I grew up thinking my mother was a prude, especially with her disdain for pornography. It wasn't that she was opposed to sex or even masturbation, she thought too many people -- including me -- were isolating ourselves by getting so caught up in images rather than connecting with real people. She feared I was getting addicted to porn and felt she had to act. She'd take my computer away or barge into my room if I forgot to lock the door, then scold me if she caught me jerking off.
"You should be going out with girls instead of locking yourself in your room," she'd scold, again and again. That all changed recently when she realized it was partly her fault that I didn't have regular dates. When she decided to split from my father, we had to move, and that meant I was forced to go to a new high school my senior year. I didn't know anybody and the girls especially were part of the problem because they didn't care to have much to do with the new guy. Back at my old school, things would have been different.
Mom offered a compromise. Rather than turning to computer screens to find images that aroused me, Mom suggested she model for me. The first time, she took off her top and her bra and before I knew it, I was stroking my cock while staring at my mother's perfect breasts. When I reached up to massage her tits, she reached down and started stroking my cock. She made me come in a minute, it was so unexpected. She grabbed a towel I had nearby, cleaned us up and left.
Over the next few days, we went further and further. The next time she came to my room, she let me cum in her mouth. After that, she showed me how to lick her pussy. And finally, she was lying back on my bed, legs spread, and my hard cock entered my mother's wet pussy for the first time.
So Mom wasn't a prude after all. In fact, that doesn't even begin to tell our story. Mom and I agreed that when I was horny, instead of running to my computer, I would come to Mom and she would help me cum. "I don't want you jerking off to a computer screen, and I don't want you screwing some ditzy school girl," she said. So I had a standing invitation from Mom. I was getting regular sex for the first time in my life -- with my own mother! -- and it was wonderful.
At first I was screwing her at every opportunity. I was afraid this arrangement wouldn't last so I wanted to make the most of it. A quicky in the shower before school, her waiting for me after school, or me climbing into her bed in the middle of the night if I had trouble sleeping. I went for quantity instead of quality. With time, though, I realized I could have her any time I wanted, so rushing wasn't as satisfying. I slowed the pace. I waited until I was really in the mood to approach her.
That all changed a few days ago when I came home from school one afternoon. I heard voices -- female voices -- coming from Mom's bedroom. She had her door mostly open, clearly wanting me to see what she was doing. I couldn't fucking believe it. Mrs. Henderson from across the street was lying in the bed with Mom, cuddling, and both of them were naked. Their nude bodies were entwined and on full display.
"Hi Jimmy, how was school," Mom asked, as if coming home to find her in bed with a naked woman was an everyday occurrence.
"It was fine," I said. "It looks like you were having a good afternoon as well."
Mom turned to Mrs. Henderson and they kissed, deep, with tongues swirling, for several seconds. "Yes, a very nice afternoon," Mom said. "We were just catching our breaths, waiting for you to get home and join us."
Joining two naked MILFs in bed? I'm sure as hell not going to pass that up. I stripped as quickly as I could, my cock already hard, and laid down between them. Mom started nibbling and gently kissing an earlobe and the side of my face, and Mrs. Henderson was working on the other side. I felt a hand reaching down and stroking my cock, but I couldn't tell -- and didn't care -- whose hand it was. The dual kisses worked their way down to my neck, then then my chest and then lower and lower, until I had the most sensational feeling ever.
Looking down, I saw Mom taking my cock in her mouth, her wet lips and luscious tongue working the head of my cock, gradually taking more and more into her mouth. While Mom was doing this, Mrs. Henderson worked on my balls, gently licking and sucking, so amazing what she was doing to me while Mom was working my cock with her mouth.