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Moonlighting, Chap. 2
by ???


 
At break Josylyn and several other girls had me walk around the halls naked with them including to the cafeteria. They all touched and fondled me with curiosity and Josylyn spent a good deal of time on my balls. In fact after break she volunteered to oil me down again. In front of the whole class she explained that I worked for her in my day job and that taking this class was giving her a whole new perspective on me and my potential uses. She stroked my stiff dick and then played with my balls while standing behind me until Ms. Krochek told her it was time for me to pose again. My pre-cum was dripping onto the stage and I could feel an orgasm ready to burst. I fought to control myself, not knowing if she wanted me to cum yet.

Moments later Amy came in and watched as Ms. Krochek wasted no time in getting me into a pose that pushed me over the edge and I was about to start spurting at any second. Ms. Krochek seemed to know this better than I did. She looked at me with a wry smile as my cum started to spurt and called “time”. Amy smiled at me and came closer with papers in her hand and said, “Well, let’s review your schedule.” I was completely out of control and facing her still partially in the pose just gushing. She watched my first spurt with full attention and said “I’m glad you’re excited that I’m here and that you want to do more work for me, now pay attention, cum over here as I tell you what you’ll be doing for us next. You do want to do whatever I tell you don’t you?” I gasped a “yes mam” and wobbled toward her still cuming as I stuggled to listen to her words. Josylyn watched listened and laughed. She pointed to the calendar on her paper as I spurt again and again struggling to focus on her. She stopped for a second and watched my cock spurt and said “Are you about finished with your orgasm - I don’t want you to jis on my clothes - or I’ll take the cleaning bill out of your pay.” I came again trying to stop what I knew I couldn’t. I felt so humiliated. “yes mam, sorry mam, thank you mam” Surpressing her hysterical laughter to avoid joining Josylyn’s, Shirl’s and a couple other girls watching the scene, she said, “Well that’s better then. Remember having an orgasm on the job is a priveledge that we allow you, but you must perform to my satisfaction - if I tell you to stop cumming then you had better stop and if I tell you ejaculate then you better spurt a load. Here in the next month and till the end of the semester we’re going to use your drooling dick a lot.” I stood there wobbly looking at the schedules pages she had in her hands holding them under my cock and I spurt again on the paper. She said “I’m glad you agree” and handed me my now cum stained schedule pages. My balls started to ache. Josylyn introduced herself to her and they started talking and left the studio together. Shirl said, “So those two are your bosses.”

The next morning it was a hard day for me and Jane – I didn’t know what to do and just went for it. When she asked me about my being shaved down – I said I thought it was a good idea based on the pictures I’d seen. I was so embarrassed that I barely got hard as I sat next to her. Jane made a point of asking the girls at the club what they thought. She ran her fingers down my hairless chest and my cock popped into full mast as she discussed the possible benefits with the girls. Then to the pool and a hard routine. She touched my skin more and I was ver excited by her attention. Then it was time for my shower and she hande me the towel - it was a smaller one than the usual one - I wondered if she switched it on purpose. It popped off as I pulled my speedo off and she picked it up as my stiff hairless dick pointed at her as I stood facing her with my sit in my hand. She stared at me holding it and we traded and she said "Well you were certainly thorough." with a giggle. I put the small towel back on and sat uncomfortably in at the juice bar waiting for her. She came out in a nice dress and handed me my sweats and I pulled them on and we finished our drinks and headed out.

The following day Josylyn told me that she wanted to review my work in her office. I walked in and she told me to strip she closed and locked the door. I was excited and embarrassed and nervous, but I obeyed and she had me stand in front of her as she fondled me. My cock was rock hard in seconds and she settled into fondling my balls as she asked me questions about my work for her and told me what she expected of me. She took several phone calls while holding and playing with my balls. I was in her office for nearly two hours during which time she had me by the balls almost the whole time. She told me that the whole group would start taking sales trips to conventions and that I’d be coming.

