Disclaimer and Legal Stuff: Don't read this if you're not supposed to, either because you live in a regressive community or you don't like erotic stories about gay sex (in which case, why are you here?). If you distribute this story, that's fine, just don't edit it, and leave my name on it. Thanks.

Simon And Sir
Chapter One
(for story list and FAQ, go to  maineboyxy.freewebsitehosting.com)

He was a guy I'd met in an Internet chat room.  We'd talked for a few weeks online, both in chat and in instant messages.  He was from a town not far from mine, about half an hour away.  I'd never met anyone from the Internet before.  In fact, not being out, I hadn't met many guys at all.  That's not to say I was a virgin, but I'd only hooked up with three guys, and at 20, that's as close to virgin as most gay guys get.  Since he lived a bit removed from my immediate, closeted surroundings, I finally gave in and agreed to meet him, sure that he wasn't someone who'd know my friends and comfortable that if I went to his town, no one who knew me would see me with him.

We'd exchanged pictures the first time we'd chatted.  He was older than I was, 26, with dirty blond hair and blue eyes.  He was a fairly conservative looking guy, clean-shaven, typical medium-length haircut, dressed out of the A&F and Banana Republic catalogues, pretty much like me.  His build was like mine, light but toned, not a gym rat but active in recreational sport.  He worked for a computer consulting firm, web site and graphics design kind of stuff, and invited to meet me at a bookstore near his house.  It would be public, he assured me, to let me get used to the idea of meeting a complete stranger who, I knew from our conversations, was interested in some kinky sex.

I was nervous as I drove over on the interstate that sunny, late summer, Saturday afternoon.  I wasn't worried so much that anything would happen since we'd agreed that we weren't going to hook up this first time, but I was nervous to actually meet a guy who was into doing some of the things I'd read on the web.  He'd told me he loved to tie guys up, and once they were vulnerable and defenseless, to tease them and bring them to the edge but not let them get off, even after they begged and swore and offered to sell their soul to him.  But he would use them to get himself off.  Over and over again.  I'd asked if he used safe words, something I'd learned about from the web stories I'd read and always got me off, because I knew he would get intense and all my experience had been vanilla:  sucking, fucking, jerking.  He said no, he liked his boys gagged if he wasn't soaking his cock in their throats, but that I shouldn't worry because he had another system in mind for my first time so I could stop a scene if it was more than I could handle.

I walked into the bookstore and went to the coffee shop area, where he'd told me he'd be sitting.  I picked him out immediately, reading an overseas news magazine, sipping from a mug.  As I approached his table, he looked up, caught my eye, and smiled in a slight, subtle way that reeked of sexual desire and wicked mischief.

"Hey, Simon," he greeted me.  "Why don't you go grab something to drink and we'll sit down and talk?"

God, he was hotter in person than his picture looked.  He had a great tan and he was wearing the bluest shirt I'd ever seen, a pinpoint button down, and it made his hair and eyes stand out -- his hair in contrast and his eyes in compliment.  As I stood in line for a latte, I felt my cock stir.  I willed it to stay calm inside my jeans, and it complied with reluctance.  When I had my drink, I returned to his table and sat across from him.  He closed his magazine and looked me over silently.  I watched his eyes as they slowly moved from my face and down my neck and chest and torso until the view was cut off by the tabletop.  They then made an equally slow return trip, and I could almost see his brain churning as he memorized the way my clothes fit my body, as he pictured what lay under them, as he planned how he was going to use me.  I think it took two minutes as we sat in silence, and then his eyes locked onto mine.

I felt awkward as he continued to say nothing.  Nervously, I looked down to the table, reading the upside down cover of the magazine.  Hastily, I raised my cup up to my lips and swallowed the hot, rich coffee.  I sat there writhing internally under his unrelenting stare and I felt my cock getting hard.  There was nothing I could do to stop it.  I was getting hard under the table, in a public café, just because he was staring at me.  I glanced back up at him, but I couldn't take his gaze for more than a second before I turned my head, looking over the stacks of books and the patrons picking through them.

"Does this make you uncomfortable, Simon?" he asked, watching me fidget.

