The Challenge

By Ian MacGregor

Published on Jun 23, 1999

Gay

Once again, I was at the bookshop. I had been here several times before. Sometimes there was no action, sometimes plenty, and last time I was here there was almost more action than I could handle. My friend and I had made a bet about how many guys I could take at one time. I had handles 10+ that day, probably more like 20, and walked away to tell the story. Not only did I survive, but I had the fucking time of my life! I never really thought I could do it, but I did. Oh, I felt like the proper little whore afterwards. I felt bad for about 10 seconds, then remembered the gratitude those men had felt after I expertly sucked their cocks to orgasm or let them cum deep inside my ass. I just knew I had to try it again as soon as I was able.

This time, I didn't tell my friend I was going to do it. He would have given me a real hard time, called me a slut, etc. And what he didn't know wouldn't hurt him. I decided to go about it the same way he had, by getting on the net and posting an ad. "All Comers" the ad read, "blah blah blah at the bookstore on blah blah blah this Friday". I was nervous as all Hell during the week leading up to it, even though I had done it once already. I had no idea how many people would respond, what kind of guys I'd attract, etc. I'm a good looking guy, 5'10", lean body, somewhat muscular, hairy chest, blond hair, nice cut 8" cock... I knew I could get a date no problem anytime, and I had no trouble attracting good looking guys. This little outing, however, was completely anonymous. I did post my pic with the ad, but I had no way of knowing what kind of guys would show up for the event. But the days wore on and I got ready for the big day. I made sure to clean out my insides good, stocked up with plenty of lube, and made sure my mouth muscles were plenty loose.

Finally, Friday rolled around. At noon I showed up to the bookstore. Last time my friend had been here with me, and he'd handled some of the traffic. This time there would be no such help. I'd have to take as many of them on as I could by myself. This was going to be the ultimate challenge. As I walked in, I could tell the place was busier than usual. There were about 10 guys up front just looking at magazines, videos, or sex toys. As I got my quarter, I saw several eyes turn my way expectantly. I just smiled and headed to the video booths. I'd described what I'd be wearing and what I looked like in the ad, so most of the guys there recognized me. I saw a few familiar faces, probably from the last escapade I had. I found a booth near the back, walked in, and prepared for company.

I stripped down completely nude, stretched a little, and slipped a quarter into the machine. Before long there were knocks on the door and frantic cocks shoving through the glory holes on either side of the booth. I slid the lock on the door open and proceeded to go down on the smaller cock of the two. No need to wear myself out too early. A young guy was the first to enter, about my age and not too bad looking.

He quickly pulled out his hardening cock, which was a good 8" semi-hard. I grabbed it and stroked it while I continued to suck on the anonymous cock in the gloryhole. He was soon joined by another man, then another until there were 3 guys in the booth besides me. It was cramped, but it was full of hard cock so it was fine by me. I left off the cock in the gloryhole and started to suck the young guy. The other two were older, both in their mid 30's or so. Both were a little out of shape, but good looking with nice cocks nonetheless. I took turns sucking them off while trying my best to jack off the other two. Soon the young guy went around to my backside and pulled out some lube.

He greased me up good and slid his big tool into my ass slowly. It was tight at first, but he took it slow and got it all in while I sucked and jacked the other guys. Once he was in all the way he really went to town.

While this was going on, I was able to sneak a peek at the gloryholes. We were definitely being watched, and obviously it was a hit with the guys with me. They were going on about what a good cocksucker I was, moaning and panting, getting ever closer to filling me with their sperm. I gave it all I had and before long both of them were cumming on my face at the same time the young guy was filling my ass with molten hot cum. Once they were finished, I cleaned their cocks off and they returned the favor by licking my face clean of their own cum. Almost as soon as they turned to leave there was a commotion as doors were unlocked for fresh cocks to come in and use me. The first batch walked out and 2 more came in.

These two must have been brothers; both were black, both were big, and both had shaved heads. I couldn't wait to see what their other heads looked like. They didn't make me wait long. The older of the two, I think, pulled his out and grabbed me by the back of the head forcing me down on it. I obeyed instantly and took all I could of his massive tool into me. He was probably a good 9", and his brother must have been about the same or a little bigger even. He pulled his out and began stroking it while I sucked his brother off. I once again began to alternate between them, but before long the older man had enough and wanted to fuck me. He moved around behind me and I obliged him by rising up to meet his big cock. With both meaty hands he grabbed my waist, then he forcefully pushed his monster cock into my ass with one shove. I was lucky his brother's cock was filling my mouth so well because the yelp I would have let out would have gotten me tossed out of the place for sure. The pain was intense for a few moments, but he kept his cock in me and allowed my ass to adjust to its size. Soon he was taking deep, powerful strokes in and out of me while his brother matched him stroke for stroke in my mouth.

