Telling Mom I’m a Crossdresser Part 9: A New First for Missy

It was a few days later after my night with Greg and being his police bitch for the night when I found myself sitting on the couch in a pair of nylon stockings, thong, bra and of course my new brown hair wig and breast forms. That night mom had to work late so I had the house to myself.

 

For the first half of the night, I walked around the house and watched some of my favorite zombie movies. Eventually, I got horny (as usual) and decided to try out that Sybian that mom had gotten me so many days ago and had surprised me with when I came home after my night with the bus driver.

 

After I had gotten it all set up, I got out all my toys and my lube and set them up behind the Sybian to help me choose. Then I went to my mom’s room again and decided to get the video camera as well and make a video for all my fans on the Missy website.

 

Once I had it all set up I needed to figure out what I needed to decide what I was wearing. I started to pick through my closet when I saw myself in the mirror. I gave a quick turn and decided that I looked pretty sexy as is and that I wouldn’t need anymore.

 

I decided to check to see how much time I had to record on the video before I started anything just in case it stopped part way through. I switched to the playback function on the camera and found a video on it already. I hit the playback button and found short clips of all the times mom had recorded me during some of my Missy adventures from my time out at the glory hole until we did our pole dancing routines.

 

As I watched my clitty cock grew hard in my thong and I decided to watch this instead of being recorded while I used the Sybian. I hooked up the camera to the television and hit play. As it started I quickly hooked up my ten-inch bendable dildo to it. As I glanced to the video from time to time and listened to it, I got the lube and added lots onto it and inside my ass before I got on the Sybian to begin my fun.

 

I took off my thong and threw it to the side of the Sybian so that it was out of the way yet still in reach if I needed it. It was very slippery and moved around so much that if I didn’t hold it up it wouldn’t be able to stand up straight so I could sit down on it. I stood up onto my feet and slowly lowered myself down onto the dildo and inserted the head. It felt warm and I knew this was going to go deeper then anything I have had before but looking at the video again I knew I wanted to try. I lowered myself more and more until I was at eight inches on the dildo.

 

By now the video was at the part of my role play as a nurse and thought I should hurry up a little because the video will be done soon. I turned on the Sybian and the vibrations shook the dildo deep inside my ass. At first, it took me by surprise by how far it could vibrate but I soon started to love the feeling as I moved my body all over with the dildo bending in every direction I could bend my body. I had to adjust my stance now because my legs were getting tired and as I moved my foot, I accidentally hit one of the switches on the remote and kicked it out of reach.

 

Now I was fucked in both meanings of the sense as the vibrations suddenly became more intense which made my entire body shudder from the pleasure I was receiving. My moans became louder and longer as I could feel the lower half of my body become numb and my clitty cock swelled drool and precum like a stream that seemed like it would never stop. I ground my hips back and forth again and again until the very point where I was about to cum.

 

All of a sudden, the vibration stopped and I was left with my clitty cock on the edge of an orgasm and had to let it subside. I couldn’t believe it just stopped and had left me aching for more like it did. I needed to check the remote to make sure I had not broken it on my first use and leaned forward so I could get it.

 

Just before I could get the remote the Sybian kicked in again and I was suddenly feeling that amazing vibration again but now it was coming in waves from slight, barely able to feel vibrations to intense waves that I could feel up to my nipples. This went on for what felt like an hour and I had come twice before it stopped again. I could feel my ass become so relaxed and throb with my clitty cock and decided I needed a break for a bit and turned it off but kept the dildo inside me. As I sat there, I felt the last inch of the dildo slip in as I felt like I was just filled with another inch of wonderful cock.

 

I completely forgot about the video I was watching and looked up just in time for the last part of my pole dancing routine with mom before the video was turned off, however, the video was not over there. Suddenly a video of mom came on and I heard a voice.

 

“I see Missy has been naughty and went into my room. I hope she enjoyed her collaboration of her sluttiest times, now she can see one of Mistress Mommies’ naughty little times,” She said on the screen.

