A Business Trip with Huge Benifits

I arrived in Chicago, traveling on business in which I have always enjoyed, not only from the standpoint that I loved my work, but I loved visiting so many fantastic cities. I checked into my hotel, took a shower, then headed to the bar for a beer. The bar was fairly filled with people, mostly men. I ordered a beer, enjoying the friendly atmosphere, when I noticed at the end of the bar a really attractive guy who was starring at me. I turned away but out of the corner of my eye I could see he was still starring. I finished my beer ordering another as I looked up he smiled at me. I was beginning to get aroused as he was amazingly gorgeous. I finished my second beer ordering a third, now having a nice buzz reducing my anxiety.

So.... this hot guy got up walking to the side of the bar where I was seated. As I watched him, his tall stature, built like a greek god, came over sitting next to me....he turned and said: "Hi, I'm Brady" "Its nice to meet you, I'm Connor." We began our conversation with him stating he was here for a conference with clients from different parts of the country. He never really told me what line of work he was in and I didn't ask. I stated that I was also on business, meeting with different IT personnel from different distribution centers from around the country. We talked about every subject imaginable. He had an incredible personality, easy going as our conversation just flowed as if we had known each other for a long period of time.

I got up to go take a piss as the beer was taking its toll on my bladder. My new found friend said: "I have to go too." We walked into the men's room walking up to the urinals. Now I have to say I am a well endowed man, but when I looked at his cock, his length plus girth even soft, took my breathe away. What a fucking cock, I never had seen one that huge. He looked at me smiling: "It's big isn't it?" "Man, what woman can take that?" "Connor, I like shoving this monster in a hot guys ass....there are guys who love it." I can't even fathom how an ass would open to take your cock....my God its not even hard.

We returned to the bar, our conversation turned sexual, as I asked him if he was gay. "Yes sir, 100% gay" "Connor have you ever experienced sex with a man?" "To tell you the true, no I haven't, but there are times when I see a really hot guy, I wonder what sex would be like with a dude." "There is nothing better than man sex....I've fucked more guys than you can count." "Wow, tell me....as I do know the terminology, are you a top or bottom?" "I'm definitely a top....it really turns me on getting a guy ready to accept my cock, then when I do fuck him, it really gets me going when he begins to take me, then begging me for more." "I also love to suck cock and be sucked, then nothing better than getting a big load of cum in my mouth, I just love the taste. "Fuck Brady, your very blunt.... I think my briefs are soaked with pre-cum with all this hot talk. "I have a suggestion Connor, why don't we go up to my room maybe showing you what your missing." 

The beer had diminished all my inhibitions so I agreed to go to his room. On the way up I said to myself: "What the fuck are you getting yourself into?" As we walked to the elevator, I felt small next him, with him being at least 6'2" compared to my 5'7". I was definitely not ashamed of my body, I worked really hard at the gym with my dedication paying off plus my bubble ass along with a handsome cock always made me confident. I had been with a lot of women, but there was never a connection.

We arrived at Brady's room….I was so nervous that my hands were sweating. He handed me a beer in which I downed quickly. We sat on the sofa because his room was really a suite also very spacious.

"He looked at me with concern: "Look if your not into this its no problem, we can talk then call it a night. "You have to understand my concern, I've never done this before. He came closer to me grabbing me by the neck pulling me into a kiss. I sort of rejected at first but his lips were so sensual and warm. He began running his tongue along my bottom lip as my mouth voluntarily opened....his tongue invading my entrance. An energy began to rush through my body, my tongue now starting to battle with his. Before I knew it saliva was dripping out of our mouths with my cock reacting to the foreplay.

Brady got up slowly beginning to strip, as I remained sitting on the sofa. When all he had left was his boxer briefs, I pulled him to me beginning to suck his cock through his briefs. "Yeah, your getting the drift of it, now pull my briefs down, show me what you can do." I pulled his briefs down slowly as his cock popped out....oh my God, its fucking huge. Not so much the length which was probably 8", but it was the girth. I just starred at it in awe as Brady said: "Well are you just going to just stare at it" I took the head in my mouth licking it then pulled his foreskin back to reveal a huge mushroom head. I began swirling my tongue all around the corona beginning to enjoy it when suddenly a huge amount of pre-cum came spewing out of his piss slit. I let my tongue rest on the side of his cock as his juice slid onto my tongue. I was really getting turned on with my cock straining against my pants. I loved the taste of his pre-cum it was salty but also sweet. I then began to consume his girth stretching my mouth to its maximum. I was determined to take him but as I got three quarters down I began to gag. "Take it easy buddy its not going anywhere." I realized that I couldn't take it all but I was happy that I could take most of it. They say practice makes perfect, but all I knew was I loved his cock in my mouth.

