Jacking for Terry Ch. 01

When I was my third year of college my father inherited a significant sum of money from a relative. Shortly after we inherited our newfound fortune, we moved into a very ritzy neighborhood into a fabulous spread. Our neighbors had equally impressive homes, and the situation was so drastically different from what I was used to, it was almost uncomfortable. I didn't come from the same background that most of the other people did, so I had a hard time relating to most of the people in our development. They were cordial enough, but they were just so much worldlier and traveled and accustomed to that lifestyle, I retreated emotionally and physically.

The inheritance changed our lives more dramatically than I can say. I decided to take a year off college to start a small business doing landscaping, and I was enjoying it tremendously. I managed the financial side of the business, mowed lawns, and employed 5-10 people. It was an opportunity to do something that I would otherwise not have had because I started the business with family money.

It also translated into long hours during the summer. It was typical to wake up at 4AM and work until after 9PM when the daylight was there. It wasn't exceptionally profitable but it was mine, and I enjoyed running the business. I handled the bookwork at home on my computer. After the business took off, we modified the upstairs to include an office area in my bedroom. It had a gorgeous view of distant hills with incredible foliage. It was incredibly relaxing to work there, and I would sometimes just roll out of bed totally nude or with very little on to do work in my office. There were no buildings of any kind visible out the windows so I had no reason to expect that my privacy was being invaded.

I had built a simple web site to showcase my business, just a few pages with some of the jobs we had done and a few phone numbers and email to reach us. It served the purpose and we'd get 4 or 5 customers a year that had seen the web site and given us a call. I got an email to give someone an estimate in a suburb about 25 miles away. I replied that we don't usually go that far and referred them to a reciprocal competitor in the area. They emailed me back an MPEG file with no title. I scanned it for viruses and opened it.

It was a movie of me masturbating in my office. In plain sight was me jerking my very hard cock while I watched some guy masturbating on my screen. It was also possible to see my face in a few frames here and there. At first I was scared to death that someone was stalking our family and we were going to be the target of blackmail, or that someone was going to break into our house and kidnap one of us, hold us for ransom. Something terrible was going to happen, I just knew it.

During my watching the movie, I got another email.

He gave me his full name (Terry) and his street address. "Go ahead; look me up in the phone book. Before you call the police, consider this: I think we have a mutual interest. Every day you give me a little treat through your window. Don't be mad at me. I don't wish you any harm nor do I want money from you. You are very attractive and I love watching you jack off. I can see into your window from mine. Maybe it is fate."

Now I knew this person was lying. You can't see anything from my bedroom window.

I replied, "You can't see me. My back yard is woods."

Another email arrived. Another MPEG, this time a window frame zooming, zooming, zooming, and there I am sitting in my office. I was floored. It was obvious that this was for real, that this person really could see right into my office.

"How long have you been watching me?" I sent.

"Two weeks."

My earlier fears were diminishing since the tone of the messages didn't seem to be harmful or combative. Now I was just baffled why I would be the target of this bizarre game. "I am not going to call the police, but I demand an explanation. Why are you doing this??"

"Like I said, we have a mutual interest. Maybe I am wrong, but I don't think so. Here's another clip for you to enjoy."

I opened the MPEG this time and it was a clear image of a man's nude torso, cock in hand. He pumped his cock hard a few times then a rocket explosion of semen raced from the tip and out of range. The next few spurts leapt vertically from the head and landed on his thick shaft as the stroking continued. The entire video only lasted 10 seconds but it was more than enough time for Terry to get his point across. He had obviously seen me masturbating while watching jack off movies on my computer. What were the chances such a thing could happen? I thought it was so private in my room, but I couldn't have been more wrong.

After looking out the window I realized that Carlton is about a mile or so away out one of my open windows. However, it's such a small town and it is so far away I never thought in a million years that you could see into my house, so I never put up blinds or drapes. The entire office was in plain view at all times.

