If You Live Long Enough

If you live long enough, you are bound to have some weird things happen to you. Diane is 33 and began working for me two years ago. She has an accounting background and had been working as an executive assistant at a local branch of one of the big financial institutions caught up in the mortgage fiasco. I had finally admitted that I needed office help managing my apartment, business space, office space and housing rentals.

The timing was perfect for me when she lost her job. She lived in one of my apartment units so I could offset her rent. It was a good deal for both of us. My little cluttered office was in the middle of the ten unit strip mall, less than a mile from where she lived.

No one would call Diane a beauty but she has that Jamie Lee Curtis type sex appeal. She is about five eight and thin as a rail. She dresses carefully to hide the fact that she has very small breasts and freckles between her breasts and on her neck. Her long legs lead up her skirt into darkness that seems to say "look here." Other than that my knowledge of her body and sexual background was very limited and just casual guesses. She definitely had not given any hints, but I guessed that she was inexperienced, dated very little and was a little frustrated. She certainly whipped all my records into shape, aggressively got control of all the payments that were due and made it a pleasure to come in to the office each day. Granted, I spent most of my time outside the office - inspecting problems, checking facilities after tenants moved, showing property and obtaining information about prospective renters.

One morning Diane was not at work when I arrived about nine. She had never been late before. I looked out and saw Harry's truck. He worked in the discount store. Harry was in his forties and did not come across as the brightest bulb in the box. He dressed very macho, emphasizing his large biceps; his shirts were not always clean and he sometimes chewed tobacco. Diane had been seeing him for a few months and she had mildly complained that he was "boring." My word, not hers. I imagined that he wanted to sit, watch TV, not go out, not talk, not dream, not plan, drink beer, fart and be served by a woman who should thankful to have him.

By ten a.m., I was worried, so I went over to her apartment. Her car was in her assigned space. I knocked; there was no answer. I tried the door; it was unlocked and swung open.

"Diane are you home?"

No answer. Everything inside was totally quiet. The television was off and would soon be worthless with its rabbit ears because of the digital conversion. All the appliances were off in the kitchen. The dirty dishes were from the night before. When I swung open her bedroom door, I found Diane -- tied, nude, spread eagle on her queen sized bed. Her eyes were blindfolded. She had on earphones, but still thought she heard something.

"Harry? Harry is that you? I'm sorry. Please, untie me. I'm getting very sore and need to go to the bathroom. Harry?"

There was some crossed strap contraption under the bed that came up on each corner and had a buckled cuff on it. A ball gag and clothes pins lay next to her head and she had a red hand print across the left side of her face. She was even flatter than I thought. She had nice sized nipples that were hard and pointing at the ceiling but no significant breast tissue. The room smelled of pussy. There was a wet spot on the bed between her legs but her cunt was dry on the outside.

"Harry? Please untie me. I'm sorry for making you do this. We never have to do it again."

I cannot recall ever taking advantage of a situation before. Usually, I did everything I could to help people in need. Her words, her uncompleted fantasy, my urges, my anonymous presence and her helplessness were too much temptation.

Those long, rigid nipples called me and demanded that I pull them, twist them and squeeze them until she responded.

"No, Harry, please untie me."

I let go of a nipple long enough to push the ball between her lips and watch it expand behind her teeth. She tried to push it out with her tongue. The little Velcro strap solved that. I went back to pulling and teasing her nipples. Her resistance wavered when I bent and sucked the right one, nursing it, flicking it and kissing it.

I left her nipples alone long enough to stroke my finger tips across her face and lips. I tenderly touched the redness on her cheek and then trailed my hands down her chest, across her belly, bypassing my true target. When I grabbed her thighs and rolled them apart to spread her, she tilted her hips toward me and groaned behind her gag. I stood at the foot of her bed and pulled her feet, one at a time, to rub into my crotch and let her feel my hardening cock. Her toes curled, trying to possess the shaft as her own.

The sound from her ear phones was a very faint whisper. I decided to try to make her cum. Hopefully, she would fight me. Hopefully, she would lose control and hopefully, her body would betray her and I could watch her climax and feel her body contract and suck my fingers.

