Moving to Boston

It was still early in the day. Already I had worked out and been fucked. There were no other plans for the day. At home I packed for the weekend. I was pretty sure it would include sex but other than that what would I need? Saving one work outfit for the next morning I packed the rest of my work clothes and a nice casual set. Guess I would have to improvise. Out of cash and my bank account nearly empty I didn't want to spend any money but I was bored.

The warm sun beat down on me and a light breeze came up from the sea. I didn't want to move, just enjoy the sun, beach and beautiful day. Wait! I opened my eyes. Jude was inches from my face blowing on me. I had fallen asleep. Damn, a nice dream too.

"Wake up sleepy head. Someone have a busy day?"

"Hi, Jude. No, the opposite. Guess I fell asleep trying to figure out what to do."

"Well get up. We have something to do, if you are interested."

"Sure. What?" I was still groggy.

We have tickets to a show but first dinner. Get dressed so we can leave.

The evening flew by. We met up with Craig and three of their friends. We ate and then went to a show that was a cross of a play and singing. Not my thing really but I enjoyed it because the guys were really hot and got nearly naked and it turned me on. Returning home Jude and I had sex and then I went to sleep excited about my first day on the job.

Showered, shaved, dressed and out the door, I was so excited to work I almost forgot to eat breakfast. Terry was already at work and greeted me with a big smile, "Ready for your first assignment?"

"More than ready!"

"Good. It's an easy one; this company has us come in once a month for the same meeting, the same guys. They are really nice, it's an easy one."

We left the office and went to the assignment. Terry called to check on the delivery of the coffee and rolls. A man in his fifties, dressed in a gray suit came into the lobby where we were waiting greeted Terry and introduced himself to me. It was all very professional.

Turned out the entire morning was very professional. There was no groping or touching, no mention of sex at all. We served the light breakfast and then sat outside the meeting room waiting to be called. This was a good opportunity to chat with Terry and learn a little bit about him. He was easy to talk with and we enjoyed two hours getting to now each other with our clothes on.

At noon the lunch arrived. Terry showed me how to set it up on the cart and we rolled it in. The men took a break to use the restroom and we placed a lunch at each chair. We remained in the room making sure beverages were filled and then cleaned everything up. As we rolled the cart out Terry smiled at me. "Now we earn our reputation."

I looked at him puzzled as to what he meant.

"We are going back in and we have fifteen to twenty minutes before they resume their meeting. We kiss, make up and slowly take off our clothes. You wore a thong didn't you?"

"No, briefs."

"Damn, looks like you are going to loose them. Normally they want us to keep the thong on so they can see our asses but briefs doesn't cut it so your will end up naked."

"Do we suck dick or fuck?"

"Nope. We just make our, explore each others bodies and when time is up we are told to stop."

"So that's it? We just make out?"

"Yep, they want to watch a couple hot young guys making out, getting nearly naked. No sex."

"Ok."

"Come on, it's time." Terry smiled and opened the door. The men stopped talking and looked at us. They knew what was happening, or what was going to happen. I followed Terry as he walked to the other side of the room. He reached back for my hand and I took his. We stopped and he pulled me close to him and we kissed. Slowly and rather sensually he kissed me and moved his hands over my body. I followed his lead. After he took my shirt off I took his off. Then the shoes, socks and pants.

Standing up so they could see us we made out and felt each other's body. I was very turned on. Terry's hand slid into the back of my briefs and he began squeezing my ass cheek, his other hand was soon inside as well. He turned us so my back was toward the men and slowly slide my briefs down showing off my ass. We continued to kiss. My cock was hard and trapped in my briefs.

"Thank you boys." The boss man said.

Terry pulled away from me and bent over to put on his socks, pants and shoes. I did the same giving the men a great view of my ass as I bent over. I noticed Terry was also hard, it was tempting to reach for his cock but I resisted the urge.

Putting on our shirts we tucked them in, put on our shoes and left.

"You did great Sam. That was exactly what he wants. Well done." Terry congratulated me once we were outside the meeting room. For the next two hours we sat and waited.

