Loss of Amateur Status Pt. 06

To fully understand the context of this narrative, I would recommend you read "Loss of Amateur Status." Parts One through to Five.

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When I next saw Agatha a few days later, she surprised me. She had a list of four appointments over the course of the coming week! I was really on the game! A couple of weeks later she bought me a smartphone that synced with her computer. When I visited her on Friday afternoon, all I had to do was drop it into its cradle and my appointments for the coming week would be uploaded into Outlook on the phone. All the names, times and addresses plus any background info she had, especially if it was a new client. She regularly included information regarding any special desires or preferences a client might have. For example the client might want a romantic "boyfriend" style experience or maybe she desired to be dominated to some degree. Fairly frequently, there was a role play element where I might play, for example, the escaped convict or policeman or pool boy. I am sure part of Agatha's sales pitch actively encouraged clients to live out their own erotic fantasies. I had an interest and background in amateur dramatics so that was just icing for me.

Next to the computer she normally also had a printout of all the previous weeks engagements with a financial reconciliation and another printout of the electronic funds transfer that she had made into my account. After I had checked that, we moved to the bedroom and, as we undressed, discussed any business matters concerning the coming week. Once naked she became submissive and I enjoyed using her body. Of course she paid full market rate.

I guess it's timely for me to make the confession that I have a bit of a thing for older women. (As if you haven't figured it out by now.) Don't know why. I can't seem to point to anything in my upbringing that could have caused this but there it is. Regardless, my own sexuality made me ideal for serving the sexual desires of middle aged women which made up the bulk of my clientele.

Over the next couple of months or so I became increasingly busy with Agatha's work to the point where I ended dropping the slate laying altogether. While my current "work" was quite physical in one way, I found that I was losing general physical condition. I mentioned this to Cruella who made a sort of bitchy comment about 'not having the merchandise going off' but she did hook me up with a female gym owner who, in exchange for one appointment a month, would give me a deluxe gym membership. She was an ex-body builder of about 40 who was probably stronger than I was. It made for some interesting sex but those bulging muscles were not really a big turn on for me. I remember once when, during oral sex, she almost suffocated me between her thighs.

It was interesting to note that virtually all the women I serviced expected me to come. I think it was affirming for them if they saw that I was turned on to the point of orgasm. Indeed there were a few women to whom it seemed that my pleasure and orgasm was more important than theirs. I still worked hard to make sure they were satisfied as well but they certainly got off when I got off. Only once did a woman call a halt after her orgasm but before mine. I couldn't exactly complain but it was rather exasperating.

One line of regular work that developed was that of international airline cabin crew. Somehow the female flight attendants of a couple of airlines got onto me (so to speak) and booked me when they had an overnight stay. The novelty of this was the age difference. They were generally but not always younger than my regular customers. Most of them could easily have picked up some young stud for free but by using me they could call the shots and get exactly what they wanted with no strings or risk attached. Some of them were quite demanding but I just about always enjoyed myself. I would slip discretely into their hotel room and give them whatever they needed. I once had a very enjoyable threesome with a pair of very close friends.

There were only a couple of women that I refused further bookings from. One was a very odd woman who was taller than me and very skinny. She had an angular face and a high pitched squeaky voice. On our first encounter she ushered me into her apartment and took me straight to the bedroom. She took off the robe she was wearing and lay back nude on the bed. No small talk required with this one; it was straight down to business. She was a bit scrawny compared my usual fare but I told myself that variety is the spice etc. Without further ado she told me she wanted straight sex and nothing else and that I was to orgasm whenever I felt the need. A very unusual service request. I climbed on and after a little work guided myself into her. She was tight, not well lubricated and totally unresponsive. Her eyes were shut and her body rigid, I soldiered on and was surprised and a little disappointed at how corpse-like she was. Given that she only wanted a straight fuck; my options for trying to get her to engage were a little limited however. I thought I would go up tempo and give her a real power fuck, so I started to really hammer into her. Still nothing. I was mildly annoyed now. I suppose my ego was bruised, I was used to a fairly rapturous response to my services. I went into top gear but the only feedback was a high pitched squeak with each thrust. I think I fucked her harder than I have ever fucked anyone before. I was starting to get a bit bored and frustrated so I told her I was going to finish. I dropped my load and she quickly wriggled out from under me and disappeared into the bathroom. To my amazement, she asked me back in three days time and again in three further days after that. Three or so weeks later she booked me again. Agatha spotted it first. "She's using you to try and get pregnant." My God, the dates fit! She only needed me around when she was ovulating. I was in no mind to start handing out my DNA on a permanent basis so that arrangement came to a barren end.

One afternoon I got a phone call from Agatha. I had never heard her so rattled. When I queried what was upsetting her she explained that Ms. Stickler was starting to talk. Rumors concerning our activities were being circulated that could cause us serious problems. When I suggested that Agatha remind Ms. Stickler that we had acquired a pair of her knickers in rather compromising circumstances, Agatha replied that she had tried that and Ms. Stickler simply denied any knowledge of the underwear or the incident.

