Convenient Arrangement

Author's Notes

Before reading this story please be aware that that some people would label this work as obscene and pornographic in nature. It contains several themes including transgendered, homosexual and lesbian issues in addition to graphic sexual descriptions.

To make the action flow more freely and the stories light-hearted, I have taken a socially naïve approach and have not included the usual protections that intelligent people would choose such as condoms, birth control and out safeguards against sexually transmitted diseases. Such risky behavior as those exhibited by the characters of this story should not be followed.

If any of these topics make you uncomfortable please look elsewhere.

If this sounds like a story you might find interesting, enjoy.

CHAPTER 1

It had been nearly a month since I had visited a few local clothing stores a few miles from my home. Business had been predictably slow on that wet and rainy Friday filled with cold drizzle. I parked in one darkened corner of the lot and sat staring at my reflection in the rearview mirror for several seconds asking myself why I was doing it yet. The shopping spree, where interesting enough I rarely fought up the courage to stand in line and purchase something, had become something of a monthly ritual for me. The reflection looking back at me wasn't one I was used to seeing but it was an exciting site. The brownish bangs hanging down near my glass frames highlighted my auburn eyes that stared out from a light combination of mascara and eye shadow. My roundish face had a touch of foundation and powder and featured a pair of pouty lips adorned in a light red lipstick. It was an attractive face but it wasn't going to draw any undue attention. The wide shoulders I possessed were draped under a dress coat made higher by shoulder pads that hopefully downplayed their size. Rounding off the look was a dress skirt, nylons in matching navy blue and a pair of reasonable pumps featuring heals that would create that delicious clacking sound against the concrete and hard linoleum I knew would be waiting for me inside if I ever made it to the building.

There was a family crawling into their van between me and the store and within a minute the had pulled away, their headlights illuminating my car as they swung past. The parking lot, for all intents and purposes was a ghost town. I took one more look in the mirror, felt my heart begin to hammer at a quickening pace and felt a strong erection swelling under the resisting pad of material I had stuffed inside my girdle and panties. I rubbed it with a hand, adorned with press on nails featuring a French manicured style, making sure everything was in place and that the hard bulge wouldn't be noticeable under my skirt. The double-breasted style of my coat hung low enough to hide anything and after checking the area once more I unlocked the door, grabbed my purse and stepped from the warmth and safety of my car into the cool, damp evening.

Making sure I had my keys safely zipped away in my purse I pushed the door shut, signaling the next stage of my trip. I strolled towards the bright lights of the first store, noticing nervously that several teens were lingering near the entrance, probably waiting for a ride. If everything went as planned, there wouldn't notice anything unusual about me and I'd slip inside without issue and spend a half hour or so lingering around the various departments, looking for something nice to buy myself.

It was one of the rare times, feeling particular courageous, that I plucked several items from the racks and slipped inside the dressing room to try on the clothes and take a few minutes to catch my breath as the adrenaline continued to course through my veins. Besides the women's restroom, there was no more inner sanctum than the dressing room and I had invaded it, not to disrupt or cause an issue but to simply relax for a minute and enjoy trying to be the woman that I appeared to be in the mirror. I had only come in here twice before and managed to slip in and out without any company but that night, a month ago, two other women who apparently knew each other, had come in just after me and were chatting and trying on clothes in two other stalls nearby.

They apparently didn't like the lighting in the changing stall or the smallish mirror and were busy swapping clothes and checking out their appearance in the larger, well lit mirror in the main hall of the changing area. I concentrated on my last few items, lingering with each, hoping the pair would complete their tasks, make their decisions and allow me an exit unseen. I had finished my own selection and had gotten dressed again while the pair continued to prance about in front of the mirror that I could see through the crack in the door of my stall.

