Stretching Routine

Yvonne's gift had been taunting me all morning. I tried being a good employee and get some coding done, but it's not easy staying focused when you have a giant butt plug lying on your desk.

Since I'd figured out a month or two ago that anal wasn't all that bad actually, Yvonne had lost no time exploring how deep that particular rabbit hole (pun not intended) went with me. The answer: Surprisingly deep.

By now I happily took plugs that would have made me balk in terror at the beginning and it had come to the point that I was even a bit disappointed if Yvonne didn't fill me up in some way during one of our sessions.

This plug was different. At a straight four centimeters in diameter (yes, I checked, you wouldn't be able to take your mind off it either) it was twice as big as the largest insert we'd experimented with so far, and since it was made of smooth stainless steel, it was going to have zero give going in. Yvonne had assured me that there was no safety concern and I believed her, but that didn't help much against my trepidation.

Still, I was determined to give it a shot in the evening once Yvonne was home. She'd promised to eat me out if I managed to get it in and that was too rare a treat to pass up on. We both agreed that I was much more adorable and sexy when I didn't get to release the tension too often, but that didn't mean I'd say no to an extra orgasm from time to time. Also, while Yvonne wasn't all that keen on giving head, she was crazy good at it.

I didn't rate my chances of success all that high, though. My didn't have much experience yet and it was still a bit of a struggle to get our (until now) biggest plugs in. Maybe I should loosen myself up a little in preparation. Or maybe I shouldn't? Was it a good idea to play with sex toys during work time? Probably not. But I was already distracted anyway, so I didn't have much to lose.

During lunch break I got my trusty princess plug and a bottle of lube. My panties would not appreciate what I was about to do, but that problem could be easily fixed by leaving them off and putting a folded towel on my chair. The nice thing about working from home was that a clothed upper body was enough to keep up appearances even during video calls.

I was still glad that there were no calls today. By now I was used to wearing the princess plug for extended amounts of time, but sitting down on it meant there was no escaping the pressure. I was also far too horny for my own good already. That wet spot slowly growing on the towel wasn't just lube.

Needless to say, I didn't get all that much done in the afternoon. Still, I was good enough at my job that even at my worst I was still producing passable code, so nobody should have noticed. It was one of the great injustices of life that I made more than twice Yvonne's salary while working fewer hours and not even having to leave the house. At least she got an eagerly submissive girlfriend out of the deal, and since I could take care of all the bills, that left her free to use her money on such import investments as this weapon of ass destruction here.

When I took the plug out at the end of my work day I questioned the prudence of my little adventure. During the last three hours I'd been far too horny to realize how sore my ass was getting and even the best lube didn't stay slippery forever. I had to grit my teeth as the plug came out and my ass kept throbbing with a dull ache. Yep, definitely not one of my better ideas, but it was too late to change it now. I relaxed my sphincter as much as possible while I cleaned up behind me so Yvonne wouldn't see what a naughty girl I'd been. Maybe it helped, maybe it didn't. Either way I'd have to work with what I had.

Yvonne came home around five, and while she noticed that I was giddier than usual, she chalked it up to my anticipation. All throughout dinner (I made us a light chicken salad; the last thing I needed today was a stuffed-full belly) she kept shooting me these hot sultry looks of hers and playing footsies under the table. When we were finally done eating I was so ready to become her perfect little plaything.

"I think it's time we had a closer look at that present I got you," she said once I'd finished cleaning up the dishes. "Your face was so adorable when I gave it to you this morning. You must be dying to finally get to play with it."

"Yes, Ivy," I replied, using the nickname that signaled I was ready for whatever games she wanted to play. As I washed the plug and carried it after her into the bedroom, I cursed myself for tiring my ass out with the princess plug earlier. It still ached a little with every step. This didn't bode well, but I wasn't going to disappoint both Yvonne and myself by not even trying.

When I came in, Yvonne already sat on the bed, somehow managing to loot like an Empress on her throne even though she'd changed into a baggy shirt and comfy pants. My thighs clenched involuntarily at the implication. Yvonne sometimes kept her clothes on during sex if she wanted to really lord it over me who was in charge here. As if to prove my point she pointed at a hard wooden chair with her toes. "You know what to do."

