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Strapped For Cash (Or How I Became A Sugar Boy!)

"How a client became my number one"

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Competition Entry: Sporty Sex Stories
My name is Mark. I had set out for college to be an orthopedic surgeon. Somewhere in my sophomore year, I realized there was no way that was going to happen. I switched gears to physical therapist, but that soon failed too. No one had told me that I just didn't have the brains for either. Still wanting to get into something to help people physically, I got my massage therapy certification and personal trainer certs. It turned out this was more my speed, plus I loved both! But I obviously had a lot of school debt.

I had been working in a local gym for a while, doing a few massages (turns out not a lot of people are comfortable with a guy therapist!), but the personal training was going pretty well. One day I see a fairly fit, slightly older guy on a machine with terrible form. I went over to him and introduced myself, and gave him a few tips on the proper form for that machine.

A little while later I was sitting at the trainers desk thinking about my own work out. I was always in good shape, but I had gotten in phenomenal shape while working at the gym. The bad form guy came over.

"My name is Tom, and I just wanted to thank you for the help."

"No problem, it is what I am here for," I replied.

"I think that I really need help with everything, can I schedule a training session with you?" Tom asked.

"Absolutely!" I said, I needed some cash! We set things up for the next day, turns out he was very motivated.

The next day, Tom came in and we started with the interview to find some history and set goals.

"So tell me about yourself, what do you want to get out of your workouts?" I asked.

"I own a business in town, and I realized the stress and workload were killing me. After it ruined my marriage, I realized I had to change. I hired another manager to give me some help and now I am here. As for goals, I tell people that I want to get healthy but in reality, I want to look like you!" Tom said smiling.

"Well thank you!" I said, slightly blushing. We laid out a training plan and got to work.

Over the next several weeks, Tom was motivated. Because of his business, all of our sessions were either early (Five am) or late (Nine pm).

One night, I had just finished teaching a spin class and was going to get changed for Tom when he got there early.

"Mark, I gotta admit, I can't do it tonight. I am tired and sore, and just no energy," Tom said looking rather embarrassed.

"No worries at all, it happens. Have you ever gotten massages? They can really help with muscle recovery, " I said, trying to drum up more business.

"I never have. I guess I was always a little embarrassed to have a stranger touching me. I am not sure I could handle getting a boner while someone was massaging me," he admitted.

"Well, I am not a stranger! And as for erections, they are actually common to happen with relaxation and getting the increased blood flow from massage. Besides, it wouldn't be something new for me to see" I said, realizing the last part might have come across wrong.

Tom said why not, and we went back to one of the massage rooms.

"I have to apologize, I am kinda hot and sweaty from the spin class," I would normally get cleaned up.

"Don't even worry about it, I like the smell of sweat, it motivated me for the gym. Besides, you look cute in those tight shorts," Tom said mockingly.

I didn't think anything about the comment, we had gotten to know each other enough to joke around.

I gave him a good therapeutic massage and when we were done, he said that he felt great!

"What is a normal tip? Tom asked.

"Ten bucks is pretty standard," I said.

Tom pulled out a twenty, "That was worth more than ten!"

The next few weeks, Tom was in four or five times a week for training and at least twice for massage.

One night, he came in for a massage. I had just finished a spin class again and the air conditioner had just gone out, so it was getting hot. I told him we could reschedule if he wanted but he said he really needed it.

We went into the room, and as I was getting ready to leave so he could get undressed, he just started to strip down naked and hopped on the table. He had gotten into pretty good shape over the weeks from my help.

"We have nothing to hide anymore," he said.

"Well you are looking great anyway, you certainly don't have anything to worry about. I am going to use a towel over your junk since it is so hot, " I said. I oddly realized I was slightly turned on!

As I was massaging him, I could see more of him than ever. I was getting really hot though.

"I am dying here, do you mind if I take my shirt off? I asked. I would never ask that with any other client.

"Not at all! I actually love looking at your body, it gave me motivation!" Tom said.

I took my shirt off, so all that I had on were short tight cycling shorts. I continued with the massage, and when it was time for him to flip over, I took the towel off but got a good view of his ass and cock as he turned. He was getting semi hard.

I massaged his pecs, and then moved to his quads. I was rubbing his thighs all the way up to the connections to his abdomin with long slow rubs. He started to give little moans.

"OMG, that feels so good!" he said with a moan.

I started to rub the sides of his abdominal muscles slowly and slightly enticingly. I started at the top of his abs, and slowly rubbed down to his inner thighs. I could see under the towel that he had a full on erection at this point.

"Sorry about that. You found what I really need, I haven't gotten laid in months! Is there anything you can do about that?" Tom asked. I looked at him and he had a hopeful smile on his face. I didn't say anything, so he pulled the towel away revealing his rock hard eight inch cock.

I was particularly strapped for cash this week, so I took a chance at getting a big tip. I started cupping his balls. I started massaging his taint and balls together, and with the other hand started lightly rubbing the length of his shaft. I gripped his cock and played with his head with my thumb, then started stroking his shaft. Within seconds, I could feel his balls start to tighten followed by streams of cum shooting out of his cock.

"Fuuuuuuuccckkk!", Tom moaned.

After he had calmed down, I got the towel and cleaned him up.

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As he was leaving, he slipped me two Fifties.

