On Saturday morning Mistress and I woke up ready for sex. As soon as we got going, Mistress started verbalizing with a lot of things she knows gets me over the edge. This story is a result of the last couple days thinking about what we talked about.
Mistress walked in the door after work. I was expecting her as it was our "date night". As she walked in she said "before we go out, I want to discuss something with you". I asked her what it was she wanted to talk about. She said, "get a bottle of wine, 2 glasses and meet me in the bedroom" and she walked out.
I went to the wine fridge and picked out a Sauvignon Blanc that she likes. I opened the bottle, grabbed 2 glasses and headed upstairs. Mistress was sitting on a bench we have at the foot of our bed. She was still in her work clothes that consisted of a mid-length skirt, blouse, and sexy heels. "Pour me a glass and get naked", she said. I blushed and poured her a glass. Then I blushed some more as I started to undress. It was awkward getting undressed as I had just dressed for our date night. Once I was naked, Mistress said "go put on your nighty that is hanging on the closet door knob." Occasionally Mistress has me wear a nighty to bed. I went to the closet and put it on. I smoothed it over my body including my cock that was now sticking straight out. "Hurry up!", she said. "I'm hungry and looking forward to sushi." I came out of our bathroom with a sheepish look on my face. I have no idea what is going on. I'm aroused but also a little ashamed. "Come over here and kneel at my feet". I do as instructed. This is something different. Mistress is not a big fan of making me kneel. I couldn't tell you the last time that she had me kneel, but I think it goes back to when we first started dating.
"It looks like someone is excited to be in your situation" she said as she looked down at my cock poking up at a 45 degree angle through my nighty. "Are you excited slut?" she asked.
"Yes Mistress, excited and scared."
"Don't be too scared, I'm not going to hurt you. When we were having sex a couple weeks ago, didn't I tell you I wanted you to surprise me with a couple new nighties?"
"Have you done this?"
"No Mistress" I said as I cast my eyes downward, embarrassed.
"Didn't I also tell you I wanted to start seeing some more feminine items under your male clothes?"
"Then why are you wearing male underwear on our date night?"
"Because I wasn't..."
"Don't give me excuses" she said as she cut me off.
"What do you think your punishment should be?" she asked
"A spanking Mistress?" I suggested.
"No, you will like that too much, plus I want you to punish yourself. I don't want to have to have tp put any effort into punishing you. Do you remember what else we talked about a couple weeks ago?" she asked.
I had a puzzled look on my face when she said "we agreed that you would eat your cum if you were edging and/or masturbating and came. Have you cum without my knowledge since then?"
"No Mistress", I said looking into her eyes. "There is no way I could do that after an orgasm. It's too gross and I don't have the willpower to do that on my own. Before I cum is one thing, after I come is another".
"That's what I was afraid of." she said. "I'm going to give you the willpower you need. I want you to start stroking. You are going to have an orgasm in your hand and you are going to eat it. If you don't cum, or if you don't eat it, you will go into chastity until you do. We will do this every day until you succeed"
I started to open my mouth to say something but before I could Mistress said, "start stroking".
I was already hard and started stroking my cock. After about 10 strokes, Mistress said, "I almost forgot something." She got up and when to her night stand. She dug around for a second and pulled out a realistic looking dildo. "Remember? A couple weeks ago you said you wanted to suck a dildo too." I thought about arguing about that being under different circumstances but thought better. Mistress came back to the foot of the bed, put the dildo in front of my face and said "open up".
I went back to stroking and Mistress pushed the dildo a little deeper in my mouth. She said, "don't let it fall out and don't use your teeth. When you are ready to cum, I want to you to ask permission with that cock in your mouth".
I continued to stroke and what Mistress did next both excited me and shocked me. She pulled out her phone and took pictures and videos of me in my nighty, on my knees, stroking my cock with a dildo in my mouth. "These pictures and videos will be my little way of reminding you of what a little slut you are. I will send them to you when you least expect it. You will be out with friends and I will send one to you. You will be ashamed inside, but will think of how I fulfill your needs."
"Also, we are going to keep doing this cum training until I know I can trust you to eat your cum without hesitation. Whether it's in your hand, in my pussy or on the bed sheets, I want you to crave it,"
"Msssttrrsss, may hh i hh cum" I mumble around the dildo.
"Not yet, let me get my video going" she said. "Yes, now you may cum, catch it in your hand, and don't you dare spill a drop."
I point my cock downward into my hand and let loose. My hand quickly fills up and I look at Mistress pleadingly for her to stop this. She takes the dildo from my mouth, takes the tip of it and swirls it around in the cum sitting in my hand. She gets a large amount on the tip and says "open up, or you can put on your chastity device and we can do this again tomorrow."
For a brief second I consider the chastity device, but realize I can't stop this forever. I open my lips and she puts the cock in my mouth. Only then to I realize that she is still filming this. I am more than ashamed. She dips it in the cum again and puts it to my lips and says "wow, it looks like someone is enjoying this. Are you enjoying this slut?"
"No Mistress." I say with a frown on my face.
"Don't worry, you will soon enough. Now lick your hand clean, put all of this stuff away, get dressed for our date and then you can have a glass of wine to wash that cum taste out of your mouth. Oh, and since you didn't think enough to wear something sexy under your clothes earlier, put on a bra, panties and some suspender stockings under your male clothes. I may want to take advantage of you when we get back"
"Hurry, I am hungry!"