I was a sissy before I knew what a sissy was pt 2

Part 1 is a true story. This is what I WISH happened after

Jim had rushed me out of his house after he came on me, and all over his sister’s clothes. He was in a panic and was worried about getting everything cleaned up. I had quickly changed back into my clothes and run home. When I walked in the house my mom asked what I had been doing. I said just messing around with Jim. She said, well you better go to the bathroom and clean up. When I looked at myself in the mirror, I saw I was still wearing rouge, eyeliner, lipstick which was now smeared all over. I looked like a 11 yo slut.
I was nervous. What could I possibly say to mom to explain this? I hadn’t planned on doing any of this at all. Jim and I were just playing around with sexy girl underwear. Then he had me put it on. Then makeup. When I saw myself in the mirror I loved what I saw. I looked like a pretty girl. For some reason, I liked looking like a pretty girl. Then Jim kissed me. It was just being silly and fun, but then he really started kissing me, and I kissed him back. Soon, I enjoyed the kissing. I liked that he was kissing this pretty girl, me the pretty girl.
But, obviously I couldn’t say any of that to my mom. I washed my face, and walked back to the kitchen where mom was getting dinner ready.
Ah, all washed up. Good. You looked lovely, but I’m not sure dad would agree. So, you and Jim must have had a good time together today.
I didn’t respond.
Did you?
No answer.
Carl, listen. I am not upset. I don’t care what you choose to be or do. If you want to dress up as a girl and kiss Jim, or and other boy, I support you in that.
Really? I asked.
Really. I love you. I want you to be happy. How love have you been dreaming of being a girl?
Uh, just today.
She looked at me doubtfully.
No, really. I explained everything that happened. Even him kissing me and then me liking it.
Hmmm, so it’s just an experimental stage. Well, we all go through that. Maybe you should try it again and see if it’s just a one time game or something you really want.
You think that I should dress up as a girl again?
Yes. I think you looked pretty.
That’s what I thought too, I confessed. When I looked at myself in Nancy’s mirror, I thought, I’m a pretty girl. I wonder if the boys would like me.
Is that what you want? For boys to find you attractive?
Yeah, I guess. I mean girls like Shelly and Angie, all the boys always want to hang around with them you know. They talk about them all the time. ‘I wonder what Shelly is doing’, Isn’t Angie sexy? I sure wish I could fuck her’. Oh, sorry mom. I got carried away. But, that’s how they talk about girls. Mom asked, “And you want them to talk that way about you?”
I don’t know. I haven’t really thought about it before today. But, I like tge way I looked.
And did you like kissing a boy? She asked.
Oh, I loved it. At first I was shocked, but when I let go, and just kissed him back it was amazing.
Damn, you’re getting me horny, mom said.
Mom!
What? You can talk about sex, but I’m not allowed?
No. You’re a mom.
Yeah, and the way you become a mom is by having sex. Believe me I love sex.
Mom!
Ok, well, we will follow up tomorrow. No more sex talk when dad gets home.

The next day dad left for work and I was sitting around eating cereal and watching tv.
Mom comes in. “Should we invite Jim over to play with you today?”
Do you mean…?
Yes, you as a girl.
I don’t know. Maybe he didn’t like it as much as I did.
Only one way to find out.
Your older sister is in California with my sister, and it’s just you and me. We can dress you up in her yellow sun dress. It’s too small for her anyway and will look so cute on you. I’ll show you how to do makeup properly. I’ve got loads of pretty jewelry. We can make you into such a sexy, pretty girl. All the boys will want you instead of Shelly.
I just smiled.
Good, she said, let’s get started.
First let me call Jim and make sure he is available.
I set a time for an hour later for Jim to come by. I told him I had a girl who wanted to meet him. Her name was Michelle.
Mom, got me all dolled up. I looked much better than when Jim and I did my makeup.
At the right time, the doorbell rang. I’ll get it, said mom.
Hi Mrs Allen, imare Carl and Michelle here? Well, Carl isn’t, but Michelle is, come in, she’s dying to meet you.
I was sitting in the living room wearing my yellow sundress, I had my mom’s blonde wig, makeup, nylons, and high heels.
Jim, saw me and just stared.
Hi, I’m so happy to meet you, I said taking a couple steps closer and extending my hand. I’m Michelle.
Wow! He said.
I chuckled. Well, I’ll take that as a compliment.
Yeah, i mean sorry. You look kinda like Carl, but way prettier.
Well, we are cousins, so I guess we look a little similar. And thank you for saying I’m pretty. You’re very handsome as well.
Come, sit on the sofa with me.
Jim sits and I sit right next to him with our legs touching.
Carl told me you were sexy. He didn’t say you were this sexy, I said as I ran the back of my hand across his cheek. I looked down at his crotch and saw that i was having a good effect on him.
Would you two like some lemonade? Mom asked.
Yes please, I said.
Mom brought lemonade and said she had to run to the store. She would be back in 1 hour.
You two have fun.
As soon as she left, I looked at Jim and said, I hope you don’t think I’m too forward, but, may I kiss you?
He didn’t answer, just wrapped his arms around me and started kissing. We passionately made out for several minutes.
Let’s go to my room, I said taking him by the hand. I want you to make love to me.
We quickly went to my room.
This is Carl’s room.
I turned back towards him, and kissed him again.
Carl?
Yes, Jim. Make love to me.
He hesitated a couple seconds then pushed me in the room and on my bed. He stood there and took off all his clothes. I licked my lips.
You’re so sexy Jim.
You like this body, Michelle.
Yes, I said. Then I leaned forward and grabbed his hard cock. Your cock is beautiful, Jim.
Suck it, baby. Suck my cock.
I instantly obeyed. My lipstick covered lips enveloped his 6 inch tool. I felt it push against the back of my throat and I gagged a little.
I’m sorry, he said.
No, i just never sucked one so big before. I had actually never sucked one at all, but know boys like to think that they are big.
Oh, you like my big hard cock he said.
Mmm yes. Fuck me please.
I pulled up my dress, and pulled off my lacy panties. I got on my elbows and knees and offered my hole. I had already lubed up anticipating this. So he slid right in.
He fucked me slowly and hard and deep, then back to slow. He finally came in my ass. I could feel it pumping into me.
Oh, Jim, I think I love you.
Good to see you kids are playing so well.
It was mom standing in the doorway. She snapped a picture with her Polaroid camera and a picture slid out the front.
Mom!
What? A mom needs to remember the day her daughter loses her virginity.
She smiled and walked away shaking the photo.
You’re mom is pretty cool, he said. I turned and kissed him again.
So, do you want to be my date to the movies Friday? All the guys will be so jealous.
I would love to go anywhere with you handsome.

🔞 Candy.AI 🔥 AI Sex Chat - Roleplay, Erotic Stories, Try for Free 🕹️

Please, Rate This Story:

(average: 4.63 out of 16 votes)