"There is more where that came if you want," Tom said as leaving. Oh, I wanted! I realized that I had a semi-hard on over the whole thing. I had never done anything with a guy, and this happened so fast. It was a turn on!

We went like this for a few weeks. Hard workouts, massages, and hand jobs.

One day, Tom came in for a late massage. I came into the room and he was already naked on the bed. I glanced over at the table and saw three one-hundred dollar bills! I looked at Tom with a question on my face.

"I was hoping for a little more than a hand job," Tom said with a worried look that he might have crossed the line. I needed the money, and I have to admit the entire experience had been hot so far.

"Okay," I said. Tom smiled and laid down.

I proceeded with the massage. The whole time, Tom had a hard on. As I was rubbing his abs, pre cum was oozing out of his cock. I figured that I might as well just jump on in! I started massaging his balls and taint again. I licked the pre cum off his cock and abs and could feel his whole body react. I was amazed that it actually tasted really good. I took his cock head in my mouth and swirled my tongue around it. I continued massaging his taint and balls and slid another finger along his ass. His body rose to my mouth and his cock slid further in my mouth. I had no idea that I was going to enjoy this so much. His cock was big and hard, but velvety smooth. I bobbed up and down on his cock. I pulled it out and smelled the deep musky scent. I had a raging hard on myself at this point. I took his cock to the back of my throat, and without even really trying, his cock slid down my throat till my nose was in his balls!

"Oh fuck," Tom exclaimed. He started raising his hips to fuck my throat. He held onto my head and didn't let me move as he slid his cock in and out of my hungry throat. I could feel him tensing up and he picked up the pace. He thrust his cock completely down my throat as streams of cum were sent deep into me. My eyes were streaming tears by now, but I didn't care. He let me go and slid his cock out. I was gasping for breath but at the same time didn't want it to end.

"Dude, that was amazing! That is the hottest thing that I ever had,'" Tom proclaimed.

"Honestly, me too!" I said with some astonishment!.

He gave me a little kiss on the lips. "See you next time!" he said as he left.

I couldn't believe what I had just done, but then I looked at the three bills and smiled.

Tom had to miss a week for a conference he attended. I admit I was totally horny while he was gone, wanting another experience.

He got back and came over immediately. I was all prepared for another hot massage and blow job.

Tom came in and had weird look on his face.

"What's up?" I asked.

"Are you cool with what we did, or do you want to make more?" he asked.

"How much more?" I asked

He pulled out five one-hundred dollar bills. I knew what that meant. To be honest, I was horny already, but the thought sent me into over drive. My cock got rock hard in my cycling shorts. Tom noticed. I took the bills from him and went to put them on the table. Tom followed me and came up behind me. He put his hands on my hips and pressed his body up against my back. I felt electricity going thru me. I could feel his hard cock thru the shorts. Tom took off my shirt and pulled my shorts down. This was the first time I was naked for him. I turned around and took his shirt off. I got on my knees and pulled his shorts over his full eight inches. I took his cock in my mouth and sucked him deep. He stood there and looked down on my as I sucked on his cock.

Tom motioned me to get up. I grabbed some of my massage oil and coated his cock with it. I handed him the bottle and turned around and leaned on the table. He dripped the oil all over my back and started rubbing it all over. He dripped more in my ass crack, and my hole. He started tracing his finger around my hole, and slowly inserted a finger, then two. I breathed in deeply, this was the first my ass had been entered. He slowly worked his two fingers around until my ass loosened, then he inserted a third. I sucked in again. He had obviously done this before, because he knew how to get things ready.

He pulled his fingers out and put more oil on his cock. I knew what was about to happen. He ran his cock head over my hole a few times, then slowly started entering. His cock was a lot bigger than three fingers and all the air got sucked out of me as his cock entered my ass. He stopped for a minute and let me catch my breath.

"You ok?" Tom asked.

"Fuck me," was my only response!

Tom gripped my hips and started to slowly enter all the way. I could feel his entire cock in me and I felt on fire. The pain was so amazingly good! I looked down and saw pre cum gushing out of my cock. Tom kept his grip on my hips and started thrusting his cock deep in me. He pushed me against the table and I laid my body on the table so he had full access to my ass. He started pounding me into the table. I couldn't believe the electric feelings all through my body.

He laid down on me so his weight was on my back. He slowly ground his hips and cock into me. He was grinding me against the bed, making my cock get more and more stimulated. He stood back up and gripped my hips again and started pounding my ass hard. I could tell he was getting ready to cum. Before he did, I felt a huge heat growing in my groin and all of a sudden a massive orgasm exploded inside me. I started bucking my hips back against him wildly. He couldn't take anymore and his fingers dug into me as he exploded inside of me.

Tom got off me and got cleaned up. He kissed me softly on the lips. I turned over and he saw my pool of cum beneath me.

"That was amazing, I guess you liked it too! That is something I could get used to," he said right before he left.

I laid there on the table in a state of bliss. I couldn't believe how much I loved everything. Then I remembered the five hundred dollars on the table!

A few weeks later after many more visits, I moved in with Tom. I became part of his "staff". He gave me free rent and $3000 per month, and I was his trainer, massage therapist and sex toy! Along with my regular job, paying off the bills became much easier!

Published 
Written by mrer469
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