Jack laughed and pushed the button again and I jerked harder. She made some adjustments and then smiling pushed the button again. I screamed and it felt like lightning went up my ass and flew out through my penis as I had a long mind numbing orgasm. Then she did it again and I screamed. After adjustments the orgasm now included my nipples and the fire started there then went down and into my cock through my balls and out my ass. This was evidently what she wanted because she did it three times in short succession. The last one my screams were accompanied by loud farts and I begged her not to make me do it again. After some rather intense negotiations it was agreed that I would do it two more times only but then would need to offer both my ladies serious sexual release with my hands and mouth. Jack pushed the button and my world shrank to just my ass cock and balls. Then she dialed in the nipples and I screamed as I poured myself out with another long orgasm that left my asshole quivering and my penis so hard I was worried.

As I was unwired and had all the toys removed from me Jack explained that while I might be sure that I had cum, I had never ejaculated. “Not to worry though my little troubadour, as soon as you are done with Sis and me I am going to take care of that.”

They helped me up the stairs and onto the bed. As it turned out, my Mistress had ideas of her own and as soon as I had brought Jack off with my mouth and hands Al mounted me and rode me astraddle as she immediately started to cum and rode me hard. When She was about done she ordered Jack, “Pop him for me I want it in me!”

Jack pulled my legs wide and soon had several fingers moving in and out in rythem to my Mistresses dance and then I exploded. I mean I literally just blew my load in an explosive, sudden and totally irresistible fashion. I filled her and then it overflowed all over me. Once she was sure that she had all there was she eased off me and allowed Jack to finish me off with her mouth and fingers. I cried like a baby and knew better than to even try to resist her. Once again I came until it hurt!”

On wobbly legs I was led to the shower where we all got clean again. Al took me back to bed where several suppositories were placed up my ass and then a large butt plug was eased in and a strap placed to hold it there. “Time for you to rest a little bit Rocky. Then we will have a little lunch and then you are going to start your afternoon enemas to prepare you for your date with Jack this evening.” My Mistress informed me. “I have a few things to take care of but Jack is going to nap with you. Be a good boy!”

“Do I have to keep this in me?” I asked indicating my anal intruder.

“Yes you will have to keep it in until we start your enemas. It is just a little one you will learn to handle much bigger ones later.” Al told me.

I was tucked in and Jack stripped and joined me under the covers. Al kissed us both and told us to be good or she would have to spank us. I grinned and started to say something but Jack put her hand over my mouth. “We will be good!” Jack assured her.

Once the door was closed I asked Jack, “What’s the deal?”

Jack laughed, “She IS the Big Sister and I can tell just from the way that she is acting that she is looking for a reason to spank me. It is a game we have always played. I will be as good as possible and make her wait and work hard to find that reason. See with you she doesn’t need a reason. She can just walk in and tell you to assume the position. With me it is different.” She snuggled up against me and to my shock she found one of my nipples and began sucking. It made me feel strange after a couple of minutes! There were little fluttery feelings in the pit of my stomach.

“Does she really bring home students for nursing practice?” I asked.

“Oh yeah! She loves to do that. She used to borrow Robert every once in a while to use as a subject. He would squall and bawl like a baby until he was introduced and then he was all theirs. A couple of times she even talked me into it! She doesn’t invite everybody, just the ones that she senses will get the most pleasure from it and actually learn and benefit from it.”

She returned to my nipple making me shiver so I asked, “How many does she bring home at a time?”

“Usually she will invite two to four for one of her special classes. She does it in part for the fact that experience really is the only way to learn most of this and then in part because it is such a turn on for her. If she wasn’t so damn persnicaty about who she picks for her playmates she would probably do it pretty often. If she keeps you and I see every sign that she is, you will be her first full time in almost 2 years. She will want you over here most weekends and most evenings until eventually she will just move you in.”

“Jesus my Mom will have a COW!” I warned.

“You don’t need to worry. When your Mom comes home she will figure out a way to meet her and don’t be surprised if she invites your Mom to help or sit in on one of her enema sessions with you almost immediately. Al hates those purgative suppositories so she will prefer to train your Mom in proper enema use instead. I’m afraid that she will probably encourage your Mom to take even better care of you than she does now. Al is very good at making other women comfortable with her and knows that even though you are 18 that you are still your Mama’s baby and in your case there are close connections. Al will encourage those connections so that she won’t be seen as competition with your Mama. I watched her do this in high school. She had a boyfriend that she ruled and she would get calls occasionally on school nights from his Mama to come over to help her punish him.” She laughed, “You will not believe how fast she will have your Mom eating out of the palm of her hand. The good news for you is that it will make it easy for you to spend lots of time over here. The bad news for you is that you will be expected to accept even more invasive and restrictive controls from your Mom.”

“What will happen this fall if I go off to school?” I asked.

“Are you set on going away to school?”

“I had planned on it as sort of an escape. We haven’t put any money down yet but I have been accepted to the state U a hundred miles from here.” I admitted.

