Expectations be Damned Ch. 02

I woke up with that gross feeling of makeup left on overnight. The warmth of my sweet seducers was nowhere to be found. In fact, it was quite cold as the covers were gone. As I attempted to reach for them I found my situation had changed quite a bit since my last moment of wakefulness.

I was tied to the bed, hands over my head and feet stretched to the lower corners. A ball gag stretched my jaw open. The silky lingerie continued to squeeze my skin. No one was in the apartment at all, just the aroma of sex from the night before mixed with the flowery scents I had used in the shower. How had they done this without me waking?

I had goosebumps all over me. Some traces of lipstick on various parts of my body. Every sensual moment of the life-changing evening ran through my thought-stream, causing me to stretch the skimpy pink panties that barely covered me. In my vulnerable state, I couldn't help but panic a little bit. And wonder what was going to happen next with all of this. I anxiously pondered what I would say when I saw those incredible women again. Oh, and when would they come untie me?!

I had plenty of time to work through all this, with no progress on what the hell to say when they arrived back. At last I heard a key turning in the door. I sighed with relief, but then my anxiety kicked back in. Oh God, what had I gotten myself into?

The door opened, letting in more sunlight than I was ready for. As I squinted toward the threshold, I realized the silhouette that stood before me wasn't anyone I recognized. An audible gasp escaped dark painted lips.

"Oh, hi there," the plump woman greeted bashfully.

She seemed to be in her early thirties, carrying a vacuum and rolling a wheeled trash bin into the room. Her pale skin reflected the sunlight radiantly. She wore a conservative uniform for her cleaning duties.

"Sorry if I'm interrupting something," she said smiling. Her confidence seemed to grow as she realized I wouldn't be answering her and obviously posed no threat in my current state.

I grew red and hot like a bowl of tomato soup. She really just stood there grinning, taking in my scantily clad and thoroughly embarrassed visage. I couldn't think of anything to even try to say, not that it would have been intelligible through my gagged lips. My cock began to swell even more at the humiliation I felt from being exposed to her so suddenly.

"I'll be out of your hair in a minute honey," she assured me nonchalantly before pausing thoughtfully. "Speaking of hair though..."

She walked over and gently brushed my messy hair off of my face. Her touch was tender, and I could see her wheels turning. Deciding if she should take advantage of me as I lay there helpless. "There we go, now I can see your pretty little face," she declared.

I was terrified and it showed in my eyes. She took pity on me, shrugging and getting to work with her duties. As she went about her weekly cleaning, she glanced over now and then unable to keep a smile from her face. She brought out my discarded male clothes from the bathroom and folded them, setting them painfully just out of my reach. Her work was done in a matter of fifteen minutes. Everything was clean in the place except my filthy body and slightly smeared face. Before she left, the teasing cleaning lady blew me a kiss and smiled knowingly. She closed the door behind her and I was alone again.

..............................................

MARA

"I can't believe you forgot about the cleaning lady," Caroline scolded angrily. "Our poor boy was left here all alone and exposed to a stranger! You know how sensitive he is about his dressing!"

I couldn't quite hold back my chuckle, but really I was truly concerned. It was obvious Caroline was taking this more seriously than I thought. "I'm sorry! I usually keep it pretty nice in here so I barely notice when she visits. It was an honest mistake," I lied. There was no way I could tell Caroline that I had done it on purpose now that I saw how pissed she was.

We'd only known each other for about a month and a half, mostly just talking on Fetlife. I was starting to feel bad for what I did, but I mean my sense of humor has always brought trouble from these sensitive types. I know our little slut just loved it though. I could tell by the way she blushed through this whole conversation. How hard her little clit was from the moment we got home.

"I'm honestly okay," the still tied up girly-boy defended, recently ungagged to tell us the story.

"Good bitch," I thought.

I had to admit I was starting to like her. I'd taken so many little sluts through the works at that point, but I hadn't really seen one so delicate and open with her emotions. Something about her undisguised struggle and exposure really got me off. Maybe the other ones were just more experienced or something. But nonetheless, that little show the two had put on the night before was really sweet and touching. Thinking back, I still had a little tear in my eye.

"Whatever, just be more careful with him from now on," Caroline replied, her anger slowly subsiding. I figured I'd pretty much dodged the bullet.

"I will, I promise!" Okay, now how do I steer this back to playing with our toy?

.........................................

CAROLINE

I ran my fingers across my sweet new boyfriend's tummy. He was so cute all tied up there, blushing naturally. Oh that poor baby, having to go through the maid coming and ogling him almost naked there on the bed. I had to admit it kind of turned me on to think of it, but I have to be careful with this boy. He's so new to this and I could tell he was just scared to death, even if he downplayed it while we were arguing. If anyone knows how anxious he can get, it's me.