I studied the pair as they went through bathing suits, skirts, dresses and a handful of other items, watching them lustfully from the safety of my stall. I could hear them getting dressed and undressed only ten feet away, perfect strangers. The erection that had grown to its full extent when I was strolling through the store because I was living life, if only for a short while, as a woman, was now throbbing when it added the additional excitement next door. I made some noise to let them know that I was around and continued to stare in jealousy at their ability to eat, live and work as women, something that appealed to me since my earliest childhood memory.

With my gear in hand and purse over my shoulder I finally determined that I had lingered long enough and after checking my appearance one last time I grasped the flimsy handle with my shaking hand and waited until each had returned to their respective stalls at the same time to slip quietly out and back towards the store. As luck would have it, another woman, a store employee, passed into the dressing room just as I stepped out of the dressing room but she made no discernable effort to look at me as she passed by.

I had decided the long line at the register was going too slow for my comfort and put back the items in their rightful place. I strolled from the store without incident, I thought, and returned to the safety of my car, the smell of adrenaline continuing to course from my pores over the scent of perfume I was wearing.

That was a month ago tonight.

Two weeks ago tonight I had arrived home to find my mail dutifully waiting for me. I had worked late, capping off another work week, and tossed a frozen dinner in the microwave as I sorted through it. Bills, coupons, newspapers; the usual stuff. Most ended up in the trash but a non-descript, letter sized envelope had caught my eye. I ripped it open as the cheese on my dinner entrée continued to bubble, half expecting another useless junk mail offer to tumble out.

I was wrong.

As I stared at the top page it's meaning came to me, the ding of the microwave punctuating the point of revelation. There were two pictures printed on the page, both in landscape layout. It wasn't high tech printing but something you'd see on any office laser printer. Neither picture was particularly sharp but I could tell from the background, the parking lot slick with moisture, that they were pictures of me emerging from the store a month earlier. It could have been anyone really but the one shot showed a woman climbing into the drivers seat of my car, the plate visible, if somewhat fuzzy. I was usually very observant while out dressed as a woman but no one watching me had caught my eye.

I had swallowed hard, ignoring my dinner for the moment and flipped through the other two sheets, featuring four more shots of me in various spots in the store that night. All were late in the trip, following the dressing room but they were me. If anyone had asked I could have easily denied that it was me or that they had been worked over with software but it was clear that someone had known it wasn't a typical woman shopping that night. The drive home had been uneventful and with traffic so thin it was clear that no one had followed me home. They either knew me or had access to the DMV computers and had tracked me down through my license plate. In either case, it appeared my secret, with who I had shared with only a small group of friends, was going to be exposed to the world in short order. I had never thought my cross dressing would be public knowledge but it appeared that the choice was no longer mine. I didn't have a lot of money but I had a job and reputation to protect and someone thought they had something to blackmail me with. It would come out sooner than later so I had steeled myself against this fact and was prepared to turn down any offer I knew might be forthcoming.

Then an email had arrived a few days later, not at my home account but at work and faced with the dilemma I was torn at whether or not I wanted my secret exposed. It had seemed like an easy decision when the letter had arrived but as I sat at my desk at work, surrounded by a sea of cubicles, with the blatantly clear email open on the screen I had second thoughts.

Did you like the pictures I sent? They weren't that good I admit but it's clear it was you sashaying around that store with your perky fake breasts and that padded ass of yours. I really liked the one of you coming out of the changing room. Priceless! Now here's what you're going to do. You're going to get all dressed up, wearing that cute little red dress of yours and matching stilettos and you're going to drive over to Hine's Park this Saturday at noon and go for a little stroll

That was it. I tried to reply to the email, wanting more information but the rejection came back in a few seconds. Apparently the sender was covering their track or didn't want to hear back from me. There wasn't going to be any type of negotiation.

Despite the circumstances in which I found myself I could feel my cock growing inside my shorts and my breathing and pulse both racing. The rush of adrenaline was striking again as I stood there staring at my reflection, manicured hands smoothing the red material stretched across my artificially curving frame.