 

I looked closer and saw in the video that she was wearing thigh high stockings, full ar-length matching gloves, a bra with soft looking pink fluff over the cups and a g-string. She walked over to the bed in her room and laid down on her side. It wasn’t long before a man walked out of the bathroom in her room wearing nothing but a towel.

 

He was tall with a shaved head with very black skin and amazing muscles. When he got to the edge of the bed they exchanged some very erotic words. I couldn’t remember what they were because at that time I was too busy rubbing my clitty cock to get it to stand again and putting more lube on the dildo.

 

Once it was inserted again, I switched on the Sybian again to its low setting as I saw my mom get on top of the very sexy black man and start to ride his cock. It was hard to tell, but his cock looked to have been a good ten inches and mom could take it all like a porn star. I switched the Sybian to high gear and I rode the Sybian in sync with mom riding the black cock. Mom and the black man were moaning furiously as was I once again.

 

This continued for thirty minutes before the black man gave a few more thrusts before cumming in mom’s pussy. She sat up off his cock and I could see his thick, hot creamy load come flowing out of her pussy as she was now on all fours and kissing him deeply. The sight of that made me go crazy and I came hard as well one last time. 

 

However, before I could turn off the machine there was a sudden rush to my insides. It felt like I had just received a massive cum shot deep inside me just as mom did in the video. It must have shot four good ropes inside me and started to flood down the shaft before I turned to find my mom holding a remote.

 

“I see Missy found my little surprise and decided to enjoy herself to it,” She said with her famous devious grin and a little chuckle to go with it.

 

“What did you think of that little finish I left just for you?” she asked.

 

I smiled and replied to her that it felt great and loved the video of her and the black man. I continued and asked what his name was and how did they meet? She stared right at me and smiled.

 

“You will see soon Missy, don’t worry about a thing,” She said as she left.

 

I just smiled and got off the Sybian so that I could clean everything up and put it away. My ass felt so used and hot as I could feel the fake cum drip down my thighs and legs. My body was still shaking from the vibrations and I felt so dirty from all the cum. Once I was finished cleaning my dildo and putting the Sybian away, I thought I should take a shower to clean myself up before bed. I took off my clothes and put what was dirty in the clothes hamper and what I could wear again I put back in the drawers. Then I got in the shower and got cleaned up.

 

After I had gotten out of the shower, I was heading back to my room when I heard mom calling me. I walked into her room to find that she was wearing nothing but a bra with her panties laying beside her on the bed and her vibrator next to that. I looked down to find a very noticeable wet spot on her bed. I guess she must have been masturbating while I was in the shower and couldn’t hear her from the running water. I asked her what she wanted to see me about.

 

“I wanted to try that Sybian you were using before and was wondering if you could help me set it up?” She asked.

 

I agreed then we went to my room and got the Sybian and set it up in mom’s room. Once it was set up, I got up to leave when mom stopped me again. She got out a new pair of stockings, panties and bra and gave them to me and told me to put them on. I did as I was told and looked at my self in the mirror.

 

The stockings were white thigh highs with lace around the top. The panties looked like a thong with black mesh around the edges and a garter belt to go with it. Finally, there was a white bra that latched behind my back but did not have shoulder straps and was only see through around my nipples and fit fairly snug but nice. I put on my wig to complete the outfit and mom said that looked great on me.

 

“What’s the occasion, mom?” I asked with some curiosity as to why she would buy me such nice lingerie.

 

She told me that it was because she saw this in the store and if she bought that she could get another set just like it. I felt a little happy and liked the idea of wearing matching lingerie with my mom but wondered what else she had planned. I looked back at mom and found she was just finishing putting on her lingerie set as well and she was right it did look exactly the same as mine.

 

Just then the doorbell rang. I was confused as to who would be coming to our house at this time of night. Mom and I went to the door and opened it. Standing at the door was the black man in the video that I had seen mom with earlier in the evening but now I got a better look at him.

