The Email

It was a Thursday morning. I had just gotten to the office, my cubicle was on the south side of the third floor. I booted up my computer, got some coffee, and sat down to catch up on the daily slew of emails that waited for me when I arrived. I had a busy day of meetings and I had been up late the night before, so I was braced for a long day. After fifteen minutes of reviewing work emails, I jumped over to my personal hotmail account to see if my girlfriend Sandra had written anything, or if my sister had sent me her promised information on our trip we were planning with her family. Nothing from them. But there was another email in my inbox, with a moniker I had never noticed before. Hmmm... I didn't recognize it and it looked like junk mail to me. But I clicked it anyway.

"I am one of four women in your life, but I won't tell you which I am. I might be Sandra, your lovely girlfriend of the last three months. Or I might be Kate, the head of the IT department in your company. Or I might be Darleen, the older woman at the end of your row of cubes who has always had a crush on you. Lastly, I could be Joanne, the head of HR. For the next week, you won't know. And for the next week, I own you. You follow my every command. If you accept, just reply 'yes'."

My instinct was to look up immediately and see who might be watching me, and I did so. But that was silly, nobody knew what I had just read in my email! Nobody was watching me. In fact, most people hadn't gotten into the office yet. Who had written this to me? Was it some kind of joke, I pondered. What did she mean "follow my every command"? I was completely mystified, and I didn't really have time for this at the moment.

I wasn't sure what I felt, but whoever it was knew who I found attractive. If a guy friend had asked me who I was most attracted to presently, these four would have been at the top of the list. Sandra, with her incredible smile and dazzling energy and playfulness. Kate, in that "I am so thin that you just want to reach out and carry me away" kind of way -- and, she exuded a secret sexuality that I just couldn't help but notice. And Darleen, who was older, confident, and had the most amazing rounded hips and neckline of any woman I had ever met. Joanne made dealing with HR issues almost impossible for me because I couldn't get the image of her naked out of my mind when I talked to her: she was taller than the others, with straight black hair that fell to her shoulders, blue eyes, and an intense femininity of the kind I fall for too easily. And I had a casual enough working relationship with each of the women at work that they would know about Sandra, my girlfriend, and I am sure I had mentioned each in some way to Sandra -- besides, she had been at the company summer party and had met each of the other three. So, that didn't give me a clue who might have written the email.

Already, I was late to my first meeting, and was distracted by the email.

I grabbed my pad, my blackberry, a pen, my coffee, and, after carefully shutting down my personal email, I bolted for the meeting. It seemed to last forever, and my mind shuttled between the conversation and the email nonstop.

By the end of the meeting, I had to use the restroom, grab a bagel, and move to my next discussion. On the way, I passed Darleen's desk, and we locked eyes momentarily. I smiled, and got a cute smile back. I felt a vibe, but I couldn't be sure. Was the email from Darleen? Did she know and that is why I got that look, or does she always look at me that way? I entered the conference room and got lost in work details again.

My third meeting, before lunch, included Kate. I had forgotten, alas. And my eyes were glued to her. She ran the meeting, and I just watched her lips move, her eyes dart, her arms gesticulating. I saw her breasts through her thin blouse, small but firm, and I think she saw me watching her. As the meeting wound up, she stopped me on the way out by putting her hand on my arm.

"You seemed distracted today, everything ok?" she asked, with a noticeable twinkle in her eyes.

I blurted out that things were fine, and dodged past her, stopped at the water cooler for something to drink, and rushed back to my desk. I wished I had a private office in a time like this, but I had no such luck.

I walked to lunch on my own, and continued to ponder the email. What harm would there be in responding? I could just say "yes" and see where it led. After all, if it wasn't Sandra would that be so bad -- she and I had only been dating recently, and we hadn't slept together yet, and we hadn't set any expectation that we were not seeing other people in the meantime. So, it wasn't being disloyal. Or was it? I shook it off, and finished my soup.

The afternoon went by in a blur, partly because I was tired, partly because I was working hard, and partly because I was distracted by the email. I worked out in the gym after work, and made it home to my apartment in the city by about 7 pm. Sandra was out with friends tonight, and so I made some quick food, and sat down to watch TV. But I noticed I wasn't interested in TV that night. My mind came back to the email.

