Telling Mom I'm A Crossdresser Part 11: Girl time
Add: 5 August 2015 / 12:16
It had been a while since my last time as Missy. I had been doing some jobs for people, nothing special mostly working on decks and mowing lawns for neighbors to not only keep up appearances so as to not give to much suspicion of where my money was coming from. This continued for what seemed like 2 weeks before and started to wonder if my fun as Missy had ended.
I walked in the door to find mom on the phone. I decided to go to get a drink before I got in the shower to cool off so I got some water from the fridge and sat down at the table. I had sat there for probably 5 minutes before mom finally put down the phone and went to the fridge for something to drink as well. I couldn’t help but notice that she was wearing only a g-string and skirt with a tank top and no bra. It made sense though considering how hot it had been lately.
She sat down at the table and opened a pepsi and drank it as we talked for a bit. Eventually she told me that tonight she was going to have a few of her girl friends over to see the stripper pole we had bought a while ago. I was surprised to hear that mom was going to show it off and not be worried about what her friends were going to think of her but I guess she didn’t care to much. I soon changed the subject in my mind to her girlfriends trying out the stripper pole which made me pretty hard.
“I’m going to need Missy’s help tonight as well.” She said as she tapped my hand.
Mom must have noticed that I was day dreaming because caught my attention before continuing.
“Tonight Missy is to put on that sexy maid outfit that she wore at that couples house over the weekend and serve everyone. I thought she would enjoy wearing her French maid outfit again.” She giggled after she spoke then took another drink of her pepsi.
As soon as she was done talking I rushed upstairs to quickly shower and freshen my body with a shave.
Once I was finished I went back to my room to take out my French maid outfit for later. I looked through it and decided I should upgrade a few minor details to my outfit. I still had some time so I thought I would pick out some lingerie to wear underneath. I found a nice pair of ass-less pantyhose and a shelf bra to give me a sexy but slutty look. One more thing I included was a black and white garter that went along with the maid outfit I was going to wear. Once I had all of that on I gave myself a look in the mirror to see if there was anything else I needed to add before putting on the uniform for the night. Just then mom knocked on my door to see how I was doing. I told her I was good and showed her what I had picked out for underneath my uniform for the night. She said it looked great but I was missing something and left for a few minutes. When she came back she had a pair of scissors and the strap-on we had used last time I was Missy. Mom got down on her knees and cut a hole in the pantyhose around my cock so that it was hanging out loose. Then she gave me the strap-on to fit over my cock. It fit great and the length was pretty long but I knew it would be sexy later on.
Now it was time for the maids outfit. I stepped into it and pulled it into place before I zipped up the back and made sure the skirt part was in the right position so that my ass could be seen when I bent over and just a peek when I stood up straight and my strap-on was plain to see. Next I slipped the rest of the dress into place and to complete my outfit I put on my blonde wig, makeup and 5 inch black high heels. When I was sure that I was presentable, I left my room to see what mom was up to.
It didn’t take long for me to find her because she was in her room preparing for the night as well. By the time I had found her she was already fully dressed and wearing a sparkling bright red tube dress that had no shoulder straps to it and was clutching tight to her skin. I couldn’t tell if she was wearing a bra or not but her panties showed up with almost every movement she made and caused her to pull her dress back down, but I have the feeling that she liked it that way. Her panties were hard to describe at first, all I could tell is that they were white with some kind of writing along the crotch. Once she had finished with her makeup, she sat me down and we discussed what was going to happen that evening.
Later on the doorbell rang for the first time that night. As instructed, I opened the door to find the first of moms friends. I have seen her a few times and recognized her as Carol, one of the girls mom often spends her spare time with and also one of the members of her group she always hangs around with. Carol was also looking fairly sexy as well in her backless dress with obviously no bra or panties but she was wearing a full body fishnet underneath her clothes which I have to admit was very erotic. I could feel myself becoming aroused and was glad I wore the strap-on to hide my hard clitty cock. She looked a little surprised at first but never broke her smile as I welcomed her in and showed her to the living room where mom was waiting. It was obvious to me that mom had been talking about me when she was with her friends but at this point in my Missy adventures I was more excited then scared of what erotic things they could be thinking to do with me.
I went back to doing my duties for the night when the doorbell rang again and once again I went to answer it. When I opened the door there was Molly and Erica, two more of mom’s friends that I had previously been acquainted with. Molly was wearing just a plain white tank top with a short skirt and matching stockings. Where as Erica looked like she had come straight from the office and was wearing a short pencil skirt with nylon stockings and blouse. Molly’s hair was done up in pigtails giving her a sexy teen appearance even though she was about the same age as mom and Erica still looked amazingly sexy even though she was in a business woman’s attire. All the women had brought their purses with them and took them inside. I couldn’t help but think to myself as to why they brought in their purses as there wasn’t really a need for them but I let it pass and continued with my duties for the night.
