Around the same time as my flashing episodes, I became aware of masturbation and self-gratification. The first time I masturbated it was completely by accident. I was laying in my bed listening to music on the radio and I was bored, so I put a pillow between my legs and started grinding my cock into it. Within seconds I was erect and all I could think was this only happens in the morning when I wake up with a piss hard on or when I would poop out a long hard turd. Within moments of becoming erect a strange sensation began to build within my balls and so I began to grind harder to the point of being animalistic, then suddenly I had an explosive orgasm. Never have I ever felt anything so primal and yet so pleasurable in my life. I liked it so much I did it again right away, and again. The first one was an accident, but every one after that wasn’t. What an incredible amount of cum everywhere. From that point on jacking off ten times a day was my goal. Even today at my age, three in one day is possible. That was also when porn became a significant part of my frequent jacking off episodes.
The trouble with that was privacy with five siblings running the house. I spent alot of time behind a locked bathroom door sitting on the toilet jacking off. Jen spent alot of time yelling at me from the other side of that locked door. I was braking one of her rules about locking the bathroom door. I also was yelled at to let go of my dick only perverts did that and to get out others needed to use it. I am pretty sure I was the only one of us four boys masturbating.
Jen worked real hard at putting fear into us and it worked. Because of her tirades I spent alot of time betting up her redhead son. Sibling rivalries ran a muck in our house with Jen behind the scenes instigating them. My brother bolted back to Kansas the day school let out for summer vacation, he was done with Jen. Her two boys quickly followed, the oldest left to visit his father and never returned. Her youngest had a guardian angel, he wanted to be G.I. Joe and a person Jen knew was able to get him into a pretty prestigious military school to be prepped for a military academy in the future and with that it was just my sister, who had nowhere to escape too and me.
The beds emptied out, the noise died down and it got more relaxed around the house. I was now comfortable enough to hang out in just a t-shirt and my tighty whities. It made getting my cock out, jacking off and putting it away when finished made it alot quicker and easier. I was becoming bolder, no longer sitting on a toilet behind a locked door I began to venture out.
Living at my father’s house, and fast becoming a chronic masturbater, I was exploring other rooms in the house. I always made sure no one else was home except Jen, who would be upstairs asleep. After trying the other rooms out, including the shed out in the back yard, I enjoyed jacking off the most in the dining room, right next to Jen’s Chinese themed ‘stay the fuck out of here at all times or I will kill you’ living room. I had a place on the carpeted floor to sit and take off my underwear completely, and a spot for my girlie mag. I could lean my back against the wall, take hold of my cock and start a slow, sensual jack off session. I would even get so comfortable at times that I would moisten the tip of my left index finger in my mouth and play with my butthole, while using my right hand to slowly stroke my cock.
Jen’s visual warning about the forbidden land had now become just my first up close exposure to a woman’s butthole, and that would always have a place in my heart and an image that, even to this day, is forever burned into my brain, in a very good way. My favorite part of a female’s body is the butt. More specifically the butthole, tucked in between a woman’s pair of beautiful butt cheeks. I like round cheeks with definition at the minimum. I love burying my face between a woman’s butt cheeks and pushing my tongue deep into their butthole. I am honest when I say I have put my tongue in nearly every girl’s butthole I have ever been with sexually. The poses of the girls in my mags were saying that this is yet another path to utter bliss, and not the forbidden land.
I was in my spot getting into it when she came down stairs, through the kitchen and to the entrance of the dining room. It was the one direction I didn’t have a good view of and she was able to come all the way up to me without me seeing her. “The fuck you are!” she yelled. Suddenly the stroking stopped and the panic set in. I frantically looked for my tighty whities, a thunderous size ten bare foot landed on them. I immediately grabbed my manhood with both hands and began to assess my predicament. I was sitting up now, looking at the floor in front of me, and she was standing directly over my left shoulder. Then she said in a strong forceful voice, “If you are going beat off in my dining room, you are going to fuckin’ finish.
