The Trade: Hooks

"Pink. It suits you better," I said. I had been eyeing the kid for a while now, he wasn't very stealthy. He'd been examining panties for the past ten minutes.

"Oh, these aren't for me. They're for my girlfriend." He said, the nervous giggle did him in, there was no girlfriend. Not today, at least.

"She have the same hips and ass that you have?" I asked, hinting that I had seen him hold a pair or two up to himself when he thought no eyes were upon him. His face darkened and I knew then that he would be mine.

"I...um, yes." He lied, and horribly at that. I almost pitied him, as embarrassed as he was. I figured he was about ten years my junior, which would put him in his early twenties. His body seemed in good shape, but under the baggy hooded sweater and loose jeans, it was hard to tell.

"You're a bad liar," I laughed, "there's nothing to be embarrassed about, either. I'm Jim, by the way."

"Sam." He mumbled, brushing an unruly strand of sandy hair back over his ear. I remembered being his age, but always I was on the opposite side of the table. I should probably explain that better, I turn boys like Sam into sluts. I train them in the art of being a sissy, which in our area was lucrative. Sam was my next project, I could tell.

"Sam, I have a question for you," it was a well-rehearsed line, I'd used it a dozen times before, "you clearly like the thought of yourself in those panties. So, here's my question, if I buy you whatever panties, bras, skirts, anything from this section, will you try them on for me?"

He looked at me hesitantly, his scrunched nose and darting eyes were tells of his growing nerves. He hadn't said no though. I watched him mull it over, all the while I wolfishly dressed him in my mind. I went through the process of it in my head. The shaving, the makeup, clothes, and the deflowering. It was shocking how none of these future whores had ever experienced the real deal between their legs. But then again, it was part of their personality. Submissive. They never sought it out on their own.

"I suppose that would be okay." Came Sam's response. I smiled, probably too wide. I could practically feel my balls kick on, readying themselves for tonight.

"Wonderful, then start grabbing until you have a full outfit." I encouraged, patting his shoulder. In my head I drifted back to my own origin as a sissy lover. I was Sam's age, more outgoing, but only slightly. I must have been about twenty two. Yes, that sounds about right.

I was bored, horny, and had a buzz of tequila going. You could call it vengeance really, jilted by the loss of my then fiancée, whom left me for a coworker. He was a jock, I was an intellectual, and she was carefree and easily persuaded by pop culture trappings. I turned my attention to the internet, feeling self-destructive in my fog. I popped over to that seediest of ad sites, clicking on the "casual encounter" section. I wasn't sure what I wanted, so I just started looking.

Recently fascinated by my discovery of shemale porn, I started hovering around the ads that contained those luscious women with a little something extra. Most, if not all, were prostitutes. Hookers in the bad part of town, where I quite literally didn't want to be caught dead. You know the ones, where they weave their phone number into the ad in misspellings or use those code words like "generous" or "donation" to tell you they're not giving handouts.

I didn't feel like shelling out money on something I'd end up regretting for free. I decided to post an ad, because, why the fuck not? I gathered my thoughts and put together a semi coherent ad seeking the first time company of a shemale. I knew it wouldn't work, it was dumb to even think it would.

Four hours and two more tequila and sprites later I got a reply. The message was from Liz, a cross dresser who, while wasn't exactly what I asked for, was eager to show me a good first time. Liz included a photo, which my bleary eyes were pleased with. The heavily made up, but otherwise attractive face was framed by meticulously shaped hair. A simple black dress was all he, or she rather, wore.

Liz and I talked for nearly an hour over the computer, I sent a picture in return. Liz told me that I looked cute, my then shaggy hair and youthful face not yet lined from that extra decade I had now. Our conversation turned towards the sexual. Liz told me that she loved oral. What a coincidence, I thought, I loved getting my dick sucked. In reality I was a little more elegant in my reply and we eventually agreed to meet.

"How about these?" Sam asked. I snapped out of my reminiscence for the time being. Before me, in his outstretched arms were a pink tank top and miniature pleated skirt. I sized up his body type and nodded in agreement.

"Throw them in my basket, then." I said to my new plaything. Sam tossed the items along with a few others into my hand cart. I didn't look, I liked the surprise every now and then. "I'm going to finish my shopping, meet me at the exit in twenty minutes." I ordered. It was a test of obedience, part of my system.

I grabbed a few groceries, I hadn't come for much today. Sam was what I was truly excited about retrieving from this journey and as I approached the checkout I could see him. His lurking, huddled body sitting uncomfortably on a bench by the rest rooms. I absently dumped my basket out on the conveyer belt, using the little plastic bar to separate my items from the woman in front of me. She had a shit ton of groceries, and my mind lingered back to that first encounter, as it always did in times like this.

