Femdom Between Friends Ch. 02

We had set the alarm clock in Karen's hotel room to go off early so we'd have plenty of time to shower, dress and get over to the Las Vegas Convention Center before the doors opened. It was the second day of the conference we were attending on behalf of the company we both worked for, and it was up to us to staff our display booth and give a presentation later in the day.

I heard the alarm go off at 6:00 am, but Karen quickly switched it off and slipped out of bed while I lazily dozed off for a little extra snooze.

About 15 minutes later she gently woke me with a hand on my shoulder and a soft voice in my ear saying, "Coffee's ready Jack, time to get up." I guess you could say I woke up and smelled the coffee, opening my eyes to see her sitting on the side of the bed in a terrycloth hotel robe and two steaming cups on the nightstand. I sat up and rubbed the sleep out of my eyes.

"Now this is a surprise," I said with a smile, "After last night I didn't expect you to be serving me coffee this morning, Karen."

She gave me that crooked grin that I liked so much and replied, "Well, this is what being real looks like Jack, why shouldn't I do something nice for someone I like?"

After working together for years as close but strictly platonic friends, Karen and I had just learned the night before that we had, much to our surprise, some very compatible BDSM fantasies... I had long dreamed of being used harshly by a dominant woman, while Karen had fantasied for years about having a man under her control.

Being real was the key, as neither of us had any interest in the theatrical kind of BDSM role play that you see so often in femdom erotica. In my fantasies, the woman in control would want to hurt me because it excited her sexually, but she didn't need to scold, insult or ridicule me while doing it; as odd as it might sound, she was nice to me about it... even apologetic.

For whatever the reason, this scenario had been the focus of my sexual fantasies for years... a nice girl who liked me enough to feel some guilt about needing to whip me to get herself off. There was something about a woman becoming aroused by hurting me -- and at the same time feeling sorry for me for having to endure it -- that thrilled me to the core.

I had pretty much given up hope that I'd ever find that woman, especially someone that I liked enough to want to suffer for her own pleasure, so imagine my surprise at learning that my colleague and good friend Karen -- with her freckles, strawberry blonde hair and girl next door looks -- had secretly dreamed since childhood of enslaving a man and even whipping him.

These thoughts went all the way back to her childhood, when she watched cowboy movies and found herself strangely fascinated by scenes of men getting whipped. But just like me, she was all about keeping it real; not playing a game of "Mistress using Slave," but simply "Karen using Jack."

She liked me as much as I liked her, so it took some convincing on my part before she finally accepted that I really did want her to whip me. And, just like in my fantasies, when she began laying into me she felt badly about it... but not badly enough to hold back from thrashing me long and hard with my own belt, violating my asshole, making me eat out both her pussy and ass and even swallow my own cum.

And after all that, we ended the night by making gentle and caring "vanilla" love, which was also very real -- because we had fallen in love.

How our secret desires developed over the years I have no idea. My parents didn't believe in corporal punishment; did some part of me think I deserved to be disciplined, so I grew up craving it? And what about Karen, did she grow up resenting the authority of her father? Or was it just that seeing a man suffering for her was a way of proving his love?

Well, I'll leave it for others to analyze and theorize. All I could think about now is that amazing moment last night when Karen and I first realized we were ready and willing to make each other's fantasies real, remembering the eagerness I saw in her eyes -- and the hint of cruelty.

She reached for one of the coffees and I did the same. After taking a sip she looked at me and asked, "Are you okay Jack? I mean, are you okay about everything we did last night?"

"I'm more than okay about it Karen, I loved it... all of it," I said. "How are you feeling about it?"

"Jack, it was... it was amazing, I've never been so turned on in my life," she said. "Whipping you for real was like, a thousand times hotter than in my fantasies. And I loved being able to make you do whatever I wanted."

"Well, I've never cum so hard and for so long... I thought it would never stop," I said.

"You did cum a lot... but I guess you learned a downside of that!"

"Yes, that is true."

We drank our coffee in silence for a minute, a perfectly comfortable minute; I always believed you knew you were really connected with someone when there was no awkwardness from a conversation going silent.

