Sylvia Did What?

This is a completely different type of story to anything I've written or even thought about. This came about because a casual acquaintance is into BDSM. We got to talking one day about limits and boundaries. Not having talked in a few years, one night she had called while I was lying in bed. First thing she said was "Tell me why I can't find someone to SPANK me the way I want to be spanked?" I was speechless, and then said, "Well, I can't because I'm 1000 miles away. Sorry!" This story is partly my imagination, and partly things I've read or been told by people.

Enjoy.

I was sitting at my desk pondering how I was going to coordinate everything that had to come together for my latest project when the phone rang.

"Don Tyler." I didn't bother with my company name or my job title. This call came in on the line I reserve for people I want to talk to when I'm busy.

"Don, lunch today. I have to tell you about my latest client!"

My friend and occasional lover, Sylvia was on the other end.

"I'm dealing with crap here at work, but I really could use a break. How about Sabatino's at 2?" I spoke.

"Cool, see you then!" She hung up, and I turned back to work.

I'm Don Tyler, system's engineer extraordinaire, and co-owner of Systemic Industries, Inc. My partner Jacob Style and I are a small, but upcoming firm specializing in, you guessed it IT Systems. We met when we were at State U and struck up a conversation and have been friends ever since. Graduating into an iffy job market, we both took a "gap year" and traveled and then came back to start our business.

I'm pretty ordinary other than my IT talents. Six foot, 180 lbs, thinning hair and average good looks. But that's not important to this story.

I wonder what Sylvia is wound up about.

Sylvia. Now there is a story. Syl and I met in college as well. She was a physical education major with a minor in kinesiology. And she played tennis, so she was pretty fit as well as having a body that turned some heads. Five six, 125 lbs with nicely toned legs and dirty blond hair that turned almost white in the summer with all the sun exposure from playing tennis, teaching tennis and being outside.

We hit it off and even dated some, but both of us were hyper focused on other things to have a committed relationship.

During our senior year, Sylvia had her awakening. She was dating this guy who seemed nice enough. One night while they were in bed, he asked her to spank him. She was caught off guard, to say the least, but did. And when he asked her to keep spanking him and do it harder, she did. And surprisingly, she found she liked doing it.

The next day she went online and started reading up about the whole BDSM world and all the different kinks people had and why and what they got out of their particular kink. What really shocked her was the realization that she too had some kinks.

To make a long story short Syl figured out that she was a Dominatrix, or at least a Top. She didn't want to have her body abused, and didn't need to be kinky to get off during sex, but there was a head rush she got from being in charge and doing things to people.

Unlike Jake and me, Sylvia had a job lined up when she graduated, but like everywhere, the pay wasn't that great and the school was in a bad part of town.

By now she had met and become friends with some people who were in the "scene" and this one older woman suggested that Sylvia join her in her business of being a professional Domme. It took some time, but eventually Syl decided to try her hand, so to speak, and she started working part time as a Dominatrix. Obviously, she had to be careful not to put her teaching job in jeopardy, and she had some pretty strict limits on what she would, or wouldn't do with clients.

At this point we were very close friends, and occasional fuck buddies. I'm not sure if our relationship desires would ever align, but it seemed like we were in agreement for now.

So, every so often she would have a client that was into some really kinky stuff. What made it really kinky, often it was pretty tame and non-sexual, but it was the idea of having a Dominatrix do it that made it a turn on for her customers.

Anyway, Sylvia would sometimes tell me all about particular kinks, and what made it a turn-on for her clients. She knew I got a kick out of hearing her stories, and I think she got off telling them.

So that brings us to lunch at Sabatino's.

"Don, you really must get out more often. You look so pale." She scolded me as she kissed me on the lips.

Syl had on a pair of jeans, low heels, and a pale purple blouse. Her hair was pulled back in a loose ponytail that made her look demure. If people only knew!

"Yeah, well there's this thing called work, and people called customers who want me and Jake 24/7."

We were shown to our table and the waiter came to take our drink orders.

"White wine for me" Sylvia ordered and promptly ignored the waiter.

"G and T please. Hendricks." This was my go-to drink. "And a bottle of still water for both of us."

"All right, spill it. What has you so spooled up that you had to drag me out to tell me? You couldn't tell me over the phone? Must be pretty juicy!"

