Jessica Ch. 04 - Vanessa Pt. 03

This is the next installment of Jessica's story. I can't write as much or as often as I'd like to, but I was able to work on this one enough to get this chapter finished. Constructive criticism is always welcome, as well as feedback. Thank you for reading!

It hadn't been easy for Vanessa. Never mind that she still had to live the part of her life in her male mode, but she was also trying very hard to live up to my expectations of her as a submissive, and that included wearing her cage as often as possible whether she was in her girly mode or not.

The complaining was constant at first. After, of course, I had made sure that she wasn't actually being hurt by the apparatus trapping and denying her impressive sissy clit. "Mistress, I'm horny!" "Mistress, I need to take this off, please!"

Every time my answer was no. "But please, Mistress! It's uncomfortable!" Vanessa would beg.

"I know it is. That's the point," I told her. "From now on, every time you ask to take it off, I'm going to add another day you're going to be caged. Are we clear?"

"Yes, Mistress," Vanessa said with a pout.

"Let's be honest here: you're horny and you don't like having access to your sissy clit denied because you want to get yourself off, don't you?" I asked.

She didn't say anything at first. "Well?" I prompted.

"Yes, Mistress, that's it. I really need to cum!" she pleaded.

"There's a big difference between need and want, my sexy sissy," I reminded her. "Just because you want to be let out doesn't mean I have any obligation to do so."

"But I'm so horny, Mistress!"

"Good!" I retorted right away, grinning. "That's exactly how I want you."

We were in her living room again, and I was dressed to the nines. I had on a low-cut white silk blouse that showed off quite a lot of my tits, and that was cut so that a decent amount of my midriff was visible. Below that was a no-nonsense leather pencil skirt that only came halfway down my thighs. I had abandoned any gaff, so that once I arrived at her place, I readjusted my cock so that it was just off to one side inside my lacy panties. This showed a considerable bulge in the front of my skirt. I was also wearing lace-topped silk thigh-high stockings and my feet were clad in very expensive black skyscraper stiletto heels. I very much looked the part of an in-control, bitchy, domme, just how I wanted to.

Vanessa, on the other hand, was wearing a simple sun dress similar to the first time we had met. Due to the prodigious size of her package I had made sure that she also had a strap to go around her waist and snap around the left and right sides of the ring of her chastity cage, so that when the inevitable nighttime erections came (or tried to), her body could try all that it wanted to get hard, but the cage would stay nice and close against her pelvis, better keeping her cock trapped.

Oh, yeah, and I made sure she was on her knees in front of me before she was allowed to speak. After waiting the three days that I required of her, she had breathlessly, immediately agreed that she wanted me to be her Mistress.

Vanessa pouted, looking up at me. "How long do I have to stay locked for, then, Mistress?"

"We'll start with a week since you're new to this," I declared. Of course, I had experience with chastity and would happily let her out right away if there were any health risks that could come from her being caged, but I had nailed the sizing on her somehow and the cage was a near-perfect fit. It wasn't solid steel; that's optimistic to the point of bordering on stupidity. Hygiene is critical with a penis in chastity, so this one was a series of circular bars with others that ran lengthwise along her shaft, all welded together to make the ideal cock prison for her. This let Vanessa—or her male version of herself—get soap and water over the skin to keep herself clean, but still kept her from being stimulated enough to reach an orgasm. There was an opening about half the size of a dime at the end of the cage so that she'd have plenty of room for urinating. She had also been diligent about applying liberal amounts of non-water-based lubricant to the area that the ring of her cage covered to protect against chafing.

"A week?!" Vanessa cried. "It's only been four days and I'm going crazy! Mistress," she appended.

"Want me to make it two?" I inquired with a raised eyebrow. It was so nice to not have to tuck, since the power exchange dynamic going on at that moment had me halfway hard.

"What? No! No, Mistress, I don't want to be locked up for two weeks."

"That's better. Now, I think you should apologize for being so whiny. I don't like my subs to be bratty."

"How can I apologize to you, Mistress?" Vanessa asked. Her pretty eyes were big, as if she was afraid she'd offended me.

"Well," I began, uncrossing my legs and spreading them as much as my tight skirt would allow, "you could use your mouth to make me feel good. A blowjob is an excellent apology sometimes," I suggested.

"Yes! I'd love your cock in my mouth, Mistress!" She was practically begging to suck me off.

"Well...now that you're that enthusiastic, maybe I should come up with something else," I said, sounding like I had changed my mind.

