Kinky Sex Stories

Boy Toy 1

Finding an apartment to rent with a private pool has always been a dream of mine but I rarely had the money so when I discovered that a mature woman was renting out her guest house on her large estate and there was free access to her pool, I jumped at the chance.

Joan was in her late 40′s and a very voluptious woman. When I filled out the rental application she asked me how I felt about lesbians.

“Well, I generally like them and find I have a lot in common with them. ” I said.

Joan explained that she was a lesbian and often had pool parties with her female friends. I became excited just at the possibility of that. Little did I know just how fun it would be and what my role at these parties would be.

Shortly after I moved into the guesthouse, Joan and I would sit up late at night drinking wine and talking by the oval shaped pool in her backyard. One night after a few too many glasses of Merlot, Joan began to ask me about my sexuality.

“Have you ever dressed up as a woman?” she asked.

“Well, maybe once or twice” I said.

“Did you enjoy delicious it made you feel?” she said.

“Well, just between you and me, I did enjoy the feeling of the tight panties around my waist. I am a submissive man and it felt very natural to wear woman’s clothing. But please keep my secret between you and me ok?”

“Come here and sit between my legs for a second.”

I shyly approached Joan and sat between her legs with my back to her large breasts that were pressed against me. She reached into her purse and brought out a roll of lip-gloss and applied it to my quivering lips.

“Now, how does that feel my little girly boy?”

“It feels very soft and smooth.” I said.

“You know, I think you would make a very beautiful woman. Come inside with me, I want to show you something. “ She said.

Joan took my hand and escorted me to her bedroom closet and asked me to pick out something to wear. I choose pick stockings, pink panties and a pink baby doll teddy

“Very nice choice my little sissy. I think you have done this before haven’t you? Now take off your boy clothes and I will pink you and pamper you my sweet boy”

I stripped off my clothes and Joan watched intensely and smiled. Once naked she asked me to turn around so she could get a good look. I was very erect and a little shy. She asked me to spread my legs slightly and bend over. I did so and this pleased her.

Then Joan began to dress me in her pink clothes. Once dressed she led me to her makeup table and applied makeup to my face. To finish it off, she found some red high heels and I slipped them on.

“You look much better like this don’t you think?” she said.

I was too shy to answer and just nodded my head a little.

“Let’s finish our wine outside now my sissy boy. “ Joan said.

Joan asked me lots of personal questions about my fantasies. I admitted to her that once my ex girlfriend had used a strap on dildo and I had the best orgasm of my life. And that I secretly thought about sucking cock sometimes.

“Come sit on my lap little sissy. Since you shared such personal information I want to give you something special now.”

I sat on Joan’s lap and she pressed her lips against my lips and our matching lip-gloss began to slide around and as her tongue invaded my mouth, I began to taste the sweetness of the lip-gloss and was engulfed in her purfume. Joan’s hand slipped down into the back of my pink panties and she began to massage my ass. I stopped kissing her and looked into her eyes.

“Oh don’t pretend that you don’t like this. Just relax my sweet boy or I will tell everyone your secret.”

I realized at that moment that I was completely under her control. I was her new boy toy and was forced to do anything she wanted with me. Secretly, this excited me so much that I almost had an orgasm.

Joan began to kiss me more as her finger worked it’s way into my tight hole. She moved it in and out and up and down and my pelvis began to buck back and forth.

“Ohh, the sissy likes this doesn’t he?”

Joan’s finger felt so wonderful inside of me and I felt so luscious in my pink clothes. Joan reached around and began to message my cock at the same time she was fingering my hole. I could feel the smoothness of the pink silk panties gently rubbing around my swollen cock. I began to cum inside my panties before I could even think about it.

“That’s a good girl, cum inside your pink panties for me sweet one. Oh you like that so much don’t you? From now on, I only want you to cum with me. You are my new boy toy to add to my stable. “

After I blew my load, Joan directed my head to her crotch and told me that now I must return the favor. I began to lick her clit through her pink panties until she began to moan and twitch. I pulled her panties off her and she pressed my head against her wet pussy and then began to cum all over my face, which cause my makeup to run.

When Joan was finished she said,

“That was a very good sissy. You have my juices all over your face now. You have pleased me very much.”

She embraced me and whispered in my ear.

“My sweet sweet sissy boy. I have many ways for you to please me. Now go to your room and sleep in your sissy clothes and meet me in the morning.”