I drove over and, after a brief strategy meeting with the anxious Agatha, marched with purpose over to Ms. Stickler's residence. After a forceful knocking, the door opened to reveal Ms. Stickler. I gave her my best leer and stated, "You have been a very bad girl."

She was clearly alarmed. Her feet started moving erratically, reminiscent of an intoxicated tap dancer. Her arms were making a sort of rowing motion, sort of pushing me away and then pulling me in. Her skittering footwork was causing her to slowly drift across the room like a drop of water on a hot skillet. This ended when she bumped into a couch and fell clumsily back onto it. I entered the room, carefully closed the door behind me and joined her.

"What do bad girls get Ms. Stickler?" Without waiting for a reply I hauled her onto my lap. The ease with which I did this reminded me of just how diminutive she was. She twisted and looked up at me. Her expression was fearful and flustered.

I lifted her ridiculous floral print dress and revealed a style of knickers I was familiar with. I used two hands to rip them off her. This caused her to shriek in what I thought to be fright. I had to be careful here or I could get into consensual issues.

I repeated, "What do bad girls get Ms. Stickler?" I gently massaged her miniature bottom. There was no reply so I gave her a sharp pinch.

She squealed and whimpered out the word, "Spanked."

"Do you deserve that Ms. Stickler?" A nod of the head. "Do you want that Ms. Stickler?" There was a hesitation and another nod. "Very well."

She sobbed, "Oh Papi, what have I done?"

My first smack caused her to momentarily stiffen like a board and then slump back down onto me. After another couple of swipes I felt her hand writhe around under her. In a change from our last tryst her attention was drawn towards my crotch. She kneaded the front of my trousers and quickly found that I had developed a rather substantial erection. This elicited a sob that sounded more grateful than fearful. She squeezed my shaft in rhythm with my wallops. A few moments later I felt her other hand moving to the center of her pleasure and begin a steady rhythm of its own. The harder I spanked the tighter she squeezed my shaft. It was all very pleasurable.

After a few minutes her bottom had changed color to stop light red so I thought I would redirect my efforts. I ran a finger up and down her little slit and was again surprised by her level of lubrication. She flinched at my touch but when I felt her redouble her attention to both my penis and her clitoris I was suitably assured of her complicity. After a few further swipes up and down her slippery little slot, I insinuated first one and then a second finger into her. She braced herself initially but then started rocking her backside back against my intruding fore and index fingers. Clearly this was action met with approval. Quite co-incidentally this left my thumb resting upon the little date of her anus. In a moment of whimsy I greased up my thumb in the oily well of her vagina and then replaced it on her tiny pucker. I began a gentle but insistent invasion. She squirmed and moaned but this was soon replaced with a low whimper that spoke more of pleasure than pain. Indeed it seemed to intensify her manipulation of her little carnal fun button. I could feel rather than see her fingers flying over her clitoris. In a few extra short moments she tensed and let out a bellow of completion. That changed to a bellow of shock as I chose that moment to fully impale her with my thumb. I felt her anal ring spasming and she bucked on my lap like a beached fish. I had my fingers in her like she was a bowling ball.

I withdrew my fingers and gently stoked her bottom. I wondered if she expected or wanted to now be fucked. My silent query was answered when she slithered off my lap onto the floor, removed the remainder of her clothes and assumed a prostrate position before me. I stood and lowered my pants and underwear but instead of boarding her, I sat back down on the couch. My very erect penis had her mesmerized. After about fifteen long seconds of intense ogling, she dragged her attention away from my member and looked up at me with a quizzical expression. Two things were clear. Firstly, the sight of a stiff penis was highly novel for her and secondly, a female superior position was not something that sprang quickly to her mind.

"Mount me," I said. Her wrinkled face creased even further with a questioning look but then she had her eureka moment and scrambled nimbly to her feet. She approached me tentatively and climbed carefully onto my lap. She was behaving very timidly. I held my penis so that it was vertical and she positioned herself so that she was directly above it. She shyly looked at me and I nodded. She gently held my penis and slowly, deliciously lowered her snug sheath down over it. She arched her back and started gasping for breath. Her tiny hands came up and grasped my shoulders with a surprising strength. I could feel her fingernails digging into my flesh. She slowly moved her body up and down, each oscillation resulting in a small gain in depth. I became impatient, badly needing to be fully inside her. I seized her shoulders and gave her a forceful yank downwards. This was accompanied by an equally vigorous lunge upwards from my hips.

Her shriek was the loudest sound I had heard her make and it made me concerned that I had injured her, but after a moment to collect herself, she started bobbing up and down in a way that clearly signaled she was keen to continue. I decided to relax and let her do the hard graft. It was very fulfilling to just lean back and watch her work away. She had an intense and determined expression. While her head was mostly cast down she would occasionally sneak a brief, furtive glance at me. Her breathing was deep and hoarse.