"It's me.," the next message said. "It's me jacking off in the video. That's my penis, that's my semen, my hand. I, like you, enjoy masturbating while watching men jack off. I'm not gay, it's just a fetish that I have. I'm married and my wife knows about it. Sometimes we watch together."

"I'm not gay either," I sent. "I guess there's no point in my denying what I like, but it's just a fantasy for me. I find it erotic to watch. How in the world did you ever find me?"

"I bought some surplus equipment from government liquidation and they sent me the wrong stuff. This is high-powered surveillance equipment, not at all what I thought I was buying. It was missing a few pieces, which I picked up later. For the past few months I have shot video of all kinds of bizarre things in my neighborhood, let me tell you. However, you are the first one that I've contacted because of our unique common interest."

Terry continued. "It is erotic to me to watch video of myself or someone else building up to orgasm, watching myself in the mirror or capturing the moment on my video equipment to enjoy later. What I would like to do is to share video clips with you."

"Terry, I don't think that's a good idea. I can't verify that you are not a minor, and that's the last thing I need. Not only that, what if someone finds out that we are doing this? My business and my family could be ruined."

"No need to fear anyone will ever know. I have as much to lose as you."

Then the tone of the message changed.

"All I want is for you to pose for me and masturbate another 4 or 5 times at a better angle than what I can get with you sitting behind that damned desk. I'll save the video and erase your face if you want me to, but I want to see that all of that dick of yours in plain view. I assure you I'm no minor; I am a 44 year old married professor at the University. You can look that up too."

I did, and sure enough there was a Professor of the same name on the web site. He looked to be about 44 so that part at least appeared to be correct. He was a professor of electrical engineering, so that sort of explained the video equipment part as well. My greatest fear now was that he was not who he said he was. It would be relatively easy to pull off thus far what he had done.

This is not happening, I thought. On one hand I was exhilarated that someone would want to watch me, but on the other, I was scared to death that it could and would be used against me. The crazy part is that I was actually considering doing this, but I needed something to level the playing field.

"I will do this on one condition. I need a clip of you jacking off, too, complete with your face. You should share the risk. You already have video of me, but if you really have innocent and voyeuristic interests and not doing this for blackmail, you will do this."

It was about 5 minutes before I got the reply.

"No way. I am not doing that. The only video of me you already have. No faces."

"Then I'm not doing it," I replied.

It was about 5 minutes later that I got the next MPEG, 5 MB this time instead of the 200-300K earlier attachments. I opened it knowing full well what was inside. There was the prof, in a comfy chair, with his big old dick in his hand, stroking away. His balls were enormous, and spilled down onto the seat, widely flanking his thick shaft. Each time he stroked upward his sac made a gentle upward rise, the two large bulbs sliding together before separating and plopping back down the descent. His cock was very thick, but only 5 or 6 inches long which made it look even more stout. The high-res video continued for about 15 seconds then it was over.

A few seconds passed and I got the next MPEG. "That was just a teaser" was the subject. The same video played only this time after about 15 seconds his bulging bone shot out a thick jet of semen high into the air, his mouth slack as the orgasm gripped his body. He was in decent shape, but it wasn't his abs or his face I was watching. I only focused on his spurting member as it recoiled again and again spraying his chest with globs of white fluid. The video ended with him approaching the camera to turn it off, come smeared on his thick dick.

"OK, I guess we're even," I sent. "I have a video camera. Do you want me to record myself or do you want to use Uncle Sam's finest technology to do the job?"

"The whole point of voyeurism is to capture the moment in the raw and deal with the actions and emotions as they are. Just keep doing what you're doing. At the rate you've set recently, I think it won't take me long at all to get 4 or 5 nice movies for my viewing pleasure."

"Wait a minute," I wrote. "I am still a little nervous about this. I need to know it's really you and not some kid. How can you prove it's you?"

"Look up my number in the phone book," responded Terry. "Pick a password and call my house."

"The password is 'impressionism'," I wrote.

I looked up the phone number, called, and the phone picked up. A deep voice said "Impressionism" and quickly hung up.

"OK, that makes me feel better," I wrote.