All the woman that had came to visit were very sexy. Molly had only about a C cup chest but a very tight and sexy ass for a woman her age. Erica and Carol both had very large breasts that were D cups like moms but Carol had more of a booty butt then Erica did but Erica’s was still very sexy. Each of the woman were a man’s fantasy just like in my head and I wanted to fuck each one of them before the night was over, but I still waited patiently to see where the night would take me.
I brought in margaritas for them to drink and I could see out of the corners of my eyes that their pussies were getting wet. Then they started to play around and slap my ass as well as hold and stroke my strap on. It felt good and I could tell they wanted more as did I. For a short while I left them and went upstairs to my room. All of their flirting and teasing my cock made me so horny I had to masturbate. I didn’t take off the strap-on and just moved it around and stroked the dildo until I came, shooting my load inside the dildo and giving it a creamy filling. Just before I headed back downstairs I decided to be a little naughtier and inserted one of my fancy butt plugs that had fake jewels on the base and the rest was silver. It felt nice and made me hard again so I could put the strap-on back on.
When I had returned back downstairs, I couldn’t help but notice how quiet it had become. I walked into the room to find all the woman were kissing and making out with each other and mom had her fingers under Molly’s skirt and Erica had her hands all over Carol’s breasts. Before anyone had noticed I slipped out and went to mom’s room to get the box of toys and put them in the same room as the stripper’s pole. Then I dimmed the lights and went back to the living room and in my most feminine voice I got their attention.
“If everyone is ready, the entertainment is ready in the next room.” I said as I pointed the way to the guest room with the stripper pole.
At this point, everyone in the room was horny and wasted little time getting to what the entertainment could be. Monica and Erica had already removed their panties and threw them at my face to enjoy, and Carol took off her red dress leaving only her full body fishnet. I couldn’t help but take a smell of the panties and savor the scents I was given before collecting them and the red dress to neatly fold and place to the side.
When I had gotten to the room, The fun had already began with the woman sitting in chairs and mom starting things off with showing off her own striptease. The woman watched in awe as I handed out drinks for everyone. Their gazes were too enticed by mom’s show so I was able to grab quick glances at each of their soaking wet pussies. I decided to tease them more and pretend like I was “accidentally” slapping them in the face with my strap-on which made them even hornier as smiles crept across their faces. It was time I broke out the toys and began passing out dildos and vibrators to the girls which they took happily and plunged them into their dripping wet pussies as soon as they got them.
It wasn’t long after that that mom had finished her dance and was left in only the heels she had put on. She walked off the stage and glided her hand up Erica’s body from her ankles to her neck and even making slight and teasing stops along her pussy and her breasts, letting her know it was her turn to give a show. Erica took the dildo out of her pussy and stood straight up and placed the dildo between her breasts then pulled mom close as they licked the head together as their massive breasts sandwiched the dildo between them.
This didn’t last long as soon mom took Erica’s spot on the chair and Erica stood up on stage and began her erotic display. I got mom a drink to and she whispered in my ear that I was doing a good job and should keep it up. Hearing that, I walked over next to where Molly was sitting so that I was between her and Carol. Then I bent over and looked down at molly using the vibrator I gave her to tease her clit then whispered in her ear.
“I see your having fun, would you like to play with me to?” I asked as I stood up and put the strap-on in her face.
She took it right away and started sucking on it and playing with it like it was my real cock. Then I felt Carol behind me rubbing my ass then giving it a good slap before grabbing at my butt plug and twisting it around inside me. I turned around to find Carol smiling as her wet pussy oozed her wetness and had a hard time choosing to stare at Erica who was grinding the pole and my glittery toy that she wanted for herself. Between the two of them I felt my body begin to quiver from all the teasing.
Before I could get to the point of my sexual high, Erica had finished her dance and now traded off with Carol. I could tell Erica was kind of a controlling type because she grabbed me and threw me onto the chair where Carol was sitting and wasted no time before putting it into her pussy and riding my strap-on hard and moaning almost immediately. I grabbed her hips and started thrusting into her juicy lips with everything I had. We were fucking so hard I was glad I wore the strap-on because with all this excitement I don’t think I would have been able to go for so long with my real cock.
