Thursday night I went over to Sounder’s house, with a couple of different goals in mind.
First, I wanted to do his full makeup. I finally had all the supplies I’d need, and I was looking forward to getting him all nice and pretty.
I got to his house and we spent a few minutes chatting, as we always do. I asked him if he was ready to become a pretty girl, and he responded by taking a long sip of his drink.
I told him not to worry, that I’d make him pretty enough that a man wouldn’t kick him out of bed, and he gave me this look that said, “Yeah, you’re not helping.”
It was great.
So we went upstairs to the bathroom, he sat down on a chair, and I got to work. I started with a super-white highlighter, because he’s pale, and went through all the contouring. Other than the contrast needing to be just a smidge darker, I was really happy with the way the contouring looked. It softened up his features and made his cheeks and jaw look way more feminine.
I could definitely work with that.
The eyebrows weren’t bad, either. I didn’t use enough glue (it’s been a long time since I’ve done MtF makeup) so it looked a little “messy,” but that’s an easy fix for next time. He keeps his eyebrows very well-groomed, as well, which helps. It’s just one of those things that I’m rusty on, and will need practice. Lots and lots and lots of practice.
The same with the liquid eyeliner. I always go for the pin-up look on myself, so winged eyeliner is something that I’m good at — on myself. I discovered that doing it on someone else is a whole different skill. And one I’ll need to practice.
But it was fun. He was sitting there, naked (because really, he just looks better naked), his little clit swollen and dripping.
It took awhile, but I finished his makeup, put his wig on, and his dress, and he just looked so cute. I couldn’t help it, I immediately bent him over and started playing with his hole.
“Do you want your pussy fucked, little girl?” I asked him, fingering him and playing with his prostate.
“Yes, I want to be fucked.”
He was so cute, and trying so hard not to say it. But he knows me better than that.
“What do you want?”
“Yes, I want my pussy fucked.”
Such a good girl.
I pulled out one of my dildos lubed it up and pushed it into him, kneeling between his legs as he lied on his stomach on the bed, moaning and squirming while I fucked him.
I fucked him for awhile, until it started to hurt, and then I put the dildo away. There was another goal I had in mind, something else I wanted to do to him.
I’d asked him once what felt good to him, if there were certain parts of his body that were sensitive, certain places that he loved being touched/licked/bitten, and he didn’t really have much of an answer. His nipples are crazy sensitive, but that’s the only real answer he had.
I got the impression that no one had really spent a lot of time exploring his body, really getting to know it. He confirmed that when I asked him, and I decided that needed to change.
I told him days previous that I could completely overwhelm and overstimulate him without causing pain at all, that I could make pleasure just as intense (if not more so) than pain.
He said he trusted me, but I wondered if he thought I was kidding or perhaps exaggerating. I was determined to show him just a hint of what I can do, what I’m capable of, and how relentless I can be.
So I took the dress and the wig off of him and had him lie down on his back, completely naked, and started running my fingers lightly over his body, watching him for reactions, to learn what felt good. It didn’t take long to learn that he liked when I trailed the tips of my fingers over the backs of his thighs, up towards his butt, and I had him turn to lie on his side so I could access that spot better.
Lying on my side behind him, I was in the perfect position to test out how he liked having his neck played with. I nibbled the back on his neck, and when he gasped and flinched, I knew I’d hit a spot that would be insanely fun to play with.
And really, he squirmed so nicely. I paid attention to his body language, his reactions, and his voice, and used that to find the spots that I knew would send chill after chill after chill down his spine.
Before long, it “started” to get overwhelming, and he couldn’t help himself anymore. He tried to squirm away from me, he tried to push his head to the side to keep me from reaching his neck, he tried turning his body, anything he could to get me to stop.
Silly boy, he knows better. I wrapped my arms around him, holding him against me, and kept going. Occasionally I would move to his ear, which wasn’t quite as sensitive, to give him a bit of a breather.
It wasn’t long after that I began to notice a change in his voice. Normally, his tone doesn’t change much when I’m using him. He’s always been very vocal, but his voice doesn’t usually get higher, like I’ve seen with many submissive men.
That started to change, the longer I played with his neck. His voice got higher, and I heard the first adorable little whimpers and whines out of him.
Which, of course, did nothing but fuel my desire and make me want to do it even longer.
He was rock-hard, harder than I’d ever seen him before, and for much, much longer than I’d seen him before. I would reach back down to caress his thighs and butt, and he’d gasp and writhe. I’d reach down and grip his dick, and he’d automatically start thrusting, grinding and pumping into my hand. I’m not even sure it was a conscious decision, I think it was more a reaction to being touched there at that point.
The longer I went on, the more he tried to squirm away. At one point, he’d turned all the way over, so he was lying on his stomach, his head almost hanging off the edge of the bed. I was lying beside him, and threw my leg over him, straddling him and using my weight to pin him down.
He’s a strong boy. He would push up against the bed, basically doing push-ups and lifting us both. I grabbed the edge of the bed, pulling myself down as he was pushing up, but goddamn he is strong.
At one point he pushed up onto his knees, lifting my entire body completely off the bed. I laughed.
“Do you really think that’s going to make me stop?” I asked.
He didn’t answer — I don’t think he could, but soon he lied back on his stomach, still gasping, moaning, and whimpering.
I have no idea how long I’d been doing it when I finally stopped. I’ll have to ask if he knows. I’m guessing it had to be at least half an hour. Probably a lot longer.
I finally stopped, lifting myself off of him and lying beside him, running my fingers gently up and down his back while he recovered. For a few moments, he just lied there panting, still writhing just a little.
Finally, he took a deep breath and sighed. I grinned. “Did you think I was kidding about overwhelming you without hurting you?” I asked as he turned over.
“I didn’t think you were kidding, but I didn’t expect that.”
When he turned over to lie on his back, I grinned when I saw that he was still rock-hard.
It had been a while since I’d let him cum, so I told him that I wanted to watch him jerk off. He obediently began stroking himself while I watched, and when he came, he made quite a mess. I was planning on making him eat it (he’s never tasted his cum, or even his precum, before), but took pity on him, and decided to give him something to look forward to next time. I’d already put the poor boy through enough.
I let him clean himself up and get dressed, and we went downstairs. I was stunned when I looked at the clock and saw that it was 11:30. He had to work the next day, so I grabbed my things, he walked me to my car, and I left.
It was a lot of fun. And I’m still not done exploring his body and finding all the little spots that feel good and can help me overwhelm him. Next time, I think I’m going to do it again, but I’m going to fuck him while I do it.