Jessica Ch. 03 - Vanessa Pt. 02

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!

I knocked on Vanessa's door again, less apprehensive than the last time that I had. In the intervening time we had talked quite a bit about clothing, how she could carry herself in a more feminine way, makeup tips, kinks, turn-ons, you name it. We had quickly become friends with a D/s undercurrent informing the dynamic. That, of course, explained the surprise for her that I had in my purse.

She opened the door and all I saw was a very pretty young woman standing there. She had very clearly taken a lot of the makeup tips and fashion advice to heart: she looked great. She was wearing white stockings or pantyhose (I couldn't tell yet at that point) and a pretty yellow sundress with light but very feminine makeup. A pair of low white heels completed her ensemble.

"Jess! Please come in," she said. Between the texts, IMs, DMs, and other messages we had exchanged in the last few weeks, she had an awful lot more confidence. She moved with a grace that I suspected was there all along but she'd been too nervous or self-conscious to feel ready to show.

I kissed her once the door was closed. "You look great!" I said as I beamed at her. I wasn't lying, either.

Little Miss Bashful was still around, and she blushed and looked down when she replied, "Thank you," in a very small voice. "You're gorgeous as always," she added.

I pulled her chin up so she could see my grinning face and gave her a quick peck. "Flattery will get you everywhere." I was pleased that she'd commented on how I looked. I had put enough effort into it, dammit! My hair was tied back in a relatively severe ponytail, I had done my makeup in a fairly dark-toned and somewhat smoky way, and I had on a black lace choker. Not quite goth, but I was going for a certain kind of dominant look. That was accentuated by the black satin blouse that covered my prodigious tits that were ensconced in a black lace bra. Below that I had on a black satin gaff that matched my blouse under a leather pencil skirt, black lace-topped stockings held up by a black satin garter belt, and a pair of black patent leather pumps with a five-inch stiletto heel completed the look.

"So, I've been thinking," I began as we sat after she'd offered and I had accepted her offer of more of that exquisite iced tea.

After a few moments of silence, she asked, "Um...what about?"

"About how you've been referring to me as Mistress."

There was another pregnant pause. I was doing this on purpose, since she would need to understand what calling me that would truly mean if she decided to continue down this path. So I figured making her a little uncomfortable and sort of forcing her to come out with it would help make that happen.

"...Um...what about it?"

"Most people who refer to me with that moniker have already agreed to quite a lot of terms," I answered in an arch tone, then said nothing more. She was going to have to work for this. Was she ever!

"So...like, what--what kind of terms?"

I paused for effect. Then, "Well, it's different for everyone, of course. But there are some themes that are always there."

I could tell she was uncomfortable but I was willing to put her through that since it would be a good indicator of how she'd take what I would throw at her if she could handle this. The submissive in a D/s relationship often feels to me like the stronger in the relationship. They accept everything and agree to do everything they and their Dom/me demand without question, giving themselves over entirely to the dominant member or members of the relationship.

"Submission. Obedience. Unquestioning obedience once limits are agreed upon. Discomfort, whether physical or being exposed to new experiences. Acceptance of punishment when they disobey or misbehave, and even appreciation and giving thanks for being shown the error of their ways. Do I need to go on?"

"I, um...I don't think so. Why are you being so...cold?"

I gave her a warm smile. "Vanessa, I'm not being cold. This is the teaser trailer. Just a tiny look into what you'll see. I'm trying to be as honest as I can and make sure you know damn well exactly what you think you're agreeing to before you go tossing off a term like, 'Mistress,' without really knowing what it means when used to address me. I don't enter into a Dom/sub relationship with someone lightly. It's one of the most intimate ways people can interact with each other, in my mind. You're not just allowing someone access to your body, and sometimes your mind and your will, no. You're giving them far much more: you're giving up control over some or all of those things. Completely. There's no saying, 'Oh, well, that's not what I really meant,' or 'But that's not what I said!' or anything like that. 'Yes, Mistress,' to me, is complete subversion of what you want to what I want.

"Do you really understand what you're asking of me? You're asking for me to not only make decisions on your behalf, sexually, physically, in a lot of ways mentally, but also to be responsible for those decisions and any ramifications that result from those decisions.

