Tech Support

I work in the IT department of a large corporation. I have a two-year technical degree and that got me the job but being able to actually do the job is what makes me a valued employee.

Most of my days are spent going from office to cubicle to office fixing things in computers that some teenagers could fix. Some of the people in the cube-farm have some knowledge but what astounds me is how ignorant and helpless the executives are.

There seems to be a correlation; the larger the office and the bigger the title the more clueless they are. I remain courteous and respectful as I get their system running, and I practically snap to attention and salute before I leave. I know full well that they will give me a great rating in the automated survey they fill out.

The company has some employees that work from home. They are set up with a special phone system that is connected into the office phone system, and they can take and make phone calls without the customer knowing that they are at home (or maybe that they are in their underwear).

They are also set up with a computer that is connected to the company network and to the internet. These folks can also have technical issues that are beyond them and they need the IT department to sort it out.

I got one of these assignments at about 3PM one day. I told the department head that I would leave now and take care of the issue on my way home. He approved and appreciated the efficiency of my plan.

It wasn't exactly on my way home, but it was in the general direction, and GPS found the address for me. I parked in the driveway and knocked on the front door.

I very pretty woman answered the door and introduced herself.

"I am Sue. I do marketing work. And you are from IT, I hope."

"Yes, I am. My name is Ray."

I followed her to the office she has in the back of the house.

She pointed to the PC on her desk and said, "I hope you can fix that thing. It is running so slow I can't get anything done."

I sat in the desk chair and got to work. I was concentrating and after a few moments she said, "Well, I can't do anything until you finish, so I am going to let my dog out in the back yard."

That was fine with me, the worst thing that happens is when the end-user watches and asks stupid questions that slow me down.

There were some Registry errors and some other system problems that seemed to be the culprit and were quickly fixed.

As I was poking around I saw a folder named "My Videos". I don't really care, but the company policy is that no personal use of the company computer is allowed. Seems chickenshit, but that's what big companies typically do.

I opened the folder and saw a long list of video files. No understandable file names, just numbers and random letters. I opened one and got a big surprise. It was porn. And pretty raunchy at that. It showed a naked guy with a huge hard-on shoving it up a naked woman's asshole.

I couldn't help myself, I watched for a few minutes.

I heard a noise behind me, and when I turned I saw Sue standing there mortified.

"Oh my god! You weren't supposed to see that!"

I gave her a look like I was her boss, which I wasn't, and said, "No kidding!"

She said, "Turn it off!"

I replied, "No way. I want to see more of it. Watch it with me."

"You pervert! I said turn it off!"

"Oh, I'm the pervert? This is your computer, isn't it?"

She was red-faced and wringing her hands and very upset.

I said, "Come on. Pull up that chair and we can watch it together."

I guess I was a little too flippant. I was just fooling around. But she didn't think so.

She burst into tears. I mouse-clicked out of the video, ashamed of myself for making her cry.

I try to behave like a gentleman, and I got up and went to her and hugged her. She didn't object, she put her head on my shoulder and sobbed.

I held her until she calmed down a little, and I said, "Let's go in the other room so you can sit down."

It was her house, but I led the way to the living room and gestured to the couch. She sat down and I sat in the chair across from her.

After an awkward silence, she spoke up.

"I suppose my job is gone now. I don't know what I will do. I am divorced and I barely make the mortgage payments on the house."

"Sue, your job is not gone. I have no intention of reporting this. I am not your boss. I just work here, like you."

She looked at me skeptically, so I continued, "Why would I want to get you in trouble? The fact that you watch internet porn is not my business."

She mulled that over, and said, "You probably think I am a dirty slut and should be fired."

"No, I don't. 90% of people will admit they watch porn, and the other 10% are liars. You probably just have a powerful interest in sex."

I meant that in a good way, but she blushed and turned away.

"Will you feel better if I told you that I like it too?"

She didn't answer so I went on, "The only thing I want you to do is to let me copy all of your videos on to a DVD and erase them from the hard drive on your PC. You can watch them whenever you want to on the DVD. If someone else ever looks in your computer your job will be safe."

