We had been chatting online for a week or so, trying to find a time to meet up.  His pics were damn sexy, mid 30's, black, 5'10, buff, about 170.  When we finally were able to meet up, I had to blow off Bi_boy to meet him, so you know I was interested.  He's staying with a relative so it makes it difficult to meet up plus he is located in the Northwest suburbs, so geographically, he is undesirable.  But I arrive at his place and he takes me to the basement.  I am a bit uncomfortable but I head down.  He immediately starts feeling me up, grabbing at my crotch and ass.  It sure didn't take long before I was ready.  He keeps at it and we start to kiss.  So far, so good.  I eventually start feeling him up and go and grab his cock and ass. Shortly after he unzips my pants and starts sucking my dick.  I let him go at it as I take off my clothes.  He has me hard as a rock and nice and wet.  He excuses himself and comes back, much to my surprise with only lube. When guys leave like that they usually are searching for a condom. He points over to the couch and I go and lay down on it.  He moves to the side and blows me so I am good and hard.  He stands up, lubes his ass and my cock and sits over me, one leg on the floor, one on the couch and guides my prick into his ass.  It is warm and tight.  After two minutes, he blows his load all over my chest.  I can feel the heat from his jizz which only makes me harder.  He is riding me like a pro and I am bucking into him.  Damn he is a hot lay.  Finally I can't take it anymore and I shoot my load deep in his ass.  Afterwards, I ask him about his scar and he says he was shot in Afghanistan.  Fuck, my first military dude and he is sitting with my boys deep inside him.  Fucking hotter now.  I wish I knew he was military before but it just got better.

stalker alert

I met this kid awhile back, June of last year.   I put out a crazy ad with some religious undertones.  I have some issues dealing with this from my childhood.  This 18 year black guy answers and has a cute face.   He mentions that he just graduated from high school.  This is usually a red flag as I don't mess with high schoolers even if tho ey are of age.  I have 2 reasons: I am slutty but not a pedophile and quite honestly,  even if they are of age, they are emotionally not ready to deal with shit. I should have followed my instincts.

The kid has a cute face so I invite him to my office.   Mistake number 2.  He arrives and I realize why I only received a face and ass pic.  He was a a young chub. Not really a chub but definitely overnight.  Mistake #3 for those keeping track.   being horned up and in a hurry,  I decide to get off and get him out of my life.  mistake #4.

We go to my office and get down to it. He wants to kiss but I say no.  He gives me head and I think about another dude.  He eventually gets up and turns around.  I grind my cock into his ass and enter him raw. He keeps moaning out my name as I pound him. I am trying to focus so I can cum quickly.  it works and I shoot a huge load of jizz up his ass. After he cums, he asks me why I came in him. I told him he should asked me to ppull out . He wants to talk but I tell him I have to go and get him out the door.  I leave and figure this is a lesson learned.

A few days later he emails me asking when we can get together.  I ignore him. He continues emailing me and I finally respond but basically blowhim off but nicely. A week or so passes and my assistant tells me about this bizarre phone call.  She says this call came in aboaut some new business and he says he's a friend. but he wouldn't leave a number just  a name, deanthony.  I play it off as some weirdo but he continues to call. After a week or so,  it stopps but he starts up again in July. This continues until the end of august and he stops until Thanksgiving.  And now he is leaving voice mail.  i ignore him until he
 starts up again at Christmas.   It continues and then stops. Until his spring break starts.  He calls again and my assistant is out so I answer. I laid into the kid about stalking me. I also figured out how he knew my name and number: he took a business card. Mistake #5.

Some valuable lessons learned.  Let's see if he he gets tthe clue to leave me the fuck alone when he is back from school.

