So there I was, in a messy diaper, inducing lactation from a woman I barely knew. Trying to wrap my head around the fact that she would soon be diapered with me and eventually my wife. It was a lot to take in. When I finished nursing, Hollie then began retesting me on my enema knowledge. After a half hour of that, she switched to the subject material covered in my lectures that day. Eight O'clock finally arrived and Hollie was permitted to change me. Despite it being a gooey, sticky mess, there was no odor. That would come later with real messes.
''Now tommy, comes the hard part, '' Hollie announced, ''five by hand, five by hairbrush and then five with your paddle.''
''My Paddle?'' I inquired.
''Yes tommy, Joyce procured a nice wooden paddle for you. It's slightly larger than a ping-pong paddle, but with holes in it, so there is no wind resistance. Just stay on your back and wrap your arms around the underside of your knees. The expectation is that you will count each stroke as follows: One Ms Hollie, thank you. Any failure to count, loss of count or changing of position and we will start over. You will remain in position until I release you. Do you understand?''
''Yes Ms Hollie.''
''Then lets begin.''
''One Ms. Hollie, Thank You.''
And so we began. The first five were not so bad.
''Now for the hairbrush,'' stated Hollie.
''Six Ms. Hollie, Thank You.''
Thus went the next five. It was with some difficulty that I maintained count. But I managed.
''Now for the paddle, tommy.''
''Eleven Ms. Hollie, Thank You.''
I almost didn't get that out. Tears are running down my face, and my face felt as red as my ass.
"Twelve Ms. Hollie, Thank You.''
My ass hurt. My legs were cramping. Besides the pain, the position was uncomfortable.
"Thirteen Ms. Hollie, Thank You.''
Now Joyce and Tonya walked in.
''How is he doing?'' Joyce asked.
''Almost done Ms Joyce,'' Hollie responded.
"Fourteen Ms. Hollie, Thank You.''
''Nice touch, making him count and thank you. I will have to remember that,'' spoke Joyce.
''I like that shade of red Hollie,'' said Tonya.
"Fifteen Ms. Hollie, Thank You.''
I hoped we were done. I could not hold back the tears or the sobs.
''Hollie you have done well, when you release him, do not diaper or cream his butt. Let the pain remind him that anything less than perfection will be punished.'' Joyce stated.
With that Joyce and Tonya left the room.
''Tommy, you may release and stand up. I do not recommend rubbing your bottom as that might make me mad.'' Said Hollie.
''Here's my plan tommy,'' Hollie said, ''I need a series of enemas. You are going to give them to me. Each mistake you make will be added as a part of tomorrows spanking cycle. I hope you have learned well.''
With that in mind, I proceeded to give Hollie a soapy enema followed by two rinses. She was totally cleaned out after the second rinse.
''You did well, tommy,'' she said. ''Now lets go to bed for your reward.''
''Now tommy, in our relationship all things will be equal between us.'' She said as she began putting on her strap-on.
This was something I had not seen before. I watched as she lubed up two pieces, one she slid into her rectum and the other into her vagina. Tightening the straps she now had a shaft protruding from her hips. It was about eight inches long and appeared bigger around than I am.
''Get on the bed, on your hands and knees. As I said, we will be equals in that I am going to have my way with your ass, and then, if you are up to it, you can have mine.''
I wasn't sure about this but did as I was told. Hollie grabbed a tube of lubricant and began loosening me up. She started with one, then two fingers, playing in, and stretching my ass. Then they were joined by a third finger.
''Someday I may open you wide enough to take my whole fist tommy.''
I just let her have her way and said nothing.
''Ok tommy, relax and push back as if you are having a bowel movement.''
And like that she was in. I felt full but not uncomfortable. Placing her hands on my hips she began to thrust in and out; in and out. Each stroke felt like she went a little deeper. Then I felt her thighs against the backs of mine. She let go of my hips and leaned forward.
''Now the fun begins,'' she whispered into my ear.
