Chapter 1
It had been probably a week now, I really couldn't tell blindfolded as I was most the time. She had kept me tied up the whole time and moved me from place to place in what I think is a house. Hands bound behind me and my ankles tied only allowing me small steps to move where she pulled me by a leash around my neck. I was completely naked and had been since I woke up the first day.
She called herself Debbie or Deb for short and called me boy even when I told her my name. She had taken pretty good care of me, feeding me and taking me to the bathroom when I needed but I still didn't know why she kept me prisoner other then for the sole purpose of 'milking' me is what she called it and fuck she was doing a hell of a job.
It all started like I said a week ago when I was walking home from football practice. It was dark and I was alone and walked home this way many times before so that's how she probably knew where I was going to be. I had just turned 18 and was graduation this spring and in the best shape of my life from all the sports I played. Anyway I was minding my own business walking home and something hit me in the neck and felt like a horsefly had bitten me. Things started to get blurry and I got really dizzy and last thing I remember I was falling.
I woke up naked and bound lying on a soft mattress with a pillow and my arms tied over my head and my legs as well down straight. The blindfold was tight and I couldn't see anything but black. I called out and pulled at my restraints but it was no use the person had me tied really well. They must have heard me call out because a few minutes later I heard what sounded like high heels on a wood floor enter the room.
"Oh you're awake, good...time for our first session then boy," said a soft female voice that shocked me.
I was not expecting a female at all and not expecting what happened next either. I tried to talk to her and find out what she wanted and to convince her to let me go but it was no use she just kept telling me she needed me for my milk. I shortly found out what she meant.
"Such a strong young body you have, perfectly formed chest and stomach, handsome face and muscular arms and legs from all that football you love so much." I heard her say as she walked next to the bed.
"And then there's the best part, such a wonderful cock and it isn't even hard yet," she said.
She then grabbed my flaccid penis and I freaked out pulling at my bonds and telling her to stop. She just laughed and told me not to worry I was going to enjoy being milked. I struggled and struggled and tried to control my penis from becoming erect but I couldn't stop. My young body was too new at sexual experiences and it felt so good what she was doing to me. She was using her palm on the underside of my penis as it pointed up on my stomach rubbing it softly up and down my growing shaft.
"That's a boy, oh yes it's growing and growing getting much bigger," she said.
When it was fully erect she stopped rubbing it and I heard a drawer open and her rummage through it.
"Now let's see how big you are shall we?" she said.
I felt a cold ruler touch my penis where it connects with my body and she pulled my cock vertical and I heard her hum with curiosity.
"Not bad, not bad at all, a full seven and one half inches and a wide shaft to match. We're going to get along just swimmingly you and me," she said.
She was taking to my cock because she grabbed it around the middle and shook it as she said the last part. I heard her put the ruler away and then she grabbed my shaft again and pointed it back up straight and I felt a warm liquid being poured over it and it ran down over my head and shaft to my balls. She worked the oil in with both of her hands in a circular motion and massaged my balls as well. Shit it felt incredible and I knew I wasn't going to be able to stop from cumming if she kept it up.
"Now boy we will get along just great if you remember to tell me when you're about to cum. If you don't and I miss some of your milk I will be very displeased and won't be as nice as I could be. Do we understand each other?" she asked.
"Why are you doing this to me, leave me along, let me go!" I screamed again.
"Do we understand each other?" she yelled over me and I felt her hand grab one of my balls and squeeze it hard.
It hurt like a bitch and I finally told her I understood. She let go of my nut and started working my cock again up and down the shaft with her hands and the pain in my nut soon went away replaced by sweet bliss as both my nuts rose up tight to my shaft.
"That's it the first one will be quick I'm sure, just let it come boy," she said as she must have noticed my legs tighten and my balls rise.
"Shit lady I'm going to cum any second now!" I screamed at her moaning as well.
She moved my cock back almost horizontal and I felt a cold cylinder go around my head just as my first blast left my cock. It had been a week since me and my girlfriend had done it in my dad's car so I'm sure it was quite a load and from what the woman was saying it was.
"Oh yesssss, that's it boy give my all your milk, every last drop. So much cum, look at your pretty cock shoot all that jizz," she said as she stroked and stroked my ejaculating member until I bucked and squirmed under her hand and emptied my balls for her.
"All done? Very nice boy now you rest and I'll take care of this," she said.
I heard her leave the room and I tried to catch my breath. My orgasm was intense, she really knew what she was doing and I just laid there spent as my cock slowly returned to its flaccid shape.
A few minutes later I heard her return to the room.
"You did very well for your first session boy, actually more than I expected. You obviously have either been tossing off on your own or you have a girlfriend. Either way you're young body is producing exactly what I need in copious amounts."
I remained silent and knew talking with her was impossible. She must have carried some thing in to the room because I heard her set it down next to the bed and then she sat next to me.
"I've brought you some food and drink, you need to keep up your strength and fluids so don't fight me on this and just be a good boy and eat. I was starving from football practice and it had been who knows how long since she knocked me out. I didn't argue with her and just ate and drank everything she offered.
"Good boy, now shall we see if you are ready for number two," she said after I finished eating.
I was shocked, it had only been maybe 20 minutes and she wanted me to cum again already. I knew I was capable, my girl and I have done it three times in one night but only once.
"Were going to try something different this time boy, so just relax I promise not to hurt you."
I felt the ropes on my legs go loose and she pulled my legs apart and then retied them spread eagle and placed a pillow under my lower back so my ass was off the bed. She didn't touch my cock but ran her fingers over my nuts and down in the crack of my ass. She felt around my hole and started pressing on it with her finger. Then I felt the familiar sensation of the hot oil and she lubed up my bum and started slowly penetrating my ass with one of her fingers.