On a senior class trip a planned sex slut failed to deliver presenting an opportunity I couldn't refuse taking.
Working Undercover
By Larry Malone
It was years ago during the annual senior class trip to Rye Beach Playland Park, NY. In those days we got there by ferry ride from Brooklyn on Long Island Sound and up the east coast to Rye N.Y. The Playland was legendary and had been around since the mid-1920s. It had everything: rides, picnic areas, skating rinks, beach, pools, concession stands, etc. The perfect place for a full day of outing for a mixed crowd.
The ferry ride was purposely slow and took about two hours since it was part of the whole day package and a treat for we inner-city kids who rarely got near water. Very few of us had been on a boat before or had ever been breathing in clean sea air. On board, and after we left the dock, I roamed around until I found a group of guys huddled around my classmate, Chris who was reclined in a deck chair covered in a blanket which I thought was strange since it was late May and very warm. Everyone was talking at the same time and agitated but quieted down when I approached since I “wasn’t one of them.” I said hi, and the guys mumbled greetings then drifted away leaving Chris alone with me. He was a little more friendly so I asked what all the talk was about. He swore me to secrecy and said that another of our classmates, Alberta, had agreed to give 10 of the guys blow jobs during the ride up to Rye if they would come up with $25 cash for her to use at Rye Beach. They had chipped in and gotten the money but Alberta had gotten seasick almost immediately when we left the dock. They were convinced she wasn’t going to be able to keep her end of the bargain. All the guys were not only disappointed but pissed.
I sat there thinking. First, I was pissed myself for not being asked to be part of the group but then I started to think of the $25 pot of money. I had very little money myself for rides and things other than what my parents could scrape together to pay for the trip and lunch with a couple bucks spending cash. The money mentioned was a lot to me and the amount sounded tempting. I casually asked Chris if the guys really cared if it was Alberta who gave them the blow jobs and his answer was “no, they just wanted a hot mouth.” Then I made him an offer, if he told no one, would he give me the money if I sucked the guys off? He asked me if I was queer, I told him, no, I was short on cash.
Chris thought it over and decided it could work since the plan was for Alberta to be under the blanket at the foot of the deck chair and stay there and the guys would each take their place sitting where Chris was sitting upright legs spread. Chris asked if I had ever done that before, I lied and said, “a few times.” He lifted up the edge of the blanket and said “show me.”
As I crawled under the blanket, he pulled down his pants and boxers revealing a rigid, cut 7” cock. Truth be told I had never done anything like that before but I certainly had seen my share of photos and porn movies to know what to do. The blanket blocked out most of the light but the strong filtered sun still made it easy for me to see. I started licking the head of his cock and was rewarded with clear pre cum liquid forming at the tip. I then started slowly sucking the head into my mouth and circled the crown with my tongue as I held the bottom of his shaft with one hand. I increased the suction and got more of the cock into my mouth. I was soon taking the entire rigid member into my mouth and hitting the back of my throat. I quickly learned to relax my throat and let the head of his cock slip in, the added tightness and my swallowing motion must have been the extra sensation that forced Chris to grab my head and shove it hard onto his cock so the last inch went in fully into my throat and I felt his cock throb his climax as cum shot directly into my stomach. I didn’t taste a thing but when I eased off his cock, licking it clean as I went, I got what was left, the taste wasn’t too bad. Slightly salty and sweet at the same time. Chris uncovered my head from the blanket and said not bad, did I really think I could do nine other guys? I told him for $25 I would do anything. He reached into his pocket and pulled out $25 in singles and handed them to me and told me not to move and to stay covered.
Chris rounded up his crew and just told them he had found a substitute but “she,” unlike Alberta who “had a reputation,” didn’t want the word to get around who she was so no one could see her or know who it was. The guys all agreed and soon surrounded the deck chair where I was under the blanket. Chris gave the guys who chipped in the most, first chance. Since he didn’t tell anyone he already had his, he let the next guy sit and get the lower half of him under the blanket. This guy just unzipped his pants, pulled them down to his thighs and tucked his BVDs under his balls. He was uncut, soft and had maybe 5-1/2” on a good day. I started to slowly jerk him off and was greeted with his meat getting hard fairly quickly as I started to suck him. His smaller size made it easier for me to suck him full strokes. I slipped a finger under his balls and touched his asshole and played with it, that got the guy really excited and he blew his load before I could deep throat him. Fortunately, his load wasn’t very big so swallowing it wasn’t a problem.
I held the blanket close to me so no one could “accidently” see who was under my end of it as the next guy got into place. This guy dropped his pants and briefs down to his thighs and was obviously black. We didn’t have too many black guys in our class so it was fairly easy to know who this guy was and who was hanging out with Chris and who belonged to the 7” uncut cock that was presented. The ebony colored shaft was a thing of beauty, perfectly formed, no curves, no bulging veins, glistening in natural skin luster. I sucked the head as I lovingly stroke the shaft worshipping a beautiful piece of human art. Before long I was mouth fucking it until it was sliding down my throat as if I was lubed up, his abundance of pre-cum helped a lot. He lasted longer than the other guy and my jaw started to get sore before I was surprised when I felt his first volume of cum hit the back of my throat. I engulfed the entire length and let the rest of the huge amount of cum shoot into my stomach. I reluctantly licked him clean and watched as he slowly got up barely able to walk.
