Vanessa

I raised an eyebrow and smiled. "Would you like me to return the favor?"

A conflicted look took over her face. "I...um...kind of. I try to just get off as a girl in girl mode," she explained. "Most of the time I don't even touch it."

"I see. How do you normally take care of it?"

"I've tried to have a sissygasm through anal a lot but I can never seem to quite get there, so I don't, really. It feels really good but I can never quite get there," she answered, looking crestfallen.

I kissed her again and took her into my arms. "I'd like to help with that, too," I soothed. I was going to be ready for more action soon, I could tell, the nanites giving me a far better refractory period than I was capable of before. "Would you want to show me what you do, or is that too much?"

"If you don't mind, I think I would like that," Vanessa said. "I'll be back in a few minutes."

"I'll ready, waiting, and eager, honey."

She got to her feet and sashayed off, I assumed to the bathroom to make sure that she was clean inside. I was starting to get hard again just thinking about what I was going to see this sexy sissy do in front of me. By the time Vanessa returned a few minutes later, clearly still just as hard as she was when she left the room, I was pretty much fully erect. She sat down across from me on the floor after laying down a towel.

"I'm a little nervous," she chuckled as she pulled her thong aside, revealing a perfect pink hole.

"I am a little, too, actually. I just want to help you feel good, though, just remember that, cutie," I assured her, making sure to always address her as female and trying to remind her that she was attractive to me.

"Thank you," she said with a cute, bashful smile.

"Thank you for sharing yourself with me," I replied. Would you mind explaining what you do? And please, if I can help with any of this, just say so."

"I usually start with my fingers just to loosen myself up," she explained, getting a generous amount of lube on her fingertips. Then she began to work first one, then two and soon three fingers into her ass. She closed her eyes as she opened herself up for me, laying on her side. "Sometimes I can find my p-spot."

"I've had trouble reaching mine on my own in the past. Do you want me to try, honey?"

"If you don't mind, I wouldn't mind if you wanted to," she breathed, withdrawing her fingers.

"Of course," I told her, unbuttoning my blouse, removing my skirt, and getting rid of my bra. "Just need to get a little more comfortable," I explained before giving her a long, sensuous kiss.

While I got some lube on my fingers, she latched onto my left nipple, suckling with just the right amount of pressure. "Mmmmmm," I murmured as I felt jolts of pleasure shoot directly to my cock. Which, of course, just made me harder.

She gave a cute little yelp as I worked a couple of fingers inside her. Within a moment I had found her prostate and was rubbing back and forth on the gland. She groaned and squirmed, gasping as she broke contact with my diamond-hard nipple. Which wasn't the only stiff part of my anatomy. "Holy fuck," she said with a soft cry of pleasure. "It's never felt this good before!" Then Vanessa went back to suckling.

"Mmmmm...I'm glad I can make you feel good," I sighed. Little bolts of pleasure were shooting directly from my nipple to my dick, which was already ready for more. "I hope I can make you come," I added.

"If you keep that up just like that I think I'm going to," she breathed. "It almost feels like I have to pee."

"Good! Let me...ohhhh...keep going and I think you'll have your first sissygasm, sexy."

A few minutes later as my arm and wrist were starting to get tired, she cried out, "Oh...oh, fuck. Oh God, I think you're gonna make me come!"

I kissed her hard and started stroking myself. Before long, her legs were twitching and her hips had begun to buck in time with my hand's thrusts. "NNNnnnnggghhh--FUUUUUUuuuucckkkk..." she groaned, her hardness jerking as it spurted. Fount after fount of thick, white cum issued forth, soon coating her belly in a warm, salty mess.

"Ohhhhhh, holy shiiiiiit..." she groaned as I slowed my motions. "That was fucking incredible!" she gasped before raising her head to mine and kissing me with a surprising amount of passion. She was breathing hard.

I grinned as the kiss broke. "It sounds like the pleasure was all yours," I smirked. "Or was it?" I asked, glancing down at myself. I was immensely hard again.

She seemed almost drunk as she sighed, "I'd love for you to fuck me, but I need a few minutes, Jess..." before dissolving into a fit of giggles.

I laughed. "Well! It looks like that experiment was a success!"

"Holy shit, that orgasm was so good I'd be happy if I died right now," she breathed.

"Just wait until I have my cock inside you," I whispered into her ear. "You're not the first gurl I've fucked into a sissygasm, and," I paused for effect. "I'm pretty good at it."

Vanessa bit her lip. "Please just give me some time to recover and I can't wait..." she trailed off, whispering something I couldn't quite make out.

"You can't wait...what?"

A barely audible whisper. "Mistress..."

I felt a feral grin spread across my face as my erection, which had been fading, returned with full force. And backup.

She dozed off for a while. I took the time to fix my makeup and to clean myself out--you never know--and also to mentally prepare myself for where I thought this was going. I made a note on my phone to order something for her, grinning at the possibilities, and soon enough she was stirring.

When she awoke, she was still too spent to play anymore but we made plans to meet up again very soon. Just as soon as I got home, I got online and ordered something that, after she referred to me as "Mistress," I thought she would probably be at least open to trying...