I have been interested in anal and Oral Sex with another guy for a while. This is a story of how I make it happen.
My name is Jim. I am a 37, mostly straight, male in decent shape. I say mostly straight because I am only attracted to women but for a long time I have been experimenting with anal play. Started out with working a finger or two in and then progressed to buying toys such as butt plugs and dildos. It has been a lot of fun, but my interest has grown to wanting more. It has felt like something is missing and a growing desire to suck cock and have an actual cock in my ass.
I have been on and off Grindr looking at my options. I have even had a few decent conversations and some not so decent (wink). But I have been apprehensive to meet a total stranger off an app and have chickened out each time.
A few months ago, I had to move out of my old house and in with my co-worker Issacc. We have worked together for a long time and are pretty good friends. He has his own house and was living with his girlfriend but had a room available for half the rent I was paying. I jumped on that immediately.
I had been living there only a few months when Issacc and his girlfriend broke up. He had caught her cheating on her and kicked her out. So now it was just me and him. That is when the fantasizing began. We would watch different movies and discuss who we thought was hot and then he would tell me about how he had dated a girl that looked like this celebrity or had fucked another that looked this one.
I had no delusions; I knew that my friend was straight. But that didn’t stop me from fantasizing about me being the one he had fuck instead of some girl he met on an app or whatever. That is when I began to scheme and try to seduce my straight roommate.
I started simple. First by wearing loose shorts, no underwear, letting everything hang free. When sitting on the couch across from each other I would have me knee up so that the leg of my shorts would slide down and he would get a healthy view of everything I was offering. The first time it happened he said, “Hey man! I can see your junk!”
I simply replied with a coy smile, “I’m sorry, that’s embarrassing! It’s just so hot it’s been more comfortable to go commando.”
“No problem, man, I totally get it. Just was a bit of a shock.”
We both chuckled and continued our night.
After that life kind of went on like normal. We would go to work and then come home and just hang out. We would watch movies, drink beer, and smoke a little weed. We had always been a little physical with each, at work and now at home. What I mean is we would smack each other on the ass sometimes, a kind of good game sort of thing. Usually, it would be a quick interaction met with grunts and laughs. But now in my attempt to seduce him I reacted differently. Whenever he would smack my ass at home, I would give a little moan before playing it off with a laugh. With not wearing any underwear sometimes his fingers would run up my crack. It was long before I noticed that his hand would linger a little before taking it away, then I would watch as he walked away and would notice him adjust his own shorts in his crotch. I knew that I was beginning to get to him.
One afternoon was in the kitchen when I heard Issacc come home. I was in my typical shorts and pretended to drop a spoon. Right as he walked into the kitchen I hinged at the waist and bent to pick up the spoon, making sure my ass was on full display. I held there for a brief second and he came up behind me and gave me a hard slap across the ass.
I jumped up and yelled, “OWW MAN, THAT REALLY HURT!!! You probably left a mark on my ass!!”
I pulled my shorts down below my ass cheeks and sure enough I had a huge red handprint on my right ass check. That wasn’t the only thing that was red.
Red faced and stammering Issacc said, “I…I’m sorry dude. I didn’t realize I was going hit you so hard.”
“It’s ok man. You can make it up to me some time. Heck, I kind of even liked it.” I replied in a slightly seductive but laughy tone.
He just gave a nervous chuckle and started to turn away but not before I noticed the tent that was forming in his pants.
The time was coming. I had to really start pressing him now. The interest was there; it was evident by the tent in his pants. If I wanted this to happen, I was going to have to start being more forward.
One night while Issacc was in the living room watching a show, I was in my room. I stripped down to my thong and walked out into the living room feigning I had just woken up from a nap to go to the bathroom and hadn’t realized I was only in a thong.
“Ooopss…. Sorry Issacc I didn’t realize you were out here. It has been so hot lately that I have been sleeping in just a thong if not just completely naked.”
“Uuhhmm… no problem, man.” He got a little shifty on the couch. “You want to get some clothes on and watch a movie?”
“Sure! That sounds great.”
I went back into my room and just threw on a somewhat baggy shirt. It was loose fitting and came down to just above the bottom of my ass cheeks, like when your girlfriend steals one of your shirts that is too big for her.
I went back out to the living room, and I could see Issacc’s eyes grow wider.
“Hey man, do you want a beer or something before we start the movie?”, I asked.
“Yeah, that sounds like a good idea.”
I could feel his eyes on my ass all the way to the kitchen. The fridge faces out of the kitchen right into the living room. I opened the fridge and bent over to reach in and grab two beers, giving Issacc a front row show of my ass and tight boy pussy. I stayed like that for a good 10-15 seconds, shifting my weight from left right giving a good show. When I stood and turned around, I saw his attention shift to the tv very quickly to not get caught staring. It may have worked if it had not been for the bulge in his pants.
