This story occurred about 10 years ago when I was still on Active duty with the military, and I have changed the names. I had a coworker that was having some serious money problems; so one day he asked if he could rent the empty guest room in my condo. We agreed on a price and he moved in.
Several months go by and things are cool, we got along well as roommates and coworkers. Then one night he comes into the living room wearing just a pair of shorts, no shirt or socks.
Let me describe him, he was 28 years old, 6ft dirty blond hair, grey eyes, nice build and toned body and going through his fourth divorce. He somewhat of an A&F looking guy and those clothes compliment his body and looks. I was 35 5ft 11ins 210 pounds, not a gym body but not fat just a few extra pounds, brown hair and blue eyes.
So this night Zach says he needs to talk with me but first needs to take a shower. So I hear the shower running, and wonder what he looks like with water running over his body. So about 20 minutes later, he comes downstairs in just some hot looking tight shorts. I knew something was up, because he never walks around dressed like this. After taking in the sight, I wished he went shirtless more often.
While he was in the shower, I fixed myself a drink and changed into more comfortable clothes, so he tells me that he is not going to be able to pay the rent that month, so I asked why and he explained that his bills were more than expected that month. He assured me that he would make it up to me in any way he could. As he said that, his right hand drifted up his tan chest to his left nipple. In the past, I have gotten the vibe from him at times that he was gay or at least bi, and tonight it was returning.
I asked what he had in mind and what he meant that when he said "any way". Well he got nervous and really couldn't come up with an answer, and when I started to walk away he finally said "I would suck your cock." I turned to look at him quickly and he couldn't make eye contact with me. I walked over to him and asked if he was serious and he shake his head yes, and I told him in a very commanding voice to say it. He said "Yes I would suck your cock".
I was getting turned on by this and I checked him out, and noticed his bugle was larger than when he first came into the living room. So I reached out and touched his left nipple and he reacted with a groan and his eyes rolled up into his head. So I knew he was mine!
I told him to sit down and let's come up with a deal, so he suggested that he would suck my cock once a week when he couldn't pay his rent. I told him to sleep on it and we can discuss this again the next day. I wanted us both to be sure about this agreement; I didn't want him thinking I forced him to do this.
So the next night after I get home Zach comes down stairs again dressed like he was last night and I can tell that he had recently taken a shower, he did smell good and clean. I thought to myself I could really get used to this, but also wondered what he would look like in a jock strap.
So he seemed eager to talk, so I was concerned he changed his mind, so I told him I wanted to change clothes and jump in the shower. So I got up to my bedroom strip and walk to the bathroom naked, and Zach is walking up the stairs at the same time. I never intended him to see me naked. But I figured fuck it. So I am in the shower and hear the door opens and Zach asks if this is ok. And I know then what his decision is. I told him I be done in a few minutes, so we just start talking about our days, and small talk.
So when I am done and open the shower he is sitting on the toilet just talking, and I notice his eyes are focused on my crotch, while I am drying off. So I finish drying off and go to my room to get some clothes on and he follows me.
So he starts to hint about the agreement, and I decide I am not gonna put on clothes yet and just relax on the bed in my towel but very loosely. And then just outright ask him if he made his decision, and he says yes. But admits he is nervous about it. I don't ask him if he has ever done anything with a guy before, so I pat the bed next to me to hint for him to sit down.
When he sits down, I put my hand on his thigh and I hear him sigh, and tell him to relax. So I ask him when he would like to start, and he said "right now before I chicken out". So I said ok, and just took my towel off.
My cock started to fill out during our conversation, whose cock wouldn't when a supposedly straight guy wants to suck your cock.
So he reaches out with his hand and take a hold of my cock, and plays with it a bit and gets it fully hard, and I tell him to just lick it like an ice cream cone and he does. He has a nice thick long tongue which feels awesome at this time. I reach into my night stand and pull out some poppers and take a nice hit. He asks what that is, and if it will show up on our drug tests, and I tell it that it won't and it helps relax you but makes you feel great. I ask him if he wants a hit and he does, so I have him take two very deep hits and then he turns and just goes down on my cock. I knew at this point he has sucked cock before, I have a thick cock that is 6.5 inches and he is not having a problem with it, like a virgin cocksucker normally would.