"The life of a submissive is not an easy one. In fact, a lot of the time, it's pretty difficult. I will always respect boundaries and above all any safe words, but outside of those guardrails, I make the rules, and," I said, leaning forward and lowering my voice, intentionally crossing my legs so my the leather in my skirt would creak for effect, "I enforce them. Transgressions are not looked upon kindly.

"Now," I continued, sitting back in a theatrical way, "if you're willing to continue this conversation, I am very much open to that. You're a beautiful young person and if you want to submit to me, I will not lie and tell you that it doesn't turn me on to have a girly person submit to my will. But I refuse to do that without both of us knowing, fully, what this arrangement will entail."

Yeah, yeah, I know. That was pretty wordy. But I did it for effect, because she'd been tossing off "Mistress this," and "Mistress, that," like she was throwing a ticker tape parade. That shit had to stop right then and there.

Vanessa was silent for about thirty seconds. When she did speak, it was that same demure but "I know what the fuck I want and I'm going after it!" voice she'd used when she had asked to go down on me the first time we met.

"It's not just because you're really sexy, or that you played my body like a violin the first time we met, or that you have this sensuality coming out of your pores that I called you that," she explained. "That's not it at all. I have always felt safe and comfortable when someone else is making the decisions." Then she fell silent.

"I can tell there's more," I interjected.

"Um--yes. It turns me on to give control up."

"But are you willing to live with the minute-to-minute consequences of what that could mean?"

She swallowed hard. And shifted a little in her seat, and I thought I caught a glimpse of her (very!) large package and it seemed to be at full mast. She swallowed again, then just about whispered, "Just hearing you talk to me that way, so dominant, has me sooo turned on right now."

Okay, you want to be a sub? I am more than happy to keep playing the Domme here.

"Show me." It wasn't a question, it was a demand.

"...what?"

"I said I want you to show me. Now."

God, I was straining in my gaff! And my nipples were hard as bullets.

"Um, okay," she said and shuffled to her feet, staring at the floor.

"Okay, what?" I demanded.

"Oh! I--um, I meant--I mean, yes, Mistress." Her face was flushed and it was driving me crazy. You could have cuttension in the room with a butter knife.

"Then show me."

Without another word, already on her feet, she did. She pulled the front of her dress up above her waist and there was the outline of her titanic member outlined in her bikini panties. She had it off to the side to contain it, which couldn't have been very comfortable, but she wasn't lying: there was a wet spot from her precum the size of a silver dollar around the tip of her very impressive shaft.

I got up and walked over to her, making sure to put one of my heeled feet in front of the other with every step and making sure there was more sway in my (I'll admit, generous, thanks to the nanites) hips for the few steps it took.

I took her face into my hands with supreme gentleness and kissed her in the softest way that I could. And I said, as I looked deeply into her eyes, "Good girl."

She whimpered. I had suspected that she was submissive in nature, at least in her girly mode, but that one sound spelled it out for me: this girl was a natural sub. Not a dominant bone in her body.

I smiled. "I see that you were telling the truth," I declared in a quiet, assertive way.

The honesty in her eyes when she answered me took me aback a little. "I would never lie to my Mistress." I even heard the capital letter.

I was actually touched. "I think you may be the most honest about this than anyone I've had a conversation like this with. Thank you for that. It's such a pain in the ass when I have to go around and around to get to the truth."

She smiled, and at that, we got onto the real conversation. Her limits, her desires, things she was sort of curious about, things she'd never heard about but thought they sounded fascinating (outside of the little surprise waiting for her in my purse), and anything in between. We also, of course, covered my expectations, rules, and the like.

"So you are okay with all of that?" I asked.

Vanessa nodded and answered, "I'm so excited I can't even take it. Yes. Yes!" Now she wasn't blushing but her skin was definitely flushed.

"Okay," I replied. "Now is the part when I tell you that I'm going to make you wait for 72 hours to make that decision."

She was crestfallen and I knew she would be before I had walked in the door. "Safe and consensual are crucial to a Dom/sub relationship, but the 'sane' part is also critical. I can tell you're so worked up sexually that you're not thinking straight. You need to enter into something like this when you are. So take three days and think about it, then let me know if you still want to. I have an idea how that will go but I will not, as a Domme, allow you to rush into being my submissive. You need to know in your heart and your soul that this is really what you want."

