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Guest
Chapter 1
90 miles left to go until we reach Portland! This trip has taken forever. Three of us are in the car on our way to a week long required training for work. Somehow I always get stuck doing the driving. My boss, Howard, is riding shotgun, and my co-worker Jacob is in the back seat. This is one trip that I was not looking forward to. Other than the open bar, and personal time after the training to explore the city, I had better things to do back at home. Oregon is a beautiful state though, so at least the scenery has been nice to look at along the way. It’s only Monday. Damn. Friday can’t come soon enough.
What I didn’t expect while driving, is to receive a text message from Jacob who is sitting directly behind me in the back seat. Keep in mind…I’m driving and our boss is sitting next to me in the passenger seat. At first I just ignored Jacob’s text message when I saw it come in. That is until Jacob continued nudging the back of my seat to get my attention! I look in rear view mirror and see Jacob mouthing the words, “read it!”
Jacob has quite the sense of humor. He is one hell of a prankster so I’m used to being surprised by his wise-ass antics. Oh here we go…I’m going to open this message and somehow it’s going to embarrass the shit out of me or scare the hell out of my boss. Either way it’s going to make me laugh…probably out loud…guaranteed!! Always does.
I click on Jacob’s message to open it, and it reads “How big is your cock???” Immediately I think “wtf?” and start laughing to myself. I look in the rear view mirror and Jacob winks at me and licks his lips seductively. My boss is oblivious to what is going on. Jacob is a 30-ish year old gay man (total top). I’m 32 and straight. Well, let me back up a little. I’ve only been with women but am very curious. Gay porn and a dildo in my ass are a guilty pleasure of mine. My first time penetrating my ass, I came hard! HARD! Jacob loves to flirt with me at work and watch my face turn red. That’s one of his guilty pleasures.
“Ding.” Another text message comes in…
Jacob: Seriously how big?? Is it tiny or huge?
Me: Lol. You’re stupid. Ok I’ll play along..it’s 8”
Jacob: How thick?
Me: wtf Jacob….ok, 8x6 dumbass!
I continue driving and texting, and by now my boss is getting agitated. “Keep your eyes on the road Tyler. We’re in a damn company car.”
“No shit,” I think to myself. “Thanks for the reminder.” All the while, penis-breath Jacob is in the back seat laughing under his breath at me. I just roll my eyes. We are almost to the hotel, where I can finally get a drink and relax. Jacob and I are good friends, but we do push the line quite a bit. Seriously though, I enjoy the flirting. He gives me a boost I need sometimes. He has warned me several times over the years, “I could blow your mind straight guy!” I laugh it off. Typical Jacob.
We finally reach the hotel and I’m exhausted. Actually this place is a high dollar resort. Absolutely gorgeous and complete with gym, sauna, bar, pool…the works. It’s definitely not a place I could ever afford to pay for on my own. The sun is going down and the Oregon air is damp and cool.
Within another 15 minutes or so, I’m finally in my hotel room. Jacob’s room is a few doors down, and Howard’s room is on another floor. Down in the lobby, I had told Jacob that I would meet him later on in the bar, around 7:30pm or so. Right now though, I’m going to turn on the TV and stand in the shower. This shower is so sexy..see through glass, a huge built in tile seat, and it is divided from the rest of the suite only by frosted glass. I could live here!
After getting cleaned up and relaxing a bit in the suite, I met up with Jacob in the bar. Thankfully Howard was yucking it up in the restaurant with a former colleague. Jacob and I had about enough of his shit anyway and it was only day one of the trip.
Jacob and I sat at a table in the corner of the bar and ordered up a couple of beers. We laughed and joked, and before we knew it, a couple of hours had passed. The music was loud, the cigarette smoke was getting thick, and Jacob and I were getting smashed. Jacob leaned over the table and said to me, “Damn Tyler, your cock is 8” huh? Your cock must be gorgeous!”
“We’ll it is Jake! It’s fat and veiny too,” I said. “I shoot big, creamy loads…10 spurts at a time sometimes!” I suddenly realized I had probably said too much. The alcohol sure as shit broke that barrier down.
“Damn bro!” Jacob said excitedly. “I bet I could make you throw 11 spurts though.” This was classic Jacob. He was always joking around, but this time I felt like giving in to him. I have known him for a long time, and I trusted him. I knew he was up for it too. He had been after me for years, and I played hard to get. Actually, playing hard to get was the easy part. I was nervous as hell. Could I really suck his cock? Would I let him suck mine? Would I let him fuck me?
“Let’s go up to my room.” I said. Jacob grinned from ear to ear, and to the elevator we went.
