I Can’t Sleep

Note: Use of the word "pussy" in this story is used for the genitals of both a cis woman and trans man. My husband personally prefers "boy pussy" but occasionally uses all lingo for his 'bonus' hole. Switch and some domme/sub dynamic. Masturbation, Mutual masturbation, and lots of fun things to come. This is my first post. ❤️

Fantasy: I Can't Sleep

I wake up for what's easily the 5th time. I can't get comfortable and I've been tossing and turning for hours, so I give up. I'd been ridiculously horny all night, to the point where I considered just taking care of myself in front of Elliot while he played Skyrim. I've been working a weird schedule, and I haven't had any release in days. I seriously debated going for it for about 15 minutes, and I wondered if he'd care, if he'd like it or be weirded out by it, and how long it would take him to notice. If I was just using my fingers, maybe a while. As soon as toys got involved, that's quite a bit more noticeable.

Then again, Elliot gets really focused when he games.

Most of all, I sat there wondering if he'd join in.

But I never said or did anything, just kind of fantasized and thought about all the things I'd do if I was a little more stoned or felt like the vibe was a little more right.

Now it's after 3AM, and he's passed out in bed beside me, looking so peaceful sleeping on his back. His shirt's ridden up his stomach, showing off all that glorious hair against his pale skin. His happy trail is one of my favorite things. He has a hand tucked in his loose shorts, giving me the best peekaboo glimpse of his pubic hair and the hidden swell of his tdick below it. Now I know he's not wearing anything at all besides a T-shirt and some flimsy cloth shorts.

The arousal multiplies. I need to do something about this before it drives me crazy.

I feel a sense of deja vu and vaguely remember dreaming of touching myself while he was asleep beside me. He rarely falls asleep before me, so it's not often that I get to have sexy time to myself without doing it in the shower.

I reach inside my shorts and I'm actually a little embarrassed I'm already soaking wet. I blush, and then feel silly. Like anyone but me in this dark room is awake and knows that I'm shamefully, almost painfully ready to be fucked in some way immediately, followed by an orgasm. Maybe four.

I circle my fingers around, teasing myself. It's been forever since I've done anything besides finger myself a little, and I have yet to use my new toy. It's big, though, so some warm up and some lube might be warranted. Should I stay in bed, or move to the couch in the living room?

The bed would be more comfortable, but I decide against it. It would be embarrassing to wake him up and him not be in the mood to find I've pulled out a good portion of my "sex drawer" to fuck myself with right next to him while he's sleeping.

I grab a towel, my new toy, my lube, a washcloth, my small vibrator, and my big vibrator. Just in case, yknow.

I get out into the living room before I look down and laugh out loud a little. I look like I have half a sex store in my arms.

I settle onto the couch with my fucking arsenal (ha ha) and take my shorts off. I just daydream for a while, alernating between rubbing my clit, adding fingers and fucking myself, slowly getting wetter by the minute. It's crazy to me how wet I actually get sometimes. Add playing with or licking my nipples and we're in flood country.

I've been thinking about the time I fingered Elliot while he was on the phone asking a DMV agent questions for his car registration when I realize I'm up to three fingers and suddenly way too close to cumming; It's way sooner than I want to, so I stop what I'm doing and lay still for a moment, feeling my heart beat hard in my chest. I recently discovered a very fast and very fantastic new way to make myself orgasm while fingering myself, and holy god. It gets away from me sometimes it's so fast. I need to be quiet, too. If I make too much noise, the dogs will bark like crazy.

I wind down for a minute and then decide to try the new toy before I ruin the edge I've built.

It's hyper realistic, so soft and smooth it looks and feels incredibly real. Six inches of beautiful cock, girthy in the best way, complete with a set of movable balls, veins along the shaft, and a velvety pink head with a little slit to tease. I've been dying to show it to Elliot, but I haven't been sure how. I want to just pull it out of the drawer at random and say, "Look at this! Isn't it great? Wanna try it out? I'd love to fuck with it, or be fucked by it. Any preference?"

I don't want to pressure him, make him uncomfortable, or make him feel any kind of negatively. He's always struggled with body dysphoria and sex, and rarely feels up for more than some quick head or a little fingering if he's in the right mood. He feels inadequate, like he doesn't have "the right equipment." I've tried for 8 years to convince him otherwise, but I think I've only chipped away at the surface of those feelings. I think he's the most attractive man on Earth, and all his equipment is perfect to me. He tends to shy away more concerning sex as a result of his dysphoria, except when all that testosterone builds up. Every once in a while he gets so horny I'll catch him in a frenzy with his hands down his pants somewhere. In the kitchen, jacking off with his back against the fridge in the middle of a Thursday morning has been my favorite so far. Sometimes he'll take charge between us and use toys on me, but he very rarely lets me top him in any way.

