Kelsey's Predicament

She saw how big it was and said, " I can't believe anyone would shove that up their butts!"

I said, "it does fit," with an embarrassed smile.

"Let me see it," she demanded.

I said, " you are LOOKING at it!"

"No! Not in your hand...in THERE."

So I stood in a cloudy haze of embarrassment as I put it in my mouth to wetten it. I turned slightly away from her, she wanted to see it. I lowered my panties and bent slightly. Slowly, I worked it in until it was in all the way to the lip of it. Her eyes were ablaze. I'm sure she'd never seen anything like that, certainly not from me.

"How does it feel? What's that like?" she said, bombarding me with questions.

"It feels full...but good, you know?"

"How can that feel good?"

"It feels like...I don't know...like a reminder of my sluttiness. I mean, you can't move without feeling it, but it doesn't hurt, per se, it's more of a fullness. It just feels like...something is supposed to go there."

"Wow. It looks...wicked," she smiled, her face flushed. "You should keep that in, while I'm here."

"What? Why?"

"Because I want you to!" she said, playfully stomping her foot. "But seriously, you need to get ready for...that, just in case."

"Ok," I peeped, embarrassed to be bossed around by my best friend in this way.

I had to wear it around the apartment as well as at lunch. I was reminded I was plugged as we both ate burgers in the Wendy's parking lot. She kept asking how it felt.

"Right now it's kind of starting to hurt," I said honestly. I saw her look of concern. "Don't worry, it's a good kind of hurt, kind of what I'd expect it to feel with a girthy cock in there," I smiled, barely able to look at her in my shame.

She made me wear it until I had to use the bathroom, hours later. I felt stretched and sore. I'd actually considered bigger ones at the adult store, I was kind of glad I had chosen this one. She made me take it out with her watching intently. Maggie and I were entering a whole different phase of our relationship. I wasn't sure I liked it yet!

She kept reassuring me, though, she kept saying everything would be fine, it would work out. She was there to help. She even said, "you are going to NEED some help with this one," in a mysterious way. I swear all this was exciting her. I had to admit, the thought of being used again...by a stranger...if it was similar to the last time? Whew...I got wet every time I imagined it or remembered it. It kind of freed me, now that I knew that she'd be around to help keep it safer.

A week went by with nothing, no texts, only constant, gnawing, excited anxiety over not knowing if anything would happen again. Maggie was "training" me, forcing me to wear the butt plug for longer periods. It was especially embarrassing when she'd take me shopping and make me walk what seemed like miles in the mall, all while feeling that pressure in my ass. She seemed to take impish delight in making me do it. We got deeper into my kinks, my desires. She seemed especially interested in my love of blowjobs.

"Isn't that gross?" she asked, her face contorted.

"Are you kidding? It's fantastic. That soft, velvety head in my mouth...the juxtaposition of the softness of the head, the skin, the balls, to the hardness of the erection. Plus, the total feeling of control. I have the power, I'm the one giving pleasure. There's nothing gross about it. At the same time it's also the height of submissiveness, that it's ONLY about his pleasure. It touches all my hot buttons."

"But what about the...cum," she said, almost choking on the thought of it. "Isn't it...yucky?"

"Well, it's not chocolate!" I joked. "But honestly, it's not bad, it's not bitter, usually. If you can drink beer, or drink black coffee, you can swallow that and the consistency isn't any worse than cough syrup."

Her face was still puckered, as if she was sucking on a lemon. "Hey, maybe it's not for everybody, but it sure is for me," I smiled.

"I'm not trying to be...a prude or anything. This is kind of why I'm asking...Brian wants me to...you know...do it more to him. I WANT to like it."

"But you've tried?"

"A few times, yes...I never let him cum that way, though."

"My advice then is, do it more often, take it slow. Build up to it. Honestly, I don't think I enjoyed it at first either. But after getting guys off that way, and discovering its wonders, well, I can say I'm now a big fan."

"Ok," she replied bashfully. "So no news on the blackmail front?" she said, attempting a joke.

"No, I haven't heard a thing since that one picture. Maybe he's happy with what he got."

"You sound a bit...disappointed," she smiled.

"I'm not...really...well maybe a little. Every time I think back to what happened I get wet. But the fear, the anxiety, the uncertainty, it's all still there. I feel like I'm on edge all day."

"Well, I have an idea that might help. You know your rowdy neighbors are having a party this weekend. They left a flyer on the door."

