Telling Mom I'm A Crossdresser
Add: 5 August 2015 / 11:43
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 until she caught me wearing her white lace bra, black stockings and her favorite 6 inch dildo with the suction cup in my ass . After that little incident I just came downstairs wearing some of her clothes one day and told her that I liked to wear womans clothing, and thought the idea of a man's cock in my ass was heavenly. She just looked me up and down and smiled and went on with her life, or so I had thought.
Since I no longer had to hide my secret, I was free to roam around the house whenever I wanted wearing some of her clothes that she didn't like anymore and just gave to me. I was happy that she did but couldn't help but wonder if she really accepted me. A few days later I saw her getting ready to go out.
"Hey mom what are you doing?" I asked
"I'm going out of town for a bridal shower and I won't be back until tomorrow morning."
"Alright, I will probably just stay here tonight, get dressed up, watch a movie and then go to bed."
She smiled then told me that I had a gift in the drawer with the clothes she gave me. I looked at her puzzled for a second as I began walking to my room when she stopped me.
"Not yet Missy, you can open your gift when you decide to get dressed after I leave."
With a confused look on my face I agreed with what she wanted and continued to just watch tv until she left. As I heard the door click, I got up and decided to take a long bath to shave my entire body and apply some perfume. When I was done, I decided it was time I opened my gift. I went to my room, and in my drawer I found a white box with a pretty pink bow on the front and a card on it.
"For Missy, wear this tonight and you will have another surprise later." The card said with a lipstick smudge on it.
I was surprised and now understood why my mom had called me Missy before. I opened the box and found a black basque with long latex gloves and stockings. I slipped those on as the latex stockings went up to my thighs and the gloves stretching up to almost my shoulders. Then I found a black latex thong with a tiny bow on the front. I stepped into the thong and pulled it up my legs. As I leaned forward I pulled it up the crease of my ass and over the top of my hips. It felt wonderful as the latex slipped between my ass cheeks and onto my already tingling hole. The last thing that was left for my present was a long blonde wig that went about the same length as my mom's hair and a bright red shade of lipstick.
Looking at myself in the mirror I felt all the way up my body, it felt great and I felt like doing something naughty while in such wonderful slutty clothing. I turned to take the empty box out of my drawer when I found a little bag as well. I opened it and found a small bottle of baby oil, a condom and a small ring with an extra bar on it. That I recognized as a cum stopper. I pulled my thong to the side of a second as I slipped on the cum stopper and lathered the sexy latex with the baby oil. Finally I sat down at my mirror and applied my new lipstick and wig as I felt I had truly become a woman now.
Returning downstairs I decided to watch another movie as I wondered what the other surprise would be. It was now about 9pm and the doorbell rang. I got up and was going to get a robe to cover up. However I decided not to since I had the lipstick and wig on anyway and just answer the door as I was, seeing as I did not have the time to take them off anyway.
Opening the door I saw a tall man, about 5'11" and built fairly big like a football player. He had a shaved head and big hands, as I looked up and down his body and glanced at his crotch, which to be honest looked like he was fairly big.
"Hi, you must be Missy," he said with a grin.
"Is your mom home?" I shook my head wondering how he knew that name.
"I'm a friend of your mom, she asked me to take care of her little Missy." He said with a devilish grin on his face looking me up and down admiring what he saw.
I just smiled and blushed as I asked him to come in. He entered and grazed his hand on my butt just before we sat down on the couch. As he sat down he had his legs wide open and I sat with my legs crossed hiding my clitty cock. He ran his hand along my leg and up my body to my cheek.
"Your mom told me you like to dress a little slutty and I see she was telling the truth," he said smiling.
He ran his finger along my lips and into my mouth. I just looked him in the eyes and moaned as I swirled my tounge around his finger as he went back and forth like it was his cock fucking my mouth.
"You want a nice big cock tonight baby, I can tell."
He lay back and unzipped his pants and pulled out a 7 inch cock. It wasn't very thick but it wasn't bad either. It didnt matter to me though because I liked depth more then width anyway.
I grabbed his cock and bent over as I started to lick up and down his shaft, and swirled my tounge around his head, tasting his precum as it coated my tongue. I bobbed up and down as I went down to his thick, hot man scented pubic hair. The smell was strong like that of a man working outside all day. I started to moan as I took deep breaths of his powerful manly cock stench.
As I gagged a little feeling his cock head rub the back of my throat, I got used to the feeling quickly. I could now deep throat his beautiful cock and I sucked him for about 10 minutes, before he told me to lead my slutty ass to my bedroom.