It was Saturday. Finally Saturday. I didn't know what to expect but it had been a long week of distraction and no matter how it turned out it was finally coming to an end. I checked the windows of my house for traffic and didn't see any immediate neighbors out so I opened my garage and drove down my street, not bothering to wave to the few people who I knew were out working in the yard. I didn't get out much during the day and strolling out in the open daylight was rare. The only saving grace I found was that the cool, overcast day seemed to have kept most people away from the park. There were few trees or buildings and the one path around the pond was wide open and the few groups in the park couldn't be avoided.

I had actually left late and it was noon, either by the digital clock in my car or the feminine watch I had strapped to my wrist. I took one look around, not really expecting to see anyone waiting for me, but studied the area nonetheless. I normally would have chickened out under such circumstances but given the conditions of my invite I climbed from the car, purse in hand and began walking the path away from my car, trying to keep my shaking legs from walking too quickly. The high heels I wore weren't made for long strolls so their height kept my speed at a leisurely pace.

No one seemed to be noticing me and the occasional jogger or two passed without notice. I hadn't spotted anyone in the area and upon reaching the back area I spied a rest area with two restrooms. I could feel my cock pumped up inside my panties and the strain was distracting. I was pondering taking a quick break inside to give it a few strokes as the pressure continued to grow when someone stepped from the men's room opening and waved me towards him. I looked around but no one else was nearby. There were homes across the street with people out so my immediate safety probably wasn't an issue.

When I turned my gaze back the individual, obviously a man who had on a baseball cap and sunglasses, t-shirt and jeans was gone. Did I know him? I didn't think so but I had looked away too quickly and he had disappeared back inside before I thought to study him further.

Steeling myself with a deep breath I strolled forward on the uneven concrete and after taking one last look around I moved into the entrance and around the concrete block wall. The bathroom itself wasn't that large, two aluminum sinks, two urinals and three stalls.

"Glad you could make it." The man said, studying me in the mirror.

As strange as it sounded, I felt out of place in the men's room at the moment, spying my reflection above his body, in the same mirror.

I nodded, not sure what I would say.

"Take off your coat and stay a while."

I set my purse on the wooden bench beside me near the exit to the bathroom and complied, slipping out of the long jacket I had on. Not sure what to do I tossed it on my purse and stood there as he washed his hands. He probably wasn't a doctor going into surgery in the next five minutes but he took his sweet time, finally drying them using the hand dryer mounted to the wall.

"So." He said, finally turning towards me and stepping closer. "You came."

I nodded again, hearing a couple people entering the women's bathroom on the other side of the wall, the area above the wall open.

"Got my emails too?"

"I tried to reply back." I said, trying to sound feminine. "But they were rejected."

He nodded knowingly.

"Have a seat Jim. Sorry I have to call you Jim. I don't know what name you're using when you're all dressed up." He said, motioning to the dress I had on.

By now, any company I had next door had left.

"Jasmine." I said.

"Jasmine." He replied, savoring the word as though tasting it. "I like it. Seems to fit you."

I smiled weakly, some how both complimented and disgusted.

"Now have a seat . . . Jasmine and I'll explain how we're going to proceed."

I did as I was told and sat down on my coat, purse at my side. He stepped closer to me, only a foot between us. I looked up at him from my seated position, hands resting on the erection that was still happening between my legs.

"You're going to do exactly as I say and then we're just going to go our separate ways, got it?"

I didn't but nodded anyway.

"That's a good girl. Now reach up and undo my belt."

I must have hesitated too long because he spoke again, a new edge to his voice.

"You want to still be here when company comes in?" he asked, nodding to the opening to the men's room. "Or maybe you'd rather do this on the picnic table outside?"

The threat was perfectly clear and my hands began to move as though on their own.

After undoing his belt I didn't stop there. My long finger nails made undoing the latch on his jean difficult but within seconds it was undone and his zipper down.

"Never did this before." I heard him ask from above me.

