- This is my second attempt at writing a story. Please let me know if you like it. None of this is true, but is based on a fantasy about a coworker. Names have been changed.
Two years ago, Josh started working in the east coast office I was assigned to. Working with him on a daily basis was great because I got to look at him on a daily basis, but bad because I was sure he was straight. Josh is a 29 year old guy, about 6'5" with an average build. He was the subject of many jack off fantasies and I would have loved to get with him for real. Unfortunately, a few months ago, I transferred to one of our midwest-based offices and I couldn't see Josh on a daily basis.
Two months ago, I was on a trip to Arizona with several people from across our offices. Josh was the representative from our east coast office. I knew I'd be spending the week shooting lots of cum from jerking off to fantasies about Josh.
The day we all arrived, we were suppose to meet in the lobby at 6:30 pm for drinks and then head out to dinner. I arrived at my hotel too late and didn't have time to jerk off before I had to meet the team so I figured it could be a long evening. I got down to the lobby and found the team. I said hi to Josh and saw him in his jeans and button-down, close-fitting shirt. I felt instantly more horny but was convinced it would just be a fantasy. We all had a couple drinks, then headed out down the road for dinner. Josh stood up and went to go clip is Blackberry to his belt. As he did, his shirt lifted up and I could see the dark waistband of his Hanes underwear. I assumed they were boxerbriefs because that's what I always imagined him wearing. I smiled, then quickly looked away so he wouldn't see me checking out his underwear. As we walked out, Josh looked over at me and smiled, the walked up to talk to a couple colleagues in front of me.
At this point, I stated to wonder if he had seen me or if it was just a coincidental smile. I quickly decided not to care and discretely watch his nice ass in front of me as we walked down the street. When we reached the restaurant, I chatted with my colleagues and let Josh escape from my head for a couple hours.
We all discussed a plan to meet up in the morning and dispersed to our rooms. We were mostly all on different floors, but Josh and I were both on the Executive floor since we both travel a ton and have high status with the hotels. The elevator ride up was quiet, but Josh kept looking over at me briefly. I was trying not to look at him so it wasn't obvious I just wanted his cock.
As we got off the elevator, we were about to part ways and told each other to have a good night. Then Josh paused and looked over at me again...
"Can I ask you something real quick?" Josh said.
"Sure, what's up?" I said back, really just wanting to go to my room and jerk off.
Josh just stood there and looked at me like he was thinking about something.
"You actually have to say something if you want me to answer." I said jokingly.
Josh laughed a little then said "I don't really want to make anything awkward - especially since we work together but were you trying to check me out earlier before we went to dinner?"
I paused kind of stunned. "Shit" I thought. I was sure I had been discrete enough. Our east coast office has more open-minded people than the Midwest office, so I figured I'd tell the truth and hope he didn't care. "Well yeah, kind of." I said. "I didn't want to make you feel awkward - sometimes it's hard not to look though."
Josh smiled. "I was hoping that's what you would say."......"Well, I know we work together, but if you ever want to check eachother out more closely, let me know - you're pretty nice to look at too."
I couldn't beleive he said that but I smiled and invited him back to my room. He accepted and before I knew it, we were in my room and on the bed. Josh and I were making out like mad with Josh on top - grinding his obviously hard cock into me through our jeans.
I rolled Josh off of me and got up to take off my pants and shirt. Josh sat on the edge of the bed and rubbed my cock through my boxerbriefs. I reached down and took his shirt off. I knew I wanted to see the rest of his underwear - what was attached to that waistband I saw earlier. I pushed Josh back, rubbed his hardon thru his jeans, then unbuttoned and unzipped his jeans. I pulled them off and tossed them aside. With Josh on the edge of the bed, I got down on my knees and started to lick his huge balls through his dark green Hanes boxerbriefs. I ran my hand up over his balls and up his cock. His boxerbriefs were saturated in precum! Josh said he precums a ton and apologized for all the precum. I told him I loved it and quickly got my mouth on the front of his boxerbriefs, sucking his precum out of the fabric.
Josh asked if I wanted to clean up together in the shower since it had been a long day for the both of us. I agreed and we quickly got the shower running, threw our boxerbriefs (wet with precum) on the bathroom floor and jumped in the shower with our rock hard cocks. We made out, pressing our hard cock together. Josh grabbed the soap and we stared to soap each other up. After we cleaned each other, Josh soaped up his hands again and started to run them up and down my ass crack. I felt him spend some time soaping up my hole and getting it good and clean. He smiled and said it felt like I had a great hole and he hoped he could play with it more. I told him my hole loved getting fucked, fingered and rimmed so he could do whatever he wanted.
