Just to refresh everyone’s memory, my name is Matt and I am continuing the story from the “The Day I lost my virginity” when I was sixteen years old. A short recap has me still bound to a chaise lounge at my sister’s friend’s house after losing my virginity first to my little sister, Katie, and then to her friend Jen. After satisfying their needs, they just left me tied up and walked away. Leaving me bound naked to the lounge chair for all to see. Fortunately dusk was settling in and due to the eventful day, I dozed off into sleep.
What was probably hours later as it was now night, I was awakened by someone both touching my cock and a cough. Opening my eyes, it was Jen’s mom sitting next to me on the lounge chair. This woman is just so, so hot looking (remember she was sun bathing in the nude in the beginning of the last episode) and waking up to her dressed in a thin white, low cut cotton dress which allowed the pool lights to pass through outlining her body underneath. Of course instantly my dick started to rise and she noticed by grabbing my cock while pulling it up right.
At that point, she looked at me and stated; “It appears that the girls had some fun with you, can you tell me what happened?” As she slowly stroked my cock to it’s full dimensions, I gave her the quick run down of what happened almost embarrassingly saying that it was the first time and then especially losing my virginity to my younger sister of all people. She laughed at that and said there could be worse ways than that.
She looked at my cock and asked if it was responding more to the events of the day, or was it because my cock was happy to see her. My response was to explain that I have never seen a woman that turned me on more, either in porno films, magazines, or in person than her. She smiled and said, “thank you, I am glad this is for me” as she squeezed my hard dick. She then asked, “you do know that I am at least twenty years older than you, do you not?” I told her that no one could tell from the way she looked and the thought of her looks, with experience, makes me want to blow my wad right now.
She then asked: “so by mentioning experience, are you looking to be trained?”
Of course my response was that, yes I wanted to learn, especially with someone as hot as her.
With that, she stood up and swung her leg over me, straddling my body, slowly raising her dress while moving her pussy over my upright dick. My anticipation was beyond belief…I was going to be allowed to fuck the most gorgeous woman in the world.
She lowered herself to where I felt the rings from her cunt just start to touch the head of my cock. Then she stopped, leaned forward with hands next to my head, and said; “before we go down this road, let us set the ground rules. First, you are still a boy, with a man’s cock that is probably a top ten percenter and the vast majority of women never have the opportunity to enjoy one like this. Second, to be gifted like this and have the opportunity to train you before you can form bad habits. Third, I could use another toy, so this excites me. Therefore, I will accept the challenge to put you through an apprenticeship so to speak. But, you have to accept 100% direction from me, no questions asked. In essence, I own you for the duration of your education. This means if you have a chance to fuck with some one else, it can only be done with my permission. I will add physical enhancements, including a brand to designate to which you owe your training. Another words, no matter what I tell you to do and no matter how revolting it might be to you, you do it and relish it. I will take your verbal word on this now, but expect you to sign a document stating this later…do you accept?”
I heard the words, but did not have to question anything as those cunt rings hanging from her pussy lips were teasing the hell out of the head of my cock. I said, “I accept…unconditionally!”
With that, she plunged her cunt down on my cock announcing that from now on it is “HER cock” and that I am to always address her as either Mrs. Cash or Ma’am. She worked her way down; the pressure on “her cock” was exquisite, the warmth, the smoothness, and the thought of being embedded into the most beautiful woman I knew in the first sixteen years of my life was too much. In a matter of five to six minutes of her riding up and down, “her cock” exploded in a torrent of sperm filling her vagina and womb. She looked down, smiled and said, “this is why you need training, but it is a start”.
With that she directed her cunt to my face, telling me to do a good job of cleaning it out. I sucked her pussy for all that I could, sucking out huge quantities of jism. Surprisingly it was not all the texture of liquid; some of it was in clumps causing me to chew. She noticed that, and mentioned that she had been at a bar trying to set up my mother (another surprise) but she did not show. So, she fucked both the guys since she was horny, and now I have the pleasure of consuming their coagulated spunk. Then she said, “first test, do you like it?” Even though it was revolting to think, I nodded my head yes.
She worked her cunt back and forth across my mouth, with me licking, sucking, and working my tongue up her pussy as far as I could. She then told me to do the same to her asshole. I complied with a relish. After fifteen minutes or so, she had an orgasm flooding my mouth with her juices. I thought…this is fantastic, it tasted so great, I would eat a mile of her shit just to have her do it again…little did I know.