Cross-dresser Teaches Me A Lesson

trulybig

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Have you ever felt too confident and then get you comeuppance? It happened to me but retrospectively with an unforgettable experience I really don’t regret. I just never imagined it would happen to me.

First and most important to this story is I have a big dick. I have known that fact for most of my adult life and have been proud of it. My sexual experiences with women have all been positive with many compliments on my size and skills in using it. Now I am not a monster sized which I am happy about. Women don’t run from me and it has fit in them, but still I am much bigger than probably 90% of the human male population. Every women I have ever been with (and there have been many) have said it is the biggest they have experienced.

I also have had an attitude about guys with little dicks or noticeably smaller than mine. Honestly, when I see a video or viewing web cam sites, I just don’t understand the attraction when I see a really attractive woman with a small endowed man. I feel like those women deserve and should demand being with a man that equals their superiority in looks possessing a bigger and better cock too. Plus, small penises especially on otherwise well built guys look ridiculous. The small size makes them look less masculine and so yes I always equated my masculinity with my bigger size. I know this makes me sound bad. Well, as you will read this superior attitude ended up teaching me a lesson in the most surprising way.

I had traveled on business and was staying in an upscale hotel in New Orleans for the week. On the concierge level at the top they had a bar for those who qualified like me. Typically, there are other businessmen and sometimes a few women sitting around having cocktails and likely bitching about their sales visits during the day or similar work related conversations. Late in the evening most have relaxed, perhaps with a few cocktails and it often is guy talk too meaning sports, etc. So people in this scene are usually casually friendly. I had a long conversation with this one guy the first night. He was a slightly built guy, short in stature, probably in his late 30’s; there was some conversation about his family, wife, kids, but mainly the other topics I just mentioned. However, New Orleans can be a wild town and we discussed going bar hopping the next night.

If you have ever been to the New Orleans French Quarter you will know they have a wide variety of bars including gay bars, transvestite bars, strip shows both male and female, and it can be a wild place. We stopped at a few different places and I guess I made some derogatory comments about the gay bars or guys there as we passed them by. My new friend, Paul, didn’t respond when I would make some of these comments. However, on the walk back to the hotel he expressed anger at me regarding my comments. “You seem very opinionated and kind of closed minded. Sort of full of yourself.” I responded that if I offended him it was not my intent but yes I did look down on certain guys. He asked me why and I said well to be candid I am pretty well-endowed and I see myself as a masculine guy. Paul laughed. I asked what was so funny and he replied, ‘Your thinking.” Now do remember we both had a few drinks and so were not holding back or filtering our conversation. I asked Paul how he felt differently.” “So you think the size of your package equals the measure of your masculinity.” What if a guy who liked feminine stuff had a larger package than you? Would that mean he should be the alpha male nevertheless?” I responded, “I doubt he would have the bigger cock.” Paul then said, “Well if the guy had a bigger one than yours does he rule, do you have to do what he says because his is bigger? I responded, “Yes, but that is not the case with me, everyone woman I have been with has complimented me on that feature.” Paul suddenly said, “I bet mine is bigger than yours?” Now again remember I wasn’t drunk but certainly was not entirely sober either. “How much do you want to bet” I challenged him. Paul answered,“Not money, but if I win, you have to do what I say. If you win, name it? Paul, what about you pay me $500. I said a large dollar amount because I knew he wouldn’t agree to that. However, instead he surprised me and said, “OK, but if I win you have to do what I say, agree?” I now was a bit nervous, but this slight short guy couldn’t be packing more I felt. “Deal” I confidently stated.

Paul said as we got into the hotel, “give me about 20 minutes and I will call you”. I asked, “How are we going to be turned on enough to show our full pride”. Paul said “I will put on some porn”, I got back to my room and starting thinking this is so crazy. But, it was also exciting as I could use the $500 and also wanted to really show up Paul now that he had challenged me. My room phone rang and Paul told me his room number and also said, “I am going to have a surprise for you.” I asked him what, but he said it would be surprise and not to worry.