Sylvia looked around to make certain we weren't going to be overheard. Sabatino's is a typical Italian restaurant and the tables are packed in there. Just barely legal occupancy for the fire code if the place as full. Today, however, was the tail end of the lunch hour, and very few tables were in use.

"Well, there's this guy, I'll call him Rich. He's been to see me a few times over the past couple of years. Maybe every 4 or 5 months. And he's pretty vanilla-ish. I mean he likes to be flogged, maybe tied up. Once I did a "medical exam" and checked his prostate, which he seemed to like. But overall, there's nothing I do to him that he could probably get his girlfriend or wife to do. He just seems to like the idea of having no control over who that someone is doing things to him."

"This time was different, though. He emailed me and said he'd like to have a massage; that he'd like to act as though I'm a professional masseuse, but would like to have a Happy Ending of some sort. At least in the context of the BDSM world. And he left it up to me to figure out a way to push his limits further."

"Well hell, I'd like to have a Happy Ending too!" I snorted. "Putting in the hours I've been keeping lately has put a hurting on my sex life."

"There's something you can do about that." She said, making the telephone motion with her hand.

About then, the waiter came back with our drinks and asked for our orders.

Sylvia said, "I'll have the Caesar salad with chicken, extra dressing on the side."

"And you, sir?"

I'm a carnivore and realized I was hungry with a capital H. "Veal Parm for me, a salad on the side and lots of garlic bread please."

Syl continued.

"Anyway, so this guy shows up, I greet him, and ask him if he has any particular muscles that need massage."

"No, just a good, all-over body massage." He says, all the while looking a bit nervous.

"Okay, Rich." I say. "Go into the room, strip down and lie on the table under the sheet and I'll be in momentarily."

"I had taken the stirrups off the exam table I use for medical play and staged it like a massage table. I go in. He's lying there on his back. I stood at his head and start massaging the back of his neck and shoulders. As I lean over his head, he lifts his head and nuzzles my tits. I tell him that is inappropriate to do to your massage therapist, and he smiles and says he's sorry."

"I continue working on his shoulders and his arms, gradually getting down to his hands. As I move to start massaging his thigh, he gropes my ass and squeezes one cheek."

"Now I'm sort of pissed, but at the same time I know he's playing a role as well. So, I tell him to cut it out, and if he continues, I'm going to have to punish him. He snickers at me and says, 'Oh, yeah, what's a little girl like you going to do to a big guy like me?' "

"Do you really want to find out? I ask him. I stare at him for a moment with my best DOMINATRIX BITCH LOOK, and then continue."

"Of course, he smacks me right on the ass, and says he always like his women to have a nice booty, and mine could use a little filling out!"

I chuckle and she glares at me. "What? Your booty is perfect! All that tennis and running. It's nicely sculpted and firm. I know from personal experience. Remember when you woke up a few months back with bruises on your ass from my fingers gripping you?"

"Yeah, it hurt like hell for two days, asshole!"

"Anyway..." she continues. "Well now, I'm really pissed. This is starting to be a bit more serious of a scene.

"So, I grab one of his hands and twist it down to the side and put one of my restraints on and then do the other side. Now his hands are tied up and he can't do that again."

"I looked at him and said 'since you're so into playing with my ass, how about I play with YOUR ass?' "

"I grabbed his foot and pushed it up towards his ass, tied it off, and did the same to the other foot. Underneath the exam table I keep an industrial size bottle of lubricant and some plastic syringes. You know the kind with no needle for squirting liquid? Kind of like giving the cat its medicine?"

"I filled one with lube, shoved it up his ass, and squirted him full of lube. Then I grabbed an exam glove, lubed it up, and stuck my finger up his ass, feeling for his prostate."

"How do you like that, Mr. big and strong guy? I stroked his prostate for all of 30 seconds and his tiny little dick started oozing pre-cum. 'Oh, does Mr. big and strong want to come?' Well, I'm not going to let that happen."

"Well, yeah, I'm sure that got a reaction." I said. "I remember this one girlfriend I had that liked to stroke my perineum when she was blowing me, which is pretty much the same thing. She just would never have stuck her finger up my asshole."