I am a verbal guy and start saying how good it feels and tell him he is a good cocksucker, and then start running my hand over his back and neck. I didn't want to face fuck him on this first time, and ruin a possible thing for the future.
So I naturally start noticing his ass, which isn't that big and doesn't show well in his every day clothing, but these shorts are tight. I pull him off my cock and ask him how he likes it, and he says it tastes good. I ask him if he needs to jack off while he is sucking me (I wanted to see what he has between his legs). He says not right now, so I put my hand on his head to signal him to begin sucking again.
I begin rubbing his back again, he does have nice soft skin, and decide to go lower and rub his ass, and when my hand touches his ass, he groans with my cock in his mouth. I usually prefer my boys between my legs while sucking me so they can play with my balls and nipples when I tell him, but I make do. After about ten minutes I announce I am gonna cum (we never talked about where I was gonna cum), so I decide to see what he is gonna do. He starts using his hand to jerk me off while he keeps my head in his mouth; this guy definitely has watched his share of porn or has sucked cock before. He pulls off of me at the last minute and some of my load lands on his face but he doesn't get any in his mouth. The rest of my load lands on me and on his hand from jerking me off, I pull his hand to my mouth and lick it off while he is watching me.
So he looks at me and asks what does it taste like, and I scoop some up and tell him to taste for himself, but he declines. I tell him he did a good job, while rubbing the top of his head, and look at his crotch and notice he is hard. So I ask him if he wants to jerk off, and he asks if I would mind. I told him no, and that I might get hard again. He asks if I have any straight porn, I look at him and ask what for? And that I don't have any in the house. He says he will take care of his problem later in his room, and gets up and adjusts his shorts and leaves.
I lay there for a few minutes enjoying the good head, which I just got from a semi straight guy. I get up and go to the bathroom (naked) and clean up my junk and put on some clothes and head downstairs to the living room/kitchen area. Zach stayed in his room afterwards. So about an hour later, I go knock on his door and ask if I could come in, and when I enter he is wearing jeans and a tee shirt (his usual attire). I wanted to make sure he was ok with what we did. So I ask him if he is hungry and want to do something for dinner. He is hungry so we decide to order some delivery food and he comes downstairs.
So we chatted about what happened, and he was OK by it, he said he enjoyed it actually. And I said I noticed he was hard and I wouldn't have minded if he jerked off while sucking me. He was a little surprised by that, and I said Zach, I am gay so it won't bother me. That broke the ice and we talked about all different subjects and he wanted me to compare him to other guys.
So he asked what I am attracted to, and I described my general idea of a hottie, and added that I like them in a jock strap, and he wanted to know why. So I tell him that it I like how it makes the guy's package look and lifts his ass cheeks. So I ask him if he has ever worn one or owns one, which he answers no to both questions. I am disappointed but wonder if this agreement goes long term, I could give him one as a gift.
So I ask him what he thought about the poppers, and he said he helped him relax. He said he like to do them again the next time. So I asked there will be a next time, and he said that money is gonna be tight for a while. This was fine by me.
Over the next few days, things are cool between the two of us, and I will wait for him to make a move, I don't want to spook him. But I know I have him hooked on cock. So just a little over a week after our first episode, I come home from work and Zach is in his tight shorts again and I know what gonna happen tonight.
So he is a little nervous about how to start this, so I ask him if he has his rent money, and he said no and he is ready to keep his promise of our agreement. So I tell him that I am gonna shower so I am nice and clean for him and he thanked me for that. And then I say are you gonna keep me company while I shower this time, and he blushed. So he follows me to my bedroom and I just get naked in front of him, like I have in front of many other guys I was about to hook up with.