I admire the "fake" cock, comparing it to real ones I've felt up close. By appearance alone I'm impressed, and I'm very curious how they've achieved the skin texture so accurately. I'd kill to make him watch me suck him off while he's wearing it and feel how nice the grind of the toy feels against him, then give him the sloppiest head of his life. Or god, to watch him suck it? Play with it, fuck himself with it? Maybe let me fuck him with it? Heaven. Probably what actual heaven is like. Even if he isn't comfortable using it with me, I'd tell him to borrow it for some him time. It's got the best damn reviews for a toy I've ever seen, and it was a very expensive treat for myself. I snagged it on sale, but still it was over two hundred dollars, before taxes and shipping. From the way it feels on my fingertips alone, I'd say it's gonna be worth it and more.

It's so soft, the combination of it plus how wet I am makes for the most sensual feeling I think I've ever experienced on my own. I don't even know how to describe it. I tease myself with the head of it, barely pushing it inside myself before backing out, creating a deeper need by the minute. It is big, but it's so smooth and wet now that on the next push, it glides almost all the way in all at once.

I know I make some kind of noise but I no longer notice or care. Holy fucking god, it feels incredible. There's nothing like being filled when you're really, really needy for it. Being fucked is a base instinct we all carry, and our bodies know what they want even if we don't yet.

The toy fills me perfectly, creating the best feeling of being almost stuffed with cock and still wanting a little more. I start slowly pumping, sliding out slowly to slam it home in my pussy. The base of the toy and the balls attached give my clit the stimulation it's crying out for. I scoot down a little further and bring one of my knees up to my chest to get a deeper angle and fuck myself to a home base orgasm. I pick up the pace and moan out loud. Best purchase ever. The cock fills up every bit of me and I think, God, why did I wait so long to do this? I'm sprawled out sideways on the couch, head almost hanging off and I don't care at all. My foot shakes and a tingle goes up my spine. So worth the money. I think I'll buy two more.

I open my eyes to watch myself and the toy, and Elliot is standing there.

I jerk, slamming the toy right into my g-spot at a funny angle. Waves of pleasure mix with a little terror and a lot of embarrassment as a loud moan and a shudder escape. Here I am, half naked and probably a sight to behold; I've got one arm tucked under my knee to spread my legs as up and open as I can comfortably get them, fingers teasing one of my nipples with my shirt pushed up to my neck, my other hand pumping a 6" realistic dildo out in my pussy without stopping, even with the interruption.

My brain fires on all cylinders again and I freeze, toy half in, half out of me. I look at Elliot, but he's looking down. I follow his gaze and realize there's a lot of my cum dripping out of me, down the length of the toy. We both watch as a drip slowly, slowly falls off the toy and hits the couch, joining a little puddle I've made on the towel I was wise to grab. I realize I'm exposed completely and spread open wide, fucking myself like a whore on our couch at almost 4 AM. I can hear my pulse thumping in my ears.

A million things fly through my brain to say, but what comes out shocks us both. "Come here. If you want."

My throat's a little dry so it comes out sexier and raspier than I thought it would. At first I don't know what he's going to do. He almost doesn't seem to hear me, and just stares. I hold my left hand out to him, motioning him closer. My right hand has resumed, slowly moving the toy in and out again. I can't help it. I think my brain has shut off and the directive we're left with is "Orgasm right the fuck now."

I motion again, and this time he comes forward, eyes definitely alert now, watching both my hands intently. I can't really read his expression, but the mix I'm picking up on seems largely positive. So good so far.

When he's close enough to touch, I reach out. His hand lifts towards mine instinctively, but I take a chance, leaning forward and surprising him even more. I slip my hand between his legs, sliding my fingers over his dick and down, over his hole through his shorts. I know intimately from earlier he isn't wearing any boxers, so I know the friction feels fantastic. There's just a little bit of fabric separating our skin.

He exhales loudly, closing his eyes. His body language tells me he wants to lean away, but his hips move against my hand softly, pressing my fingers against him more firmly as I slide them back and forth and tease him through his shorts.

"I want to try something, just bear with me," I almost whisper. He tenses and I think for a second he's going to bail, and I flick my thumb over his dick through his shorts, once, twice, until I have a light pattern going. His hips buck and he's leaning his hips forward, grinding up against my hand, anxiety forgotten for now. He's loving the touches. I use enough pressure to rile him up, but not enough to take him further than I want him yet. I sit up a bit on my left elbow and glance up, making sure his eyes are still closed. They are, and his breathing has gotten hard enough that every time I rub in a line over his cock and against his hole, he fogs up his glasses a tiny bit. I pull him closer a little at a time, until his hips are level with my face on the couch. The angle is much harder to use my hand, so I brace for the next phase. I let go of my toy with my right hand, and in one motion I lean forward, pull down Elliot's shorts, and duck my head. I swirl my tongue around the head of his dick, grabbing behind his thighs to hold him in place right as he wildly jerks his hips. In surprise and great pleasure I think.

I think correctly.

I'm rewarded with a groan loud enough to set the dogs off barking. I push his legs apart a little further, allowing me to slide my tongue along his hole, which is wet and ready after just a couple of minutes. I give a few gentle flicks, and his legs shake. One of his hands reaches down and grabs my hair and I smile against his thighs. God and 8 years on testosterone have blessed him, that's for sure. When he's aroused, his T-cock can grow almost 2 inches long and gets hard enough to suck on easily. Coupled with his ever tight hole, he's a dream in bed. Boy pussy is the best thing on the planet. Elliot's boy pussy is so nice I want to follow him around 24/7 trying to fuck it or lick it constantly.

