Close Friend

I've grown up feeling accepting of pretty much anything, just being passive and not really arguing unless its something that truly affects me or endangers me. Because of this, at an early age, I learned it was ok for buddies to watch porn together. I don't see anything wrong with it. I've watched porn with a number of friends, it would occasionally feel awkward but I figured that was just cause we were hard around each other. I have this one friend who was always looking for an excuse to watch porn with me, weather I found something new or he did. One day while watching porn, he asked if I would be comfortable with him playing with himself. It's not gonna hurt or affect me, so I said sure. I thought he was just gonna reach in his pants and do it, but as soon as I said sure he unzipped and pulled his dick out. I was a little nervous and curious at the same time. I'd never been in this situation, and was unsure what to do. I wanted to look but didn't want him getting mad, so I kept trying to look out the corner of my eye.

Him: I hope this isn't weird, I just been wanting to try it cause I think its exciting. are you sure it's ok? you seem a little tense.

Me: i'm fine man, i've just never been in this situation.

Him: we are cool, just relax. no one is ever gonna know this is between us. you can pull yours out if it'll make you feel better.

I sat there a minute or so then decided it wouldn't hurt, but then I remembered I had on sweats. no zipper, I'd have to pull my pants down to join him. reached up and grabbed the waist band, then held it a moment.

Him: forgot you had on sweats man, ill just pull my pants down some, that'll make it even.

he stood up and pulled his pants down to his knees, then sat back down. while he did that I was able to get a decent look at his dick. it looked nice and smooth, about average in length and girth. I wanted a better look at it though. I looked back at the porn as I slid my pants down to my knees without getting up. out the corner of my eye I could see he was slowly stroking, and looking over at me. I reached down and pulled my dick out from between my legs, then started slow stroking. he kept staring though which made me nervous and proud.

Him: I hope you don't mind me looking, i've never seen another guys dick before. just wondering how it looks in person compared to mine. I mean I saw you peeking out the corner of your eye so I know you're curious to.

Me: its fine man, and yeah I feel the same its different and i'm curious.

with that I decided to take a straight look at him instead of trying to sneak one. he was staring at my dick while stroking himself, as I started studying his dick. I was mesmerized, being allowed to look at it like this, it looked smoother than mine, mine is veiny. we are both circumsized, mine seems to have some extra skin though. we are shaped about the same but I think im a little bit bigger, not sure.

Him: you got a nice looking dick man.

Me:.....ummm thanks man, so do you.(not sure how to feel about that)

Him: hey I know we normally go to the bathroom and finish separately, but I was wondering how'd you feel about cumming in here. I jerk off onto my stomach all the time.

Me: im not sure. you can, and maybe I will to, but I can't say for sure.

Him: ok, sounds good to me.

I expected him to turn back to the porn like I did, but he keeps staring at my dick, slowly stroking. I decide to join again. so I start looking at his dick again, while I stroke. we sit like that for awhile, then he speeds up and pulls his shirt up exposing his stomach. I do the same, I just enjoy going with the flow. it turns me on more than I expected, having a guy stare at my dick and jerking his. im getting rock hard and I can feel my orgasm building. he starts breathing harder, and stroking faster. every time I notice him being more turned on or excited, it really gets to me. we are both stroking really fast, he tenses up and starts cussing. I stare at his dick as it starts shooting streams of cum onto his stomach which sends me over and I start cumming on my stomach. id never done that before, didn't know it was so warm. we both stop and catch our breath.

Him: damn man that was nice, much better than jerking off alone.

Me: I have to agree man, I didn't expect it to feel that good.

Him: we can do this every time if you want, I wont mind at all, hahahaha

Me: sounds good to me, i'm up for anything that feels good.

he just smiles at me, then we clean up and just hangout the rest of the day.

this goes on for about a month or so, during the time he started taking his pants all the way off, then his shirt so he is completely naked. I slowly follow, so it doesn't seem awkward. it just becomes normal and natural, to just be naked together. we do it when ever we hang out not just to jerk off anymore. sometimes while playing video games together we will be naked almost side by side, and we will stop in the middle and start looking at each others dick, then jerk off together, without porn.

one day, he ask if its ok to bring some alcohol. of course I say yes, I like drinking occasionally. he comes over and we knock back 3 shots of vodka together. then we get naked and start playing some xbox, call of duty black ops, we love killing zombies. we stop after each play through to get another shot. after a total of I think it was 6 shots, he decides he wants to watch porn.

