The next four weeks were fun in terms of our dates. We went on an overnight hike, a few museums, and even did a couples night out. At every moment, however, nothing sexual except kissing, and on our overnight hike and had me go down on her until she came. You can imagine my disappointment when she then turned over and said good night. I didn't get more than 2-3 hours of sleep that night.
I was getting more and more desperate and she definitely knew. She would occasionally have her hand brush against my ass or my penis. I know it was intentional because she sometimes would then grin at me and say "still upholding your promise, right?" And I'd say yes. And, in fact, I really hadn't masturbated at all. I was leaking precum in buckets every day, but I hadn't you had myself. It got to a point toward the end of 4 weeks that I fully expected to have a wet dream. I was hoping for one, just to get some relief.
Finally, one night in her apartment, she said it was time for a release. We had just finished dinner and sat down on her couch for a movie.
"I can tell you've been honest about not touching yourself John." Then she cuddled up to me and whispered in my ear. "I'd like to give you a release tonight. Get those cummies out." Her voice turned almost into a mommy kind of voice. I used to think it was weird but now I loved it because it felt nurturing given my desperation. "Would you like me to do that? To help get your cummies out?"
"Oh my god, you have no idea!" I said. She smiled when she say my excitement.
"Good boy. How hard was it to not touch yourself?"
"So hard!" I then explained to her how hard it was and how I had been hoping for a wet dream. She stroked my head and rubbed my thigh as I told her. I was rock hard.
"Awww my baby boy. That does sound very hard. I do want you to text me if you ever have a wet dream though...like as soon as it happens. Ok? And as for not jerking off. This is why I wanted you to read about chastity cages. I know they seem silly but they can really help. You can't get hard in them, so it makes things far less tempting."
"I did read about them," I said. "I'm a little nervous to try though. I think it would hurt at night. And I don't think I'd want to sit down in the toilet to pee!" We both laughed a little.
"I understand. Maybe we can talk more about it later. Right now I think my little one needs a release." And with that, she told me undress. I thought she was going to tell me to go into her room and get in all fours like the other times, but this time we stayed right on her couch with the movie paused.
I stood in front of her naked while she sat on the couch in her tight jeans and a loose blouse. I hardly ever got to see her naked but her body was perfect.
"I see you're very hard, little one. Let's see if you can cum with no touching." She told me to get on her knees. She went into her room and came back with a few items: lube, a dildo that looked like the one she first used on me, and what appeared to be her underwear. She shoved the thong into my nose.
"Breathe it in John. Smell my pussy. I wore these yesterday and worked out in them last night, right before I masturbated." I instinctively reached for my dick to stroke it. If I had stroked it a few times I'm pretty sure I would have cum right then, but before j could touch it I felt a hard slap across my face and I let out a small cry of pain.
"Do NOT touch yourself unless I tell you to! Do you understand, John?? Do you want me to stop this, John?!"
"No! I'm sorry, I forgot. I'm sorry." I was embarrassed that I just sat there on my knees and accepted the slapping. What kind of man does that? Also, it really hurt.
"I understand you haven't cum in a month. I know you're eager. But you do as I say." She then told me to turn around and put my hands on the coffee table facing the TV with my ass facing her. She put in her gloves and slowly inserted her finger into me. Just like the first time it hurt a little and then felt amazing as she inserted the very small dildo and passed some kind of barrier inside of me. I'm not sure what it is, but when it enters after a certain point it feels so unbelievably good. She slowly pushed it in and out. I couldn't help but moan.
"Oh good boy John. I can tell you really enjoy having this in your ass. And my gosh, look at all the dripping you're doing! I'm so proud of you little one."
I hated that she called me little one but when I was in this mindset - subspace I think it's called? -- it actually was both a turn on and comforting. I looked down to see what she had been talking about. I could see precum slowly dripping all over her coffee table. A long strand of it connected from the tip of my penis to the table. Underneath was at least a teaspoon full. I moaned at the sight.
"Are you a little ass slut, John?"
"Mmmm yes" I said.
I stayed in that position for another few minutes until she told me to turn around.
"Ok John. I want you to sit on the couch beside me. But I want you to lean way back and spread your legs. Put your feet up on the coffee table. I did this and she sat right beside me, still in her jeans and blouse.
"Ok. Now, life your knees back to your shoulders." This time I felt more vulnerable and more embarrassed, because I was facing her. Normally I was facing away from her. She then stuck the dildo back into me as I held my knees up as far as I could. I felt very embarrassed but the dildo felt so good and I was so desperate to cum. It's hard to explain, but I felt this relentless tingle at the tip of my penis, as if I would cum at any moment....but without anything touching it, it was just permanently like this.
"Mmm that feels good doesn't it John? I'm going to give you a treat now for being such a good boy and not touching yourself for a WHOLE month!" Her voice seemed so sincere but also so condescending at the same time. The thing is, I didn't feel like she was really talking down to me. It really felt like she was proud of me, and that made me feel good.
She unbuttoned her blouse and undid her bra. She then let her beautiful perky breasts exposed for me to see. Her nipples were very hard.
"Here you go, baby. I wanted to give my good boy a nice treat. Help you get those stubborn cummies out, right?"
"Yes! So much."
"Good boy. Now what do you say?"
"Thank you. So much."
"Good boy. Thank you ma'am. That's what you say."
"Thank you, ma'am." Again, awkward. But I would have said anything in that moment.
"Not outside of the metaphorical bedroom, John. But inside, it's ma'am from now on." She then took two fingers and lightly started stroking me as she pushed the dildo in and out of me with her other hand. I couldn't stop staring at her tits.
