Mistress Maggie

Slowly she pulled her gown up, exposing a very well endowed cock and balls, it was just beginning to become engorged, beautifully framed by a delicate lace garter belt I had only seen in exclusive catalogs. Her package appeared it might easily reach 9 inches before it was finished. The techno-pop music booming in the background made the whole experience unreal. I found myself swallowing hard, not sure what to do... then reaching my decision instantly as each and every heartbeat made her cock get bigger. Her left hand began pushing on my right shoulder with a constant pressure, she made her needs known, and I was to suck her from my knees.

Once I was eye level with her cock, I touched it gently with both hands, then began stroking it back and forth, getting a long moan from Nona. The small crowd that had been casually gathered around her, now created a protective screen, keeping prying eyes out, and me in. But I didn't want out, certainly not yet, as I took a few inches of her down my throat, and licked as much as I could as it went down. Once again, she moaned...

"Oh you sweet, sweet... ugh," Nona was saying, "Sweet young cock sucka... Oooh... Fuck!"

I gave it everything I had, trying to remember every porn video I'd ever seen and reproduce it here for Nona if I could. She had rotated in her seat just a bit and had her hand on the back of my head, as she now began face-fucking me in earnest. Now the sensations we're mine as I felt my own orgasm building with Nona in control. She was pushing my mouth relentlessly down onto her 9-inch fuck toy. And she was telling me exactly how she was feeling as well...

"Yeah," Nona exclaimed, "you like being fucked, doncha lil' slut? Well, you keep me deep throated baby... that's right, breathe through your nose lil girl, that lovely mouth has other duties right now... sh-shit... gonna cum sweetie... gonna cuuuummmm!!"

I had been rubbing my own cock during most of this, and with a gut wrenching scream, I felt 3-4 streams hit the back of my throat just before she relaxed. I swallowed all that she gave before pulling herself from my mouth. I couldn't believe what I'd just done, or had allowed to be done to me, but now after I'd had my own orgasm, I fell to my hands and knees exhausted. A minute or two after that, I began feeling hands helping me to my feet, and saw the joy on her face, as I realized I'd also thoroughly enjoyed myself, and the small crowd that had surrounded us now gave up a thunderous ovation, whether for me, for her, or all of us, I wasn't sure.

"Oh baby," Nona purred, "Thank you... you know how to make an old Dom happy sweetie, that's sure. Hey Bobby? Take young Fancy Pants here down to the lockers and help him get cleaned up huh? We'll meet again in my private rooms... Bobby here will bring you back to me, okay sugar?"

As we went to get me cleaned up after cumming in my pants, I asked 'Bobby' a couple questions about Nona, and who she was in relation to the club. His answer was another head turner, she was a part owner now, ever since Maggie left. He explained that Maggie had bought the club a couple months ago, and made sure the 'regular gurls', or shemale Doms, that had been with the club for years would always be taken care of for as long as they lived, by splitting ownership into as many pieces as there were gurls. If one died, the others simply got a larger share, so no survivors would end up owning part, and thereby dividing ownership of the club, only the old shemale Doms that started with 'Sisters' could be owners. There were five, and Nona was one of these remaining original owners since Maggie bought it. Suddenly an obvious question came to my mind, and I asked it as non-judgmentally as I could, was Maggie a transsexual?

Bobby was a large black man in his middle/late thirties, whose Philly accent revealed his roots, and Trilby hat revealed his fashion sense. He laughed for a minute, and told me that was what nobody could really understand. Everyone knew she was a bisexual genetic woman, and yet she cared so much for these shemales, that she bought this whole place for 'em... quite a puzzle indeed. He went on to explain that no one had either enough of a reason, or guts for that matter, to ask her why. And it was such a popular thing, that no one really cared why either.

After getting cleaned up, Bobby took me back. Nona was now in a long silk dressing gown, and reclining on a divan in the corner of the room. Bobby asked if I needed a drink, and I asked for water, then he brought a chair over next to her for me to sit in, and left the two of us alone.

"Please," Nona motioned for me to sit next to her, "please dear, have a seat and tell this poor old woman how she can help a bright young thing like you... you say you want to write a story 'bout the 'Sisters'? ...Really?"