After several minutes of this mutually satisfactory activity, I decided to change things up. To telegraph that there was a change in the wind I grasped her shoulders and gave her half a dozen powerful pelvic plunges. Her body flailed and she wailed. I then grasped her waist and lifted her off my cock. Again I was struck by how diminutive she was. The other small surprise was the sucking pop sound that her vagina made when she was lifted off my penis. An audible telltale of just how tight the fit was. I started rotating her and eventually she understood that I wanted her to face the other direction. Once she was remounted she again began her enthusiastic bouncing motion. My hands roamed over her back and reached around to interfere with the two little raisin-like objects that were her nipples. I gave each a firm squeeze which elicited a sob and a faster bobbing motion and another moaned comment about being a bad girl. I experimented with my tweaks. After each pinch she took off like a horse goaded by spurs.

After a few further very agreeable minutes of watching this miniature gilf bouncing up and down on my lap, I reached into the pocket of my adjacent discarded trousers and surreptitiously removed my phone. I sent a quick text message and then returned the phone. Ms. Stickler remained oblivious. What I did next however, she became instantly aware of. I put my hands under her knees and stood up. The forceful movement thrust me even deeper inside her and she made a whooshing sound like I had driven the air out of her. I then turned towards a mirror that I had noticed on an adjacent wall.

The image we created together was truly depraved. I held her legs even further apart to illustrate her impalement even more graphically. We could both clearly see my shaft sliding in and out of her body. Her inner thighs were slick and shiny with her fluid and her pubic hair looked disheveled and matted. The reddened look of her nipples caused by my manipulation also looked clearly unnatural. I found it novel to see that, because of our height disparity, I could see clear over her head. Indeed I could rest my chin on the top of it. As soon as Ms. Stickler saw our reflection she averted her eyes and started sobbing. I gave her a few solid thrusts to get her attention and within only a few seconds she reluctantly returned her gaze to what could only be described as representing her complete degradation. As I kept hammering up into her, her look of shock wilted. She appeared unable to resist giving herself up to the sensations of intense sexual pleasure. I watched with satisfaction as her hand moved to her crotch. With a murmured, "Oh Papi, what have I done," she started to feverishly stimulate herself.

I heard a snick behind me that indicated that the front door was being opened. Another snick swiftly followed. I hoped that a particular person had just entered the room and closed the door behind her. I looked over my shoulder and saw Agatha. The expression on her face was priceless. Amusement and amazement. She gave me a quick double thumbs up and then picked up the camera that was hanging around her neck.

This may have been a bit cruel of me but I waited until I sensed Ms. Sticker was just starting to orgasm before I turned to face Agatha. At first she was insensible to Agatha's presence but when she realized she was on full display and being photographed, she started convulsing in a futile attempt to flee. Her gyrations simply added to my pleasure.

Within a minute she surrendered and slumped motionless in my arms. I was, not unsurprisingly, rather aroused by all that had occurred and had no intention of not reaching my completion. In a moment of inspiration and innovation, I raised my hands up to the back of head which forced her knees to her shoulders. I think the position is named after a wrestling maneuver; a nelson or half-nelson or something similar. This pose drove Agatha into another flurry of photography. Given that the position resulted in my hands forcing Ms. Stickler's head forward, I generously leaned back so that Ms. Stickler's face could clearly see and be seen. After a brief photoshoot I turned to the mirror. I was eager to see what this novel coupling looked like. My co-wrestler stared mesmerized like a possum in the headlights of an approaching car.

I admit it is a fault in my character but the humiliation described by our reflection spurred me on to an intense flurry of thrusts which shortly resulted in a mind draining orgasm. After I had regathered my breath, I turned and faced Agatha. I gave her a wink and slowly lifted Ms. Stickler up and off my now limp penis. My photo journalist sensed a scoop and moved in closer and took a sequence of photos that recorded a small but stretched vagina discharging an impressive volume of ejaculate. When I later saw the photographic evidence, I was actually rather proud of the amount I had discharged inside her.

I was then at something of a loss. I was holding a bundle of naked, leaking, female sexagenarian. I was thankful when Agatha pointed towards a corridor that I found led to what must have been Ms. Stickler's bedroom. In a moment of tenderness, I gently lowered her to her bed. She lay unmoving which was a little concerning, but as I leaned over her, I could hear ragged breathing and a very quiet, repeated murmur, "Bad girl. Bad girl. Bad girl."

I returned to the front room where Agatha handed me my clothes. With words that reinforced the smirk on her face, she mused as to how Ms. Stickler could possibly dismiss such compelling and damning evidence. Any one of the photos would irrevocably devastate her carefully composed reputation.

The next day when Agatha met with Ms. Stickler and showed her some of the exceedingly explicit photographs she had taken, the star of the photo essay went ashen white and pledged to be exceedingly discreet and not spread any further rumor or innuendo whatsoever.

But there were two other rather unexpected outcomes from this meeting. Firstly, Ms. Stickler wanted copies of all the photographs. Given that this would clearly not hinder our blackmail, we could only conclude that she wanted them for her own sexual gratification and secondly; she wanted to make a permanent monthly booking; an encounter that included a spanking and vaginal intercourse. Ever the professionals, we took her reservation.

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