Memories of a Street Rat - 3. More Than A Trick

It was well into the first full summer of living on the streets and two months from my seventeenth birthday. Injuries I’d received on a job gone bad were finally healed up. A client at a cheap motel with an unexpected friend waiting in the room is always a risk and rarely ends well for me. It wasn’t the first time and certainly wouldn’t be the last something like that happened. Even being careful with what funds I had managed to save, I needing to earn some money, so it was back to how I had learned to survive. The warm weather afforded a chance to wear a little less. Nylon shorts were popular for their ease of access, while a pair of tight fitting shorts would attract attention for a different set of men. Both highlighted what was for sale in different ways. A form fitting tank top or an open side sleeveless muscle shirt usually rounded out my uniform.

I’d gotten good at finding small items of clothes that wouldn’t take up too much of the limited space in my backpack, yet be able to catch the eye of the men looking for someone like me. Having been in the store several times most of the workers recognized me. The women were polite but watched me carefully. I always thought it was thinking I’d steal something. The men were friendlier and more helpful. After browsing at one of the stores I frequented and finding a couple things I liked, I told one of the men I’d have to come back after I got some money. It wasn’t unusual for that to happened, but was the first time one of the men suggested that they could hold my purchase for a day or so until I came back.

A couple of my cruising spots were nearby and I figured I could find some trick to pay me so I didn’t have to touch my savings any more than I had recently. When I went into the changing room to try on something that I thought my customers would like, the curtain wasn’t fully closed. The worker got an eye full and wasn’t bashful about letting me see he was watching. He walked over to suggest a trade. Ten dollars in clothes was a little below my going rate, but I let him blow me for a few minutes. He was disappointed when I stopped him, but politely mentioned there would need to be a different exchange if I let him finish me off.

It became a regular thing when I needed new clothes at two of the thrift stores in town, with me sometimes trading my services for a couple items of clothes. One of the men didn’t mind buying some of my old clothes in the process. If there was no one else in one of those stores, the male workers were more than happy to assist me in trying things on. The more helpful guys tended to pick things that were tight and form fitting. At times I suspected they held items aside in the hopes I’d come in. They knew I was hustling and had no issue with it. I could have pulled money out of my savings before going into the store, but sometimes I was really just looking around to see what they had before I did.

******

Out on the street the uniform of the day was a muscle tank top, nylon shorts that showed well both front and back that the thrift store had helped me pick out, plus some well worn sneakers. Mid afternoon I was in the downtown area of Richmond. I’d had some luck there with men looking for fun during their lunch break. I noticed I’d caught the attention of a man in a nice business suit. His hair was perfectly styled without a single strand out of place. He was handsome and seemed like a definite step up from some of my usual customers. I was sweating in the summer heat and humidity as I leaned against the side of a building. The man walked past me twice and smiled both times; I smiled back. The third time he past I nodded and he tipped his head for me to follow. I figured, what the hell, and stayed a little ways behind him. He entered an office building and went to the elevator. By the time I caught up, he was holding the doors open for me.

He pushed a button for one of the upper floors and as soon as the doors closed, he grabbed my arm, leaned down and buried his face in my arm pit. I’d run out of deodorant the day before and hadn’t gotten around to buying any, so it was nothing but me that he smelled and apparently liked it. Before he pulled away, he ran his tongue through my pit. He straightened himself up and watched the elevator numbers climb without looking at me again.

When the elevator reached his floor he guided me to a door that he unlocked. It led to a plush office with a large wooden desk, an array of computer monitors sitting on it, and bookcases filled with books and awards. Off to one side sat a leather couch and a couple matching chairs in front of large windows with an impressive view of the city. He picked up his phone and told whoever was on the other end he was working on some project for the next couple hours and didn’t want to be disturbed. After hanging up, he went to one of the other doors and locked it.

He came back over to me and stood there. The man was ruggedly handsome and I guessed a little over six foot tall. The broad shoulders looked good under the tailored suit. Kind of the daddy type, but at my age a lot of guys qualify as the daddy type. Looks wise, he was the type of trick that I didn’t mind getting picked up by as long as he didn’t get out of control. When he didn’t seem to make any move, I took the initiative and lifted one of my arms again exposing my armpit to him since he liked it in the elevator. I had a feeling I knew his type based on his hesitation and figured it could be fun if I was right.

I glared at him and took control of the situation as my initial contempt for him seep into my tone. “You had no issue going for my armpit in the elevator, get over here and finish what you started.”

