John

It was a few days after my round-the-world excursion with Caroline. She'd been texting me daily in anticipation of bringing Angela over for an evening of three-way fun. The texts always included risque pics taken at her office, where she was the accountant for a business. She'd taken to going pantyless since our encounter and sent me multiple pics and her splayed and fingered puss throughout the day. I'd encouraged the activity with our first texting session after our sexual journey, and she'd taken to it like it was a natural thing.

In our chats, it seemed that Caroline was tired of the same old boring dates and fucks and wanted something to push her limits. The more she talked of her desires, the more I encouraged her to express them through dares. The first order of business was to dispense with the wearing of pants completely. Only dresses and skirts could be worn from now on, and nothing that went past the knees. Apparently, this was a big adjustment for her, but she took to it readily.

On the first day of her new rules, I had Caroline take pics of her breasts and puss in the safety of her office. On the second day, I pushed her to take upskirt shots as she picked up copies from the main office printer even while others were around. I did allow her to silence the shutter on the camera on her phone for the more public shots. Each successive dare required a little more of her, such as touching herself during company meetings while sitting amongst her colleagues and sending me photographic proof.

At first, I would send the orders randomly while she waited patiently for the next. By the third day, Caroline was texting me to request another command. She thrived on the thrill of it all and wanted more and more.  

"How's your schedule for the afternoon?" I called for the first time in our exchanges.

"It looks fairly light after three. What do you have in mind?" Caroline inquired.

"Set up an appointment for me to visit at four this afternoon. You're going to give me a blowjob in your office," I said matter-of-factly.

"Okay, but I'll need a name to give them, and you've never given me yours, so what shall I tell them?"

"It's John Simmons, and don't worry. I would never do anything to get you fired. I only want to give you that rush that you obviously desire."

"Thank you!" she screeched.

"While you wait, feel free to finger yourself to orgasm as much as you want. I'll see you at four. Have fun until then, and send me pics of your cum-coated digits," I insisted before hanging up the phone.

It wasn't thirty seconds later when my phone began to ding with photos of her splayed legs allowing two fingers to enter her drooling slit. They kept coming for twenty minutes showing not only pussy play but anal as well. I had to free my cock and was tempted to bring myself off, but opted to taste my own semen as it percolated from the tip of my hardened prick. Caroline also added commentary, such as, "See what you've done to me? I've become nothing more than an attention whore, wanting to feel your cock in all of my holes again."

"Don't worry, you'll get all of that and more this Saturday when you bring Angela over to play. Until then, I'll keep you busy with ways to show off your masturbatory skills to me and maybe a few others," I texted in reply.

"Wait, what do you mean by a few others?" Caroline questioned.

"I was thinking that we'd go out dancing Friday night and show you off a little. Don't worry. We'll head out of town to minimize the chance of you being recognized."

After a long pause, Caroline finally responded, "You're going to ruin me for other men, you know that, right?"

"Maybe so, but this is what you need right now, and I have no problem giving it to you. By the way, if you don't have a slinky little club dress, then make sure to find one before Friday. No undergarments are allowed, and it can't be more than three inches below your crotch."

"I understand," was all she managed to type. About a minute later, I received a pic of her pussy and fingers coated in her nectar from what must have been an overpowering orgasm.

As four o'clock neared, I dressed in and suit and tie, less underwear, for my meeting with Caroline. I arrived a few minutes before our meeting time and checked in with the receptionist. She promptly led me to Caroline's office, where she knocked before entering.  

"Come in," was heard by both of us before the young lady opened the door and shuffled me to a chair. Once she disappeared, I placed my small briefcase on Caroline's desk and showed her the contents. There was a Rabbit vibrator, a pair of nipple clamps linked by a long silver chain, and a small towel. I rose from my chair and pushed it around until it was next to hers.

"I want you to go to the restroom and attach the nipple clamps and then return. Once you're back, slip under your desk and remove your clothes. You'll suck me while fucking yourself with the fake dong. Any questions?"

Her eyes were hazy from the thought of all that was to come. Standing with the clamps balled up in her hand, Caroline practically ran out of the office without a word.  

Caroline

I was floating on an orgasmic high that had lasted most of the day, and it was only going to get better if I dared to do what John asked. Entering the bathroom, I slipped into a stall and locked the door before lowering the straps on my dress and pulling down my strapless bra. I'd used nipple clamps once before with a college girlfriend, but she'd been so rough that I never tried them again.