"We can try it sometime! Maybe get over your tendency to pucker up when I let my fingers roam." Sylvia was always trying to get me to let her.... Not happening.

"He's getting some..." Syl stopped talking as the waiter arrived with my salad and some bread for her.

"Anyway, he's getting some pleasure out of this, even though I know he's got to be dying to cum. I stop stroking his prostate. About then he says, 'Those sexy red lips of yours would look pretty nice going up and down on something, if you know what I mean.' "

"I looked at him and slapped him across the face."

"Don't you ever suggest such a thing, you scummy, little dicked, pussy of a man. My lips would never be degraded by doing such a sick thing with you. But since you like the idea of lips around a cock, that give me an idea."

"I then took a prostate vibrator and stuffed it up his ass and hooked the cock ring around his willy to hold it in place. He might get some pleasure out of that, but eventually it will become annoying."

"I put a collar on him, clipped the leash on, and then untied him. Leading him over to my custom bench, I had him draped over the trestle and cuffed his wrists in the front while he was standing on the back side."

"I started flogging him and talking smack to him, as much to humiliate him as to burn off some of my very real pissed offed-ness."

"Oh, so you think seeing my lips wrapped around your puny dick would be nice? Well, I've got something for YOU to suck on."

"I stuck an 8" dildo on my strap-on harness, put a condom on it, and walked around in front of him telling him to "Open Wide!". He shook his head and wouldn't open his mouth, so I just pinched his nose and waited. And waited."

"He, of course, eventually had to open his mouth to breathe, and I stuck the dildo in and told him to suck. He started slobbering all over it, and gaging when I grabbed the back of his head and made him deep throat it."

"You are nasty." I said, looking at her and shaking my head.

"Well, you have to understand. He's there for a reason, which is to get punished. But he's really driving things and provoking me to do things to him. It's called topping from the bottom. And I know this; he gets off and leaves satisfied. The thing is, after several visits, I pretty much can predict how things are going to progress."

"What I needed was something to stir things up, and really push his boundaries. And that's when it came to me."

The waiter was walking our way with our food, so I tilted my head and signaled to Syl with my eyes, and she stopped talking.

We each took a few bites of our food, and made some small talk as the staff was cleaning up the nearby table and setting them for the evening crowd.

Finally, Syl was able to continue her story.

"The business next door to my dungeon is a graphic design shop run by Tino, a really sweetheart of a guy who happens to be gay."

"So, I'm face fucking this client with the dildo, and I hear Tino pull into the parking lot in his souped up '69 Camaro. And all of a sudden it comes to me."

"I pull out of dickwad's mouth and grab a dildo gag to strap on him."

" 'Don't go anywhere!' I tell him, like he could if he wanted! And then I blindfold him."

"I went to the front door in my office and opened it a crack to call to Tino to come over. He knows all about me and what goes on in my 'studio'. I told him what I had in mind and he agreed."

"I stood behind the door to let him in and his eyes popped as he took in the sight of me in full Domme get-up."

" 'Damn girl, I'd let you fuck me with that schlong you've got there!' Tino said to me."

"Shush! I told him to take his clothes off in my office and wait 5 minutes and then quietly come in to the dungeon."

"Oh, I think I see where this is going! You are evil. How's your salad? Need another wine?" I asked.

"Nah, I'm fine. How's your tortured baby calf?" Syl rarely eats meat, and just couldn't resist getting a jab in regarding my eating habits.

"Delish! Please continue." I motioned.

"So, I went back to my trussed up, gagged client, and whispered in his ear. 'You remember what your safe word is?' He nods. I ask him again, you sure? He nods again a little more vigorously."

"I run a Wartenburg wheel up and down his back, and around his front, making him twitch and tense up a bit. Then I flogged him a few times, making certain that a few of the leather strips smacked around the front of his leg."

"That makes me wince just thinking about it. Don't ever get any ideas we're going to play like that." I wasn't into kink like that, even though Syl wanted to do some things with me.

"Oh, come on, if the strips aren't too thin, it feels kind of 'thuddy' and actually feels good." Syl grins.

"Back to my story. I took the dildo gag off and told him that I thought he did a really piss-poor job sucking on my cock and that I knew he could do better. He said he was sorry and would try harder. I also told him that since he was so enamored of my red lipstick, that seeing his red lips wrapped around my 'cock' would be nice. I had grabbed my lipstick while I was in the office with Tino, so I squeezed his jaw and slathered some lipstick all over his mouth."