"Fuck it," I muttered to myself. I would give this a try.

I booted up my PC, logged in, and wrote back, "yes" to the anonymous sender. Silly of me, but I actually waited in front of the PC for a few minutes refreshing my email expecting an instantaneous response. But nothing came. Not after two minutes, not after ten more. I gave up, and woke up several hours later. I must have fallen asleep on the couch. I looked up at the clock and it was almost 1 a.m. I stood up to go to bed and glanced at my PC. There was an email in the inbox:

"Congratulations. Welcome to your adventure. I look forward to torturing you! Here are the ground rules. 1) No orgasms without my explicit permission. 2) Wear no underwear until you are told otherwise. 3) Follow all other instructions you receive, no matter when or where. Enjoy!"

This was too much! No orgasms, no underwear, follow all instructions! I loved it. I had never heard such a thing before.

In the morning, after showering and dressing, I remembered the no underwear rule. I took my pants off, removed my boxers, and put my pants back on. Things swung a lot more losely, I immediately noticed, and only partway to the office I could feel an erection growing because of my penis rubbing on the inside of my wool trousers. I quickly ran my hand into my pocket and adjusted things so as not to look absurd. I tried to take my mind off the erection by focusing on work, and dove into my work routine the moment I got into the office.

Joanne surprised me when she put her hand on my shoulder.

"Can we talk?" she asked.

I jumped out of my seat, and followed her back to her private office. She walked ahead of me and I watched her blouse breezing around her back and focused on her strong calves (she had joined a rowing club early in the summer and was in excellent shape) and her tight skirt on her hips. I almost bumped into her as she stopped and turned into her office.

She was worried about my coworker, and asked me if I knew what was going on. I told her that I really didn't realize that there was anything to be concerned about, and couldn't help but let my eyes dart from her blue-eyed gaze down to her breasts and back to her lips, trying not to get caught in that way that I (and probably every other man on the face of the earth) had perfected -- timing every glance to when the woman turned away or shifted her eyes from mine or glanced down at her paperwork or computer.

Her breasts were heavy, and high, and I could almost imagine running my tongue down the crest to each nipple.

I shook myself out of my reverie to discover the erection had formed again, and the tent was somewhat obvious. I raised my voice to distract her and tried to subtly shift my penis with my hand in my pocket, while moving my other hand in a gesture to distract her.

She said that I had been helpful, and to tell me if I learned anything else about my co-worker. I stood up and she reached her hand out and touched mine.

"Would you like to go out to dinner sometime?" she asked, blushing.

I knew she was married, she wore a huge diamond, and I was flabbergasted by her request.

"You can't take your eyes off me, and I have a crush on you as well, so I thought we should at least discuss the situation," she smiled, both bold and embarrassed at the same time.

I coughed, shrugged, and sputtered something about how I was really busy, turned and walked out.

Maybe it was Joanne after all. She was obviously interested in me, and she seemed to have the trait of someone that would write such an email to me -- being so direct and aggressive. I couldn't get over the fact that she was married and asking me to dinner! I just put it behind me and focused on the rest of my day.

After an hour at my desk, and two more rounds of fighting back my erection because of my mind wandering to Joanne, I got a new email.

"Go to the bathroom as soon as you get this email, go into a stall, stroke yourself hard ten times. No orgasm. Return to your desk."

Oh my god I told myself. Is this for real? She is going to tease me? But I was committed.

I was hard before I even got to the bathroom, and I entered the stall. I had masturbated in the bathroom once in high school, but this was a strange feeling nonetheless. I unzipped, and my heavy cock fell forward, then bounced upward. I reached out, trying to imagine Joanne. But the other three women swirled in my mind, and I started stroking, slowly and tightly. I got to ten and felt like I would die if I didn't continue. I had once counted how many strokes it took to get to an orgasm, and at least the time I tried it was six hundred give or take a few. So ten wasn't going to do it, but I sure wish it had! I zipped back up, and left.