I came close to cuming several times but then she’d yank on them as she spoke to people on the phone and my urge would dramatically lessen. Finally she stroked me to the point of cuming so that I couldn’t stop my self and then said sign this here and here as she held my balls I started to sign as I came and she asked me as I was cumming you’ll do whatever I tell you won’t you? I gasped “yes mam” as I came on the papers she was having me sign on her desk as she squeezed my balls.

Then she said “Go back to your desk and get some work done.

That night she had me take my pants off in her car for my ride to school where she held my stiff dick like a stick shift the whole way till we got to the school where she told me to “keep it up” (her new terms to me were “get it up or keep it up” she said it to me particularly in front of the girls in the department instead of get going or keep up the good work.) She released my cock in time to let me pull my pants up and hop out of the car to get to class. I was incredibly hard and turned on. My cock throbbed and oozed and pulling my pants on was as much a chore as it was with Jane.

I went into the building and to my locker and happily stripped freeing my throbbing cock. It wouldn’t take long for me to cum tonight. I put my robe on and went in to check-in with Amy - excited that my cock was already at full mast and hoping that she would be interested. I stood near her desk with my paper in my hand. As usual there were half a dozen girls in there doing things or waiting for someone. She glanced at me and then looked disgusted and said “well? are you going to be posing in that robe tonight?” I shook my head and removed my robe and walked across the room to hang it up - my body still completely shaved and with my cock standing full out before a gruelling class. The girls in the office commented on my body and she answered her phone while I calmly stood at the position of attention before her with my cock jutting out in a hard-on that felt alive. She watched my dick throb as I stood proudly at attention before her, and as it started to flag a little she got off the phone and smiled - “don’t make me have to correct you again - you are to report to me ready to work.” and she swatted the tip of my cock with her ruler alternating top and bottom with each word for emphasis, the girls in the office giggled. It hurt but not enough to make my woody wilt - it actually stiffened to 110% again. I said “yes mam - it won’t happen again” and put my robe back on and headed to the studio to start my rhoutine. Ms. Krochek seemed happy when I got on stage already hard and ready to work.

From the stage in the studio, I thought I could see Sue, Louise, and Kim get out of a car and start toward the building. The girls looked up and saw me and stopped. They pointed and waived and it looked like they took my picture with a camera, a few minutes later they were sitting in the studio in front of me smiling and sketching, as if they knew how...

I was stunned. I held my poses and soon I had to cum right at them - I spurt and my jism landed right at Sue’s feet. She laughed and put the toe of her shoe in my cum. I felt so trapped, naked and vulnerable. At the break I had to clean my mess and Ms. Krochek left the room. They played with me and tormented me. Laughing and giggling, they pulled my balls, slapped my ass poked my asshole and the some of the other girls watched and laughed. “We knew you’d be happy to see us. Let’s see if the photo came out from the parking lot? “ They showed it too me on the polaroid. It was fairly clear, though my figure in the window was a little blurry, but it gave me the picture that people outside in the parking lot, on the sidewalk and driving down the street could see a naked hairless man was posing with an erection pretty clearly. Finally, Ms. K came back and had me up into another pose. They all sketched me and then left as soon as class ended. I stood before Ms. K at attention for her signature; I was shaking a little but managing to appear fairly erect. She smiled and told me that I was doing fine and to make sure I stayed clean shaven for all of her classes that I was assigned to. I thought about Jane - Josylyn was right she would see me as nude model - what would I tell her.

I walked back to Amy’s office hung up my robe and stood naked and hard saluting her at her desk with my timesheet. She smiled, “Better.” She stroked my dick with her finger.

That morning when Jane picked me up – we started with some stretching which got me hard almost the instant she touched me. We went at it for awhile and then to the swimming, running and biking and more stretching.

In the office, the girls were comparing lousy sketches of me with Josylyn and telling the stories to the rest of the department. Then it started, Sue said, “Now I know I was right yesterday - you should just work naked for us” Pat looking at the lousy sketches and the blury photo said “I’d like to see more” Kim said “Forget that thong - if you can work naked for the art school - you should for us too - it’s not like we’re going to let you meet any customers.”