90 miles left to go until we reach Portland! This trip has taken forever. Three of us are in the car on our way to a week long required training for work. Somehow I always get stuck doing the driving. My boss, Howard, is riding shotgun, and my co-worker Jacob is in the back seat. This is one trip that I was not looking forward to. Other than the open bar, and personal time after the training to explore the city, I had better things to do back at home. Oregon is a beautiful state though, so at least the scenery has been nice to look at along the way. It’s only Monday. Damn. Friday can’t come soon enough.
What I didn’t expect while driving, is to receive a text message from Jacob who is sitting directly behind me in the back seat. Keep in mind…I’m driving and our boss is sitting next to me in the passenger seat. At first I just ignored Jacob’s text message when I saw it come in. That is until Jacob continued nudging the back of my seat to get my attention! I look in rear view mirror and see Jacob mouthing the words, “read it!”
Jacob has quite the sense of humor. He is one hell of a prankster so I’m used to being surprised by his wise-ass antics. Oh here we go…I’m going to open this message and somehow it’s going to embarrass the shit out of me or scare the hell out of my boss. Either way it’s going to make me laugh…probably out loud…guaranteed!! Always does.
I click on Jacob’s message to open it, and it reads “How big is your cock???” Immediately I think “wtf?” and start laughing to myself. I look in the rear view mirror and Jacob winks at me and licks his lips seductively. My boss is oblivious to what is going on. Jacob is a 30-ish year old gay man (total top). I’m 32 and straight. Well, let me back up a little. I’ve only been with women but am very curious. Gay porn and a dildo in my ass are a guilty pleasure of mine. My first time penetrating my ass, I came hard! HARD! Jacob loves to flirt with me at work and watch my face turn red. That’s one of his guilty pleasures.
“Ding.” Another text message comes in…
Jacob: Seriously how big?? Is it tiny or huge?
Me: Lol. You’re stupid. Ok I’ll play along..it’s 8”
Jacob: How thick?
Me: wtf Jacob….ok, 8x6 dumbass!
I continue driving and texting, and by now my boss is getting agitated. “Keep your eyes on the road Tyler. We’re in a damn company car.”
“No shit,” I think to myself. “Thanks for the reminder.” All the while, penis-breath Jacob is in the back seat laughing under his breath at me. I just roll my eyes. We are almost to the hotel, where I can finally get a drink and relax. Jacob and I are good friends, but we do push the line quite a bit. Seriously though, I enjoy the flirting. He gives me a boost I need sometimes. He has warned me several times over the years, “I could blow your mind straight guy!” I laugh it off. Typical Jacob.
We finally reach the hotel and I’m exhausted. Actually this place is a high dollar resort. Absolutely gorgeous and complete with gym, sauna, bar, pool…the works. It’s definitely not a place I could ever afford to pay for on my own. The sun is going down and the Oregon air is damp and cool.
Within another 15 minutes or so, I’m finally in my hotel room. Jacob’s room is a few doors down, and Howard’s room is on another floor. Down in the lobby, I had told Jacob that I would meet him later on in the bar, around 7:30pm or so. Right now though, I’m going to turn on the TV and stand in the shower. This shower is so sexy..see through glass, a huge built in tile seat, and it is divided from the rest of the suite only by frosted glass. I could live here!
After getting cleaned up and relaxing a bit in the suite, I met up with Jacob in the bar. Thankfully Howard was yucking it up in the restaurant with a former colleague. Jacob and I had about enough of his shit anyway and it was only day one of the trip.
Jacob and I sat at a table in the corner of the bar and ordered up a couple of beers. We laughed and joked, and before we knew it, a couple of hours had passed. The music was loud, the cigarette smoke was getting thick, and Jacob and I were getting smashed. Jacob leaned over the table and said to me, “Damn Tyler, your cock is 8” huh? Your cock must be gorgeous!”
“We’ll it is Jake! It’s fat and veiny too,” I said. “I shoot big, creamy loads…10 spurts at a time sometimes!” I suddenly realized I had probably said too much. The alcohol sure as shit broke that barrier down.
“Damn bro!” Jacob said excitedly. “I bet I could make you throw 11 spurts though.” This was classic Jacob. He was always joking around, but this time I felt like giving in to him. I have known him for a long time, and I trusted him. I knew he was up for it too. He had been after me for years, and I played hard to get. Actually, playing hard to get was the easy part. I was nervous as hell. Could I really suck his cock? Would I let him suck mine? Would I let him fuck me?
“Let’s go up to my room.” I said. Jacob grinned from ear to ear, and to the elevator we went.