She looked at me with puppy-dog eyes and said, "You are very kind. Thank you."

"Just sit here. I will be right back."

I went back in the office and quickly did the DVD copy and used a software utility tool to totally erase the video folder. I did not just move it to the Trash folder where it could still be found.

I went back in the living room and handed the DVD to Sue.

She took it and said, "I can't believe you are so nice. Thank you."

I sat across from her again. We just smiled at each other for a few moments.

I said, "Can we talk for a little while? It's after five and we are off the clock."

"Sure" she said warily.

"I am just curious about a few things. I don't know how watching porn affects a woman. I know how it affects me. I wind up blowing my load in a paper towel."

She was silent and red-faced again.

"I am not trying to embarrass you. I am genuinely interested in why you watch it and what it does to you."

Almost angry, she replied, "All right! I admit it. I masturbate too. I guess I have to endure this inquisition, so you don't get me fired."

"Sue, I am not coercing you. If you are not comfortable talking about this we can stop."

After a moment she said, "No. It's OK. We can talk."

I dived right back in, "Does it give you an intense orgasm? Better than when you actually do it?"

She reacted as if I had slapped her.

"How would I know? I have never done anything like that! You do think I am a pervert, don't you!"

Oh my god. I keep overstepping.

"No, I don't think that. I was just trying to understand women a little better. You don't have to answer."

She glared at me, so I went on, "I don't want you to feel that I am interrogating you, while I am not willing to share. I will tell you that the porn provides a relief for me, but the real thing is much better."

That sank in, and I think she was visualizing me fucking some woman up the ass. She blushed but this time I think it was arousal.

"So, you have done it. Do you do it frequently? With lots of women?"

"I don't think it's polite to talk about sex with other women, but let's just say that I have some experience."

Her fantasy machine was now red hot, and the look in her eyes gave it away.

She wanted to re-direct the conversation, so she said, "As you said, it's after five. I am going to have a glass of wine. Would you care for one?"

"I would rather have a beer if you have one."

She went to the kitchen and returned with our drinks.

She went to the back door and let her dog in, a big friendly female. She came right over to me and licked my hand.

We had some small talk as we enjoyed our drinks. We talked about the dog, her nice comfortable home, etc.

But of course, I couldn't let it rest.

"Sue, a fantasy life is a good thing, but I think you should experience real life. I think you should act on your urges and cravings and get what you need."

I let that drop down the well of silence and waited for her to respond.

"I do want it, and maybe even need it, but I do not have a man in my life right now. And even if I did I have no idea how I could bring it up with him. I would be too nervous and embarrassed."

I waited for her to do the math and realize that I was right here. If that was in her mind she hid it well.

She seemed flustered and looked everywhere but in my direction.

"I think you need to overcome your sense of modesty and ask for what you want."

She mumbled, "Maybe."

Once again she seemed nervous or agitated. She was blushing and avoiding eye contact. Something was on her mind.

She was still holding the DVD disk.

"Do you know how to use that? Let me show you."

She handed it back to me and we went to the office. We sat side-by-side at her desk.

I loaded in the DVD and showed her how to open it.

"Here are all your video files. Just double click on one."

She did, and the video started.

"OK. I see. Please will stop it."

"Well, before I do that, do you know how to jump forward or back to go to different parts of the video? I am not interested in the interview of the actress, or all the striptease. I just like to jump ahead to the action."

She seemed interested so I showed her. I jumped over half-way into the video and it went (accidentally) right to the scene where the guy first shoves his meatpole up the girl's asshole.

"OK, I know how to do that now. Shut it off please."

I answered, "No, wait a minute. I haven't seen this one and I would like to watch a little."

She acted annoyed but since I was being so helpful, she couldn't object.

The video continued. The woman got on her knee's doggy-style, and the guy touched her asshole with the tip of his cock. He started to push, and the head and more disappeared up her asshole. He kept pushing until it was in all the way up to his hairy balls. Then he started to fuck her, in and out rhythmically. The woman's expression was one of ecstasy.