“Is that a banana in your pocket or are you just happy to see me?”
“What!!?? Oh no, that? I was just talking with one of my latest conquests, she sent me some pretty hot photos.”
“Oh yeah? Let me see!!”
“Oh uh, sorry I can’t. I promised I wouldn’t show anyone.”
“Alright man, I won’t make you. What movie did you choose?
“I thought we would watch Thor.”
“Yeah, I like that one.”
We watched the movie and kept drinking beer. I was beginning to feel the effects of it and so I figured he had to be as well.
“Natalie Portman is so hot!”
“She really is.”, I replied.
“I fucked a girl that looked just like her!”
“No way!”
“I swear, it was just a couple weeks ago!”
“Alright man, I believe you. You know who else is hot?”
“Who is that?”
“Chris Hemsworth! I mean check out those abs, I wish I had a body like his!”
Nervously Issacc replied, “Haha… Yea, I suppose. If you’re into that sort of thing. Also, you don’t have that bad of body.” Issacc got red faced and clammed up quickly, fixing his gaze on the TV, as if he had just let something slip, he didn’t mean to. “Sorry bro. It must be the booze talking.”
“That’s ok! I’ll take the complement. You look pretty good yourself. Judging by what I have seen of the bulge in your pants I’d say you’re not leaving the girls disappointed.”
I don’t think I have ever seen anybody’s face that red before, “Wow… Thanks, I guess. I don’t really know how to take a complement like that from another guy.”
“It’s nothing to be embarrassed about, we are both guys right and we both have dicks. Why can’t we complement each other. What are you working with down there anyway?”
“Dude!!! I’m not going to talk to you about that!!!”
“Why not?? It’s just a cock. I’ll show you mine.” I stood up pulling my shirt off and removing my thong, letting my 6 inch, hardening cock spring up over the waist band.
“Dude what are you doing!!???”
“What’s the big deal? It’s just my cock. Let me see yours!”
“No! I’m going to bed.” With that he turned off the tv and went upstairs, leaving me standing in the living room, bare ass naked.
That night was a particularly hot night. I didn’t bother putting back on any clothes, I just turned out the lights and went to bed naked. I was awoken in the night by a knock on the door to my room.
“Hey Jim, you awake?”
I got up and opened the door to find Issacc standing there in a pair of boxer briefs and a white t-shirt.
“Hey man, what’s up?”
“Oh sorry, I didn’t realize you were sleeping naked!”
“It’s all good man, what’s up?”
“Ok, well after the movie earlier and everything that happened, I was having a hard time sleeping. To be honest I have been struggling a lot lately. I haven’t had sex since my girlfriend moved out seeing you dressed the way you have been has had me really confused. Tonight, just pushed me over the edge and I wanted to apologize for how I acted. I’m cool if you’re into guys but I have always been into girls. Always will be.”
“No worries, dude!!! Why didn’t you tell me you have been having a dry spell?”
“I don’t know to be honest. I guess I was a little embarrassed and just trying to save face.”
“Well just know you never have to pretend around me. By the way, I’m not gay.”
“You’re not? With the way you have been acting and dressing lately you could have fooled me.”
“Nah man. I am totally into girls. But for a while now I have been experimenting with some anal play and have been curious about what the real thing would be like. Maybe a bit bicurious. Judging by that bulge in your underwear you are a bit curious yourself.”
“UUHHH… It’s just like I said, I haven’t gotten any action in a while so it kind of just happens.”
“Don’t sweat it bro. Do you want me to help you take care of that?”
“Oh… I don’t know man.”
“Come on!! We both get what we want. You get a release and I get to see what the real thing is like.”
“I’m still not sure.”
I reach down and grab his hand pulling him into my room with little resistance, “I am.”
He follows my lead into my room. I turn him around, so his back is to the bed and give him a gentle kiss on the lips. He pulls away at first, but I can feel the tension leave him and he begins to lean into the kiss. Our lip’s part and are tongues being to intertwin with each other. We in a full in make out session now, our bodies pressed tightly together. I can feel is rock hard cock pressing against me.
I grab the bottom of his shirt, our lip’s part just long enough to get the shit over his head and we are back at it. I must pry myself off him and push him down onto the bed. He is laying on his back, and I begin kissing his chest, alternating from left to right nipple. As he begins to moan, I trace my kisses down his stomach to the top of his underwear. I grab the elastic with my teeth and hook my thumbs into the waist band and begin to pull his underwear down.