I took him around the corner to my room and closed the door. Grabbing the baby oil and condom my mom had left me. I handed him the oil and bent over the side of my bed while still standing up, bracing my hands on my sheets. He pulled my thong down around my thighs as he squirted the oil all over my ass. Then he pressed the end against my hole and gave the inside a good squirt to lube up my insides. It felt wet and wonderful as it made me even hornier for his big cock inside me. I felt his hand rub and massage my tight little hole, rubbing around the opening and gently dipping his thumb in and out of my hole.
I then turned around, got down to my knees and pulled down his pants to around his ankles as he kicked them to the side along with his shirt. Taking the condom out of the wrapper I put it in my mouth between my teeth as I rolled it onto his cock without using my hands until the end reached the base of his cock. Then I was deep throating him, taking in that wonderful smell once again.
He smiled at me and pulled me up to my feet. Then he pushed me back onto my bed where he grabbed my ankles and lifted them up to my shoulders, with my legs spread wide open giving him easy access to my oil dripping ass.
"I hear sluts like it rough and kinky. How kinky are you?" he asked with a lustful look in his eye.
"I'm a dirty slut and I love it anyway you want to give it stud." I said to him as I ran my tongue along my bright colored lips.
He slid his wrapped up cock to my ass, pressing it against my hole. Pushing against me a little harder as I braced myself for what to come. Suddenly, I feel a pop as his cock went deep inside me, my ass sucked in his full length as the baby oil inside me spurted out the side running all over both our cocks and balls. I moaned as he started to pump into me hard and deep yet going slow to not tear me apart because I was so tight.
Getting up onto his feet while still on the bed he started fucking me harder and deeper yet still keeping the rhythm. I started to pant heavily as I held onto the bed, beads of sweat starting to form on my sexy stud's forehead.
"Yeah slut you like that cock in your gaping ass don't you? Take it, Take it hard you whore!"
"Yes, Yes I'm your slut, I'm a slutty tranny hooker that my own mother sold me to be fucked and profit off my man cunt!"
That made him harder as he fucked me for another 10 minutes before he said he had to stop and change positions because his legs were getting tired. I told him to get off of me and the bed, as I grabbed him by his cock with a condom full of precum then led him to the kitchen with my thong still around my thighs.
My cock throbbed as the cum stopper I wore kept everything inside which made me feel so hot and sexy. I bent over the kitchen table, removing my thong as I reached and grabbed the opposite side of the table. He knew exactly what to do as he grabbed me by my hips and spanked my ass repeatedly before shoving his cock back in my ass making me scream loud. By now, my ass had gotten used to the feel of his cock and I loved the feeling of him taking me bent over my own kitchen table because now it had become the greatest thing I had ever felt.
"Bad slut! Bending over for a strangers dick presenting your ass without caring of the consequences."
I only moaned and rolled my eyes back as he pounded me harder and faster, swishing my insides as I held onto the table making it rock and bang on the tile floor. I was so loud the neighbors came to the window and saw me getting fucked, before shutting the blinds out of embarassment for being caught and walked away from the window.
He fucked me like that for 30 minutes before groaning loudly as I felt his throbbing cock fill the condom and swell inside my drooling ass. Pulling out he rubbed his cock, squeezing the last few shots of cum from it before pulling the condom off his dick and tying a knot in the opening and tossed it on the table. I panted and flipped over now laying on the table. He just watched then helped me up as he spun me around and smacked my ass one last time hard as I moaned. Now my clitty cock ached as I couldn't wait for him to leave so I could strip naked and stroke myself limp.
"Go get your thong and my clothes and meet me on the couch you whore!"
I did as I was told and I bought him his clothes back down the stairs, feeling my sore ass as he sat on the couch. He dropped a box on the couch with a bow on it similar to the one my mom left me.
"Your pimp said to give this to you afterwards."
He put on his clothes, left $200 on the box and left as he said "I'll be back again next week to fuck that tight ass again."
I couldn't help but smile as he left and I put the money in my basque between my tits and opened the box. There was tranny porn and a butt plug in it with a note as well.
"Insert the toy and leave your cum stopper back on as you watch this video. Do not touch your clitty or man pussy until I say so."
"Your Pimp, Mistress Mommy"
I did as I was told and waited for her return watching the hottest tranny porn I had ever seen, thinking that I just experienced the same thing without even getting his name.
To be continued?