"What about you?" I asked. "Are you going to be sending any more interesting things my way?"

"If you want them, I will send them to you. I am not doing video exchange with anyone else right now, so I am in uncharted waters as it relates to courtesy, but I think one-for-one is fair."

I sat down in my office chair in my boxers and thought about what I just agreed to do. My heart was pounding out of my chest in anticipation of what I would do next and what would be sent to me. I reflected that in essence I just permitted, in writing, another individual to watch my every move in my office and to record me masturbating. I never thought I was an exhibitionist, but that part of my brain and personality sprang awake and alive in an instant.

It was about 8:30 PM and it had rained heavily that day, so work for the next day would start late. This gave me the green light to stay up late and play.

I decided to walk around naked for a little while to get warmed up. I was already raging hard from the emails and just the thought of jacking off and letting someone record it to watch later. Thoughts of people watching me spurt semen out of my cock was thrilling me almost to the point of orgasm as I paced in my office, my stiff bone shaking and pulsing with excitement. Clear seminal fluid had oozed out of the tip of my penis and left a shiny trail along the front of my shaft. I dipped my finger into the liquid and brought it to my lips. I secretly hoped that this was recorded; personally I think that watching someone taste pre-cum is more erotic than watching them swallow a load of semen.

I sat down in my chair, legs spread, and faced the window. I slid the chair away from the desk and adjusted the angle so that my hands had room to stroke my dick as I clicked through website after website. Most importantly, it afforded an onlooker an unobstructed view of my penis and scrotum.

I started with an older gal web site. The first video was of a 50-something redhead sucking a few black cocks and the next few were of her getting filled in each of her openings. After watching a few grannies get it on together, I moved on to some tranny sites where the she-gals were giving and getting head as well as offering themselves to a few guys brave enough to plant their members in their tight asses. There were a few halfhearted come shots, but one in particular really excited me. It was a tranny with a huge dick sucking away and getting in the ass at the same time. As the guy in her mouth started to come, her dick exploded and a few droplets made it all the way to her tits.

After my periodic tranny fix, I settled into my favorite jack off site. Today's offerings were much of the same, guys masturbating until semen oozed and spurted from their long, short, thick and thin cocks. Once in a while a kinkier video would show someone jacking off then flipping their legs over their head to blast their mouth and face with come. I don't need all that. I just want to see someone stroke their meat, watch it get hard and thick, then pulse and orgasm.

I began watching video after video of masturbation, ejaculation, semen, penis, and scrotums. I focused on details of the skin of the scrotum, whether it was thickly gathered in a small sac, swinging free, or tightly packed against the body. I became increasingly aroused and sensed my orgasm approaching. I patiently leaned back to enjoy the ensuing bodily function. My cock tensed so hard it hurt as lightweight droplets of come flew out of my cock and over my left shoulder. I knew this orgasm was going to be one for the books as the next wave came over me. I stroked hard and held back, finally releasing the pressurized fluid from my balls. In a pace closely matching my heartbeat, my glands pumped a monster load out of my tip vertically as high as my head. Only a few times in the past has such a thing happened and my eyes were big as saucers as I watched gravity pull the giant rope of semen back down into my lap. I continued stroking and ejaculating but nothing came close to the first launch. I stroked the remaining semen into a frothy blend on my shaft as my orgasm subsided.

It took a few minutes for me to relax and return to my senses as I sat motionless in my office chair, windows wide open into the evening sky. Naturally I thought about Terry the entire time, wondering how this remarkable orgasm would appear on video.

After a few minutes I got an email. "I'm ready to get started when you are."

"What!" I replied. "You didn't get that! I just spent 30 minutes and a giant load!"

"I went to the store," was the reply. "There are things other than you jacking off going on in the world, you know."

I don't believe this, I thought. My fantastic, first erotic release was wasted.