I really want to try something, but I don't want him to react badly. He's closed his eyes again- I haven't really been watching his face to see if he ever opened them. He has his head tilted back, mouth slightly open on a pant as I suck gently on his cock. I'm always enthusiastic when I give him head, but I want this to be unforgettable.

My head is propped comfortably against the arm of the couch and a bunched up pillow, allowing me a comfortable angle to keep my neck like this for a while. But what would be even better...

I decide to say fuck it and risk it. With both hands I gently grab and move Elliot closer, pushing one of his legs up. At the same time I suck on his dick harder, and he's lost in the moment and barely paying attention to whatever else I'm doing. I pull him over more, pushing his left leg up and putting his foot down, between the back of tbe couch and my shoulder. I move one of my hands up to stroke him so I can get a good look. From this angle, the position of his legs has him spread open for me completely. His T-dick is bright pink against his dark brown pubic hair and all the dark fuzz on his thighs. It's pretty swollen with the love and attention I've paid it so far, and has already grown an inch since I started. His folds are slick and his hole is slightly open and glistening. I give into my urge at last. Cupping under his ass, I lean forward and suck his dick into my mouth, letting my tongue dip and rub against the ridge of it. I move my hand, pulling it around his thigh so my thumb can tease his sweet hole. I haven't done this in forever, and I hope he's loving what I'm doing. I tease him with my thumb while I suck his dick, lightly at first with little flicks, before I dip my thumb inside him once, twice, before pulling out to rub a circle all around the edge.

Another groan, so loud it echoes off the walls a little. I tilt my head back and watch him breathing harder, a red tint creeping up his neck. His glasses are half fogged up now, which is so silly and so sexy at the same time. His back is arched, hips thrusting down to meet me touch for touch, obviously desperate for more friction. I love that he's enjoying this as much as I am. I still have the toy inside me, and I can hardly believe I'm still dripping steadily despite the lack of stimulation. The thought that I'm cockwarming my toy while Elliot grinds his pussy on my face makes me a little dizzy.

I'm so turned on I'm acting on horny instinct now.

I guide Elliot to grind against my tongue and tease him a little more with my thumb, getting bolder and steadily fucking him gently. He complies readily, and both his hands are tangled in my hair, pulling so desperately towards more, more that I giggle a little around his dick. He jerks and moans and I begin to hum a little to fuck with him even more. I keep my thumb where it is, but I pull back a little. I start rubbing his dick with my wet thumb, trailing slow circles. I ask, "What do you want, baby?"

He moans again, softly, bumping his hips against my hand. I squeeze one of his ass cheeks, smiling when I realize he's so turned on he's dripping down his thighs a little.

I blow on his dick, knowing it's just enough stimulation to keep him crazy with need while not progressing his orgasm any further. I want to know what direction this train is going.

I blow gently again, and the air on him elicits a higher pitched noise this time. The dogs go crazy again, scratching against the door.

The door?

I go back to rubbing slow, tiny circles on his dick, while I process that. How did he know to close the bedroom door so the dogs wouldn't come in here while we were doing this? If he had just woken up and walked out to find me like this, he would've just walked right out of the bedroom, maybe pushed the dog food container to block the doorway. But he wouldn't have closed the door. Unless... unless he came out, saw me, and then walked back to close the door before crossing the room to get to me.

How long did he watch me?

Ooh. Now I'm very intrigued.

I ask again, voice a little raspy once more.

"What do you want, my love?"

He opens his eyes a little and looks down at me. His eyes are a little unfocused, and he looks so cute and almost confused.

"What do I want?"

"Mhmmm," I hum. I pull my hand away from him and laugh softly as his hips buck forward automatically, searching for the missing friction. "What do you want, my love? I could continue with my very fun course of action I'm on right now and very happily fuck you, I could pull you down and have you grind yourself against my tongue while I fuck myself with this magnificent toy... I am so happy to fuck you senseless in any capacity, honestly, the possibilities are endless." He's flushed down his chest now, sweating just a little. I hope I haven't freaked him out. I plunge on. "Did you like what you saw before I noticed you? You should really try out this toy sometime. It's incredible. It feels so real it's a little crazy."

His eyes dart down and I feel the heat in his look as he realizes again that I have a very realistic fake cock 3/4ths of the way in, beads of precum glistening on my pussy and the toy inside me. I've made a pretty big wet spot on the towel underneath me, and I'm positive the couch is wet now too. Oh well. I'm well past caring.

I wait, holding my breath a little. I rub the inside of his thigh and admire the sight before me. He's backed up a little, making it a little easier to talk. He still hasn't put his leg down though, and his dick is swollen. It's grown twice its size since I pulled down his shorts. His hole is pink and wet and pulses just a little when I gently run one of my fingers against the underside of his swollen dick. God, I want to make him come undone for me so badly.

