As a 25-year-old young gay man, I was always horny. Masturbated all day long, trying to find hookups and so on, but I was always ready to try new things and experiment. I’m thin, almost 6 feet tall, with dark hair, brown eyes, pretty fit or I like to think so, average size cock, almost 6 inches. So going back to 1 sunny day, I was masturbating at home, I was horny but bored and I could not cum fast. I decided to go out on the balcony for the fresh air and feel the sun on my body and cock, maybe it will get me in the mood. And I do love the feeling of the light breeze hitting my naked body, I was still bored. I kept jerking off on the balcony, no one was around to see me when I had the idea of going outside of my front door naked. This was still the beginning of my more brave gay life so I was afraid to do anything risky. But the desire to try something new took over and I decided to step outside of my door. Luckily the door does not lock so I could jump inside any time I wanted. It was the middle of the day and everyone was at work. I stood outside my door for a minute, covering my cock with my hands, but after I got some courage I let it go and started to walk toward the stairs.
I was living on the 14th floor at the time, so when I reached the stairs I looked down and up to see if anyone was around, luckily for me I was alone. I started to jerk my cock at the edge of the railing, to cum all over the stair, and go back inside, but then I hear the elevator move. I jumped at the sound but then I watched as the elevator started to go down, once it reached the first floor it stopped and started to move up again. With every floor closer to me I got more aroused and scared at the same time. It was getting close and I genially thought it would stop on my floor for a second, but then it stopped on the 11th floor. I was watching it for maybe 2 minutes not moving before deciding to call it up to me. When it arrived I jumped inside. My new plan was to cum in the elevator and run back home. I started to jack off with speed and determination when suddenly the door closed. I froze, I was naked in the elevator and it was moving down. I even came up with a story about how my friends dared me to do it. Five floors later on the 9th floor, it stopped and a middle-aged man walked in. He was around 35, dressed in a suit. When he saw me naked in front of him, he was very startled. I tried to make out a story that friends were messing with me and pushed me naked in the elevator as a prank, but my hard cock gave me away. He pulled me by the back of my head and led me out onto the landing. I did not know what he was going to do. I was a little scared, but also quite excited - I was standing naked in front of an unknown man. Without saying a word, he unbuttoned his pants, took off his boxers, and his big piece flashed in front of me. I immediately guessed what he wanted. And since he was so serious, I decided that it was better not to be too open, but to do what he wanted me to do. I crouched down and took his cock in my mouth. He just grinned. And he started to fuck me in the mouth. It was super cool. I was squatting naked on the landing in front of the elevator blowing on a stranger. I would burst with excitement. After about ten minutes he was done. I tried to pull it out before it emptied down my throat, but he pressed down on my head and there was no getting out. His cum was delicious and warm. I stood up and looked at him questioningly. I thought he was going to want to fuck me, I couldn't run anyway even if I wanted to. He just looked at his watch and opened the elevator door. He was obviously in a hurry to get somewhere. He pushed me in and he got in too pressing the button for the first floor. When we reached it he got out and I pressed the button for my floor. On the way up my erect cock was finally ready so I blew my load on the elevator floor and got back home, savoring the starter’s tasty cum in my mouth. This was my first elevator experience.
Three years later I was now much more experienced and much more brave than before. From time to time I would remember my elevator blowjob and reminisce how good the stranger's cock felt in my mouth, or how sweet his cum tasted. I had also embraced another side of me which was that I like to wear women's clothes. I liked how they made me feel, how they felt over my body, and how hot I looked at them. Not that I wore them often or in public, but I just had the feeling of them on my body. Anyway, I was traveling to Sydney one day, on a business trip, but the work was done ahead of schedule so I had a few free nights to relax and enjoy. I didn’t know anyone so I spent most of the day walking around the city. It was getting late and I decided to stop at a bar near my hotel, for a drink and then call it a night. I sat on the bar and ordered a fruity pink cocktail, which is probably what gave me away. Thirty minutes later a handsome, tall, blond guy sat next to me on the bar. I admit I tried to get a good look at him a couple of times, which I think he noticed. He ordered a vodka tonic, and after the first one, I guess he got some courage because he said hello to me and asked me if I was alone. I was not used to talking to random guys at bars, it was mostly dating apps. I guess he could tell that was not local since he asked me where I was from and so on. We started talking and after he proposed to buy me another drink and another we hit it off. We end up sitting at the table in the corner of the bar. He was putting his hand all over my legs all night, whispering in my ear how hot I was. We were both drunk and so the more dirty and honest stories started to flow. Of course, we knew we were both gay at the time. I told him a few of my personal experiences, but it was nothing compared to his wild stories. From casual hookups in parks to massive orgies. Even though we were the same age, he had a lot more experience than me and I liked that. Being drunk and trying to impress him, I also revealed my fetish for dressing up in women's clothes, although I exaggerated a bit. But to my surprise, he told me he dresses up on occasion as well, he liked how it made him feel. And with some makeup and a wig, he would go late at night to straight bars, and pick up straight dudes to fuck him. They would be too drunk and horny to tell, and he was a lot skinnier when he did it so it was easy for him to pass as a girl. Sometimes they would fuck him in the bathroom or just wanted a blowjob and they would even realize they were with a man. His stories were wild. And a bit surprising, since all the other stories he told me before I pictured him more of a Top than a bottom, but guess he liked to swing both ways. Although he didn’t do that anymore, he started working out and now he looked more muscular and big than before, which I didn’t mind at all. A tall, fixed, blond guy, with blue eyes, he was perfect. It was getting pretty late so he told me he had to go, as he was working in the morning, but we swapped numbers, and he told me to text him tomorrow. He had a great time meeting me, and so did I. I was hoping things would get more physical, but no luck tonight, and that was a good thing, otherwise the next day might have not happened.