 

He was the same height as my mom with braided corn rolls in his hair and a goatee for facial hair. He had some muscles but no abs and a stomach on him but you couldn’t say he was fat. Altogether, you could say he was medium built but when I looked down at his sweatpants I saw his semi-hard cock. It went almost down to his knee and it was easy to tell that he was at least ten inches long.

 

Mom welcomed him in and we got on both sides of him and felt up and down his body as he caressed our asses and felt us all over. I could feel his finger gliding up and down my ass then press to my hole as it slid with the thong into my ass with ease after using the big dildo on my ass. Then I looked over and saw him put a couple fingers in my mom’s pussy and rub her clit through her thong.

 

Needless to say, he was trying to get us horny and ready for a good fucking. He looked at my mom and gave her a kiss on her neck then he turned and looked at me then back at her.

 

“You two seem to be ready, I can slip my fingers deep in this sluts hole and your pussy is dripping wet,” He said with a smile as he smacked my ass and put two fingers in mom’s pussy.

 

“My names Lemar, what are your names, sluts?” He smiled, squeezing my ass tight.

 

“I’m Missy and I am a dirty little whore. This is my mom but you can call her a tight little fuck.” I giggled after I said that then continued. “Will you fuck us with your big black cock?” I asked as I felt along his length and mom rubbed his big cock head.

 

“I’m going to ruin all of your holes. Both of you!” Lemar smiled and smacked our asses before demanding we lead him to our bedroom.

 

We pulled his cock from out of his pants and revealed his now completely hard monster cock. It was now twelve inches long and almost as thick as a beer bottle. I felt my whole body quiver at the site of such a big cock. I grabbed onto his shaft and stroked him a little and mom rubbed his head as we took hold and lead him like a dog on a big meaty leash upstairs. At first I thought we would go to mom’s room but instead, we went into mine. I didn’t mind but it was a nice surprise.

 

Mom and I got onto the bed, I was on my knees and wiggled my ass toward Lemar and mom laid on her back with her legs spread wide open in the air and rubbing her pussy a little. As I looked back at Lemar, I saw him smile and stroke his cock before he spoke.

 

“I have an idea, there is nothing sexier than a couple hot little sluts stacked on top of each other while they are being fucked,” He said with a grin.

 

Lemar picked me up with ease and then set me down on top of mom. Now I was still in the doggy position with my legs spread wide open but now my thighs were holding open mom’s legs and my cock was rubbing on her stomach. As I squirmed and drooled precum on mom’s body, I could feel her pussy get hot and Lemar’s cock running up and down my ass and mom’s pussy which made me so horny. I couldn’t sit still and rubbed my fake tits against mom’s soft real ones. I could tell she was enjoying it too because when her pussy was rubbed she moved and her nipples rubbed hard against mine and she moaned even louder.

 

Suddenly mom gave out a very loud moan and I could feel Lemar press up against my ass. I looked down between my legs and saw Lemar’s cock plunging deep into mom’s pussy. My jaw instantly dropped and I looked back at mom then turned around and looked at Lemar. Then he stuck two fingers in my ass and glared at me in the eyes.

 

“That’s right slut, I don’t go easy on the holes I fuck and I’m gonna shove this entire cock into your ass until my balls slap your ass,” Lemar said as he pushed in another finger and rammed his cock into mom harder.

 

I looked down and mom again and she had her mouth wide open and her eyes were rolling back into her head. Mom was definitely in for a great fucking as I am sure I was as well. Lemar continued finger fucking me and fucking mom for fifteen minutes with all of us moaning, screaming and begging for more until mom gave a loud yell and flooded my bed with her pussy juice.

 

By now her body was covered in sweat and she laid back in exhaustion. Before I could take in what had just happened, I felt something get inserted into me followed by a flooding feeling of warm liquid. I knew immediately it was lube and it looked like Lemar was going to make sure he could slip all twelve inches into my ass.