"I... I watched you for a couple of minutes, before you pulled that toy out," he admits. I adjust my legs a little and the toy slips out, just a bit, and he watches it intently. He looks horny as hell and I'm so excited, but I keep quiet and hope he continues.

He takes a breath and says "I woke up when I heard a noise and Obi Wan boofed a little. I looked for you, but you weren't in bed, so I came looking for you. I stepped out here and saw you and didn't know what to do... It was really hot, watching you. I came back and closed the door so the dogs wouldn't get out. I wanted to say or do something, but I didn't want to scare you. I just stood here, torn on what to do. Honestly it was fun watching you, I got distracted completely."

I'm speechless. I had the toy out for a good minute before I saw him, not to mention all before that. Who knows what I said or did. I was so into fucking myself I'm pretty sure I was having a sex conversation with him half out loud, half in my head. What did I say?

I don't realize I've vocalized that thought until he says, "Well... a lot of stuff that sounded pretty good."

"Oh yeah? Like what?" I'm massively intrigued. The DMV? After? I vaguely remember thinking that god, I would kill to either fuck Elliot with this toy, or watch him fuck himself with it. It felt so fucking good I would die to see him experience how good it feels himself.

I think I'm right again. He goes completely pink in the face and looks embarrassed, a little scared and a lot turned on by the thought. I see him look down again at the dildo and I lean down to pull it out. It slides out with a "plop!" that makes me laugh at the noise, a little shakily from the sensation. I feel empty immediately, my edge of an orgasm a steady hum in the background now. Not gone, just constantly, mildly there.

The toy is wet as can be, dripping with my precum all the way down to the base. I start to wipe it on the towel and reconsider. I decide to just use my mouth and clean off the toy, sliding my tongue along the sides and down to the base until I've gotten most of it. I turn my head and make eye contact with Elliot, who's staring at me, eyes wide and a little glazed again. I decide to feel proudly slutty instead of embarrassed and wiggle my brows at him. His gaze flickers back between me and the toy and I can almost see how badly he wants to do something, and can't decide which thing he wants to do. He smiles and slides his hands along the inside of my thigh. "Having fun, are ya?"

I smile back and lean forward to lick a stripe along his dick. "Way more fun now that you've joined me." I lift the dildo up. "You want to feel?"

I read in his eyes that he really wants to try out the toy, but he's feeling extremely conflicted. He usually has a lot of body dysphoria about having me fuck him; I rarely finger him, and he's never let me fuck him with a toy or attachment besides a very small vibrator in a fun assist. I want to tell him easily that I think no less of him as a man; the complete opposite. I think he's the most perfect man on earth. Him having a gorgeous, tight boy pussy is the sweetest icing on the cake. Trans guys are fucking incredible. They're sexy and masculine, wild and experimental sometimes. They have fucking fantastic dicks that grow sometimes two to four times their size when they're horny, and they have wet, dripping, ready bonus holes to fuck? Perfect beings, truly.

I can see the conflict in him warring with all the blood that's rushed to his lower body. His horomones are roaring in his ears as much as mine are, so I know he's closer to giving in to what he actually wants rather than what his dysphoria is always telling him and holding him back. I tug lightly on his hand, pulling him around so he sits down on the couch next to me, left leg over my right leg. He starts breathing a little hard again, but I can tell its out of more excitement than anxiety as he lets me force his legs wide, hooking his bent leg over my own. He's happy to let me be completely charge in this moment, taking away the need for a decision so he can enjoy it and not overthink it. I move slowly in case he's uncomfortable, but I don't meet any hesitation from him. I rearrange our limbs so we're side by side, touching by our overlapping arms and legs. We're both spread open, mostly sitting on the towel. Honestly, who cares?

I lean against him and take his right hand, twining our fingers as we reach between his thighs. Our fingers both make contact with his dick, slipping a little against the wetness I've helped him achieve. He gasps and moans, but before he can lean his head back and close his eyes, I slip the toy into his open left hand against his knee.

"Holy shit, it does feel real!"

I laugh. "I know right? Once it's in contact with body heat and a little wet I couldn't tell a difference, except maybe it's not as hot or firm in places as it might be. But I gotta say, really, really good quality."

He makes a face. "Was it crazy expensive?"

"Well, it wasn't cheap, but I can attest it is worth every penny."

He isn't expecting it when I guide our hands holding the toy down, rubbing it firmly against his dick and hole. That earns me my favorite noise so far. I can't decide if it's more of a moan or a whine.

"Oh god," he gasps a little. As I pick up the rhythm, he's actually panting. I have my hand wrapped around his, and he has his eyes glued to our fingers wrapped around the girth of the toy as we make it wetter by the second with his precum. Our right hands are still touching him too, and I guide our fingers to play with his hole a little while we rub the toy against the head of his little cock.