In an instant he bent over with his nose where he was told and was breathing in deep. All he did was inhale before letting out a little moan. I let him do this for a couple minutes before issuing my second order. “Taste it. One lick only though.”

He ran his tongue very slowly and methodically through the entire area in one continuous lick before pulling away.

“That’s the last taste you get until you show your gratitude for me allowing you lick the sweat out of my pit. There’s still another one you haven’t touched yet and a few other places I’m sure are sweaty.”

Even under his dark slacks, I could tell he was boned up. It didn’t really matter to me at the moment. This was business and I’d pretty much figured out what this customer wanted. He pulled out his wallet and took two bills which he promptly handed me. I pocketed the money with just the slightest glance at it and lifted both my arms, placing my hands on the back of my head. “Good boy, now get to work.”

“Thank you, Sir.”

I didn’t expect him to call me Sir, but there was a rush that went along with it. Kind of a power unto itself that I had over this man who I guessed to be at least twice my age and much larger. I had found a few men already that got off on being dominated. My size and age appeared to intensify their desire to submit. I found it was something I enjoyed as well as seemed to be good at. With this type of client there were fewer risks of me getting hurt and they tended to be more generous than the typical trick I’d deal with in a car, bathroom, or alley. He leaned into the other side that he hadn’t gotten to yet and inhaled my scent like he was checking fine cologne. With what he paid me, if he wanted to sniff my pits and smell any other part of my body for a while it was fine by me.

When I decided I wanted to feel his tongue instead of just his nose running through my pits, I gave him a simple command to lick. He spent the next half hour alternating between each side.

I finally pulled back from him and he actually whimpered his disappointment that I made him stop. I made a slow show of pulling off my muscle shirt and dropping it on the floor next to him. I walked over to the leather couch and sat in the middle with my legs spread wide. He picked up the shirt and folded it before approaching like a puppy and kneeling between my legs.

“Remove my shoes and socks.”

He leaned down and untied one shoe before pulling it off. Lifting it to his nose he inhaled deeply before running his tongue over the top of it. When he finished with the first shoe, he placed it on the coffee table behind him and did the same with the second one. Likewise with each sock, when he took them off, he would cover his nose with them and breathe in deeply. Picking up one of my feet off the floor, he looked up at me for permission. I maintained a disinterested look, but nodded as he smiled and began to run his tongue all over my foot while massaging it with his hands. I admit it felt damn good. He proceeded to the second foot when he felt the first was completely clean.

“Loose the jacket and shirt, but keep the tie on.”

He pulled off his jacket and laid it across one of the chairs before unbuttoning his shirt and placing it neatly with the jacket. The man had a nice chest that was covered in dark fur. It was obvious he worked out regularly.

“Now the pants. Keep your underwear and socks on.”

He stood to unclasped and unzipped his slacks as he toed off his dress shoes. Folding the slacks, he added them to the chair with his other clothes.

“Nice body, boy. I’m glad you don’t shave or trim your chest.”

“Thank you, Sir.”

“I could use a hand removing my shorts.”

He knelt between my legs again and gently reached out his hands. Raising his eyes slightly to mine, he waited until I nodded before reaching for the waist band. I lifted up enough that he could pull them down. All of his attention had gotten me excited, not that it took much at almost seventeen. He looked at me for permission on my boxer briefs that were bulging obscenely and I nodded again. When he had them off, he held them to his nose and inhaled a few times before setting them with the rest of my clothes.

Looking to me apprehensively he apologized. “I’m sorry I did that, Sir, without asking permission.”

“I’ll punish you later for that. You did that with my socks too. Right now, you have some more sweat to lick up.” With that, I leaned back on the couch and pulled my feet up onto it.

He got the idea of what I wanted him to do and smiled happily. “Yes, Sir. And thank you, Sir.”

I had to give him credit, he was very good with his tongue. He stayed clear of my shaft or since he hadn’t been given permission. With more deep inhales his tongue started on the skin of my crotch and soon worked under the balls, going as low as he could reach with the way I sat. It took a lot of effort on my part not to moan with pleasure. His tongue felt good on me as I relaxed and enjoyed the attention. Glancing at the clock on the wall and I noticed over an hour had passed since I’d arrived. Most jobs were over in ten minutes or less and I couldn’t wait to leave no matter the scene.

As good as his tongue felt to me and as willing as he was to keep going, I decided I wanted more, so I lowered my feet to the floor and issued my next order. “Suck it.”