"Please, Mistress! Please let me use my mouth on you! I really want to suck that gorgeous cock you have, Mistress. Please?"

"I don't know..."

"I'll stop asking to be let out, I promise!"

"Hmm..." Now I was playing with her. Of course, I wanted a blowjob! I already told her the first time we had played that it's my absolute favorite way to get off. But she seemed too happy about it for me to just agree to it. "I know how much you enjoy it, too, though. An apology should mean you have to do something you don't want to, to show me how sorry you are that you're willing to endure something unpleasant as atonement," I explained.

"But if I can't get off myself, I'm so horny I want to have some kind of sex! Please, may I suck your beautiful cock, Mistress? Please?"

With a deep, theatrical sigh, I said, "Well...I guess so. Get over here."

"Yes, Mistress! Thank you, Mistress!" Vanessa played perfectly into my hand. She was already on her knees so after she crawled to me, I made her hike my skirt up to my hips and then pull my now full erection out of my straining panties.

She was just looking at it.

"You're beautiful," Vanessa breathed before taking nearly my entire length into her mouth, pulling my foreskin back as she did.

"Oh—fuck!—good girl!" I moaned, her soft, wet mouth suckling me. It was heavenly! If her first performance sucking me off had been very good, this was straight up legendary. She wasn't kidding about how horny she was! I'd been caged for months at a time and knew full well how the denial could mess with your head, and this little sissy was already deep into it. She was a (n almost) possessed woman, using her tongue, lips, suction, and hands to get me as hard as I've ever been. "Oh...keep just doing that," I breathed as she ministered to me.

"Mmmmmmmm..." she hummed.

"You're doing a good job of making up for all your whining, you sexy bitch," I sighed, pulling my full tits out of my blouse and tweaking my nipples. A little pain always spiced up pleasure, whether I was being dominant or submissive.

"Thank you for letting me suck your cock, Mistress," she gasped before taking me all the way into her throat.

"Fuck! Good girl!" I cried as the impossible tightness of her throat massaged my glans. This was turning into one hell of a blowjob!

"MMM!" she groaned when she pulled enough of me out of her throat so that she could breathe. Then right back into her esophagus I went.

"Damn...I'm going to fill your horny, sissy mouth with cum," I groaned. Vanessa just swallowed over and over around me in her throat, her tongue working my length at the same time that she stroked me. "Oh, fuck, sexy...are you ready for me to cum in your mouth?"

After removing me from her throat, I got a, "Mmm-hmmm!" from Vanessa.

"Good, because...fuck—here it comes! Gonna cum in your mouth, sissy!" I cried. And then it was upon me. "Fuck! Fuck! Fuck!" I repeated as I pulsed and pulsed in Vanessa's mouth.

"MMMMMMM!" she moaned as I watched her Adam's apple (what little of it there was) as she swallowed each spurt of my issue. Ever since the nanobots took my body over, my sperm production was off the charts. Or at least the volume of cum I produced every time I had an orgasm.

"Shit, you have to stop!" I ordered as the final pleasure passed from my dick.

"Aaah...thank you, Mistress!" Vanessa gasped after releasing me. She was beautiful: tears in her eyes from stuffing my cock in her throat, she was flushed with arousal, and her chest was heaving.

"Thank you for an excellent blowjob, my sexy sissy," I praised. "Now stand up and show me your sissy clit."

"Yes, Mistress," she said and got to her feet, lifting the front of her sundress. I smirked.

"That's quite a lot of precum that you're leaking, isn't it, my sissy girl?"

She pouted. "Yes, Mistress. I'm so horny! Sucking your cock and swallowing your cum didn't make me any less turned on, either, Mistress."

"Good girl," I cooed. Another fun thing about the nanites in my bloodstream was that they reduced my refractory period to next to nothing. I was already getting hard again seeing how hard her denied clit was trying to get. There was the telltale bulge behind the ring of her cage, so I could see that the erectile tissue trapped inside her body was engorged. Then there was the line of precum dripping from the end of her cage that bounced as she clenched her PC muscles. Oh, I forgot, didn't I? Before I arrived, I had her stuff the biggest butt plug she could take into her ass and so it was rubbing on her prostate gland.

"Thank you, Mistress. I'm still super horny, though..." she added.

"Then go take that plug out of your sissy ass and get back here. By the time you're done I'll be ready for more," I ordered. Seriously, I was already getting ready for more. And it occurred to me that she'd had her cock in my ass for the fantastic fuck fest we'd had before I caged her, but I hadn't yet penetrated her other than her mouth. I wanted to plunder her ass in the worst way.

