Guys Trip, Lace Causes a Stir Ch. 04

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A friendly wager brings thrilling consequences.
9.9k words
4.66
16.6k
15

Part 4 of the 6 part series

Updated 06/15/2023
Created 06/10/2017
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trybiman
trybiman
98 Followers

I wake up a little more rested this morning than I was yesterday. After having had more amazing sex with Steve we made a conscious decision to sleep separately so we wouldn't be all over each other for the whole night. We did stay up for a little while ironing out the details of the bet that were going to put into place starting today. The last thing that I remember before drifting off was that I was really nervous about how things are going to go with Ben and Ryan today. Fortunately, I was tired enough that it didn't prevent me from falling into a nice, deep sleep.

With eyes still half closed I reluctantly start to get up. As I move over to the side of the bed to get out I feel the sheets slide across my almost naked legs. It feels amazing when the sheets caress my legs through the pink stockings that I'm still wearing.

Pushing that thought to the side I get up and walk, a bit wobbly, out of the room to go use the restroom. Before returning to the bedroom I decide to brush my teeth to get rid of my morning breath. I'm not a huge fan of walking around with my cock and balls hanging out so I consider pulling on the thong that is laying on the floor before heading back to the bedroom, but instead decide to just let it be for now. I'm not totally ready to get up yet so I'm looking forward to sliding into bed and falling back to sleep for a while longer, so with eyelids still tired and heavy I walk toward the room and my bed.

As I enter the room I glance across and see that Steve must have been as tired as me because he's still sound asleep. He's sprawled out on his back with his sheets barely covering one leg. My eyes open the rest of the way when I see all of his bare skin, especially his naked cock laying across his hip. Right now, it's at about halfway between its fully soft size and how far I now know it can grow.

All thoughts of sleeping leave my mind when I realize that there are more important things to think about right now. I've barely opened my eyes and I'm already starting to be overcome with lust. I know exactly what I need to do so I quietly head straight toward his bed. I don't want Steve to wake too soon so I gently climb on at the foot of the bed.

With one hand on each side of his legs I crawl up on my knees, my left in between his and my right to the side. I inch my way up, careful not to jostle the bed too much or touch him on the way. I stop once my head passes his thighs and I drink in the closeup view of his manhood, the ridge at the base of his glans, each and every contour of his shaft and his smooth balls beneath the base.

Unable to resist any longer, I lean down and run my tongue slowly from between his balls up the length of his meaty shaft. I continue until the tip of my tongue presses against the hole where his cum will hopefully soon flood from deep into my mouth. I circle all around the head before dropping back down to his balls, taking each one into my mouth and running my tongue around as I gently suck on them.

The more time that I spend near his loins the hungrier I get. I take my mouth from his balls and lift my head slightly to look at his cock again before diving back in. It isn't fully hard but it has grown enough to now be standing partially erect on its own. Full of lust, I take it in my hand and guide it toward my mouth as I lower back down.

I want it deep in my mouth but I force myself to be patient, to savor every moment and every warm, delicious inch. Even though he isn't fully hard, the head of Steve's cock is already glistening with its first serving of pre-cum. Seeing it almost breaks my resolve and prompts me to dive in and engulf him completely, taking him deep into my mouth, but I am barely able to resist.

Instead, I circle around the head and take all of the nectar into my mouth, bathing my tongue with it. Then I take the tip into my mouth, just back to the ridge, as I gently squeeze his shaft with my hand and I firmly suck on the tip to milk any more pre-cum that is ready for me. My efforts are rewarded as another surge of pre-cum coats my tongue and a moan escapes Steve's skilled lips. He's starting to stir but, more importantly, so is his cock. I can feel the thickness increasing in my hand and the added girth is pushing back against the grip that my lips have on the spongy helmet in my mouth.

I'm now softly stroking his shaft and holding my head still, continuing to suck, as he slowly grows and reaches further along my tongue. Unable to hold out any longer I move my hand from his shaft to his balls, holding them and caressing them with my palm and fingers. Now that my hand is out of the way I start to lower down onto his cock, plunging more and more into my mouth, taking the time to work my tongue all around the sensitive underside as I go.

