Damselfly

A profile of an older straight guy messaged me. The first thing you read on his profile is that he likes those who present fem, and that he loved trans guys in particular. I know I shouldn't get excited by that but I do. That along with the fem thing made me ask outright if he was sure he was interested in me because my body is definitely not fem. Dressing fem only highlights how not fem I am.

He was definitely sure. Later when I met him in person I asked what he liked so much about trans guys. At this point he was already feeling up my cunt. He told me its because we have soaking wet pussies... I'm definitely known for that. While T can dry us out some of us are exactly what he described. Hell, someone can probably drill me as my juices funnel into a jar to be kept as lube or something. I've leaked through denim before.

He could have been dodging the question but seeing as how he enjoyed me grinding on his hand towards the end, I don't think he was.

While feeling up my cunt he figured out how easily I cum with my dick being played with. After he realized this, he didn't stop playing with it. The first five orgasms were good but after I got more and more overstimulated.

I am a sub that likes fucking compared to masturbating because I can be pushed beyond what I'm completely comfortable with. The second I put my pussy in the hands of a dom, they have the most possession over it. If they want to keep rubbing me as my moans get deeper and I start squirming more, until I'm shooting blanks, the last thing I want to do is take that from them.

So even though I was getting overwhelmed I didn't tell him to stop. He would thrust into me for a little bit before going back to my dick, moaning as he felt me contract during orgasm, and starting thrusting again.

After a bit of that pattern I felt something poking at my ass and told him he could stick a finger in there. He wanted to stick his dick up there and asked if he could. I love anal but I'm also really tight, so I said maybe but we may stop as soon as we start. He asked if he could take the condom off if we did anal and while I didn't verbally consent I still presented myself to him on the edge of the bed.

I felt him trying to stick it in my ass and realizing that I was too tight. I felt him stick it back in my pussy, without asking.

By this point the main thing I felt was pleasure from being penetrated again. My head was so fuzzy all I wanted was the feeling of dick in my wet cunt. After a few seconds I remembered he didn't have a condom, and asked myself "does it really matter? Just let it happen" from how much I was enjoying the moment. I was able to get my rational brain to pick up and ask him if he put the condom back on, and he told me he didn't but won't cum inside.

I know that precum can make me pregnant, I know stds exist, but I was finally getting consistent thrusting and didn't want it to stop. I reminded myself that I felt a cock ring that was probably being used to keep from orgasm, that he won't cum inside me, even though he's a stranger. Every part of me wanted his dick inside me and by then rationality couldn't win me over.

After a bit we changed back to our prior position where he played with my poor overstimulated dick before fucking my hole again. My voice got lower as I got more overstimulated and he grabbed by leg to hold me still as I continued to cum on his cock.

I eventually told him I was still nervous and wanted the condom back on. He insisted he won't cum inside again and, yes, by this point I knew I was in gray consent territory, and gray consent should default to no consent. After I urged a little more he pulled out and started jerking himself off.

I got closer to him to get into a cuddle position before he reached over my back and continued to finger my pussy and dick. I was exhausted but wanted to let him play with me as much as possible more than anything, so I spread my legs wider to let him.

He used my wetness as lube on his dick, he did this when we first lay down to get himself hard as well. Sticking his fingers into my cunt to feel my wetness on his dick.

As he started getting close he couldn't focus as much on me and, despite going for at least 30 mins, despite being exhausted, I instinctively starting humping his leg. He told me how hot my wetness was before cumming.