I sat there for about an hour, the evening light of late summer dwindled into long shadows. I had agreed to meet on my college campus of all places. I had graduated, but lived nearby. It also proved a good cover story for me, and my not wanting to meet Liz at my place. It was a new experience and I was dangerously over cautious.

I paced back and forth, walking the same stretch of sidewalk a dozen times. I finally told myself that this was stupid, and agreed to leave.

"Jimmy?" Came a husky voice. I could hear the faintest trace of whomever Liz was in everyday life, but it was near perfect in its feminine impersonation. I turned and saw her, thin legs wrapped in tight, low cut jeans. A slim, flat tummy exposed by her too small tee shirt. Flat chested, but not unusual for Liz's body type, if she were a woman. Her dark hair was pulled into a messy pony tail, her face was lightly made up in lip gloss and eye shadow.

"Yeah," I said, sobering up at the reality of my predicament, "Liz I take it?" She smiled and gave me a hug...

"Girlfriend's?" Asked the cashier as she scanned Sam's clothes through. I had spaced out again.

"No, they're mine." I replied with a smile. She laughed and told me to swipe my credit card. I had learned a long time ago that the best way to reply to buying women's clothes was with humor and confidence. Liz had taught me that.

"Hey." Sam muttered, he shuffled up to me like a puppy when I was checked out.

"Ready to try these on?" I grinned back at the blushing face that peaked up at me through his tangled locks. He nodded meekly and we strolled out to my car. Sam was starting to ease up around me, and I did my best to facilitate him in coming out of his shell. "I think you're going to have fun today." I could see him open up a little more beside me. I started the engine and pulled out of my spot in the parking lot.

"So, Sam," I started once we were on the road, "have you dressed up before?" I was positive that I knew the answer.

"Yeah." He said, but then after some thought elaborated, "my sister has some clothes that I wear from time to time." That was the typical response. It was always a sister away at college, a mother's panties mixed up in the wash, or the girlfriend's items left behind.

"I see, and you like it so much you want your own clothes." I made sure my tone was both accepting and persuasive. There was no question in my voice, Sam liked it.

"I guess so," came the weak response from the seat next to me, "it makes me feel..."

"Sexy?" I finished when he could not. We were almost home now, the ticking of my turn signal heightened my adrenaline.

"Yeah, I suppose." Sam said. It was an introspective tone with which he spoke, he was coming to terms with it, he liked the way a pair of panties cradled him.

"Don't worry, Sam. Today you're going to be a goddess." I assured as I pulled into my driveway. I shut off my car, snatched the bags and lead Sam to the door. He seemed uneasy about entering, and I related. The first step into this world is a scary one. He swallowed and stepped inside, I closed the door behind us.

"Nice place." He complimented awkwardly.

"I'll be blunt, Sam," I spoke, "I would love to see you in these clothes and I'm sure you would too, but I have to ask, how girly are you under those clothes?" This part was truly difficult. Sometimes the sissy sprang forth, other times it was a process of chipping away at the boyish exterior. Sam was a prize.

"What do you mean?" He asked, unsure of my question.

"Are you shaved? If so, how extensive? Do you take care of your skin? Any toenail polish, what are we working with?" I threw examples out and he nodded back at me, absorbing my questions.

"I have some hair, my pubes are shaved though," he added, "I use my sister's lotion on my body too." It was a fair head start.

"Would you be opposed to shaving yourself for this evening?" I asked, being polite.

"I'm not sure." He said, unsure of nothing but his own commitment to the idea him feeling sexy in women's clothing.

"Well, the bathroom is down the hall," I started, handing him the bag of clothes, "you can change in there. If you feel like shaving or primping, you're welcome to use the shower." He nodded and shuffled quickly towards the bathroom. My mind wandered, relaxing into a state of remembrance when I heard the shower start. After Liz and I met, we snuck into the science building. It was almost time for the last of the evening classes to let out, and we scrambled to find someplace secluded. We ended up in an empty lab room. The door had failed to shut properly and allowed us to sneak in undetected.

"It's fucking dark." Liz whispered to me, I was freaking out in my own silent way. I half expected everyone I had ever known to be hiding in the room with us, waiting to flip on the lights and catch me with a cross dresser. It was just us though.

"Yeah, it's kind of exciting." I whispered back, she found my hand when I spoke. She pulled me close to her, and snaked her hands around my waist. I did the same on instinct, and with her glossy lips centimeters from my own, she spoke.

