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The leather tongue of the riding crop came down on my proudly erect left nipple, forcing me to cry out. My feet scrambled for purchase on the floor as my whole body reacted to the slap on my tit, but I was too high off the ground. The handcuffs cut into my wrists until I could still myself enough to get my toes back on the cool cement. I hung there, my arms going numb as they stretched to the ceiling, forcing my large breasts to stand out before me almost in defiance of gravity, while being forced to stand on my tip toes had the same effect on my legs and ass that a high pair of stilettos would. That big ass was on full display, the cool air soothing against the red skin from where the crop had struck before, and undoubtedly would again.

The crop was in motion again, I could hear it cutting the air. It landed at the top of my right breast, just where the skin begins to pull away from the pectoral muscle. Air rushes out of my lungs and my vision goes white. I haven’t even begun to recover when I feel a mouth gently close around my left nipple and suck. Then there’s a hand on my pussy, softly rubbing those lips together. The pain slowly fades into pleasure, my scream turns into a moan.


So yeah, that’s where things are right now, how I got there is a different story. After my morning with Yuna and evening with Michael, I called in sick for work the next morning. When I’m not in a relationship, I’ll use a vibrator one or twice a day, but that wasn’t necessary. I was completely sated. My morning consisted of cereal, milk, and Darkwing Duck thanks to my Disney app. Then there was some light reading, I love the old gangster movies with Jimmy Cagney, so Selena had given me a book about crime in the twenties and thirties. Lunch was a peanut butter sandwich and a tv medley that included scifi, anime, and even a telenovela with the subtitles on. Dinner was roast chicken and vegetables with a white wine and Firefly. Nathan Fillion is my husband, I just haven’t told him yet. After dinner there was a nice long bubble bath. The hot water soothed everything, like the most giving of lovers. I had thought I might masturbate a bit before bed, just to completely relax everything, but I was asleep the minute my head touched the pillow.

Then there was yesterday, the day where it seemed everything that could go wrong did. The fast food place screwed up my breakfast order so I had a bran muffin instead of my breakfast burrito. Then when I got to work I found out that all the work I had done after Yuna was done wrong. I apparently sent an erotic novel to one library that had requested a theological treatise, a historical mystery to one that had requested a book on current events, and a biography of the Marquis de Sade to someone who asked for a self help book.

So apparently Horny Cassie shouldn’t be trying to handle Work Cassie’s job. Not a problem. The other day was a once in a lifetime occurrence. I mean who hasn’t had a passionate lesbian encounter and then taken a man’s virginity in their place of work at least once? All that was out of my system, I’d hit a bar or club tonight and pick up someone and take them home. Fuck that person in my bed, to get the smell of my dumb ex out of the bed if nothing else, and keep work for work. It was a plan that was sheer elegance in it’s simplicity.

“Ms. Cassie, can I have a word with you?” Bob, our janitor, asked. I was busy emailing apologies for my mistakes and happy for the distraction. I turned to face him, Bob is a silver fox. Tall with broad shoulders and a square jaw. If you put him in a suit he’d look like he stepped out of an episode of Mad Men.

“Sure Bob, what can I do for you?” I should have noticed something was different. Normally Bob is the most polite person you can imagine, never ogling the women, but as I sat there his eyes seemed to feel up my body before finally finding my eyes.

“You know I’m the only person ya’ll got to clean up around here? I work in the mornings, leave around ten, then come back at six in the evening and clean till about ten again.” he said it like I didn’t know his schedule. How many times had he walked me to my car at night? It was one of those wonderful gentlemanly things you just couldn’t deny from a man his age.

“Well I just bring it up because the other day I had these two weird wet spots…”

I didn’t hear much more after that. I’m a fucking idiot. I’ve yelled at men before about being so obsessed with sex that everything else goes out the window, well here was proof that I’m no different. How could I have forgotten to clean up, or that Bob would have been there that night.