"Good, right?" I laugh again and press a kiss onto his shoulder. I extract my right arm so I can shift and control our left hands with the toy. I leave Elliot's right hand where it is, pressing two of his fingers into his pussy before I detach. He arches his hips and slips his fingers inside, immediately establishing a rhythm. A very good boy in this picture. I actually think he's getting so into it he might cum soon. I want to see him fucked by this cock before that happens. He's breathing hard and I tap his right hand, a signal to slow down his fun just a little. He obeys, but I'm delighted to see his fingers still pumping steadily in and out of his tight hole, if much less intensely. I don't want to risk the big moment I'm hoping for, but I'm almost drooling at this very rare sight. I drink it in and commit this to memory.

Repositioning our bodies so I have a better angle, I hitch his left leg a little higher so he's spread as wide as he can be, hips tilted up so we can fuck him deeper. He's trembling, and I can tell he's excited, but it's nerve wracking for both of us. I kiss his shoulder again. "I love seeing you like this. You look fucking perfect, spread open like this. I want to memorize every detail of it after I make you cum for me a dozen times."

He closes his eyes again, and I worry for a second that I've ruined it and made him uncomfortable, crossed a line and made him dysphoric. I'm pleasantly shocked when he makes another sound between that moan and whine, pushing his hips out so his hole is completely on display for me while he plays with it. He's added a third finger at some point during this, and seeing his hole stretched open by his fingers is so hot I can't move for a second. I tap his hand again and his hand stills, fingers filling him up but not moving. He's so tense, I know he's close to cumming and is dying to move his fingers, but he really wants to find out what can happen next.

He's ready now. I grab the lube and add a little to the head and down the shaft of the toy, though with how big the spot under Elliot's side of the towel is getting, I don't even need it. It'll be bonus points in the friction department when he feels like contrast of the cool lube inside his warm pussy.

I tap his hand again, and though I'm pretty sure his eyes are fully closed and he can't see me, he knows what I want. He removes his fingers and rests his hand on his thigh, a string of wet webbing between his fingertips. I press the head of the toy against his hole, and inch by inch I slowly push it inside him. Instantly he tenses up. The toy isn't much bigger than his three fingers, but it fills him up in another way and I know a little panic is setting in. I search for a way to distract him. I lift his right wrist and guide his fingers to his mouth, pushing them slightly against his lips. They're still really wet from fucking his pussy, and the distraction I need. I go for surprising him in a really kinky but hopefully good way.

"Here, baby. Lick your fingers and clean them up for me while I help you. Move your hips, mhmm, there you go." Elliot's eyes are wide as his tongue flicks out, but sucks his fingers clean and I know I've hit my mark. He moans around two fingers as I push the toy deeper, rocking slightly to get him used to it so he can take it all. It's a tight fit, and the view is mind blowingly hot.

I nudge the toy up inside him, searching for that magic spot again. I know I've found it when I finally get a real scream out of him, muffled around his hand. Two thrusts against his g-spot and he's humping up as I pull the toy out slowly, pause for a heartbeat with the head just a whisper against him, and then thrust it all the way inside him. The balls slap against his ass and the wave of wetness down his thighs and cheeks magnifies the sound. A loud moan rips out of him and his fingers are back, trying to rub his dick to get there faster.

His mouth open slightly and eyes fixated down on the toy, he's making these little noises and twitching his hips up every moment he thinks will get him closer. I know he really wants to cum, and I slow down to edge him even further. He's getting a little desperate now, and the noises shift to whines and the cutest little breathless gasps as he realizes I'm dragging this out. I think about how I felt earlier, that same desperate need to be fucked and have some goddamn release immediately, down to my core. I feel just a little bit bad I'm teasing him so much. But I know that I can give him the best orgasm he's ever had, and I have one more thing I really, really want to try.

In a matter of maybe 45 minutes (but who the fuck is keeping time right now?) I have seen my nerdy, quiet, introverted husband turn into quite literally a dripping wet whore for cock. I think I could ask him to do quite a bit right now and his need to cum would override any inhibitions he usually has right about now about his body.

My tempo fucking him is excruciatingly slow right now, and he's slowed his stroking his cock to match after a touch from me. I pull the toy all the way out, running the length of it along his slit as I do. Softly, like I'm trying not to spook a deer, I say, "Stand up for me, baby."

Elliot freezes, uncertainty back in his eyes. I've disturbed the fog a little.