I continued to suck the rest of the guys one by one including Chris who was the last guy. He enjoyed my mouth so much he wanted seconds. He shot his load just as the announcement came over the load speaker that we were close to Rye Beach and to start gathering our things and get ready to debark. Chris told his crew to leave and he would meet the guys at the debarking gang way, “he wanted to catch his breath.”
When everyone was gone, he pulled the blanket off us and helped me to my feet. I was a little stiff in the legs but none the worse for wear. He told me some of the guys had asked him if our unseen slut would take care of them on the way back and maybe give them a fuck for extra money. I thought about it and since I sort of enjoyed what I did, I said I would suck them again for the same amount but I had never gotten fucked by anyone and I didn’t know how we could do that without them finding out I wasn’t a girl. Chris said let him think about it and we would talk later.
The rest of the day was fantastic, for the first time in my life, I finally had enough money to enjoy all the rides I ever wanted, and treated myself to things I always wanted to try and had money left over. At lunch time when we all ate together as part of the package deal, Chris found me alone and said he figured something out. Three of the guys wanted blow jobs again and already gave him the money. Three others wanted a fuck and were willing to pay $5 each and he figured if I was willing, he would tell them “the girl still wanted to be unknown and stay a virgin but she would be willing to take it in the ass instead.” He said, that he also wanted to fuck my ass and would pay the same. He said he would see that I got another $25 in total if I agreed.
The money was tempting but I wasn’t sure I could take a cock in my ass. He said there was one way to find out, was I interested in trying before we headed back? I thought about it and said let’s try. He said he would be right back. He went over to one of the concessions stands, talked to the vendor and then came back. He told me to meet him by the bleachers near the nearby soft ball field in ten minutes.
At the bleachers, he took me to the end that was over grown with bushes and hidden from view. He told me to drop my pants and briefs and bend over. He took his pants and underwear off, and reached into his pocket and took out some pats of butter he got from the vendor and started to coat his rigid cock with some and place some into my asshole. He eased it in with his fingers and put two pats in using two fingers asking how I felt. I told him I was uncomfortable at first but by the time he got his second finger in it was feeling pretty good. That’s when he said, to relax and just breathe as his placed his greased cock head at my opening and started to press in. It was a little uncomfortable being stretched open but he went slowly and I was finally able to relax and open up. When he was fully in, he paused to let me get use to the feeling and then started to fuck me full strokes. It started to feel fantastic and after about fifteen minutes he plunged in deeper and shot a load deep into my ass. He handed me a face tissue and told me to use it as a plug to keep the load of cum and butter in as lube for the other fucks. By my satisfied grin, he already knew I enjoyed myself and was going to earn the extra money on the trip back. He also gave me a couple of pats of butter and told me to re-lube my hole before the guys started to fuck me.
When we left the Playland and got on the ferry, Chris wasted no time setting up his deck chair and blanket in the same area as before but told the guys not to start coming over util we got out into open water giving me a chance to get there and slip under the blanket. I took off all my clothes and neatly placing them under the chair and spread out face down on the deck chair covered by the blanket.
When the guys arrived, he had the ones who wanted blow jobs to go first since they would shoot their loads the fastest leaving more times for the “fuckers” who paid more money. For the blow jobs, the guys sat on the deck chair as before and I shifted positions completely covered by the blanket, with my face in their lap and I sucked them until they came. When it came time for the guys to fuck me, Chris made his instructions clear: “before or when you get under the blanket, get your own cock hard and “she” will place it at her hole so there would be no accidents entering the wrong opening.” The guys had no problems with that. I laid face down and tucked my cock and balls under me and made sure nothing could be seen from behind me. When the first guy got under the blanket, luckily he was only 6” uncut. I had placed the extra butter at my hole when I removed the tissue and was glad, I could feel Chris’ load still inside for the most part. I was hoping that load and the added butter would provide enough lube and I was right. The first guy slipped into my hole in one push and I clamped my internal muscle down hard to make my hole as tight as possible. He started immediately to fuck me full strokes and tried to reach under me to grab my “breasts” that I slapped his hands away and he kept them on my hips until he plunged and shot a load deep into my ass.
The next guy was the black guy with the 7” cock. I was glad I had taken two other cocks before his, I was relaxed and had no problem taking all of him. His added length really added to my enjoyment and he was obviously an experienced fucker and enjoyed working his cock in my ass. I felt the load he shot was bigger than the others and it felt nice to feel cum oozing out of my asshole, down my crack and onto my balls, it was all good. The final guy must have been someone new since as soon as he got fully into me, he shot his load. The others had all shot a load in the morning so it took a little while for them but this guy barely got in me and he shot so I let him stay in and fuck me some more in his slippery load before he pulled out.
After the last guy fucked me, Chris told his crew he would meet them inside and when they left, he uncovered me and helped me get dressed, offering me his handkerchief to pad my briefs to soak up some of the cum flowing out of my ass. Chris said he really enjoyed my blow job and ass fuck and our deal with the other guys, it made him look good and hoped we could somehow keep it going later on. He suggested that when we got back to school, I could become part of his crew somehow and we could work something out. Days later I had his handkerchief washed, cleaned and ironed and slipped it to him in the hall. He kept his word and we became “new” friends and the guys in his crowd never needed an “Alberta” again, but that’s another story.
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