"Yes, Mistress!" she said and headed for the bathroom.

I gave my nipples a savage pinch and groaned a little, feeling my cock surge. "Don't forget the lube!" I added.

"I won't!" she called from the other room.

Within a minute or two she returned, lube in hand. "Good girl. If you haven't already lubed your sissy pussy then do it right now," I demanded.

"I'm all slick for you, Mistress. Do you want me to lube your gorgeous clit up?"

"That's the right answer. Yes. But suck my nipples while you lube me up," I directed.

"Yes, Mistress!" was her immediate answer. She popped the top open and put an impressive amount of the lube into her palm. Then, she knelt on the couch next to me and gave me a wonderful handjob, working the lube all over my length, while she sucked and nibbled on my nipples. By the time I told her to stop I was as hard as titanium.

"Now ride my cock, you sexy sissy slut," I ordered.

"Yes, Mistress!"

"After you take that dress off," I added. "I only want you in your bra and panties."

"Yes, Mistress," Vanessa replied, removing her dress and tossing it aside. I set that, well, aside, for later.

Then she pulled the thong from her ass crack to the side. It was a specially made one with a pouch for people born with a penis. Then she guided my throbbing erection into her ass. It turned out that even after being plugged for over an hour, her ass was supremely tight. "Uhnf!" she grunted as I stretched her open, the pain of being stretched clear on her face. But as she settled down on me, it melted into an expression of bliss.

Before long she had taken all of me inside her and her smooth balls were resting on my pelvis. "You're pretty big, too, Mistress," she moaned.

"I think it feels that way—Mmm!—because your sissy pussy is so tight," I breathed. Her muscle ring was gripping my hardness in the most delicious way. "It's not going to take long for you to set me off," I told her.

"This feels so much better than a dildo!" she moaned. "Thank you for taking my virginity, Mistress..."

"Thank you for giving it to me, sexy girl," I said after stopping her movement and looking her in the eyes. "It really means a lot to me that you let me be your first."

She gave me the softest of kisses. "I can't imagine anyone better to take me. You're my Mistress, after all," she said with a moan as she lifted her hips up, her tight muscle ring massaging my shaft.

"Fuck..." I groaned. "It feels so good to be inside you," I breathed.

"It feels sooo good to feel your beautiful cock inside me, Mistress!" she cried as she sank back down. I saw her cage twitch inside its satin thong covering, and another drop of her precum soaked the material. It felt even better as she re-impaled herself on my tool.

The sounds we made from that point on were just a series of moans, sighs, groans, and grunts as Vanessa picked up the pace at which she rode my stone-hard cock. She sounded just like a genetic girl with her high-pitched squeaks and sighs, and it was driving me crazy.

"You're gonna make me cum soon, you sexy little sissy," I moaned a few minutes later.

"I can't wait to feel you cum inside me, Mistress!" she enthused.

"Are you getting close to cumming?"

"I'm close, I think...it feels like it did when your fingers made me cum...please let me cum, Mistress!"

"Only if you cum before I do," I groaned. I was getting really close.

Seconds later Vanessa cried out, "Fuck! I'm gonna cum for you, Mistress!"

"Good girl, cum for me, you sexy sissy!" I groaned. Her ass gripped me like a vise, and it was too much. She kept flexing her muscles, massaging me. She'd stopped riding me, but I was still thrusting up into her incredibly tight hole and I erupted, grabbing her hips and slamming her down onto me over and over as I pulsed spurt after spurt of my cum into her.

"Fuck!" she cried out as I filled her with rope after rope of my cum. Like I mentioned, the nanobots help my body make large loads very quickly. My orgasm lasted almost fifteen seconds while she shook and moaned. I watched the small wet patch on the front of her panties grow a lot larger as her trapped cock pulsed, dribbling her own load out, soaking her panties.

She stopped once I finished thrusting into her and filling her, panting. "That was so intense, Mistress, thank you!" she told me.

I flexed inside her, making her squeak. "That's the only way you're having orgasms for a while, now, now that I know you can do it," I declared. "And you really made me cum hard," I continued, flexing again. She squeaked again and flexed around me in response.

"I've wanted to be able to cum this way for so long, thank you, Mistress."

"You're welcome, pretty girl. Is it different?"

