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Windy City Initiation
Hard Way to Gay It was my first assignment outside of Wyoming. I had never been to Chicago, but was anxiousley looking forward to the bright lights, big city, and of course, the extra pay that road assignments offered, with unlimited overtime. I got just what I was hoping for, working 7 days a week for several weeks straight without a break in downtown Chicago. The hotel was so close to my work that I walked to and from work everyday. I had been passing by what seemed to be a very nice little bar, for several weeks thinking I might stop in for a beer or two, sometime if I got off from work early enough, that I wasn’t worn out from exhaustion. Finally the project slowed for lack of materials, the crew leader advised, we all had entire 3 day weekend starting Thursday afternoon. I was walking back to the hotel early in the afternoon, and in passing the little bar again, I thought tonight I am going to have a couple of beers and relax. First I had to call the wife, and chat with her a bit and get a shower and some dinner. Later that evening after having completed what I wanted to get done. I walked down to the little bar. Upon entering the bar, I didn’t give much attention to the fact that for such a small bar it was quite busy, and that it was almost all men, there were a couple of women sitting together but I didn’t give it much notice. I sat down on a bar stool and after a few moments the bartender asked me if I was sure I wanted to be in this bar. Being quick and short with my response I replied with a question of my own, asking if they sold beer in this here bar. The reply was a bit less than friendly, but was of course they sell beer it is in fact a bar, and he took my order. Moments later he returned with my beer, and 2 shots of tequilla, advising that the gentlman seated at the end of the bar wanted to each buy me a drink. I thought what the heck, tell them I said thank’s, I lifted my beer and told them thanks, not they actually could hear me over the noise in the room. A few moments later I drank the 2 shots and chased it with the beer, they seemed like they were rather large shots though I was thinking. Within a few moments of finishing my beer the bartender reappeared in front of me, wanting a little chit chat based upon his opening discussion. Your not from around here, he asked me. I am thinking must be the jeans jacket, and pants, giving me away. I replied no I am from Wyoming, and proceeded with brief explanation of what I am doing in the windy city. Anyhow the bartender leans a little closer over the bar and says to me you do know this is a gay bar, don’t you. I replied, I wasn’t actually aware, however seems like a nice place, and the fact that I am straight, shouldnt be a problem I asked. No problem here, he advises, and brings me another beer. Within a few minutes a couple of more shots arrive in front of me, the ol bartender tells me there from the same 2 guys at the end of the bar. Thinking I probably should not accept, not wanting to give off a wrong signal, but not wanting to be rude, I thanked them again. After finishing the shots, and the beer, I had to find the toilet, after looking around a bit all I could see was a set of stairs going up. In asking, I was told the toilet was up stairs. When I reached the top of the stairs I noticed it was quite dimly lit another bar, and sure enough far at the end of the room I could see the restroom. After relieving myself, and returning back out into the upper, dimly lit bar, I thought maybe a good idea to sit up at this bar for another beer before I go. I was at the point where I was aware that I was just about at my limit, I had to walk back to the hotel yet tonight, even though it was close I wanted to walk not crawl, and absolutely was not up for drinking too much and getting sick. Anyhow I took a seat at the far end of the bar, ordered me another beer. It wasn’t more than a matter of minutes the 2 guys from downstairs appeared, both of them sitting down one on my left and the other on my right. They started with a little chit chat, and before I knew it several more beers, passed, several more shots, a couple of more hours and I was plastered, still