"Yes, Ivy," I repeated and took off my clothes. We'd been together for a good half a year now but I still couldn't help getting a little self-conscious when she fixated me with such an intense stare as I undressed. I pushed through the awkwardness and made sure I didn't cover myself or turned away as one piece of clothing after the other dropped to the floor. My body was great and my girlfriend was great and they both deserved each other!

Once I was fully naked I sat down. The familiar feeling of the cool, hard wood pressing against my skin conjured up flashbacks to all the other times Yvonne had made me squirm in this chair. We'd barely even started and I was already ridiculously horny. When I spread my legs to give Yvonne a perfect view of my body, my thighs already felt sticky.

"What are you waiting for? My present is still missing a nice layer of lube."

I was about to get up again to fetch the bottle of lube, but Yvonne put a foot on my chest and pushed me back down onto the chair. "Stay! You already have all the lube you need at your disposal."

Heat washed over me. Surely she didn't mean... but no, that lecherous smirk was unmistakable. "It's so big," I pleaded hopelessly. "It's gonna take forever."

"Do you have any other plans tonight? Because I don't."

I didn't argue any further. Yvonne had decided she wanted so see me squirm, so squirm I would. I reached between my legs and let out a little gasp when it hit me how horny I was already.

It was a sexy little game we'd come up with a couple of weeks ago. A fun way to make use of the particularities of my body. You see, I get wet easily. Like, really easily. It barely takes any foreplay at all to open the floodgates, especially when the tension has had several days to build up.

In the beginning Yvonne had struggled with feelings of jealousy and inadequacy because her body wasn't as cooperative. She'd half-jokingly told me that this ability was wasted on me since I didn't like penetration anyway (never managed to make it feel anything other than kinda weird and uncomfortable; it's a major contributor to why my bisexuality has shifted further and further towards one end of the spectrum over time). Then I'd said something along the lines of "at least I'm a good lube dispenser" which had let to some curious experimentation and the result that, yes, I can be a lube dispenser. Not a good one, mind you, as I need to tease myself forever to get the quantity needed for anal play, but with the right mindset that bug can be made into a feature.

I slowly circled my fingertip around my clit. Better pace myself now or it would be so hard later. Hell, it would be plenty hard whatever I did. By the time I'd finally produced enough wetness to fully cover that monstrosity, I'd be half delirious with need.

At first I tried running the plug between my folds. For about a microsecond or so, before I shrieked and ripped it away again. Fuck, that thing was cold! It had felt pretty normal in my hand, but that didn't count for much once you placed it onto more sensitive places.

"That was kinda adorable." Yvonne chuckled. Well, at least my blunder had been good for something, even if that something was just Yvonne's amusement. I closed both my hands around the plug to warm it up. It was crazy how much space it took up between my palms. This monster was supposed to fit inside me?

When I'd finally gotten the steel up to a comfortable temperature, I ran it between my legs again. It didn't feel half bad to drag that big, smooth thing between my folds, but predictably all my available wetness barely put a shine on it. I was going to need more. Much more. I put the plug down on the chair (its cutesy heart-shaped base was flat enough that it could stand upright on its own) and got back to circling my clit.

It didn't matter how much I tried to pace myself. Yvonne's intense stare at my hot, naked body and the knowledge that I'd have to tease myself for God knew how long drove my arousal through the roof. Already my clit had started with those sharp throbs that left this weirdly floaty ache as a signal that it was getting oversensitive. Every time my finger brushed over it directly, the sensation made my head swim for a moment. Despite the room being warm at best, I was already sweating. At least my heightened state brought with it copious amounts of wetness.

From time to time I stopped to gather the sticky fluids up with my finger and smear them over the plug. It was starting to get a nice shine, but it wasn't even halfway to a point that I'd call a good coating. And I needed at least a good coating if I was to stand any chance to slide it inside my sore ass. Distracted by this thought I slipped up and rubbed my clit much harder than intended.