Steve is definitely awake now. I haven't looked up to see his face but I can see his left hand out of the corner of my eye with a tight grip on the sheets and suddenly feel the fingers of his right hand running through my hair.

As if that weren't enough encouragement already, Steve reinforces it verbally, "Oh yes Jimmy! Fuck, I could wake up like this every day."

I pause my descent briefly to tilt my head and look up at him. His eyes are barely open, his obvious pleasure written all over his face. He catches my eyes with his when he feels me hesitate and begs, "Oh god, please don't stop."

That's all I need to hear and I smile around his cock. He probably can't see it from my mouth but I'm sure he can see it in my eyes until I look away and back down to continue with his wake-up call. In my primal hunger I can't help but moan as my concentration goes back to the now fully engorged treat in my mouth, "Mmmmm."

Spurred on by Steve's approval and my own lust I resume. Working my tongue around his shaft I continue down, plunging him deeper into my mouth until the tip reaches to the back. Even with my mouth completely full, the pressure against my throat obvious, there is still distance between my lips and the base of his cock.

Just two days ago I'd never even held another cock, let alone had one in my mouth, but now I have one buried completely in my mouth and the exposed skin still has me not yet satisfied. For what is at least the fourth time this weekend I try to relax and open my throat, amazed at how far I've come. As ready as I'm going to get, I push on again. My throat resists the intrusion but I start rhythmically swallowing which serves to suck the head down into my tight oral canal until my nose bottoms out against his pelvis.

When he enters the even tighter space Steve's hips buck and his cock stiffens and throbs hard in my mouth. His hand closes on my hair, pulling it slightly, and he calls out, "Uhhhh! Yes!!"

When I started I was wondering how long this would last since we just went at it last night. Apparently not too long! Rather than take his load straight into my throat I pull my head back until only the tip is left inside the confines of my mouth. I take his shaft in my hand and start to pump it as I suck on the tip, anxious to feel and taste the thick ropes of his cum as it pours across my tongue and into my throat.

His cock continues to throb and pulse in my mouth, accompanied by a constant stream of moans coming from his mouth. I'm exhilarated as floods of creamy, white seed surge forward to cover my tongue and fill my mouth. Eyes closed, I keep pumping and sucking as I work to milk his rod completely and savor every last drop. His load is smaller than the one that he covered my body with last night but there is still plenty to alleviate my hunger and leave both of us satisfied for different reasons.

The object of my lust finally begins to soften in my hand, shrinking between my lips, and I can tell that I've taken all it has to give...for now. Knowing I've completed one of the best wake-up calls that a man could ask for I lift my head from his groin, look up with a smile and simply say, "Good morning."

Steve smiles in return and responds, still out of breath, "God! What an amazing way to wake up!" then lays his head back onto the pillow, closes his eyes and breathes deeply to try and catch his breath.

Satisfied that my job is done, extremely well I might add, I get up from the bed and head back over to my own. I smile at the sound of his breathing, still heavy, then crawl into bed. I don't expend any extra energy pulling on the sheets or even rolling over. Instead, I just sink down to relax for a little while longer until I'm ready to get up and start the rest of the day, my semi-hard cock trapped between my stomach and the soft bed.

My eyes are closed but I'm not going back to sleep so it's easy for me to hear the rustling coming from the other bed as Steve gets up and heads into the bathroom himself. It's only a few minutes before I can hear his footsteps returning into the room as he shuffles between our two beds.

About halfway up the sound of his footsteps stops. After a short pause I feel his hands on me, gently spreading the round globes of my smooth backside. He is so gentle as he spreads them apart to expose the pink pucker hidden between.

This is exactly what I had secretly hoped for when I climbed back into my bed!

Steve doesn't disappoint. He doesn't keep me waiting long, quickly following his tender hands to give my backside even more attention. I feel his breath as he moves in to kiss and lick first my left mound and then my right, before diving into the canal in between. His tongue snakes its way down and I quickly become fully engorged when I feel it press against my entrance, circling slowly before prying me open slightly as he pushes the tip in.

I can't help but moan as he begins to thrust his tongue into me as deep as it will go. His hands still keep me spread, his fingertips now helping to open my hole so he can plunge more of his tongue deeper inside. I arch my back and push up and back into his face, trying to force him deeper inside me.