Him: I found this new kind of porn that I really like, its called sissy porn. have you heard of it?

Me: no can't say I have.

Him: it has transgenders in it, or the common word is shemale. ya know chicks with dicks?

Me: well ive seen some of the shemale porn, but never come across the sissy stuff.

Him: man it's awesome, ill put some on.

he uses the web browser on the xbox to find some, then he just smiles at me before hitting play.

Him: this one is laid back, its mostly just a compilation of sucking and fucking.

Me: ok man.

we sit there watching and its like he said, its just shemales sucking dick and getting fucked in the ass. ive watched this kinda stuff before, but i've never told anybody cause I didn't want them judging me. I look over and he's already touching him self, not jerking off, just running his fingers along the shaft. the video was over quick, only a 3 minute video.

Him: what ya think?

Me: it was nice man, ive seen that stuff before.

Him: ok, I was just checking to see if you were ok with that kinda stuff. now ill put on an actual sissy video.

he searches again, the one he picks is labeled "sissy maker". it has music instead of the the normal sounds of sex. it flashes shemales sucking dick, and getting fucked, but it also has captions. the captions flash on screen saying stuff like, " stare at cock" " you love cock" "touch cock" "love cock". just all kinds of stuff, then it gets vulgar, and starts talking about " you should suck cock" " let men have your ass". I look over at my buddy, he is still just rubbing his dick staring at the porn. I start slow stroking cause my dick is way to hard not to touch. im feeling a little fuzzy from the alcohol, and im kinda thinking about what the porn said, " touch cock". im staring at my buddies dick, wishing I could touch it just to see if it feels like mine.

Him: aren't you gonna watch the porn?

Me: I am a little bit.

Him: I have an idea, just don't freak out.

he scoots over until our legs are touching, which immediately turns me on, to make contact skin on skin.

Him: weve been watching porn together for awhile, and ive been kinda wanting to try jerking each others dick. is that ok?

Me: honestly I was thinking the same thing, just didn't wanna make it weird.

He reaches over with almost no hesitation and grabs my dick, it feels so much better when someone else touches me. I just enjoy the pleasure for a moment, then I stare at his dick and slowly reach over. he makes it jump just before my hand touches it, made me snatch my hand back a little.

Him: hahaha just playing man, go ahead and touch it.

I reach on over and slowly wrap my hand around his dick. its so different touching someone elses dick, its like touching mine but I don't get the pleasure sensations. I do feel excited and turned on touching him though. we both start slowly stroking each other, occasionally looking at each other and giggling.

Him: it feels so much better having you jerk me.

Me: same here man.

Him: your hands are a lot rougher than mine though.

Me: im sorry

Him: its ok, still feels good.....I don't know how youd feel about this but, you could spit on it, or get some lube.

I don't really wanna let go of him, which makes me feel weird. so I lean my head over his lap and spit so it lands on the head of his dick, then I smear it around and continue stroking him.

Him: oh yeah, much better.

I just smile, then lean over again and spit some more. its nice and wet now, making a wet sliding noise. I keep staring at his dick, honestly starting to wonder how it would feel to suck it. I cant believe im thinking this way, so I stop for a moment.

Him: everything ok?

Me: yeah I just want another shot.

Him: good idea, me too.

we knock back another shot together, then I start rubbing my eyes trying to clear my head. I kinda don't mind having the thoughts im having but im not sure how he would feel about it. he reaches over and starts stroking my dick again, then I reach over and start on his again. this time I decide to watch the porn which doesn't help. it has messages on the screen about, "submit" "give in to cock" and there are shemales sucking dick passionately. slowly licking the shaft, or sucking on the head and stroking the shaft, then a couple are deep throating. it is making me think about sucking my buddies dick even more, but I don't think im ready and im not sure if he wants me to.

Him: hey why don't you go get some lube so you dont have to keep spitting on my dick?

Me: I guess I can.

I go get the lube and a couple small towels. I sit back down, and start stroking him staring at his dick, then I reach for the lube. before I can get any on my hand though.

Him: wait....I have another idea.

Me: ummm ok, what would that be.