"Very." Was all she said and planted a kiss on my lips. My mouth opened in time for her to dart her tongue across mine. I pushed back, our tongues wrestling. It wasn't long until my hands slid down over her petite ass, gripping it in handfuls over the denim. She liked it enough to nip at my lower lip playfully. Her fingers traced along the top of my boxers, coyly dipping deeper into the elastic waistband as they neared my now engorged rod. I could feel her growth too, straining against her skinny jeans, nuzzling against my thigh as we embraced.

She broke from our kiss, looking at me with a hunger that made a surge of blood shoot through my body. I could barely see her as she sank to her knees before me. My cock was out of my pants and in her mouth within a second. She took it to the base, washing its length in her mouth. Liz was a pro, and once she knew she could throat it easily she began to piston her mouth along my cock. Never in my life had I been sucked like that. She didn't change her rhythm, the quick thrusting bobs of her head were rough enough to loose strands of hair from their pony tail. I was already close, my balls were bursting whether I was ready or not.

"I'm going to cum!" I blurted out, she laughed at me with her mouth full of meat. I felt my knees give out and I sank back against the desk behind me. She kept it up, even as I sprayed my load into her mouth. I could feel the warm, sticky fluid adhering to my dick as she continued to coax every bit from me with her jackhammering lips. I was afraid she was going to suck the head from my shaft, but it remained intact.

When Liz was sated, she tipped her head back, slurping the dribble of cum that dangled from my cock. She opened her mouth and present the bubbling jizz to me, then turned and spat it all over the tile floor. I remember looking at it while she giggled. Someone was going to step in that in the morning.

"You got a nice cock, Jimmy." She said while she rose to her feet. She surprised me with another kiss, and hesitantly I allowed her to do so. It was my fall, the moment I was sent to the dark side. There was something about that second kiss, how forbidden it felt with the remnant of my musk on her tongue. I would have kissed her like that for hours.

The shower had shut off a while ago, and I now heard the creaking of the bathroom door as it opened. Again I came to the present, eager to see what Sam was able to accomplish on his own. There in the hallway I saw him peak his head, his hair had been straightened. His shaggy mess ironed and sprayed into a modest but girlish style. I was seeing a side of Sam that nobody had before, Samantha

The rest of Samantha slid from the door. Black, knee high socks encased her smooth legs. The milky skin of her thighs stood out between the socks and the skirt which only stopped an inch or so below Samantha's bottom. Her pink shirt clung tightly to her torso, outlining the bra she had on underneath.

"Beautiful!" I spoke breathlessly. Samantha smiled, that same timid smile I had been getting from her counterpart. There was still some of him left to remove, but for Samantha's first emergence outside of the solitude of Sam's room, it was a good start.

She mumbled a thanks while meekly brushing back her bangs. I held out my finger and motioned for her to approach me. She did, I was impressed with how quickly she responded to my request. Her personality was that of innocence and modesty, a great combination for a sissy to have. It made for a relatively pleasing experience for the master.

"Turn around for me," I said when she was directly in front of me. Samantha gave a twirl, her skirt fanning as she did and allowing me the pleasure of viewing the pink cotton panties that she had on now. "Very pretty, Samantha." I called her that, knowing that it had to be what Sam called this persona. I was right, and she paused when I called her that.

She looked up at me, her blue eyes tinged with lust. I wanted to kiss her, feel the gasp of shock as she felt the lips of a man against hers, but it wasn't yet time for that. I wanted to feel that creamy skin grinding against me, explore her body, but it was too soon. I restrained myself. Now it was time for the hook.

"It was a pleasure to meet you, Samantha." I said, giving a short bow, "but I said that I would look, and I don't want to go back on my word. So look is all I will do." I could see a little relief in Sam, but underneath I saw disappointment in Samantha. "If you could be so kind, my dear, I'd like to take Sam back to his car now."

The moment was almost painful, having to watch this beautiful creature recede back into the form of a boy, hidden beneath layers of denim and cotton. The hook was almost set though, and I'd done this long enough now, I knew I'd be seeing Samantha again.

I escorted Sam back to the parking lot, pulling up next to his car when he pointed it out to me. He was silent for the whole ride back. No doubt arguing with Samantha in his brain. He thanked me one last time as he opened the car door. I responded by handing him my business card and smiling. I saw him look at it when he closed the door. The first step was complete. I drove back home, allowing myself to finish the thoughts that had plagued me all day.

My evening with Liz concluded with us parting ways. We had to sneak out of the science building together, which proved amusing. When we made it outside, she gave me one last kiss. I felt her slip a hand into my pocket and retrieve my phone. She put in her number and slipped it back in, without a word. With a wink she was gone.

When I got home from dropping Sam/Samantha off, I pulled my phone from my pocket. I couldn't help but grin when I dialed her number, "Hey, I got us a new one. No, I used the card. It always does, talk to you then."