A few seconds later I received a mail message with attachment. I knew it; he was jacking me off, pun definitely intended. I opened the MPEG and watched in amazement as I grabbed my cock just as I remembered and hammered away at myself. The video definition was incredible and the camera zoomed in on my scrotum several times as I masturbated for the imaginary camera. Then, captured on video, was the wonderfully large ejaculation that I experienced earlier. It was like I was reliving it even more so than if I had recorded it for some reason. I have videotaped myself but it always seems so sterile. This video had life because I was seen through a new set of eyes.

"You have a wonderful scrotum. It looks so soft. I bet it's great to touch it."

"Thanks. It is great to touch it. It is soft and the skin tightens up a lot when I get really excited, then right before I come, the skin gets loose again. When I am having sex with a woman, it feels great to have her stroke it, it's so sensitive. When I do her ass from behind it feels great to have her reach back and lightly touch me."

"I don't get to do women in the ass. I'm married," Terry replied.

"Sorry to hear that. It's great being single, but I have to be careful. I love fucking chicks in the ass but I don't want a death sentence. I've had a few girlfriends that take it in the seat, but not all of them."

"You're pretty thick. I bet you get some resistance, either verbal or physical, when it comes to anal."

"About half go for it. Of those about half like it. It's important to be gentle and slow. Many times women have had a bad experience once and don't want to repeat it."

"Let's talk about your balls some more. Do you have any memories, like vivid ones, of women giving you head or playing with them?"

"Absolutely. I had a neighbor a few years ago that was recently divorced. She was about 45 or 50, I don't remember. I used to mow her lawn and she'd give me head plus 10 bucks. How could I say now? She was un-fucking-believable. She would do this thing with her tongue when she sucked me off, right before I would come. She'd put her tongue out with my cock all the way in her mouth. Somehow she would lick my balls as I started to come. It was amazing. My eyes would roll back in my head she was so good. I have never met her equal. She wasn't much to look at but the majority of what I remember was the back of her head and that looked just fine to me! She also gently played with them every time we had sex or before she sucked my cock. It was her brand of foreplay. That was great, too. She often said that the scrotum is the most overlooked erogenous zone. I couldn't agree more. When I jack off, I pay a great deal of attention to mine because it enhances the experience so much."

"I know exactly what you mean. As you saw from my video I have a very large scrotum and they feel great to be touched. I'm going to tell my wife to pay more attention to them next time! I like to play with mine a lot when I masturbate. It's a great way to add to the erotic nature of the experience. Sometimes I imagine touching another scrotum."

"I do, too, sometimes. That's the greatest thing about fantasies: seems like the ones you never act on are the best ones of all."

"Well, I guess I better get back to work. One down, 3 to go."

"Or 4. We'll see how you do. In the mean time, here's one for you."

It was a really long video this time, over 2 minutes. Terry was on a thin bench and was stroking himself. He was getting hard, but not there yet. He disappeared off camera then returned with one of those porn star pussy and ass latex casts. He repositioned the video camera so that as he straddled the bench it taped him from behind. He positioned his cock at the entrance of the latex pussy and pushed inside. He used a remote control while he fucked the fake pussy to zoom in so that his balls filled the top half of the screen as he banged away. A few seconds later he pulled out and smeared up with KY jelly and put the tip of his thick bone at the entrance of the fake asshole. His thick dick bent a little, and then pushed inside the tight hole. You could hear him moaning as he drilled slowly into the porn legend's charlatan chute. After several deep, hard strokes his cock re-emerged, pointed downward at the latex mold and sprayed a light drizzle of semen over the object. It was decidedly more erotic seeing someone I "knew" do this; I was hard again and had subconsciously started stroking off again while I watched the video.

"Yes, yes!! Watch it and come again," Terry wrote.

I started masturbating again in earnest and a few short seconds later had an extremely powerful but outwardly uneventful orgasm. Only a small amount of fluid trickled out, which was nothing compared to the porno-sized portion I had excreted earlier.

A few minutes later another email arrived. "That was nice. Here's the finished product." Another MPEG was attached showing me in full view, unabashedly masturbating for an audience. As I had thought, this was a no-never mind orgasm to the casual observer since it did not have much of a come shot.