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My First Dominant Girlfriend Ch. 05

Story Info
John tries chastity and gets rewarded.
3.1k words
4.65
18.6k
25

Part 5 of the 26 part series

Updated 06/24/2024
Created 04/11/2024
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So for the next week or so I wore a chastity cage. I hated it. Everything about it. I hated how it felt all day and night. Nighttime was the worst, since normal nocturnal erections couldn't happen (which worried me), and sleeping was difficult. I woke up angry and tired every morning. But the absolute worst part was having to sit down to pee. This was embarrassing on a whole new level...it didn't turn me on or make me feel like I was part of something fun and sexual. So, that was my first week in chastity.

Through the week, Rebecca would occasionally text me to ask how "it" was going. I would typically respond with a short message, like "I really don't like it" or "not great". She wouldn't respond directly to those, but instead change the topic. I was convinced that when we got together next I was going to get the key from her and take it off. I didn't care about the consequences, I hated it. And, if she couldn't respect that, I wouldn't want to be with her anyway. This is what I thought.

Turned out, the following weekend we had plans to be together was suddenly canceled because she had to take a last minute flight to visit her family--her grandmother had fallen and was in the hospital for a few days. So, I was stuck in his cage for another 3-4 days at least. I asked her if I could drive by her place before she left to get the key and she pleaded with me to just keep it in for a few more days. I agreed.

That Friday night I received a long text from her that read:

"Hey John, just landed. I'll call you once I'm settled. I was thinking on the plane and I want you to know that I know this has been hard for you but you're doing a great job and I'm very proud of you. I PROMISE it will get easier...I know it's weird but it really really really makes me happy and it makes me feel closer to you. You're seriously so attractive and fun and caring... my heart gets beating so fast when I'm with you. When I finally get back I will reward you :) I want us to make love. Over and over again. Love you, John. With all my heart."

Just the previous Sunday we had both proclaimed our love to each other. I can't lie, her text made me feel so good. She really was perfect for me. I know I talk only about the sexual part, but outside of that we were excellent. We loved all the same kinds of activities, similar world views, had great friend groups. Not to mention that I'd never been with someone as attractive as her. My buddies joked that she was out of my league.

So, after receiving that text I met up with a few friends and had some drinks and decided to stick with it. Of course, I questioned that decision as soon as I found myself back at home after a cab ride sitting on my bathroom toilet to pee. I was semi-drunk. I don't know why but this time I felt my dick getting hard (or trying to) as I flushed the toilet. I wasn't sure why, but I think it was from the feeling of being submissive. Having to sit and urinate made me feel submissive but why? Well, because that's what women do. But women aren't weaker. I suddenly recognized my own bias. Maybe this was Rebecca's point? She was an attorney and was a bit of an outspoken feminist of sorts. She was very smart, so I wouldn't put it past her to have been intentionally making this a lesson. In any case, my dick pushed hard against the pink plastic cage. I wanted to cum so bad. I don't think I had gone this long without an orgasm since I was 14. Well, that night I got my wish.

Not exactly the perfect wish, however. I got my orgasm, just not in the best way. I woke up from a dream around 3am and was shaking a little - I had had an orgasm in my dream! I never had that happen before. Usually right before I'd be close to cumming in a dream is just wake up hard. This time I woke up from dreaming about fucking Rebecca and I actually had an orgasm. I laid still with my eyes open. I felt cum coming out of my dick, but it felt different-more like peeing with a good sensation. I brought my hand down and was quickly reminded that my cage was on. So I gad an orgasm without even having a hard on? all around my cage and on my sheets was drenched in cum. I got up and turned the light on. A huge stain of cum was on my bed and some was dripping down my leg and out of my cage. I couldn't believe it. It had felt great but also very different.

I cleaned up the sheets and took a shower. I kept ruminating about what happened. I guess I had so much cum built up that my body felt it was time to go. I remembered that Rebecca told me to text her whenever something like this happened so I did:

"Hey love. You told me to text you if I ever had an orgasm without you. Well I can't believe this but I actually had a wet dream lol. I've like never actually had one of those."

I laid back in bed and go my surprise I got a quick reply.

"Hey!!! I forgot to turn my phone off and heard your text. Thank you for telling me...and I'm not mad or disappointed at all. These things happen when your cummies are all backed up :) clean up and get some sleep. Can't wait to talk to you later in the morning, love. And I can't wait to make love to you when I get back. Our first time!"

I hated when she said "cummies" but I was glad she wasn't mad.

The next day we talked. To my disappointment, she had decided to stay the whole week to help with her grandmothers transition. I secretly rolled my eyes when she told me. Another damn week in this fucking cage.