"Shhh," I say, a little above a whisper. "Trust me." I sit up a little, lifting his hands and untangling until we're both standing. I sit back down on the couch with my feet planted on the floor, pillows behind my back and hips. I pull Elliot so he's facing me, legs splayed and hands anxiously rubbing against his thighs. I know he has no idea what I'm doing, and I think he's disappointed because he thinks I'm swapping the dynamic and making him use the toy on me now. I tug on his hands until his legs are against the couch. I lean forward and place my hand under his knee, and he's confused. He has no idea where I'm going with this until I've completely pulled him into my lap, straddling my right thigh, raised up on his knees on the couch. When I grab the toy and position it with the base against the top of my thigh, I see the light flicker on and he realizes. I pull his hips down a little until the head of the dildo is directly below him, maybe an inch or so from rubbing against his dick and giving him the friction that he wants. I know he's fucked himself like this and ridden one of his own toys, and he definitely likes this position. There's a moment between us as I pull his hips down the rest of the way where I think he's going to bolt. The tension melts away to desire as the silky head of the toy makes contact with the silky skin of his own cock, and I'm so glad I took this chance. His pupils are huge, high on the fog of lust he's experiencing. I hold the toy in place, at first guiding him to gently grind against it, before he finds his own rhythm and I'm ready to watch him ride me right the fuck now. He seems to read my mind because he lifts up a little and makes his legs a little wider. I position the toy at the entrance to his hole and push up into him as he pushes down to meet me. It's the best thing in the fucking world when he bottoms out and the hot wet skin between his thighs touches my leg, complete with a breathless moan from him. I reach up and take his glasses off, and he's confused again, right up until I set them safely on the coffee table. When I sit back, I wrap my hand around his thigh and cant my hips up hard, fucking the toy into him deep and fast. He gasps, choking on a laugh and a moan as he realizes his glasses might have bounced off his face. I have another idea. I sit up a little more, forcing him to press his legs on either side of mine and get a better seat on me and the cock inside him. Toy trapped between us, I have the perfect angle to fuck him how I want to, even without a harness. I run my hands over his ass and grab his his thighs below his cheeks firmly and begin to rock up into him, hitting as close to his g spot every time as I can. It works! He grinds down against the toy and wraps one of his hands in my hair as I fuck him. I plant my other foot firmly on the floor and feel secure enough to pick up the pace. I feel him match me as I fuck him until he's bouncing on the toy with abandon, panting and saying half sentences featuring a lot of the word "Please!"

I roll my hips hard, hitting that sweet spot inside him. "Please what, baby?" I do it again, and this time he almost wails,

"Please!"

Oh no sweet boy. I want him to say it.

I grab his waist and stop him, so completely and fast I think he sobs a little from the sudden lack of contact and feeling. I reach behind him and pull him flush against me, tensing my thighs. He whines a little but doesn't use his words, just waits with wide eyes that scream how badly he wants release right now. I rock, ever so slightly up into him, then go still. He shudders, moaning from the sensation. I wait several moments for him to say what he wants me to do before I reach down and flick his dick with the tip of my finger. It's so plump and sensitive from all the teasing and fucking that he bucks his hips hard at the contact. I'm betting he's so close every individual thrust is a killer tease, and the loud whine and the shiver that goes down his back he gives me tells me I'm right again.

One more time. With a slow roll of my hips, I ask again, "What do you want, baby? What is it?"

Head back and breathing hard again, he's either being stubborn in a bratty submissive way, or he's embarrassed. Hm, maybe a little bit of both. Regardless, I don't get an answer, so I change tactics.

Before he can open his eyes I've wrapped one arm around his waist to hold him steady, and with the other I've grabbed the back of his neck. I thrust my hips up hard once, twice, into a hard and fast pattern. He goes wild, grinding down against me and moaning again, wiggling around to get that cock at just the right angle to make him cum. I fuck him like that for 15 seconds or so, and just when I think he's right on the edge I slam him down and stop with a hard wet slap that's music to my ears. I tighten my grip around his waist so he can't wiggle and lean back, forcing him to lean forward with me. I crane my neck to look around his waist and admire the sight. At this angle the toy is half in, half out of his pussy, soaked from how wet he's been this whole time. He has his own precum in a long drip down to the base, puddling near his knees on either side. He's breathing hard, and lets out a frustrated groan, indignant that I've stopped when he knows I know he's this close. I want my answer though, and we both know how stubborn I am. I let go of his neck and rest my hand on his perfect round ass, fondling one of his cheeks and nudging a little close to his asshole. He tenses a little but doesn't stop me. I wonder for a second if he's fantasized about being fucked in both holes at the same time. We don't normally do anal, but then again, we don't normally do this either. Another day's adventure.

When he relaxes again, I ask for the last time, "What do you want, baby? You've gotta tell me. I want to hear you say it."

Out of stubborness, brattiness, or another motivation, Elliot clamps his mouth shut and looks over my shoulder at the wall, still trying to subtly fuck himself on the toy still inside him. I hmm a little and then laugh softly to myself. Elliot takes this the way I expected he would, like I'm going to give in and make him cum because it's my favorite thing in the world. While it is, I'm determined to see how far my little slut is willing to go to cum tonight. He leans into me, and he's almost fully relaxed when I raise my hand and bring it down in a hard stinging slap on his ass. He jerks, completely surprised. I use the moment and take his neck back, wrapping my fingers around his throat and squeezing just a little. I see a mixture of emotions across his face and one expression stands out: he likes this. He likes this a lot.

I only spare a moment to wish I'd done this years ago before I smile at him, press a kiss against his shoulder.

"You and I both know what you want. You're just so dang stubborn, you can't or won't say it. But I know it, and you know it. You want to cum. And I want you to say it. But not just that, not now that you've dragged it out. I want you to admit how you feel right now. You love this. Your hole is stretched around a thick cock and you want to cum so badly you can hardly stand it. You're an enthusiastic and talented cockslut, and you love being filled and fucked. You love being reduced to a wet hole. Am I right?"

