Last night, another opportunity to meet a man for Mommy fell through. Mommy was teasing me all day, sending me screenshots of her sexy conversation with this man. Later, she gave me her phone and let me read the entire exchange. If my cock weren’t locked away, I would have masturbated several times yesterday to the images she sent.

We tried to make plans to meet for drinks. Mommy told him that I am a cuckold, and apparently he was involved in such a relationship once before. He wanted to meet me too, which I thought was interesting, and surprised me a little. Aside from a few other anonymous submissive men I’ve chatted with online, I’ve never had a man know my secret. And then I would be forced to look him in the eye, shake his hand, and pretend to be a normal person in public. This would be an entirely new level of humiliation for me. It would definitely take my already low self-esteem down a few pegs, which I deserve and need.

It was unclear whether we would all be at the same table, or whether I would be at my own table, away from them, but able to see them enjoy each others’ company. Either way, I would be paying for them and myself, which would be very humiliating if I were at another table. What would the waiter think? As Mommy was making the arrangements, she texted me to find a good spot for drinks in the town we would meet in. I chose a nice casual pub where Mommy and I had our first date.

She then instructed me to pick out clothes for her to wear on the date. I chose jeans that looked small and stretchy, and would fit her tightly. A seductive black top, and pink thong panties. From the text messages I read, he is an "ass man" and said that he loves a woman in thongs, so I picked those pretty panties out specifically for him to enjoy. Again, if my cock were free, I would have rubbed those panties up and down my stiff cock.

Unfortunately, we couldn’t agree on plans in time, so hopefully we will do this another day. I’m not sure if Mommy is ready to do this yet or not; she may just want us to go on a date to see me squirm in humiliation. But in her text messages, she made it very clear to this man that she was interested in a sexual relationship. They flirted by text very seriously with each other. Maybe she is testing me? Maybe she is easing us into it? Or maybe the first date is the last date in her plans?

As Mommy and I talk more about cuckolding, and the possibility becomes more real, I can’t help but wonder if she is doing it more for me, to fulfill my desires, than to fulfill her own. She doesn’t seem entirely comfortable with the idea, and obviously, I don’t want her to do something she doesn’t want to do, nor do I want her to do something she is indifferent to, simply because she thinks I want it. We’ve discussed this, and she has assured me that she wouldn’t do anything she doesn’t want to do. Still, she sometimes seems conflicted.

I need her to want it too. I need her to cuckold me because its something that she would get sexual fulfillment from. I want her to do it not out of a desire to give me an experience I crave, but out of a desire to truly hurt me emotionally. I don’t think she yet fully understands that the more she destroys me, the more devoted I will be. How can you not completely worship a woman when you see another man’s cock enter her?

I think she also worries that her own feelings toward me might change if she does this. She talks about wanting to build something with me, like she has to choose one relationship or the other, whereas I think the two can go hand in hand. And if I become more attached to her, and she were to become a little bit detached from me, that may be a natural evolution of our relationship too. She would have more control over me, and she might be more comfortable exercising that control. How can a Goddess love a slave? How can a slave not worship his owner?

It may be that once Mommy does this once, or perhaps after a few times, her current socially programmed hang-ups about "cheating" will fade and disappear. After all, we are creating our own rules to live by now. I hope that she can eventually come to enjoy cheating on me even more than I do.

But instead, we started the night in. I worshipped her ass as I typically do, rubbing my face on it, kissing it, sucking on it, then licking and fucking her ass with my tongue. She really responded to having my tongue in her ass last night, arching her back to push my tongue deeper. Then she rolled over, and I used the Magic Wand on her while trying to lick her clit around the device. She came very hard twice.

Then Mommy made put on a blindfold and I got on my knees on the bed with my head resting on the bed also, so that my ass stuck up in the air. Mommy used a prostate massager on me. This is something I have experimented with a few times in the past, but never got a lot of satisfaction from. Although it’s small, it was a little painful going in, but at a certain point, my ass seemed to swallow it. Mommy experimented with moving it different ways, and there was a time for about ten seconds when it did seem to hit my prostate squarely, and I instinctively arched my back more and embraced this new sensation. It was strange, but felt good. But after a while, my ass began hurting, so we stopped.

But Mommy has begun slowly training my ass. Maybe someday that will be the only way I get any sexual contact and hope for some relief. Just as I have become accustomed over time to only think of my mouth as the way I have sex, maybe I will start to think of this too as the natural form of sex for me.

Afterward, I took Mommy out to dinner. We went to a local brew pub that she hadn’t been to yet, and we shared a few plates of food along with a flight of five beers that they brew on the premises. I told her what little I know about the different styles of beers. Then we walked outside for a bit, the temperature was perfect. Throughout the evening, I had many opportunities to exercise the rules that Mommy had given me a few weeks prior. I opened doors for her, pulled out her chair for her, and rose from the table when she left, and when she returned, I got up, and pulled out her chair for her again. I noticed that that last act drew the attention of a woman a few tables away, and she kept looking over at us until we left. I wondered if she were thinking that she wished someone would treat her like a prize the way I did Mommy.

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