Noise from the room indicated the men were standing up. The meeting was over. As they filled out we stood and smiled not saying anything. Not one made a comment outside of a thank you. Anyone watching from outside the meeting room would have no idea we had made out and gotten nearly naked, it was all very professional and straight forward.

The last man out of the room was the boss. He stopped and shook our hands and thanked us for our help. No word about what happened. I found it a little strange but didn't say anything. Once we were on our way back to the office Terry explained that this was how it went every month. There is no sex, no contact with the attendees and the boss never asks for anything more. I told him it seemed odd and he replied that our reputation was not as prostitutes or rent boys or some such thing, just very good looking young men who help out. We are eye candy.

The conversation turned to my next assignment. Terry suggested I go home and take a nap but not to be late to the hotel. He also suggested I clean out. "This assignment is the other type of service we provide. Ed is typical of the clients who come into town and want company when not working. Some guys really just want someone to talk with to keep from being lonely or bored. Others, like Ed would want sex, which is why I was staying until he left on Sunday.

"So I am the rent boy on this one." I felt like I had him.

"We don't use that term professionally but yeah, he is paying for your time. It just happens that it will include sex. Treat him well Sam, you can't fuck this up."

At home I took a short nap before getting my bag and heading to the hotel.

It was nearly eight when I walked into the hotel, feeling obvious to the world I was coming in to have sex with one of the guests. The elevator ride to his floor made me nervous. It wasn't the elevator but not wanting to fuck it up. I walked slowly to his room and knocked on the door. After a moment he answered. "Sam. Come in. So glad to see you."

The room was very nice, not too large but ample room for an extended stay. Ed kept things professional, telling me to be comfortable and where to place my bag. He mixed us each a drink and we sat and talked for a while. When the drinks were done he asked if I wanted to see the suite. Standing up I could feel the alcohol hit me. Damn it was a lot stronger than it tasted.

As we walked past the bed I felt a sharp pain in my gut. He had punched me! I didn't even see it. Doubled over he pushed me onto the bed. Fuck it hurt, why did he punch me? In seconds my feet were bound together and he yanked my left arm out and pulled me onto the bed. Before it registered me arm was tied to the post. He moved to the other side of the bed and grabbed my right arm and yanked that one out. This time I watched, still in some pain from the punch, as he placed a leather cuff on my wrist and hooked it to a strap on the post. He moved back around and placed a cuff on my left arm and re attached my arm to the post.

What the hell was happening?

He didn't speak the entire time. His back was towards me and he laughed. "Damn I am going to enjoy this." He said and turned. He had something in his hand. Moving deliberately he approached me and placed a rubber ball in my mouth, forcing it in the lifted my head and hooked the straps together. A ball gag, cuffs and I was helpless.

"What are you? Nineteen? Twenty? Bet you have had more than a few cocks in you already. Wouldn't be surprised if you spent the morning on your knees. Slut."

He got onto the bed and straddled me, sitting on my abs that were still sore from the punch. "Ever been tied up? Restrained? Raped? After tonight you will be." He leaned in and licked my cheek. "I hope for your sake you have had plenty of cock in that ass of yours, otherwise this is going to hurt real bad Sam. I saw your boss fucking you. He was gentle compared to what I am going to do. I am going to show you what it is really liked to get fucked my a real man."

I was afraid.

He scooted down and sat on my legs, his weight caused some pain on my knees. Roughly he started grabbing and feeling my body through my clothing. He pinched my nipples and squeezed my arms. He wasn't being gentle. He wasn't being sensual. He was being forceful. Reaching up he grabbed my shirt in both hands and ripped it open. Buttons flew, the sound of clothing ripping, I jumped, or tried to. He laughed.

"Scared are ya? Good." He snarled and his hands reached for my nipples. "Nice and small, perfect for pinching." He said as he pinched them both and twisted. I screamed but the ball gag muffled it. He then squeezed my pecs, moved to my abdomen and grabbed at it trying to get a handful and squeeze. He pressed on my stomach.

"That hurt boy? My punch hurt too didn't it?"