He wasted no time and was doing an above average job of take it all. I had to admit that if all my clients were like this guy, I think I could actually enjoy whoring myself out. Unfortunately, he was the rare exception but when you find a unicorn you don’t question it. He worked diligently for a good half hour. It appeared he was a good judge of when I got close and would slow down, edging me until I grabbed his head and I let him swallow his prize. He nursed it, trying to get everything he could. When I didn’t go soft, I finally pulled him off and reached for the side pocket on my backpack where I kept condoms and lube.

“Loose the underwear and bend over the arm of the couch.”

“Yes Sir.”

The view of the front was as nice as the one of his butt. It seemed like he jumped into position with his ass up and waiting. I pulled the belt from his slacks and gave him ten good lashes spread across both cheeks. “That’s for sniffing my underwear and socks without permission.”

“Thank you for correcting my earlier actions, Sir.”

I tossed the belt aside, rolled on the condom, and lubed up. Since I’d recently cum, I took my time. We kept changing positions with him bent over the arm of the couch, doggy style on the floor, on his back, lying back on the couch, even him riding me. He stayed hard through all of it and to his credit, never reached for himself. When I finished I dropped the used rubber into the trash.

He looked down at it and then to me. “Sir, may I?”

I didn’t quite understand what he was asking for at first. “What is it you want, boy? Say it.”

“May I suck Sir’s load from the rubber?”

Something about him asking permission and the amount of time we’d already spent together made me think for a moment. “You only compensated me for one load.” I really didn’t expect any more from him and figured at most he’d tell me to fuck off now that I assumed we were done. He practically dove for his wallet and pulled out another bill that he laid on the table. I simply nodded and he reached into the trash bin to pull out what he wanted before sucking out its contents. That was a first for me, at least with me knowing about it.

“There’s a shower in the private bathroom if Sir wants to clean up. Would Sir allow his boy to get off though?”

“You have three minutes. If you’re not finished, you don’t get to cum today.”

I watched as he leaned back, running his hand up and down the shaft. He finished in two, covering his chest nicely. Surprise hit me that I kind of wished I’d helped him.

The shower was large enough for two, maybe three people. I’d never seen a private bathroom in an office before so had nothing to compare it to, but I’d also never seen an office like his before either. It seemed strange to me; nice as hell, but strange. He adjusted the temperature to what he thought I might like and waited for me to step in. “Would Sir allow me to wash him?”

I nodded and we stepped in. Between the sound of the water and the feel of it hitting me, after having gotten off twice I suddenly needed to take a leak badly. I figured with everything else he’d done so far I had nothing to lose and he might enjoy it. As he was reaching for the body wash and a sponge, I ordered him to kneel which he quickly did. I relaxed soon enough and he smiled as I sprayed him down, leaning in a few times to get a mouthful to swallow. Until I saw his reaction, I had been prepared to turn away from him. It was another odd feeling with this man of not wanting to degrade him, but add to his pleasure. The contempt I felt at the start of our meeting had changed to something I was unfamiliar with. Once I finished, he stayed kneeling as he began to wash my body from the feet up. After he stood, he massaged my shoulders and then lathered up my hair with shampoo. He finished by drying me off with a big fluffy towel that he then used on himself.

While we were getting dressed out in the office he looked almost bashful. “Sir, Thursday afternoons are usually my slowest time of the week if you would have any interest in coming back, I’d be grateful to see you again.”

“I’m sure we could work something out that’s agreeable.” Even though I did have some regulars, in all honesty I didn’t expect to see him again after I left.

It looked like he emptied what cash he had left in his wallet and pushed it into my front pocket with the other bills he had already given me. I hadn’t intended for him to pay me more at that time, but was merely suggesting future payments.

“I’ll be by next Thursday about the same time as we met today and knock on the door.” Testing the waters with the way he was acting I made a suggestion. “Between now and then, if you jack off at all while thinking about me, I expect you to put what you think’s appropriate in an envelope and have it waiting.”

“Yes, Sir. It would be my honor, Sir.”

“Also, if there’s a pair of new underwear and socks, I might let you keep the ones I’m wearing since you like the smell of them so much.”

“Thank you, Sir. I would be grateful for that.”

As I turned to head for the door, he handed me his card. “That’s my private line and my cell number, Sir. Just in case Sir has any additional orders for me. I’ll be happy to add to the envelope for each order given.”