I shrugged.  "I've never had a meeting like this before," I answered, still avoiding eye contact.

"A meeting like what?" he countered.  "A meeting with a guy, a meeting in a public place?  I mean, we've talked and I know you're not a virgin, so you've met guys before, right?  I know you're in the closet, but you're miles away from where anyone knows you, here."

I quickly cast about, checking to see if anyone was in earshot.  There was, a thirtysomething soccer mom with her elementary school aged daughter was sitting two tables over.  I squirmed.  "No," I stumbled, "I mean, I've never met a guy and had it start like this."  I barely spoke above a whisper.

"Don't worry about her," he said.  "So what if she overhears us?  So what if she knows you're gay?  You are, right?  Do you recognize her?  Does she know you?"

I glanced over at her as soon as the word "gay" left his lips.  She had no reaction, if she had heard, but the blush still spread over my cheeks.  "No, I don't think so," I answered quietly.

"Well, it shouldn't matter then, right?  It shouldn't matter that you're in a bookstore, sitting quietly, having coffee with a guy you want to go home with and whom you want to tie you to the bed and have sex with?"

My jaw dropped as my head whipped around and I looked at him.  His stare was so intense I had to drop my gaze to my hands.  My fingers were shaking.

"Because you do want me to take you home and tie you to the bed and have sex with you, don't you, Simon?"

The hair on the back of my neck and forearms was standing.  I couldn't believe he was saying this stuff in the coffee shop of a bookstore, as this woman, who by now had looked over at us, frowned, and stood to leave, heard every word he spoke in a normal tone of voice.

"Don't you, Simon?" he repeated.  I nodded softly.  "Don't you, Simon?" he asked a third time.

"Yes," I answered meekly, almost mouthing the word.

"Yes, what?"

"Yes sir?" I offered.

"Yes sir, what?" he persisted.

"Yes sir, I want you to take me home and tie me to the bed and have sex with me?" I tried.

"Hmm.  I didn't quite hear what you said, Simon.  Could you repeat that a little louder?"

I shifted in my chair.  I turned my head slightly and stared at a small stain in the carpet.

"Yes sir, I want you to take me home and tie me to the bed and have sex with me," I said, almost in my normal speaking voice.

"Who are you talking to?  That stain on the floor?"

I looked up at him.  His face was completely impassive.  His eyes, set into his beautiful, angular face, burned into mine and I fought the urge to cringe before him.  "Yes sir, I want you to take me home and tie me to the bed and have sex with me," I forced myself to say.  The volume of my words matched his, but inside, my stomach turned somersaults.  A wide smile, an easygoing, friendly smile broke out across his face.  It was the smile he'd worn when the picture he'd sent me had been taken.  His eyes immediately softened and sparkled.  It was a smile that tempted me to rest at ease, and somehow, the fact that I'd just openly declared my lust in a public place was pushed to the back of my mind.  Subconsciously, I grinned sheepishly.

"That wasn't that hard, was it?" he asked.

"Yeah, actually it kind of was," I replied good-naturedly.  His smile instantly vanished, wiped away by the impassive, expressionless stare.

"What?" he asked.  I froze.

"No, it wasn't?" I offered, unsure of what had happened.

"Don't lie to me, boy!" he retorted.  His face had clouded over.

I looked back down at the center of the table.  What did he want me to say?  It dawned on me.  I looked back up at him.  "Yes sir, it was, sir," I answered.

He smiled again and nodded.  "You're learning.  This is why I wanted to do this in public, both to make you get used to the fact that you're gay, even when you're out in public, and so I can start to train you without freaking you out.  If we'd done this in my apartment, you'd have panicked by now, but here you know you can walk away.  >From now on, when we talk, either face to face or on the phone or online, it's Sir.  Do you understand?"

"Yes sir."

"Good.  So you want me to take you home and tie you to the bed and have sex with you.  Well, I am.  But not today.  You didn't want to do it the first time we met, and based on this meeting, I think you were right, even though not for the reason you think.  In fact, I bet that right now, you'd be willing to forget all about that and go home and play today, wouldn't you?"