The rest of my afternoon was hell. I couldn't focus, and kept fighting back my erection. Kate was in my mind now, and I wanted to lift her up and hold her in my arms while my cock grazed along her back, wet at the tip, and seeking her tightness. I bit down hard on my pen to focus myself, and went back to work.

By the time I got home I had to quickly change to go to dinner with Sandra. I was hard again, and I reached out to stroke, but ignored my cock and put on jeans and a t-shirt to rush to a local diner for dinner. I stopped briefly at the computer and there was a new email:

"No orgasm with Sandra -- no matter what. None allowed."

Given that we hadn't even been sexual yet, I figured that wasn't a problem and smiled. I walked quickly up to the restaurant, running a few minutes late.

Sandra looked great, and was smiling waiting for me. She wore a green sweater and her work slacks, and she had on a pair of earnings I had gotten her as a gift the week before. We ordered pancakes for dinner, a favorite of ours, and shared a stack of four. We chatted about our days. She asked how I was doing, her hand on mine, flirting. The pancakes were great, and we left for a bar where we each ordered a glass of wine. We talked about her job as a copy editor at a non-profit, about her colleagues, and about my two major projects that were behind schedule. As the wine ran low, she asked if she could come over to watch some TV. I liked the idea, and we walked to my condo together.

After getting in, she pushed me against the wall and kissed me hard. We had kissed before, but this felt more urgent. It was wonderful, and she pulled my hand up to her breast. She was being aggressive and I could tell that I was responding powerfully to her advance. She held my hand over her breast, then lifted her heavy sweater and placed my hand directly on her skin -- she had no bra and her nipple was hard under my palm. I redirected my hand and had her nipple between my fingers in a flash and she moaned into my mouth as her body pressed up towards mine. Her hand was on my belly and before I knew it she was rubbing my hardness through my jeans.

Suddenly I remembered the email and I pulled back just enough to say, "Sandra, this is wonderful, but can we wait a little before things get completely sexual? I am totally attracted to you, I want you, but I also want to take this a little more slowly if that is OK with you?"

She smiled, then pouted, then laughed.

"I thought you might say that", she replied, "I had a feeling you were a take-it-slow kind of guy. You shy? Everything ok? I love feeling your body, and I want more of it not less".

I couldn't tell if she said it from the perspective of the author of the emails, knowing I was on hold, or not.

I explained that I was feeling fine, that it had nothing to do with not wanting her, but that I just wanted to take it slowly. She nodded, and put her lips back on mine, and we kissed for a long time, and chatted, and purred into each others' ears. She eventually left after a TV show, and I was left to a cold shower and a bed alone, with images of her amazing breast in my mind all night long.

Work was hard the next day. I had an early flight to Newark, a long cab ride to our client's office, a boring meeting, and then I had to do it all in reverse to get home. I made it back to the office just before 5 pm, and was getting ready to head home when I decided to check my email. A new message was waiting for me:

"I hope things with Sandra remained under control. Have you been a bad boy and had an orgasm? You better hope not. New instructions. 1) At home tonight, stroke 1,000 times, but in such a way that you don't have an orgasm. 2) When you get the package in the mail, open it and follow instructions exactly."

At that exact moment, with the email open on my screen, I heard a voice from behind me.

"How was Newark handsome?".

It was Darleen, and I swirled around, blocking her view of my screen, slightly red in the cheeks, and trying to digest the email at the same moment that I entered into the conversation with Darleen.

"Newark is Newark," I said lamely, trying to smile. "Glad to be back."

Her "handsome" statement had further thrown me off -- she and I flirted sometimes, but this was new, and more forthright. She smiled, and asked if I would like to walk to the subway with her. I knew she took the same subway, but in the opposite direction, because I had met her several mornings arriving at the station.

"Sure, let me just shut things down", I replied.

I quickly turned, killed the power on my monitor, grabbed my bag, and we walked out together.

The walk was four blocks, but in that time we chatted about the weather, work, her 8 year old son who was misbehaving recently. As we got to the station, she turned to me, and I stopped to talk, awkwardly.

"I have been meaning to tell you... I know you are going out with Sandra... And she seems really nice... I um. I hope you two are getting on well. And, I, um," she stuttered.

