I just watched my new best friend masturbate in front of his mom, and she clearly enjoyed watching him.
My name is John. I met Toby the year I turned 12. His family moved into the area from out of state and he was the new guy at school. Because we only lived a couple houses apart, I’d befriended him on his first day there, and we became best buddies after that.
We quickly get into the habit of going to his house after school, because my parents didn’t get home until after 6, and he had a stay-at-home mom. My parents thought it was a great idea that I had supervision, so they didn’t object.
I remember the day everything got topsy-turvy for me. We were watching some TV movie on HBO. Me, Toby and his mom Linda. It was an R-rated movie, and I was a little surprised Toby’s mom was letting us watch it.
There was a scene that showed a topless woman. I had only see boobs a couple of times before, in pictures, and I could feel myself getting hard.
It was what Toby did that really blew me away. “Damn, those titties are giving me a stiffy.” He said, out loud.
“Check it out.” He said as he stood up and pushed his sweat pants down to his knees. His penis popped out and slapped up against his stomach. He wrapped his hand around it and began stroking.
I was in complete shock watching him do this, but his mom seemed perfectly cool with it. She just watched him, smiling.
Toby continued to masturbate for not more than three minutes, before he started to moan and said, “oh God, I’m going to cum.”
He held his hand out, palm up and aimed his penis at his open hand. He continued stroking, as two or three small squirts of clear liquid came out of his penis. I was impressed, I wasn’t squirting yet.
Toby also had some hair growing above his penis. Something else I noticed right away was, his penis was a lot bigger than mine.
“Oh, that looked like a good one honey.” His mother said, smiling at him proudly.
“It was Mom, and I’m still hard, see?” He said, holding his hard penis between his thumb and finger, waving it around like a wand.
“Yes, I see that. You have such a beautiful penis honey. It looks just like your father’s, rest his soul.” His mother said.
I didn’t know what to say, or think for that matter. I just watched my new best friend masturbate in front of his mom, and she clearly enjoyed watching him.
Then Toby turned to me and said, “don’t you have a stiffy too John? Go ahead and take it out and jerk off.”
I didn’t know what to say. I was sitting there stunned, when I heard Linda say, “don’t feel embarrassed John, it’s perfectly okay if you want jerk off. Besides, all young boys do it”.
“Come on John, take out your dick.” Toby persisted.
Actually, I was hard as a rock. I couldn’t deny the fact that I really needed to cum right now. But damn, I had a little boy penis where as Toby had more of a man penis. I was embarrassed to let them see it.
I was starting to get the distinct feeling that I was not going to leave without jerking off in front of his mother. It was hard to tell who wanted this more, Toby or his mom.
I stood up and unbuckled my belt, unsnapped my pants and lowered my zipper. I pushed my pants down to my ankles and stepped out of them, then stood there in my tighty whities. My little boner tenting the front.
Linda’s eyes were locked on my crotch, and I thought I saw her licking her lips, but I wasn’t sure. I put my thumbs in the waistband and pushed down, being careful to pull the front out over my erection.
Then I stood back up, naked from the waist down, with my little 3″ penis pointing at the ceiling.
“My my, that’s a very cute penis John. May I touch it?” Linda ask me. I moved over to stand in front of her, and she reached her hand out and took the head of my penis between her thumb and finger and gently squeezed it.
“Ohhh god.” I said as my penis was being touched by a different person for the first time. She moved her thumb and finger along the shaft down towards my balls then back up to the head. She did this a few times, before she took her fingernails and gently scratched my scrotum. I could see my penis throbbing with my heartbeat.
“Let me see you masturbate John.” Linda said. By this time, I was so horny that I didn’t think twice. I grabbed my penis and began stroking.
“Oh man, don’t cum. I want to make you cum.” Toby said, as he took my penis in his hand. I was watching Linda’s face closely, and I could see her focus was intense. She was staring at her son’s hand, stoking my little penis.
It didn’t take me long, before I felt that tingly feeling in my balls start. “Ahhh, I’m going to cum”. I said between breaths. Linda watch me with a big smile on her face.
Toby not only didn’t stop stroking me, he started moving his hand faster. About 30 seconds later, I felt my penis jerking in his hand. He kept stroking, until I had to push his hand away because it was starting to tickle too much.
After he finished, I pulled my pants back up and Linda got up to go start making supper.
“Dude I can’t believe we just did that in front of your mom.” I said to Toby, as soon as she was out of earshot.
“Why, what’s the big deal?” He asked me.
“What’s the big deal? I’ve never jerked off in front of my mom. I don’t think I know anybody else who has, except you.” I replied.
“Who do you think taught me how?” Toby said, laughing. “Besides, my mom likes watching guys play. Once she gets used to having you around, and watching let’s play with each other, she’ll probably show you her pussy. She showed my friend Steve her pussy.”
That had my head spinning. Just thinking about the fact that I might get the chance to see an adult woman’s pussy.
It was time for me to go home so I packed up my stuff and left. That night, I jerked off in bed again thinking about Linda. In my fantasy, she was laid back, legs spread saying, “here John, come look at my pussy”.
The next morning at school, I found Toby right away. “I was thinking, can we go to your house after school today and maybe this time I can suck your penis while your mom watches?” I asked him.
Toby started laughing and replied, “yeah, you want to see my mom’s pussy don’t you?”
“Of course, have you ever seen it?” I asked him.
“Sure, sometimes she rubs it while she’s watching me jerk off.” He told me.
I walked around that entire day with an erection. All I could think about was being Linda’s pussy.
As soon as the bell rang at last class, I bolted out looking for Toby. I found him, and we started walking home.