” I scanned slowly up her leg, right up to her hairy pussy that was only a foot or two away from my face, and I stopped right there. She again spoke, now yelling, “You fuckin’ heard me! Now finish what you started!” I realized now Jen wasn’t yelling at me for jacking off, but for stopping. My eyes went from her hairy pussy, up her soft jellyroll belly, in between her sagging D-cups, then to her eyes. I am pretty sure I had a look of complete confusion on my face. “Right now, finish!” she said. I still continued looking at her, confused. “You think you are a grown man, now you can show me how grown you are. Now lean back and finish beating off!”
At this point I am completely confused, because she wants me to jack off right in front of her as she stood over me naked. Her being naked several months after my arrival wasn’t new, but her standing there watching me jack off was. I complied with her demand and leaned back against wall. I stretched out and spread open my legs. I hesitated for minute but didn’t remove my hands from my cock. “What the fuck are you waiting for?!” she bellowed. I was feeling a bit embarrassed. I slowly pulled my left hand away, but kept my right hand securely in place. “I don’t have all day now, get busy!” she said. I pulled my right hand away, slowly exposing my cock. Then she said, “You think you are a man, but you still have along way to go. I suggest you hold it a lot tighter and pull on it a lot harder – maybe that will help it grow.”
What Jen said about my manhood didn’t register with me until a long time later. I took a hold of my cock and began to stroke it. “Get busy!” Jen said. My poor limp cock wasn’t cooperating at first, but Jen continued with the comments and directions on my performance. “What’s wrong? Is your dick shy? Maybe you should put your finger back in your ass, you looked like you were enjoying it before you sissy boy.” I kept trying to get an erection and it just wasn’t happening. Jen was determined I finish what I started, so she continued to taunt me. “I know you heard me! Take your finger and put it back up your ass sissy boy!” I did just what she told me to do and began to gently rub my butthole with my left index finger. My state of embarrassment, shock and confusion was starting to subside and was being replaced with a feeling of comforting relaxation.
With a big exhale, a feeling of relaxation overtook me, and into my butthole slipped my finger. My erection began to come back. “Well would you look at that – you really are a sissy boy, you like it in the ass.” Jen stepped forward, took her right leg and stepped over, and now was straddling me. I looked up at her slightly dimpled butt. Jen put her hands on her hips and said, “Maybe if I give a closed up of my dirty sweaty ass, it’ll help speed you up. I don’t have all fucking day kid, lets go!” She slid her hands down to her butt cheeks spreading them open, bent forward slightly and squatted within inches of my face. My eyes instantly locked onto her round wrinkled protruding butthole pucker.
Jen was right, the fragrance emanating from between her legs was a combination of sweat and female musk that hadn’t been bathed away for a couple of days. It was the first scent of any woman, yes I do mean first scent of any woman, that I ever inhaled. It intoxicated me, and I knew instantly that was going to be a lifelong pursuit. My cock instantly got hard, my pace quickened and with one last mighty inhale of her sweaty musk, a load of cum shot out of my cock all the way up to my chest. I didn’t stop stroking, I continued, because it stayed hard and few moments later, I shot a second load onto my chest and stomach. “I’m impressed. Every man I’ve ever been with was good for only one,” Jen said. She stood up, let go of her butt and headed into the kitchen.
She poured herself a glass of iced tea from the pitcher in the refrigerator, grabbed a bottle out of the cabinet, topped off her tea and came back over to me. Jen then began to lay into me again in her own special way. “Get this fucking mess cleaned up and don’t ever let me catch you beating off anywhere other than the bathroom!” With that Jen turned and headed upstairs. She bellowed once again, “And don’t forget to lock the fucking door – nobody wants to see you doing that!” She went to her bedroom and a minute later I could hear the faint sound of Jen’s vibrator buzzing.
It was told to me later a second person watched the whole episode between Jen and I.