Eager slut

I met up with this interesting dude.  We had hooked up before, about two years ago, pretty much your run of the mill hook-up.  He's cute, thin, in shape, attractive, 5'7, 130 pounds, Spanish Arab mix, late 20's.  I didn't recognize him from his pics but did when we met up.  Not sure if he did.  It wasn't brought up.  We went up to my office and he's all excited as he says this is a fantasy of his.  I play along, me too except I've done it a few too many times to be a new experience but I am always fantasizing about the next one.  We get up and we feel each other up.  He has a nice taut body.  I kiss his neck and grab his ass, pulling him into me.  We start undressing each other.  Once we're naked, he starts giving me heading.  He's pretty good at it and I take advantage and start fucking his mouth, pulling on his longish hair.  After a bit of me working over his mouth and enjoying my pre-cum, he stands up and turns around.  I know where this is headed.  I bend him over a bit, grab some lube and stick my dick in him raw.  He has a nice ass.  Silicone based lube is feels so good when fucking bare.  He's pretty vocal.  No one is here but you never know so I tell him to shut the fuck up.  I'm not really all that verbal when I'm fucking, I usually like to concentrate and fuck.  Recently, I've taking a liking to talking smack to a guy when I fuck him.  He submits and I start calling him names. Telling him he's a dirty slut.  He's getting off on it.  Eventually, he moves to a chair I have against the wall and gets in it. Now I really start pounding him and he loves it.  He tells me he wants my cum in him. I tell him he's going to have to work for it and keep pounding his ass.  Letting up at times so I don't cum too quickly.  I want to really fuck him long and hard and take it out on him.  He's definitely game.  He's getting loud again and as I keep pounding him, I smack the back of his head and tell him to shut the fuck up.  He's totally surprised and really goes back on my cock as he tightens up.  That's it.  I grab his little hips and pull him back as I thrust and shoot a load deep in his ass.  He tells me he can feel my hot cum in him and it's a huge load.  He cleans up and leaves.  About an hour later, I check my email and he's already sent me an email about fucking him again.  I like an eager boy but not that eager.

A surprise visit

You guys know that I like Lewis alot.  He's hot and a good fuck.  The only problem is that it takes too long as I either have to pick him up, drop him off or both.  He texts me and lets me know he is going to be downtown.  Perfect, I can host.  He comes over at lunch time.  We don't waste too much time.  He starts undressing me and gets right down and starts sucking my dick.  He's alll into it and loves sucking it from my suit.  He unbuttons his pants and takes his out to stroke.  He's sucking me for a bit when I decide to dick slap him around.  As I am whacking my cock across his face, he shoots his load.  That was fast.  He starts sucking again and I tell him that I want to get undressed and fuck him.  We both get naked, I grab the Vaseline and lube up my cock and his hole.  I approach from behind and push him forward and line my cock up and stick in raw.  It feels good and tight.  I fuck him for a bit, pushing him forward so that he lies across the desk.  I am pounding his, making sure that when I feel too excited I slow down so as not to cum.  We go at it for a bit when he asks to change positions.  He turns around my chair and gets in it, and I push in from behind and fuck him from behind. I am giving it to him good and hard and after a bit, he says he can't take it anymore.  He starts sucking me off and I throat fuck him, good and hard.  When I get close, I tell him and blow my load in his mouth.  He keeps it in there for a bit, getting it all up and eventually spits the rest out, saying I had a huge wad for him.  It was a nice, unexpected visit from my little thug.

Some virgin ass

I met up with this black guy on the DL. He had been with guys before but only getting his dick sucked or topping. I am all for giving head but I was not about to take his 10 inch cock. We meet up and decide to play even though it may just be oral and we both want more. He's cute, 6'0, 150, shaved head, dark skinned, and a big one. He has a nice tight body. We get at feeling each other up and soon are naked. His dick was all he said and more. Big and thick. I was sucking him for a bit and started fingering his ass. It was super tight. He told me he's never had anything down there before, dick, finger or toy. I asked him how he liked it and said he did. I asked him if I could fuck him and he said maybe but only if I let him fuck me. He said only if he could fuck me. I said yes mainly because I know these donkey dick dudes have a hard time keeping it hard and could tell that was going to be the case with him. I put the condom on him and I was oddly turned on. While he was laying on the floor, I got on his chest and stroked his dick. He reached up and started sucking my dick, which got him hard. He was not good as he kept scraping his teeth on my cock. When I pulled out, he apologized saying that he had never sucked a dick before. I noticed that he went alot softer as soon as he stopped sucking. I told him that he isn't hard enough to fuck me. He agreed and I said, how about I fuck you. He asked me to go slow. Sure. No problem. I turned him around, lubed up his ass and my cock and stuck it in him raw. Not only was he getting his first cock, but his first raw cock. I wasn't in him for long when he started complaining about it hurting. I wasn't surprised cause his hole was tight. A nice, small piece of chocolate. I tried a few more times, but he was never able to take it for more than a minute. Eventually, I starting rubbing up against his ass and when I was getting close to cumming stickin it back in, getting some cum in him, the rest all over his hole. He was turned on and came all over the rug shortly after. Love fucking and breeding virgin ass, even if you have to deal with all the bs of them not being able to take it for long.