Molly must have been feeling a little left out because mom got off of her chair so she could get on her hands and knees in front of Molly. Mom spread her legs wide open and buried her face into Molly’s pussy and started eating her out, licking, slurping and sucking so hard I could hear them over the music which made my thrusting even more intense with my growing lust. By now Erica was almost at her limit and she was leaning against my body as I pounded her hard and kept slapping her ass while calling her a dirty little slut. I took control over her and she loved every minute of it. I knew she would because someone who likes to control as much as her will lose their mind when they suddenly lose all their power over their partner.
Finally, Carols dance was over and got off the stage and slapped mom’s ass a couple times before lying on the floor underneath mom and eating her pussy. Molly got up and took her turn on the pole just as I made Erica erupt like a volcano, soaking my strap-on with her juices and collapsing on the chair. I managed to get up and decided it was now time for Carol to feel my big toy in her pussy. I got on my knees and rubbed the head along her lips. The sudden feel of my dildo surprised her and she stopped for a second to look at me. Carol smiled and went back to licking her pussy. Mom was moaning loudly as Carol stuck a finger into her ass and shoved her tongue deep in mom’s pussy. I gave my mom’s ass a little slap and she turned around with a surprised look on her face. She must not have noticed me playing with Carols pussy with the strap-on. Mom turned around and sat on Carol’s face, grinding her pussy hard like Carol’s nose was a cock. Just then I shoved the strap-on balls deep into the dripping wet cunt just inches from my body.
I wasted no time and thrusted as hard and as deep as I could, filling her with the plastic of my toy and mixing Erica’s Juices with Carol’s. Slapping noises could be heard and Carol gave out muffled moans that vibrated mom’s pussy. It didn’t take long until Carol orgasm as well with her whole body quivering. This sent mom over the edge and she came hard and all over Carol’s face and mouth so much that her makeup was running when she came up for air.
By this time all the women were naked, leaving only their heels on their feet and no other form of clothing. Molly was finished her dance and was fingering her pussy on the edge of the stage. I laid on the floor and wiggled my finger for Molly to come closer. She did and hopped on my strap-on, pressing her breasts up against my face as she rode my dick hard and inserting the full length over and over again. Molly was like a bitch in heat, aching for a big dick inside to satisfy her animal needs and my dick was just the tasty treat her lips needed. Molly came the quickest out of all of them and by now the strap-on was dripping down to my real balls and even my ass. All the excitement even got me close to orgasm and I took off the strap-on and started to stroke my cock. The 3 women all wanted a taste and got close to me as they took turns sucking my cock that was coated in the cum from when I went to my room to masturbate. Oh my god it was like heaven with each one of them working my most erotic zones.
After a few minutes with them giving me a reward for all of my service that night, I layed with my head to the side to see mom was back at our sex toy box and was looking for something. However, I didn’t care I was about to cum and cum I did. I shot big thick loads over and over, getting each of their faces a shot of my cross dresser spunk on their faces.
They gave me a few minutes to rest but they decided to keep on playing. Mom got a double ended dildo and started licking and sucking on the ends. They gazed deep into the others eyes as they deep throated the length at both ends until they were kissing in the middle. Erica was the one who broke the kiss and put mom on her hands and knees. Then she got behind mom and slowly inserted the dildo into her pussy and once it was in and mom began to moan, Erica got on all fours as well and inserted the dildo into her pussy as well until their asses were facing each other.
“Are you going to kiss with those lips now girls?” Molly said with a giggle as she rubbed Carol’s pussy.
They both smiled as they began to push back into the other, inserting the dildo deeper into not only the other girl but also themselves until their asses were touching and then their lips. As soon as Mom and Erica felt the others lips they moaned and started grinding the dildo hard.
At the same time, Molly and Carol started to 69 licking the other’s pussy and ass until it was clean and soaking wet. Molly kept giving little giggles and moans as she fingered both of Carol’s holes while Carol buried her tongue inside Molly.
Watching all this made me want to play to but I wasn’t able to get hard yet but that never stopped me before. I turned on my side and pulled out the butt plug and started to go back and forth between rubbing the opening and fingering my ass.
It felt incredible to wiggle my fingers inside my ass and watching all the busty older women playing with their pussies just enhanced the pleasure. I grabbed one of the toys the girls were playing with and started licking and sucking it. I could still taste their delicious juices that coated the toy and couldn’t help but start to deep throat the toy so I could lick it clean. Once it was wet, my first thought was to fuck myself with the toy but instead I decided to get in on the lesbian action with my little toy.
