My Friend's Brother Pt. 05

Like my first day in NYC, I went straight to my client's office in Chicago. All standard stuff, meetings, lunch, more meetings. Back at the hotel, I checked in and showered. I knew I was going to jerk off, but wanted to get a bite to eat first. I had already decided that I was going to video chat with Dawn when I jerked off hoping she would pick up where she left off last night in making me her slut. It was all I thought of all day long. I just needed to get through tonight and some meetings in the morning so I could travel home for the real thing.

I was tired so I decided to just go to the hotel bar for dinner. It was pretty nice and had a decent menu. I figured I'd get a steak and a couple of vodka tonics then head back to my room and call Dawn. I found a seat at the bar and waited for the bartender.

"Excuse me, is this seat taken?" the person next to me asked.

"No, it's not. Feel free to take it," I said as I turned my head to him.

"What the fuck?" I said

Standing in front of me was Tom.

"Surprise," Tom said with a smile.

"What the fuck are you doing here? How did you know I was here......What the fuck?" I was completely confused about what was happening.

"Slow down Mark," he said laughing. "I can see you weren't expecting to see me so the surprise worked," he said.

"Well, of course fucking not! How did you know I was here and what are you doing here?"

"Before we get into details, I have another surprise for you," he said.

Tom looked past me and further down the bar. He gave a nod of his head to someone and smiled.

I turned to look at who he motioned to, but there were so many people that there was no way to determine it so I turned back to Tom.

"Who are you motioning to? Is Dawn here?"

"I wish," he responded. "I would love to get back inside her. By the way, I've hooked up with another woman since our adventure. I think I'm officially bisexual!"

"Me too," I laughed.

"Mark, I'd like you to meet my friend William," Tom said, gesturing to someone on the other side of me.

I turned to look and found an indescribably handsome man standing beside me. He was at least six feet tall and very well built. He was very well dressed and certainly filled out his tailored clothes with his muscular body. His skin was dark black and from what I could see in a dimly lit bar, without blemish. I rose from my seat to greet this specimen.

"Hi William, I'm Mark. Very nice to meet you," I said, reaching out my hand.

"Yes Mark, nice to meet you as well," he said, clasping my hand.

His hand was large and powerful. I couldn't help but notice how crisp and clear his eyes were as I looked into them while shaking hands. When Tom described William to me and Dawn during our threesome, I thought he was exaggerating. He was not. I couldn't get over just how perfect this man was.

Looking around I could see there weren't three seats together at the bar. I glanced over the main seating area and saw plenty of tables for us.

"Do you guys want to grab a table? You have some explaining to do about how you found me," I said looking directly at Tom.

"That would be perfect," said William.

I watched the two of them walk to grab a table while I settled up with the bartender. While waiting for my change I couldn't help but stare at William. My god, his face and body were perfect."

"Alright, let's hear it," I said as I slid into my chair at the table.

"There's really not much to hear," said Tom. "You told me you were going to be here a few weeks ago," Tom said with a chuckle.

"What, I told you? When?"

"We were chatting about setting up another night with Dawn. You said you were traveling this week and it wouldn't work. We talked about where you were going and where you were staying. You don't remember talking about hotels in Chicago and where I stay when I come here?"

"Vaguely," I said. "What about William, why is he here?"

"Actually, I'm here because of William. He has family in Chicago and I came with him for a visit. It just so happens that the dates coincided with your business trip. I thought it would be nice to surprise you," Tom explained.

"Yes, Tom has talked quite a bit about you so I was curious to meet you. It sounds like you two have quite a history," William said.

"Wow, this is a lot to handle. Surprised, fuck yeah I'm surprised. "How did you know I'd be in the bar and not out to dinner with a client?"

"I didn't, but I was hopeful. Look, the worst case scenario was that I couldn' find you and William and I go out for a nice dinner," he replied.

"Well, thanks for coming, and William it's certainly a pleasure to meet you," I said.

"Likewise, I hope we have the opportunity to get to know each other," he said.

"Does Dawn know you are here," I asked Tom.

"No, but I would love to have brought her," Tom laughed.

"She'll never believe this," I said as I got up from my chair. I circled the table so that I was between Tom and William.

"Squeeze in so that I can get a picture to send to her. She was just making me promise that I will get you back to the house, Tom. She's going to shit when she sees this."

