Jessica

Chapter 4

Jessica made the arrangements for our trip to Orlando in her typically efficient manner. The weekday portion of the trip was mainly business, with Jessica, Ms. Gruer and I all staying in our respective separate rooms. I would report to one of the women's room for special training every evening after dinner, but return to my own room to sleep. The weekend, however, was different, as we all moved into a suite. One suite was certainly cheaper than three separates.

My two mistresses decided that the emphasis for this road trip was to be erection discipline. The primary tool they would use to train me were the women's bathing caps. Jessica told me that they had a tough time coming up with bathing caps even in a resort area like Orlando. She said to Ms. Gruer, "You know I never see anyone actually wearing these things. I wonder who really buys them, and what they really do with them."

Because of the scheduled meetings, I didn't get my normal Tuesday and Thursday "milking" and the women had no interest in masturbating me in the evening.

Jessica taught me how to meditate and do the male equivalent of Kegel exercises to get me erected. I soon learned how to get an adequate erection with very little coaching from my mistresses. They sent me to my room with instructions to practice. They told me that they could tell by my lack of performance if I failed, or if I got too carried away and jerked off.

I was a good boy. I didn't cheat. I wanted to please my mistresses. I could get myself up in under a minute and have my penis bobbing up and down in a nice rhythm. I even got to the point of producing precome without any external stimulation. I was so proud of myself.

It was on this trip that the women also taught me the subtle hand signal which meant, "stiffen up." I was to obey this signal any time they flashed it at me, even outside of "playtime." It became quite embarrassing when I was in the midst of a presentation and I'd see Ms. Gruer or Jessica give me the sign. Likewise, I learned never to wear tight-fitting or light colored slacks in the office. Standing up from a conference table with an obvious bulge and precome wet spot in your lap does not make a good impression on the rest of the staff.

The women taught me how to perform my hard-on magic in only one week. Our limited lunch hours at the conference were spent inspecting my penis to make sure I had a proper erection. To make sure that I was doing it properly, Jessica made me wear a rubber which she checked during our break times. She expected it to have a small quantity of the clear precome (but definitely not full of cloudy semen), and I didn't disappoint her. Jessica and Ms. Gruer supplemented my training during these rubber checks. They used a rubber ball to bring me to the edge of orgasm as a reminder if they felt I got lax.

However, the bathing caps were the real key to disciplining my erectile urges. Jessica used a very frilly and feminine cap for my erection training. First, she made a harness of sorts out of daisy-chained rubber bands. Then, she turned the cap inside out, and placed it over my cock and balls. Finally, she held the bathing cap in place by attaching the rubber band harness to the chin strap snaps and looping the harness around my waist and legs.

My penis nestled into the folds and flaps formed by the petals and leaves in the design of the cap. Just the thought of having my organ swathed in so much rubber was enough to cause it to jerk involuntarily. This caused it to burrow itself deeper into the folds and to rub against the inside of the cap. As it was gently massaged by the soft folds of rubber, it became more excited, and would twitch again.

I was caught in a continuous stimulus-response chain reaction which kept me in a constant state of arousal. It was never enough to make me ejaculate, but it did produce a steady stream of precome. Even after being "in the bag" for hours, I still had a steel-hard erection, and was ready to do (or have done to me) anything the women desired.

Ms. Gruer explained the importance of erection training, "As you know, we already control how and when you will ejaculate. We want complete control of everything leading up to ejaculation as well. It's your responsibility to have an erection on demand. A male shouldn't keep a woman waiting on such an important issue. Jessica and I shouldn't have to work for or wait for you to have a hard-on. Having an erection is merely one more way you can show your subservience to womankind. You have to be taught that relief from the erection is not automatic and you will only be allowed to come if you deserve it."

In addition to my evening erection training, the women also trained me to provide personal services. The most basic of these was giving massages. My penis spent every evening "in the bag" as I learned my other new skills.

When it came to massages, I remembered the seventh commandment of a male sexual slave, "My mistress' body is sacred. Only with my tongue, and at her bidding will I touch it. My body is hers to do with as she pleases." I appreciated the special dispensation my mistresses were allowing me.

Ms. Gruer lay naked on her stomach on the bed. Her body was not what I expected. Although short and slightly overweight, she wasn't fat. There was muscle on that frame, and although she didn't curve in and out in the proper female places, her body had a certain surprising appeal.

Unlike Jessica's body which was a fitting shrine to contain the goddess within, Ms. Gruer's body wasn't one built for graceful movement or speed. It was built for endurance and strength. She had a body that resembled a scaled-down version of a football lineman.

I had no idea how to give a woman a massage, and Jessica was quick to point this out.

"Always start at an extremity and work your way towards the heart." she instructed me. "Imagine how the muscle striations go, and move along the groove. Apply range of motion to the body parts."

I looked at her with a question on my face. She read it and answered me without my having to ask. "My mother was a nurse. I got to get into her anatomy books. What's even better, she worked in the 'penis palace,' as nurses are prone to call the urology ward. Hell, by the time I was 12 I knew more about penises than most men will ever know about this most sacred organ of theirs."

That explained a lot of things.

Jessica continued, "Now, so much for the history lesson. It's time for you to learn something new. Get over to the bed and take care of Agnes."

I started with Ms. Gruer's toes. I remembered the last time I licked and kissed them, and felt my organ stir within its rubber prison. I held each toe delicately in my fingers and gently flexed it several times before rotating it slowly in its socket. I used my thumbs and forefingers to strip the blood out of the veins in each toe, turning it white, and watched as the toe "pinked up" as the blood returned.