"Careful there, we don't want any accidents," Yvonne teased me as I tried to calm myself down with slow, deep breaths. Fuck, that had been close! I'd already felt the first contractions starting, and now that my clit realized there would be no release after all, it punished me with a hot, almost itching sensation. The need cornered my mind. Had it really only been four days since my last orgasm? Usually it took me at least a week to start getting desperate, but I was already tempted to just give up and beg Yvonne to let me finish.

Not that I would actually do that, of course. I was a good girl after all and good girls didn't complain about their sexy punishments. So I gritted my teeth and tried not to let the burning need take over my mind as I very carefully traced my fingertip around my clit again.

"Are you close?" Yvonne asked innocently. She was looking down at her nails, knowing perfectly well what her feigned disinterest in my plight did to me.

"Yes," I moaned. I was so incredibly close. Every little touch was becoming torture, but I kept going anyway and not just because Yvonne had told me to. Teasing myself was intense, but it was also the only outlet I had. Stopping all touch and suffering the frustration with zero stimulation would be so much worse.

"Aww, you poor thing. It must be so hard, having to edge yourself just for a few drops of lube."

I groaned and briefly slowed down to a stop. Yvonne's mock-sympathy had almost sent me over again. It was just too hot when she was this sadistically cruel to me. And she was far from done yet.

"You look like you could use a little help. And I know just the thing that never fails to get you all drippy." She stood up from the bed and leaned over me, closing her lips around my nipple.

I almost died right then and there. My nipples are crazy sensitive and Yvonne sucked like it was a drinking straw and she wanted to get the very last drops out of her cocktail. I clasped my hands over my mouth so I wouldn't scream as I felt my nipple stretch under the force of the suction.

"Don't stop touching yourself," Yvonne said, taking a quick break from torturing me. "We want to go for maximum production, don't we?"

"Yes," I managed to get out. Yvonne wasn't sucking right now, but the way she ran her tongue all over my breasts and nipples was no less mind-melting. I reached between my legs and yelped when the sensations hit me. The combined assault on my breasts and pussy was too much. I bit down on my other hand in a desperate attempt to get a grip on myself and not explode right then and there.

"You're far too tensed up," Yvonne teased me. "Aren't you having fun?"

"I am," I mumbled through my hand. "But it's hard."

"Of course it is. It wouldn't be fun if it was too easy." Yvonne licked one nipple and flicked the other with her finger at the same time, making me yelp again. "Just try to relax. And don't forget to breathe."

Right, breathing. Maybe I should start doing that again. I took my hand out of my mouth and forced myself to take deep breaths. It helped, at least a little. My other hand was still between my legs, barely moving because any sudden touch of my clit might send me over, and the need was no less intense than before, but I slowly felt myself getting in control again.

"Good girl!" Yvonne's smile made me melt even more. She, too, reached between my legs and I sighed with bliss as she ran her fingers between my folds. When she brought her hand up again, glistening strands of my juices hung between her fingers like the world's sexiest spider net. "Look, it's working!"

She wiped her fingers on my chest. It took me a moment to realize what she'd just done. That was so much lube she'd wasted there! "Hey!"

"Is there a problem?" she asked in her sweetest voice.

"No," I said, quickly gathering up my remaining wetness before that, too, could be taken away. Yes, Yvonne was being unfair, but she was also right: It wouldn't be fun if it was too easy and fair. Even if it meant that that I'd have to keep edging myself even longer.

Several more hot, sweaty minutes passed. Both of my nipples were tingling from Yvonne's skillful tongue and the tension was absolutely killing me. As much as I tried to keep my breathing steady, every time my clit twitched it threw me off balance. I had become so sensitive that I could barely touch myself at all and my whole lower body was throbbing with need.

It was effective, though. God, was it effective! My pussy was gushing continuously. As much as I tried to gather everything, there was a big stain on the chair already that I'd have to clean up later. At least the plug was coming along nicely. It's surface sparkled evenly as I rotated it in my hand. Even with gravity against me and a good part of my juices uselessly flowing down to the base, there was still a thin slippery coating over the entire thing. Not as much as I might have used if Yvonne had allowed me the industrial lube, but every time I'd used a similar amount of my juices on the princess plug it had popped in without much struggle.