I was finally calming down, but I had asked Mara to give us some alone time so I could make sure he was okay. I don't know about that girl. She's a lot of fun and I can't thank her enough for what she did for me, but she has such a tendency to be reckless.

Moving up to his face, I wiped off Charlie's smeared makeup with a gentle smile. I was straddling his body seductively while I did all of this and I know it was driving him wild. Every now and then I would bring my crotch down to barely touch his dick, causing him to moan a little bit. I couldn't help but be just a little bit evil while I took care of him, after all I think he really likes a bad girl. I know I can make that fantasy come true for him. I've been practicing my bitch voice and have to say it's coming along quite nicely.

It's been a week now since that first night together and everything is coming along nicely. I have special plans for him tonight. He's supposed to come over to my place at 8 o'clock sharp! I can't wait to show him what I bought for him. Maybe I splurged a bit but darn it, I just can't help myself when it comes to him. Last week after we got started I ordered all kinds of feminine body padding for him to wear. It's gonna fill out his figure so nicely. Complete with a pair of double D breast forms. He's gonna love it!

.......................................

CHARLIE

I stepped out of the yellow cab at 7:35, shutting the door hurriedly behind me.

"Good," I thought. "I have twenty five minutes to calm my nerves before I knock on the door." I had been instructed by Caroline to wear purple panties under my normal clothes. I don't know if she expected me to already have variety or something, but after work I had rushed off to the strip mall to search something out. It was absolutely humiliating.

I browsed around the store awkwardly, trying to walk past the women's section as if I were on my way somewhere else. But I had the feeling eyes were on me as I looked over at the most risque items. Eventually I found what I was looking for, grabbed them quickly and made my way to the front. I feel that this maneuver was especially noticeable in hindsight.

Waiting in line I tried my best to hide them in my hands, but there was nowhere to put them. I actually ended up picking up a nail trimming kit from the last minute items shelf just to look like I was buying something else. I swear the sales girl knew they were for me, but I had to follow my Mistress's orders. She could be really pushy and direct. It kind of surprised me. If I had any doubts, right before I walked away the sales girl lingered as she place the panties in my hands and gave me a wink. I speed walked out of there, looking like a fool.

I knocked on the door at 8pm exactly. My cock was rock hard, but I left it bulging out for Caroline to see. I knew she would like that.

The door creaked open, warmth spilling through the crack from the inside. It was her warmth. I saw her smiling at me affectionately and blushed. She changed her demeanor suddenly.

"On your knees, bitch," she said shortly. I dropped to my knees right there in the doorway, still visible to the outside world.

"You may crawl inside," Caroline suggested. I followed suit and was soon behind her closed door. "I'm all hers now," I thought with a feeling of relief.

"Did you follow my instructions?" she asked in what I had begun to refer to as her Mistress voice.

"Yes, mistress. Thank you for helping me choose what to wear,"

"Hmmm, Let's see." She seemed to be a bit more playful now. It really was strange how she could switch it up in a second. I couldn't decide which side I liked better. She pulled up my shirt and slid her hand down into the back of my pants, making as much contact as possible. I felt like she was taking in the feeling of my skin as she felt for my panties. Then she yanked the top of them up into her view. I gasped daintily at the sudden wedgie of her panty-check.

"Very good, little girl," she cooed. Mistress patted my butt and then commanded me to strip. I took everything off except the purple thong panties with lace trim and a small pink bow. As she continued to caress my cheeks she slid something around my neck. It was the same collar I had come to know over the last week. Grabbing the lead, my lady pulled me into her living room still crawling on all fours.

When we arrived there was a box sitting on the floor. Purple with a big pink bow. It was actually quite a large box and had a little yellow tag attached that read "Krista".

"Well, I think you know what to do."

I excitedly began untying the bow to find out what secret waited inside. As I moved the tissue paper aside I began to blush uncontrollably. On top was a pair of giant breast forms. I couldn't believe it, she was going to give me tits that would bounce around as I fulfilled her every command. Looking deeper into the box, I found more padding, all designed to give me a feminine physique that would make any girl jealous. Every bit of the squishy padding emulated my skin in every way.

She had matched my skin tone perfectly! I couldn't believe it. She must have spent a fortune on these.

"Thank you so much Mistress!" I gushed enthusiastically. I wanted to play coy but this was just too much. More of my dreams come true.

At the bottom of the box I found a bottle of adhesive made specifically to gently stick it all on.

"Let's get started," Mistress Caroline whispered.

..........................................

CAROLINE

There she was, my perfect little cutie all tied up. Legs in the air. I had found this bondage technique in a video online. These cute gay guys showed me humorously how to suspend the legs by tying them to each other, routing the ropes firmly around the neck and under the shoulders. She was open to my plans, and not just because of my newfound rope skills. I could tell she was an eager and willing slut for me.

Her lips pink and eye shadow a deep and bluish purple. Those lashes that seemed to lead all the way from the sky to her nervous green eyes. She didn't need any blush, for obvious reasons.