I blushed as I felt myself now trapped in my own lies. And just as suddenly as I had decided to suck her cock, I dumped everything on Nona, this time the truth... about how I'd first seen Maggie, how I'd fallen for her, and how I'd do ANY thing to be with her.

"Mmhm," Nona was again purring, "now we hearing the truth. I've known a thousand young ones like you, Nona always can tell. But you... you're not even sure... you don't even know your own mind yet... on your own gender... how you know Maggie what you wanting?"

I sighed as heavily as I ever have, because it was the only damned thing I really DID know... I wanted this woman, needed her, I would do anything for her... but... how to explain? At this point, my body performed the function that my mouth couldn't.

"Wha... are you... oh," Nona was staring at me now, "Oh my dear one, I'm sorry. Nona has gotten old and should have seen... tears always tell the best story, hmm? Alright, let me tell you what I can about Maggie, I don't think she would mind after seeing those tears."

And so she did, Nona was every bit as true to her word as could ever have been expected. It turns out that Maggie had been a 'Pro' Dominatrix in the S&M community in and around Philadelphia for a little over 11 years before she dropped out of contact with others in the community as Mistress Magdalyn. She was also a 'switch', which means she also used the services of Pro Doms in the area as a 'sub'. She had been brought into the community and learned everything she knew from a Mistress Cynthia, another Pro Dom, albeit a true 'top'. Nona didn't know much of her background before this, indeed nobody seemed to know anything, not even where she was from, went to school, nothing from her early life.

But the rumors... they were rampant... the one that Nona gave the most credence to, was that she had been kicked out of her family home, and was forced to learn the hard rules of the street at a very young age. And something... something terrible had happened to her that would not allow her to speak of that time in her life, to anyone. Nona spoke in hushed tones about the few times she had seen Maggie show real emotion during an S&M session, explaining it as an almost religious experience. Finally, she explained her later years, becoming what can only be described as a den mother to the various Doms in the local scene, she always would make sure any Dom that ran into health problems was taken care of.

Suddenly one day Maggie got very ill, dropping out of sight, and not telling anyone. But she discovered one of her subs named Henry was the CEO of a huge medical company and when she finally told him, he hired all the best doctors that he could for her. Eventually she got better, some kind of a cancer they said... anyway, she and this CEO were married, he becoming her 'pet' of course. But once again, just as it seemed she'd found herself some happiness, her Henry turned up dead in a hotel room somewhere, with the police saying it was a heart attack. So... for whatever reason, Maggie decided to buy 'Sisters' outright with her husband's life insurance, and gave it to all the shemale Doms that worked down here at that time...

"Believe me," Nona finished after a long sip of water, "the name Maggie is said with great reverence in this building, if they ever come up with a saint of Dominatrix's, I know a lot of folks who will insist Maggie's name be placed first on the list, ha-ha!"

I clicked my pen shut, and folded my notebook closed. Then looked at the woman who had given me all of this information, as I stood up, leaned into her, and kissed her gently on her lips. The tears welling in my eyes were something hard to define, I don't know if I could explain what they were all about, but I knew how they got there, and was determined to use that emotion to get closer to the woman I'd fallen so hard for. As I turned to go, I got one more question.

"And so little one," Nona was asking, "now that you know these things about Maggie... was it worth your effort finding it?"

I turned my head to give her my biggest smile, and with tears rolling down my cheeks... I knew that they gave her all the answers she needed.

***

I spent the week after graduation trying to come up with a way to somehow let Maggie know that I knew her background, and convince her to take me as a sub. Two major problems came up immediately, first I'd somehow have to make sure she knew I was not a threat of any kind, otherwise I could end up in the bottom of some river somewhere, second I'd have to convince her to become something she'd already given up, a Dominatrix!

I studied this problem for weeks, in every formulaic way possible, and could not come up with a solution. I would finish my regular work, then start pondering how to go about this huge task I'd given myself. Eventually though, I found a few people who, while they had no idea of Maggie's Dom and sex club background, knew quite a lot about what had happened after she'd been married to the former CEO of this company.

