Renter's Insurance Ch. 04

IV

This situation had gone on long enough. I knew Bonnie was going to find ways to keep me on the hook as the building gigolo and while I had nothing against getting laid now and then, I hated to be manipulated. I picked up the phone and dialed Bonnie's number.

"Hello."

"Hi Bon," I said knowing she recognized my voice "Listen, I'm not going to do this anymore. I'll find another way to get you the cash, and I'll get it for you today, but I'm not going to be hanging around at your beck and call any more."

I paused and there was a moment of silence on the other end of the phone.

"Ok, Sweetie," she finally said, "I wish it hadn't come to this."

The phone went dead.

I sat for a few moments contemplating what she had said then decided that no matter what she had meant, I needed to get her the cash or I wasn't going to be in any kind of bargaining position whatsoever.

After spending the majority of the day tracking down the contractor that I had finished a job for a few days earlier and convincing him to pay me before it had been inspected, I stopped at a bar and had a few drinks thinking about how I was going to approach Bonnie. I considered just slipping a check under her door or dropping it in her mailbox, but she could always claim that she hadn't received it. With her cryptic comment on the phone that morning, I wasn't putting anything past her. I shot a couple games of pool and had another beer, then decided to face the music. I was going to have to do this face to face no matter how mad she got. When I pulled into my parking space, I noticed a police car parked in front of the building. My first thought was that Bonnie had gone ahead with the eviction, and there were cops with an eviction notice waiting to escort me out of the building. I slipped into the back door and made my way to my apartment, but the hallway was empty and there was no notice on my door. After checking inside, it was apparent that no one had been there, so I figured I was just being paranoid

"She doesn't have the guts to pull anything like that." I thought

I grabbed the cash and headed to Bonnie's apartment to put an end to this situation for good. When I reached her apartment, I saw the two cops standing in her doorway, one with a pad out taking notes, the other standing with his hands on his hips listening to Bonnie explain something.

"Oh Hi, Sweetie." Said Bonnie to me interrupting whatever she had been explaining, as the cops turned to look at me.

"Hi Bon," I said tentatively "What's going on?"

"That sweet new tenant Terry in 239 had her apartment broken into last night." Then turning back to the police she asked "Is there anything else you need from me?"

"No Ma'am," the one said "I think we have everything. Give us a call if you think of anything else, or if you can figure out what happened to that video."

I felt my knees get weak as I contemplated what was going on. I hoped I hadn't lost all the color in my face. My mind spun trying to figure out what Bonnie was doing.

The cops turned and Bonnie walked them out the entryway of the building chattering at them all the way. When she returned, her demeanor had changed dramatically. She looked at me icily. I held the envelope with the money in it up for her. She looked at it but didn't take it.

"Come here," she said coldly "I want to show you something."

I followed her into her apartment. She went to her television and replaced a videotape in the VCR with one that she removed from the cabinet underneath.

"Terry in 239 had her television and some jewelry stolen last night." She said not looking at me "I don't suppose you know anything about that?"

"You know I don't"

"No," she said "All I know is what the police would think if they saw this."

She pushed "Play" and I saw an image of a hallway in the building. There was nothing for a while, then suddenly I saw an image of myself walk out of the stairwell. My heart sank.

"Do you remember that security system we had put in last year?" she said mockingly "No, I guess you weren't here then."

I had always been aware of the cameras, but Bonnie had once told me that they were non-working decoys. The building owner had been too cheap to install a real security system. I watched the image of myself as I walked to apartment 239, and tried the knob. With the lights having been on, my face was well illuminated and unmistakable. The counter in the corner of the screen showed today's date and read 12:34 A.M.

"You set me up, Bonnie" I said sinking into a chair

"Oh Sweetie," she sneered condescendingly, "you did it to yourself. Look."

On the video, I turned and looked both ways down the hall, then looked closely at the door catch, fumbled with it a bit then rather forcefully opened the door. Bonnie switched the tape off, and looked at me.

"True," she said, "It doesn't show you walking out with anything, but it does show enough to put you in jail. Oh Hi Terry," she said suddenly looking up at the door.