I walked around that weekend furious. I thought about getting some tools and just breaking the cage off. I actually sat down thinking. Would Rebecca REALLY get mad? I mean, come on. Ultimately this was all some crazy sexual game right? If I told her it was hurting me or something I couldn't imagine she would actually be angry. How serious was she anyway? I honestly wasn't sure. She seemed pretty damn serious in the moment. I sat and contemplated for about an hour. And then it hit me: we were in love and had now been together for a few months, and guess what? We had never actually had intercourse. That's why she said making love when she gets back will be our first time. Of course, I was well aware of this fact. It was odd and it pissed me off. But what hit me was the level of seriousness it implied. If she was doing this all for a bit of a fun sexual game, she'd still want to actually have sex. I sighed. Ok, John. One more week.

And, as it turned out, things did get better. I even told Rebecca that it wasn't as bad as last week. The toilet sitting still bothered me, but I started to sleep better (unfortunately no more wet dreams) and during the day I had started to forget it was there unless something made my dick want to get hard. I still didn't love it, and I was dying to cum, but it really stopped being so bad.

Finally, after 2 weeks, we got back together at her place. We had dinner and wine and talked about her grandmother and work and everything else. It was great to see each other. We missed each other like crazy, as young lovers do. Then, as the night wore down, her tone changed. We were kissing and she said into my ear:

"Ok little one. Go into my room and strip." I did as she told me. I could feel my dick pressing so hard against my cage trying to get hard that the skin of my penis was bubbling outside the cage vents.

She came into the room and I stood there naked. She was wearing a low cut summer dress. She looked down at my cage and then bent down and wrapped her hand around it.

"I'm so proud of you John. I know it was so hard but it made me SO happy. Now let's give you a little break." And with that she took out the key and took off the cage. I was instantly hard.

"Wow John! I don't think I've seen it this hard before." She gave me a big smile and then took her dress off. She undressed completely and told me to fold her clothes, which I did. She didn't do anything weird. It felt normal. She then crawled into her bed and patted the side next to her.

"Ok John, I want to give you your reward. Come over here and kiss me."

I eagerly jumped into bed and wrapped my arms around her and we made out. It felt amazing. She positioned herself underneath me and wrapped her legs around me. She was very strong. She had stronger thighs than I did. As we made out passionately, her hand touched my dick occasionally, not to stroke it but almost to check that it was hard.

Our breathing became heavier and I could feel her wetness against my leg and my genitalia- basically whatever part of my body rubbed against her smooth pussy. She then stopped kissing me and gently grabbed my face.

"Ok John. I want you to make love to me. I'm on birth control so you can cum inside of me ok?" I said ok. "Are you excited little one?" Ugh, why did she have to say Little One? It bothered me for about a second but I was so excited for sex that I didn't care. I was also excited for real sex with her because in all honesty I was pretty good in bed -or so I thought- and I wanted to show her.

"Yes, so much, Rebecca".

"Good. Now put it in." And with that, she spread her legs. Her hand grabbed my dick and guided it between her legs. I felt the tip touch her labia and expected some resistance but it entered her very quickly. She was very wet and warm and I guess my skinny size didn't create much friction. Still, for me, it felt tight and oh my god it felt like sex for the first time.

She didn't moan or really make any noises which I remember thinking was weird, since that had always been my experience with sex. Women always moaned as soon as you entered them, right?

She kept her arms wrapped around me as I rocked up and down. Her eyes stared at me lovingly.

"There you go, baby. Theeere you go. Come on, keep humping me. Does my pussy feel so good baby?"

I moaned yes. It felt so fucking good. I stared going in and out faster....

"Yes, good job baby. I can feel your penis. ok now go faster if you want and--"

I couldn't believe it. I suddenly came. I came very hard and moaned loudly. "Ahhhh, oh my god". I was breathing so hard.

"Wow John!" She wrapped her arms around me and giggled. "Oh baby I bet that felt good. That was SO fast. Good job baby." And she kissed me several times on the cheek.

It felt so good but a massive wave of embarrassment washed over me. I'm not exaggerating when I say that I couldn't have lasted longer than 60 seconds. I lasted longer when I lost my virginity! But it felt so damn good.

"What do you say John?" She said lovingly.

"What? Oh. That felt soooo good!" I said.

"John. What do you say." Her tone control changed. She was stern. I realized my mistake but also this indicated to me that our night wasn't over, even though all I wanted to do now was fall asleep.

"Thank you, ma'am. That was amazing."

"Good John. I'm glad you liked it. That will not happen often. Now it's my turn sweetie...I want you to go down on me."

I didn't hesitate. I knew I had just came inside of her but I also knew to keep my tongue only on her clit. I went between her legs and instantly started licking her clit gently. She moaned.

"Oh John that feels great. I thought I'd maybe cum with my fingers as you fucked me but you came so quick with your skinny dick."