having my wits about me somewhat. In being busy drinking and chatting I hadn’t really noticed the hour, nor had I really bothered to pay attention, to the fact that the upper bar had mostly cleared out. The 2 guys both middle aged mid to late 30’s same as me average shapes, and build, the one on my left Jim, and the one on my right Tony, had kept me well supplied with drinks, and comfortable conversation throughout the evening. Tony had to get up and step to the toilet, in his absence I was sitting there alone with Jim, and a quick change in conversation, to the question of, had I ever had my cock sucked, by a guy, or ever considered sucking a guys cock. I quickly replied no to both, and the talk ended as quickly as it had started. Within a few minutes Tony returned, and Jim, got up to go to the toilet. Sitting there and not talking much for a couple of moments, Jim reached over and put a hand on my leg without saying a word and quickly moved it to stroke my groin. I was instantly aroused, by the move, and at the same time I felt a lot uneasy about the stroking that continued, and at the same time I had a ragging hard on straining my jeans, so fast that I was definetly getting turned on, and I was getting extremely horney. It had only been a few moments and sure enough Tony, returns and notices that Jim is stroking me through my jeans. A few more drinks arrive, and I decide that I am getting a turned on enough, that the thought of maybe getting a blow job might not be so bad even if it is a guy. The 2 of them continue with the stroking, and rubbing my leg, and the drinks seem to become so smooth going down, before I even realize what happened, my pants are unbuckled, and Jim has my cock in his hand. I am thinking even though I am way drunk I am going to jail for sure, and put up a little resistance with the explanation that we are in a public bar. At that point Tony advises that the bar is actually now closed, and only private guests remain and most of them are all downstairs, and that this happens frequently here in the bar, and that there is nothing to worry, or be concerned about. Before I know it my pants are at my ankles and Jim is on his knees sucking on my cock. A few minutes pass by, and Tony stands up with his pants dropped and a massive hard cock hanging there, that I thought must belong to horse. Tony was stroking on his cock while Jim, was sucking on my cock. Tony stepped closer and started rubbing his huge cock over my face cheeks, and I am thinking he is going to be trying to stick it in my mouth, and sure enough without missing a beat he stuffs it in my mouth grabbing the back of my head, to ensure he could hold my face from escaping his cock getting into my mouth, leaving me no ability to argue the action. I was only seconds into having a cock in my mouth, and simoltaneousely, receiving an amazing blow job, and I realized that I was actually getting hornier, and the cock in my mouth, was not as uncomfortable, or as repulsive as it first was, even though I was being gaged, from the sudden impalement and depth of reach that the huge cock had, pounding the back of my throat. It was in my mouth, and was starting to think it was quite enjoyable. A few minutes seemed to pass which, was in all reality probably a few seconds, and Tony, grabbed my hair hard, uncomfortably hard, and he shot his load right into my throat, giving me no option but to swallow. At almost the same moment, I shot my load into Jim’s mouth. Tony, romoved his cock still dripping cum and rubbing it onto my lips, saying what a good cock sucker I was for a first timer. I instantly felt this overwhelming anger at myself, for what I had just done, and allowed to be done to me, yet at the same time I was still sitting there with Jim, sucking on my cock, ensuring he was getting every last little drop of my cum. Tony handed me drink to wash down the cum that I had just swallowed. And within a few minutes, the room seemed to be spinning and I was thinking I was going to be sick. Tony said that maybe I should stretch and relax on several of the bar stools for a bit. I managed to get my pants back up and staggered to the bathroom after relieving myself and splashing water onto my face I was feeling much better.