In the doorway stood the stunning redhead I had fucked into a state of bliss early that morning. She gave me a sneering smile, then turned to Bonnie.

"I saw the police leave." She said

"Oh, yes." replied Bonnie, "They were very helpful. I explained the mix up with the security camera tapes and they gave me a number to call if anything turns up."

Bonnie walked to her bedroom and returned carrying a small television with a jewelry box resting on top.

"You just have to be so careful anymore," she was saying "you just don't know who to trust."

"I guess not." Replied Terry taking her 'stolen' items from Bonnie. "Let me know if you need anything else."

"I sure will."

"See you around, Lover" Terry sneered at me as she walked out the door.

"Take your money and go home." Bonnie said to me forcefully, holding the door open "Be back here at 10:00 tonight, and we'll work out the details of your arrangement."

I left her apartment and walked back to mine, wondering what was in store for me tonight.

I sat around my apartment that evening contemplating the situation I had gotten myself into. Bonnie had been one step or more ahead of me the whole time, and I had walked directly into her trap. Now I was doomed to spend who knew how long in her services. Merely raising the rent money wasn't going to buy me out of this, I had to think of something else or I was going to spend the remainder of my youth banging fat, old ladies at the whimsy of this pseudo-madam.

As the clock approached 10:00, I cleaned up and headed towards Bonnie's apartment wondering how bad this was going to be. Bonnie answered the door in a remarkably sophisticated dress. I was a little taken aback since I had only seen her fat ass stuffed into outdated summer clothes that were several sizes too small for her. Additionally, there were 10 other women in the room, all in nice dresses and acting very proper. Each had a drink in her hand and appeared to have stopped in mid-conversation as I entered. I saw Terry among them with a lascivious smile on her face, and the others I recognized as building residents from passing in the hallway and laundry-room. 8 of the other 10 were well into their fifties or sixties and showed varying stages of being overweight, but the one that Terry was talking to was fairly short with large hips and a big ass, wearing a tight-fitting black cocktail dress. She was younger than the others and fairly toned. With out a doubt, this had been my first appointment in the dark apartment on the 3rd floor. The recognition must have showed on my face, and she gave me a little knowing smile.

Bonnie took me by the arm and led me through her apartment as the women began returning to their conversations. I noticed several trays of finger sandwiches on the dining room table as well as a tray of champagne flutes. All the women were dressed in very nice evening gowns or cocktail dresses and I suddenly felt under-dressed in what could have been a country club reception. I had no idea how under dressed I was going to feel. We entered Bonnie's bedroom, and she closed the door behind us. Still holding her champagne glass, she sat on the edge of the bed and motioned for me to sit next to her.

"Now Sweetie," she began, "let me tell you how this is going to work. You see all these women know about our little arrangement and each of them have their own desires which they are willing to compensate us for. However, with the exception of the two you know, they are curious to see what they will be getting and if you can satisfy there expectations."

She paused for a drink, then continued. "Now, I assured them as I assure you now, that you WILL meet there expectations as you will meet mine tonight."

"What do you expect?"

"Nothing more than serving us sandwiches and drinks and doing what is asked of you. You will be polite and courteous. You will address each of them and myself as "Ma'am", and you will speak only when spoken to. Abide by these rules, and this evening will be over before you know it. Am I clear?" I couldn't believe the transformation that had taken place in Bonnie. I had always considered her only a few steps removed from "White-trash" and she had done nothing to dissuade my opinion until now. She fit the bill perfectly of a conniving, manipulative socialite. I had no idea what was real and what was a facade anymore.

"Yes" I replied

"Yes, what?"

"Yes Ma'am" I said sheepishly feeling the blood rise into my cheeks.

Bonnie smiled and said "Good, I'm so glad we have an understanding. We'll work out the compensation portion later after I see how well you perform tonight."

She stood up and retrieved a black bow tie from the dresser and tossed it to me saying "Here. Wear this."

I took it and looked around. Seeing nothing, I looked back at her and asked

"What else should I wear?"

"Nothing, Dear," she said with an evil grin "That, and ONLY that. Now, go on, get out of those clothes."

Vowing in my mind to somehow make her pay for the humiliation I was no doubt going to face, I stood and began removing my clothes. When I stood in front of her completely naked, she helped me put on the tie then stood behind me examining me in the mirror.