"It's so different! Usually after I cum the normal way I'm done feeling girly. But since you just made me cum like a girl, I feel even more girly! And it's different because I want to do it again. I'm almost always done after I get off any other way."

"Good," I replied, flexing again and earning another adorable squeak from her. "Because I'm ready for more, too."

Her eyes went wide. "Really, Mistress?"

"Yes, really. I'm going to fuck you again," I told her as I lifted both of us up and put her on her back on the couch.

"Oh, wow," she moaned as I started plowing in and out of her ass a second time. I hadn't even pulled out or gone soft thanks to the nanites.

"Your asspussy is still so fucking tight," I grunted. Vanessa was just letting out a high, girly grunt every time I hilted myself in her, eyes closed and fully enjoying the fucking I was giving her, embracing the sissy bliss I knew she was feeling.

I leaned down so I was laying on top of her and put my head on the back of her head. "Suck on my tits while I fuck you, sissy slave," I demanded.

Her eyes opened slowly, and she answered, "Mmm, I'd love to, Mistress," and she did as I had instructed.

"Fuck, that feels soo good," I moaned as her mouth began suckling and nibbling on my left nipple. I got even harder and thrusted faster as she licked my big boobs. I didn't even have to tell her to, she would switch between my nipples every few seconds as I railed her.

She stopped shortly after starting, though. "Mistress...am I allowed to cum again?" she moaned.

"Cum for me, my sexy sissy bitch girl," I grunted.

"NnnnnnNNNG! Thank you, Mistress!" she yelped and then clamped down on me again. I looked down and saw her cage moving as I fucked a second sissygasm out of her.

"Yeah, that's a good sissy for me," I panted. "Having a sissygasm from her Mistress fucking her, good girl!"

"Oh, holy shit...please keep fucking me, Mistress!" she begged. "I think I'm gonna cum again if you keep pounding me!"

"Not if I cum first," I countered. But I could feel that I still had a little bit to go before I did. Fucking someone on a couch is high heels takes work! Within a few moments she was whining and grunting again as she suckled me again.

"Gonna cum again, Mistress! Please, can I?"

"Cum on my cock like a good sissy for me," I ordered. "I want to see you have another sissygasm."

"Oh, fuck, fuck, FUCK!" Vanessa wailed as I wrung another prostate orgasm out of her. Feeling her clamp down on me the third time did me in and I came inside her again.

"Aaaaahhhhh!" I moaned as I shot what I could feel was another big load inside her. I shot twelve or fifteen heavy spurts into her. My legs were tired by then, so I had to pull out. But I made sure her plug was nearby and slipped it back inside her before my loads of jizz could leak out. She moaned again when the plug's flared thick part stretched her wide again, then sighed when it settled inside her.

I flopped down on the couch next to Vanessa, panting just as much as she was. "You were a very good girl for me just now. Now take your panties off."

"Yes, Mistress," she replied and did so. "Why?"

"Because now you're going to lick the three loads of sissy cum you just dumped into them off and eat them."

"Mmm...that's sexy, Mistress. I've always enjoyed that when I'm in girl mode," she replied, complying with my direction.

"It is sexy, but now you're being rude," I said.

"I'm sorry! What am I doing wrong?"

I cocked an eyebrow. "You're not sharing."

Vanessa grinned. "You're right, that is rude, Mistress. Here," she replied, holding her panties out to me. They were absolutely drenched with her sissy loads. I sucked a little of her cum out and she tasted great.

"Much better, my sexy sissy," I told her. She preened a little.

"I guess I don't mind being caged as much now that you fucked three orgasms out of me, Mistress," Vanessa said after we finished eating her cum loads.

"They're sissygasms," I corrected. "That's the only way I want you to refer to you dribbling your sissy cum out of your cage."

"Now that you fucked three sissygasms out of me, Mistress," she corrected. "I like that term."

"You are my pretty sissy sex slave, aren't you?" I asked.

She bounced her eyebrows. "Oh, yes, Mistress. I love being your submissive sissy sex slave girl. It makes me feel so feminine for you to have total control over when I get to cum or not."

I twitched, already getting ready for more action. "And I love hearing you say that," I admitted. "How sore is your jaw?"

"My jaw is fine, Mistress. My ass is pretty stretched out, though."

"Then get over here and get my cock in your sissy mouth," I commanded.

"Yes, Mistress!" she said with enthusiasm. "I can't believe how fast you can recover."

"Is that a problem?" I inquired with a raised eyebrow. I was just about fully hard again at that point.