My Boyfriend, MY Sissy
When I came back to bed, Colleen was holding a small plug. It had a cord that ran to a battery box.
“This is a butt plug. Guess where it goes?”
“My ear.”
She laughed.
“It goes in your butt and it vibrates. It will stimulate your prostate and let me have both hands free, which I promise you'll be thankful for,” she leaned close and spoke into my ear. “Because I'm also great at hand jobs.” She coated the plug in lube and, after a little difficulty, got it into my ass. She switched it on. I felt a tingling vibration that spread up and down my body. I laughed.
“What?”
“You’re amazing.”
She kissed me. She put lube on her hands and started slowly, softly rubbing my penis. She worked her hands up and down the shaft with such a light pressure that I thought I would go insane.
“Doesn't that feel good?”
“Oh my God! Yes it does.”
“My Michelle likes having things in her ass, doesn't she?”
I didn't respond. Colleen took her hands off my dick.
“Doesn't she?”
“Yes, I do.”
“Yes she does?”
“Yes, she does.”
Colleen put her hands back on me. She slowly, lightly, traced her fingers along the veins up and down my cock. She rubbed right below the head in a small circle. It felt like she was touching each and every nerve ending in my body. Colleen sensed I was getting close and slowed down.
“Not yet sweetie. I want this to last. Don't you?”
“Yes.”
“Good girl.”
She kept bringing me close to the edge and backing off just in time. The pleasure overloaded my senses and I just lay back and stared at the ceiling. I felt drool run down my cheek. I opened and closed my hands. I don’t know why, but I kept doing it.
“You're being such a good girl, aren't you?”
I didn't answer. Colleen stopped stroking.
“Yes. I am.”
“Yes you are what?”
“Yes, I'm being a good girl.”
My erection pulsed. She put her hands on me again and stroked slowly and delicately. But this time, she didn't stop when I got close to cumming.
“Cum for me. Cum for me, now!”
I exploded. For the first time in my life, I screamed while cumming.
Colleen kept stroking me as I bucked my hips and made strange moaning sounds, until the pleasure turned to pain. She kept stroking me.
“Ow, please Colleen, stop!”
She stopped.
“Does it hurt?”
“Yes! It hurts!”
“I’m going to give you five more strokes. You’ll take that for me, won’t you?”
“Why?”
“Because I said so. Ok?”
“Ok.”
She gave me five fast hard strokes. I jerked and writhed. Colleen laughed. When she was done she threw herself on me and kissed me all over my face.
“That was so nice! You really let go and allowed yourself to feel pleasure.”
“Oh my God, Colleen! You’re the best!”
“You get extra pleasure when you do what I say. Understand?”
“Yes.”
“Yes what?”
“Yes…Colleen?”
“Good girl. Now don’t move. I’m going to get a washcloth.”
When she had wiped me clean, she turned me on my side and spooned me. She rubbed my chest and told me to go to sleep. As I lay there, I felt weird about letting her call me a girl. And why did I say I was a good girl? Just thinking about it made me blush. I thought maybe I should say something, but I decided it was best not to. It wasn’t a big deal: her calling me a girl in bed. I just wouldn’t let it go further.