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This was said to me by my friend, Ross, but also number one rival. This story begins to explain how he found out and the unpredictable consequences that eventually occurred.
We were students and had grown up together as neighbors. I say we were friends but the relationship was always strained and competitive. For instance, in high school we both played drums in the band and fought for first position. We had rivalries over grades, and dating, etc. The worst for me was Ross was the first one to have a real girlfriend and sexual relationship with her. He would flaunt her and that relationship in my face. I also learned he had an encounter with a girl in my neighborhood that I liked a lot but never showed that interest of me in return. I did consider myself better looking and it was always depressing that he was having the successes that he was experiencing while at the same time I was striking out.
The worst situation for me came a bit later. Ross had dated a girl, Beth, who sort of was part of a group of friends where all of us would occasionally do things together. I guessed they had sex but I never was certain. At some point, however, they seemed no longer an item as Ross was now flaunting a new relationship with an absolute buxom beauty. Beth and I grew a bit closer and eventually started dating very soon thereafter.
Beth had her own apartment and after going to a movie one evening we ended up at her place and started making out. She became fairly aggressive and things were progressing toward obvious sex. However, as we got more and more intimate I had to put a stop to it as I did not have any condoms and was not willing to take a chance on pregnancy or other things. Of course I was horny as hell and hard as a rock but had to force myself to stop until I could get protection. Plus, truth be told, I am somewhat a premature ejaculator if things are bareback or even with oral that I had once or twice. So, with a condom I feel more control and confidence. Beth of course was confused at first as to why I was slowing down in a very heated situation. She seemed hurt asking what’s wrong and it was evident I was going to blow the whole relationship so I had no choice but to tell her. She laughed and said, “I have some.” I kind of laughed back which was a mistake as she looked annoyed that I did so. “Ross, left them, I mean you know he and I were a thing for a while, right? It’s over you known and that’s not a problem is it as I know you two are friends.” I responded explaining of course not and that actually we were not that close (although I didn’t share our rivalry either).
Beth reached into a drawer and pulled out a condom in the cover. We started kissing and got very intimate slowly shedding our clothes. Eventually we were naked of course and I first moved and went down on her until she seemed to climax. She then moved to suck my cock and then I grabbed the wrapper pealing open the condom placing it on my fully erect cock. She stopped and said, “I think this is not the right size for you”; as it was a magnum and was too loose with a long amount of the condom hanging off of me. She frowned and added, “It’s not going to stay on is it?” I grabbed it easily pulling it down with the extra folds that were too long and was frantic to make this work but she was right as soon as I started to enter her it folded up and when I pulled back the condom slipped right off. It suddenly occurred to me that Ross was using a magnum. I inquisitively asked, “These fit Ross?” “Oh my god” she laughed, “He complained they were tight on him.” “I mean you know Ross has that monster sized cock.” She actually used that word, “monster” and it was very intimidating and I started to immediately lose my erection.
You guys have seen each other naked,” Beth said straight forward like none of this mattered it just was the facts to her. Beth, I responded, “We don’t go around like that and no I haven’t seen Ross before without his clothes on.” “Oh,” Beth said in a voice like someone making a scientific discovery. She continued, “When I saw Ross naked for the first time it was shocking. I mean he is not some big muscular guy so you don’t expect to see something so big and out of proportion with the rest of his body like that.” Of course hearing this was very upsetting. My rival was being described as a very well-endowed guy whereas I knew mine was average at the very best and maybe slightly less from videos I had seen. I felt embarrassed that she was seeing my size which apparently was a lot smaller than Ross. Beth meanwhile said, “Let me get you off in another way and maybe you can buy some condoms that are right for you.” She reached down to grasp my penis and saw that I now was completely flaccid and not responding to her touch. She stroked my cock and then started sucking it but I wanted to get out of there now feeling that I could never compete with Ross sexually. Beth of course could not help but notice my lack of response and started tugging harder which only made it worse. “Have I upset you, what’s wrong” she asked. “No, everything is OK, maybe I am tired now,” I said giving an obvious lame excuse. Beth was not stupid and with a slight tone of annoyance said, “I hope you are not one of these guys worried about the size of your dong” using those exact words. “You know it doesn’t matter, right, from what I saw earlier yours is fine.” Of course Beth could not understand being a woman that yes it did matter and especially how she described Ross, the guy that mattered most to me in a rivalry having a monster cock and mine being not even in the larger than average category. It was upsetting to learn.
Beth eventually gave up as I was not responding to her oral attempts and her hard tugging didn’t feel good either. “Just hold me” she finally said and we lay there quietly more or less cuddling although inwardly I wanted to be somewhere else still feeling embarrassed about my size and now inability to respond. I finally said, “Beth, will you be honest with me, I mean totally honest no matter what?” Beth looked at me and said, “I am honest, sometimes people will say brutally honest.” I told her,” I never knew what you shared about Ross, how big is he?” “Really, you want me to talk about him” Beth asked but now with a more relaxed conversational tone. “Yes”, I said, he and I have known each other a long time but I never knew about that aspect and I am curious what sex is like with someone that way.” “I won’t lie” Beth said. “No, I don’t want you to lie” I again re-stated.