"I...yeah, that makes sense. I guess I'm just getting carried away. I have to wash these panties I'm so turned on," she admitted in a much lower voice, so low I barely caught it.

"So take them off now and wash them," I tossed off casually.

"What?"

"Vanessa. I said I wouldn't take you as a submissive until you have had time to think about it. I never said we couldn't fuck."

The profanity took her off guard which was entirely the point. "Uh...what?"

"If you're turned on then you'd like to have sex, right?"

"Well, yeah, I guess."

"Do you or don't you?" My directness was keeping her off-balance, just where I wanted her to be.

"I--I do," she confirmed.

"Then take those pretty panties off, wash them now if you have to, and we can have sex as long as you want it with me," I declared.

A small smile twitched the corner of her lips. "What if...what if I keep them on and we do?"

I smiled as warmly as I could. "If that's what you want then that's fine, too." My gaff was uncomfortable at this point. I smirked internally "Just let me know what you want."

"I...I want you to fuck me," she said in her cute, bashful way.

"That's what I want, too," I told her, although I would've been happy to take her monster if she'd been of the mind to be the top. "Are you sure you don't want to fuck me instead?" I asked. "It might be the only opportunity you get for some time if you decide to take the plunge."

"I, um...I...are you sure?"

"I'm positive. I'm a switch in every sense of the word, Domme or sub, top or bottom."

"I don't normally like to, uh, be on top," she almost stammered, "but if you would like it I think I'd love to try it."

"I made sure I was clean just in case things went this way," I told her with a smile as I kissed her softly. "I've never seen your bedroom, would you like to show me?"

She bit her lip and I was at that point very much looking forward to taking this gaff off. It was doing a great job of hiding that I wasn't 100% biologically female but was really uncomfortable. The good news is that it was looking like I would get to take it off very soon.

Taking my hand tentatively, Vanessa said, "Follow me?"

"Lead the way," I said with my brightest smile. She led me into her bedroom, which was a fairly masculine affair.

"Sorry about how, um...dude it is."

"It's not a problem. I started out as a man, too, remember?" I reassured her. "Besides, you're not living full-time as a woman, are you?"

She blushed a lot at that. "No, this is just fun to do sometimes."

I kissed her again, this time using my tongue to probe her lips enough to get her to open them up. Our tongues danced for a second or two then the kiss broke. "Then let's have some fun," I prompted, lifting the hem of her sundress.

"I can't believe this is happening," she breathed between kisses as I slipped my blouse off.

"I wasn't expecting to be the bottom on this, but it's a welcome surprise," I replied. "With the heat you're packing I'm sure I'll enjoy it!"

Vanessa blushed again, moving to cover her turgid member under her sexy panties. "It's not that great."

I stopped her and got her to look right into my eyes. "Vanessa, that is one of the biggest things, if not the biggest, I've ever seen in person. I'm fortunate that you're willing to share it with me, and especially if you want to use it to fill me up," I explained, this time biting my own lower lip. I had to admit the thought of her stuffing that massive dick into my ass had me leaking some precum.

"Um...thank you?" she laughed. "It's not like I had a say in the matter."

"I know, neither did I," I said after a brief kiss. "But it's gonna make me feel really good."

"I hope so," she whispered as my skirt slid down to the floor and I stepped out of it. "Wait," she said when she saw my gaff that looked just like a sexy pair of black panties. "Where is it?"

I chuckled. "This, my dear, is a gaff. It's one of the most concealing I could find on the market," I explained as I slipped it down from my waist and allowed my very turgid erection to be free. "I'm surprised you've never heard of them, but I have a few and I'd be happy to let you borrow one if you want."

She smiled and said, "There she is. And thank you for the offer. I've never gone out in public so I never had a need to learn about them. It's amazing how well it keeps your...um...how do you want me to refer to it?"

"My cock?" I asked with a smirk as I gave it a few strokes. "Cock, dick, I'm not too particular about it. I do refer to it as my 'womanhood' sometimes, though."

"Thanks...it's amazing how well it keeps your womanhood hidden, even when you get excited," she remarked, licking her lips without realizing she was doing it.

