Sissy boy erection in short shorts tubes Usually the very first day

Sissy boy erection in short shorts tubes Usually  the very first day
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Background: I was 14 when this happened. Probably about 5'4" and 135lbs, 5" dick. My neighbor Justin was about 5'11" and 160lbs, and a big thick 7.5" dick. Justin had red hair and freckles. He was a pretty cute kid, but most people at school didn't like him. He always seemed to say the wrong thing at the wrong time. I was pretty good looking, but by no means was I in the 'cool' crowd in school.

One day I was riding the bus home with Justin and the conversation turned to porn. At that time limewire was pretty popular, and we discussed that we both downloaded porn on it. He was telling me how he used to download porn but then his mom caught him once. I told him I just would download and then delete it after everytime which was kind of a pain. We were talking more about it and he mentione how awkward it was when he got caught.

He said he would always use tissues to clean up and she found a bunch laying around after he had been caught and made a joke about him being old enough to clean up his own room.

Anyway as the conversation went on, I found myself getting pretty turned on. I knew I was as interested in guy's dicks as I was girls, but had trouble finding someone to act on that with. He mentioned how much he missed downloading porn, so I offered to burn him a cd if he wanted.

He said that would be great. So I said he should just come to my house when we got off the bus and I could find him some videos. When we got off the bus, I had a hard time not getting an erection at the thought of us maybe watching porn together.

We went into my house and I asked if he wanted anything to drink or eat and he said no and seemed eager to go up to my room and check out the videos, so I was very happy to oblige him. I typed in some usual searches "girl on girl" "guy fucks girl" "girl blowjob". He said "I'm not as interested in the blowjob videos. Isn't that kind of gay?" I was like "What is gay about a girl sucking a guys dick? I love those." "Idk pretty much are staring at a dick the whole video." I knew he was right, and I knew that was part of why I watched them, but I tried to spin it.

"I just imagine I'm getting my dick sucked. Have you ever had a blowjob?" "No, I wish" he replied. "Dude its the best feeling in the world. Like nothing feels better." I lied pretending I had had a blowjob. "Who gave you head?" He asked. "Denae last year." I lied. "Oh damn dude, thats crazy. Youre so lucky" At this point some of the videos had finished, "here, check this video out and tell me its not great." I said as I played a "heather deep throats" video that had a cumshot at the end.

It was only about 4 minutes long, and I had a hard time concentrating on the video as I was mostly staring at Justin's jeans trying to tell if he had a boner.

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I couldn't tell if he did, and I didn't want to be too obvious. I asked him what he thought and he said "that was pretty good. But not enough tits or ass." I said "okay, I hear you, check out this one." And played another one with the same girl, but where she undressed first and then plays with the guys dick on her boobs. Before sucking it." At this point I could see clearly that Justin had a boner stick out his jeans. I had been hard pretty much the whole time we had been at my house, and had been hiding it.

I pretended not to notice, as I didn't want to scare him off, and asked what he thought. "dude that one was great. Can you burn me that one?" "fo sho man! Lets check a couple others to put on the cd." I decided to play one where two girls take off their shirts and suck a guys dick.

It was a little longer, about 8 minutes. Half way through Justin was kind of fidgeting and put his hand on his crotch to kind of adjust his boner. Atleast once I was pretty sure he caught me looking at his crotch, but I quick looked away. I couldn't tell how big his dick was, but it definitely looked like he had a full hard on. After the video was over, I asked if Justin liked it. He said "Holy shit.


My dick is about to hit the ceiling." I laughed and said "haha you wish. That little thing." teasing him. He responded back seriously "dude, I guarantee my dick is bigger than yours. I am almost a foot taller than you." I was kind of put off by this, as dick size was a big manhood thing, and I had just been teasing him and he went all serious.

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But that was how Justin was, he was brash and kind of an ass. But another part of me was super turned on by the thought of him having a bigger dick than me and taunting me about it. Something about him being 'more of a man' than me made me feel so hot so I decided to keep teasing him. "Dude, no way. Mines bigger, I bet you have a little baby dick." I laughed back. Then said "no I'm jking, I'm sure its whatever.