The three of us squeezed together for the photo. William and Tom wrapped their arms over my shoulders. I could feel the strength in each of their arms. I felt safe and secure. I also couldn't help but notice how good William smelled. This man was unbelievable. As we broke from the picture Williams hand fell from my shoulder and lightly brushed down my back and over my ass. I'm not sure if he meant it, but it sent a jolt of sexual tension through me.

I sat back in my seat and sent the picture to Dawn. I couldn't wait to see her response. My wait wasn't long as she responded within seconds.

"WTF, please tell me that is WILLIAM!!!!"

I laughed out loud causing the guys to look at me.

"Let me guess, she responded, right?" asked Tom.

"She did, and apparently William has a fan," I said laughing as I turned the phone for them to see.

"Doesn't surprise me," Tom said. "I mean look at the fucking guy."

"I have been," slipped from my mouth. "I mean, obviously I have to since we are all sitting together," I stammered.

Tom and William exchanged glances and shared a chuckle.

"How are you going to respond to her," asked Tom.

"What do you mean? I'm just going to say it is," I said, trying ro respond to him like it was no big deal that I'm sitting in a hotel bar with William and him.

In reality, it was a very big fucking deal. I mean, it's obvious why they are here. I was nervous to think of where this could lead. What do I do if the opportunity presents itself? I promised Dawn I would only hook up when she was part of the mix. God, the thought of William and Tom in bed with me might be reason enough to break my promise. She'd have to understand, right? My thoughts were interrupted by the buzz my phone makes for incoming text.

"Is it William? It has to be William. Who ever it is, he's fucking hot. Tom looks good too," she texted.

"Yes it's William and he is fucking gorgeous. Wish you were here so we could all hook up like we talked about." I responded.

"Me too. Listen to me. Don't pass this opportunity up. If things go down that path, DO IT!"

"But, our promise???"

"As long as I know it's happening I'm fine - DO IT!!!........I WOULD!!!"

"Hey Mark, are you with us here?" Tom asked.

"Ah yes, yes, sorry, I just have to finish this text with Dawn. Apologies for being so rude," I said.

"Please, not a problem at all." William interjected. "Please take the time you need for your wife. I'm sure she is as confused as you were upon seeing us."

"Thank you, William, that is very kind of you. Let me just fire off one more text. I feel bad that I'm staring at my phone when I have two very attractive gentlemen in front of me," I said with a smile.

I saw William and Tom glance with a smirk at each other again.

"Let's just see where it goes. I'm not comfortable going back on my word," I texted back to Dawn.

"Fucking do it and enjoy it!!!!" was her response.

With that I put my phone away and focused on Tom and William. It was hard to believe I was sitting here with these two incredibly handsome men. It made me stop to think how far I have come in terms of my sexuality. I think my turning point was the passion I felt when making out with Tom a few months ago. It felt like there was more there than just the lust for sex. I truly could see myself in a long term relationship with a man. But, on the other hand I could not see myself without Dawn.

"So, you two must be pretty serious if you're coming out to Chicago to visit Williams's family," I said to Tom.

"We are, but we're not exclusive. We're open to exploring outside our relationship which, if you haven't already figured out, is why we are here. But, you know that right, Mark?" Tom asked.

"Yeah, I had a sense that you didn't just come to say hello," I laughed.

"Mark told me all about his night with you and Dawn. It sounds like it was one hot fuckfest," William said.

"Yeah, it was certainly a night to remember. It changed my life and Dawn's life too."

"It turned me bisexual!" Tom blurted out. "Seriously, it did. I look at women differently now. I actually crave pussy! But, nothing is better than a good cock, especially his." Tom said, pointing at William.

"Yes, I heard you are very well to do in that area," I said to William.

"Well, let's just say I've never heard anyone complain," William said laughing. "But, if I am to be honest, I was really hoping your wife was here. After hearing about that night, I was hoping that she would be interested in doing the same with me."

"Interested, are you fucking kidding me? William, my friend, your name comes up everytime we have sex. She would do anything to get a hold of you."

"Oh, wow. That's cool. Too bad she isn't here." he said.

I picked up my phone to see if Dawn sent any more texts. Of course she did.

"Well, what's happening? Keep me updated!" she texted.

"William, would you like to meet her?" I asked.

"Of course, but how?"

"Hold on." I said.

I typed Dawn's number into my phone and waited. After a couple of rings her face appeared on my screen.