I smiled. "Do you want to lay down on the bed?"

"Only if it's next to you," she replied, her eyes downcast.

"I love it," I said as I unclipped and removed my bra.

We both laid on the bed, her in her panties and garter belt holding her stockings up, me completely nude, and embraced as we began kissing. Our kisses were much deeper than they had been the first time we'd gotten together, and I was impressed at her ability to hold her own, since I was still in domme mode and was taking control despite my willingness to bottom for her. Vanessa rolled with the punches but matched what I was doing. I was rock hard.

"I need you in my mouth," she breathed as she kissed her way down to my tits.

I gasped as she nibbled on my right nipple. "Then I want you in mine, too."

"Mmmm!" she exclaimed as we rearranged our bodies. She was on top of me as she straddled my head, so I pulled her precum-moistened panties to the side and took her thick shaft into my mouth. She groaned as mine entered hers. This time wasn't as sensual and was much more sexual, but no less skillful. I groaned around the three or four inches of her I managed to stuff into my mouth when she began swirling her tongue at the same time she bobbed her head and slid my foreskin up and down.

Her big clit was as hard as granite as I made love to it with my mouth, and I could taste her precum the same way I was sure she could taste mine. "If you're going to fuck me I want you inside me now," I said.

Vanessa said, "I can't wait to fuck you, Mistress."

I smiled and spread my legs for her. We got ourselves properly lubricated and she knelt between my splayed legs and rubbed the head of her impressive fuckstick on my entrance. "You're really big, so go slow, baby," I asked.

"I will, Mistress," she replied as her crown breached my entrance.

I gasped. She was fucking HUGE! "Wait!" I gasped, my hand on her lower abdomen. I wasn't some blushing virgin. I'd had some pretty big things stuffed in my ass before for sure, but her monster was stretching me quite a bit.

After a minute or so the discomfort subsided and I had my breath back. Her hardness hadn't subsided a whit, which felt very flattering.

She suckled on my left nipple as I got used to her size before I sighed, "Go ahead and push in, baby."

She moaned and thrust into me a little more, making me yelp at how good her intrusion into my ass felt. "You're so tight..." she whispered.

I smiled and kissed her. "I'm not that tight, your sissy clit is enormous."

"Thank you for letting me inside you, Mistress," she sursurrated before sinking the rest of her length inside me.

I gasped when she bottomed out. "So fucking big!"

Vanessa giggled and said, "Thank you for letting me take you, Mistress."

"Thank you for being willing to be my girl," I replied with a smile, and kissed her. Her shaft, simply by virtue of its size, was rubbing against my prostate. I felt myself start leaking precum the moment she started rocking her hips. I was as hard as I've ever been. "Yeah, start slow. That's good, my good girl," I cooed. "Suck on my nipples while you fuck me," I ordered, my dominant demeanor returning.

"Yes, Mistress!" she moaned and took my pebble of a nipple into her mouth. I couldn't help but moan.

"Yeah...be my good girl and fuck me," I urged as her strokes became longer and harder. "Make me cum with that gigantic sissy clit of yours."

"I want to make you cum," she moaned. "Is this going to make you cum, Mistress?"

"Oh, fuck, yeah," I moaned as she resumed suckling me. "Just keep going and you're going to make me cum so hard!"

She groaned and picked up the pace a little. By now any pain or discomfort had evaporated and I reveled in how good it felt to have her thick, long hardness sliding in and out of me. I had had a few p-spot orgasms in the past and could already feel one coming on.

"Yeah...fuck me," I encouraged her. "Make me cum from servicing me, sissy girl."

"Oh, fuck, I want to make you cum so bad, Mistress!"

"Then keep fucking me just like this and keep sucking on my nipples," I ordered.

Before long I could feel my toes starting to curl. I realized my legs were wrapped around her waist, imploring her to keep thrusting into me. "Fuck...Vanessa, you're going to make me cum..."

"Please cum from me being inside you, Mistress..."

Then it hit. I cried out, feeling my hard dick pulse over and over as the ecstasy rolled over me. Vanessa didn't change anything so her thick shaft kept milking spurt after spurt of my girlcum out of me until there was a small pool on my abdomen, and, I became aware, a few drops on my tits.