 

Then he pulled out what he was using to put lube into my ass, I felt my insides tingle as the wet slippery lube made its way all around my insides. Then I felt Lemar put a finger to my ass. At this point, I was begging yet still felt a little nervous about having his cock inside me. His finger danced around my opening and I could feel him rub my ass with his other hand. Just the touch sent my body into shivers and I started to back up into his finger and moaning as I asked for more.

 

Without saying a word he grinned and placed his cock between my cheeks lengthwise and let it rest as he squeezed my ass cheeks together to grip his cock. I could feel the lube start to rub out of my ass like mom’s pussy dripping juices like it was before. I spread my cheeks wide and some drooled out a little and I looked back at him and begged for his big black cock.

 

“Please, baby, I want to feel that big monster dick inside my little boy pussy,” I said moaning in lust.

 

He started to rub his cock head around the opening of my ass and I almost came from just that little tease. Then the pressure increased as his cock head was pushed harder and harder until the head popped into my ass. The pain shot through my body and I told him to wait for a second before continuing so I could get used to his width. Then mom got into the action as well and wrapped her legs around my waist and her arms around my neck as she pulled me in close. She gave my ass a couple smacks then told Lemar to pound me like a dirty little tranny whore.

 

Lemar didn’t say a word as he thrust his cock into me, he must have gotten halfway into me before he stopped. I screamed as his massive girth ripped through me and stole my breath. I could feel his cock pulse inside me as my ass squeezed tight then struggled to relax and just as I felt I had relaxed my ass somewhat, Lemar shot the rest of his girth inside me.

 

At that moment I had never been so happy that I used such a big dildo and the Sybian before getting fucked by my very first big black cock. Once I could breathe again it was impossible for me to be quiet. Lemar began to twist his cock inside of me and grind with his cock balls deep inside getting to places I never thought a cock would reach.

 

I started to combine my breathing and my moans into a wheezy noise as my legs shook more and more and my clitty cock dripping and squirting precum and regular cum uncontrollably with every movement he made. I could feel mom rubbing against my body as my cum coated her stomach and even up to the bottom part of her tits as it did on me as well.

 

Once Lemar got a good rhythm going, he started to go in and out of me at a steady pace. This lasted for twenty minutes before Lemar announced that he needed to cum soon. By that time, mom and I had become incredibly sweaty and our fronts coated with a thin layer of my cum. Our big cock stud pulled his massive meat stick out of my ass then stroked as he demanded we got on our knees and sucked his cock to orgasm.

 

We got down on our knees right in front of him and started to suck and play with his cock and balls, taking turns as one of us sucked on his big cock and deep throated as much as we could while the other sucked on his balls taking one at a time then both as we swirled our tongues over every inch of his dark manhood. It wasn’t long before Lemar was finally at his limit and he needed to cum. He pulled away from us and mom and I got in close as he stroked his cock.

 

Finally, he came shooting long, hot and thick ropes of cum over and over again getting it all over our faces and hair and some even dripped down onto mom’s chest and my clitty cock. When Lemar shot his last load of cum, me and mom each gave his cock a few licks to make sure he was clean before falling over onto the floor and going to sleep.

 

When we woke up a couple hours later, Lemar was gone and he left an envelope on the table. Mom and I opened it to find two thousand dollars with a note inside it. We took the money then picked up the letter to see what it said.

 

“To the hot little sluts, I reamed out.

 

It was fun fucking your tight little holes but I couldn’t stick around. I left a bit of cash and wrote down the number of your phone, maybe we can have some more fun some time. Who knows, maybe next time I’ll bring a few friends next time.

 

From Lemar.”

 

Mom and I smiled and said nothing as we put the money and letter in a safe place and made our ways up to our rooms. Both of us had a tough time walking and I knew it was going to be like that for a few days but I did not regret it as I tasted more of the drying cum on my face. Just as I was about to go into my room mom stopped me.

 

“Your bed is still wet from my turn, why don’t you sleep with me in my room tonight? That way we can clean each other up like a couple of kitty cats,” She said with a giggle.

 

I smiled at her and gave a little purr and said to her

 

“Meow.”

 

To be continued.