Jessica Ch. 03 - Vanessa Pt. 02

"Good girl! You made me cum just from fucking me," I praised.

She kept thrusting and I wondered at how good it felt, to have been able to have an orgasm from my male parts but not feel the oversensitivity and need to stop like I feel when I'm the one doing the penetrating. "Yeah, lick my cum off my tits," I told her as she cleaned me up.

"Should I stop?"

I pulled her head up and drew her into a fierce kiss, amazed at how hard she still was. "Fuck no! Keep fucking me, let's see if you can make me cum again!" I cried.

And she did. After a couple more minutes of that steady thrusting in and out of me she milked another prostate orgasm out of me, making me almost scream. I held her head tight to my breast, keeping her mouth working my nipple, as my rock-hard girlcock once again spilled my issue onto my belly.

Just as I had passed the apex of my orgasm while I was still pumping cum onto myself, she groaned and her thrusts got a little less regular. "Can I cum in you, Mistress?" Vanessa asked.

"Fuck, do it, cum in me!" I urged her.

"Aaaaaahhhhh!" she grunted as she spent herself deep inside me. I could feel her surge as she pulsed over and over again, painting my insides with her jizz. That only prolonged my own climax by a few seconds and I loved her for doing that.

"Unh! Unh! Unh!" she groaned as she finished in me, finally coming to rest with her thick lady cock buried to the hilt in my ass.

We were both trembling as we reveled in the feeling of the perfect end of an intense lovemaking session. She was still completely engorged as I pulled her head down for a gentle but passionate kiss. "That was amazing. Good, good girl, Vanessa. I think I know how you're going to decide but I really hope that I'm right. It's been a long time since someone has fucked not one but two orgasms out of me."

She flexed her PC muscles and it made me utter a quiet yelp. "This...this is the only time I've ever been on top in girl mode. I used to think that they couldn't go together but this proved me wrong, you made me feel so feminine and so good and thank you for that." My heart melted. This sissy with a huge cock that was still buried inside me was misting up.

"I'm so glad I could help you feel more comfortable, sweetie! I can't say the pleasure was all mine," I grinned as I ground down on her with my own PC muscles, making her squeak, "obviously, but you did fuck me to two orgasms. Thank you for sharing yourself with me, my sexy sissy girl," I said as I kissed her again. "You're so femme and still fuck so well with that monster!"

She blushed again. "Thanks...this is actually the first time ever."

Gobsmacked. Flabbergasted. Speechless.

Wait, this gurl just let me take her virginity!?

"What?"

She got mistier. Then Vanessa continued. "This is the first time I have ever been inside anyone else."

"Oh, wow! I...just...Vanessa, thank you so much for choosing me!" I gave her another long, passionate kiss and squeezed her somehow still stiff cock with my muscles. "This is an honor. I've never been anyone's first before, and for you to be asking to give yourself to me and then give yourself to me the first time is really something special." Now I was choking up. Damn female hormones! Those nanites really were something else.

"I really am honored, sweetheart. Thank you for making it me."

"I have a huge crush on you and you're so sexy and so feminine and you still have that clit of your own and thank you for letting me feel so good!" she gushed as she started to cry a little.

Of course, I started to cry a little in sympathy. "Come here," I whispered and held her head to my chest. "Thank you."

I could tell she wasn't sad, just very emotional, and I wanted to make sure that it was still a good experience. "You're such a sweet girl, I'm really glad your first time was good. Wait, it was good, right?"

She sniffled as I felt a few tears drop onto my skin. "This is amazing!" she exclaimed, her softening cock still surging inside me.

"Good." I chuckled. "This might be the only time anyone's cried on my shoulder while they're still buried inside me," I remarked, grinning.

Vanessa laughed and sniffled again. She met my eyes as she said, "You feel really good and make me feel sexy."

I paused. "You're still pretty hard. Wait, you're not ready to go again, are you?"

"...Do you not want me to...?"

I laughed, full of joy and happiness, and the source of those feelings, Vanessa. "We may need to lube up more, but if you can go again and do that to me again, I am more than on board!" Holy shit, this sissy was full of surprises! Not only was she packing serious heat but she was an amazing top. My surprise for her may not be used as much as I thought, I realized.

She grinned and kissed me and thrusted a little again. I yelped as I felt her start to harden up again. Ah, youth. When I was younger I had been able to keep it up like that.

"I want to make you cum again, Mistress," she sighed after we'd reapplied more lube.

"Why don't you clean up the mess you already made me make first?"

"Mmmm! That's sexy," she said as she bent down, only needing to withdraw so her crown was still inside me, and licked up all of my issue as though it was the only thing that could slake her thirst.

"Good girl," I said softly, then gasped as she kept thrusting into me but took me into her mouth. "Oh, holy shit!"

"Mmmph," Vanessa groaned as she simultaneously fucked me and sucked me off.

"Fuck...I'm gonna come real fast if you keep that up," I gasped. She was sucking me off with her expert tongue work at the same time her thick, long clit was sliding in and out of me.