Him: look everything stays between us right?

Me: yeah man, of course it does. especially this stuff, hahaha

he stands up

Him: ok, well I noticed how much you enjoy staring at my cock and how the video has been affecting you. so I think that from how you are acting you might be willing...

then he steps one foot on the couch right beside me, so that he is straddling me and his dick is only a few inches from my face.

Him:....to try sucking my dick.

I just stare, not sure what to say or do. I swallow hard and feel the urge to suck it but I cant bring myself to do it.

Him: this will stay between us, no one will ever know, I promise.

he starts waving his dick around, laughing. then he reaches down and grabs my hand to place it on his dick. I wrap my hand around it and slowly stroke him, trying to build up the courage to suck him.

Him: you seem so nervous hahaha, I am to ive never had a guy suck my dick. just answer me this this, do you want to suck my dick?

Me:....................yeah

Him: that's all I need to hear.

he smiles, then shoves it closer so that the head touches my lips. I go to lick my lips and end up licking the head.

Him: come on open up, you said you wanted to. all you have to do is open up, ill push it in first.

im so nervous, I really want to, I just cant bring myself to open my mouth. I keep parting my teeth but I never part my lips.

Him: you said you wanted to so...

he starts rubbing the head on my lips, until he gets between them. then he starts pushing, my teeth were still parted. his dick slowly slides in to my mouth, until it hits my throat and my nose is buried in his pubes. I unfreeze finally, and start moving my tongue around his dick while sucking a little.

Him: hmmm there you go, do be shy.

I grab the base of his dick and pull all but the head out of my mouth. then I start sucking the head swirling my tongue, and stroking the shaft.

Him: ohhhh goddd yeah!!! damn that feels good.

I love hearing him say that, but ive always loved talk during sex. I continue for awhile before I start trying to throat him, which ive only ever done to a dildo, so I have some practice. he grabs the back of my head and starts humping and moaning.

Him: you are so good at this. damn I should have convinced you to try this sooner. mmmmm......

after a few minutes

Him: ohhhh god im starting to get close, mmmm I wanna cum in your mouth!!!

I pull away from him, and catch my breath.

Me: no....not yet....im not ready for that just yet.

Him: oh, well that's fine man, maybe next time.

Me: maybe.

Him: ok, my turn to work on you some. scoot your butt to the edge of the couch.

I scooted forward so my butt hung off a little. then he got down between my legs.

Him: now im just gonna do whatever, but if I do anything you don't want, just tell me to stop and I will, ok?

Me: sounds good to me.

he smiles at me then reaches out and starts stroking me with one hand and fondling my balls with the other. I just lean back and enjoy myself. he stops after a moment, and gets the lube. he squirts a generous amount in his hand, then more on my dick. he starts stroking me and fondling my balls again, this time it feels so much better.

Me:mmmmm

Him: feels good doesn't it?

Me: yes it does, dammit

he grabs the lube again and adds a couple more squirts. so much that it runs over my balls and down to my ass crack. which makes me shiver a little. he starts stroking me very slowly, but this time his other hand rubs my balls a moment then heads for my asshole. he starts massaging the lube around my hole then slowly running his finger over my hole. when makes me shiver and jump occasionally.

Him: you like that too huh?

Me: uh huh..

Him: yeah I know you do. I noticed how you would sometimes touch your ass when we masturbated together. figured you wouldn't mind me playing with it some.

he keeps circling my hole occasionally rubbing the hole itself. then he picks my legs up so my cheeks spread.

Him: hold your legs.

I grab under my knees and hold my legs up. he isn't even touching my dick anymore, just my ass. he adds more lube, and starts rubbing harder applying pressure on my hole. I feel a finger stroke my hole a couple times, then the tip starts pushing then stopping then repeating.

Him: yeah, you have a nice tight hole, that begs for attention don't you?

Me: uh huh.....

Him: it likes the attention im giving it doesn't it?

Me: yes.

he starts pushing harder, until his finger starts sliding in me. he works about an inch in then pulls out to play with the hole some more. he repeats this until I feel his knuckle against me.

Him: I can feel your legs shaking, why don't you just bend over the couch, instead of holding your legs. itll also make it easier for me to play with your hole.

I get up without a word and bend over the couch, poking my ass out. this is much more comfortable, than holding my legs.