Beth held her hands apart at a significant distance and said, “Like that and very thick, I was not kidding it was a monster.” Oddly enough when she did this hand gesture my penis began stirring and jumped a little. She added “I honestly was a bit intimidated as I thought it was going to hurt but he took his time. Like I said, size doesn’t really matter but it is always nice.” With Beth adding that last part on size being nice my penis began quickly growing erect. “Oh this is turning you on” Beth smiled. I said nothing so she continued. “OK honestly once I relaxed and we got into it, it was amazing.” Now my cock was hard as a rock. She began jacking my cock and moved between my legs and started sucking my cock and holding onto my balls. She would suck my cock for maybe 10 second or so and then look up continuing to talk. I actually was somewhat perplexed at my reaction to all of this. I was very turned on but felt shy about it and also somewhat questioning of myself as to why it was such a turn on. I thought the fact that she was talking and openly sharing had a lot to do with it but also I wondered if I was secretly fascinated with Ross’s cock. Now that I was fully erect I said to her, “show me how much longer his is than mine.” “You want me to compare your cock to his” Beth asked in a somewhat surprised voice. I now was having to hold back from cumming I was so excited. I barely could speak and with a stammer said “Yes.” Beth responded, “OK I told you I would be brutally honest.” She held her finger way above the head of my cock and said, “Maybe 3 to 4 inches longer, what is yours around 5 inches? Beth explained, “Ross bragged to me when I was shocked by seeing it that he was a solid 9” long She looked up at me and said, “It was a lot fatter than yours too.” I couldn’t help it any longer as I shot an intense load which went flying up into the air some of it hitting the right side of her face and the rest almost shooting as far as right under my neck. I was super charged and super turned on. Beth smiled and said, “wow” now that was amazing.”
We again lay still for a few minutes and I said,” Beth, I will buy some condoms if you still want me to have sex with you.” “Of course” she responded and we kissed and hugged. Now that my sexual desires had subsided with my climax I did feel some shame of her knowing what just turned me on. Yet, I also knew that I wanted her to compare how I felt fucking her versus her experiences with Ross. Little did I know that a few months later that our sharing ended up betraying me in a way I never imagined and what that would lead to (to be continued?)
We were students and had grown up together as neighbors. I say we were friends but the relationship was always strained and competitive. For instance, in high school we both played drums in the band and fought for first position. We had rivalries over grades, and dating, etc. The worst for me was Ross was the first one to have a real girlfriend and sexual relationship with her. He would flaunt her and that relationship in my face. I also learned he had an encounter with a girl in my neighborhood that I liked a lot but never showed that interest of me in return. I did consider myself better looking and it was always depressing that he was having the successes that he was experiencing while at the same time I was striking out.
The worst situation for me came a bit later. Ross had dated a girl, Beth, who sort of was part of a group of friends where all of us would occasionally do things together. I guessed they had sex but I never was certain. At some point, however, they seemed no longer an item as Ross was now flaunting a new relationship with an absolute buxom beauty. Beth and I grew a bit closer and eventually started dating very soon thereafter.
Beth had her own apartment and after going to a movie one evening we ended up at her place and started making out. She became fairly aggressive and things were progressing toward obvious sex. However, as we got more and more intimate I had to put a stop to it as I did not have any condoms and was not willing to take a chance on pregnancy or other things. Of course I was horny as hell and hard as a rock but had to force myself to stop until I could get protection. Plus, truth be told, I am somewhat a premature ejaculator if things are bareback or even with oral that I had once or twice. So, with a condom I feel more control and confidence. Beth of course was confused at first as to why I was slowing down in a very heated situation. She seemed hurt asking what’s wrong and it was evident I was going to blow the whole relationship so I had no choice but to tell her. She laughed and said, “I have some.” I kind of laughed back which was a mistake as she looked annoyed that I did so. “Ross, left them, I mean you know he and I were a thing for a while, right? It’s over you known and that’s not a problem is it as I know you two are friends.” I responded explaining of course not and that actually we were not that close (although I didn’t share our rivalry either).
Beth reached into a drawer and pulled out a condom in the cover. We started kissing and got very intimate slowly shedding our clothes. Eventually we were naked of course and I first moved and went down on her until she seemed to climax. She then moved to suck my cock and then I grabbed the wrapper pealing open the condom placing it on my fully erect cock. She stopped and said, “I think this is not the right size for you”; as it was a magnum and was too loose with a long amount of the condom hanging off of me. She frowned and added, “It’s not going to stay on is it?” I grabbed it easily pulling it down with the extra folds that were too long and was frantic to make this work but she was right as soon as I started to enter her it folded up and when I pulled back the condom slipped right off. It suddenly occurred to me that Ross was using a magnum. I inquisitively asked, “These fit Ross?” “Oh my god” she laughed, “He complained they were tight on him.” “I mean you know Ross has that monster sized cock.” She actually used that word, “monster” and it was very intimidating and I started to immediately lose my erection.