After several more classes Josylyn, Pat, Kim, Louise, and Sue showed up to the weekly open session. Josylyn dropping me off and the other 4 showing up. Three weeks in a row all 4 went to the session together and I was their model. Amy seemed very pleased with keeping me in the open session as most of the students changed out frequently, so there was no need to maintain a heavy model diversity – as long as the numbers kept attending. She teased that I’d developed a little following and that she’d made Josylyn a package price for the company. Amy would simply call Josylyn’s assistant Shelly to confirm my schedule and that got included in my calendar for everyone to see.

After a month the rumors had spread and the ladies seemed to have fun comparing their drawings of me around the office.

Louise said “Hey, how about posing for us at lunch so that we can practice for class?”

Josylyn said “What a great idea, Shelly reserve the conference room and schedule the open department meeting for an hour and the weekly meeting immediately following. We could use the practice and he’ll do whatever we want him to for us. Won’t you?” I was stunned as I nodded to her realizing that my life was now in their control. The whole department of 12 women would be able to see me naked, and since it was an open meeting – anyone in the company could pop in. Now they were all going to be in on it. I was terrified that my secret was out and that I was going to be completely exposed at the office. At lunch time a couple of the girls were instructed to get the group’s lunch from the cafeteria and bring it to the conference room.

I was hearded in where I stripped before Jacqie, Sue, Louise, and Kim, in came Pat. I wasn’t hard yet as I was nervous and scared. Pat said, “Nice, he’s doing a fine job of staying smooth.” She reached out and stroked my leg - “almost as smooth as mine” she jibed. Josylyn walked over to me and grabbed my balls in front of Pat and said “Check these out” holding them for her to touch. To me she commanded “stretch out a bit and get it up while we wait for the rest of the department to arrive with lunch” She held my balls smiling and tugged them from behind me as I knelt on the conference table for all the girls to see as they came in.

Sue, of course, said “Look at that weaner grow” and Louise chimed agreement “Yeah...”

They started touching me and soon I was stiff and throbbing; Sue cheered. Suddenly the two girls assigend to lunch arrived and walked in with a bit of a shock as I was frozen in a stiff pose for the group with my cock jutting out, kneeling on knee and my other leg straight out with a torso twist. Kim brought out the camera and took several pictures of me. Once everyone was seated Josylyn stood up and said “watch this” and she started moving her finger. She made me do the dick ups that Ms. Yoyo made me do in front of the coordinator.

Soon it degenerated into them having me do dick-ups, slapping my ass and balls, and debating on whether to let me cum and how many times and/or strokes... By the end of the extended lunch hour, I was their play thing and had cum on the conference table in front of all of them while Jacqie talked about something and yanked on my balls. A few sketches were actually done, but it was clear that I was no longer just a nude art model for them. It became a regular weekly thing for me to pose for them and I feared that soon Jane would pop in on a session.

It was the following week at the meeting they’d all built me up to a throbbing frenzy and in walked Jane. I was in horror. She sat down and they made me cum on the conference table as they played with me posing for them while I gave my report to the group. I was peppered with questions as I started cuming and was barely able to grunt out answers as I was jerked by Jaquie alternating with Sue.

The next morning after that session, she knocked on my door instead of honking the horn. I let her in and she’d said make me some coffee and sat down. “Well, why are you dressed?”. I stripped down to my speedo as I went to the kitchen and started her coffee. She looked at me and said “You didn’t have that on in the meeting yesterday.” I had my speedo off and was hard in seconds - my dream girl just told me to strip and make her coffee instead of leaving for the club. Now I need something more in this. I stood at attention facing her with my dick hardening to steel and said “For you anything” She looked at me and said “good - then how about your nuts. She grabbed my dick and pulled me over and raised the hot coffee cup on the saucer up and slowly raised it immersing my nuts in the hot coffee. It hurt, but not horribly. I was stoic and held still “yes Jane anything you want” Then she started pumping my dick and slowly my orgasm built and she said “now I want you to cum in my coffee and stir it with your dick - be neat don’t spill any.“ I obeyed and loaded her cup with my semen. Good now massage my feet. I removed her shoes and gladly complied - I wanted to lick her ass too.