“We’ll see. See you next Thursday, boy.”

******

I left and went straight to the bank. As I counted out what I had to deposit, I was shocked to see that he’d given me about five hundred dollars. It felt weird that during the entire exchange with him, I had never said a price on anything like I normally would, he just paid what he thought was appropriate and it was far more than I usually could make. I didn’t care that I was taking his money since he didn’t mind handing it over. Anytime I had asked for extra on something I just told him to give what he thought it was worth. It wasn’t worth me over analyzing and he seemed to get what he wanted and enjoyed himself. Surprisingly I actually enjoyed myself too. It made me smile thinking about having a trick whose dick jumped every time I gave him an order or he handed me more cash. I didn’t plan to abuse it, but figured it could be fun if there was actually a repeat and he could definitely afford it. I would have actually charged him less than I’d received just for how nice and attentive he was to me, if I’d gone by my normal rates.

I called him twice during the week and gave him a couple minor orders. I didn’t really think much about it, but if he could become a regular I wouldn’t object. When I arrived at his office the following Thursday, I knocked once and he quickly let me in. After I stepped inside he called someone to say he wasn’t to be disturbed. Setting on the coffee table was an envelope, a pack of new socks, underwear, and shoes. The shoes were nice, but not overboard thankfully.

I walked over and inspected his gifts. “I guess you get some underwear, socks, and shoes from me today. I also made sure not to wear deodorant again today.”

He appeared happy as he knelt before me and awaited permission to touch me.

I focused my gaze onto his eyes. “Before this goes any further, you’re to explain your desires here to me. What is it you want from this?”

“Yes, Sir. I’ve wanted to be dominated by a younger guy for a while. I’ve fantasized about guys like you being in control of me.”

“Okay. I like the sound of that and have no problem with that. What’s the deal with the cash? It’s more than most pay for a rent boy, not that I’m complaining, but you seem to get just as excited from being dominated as you do in paying.”

“The thought of Sir being so much younger, using me how you like and taking what you want from me turns me on big time. I almost came last week from Sir telling me I needed to pay more to suck the load out Sir’s used condom. Also every time I thought about Sir’s order if I jerked off thinking of you, it got me hard and I’d add something to the envelope as ordered.”

“Technically I didn’t take anything. I just suggested you compensate for what you were doing. So you want me to use you when I feel like it and how I feel like?”

“Yes, Sir. If it would please you, Sir.”

“Did you realize you were brining a rent boy up here last week when you were cruising me on the street?”

“No, Sir. I actually thought you were a courier at first that took off your shirt to cool down.”

“So, you thought you were just picking up some messenger off the street. Is that a regular thing for you?”

“Not regular, but it’s happened before. Some demand cash for me to blow them, others don’t. When Sir said I couldn’t lick his pits again ‘til I showed my gratitude I knew you were different and it was well worth it.” He glanced down at the floor for a moment. “You’re hot and seemed interested. It was too good to pass up when you nodded at me. When we got in the elevator, you smelled so hot and sexy in that small space. I just thought it would be quick sex until you gave your first order.”

“Just out of curiosity, how old do you think I am?”

“You look young, but I figured where you were possibly eighteen.”

“I’m sixteen. I’ll turn seventeen in September.” It was difficult to gauge his reaction and I was ready to leave if asked. “You were exceptionally nice to me and more than generous so I don’t want to cause you any trouble by me being underage. I’ll leave now and we can pretend this meeting never happened if that’s what you want.” Taking out his business card, I placed it on the table as a sign of good faith.

“I’ve only picked up legal age guys before. I knew you looked young from your size, but like I said, I thought or maybe convinced myself that you had to be eighteen. You looked so hot the way you were dressed and since you showed interest, I couldn’t resist trying. It’s difficult to find young guys into domination and you’re exceptionally good at it. With you being so much smaller than me and taking control the way you did, well you’re a fantasy come true.”

“Well, you seem to make a good boy and I’m happy to help you with your fantasies. I’m sure we can keep each other satisfied and help one another with our needs. So, I guess I’m just coming here to visit my uncle while you work. Does that sound about right, Uncle?”

“Thank you, Sir.”

“Now Uncle, if you’re going to kneel if front of me, it’s time to show your gratitude for me giving you my time before you get to lick out my pits again.”

