Telling Mom I m A Crossdresser Part 16 Hot talk With Mom
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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 theTo continue reading this story you must be a member. Join for FREE here.
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Sorry not much sex in this one but its a lead up to 13.5 and I hope you enjoy both of them. Once mom and I had gotten our car back, we took it out for a spin and I have to say it worked and looked like new. It had everything from a new paint job to new parts in the engine. Now in all honesty, I did have to go back a few times and give Ray a few blowjobs to help pay for them but it was definitely worth it and I didn’t mind sucking his huge cock anyway. Mom helped as well by going over to...
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My mom and I spent the next few days practicing and exercising with the stripper pole until we felt confident and extremely sexy while doing it, which I have to admit did not take long. One night I came home late from my part time job I had at a local restaurant and took the bus home. I didn’t have a car because I hadn’t decided on what car I wanted to get yet and what I could afford. I was sitting at the back of the bus and saw how there wasn’t any other person on the bus besides me and the...
Up until now, I have enjoyed my time as Missy. My mom had kept me busy with clients and we pulled in a lot of extra income and I was able to experience a lot of different fantasies, However I had not had the chance to try anything involving BDSM, or not yet at least. One day I came home from mowing the lawn for an elderly woman when I walked in the door to find my mother smiling deviously at the kitchen table. I instantly knew that Missy had been hired for another job. I sat down next to my...
Italy, september 2011. Sorry for bad english, I try to write correctly but don't know if I did. From tonight, I was a crossdresser. I'm been crossdresser from 12 to one day before my 27th birthday. Irony. I begin to have an answer to the question: "What feel girl?" Yes, a simple question. What feel girl when wear panty, tights, dress, skirt? What feel a woman in heels, purse, with her hair falling down the shoulder? What feel a teenage when begin to make up herself? When wear lipstick,...
Elizabeth embraced our night together like it would surely be our last. She said she believed me when I told her that Tuck had endorsed our sleeping together. She was concerned that he wouldn't remember asking me to fuck the bitchiness out of his wife when he woke up the next morning. It was after two-thirty when I climbed in bed with her, and I dare say it was after three when I went to sleep. Elizabeth let me sleep until eight-thirty before I woke to find her sucking my cock. "I still...
When my mom and I had gotten home, I immediately ran into the house to take a shower and change as quick as I could. I re-shaved my entire body and removed my makeup so that I could start from scratch and apply it again. Once I was finished with my makeup, I see a new outfit laid out on my bed. This was a cute nurse outfit with a short tight skirt that barely covered my ass. It was also pink with white stockings and long lace gloves that went up to my shoulders. Finally the top was like satin...
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...
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...
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...
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...
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...
CrossdressingWhen 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...
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...
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...
She stood at 5'6 with deep reddish brown hair. She was very skinny but she had the type of body designed to be small. Of course I wanted her, I wanted to do things that would make a trucker blush. But I couldn't at least not tonight; she needed me to be in charge. So I was, she had gone out again to find someone to replace the sorry excuse for a husband she had. She had 2 kids Sam and Kristopher, Sam being the oldest was 5 and Kristopher whom we called gopher was 2. That night Missy was...
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...
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...
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...
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...
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....
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...
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...
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,...
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...