The next morning I woke up late with a bit of a headache back at my hotel room. When I started to wake up a little I checked my phone. I got a few messages from Dan ( the guy from last night). He told me what a great time he had and hoped we could meet again before I left. He had also sent me a few pictures of himself, related to our conversation he said. I opened the images and it was Dan, dressed up like a girl, he looked a lot skinnier than now, almost like a different person. I was a bit jealous, of how good he used to look and how good he looks now as well. Scrolling true the pictures got me hard as a rock, but I didn’t want to masturbate just yet, so I send him a picture of my cock, telling him what his pictures did to me. He sent me a couple of hards and told me we needed to do something about that. Well since he bought me drinks last night, I invited him to my hotel for a drink later tonight and he agreed. I planned to rest and prepare for tonight, but first I needed some food. After a coffee, I got dressed and went outside to find food. While I was eating at a small local restaurant I found I got some more text from Dan. He texted he had a crazy idea, we proposed we both wear a dress tonight to our date, it will be like two bitches on a date. I told him it was crazy and I didn’t want anyone to see me, but he made a good point that no one even knew me, and besides, why not live while I can? He made a good point, but I still didn’t have anything to wear, so I made another excuse, he sent me the location of a local shop where I could go and buy anything I wanted. I agreed but only if he whore his little blue dress, with one sleeve covering his left shoulder, he look really good in it, in the pictures he send me. He agreed and so I also needed to buy a dress. I was skinny so it wasn't too hard to find anything I liked. So I ended up buying this little black dress I found in the store he sent me to. It also sold wigs and shoes, so I bought a wig to match my hair, just making it longer, and also a pair of black heels, I wanted to be taller for him. I didn’t find any panties I liked so I decided to go commando, even though I didn’t know how much my dick would stick out under my dress, but I decided to risk it.
Back at my hotel room, I prepared myself and made sure I was all clean and shaved for my date tonight. Put on the wig and dress, I loved how my legs looked in my new black heels. The dress had holes on the sides, and was tight around my ass, which made it look juicer, which I loved. I must have spent almost 2 hours dressing and mostly posing and taking pictures in front of the mirror because it was almost time to get down to the hotel bar. At the lobby as soon as I entered I saw a blond girl in a blue dress sitting at the bar and I knew that was Dan, I recognized that dress anywhere. I moved towards him and sat next to him at the bar. When he saw me he almost spit out his drink, he told me I looked amazing, asking me to turn around for him so he can get a good look at me, with me bending over to show him how good my ass looks in this dress, and he agreed. On the other hand, he also looked stunning, with his blond wig and blue dress, he also had black heels on but a bit shorter than mine. I was surprised how easy he walked in them, it was a lot of struggle for me. After sitting down and grabbing a drink as well, we got to talking and the time flew by. He had plans for us to walk around like that, to show me off to the public, but we both agree we were too horny for that now. And also my dick was already pocking under my dress, no way I could walk around like that. After maybe 2 hours of talking and drinking I proposed it was time to get up to my room and he agreed. I grabbed his hand and led him to the elevator, carrying my shoes in one hand, good thing I got them and wore them for almost 5 minutes. I was feeling him a little tall at the moment, so while we were waiting for the elevator to come down, he took his shoes off as well. We were exactly like 2 broads walking home after a long night, both bare feet. We complimented each other while waiting and when the elevator arrived, we were busy hugging and touching each other bodies, and looking in the mirror, so we forgot to press any floor button. We admired each other asses, and how good we looked, Dan even lifted his dress, exposing his ass in a little pink thong string running over his hole. I lifted mine as well, just the back, exposing my bare ass to the mirror, which Dan grabbed and smacked, before sticking his tongue down my throat. We started to kiss when the elevator stopped and the door opened. A couple entered the elevator and we got off, with Dan's hand over my butt. As we moved off his middle finger moved over my hole and just then he realized I was not wearing any panties, which he whispered in my ear in surprise. As soon as we were out and the door closed, he kneeled in front of me and lifted my dress, exposing my hard cock to his face. Without hesitation, he took my cock in his mouth and started kissing and sucking on it, right there in the middle of the hall. His lips around my dick felt amazing, I loved how easily he took my cock balls deep in his mouth. As amazing as this felt we had to stop as we heard footsteps approaching, so I pulled my dress down, barely hiding my erection and we stood in front of a mirror taking some more pictures while a guy walked behind us. As I led Dan to my room I just realized we were on the wrong floor, it was the 14th and I was on the 26th, so we laugh it off, no surprise since we were so horny so we got back in the elevator.