We haven't had the chance to discuss what we like but he seems to know my body so well already that there hasn't been a need. Still plunging his tongue into me, he takes his hands from my ass to reach around, grab my hips and pull me up and back. I'm up on my knees with my hips up high so he is able to reach through my legs and take my rock-hard cock into his left hand. He begins to stroke it soft and slow while his right hand goes back to squeezing and caressing my cheek.

He doesn't wait long before he slides his thumb back into my crack, pulling sideways to open me wider for his tongue to continue its welcome assault. I'm in heaven, pleasured from the front and from the back, and I start to moan. I don't move at all, trying not to disrupt what he's doing to me, one hand stroking my cock and his tongue in my ass, but it doesn't last long anyway.

He pulls back slightly, his tongue retreating but before I can register any disappointment it's replaced by his thumb. He is circling my pink rosebud, soaked with his saliva, the tip of his thumb working in, stretching me more and pressing past the resistance of my tight entrance. Once I feel the tip of his thumb inside I can't stay still anymore. I push back against him until he can't reach any deeper.

It doesn't slide in as easily as before but the pressure on my prostate makes me quickly move past the discomfort as I grunt with pleasure. Steve must have felt the friction as well because he takes his hand from my cock and reaches to the nightstand to grab the bottle of lube that he tossed there on the way to bed last night. He doesn't waste any time at all and, after a click of the top, I feel the cool liquid pouring down my crack.

Before it completes its journey, he pulls his thumb out, leaving me open and empty which allows the lube to coat my hole and a little bit to leak inside. I can sense his hunger. After a short pause his hand returns and I feel the tips of two wet, slippery fingers working the lube around and pressing against my pussy. I'm now so slick and horny that they slide in fast, barely any resistance as he slowly presses forward to bury them to the hilt.

Rather than thrust in and out he keeps them in deep and works the tips back and forth against my g-spot, sending waves of pleasure through me. I'm lost in the pleasure, moaning as I clamp down on his fingers and pre-cum steadily oozes from the bulbous head of my cock.

Not one to disappoint Steve pushes against the side of my hip, rolling me over first to me side and then completely onto my back, all the while keeping up the pressure deep inside me. I'm now laying with my legs bent and spread wide, fully exposed with his fingers probing and my cock twitching and dripping on my stomach. He looks up to my face and smirks seductively before diving down to lick slowly from my balls to the swollen head of my cock.

I know this won't last much longer once the warmth of his mouth engulfs me completely. "Oh god!" is all I can manage when I feel his lips against the base of my rod and his throat tight around the head.

After only a few times of him backing off to my swollen tip before plunging down to take me into his throat, his fingers still milking my prostate, I call out "I'm cumming! Oh god, I'm cumming!"

It seems so unimaginative, the old "I'm cumming". The phrase seems so overused but I realize that there is nothing else that conveys the lust and passion that has overcome me in this moment.

Steve pulls back to the tip as I start to blast ropes of cum into his mouth. I can't believe I have this much left after the amount that I lost last night, but as my ass clenches around his fingers my cock continues to pulse and flood his mouth with my seed.

He pulls his fingers from my canal, leaving me empty once again, but he continues to suck until I'm completely drained and I reach the stage where my cock has become ultra-sensitive and a little uncomfortable. I can see the smile in his eyes that tells me that he knows exactly what he's doing at this point so. With a little laugh, I push his head back away from my shrinking member.

Spent from another fantastic orgasm I roll over and let my head sink into the pillow. I'm unsure what's in his head but I leave room for Steve to lay down and relax if he wants. Without hesitation he turns to lay back as well, his body tilted ever so slightly toward me, arm up with his hand under the pillow behind his head. I can see the look of contentment on his face as he stares absently at the ceiling, clearly tired as well.

I can feel myself getting more and more relaxed and I'm pretty sure I'm going to fall into a post-orgasm nap. Some things never change...it's either a snack or sleep for me almost every time.

Before I fully submit to sleep I inch back over until my body is next to Steve and the full length of my right leg is laying against his left. Finally, I reach over and lay my open hand softly on his crotch, loosely cupping his fantastic cock and balls. I'm not looking for anything more, just wanting to feel them and keep them close.