I worry again I've gone too far when Elliot ducks his head, but then I realize he's leaning against my neck, his mouth by my ear. He grinds against the toy a little with the movement and moans into my ear. I shiver a little. I want him to cum as badly as he does, almost.

"Yes, yes, I do. I love it. It feels so fucking good to ride you like this. This cock feels so good inside me. It feels amazing. I wish you would have done this the day you got it. I wish I would've let you fuck me like this years ago."

I bump my hips a little, rewarding him for the honesty. He moans and I smile. I love fucking him. I love seeing him come undone like this. I tell him so.

"And... I'm ready to make you cum."

He lights up and groans, squeezing my thigh with both of his.

"Yes, please."

"Okay. Get up a little and lay down on the couch."

This time he obeys immediately, and I'm lightheaded when I notice he keeps the toy inside him without dislodging it at all or moving his hand, cockwarming the entire time. I almost orgasm from the sight of it alone.

I position how I want him, putting one foot up on the back of the couch and his other foot planted on the seat, so I have a wide open view of the base of the toy, hand clenching it tight in his hand. The dildo fills him up, stretching his pussy perfectly around it, the skin shiny and smooth. The balls sit against the bottom of his asscheeks, and his other hole is on display. He's covered in fuzzy dark brown hair all over and I love it. Coupled with the image of his abused pussy stuffed full, it's the hottest thing I've ever seen. So far.

"Perfect. Now take the toy out. Put it

down."

The look on his face is comical. He looks like he wants to argue, whine, or disobey, but he thinks better of it. With major reluctance, he pulls the toy out slowly, moaning as the shaft rubs along the walls of his already sensitive hole. He looks at it longingly for a moment before putting in down, turning to me with an expectant expression that almost makes me laugh. We went from shy and totally unsure to eager and ready for cock in a very short amount of time.

His hole is bright pink and a little puffy from all the stimulation. It's gaping open just a little from the toy stretching him, peeking a view of the soft wet walls inside. Beads of precum are already dripping down and I know I have him where I want him. He's been fucked a lot tonight, and I'm not done yet.

Taking his ankle, I lift his leg a little to bend his knee and spread him open wider, and he gasps as a bit of wetness drips straight out of his pussy, sliding down between his cheeks. I replant his foot on the seat of the couch and admire him for just a moment; I don't want to wait too long and risk him getting self conscious. I reach down and flutter my fingers against his dick, then dip two of my fingers in to fuck him a few times. He arches his back and moans, "Please, please!"

"You wanna cum?"

"Yes!"

"You want to cum for me, right? You want me to fuck you a little more and give you want you want?" I punctuate this by bending my fingers, making a "come here" motion against his g-spot. He chokes out a moan that sounds a little like a sob again, nodding furiously and thrusting his pussy towards me as much as he can, trying to meet me for a deeper angle.

"Yes! Please, I want to cum so bad!"

"Okay baby."

He's panting a little again, and I know I've finally reached the point I wanted to with him. I scoot back, getting on my knees in front of him. I grab above his knees and bend my head, trying to see as much of his face as I can as I do this. When my tongue slides between the folds of his pussy and into his hole, he almost screams. Wrapping a hand in my hair, he starts trying to change position to grind against my mouth. I give inside of his thigh a light slap, keeping him where he is. I'm nowhere near done. I change tactics constantly, giving him just enough stimulation to keep him close to cumming, without approaching lift off just yet. His legs have started shaking uncontrollably, one thigh bouncing lightly against me.

Finally I pull back, and he gasps again on a half sob. I wonder if he's close to crying out of desperation. What a fun avenue to explore one day. Can I edge him until he actually cries and begs me for release?

The temptation is real, but I push it away. He's had enough, for tonight at least. Tomorrow is another day.

I lick my lips and he watches me, chest rising and falling, his mouth a little pink and fuller than usual. He's a vision like this, vulnerable, exposed, and so needy we both know he would do almost anything I asked right now. I could probably bend him over the couch and fuck his ass with that big toy and he'd beg me for more, more please!

I pick up the toy and hold it out to him. "I'm going to play with you and watch you while you fuck yourself with this. You can control the tempo, and how hard you fuck yourself, as much as you want until you're ready to cum."

I expect a little shyness or hesitation, but a light comes on behind his eyes. He's knows exactly the right angle to fuck himself to cum, right the fuck now. We're completely past any shyness. He takes the toy and positions it, running the tip along his wetness until I speak again.

"But. I want you to tell me when you're close, and ask if you can cum first. If you cum without saying anything or without permission, I'll ruin your orgasm and then fuck you myself, maybe bent over the back of the couch."

He almost looks like he's considering that, but he's been ready to cum for a while now and I know he won't give that up. He nods. "Okay."

He leans back against the pillows and tilts his hips up as he pushes the toy slowly back inside himself. Inch by inch, the toy disappears inside his hole and my head reels a little bit. I'm so fucking happy he agreed to this. I've seen him use his fingers, but I've never seen him use toys like this around me.