That week, she had me naked under desk for an a morning meeting, while I licked her pussy – she talked on the phone and discussed things with quick visitors.

The following week Lori came for a department meeting. I was the only one who didn’t know it was actually going to be a meeting instead of the usual fuck around with me session. I was naked and hard and the girls were all making sport of me. She walked in as the girls were having me do dick ups. She looked at me like she wanted to rip me apart and everyone said “Hi Lori” She said “I hope I’m not interrupting anything - please continue” They had me go up and down and side to side and she stood and watched with her arms folded sneering. Finally, I was sweating and she said “let’s begin.”

I was told to stand straddling the corner of the table next to Josylyn at my usual spot with my cock and balls on the table for all to see and for Josylyn and whoever was close to her to slap for emphasis. Sometimes one of the girls would just absent mindedly stroke my stiff cock as they talked. There were always odds on when I’d jis and the one who made me do lose it at the wrong time lost and would have to clean it up - I never knew what the right time was so I was no help and as a result the beautiful fingers grasping my stiff cock would sometimes come down as a fist on my unsuspecting nuts to keep me from cumming.

Lori sat to my other side set a plastic cup in front of my dick and Josylyn alternated pumping my dick and patting my ass keeping me unbelievably close to the edge. Lori conducted the meeting as if I was merely an amusement toy and finally grabbing my ass cheeck with her hand addressed me saying “You may ejaculate in the cup now.” I grabbed the cup and she held my ass cheek and Josylyn directed my dick to spurt in the cup. “That’s not enough do it again - keep it up” Finally when I was limp and could do no more she put the top on the cup and continued the meeting.

I was fast becoming naked slave instead of a salary slave. Jane now met me in the morning and I’d service her and stay naked for her until we got to the club. She’d have me running from the pool complex to the office building in my speedo and in the office I could only put on my sweats at my desk after saying good morning to the entire staff – they insisted I shower before entering the department and leave the towel in the bathroom.

Whenever Jane called me to her office – I had to report to her naked and hard. Then at lunch I’d be run by them on bikes and me in my speedo until I dropped. The next day’s lunch was naked posing.

Shirl called me over to her place again and she had me shaved by Roxy again and then they put a bow tie around my neck and serve them drinks. Then the doorbell rang and they told me to answer it - I was scared - Shirl slapped my ass and said “move it” and I complied and it was a couple more ladies they looked at me and laughed and said pleased to meet you and grabbed my dick as a hello gesture. Soon I was entertaining a house full of women and then they had me practice stripping for them. They had me dress up in various outfits and dance and strip to different songs rating my performance. I licked and fucked for hours. Some of the women were as pretty as Shirl and others weren’t. It was truly wild and weird.

When her daughter came home from school I’d been used and abused. Shirl had me do another strip tease so her daughter could watch my performance - she even made me do dick ups for her. I felt naked, exposed and embarrased. Shirl had me stay naked and start cleaning up. When most of the guests were gone, she showed Flo how to scrub my cock and balls clean from all the activity. Flo had seemed to put in great attention to detail as she held my cock and balls washing and scrubbing them repeatedly. They were bright red and very sore when she was done. Then it was time for me to scrub her floors. Then she told me to clean Flo’s room too. Flo smiled and put me to work, it was hours since the party and I started to feel like I could get excited again. Shirl just laughed and periodically watched Flo make me do dick ups for her interspersed with talking with her remaining guests, whom I was still responsible for getting drinks... Soon Flo had me back into a full erection - even though my cock and balls were sore to even touch. Flo liked seeing me hard and had me stay that way the rest of the evening until Shirl dismissed me.

Jane met me every morning at my place for me to service her needs. I licked her pussy and massaged her body before we went to the club. I’d also make her whatever she wanted to eat or drink. She came to a class with Sue, Josylyn, Kim and Louise and met Amy. She took me home that night and fucked me. I was so the happy. The next morning I tasted my cum in her pussy – that was strange but I was glad it was mine. I remembered the situation with Shirl and her friends and the various pussies with different tastes and smells. Jane’s was intoxicating.

