Becoming My MotherÂ’s Lover, Part two

Billy Williams was my best friend at that time and we were virtually inseparable. Billy was a few month’s younger than me, tall and slender, with fairly long, light brown hair. We’d pal around and do all kinds of things together. Yes, as horny teenagers, we had even masturbated together and had “jack off contests” to see who could shoot first. Anyway, my mother was always friendly and happy around Billy. She was always willing to play popular board games and cards with us. Enthusiastically getting into the excitement as the competition became more intense. She was particularly deadly serious when we played “cut-throat” hearts.

Mom also said that as teenagers we certainly needed to know how to “slow dance,” if we were ever to have girl friends. Consequently, she would frequently give us lessons on slow dancing, holding us close and swirling us around the living room to music played on the hi-fi. This latter activity! proved to be particularly interesting. Both Billy and I would get tremendous hard-ons while my mother would hold us tight as we danced. I frequently noticed that Billy almost always had an obvious erection after my mother would grind her pelvis into his groin during our dancing sessions. Billy would anxiously try to disguise the fact that he had a full-fledged erection. I’m sure my mother had noticed that as well, which led to another strange change in my mother.

After Billy left to go home one afternoon, my mother asked me a number of questions about him. The conversation eventually rolled around to sexual topics and just how much Billy knew. Now, Billy was younger than me and barely sixteen years old. As I mentioned before, although we’d done the usual boy experimenting and jacked off together, I knew that he was every bit as naive as I had been before my mom and I began to fool around. We talked for a while and my mother suggested that it would be nice to have Billy come to our house for a special sleep over. I was shocked. “Mom,” I said “are you going to try to play around with Billy, too?”

She just smiled softly. “Well, we’ll just see what happens. Later that week she called Mrs. Williams and invited Billy to spend Friday night with us. Mrs. Williams was delighted and promptly agreed, telling my mom that she’d drop him off about four on Friday afternoon. She did just that and another new adventure was about to begin.

I remember that first sleepover night vividly. Mom, Billy, and I played some board games after he arrived and we talked about school, sports, and about the girls in our class. After a while mom went off to fix dinner and set the table while Billy and I watched television. Later we ate mom’s delicious tuna noodle casserole and then we helped her clear the table and assisted her by wiping the dishes as she washed. We watched TV for a while, but the TV shows that night were not all that interesting and soon my mother started asking Billy more questions about girls.

I was really surprised how direct she was. She asked if he dated any girls and did he have a special girlfriend. At sixteen, Billy had a few dates, but didn’t really have a regular girlfriend and by the way the conversation was drifting, I could see that he was more than a little uncomfortable. Regardless, she continued to press him, becoming ever more probing … how far had he gone with them and she even asked if he had ever seen a girl naked.

Billy was confused and at a loss, thrown off by the prying questions of his best friend’s mother. Then she asked him, “Billy, do you ever got erections? I know that Tommy does get really big hard-ons.” This was certainly a lot more probing than I ever expected from my mother. “Billy, you’re a normal growing boy,” she continued in a soft, soothing voice, “Now, you’ve had your penis get hard, haven’t you?”

Somewhat embarrassed, he stammered, “Well, yes, I have.”

“Have you ever masturbated … jacked-off? Tommy does it a lot.” By now Billy was beet-red and bewildered as he looked at me. He didn’t know how to answer my mother’s questions. I wasn’t ready for the next one: “Do you like to do that? Does it feel good when you masturbate?” Billy couldn’t answer her but just slowly nodded his head. She continued in the gentle calming voice, “… and do you cum when you jack off?”

He paused quite a while looked at me and then quietly answered. “Uh, huh, sometimes.”

“Oh, doesn’t that feel good!” she enthused “Do you like that, too? Tommy certainly does.”

He timidly looked back at her and said, “Ah …, ah …, well, Mrs. Watkins, … it feels really good.” I could feel my own dick getting hard in my jeans, excited by this discussion between my mother and my best friend. I quietly reached a hand to my pants in order to rearrange my dick.

Mom kept on as she continued to softly ask Billy probing questions. “Billy, what does your cum look like? Is it creamy and white?”

After a pause, Billy continued. “Yeah, I guess so,” he quietly answered.

“Why don’t you show me how you do it. I’d like to see you jack off. Would that be all right with you?” Billy paused again before answering, shooting another furtive glance in my direction. He couldn’t believe what she was asking. This was his best friend’s mother!

“Ah, ah, well, I guess so,” he murmured. I could tell he was hesitant, but also getting pretty hot and excited by my mother’s questions and comments. I could also see he had a stiff dick in his jeans, anxious to be released. As hesitant as he was, I knew that he would enjoy jacking off, particularly in front of my mother. He slowly unbuckled, slid his jeans down, and pulled his jockeys to his knees.

“Oh my,” she said, admiring his long, slender dick. “Now, show me how you jack it off.”

“Okay,” he mumbled and started pumping it up and down. Moments later, his tempo quickly increased and soon he closed his eyes as he enjoyed the sensation. I knew that he was also absolutely enjoying the fact that my mother was watching while he masturbated. By now I couldn’t wait and pulled my own jeans and boxers down to my ankles.

“How does that feel, Billy? Does it feel good?” mom asked, her eyes on his hand as he rapidly pumped his dick.

“Oh Mrs. Watkins,” he murmured, “It feels good real good!”

“I want to touch it,” she purred. “Would you let me jack it for you? Billy didn’t answer, but she just gently moved his hand aside.