Finally Karen set her cup on the nightstand, looked at me and broke the silence. "Can this really work Jack? I mean, can I be your girlfriend and dominatrix at the same time? Do I have to be one or the other, and then how do I know which one to be? I'm feeling a little confused about it."

I thought about it for a moment and said, "I think you can be both Karen."

"But what if I'm really feeling like I want to do things to you and you're just not in the mood, or it's not a good time? Or if you want me to whip you or whatever and I just don't feel like doing it?"

"Well, doesn't any couple have the exact same issues about when to have regular vanilla sex?"

She thought for a second, then laughed and said, "Well, duh, I guess that's true!"

"Being real about it means we can, you know, just ask," I said. "You can ask me whenever you feel like playing, and I can ask you... I think we communicate well enough for that."

"Yeah... you're right Jack."

"And as for being my girlfriend," I said, taking her hand, "I want you to be that all the time."

She smiled and squeezed my hand. "Jeez, I'm still getting used to this... maybe I'll write my autobiography and call it 'One Dumb Domme', what do you think?"

"I think you knew exactly what to do once you got going last night, Karen."

"Yeah, I went pretty crazy, I really got into a state... you're sure it wasn't too much?"

I put my coffee cup on the nightstand and pulled her to me. I kissed her full on her lips and said, "No Baby, it wasn't too much. You can go even further if you want to."

We kissed again and she whispered in my ear, "I think I want to, Jack."

"Do you have anything particular in mind?"

"Oh, you'll find out soon enough. We're still going shopping for toys after the conference today, right?"

"Yes, and speaking of the conference, we better start getting ready."

I drained my coffee and got out of bed, and went to retrieve the jeans and shirt that I left on the floor of Karen's hotel room last night. As I passed by a mirror I caught sight of the redness of my ass and the backs of my thighs where Karen had worked me over. Looking down at my cock, which was not spared a lashing either, I saw it was still red as well.

I put my clothes on and kissed Karen goodbye before heading to my own room to shower and dress for the conference. An hour later we met up in the hotel restaurant, both of us in now our best business attire, and sat down to have a good breakfast before the full day's work ahead of us.

When we finished eating I told Karen I was going to use the restroom before we headed out and stood up. "Hold on Jack," she said, "I have something for you." I walked around to her side of the table she as reached into her purse and pulled out a handful of small but very wide rubber bands, each probably just a little over an inch in diameter but maybe 3/8ths of an inch wide. She motioned for me to bend down so that she could speak quietly into my ear.

"These were holding bunches of those pens with our logo that we had made for the show," she said. "Would you do something for me Jack?"

"Of course," I replied.

"Could you take these into the men's room with you," she said, pressing them into my hand, "and put them on your cock? I think you could probably fit three or four of them on."

I pocketed them and headed off to the restroom. Once there I entered a stall, and after relieving myself I left my cock out as I retrieved the rubber bands from my pocket. They were brightly colored in yellow, blue, green and pink, and I began fitting them over my flaccid penis.

I was able to fit four of them on so that my entire shaft was covered up to the head -- I'm circumcised -- and the only tricky part was getting them on so that none of my pubic hair was caught underneath them. I put my cock back into my briefs and returned to our table.

Karen looked at me and asked with her eyes if I had completed my task.

"Done," I said.

"I'd like it if you wore those all day Jack, that way I know you'll be thinking of me."

"All day? Even during the presentation we'll be doing later?"

"Especially during the presentation," she said, grinning. "We better get going now."

Ever the gentleman, I held her chair as she stood up. We walked out of the hotel and made our way to the shuttle buses ferrying conference attendees over to the Convention Center. As we boarded the next bus leaving, Karen said, "Let's sit in the back."

We made our way to back of the half-full bus and sat down in the back. Karen turned to me and quietly asked, "How do they feel on you, Jack?"

"A little strange," I replied.

"Are they uncomfortable?"

"Not really. I definitely know they're there, but they wouldn't be uncomfortable unless I, you know... got excited."