"I stuffed my dildo in his mouth again, and he started sucking. About this time, Tino comes in and stands there naked."

"I told dickwad that I thought he was doing a little better, but maybe he needed some motivation; that maybe my dick just wasn't good enough for him. I pulled off the blindfold and said, maybe THIS is what you need to suck on!"

"He took one look at Tino and you could see the panic in his eyes. He closed his mouth and started squirming and pulling against his restraints."

"Oh, come on now Richie? What's the difference between my dildo and this magnificent real-life cock here? It's not even as big as my dildo, but it does things my dildo can't. And if you swallow all of his cum, I'll make it up to you!"

"He mumbled, 'but I don't want to'."

"I said, well, you know the way out of this. That's what safe words are for. You just have to say the word. I'll untie you and you can walk out the door. Just don't call me again. It's your choice."

"Tino stepped closer, and I grabbed the guy's head and turned it towards Tino. He looked at me with pleading eyes, but didn't say a word. I told him to just say the word.... He didn't, so I pushed his head to the cock. He opened his mouth and took Tino's dick."

"Wow. You really did that?" I was flabbergasted. "He actually started sucking his dick?"

"He not only sucked Tino's dick, he was doing a pretty good job. Tino was getting aroused and harder. I took my hands off dickwads head, and he continued slurping away. I could see he was using his tongue as well as sliding his lips up and down Tino's six inches. While that sounds average, Tino's dick is a bit thicker than average, so I know it filled up his mouth!"

"Wait a minute, so Tino was bareback?" I was surprised. I knew Syl was religious about safe sex in her dungeon.

"Yes, I thought that needed to happen to make the scene more intense. Nothing to worry about; Tino is even more cautious than I am. In fact, Tino has been celibate since he broke up with Ronnie last year. He never was promiscuous, and the break-up really soured him on dating."

"Well, I stepped back to watch for a moment, and then stepped around behind where he was standing on the pad, still leaning over the trestle, sucking away. I lubed up my dildo and slid it in his ass. Now he was getting spit roasted."

"It was pretty clear Tino was about to cum, as he started thrusting and breathing heavily. Our boy was almost into sucking by then, and was doing a pretty good job. He was even thrusting his hips into me as I was butt fucking him."

"About this time, Tino came and it must have been a gusher, as Richie had some of the cum leaking out of his mouth and dribbling down his chin. He was definitely swallowing, though!"

"SERIOUS?" I almost dropped my fork. "You're telling me that not only did this Richie guy suck dick, but he swallowed cum? All while you're porking him from behind?"

"Yep!" Sylvia nodded and took another bite of her salad. "I was actually surprised how into it he got, because he had never indicated that he was open to anything like this. I only went this far because he was pushing my buttons, trying to control things in the scene."

"Things had gone on long enough. I motioned Tino he could leave, and I told Richie he had done a 'good job', and stroked his back as I pulled out of his ass. I untied him and led him over to the bed in the corner. I told him to lie down. I knew he was going to need some serious aftercare after such an intense scene, so I held him close, told him he did well and I was proud of him."

"He relaxed and starting blubbering that it was almost too much for him and he couldn't believe he did 'that'. That he never would have thought he could suck a dick."

"Finally, it was time for him to get dressed and leave. I was actually drained and in disbelief at how far I had pushed things. I'm not sure I would have planned to do this, but in the moment, things just flowed. I don't feel bad for doing it, as I repeatedly gave him the out of using his safe word. That is one thing that is so important when doing a scene."

"I gave him some cleansing wipes to clean his mouth and face and showed him to the bathroom. He left a few minutes later."

"Wow. Well, just remember, my safe word is NEVER!" I shook my head. "I know you'd like to play around some, but I can't wrap my head around the stuff you do in your dungeon."

"Aw, Tyler, Tyler, you need to live a little. You might like some of the toys I have in mind for you! But I will always stop if you use your safe word."

Just then, the waiter came by to see if we wanted dessert. I could tell he heard the last part of what she was saying about a safe word as his eyes got wide and he stared at her.