As I rinsed my hole clean, Josh said that it sounded hot to do any or all of those to me. He said his hole loves getting rimmed but only rarely takes cock. He said he was mostly a top but every once in a while he had a urge to take a cock in his ass. I instantly got harder at the thought of rimming his undoubtedly tight asshole. I grabbed the soap and work his crack to get him good and clean just like he did to me.
After he rinsed off, I got on my knees and started to give Josh a blowjob. Taking his 7" thick cock all the way in my mouth. Josh was in heaven and said it felt so good. I stopped sucking Josh's cock and told him to bend over a little. I dove in and started to lick up and down his crack - flicking my tongue across his hole as I passed. I focused in on his hole and gave him a brief rimming.
I stood up, we kissing and we turned off the shower - ready to move back to the bed. Josh dried off first and headed off to the room. I finished drying off and quickly wandered out to the room. Josh had pulled the covers back and was on all fours with his ass out towards me.
"That's a great view! What is it you're wanting there Josh?" I said.
"That tongue in my ass felt so good! I want more of it!" Josh said.
I didn't need to be told twice - I got down behind Josh and started licking his hole. Running the tip of my tongue back and forth over his hole. I wanted to try to tongue fuck him a little but he was too tight. I told Josh to relax his hole and he did as he was told. I still couldn't get it in too deep, but flicked my tongue into his hole. After several minutes of rimming him - i decided it was time for him to service me for a while. As I pulled my face out of his ass, I licked the back of his balls and noticed the huge puddle of precum he had dripped all over the bed while I was rimming him.
We kissed a little bit then Josh started giving me a blowjob. It felt amazing - he definitely knew how to give good head. That said, I knew what I really wanted - Josh's tongue in my asshole, followed soon by his big, thick cock. Josh must have sensed what I wanted because he let my cock fall from his mouth, pushed my legs up in the air and started to eat out my ass.
It felt so fucking amazing - he knew just the right combination of light licking and deep tongue fucking. Soon his long fingers were working my hole deep getting me opened up for his thick cock. He asked where my condoms were and I told him where to find a condom and some lube in my bag. He said he's not very good at pulling out and cumming on a guy so asked if I minded if he came into the condom while he was in my butt. I had no objection.
He started to fuck my tight hole nice a slow - working his thick cock deep into me. He picked up his pace more and more. Soon he was pounding my hole hard and deep. It hurt a little but it was such a great feeling to have his big thick cock pounding deep into my butt. Josh pulled out and said he wanted to fuck me doggie style.
I got on all fours and Josh mounted my butt and shoved his cock deep in me. Having a total underwear fetish - I had grabbed our boxerbriefs and brought them out of the bathroom with us. I grabbed Josh's boxerbriefs and tossed them on the pillow - burying my face in his dirty underwear as he pounded my butt. After about five more minutes of fucking - I knew I was going to cum. I didn't want to drench the bed I was about to sleep in, so I grabbed my boxerbriefs and wrapped them around my cock. I started to unload my big load into my boxerbriefs and my hole wrapped even tighter around Josh's thick cock. The extra tightness sent him over the edge and he shoved his cock deep in my and started to shoot his nut into the condom.
Exhausted we collapsed onto each other. After a minute or two Josh pulled his cock out of me and rolled off me. As I rolled over, he grabbed my cum soaked boxerbriefs and started to lick up my load. While he was cleaning up my load, I knew I wanted to taste his cum. I got down and slowly pulled his condom off - making sure that all the cum came out all over his cock. I promptly started to lick up his tasty cum off of this cock. When we was all clean, I gave his big balls an extra lick and went back up to make out with him.
I asked Josh if he wanted to stay or if he was going to go back to his room now that we had gotten off. He said he wanted to cuddle with me all night so we turned off the light, cuddled up naked and fell asleep. In the morning, Josh went back to his own room to shower and clean up. We knew if we got in the shower together - we'd end up having sex again and be late for our meetings.
We were in town for another three nights and we fucked, rimmed, sucked and slept together the rest of the time. The last night Josh fucked me for a while, then told me he wanted to feel my cock in him. I boned him hard and made him shoot his load all over himself. Every night we cleaned up each other's cum.
Since that trip - I've been out to the east coast office twice and I've gotten Josh's hot bone in my ass both times.