Do you remember the first time you masturbated? I mean really did it the way you still do it today?
I do, I was just turned fourteen and was showering after gym class. I was in there with Steve Kenny, my best friend and there was another guy over on the other side that I saw who had his hand around his dick going at it. I nudged Steve and we watched out the corner of our eyes as it happened, arcs of white cum went flying up out the end and went swirling down the drain as we heard him groan in delight.
It was rather amazing to watch and about a week later, we were at his house, up in his bedroom, when he asked if I wanted to try what that guy was doing. Well, we both were rather amazed by what we'd seen so we were soon out of our clothes and had our fists going like we'd seen him do in the shower room.
It did feel good, really good, at least until his door opened and his mother walked in with an armload of clean clothes.
"Oh, geez," she barked, "get dressed you two. Then, Andy, it's time you went home," and she turned around and pulled the door closed.
"Oh, shit," he said, "I'm dead now. Oh, crap. What if she tells your Mom and Dad? They might think we're gay or something."
"I hope not. Maybe you can ask her not to tell them, I mean this is bad enough," and I got my clothes on and left.
We didn't really speak about it at school, it was just too embarrassing, and about a week later, he called asking me to come over the next Saturday. I asked him about his mom and he said she had a talk with him that same day but there had been no mention of it since. He even said that she'd asked why he hadn't had me back over to his house.
So, on Saturday morning, about ten, I rang their bell and Mrs. Kenny opened the door, standing there in her robe.
"Oh, hello, Andy, if you're looking for Steve, he's not here. But, come in, I want to talk with you," and I came in and we went into the kitchen and sat at the table. I just knew this was going to be bad.
"Are you still masturbating, Andy?"
"Am I what?"
"Masturbating? You know, playing with yourself, rubbing your penis like I saw you doing?"
She just asked me that like she was asking about the weather.
"Um, uh, well, yeah, kind of, a little."
I knew she was now going to tell my parents and that life, my life, was essentially over.
"Well, I've been thinking about what you and Stevie were doing and I think it's something I should tell your parents about."
"Oh, please don't do that. They would be pretty upset and, well, I'd be in a huge amount of trouble, please, I'll never do it again," I promised.
She sat there silent for a minute as I felt my whole life ending, then she said, quietly, "Well, Andy, I guess I could change my mind about telling them. Maybe if you did something for me?"
"Oh, I will, anything, chores, mow the grass, whatever."
"Well, when I walked in and caught you two the other day, I did think that what you were doing looked nice. I'd like to see you do it again, Andy, and watch you do it."
I just sat there stunned. She wanted to watch me jack-off. I'd been doing it some since I saw the guy in the shower room that day and now Steve's mother was asking me to do it so she could watch. Or, she might tell.
"It's not such a big deal, Andy. Just let me watch you do it, come on, we can use my bedroom," and she took my hand and led me up the stairs where we turned the other way from Steve's room and went in her room.
She pulled the covers back and stood next to the bed.
"Maybe this will help," she said as she pulled her robe open and let it slide back off her arms and on to the floor.
Omigod, I thought, the first naked female I'd ever seen. I knew then that she would not be telling my parents anything, that she was now taking this further than ever, that I was in for sex with her, I was now just sure.
"Now, your turn, Andy," she said as I began pulling off my teeshirt, then got my shorts off and stood there with my briefs all poked out. She reached out and took my dick in her hand, gripping it through my briefs and squeezing, then knelt down and pulled them to the floor. She looked up, then leaned forward taking it in her mouth and sucking it.
You know that I've jacked-off, I've told you that. But, oh, man, this was so better, just the best thing I've ever felt, I almost melted into the floor as I stood there being sucked by Steve's mom.
Then, it stopped. She stood up and said, "Well, Andy, let me see how you get yourself off. I want to see your cum shoot out," and I went over to the bed as she handed me a small bottle of clear, thick liquid, telling me I could use that if I wanted.
I dribbled a bit on the head and began.
She sat next to me, her hand softly rubbing on my chest and stomach as I ran my fist up and down. This was so sexy, just the hottest I've ever felt jacking-off. She then bent over and kissed me, putting her tongue inside my mouth and moving it around as her breasts grazed my chest. She moved my free hand to her breast which was so soft and nice and warm.
She raised back up as I went on jacking up and down, getting nearer and nearer, as I began speeding up, then my whole body like froze and my cum went shooting up in the air, even farther than I'd ever seen before and it seemed like there was more of it.
I groaned as she put her hand around mine and kept jacking me up and down.
"Mmm, beautiful, just beautiful. I love how boys cum," she said as she kept masturbating me with my hand in hers.
"Are you still hard, you still feel like it?"
"Yeah, I guess so," I told her and she pulled my hand away to see my dick still standing tall, still hard and erect.
"Would you like to touch me, Andy? Anywhere you want? Here, I'll let you," she said as she lay down on the bed, spreading her legs open making it pretty obvious that I could explore just about anywhere I desired.
"You can look and touch me anywhere, make me feel nice, okay? I'm yours for whatever you want."
I felt her breasts first knowing that seemed the safest thing to do but she let me touch her just about any place and I was soon down looking between her legs as she opened fully for me.
"Touch my pussy, Andy, you can put your fingers in me," she said softly as I ran my fingers up along the split between her legs. Her pussy was shaved except for a trimmed part right above and there was some slippery wetness along where my fingers were tracing.
I put the tip of my middle finger on her opening and gently pushed inward as I watched it disappear up inside her. She was all warm and slippery in there as I began finger-fucking her as her hand went down to take my dick.
"Mmm, feels good, Andy, you like this?"
"Yeah, I never expected, well, I never thought anything like this would happen, Mrs. Kenny."
She laughed and when she did, I could feel the inside of her pussy contract around my finger as she did.