Tentatively, I surrounded my left nipple with the first clamp, noticing that it wasn't hard to open. As I gently let it close, I felt a twinge of pain that traced its way to my already sensitive clit. Without hesitation, I moved the second clip to my right nipple and released it willingly. A bit of cum pulsed from my uncovered puss and proceeded down my inner thigh before I scooped it up and tasted myself.

Pulling my bra and dress back into place, I walked to the sink, feeling the delight of my bra rubbing my tender nips. After a quick washing of my hands, more for show than anything else, I moved hastily back to my office. Each hurried step sent another shock from my nips to my clit, releasing more of my carnal fluids. I sat at my desk momentarily while trying to catch my breath and willing my impending orgasm to abate.

John could see the state I was in and waited patiently until I was ready. With things mostly under control, I grabbed the rabbit and slid to my knees. John adjusted the position of his briefcase to block the view of my head above the desk before assisting me with the removal of my dress. He folded it neatly and placed it on my chair as I unsnapped my bra and added it as well. Moving under the desk, I turned to face John's crotch and released his swollen member from his pants.

With his cock in my mouth, I sat on my knees in position to suck him before raising my pussy and easing the dildo inside. Using both hands, I turned on the vibrator and lined it up properly with my clit before sinking down until it vanished inside my needy little cunt. I growled around his cock as the vibrations tingled inside me. It was then that John took ahold of the chain and pulled until it was taut. The added stimulation pushed me over in a big way as I came hard around the faux cock.

John's cock was still in my mouth as my head cleared. I focused on him to try and speed up the process. Part of me wanted this all done so that I could go back to work, while another part wanted to be exposed for the hungry little harlot that I was. At the moment, I was just wanting to give him pleasure before someone walked in looking for me. Seconds later, that exact thing happened. I was under my desk sucking this wonderful man's cock when there was a knock on the door.

John didn't hesitate. "Yes, come in," he stated. I froze for a moment as a cool rush of air passed my naked body, sending chills across me and swelling my clamped nipples in the process. Between the added stimulation and the adrenaline forcing its way through my veins, I heard nothing of the balance of their conversation. After another woosh of air, John noticed my situation and tugged mildly on the chain, which pulled his hard-on deeper into my mouth and pushed me beyond the edge.

My cum sprayed around the embedded phallus as I sucked John into my throat before feeling the surge of his baby batter down into my belly. He eased off the chain and let it dangle between my breasts while I backed up enough to clean his cock. He slipped it back inside his trousers before pulling me forward so that I could ease the dildo from my sloppy puss. He took it from me while handing me the small towel that had been in his briefcase. I used it to clean my lower extremities as best I could while in my position.  

John licked the vibrator like a lollypop as I removed the nipple clamps from my tender tits. Still on the ground, I took my bra and slipped it on gingerly before grabbing my dress to do the same, all while John continued to suck my juices from the dong. When I was ready, John helped me to stand just before there was another knock on the door. As if we'd practiced it a hundred times, we tossed all the items back into his briefcase.  

"Yes," I stated firmly as the door pushed open. It was one of my colleagues that needed a quick signature. I motioned him forward and, after a quick glance, signed the document and handed it back to him before he briskly vanished, closing my door behind him. I dropped to my chair and huffed.

"That was fun, wasn't it," John said while leering at my exposed and puffy labia.

"It was terrifying and exhilarating all at the same time. Is this what tomorrow night will be like?" I questioned.

"Probably less scary and more intoxicating since you won't know anyone and will have a had a drink or two. So, how were the nipple clamps? Too tight?"

"Actually, they were perfect! But I don't think that I could wear them much longer than I did. The stimulation overload was hard to cope with, especially with that sublime rabbit hitting all the right spots."

"Well, I can loosen them up a bit more and add an attachment for tomorrow night. What do you think?"

"What sort of attachment are we talking about?" Caroline said with a questioning look on her face.

"Don't worry, you'll love it, and so will I, my sexy little MILF."

With a quick swipe of his middle finger through my puffy pussy lips, John stood and walked out without another word. I spent the rest of the afternoon playing with myself at what would come of tomorrow night, not to mention Saturday with Angela.

To be continued...