He was right.  Seeing him there, absolutely fucking hot.  The hard rod in my jeans that hadn't gone down since he'd stared at me, through the entire embarrassing conversation.  The hormones pumping in my blood.  I was willing to go to his place and do whatever he ordered me to do, right then.  "Yes sir," I agreed.

He shook his head, still smiling.  "No, you're not ready yet.  You think you want it, but you're not ready for it yet.  When we got to my place, and I started tying you down, and you realized that you were helpless and no one knew where you were or whom you were with, and then I popped the gag into your mouth so you couldn't even scream?  You'd be gone.  You'd be worried that I was a psycho, and everything I tried to do would be second-guessed and analyzed to death.  You'd have no fun at all.  And if you don't have fun, I can't have fun.  So it's not going to happen today."

Inside, I felt disappointed.  But I knew he was right, and it made me trust him.

"What I will do, though, is drive you over to my place so you can see it," he continued.  "You can follow me in your car, we'll go inside, and I'll leave the front door open.  I'll stay on the inside of you, so you know you can run if you have to and I can't block your way.  That way, when you go home today, you'll know what my place looks like and it will help you get used to the idea of what we're going to do and where you'll be when it happens.  Sound good to you?"

It was amazing the detail he thought of.  It was like he pre-empted every concern I could have, like he not only knew what I was thinking, but he knew what I would think and how I would react to something that hadn't even happened yet.  He was right, I would have gone to his place with him, and I wouldn't have even thought about anything sketchy happening until he'd followed me inside and shut the door behind me, and I'd heard the lock click into place.  And then, if he'd been the wrong kind of guy, it would have been too late.  "Yes sir, that sounds good to me," I agreed.

"Good.  Go put my magazine back and meet me outside.  It belongs over there," he pointed.  I turned and saw the magazine rack behind me, all the way across the store.

"Sir!" I leaned in and whispered.  "But, I'm hard."

He chuckled.  "I know you are, boy.  Now go do it.  And I'd better not see you put your hands in your pockets or holding them in front of your crotch.  You're going to walk all the way over there and all the way out to your car with your cock tenting your jeans and boxers.  And anyone who wants to see it will."  He picked up the magazine and held it out to me as he stood.  He was taller than I was, well over six feet.  He stared down at me, smirking, expectation in his eyes.  I took the magazine and stood.  I followed his eyes to my crotch, and there was my cock, the tube easily noticeable as it pressed firmly into the cotton and denim down my leg.  I looked back at him, pleading with my eyes.

"No," he said to my unasked question, amusement written all over his face.  "No I'm not going to change my mind, and no you can't adjust it, and no you can't hide it.  Now go."

I groaned inwardly and I knew that my face was glowing with shame.  I could try to think it down, but it would be futile.  I walked out of the café area.  I noticed some girls, roughly my age or a little younger, sitting at a table in the corner, point me out and start giggling.  I bowed my head, but that only meant I could see my own hard on.  I looked back up and picked a spot on the wall by the magazine rack and fixed my eyes on it.  I tried to ignore everything around me as I walked quickly over to it and replaced the magazine in its rack in the proper place.  Nevertheless, I knew that I was obvious to anyone who even glanced in my direction, and I knew that with all the customers perusing the stacks, odds are a lot had at least glanced.

After I put the magazine back, I stood still, facing the rack.  I didn't know what to do with my hands!  From the café to this spot, I'd clutched the magazine like a life preserver, in both hands in front of my chest.  I balled them into fists and held them stiffly by my hips, elbow slightly bent, and turned.  My eye caught his instantly.  He hadn't moved from his spot beside our table.  He looked at my maroon, burning face, and then down to my crotch.  He needn't have bothered, my cock was still rock.  But when I saw him glance at it, it throbbed.  In my peripheral vision, I'd glimpsed the girls in the corner, still staring at me, see it too, and they followed my line of sight back to him.  They knew.  They knew it all.  They were rolling with laughter now, covering their mouths.  I turned to the door, picking the spot chest high where the store hours were embossed on the glass, backwards from my perspective, and stared at it as I walked quickly through the open space in the center of the store, through the door, and outside.