You guys have seen each other naked,” Beth said straight forward like none of this mattered it just was the facts to her. Beth, I responded, “We don’t go around like that and no I haven’t seen Ross before without his clothes on.” “Oh,” Beth said in a voice like someone making a scientific discovery. She continued, “When I saw Ross naked for the first time it was shocking. I mean he is not some big muscular guy so you don’t expect to see something so big and out of proportion with the rest of his body like that.” Of course hearing this was very upsetting. My rival was being described as a very well-endowed guy whereas I knew mine was average at the very best and maybe slightly less from videos I had seen. I felt embarrassed that she was seeing my size which apparently was a lot smaller than Ross. Beth meanwhile said, “Let me get you off in another way and maybe you can buy some condoms that are right for you.” She reached down to grasp my penis and saw that I now was completely flaccid and not responding to her touch. She stroked my cock and then started sucking it but I wanted to get out of there now feeling that I could never compete with Ross sexually. Beth of course could not help but notice my lack of response and started tugging harder which only made it worse. “Have I upset you, what’s wrong” she asked. “No, everything is OK, maybe I am tired now,” I said giving an obvious lame excuse. Beth was not stupid and with a slight tone of annoyance said, “I hope you are not one of these guys worried about the size of your dong” using those exact words. “You know it doesn’t matter, right, from what I saw earlier yours is fine.” Of course Beth could not understand being a woman that yes it did matter and especially how she described Ross, the guy that mattered most to me in a rivalry having a monster cock and mine being not even in the larger than average category. It was upsetting to learn.
Beth eventually gave up as I was not responding to her oral attempts and her hard tugging didn’t feel good either. “Just hold me” she finally said and we lay there quietly more or less cuddling although inwardly I wanted to be somewhere else still feeling embarrassed about my size and now inability to respond. I finally said, “Beth, will you be honest with me, I mean totally honest no matter what?” Beth looked at me and said, “I am honest, sometimes people will say brutally honest.” I told her,” I never knew what you shared about Ross, how big is he?” “Really, you want me to talk about him” Beth asked but now with a more relaxed conversational tone. “Yes”, I said, he and I have known each other a long time but I never knew about that aspect and I am curious what sex is like with someone that way.” “I won’t lie” Beth said. “No, I don’t want you to lie” I again re-stated.
Beth held her hands apart at a significant distance and said, “Like that and very thick, I was not kidding it was a monster.” Oddly enough when she did this hand gesture my penis began stirring and jumped a little. She added “I honestly was a bit intimidated as I thought it was going to hurt but he took his time. Like I said, size doesn’t really matter but it is always nice.” With Beth adding that last part on size being nice my penis began quickly growing erect. “Oh this is turning you on” Beth smiled. I said nothing so she continued. “OK honestly once I relaxed and we got into it, it was amazing.” Now my cock was hard as a rock. She began jacking my cock and moved between my legs and started sucking my cock and holding onto my balls. She would suck my cock for maybe 10 second or so and then look up continuing to talk. I actually was somewhat perplexed at my reaction to all of this. I was very turned on but felt shy about it and also somewhat questioning of myself as to why it was such a turn on. I thought the fact that she was talking and openly sharing had a lot to do with it but also I wondered if I was secretly fascinated with Ross’s cock. Now that I was fully erect I said to her, “show me how much longer his is than mine.” “You want me to compare your cock to his” Beth asked in a somewhat surprised voice. I now was having to hold back from cumming I was so excited. I barely could speak and with a stammer said “Yes.” Beth responded, “OK I told you I would be brutally honest.” She held her finger way above the head of my cock and said, “Maybe 3 to 4 inches longer, what is yours around 5 inches? Beth explained, “Ross bragged to me when I was shocked by seeing it that he was a solid 9” long She looked up at me and said, “It was a lot fatter than yours too.” I couldn’t help it any longer as I shot an intense load which went flying up into the air some of it hitting the right side of her face and the rest almost shooting as far as right under my neck. I was super charged and super turned on. Beth smiled and said, “wow” now that was amazing.”
We again lay still for a few minutes and I said,” Beth, I will buy some condoms if you still want me to have sex with you.” “Of course” she responded and we kissed and hugged. Now that my sexual desires had subsided with my climax I did feel some shame of her knowing what just turned me on. Yet, I also knew that I wanted her to compare how I felt fucking her versus her experiences with Ross. Little did I know that a few months later that our sharing ended up betraying me in a way I never imagined and what that would lead to (to be continued?)