"Well are you guys fucking yet?" she said when answering.

It was loud enough that both Tom and William heard her. We all looked at each other and laughed.

"And hello to you too," I said.

"Sorry, I just want to hear about William and if Tom's cock description was true."

"Well, why don't you ask him yourself," I said as I flipped the phone view so that it was on William and Tom.

"Oh, my god, I'm so embarrassed," I heard Dawn say.

"Please don't be," said William. "It is very nice to meet you, Dawn."

"Nice to meet you too. I'm soooo sorry for my comments. That was really rude of me."

"It's not the worst thing I heard you say," Tom said laughing.

"Shut up, Tom," she said laughing as well. "How are you doing? I miss you."

"I miss you too. Hey, remember how I said I had some female friends that would be interested in meeting you?"

"Of course I do," she responded.

"Well, there is one that is very interested. Her name is Becca and she is fucking hot. I mean smoking hot. She's a light skinned red head with a perfect set of tits and an ass your husband would love to get a hold of. What do you say I bring her by so you guys can meet?"

"Yes, without a doubt, yes. I still haven't been with a woman and Mark knows how much I'm dying to try it."

"Perfect, I'll send you her contact info so you can chat beforehand. That way you can skip all the awkward chit chat and get right to the sex when you meet in person. I can't wait to see you two hook up." Tom said.

"Same here!" I jumped in.

"Who knows,maybe Tom can take care of you while I take care of Becca," said Dawn.

"Works for me," Tom responded.

"Sounds like fun, but what about me?" joked William.

"Oh William, Mark and I have plans for you. Don't worry," said Dawn. "Speaking of plans, I assume you and William are not just visiting Mark to say hello. Why are you still in the bar? I figured you'd be in Mark's room by now."

"Well Dawn, you are right. We are not here to just say hello. In fact we were just discussing our lovely night together and how much you want to get in William's pants," Tom said

"Absolutely true!" she blurted out. "I'm not ashamed to say it. I want your cock William. There I said it."

"Well, um okay. I would like for you to have it," said William, not sure how to respond to Dawn's direct comments.

"I also want my husband to have it. So this is what the three of you are going to do. You are going to hang up with me and go upstairs. Mark, you are going to call me from your laptop and set it in a place where I can watch you guys enjoy each other. Deal?"

The three of us looked at each other and smiled. We all knew we were eventually going to move to my room, so what is delaying us.

"Why are you still there?" I heard Dawn ask.

"We're leaving now," I responded, figuring someone had to make the decision. " I Love you, honey. Thanks for the push. I'll call back when we get to my room."

"Well gentlemen, it sounds like we have our orders," Tom said, rising from his seat.

We all agreed and began our ascent to my twelfth floor room. It was awkward to say the least. When Dawn and I hooked up with Tom we were at a minimum quite buzzed. Not the case this time, I was stone cold sober. No one spoke as we made our way to the elevator. I pushed the button and we waited in silence. I was nervous, but excited. The doors opened and we entered. We were the only ones on when the doors closed behind us. When they did, William spoke.

"So Mark, Tom tells me he took your anal virginity."

"Yes he did," I responded

"Too bad, I was hoping I was going to be your first. I suppose second isn't too bad though," he said with a smile.

The doors opened and we exited the elevator. My room was a short walk and we were there in a matter of seconds. Still no talking other than William's comments on the elevator. I found my room card and went to insert it into the reader when I noticed how much my hand was shaking. I wasn't the only one to notice.

"Relax Mark, we're all friends here. We are going to have fun and do as much or as little as you want," Tom said, grabbing hold of my hand to steady it.

"I'm sorry if my comments in the elevator worried you," William said, also grabbing my hand. "You don't even know me so I shouldn't have said that."

"No, no it's fine," I told him. "That's not it at all. I don't feel threatened, I'm just nervous. I'm really excited for this, but to be honest, I'm concerned about the size of your cock and how I'm going to take it,"

"You haven't even seen it!," William laughed. "Let's take baby steps. Once you see it and if you think it's too much we won't do it,"

"Just so you know Mark, he is incredibly gentle and goes as slow as you want," Tom said.

I turned the door handle and pushed it open. I entered first followed by Tom and then William. I went right to the window and drew the curtains closed. I then turned on a couple of lights so that we could see. There we stood like three lost souls not knowing what to do next. Again, silence.

"Do you mind if I use your bathroom?" William asked.