I kept licking her clit but in my post orgasm clarity I didn't like hearing what she was saying. It was all true. But then she said someone hurtful. I pretended not to hear and kept licking.

"You fuck like a boy John. Like a teenage boy doing it for the first time. It's actually very cute, and expected. But now I need to cum hard, enough games."

She then flipped around faster than I could figure out what was happened and suddenly she was sitting in my face. Her clit shoved against my mouth.

"I want to cum hard John. But first I want you to clean me." Before what she said registered, she grabbed my head with her hands and pushed into me. I thought she was going to have me lick her ass but instead she stopped right at her pussy. At the opening. Now I knew what she meant.

Cum came gushing onto my face and into my mouth. My own cum.

"Clean your cummies John. This is your mess to clean." And then she moaned. I might have pushed her off me thinking it was all a joke but her tone and her moaning made me realize how serious she was.

It grossed me out but I did it. I swallowed my cum and her juices. She held me there for 5 minutes. I guess I came a lot because it kept coming out. It was almost like she could control the flow. Toward the end of the five minutes I was already rock hard again.

"Good job baby." She then moved backwards slightly and positioned her clit onto my tongue and I gave her a very strong orgasm.

After we finished we laid together in bed. I was hard and frustrated. I wanted to cum again. She could sense this as I was subtly pushing my dick against her leg.

"Oh poor boy. I know you still have cummies backed up. I will let you cum one more time but then we put the cage back on, ok little one?"

I agreed. I would have agreed to anything. Her voice then changed again - it was not so much that she was mad, but just stern and cold. As if she was just performing a chore or task that she knew needed to be done.

"Ok, up on all fours John. Face the wall. Ass up." She grabbed lube and I heard her out on gloves.

She walked around and stood by my face. "Open your mouth." I did, and she shoved her thong into my mouth. "Smell these and taste these." I could tell they were from just that day because they were still heavily scented and warm.

I then felt her finger in my ass. It wasn't done gently or warmly as it had before. For example, she didn't massage my ass cheeks or rub my legs or even say anything. I moaned loudly even with her thong in my mouth. I could tell I was leaking buckets of pre-cum. Then I felt the dildo. It felt so amazing as it entered all the way. I realized in the last two weeks that not only had I missed being able to cum, but I missed....

"Oh, you missed having something in your asshole didn't you, John??" Yes. That. It felt so good. She reached down as she pushed the dildo in and out and grabbed my dick with her whole hand. Almost too aggressively. She stroked very hard and fast.

"Ok John I want you to -- ". And then it happened again. I came in less than 30 seconds.

"Wow! Again baby boy! Look at all those cummies. Good boy. So fast for me. I'm proud of you." I couldn't believe how fast I came. She pulled out the dildo and told me to stay on all fours, which was annoying because I was tired and also had that post orgasm clarity.

I started to say something when suddenly her gloved hand was shoved into my mouth and I tasted cum. "Clean it up John." I sat up and pushed her hand away. That was a mistake. And instantly slapped me with her other hand. Twice. I sat there not knowing what to do. She stared at me and I stared at her. I mean, it really hurt. For a moment I thought I might cry. I put my hand I'm to my cheek that she slapped. Still staring at each other she said, "clean it up." In a loving voice. I could tell she felt a little badly about how hard she'd hit me.

To this day, I don't know what made me do it -especially because I wasn't horny at that point--but I think it was because I sort of knew that if I had just walked out I'd never see her again. So I grabbed her hand with the cum and out it into my mouth. I licked the cum off of it completely. When I was finished she said "good John." Almost in a whisper.

We then fell into a deep sleep. When we woke up I cooked breakfast and we planned out our day. I sort of pushed the night - especially the slapping--out of mind. Until right before I was getting into the shower, Rebecca came right up to me and said "Here. Take this. I want you to cum once more in the shower. When you come out I'll put your cage back." And then she kissed me on the lips and handed me the dildo. So awkward.

I couldn't resist. 2 minutes later I had the dildo in my ass and I was imagining the previous night. And not about entering her. I was remembering her sitting on my face and cum drizzling down mouth. I exploded with an orgasm.

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5 Comments
AnonymousAnonymous4 months ago

Great story.

Please keep writing!

journeyofselfjourneyofself4 months ago

Thank you! great story, i passed the link along to my wife and her boyfriend. They'll use some of it to humiliate me, I'm sure.

reader796reader7964 months ago

Amazing story, loving the humiliation. Loving that the chastity cage is here to stay now. Looking forward to see Rebecca increase her control. Hopefully it will eventually spill over to outside the bedroom as well.

Will527Will5274 months ago

Hate the idea of a cage for any reason or any time, no woman would be worth it. BUT the rest of this was awesome. Well done.

FailedscoutFailedscout4 months ago

This has been the best chapter so far.

Thank you for writing and posting here.

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