“Do you think that you will want to escape Al’s clutches in a couple of months?” I shook my head and Jack continued. “The local university is better. It is also a lot more expensive but that won’t matter for you because Al will arrange for a scholarship for you or pay for it herself. Believe me, your Mama is going to just LOVE Al! Her Baby won’t be moving a hundred miles away. Her special rights over you will not only not be terminated, Al will reinforce them expand them and encourage her to play a part in your continued personal growth. If you blow a test because you didn’t study, Al will have her over here to spank you and “supervise” your correction. In short order she will see that by giving you over to Al, she doesn’t have to give you up at all like she would if you were involved with someone more your age because Al will respect her age and experience.” I shivered and Jack patted my ass. “Don’t worry Rocky, you will love all the attention. I can see that already. Now nap time!!” She pulled me down gave me one of her nipples and put me too sleep.

A couple hours later I woke up alone but it was only for a couple of minutes. I felt the bed move and looked up to see Al there crawling in bed. “Jack says that I need to talk to you about our future.” I just looked at her wide eyed. “I know all of this is fast too you but I have indeed decided to keep you. You are very special and I am going to make sure that you are not messed up. I want you! Do you have any problems with this?”

“No Ma’am.”

“You don’t think that you might like someone younger maybe prettier?”

“I’m sorry, but be REAL!! Nobody is prettier than you! You will teach me in what to enjoy and how to please. I already know that I could never find the special things that you have already given me with anyone else. Will you marry me? I’m serious, till death do we part! If not that can I contract myself into your service?”

Al looked at me and a tear coursed down her cheek. “JACK GET IN HERE!!!” She called and in seconds Jack was in bed with us. “We are going in a new direction with Rocky. The Mistress idea was fine when I didn’t know him. I had planned on keeping him and playing with him for a bit and then send him on his way. That has changed! Rocky, from now on you will call me Al or Alicia the mistress thing could create problems for us in some of the upcoming meetings such as with your Mama. You can still say Ma’am but not Mistress. Ok?”

“Yes Ma’am. Alicia.”

“Jack, I have decided to keep him. Eventually we will even legitimize it but I want him to graduate first.” Tears began to flow and Al fell against Jack. The silly little shit wants to marry me!!”

“What did you expect? He was a virgin and you gave him pussy!! Of course he wants to marry you. He’s just a baby. In another few years he will still want to marry you but at least then it will be for reasons he understands. I think you need to collar him and play the boyfriend/girlfriend thing for a while. Honey you are not exactly ancient you know. I doubt that at first his Mom will even realize that you are a little older than her Baby. What are you blubbering about anyway?”

“You didn’t see him or hear him when he asked me to marry him Jack. He was deadly serious and the way he did it, it was the sweetest thing that anyone has ever said to me!”

Jack laughed, “I have to agree, he is excessively cute!! Now, let’s wash him out so I can fuck him!”

Al took my strap off and eased the butt plug out of me. While Jack got me into the bathroom Al mixed me a BIG soapy enema. The nozzle she attached was even bigger than the butt plug was! Jack placed me with my ass up and lubricated my relaxed ass and then let Al slowly plant the big nozzle into me and explain to me why it was being used. “This big nozzle will help get you ready for the dildo Rocky. This is a big enema you will need to take it all and then hold it for ten minutes. After this one you won’t have to hold the rest of them.”

I closed my eyes and breathed in deep through my nose and then slowly out through my mouth. I didn’t even look or ask how much there was to go. When I cramped the enema slowed and then when the cramps passed the enema was resumed. Eventually Al told me that I had done well and that it was done. “I’m going to leave the clamp open so that you have a little extra give when the cramps are bad.” I whined and moaned and it was the worst enema ever as I struggled to squeeze the nozzle tight and hold the enema in. After an eternity I heard the clamp close and Al told me that I needed to move onto the toilet. She put on a long glove and made me bend forward before she removed the nozzle. It was so big that when it was removed the enema rushed from me and I couldn’t even slow it!

Al changed the nozzle to an even larger one and then when I had drained she inserted it as soon as I was off the toilet. The following three enemas were all given in such a way that I cramped a lot and struggled. After the last one was in me Al explained that one gallon enemas are pretty large for a novice like me and that she was extremely pleased with how well I had done. She kept me on the toilet for a long time and then walked me several times and then would return me to the toilet where she would finger me and try to force any last remnants of the enemas in me to come out. When she was done I was washed bathed and she took me to bed. I was allowed to go down on her for a while before I was led to mount her missionary styled. After a few very pleasant humps and bumps, Jack held me still and came to my ass on her knees. I looked back and saw the dildo and wished that I hadn’t. Al pulled me deep into her and held me tight with arms and legs. Jack lubricated me and then began to carefully work her way into me. It turned out to be a lot easier than I had feared and I moaned as she passed the head through and then slowly sank into my cleared depths. She was slow and careful until I adjusted and then I got impatient and met her more than half way. After that she gave herself over to it as did I and together we fucked each other and Al with total abandon. I came into and with Al pretty quick but that had no effect on what Jack was doing and it just went on and on until I hardened, fucked, came again and then started to beg for Jack to have mercy. Mercy when you are getting butt fucked means, evidently, that they need to do it harder, faster and deeper because that is what Jack did when I began to beg and scream.

Al held me and watched me. She laughed when my eyes literally crossed and were stuck that way for a second. I will tell you for a fact that anal virginity is a lot harder to shed than my previous other virginity! Jack was up for it though and in great condition. She fucked me STUPID and then some before she came and was unable to do it anymore. Even at that point she stayed in me! When she parted from me though it was like she had started me all over and I screamed for some few minutes even after she was gone. Al held me and laughed!