He told me to get up and strip which I eagerly did. My nerves seem to be disappearing also realizing that I wanted this. Brady got on his knees pulling my briefs down, instantly taking my cock into his mouth....within seconds he had my whole cock buried in his throat. "Fuck yes.....awe....mmmmm, never felt anything like this." My cock popped out of his mouth as he said: "Are you ready for what I've got for you?" I looked at him then it hit me, he was going to put that elephant cock in my virgin hole. "I guess I'm as ready as I'll ever be."

He told me to lay on the bed on my stomach then spread my legs. He began rubbing my ass crack with his fingers, as his fingers touched my hole, I felt incredible sensations from my perineum to my balls. He lubed his fingers, placing one finger, then two as he worked my hole, then three as I gasped in pain. After some time working my hole, he used two fingers from each hand spreading my hole wide open as he took his tongue devouring me as I moaned with pleasure.

He told me to get on my knees as he placed his torpedo at my entrance. He pushed into me passing my sphincter as I yelled: "Fuck Brady.... stop your killing me." He stopped, telling me to relax, slowly he began pushing in again. "Oh fuck....I feel like I'm going to rupture." "Do you want me to stop Connor." "Fuck no, just go slow." He began once again until he was balls deep into me than once again stopped. "Okay, the pain isn't to bad, now fuck me slowly. His strides began to intensify when suddenly he hit my prostate sending me in a frenzy of lust. "Okay now fuck me." He began sliding in and out of my tortured mancunt, but I was pleasure bound. "Your tight hole feels so good, as your ass muscles are working my cock.

He pulled out telling me to lay on my back. "Before I do, I want to suck your cock....I took him in my mouth as I could smell his musky manly scent which excited me. I grabbed his huge balls, took my mouth off his cock, taking his balls washing them with my tongue. "Oh fuck yeah, your a fast learner." His taste was putting me in a pure state of nirvana, as my mouth began to expertly suck his balls, then back to his cock. "For a guy with no experience your a natural." For some reason I loved what I was doing to him, wanting to show him that I was inexperienced but I could make the mark to be just as good as anyone else he had been with.

He had me get up, pushing me against the wall as he rammed his one eyed monster in my mancunt. This position was difficult due to our difference in height, but he squatted down, making it work. He then picked me up holding my legs in his arms as I placed his cock at my hole penetrating me, the fullness was overwhelming. He began bobbing up and down as I began to kiss him like a crazed animal.

The feelings that were racing through my body were evident as I began to yell: "Yes, fuck me....mmmm....ooh....yes." I never experienced anything like this with a woman. After fucking me in this position he carried me to the bed telling me to stand up putting one foot on the bed. He penetrated me from this position, the fullness in my ass was taking me over the edge: Brady, I'm going to blow soon." "Me too, lets go for it" He began thrusting into my gaping hole, reaching around stroking my cock. "Fuck I'm cumming….OMG....yes....fuuuuuuuuuuck." "Get ready, I'm going to fill your sweet ass with my spunk, Oh fuck...….uhh….mother fucker....mmmmmmm." We fell on the bed, the smell of sex permeated the room, our bodies sweaty as we clung to each other.

You little fucker, your an awesome fuck, are you okay." "Yeah I'm good, but I don't think my asshole will ever be the same." "Believe me Connor, your ass will be fine, its very resilient."

We took a shower together, he grabbed me, "thank you, you made my first night more than I ever planned for" "I thank you too, never expected to loose my virginity on this business trip." "Hey Connor, I'm having meetings also a business dinner tomorrow evening, but the next day I thought we could have dinner then enjoy a nice evening together. "You just want more of my ass." "Well, do you blame me, your hot....that ass of yours was meant to be fucked." I got dressed hugging Brady then left for my room.