Issacc raises his hips to help me get his underwear off. His beautiful seven-inch cock sprang free from the confines of his underwear. His cock is standing erect, he is bigger than me by only an inch, but he also is much wider and veining. I think it was love at first sight.
I grabbed hold of this masterpiece of a cock and Issacc’s breathing increased. I moved my face closer to my prize, taking in every moment. I kissed the tip of his cock and Issacc’s body shuttered. I continued to tease him and licked his cock from base to tip. Then I went back down and began sucking on his testicles. First sucking in one then the other.
“Man, you’re driving me crazy!! How do you know how to do this?”
“Lots of porn and online forums.”
Now it was time for the next step. I positioned my mouth right over the tip of Issacc’s cock and waited. I wanted to him to ask me for it. He didn’t disappoint.
“What are you waiting for? Put it in!”
On his cue I lowered my head and slowly filled my mouth with his cock. I took my time with every inch, feeling each vein with my tongue. I gaged when I got to about five inches, but I wasn’t going to let that stop me. I wanted it all, I paused and let the sensation pass and then took the rest. I finally had all seven inches in and just held it there.
I slowly started bobbing my head on this delicious cock. I began to moan around it, and Issacc began to lose it.
“Man, I’m about to cum!!”
I pulled off and told him, “Hold on, not yet!”
“What? I thought that was the deal?”
“It is but this isn’t all I want!”
With that I got into my bed side table drawer and pulled out a bottle of lube.
“AHHHH, I see!”
Issacc and I swapped spots. He stood up and I got on the bed on all fours, face down and ass up. That’s when Issacc found another surprise.
“Ahh a but plug, you do come prepared.”
Issacc took the plug out with a satisfying pop. But now I felt empty; to entice him I shook my ass at him.
“Calm down it’s coming.”
With that I felt a drizzle of lude run down my ass crack and then Issacc put some lube on his and began stroking himself to get it worked in. I could feel the tip of his cock at the entrance to my ass and my pulse began to race. This is it; this is what I have been waiting for. With small push his cock was in my ass a good three inches.
“Don’t hold back,” I told him, “I can take it. Give it to me!!”
“If you’re sure!!” and with that he rammed the remaining four inches into my ass, and I could feel our balls slap together. It was a bit shocking and a little painful. But it was worth it. I have never felt to so full before and I was loving it.
Issacc gave me a minute to adjust and then he asked’ “Are you good?”
“Hell yeah, I’m great!!! Let’s do it. Fuck this boy pussy of mine!!”
“Wow I love hearing you talk like that!!”
“Good daddy! Now give me a good fucking!!”
“As you wish.” Issacc pulled almost all the way out to where just the head was left in and then slammed all seven inches in. I gave a hard grunt mixed with a moan. Then he did it again. Then again and again. Each time increasing in speed and intensity, each time my grunts and moans turning to sounds of pure extasy. Every thrust sent shock waves through my body, hitting my spot each time and I was building to climax.
“That’s it daddy!! Give me that big cock!! Fuck this boy pussy right!!”
“I love your boy pussy, it’s so tight!!”
“You are my first. I knew I was waiting for someone; just didn’t know it was you!”
Issacc kept fucking my ass and I was in pure bliss. I began milking his cock with my ass by tensing up, squeezing his cock with my ass.
“This is amazing, I don’t know how much longer I am going to last!!!”
“Let me flip over. I want to look in your eyes as you cum inside me!!!”
Issacc pulled out but as soon as I was on my back he had my legs on his shoulders and rammed is cock in my ass. From the angle I could the pleasure building on his face and my own cock was solid as a rock, swaying with every thrust.
“Here it comes, man!!”
“Come in my boy pussy daddy, make me your slut!!””
With one more powerful thrust Issacc held his cock in my ass and shot his load. The sensation of with hard cock shooting it’s hot, sticky load in my ass sent me over the edge. I had the biggest orgasm of my life and shot loads of cum all over my chest.
“FUCK YESS!!! Dady fuck yes. That was amazing!!”
“Wow, that was really amazing. I can’t believe we just did that, why did we wait so long?”
“That doesn’t matter anymore. This boy pussy is yours from now on. Whenever you want it however you want it. I am your personal slut!!”
“That’s great!! You might want to just keep not wearing underwear because I am going to want it every day, multiple times a day.”
“Better yet, why don’t neither of us wear any clothes? I’m going to want to suck that cock whenever I can.”
“Sounds good to me. But why wait.” I looked down and saw that Issacc’s cock was already starting to get hard again.
“Looks like it’s my lucky night.” I went down, taking his cock in my mouth and started round two.