Monday morning she showed me an ad for this penis enlargement stuff with a prize and she entered me and ordered the stuff. When it came to the office to her attention – she walked it over to the open lunch meeting where I was posing naked and hard for 8 co-workers. She made 9, but she wasn’t drawing. Josylyn was there. Jane reviewed the rules and the directions for everyone and the idea met with complete approval. The photographed my dick in several poses with rulers and everything.

I was measured weekly with an additional set of photos.

She was my body coach. By summer the stuff had worked and my dick was nearly 50% bigger 10” long when stiff and it had gotten thicker too. Fucking Jane had become awesome. Wearing the speedo for runs was almost silly, but it was what they insisted I wear for the race and at the start I was hard as a rail. The water was cool and I lost my erection. However, by the time I finished the run I was filled out.

Amy told me that one of the ladies at the school had inquired about using me for somemore private sessions and that she'd arranged for me to pose for them. I complied not even considering whether she should’ve asked me about it first.

I arrived at the address not even knowing the lady and drove down the long driveway to the large house. I knocked and was met by a midde-aged lady who said you must be… I didn’t recognize her but then I’d posed for so many. I followed her in and she told me where to disrobe and to leave my things there and asked for my car keys in case they had to jocky vehicles later. I complied and followed her naked through the large house to the large living room that she said they would use as the studio. She told me to stretch and then she was gone and returned with another lady and the bell rang again and soon everyone was there. There were 7 of them and I posed as instructed – I got hard and that seemed to make them happy. After awhile – they had me take a break and we had some tea. I ended up serving them tea and stuff by accident and that was the way. By the end of the afternoon they said good bye and that they may have me back again. I ‘d reocgnized a few of the ladies from the school. I was called back again a few weeks earlier and she met me at the door and said “Leave your thing in the car and bring your keys back.” I complied and she led me around again. This time she had me move some furniture and then the bell rang. She said, “I’m pressed for time today –go answer that – you remember your way.” I complied and met the first of the ladies at the door. She seemed happy to see me. I carried her stuff for her to the room. On and on. Then the ladies were all there and posing I was on and I was hard and I came and they called break and had me serve them all tea and I got hard again and I was back to posing. Then it was raining so they had me go get each of their cars and bring it to the front for them. The warm rain felt wonderful on my skin. Finally, they’d all left and she handed me my keys and some money and said goodbye.

Their sketches and photos of me were on the walls around the department and the pool party it was decided would be my coming out. They voted on whether I’d be allowed to wear anything and it was deemed that I would continue to be well shaved for the party and that I would be Lori’s slave, since the party was at her house. I was to be dropped off naked by Josylyn Friday night and to do whatever I was told by Lori to set-up the party and work for the day, serving all of the girls for the party and then clean-up afterwards. I would be under her total control. On Monday morning, she would bring to work in whatever she decided she wanted me to wear for the day.

That Friday, after being teased all day about my on-coming weekend of slavery, I had to work until after hours, when nearly everyone was gone except for Jacqie, Sue, Kim, Pat and Louise. I was terrified and turned on. They had me strip in Jaqcie’s office and all my clothes went into a bag which went into the filing cabinet in Josylyn’s office including my wallet and house keys. I stood naked in the middle of the office.

Then “Ok slave boy get that thing up” and as I started to masturbate. They yelled “stop” and Josylyn grabbed my dick and yanked and squeezed and shook it as she said “you aren’t allowed to touch yourself slave, don’t let Lori catch you doing that” as each of them grabbed my balls and wacked my ass. I was hard in a jiffy. Josylyn buzzed Jane “he’s ready.” She walked into the department and grabbed my stiff dick “Have great weekend slave boy – work hard. Maybe I’ll see you Sunday. Tonight I have date.” She’d pumped my dick with each word. Her words kicked me in the nuts. They had me walk around the inside of the building each second wondering if anyone else was working late. I was excited and terrified and then out to the deserted parking lot where I had to March to their cadence to Josylyn’s car with my stiff cock wagging and waving and then drive her as a Chaufer to Lori’s.