Of course the princess plug was much smaller and I needed all the help I could get, but the thought of milking myself even longer made my stomach churn. My clit was absolutely killing me and I could only pray that I'd get the plug in and earn myself the reward. I doubted that I'd last more than a minute once Yvonne started to eat me out, but that didn't matter. The orgasm would be glorious either way. If, on the other hand, I failed... no, I couldn't allow myself to even think about it. I needed that orgasm. If I didn't get any relief from that acidic burn in my clit, I might just die.

"Let's do this!" I tried to feign a little confidence, but I couldn't even fool myself. My voice had to sound just as desperate as I was feeling.

Yvonne returned to her vantage point on the bed. I thought it would be a bit easier to think straight now that she wasn't teasing my nipples anymore, but my breasts didn't like that sudden absence of stimulation either. My nipples were uncomfortably hard and the need to grab my breasts, play with them, really dig my fingers into them, was only topped by how desperately my clit screamed for more when I stopped touching it.

No matter how desperate I got, I would never finish myself off without permission; Yvonne's good girl wouldn't do that. But if I didn't get that orgasm, I wasn't going to get much sleep that night. There was no way I'd be able to keep my hands to myself in bed, even knowing that it would only make things worse.

I got off the chair, intimately aware of the squelchy sound it made as I lifted my hip. That was no stain anymore, it was a little puddle. My thighs were all sticky as well and it didn't help that the ordeal had heated me up to the point of sweating all over. I'd so need a shower later.

I got down on all fours, my back to Yvonne so she'd have a perfect view. Theoretically it might have been possible to try and get the plug in while sitting on the chair, but it always felt so much easier when I was in this chest-down-ass-up position and I needed every advantage I could get. Also, I doubted that Yvonne would mind the extra eye candy.

It felt like in the few seconds since I'd left the chair, the plug had lost at least half of its lube. Or maybe it was just my nerves playing tricks on my mind because I was one hundred percent convinced that I'd never manage to fit that thing inside me. However, I'd felt the same way about the first plugs we'd tried and those were so small that I barely even noticed them anymore. So maybe, just maybe, Yvonne was right and I was actually ready to graduate to this big boy. Well, I had to be. My reward, and by extension my sanity, depended on it.

I wetted my finger between my legs again before reaching down to tease my back entrance a little. Just as I'd feared, I was still sore from my earlier escapades and my ass didn't appreciate being played with again so soon. Still, my finger slid in without much issue. I slowly pumped it in and out a few time, trying to spread my juices as evenly as possible.

Then it was time. I couldn't stall any longer, especially since the plug was only going to get less slippery. I placed it right against my hole and slowly started to apply some pressure.

Fuck, that thing was big! I barely made any progress and already my sphincter felt like it was reaching its breaking point. The princess plug felt similar, but only for a second or so before it popped in and my ass could relax around its thinner base. Here, however, there was no end in sight. That thing was only going to get wider and wider until my ass exploded.

It brought back vivid memories to the first time Yvonne had used a plug on me. It had been so tiny in hindsight, and yet it had felt monstrous and there had been this weirdly uncomfortable feeling, something between a dull ache and the need to take a big shit as my body was unsure what to make of this new sensation. This plug was turning me into an anal virgin again.

I allowed myself to relax for a moment, even if that meant that the plug slipped all the way out again, losing what little progress I had made. It wasn't like the attempt would have been successful anyway.

"Looks like there's still too little lube." There was a mocking tone to Yvonne's words that cut deep into my soul. She knew exactly how to push my buttons.

"Please!" I wasn't even sure what exactly I was begging for. All I knew was that I didn't have the willpower left to edge myself even more. As much as I wanted to be her good girl, I was far too close and my pussy throbbed and clenched already like it had a mind of its own. If I started playing with myself again, I'd go over for sure, disappointing both of us.

"Don't worry, I'll help you a bit." I heard Yvonne standing up again and a second later she took the plug from my hand. I got ready for her to try and stick it in, ideally after a little help from the lube bottle, but instead she crouched down beside me and leaned in until her lips brushed against my ear.