I returned to the bar, and mentioned that I should be going soon back to my hotel, and Tony, and Jim, both insisted that in my condition they should walk me back ensuring that I got to my room ok. Thinking that might be a good idea, late at night and dark city streets of Chicago and all, but before they left, they both insisted and wanted to have just one more drink before we left. I grumbled a bit but agreed, to just one more drink and that was it. The one more drink arrived, and was in a tall tumbler glass and I was sure there was no way I was drinking that much more alchol tonight. The one more drink returned me back to my very horney, and very drunk, stage after a bit more of jean stroking and once again my pants were down at my ankles, and moments later completely off. Jim decided that I should try being rimmed, not exactly sure of what he was talking about, he got me to bend over the bar stool, where he promptly spread my ass cheeks and buried his tongue into my ass. I was instantly turned on, and while Jim was working my ass, Tony was what appeared to be uncomfortably reaching around around stroking my cock, and I continued to enjoy the pleasure of Jim tongueing my ass. Tony had stopped stroking my cock and stepped in behind Jim, who got up and came around in front of me with another large cock shoving it toward my mouth, this time I willingly opened my mouth and allowed Jim to shove his cock in and I started sucking. Tony had started playing with my hole with his fingers that was turning me on more and more, all the while I was sucking Jim’s cock. I was just truly enjoying Jim’s cock and the ass fingering I was getting when I felt Tony pushing at my ass and this time he was shoving his massive cock into my ass, I was usre I was being ripped apart, and wanted it to stop but Jim had grabbed the back of my head, and being bent over the bar stool I had no way of arguing the screaming pain, after a few moments the pain that was at first so intense, was slowly dissapating, I thought for sure Tony, had shoved his massive cock all the way in me. Tony was starting to work my ass with his cock, very slowly in and out, and it was starting to feel really good, when he told me to nod if I wanted more than just the head of his cock, in me. I thought he was fully inside of me, my ass was feeling so good all I knew was that I wanted more. Without hesitation Tony, continued to ram his cock deeper, and deeper into my ass, the sensation of being ripped in half tripled in affect, and the pain was almost unbareable. Jim continued holding the back of my head, face fucking me harder and harder, making sure I was not going to argue the moment. Tony continued pounding his cock into my ass, and with Jim having his cock in my mouth I had not noticed that about a dozen additional men had gathered around the action of the breaking in of my virgin ass, and the initiation of me to gay sex. Within a few minutes Jim started pushing harder, and leaned back, and cocked my head so I could see his face as he shot his hot load of cum into my mouth. Jim then got aggressive in tone, and started telling me swallow bitch, swallow, I decided to comply. Just as I am swallowing Jim’s cum, I feel Tony start to shudder as he grabs at my ass cheeks, slaps them, and shoots his load deep into my ass. Just as Jim pulls his limp cock from my mouth another gets stuffed in before I had a moment to catch my breath. The same happens with my ass, Tony pulled out and another much smaller cock was quickly slambing in and out of my ass. A few moments and the person that was fucking me had cum and finished, just as I was thinking this was almost over another large cock, slammed into my ass, with a few quick words of being told to be happy slut your getting what you really want and truly like, I relazied the large cock in me was Jim. Within a few minutes of being deep stroked by Jim, I started cumming, and cumming, I felt like I must have cum a gallon for sure but could not see from the position I was in. After having cummed I really wanted to be done with this and get up and go to my hotel room. My ass was starting to ache, and after I cum I usually always get way sensitive, and like to shower and relax. But after cumming, I still had Jim deep stroking my aching ass, and this other guy fucking my face. So I knew I was going to have to endure more for a little longer. Within a few more moments the guy fucking my face grabbed the back of my head, and told me prepare to swallow slut, just as he shot his gooey, hot load deep into the back of my mouth. At this point the ache of my ass was subsiding and the guy with his cock in my mouth stepped away. I was looking up at the guy that had just finished fucking my face, when I heard several of the other guys laughing wondering if they should let the slut have a break. Jim stopped fucking my ass just long enough to say as long as I was not arguing they should all enjoy the bitch, with that said another cock was in my mouth. Jim finished as did about nine, other guys in my ass, and at least six more, fucked my face, I was to the point where my jaw was aching. Tony, and Jim helped me up, and cum was running down my thighs, from my well lubed ass, I managed get my pants on and then Tony, and Jim, walked me out to see that it was becoming daylight. I had sucked, and been fucked all night long and when I finally got into my hotel room, Tony laid me down on my bed, I must have slept the entire day away, and was half asleep when I was startled awake by someone rubbing my cock, I realized upon opening my eyes it was Tony, he noticed I was startled, and quickly asked if it was ok if he continued, and I agreed. He then asked if I was honest about having never had sex with a man until last night, I replied absolutely last night was the first time ever. Tony, smiled and said welcome to the otherside of life, and proceeded to fuck me long and hard for the next several hours, pumping a load into both my ass and my mouth.