"Not bad," She said looking me up and down, "but something is still not quite right."

She opened a drawer and removed a bottle of baby oil. Starting with my shoulders, she began rubbing it into me until I glistened. She worked her way down my back and took her time on my ass. She then moved around front an began applying it to my chest. As she worked her way down over my rippled stomach of which I was very proud, she kept her eyes locked on mine, smiling as though waiting for some reaction. She filled her hand with more oil, and began stroking my cock. The slick stimulation soon had my member hardening, and when it was semi-erect, she stopped and examined it. It appeared very large, but still hung slightly.

"Perfect", she said wiping her hands on a small towel. Then she took me by the elbow and led me through the door.

"Ladies," Bonnie announced loudly as she positioned me in front of them "I give you this evening's entertainment."

All 10 of them stood speechless, eyeing me up and down with expressions that ranged from smugness to awe. I felt my face flush as I stood there completely exposed. Then, one and eventually all began to clap lightly. Bonnie took me by the arm and led me to the dining room table with all eyes following us. She picked up a tray of sandwiches and handed it to me, then motioned to the assemblage. Realizing that my best option at this point was to perform as well as possible, I took the tray, bowed slightly and boldly moved into the crowd.

As I circulated through the crowd offering sandwiches, some still gawked, but most played their roles perfectly and barely acknowledged my existence as they took sandwiches or placed empty classes on the tray. After a while, I became more comfortable, if that was possible, gave polite "Ma'am?" as I offered champagne or food and "My pleasure Ma'am" in response to occasional thanks.

Bonnie glowed as she moved from conversation to conversation with each one she stopped at turning to look at me as they continued their discussions. Most smiled approvingly as they talked about me, yet some still held their condescending sneers. I couldn't help wondering what was on their minds. I had opened 5 bottles of wine, and many were beginning to show obvious effect. All had become accustomed to me walking around in my current state and some began touching me as I went past. As I approached one particularly large woman in what I guessed to be in her late fifties, she grabbed my cock and began stroking it.

"I wonder what else you can do with that thing besides wag it in front of us."

"What ever you like Ma'am" I said submissively

She gave it a few more strokes then turned towards her friends saying "We'll see."

They all started laughing and I flushed a bit, but quickly regained my composure. I stole a glance at Bonnie and saw that she was simply beaming.

"Keep smiling Bitch." I thought "You'll get yours."

With the fat woman's advance, the ice had been broken, and now nearly all the women touched me in one manner or another as I approached them. Some cupped my balls and others stroked my cock keeping it in a state of semi-erectness, while the more reserved ones rubbed their hands over my chest, stomach, or arms cooing and nodding approval.

After an indeterminate amount of time. Bonnie stood at one end of the room, beckoned me to stand beside her and announced "Ladies, may I have your attention."

When all eyes had turned, she continued

"You've all seen the product, and some sampled in various ways. Are there any questions before we conclude this evenings activities?"

After a few moments of silence, a fairly diminutive woman shyly raised her hand.

"Yes?" asked Bonnie

"How big is it when it's...you know...uhmm...all the way?"

There were some snickers and giggling, and the woman became rather red in the face.

"Would you like to see?"

All nodded and muttered their agreement.

Bonnie stood back and looked at me. Not understanding, I looked quizzically back at her. She raised her eyebrows slightly and nodded towards my cock. I set down the tray I was holding, then took a deep breath and began stroking my dick. I felt all eyes boring a hole into me, and I stroked faster. Quickly, I was hard as a rock, and I heard Bonnie clear her throat.

I stopped and dropped my hand to my side allowing an unobstructed view of my rock-hard member. Some gasped slightly, and all nodded their approval. One even began clapping lightly, obviously enthused and quite drunk.

Bonnie opened her hands asking if there were more questions.

"Will he do whatever we ask?" asked another woman

"Of course he will." replied Bonnie

"Even the more, shall we say, bizarre?" asked another

"Absolutely. What did you have in mind?"

"Would he, you know, use his mouth?"