They're probably the same." He dead seriously responded back "dude mine is way bigger than yours. You're just embarrassed cuz you probably have a little dick." I knew that Justin was getting kind of pissed, as he got mad easily, but I also loved making him argue like this and it was turning me on so much.

So I looked down at his bulge very obviously and said "doesn't look like much to me." I was shocked when he responded "you want to see it. I'll fucking show you." I said "no way thats gay dude. I don't want to see your little dick." Justin then started undoing his belt. I sat mesmerized as I watched him unbotton his pants, pull the zipper down and then pull his jeans down. At this point I could see that his dick looked huge in his boxer briefs.

He grabbed his dick through his boxers and showed me the outline and said "does this fucking look little?!" Practically drooling I said "looks average. But your just using your boxers to make it look bigger." "Your fucking retarded" He said as he pulled down his boxer briefs and exposed the most beautiful dick I had ever seen.

It was 7.5" and pretty thick. He had a light red bush and hair on his balls and thighs all over. His dick was light skinned and the head was a light pink that was perfectly shaped. If dicks could enter beauty pageants his cock would have won miss america. He grabbed his big sexy hard on and gave it a few pumps and said "I bet this is about twice as big as your little dick." Feeling light headed at how close I was to something I wanted so bad I could barely think of anything to say "no its not." "Whip it out then." "No thats gay." I was pretty embarassed to show him my dick that was a good 2.5" smaller.

"Dude you talked a big game. Like you always do. You're such a little bitch, but you think you're the shit. You probably have like a 2 inch needle dick." Dude "I was just messing around with you, I dont know why youre getting so mad" I replied.

"Because you always talk shit, and you think you're so cool and act like you're way cooler than me cuz you have douch bag friends, but really you are just a little dicked bitch." I was shocked at how brash he was being.

I knew that sometimes Justin resented me, and I did definitely act like I was too cool to hang out with him at school because he wasn't very popular. But it was so shocking to hear him call me out like this about something in which he was so clearly right.


He did have a big dick. And I was embarassed about how much bigger it was and trying to save face. But at the same time I was so turned on by how much I loved him talking down to me and being the alpha male. I wanted nothing more than to get on my nees and suck his dick until he came all over my face.

I wanted to be his slut, and I wanted to inhale his red bush. I wanted to lick his balls and gag on his dick while he called me his little bitch.

But in reality I was stuck trying to save my dignity "dude youre right man yours is bigger by a little bit. My bad man, I didn't mean to be a dick or anything I was just kidding.

Sorry." I tried to difuse the situation.

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"Okay atleast you admit it. But I don't think its a little bigger. I bet you have like a four inch dick." "Dude I do not, whats your problem." "then lets see it." "Dude thats gay." "You are the one that is staring at my dick.

I just want to see it so I can prove how much bigger mine is." He said. "Do it or I'll tell everyone I saw yours and you have a four inch dick. "Dude, no one will believe you!" I shot back terrified at the thought of a rumor about me having a small dick going around high school. That was the last thing I needed. "You're a midget, people will believe me. Plus people wont think I am lying because it sounds weird to say I saw your dick. But I dont care because I get so tired of you thinking you are the shit, and people treating me like a loser." I knew he had a point.

"Okay, okay. I'll show you, you're a little bigger." I said as I began to undo my belt. I was so nervous but so turned on at the same time. I knew he would realize that his dick was monsterous compared to mine, but at the same time this was turning me on so much. I was leaking like a faucet. I stood up and pulled down my jeans exposing my tented boxers. Then in one swoop pulled down my boxers. Justin laughed "hahahaha I knew it!" I said nothing back. I just stood standing with my t shirt on and my pants fully down and my rock hard erection protruding out.

"Lets measure them." Justin said. At this point, I gave up trying to act macho and just decided to go with this. I didn't really think we would fool around, but just being with him with our pants down and full boners, was giving me jack off material for a year. "Go get a ruler, little dick. Thats your new nickname littledick" Justin said. "Dude its not little.