I should have realized what was going to happen the moment those words left my mouth.

"Let's see," Karen said, discreetly slipping a hand under the messenger bag that lay across my lap and quickly locating my cock. She began teasing it through the thin fabric of my dress slacks, and it didn't take long for me to respond.

"How are they feeling now?"

"Not good... they're squeezing me pretty tightly."

"Mmm," she said, whispering in my ear, "it turns me on to know that. I'm sorry to have to tell you that your cock is in for a much harder time later on."

"A harder time?" I asked, sarcastically.

"No pun intended," she said, giving it a sharp squeeze that made me wince.

She continued to discreetly play with me until our bus pulled up to the Convention Center, and although the rubber bands felt quite unpleasant I was thankful they kept my cock in check well enough that I didn't have to worry about standing up to leave the bus.

The doors opened a few minutes later and we filed in, found our display booth and started setting it up for a day's work.

It was a crowded conference and we were both kept busy speaking to the stream of attendees stopping by our booth, discussing our products, handing out brochures and exchanging business cards.

Occasionally I would look over at Karen and marvel how this charming and professional-looking woman, her hair neatly tied back and wearing a crisp navy blue business suit, had only last night driven herself into a sexual frenzy by whipping me until I cried. Even more amazing was knowing that she had every intention of doing it again, and might even now be thinking about other ways to use me.

I watched the men and women engaged in conversation with her, musing on what they would think if they could have seen her unleash the fantasies she had been nurturing for years. Of course I also couldn't help wondering what they would think of seeing me, a polished and well-dressed businessman, naked and bound to the back of a chair while being whipped to tears.

The morning passed into afternoon and the time arrived for our company presentation. Karen and I stood in the wings of the small auditorium stage as we were introduced, and as we waited her hand moved to the front of my slacks and her fingers found my cock. Once more I was thankful for the rubber bands keeping my erection down even though I was again being uncomfortably squeezed as we walked out on stage.

Our presentation went very well. Karen and I were both good speakers; we had prepared well and our slides were engaging, and we believed in our new product line enough to evangelize it convincingly. We finished on time and spent the next hour chatting with the attendees who wanted to meet us and learn more about our company, or pitch their own services -- the usual networking stuff.

Finally the day came to a close and the end of the conference. We packed up all of our materials and now had the evening ahead of us, as our company was generously allowing us to spend another night in Las Vegas and fly back the following day.

"Shall we go shopping before getting dinner, Jack?" Karen asked me. "I found an interesting store." She showed me the place on her phone and it looked like it filled the bill; I had known we wouldn't have much trouble finding a place in this city that had the items Karen had in mind to buy. "Looks good," I said, "let's go."

A half hour later we found ourselves in the Las Vegas Adult Emporium, me with a red plastic shopping basket in hand, and we were like two kids in a candy store. I thought I'd been around the block a few times but I was seeing things I didn't know existed and I'm sure Karen was too. Of course many of the items had very obvious purposes, sometimes not necessarily pleasant for whoever was on the receiving end.

It didn't take us long to pick out a collar and leash set, the first toy I had suggested last night to Karen's enthusiastic agreement. We found a simple black leather collar with a chrome ring attached to it and a nice chain leash with a leather handhold, and as I looked at it in my shopping basket I felt light headed thinking about wearing it. I knew Karen would have me doing many things later on, but even just the thought of being on a leash held by her hand was intoxicating to me.

We then picked out a nice set of padded leather wrist and ankle cuffs, and naturally they had large rings on them for tying the wearer in any way desired. Karen also grabbed a large bundle of soft cotton bondage rope, and then surprised me a little by adding a set of very traditional looking police handcuffs to our basket. "Have you fantasized about arresting someone?" I asked her with a smile.

"My father was a cop," she replied, "and every time I saw the handcuffs he wore on his belt I couldn't help thinking about what it would be like to snap them on my lover's wrists."

"I guess you're going to find out," I said. "Yep," she replied, giving me that crooked grin.