"Oh, but of course Dear. I thought you meant something really off the beaten path. Yes, he is more than you bargained for in that arena. What Else?"

"Does he have stamina? I know these young bucks spend themselves pretty quickly."

"You may have to prep him a little first, but he'll go as long and as often as you would like him to."

"What do you mean 'prep" him?"

"Well, " replied Bonnie, "you may have to have him burn off some energy before you get started, but then, that can be part of getting started now can't it?"

"How exactly do we do that?"

"Either you can have him do it, or you can help him along, either way, just a little prelude."

"Help him along Hmmm?" said the large fifty-ish woman walking towards me with a slight stagger, "Do you mind?"

"Not at all." Said Bonnie stepping back and extending her arm towards me The woman stood in front of me gazing drunkenly into my eyes as she grasped my dick and began stroking it.

"Hmmmm, nice and hard. I bet his DOES feel good."

She began stroking faster and even in spite of all the attention, the sexual tension in the air began driving me towards the edge. My hips bucked a little involuntarily and she gripped harder. She quickly handed me her champagne flute and releasing my cock said "Here, in the glass, don't make a mess."

With glass in hand, I grabbed my cock and with a few quick strokes, felt my self cumming. I bent over slightly, held the glass in front of my dick and shot stream after stream of cum into it.

I regained my composure and stood up again, holding the glass in front of me. The woman took the glass from me, and keeping her eyes locked on mine, drained the cum laden champagne in a single gulp. She wiped her mouth and smiled stepping back. Bonnie extended her arm like a ringmaster, and all the women stood clapping. When the applause subsided Bonnie asked if there were any more questions.

"How long till he's ready again? Asked one who I had not here speak until now.

"I believe he's still ready." Said Bonnie motioning towards my still hard cock

There was a few moments of silence while the women considered other questions. I wondered what kind of deal Bonnie was offering them that they had to think so deeply about. Finally Terry stepped forward and said. "What about the things that DO range toward the more bizarre, and how do we know he'll do them?"

"I'm not sure I understand" said Bonnie

"Well," continued Terry, "you're the only one here who has received his, shall we say, alternative treatment, and if I'm not mistaken, one of us has already been disappointed in that arena."

"I was kind of hoping this would come up." Said Bonnie with a smile and walking to the fortyish woman in the black dress "you may have heard that this young woman was slightly disappointed in the treatment that she received. Now I have learned from her that in addition to that facet of her desires, she also has a penchant for public display. So now to make amends to her as well as to dispel any doubts the rest of you may have, she has agreed to receive a complimentary treatment here for you all to observe." An excited murmur ran through the crowd and I gawked unbelievingly at Bonnie. Jerking off was one thing, but she apparently wanted me to fuck this woman in the ass while the others watched. Bonnie shot me a quick glare, and I dropped my glance.

The women began clapping, and Bonnie produced the baby oil and handed it to me.

"Here?" I asked

"The table should be sufficient." Bonnie replied leading the woman to it

"You're going to love this, Dear." Bonnie said gently to her, "now place your elbows here, and just relax."

Bonnie stroked her back comfortingly then beckoned me with a nod of her head. The woman's generous ass was jutting out towards me and I thought she was going to die of embarrassment as Bonnie slowly slid the woman's dress up exposing it but I saw her wetness running down the inside of her thigh. She really was getting off on this display. She wore no panties, so either she was a flasher, or this had been planned. I reaffirmed my conviction to make Bonnie pay for this as I lubed my cock and approached the wiggling ass in front of me. The women crowded around excitedly, and I poured a bit of oil on the small of her back and allowed it to run down her ass-crack. I worked a thumb up and down her ass-crack until I found her little rosebud, popped it in just a little to ensure that it was lubed. She let out a small gasp and many of the women giggled, but most were just mesmerized. I began working my cock-head up and down her ass crack until I found my target, then gently, I began pushing my well-lubed cock up her ass. She gave a slight groan, and I stopped, but when she wiggled a bit I knew she wanted more, and I worked it farther in. In a few minutes, I was pushed all the way against her big butt, and I held it momentarily letting her become accustomed to the size. She wiggled some more, and I began to stroke. Gently at first, with small strokes, then gradually faster and with more length.