After which I cuddled into him to rest. I could feel my upper body twitch a bit from how much I've been thrown through the ringer.

~~~~~~~~~

When you sneak into the royal chambers that night, you weren’t expecting the princess to be passed out. Like, slumped over on her bed, only about halfway into her nightdress. Her position—knees on the floor, bent over at the waist, face pressed into the mattress— made you choke. No one else could see her like this. You rushed over, hands hovering for a moment, unsure of what to do.

You typically just come in to watch, gather details for your fantasies. You’ve never really touched her before—never given yourself permission. You know you’re too indulgent, too likely to give in to temptation. But there she was, with ruddy cheeks and heavy limbs, clearly passed out from drink. You could smell the wine on her breath, vestiges of the night’s festivities. She wasn’t one to indulge on wine, so there must have been some reason she did not want to be sober.

“Overdid it a little, didn’t you Princess?” You breathe as her eyelids flutter and her limbs twitch. She does not awake, not even as you grip her firmly under the arms and pull her to her feet. Your cock is pressed against her back and you groan hoarsely, loud in her ear, but still she does not wake.

It’s not like you planned for her skirts to ride up while you tried to put her to rights. It just happened. And she’s not wearing anything underneath. You can smell her wetness and before you think to stop yourself, you have her on her back, skirts bunched at her hips and your hands holding her knees apart. The moment is lost as you stare at her pussy, just imagining how hot it must be inside. You couldn’t do that of course. You had to think of her virtue or honor or something like that. It was hard to think, but you had enough wits about you to think better of following through on that particular thought. No, you couldn’t even touch her pussy. It would be too tempting to bury your cock inside and breed—

With a rough inhale, you drop her knees too quickly. Unnerved, you glance up to her face—but she still sleeps. You release your breath, almost amused at her persistent unconsciousness. You run your fingers daringly along her legs and up to her thighs, gently squeezing her soft flesh to see if she would wake.

She didn’t.

Maybe if you just. Maybe if you just use a different hole, that would be fine. Right? Like, if you just put it in her mouth or her ass or something, that wouldn’t be stealing her virtue. And she’s not even awake right now, so no harm done. Just once, you could see what it felt like and like, not come inside, and that would be fine.

You hadn’t really even convinced yourself entirely before you were turning her over onto her stomach, repositioning her head so she could breathe properly. She’s so out of it, she barely stirs. You push her skirts out of the way again, petting her hair tenderly. The poor thing must really have been drinking a lot. Even as you frowned in pity, you realized this meant you could go about this properly. With a squeeze of her ass cheek, you left the bed and knelt to pull a small box from underneath it. This box had featured in a number of your fantasies, as it was something you had seen her use before. You knew it held at least a toy and hoped you might find—

Yes, a bottle of lubricant. And underneath it a single condom. You glanced around the room, almost suspicious of your luck. This was good. This was very good. You could replace the condom, surely. It would be better after all if you used one. For her virtue, you reasoned.

Finding the lube solidified the reality that you were really were going to put your cock in her ass. Before it was a passing desire, a ridiculously hot fantasy. Before you could convince yourself you wouldn’t really do it, not with a dry cock in a virgin asshole. But now… now you were prodding her tight hole with a lubed up finger, surprising yourself when it slipped in to the first knuckle.

It was hot inside and so fucking tight, it made you lightheaded. You let your mind race as you gently coaxed your finger deeper, wiggling it to help her loosen up. Your other hand palmed your dick through your clothes, mentally comparing it to the tightness of her ass. She was taking your finger well, thanks to the drink relaxing her body. You added a second finger eagerly, pressing a soft moan out of her. You stilled, trying not to lose yourself in the feeling, unsure if the sound meant she was waking. But she did not stir. You scissored your fingers gently, listening. She moaned breathily, almost a sigh.

With those sweet sounds you could almost convince yourself that she was enjoying it, the dirty girl. Heat pulsed low in your stomach as you fingered her tight asshole, listening to her occasional grunts and sighs. You rolled the condom on your dick with your free hand, messily spreading some lube on it while you watched your fingers disappear inside her. She let out little puffs of air and her face seemed even more flushed.

At last you pulled your fingers free with a wet sound and a groan, stroking your cock before pressing the tip to her asshole. It gave way slowly as you sank into her tight, heat. God, it was dizzying. The head of your cock disappeared as her asshole took you in, spreading sweetly for you. Her body stayed limp despite the intrusion, almost as if it were used to taking cock. The thought had you rocking into her, taking permission from her pliant body. Surely she was enjoying it, you reasoned, and that meant it was okay to go a little faster. To fuck a little deeper.