I head towards the bathroom and start the shower and we are just bullshitting about this and that, nothing really important. And I ask him if he wants to join me this time? He looks a little bewildered but considers it, and says that might be moving too fast. And I think too fast? Fast for what? But I know someday he will be doing more than suck my cock.
So I clean up and start drying off and notice he is looking at my junk again and that he is hard. So we head to my bedroom and I put on some porn (gay of course) and we get on the bed. So he starts playing with my cock but I do notice he is paying attention to the porn. And then he asks for some poppers, he says it helps me suck my cock. So he takes a couple deep hits and starts licking my cock, and then I suggest he should get naked.
I said with the straightest face I could that it would help me feel more comfortable if we were both naked. He considers this for a few seconds and takes his shorts off, and I notice that he has no tan line, and I find this hot and tell him so. He was shocked but appreciated the compliment.
He goes back to sucking my cock and I am telling him how good of a cocksucker he is, and rubbing his back and start working my way towards his ass. He groans again when I touch his ass, and I ask him if he likes that I enjoy his body. I tell him he has a nice body that I could have some fun with. I offer him some poppers and then ease him back onto my cock, and he is sucking it with more effort than he was. I tell him to keep that up and I will cum soon and I start rubbing his ass while telling him he has a nice ass. I decide I won't play with his boy pussy yet, but I will eventually get my cock in there.
The thought of fucking his ass, brings me over the edge and I announce that I am about to cum, and I put my hand on the back of his head, I am not holding his head down, and he could easily pull his head up if he wanted to. This way I can give him an excuse for taking my load. A big step on our second session, he takes it like a champ and swallows his load. He keeps my cock in his mouth and is licking, I have to pull him off of me, since my cockhead get extremely sensitive after I cum.
I ask him what he thought about the taste and he said it wasn't bad, and he was glad that I encouraged him to eat my load by putting my hand on his head. He rolls over and I see he has a nice cock, longer than mine but not as thick. I tell him to jerk off for me, I wanna watch, and I see he gets that excited look in his eyes, and says really? So I take a hit of poppers and offer him a hit and we start jerking off together, between watching each other's cock and the porn on the TV we aren't going to last long. At that point I start to run my hand over his chest and play with his nipples and he groans when I do that. I ask him if he likes that and he says yes, he wished his ex-wife's would have played with his nipples, and I tell him I like playing with nipples.
We both cum and just lay there catching our breath, he shot a big load and it makes me wonder how long he has been holding that load in. I reach over and take some on my finger to get a taste and notice he is watching me. So he asks how does it taste, and I tell him I like the taste and wouldn't mind cleaning up his mess. He is shocked by this and says go ahead, so I lean over and start lapping at his load which is on his happy trail and pubes and notice how good he smells. I lay my hand on his leg and slowly slide it up his leg and stop just short of his cock. I am not sure how far he is willing to go today.
I am not sure how long we laid there next to each other, it kind of felt good and normal, after a while I ask him if he needs to take a shower and he says yea, and wonders if I do also. So I ask him if he wants to shower together, and he says sure. I think he wanted to try it when he asked me, so I tell him the rule about showering with another person is that you can't wash or dry your own body. That we will have to wash each other bodies. So we get up and head into the shower, and I tell him I will start this and show him how it's done.
So I put some soap on a wash cloth and start lathering up his back and work my way down his back and get in between his cheeks which surprised him, and I tell him to lean forward and he follows my directions without hesitation. So then I have him turn around and I start on his chest, we are standing very close to each other and I am starting to get hard again. So I work my way down his body and clean his cock and balls and his legs and I know he is enjoying this. I make a comment about him getting hard and he gets a little embarrassed. But I tell not to, that he has a nice cock and it is enjoying the attention. I rinse him off and say now your turn. He is a little hesitate at first but gets into it, he got his fingers into my ass crack and I leaned forward to him and he hit my rosebud which just made me moan. He asked if I was ok, and I said it feels good and to continue, so he rubs his finger on my hole again and then starts on my chest.