I knocked on his door and I heard a higher pitched voice say it’s open and to come in and shut the door behind. I entered the room which was dark but enough light to see a figure sitting in a recliner chair. As I walked closer, I could see an attractive woman with long blond hair and a skirt on with heels. I knew I was in the right room but quickly looked around for Paul not seeing him. “Um, I stammered, where is Paul.” I heard that higher pitched voice say I don’t know about Paul, I’m Pauline. I looked and to my utter shock now realized it was Paul. I didn’t know what to say. Paul/Pauline said, “See how I look, I like to dress up sometimes in women’s clothes but I am a masculine guy too and will be an Alpha to you.” I will admit as Pauline, Paul looked pretty good but this was too weird for me and I turned around and started to head for the door. Paul now shouted, “Hey our bet.”

I stopped at the door and to this day I am not sure what influenced me, my desire for the money, my curiosity, my somewhat inebriated state, and perhaps will never know for sure. However, I turned around and said, “Well beat this” and unzipped my fly. However being nervous and somewhat uncomfortable with Paul’s appearance, I was only slightly hard. Paul still sitting instructed me to come closer so he could have a better look. I did and told him I wasn’t even fully erect yet. “It’s impressive “Paul said, and reached out and grasped my cock. “Whoa, I am not gay.” Well you’re with Pauline it’s OK and so quickly she leaned forward and sucked my cock right into her mouth (yes I said her). I couldn’t believe I was doing this but the sucking felt really good and I grew to my full erect size very quickly. “See it’s a man-sized cock, isn’t it” I proudly said. Pauline got up and lifted up her skirt and out flopped a super long penis a good inch and a half or longer than mine. “Holy shit” I said. Now I am well-endowed but Paul’s penis definitely beat mine and looked a bit thicker too. I can’t begin to explain the feelings I had. It was a monster attached to this slightly built guy dressed as a woman. It made little sense. Yet, In fact, I had certainly instant feeling of submissiveness to the superior penis as women had always been to me or how I felt about smaller men not being as masculine as me. My mind raced. How is this possible that a guy who dressed up like a female is more of a man than me?

Paul laughed and said, “Well did I win the bet?” It was obvious. “Well?” Paul repeated his question forcing me to acknowledge him as the winner.(to be continued)
 

LilJock

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Fantastic story. Great premise.

. . . I also have had an attitude about guys with little dicks or noticeably smaller than mine. Honestly, when I see a video or viewing web cam sites, I just don’t understand the attraction when I see a really attractive woman with a small endowed man. I feel like those women deserve and should demand being with a man that equals their superiority in looks possessing a bigger and better cock too. Plus, small penises especially on otherwise well built guys look ridiculous. The small size makes them look less masculine and so yes I always equated my masculinity with my bigger size. I know this makes me sound bad. Well, as you will read this superior attitude ended up teaching me a lesson in the most surprising way. . .

This paragraph really struck a double cord with me. As a good-looking, well-built guy with a small penis, you coulda been talking about me. Not just regarding the feelings of superiority you expressed regarding size, but that I too have harbored similar feelings towards "effeminate" males, and therefore have been subject to the same comeuppance you experienced when encountering one noticeably better endowed, but, in my case, even more so.

Will be fun seeing where you go with this.
 

trulybig

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I can’t exactly explain all my feelings occurring at once. I had always been the guy with the biggest dick, the alpha dog, and enjoying the admiration of others when seeing it. To me, having a big penis reflected my superior degree of masculinity, I had sexual confidence, and yes pride. Yet, here I was with a person in feminine attire, with a penis clearly larger and better than mine. Paul had returned to a masculine figure for me despite the attire. Here he was in front of me with his better penis than mine extended impressively erect and throbbing directly at me. His was pure masculinity in my view big powerful and overwhelmingly large

