Kinky Sex Stories

Forced To Feminize. Crossdressing With My Step Mom. Part One.

By Tyronne Wilson.

This is a real and true story about how I was forced to feminize and began crossdressing with my step mom. I have wanted to share this for a long time.

 

It all started when I was a teenager. My father remarried a beautiful blond woman named Suz. Shortly after that, my father died and I was left with my step mother to raise me. My step mother was a very powerful and strong dominant woman who was a bit of a feminist. She was a large and voluptuous woman in her mid 40’s and although I know she loved me, she would often tell me that she wished she could have had a daughter before my father died, but instead she was stuck with me. My step mom and I lived in a large house in Seattle overlooking the city and she was very active in women’s organizations so there were always social gatherings, parties going on, and beautiful strong women in our house.

 

My step mother pulled me out of all of the sports I was involved in and began to take me to the women’s groups and social functions instead. Soon, all my friends were older woman who were always telling me how cute and sweet I was.

 

Looking back, I can see now that my crossdressing started the day my step mother gave me a pink thing panty to wear as a bathing suit. It was summer, and we had a nice pool in our backyard and all the women were over swimming and sun bathing. I remember I got to put sun tan lotion on them all and it gave me a huge hard on.

 

“Sweetie,” my step mother said. “Your bathing suit is ugly. Let’s go inside and get you a better one.”

 

We went into her bedroom and she abruptly yanked down my swim suit.

 

“Mom, I’m naked. I’m not a little boy any more.” I told my step mom.

 

“Quit your wining. I have seen your penis before. Now stand there and let me put this cut little swimsuit on you.” She said as she spread my legs apart and I stepped into the pink thong bikini.

 

“It’s a good thing you are not too hung. If your penis was any bigger it would be coming out of your thong. Now turn around and let mom look at you. Very nice. Your butt looks good in that pink bikini. All the ladies are going to love you in it.” My step mom said and she took me by the hand and led me into the backyard where all the ladies were swimming and sun bathing.

 

“Ladies,” my step mom announced, “my sweet pretty boy here has found a wonderful pink bikini to wear for you today. I am going to pass him around so he can put sun tan lotion on all of you and you can put lotion on him too if you like. Think of him as your personal assistant and if he does not do as you wish, you have my permission to spank him.”

 

“Now honey, I want you to do me a favor today and do anything the ladies ask of you ok?” My step mother told me and gave me a good spank which turned my bottom red.

 

My step mother was all I had and at that moment, I didn’t think much about her behavior towards me. To be honest, I enjoyed all the attention of those beautiful older and mature women whom I got to rub lotion on, and they rubbed it on me. Some women spanked me, one even took me over her lap and spanked me hard many times, then spun me around to show everyone how red my bottom became.

 

But it was my step mother’s friend June that I remember the most. She threw me into the pool and jumped in after me. She chased me in the pool and when she caught me, I tried to get away but she was too strong for me. She held me there for several minuets just laughing at me.

 

“Your not so strong are you?” June said. “Your more like a little sissy. A young boy like you can’t even get away from me.” June reached into my pink bikini and grabbed my cock and balls. “You won’t be needing these anymore little sissy. And it’s a good thing too cause your penis is not very big. From now on, your penis is going to be your clit.” June said as she squeezed my ball sack a little.

 

I remember that it turned me on a little bit to be man handled in this way. I was still a virgin and any contact with women turned me on.

 

June held my cock and balls and stood behind me in the pool. We were in deep enough water that no one could really see what she was doing to me. June stood behind me and then began to slid her finger up my ass.

 

“Now hush little sissy, don’t say a word. I am going to give you a very special treat right now.” June said as she slid her finger up my ass as far as it would go.

 

“Relax, yes, that’s nice, very good, I can feel your sissy penis getting hard. Your boy clit is very hard because you like it don’t you?” June said.

 

After fingering my asshole for awhile, June dragged me out of the pool and then showed all of my step mothers friends my hard on that was poking out of my little pink bikini.

 

“Look what the sissy has to show us.” June announced to everyone. I was completely humiliated as they laughed at me. I ran inside and cried on the bed.

 

Shortly after the pool incident, my step mother began to crossdress me. It all started one night after I took a shower. She came into the bathroom and too my clothes and said that she had to wash them and would leave me other clothes to wear laying on the bed. The clothes she left me were girly clothes. Panties, a bra, a slip, stocking, and a little teddy.

 

“I can’t wear these girl clothes mom.” I said.

 

“Oh don’t worry. No one is here to see you except me, and I think it would be fun to dress you up as a girl. Besides all your clothes are in the washer and if you don’t wear these, you will have to walk around naked all night. No come here and let me dress you up.” My mom said.

 

My step mom first slid the lace panties up my legs. Then she fastened the bra which felt strange. Then she slowly slid the stockings up my legs, and finally added the lace teddy.

 

“Now stand up and turn around for mom. Very good. You make such a lovely young girl. You look very innocent and submissive. Lets finish you off with a little make up from mom’s make up.” My step mother said as she took me by the hand and forced me into womanhood.

 

I stood in the bathroom with my step mother applying my make up. After she put red lip stick on my lips she stuck her finger in my mouth.

“Now show me what those beautiful red lips of yours can do. Suck on mamma’s finger little sissy.” She said while I sucked.

 

“Oh you look just fabulous. Lets go into the kitchen and talk until your clothes are done.” My step mother said.

 

We walked into the kitchen and then my step mother took lots of pictures of me. Asking me to pose in various positions. It felt a little strange but it was kinda fun to be dressed up as a girl. Just this once I thought.

 

We talked all night and then when it was time to go to bed my step mother said, “Listen, sweetie, your clothes are still not dry yet, you are going to have to sleep in your girl clothes tonight. But I want you to sleep in my bed because it makes me so happy to see you dressed up like a girl.”

 

My step mother took me by the hand and into her bedroom. She undid the bed and pulled me into it held me for a long time before we fell asleep.

 

“This is nice isn’t it? We should do this more often. Mommy likes it when her little girl sleeps with her at night. Mommy has been very lonely in bed for a long time.” My step mother said as she held me tightly and caressed my lace teddy and fondled my bra.

 

I was a virgin then, and the feeling of having big tits pressing against my back, her hands on my hips and rubbing my chest, and the smell of a woman was wonderful. I had a hard on and didn’t want my step mother to find it so I pushed my dick between my legs and soon feel asleep in my panties and bra laying next to my step mother.

 

Forced To feminize crossdressing with my step mom part one.