"No, of course not. It's right there," I said pointing to it.

William disappeared into the bathroom and closed the door behind him. I could hear his urine splashing into the toilet as he relieved himself. I looked over and saw Tom looking at me.

"I missed you," He said, approaching me.

Tom reached out and grabbed my hips to pull me closer. I leaned in and our mouths met. He pushed his tongue between my lips and into my mouth. He kissed me hard and I loved it.

We broke our kiss as William came out of the bathroom holding my dildo in his hand.

"You should really put this away when you leave the room or you may come back to find the cleaning people using it," he said, causing us to laugh.

"Are you taking that whole thing, Mark?" Tom asked.

"Yes," I said, somewhat proudly.

"Well done. It's bigger than me. I hope you're not too loose for me now," he said laughing.

"Oh shit, I forgot to call Dawn," I said, grabbing my laptop.

I typed in the number as Tom and William made themselves comfortable. Dawn immediately appeared on the screen. She was in our bedroom and laying on our bed.

"Hi sweetie," I said.

"Hey babe, is everyone there?" she asked.

"We're here," Tom and William said in unison.

"Let me see," she said.

I flipped the camera so it was focused on Tom and William laying on my bed. William still had the dildo in his hand and was casually tapping it on his leg.

"Why the fuck do you guys have Mark's dildo out? You have three beautiful live cocks there. Do you know what I would give for that right now? I have my dildo, but only because I have to," She said.

"Oh no, I found it in the bathroom and told Mark he shouldn't leave it out," William responded.

"Ahh, I see. Yes, I had the privilege to watch Mark, fucking himself with it last night. Very hot to watch him have his first handless orgasm. He came like a fucking geyser," she explained.

"Really?" said Tom. "Well I hope you replenished the well for me and William."

"Well he drank it all down so he should be replenished. I also confirmed a suspicion that I've had for a long time last night that may be helpful to you guys as you begin your adventure," she said.

"And what might that be," Tom asked.

"My dearest husband admitted that he is a bit of a submissive."

"Really?" questioned Tom. "Like how submissive?" he asked excitedly.

"It's more about being directed what to do. I like to serve and give pleasure. Talk dirty and call me names if you want, but I'm not okay with hitting and watersports," I clarified to everyone.

"I like to call him my little cumslut," Dawn chimed in.

"You've always been a cumslut, Mark," Tom said. "William, he swallowed more of my cum in two years than you would ever imagine so I think the name cumslut fits perfectly."

"Works for me," said William. "Cumslut, come on over here."

I placed the laptop on the desk so that it was focused on the bed where Wlliam was lying. He was still tapping the dildo on his leg as I stood at the side of the bed. I could see Dawn intently watching when I looked over at the laptop. I didn't know what William wanted as I waited patiently. He was staring at me and kind of making me uncomfortable.

He reached up and put his hand on my hard cock. He was grabbing and rubbing it gently as he continued to stare at me.

"Feels nice," he said. "Pull it out," he instructed.

I reached down and unbuttoned my pants. William pulled my zipper down and then grabbed hold of my pants at the waist. He pulled downward and in one motion my pants and boxers were at my knees.

"Very nice," William said, staring at my hard cock. "Tom told me it was nice and he was certainly right. Did he tell you how much I love sucking cock?" he asked as got to a sitting position in front of me. He gently placed my balls in his hand and guided my cock head into his mouth.

"Mmmpfff, that feels so good William," I moaned.

His head bobbed slowly as he gently kneaded my balls. The contrast of his deep dark skin against my whiteness was an incredibly beautiful site. I felt Tom come up behind me. He grabbed hold of my shirt and pulled it over my head. He then squatted down behind me pulled my pants and boxers to my ankles. I stepped out of them so that I was now completely naked. As he slowly rose back up, he planted kisses on the back of my legs until he found my ass. He kissed and licked my cheeks before spreading them open. A slight flick of his tongue on my hole sent a jolt through me.

"Oh god, yes," I muttered.

Tom didn't spend long on my hole as he rose to a standing position. William was still slowly sucking me as Tom's arms wrapped around me and pulled me close to him. I could feel the warmth of his naked skin on mine and the stiffness of his hard cock against my ass. His right hand made its way up to my neck and he wrapped his fingers around my neck in a slight choking motion. He guided me to turn my head and kissed me deep and hard. He then released my mouth and whispered in my ear.