He gets back into it immediately, starting with slow strokes. I grab his left hand and position it on his dick, and without further prompting he takes over and creates a rhythm. Small circles over his dick match the pace of the toy fucking him. I lean forward and flick my tongue over the little head of his dick between his fingers, right as I use my other hand to grab his with the toy. We thrust the toy all the way inside him and he throws his head back and moans loudly.

This was all the push he needed. I lean back to enjoy the show as he picks up his pace, adjusting himself so one of his knees is pulled up to his chest. He's really into it now, and pistons the toy in and out faster. The slapping noise of the toy fucking his very wet hole is fantastic, and it's soon joined by little moans and gasps as he rolls his hips.

I grab my small vibrator right as he closes his eyes. I think he's close, and I want this to be explosive. He's rubbing furious little circles on his dick and humping against the toy inside him, trying desperately to reach his peak. I turn the vibrator on and press it to the underside of his dick and his moans bounce off the walls. He uses both hands on the toy now, slamming the length of it home inside his pussy. The tempo is hard and fast and I've never heard some of these noises come out his mouth, but I definitely want to again and again. He's almost mewling as I turn the vibrator on high, the buzz of it nearly lost against the louder sounds.

"I-I'm close! I'm really close!" he gasps.

"Look at me," I say. I lean forward and lightly grip his throat. "Are you ready? Do you wanna cum now?"

His eyes are wild when they lock with mine, his nod jerky. "Yes, yes, please! Please, can I cum now?" The toy is a blur between us, pounding his hole harder with every thrust.

I smile. "Yes baby. Now you can cum Keep your eyes on mine." I squeeze the sides of his throat and his breath catches. He pumps the toy in his pussy as hard as he can and his hips begin to stutter against the vibrator. He throws his head back, yelling and moaning as he comes. I grab his throat and force him to look at me as I keep the vibrator on his dick, locking eyes with him as we both make him cum together. His entire body is shaking and he's making broken, needy noises, gasps and moans ripped out of his mouth. The intense tremor in his legs increases, one of his feet shaking uncontrollably off the couch. He pulls the toy out abruptly on a scream, shoving his dick up against the vibrator as a stream of cum squirts out of his pussy. It happens again and again, little and big drips of cum gushing out of his pulsing hole as he writhes against the vibrator and tries desperately to clamp his legs shut. I band my forearm and hands down on him. It's much too late for that now. His eyes are wide locked with mine, thick lashes fringed with desperate tears from all the stimulation finally getting to him.

I take my hand off his throat, and he smiles faintly, thinking it's almost over and he feels incredible.

I lean forward abruptly and shove three of my fingers inside his pussy and piston them in and out, reaching his g-spot with each stroke. It's hot and so fucking tight, his walls clamping down on my fingers. His hands clutch my shoulders, and I maintain eye contact with him as I milk another orgasm from him for all he and his hole are worth. I had no idea he was a squirter, but from the very intense blush across his face and neck, I think he did. He cums again and again, bumping his hips against my fingers and shuddering as more cum streams out of his pussy, dripping down his asscrack and onto the couch. We're a slippery mess and it's the best fucking thing. He breaks eye contact with me, shutting his eyes tightly as he cries out from how it feels.

I reach down with my pinky and swipe some of his cum against his tight asshole, where a little puddle of it has gathered.

He jerks, eyes flying open as his head snaps up level with mine. He's panting hard and sweating, legs still shaking so hard his whole body is trembling. The contact against his other hole unlocked a new sensation in the mix and he's wild with all the shocks of his orgasms. I slow my fingers fucking him a moment to a steady beat.

"Break eye contact with me again while you're cumming and I'll fuck your ass and abuse your holes until the sun comes up tomorrow. Look, you've already made it so conveniently lubed up for me." I push my pinky against his asshole, playing in all the cum that's pooled. It twitches and gives a little, allowing my pinky to push some of the cum inside. He bucks his hips but his eyes don't leave mine for a second. His expression is a mix of fear and lust. He shocks me completely when he says, "I jack off sometimes and think about doing this. I've always wanted to let you fuck my ass while I fuck my p-pussy. I've always been too scared to cross this line at all, but it's felt so fucking good to let you fuck me. I-I wish I would have done this forever ago."

It's everything I wanted to hear and more.

I return to my fast pace, fucking him harder. He smiles gratefully and moans, arching his ass and pussy as close to me as he can get. I give him the vibrator to use on himself, repositioning so I can use my free hand to play with his asshole a little. I love the sound that comes out when I push a finger inside and fill both his holes as he rides out the last waves of his orgasm. Maybe after a short break he'll let me fuck his ass with another toy from the sex drawer while he fucks his pussy for me. I'd love to see him ride me in reverse so I can see the toys fuck his holes up close, especially after I get a vibrator against my clit and finally cum myself. I can't wait, and I'm already thinking of all the fun possibilities and positions.

We'll see if he can walk after this first.

I smile wide as he shivers again, pussy and ass clenching around my fingers.

This is the best night ever. Day? Who even knows what time it is. The curtains and blinds are blessedly closed.