This time I pressed the button, but as we were going up, and pressed the stop button someone was between the 22nd and 23rd floor. Dan looked surprised, but not for long since I got down on my knees, and lifted his dress. The front of his panties was see-through with little hearts on it, I also saw his cock smooshed inside of them, with the head sticking out. I see why he needed panties, to hold his cock in place, he was bigger, not by much maybe 7 inches, but I would stick out much more than mine. I took his panties with my teeth, holding them in my hand before I started to suck on his cock. This is the second time I just start to suck on a guy's cock in an elevator, with him being silent and accepting it. And once again it tasted amazing, it felt amazing and I was rock hard and ready to explode. As was Dan as well, since after a few minutes he pressed to button to keep moving and told me to stop or he was going to explode. We were finally on the right floor and we were walking down the hall, to my room. In the middle of the hallway, he grabbed me by the neck pinned my back against the wall started kissing me passionately. We made out for a little, with me holding my shoes and his panties in one hand and grabbing his ass with the other. He was also holding his shoes, but his other hand moved from my neck down to my cock which he started to rub. He lifted my dress a little, so now I was moving with my cock out toward the room, finally managing to unlock it so we can get inside.
Inviting him in and closing the door, I saw him down on all fours walking toward me, telling me he wanted to taste my ass, which I let him. After he eat my ass, we started to move to the bedroom, but there was this big mirror in the hall. We stopped in front of it and I ordered him to get down and suck my cock, which he gladly did, playing with it, licking and stroking its head, while looking himself in the mirror. We finally got dressed and we were completely naked heading toward the bed. We started by making out on the bed, and soon I was on my back with Dan on top of me. I had my legs spread aside, with his legs between mine. Our cock was facing each other, and Dan grabbed them and started to rub them again one another. All the precum leaking from the got us both nice and wet. I was expecting him to penetrate my ass, but to my surprise, when he pushed me down, he spit a few times in his hand and rubbed it on his butt. Then got on top of me, and slid down on my already wet, leaking cock. He adjusted it toward his ass and slowly slid my cock inside his asshole. He was facing me with his hand around my neck, while he was impaling his ass on my cock. He felt so tight and yet he took it so easy inside of him. I could feel his heavy breath and saddle noises as he kept fucking himself. I was now laying down, with him still impaled on my dick. He leaned back, with his legs squatting and jumping on my cock. His left arm was behind him supporting his body, while his right arm was vigorously jerking his cock. It was just the toy he was using at that moment. All that excitement all day was making me ready to cum. As I was close I scream I was going to fill his ass, and he started to beg me for it. With his still jerking his cock, soon I felt his ass muscles tighten and I had no choice but to fill his beautiful little ass with my seed. With me starting to cum in his ass, soon he also started to cum all over my body and my face, shooting his load all over me. He then collapsed on top of me and we started to kiss, licking and exchanging his cum between us, playing with it without tongues. My now softer cock felt out of his ass, and I could feel my sperm leaking down his hole, all over my balls. We lay like that for a few more minutes before getting up to wash up, as we were not yet done. Laying next to each other for the next 30 minutes till we had the strength to go again, we again started to share stories, and soon we got horny and ready again.