He emerged seconds after I did, beaming.  He put a hand on each of my shoulders as he came up behind me, pointing me and my hard on out into the parking lot.  "You did great, Simon!  Perfect!  Pity you missed the look that old man and woman gave you from the music section, though.  It was priceless!"

"Oh, God," I groaned.

"Where'd you park?" he asked.  I pointed out my Civic.  "I'm in that," he pointed to a silver BMW convertible, top down.  Damn, so much for the dot-com bust!  "Just stay behind me, it's only a couple blocks."

I got in my car and backed out of my parking space, pulling up behind him at the traffic light to exit the strip mall.  I saw his license plate for the first time.  "ROPE EM."  Two of those sliver style rainbow stickers had been meticulously centered on the license plate frame, one above and one below the plate.  I stayed behind him as we drove down the main thoroughfare, then turned off onto a side street, and then pulled into an expensive looking, yuppy apartment community.  Manicured lawns stretched out between the buildings, clusters of four apartments stacked two high, the two apartments on the upper floor each with a balcony.  The hedges were expertly shaped, and I parked beside his car as he stopped outside one building at the end of a cul-de-sac.

"Wow," I told him.  "This place is impressive."

"Yeah, it's not a house," he shrugged, "but my down payment was adversely affected by downward market pressures."  He impersonated a cable news business reporter perfectly and I laughed with him.  He led me and my erection up a flight of stairs to a landing, then opened the door to his apartment.  I stepped inside, and true to his word, he walked into his living room ahead of me, leaving me a clear escape route through the open door.

"This, surprise!, is the living room."  Through the open curtains of the French doors opening onto his balcony, I could see what looked like a park stretching out below his apartment.  There was a big screen television in the entertainment center, along with a DVD player and VCR.  He picked up a remote from the steel and glass coffee table in front of the trendy sofa and clicked the stereo on.  The surround-sound speakers began very softly piping some sort of electronic ambient music I'd never heard before.  There were a lot of photos on the bookshelf on the wall of the living room, photos of him and his friends in various places, skiing or swimming or sailing.  That easy, white smile was plain in each of them.  He began walking down the hallway and I followed him.

"Kitchen there," he pointed nonchalantly, continuing down the hall.  "Dining room there," he pointed to the other side of the hall.  "Bathroom here."  He paused at the bathroom.  He thought about something for a moment and then announced, "OK, I want to show you something, but I'm still going to stay on the inside of you."  He walked into the bathroom, opened the sliding shower door, and lifted one leg to rest inside the shower.  "Open the cabinet under the sink," he instructed.

I opened the door and there was an enema kit.  "It hooks up to the shower here.  Does that bother you?"

"No sir," I answered.  He smiled again and nodded when I answered in the correct form.

"Have you ever had it done to you before?"

"No sir."

"That will change on your next visit," he explained.  "Now go back into the hall back towards the kitchen."  I stepped out of the bathroom and retreated a few paces as he stepped out of the bathroom and into the hallway.  After a few steps farther in, the hallway broke off into a T with a door directly in front of us, and one on either side.  The two side doors were open, and one was obviously his office.  We walked in and he had a laptop connected via a docking station to a color laser printer, a scanner, a huge flat screen monitor, a CD-RW tower, and equipment I didn't even recognize.  There was a wooden filing cabinet and another bookshelf, this one full of technical references.

"I do a lot of work at home, so the setup I have here is pretty much just like at the office," he explained.  He motioned me back down the hall.  I walked down to the far end, and he followed me as we stepped into his bedroom.

"Simon?"  I turned back to him.  He scowled.  "You're on the inside of me.  I told you I wanted to stay on the inside of you.  I'm going to take it to mean you're getting more comfortable, which is good.  It also means you're getting a little careless, though.  You need to remember that when I say something, I say it the way I mean it.  There won't be any repercussions this time, but beginning with your next visit, if my instructions are not followed the way I issue them, there will be."