And by the time he got to my cock which is almost fully hard and he mentions that, but cleans it good and rinses me down, I turn off the water and open the shower stall and grab a towel. I told him that we can try and dry each other at the same time or separately, and he says he liked the attention I gave him while washing his body and start drying him. He moaned, and he eyes rolled back and his head tilted back a little. So I made extra sure his cock and balls were dry and really enjoyed rubbing the towel into his nipples when I was doing his chest. When I was done he started to dry me with vigor and really was paying attention to my ass and cock.
When we were done, we stepped out and I asked him if he was hungry and wanted to watch a movie or something, and we agreed on pizza and a movie and to our bedrooms to grab clothes. I make the comment that I wouldn't mind staying naked, he said "really?" I explain that before he moved in that I enjoyed just relaxing at the house naked. He said he never was able to do that.
So we order pizza and just chatting, I feel like our friendship was expanding due to the sex. So he asked if I was serious about watching the movie naked and said if it wasn't gonna make him uncomfortable I was game for it, the grin on his face was like a kid.
As soon as the door closed after the pizza was delivered he took off his clothes, he was like a kid without mom and dad home. So we eat pizza and watched a movie naked and just chilled. We both were checking each other out during the movie. I wasn't sure if he wanted to play more but I sure as hell did, but didn't want to spook him. So after the movie I head to bed, I just pick up my clothes and head upstairs, and brush my teeth and lay in bed reading a book.
After a few minutes Zach knocks on the door and comes in, still naked and looking good. I pat the bed and he sits down, I can tell he wants to talk. So I ask what's on his mind and he said today and last week. My heart jumps to my throat, I think he is gonna freak, but he said he really enjoyed today. The sex, the shower and especially the hanging out naked, and then he asked if I was checking him out and I said of course. I think you are good looking and have a nice body.
He just sits there quietly and an awkward silence begins so after a minute or so, I ask him if this is the first time he has messed around with another guy? He can't come out with an answer, so I just put my hand on his and ask and told him don't worry.
So then he started asking me about past experiences, and I notice he is getting hard, and ask him what interests him.
He says he wonders what it would be like to kiss a guy, and have a guy suck his cock. I know I got him now, its gonna be easy street from here on in (his boy pussy). So I move on the bed to make room for him and he slides on further and lowers his face to mine. He puts his lips to mine and just touches and pulls back, and I am thinking what are we in the third grade?
I put my hand on the back of his head and pull him to me, and we start making out like teenagers, I am under the blanket on my bed and he is on top but I am feeling him up good and he is groaning like he enjoys it. I break the kiss and pull my head back and look at his face, to find him smiling. And I notice that we are both hard, so I take the dominate role and push him on his back and turn around and start licking his cock and balls.
Once I have him very hard, I take the head in my mouth and run my tongue over it. He just groans and says oh my god several times. I am running my hands all over his body, his chest his legs, and playing with his balls. I take my mouth off his cock and you had to see the look on his face, but I just tell to stay where he is, and get the poppers out of the nightstand. I take several deep hits and pass the bottle to him and then continue to suck his cock. I can hear him huffing the poppers and then feel his hand on my head and know he is enjoying this blow job.
A few minutes later he shot his load in my mouth and I got in all down. He started to apologize for cumming in my mouth and for not warning me. But I told him it was my pleasure to take the load, and that it tasted good. So I crawl up towards his head and we start making out and I grab my cock and jerk off while kissing him. A few strokes later I cum all over myself. Zach is breathless and says that was awesome and has this huge smile on his face, so I grab my blue boxer briefs and wipe up my load and invite him to spend the night in my bed.
He hesitated a few seconds and says "you sure?" and I pull back the sheets for him, and he climbs into bed. We kiss a little bit, and I said if we keep this up, we won't get much sleep. So we fall asleep shortly after that.
We are awaken by my alarm, and he seems a little confused and nervous, until I reach out and touch him and say good morning. We kissed a little and discussed how we slept, so we get up to get ready for work and he showers first. He seemed a little surprised when he came downstairs after showering and I was still naked. I reminded him that I enjoy that. He takes off for the office and I head up to shower.
