"Sooooo...what if I decided to cuckold you...."

I don't want to sleep in there...

You haven't posted since Saturday?! Gasp! We'll I'm here now, I've simply been terribly busy the past few days as has Mistress. Saturday evening panned into a wonderful surprise for both of us, no it did not involve her beating me or me wearing diapers in public. We went to a local restaurant with new friends, and then took a long walk; perfect evening. When we arrived home I could tell Mistress was horny, very horny. I made a suggestion which I'm not supposed to do that we should try the condoms and numbing cream this evening; she had been preluding to milking me all week so I thought just maybe I might get off! We'll with a cautious glare she agreed to give it a go; I was so excited! Not sure if the numbing cream worked fully, though I think it did. It was too late to tell by the time she threw her curve ball into the equation. "You can have sex with me, as long as I'm on top...but I'm adding something else to your dick; Icy Hot".  I've had Icy hot before for muscle aches, how bad could it actually be? She took a huge amount and rather than rubbing it on my dick, rubbed it into my balls. No words can describe the following pain, thank God she didn't have me tied up! I can't even imagine! She quickly slid the condom on and walked out of the room; I couldn't take the pain, the heat, the piercing feeling ...it was too much for me to take. I jumped out of bed and into the bathtub and turned the water on to get it off. She was not amused and she starred at me with a very judgmental glare. "Seriously....like....really?" was all she said leaving me to rinse off the Icy Hot, entering the other room I could here her preparing my diaper. "I tell you you can fuck me, and this is what you do....again it's no wonder you need diapers....get in here I don't care if it's still on you, get on your damn diaper". She was not happy. I begged her to try again and not put it on my balls, she was having none of it.  "I want you to get back on the ball and find me a crib, like yesterday. This is ridiculous." she said rolling over to go to sleep. "But you told me I would get relief today?!" I stammered as she went to bed. Laying it bed I felt humiliated, for everything...I blew my chance to get the one thing I wanted...sex. I was frustrated as hell, horny and exhausted, as I began to dose off I filled my diaper without thinking about it, adding to my frustration. Waking up Sunday to her changing a messy diaper just gave her more ammunition for humiliation.

I don't want to not get to have sex....I really don't wanna be sitting in a diaper watching Mistress get it!

Sunday I ran out of town to take care of some things and upon arrival back home gave Mistress a hand with unloading her car, exciting right? We'll we had a massive family dinner planned for Sunday night and once it was over we headed home and had a long talk. She was mad that she let me have a "break" and that it lasted two days longer than she had planned. She also broke down to me about finances, admitting she needed my help. I'm great with money, she's not. She also needed help with her side business...she needed her boyfriend, not her sissy. Once I explained it to her, she began to see this break was going to have to last a little longer, for her own sake. She was mad she didn't come to me during my time off, I explained to her over the course of this week I would help her get on track, become organized and teach her to stay in a good rhythm. "Your still wearing your clit cage...and diapers at night....and calling me Mistress...and cleaning the house..." she said. I knew all of that, it was clear she needed my help though. I set her up on my financial software, and thought I could rest for the evening until she came out of the bathroom wearing her strap on. "Turn over and assume the position" she said. About ten minutes into pounding me she unlocked my chastity device and began stroking me. She did me in several positions then finally had me hold a cup in front of my dick. "I want it in the cup, all of it." she said continuing to pound away. When I got off it was wonderful, it felt so good! It had been several weeks since I truly had a real orgasm. I was ready for my diaper and a cosy bed, but that was halted. "Drink it" she said calmly. I came up with every excuse in the world, I knew I would throw up if I did, I couldn't do it. She demanded I drink it and when I wouldn't listen she put my chastity device on me and proceeded to diaper me, something she never does because she knows I won't sleep. I didn't dare say a word, I could tell she was not happy. "I don't know what it's going to take for you to start listening to me, but it better happen soon".  She poured the cum into the container along with the rest she had collected before and placed it back in the freezer. I laid in bed in silence while she made yet another comment about it was time to move me to a crib to fit my behavior as of late. "Your a sissy, sissies drink cum...period." She went to sleep, and I had trouble dozing off given the talk we had.
So that's where we are, Monday and today I've spent all my time at home cleaning and helping her control her finances and map out a plan for her financial goals. I apologize it's not the most exciting update, but I feel this is an important part of the process. She cannot fully focus on becoming a better domme if she has all of these underlying stresses in her life. So no, I don't view this as a set back. Rather this is how progress is going to happen! She did bring up something...interesting though. She asked me the other night how I would feel if she cuckolded me in a few years, I told her I viewed it as cheating. "You'd be present, in your crib, in your diaper....it wouldn't be cheating", I was so puzzled why she would ask me that. "I thought you weren't interested in that..." I asked cautiously, she replied with "I'm not right now, but I may be... don't worry thats a ways away and we'd be married then, lets get your diaper on sissy." And that was the last she said of it.

Debbie