I could feel her breasts against my back, her thighs smacking into mine as she began to slowly fuck me with long strokes. Reaching around me she began to play with my nipples as well. The pace of her thrusts increased; I was in sensory overload. She let loose of one nipple and grabbed my shaft; moving in concert with her thrusts. It was as if she was masturbating her own prick. As she sped her pace up, I lost it. One minute I was feeling good, the next I was aware of nothing. I PASSED OUT!!!
I awoke an hour later in bed, with Hollie caressing my head.
''What happened?'' I asked.
''You came so hard you passed out. A combination of an anal orgasm as well as my stroking your cock and playing with your nipples was more than you could stand. So I diapered you and got you into bed. We have all day tomorrow to pick a time to play.''
As she said that I reached between her legs to find my final surprise of the evening.
''Yes tommy, Joyce thought it fair that I return to diapers along with you. The same rules apply, I cannot change myself, only you or one of the others may. In addition, we are both expected to have at least one dirty diaper a day, unless we both have dirty diapers, Joyce and Tonya will forbid us to have sex that day. To make things more uncomfortable, that harness you saw me put on, I am still wearing under my diaper. So I am being stretched and filled at the same time.''
Hollie then guided me to a nipple and said, ''Sleep now, tomorrow is another day.''
And so began my retraining or was it my un-training? Diaper change expectations became clear over the following days, two wet and one messy change a day. I learned to get use to and even enjoy a wet diaper. One the other hand messy diapers I never can get used to.
As this routine of diaper changes continued, so did my school classes and spankings. The important part, from my perspective was I had never preformed as well in class as I did now. I was receiving A's in both classes.
Then came the day I decided to ''go for it''. I had been teased a couple of times by Margurite to stay dry, or asked about why I was wearing baggy clothes. I believe she knew something about what was going on. So one Thursday morning, after my morning diaper change, I messed. I had held back for a reason; I wanted 24 hours free of diapers with Hollie. I came down to breakfast followed by an odor.
''Hollie, I thought you were going to change him?'' Joyce asked.
''I did, Ms Joyce,'' she replied.
Looking at me Joyce asked, ''Is that correct tommy?''
''Yes Ms Joyce, today I go to class wet and messy,'' I replied.
Joyce looked at me again, smiled and that was that. After eating Hollie took me to our room to finish dressing; pulling open my diaper she proceeded to fill me front and back with baby powder.
''This will help mask the odor, tommy,'' Hollie said.
Classes that day felt like they lasted forever. Thankfully the powder did mask the odor. Margurite commented that someone smells like a baby and then gave me a playful swat on the ass. She had to know what I was wearing. As I later found out, she was at the seminar as an unattached mommy. I hope she found what she was looking for as we lost touch with each other over the years.
Finally class ended and I returned home. Once there, Joyce checked to make sure I was still in the same diaper. Of course i was.
''Hollie, clean him up and I don't want to see the two of you for 24 hours, except at meals. Have fun you two.'' Joyce announced.
Hollie led me to our room, cleaned and spanked me. It was a lite spanking, more for play and arousal than discipline; then the fun began. We made love, we fucked and we made love some more. We gave each other enemas and then enjoyed giving and receiving anal sex. Some where during all this we stopped to eat.
As our free time ran out Joyce appeared and announced, ''Hollie, when you diaper him, it is time for the next part of his training.''
''Yes Ms Joyce.''
Hollie took me by the hand and led me into the bathroom and opened the door to the adjacent room. WOW!!! A baby's paradise. Changing table, cribs, play pen and toys galore. Shelf after shelf of cloth and disposable diapers. Drawers of plastic and rubber panties. A large walk-in closet of Adult Baby Clothes. Guiding me to the changing table, Hollie quickly had me diapered in thick cloth diapers. She then helped me up and assisted me with the plastic panties. As she pulled them up and ensured that my diapers were tucked in she explained.
''These are satin rumba panties, plastic panties with a satin exterior. While you were in class today Ms Joyce informed me of one change to the seminar. There will still be a baby boy and girl, you will be dressed as the girl and I as the boy. From now on you will be dressed as a baby girl while in the house.''
She pulled a t-shirt over my head, laced ruffled socks on my feet and led me to the playpen. So here we are, back where I started this tale. Diapered, in rumba panties, in a playpen.
What will happen next?