After Maggie got over the pancreatic cancer that nearly killed her, she became fascinated with the science behind some of the drug treatments she had been given, as well as the devices that helped to give it in the right dose and the right time. She crammed 4 years of pharmacology into 1 and her husband eventually hired her to be his development group's director. Apparently, at some point within the next 2 months, her husband had turned up dead in a hotel room, and no one even knew what he was doing there. After his death, there was a take-over bid for the high tech company he'd worked his whole life to build, which Maggie was fighting. Now it seemed she was not only fighting for their company, but even her job. How was I supposed to gain this woman's trust with all of this intrigue swirling around her?

On one particularly hot august evening, I found myself alone in my cubicle, with the kind of super-humidity you can only find in Philadelphia. I couldn't face going home to another sticky sleepless night. And just to top off my problems, my summer internship was drawing to a close as well. In total and abject frustration, I threw my pen at the cubicle wall, unknowingly scaring a poor cleaning woman who was dusting on the other side, I heard her give a loud gasp.

"I'm sorry," I apologized, "I didn't realize anyone was here."

"Aye... that's sure me boyo," she replied in a thick Irish brogue , "nearly scared me outta my everlovin' mind, that did!"

I smiled up at the very matronly looking woman as she seemed to smile back. Perhaps in her late fifties, there was a remarkable twinkle in her eyes and while she was small in stature, anyone could see the strong character underneath.

"Well, you seem in a fine state," she was saying now, "What's got such a young buck's nerves all in a bunch, eh?"

"Oh, I dunno," I replied, almost wanting to tell her, "um... it's... just a personal problem."

"Wot!" she exclaimed, "You should be out at a dance club... one of those um... discees... wait, discos! That's what I was lookin' fer... flirtin' with the girls, eh? Now... I have a niece..."

"Thanks," I laughed, amazed the banter had gotten so far, so fast, "but I know who I want... just don't know how to get her attention is all."

"Ah-ha!" she exclaimed, "Co-worker is it then?"

I shook my head up and down in a 'yes', and once again, my eyes welled up thinking I might never find a way for us to be together. And suddenly lightning struck, as I looked into this cleaning woman's eyes... and then her chest, where a nametag hung that I could barely see.

"Wha... what's your name?" I asked in a hushed voice.

"Oh dear... it's Maggie," she replied while adjusting the tag, "Damn thing's always falling off!"

"So Maggie," I was standing now, as something seemed to have pinched me in my very soul, "if you were being pursued by a much younger man, a young man that knew he loved you. Yet you had to be careful of them, as they might be up to no good. What would it take to make you trust him enough to at least know he wasn't a threat, and that he might even be in love with you?"

I wasn't sure what exactly had come over me, I suddenly had complete trust in this cleaning woman to help me figure out a way to get closer to the love of my young life. For the first time I think I saw the incredible chances I was taking to find a way into this woman's heart.

"W-well I," she stuttered, "W-what do ya mean... how could you be up to no good?"

"Maggie, I need your help," I was trying hard to explain myself, "I've fallen in love with Maggie O'Shea, do you know who she is?"

"Oh, you poor lad," she cried, "of course, everyone whose worked here as long as me, knows Maggie O'Shea! Love is it? Are ya sure?"

I stared back at her, not knowing what else to say, was it so terribly crazy for me to have fallen in love with this beautiful older woman? My eyes dropped, along with a single tear...

"Alright," she sighed, "I shouldn't be doin' this... but you seem to have a kind soul, I can see that at least... here... tell ya what we'll do. I clean her office every morning, and wot I'll do is every morning, I'll leave a solitary flower in a vase on her desk. When you're ready to reveal yourself... that is... when she is just about out of her mind from wondering who's sending these flowers, all you'll need do, is walk up to her, and place one of the flowers in her hand... she'll be ready to know more about you by then, I guarantee it!"

"Really?" I could only stutter out, "B-but, well I mean... what kind of flower should we use?"

"Oh saints be ta..." she yelled up at the ceiling, then with a loud sigh, shook her head looking back at me, "and such a bright lookin' lad too! For an Irish lass... an O'Shea... a wild Irish rose? Why... what else? A rosebud, me darlin'!"

***

After two weeks of having a fresh red rosebud placed on her desk every morning, the whole thing had hit the water-cooler circuit. Apparently, Maggie (O'Shea) still had no idea who was leaving them for her. They even said one of the cleaning ladies was involved and that the director of development refused to have her fired when she wouldn't say who had put her up to it. The day after she was confronted, after a planted camera caught her placing the rosebud at her desk... Maggie the cleaning lady walked by my cubicle and smiled, then winked. That was our signal that it was probably a good time to reveal myself to her.