"Mmmm!" she groaned.

"Come with me, sexy girl," I implored. She only groaned approval.

Within a couple of minutes I could feel my crest approaching. "I'm gonna cum!" Vanessa only doubled down both her fucking me and on sucking on my cock. "UhhhhhhHHHHHHHH!" I screamed as my third orgasm slammed into me. I shot rope after rope into her eager mouth and I felt her tense up and start shooting her own load into my ass.

We stayed that way for a moment after we finished, then she let my hypersensitive member slip out of her talented mouth.

"That was fucking insane," I laughed, giddy from how good I felt. "You are amazing."

"Thank you...Mistress," Vanessa replied. "I would've been more eager to be the top if I knew it felt this good."

I kissed her. "Thank you, baby. It's not often I cum that hard, especially not three times in a row!"

We snuggled for a few minutes after that, after she withdrew from me and we cleaned ourselves up.

"Do I really have to wait another three days before you'll agree to become my Mistress?" she asked quietly, her voice slightly muffled by my right breast where her head laid.

"I think that's the smart way to go about it," I answered. "I need you to have time to really think it through. Besides, this won't be the first time I make you wait.

"Speaking of which, I have a surprise for you."

"For me? What is it?"

I disentangled myself from her and retrieved the item from my purse. Vanessa only looked confused when I handed it to her. "What is this?"

"That's a chastity cage," I explained. "The ring goes behind your scrotum and the cage contains your clit and keeps you from using it. I think I got one that'll fit your impressive body part." I then handed her the contract that detailed our roles and the rules for both of us.

"So I can't use my clit at all in this thing?" she asked, turning the stainless steel tube over in her hands in fascination.

"Not unless I decide that you can. After that performance I may do that a little more often than I had in mind, though," I chuckled. "You're an artist with how you fuck."

She blushed a little. "So...is this part of you being my Mistress?"

"Assuming that you decide to submit to me, yes. That's what I was talking about earlier. If you choose to, you will be giving up control over most of your sexuality. That includes whether you can use your equipment for anything other than going to the bathroom. Are you okay with that idea?"

She thought for several moments. As she did I noticed her impressive girlcock stirred, then started to engorge. By the time she answered she was at least at a semi. "Yes, I am. I want you to control me and this is one hell of a way to do that," Vanessa expressed. She read through the contract and looked up at me. "This is a really sexy idea, I had no idea there was anything like this out there."

I gave her a kiss and asked, "Do you want to take it for a test drive?"

"Right now?"

"Right now. I have plenty of experience with these things."

"What do you mean?"

"I told you that I'm a switch. There have been times that I've been a submissive to a Mistress of my own in the past. There were a couple of times that I was caged for quite a while," I explained. "It's going to be a lot different than what you're used to. Why don't we get you into it?"

"Okay. How?"

"Follow me," I directed, leading her into her bathroom. I explained how she would need lube that wasn't water-based around the ring and that she might have to apply it several times a day to keep her skin from getting damaged, and what to do when she has the inevitable nighttime erections, and how to hide its large outline since she was so well endowed.

I set an envelope on the counter. "I will be your keyholder but since we're not living together you need a key in case of an emergency. You can see I signed my name over the flap so I can tell if you have used it. I will keep the other key," I told her, putting a necklace with the other key around my neck. It hung low enough that the key was framed by my breasts.

"Now let's get you in this, as long as you're still comfortable. Are you?"

After Vanessa took a deep breath she looked me in the eye and answered, "Yes, I am, Mistress."

"Good. I'll be right back." I got an ice pack out of her freezer and returned. "First we need to get that erection gone," I told her. She gasped when the cold plastic touched her stiff member. Within a couple of minutes she was flaccid as can be. "There we go," I said, and showed her how to apply the lube and slide her testicles into the ring once at a time, then push her member through. Then I showed her how to work her penis into the cage itself, and I highlighted how important it was to get her urethral opening lined up with the opening at the end of the cage, and how she needed to do everything she could to keep herself clean while caged.

"Oh, that's strange," she remarked as soon as I slipped the lock into its slot and turned the key.

"What's strange?"

"I'm getting really turned on but this thing isn't letting me get hard. This is getting uncomfortable, Mistress."

I stood and kissed her. "That's kind of the point. Is it painful, though?" I had really lucked out on guessing the size since it was just about a perfect fit. Just big enough to hold her member when she was completely soft so it didn't have anywhere to go when her body tried to get erect.

"No, but this is a weird feeling. It makes me feel like you already own me," she replied.

"Good girl. Since you aren't formally my submissive yet this is a test drive, so to speak. You are welcome to take it off if you have a serious problem coming from the cage, but you have to let me know the moment that you do. After it's dealt with we'll figure out what the cause was and what we'll do going forward. Do you understand?"

She swallowed then looked into my eyes again. "I understand, Mistress."

"Good girl."