I mounted his face with my ass. First I started to feed him my cock, pulling it down to his mouth and face fucking him, then he moved on to my balls, licking one after another, pulling on the with his teeth, before burying his face in my ass. His wet tongue penetrated my tight asshole, and the amount of saliva I felt on my ass, made me wet like a woman's pussy. I flipped myself so he can keep eating my ass, but I needed to taste his cock now. I grabbed that hard stick and started sucking on it, spitting saliva all over his balls and dick. I was sucking on that cock like my life depended on it. After he had me doggy style on the bed, and he pushed two fingers inside my asshole, he was finger fucking me, while with his other hand jerking my cock under me. I needed to feel him inside of me so badly, but I was beginning to wonder if I could even hold on till he penetrated me, I was close to bursting. Thank goodness he stopped, but as I was ready for his dick inside of me, he flipped me over on my back and started to kiss me again. Penetrating my ass with his fingers once again, while we were kissing. He was fucking me like crazy with just two fingers, I felt like his bitch who is getting her pussy finger fucked. He kept going while lifting one of my legs, and licking my foot all over until finally I had both of my legs up together, he was holding me like that and I felt the head of his cock on my ass. He started slow, just pushing the tip in, but I was so horny and wet at that point that he soon slid his entire cock, balls deep inside of me. He was pulling it all out and would go fast deep inside of me until his balls slapped on my ass. I could feel every inch of his cock going in and out of me. Swoly he started to pick up paste until he was fucking me hard, and I was screaming from all the pleasure under him. I wanted him to feel what I felt, so as soon as he started to get tired, and that took a long time, and my ass took a good pounding before that happened, I flipped his over. He was on his back, legs up in the air before I started to eat his hole, the same way he ate mine, very wet. Then I stood on my feet on the bed and slowly lowered my hard cock in his ass, and I started to fuck him like that, looking right at his eyes. He was looking back at me, begging me to keep going. Now I was getting tired and could not keep the position, so the moment I got weak in the legs, he pushed me down on all fours and started to ram my ass again. He grabbed my neck with both hands and was shocking me while slamming my ass. I had trouble breathing, and moaning like crazy, so I had my tongue out, like a dog, licking saliva from my mouth, between the moans, and the attempts to catch my breath. I was having the time of my life, my cock was spraining precum all over the sheets. I finished on my back, with his sitting on my chest, feeding me his cock, and jerking mine with his hand. Soon he started to cum, filling my mouth with that delicious juice, and me swallowing every last drop. While that was happening he kept jerking my cock, until I started to cum, shooting my load in the air, all over us, with his hand getting soaked, but still kept moving over my softening cock. We fell asleep, all covered in sweat and cum.
The next morning I woke up early and went to freshen up in the bathroom. While washing my face, I knew he would have to leave soon and I had a plane to catch, but we still had some time. Going back in the room, I laid next to Dan in the bed and started to kiss him, to wake him up, before noticing his cock starting to get hard again. I needed to feel him inside of me one more time before we left, so I leaned down, place my shoulder on his belly, and started to work and suck on his cock. Soon he was grabbing my hair and pushing me down on his dick, forcing me to suck it faster and deeper. Making me deepthroat him. I was soon laying next to him on my side, with my back facing him, and he adjusted his cock, and started to fuck me like that, with my head spun around so we can kiss while he took my ass. I had one leg over the other and moved a little forward, so he has perfect access to my asshole. He then moved over me, fucking me like that, choking me with one hand, I guess he loved to choke someone he is fucking. Soon I was getting rammed. He was fucking me so hard, he was lifting my ass with his cock. I had my feet on the bed, lifting my ass in the air, with him holding my tights and my ass with his strong arm while fucking me. My shoulders were down on the bed, and all I could do it scream like crazy, and watch his concentrated face, looking down at my cock, which was bouncing up and down, slapping on my belly, and he's going in and out of my ass. The sound of our bodies slapping against each other drove me mad. His dick hit my prostate in the perfect position I lasted as long as I could, but at the same point I let go, and cum started shooting out of my bouncing cock, all over the room, the bed, all over my own body, there was sperm everywhere, but Dan didn’t slow down, he kept going, holding me in place while I was spasming from the orgasm I just experienced. He kept going until he was finally close, slowing down and jamming his cock deep inside of me, releasing his seed. I could feel his hot sperm, filling deep inside of me, with every shot I twitched a little, feeling it hitting inside my body. When he was finally finished with me, he leaned back, legging my ass finally down on the bed. Hot sperm started to leak from my ass, but I was so tired from all of it, I could move I just laid there letting it slowly drip down, until I felt a wet spot under my ass.
Dan got up to shower and get dressed, he leaned down to kiss me goodbye and left me to rest covered in both of our cum. I knew I needed to get up, but the orgasm that I felt made my legs soft needed some time to recover. On my way to the airport, I received a text from Dan, he sent me a picture he had taken of me, lying there helpless and covered in juice, he told me this was his new favorite story and he would show everyone what he did to me that morning.
