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Telling Mom I'm A Crossdresser Part 3: Missy's Weekend

Part 3 of my Missy series :) enjoy and please rate and comment.
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. As she spoke I couldn’t help but smile and blush at being at the command of 2 strangers.

Friday came and I got dressed a little slutty and like a hooker as per the request of the couple. I wore a black tube top that read sex object on the front over the breastforms I had underneath. I also wore a red miniskirt that barely covered my ass and panties as I walked and finished my outfit with some fishnets and 6 inch heels and my blonde wig.

My mother then drove me to their house that night as she kissed me goodbye and told me she would pick me up on Sunday night. I walked to the door feeling my heels click all the way up as I gave my ass a good wiggle just in case my new master or mistress were looking.

I knocked on the door and a tall, very tanned, muscular male opened the door. He seemed to have been in his 40’s with short hair and if I could guess, I bet he would have been a body builder.

He told me to enter and called his wife. She was not as tall as him however she had what I bet was a good 40DD chest and 38 hip size with a slender waist. She seemed a little younger, Maybe in her late 30's as they both came to the door in towels and were now leading me to the living room where they both had put on some of their underwear. I just looked at them as my eyes kept going back and forth between the woman’s beautiful tits, ass and pussy and the man’s hot abs and 8 inch cock. They introduced themselves as John and Jamie. I introduced myself as Missy and that I would be the one to serve them this weekend as I curtseyed but soon dropped it as I forgot my miniskirt was very short.

They smiled and giggled a little as they walked closer and started feeling up my body and my sexy clothing. Jamie had gotten in front of me and started to kiss me as she massaged my tits and my cock while John watched. Then she broke our kiss, turned me around and smacked my ass hard.

“Mmm You’re a cute one, my husband and I will have lots of fun with you,” she said with a playful voice, rubbing her pussy and my ass.

I just moaned as I looked up at John who was starting to rub his cock in his pants and smile.

“Get your bags and go upstairs you little whore,” he commanded.

I turned around and bent over showing them my ass as I picked them up and wiggled my hips again as I made my way up the stairs. As I did they told me to put on my new uniform that was in my room to the left. I proceeded up to my room and found a sexy maid's uniform with a skirt that went to my thighs and I recognized as a ditzie micro maid dress that I had seen in some tranny clothes and role play catalogs. I put on the dress and then waited.

A few minutes later, Jamie came in wearing a pair of sexy white lace panties and bra with matching stockings. I looked at her and she looked at me before she pounced on me and started grinding her soaking wet pussy onto my crotch. I grabbed her tits and started massaging them as gently pinched her nipples and rubbed all over her body again.

Jamie leaned forward and told me to start licking and sucking her nipples as she took off her panties which I happily did. I lapped all around them, kissing and gently nibbling each one with tender loving care as I felt her slip her panties off from her body. As I continued to suck her hard delicious nipples, I felt my panties were coming down as well allowing my cock to spring free. Then I felt it, her warm pussy wrapped itself around my cock as she started to ride me hard thrusting down on me like she hadn’t had a good fuck in ages. She moaned and screamed wildly as was I for another 10 minutes before we changed positions and she bent over the bed. I shoved my cock right back into her and thrusted into her hard as I felt her warm juices and wonderful tight pussy clamp down on me hard. We continued to fuck for another 15 minutes before she stopped me to change positions again.

She sat on the bed before falling backwards over the edge so that her back was propped up against the side of the bed with her knees to her shoulders and her legs spread wide open.

“Come here you little whore, I want to feel that big tranny cock in my dripping wet cunt,” she said in a lustful and demanding tone.

I didn’t hesitate to comply as I made my way over and started pile driving her with my dick. She moaned wildly and begged for more saying everything she could to get me to keep fucking her.

“Oh god yes baby fuck me, fuck me hard. Oh yeah just like that. Keep going. Don’t stop, keep fucking my hot pussy until we cum.”

Hearing her say that made me so horny I fucked her even harder for another 30 minutes before we both exploded into a huge orgasm. I pulled out my cock and shot her load onto her tits while she squirted like a geyser completely soaking me in her pussy juice. We laid on the floor panting like tired dogs as I then felt a hand grab me by my wig so deep even my real hair was being pulled on. I looked up to find John naked and semi hard.