Chastened, I stepped aside and let him walk around me.  He had a large, king-size bed, a walk-in closet, dresser, and night table.  Except that the walls were painted a deep blue, almost as blue as his shirt, where the other rooms were sterile, apartment white, the bedroom was the most unremarkable room of the apartment, especially considering his interests.  I think he read my reaction and smiled.  "This room you may spend some time in, but not much, and not on your next several visits.  Where you'll be spending most of your time is in the only room you haven't seen yet."  He motioned me back into the hall, and this time, I stepped aside towards the bathroom to let him open the door and precede me into the next room.

The walls of this room were painted charcoal and, unlike all the other rooms, its window was not draped with curtains but blocked off with some sort of thick, black cardboard, making it as dark in appearance as in mood until he clicked on the overhead light.  A bed stood in the absolute center of the room, simply a frame, box springs, and mattress.  He stepped inside the room and when I moved to follow, he stopped me at the doorway.  "You don't come inside here except under the rules.  You'll learn the rules later.  I want to show you the room and what's in it now, but even for the introduction, you don't get to come inside."

He walked over to the bed and reached down to each of the legs.  Each had a leather strap fastened to it with a steel clasp, and each strap ended in a lined, leather cuff, which he picked up and placed on the mattress.  He walked over to a large armoire that stood behind the head of the bed and opened it.  From my perspective in the doorway, I could easily see what it held.  Whips, floggers, riding crops.  Cock rings.  Ass beads.  Dildos and butt plugs of assorted sizes.  Tit clamps.  Candles.  Bottles of lotions and oils.  Devices I couldn't even imagine.

My cock, which had slowly softened during the tour, sprang back to full erection.  He turned back to face me, watching me stare into the cupboard.  "Does it scare you, Simon?" he asked.  I swallowed and nodded wordlessly.  "Does it turn you on?" he asked, glancing down at my crotch to see my bulging cock.

"Yes sir," I answered.  He closed the armoire and walked around the bed to stand in front of me, only inches away.  I looked into his face as he slipped one hand between my thighs and slid it slowly up to my crotch.  I closed my eyes and licked my lips.  I felt his breath on my ear as he leaned in.  His fingertips had traced down my cock to the head and were firmly rubbing circles into the underside of my glans.  "You want it now, don't you, Simon?" he whispered into my ear.

"Yes sir," I whispered back.   He continued rubbing and I began to rock my hips gently, feeling precum dripping from my slit onto my thigh.

"But you're not ready for it yet," he whispered.

"Yes, yes I am sir," I whispered urgently.  He felt him pull his face away, and opened my eyes.  He was staring into them, our noses two inches apart as he leaned down.  He took his hand away from my cock and put it on my hand.

"No you're not," he replied, shaking his head.  He pressed my palm into the crotch of his khakis and I felt his hard cock.  It felt huge, not just long but thick.  I gasped.  "I want to give this to you.  But you're not ready for a scene yet."  I knew he read the disappointment in my eyes, but he leaned in and kissed me softly on the lips.  Then he turned and walked into his office, closing the door to the dark room behind him.  He returned with two cards.

"This is my business card," he began, holding it out to me.  "It has my name, number, and email address, the company I work for, and the address and web site.  I've written my home address, number and email address on the back.  This is for you to put somewhere that you think is safe.  Someplace that you know that it would be found if you were to disappear.  That way, you will always know when you come here that if something terrible happens to you, at least the police will find me.  This card," he held out the other as I took the first, "has a web site address.  My web site address.  Not the profile site you've read, not my home page.  It has the rules.

"You're going to leave now.  You're going to go home and, sometime, you're going to go to the web site.  When you've read it, when you've absorbed every page, when you've thought about the gray room and what's in it and what happens there, and when you've thought about me, and you decide you're ready, call me.  You may never be ready.  But in no case are you to think you're ready before next weekend.  Because you won't be.  Now, I want you to leave, and close the door behind you."

"Bu..." I started.

He held up his finger.  "Simon?  When I give you an instruction..." he reminded.  I looked down and turned, my cock pulsing out precum I could feel collecting on my thigh and beginning to run slowly down my leg, and walked out of his apartment, closing the door behind me.