Him: damn you have a nice ass, better than a lot of women ive been with.

he starts rubbing my ass and grabbing my hips, then he slaps my ass. which I loved more than I thought I would. I hear him getting more lube, then I feel his fingers rubbing my hole again. he slowly works that finger back in to the knuckle, then wiggles it around. it even feels better in this position.

Him: im gonna try 2 this time, ok?

Me: ok

I feel 2 fingers touch my hole and apply pressure, its mildly un comfortable but still feels really good as well. it takes a little time but he works them up to the knuckle too. then he starts moving them in and out slowly fingering me until it starts to feel looser and a lot better.

Him: mmm hmmm this ass loves being played with. your dick has stayed hard, and you keep moaning. youre loving this aren't you.

Me: yes

Him: how good does it feel?

Me: it feels sooooo good!!

Him: yeah, this ass needs to be filled. how does 3 fingers sound?

Me: I don't mind at all if you wanna try it.

Him: that's what I like to hear, your hole is just hungry.

he gets more lube, and starts working 3 fingers, which kinda hurt a little at first, but he was very gentle and slow so I was able to relax in moments. he couldn't get it to the knuckle, so he stopped and fingered as much as I could take, until my ass relaxed and allowed him to go knuckle deep.

Him: yeah, I love playing with your ass, its so nicely shaped, and I love how hungry it is to be filled. are you still enjoying it?

Me: mmm hmmm

Him: yeah you are still rock hard.

he grabs more lube and starts rubbing my hole then he puts one finger in, and fingers me a little. then two fingers, and works that a little. then he does the same with three. he starts rubbing my ass cheeks, squeezing them then slaps them a couple times. he keeps squeezing one cheek while fingering my ass.

Him: hmmmm your ass is perfect, it makes me hard just looking at it.

I shake it a little and wave it around.

Him: ohh hooo you little tease. you love this don't you?

Me: uh huh

Him: I bet youll love this too.

he pulls his fingers out of my ass and starts rubbing the hole really hard, then I hear more lube as he keeps rubbing my hole. he starts grabbing both my cheeks, spreading them then pushing them together. he repeats this a couple times, then he starts rubbing my hole again and slowly applies pressure while squeezing one cheek. but stops before penetration.

Him: im not putting my fingers back in until you beg me to.

Me: really?

Him: yep I wanna hear you beg.

Me:....please

Him: not good enough

Me: dammit........I love having your fingers inside me, please put them back in me please!!!

he squeezes my cheek then starts applying pressure again. as he starts breaking through, I feel his other hand grab my other cheek. I realize its not his fingers this time, as his dick slowly slides in my ass. every inch feels amazing, he keeps working my cheeks as he slides in. he goes deeper than his fingers, then I feel his pubes against me just before his hips meet my cheeks.

Me: mmmmm

Him: I thought you might like this. I swear your ass has been begging for my dick. and my dick has been begging for your ass. mmmmm you feel so tight, your ass is perfect, and needs a nice fucking. doesn't it?

Me: uh huh mmmmm

Him: say it.

Me: please fuck me....

Him: as you wish hahaha

he starts working in and out of my ass slowly, until ive loosened up where he slides easier. then he pulls out and adds more lube.

Him: I think youre open enough for me to fuck now, don't you?

Me: yes, give it to me.

he grips my hips and starts pumping me a little faster, then a little harder so it makes a slapping noise.

Him: god this ass feels so good.

Me: yes and your dick feels amazing!!!

Him: yeah, you love this dick don't you?

Me: yes, it makes me feel so good.

Him: everytime I come over you should let me fuck this ass.

Me: anytime you want it you can have it, my ass is yours

he really starts pounding me, I love feeling him slide in and out of me, pushing hard like he wants to get more in me. his balls slap above mine. I reach under me and start rubbing his balls when they slap me. I feel like im about to cum just from him fucking me, so I clench up trying to hold off.

Him: did you just get tighter?

Me: a little, don't stop please don't stop.

Him: ohhhh goodddd!!!! oh im gonna cum, you feel to good I cant hold anymore!!

Me: I want you to cum inside me, please I wanna feel it.

Him: yeah?! you want me to fill you with my cum?

Me: yes please!! cum inside me, fill me up!!

Him: ohhhh yeahhh here it cums!!!!