There’s a strange silence and manisa escort I look up at Bob, finally coming out of my own little world. I know I’ve missed something important, he’s giving me that look that says he knows I was ignoring him. “Could you say that again?”

“Well, I was hoping we could come to an arrangement. If you do two things for me, I don’t have to tell Selena about your recent activities.” He said, leering at me. And to think I thought he was a gentleman.

“Like what?” I ask, afraid I already know the answer.

“Oh, nothing illegal, in fact I think you will enjoy it. But I will need the answer first. I would hate to have to interrupt Selena’s lunch.”

“I can’t believe that you would blackmail me!” I try to keep my voice down but it went up involuntarily.

Bob looked around to see if we caught anyone’s attention, then turned back to me. Most guys stare at my tits, they’re the easiest ones to catch, I’ve caught men staring at my ass, but Bob is the first guy who seemed to be trying to x-ray vision a glimpse of my pussy. “Blackmail is such a harsh term. Think of it more as persuasive coercion to do what you’d like to do anyway.”

“Rape by any other name…”

That brings his eyes up to mine. He actually looks offended! “I would never do that,” he says in an angry whisper, “if you say no, I would never force myself on you. No one is putting a gun to your head, you might get embarrassed or have to change jobs, but that would be the extent of your problems.”

So my options were limited but at least I knew one threat was off the table. As he waited for my reply, his eyes wandered down my neck, onto my ample bosom, before finally resting on my lap again. For all the change in him, this was still the guy I’ve known for years. And I have had at least one Entrapment based fantasy where Bob was the Sean Connery role. And that stare into my snatch is hitting my voyeur fetish hard. He’s got my job and my lust in one hand, my integrity in the other.

“What do you want me to do?”

He looked at me and smiled, “Tomorrow will be a long good day for you. Get here at four in the morning so that I can punish your flesh. You have been such a bad little girl. I’m going to string you up and whip you for being such a slut. Then you will stay late, my son and some of his friends are going to come over and my now properly admonished little slut will fuck them all.”

My mouth just hung open. Bdsm and a gangbang? I was outraged, horrified, and damn it, getting wetter by the second. Somehow he seemed to sense that last part most of all. “Don’t worry Ms. Cassie, Ol’ Bob here will take good care of you. No harm will be done, just some good old fashioned fun.”

“Yeah if you were Caligula.”

We both laughed at that. Ground rules were established, I gave him my safe word and he left making me promise to be completely chaste till tomorrow.


So that’s how I got to be here, in one of the maintenance tunnels under the library. A chain attached to one of the water pipes along the ceiling of the tunnel keeps my arms raised by the handcuffs around my wrists. Then there is a length of rope which he has tied in a cross harness around my breasts. It’s actually more supportive than some bras I’ve tried, he has it tight enough to hold the big girls in place and restrict the blood flow a bit, but not enough to make them go numb. He wants me to feel what he’s doing.

Bob steps back from me and goes to his black duffel bag, “You know Ms. Cassie, you may not like how I got you here but I want to thank you for coming anyway. It has been a very long time since I’ve had a chance to enjoy these things.”

He’s grabbing several items that I can’t see, there’s a nervousness in my belly at the uncertainty. I’m uncomfortable but horny as hell right now, but I still don’t know how much further to let this go. “You don’t have anyone in your personal life who likes this?” I ask trying to waste time. I don’t know how much longer till opening but surely he will stop by then, I hope.

“Not any more.” he says quietly and turns around and walks over to me. I still can’t make out the items he has before he is in motion. He holds up a squeeze bottle and sprays my chest, belly, and groin, then goes behind me and sprays a generous portion on my ass. I yelp at the cool sensation of the viscous liquid on my skin and I’m expecting it to do something before it dawns on me that it is just lube.