The older one came first, almost yelling out as he took one last stroke and filled me full of cum. His brother wasn't done yet, and he moved around to quickly take his brother's place in my ass. As he started to fuck me, the older one got on his knees and sucked my cock while roughly pinching my nipples. The guy fucking me began to get rough, too, slapping my ass cheeks and pounding his big dick in and out of me with no mercy. To keep my voice down, the older one told me to put a cock in my mouth, looking over to one of the glory holes where a hefty cock protruded. I greedily complied and was once again sucking a cock while getting fucked. The older one went back to sucking me as best he could, and by then it didn't take long for the younger man to shoot his hot load up in my ass. They both cleaned up and left while I was still working on the cock in the gloryhole. As they walked out they both slapped my ass cheeks forcefully and said "nice job, man". They walked out and left the door wide open for the next group to come in. They quickly took the cue and I was soon joined by 3 more guys. One was black, the other two white. All were young and looked to be well hung.

Frat guys I would guess. Probably taking a dare or something, but they looked serious although a bit nervous. I pulled off the cock in the gloryhole, but didn't want to lose it because it was so nice. So I turned around and pushed it into my ass. Then I told the guys to line up in a row with their cocks out and that I'd do all the work. I shoved my ass up hard against the gloryhole and went to work on the new guys. All were nicely built with nice cocks, one about 7", the next the same, and the black guy slightly bigger with 7 1/2". It didn't take them long to cum, each almost at the same time. They each aimed for my mouth, but some cum got on my face and some on the floor. Luckily I'd brought a towel, because these scared little rabbits zipped up and were out the door quick as a flash without so much as a thanks. So I grabbed the towel and wiped off while turning my full attention to the great cock fucking me. He'd been long dicking me for a while now and I wondered how long he could go on. But I was cut short in those thoughts by a new sight coming in. It was a guy and what looked to be his girlfriend, although she was considerably older than him. He was maybe 30 while she was probably closer to 45. Both were good looking though, and I didn't object to their joining me. The man turned and locked the door, then they both proceeded to strip naked. I didn't know what they expected from the arrangement, but I was intrigued to find out. The man had a nice body, a little chunky but with nice bulk and an even nicer cock. It was only about 6 1/2 inches, but it was thick as my wrist. The woman also had a very nice body for her age, with nice large breasts and a shaved pussy. They kissed a while in front of me while I was being ram-rodded by the gloryhole cock, then they came over and began to caress me and kiss me all over. The man gave me his cock and I sucked him while the woman kissed him and felt his ass. He fingered he pussy and I lent him a hand at it.

He pulled out and backed away, then she got between us and went down on him while exposing her ass and pussy to me. I pulled her to me and licked her up and down. She had a nice clean pussy with a sweet taste.

They kept this up for about 5 minutes, then She bent over the bench and he stuck his cock up her pussy and began to fuck her like crazy. It didn't take him long to get ready to cum, and as soon as he was ready she got up and came around to lean over beside me. He positioned himself in front of us and let fly with a big wad of sperm. Both of us got bathed in it, catching what we could. Once he was done, we licked eachother off. They stayed a few more minutes watching me and getting dressed, and then left smiling.

The rest is about the same, with the one exception of the man and woman. More guys fucking me, cumming in my mouth or ass. The gloryhole cock fucked me for close to 45 minutes. Others were not pleased to be cut out of that pleasure, but I wasn't about to give up until he came. He waited for me in the lobby after all was said and especially done, and he gave me his number. He had a great cock, but that was all he had. No offense, but if I'm gonna see a guy more than once, he's gotta have something more than a nice cock. But I do hope I get the chance to get fucked by him next time, and there will be a next time. I estimate that I did more this time than last, probably closer to 30. I was exhausted, but I had cum 3 times and swallowed close to a gallon of cum, as well as all the cum that flowed out of my ass when I was done. Call me a slut, I don't care. I know what I like and I got lots of it.


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