By now Erica and Mom had stopped with the double doggy position they were in and were now facing each other and thrusting their hips towards the center of the toy as they just stared into the other’s eyes and panted and moaned in ecstasy. I went to the toy box and grabbed some lube and another double ended dildo and made my way over to where they were fucking. I told them to lay flat on their backs and lubed up the toy with a generous amount of lube then I slowly inserted it into both of their asses. They loved it and now they were filled in both of their holes and were rolling their eyes back into their head like whores getting fucked silly.
I hadn’t forgotten about Molly and Carol, I went back to the box and got two of those battery powered “magic wand” vibrators that I had seen porn stars use on their lips and clits to bring them to a squirting orgasm. I gave one to each of them and to get into the double doggy position that Mom and Erica were just in. They did as they were told and just smiled as they turned it on and began to moan. I squirted lube on their assholes to but not as much as I did with Erica and mom since they were already soaking wet anyway. Once they were ready, I took the two dildos I had in my hands and got down onto my knees between the two horny sluts. I slowly pushed the dildos into their asses then moved them in and out fast and hard almost as soon as I got them in. They both cried out at the same time and I looked at them then back at Erica and Mom to realize that I had all four woman wrapped around my little finger and wanting to cum at my command.
“Cum you dirty little whores! Squirt all over each other and drench those tits in your pussy juices!” I demanded.
I knew it would turn them on but I never thought saying that would send them over the edge at the exact same time. In one loud scream, they pulled out and took away their toys and they squirted like four horny, soaking wet fountains flowing in tandem then collapsing as they panted on the floor in exhaustion. I began to clean up the toys, licking each one and getting a taste before putting it in the box to be washed later. Once I had picked up the last toy and even including the strap-on I had for most of the night I had realized that I never got my ass fucked that night yet. I just kind of huffed to myself in a peeved and disappointed mood, but then I looked around to see the women getting back in the chairs they sat in while watching each other do their strip teases and I told them I would bring them some water.
I took the box and went out to the kitchen. I set the box down next to the sink and put them one by one into the soapy water. Instead of water I thought the girls may enjoy a few mojitos with ice that would help them cool down and keep them all in a good mood for the rest of the night. Earlier in the day, mom and I made sure that there would be a place for the girls to sleep seeing as though they had planned on drinking tonight and no one needed a criminal record or to get in an accident. Anyway after I finished with the drinks and realized I was missing one of the dildos still. I looked through the toys again and counted to find that there was one missing and it was one of Mom’s.
I picked up the drinks and went back to the room where all the women were talking. I started passing them out one by one and when I gave the last drink to Mom, I looked to the stage to find the missing dildo. It wasn’t anything very impressive, just a simple average size white cock with a suction cup base.
“When you were getting your cock sucked I stashed this one away for later cause I wanted Missy to finish off our night.” Mom said.
I put down the tray I used to carry the drinks and got up onto the stage. Music started playing and I began my own little strip tease. It didn’t go to far and I made sure to keep on at least my ass-less pantyhose, shelf bra and garter that I had put on. At the very end of my dance I took off my garter then I through it into the crowd like at a wedding, and just like at a wedding, the woman all tried to grab for it and cheered and hooted at me. I have to say I loved it very much. Then as the music kept playing, I got down onto my knees and let the dildo slide into my ass.
I started to ride it, slow at first and gradually pick up speed and pumping the full length into my ass. Eventually that started to get boring but still felt good so I got up onto my feet for a reverse cowgirl position and rode it until I orgasmed.
The women told me that my show was very erotic and they loved everything Missy did that night. I told them they were very hot as well and loved how much fun it was to play with them that night. They also agreed and we continued to chat for a while.
A few hours later I looked at the clock and saw that it was now 3am. We asked if Carol, Erica and Molly wanted to just stay there that night but they declined our offer and said that they were alright to drive home. As I escorted them out, they gave me each their panties and bras as a souvenir for the night. I blushed and said thank you and they left giving me a kiss on the cheek as they walked out the door. When I looked at the panties, I saw there was a note in one of the bras and I opened it. I looked at the note and realized it was the cell numbers of each of the girls with “call us” at the bottom with lip stick smudges.
I grinned happily then heard mom upstairs taking a shower. I used this opportunity to go back to the stripper pole room and collect my things as well as the hidden camera that I set up without even mom knowing. I removed the memory card and brought it upstairs as I changed into my g-string and camisole for bed. By this time mom was in bed and I fired up my lap top. On the memory card was a complete video of the night from the time we walked into the room until my finishing striptease dance. I saved it to my lap top and stored the phone numbers away so that mom wouldn’t find them as I said to myself.
“These will be for my enjoyment only. Who knows, I may even call up the girls again sometime. Until then, I still have you two.” I said after I put away my other items then kissed my pink vibrator and flesh light I had under my pillow.
To be continued.