The empty bottle clatters to the ground and I feel him come up behind me. He must have stripped at some point because all I feel is his flesh on mine. His hands roam mavişehir escort over my body, making sure to spread the lube evenly. As he works his hands all over my breasts, I can feel his dick press against my left ass cheek. Not bad Bob. I rub against it as best as I can as he pays particular attention to my nipples. The thick pink points are fully erect and I’m really enjoying the way he is running them through his fingers. With the lube when he goes to pinch them they just slide out of his grasp, so I just feel a little jolt of pressure.

“Stop rubbing like that.” he says as his hands now trace down my torso.

“Why? You afraid you might decide to stop playing and we can get down to just good ol’ basic sex?”

His hands are now down below my waist. He uses the lube he squirted there to comb my pubic hair up and away from my pussy, then his hands go further down and the lube is mixing with my natural wetness as he makes sure to get his fingers everywhere.

“We won’t be having any sex like that. I only did that with my wife.” he says loud enough I can hear him over my involuntary moans. His hands don’t stop and I feel an orgasm on the horizon. Yet what he said bothers me.

“I didn’t know you had a wife Bob. Does she know what we are doing?”

“Depends on what you think happens after death.” he says and his hands slide around my hips to run down and up my ass.

“I’m sorry Bob, I didn’t mean…”

“It was years ago, by the time we found out she had cancer it was too late. But at least she wasn’t sick long. Emma would have hated that. She’s the one who got me into this. You actually look a bit like she did when we first met. Emma wasn’t as tall or have as big of a bust, but your ass and hers, damn. I didn’t think I’d live to see another like hers again. Then there you were in the study hall with that young guy, naked as the day you were born and all I could think was, I found Emma’s ass twin. It was worth it all just for this.” the whole time he spoke he massaged and kneaded my ass. It was kind of sweet, the way he spoke with such love for his wife, while feeling me up.

Suddenly his hands were gone and I saw him step around to stand in front of me. I didn’t have time to check him out though as his hands came up to my chest and then there was a sharp pain and I shrieked as it didn’t stop. My nipples felt like they were on fire and I strained against the handcuffs and chain as I tried to reach down and feel what had happened to them. Bob grabbed me and held me still then forced my thighs apart and pain exploded from my pussy.

The pain slowly subsided and the stars cleared from my vision. I felt a strange pressure from my chest and between my legs. Looking down, I saw that a clamp had been applied to each nipple and I could feel the cool metal chain down my stomach connecting to what must be a clamp on my clit.

I looked at Bob, fixing to say something, but he just reached out and pulled lightly on the chain. The sensation of having my nipples and clit pulled on at the exact same time was painful and erotic in a way I can’t put into words. Some how the riding crop was back in his hands and he stood off to my left, playing with the chain and bringing the riding crop down on my butt cheeks with small but strong strokes. I was yelling for him to stop, I was screaming for him to keep going. I could feel the orgasm coming, every inch of my skin felt like it was all a sex organ and my eyes were shut tight as if any more stimulation would be too much. Then everything stopped, just as I was hitting my peak.

“Oh come on I was almost there!” I complained.

“Patience is rewarded.” he said and I heard a snap and then a humming. Next thing I knew he was kneeling next to me and threw my left leg up over his shoulder. I was thankful for all his attention with the lube as he shoved the two vibrating dildos up into my pussy and ass. Another scream tore from my throat and then he was standing again yanking on the chain and spanking me with the riding crop. It was all too much, the vibrations and the clamps and the crop, it wasn’t an orgasm so much as just my whole body started convulsing. Bob let go of the chain as I thrashed about, my huge chest bouncing pulling harder on the connecting chain than my tormentor had. I tried to keep my legs under me but the muscles wouldn’t respond and as the thrashing stopped, my shackled wrists were the only thing that kept me from hitting the ground.