We added to our basket a beautiful Scottish tawse, hand-made with two long and heavy black leather side-by-side straps, with a brown and black pattern on the handle. I had the feeling I would be having a love-hate relationship with this item that would start tonight and continue for a long time to come.

That feeling was reinforced when Karen tossed a ball gag into our basket. I glanced at it and then looked up at her. "We'll need to keep the noise down tonight," she said, letting some butterflies loose n my stomach.

Next we came to a display case with an assortment of butt plugs, which I anticipated Karen would want to use on me. As we looked them over she asked, "What size should we get, Jack?" Since I had never had anything in my ass before her insistent fingers the night before, I mumbled something about starting small. "That's fine Baby," she said, "but let's get a larger one too... we'll work up to it."

Then it was time to choose a strap-on harness, which Karen had said she wanted to try wearing to further violate me. It didn't take long for her to decide that one in particular had a realistic penis dildo that closely resembled my own in size and shape. "You're going to find out what it would feel like to be fucked in the ass by you," she whispered to me, setting my cock swelling against the rubber bands I still wore.

This harness had the added bonus of another dildo on the inside that would go inside her vagina, and I thought to myself that this would inevitably lead to her fucking my ass long and hard enough for her to cum herself.

After grabbing a tube of lubricant expressly designed for anal sex we made our way to the store cashier, an attractive young woman with a severe haircut and rather extensive tattoos and piercings. As we placed our items on the counter I wondered if she was curious which one of us would be on the receiving end of all this gear. "Did you find everything you were looking for?" she asked us.

To my embarrassment Karen quickly settled the question of who the sub was by replying a little nervously, "Actually no. Do you have, like, a small flogger that would be good to whip a penis with?"

The cashier replied that she did, and went off to retrieve the item she had in mind from a nearby display case. She quickly returned and presented us with a very short flogger having only 4 thin leather strips at the business end. "This works really good," she told us, and smiled at me while adding, "it's small enough that you can aim it exactly where you want it to go. Anything else?"

"Um, do you," Karen began, "have anything that would, uh, make it hurt when he got hard?" My face was probably turning a little red at this point.

"Well," the cashier said, "a lot of people use the Gates of Hell, but my boyfriend says they just squeeze him and don't really hurt. Maybe you'd like to try this," she said, and reached down below the counter.

What she brought up was the most menacing-looking sex toy I had ever seen. It was a hinged stainless steel cock ring, more like a sleeve really, being at least an inch and half long with dozens of pointed screws that would be aimed at the hapless cock inside it. A tiny padlock kept the device closed around the penis, and it even came with a small hex key to adjust the depth of the screw points.

"I love this, my boyfriend says it hurts like hell when I start getting him hard," the cashier said, again looking at me and smiling, clearly knowing what I was in for and enjoying the thought.

"Oh... well this looks perfect," Karen said, "I think that's everything for now."

Our purchases added up to a pretty penny; this stuff was pricey. "I guess we can't expense this," I said, and Karen laughed.

With our shopping complete and our new toys bagged I started to leave, but Karen had another idea. "Do you have dressing rooms?" she asked the cashier.

"Yes," she said and pointed the way. "You can try things on in there but no actual sex is allowed." I then noticed the small video monitoring screens behind the counter and realized that nothing would be private in those dressing rooms.

We made our way back to the dressing rooms and went into the nearest one. After closing the door Karen said, "Jack, don't you love this stainless steel thing? Let's get rid of those rubber bands and go ahead and put it on you."

As she was taking it out of the package I lowered my pants and briefs and took the rubber bands off of my cock, grateful to finally be rid of them but also knowing that something worse would momentarily replace them. I glanced at the small camera mounted up high in the corner and began to get aroused thinking the cashier might be watching. "Karen," I said, "I'm too hard to put this on now."

She looked at my erection and said, "I'll have to fix that, Jack" and took out her brand new little flogger. Before I could utter a word of protest she took the head of my hard cock in her hand and brought the flogger down hard on my shaft, making a loud snapping sound that I was sure could be heard in the store.

"Jeez," I gasped, "that really hurts."