“Now that Jamie has had her fun, you now have to serve my needs you little maid whore. Get on your knees and suck my cock to make me hard.” John said as he pushed me to my knees right in front of his cock.

I began by kissing his tip and slowly licking up and down his shaft before stroking him a little and sucking his balls. His smell was intense and very manly the same as his wife but with a more womanly fragrance. I continued to lick all over and play with his cock until he was hard as steel before putting him in my mouth. I bobbed my head for 10 minutes before he pushed me off and told me to get on the bed.

“Yes master.” I replied

As I laid face down on the bed with my legs spread wide open I felt him apply lube to my ass before shoving 2 fingers inside and smacking me on my ass and calling me a whore.

“Mmm, yes, master, I will do what you tell me. I am your little whore and I will do everything you and mistress tells me.” I moaned as he fingered deep into my ass and twisted.

He then got on top of me in a laying down doggy position and started to fuck me. His cock was too big for my ass as he forced it in little by little while I held onto the pillow and sheets while screamed in pain but then turned to pleasure. He started to pound me as I turned and saw his wife was licking up my cum and rubbing her pussy with 6 inch dildo which I can assume was suppose to be my cock.

“Take it whore, ahhh yea you like that don’t you? Uhh you got a nice tight ass, I will enjoy fucking you all weekend,” he grunted and groaned while fucking me hard and deep.

“Yes oh fuck yes your cock is amazing master! I love your big cock and thank you for giving it to me, it feels so good and my mistress's pussy is so hot and soft and wet. It makes my clitty cock feel good. Thank you for making me your toy this weekend.” I screamed in ecstasy.

He continued to fuck me for another 30 minutes before finally cumming deep in my ass. I looked over and what I said must have sent Jamie over the edge as well as she let out a large moan and came with her dildo inside her as well with my cum still glistening on her face and tits. We all laid on the bed with me in the middle as we all fell asleep to rest for the next day.

Over the course of the weekend, we continued to fuck, suck and lick each other to orgasm over and over only for me to clean the house and change my clothes for them in between.We tried all kinds of different kinks from BDSM where the wife and I took turns being spanked and used while the other watch, to erotic roleplays where I was a tranny patient getting my dose of cum and pussy juice from my sexy nurse and doctor. However I think my favorite parts were when I got my 50cc's of cum and pussy juice obtained orally and anally. I also think I enjoyed watching Jamie getting tied up and told to fuck her pussy and mouth while she was helpless and John stroked his cock before fucking her ass as well.

Finally Sunday night came and my mom called my cell phone to say she was going to pick me up. When my mom had gotten to the house, she came in and asked what we did over the weekend. I told her in great detail as she smiled at me then at them. I could tell she loved the idea as her nipples got hard through her shirt. She was definitely not wearing a bra.

Then she walked up to the couple and asked for $3000 dollars. My jaw dropped when I heard that price but the couple just smiled and wrote her a cheque.

“Worth every penny,” they said with a grin.

My ass and cock were still sore from the weekend as I walked towards the door. However, before I could they stopped me and handed me the maid dress I had worn for them.

“We thought you might enjoy keeping your uniform since you seemed to have a lot of fun it in. Maybe others can have fun with you in it as well.” Jamie said with a wink and a giggle. I smiled and thanked them as we left and got into the vehicle to drive home.

My mom looked at me and asked how my weekend went.

“It was good, I have never felt the best of both world before but this weekend was amazing.”

“Mmm, well I am glad that you enjoyed your weekend, however we need to be getting home,” she said with a grin and rubbing her nipples.

“Why is that mom?” I questioned with a puzzled look on my face.

“Do you remember Missy’s first client that came to our house when I went to the org… I mean bridal shower? Well his name is Stan and he wants to see you again.”

My eyes lit up and I smiled. “Missy needs to take a shower and find something sexy otherwise she will be ready.”

To be concluded. (Maybe ;) )

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Continue reading Telling Mom I’m A Crossdresser Part 4: Repeat Business and Roleplays

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