Teaching Caitlyn
- 2 years ago
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A few days later, I was on my bed reading when there was a knock on the door.
"Come in," I said figuring it was Lily.
It was my older sister dressed for bed in a similar oversized pajama top like her sister wore before. I couldn't tell if she was wearing panties or not.
This was different. We hadn't ever done this before. She laid on the pillow next to me, cuddling up close. She was so quiet I thought she had fallen asleep. I carefully put my book up and placed my arm around her. Unlike her sister, she had nice big breasts. It, being nighttime, it appeared, she didn't have a bra on either.
After I got up to turn off the light in the bathroom, she shuffled a little and cuddled up close again.
"What do you think of John Dickson?" she asked.
"How do you mean, Jaki?"
"He's kind of cute. Don't you think so?"
"No, I don't. If you think, he's cute, then tell him. Maybe he will say it back to you."
"Do you think I'm cute?" Ah! There it is.
"I think you are very attractive, charming, delightful, captivating, delicious and sexy," I answered.
"Sexy? How am I sexy?" she said.
"I will tell you the same thing I told your sister the other day. This is the absolute truth. If you weren't my sister, I would be at the front of the line of boys who wanted to date you. Your pretty face, your turned-up nose, your grin that makes me smile and the couple of grapefruits you seem to have in your bra all makes you sexy."
"You sweet brother. If you weren't my brother, I might just let you ... never mind."
I rolled over to see her face to face. "Don't tell her I said this, but you are prettier than Sarah. Her I can date, you, I can't."
Instead of responding to that, she rolled over on me a little and gave me a really nice kiss. I felt her bosoms loose up against me. Everything together got me hard.
She must have felt it because she got off and said, "I'm sorry?"
"Don't be. It's a reaction to any hot girl who gets within a foot of me. It happened a little with Lily."
"It did?"
"Yes, that is what generated my request to her. Have you and John kissed yet?" I asked rolling a bit on her.
"No, he seems nervous. Maybe he will come out and say something to me. I have to start all of our conversations. He seems worried about his sister Sarah. Always talking about her. If I didn't know better I would think he cared about her."
"She's his sister. Why shouldn't he care about her?" I said.
"No Ken. I meant care, like in love with? Can you believe that, a brother and sister in love?"
While we were talking, our heads were sharing a pillow. Her talking about love got my smile and my muscle engaged in the conversation.
"Jaki, I love you," I said kissing her nose.
"I know," she said kicking her lips.
She pushed her lips against mine, and crawled up on top of me, up against my burgeoning erection. This was wrong, completely, totally, and disgustingly wrong.
She took off her shirt, and I saw and felt her breasts for the first time in my life. I couldn't resist and starting sucking on her breasts and licking her nipples. She was enjoying this as much as me.
We heard a sound. She pulled her shirt back on and ran into the bathroom. Nothing came from the sound as she walked in.
"Did you like that as much as I did?" she asked.
I lowered the blanket and then my pants to show how much I like it. She touched it – the very tip – and I came all over her hand. I hoped that hadn't disgusted her too much. She got up, back into the bathroom and got me a moist towel.
"Sorry?" I said.
"Don't be, I play with myself all the time. Do you always cum so much?"
"I hadn't ... er, jacked off in a while. Are you sure that you are OK?"
After cleaning me up, she kissed the tip and kissed me then left.
Hoy crap, I came in front of my sister!
John and Sarah came over. I noticed them holding hands after getting out of the car.
We were sitting all together in Jaki's room.
"Can I ask you a question?" I said to John.
"Sure, go ahead."
"Do you like my sister?"
Jaki hit me on the shoulder. "Kenny!"
"Yes. As a matter of fact, I do," he responded.
"Do you want to date her?"
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FLAT MATES Part 3 - Chapter 11 - Summer in Manchester It was summer and the end of my first year at the University of Manchester Institute of Science and Technology. All through my last year at school I had looked forward to getting away from home for the first time and going to University. Don't misunderstand me, there was nothing wrong with my family life; Mum, Dad, my two sisters - Madeleine and Fiona - and I enjoyed a close, loving relationship at our home in Scarborough. It...
I was just walking alone in the park at night when I just so happened to walk into an old friend of mine. His name is Dale. Dale has short cropped brown hair and sexy brown eyes. He is roughly 6 feet tall, taller than me.Dale was one of those guys in high school who would make friends with a girl and toy with their emotions. Trust me I was one of them. But he was a very passionate guy. I used to like him before I found out he was just trying to score in my panties.I was hoping he wouldn't...
First TimeChris Hudson's world had changed in ways he could have never imagined. A few weeks ago he was a typical teenager, trying to get into his girlfriend's pants, partying with his friends, and playing lacrosse for his high school team. Suddenly he was a more mature, if still young man that was more than a little infatuated with his thirty eight-year-old mother. He no longer cared that he didn't have a girlfriend. In addition, lacrosse, always his first love, didn't mean that much to him any...