Every indication said she wanted to experiment with being helpless, being taken, being controlled. I would be rough. First one clothes pin on one nipple. She did not react so I squeezed it tighter until she rolled her body and grimaced in pain. She knew the routine when it was the other nipple's turn. She gasped before the prongs closed on her nipple. When I squeezed, she arched her chest, challenging me to do more.

I opened the lips of her pussy with the fingers of my left hand and pushed just the middle finger of my right into her. It went in smoothly and my finger tip rested on her very pronounced g-spot. This was going to be fun. For a minute I pushed and stroked just that spongy spot until I could see her belly tighten. A few pinches at her clit, brought her down from her inside stimulation and promised something different.

Her sheath wasn't filled with cum, only her own juices were inside. I bent down, licked at her pussy, licked upward and then sucked her clit into my mouth and nursed. I pulled my finger out of her and replaced it with two. I moved to the side of the bed, placed my left hand firmly on her belly and began to thrust my two fingers into her and pull up into her magic spot on the out stroke. Ten, maybe fifteen, thrusts and she was rising to welcome me. Another few strokes and her insides contracted. I jerked my fingers away and she squirted. In again for a few strokes and then jerking away again so more liquid rained from her. Her body began to spasm, twitch and roll. Again, I thrust into her and kept up the abuse for two dozen strokes. When I jerked away this time, I left her totally untouched and she flopped around the bed for a good thirty seconds, squirting, trying to breathe and being led by the strongest orgasm of her life. I wondered, "Will she stop?" "Will she suffocate?" "Will she guess who is controlling her?"

Diane survived. Slowly her body came down. I did not touch her again. I was still worried about her breathing, so I undid the gag and removed the ball while she was lost in bliss and not caring about life.

It would be best to leave and return in a few minutes to play the "gallant white knight" role. I needed to cum, to push my dick inside her, feel her cervix beg and then be completed when my body released everything deep at the mouth of her womb. That was not to be, not this time.

I left and went down to the first floor maintenance room. Luckily the roll of paper towels was where it was supposed to be. It only took a few seconds of imagining my cock sliding over Diane's tongue and watching my cum spurt out to be swallowed hungrily and her mouth open again so I could see another rope coat the roof of her mouth and string onto her tongue and lips. I fell back against the wall and rattled against some buckets. The roughness of the paper was almost too much to bear when I wiped away the last of my cum. As my body winced, I smiled and planned my second grand entrance -- a loud one this time.

"Diane. Diane. Are you all right? Diane this is Will. Where are you?"

When I burst into her room this time, I was a flurry of helpfulness, untying her, soothing her, pulling the comforter up to cover her. She had peed and soaked her bed a second time in thirty minutes.

Diane was very embarrassed, blushing and self-conscious. She would not tell me who left her in such a state, did not want to call the police or go in to a clinic to be examined. I helped her walk until her stiff muscles cooperated and then got her into the shower. She had one of the few apartments with a washer and drier, so I started the first load of bedding and then started putting a breakfast together for her.

While she struggled through her toast, eggs and coffee, I quizzed her,

"Do you want to stay a few days with me or a friend?"

"Do you feel safe here?"

"Do you want to take a few days off and go visit a family member?"

The answer to all my "concerned" questions was, "No."

I went to change the wash to the dryer and start another load. When I returned, Diane was ready.

"Will, I don't know what you think about me after what you saw?"

"Diane, don't worry. First I won't say anything to anyone. Second, how you play and enjoy your body and sexuality is strictly up to you. We all get wild and playful. You and I have never talked about such things. I might be different than you imagine, also. Just relax. It's only me. We've known each other for a long time. This changes nothing, except how we might kid each other during private moments."

She blushed again, pulled her robe tightly around her and got up to go get dressed. I cleaned up her kitchen and saw to the wash while she rattled around.

"Take the rest of the day off. Or as much time as you need." " No, I would like to work this afternoon, if that is OK with you."

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Late that afternoon, Diane said, "Thanks for coming to look for me today."

"You're welcomed. You were not here when I got in. Harry's truck was in the lot. I was worried about you."