Its average." "Hahaha then I must have a king kong dick, if yours is average." I got up and looked for a ruler. I caught Justin checking out my ass. I did have a nice ass. Kind of a girly ass, as I had no hair and it was a plump bubble butt. I really made a show looking for a ruler.

I bent over and looked under the bed. I got on my knees and bent over to look under my dresser if there might be a yardstick.

Everytime I looked back at Justin I caught him staring at my ass. "I cant find one man." "Fine I know a way to tell how much bigger mine is. Stand up." At this point, I pretty much would have done anything Justin told me. I felt like putty in his hands. I wanted so bad to see him cum. I stood up and Justin did the same. As he walked over to me I stared at his dick sticking straight out and wagging back and forth as he moved.

His t-shirt was resting on his dick and covering most of his ass. He walked right up to me about a foot away. I kind of caught my breath as I didnt know what he was going to do and I was so nervous while also filled with desire. He stared down at our dicks and spread his legs and kind of waddled forward until his dick was pushing on my stomach. Then he crouched down so his dick was next to mine and grabbed them both.

I gasped and let out a little moan at him touching his dick.

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"Look how much bigger mine is." He said. I could barely concentrate. It felt soo good with his hand on my dick and his dick rubbing against mine. He was so warm.

I was afraid to do anything so I just stood there motionless and silent. "Did you hear me? Can you admit that your dick is a joke compared to mine." I still said nothing. "I'm waiting." He said. I cleared my throat. "Yeah.yours is is.huge.its awesome man." I didn't know what I was saying, but I don't know if I cared.

"hahaha yeah? You in love with my big dick?" He taunted. I said nothing "hahaha you want it dont you." My silence was confirmation enough. He reached around behind me and grabbed my ass and stuck his dick into my stomach. He kept grabbing my ass and really kneading it and feeling it with both hands. He started grabbing it harded and harder, and took one hand off of it to lift my shirt and put his dick facing upwards.

Then he started humping, rubbing his dick up and down my stomach while grabbing my ass with both hands. Then he said turn around. I did as he asked. He came up behind me and kept grabbing my ass. Then he started rubbing his dick up and down on my ass.


It felt sooo good. His hot soft yet hard dick rubbing on my butt. "Bend over." He commanded. I did as he told me too without saying a word.

He slapped my ass. I said nothing. He slapped it again. Silence. SLAP! SLAP! SLAP! SLAP! SLAP! "Ow stop!" I said.

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He just grabbed my ass and slapped it again softer. Then he grabbed one of my hips and put the other hand on his dick and tried to guide it to my ass hole. He rubbed it around the hole which almost made me cum right there. Then he tried to shove his dick in my virgin hole. Without lube this was not going to work. Nonetheless he tried to jam it in. "OWW!!!" I yelped.

And quick turned around. "No" I said. He pushed on my shoulder without saying anything as if telling me to get down on my nees and suck his dick. I needed no further invitation. I got down on my nees with his throbbing one eyed monster staring me in the face. I grasped it with one hand, feeling its warmth and girth for the first time. I gave it a couple of quick strokes before licking the head. A drop of precum came out and I licked that up.

More oozed out, and I licked it all up. I licked all the way up one side of his dick then licked all the way the other. I licked his balls, and got his dick nice and went licked it all over before finally putting it in my mouht.

I tried to go all the way down on it but could only get about four inches before I started gagging. I took it out and looking it all over and used my hand to slowly jack him before putting it back in my mouth. I tried to go back down and use my hand to get the rest and take it back out, I did this three or four times before he pushed on my shoulder. I took it out my mouth and looked up at him concerned, not wanting to stop.

He pulled my hand off and moved over to the chair and sat down. Without saying a word I followed him over and got between his nees. I licked his balls and put one in my mouth, before going back to work on his dick.

I hadnt done but 30 more seconds of sucking when he pushed me off again. I kept stroking him slowly looking up at him wondering why he stopped me, when his dick jerked and he exploaded all over his stomach. It felt like it had been less than two minutes.

I kept jerking him and more and more cum kept coming. It was the most jizz I had ever seen. I stroked a few more times getting every last drop out, then whiped my hand on his balls.