I shook my head, working the jeans down his legs until they dropped at his feet. Sounds could be heard outside and I paused, wondering if were about to be interrupted and how I would react to it. A few seconds later I could hear the stall, again in the women's room next door, closing.

"Keep at it Jasmine."

I did as I was told as reached up to his briefs, the sizable cock fully erect under the thin, white material. I pulled at the elastic at his waist and unsheathed his erection when his underwear dropped onto his jeans. Following through I reached up and stroked it gently, face to face with something I had always wondered about.

"C'mon and suck it already. Not going to suck itself."

He edged forward and I had my back to a wall both physically and psychologically.

Licking my painted lips I leaned forward and tentatively wrapped them around his shaft, feeling his flesh on my lips. I pushed them down further and could feel his cock on my tongue, sliding on the roof of my mouth, pushing against the insides of my cheeks. My saliva began to flow as I pulled back and repeated the cycle, going further and further as I became accustomed to the new sensation.

"You're a natural Jasmine!" he moaned, helping me along with a pair of hands on the back of my head. He had stepped a few inches further, his legs cradled between my wide open thighs, face buried in his hairy crotch.

"Oh yeah." He continued, my jaw beginning to feel sore from the activity. I could feel the first few drops of saliva forming on my chin, dropping into my lap, caught by the hem of my dress.

My left hand continued to stroke his cock as my right moved up under his balls and stroked them gently, knowing how good it felt.

"That's it girl. I guess having a cock makes you privy to knowing how to handle it properly. Should introduce you to my girlfriend who could use a few tips!"

I was in automatic mode now, my brain wheeling from the fact that I was seated in a public restroom three miles from home giving a blowjob to a complete stranger who was toying with my life.

We had been at it for a couple of minutes, he voice raising every so often as he continued to waver in unison to my own moves when I heard, not saw, activity around us. I open my eyes and although nearly my entire field of vision was filled with a close up view of his crotch, I noticed movement off to my right.

"Don't stop." He commanded, sensing a change in the air.

Two men, thankfully no children to be seen, were standing at the urinals, relieving themselves. They were both looking over their shoulders at us as I continued so suck and stroke the cock in front of me. Laughing, they flushed the urinals and stepped to the sinks continuing to watch in the mirror, their eyes matching my stare through the mirror. They had no idea that I was a man, which may or may not have turned them off, but the lust in their smiles was easily read. It was clear that both were fully erect as they walk by us again, one even stroking himself as he exited.

We were alone again. I was hoping they hadn't done anything like call the police. The indignity would have been more than what I could have withstood but on the other hand, I'd know who this man inside me was and that would be a step up on getting out of this situation I found myself.

Just as I was beginning to wonder how long this would go on, and how much more my jaw would take of the abuse, I could feel his tight body stiffen further and for the first time the thought of what was coming struck me. I tried to back up but his hands held me in place and his hips began to thrust hard, his cock pushing more forcefully into my mouth. I was wondering what I could do just has I felt the first explosion of hot cum into the back of my throat, the first wave inundated by following waves of the sticky fluid. My reflexes kicked in automatically and the muscles in my neck began swallowing his seed until finally he slowed and stopped, hands dropping from the back of my head.

He exhaled heavily as I pulled back and let his cock fall from tired lips, a string of semen dropping across my chin. I could still taste him in my mouth as I did, without provocation, reached down and began dressing him again until finally the belt was tightened back in place.

I sat there again, hands in my lap, my own large erection still swollen from the events that just transpired. It had been revolting yet delicious in the same moment, believing I had done it against my will. Once the guilt was removed, I was able to do it and silently enjoy it, even the 'interruption' of the two men heightening my duty.

"Wait here for two minutes and then you're free to go." He commanded and stepped from the rest room.

I sat there for a few seconds before I realized I didn't know if he meant free to go or free from his blackmail now that I had done what he wanted. I stood up on wobbly knees and took a step towards the exit before I realized he could be watching; waiting. Best not upset things now that I had serviced him and he seemed pleased.