We had a normal day at work, I don't recall any unusual moments at work, and I think we were both happy for that. So after work, I hit the gym before I get home. When I get there Zach is sitting in the living room watching TV. So we just shoot the shit for a little bit and discuss dinner. We both want pizza and order delivery again.
So Zach asks if we are gonna eat our pizza naked again, and I tell him only if he answers the door in his underwear. He looks at me like I am crazy but I know that he is thinking about it. So I dare him to do it, and tell him if he does, that I would suck his cock again and let him cum where ever he wanted to. So he gets up in front of me and starts to undo his pants, I tell him to slow down so I can enjoy this. He blushes and asks if I am enjoying his stripping, and of course I am.
I push the coffee table out of the way and he comes closer to me and starts to dance what most guys think a stripper does, and pulls his zipper down and turns around with his ass facing me, so I just reach out and touch palm it. He says that management doesn't allow touching. We both laugh and he bends over while he pulls his pants down. When he turns around I notice that he is getting hard. And I let him know that I wasn't the only one who enjoyed that. He told me that it was fun and kinky, and that he is enjoying all his new experiences.
So he gets his pants off and I have to say I love the underwear he choose, he choose a grey pair of 2xist posing briefs, they do his package and his ass justice. I lick my lips when thinking about eating that boy pussy of his. But I am torn whether I like him naked or in his briefs. But he chooses to get naked for dinner.
So while eating he asks a few questions about man on man sex. Like is anal sex painful, and is face to face sex possible, like that. I wasn't sure where he was going but let him talk. So after the movie, I decide to turn in. So does Zach, a few minutes later he knocks on my door and I tell him to come in, but he put his underwear back on.
Zach asks if he can borrow the porn from the night before, he said he wants to see them fuck, so I tell him to take it out of the VCR and enjoy it. I asked if he wanted me to suck his cock, a deal is a deal but he said he take a rain check, which was fine with me.
The next night when I get home from work, Zach is in the living room watching TV fully dressed, we chit chat about our day and decide on dinner, it seems like we are having dinner together almost every night now. So we cook some chicken and stuffing and share a bottle of wine, this is the first time I have seen him drink. So while cleaning up, Zach asks if I was serious about sucking his cock, and I told him of course I was. So he tells me he wants me suck his cock while he watches porn, and I said "When?" He laughs and blushes a little, he is cute when he has slightly red cheeks.
He wanted it to happen that night, so I told him cool. And we both took showers and we put the porn in downstairs and watched it for a while, we were both getting hard. And then I reached over and started to play with his cock and then got on my knees in front of him and started to lick the inside of his thighs, and he starts to moan and said that it felt great. I had to push his hand away from his cock a few times. Then I start to lick his balls and his cock and until he reminded me that I was supposed to suck his cock.
So I take the head in my mouth and run my tongue all over it and suck on it hard while playing with his balls. I notice he is enjoying it and opened his legs wider for me, so I slide a finger up behind his balls while I take as much of his cock into my mouth. I take my hands and put them on his chest and start playing with his nipples and then run my hands all over his body, and he asks if I like feeling him up. Damn he is getting verbal with me and turning me on even more.
I am running my hands up and down his legs and I feel his hands on my head, and he says something like yea take my cock. I look up at him and he is watching the porn, it's so hot that I am just there for his cock. So after a few minutes of this, he pushes me off his cock and asks me to move over so he can stand up, and as soon as he does he guides me back onto his cock, but now he is face fucking him and I grab him by his ass. I pull his cheeks apart and run my finger over his hole and he says to do it again, so I just keep my finger on the outside of his hole until he announces that he gonna cum and shoots in my mouth, and I swallow it down. He pulls his cock out and bends over and kisses me, this totally surprised me since he has never initiated a kiss, but has enjoyed them. He kinda falls back onto the couch with this look of relief and satisfaction on his face, and tells me that it was hot and he wants me to play with his ass again.