Paul said in a very demanding voice, “I won the bet now suck it.” One might imagine that I could have immediately turned around and left the room. What could he do about it anyway? That might have been exactly my thinking, but with my heart racing and a mind of mass confusion I instead reached out placing my hand around his penis quickly getting on my knees and then carefully moved his penis to my mouth. I thought this is how a woman must experience being with me. How else could I explain it? This giant somewhat frightening big male organ with its dominant appearance compelled me to revel in the power it held. I had never imagined doing oral but again just felt like I am going to suck him how a woman does to me. The warmth and fullness of the head of his penis surprised me and that you could feel warmth when sucking it. I closed my eyes like a baby and began sucking his cock like I enjoyed mine being sucked. Many of the sensations surprised me. I could feel it move and throb in my mouth. I tried to go deeper on it but it was so long that not even that far down I choked and had to pull back a bit. However, again in my desire I wanted to possess it all so I then took both hands placing them on the shaft and started moving the soft skin back and forth as I continued exploring how to suck it. It actually bothered my jaw a little after only a few minutes and I thought once again is this how women experience doing oral. It wasn’t all as easy or I never had given that aspect the first thought. But, there was a great feeling of the power that emanated from this big penis. A power of maleness I thought as I found myself truly enjoying taking care of this instrument of his. He was the alpha male like I had always been and it all seemed correct. Paul then pulled away and said “I am going to fuck you”!

OK this was a bridge too far. “No way” I am not gay I said to Paul. I added, “I have never done anything like that, not a chance.” Now you have to imagine this crazy scene as it was. Here is this guy in feminine attire, with a big penis sticking out probably 10” (I know that sounds like B.S. but it was bigger than mine and I am no slouch). “Try it,” Paul said, “If you don’t like it we can stop.” We debated back and forth with me saying no and him saying yes basically. However, there again was this part of me that I either had never been in touch with or like I shared, seeing the alpha male as the one to submit to, I knew I was going to try this. When I asked Paul if he had a condom, his face smiled as he knew I was going for it.

Paul told me to get on the bed and I was in the bottom missionary position like a woman. He moved between my legs, had put on a condom, and took my legs at the knees and pulled me slightly up. He was going to fuck me just like a man does to a woman in the missionary position. He looked down at me and said, “When I push in don’t pull away, just squeeze down on my cock for as long as you can and then totally relax. I was somewhat embarrassed of course in this position but I also had no feeling to resist and just accepted this all was going to happen. He took some type of lube and really coated his cock with it and then I could feel him maneuvering his penis up and down to find the hole. Suddenly, he pushed and I felt him slide inside and it hurt.”Stay still, squeeze like I told you,” Paul said in a demanding tone. I followed his instruction squeezing myself on his cock like working out at a gym. I held that for as long as I could and then relaxed not being able to hold the muscle tight any longer. I immediately felt the sensation of his big long penis sliding inside and it was an odd sensation especially at first. Paul then said, “Wow that was much easier than I thought.”

I looked up and asked, “Are you all the way in?” Paul responded, “Pretty much, we will just hold still for a minute so you can relax and get used to it, how does it feel?” I told him I was uncertain. We were like that for a good 20 seconds and then Paul slowly started moving back and forth. I found the sensation still different but oddly relaxing. In about another minute Paul then took my legs and wrapped them around his back. He now started fucking me harder. Again, my thoughts as my eyes closed was this is exactly how a woman experiences things, he is in control, he is fucking me, I am holding my arms around his back and legs around his thighs. In this position he started using more and more force so now I could feel his balls slapping against mine and that felt good. I liked what was occurring and found it becoming more and more pleasurable. I kept my eyes closed now lost in the total sensations of being fucked and just having someone in total control. His big penis felt great as there was so much of it to slide back and forth. I then started talking dirty which was if someone else now was inside me. “Fuck me, yeah fuck with that big dick, yours is better than mine, you are the alpha male,” and all kinds of similar comments. I kind of laughed to myself too as here I was being fucked by a superior male who is dressed as a woman and I am loving it. My sexual talk was somewhat breathless as I was also without even first realizing it jacking my cock which had grown fully erect rubbing on his stomach. Without warning, I suddenly announced I was cumming as this huge wave of an orgasm erupted. I think my response impacted Paul as very quickly I could feel his cock pulsating and his moans and grunts told me that he was cumming too. Here was this guy cumming inside me while fucking me. This was an experience I never could have ever imagined but afterwards I had no regrets. It was awkward once things were over and I quickly got up to dress and leave without speaking. We never saw each other ever again.