I moved up her foot, caressing all the toes as a unit one final time before working on both the arch and instep. Using both hands on one foot, I pumped her foot several times, squeezing down with my thumbs and up with my fingers. My fingertips found the grooves under her arch and I worked them from the outside to the center in a coordinated motion. I applied enough pressure to flex the bones in her foot without hurting her.

As I moved to her ankle, I supported it with one hand, and rotated and flexed the foot as a whole. I could feel the tendons in her foot contract and relax with the motion. There was nothing to do with her ankle but run my thumbs up ether side of them repeatedly, always putting pressure on the upstroke (towards the heart) as Jessica suggested.

By the time I finished the first foot, I could feel the trickling of precome in my penis. Tiny, almost imperceivable rivers of pleasure were running inside the shaft. The wetness they produced coated the rubber surrounding my organ. The head of my penis was being licked slowly with an almost below-the-threshold-of-feeling swab of a wet rubbery tongue.

After completing the whole procedure on the other foot, I moved up Ms. Gruer's calf. My first act was to lift the entire lower leg pivoting it at the knee, and bending it back on the upper part of her leg. This contracted the muscle, putting pressure on the veins and drained the blood that pooled there. I did this slowly a couple of times before returning it to the relaxed position.

I could feel the tightness in her muscled legs and identified the two muscles that constituted her surprisingly shapely calf. I placed my thumbs between them and hooked my fingers on the outside and ran my hands up the muscles collecting the flesh in my palms feeling her silky skin against mine.

I leaned over her body like a wash woman on her knees scrubbing a floor. In this position, the forward and back motion of my shoulders and torso as they rocked back and forth on my knees caused the underslung bathing cap to stroke up and down on my penis gently fucking the swollen organ. It was like having intercourse with a vagina that just barely encased my penis. No matter how I tried to twist and turn, it twisted and turned with me always tickling just one nerve ending at a time. I could never get the pressure I needed to stimulate an ejaculation, but I could never be free of the reminder that I was being sexually controlled.

I massaged her leg with a couple of long, slow, continuous strokes before varying my technique -- I started to pump and kneed the muscles in my hands. Ms. Gruer actually moaned with pleasure. My reward was a even tighter erection caused by the knowledge that I was pleasing her.

"Scratch her legs," Jessica commanded. I did, feeling the skin come alive and watched as it flushed with blood rushing to the surface in response to the stimulus.

I was surprised by what I found when I finally got to the back of Ms. Gruer's knees. The two tendons that run up either side of the back were extremely sensitive. She flinched and giggled as I touched the area inappropriately. "Careful, boy," Jessica admonished, "that's a very erogenous area you have there." The key here was to maintain a constant, steady pressure with the thumb and forefinger while using the other fingers to rake the muscle behind the knee.

I continued working my hands onward to the upper portion of her leg. I treated these with the same care as I administered to her calves except on a larger scale. I used both hands on each of the muscle groups here.

I finally got to worship Ms. Gruer's generously proportioned butt. The office joke was how she was such a hard ass. Nothing could be further from the truth! It was smooth and supple. The skin was white and soft to the touch. The mixture of firmness and tenderness that I found in my hands excited me.

"Stay away from her vagina and anus. We'll teach you the proper way to service them at some other time," Jessica warned me. I was disappointed in not being able to touch, but the look and faint aromas coming from these areas sent my penis burrowing into the cap even deeper. I had a cramp in my groin that was crying for release. Unlike a normal muscle cramp, for which I'd beg to have the muscles relax, I need this one to contract even further.

My mind was focused on these two holes from which future pleasure was promised. However, all I was allowed to do now was to use my fingers to radiate and stretch the skin outward, while alternately kneading her largest muscle with my hands. I spent a lot of time rubbing my palms against it and scratching it. I gave Ms.Gruer's bottom all the attention and adoration it deserved. I wanted to kiss and tongue it but I knew that it was not allowed.

"Come on, boy. We haven't got all night." I heard Jessica say. I was so lost in admiring Ms. Gruer's tush that it almost seemed if her voice came from a great distance in a dream. "Move onto her back," Jessica said, as I came to fuller consciousness.

The human back is a complex collection of muscles. There is a group of them that run vertically up the spinal column, and another symmetrical group that runs off either side enveloping the back of the ribs. I traced each one of them with care.

The back was another large skin area that deserved surface stimulation. So in addition to repeatedly tracing the muscles with my strong fingers, I scratched and rubbed it into life. Ms. Gruer sighed with relief. I was glad I was pleasing her.

I was totally distracted. It was difficult concentrating on working my hands on someone else's body when I wanted more than anything else to be able to touch mine. There's a certain point when a man masturbates when he has to quicken his stroke and drive through a barrier. It's like a runner coming up to the top of a hill. There's the drive to quicken the pace and get over the top. Adrenaline is called up. Muscles are urged to perform at better than 100%. Lungs gasp, and the heart pounds. The mind concentrates on managing the pain and tenseness as the body gives just a little more for the final effort. The rest of the world slips into a haze.

That's what the rubber bathing cap was doing to me. I was there, almost at the crest of the hill. Pushing. But like trying to run in a bad dream, I was never quite getting there.

I drifted out of this dream by the time I started working on Ms. Gruer's shoulder. I could provide a limited amount of range of motion for her shoulders by moving her arms and by placing my palm on her shoulder blade and pushing it. This procedure allowed me to move the arm gently in the socket. I massaged her muscular arms starting with her fingers and working towards the heart like I did with her lower extremities.

I spent over an hour working every muscle and tendon on Ms. Gruer's body. I was exhausted physically. My arms hurt. My hands were crampped. My reproductive system felt like it was run up and down a flight of stairs nonstop for the entire time. That's when Jessica handed me the lotion, and said, "Good dry run. Now let's do it for real."