I sat in the car, looking at the two cards he'd given me.  One was an elegantly engraved business card bearing all of his professional information.  "Senior Technical Consultant" was the title it bore.  I flipped it over and looked at the personal information he had written.  The address I knew was correct, and so too was the personal email address; it was where I'd emailed my picture when we'd traded.  I concluded that even if the rest were fabricated, the address alone would track him down, if it ever came to it.  The handwriting was refined and precise.  I looked at the second card.  It was plain and white, except for the URL in black letters printed on the front.   I started the car and sped home, knowing I had to see what it held.

On returning home, I raced up to my dorm room, hands plunged into my pockets to hide my hard on from the guys in the hall.  I sat down at my computer and typed in the URL he had given me.  A Flash animation opened, fading in the door I had seen in his apartment, closed, from the perspective of his hallway.  The button beneath it said, "Enter," and I clicked it.

"Rules for Scenes" the text said, as the Flash animation continued.

"Rule 1:  The boy will be naked.  He will be clean, inside and out, and properly groomed.  His face will be clean-shaven.  His fingernails and toenails will be trimmed.  His body hair, from the neck to the knee, will be removed, with the exception of the arms from the elbows down."

I knew now why he had shown me the enema kit in the bathroom.  I didn't have any hair on my chest, back, or upper arms anyway, but I would need to shave my pubes, ass, and thighs.  That would be an interesting feat in the communal showers of my dorm.  I wondered whether he would let me shave in his bathroom, too.  I clicked next to continue the animation.  The slide dissolved and the next appeared.

"Rule 2:  The boy will have no toxins in his system.  The boy may not consume caffeine, pain medication (including over the counter), herbal or dietary supplements, or tobacco at any time on the day of his visit.  The boy may not consume alcohol or any controlled substance (including by prescription) on the day of his visit or the three days preceding it."

This wouldn't be a problem.  I didn't smoke or anything, and I rarely drank.  I definitely didn't do drugs.  I'd have to remember about the caffeine though.  I clicked next.

"Rule 3:  The boy will not speak.  The boy will not ask questions.  The boy will not beg.  The boy will not plead.  The boy will be gagged except when his mouth is required to serve a function pleasing to me.  The boy may attempt to scream, moan, groan, grunt, sob, or cry whenever his mouth his full.  In fact, the boy is encouraged to do so."

This one scared me.  He'd told me that he gagged the guys he was with.  He'd told me that I would be gagged, too.  I thought about whether it was a deal breaker.  Then I remembered that he'd told me he'd have an alternative to a safe word I could use if a scene got too intense for me.  It dawned on me that, since he lived in an apartment, he probably gagged guys so that they wouldn't disturb the neighbors.  That seemed logical to me.  I clicked next, and the slide dissolved.

"Rule 4:  There is one limit:  The boy will be not permanently damaged.  There will be no permanent marks.  There will be no disfigurement.  There will be no infection with disease.  Beyond this, there are no limits."

No limits.  Wow, that left a lot to the imagination.  Did that mean he really intended to do some really far out shit, or did that just mean he wanted me to think he did?  I'd read a lot of porn in the web, and there was some really wild stuff out there.  Tit torture.  Cock and ball torture.  Watersports.  Scat.  Blood.  Electricity.  Some of it hadn't turned me on at all.  Some of it had turned me on reading about it, but I'd never thought I'd want to try it.  No limits.  Some of it had turned me completely off.  Could I do no limits?  I remembered again that I'd have some way of communicating to him when a scene was too intense.  This was obviously a test to see whether I trusted him.  After a long pause, I clicked next.

"Rule 5:  Having been informed of the rules, the boy will not cum without permission.  This is the last rule, and it takes effect now."

I groaned.  I'd been so hard!  I looked down in my lap and saw my cock throbbing in my jeans.  FUCK!  I hadn't jerked off since Thursday, and today was Saturday!  And he'd told me that I wouldn't be ready before next weekend, no matter what I thought!  Fuck, he wanted me on edge for a week.  He knew I'd go straight home and read the web site.  Fuck, fuck fuck!  Maybe I could call him or email him, and explain that I hadn't cum since Thursday, so I should get one today, just because he hadn't known I'd had a two day head start already.  Yeah, he would buy that, I thought sarcastically.  FUCK!