My First Dominant Girlfriend

As you nay recall, Rebecca and I had made a deal. And as embarrassing as it felt to have worn those stockings, I didn't care because all I could think about the next few days was having sex with her. Finally I'd be able to put my dick inside of her. We'd been dating at this point for almost a year and had only had my dick inside of her once (twice with the cock sleeve but not sure that counts).

That day she had texted me while work. I was cleaning and running errands, fulfilling her daily list of tasks. She wrote "ok little one. Tonight's the night! Are you excited?" I wrote back that I was very excited. She responded "let's see if that penis of yours can last more than a minute this time LOL."

I didn't laugh but my dick started to push against my cage with excitement. I wanted more than anything to be able to last a long time. Not to please her, because I realized at this point that my dick was too skinny to give her any pleasure, but so that I could thoroughly enjoy it!

I responded "haha, I hope so too, because it feels so damn good."

Her response: "oh poor baby. I have something that might help."

I wasn't sure what she meant but I continued with my tasks. When I got home I showered and had dinner ready when she got home. While we sat and ate I couldn't help but stare at her breasts. She was wearing a work shirt with a women's blazer, but the cleavage was immense. It was the first time I realized that the men she worked with must check her out every day. There was no way she wasn't the hottest woman in her office.

After dinner she told me to take my cage off and relax. We watched a few of our favorite shows. I could barely hold my excitement. Rebecca didn't seem to be thinking about it at all.

"We are still having sex right?" I asked.

"Yes John. Don't beg."

"I'm not begging!" She shot me a stern look. I realized at that moment that she was not looking forward to this as I was.

"Fine. Let's go." We got up and went into the bedroom. We both undressed and she unlocked my cage. I eagerly jumped into bed with a big smile. "Settle down John. There's something you're doing before you stick your pencil dick inside of me. I think it'll help you last longer. Maybe."

She took out a very large dildo. This was a new one. It was black - or dark purple maybe - and I guess I must have made a very frightened look, because Rebecca immediately laughed.

"Don't sorry little one, this is for me. I want you to put some lube on it, and put it inside of me. Slowly."

I did as she said. And laid on her back and spread her legs. I slowly inserted it into her smooth, bald pussy. She gently rubbed her clit as I did this. It took literally 5 minutes to go all the way in, but as soon as it fully entered her she let out a long moan and her eyes squeezed shut.

"Oh my god that feels good. I forgot what a good cock feels like. Push it in and out John. Faster!" As I did thrust it into her with my hand she rubbed her clit faster. The dildo, which was in a shape of a cock and slightly curved, started to go into her very easily. There was almost no resistance.

Meanwhile, I could feel my precum leaking out of me and all over my stomach and the sheets.

"Faster John! Haaaaaarderrrrrr!" And rubbed her clit vigorously and her breathing got faster and faster. "Harder John! Fucking harder!" I didn't know what to do, I was thrusting into her very hard already. I didn't want to hurt her but I did as she said. I started using two hands and started to pound her with it. I seriously thought I was going to hurt her but within 30 seconds of doing that she let out a scream.

"Ahhhhhhhh!" She came and her legs shook violently on the bed. Her fingers grabbed the sheets. I could see her eyes were watery. I smiled as she looked so immensely satisfied.

I started to pull it out but she opened her eyes and looked at me. "No, not yet John. Leave it in."

And then pulled me up and gave me a long hug and we kissed. She rubbed my back.

"Thank you for that John. Maybe we should do that more often. It felt amazing. But I know you're probably very excited so now it's your turn. I want you to pull this out and enter me. I'm hoping now it won't be as tight for you so you can last longer and enjoy it more."

So THAT had been her plan. I was impressed with how thoughtful she had been. And it turns out she was right. Or mostly right. I did think I'd last longer. I got in top of her and expected to slowly enter her, but as soon as my dick began to enter her it slide right in. She was not nearly as tight, as that huge dildo had stretched her right out. Nonetheless it felt so fucking good.

"That's it baby. Now give me those little pumps you like to do." Her legs were spread but she had both her feet planted. She rubbed my back. Absolutely zero moans from her. And was just interested in watching me enjoy this.

"Come on little one. Pump that baby dick into my pussy. Doesn't it feel as tight now does it?

"No, but it feels so good." I started pumping faster and breathing heavier. In the back of my mind I remember thinking that yes, I knew I could last longer. I started pumping with more confidence. But then she said something that totally made me lose my control.

"Good boy. Keep pumping into me. You've already lasted more than a minute. That's because I'm not as tight right now....because your baby dick can't last when it's too tight can it?" I pumped faster as she whispered this into my ear. "This is what it feels like to be inside me after I've been fucked by a good sized cock, John. After I've been satisfied."

I completely lost control. "Ooooh!" I moaned. My cum exploded inside of her. She let out a little moan as she likely felt the hot squirting inside of her.

"Good boy! Such strong squirts. Give me those cummies." I still hated when she said cummies. It made me feel so small and vulnerable...and babyish. But by now I was used to it and I collapsed into her arms. Tired and satisfied.

She rubbed my back. "Very good job. and you broke your record!" We both laughed. Boy, did I truly love her. Despite feeling less like a masculine male, and dealing with all those mixed feelings, I truly felt at peace and taken care of. It felt like all my needs were being met. In retrospect, this was the most at peace with myself I had ever been.