"Oh god, what's your idea?" I said reluctantly. We'd already discussed what we thought those college boys would've done to me, if they'd found me tied up like that.

"Oh, don't worry, I'm not talking about any gang bang thing. I'm talking about discovering your elusive "lover." I have an idea how to flush him out."

"Wow, really? That'd be awesome! How?"

"Well, you know that we think he's someone we already know, someone from around here? We should go to that party, flirt a little then...well, get some of your anxiety worked off...in the manner in which you enjoy."

I loved the way she talked, "in the manner in which you enjoy." She couldn't just say, "just how you like it." "Oh god, Maggie, what? what?"

"Well, we are assuming it's someone we know, someone from around here. I'd bet it's one of our friends, or neighbors. So why don't we go to the party, you chat, you flirt...that might get, "whoever it is" interested. Then, you got do your "helpless bondage thing" somewhere and we see if he shows up to take advantage."

"You think that would work?"

"I believe if it's actually one of the guys at the party, yes, I believe he'd keep close eye on you, wherever you go."

"But how do I do it? If I use the laundry room again who is to say those college dudes don't all find me down there and..." I shuddered at the thought.

"I don't know, that is YOUR thing, I'm sure you'll figure it out. Wear something sexy...which is a no-brainer for you, flirt, then slip away, put yourself in one of your predicament situations and see what happens. I'll be around too, remember. That way I'll be able to catch him in the act!"

"Well that is a bit more comforting, knowing you'd be able to keep it from getting out of hand."

"I didn't say I'd stop it," she grinned mischievously, "but yes, I'll make sure you are safe."

I had that typical conglomeration of anxiety and arousal, the buildup was putting me on that sexual edge.

She came over late Saturday afternoon, pre party. She rummaged through my wardrobe trying to help me find just the right outfit. She wanted something for advertising. I couldn't help, I didn't know if she wanted full slut mode or classy, demure, girl next door, sexy. It was late summer, and there was still enough warmth to wear anything she wanted. She chose a cute, pink spaghetti strap top and soft, silky running shorts which she thought highlighted my ass nicely. I was a bit suprised by the "no underwear" rule she laid down. My nipples were going to show, but she wanted that.

"How is any of this going to get me...in a compromising situation, or find out who "Mr Girth," is?"

"Trust me," she cooed. Lightly, she brushed her hand across my tits through the material, causing my nipples to rise to the occasion. "That's more like it," she grinned.

I should've surmised it but, just before we walked over to the party she shot me the most evil, sexy grin and told me to bend over.

I sighed. I should've known. She peeled my shorts down over my ass. I heard her sigh. "That fucking ass, Kelsey, JESUS." I heard her lubing the plug up with her mouth before she worked it slowly into my behind, with my help. I was already in such a state of lust, this only ratcheted it up another notch.

"Yes, I want you to feel that the whole time you are talking to guys, wondering if they are " the one," or what they might do to you if they discover that secret."

The first hour of the party was uneventful, Maggie hung out close to me, we talked to pretty much everyone that was there except for my "crazy eyed" nearest neighbor. I shuddered to think that maybe it was "him."

The beer was flowing by now, the guys were getting liquored up and their flirting became more sexual, many of them pointing out my obvious "points" sticking out. Maggie just laughed and encouraged them. She didn't allow me to drink, however, she wanted me to experience whatever was going to happen, clear headed. I was kind of wet already, with each guy chatting me up, my butt plug causing me to throb, all the while wondering if this was going to be THAT guy.

After each guy she'd pull me aside and ask, "Do you think it's him? Did he say anything to make you wonder?"

"Honestly, pretty much all of them said something sexual, especially the drunker they get. No one has tipped me off, though."

She smiled, "it's ok, we have all night." I noticed she was spending less and less time around me. I think it was because she wanted whoever it was to have more chances with me. That left me with the vultures. They were circling around me like roadkill. Being short, they all could look down. It was a good vantage point to see down my top and see that I obviously wasn't wearing a bra, if they couldn't already tell by my nipples.

"Fuck, I need to get laid," I whined in my head. The butt plug, the situation were removing my last vestiges of defense.

Two hours in I was so worked up I actually thought about going back to the apartment and getting myself off, to take off some of the edge. Maggie interrupted by whispering in my ear, "it's time, go do your thing."