The world narrowed to the space you were fucking. The world consisted only of you fucking her ass. Her moans were more frequent now, pressed out of her as you thrust with quiet insistence. The wetness between you increases, easing the slide of your dick in her ass. With your cock still inside her, you rock her onto her side and lift her right leg. Her cunt is slick. If you didn’t know better, you would say the Princess was getting wet from having her ass fucked in her sleep.

The thought had you reaching down to test it before you could think better of it. Hooking her knee over your shoulder, you freed your hands to inspect her. The Princess was wet from being fucked in the ass. In fact, a trail of cum had dribbled down onto the mattress. The feeling of the slick under your fingers chased away what little self control you were clinging to. Your fingers pressed into her pussy before you could remember the rules you set yourself before starting. You weren’t fucking her pussy, so it was okay, you reasoned. You were just helping her feel good while she made you feel so good. Yes, that was it. You toy with her clit as well for good measure before sliding two fingers back inside her slick heat. It wasn’t long before you were fingering her in time with your thrusts, curling into her g-spot to make her tighten around your cock. When her pussy tightened like a vice around your fingers, you buried your cock deep in her ass, unloading inside without a single thought beyond her holes.

A breathless moment passed with your cock twitching and pulsing. Part of your brain was grateful for the condom, considering you hadn’t meant to come inside. Or maybe you had meant to from the moment you saw the condom and knew you could get away with it. As you come down from the high, you realize you are murmuring apologies to the Princess while you continue to finger her cunt.

“I’m sorry Princess, you just felt so good inside. I couldn’t help it. Your body is just so warm and wet, you see? I couldn’t help myself. Not when your cunt tightened like that, you know I couldn’t resist.”

You’re still hard when you ease yourself out of her ass and remove the condom one handed. The other stayed where it was, as if you were unable to remove your fingers. It’s just so wet, she must have really enjoyed having her ass fucked by you.

“You’ll forgive me right, Princess? Since I made you feel so good…”

You’re fucking her hard now with two fingers, intoxicated by the sounds her body Is making. Addicted to the little moans and sighs she makes in her sleep.

You glanced around the room again, all too aware of how close your bare cock was to her dripping holes. It’s painfully hard, straining forward and leaking. Cautiously, you pushed your hips forward until your brushed the shaft against her. You moaned, rocking forward to spread her pussy lips apart with your length. Just rubbing against it, you told yourself. Just getting your dick wet so you can jerk one off and come one more time. Just one more time before you go.

It's the perfect plan, you tell yourself. She is soaked and you need something to wet your dick with… you wouldn’t want it to be too dry. It needs to be good and wet so you can jerk it hard and swift and give her your cum. Respectfully, of course. You turn her completely on her back, sliding your cock repeatedly against her wetness. It’s like a compliment to come on her tits or her face or her ass. It’s a show of devotion that you can’t put your dick away. You just need to get it wet and then you can come. Using her slit just made the most sense, right? With your dick so close and with all that slickness available.

“I’m just going to put the tip in, Princess.” You tell her, making up your mind suddenly. There wasn’t another condom, but that was alright. You weren’t actually going to fuck it, you were just going to put the head in and see how warm it was. See if her pussy likes it as much as her ass did.

There’s no resistance and you slide halfway in without meaning to, choking on your own breath at the dizzying quickness. Unlike her tight asshole, her cunt was actually made for fucking and welcomed a cock inside. You had pushed further than you meant to—as you told yourself, you had only wanted to press the tip in. You would have pulled out after a few moments. After all, this is the Princess. You’re not supposed to be fucking her royal cunt, you’re not even supposed to look at her.

But, you tell yourself, you’re already inside. You can probably get away with fucking it a little bit. You won’t come inside, of course, that’s not allowed. But-- you begin thrusting shallowly—you can always just fuck it a little bit.

“I’m sorry Princess, I’m just going to keep my cock warm just for a moment,” you say, even as you push a little deeper and listen for her sigh of pleasure. “Don’t you worry, I won’t be long.”

She takes cock well, your little Princess. Your length disappears inside and you release your own moan, barely suppressing your own pleasure any more. She’s not going to wake up, clearly. Her body is enjoying the activities, even if she is unaware of them. There’s nothing wrong with taking your pleasure too.

You huff out a chuckle as you settle in with deep, firm thrusts. Her cunt draws you in, squeezing and milking your length like it was meant for this. “And it is, isn’t it, Princess? You’ve got a lovely cunt made for fucking.

“You don’t mind that I’m using it, do you Princess? I’m sure you don’t mind. Besides, it’s okay—I’m not going to come inside.”

Your thrusts pick up and you grab a handful of her ass, lifting her hips slightly as you thrust harder. “I’m not going to breed this tight little pussy, I’m not. I won’t come inside, I’m just going to fuck it until I’m ready, okay? I’m not gonna breed you, your highness. I’m not going to press my cock deep inside when I come so you take it all.