It just so happened that the next day was her secretary's birthday, and the whole development group was scheduled to go out to lunch to celebrate. Even better, the restaurant we were going to was the Smorgasbord (an Old Dutch term for 'all you can eat') which would leave many opportunities to get a few seconds alone with Maggie, and give her the rosebud, it would be up to her what happened after that.

A sultry august morning was beginning to feel the sun's true heat as the development group all gradually made it inside the air-conditioned Smorgasbord. We were all eventually seated, after which we ordered and received our drinks, then had a toast to Maggie's secretary Janie, being one year older. Soon enough, people were disappearing to grab platefuls of food and bring them back. Maggie seemed disinterested and ended up alone at her table, obviously concerned about something, she was staring into her water glass.

Walking back from getting some frog's legs, I took my chance.

"Here Miss O'Shea," I said quietly, always using her last name and Miss as a sign of respect, "I found you some frog's legs, didn't you say you wanted to try some?"

I used the plate of croaker appendages to distract her, placing a rosebud in her water glass.

"Thomas!" she cried, "I said I'd NEVER try them, not that I wanted... oh never mind!"

I sat down properly dejected, and she finally laughed at me, giving me the most radiant, beautiful smile I'd ever seen in my short life. That seemed to bring her mind back to the party, and she began picking up her water glass for a drink. But spotting the small flower floating where before there had been none, she yanked the glass back from her lovely lips so hard that its contents flew everywhere. Her eyes became riveted on the rosebud... then they narrowed... and then I got a look that I would remember forever... it scared me that much. Ever so slowly, she took the rosebud out of the glass, and began twirling it between her thumb and forefingers, all the while watching me without ever blinking once.

Eventually I saw her coming to a decision... she had realized what she needed to do, standing up and leaning over towards Janie, she said a few words into her ear and reached down for her handbag. Pulling out her wallet, she handed her a company credit card all while continuing to stare at me. Closing her wallet and placing it back into her purse, she quickly looped the purse's handle over her forearm and walked over towards me.

"Mister Huntsley," she said quietly, emphasizing the 'mister' in her beautifully low and sexy voice, "I think you and I need to have a talk... care to join me?"

Time seemed to slow down, all the activities around me were still occurring as before, but it felt as if my heart was going to beat itself right out of my chest. A serious chill hit my spine as I stood up and carefully avoided her deadly gaze.

"Y-yes Ma'am," I somehow managed to squeak out, "I believe I owe you an explanation."

There was a glass exit door nearby that opened onto the back patio of the restaurant. Under better conditions, the large patio area was used for open dining. But this late in the summer season, nobody used it, nevertheless it was still under some shadow this morning and Maggie walked to a secluded area with a concrete picnic table and chairs. It was far enough from the main dining room windows so we could not be seen, but still just cool enough that we wouldn't melt in the noonday heat. Maggie dropped her purse on the table, pulled a chair out where she wanted... no, make that REQUIRED, me to sit, and sat down next to me.

"Alright Thomas," she said enigmatically.

Indicating with an underhand movement that I should continue to explain myself, she paused. But then, after a moment of confusion, where I suddenly decided I needed to be elsewhere, she once again spoke... this time much more clearly.

"Do you have ANY idea the upset you've caused?" she exclaimed, "Well... DO YOU?!"

Somehow, I managed to swallow, and found enough courage to begin explaining.

"Y-yes Ma-am," I started saying, "I know... I kn-know a lot more about you... y-your past that is, than you probably know... um, I know"

That 'look' was back again, a look of death, certain death, at which she seemed to be an expert. But now that I'd started, there was no turning back, so I sighed, feeling the small loop of cool leather in my pocket... it was hard to start talking again, but it had to happen, it just HAD to.

"P-please Ma-am," I began again, "I... I've found you beyond attractive, almost irresistible, ever since the first day I saw your picture on the company website. It made up my mind as far as which company I wanted to work for, and then when I knew you had taken a special interest in me during the interviews... well, I just knew I wanted to know more about you."