After a moment Bob unhooked the clamps from my nipples and clit. He walked the chain back over to his duffel bag and then began moving some large contraption over menderes escort to me. I just hung there like a slab of meat, the two vibrating dildos doing their best to rekindle my arousal. I was barely aware of what Bob was doing till I felt a plastic cup on each breast. The cup dwarfed each areola and each nipple fit neatly into a plastic tube connected to the cup. “Oh shit! You can’t be serious!” I managed to say before he flipped a switch and my breasts were consumed by the milking machine. My nipples stretched down the tube, retreated, then stretched further, each time taking more of my breast into the cup.

My mouth just opened wordlessly as I could barely comprehend what was happening. Bob then turned a dial and the machine began sucking faster. He pressed a button on a remote and both dildos changed to a higher frequency of vibration. Then he went behind me, roughly grabbed my ass, and began hotdogging himself. Of all the weird sensations my body was going through, I have to say that was the weirdest. Just feeling his big dick sliding between my ass cheeks, no attempt to penetrate.

“You are such a beautiful woman, this big ass feels great against my cock. So much to grab onto! I love the way the skin moves between my fingers when I grab it real hard like this. Can you feel what you are doing to me you bad girl? Can you feel my balls tighten as I thrust forward and they slap those thighs? Can you feel my dick twitch as I try not to cum between these two amazing slabs of meat? I can feel the vibrations in your pussy and asshole in my cock. Are you going to cum again? Are we going to cum together?”

Damn if his dirty talk didn’t send me over the edge. I just moaned over and over again as the waves of pleasure came over me. He thrusted even faster till he finally stayed forward and squeezed my ass together as hard as he could. I felt his hot semen spray all through the crack of my ass and on my lower back.

As soon as Bob recovered he moved to turn off the machine and unhook the suction cups from my breasts. Then he grabbed the remote and turned off the dildos. The sex toys finally going still felt almost as good as now as the vibrations felt earlier. He pulled the one out of my pussy and put it back in his duffel. When he came back to me he had something in his hand.

“I’m going to put this in your ass, trust me, you will thank me for it later.” he said and then disappeared. I felt the dildo slide out, then gasped as I felt the butt plug go in.

He grabbed a washcloth and cleaned up the mess he made, then began the arduous process of getting me down.

“So was that so bad?” he asked as we cuddled on a blanket on the ground. He ran his fingers through my hair absentmindedly. It was a nice bit of tenderness after everything before.

“There were some great moments, I’m not going to lie, but I think I will just stick with regular fucking.”

“Well you’ll get that tonight.”

“I don’t know if I’ll be up for that.”

“Sure you will. You got the whole day ahead of you. In fact we better start getting dressed.”

I was glad that I opted for comfortable baggy clothes today. For the first several hours of the day I was sore and uncomfortable, but around lunch the weariness went away and I felt relaxed in a way I never had before.

Selena and I went out for lunch to a little Mexican place. She looked different today. I mean she always dressed nice, but her taste always ran a bit more conservative. Always trying to downplay her size. Today though her navy blue dress was low cut and she had apparently picked a bra that could actually hold those mammoth tits up. The red sash around the waist helped to emphasize her ass. Even her makeup was done in a way to highlight her beautiful brown eyes. I squirmed against the plug in my ass as my thoughts turned steamy.

“So Cassie, how have you been?”

“You don’t want to hear about my boring life, I’m much more interested in your make over.” she actually blushed when I brought it up.

It took her awhile to get going but she eventually spilled. One of our long term patrons had finally worked up the nerve to ask her out. They went out last night, one thing led to another, and they spent the night together.

I couldn’t take my eyes off of her as she talked about that night. Her face was a bit flushed but her chest rose and fell faster as she described the night and her eyes locked with mine. Before I knew it we were holding hands as she told me every intimate detail. She was using her night of passion to seduce me and it was working.

“Would you like to go out with us sometime? I don’t like the idea of you staying by yourself all alone.”

“I don’t know about the both of you, but would you be interested in a girl’s night?”

“How about tonight?”

I made up some excuse to get out of tonight but made a date for the weekend. The rest of the day went by in a blur. All I could think was how would I make it through tonight.

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