She cringed when I mentioned Harry.

"Did Harry leave you tied up and helpless like that?"

"Yes."

"Was he going to come back or leave you to starve?"

"I don't know. He got mad."

"Well, let him cool off. Come over to my place for dinner tonight. You can go home any time you want or even stay in a guest room if you want."

"No girlfriend to object?"

"Just me. One thing though."

"What's that?"

"If you stay over, don't pee in the guest bed."

Diane blushed again and slapped me on the arm.

"I'm going to mix up all your files, if you mention last night again."

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Diane had never been to my house. It wasn't anything grand. I had moved into a very nice, professionally decorated, 2500 sq. ft. manufactured home on one in town acre three years ago. The massive Victorian that my deceased wife and I had shared for so many years was in the process of being renovated into four future rental units. She liked the spacious house and grounds. I did not really give her a tour. She did not ask about the closed doors to my bedroom or office. We cooked together, shared some wine and talked until about nine.

"Diane, remember last year when you helped me with my personal taxes?"

"Yes."

"I would like for you to help me again this year but I'm not as organized as last year. The structure and routine will be about the same but I would like for you to help me a few days in my home office. I'm going to incorporate this year but everything folds to my personal return for the year just ended."

"Sure, when do we start?"

"Today's Thursday. Let's get everything under control at the office through Monday and start here about ten on Tuesday."

"Sounds good."

"Will you be OK at home until then?"

"Yea, I'm fine."

"If Mr. Macho causes you any problems, call or come over here."

"Thanks, but I'll be all right."

I pondered for a couple of days whether or not to let Diane know much about my personal life. I decided a few baby steps were in order. I changed out a few of the more hard core pictures in my office and bedroom, hid my volumes of stories, set some blocks on my computers and staged our mammoth tax project. I had changed computers half way through the year, lost some data, had lots of unfiled items and mixed up categories on much of my data. Luckily the final return would be very much like last year's.

I was ready to head out when Diane showed up on Tuesday morning. We had a quick coffee while I told her about sorting the stacks of receipts, paid bills, etc. into the business tax categories to match TurboTax and Quicken. I told her to put everything else into groups that we would sort together in the next few days. Then I threw her to the wolves. More specifically, one wolf -- me. I knew she had the work well under control.

When Diane entered my home office for the first time she was totally unprepared for what she saw hanging on the walls. She did not know I collected fetish art, mostly classy bondage pictures but some lithographs of water sports, food play, sexy vampires and beautiful women giving and receiving abuse from cat-of-nine tails, ball gags like she had, clamps and butt plugs.

When I returned about three, Diane had not made as much progress as I would have expected considering how much she usually accomplished during her work days. Her face was flushed and she straightened her skirt out as I walked into the room. The room was warm and smelled of excited woman and stale coffee.

I was curious how she would react if I came on to her. I'm twenty years older than she is. I'm tall, thin and rugged looking, more of a Charles Bronson than a handsome model.

She was standing by the desk and I walked directly to her and took her hands into mine. They were warm and moist. I held her fingers to my lips and inhaled through my nose. The fragrance was unmistakable.

"You have been playing with your pussy. How many times have you climaxed today?"

"Will, I......."

"It's alright; I had you work in here so you would know that we share some of the same interests. I have thought of your body many times since I found you tied up. I have to do one thing. Then I will never do anything like this again, unless you have an interest in me."

I kissed her still damp fingers, savoring her, accepting faint tastes when I wanted to lap at her wetness. As I pulled away, I noticed her light blue panties protruding from the top of her purse. I retrieved them and showed them to her.

"You do not have on any panties. Is she wet and running down your legs?"

Diane had been shocked when I sucked her fingers, but now seemed to relax and let out a long breath. I sensed that her heart was racing. She leaned back into the desk, spread her legs just a little, closed her eyes and said, "Why don't you check and find out?"

There was no resistance when I pushed two fingers into her soaking cunt. She did not resist when I pulled her head back using her hair. She opened her mouth when my lips touched hers. I licked her lips and her tongue flicked at mine.