We both watched transfixed without saying a word for several minutes.

I asked Sue, "Does this turn you on?"

She snapped back, "Does it turn you on?"

"As a matter of fact, it does. Let me show you."

I unzipped my jeans and fumbled and struggled to get my cock out. As soon as it was free it began to stiffen and grow.

"My god! Put that thing away!"

I just held the shaft near the base and pointed it straight up in the air.

"See, it definitely turns me on."

She acted as if she was offended but she couldn't take her eyes off my raging hard-on.

The video continued with the guy steadily fucking the actress's asshole.

I said, "Please help me with this."

I took her hand in mine and led it to my cock. She tried weakly to pull away, but she clearly did not want to. I put her hand on the shaft and gently wrapped her long, slender fingers around it. The sight of her delicate feminine hand clutching my boner was priceless.

She said, "What am I supposed to do now?"

"Just this", I said, moving her hand up and down, jacking me off.

She said, "I should call the police on you."

I replied," Not until I finish, please."

I guess she finally understood my sense of humor, because she smiled and we continued, me jerking off using her hand.

The guy in the video had lasted a long time, but now he pulled his cock out and blew his load all over her butt-cheeks.

She started to stroke me faster without my help. She was aroused. Watching the video and playing with my cock worked like magic. Probably seeing the guy cum about a quart and a half helped.

I said, "We better stop before we make a big mess like that."

She asked, "Do you produce that much stuff?"

"Yes, I think so. But I don't pull out and make a mess like that. I put it as far in as I can."

"Doesn't it gush back out, like an enema?"

"Not if I get it in far enough."

I could see her thinking that over while she still held on tightly to my cock. She stared directly at the small hole in the tip. I think she was visualizing a geyser of cum shooting out of the hole and imagining what it would feel like squirting deep up her ass.

I was certain now she was aroused. I think I am making progress here.

"Maybe you should let go now. I don't like to waste it."

She was disappointed but she let go of my cock.

I really had to struggle to bend it to get it back in my jeans, but I finally did. I closed the video and gave the DVD disk to her.

"Put this in a safe place, like your underwear drawer under your panties."

She smiled and left the office. After a few moments she called to me from the living room, "Ray, join me in here."

She had poured herself another glass of wine and brought me another beer.

"Thank you" as I accepted the cold brew.

We enjoyed the drinks for a while with more small talk. I thought she might just be trying to move on and erase what had just happened.

After a few more sips of wine Sue said softly, "So you really think that I should try that."

I almost dropped my beer, but I maintained control.

"I guess I did say that."

"You said exactly, 'I think you should act on your urges and cravings and get what you need.'

I carefully said, "Well yes. It might at least help you to accept your preferences. You might finally decide to be honest with yourself."

"But do you really think that I might like it?"

Once again I had to control myself and not overreact.

Cautiously I said, "Yes, I do. Many hundreds of millions of women do."

She let that sink in, and then said, "You probably do things like that a lot. I bet there is a steady parade of women in and out of your door."

I just laughed and said, "I do OK. When you get to be my age you understand that the dating game is not much fun anymore. So, we make other arrangements."

She insisted, "But do you have women friends to do that with or not?"

"A gentleman never tells. I would not put any woman in a compromising situation by talking about what we did."

I think she realized that would be a good thing for her reputation. I kept building the case that it was OK for her to let me fuck her anally.

She said, "I'm sorry. I don't mean to pry into your private life. I was just hoping you could tell me a little about your experience with, umm, you know."

I smiled and answered, "What do you want to know?"

She blushed and said, "I am embarrassed to ask you."

"Go ahead and ask. I will answer if I can."

It took her a while to work up her nerve to say what was on her mind.

Looking down at the floor she said, "Is it uncomfortable for the woman if it is their first time? Or worse is it painful?"

"Well it can be a little uncomfortable for a few moments right at first, but then they usually say it feels good."