I was starting to learn that despite my eagerness, sometimes the sexiest thing to do was wait. So I stood there, watching her melt under my gaze. My pussy grew wet in its container. I looked down to see my feeldo strapon cock dangling from the harness. I admired the longing that I felt to be buried inside her as it rose before me. Such a lovely feeling, less menacing since I knew I had control. I could just follow it as a thin tendril stretching into her own cute little head, full of matching desire on the other side. Tying us together in a shared inevitability. Oh yes, everything was right. 100% Yes. Now to set the mood.

"Do you want my dick inside you sweet girl?"

"Yes, Mistress."

"Hmm, I'm not so sure you really want it. Tell me more little one."

"Mmm...mmistress, I need your cock inside me more than anything. Please fill me up and take me!"

"So you mean to say you have a greedy little hole and you feel empty without me?"

"Yes Mistresss, pleeease!"

I just loved playing with him like that. Call me corny, but I walked away slightly from his lust and dropped the needle on a Marvin Gaye record. Sweet love makin' music. Then before either of us could think I was against his entrance, hands on his hips ready to work my way in. I looked down to see panic on his face.

Puzzled for a moment, I wondered why something didn't feel right. Oh! Silly me, I was so excited I almost forgot to lube him up!

"I'm so sorry baby!" I gushed without considering my usual domineering facade. "Get control of yourself girl," I thought as I reached for the lube.

Back in my moment, I slowly worked the slippery liquid into his little hole. Her little hole? Mmmm yes, hers. I liked to see my baby that way when she was all done up. After all, what was all that work for anyway? I was enjoying the feeling of her delicate skin against my fingers. As they slid around in the oily texture. I smeared it onto her hips, wider than they would be naturally. But the pads were on there perfectly. And the texture felt just the same.

Yearning for the electricity of true skin, I allowed my slippery fingers to fondle her girl cock. This definitely had a response. I chuckled to myself, not terribly surprised. As my gaze drifted back to her face, I leaned in for a kiss. At the very same time my dick rubbed against her. Right as my lips met hers, my dick met her entrance. She moaned sweetly. I devoured her lips, nibbling with my teeth.

"Are you ready now, baby?"

"Mhmmmm"

I could barely hear her response but it released the tiny bit of resistance that was holding me back, like a hair trigger. I slid into her tight opening, slowly. Gently. Decisively. She needed my direction, poor thing. I remembered all the times she had looked at me and shied away in our early days of knowing each other. It was so clear to me she liked me. Back then I just couldn't be sure she was a she? I thought it was extremely unlikely. I mean how many guys could really be that freaky?

Returning to myself again, I became aware what exactly I was filling her with. I was filling her with me. And so began to think just the sweetest thoughts I could, pumping slowing in and out of her still. My lips against hers, then on her neck. Her goosebump surrounded nipple. I bit it sharply. It was only then I realized it wasn't her actual nipple.

Krista felt it somehow though. She inhaled deeply in a quick spurt, and I was ready. At that moment I filled her with my breath and my cock together in unison. I just kept filling her with me. So pliable she took me inside her. My stomach rubbing against her girlcock as I picked up the pace. Her double D breasts began to bounce with my rhythm.

"Awww, baby. You're taking my dick so good."

"Mmmm, thank you. *Squeak* Thank you Mistress. You fill me so perfectly. I just want all of you in me. Your perfect feminine essence."

I smiled at him playfully, reveling in his compliment. Keeping up the rhythm. Laughing a little bit at his innate girly mannerisms. His innocent eyes fixed on me.

"Alright Shakespeare. Enough talk. I wanna hear you squeal."

I picked up the pace again. The animal in me taking over. I would push all the way in. Moving the little piece behind the harness that pierced me so I could feel it too. I gyrated against it before pulling out and plunging back in again. And squeal she did. And holy shit was I moaning too. My pussy began to contract and squeeze as I was filled with immaculate orgasm. I rode my climax through and was working toward another, insatiable.

I grabbed her clit and stroked it up and down, matching the pace of my fucking. I could feel it pulsating, filling with more and more blood. It was already stretching the bonds of it's skin. Impossibly still pumping fuller so I thought it would explode. Well, I wasn't wrong. She couldn't last through much of this before my sweet Krista began clamping her pussy around my cock, her big clit erupting sweet milky liquid all over her body. This unbelievably sexy display cause me to reach my second climax as I ground the hilt against her. Finishing every last drop of her cum. I smeared it onto her skin. Took a nice bit to decorate her slutty face. And smiled deviously.

Deep inside her, I moved my mouth to hers. Just resting my lips against her lips, completely still and spent. In utter ecstasy, fulfilled again. I rubbed my lips on hers gently, then licked her cum off her face possessively.

"I'm so glad you're mine, Krista."