Each of them said good bye while grasping my stiff dick and squeezing as they warned me to be a good slave and then slapped my ass. Finally, I was sitting in Josylyn’s car and she grabbed my dick and said forward. If you cum in my car before we get to Lori’s I will fire you, tell her that you are unreliable, and leave you in the park. She said this gripping my 10” dick like a vise - so hard that it hurt and my need to cum subsided a little. Finally we got to Lori’s and I opened Josylyn’s door for her and she dragged me by my cock to the front door where she rang the door bell with my cockhead, commanded me to stay, and went back to her car. I was terrified of Lori, she was mean to me and always seemed to know how to humiliate me to the point of tears. No one answered the door. I stood at attention on her uncovered porch naked, shaved and hard on the verge of orgasm waiting as Josylyn left laughing loudly.

Suddenly, Lori opened the door wearing a blue and white cotton dress and pumps, looking demur and pretty. She slapped my face and yelled “what’s the matter with you, you’re only allowed at the service entrance!” and as she yelled she grabbed and twisted and shook my cock head with her fingers pinching it with her nails - my need to cum subsided a bit. She scraped the pre-cum from the tip of my dick and wiped it in my hair -”don’t drip.” Then she ordered me to walk around to the back of her house and went back inside slamming the door. Any fear I’d had was more than justified.

She had a large house at the end of culdasac in a development, There were several other houses on the culdasac. Standing on the porch I wondered if those people were home and if they saw me walking around her house naked and hard. I got to the back door by the garage and rang the bell again and she came to the door and let me in saying its about time - “now get in there boy you have work to do” Now spread your legs and bend over - you must be disciplined for your stupidity (I thought I already had been) She grabbed my balls with her left fist and started to spank my ass very hard with right hand. With each swat she yanked my balls to bring my ass back to meet her spank. My ass cheeks burned and my balls ached from her yanking. Finally, after what seemed an eternity, she stopped and told me to follow her and she led me to the kitchen where she told me fill some glasses with wine and to carry the tray and follow her. I did and we walked to her patio where there were several ladies that I’d never seen before sitting on the patio in lounge chairs near the pool. They were dressed in jeans and business suits. I was stunned and almost stumbled. Lori introduced me to the ladies as her new slave-boy explaining that I was trying to prove my usefulness. They approved and I was introduced to each one as I gave them their wine, as I did so each off them fondled my cock as if inspecting it. Several kissed it like a man would the hand of a beautiful woman. They were all dressed in business suits or casual- but-elegant-clothing. I felt very naked.

After I served her her wine, Lori told me to bend over and to the ladies said, “let’s see how well he picks up for me. She grabbed my balls with her fist again and motioned me forward, her grip was as tight as before and left me no room for play. She had her wine glass in her other hand and maneuvered me around her pool. I picked up any scrap of paper or twig... She teased me that she’d always had me by the balls and that I loved it and was just beginning to find out what it meant to be her slave. She pulled, twisted, yanked and squeezed my nuts all the way around the pool while periodically poking my exposed asshole with her thumb nail. My dick was stiff as a rail and aching to cum.

The door bell rang and Lori told me to go get it and if it was a guest to attend to their needs, and bring them back to the patio.

Her girlfriend dispensed my semen from my dick into each glass in front of each guest to her satisfaction one squirt or two, while allowing me the minimum of pleasure. Her new guest had the ability to dispense my cum without allowing me an orgasm. Upon completion of my usefulness she released me. I had the huge urge to jack- off to get some sort of orgasmic fulfillment, but they had me stand in service. My dick was still stiff and drooling and my balls ached from the sense of being filled, squeezed and emptied.

I kept getting demoted so that I became Shelly’s assistant and my uniform became a leather harness with rings and a buttplug assembly. I was kept shaved and dropped at the school whenever Amy and Josylyn agreed.

Jane had me get rid of my apartment and I was traded between her, Lori, Josylyn, Amy, and the others as a night or weekend houseboy. I was easy to trade since I had no luggage.


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