I got back to my room, sat on the bed thinking about what happened. Fuck, am I bi, am I gay, fuck....I never felt this way with a woman. It was really weighing heavy on me, not to mention my asshole was killing me. I decided the lay in a tub of hot water. As I laid back, the hot water soothing my ravaged ass. My brain keep racing, is this what I want? I keep a conversation going with myself. I think this is what I want because it awakened something in me....loving every part of the sex I shared with Brady. Yes at first the pain was horrible, but once it passed it became glorious, explosive, the likes in which I've never experienced. I began chuckling as I got out of the tub drying myself, wow its a good thing we aren't getting together tomorrow to give my asshole a rest.

The next day I had several scheduled meetings with IT associates from different distribution centers. I tried to remain focused but all I could think about was Brady's gorgeous cock. My ass felt much better but as I thought about him I got amazing sensations in my asshole, causing me to get an erection.

That evening I found an adult store, walked in looking a different dildos, but what caught my eye was butt plugs. I decided to purchase one (a large one) also lube. I figured when we went to dinner I would wear the butt plug to stretch my hole.

After a busy day with more meetings I rushed back to the hotel, showered, cleaning myself well, lubed the butt plug, sticking it in my ass. I hoped it wouldn't be uncomfortable but after it being wedged into my hole for about an hour, it felt pretty good. I went to the bar, ordered a beer waiting for Brady. He arrived with a gleam in his eyes: "Hey Connor its good to see you, I'm hungry, do you want to eat here or go somewhere else?" "Let's eat here, have a beer before we head to the dining room."

We finished our beer, then we went to eat. As we sat there talking, the butt plug was working my ass giving me some incredible sensations. Looking at Brady, the butt plug was doing a dance in my hole, I became hard slowly moving my ass on the chair. I began to laugh: "What are you laughing for?" "You won't believe it, I have a butt plug shoved in my ass, it feels good getting me hard and horny as hell." He began laughing also, "Well I'm glad you will be prepared." We were both horny rushing through our dinner then headed up to my room.

As soon as we entered the room Brady grabbed me: "So have you been thinking about me?" "I have to say I have definitely been thinking about your cock." "Well, lets not waste any time." In a flash we were both naked, laying on the bed. "Brady, I would like to try rimming." With a smirk on his face, he laid on his stomach, spread his legs and said: "It's all yours little man." I laid down moving up to his hot ass, spreading his hairy ass cheeks, admiring his pink pucker. I licked around his hole taking in his manly scent, then went for the prize, his rosebud. I really loved rimming. I was working my pelvic muscles, moving the butt plug in me, sending waves of mind blowing sensations through my ass. "Oh yeah Connor, suck that ass, make it yours.

I got up, sat on his chest as I leaned down sucking his face, our tongues becoming entwined in saliva, the kissing dirty, obscene, full of lust. I pulled the butt plug our of my ass, took the lube, lubing his cock then more on my asshole. I took his mammoth shlong, placing it at my entrance, sliding down without any difficulty. Oh yes I had this incredible fullness, but fuck it felt good. I began bobbing up and down his shaft, there was electrical sensations racing through my body: "Fuck yeah, oh I want this cock, yes, mmmmm." "Yeah baby, ride that pole, you are on fire tonight." "With his cock buried in me, he maneuvered me onto my back, then continued pounding my ass. "Fuck yeah....mmmmm….oh shit....fuuuuuuuuck." "Brady, please cum in my mouth." He pulled out of me, got on my chest, stroked his cock three or four times then exploded. "Shit oh fuck, here it comes, oh yeah, mmmmmmmmm." My tongue was hanging open like a dog as he shot six maybe seven blasts of cum. Every shot went directly in my mouth....I took the massive load, then swallowed. I then licked and cleaned his cock as he gasped: "Conner, like I said I've been with a lot of guys, but you are at the top of my list." "I'll take that compliment, continuing with my learning, but I can tell you this business trip has changed my life, I know now that I'm gay." "I think your a great guy, if in your transition you need someone to talk to, I'll always be there for you."

We cleaned up, exchanged phone numbers, then said our goodbyes. I left the next day, but Brady and I remained friends, talking at least once a week, also made plans to visit each other. You just never know what kind of twists and turns you will experience in life.