She seemed a little nervous, which was new for her. My eyes were taking in her neckline, her amazing neck itself -- somehow so attractive to me, its curve, thinness, her hair coming down to meet her neck.

"Yes?" I inquired.

"Well, here's the deal. I um, um, I find you very attractive, and, this is hard for me to say given how different we are in age and, um, but, if you wanted to go on a date sometime, just to try, I ah would be open to that, you know?", she stammered.

She was normally so confident, and secure with herself. I had never seen this side of her. She was either putting on a show, or she was genuinely anxious about her display of interest.

Red again, and feeling my erection once more entering into the picture, I swung my overcoat over my crotch, and said, "Darleen, I don't know what to say. I love the idea really. I am seeing Sandra, but that is casual. I love the idea of going out, like on a, um, date. Why don't we do that? You pick a place and time?"

Now I was stuttering! It must be contagious, or maybe we were both just nervous.

"I look forward to it, I will send you an email", she said, suddenly much more confident. And she gave me the wink as she twisted on her heels and entered the subway. She was gone before I could really say anything more.

This was getting to be too much, I thought to myself. Darleen wants to go on a date! And I have to go home and masturbate 1,000 times? I was starting to feel tortured. Maybe that was the point, I asked myself. I looked down and noticed my erection forming again. After several days of this, I was finding erections beginning at awkward times, in meetings, in the bathroom, after working out, in the morning in bed, in front of Darleen. But I was willing to go with it some more. I could always bail out if I wanted to, after all I was my own man and no law was written that I had to follow all email instructions I got!

I got home, showered, left my suit and tie strewn across the sofa, and called Sandra. She was in a bad mood about work, and we talked for awhile. She brought up the previous evening.

"At least you got to work out yours sexual energies after I left, right?" she said.

I replied, "Yah, right, sure..." and quickly changed the subject.

We agreed to meet for a bike ride on Saturday, and I hung up.

Now for the real challenge I told myself. 1,000 times. I got in bed, turned out the lights. It was too dark, I thought, so I opened the window blinds.

The erection was fucking waiting for me, down there! I didn't even have to fantasize -- it was just standing at attention. Alas. 1,000 eh? I guess the counting will distract me I thought. So, I started. Slowly, I got to 47 and suddenly felt my balls tighten up against me, a sure sign of my orgasm starting to construct itself. Damn it!

I stopped, and sat up in bed. How is this going to work? If after only 47 I am in this state, what is it going to take to get to 1,000? Well, it took over two agonizing hours. I would stroke, get close, and wait, stop, change positions, let my erection subside a little, and start again. After 20 cycles of almost cumming, I reached 1,000.

At this point, my cum had dripped from the tip, my hand was a little stiff, and my cock was aching for release. Just aching, dying, desperate, needy. It literally needed release and quickly. But I couldn't go there. I decided to "stay with the program". Like a diet, I told myself. I finally rolled over to go to bed.

Just as I was fading to sleep, I remembered the package. I hadn't looked in my mailbox when I got home. And here I was naked in bed, but I couldn't sleep without checking. It would distract me. So I got up, put on my jeans and a tshirt, and went out to check the mail. It was a warm evening, and the stars were out, which calmed me. I was still shaking from the torture session. Sure enough, in the mailbox was a package, about the side of a book, in cardboard, no return address.

I took it into the kitchen and cut it open carefully.

Inside was a note, type written, and a small plastic ziplock bag. I folded open the note:

"Wear this at least 30 minutes each day."

I glanced at the bag. Inside was a black rubber-looking ring, about the size of a giant plumbing gasket. Oh boy, I told myself. I had never tried something like this, but I immediately knew what it was: a cock ring. She wanted me to put this on for 30 minutes a day? That sounded easy enough, in reality, given how large the ring was. The trouble would be keeping it on! I laughed. I thought things were going to get harder, not easier! And that realization made me sleep like a baby, for the first time in over a week.

Friday went easily. No travel, no trouble from my boss. I had lunch with some workmates, and was diving back into work when I happened to check email.

"I assume the package has arrived. I hope you enjoy that! Starting today, no touching yourself. None at all."