"Really?" I whined. It was all a pointless act, I knew I was going to do it, I knew I wanted to. All week I'd exhausted ideas on how to do it, how to put myself in that kind of predicament. All the while realizing that it was going to be a large party, with so many guys just hanging "around." It needed to be somewhat safe, while still being close enough to reel someone in. I found the spot and the idea, which always excited me.

As covertly as possible, I slipped out to the parking lot. I walked to the very end, by the dumpster. There was a service truck parked next to it, belonging to the complex. I walked around back to where I'd already had things prepared. I slipped off my top and my already hard nipples reached a new level of excitement upon being hit with the cooler air of the evening. I wanted them free, easy access, if I was "caught."

I'd already stashed a bag under the truck. I took out the handcuffs, the metal kind. I just wanted this time to feel more raw. I didn't bother removing the skirt, it was no obstruction, all anyone had to do was just flip it up and go to work, since I wasn't wearing underwear.

After an earlier discussion with Maggie, I took a blindfold out of the bag and put it loosely over my eyes. We figured that we didn't want to "scare" anyone off. It was better him think that I couldn't identify him. I'd purposely left a little space at the bottom to be able to peek out. Finally, I lifted my arms and cuffed myself to an eye bolt on the truck's loading door. It was well above my head. It was one of my favorite ways to be bound, standing, hands above my head. It was a favorite fantasy of mine. One thing I'd misjudged, though, was how high it was. It made me have to reach, it put me on my toes.

I could feel the cold steel (aluminum? hell, I'm not a metal expert!) against the back of the truck. I was completely hidden from view. I was in the darkened parking lot, around the building where the party was happening. The truck backed up against a boundary fence so there was no chance of anyone approaching from that side. There was always the possibility of guys doing what guys do and use the area as their urinal. But, being caught IS always a dark part of the fantasy, sooooo.

I could feel my nipples filled with blood, they were so hard. My pussy? I didn't even want to know how wet it was right then. It wasn't two minutes when I felt someone in front of me. They must've crept up, I hadn't heard a thing. Then, I heard a soft, low whistle. I felt a hand, a man's hand trace from my wrists, down my armpits and my sides. It made me writhe from the tickling. Suddenly, I realized it was him. He'd done the same thing last time. He knew my reaction to being tickled. "Fuck," I thought, "where's Maggie?" I hoped she was ready. I figured she was close, though.

I felt his hand around my head and much to my horror, he adjusted the blindfold, pulling it down further. I could no longer see any light, it was like I'd been caught being sneaky.

I heard him whisper in my ear, "I knew I'd find you again like this. You really dig the kinky shit eh?"

I couldn't place the voice, it was just a whisper, plus, it appeared he was purposely altering it, making it lower. His hands found my tits and he played with them freely, the shirt would've only been ripped off of me, I assumed. He squeezed my nipples hard now and again, just to watch me squirm.

"Please, just let me go, I just wanted to know who you were," I begged.

"You don't seem to be in any negotiating position," he again whispered softly. "In fact, you just got in even deeper." I heard him taking pictures with his phone. I could see the flashes, even through the blindfold. Then, after a few minutes of him enjoying mauling my bare tits, I felt my skirt being lowered, even as I tried to kick, hopelessly, to avoid his hands. It was no use, it was completely off in seconds. I was nude, totally. I couldn't scream, I'd have the entire apartment complex finding me like that.

"That's better," he rasped. He took more pictures of me like that.

"Where is Maggie?" I wondered. I thought the idea was to flush him out, then surprise him by showing up and chasing him off. Then I remembered her words, "I didn't say I'd stop him..." that thought created a flush in my pussy. She was probably watching from somewhere.

He kicked my feet apart. I felt his fingers on my pussy. I sighed, involuntarily. He probed me, he rubbed my lips, exposing my embarrassing wetness. Then, he inserted two of them in me. I gasped. His fingers were as thick as his cock, it seemed. I made a mental note to pay attention to guys hands from now on, "I might even be able to identify him later," I thought.

"Hmm, you seem to always put yourself in a position where you can't suck cock," he pointed out. "Guess I'll have to take something else, then," he said gruffly, still in disguise.

He spun me around. I knew what he meant. "Oh god, oh god...I'll suck you, I'll suck you!" I begged.

"I don't see how. Plus, that ass...SO inviting, so perfectly tight and round...no way I'm not tapping that."

I'd left the cuff key in the bag under the truck. I supposed I could tell him where it was, it just felt more embarrassing, more natural to let it play itself out. Still, I was beside myself. I was about to be taken, like that, in a dark parking lot, next to a dumpster. I was still fighting against my cuffs and his gropes.

