have a little fun while she was gone and got out some of the tranny porn she had given me but first I decided to get dressed in something sexy. After searching through some of my clothes I had decided on a nice pair of lingerie. It had a nice black bra and panties with pink mesh with some black fishnets and a cute leather twinkle collar that had bells on it and was pink colored. It matched nicely with my bra and panties. I finished with some lipstick and mascara, a pair of 5 inch platform heels just like what strippers wear and my blonde wig. Then I grabbed my new dildo, the small bottle of baby oil I had and a porn video. I stopped and thought it would be easier to clean this thing if I got a condom to put over it. I went to my mother’s room and got one, then I headed to the living room so my fun could begin.

I put the dvd in the player and sat down on the couch as it started. As I continued to watch the video I started to become horny as my cock got hard in the panties. I rubbed my cock and laid on my side with my panties off so that I could rub my hole and lube my ass.

It felt so slippery as I dipped my finger in and out feeling my ass enclose around my finger and try to pull it in as I took out my finger just to welcome it back again. I stuck in another finger to accommodate the width of the dildo and started to move back and forth and spreading my fingers till I was loose enough to for it to enter. I moaned as I looked up and saw an incredibly sexy shemale on the screen sucking a man’s cock.

I decided to do the same and put the dildo in my mouth as I fingered my hole deeper and deeper making myself moan even louder. I went on like this for about 10 minutes before applying the condom and have some fun.

While still laying on my side, I put the dildo up to my ass and started to push. I moaned as the dildo passed my opening and made its way into me. I could feel my ass suck in the dildo as it slides through my fingers and into my ass till it was 6 inches in. I moaned as I started to move it back and forth stroking my cock as I did.

I continued for about 15 minutes before that position had gotten boring. I went to the kitchen to retrieve a chair and put it in the middle of the floor so I could continue and still watch my movie. I stuck it hard to the chair straight up so that I could ride the dildo in the chair like the shemale in the video who was taking the man’s cock inside her so hard. I leaned forward and rubbed it along my cock pouring lube all over it while it was still in the crack of my ass. Then I went up and sat down on it, making it slip inside me up to the 6 inches I made it to before. I decided to go deeper as I spread my legs wide and slide down until my cheeks touched the chair.

I took a few deep breathes as I got used to it being inside me. I quivered as I could feel my ass throb around it all the way down. I started to pump up and down on the shaft as I stood on my heels using my smooth shaven thighs and legs to let my pretend stud go in and out of my ass, grinding on it deep and hard then pulling it out up to the head then thrusting all the way back down making myself moan and scream as I almost reach orgasm.

Then I hear a door click, frozen I don’t move as my mother walks in and catches me masturbating with a dildo again. She just smiles at me and says she had been watching me for a while. I look down at her pants which are soaking wet and her nipples that are hard as rocks sticking through her shirt.

I don’t move from my spot as she goes upstairs to take off her clothes and retrieve her toys as well to join me. She comes down in a pair of white stockings, garter belt and panties with a white basque that did nothing to cover her big beautiful tits. She held up her Jelly dildo and sucked on the end while she rubbed her pussy.

She sat down on the chair beside me with her legs up in the air spread eagle and running her dildo along her pussy lips and onto her hole then back up to her clit. She pulled off her panties and started running her toy in and out of her pussy as I watched, I got hard instantly. As I felt my cock grow hard again I started to feel the dildo in my ass feel even better. I started to ride the dildo like I was before when my mom got up in front of me. She buried my face into her pussy as I started licking her, sucking her clit and burying my tongue deep into her dripping lips as she moaned.

I got up because my legs were getting tired and started sucking on her nipples while she stroked my cock. I ran my hands up and down her body feeling her sexy lingerie as she felt all along mine. She went around and grabbed my ass putting her fingers in me as I put fingers into her pussy then glided around to her ass. She moaned loudly as she stretched my hole open making me so horny I just buried 2 fingers into her ass and 3 fingers into her dripping pussy.

She pushed me off and told me to get on the floor on all fours. I did as told and watched as she took our 2 jelly dildos and stuck the suction cup end of mine onto the base of hers making a double jelly dildo. I watched as she got down onto her knees as well and inserted one end into her ass as deep as it would go and pressed the other end to mine. I couldn’t last anymore as I backed into it hard just as she put the end to my hole and went right back to the suction cup, pressing into her more as well.

“You naughty little slut Missy, are you that impatient for a cock in you?” She says pushing back into me making me moan loudly and her quiver. We started to push our sexy asses back into each other making the dildo thrust into the other moaning loudly with me stroking my cock and her rubbing her pussy as we both squirted onto the floor.

I turned around and smacked her ass then held onto the dildo as I thrust back deeper into her until she was at the suction cup to. She screamed as that put her over the edge and her pussy squirted all over the floor and onto my balls. I could smell and feel her juice and the scent of her wet pussy which made me crazy. I fell to the floor pumping the dildo into her more as it mixed with her juices. Then my mom pulled the dildo out of her and grabbed me by my choker as she pulled me back smacking my ass hard.

 "Bad girl Missy, You made your mistress cum before you. Such a naughty slut you are!"

She laid on her back and put her legs wide open in the air as she told me to do the same. I felt as she inserted the dildo back into my ass and hers as well. We both sat up at the same time and thrusted our hips into eachother watching eachothers genitals leak our juices like two girls sharing a dildo in one of those lesbian movies I watch when im not Missy. We stared at eachother with lustful eyes before I grabbed my mothers ankles in my hands with the dildo still inside me and got on top of her. I started riding the dildo Like I was in the chair, but this time it was plunging into my mother's asshole. We both moaned like little sluts as the dildo went in and out of us with furious motion making both of us want to cum buckets of pussy juice and cum.

Finally we were just about to cum when the dildo slipped out of our asses and fell to the floor. My mother grabbed me and stuck my cock deep into her pussy, making me fuck her wildly like an animal as we kissed with deep emotion until she let out another orgasm as did I deep in her pussy.

She pushed me on my back and laid me down as she straddled my face and pumping the dildo in and out of my ass. I spread my legs wide as she fucked me harder calling me a slut.

 "Eat my pussy you dirty girl. If you enjoy making my pussy cum so much you can eat up my juices afterward."

I lapped up her pussy as she sucked my cock making me hard and moan while still pushing the dildo in deep until I needed to shoot my load of cum into her mouth. She held her mouth there until I was done and cleaned me up. Each shot hitting the back of her throat while she licked all around my head. Then my mother turned around and kissed me deep making me taste my own cum and swirling our tongues together before she took the cum back and swallowed it all.

"Get on the couch and wait for me you slut. I will be right back with a friend." She said with a grin savouring the flavour in her mouth.

I watched as she walked away and her juices flowed down her thighs. I licked all around the inside of my mouth tasting all the delicious flavours.

It wasn’t long before she came back wearing only her white stockings heels and a big strap-on with one of the jelly dildos secured in it. She picked me up by my hair and smacked my ass all the way to her bedroom. She threw me down next to a little box that felt cold. She picked it up and opened it to reveal 6 condoms full of cum. Then she went over to her dresser and startedTo continue reading this story you must be a member. Join for FREE here.

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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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Mommas new toy

I have acquired a new toy for us, an elaborate cock for us to play with... one end is an average sized cock (you know why soon enough) and the other end is cock shaped except for the many, small sensor like dots that cover the entire half... the half that will slide into that sweet, juicy pussy of yours. the sensors transmit whatever is done to the part thats not going to be in your succulent love box, as we cuddle and kiss each other, leading up to what you think will be our normal round...

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...

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
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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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...

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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