She hesitated and finally said, "But the big tip, I don't understand how that can even go in. The asshole is so small." She cringed when she realized what she had said and revealed what she was concerned about. She thinks her asshole is too small. Should I tell her it will be permanently stretched open after the first few times?

I almost laughed but I controlled myself, and said, "Trust me, it goes in. Like I said, maybe a little uncomfortable right at first, but then most women enjoy every inch of the rest of it as it goes in."

I could see her thinking about that. I think she was having a vivid fantasy about feeling a hard cock slide up her ass.

I said, "So did I answer all of your questions? It seems like you're not sure what you want me to do."

After an awkward silence, I went on, "Just tell me what you want."

More awkward silence.

She said, "Alright then. Let me get to the point. Would you be willing to do that to me? I don't mean love and romance. I just want to understand myself better. I don't want to think of myself as a disgusting person. You are a mature and experienced man and I am sure you know what to do."

She continued, "I have been thinking about it for a long time now, ever since I found those porn websites. Fantasizing about it, in fact. Just last night lying in bed, I got kind of hot."

She probably thought she had said too much. Most women won't admit that they masturbate. It was a hot visual for me.

"Sue, I would love to give you your first anal experience. But understand, you must finish it once you start. It is really important that I finish inside you, and you feel what we were talking about."

I could see her slowly understand what I meant. Her fantasy must still be vivid in her mind because she flushed, with arousal and not from embarrassment. She was imagining receiving a load of my semen in her asshole.

I said, "Well, how about it?"

Now she started to fidget and nervously wring her hands.

"Sue, you said you wanted to try this. Don't back out now."

She was blushing bright red and avoiding eye contact.

"I know. I'm sorry. I don't know you that way. We are not even friends. I am uncomfortable."

After a few moments of silence, I said, "Well, you don't have to be in love to have sex. Lots of people do it."

That seemed to convince her.

"I am too shy, I guess. I am worried about you seeing me naked."

"I will be naked, too."

At that moment I didn't know if she was going to do it or tell me to leave.

She was visibly conflicted. There must be a switch flipping back and forth in her mind between "I am a nice girl and I shouldn't do this" and "I really need to feel a stiff penis up my ass".

The latter thought must have won out, because after a few moments, she whispered, "OK."

I didn't hesitate because I didn't want to give her a chance to change her mind.

"Show me to your bedroom. We are not going to do it on your living room floor doggy-style."

She took my hand and led me down the hall to her bedroom. She has a nice big King Size bed with lots of room to fuck her.

"Please take everything off and get on the bed face-down."

I watched as she reluctantly stripped down. When she was down to her bra and panties she stopped.

"Keep going."

"I'm embarrassed." But she did take off the bra and pull her panties off. She has a nicely trimmed patch of pubic hair so she must have been expecting that someone would see her naked. Maybe it's part of her fantasy.

Sue is maybe 110 pounds and barely over five feet tall. But she is perfectly proportioned. She could work as a nude model for an Art School if she was a little less inhibited. She has the butt of a teen-age girl.

I quickly stripped down and my cock was stiffer than a board. She looked wide-eyed at it and then averted her eyes. I just stood there and soon she took another furtive look, and quickly looked away.

"You saw it before, watching the video. Don't you like it?"

She gazed intently at it and said, "It's just that I have never seen one so long. And the tip is so big."

"My ex-husbands was not . . ." and she trailed off realizing that it was too much information.

She continued her inspection, and then said, "I don't think that will all go in me that way."

She was so aroused that her pussy was moist. I could clearly smell it as she stood in front of me naked.

I was a little annoyed, but I tried not to show it.

"Won't you just try it?"

Still equivocating, she said, "Yes. No. I don't know. Maybe."

She was apprehensive and softly said, "Will you stop if I can't take it all?"

So that must be all that is holding her back now. I lied like a politician and said, "Sure."

She stared at my erect cock intently. I believe she was imagining it sliding up her ass, inch by inch.

She looked in the drawer of the nightstand and brought out a tube of lipstick.

I said, "Sue, you look fine. You don't need that."

She mumbled, "Just let me do this."