He unbuckled my belt and with force pulled it out of the loops ripping at least one of them. "Ever been belted? I love belts." He laughed, grinning the entire time. He folded my belt in half and raised it to his nose and took a deep breath. Leather, good. Plastic really hurts, it can cut. Leather, it just leaves beautiful red welts." He tapped it across my chest and stomach. It wasn't hard but I jumped each time.

He got off of me and reached for my crotch and squeezed. I screamed again into the ball gag. Fuck, no one would be able to hear me. "Like that boy? Like having that boy cock squeezed? Like those pathetic boy balls feeling the pressure of a man's hand gripping them?" I shook my head no. Mistake. "No? You want more huh." And he squeezed harder. Fuck? Would he break them?

He walked away and returned with a knife. My eyes grew wide. The fear was real. That too was a mistake. He smiled. Reaching towards my legs with his free hand. He raised my legs and bent them all the way back until my knees were in my chest. Sing his arm to keep them there he prevented me from seeing anything. Then I felt the knife on my ass. He ran it along my crack and then, slowly, he started to cut the fabric. Tears poured out. I was terrified.

I felt the fabric give way. He didn't cut much of it. Putting the knife down, making sure I could see it he laughed again. "Thought I was gonna cut ya didn't you. Nah, that would make a mess. Besides, I want you whole." His fingers reached into the hole and he ripped the pants open. My ass was exposed.

"Wearing underwear are ya? I thought I told Michael I liked my boys commando." His hand was poking at my hole. He moved and my legs feel to the bed. He reached for the waistband and using both hands yanked the pants open. The button flew and the zipper ripped. Moving to the end of the bed he grabbed the pant legs and pulled them down. A zip tie was holding my ankles together. The pants stopped at the tie. He reached for the knife and cut the zip tie. My legs were free and I tried to kick. Another mistake. He grabbed one ankle, not pleased with my actions and pulled pants off. Moments later an ankle cuff was on and my leg attached to something at the corner of the bed. He did the same with the other leg.

Spread wide, unable to scream or move I was breathing heavily. He wasn't kidding when he said rape. His hand reached for my crotch again and he squeezed. Fuck it hurt. Tears once again. Taking the knife he slide if, dull side down, along my leg, he circled my cock and balls and went down the other leg and back up. The tip of the knife went under the leg opening of my briefs and he cut the side open. Pulling the other side of the briefs down to my ankle I was now fully exposed.

"Sam. You get to choose. Belt on the cock or ass first."

I stared at him, of course I couldn't answer.

"Speaking isn't easy so nod. Cock or ass? Cock?" He paused. Fuck, what do I do? I shook my head no. "Then ass it is."

He unhooked my left leg and pulled it over to my right, hooking it to the post. He did the same with the left arm then unhooked my right arm and pulled it, turning me onto my stomach and hooked it back up. After switching my right ankle to the other side he laughed. "Nice ass boy. Wait until it's red."

The impact of the belt, my belt, on my ass was swift and it hurt. Tears were flowing as he repeatedly slapped my ass with my belt. He didn't stop there, he moved to my upper legs and my back. Sobbing and in pain I could do nothing. He stopped and spread my sore cheeks open. He spit on my hole and roughly shoved a finger in. He took his time raping me with his fingers; thankfully he kept spitting to easy the friction. The entire time he was speaking, calling me a whore, slut, among other things. He said I was eager to be raped and deserved it. Then he stopped. I couldn't hear much of anything, I was still terrified and in pain. I felt the bed move, he was climbing on. His cock pushed between my cheeks, I could feel it slippery and cold. Once at my bud he forced his head in and stopped. Then he leaned in and drove his entire cock in. I passed out.

"Wake up you shit." His voice brought me out of my fog. "Good." And he continued to rape me. He pounded away at my hole, it hurt. There was nothing pleasurable about it for me. When he stopped I heard him grunt. He grunted a few more times and then started driving his cock in and out again. He must have cum.

When he finished he pulled out and got off the bed. I heard the shower. Laying there, in pain and still scared but relieved it was over I waited. Would he do it again when he returned?