I mutter in a groggy, pre-sleep voice, "I'm going to take a little nap."

I think he replies back with "Sounds good" but I can't be sure because I quickly drift off to sleep.

After about an hour I wake but it feels like I was only out for a few minutes. Feeling a little disappointed I notice that the bed is empty beside me, but Steve has thoughtfully pulled the covers up over my naked body.

It's dead quiet in the room so I know it's time to get my lazy butt out of bed. Even on vacation, there are still plenty of things to do and that's not going to happen with me sleeping all day.

Somewhat reluctantly I fold the covers back and climb out of bed. Once I'm standing I notice that Steve's bed is made so it's easy to see the small pile with a note resting on top. I assume it must be for me so I walk over and pick it up without even looking at the clothes underneath.

"Jimmy, I'm heading down to grab some breakfast. You looked so peaceful so I didn't want to wake you yet. I'll make sure to bring some food back up for you. I'm already showered and dressed and ready for the day so it's about time to put our little wager into action.

"Here's your outfit for this morning, or however long you feel you need to wear it to do your part. Go ahead and get showered and dressed and I'll be back up soon. From my thorough examination of every inch of your body I can tell that you're not in need of a shave;) This is going to be an interesting day!"

I finally look down and I see why the pile of clothes is so small. It's the skimpy, slutty French Maid costume that they left for me yesterday. It's a full ensemble, complete with insanely short skirt, white mini apron that would cover absolutely nothing, long sheer halter top, thigh highs, and a mesh & lace thong. And of course, the pair of black stiletto heels. Steve's not fucking around.

As I turn to head in to take a shower I notice that my heart is pounding in my chest, both from excitement at getting to wear this new, sexy (slutty) outfit and from the huge amounts of anxiety I'm feeling about what will happen when I'm seen with it on. Steve has assured me that everything will be fine so I try to grasp on to that so I can relax a little and get ready.

Not wanting to waste any more time I crank up the shower and hop in as soon as it's warm enough. Once in I quickly, yet thoroughly, clean myself up both inside and out, wanting to be ready for whatever the day might bring. I know Steve said his examination didn't turn up anything but I decide to do a once over with a razor to make sure I'm completely smooth from head to toe.

Sure that I'm smooth all over I shut off the water and step out to get dry and dressed...if you could call putting on this tiny little collection of barely there items getting dressed. Once dry I start by pulling on the thigh highs, followed by the thong. There's almost no point, since now that it's on I notice that it is extremely transparent. At least it holds my cock in place, tucked back in between my legs as much as I can manage. Next comes the little skirt which isn't a whole lot better.

The bottom third of my ass is visible and you can even see the bottom of the thong in front. Looking at it I'm happy to see that I've done a respectable job of tucking and, without looking closely, you can't even tell that I'm hiding a special treat inside.

Happy that I'm all set I head back into the main room just as I hear the door open and Steve cross the threshold. I can see the devious smile on his face as he turns toward me after closing the door. He grins and holds up a key card in one hand and a box which I assume has my breakfast in the other.

Quickly he offers me the box and says, "Eat up quick so we can get this show on the road."

I grab the box and start to head over to the small table to eat a little, although I'm really not hungry with how nervous I am right now.

While I'm getting settled he follows that up with his plans, "I snagged Ryan's key card while we were at breakfast. He's going to be down in the Casino getting an early start before we head out for the day. Ben is on his way to their room to shower and get cleaned up. Once we're ready you can sneak into Ben's room and I'll head back down to meet Ryan in the Casino. I plan to ply Ryan with some drinks so I can get him loosened up and talking!"

My eyes light up when I hear what Steve has worked out. I'm still nervous but now my lack of appetite has more to do with how excited I am at the prospect of surprising Ben. After a few more minutes at the table and a few more spent brushing my teeth and doing a last once over in the mirror I'm ready to head out.

Steve can't resist a light swat on my ass as I'm walking to the door, "God, with how you look right now I'm tempted to bend you over and have my way with you one more time before we head out!"

trybiman
trybiman
98 Followers