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."