******

This arrangement/relationship went on for almost three years; well after I’d walked away from hustling and living on the streets. Things eventually expanded to me meeting him at his house and I rarely went by his office unless he specifically asked for that. In time I opened up to him about my situation and how I got there. I stayed at his place on several rainy and cold winter nights. The first time or two I had him sleep on the floor while I took his bed, but I eventually allowed him to sleep with me as long as he was cuffed. In a short amount of time though, if I spent the night he’d cuddle with me after we played and it did feel good to be held. Several times he held me after a bad nightmare left me sweaty and shivering while he tried to sooth me back to sleep. Like a couple other important people in my life at that time, he tried to figure ways so I could legally live with him. As grateful as I was, I thought I’d be taking advantage of his kindness.

With my other clients, regulars or one timers, I remained detached from what we did and just went through the motions of sex, since it was strictly business. With him it was more almost from that first encounter. I did allow emotion to creep in and couldn’t deny I liked him. Unlike with my tricks, sex with him was always enjoyable and I started doing what I could to make sure he enjoyed it as much as he made sure I enjoyed it; and I did like dominating him as well. There was no way of stopping myself from breaking one of my major rules and allowed feelings to develop for someone. He helped me learn different aspects of domination and submission to enhance our sessions and introduced me to a few men who didn’t ask age related questions that guided and mentored me in becoming a better Dom.

Whenever I stopped by his office or house there would always be an envelope for me with money from anytime he used me as jerked off material between visits or from orders he received. I never looked in it while I was with him, but I’d find some way to reward him. Sometimes I walked out with the envelope in my pocket and other times I didn’t touch it; it depended on how my funds were doing at the time. He replaced my socks and underwear with new ones each time he saw me so he could keep the old ones. He was particularly fond of the jocks he’d buy me and loved the scent after I’d worn them for a while. When I started college he helped me out some and tried to get me to cut back on hours from three jobs I was working so I didn’t burn out. Even though I still was accepting money from him, he’d long since stopped being a client, instead a close friend.

After my last suicide attempt, he was among a group that helped me moving away from Richmond. I kept in contact with him after I left. Packages still arrive every other month with a new pair of shoes, several new jockstraps or occasionally some sexy underwear, and a pack of socks. In the box is always a return shipping label and I send him back the well used items. Well, he doesn’t get all the jockstraps returned. Cash is no longer exchanged, though he says at times that he wished I’d allow it. He jokes that I am still is favorite and only Sir. The envelope I once ordered him to add to every time he jerks off, he says he hasn’t stopped adding to, even if it’s no longer an envelope. There have been many times he told me if I return to Richmond he’d like to share his home with me. It’s become a joke between us that the account he holds for me is rightfully mine and he would be happy to send it to me if I ordered it. I just laugh and give him another order; usually that he’s not allowed to send me money. That hasn’t stopped him from buying me a gift from time to time.

I’ve asked him a few times if why he hadn’t found himself a full time Dom or someone else to use him like I did since he got such a sexual charge out of it. He tells me while he still finds the idea hot, I’m the only one he connected on that level with. And he doesn’t want anyone else to have that hold over him. He got his fantasy and became submissive to a teenager. While a few times he would have liked me to be more demanding about money or other orders, it was also a huge turn on for him to be told to gauge what he thought he should donate and risk being punished if it was too low; not that it ever happened... much. As for a full time Dom, he just says the right guy isn’t available.

He’s flown out several times to see me since I moved away from Richmond and it’s more like a date than anything else: nice restaurant, concert of some type, walking along the beach, lots of cuddling. Money is never discussed or hinted at in person since he’s happy that I’m out of that line of work. He knows Richmond has a lot of bad memories for me, especially with how many nightmares he’s held me through. As much as he wished I would, I made clear I couldn’t go back, even to have such a wonderful man as my boy or my partner. His life is tied too much to the Richmond area through his business to leave that area. He’s happy I’ve finally found peace and happiness in my life though.

Yes, he had sex with me while I was only sixteen. No matter if he thought I was legal age or not the first time, I’ll never consider him in the same category as the other tricks who picked me up during that time. His kindness, caring, and even love for me were never faked or used to take advantage of me. I still enjoy the exchange that goes with domination and submission and the guys I find that are up for that enjoy the skills I’ve learned because of him. Doing it for the mutual enjoyment of us both is far more rewarding than doing it for money. There’s a collar hanging on my wall with his tag on it. No one is allowed to wear that one but him. There are a few memories from the streets I can look back on with some fondness, and in the case of one trick who became one of my closest friends and someone I love, he’s one of those good memories.