I gave her, her first sexual order, "Suck" and pushed my tongue as far past her lips as it would go. With each thrust of my fingers, I thrust my tongue and she sucked it even deeper before releasing it, asking for another thrust.

Within two minutes she came wetly into my hand while sucking almost painfully and moaning into my mouth. The desk, my grip on her hair and two fingers thrust as deeply into her as they would go, kept her from falling. I felt her swallow the saliva she had sucked from me. Her body relaxed and I guided her to lie back on the desk. Her eyes were dreamy but full of questions.

"You will be sensitive. Hold on to the edge of the desk."

I lifted her legs so her feet were on the desk. She was spread wide like in an OBGYN's office. Her pussy's lips were gaping slightly, shinny, swollen and wet. She flinched when my mouth sucked one lip clean and then the other. Her hips tipped to greet me when I opened her even wider with my thumbs and licked her from her rosebud to her clit. Diane was getting wetter and wetter -- sloppy. Her entire body surged upward when I pushed three fingers into her cunt and she screamed, "Yes, stretch me, make me cum."

I slowed and lightened my touch. She whimpered. Twice more I speeded up and got rough enough to bring her to the brink before backing off. Her belly was wet, her cunt was slippery. With my left hand I opened my pants, stood and pushed my rock hard cock into her in one firm, jolting thrust. Her response was, "God, Yes, take me hard."

I thrust twice more, then stopped.

Her mind must have flashed back, "No, please. Please don't leave me like this. Please make me cum."

"What can I do?"

Her voice was strained, raspy and panicked, "Damn you. Do any damn thing you want to me, just make me cum."

"Put both your hands on your cunt."

Diane released her death grip on the sides of the desk and grasped the base of my cock where it entered her. The added friction almost made me lose it.

"No, push your fingers along the side of my cock and slip them in as deep as you can get them."

My cock continued to push against her g-spot with even thrusts while I felt her stretch the mouth of her pussy and work a finger from each hand on either side of my cock. Her juices were flowing out of her, down her ass, over my balls and dripping onto the desk.

"Rub her harder. Touch your clit."

Diane was groaning continuously now. Almost there. She was enjoying the extra stretching; the extra pain.

I pulled my cock out of her.

"No, No, please, No. Put it back. I need it inside me."

"Anything I want?"

"Yes, just put it back."

I lined up the head of my cock with her asshole and pushed firmly. She was very tight but not tight enough to cause the blood curdling scream that echoed off the walls of my office. I pushed again. Half of me was imbedded. She had pushed two fingers from each hand into her cunt and I could feel them through the thin membranes. Her thumbs were violently molesting her clit. I thrust again and all of my cock slipped into her bowels.

Diane, was raising her hips and slapping them back down on the desk. Her legs were trembling and I feared that she would rip her cunt open. I pulled almost out of her ass and then thrust back in. I set up an even rhythm in contrast to the near spastic jerks of her hands and hips. Her belly tightened; she held her breath; sweat poured from her neck and she screamed even louder than before.

Her legs relaxed and slipped heavily off desk. I caught them so I could continue to thrust into her. They were dead weight. Diane was perfectly still. Her eyes were almost closed. Her head was turned far to the left and drool strung from her mouth. Her expression was blissful but she had passed out. l pushed her legs high and used her tightness to jerk off in her ass.

I left her that way on the desk while I washed up and dressed. I covered her with a throw from the couch, turned on the television, got a soft drink, sat in the overstuffed chair and waited. In about fifteen minutes, she awoke with a start. I went to her.

"You are OK. You and your body are beautiful. It was wonderful to watch you cum. Relax. Let me hold you."

Diane did relax for another few minutes but then she started to realize that she had saliva on her face, that her back hurt with her legs dangling and that every part of her was wet. She struggled to sit up and regain some dignity.

"Will, I have made such a mess."

"Don't worry; I'll save it all for you to clean up."

"I'm sore and embarrassed."

"Why? Wasn't that a little of what you wanted to experience?"

"It was a lot more than I expected. I totally lost control."

"I liked you losing control and seeing pleasure flow through your body."