"Shhh, you don't want anyone else around to watch, do you...maybe take their turn? Wait, maybe you'd actually LIKE that," he said cruelly.

I knew dozens of guys at the party would, in a heartbeat. I pleaded, I begged. Finally, I knew the best thing to do. I gave in.

"Ok, do it, just be slow...please..."

"Oh, I'll take it easy...at first," he replied coolly.

He found a surprise, the butt plug. "I KNEW you were into some kinky shit! God, you fucking were warming that thing up FOR me!" He pulled it out and laughed when I squealed. "Here, hold this!" He said coldly. He shoved it in my mouth and held his hand over it, forcing me to take it until I just let it happen.

"Don't spit it out or I'll take off my belt and whip your ass in to tomorrow," he growled. It didn't go that deep, it's just that...well, it had been in my ass.

He used my ridiculous wetness to soak his cock, he even lifted me off my feet and slid his dick into my pussy and gave me a few strokes before pulling out.

"Now for main attraction," he joked. "But first..." he said ominously. I felt him drag something and put it at my feet. It was a box of some kind. He made me stand on it. It helped him line up properly, with me being so short. Then, I felt that fucking thick cockhead at the opening to my ass.

"I have wanted this thing since I first saw it, hell, EVERY man who sees it wants it."

I was sobbing softly, it was all so much. To have my ass penetrated for the first time...like THIS? Still, I was helpless, as I'd always dreamed about. I just couldn't believe it was about to happen. "Where the fuck is Maggie?" I yelled in my brain.

The screaming in my head had only begun, however, when that cock started to pass through my anal ring. I almost had to bite my tongue to keep from cursing. To his word, he worked it in slowly. Fuck, he was thick, thicker than my butt plug, but probably because of how I got used to it, I was able to take it.

"Fuck," he grunted. "And I thought your pussy was tight..."

Slowly, with cautious strokes, he worked his way all the way in...and backed out just as carefully. Little by little, with increasing fervor and insistence, he worked up to a pace which rocked me back and forth on his dick. It felt cosmic, I actually had a mini orgasm on his dick, I could feel my clit buzzing.

He was berating me the whole time. "Yeah, that's a good little whore, taking it up the ass. I'm going to have you in every fucking way, you fucking little tease. You'll never tease me again, you slut," he groaned urgently. Now, it was primal. He wasn't concerned at all about my feelings, he was really ramming me good. It felt like I was going to get split open, but surprisingly, it kept me on the edge of orgasm the whole time. The feeling was indescribable. I think if he'd have used his fingers on me like last time, I'd have fucking exploded. Instead, he just reamed me until he finally couldn't stand it. He blasted off, holding himself deep in me until he'd shot it all in me, DEEP in me.

He pulled out with a "pop." He took a few more pictures. "Until next time," he joked cruelly. Then he was gone, leaving me hanging and dripping. I hadn't counted on this, being left unattended. While it wasn't likely I'd be discovered I knew it was still possible. "Where the hell is Maggie?" I wondered. I finally spit out the butt plug. I could feel the cum all the way down to my ankles by the time I heard her arrive.

"Oh my god, oh my god," she said with apprehension. "Is it over? Oh my god, did it already happen?"

"Fuck, fuck, fuck," I hissed. "Are you kidding? You missed it?????"

"I am SO sorry," she said, while quickly unlocking my hands. "Your stupid landlord cornered me, you know how he likes me, I could NOT get away from him...or his hands."

"Oh fuck."

"Did you get a look, under your blindfold?" she asked hopefully.

"No, the first thing he did was make it tighter. I couldn't see shit!"

"Fuck, fuck. Did he...take you...back there?"

"Yes, Maggie. He fucked my ass. Some dude who I can't even identify now has cum in my pussy and my ass!"

"Did it...hurt?"

"Yes! Well, kind of...not like searing pain or anything...actually...it kind of felt good...fuck," I said, embarrassed. "I actually came a little with it in there."

"You did? That's amazing!"

She helped me up. She guided me back to my apartment, still naked, shielding me with her body. She needn't have bothered, pretty much everyone but the cat lady was around the other side at the party. She helped me again into the shower. This time she didn't help, but she watched me try to scrub my sins clean. It smarted every time my finger grazed my hole...reminding me of it's use. She helped me dry off and walked me to the bedroom.