Running out with my pants undone

I know I said that i was done with him as he was just too difficult to manage. But hey a guy gets horny and he's persistent. I guess wc here likes a guy to chase him. Not really. he texts me early in the morning and i was up and going to the office. he says he has a place, so i pick him up. it's his old apartment building. We go and walk around through what feels like a maze. we end up in this back hall near the fire exit. he pulls down his pants and i do the same. he asks me if i have a condom and i say no. he's says OK and pushes his ass back and grabs my cock. he usually makes me wear a condom so I'm really excited. i enter him raw and his ass feels like silk. i start pounding away on him. we're fucking for about 2 or 3 minutes when we hear this door open and foot steps. the next thing i know, we are running out of the building, undressed. i stop by a garbage dumpster, make it seem like i am taking a piss and get my shit together. waiter boy ran the other direction. seriously, wtf, i am too old for this shit. running down and alley in a suit before 7 am.

Fem hotel boi

I'm sitting at the pool working on my tan when this twink catches my attention. You really couldn't miss him. He is obviously not in Mexico working on a tan with a big straw hat, milky white skin and an obvious I'm a big sissy boy attitude. That being said, he's striking. Pretty actually. I make a note and see him the next morning at the restaurant. I give him a look that let's him know that I am checking him out and a subtle nod. I can see him thinking and he starts smiling as I walk away. He makes a point to follow me. He asks me what's up and we make some small talk. Before this goes any further, I ask him how old he is and he says 18. I tell him I need to see some proof and he says, .."well, my passport is in the room. If you really want to see it, I'll show it to you." I'm game but tell him I have to go back to the room and touch base with my boyfriend. He gives me the villa number and I tell him I'll be there in 10-15 minutes. I get there and he answers the door naked. He pulls me in and is making out with me, forcing himself on my. I kick off my flip flops and we end up on the couch. He is pulling my trunks down, grabbing my dick, a little too aggressively. I take my shirt off and pull him into position. I spit on my cock and get enough for his hot smooth, pink hole and stick my dick in raw. I fuck him for a bit on the couch when he says the position hurts. I ask him which bedroom and he tells me, but makes sure I know that he doesn't want my dick to come out while we go there. I pick him up and he wraps his legs around me as I get to the bedroom. I'm careful not to drop him or let my cock slip out. I put him on the edge of the bed and start fucking away. I can feel my boys letting me know that I'm getting close. I pull out cause I want pound this little bitch more. I turn him around and get him doggy style, just off the bed. I push all in without stopping and he gasps. I pull him closer as I pound away at his tight little ass. It feels so good. I can tell he doesn't have a lot of experience but he's taking it like a man. I pound him for a bit longer before I fill his ass up with my cum. I pull out and let him know I have to go. I took off pretty quick, leaving him dripping cum onto the bed. Hot little fuck, just hope he doesn't come to me and cause a scene at the pool.

We're not related, are we?

I was in my office working on a Sunday and I was horny, shocker. I end up meeting up with this 24 year old. He's totally my type, 6'1, 165 pounds, dark brown hair, brown eyes, nice smile. He comes over to my office and he was even hotter than his pics. The first thing he tells me is that he is just back from brunch and is buzzed. Hot and drunk, perfect. We start kissing. He's an incredible kisser. You can tell he is into kissing as he knows how to use his tongue and not be sloppy. We make about for about 10 minutes while we feel each other up. Eventually, we start taking off clothes. He has a nice body, some hair but not too much. And of course skinny with a nice cock, about 7.5 inches. He goes down and starts giving me head. He is pretty good at it. We trade head back and forth until I get him on his back. I start making out with him as I grind my cock into his body. He's totally ready to fuck. I bring his legs over his shoulders, spit on his hole and my cock, and slowly inch my prick into his hole raw. It's nice and he's ready to fuck. Once I am all in, I let him feel my cock inside him. Then I start moving it from side to side to stretch him out a bit. Now that I have him ready, I start to fuck. I get a nice pace going and pick it up. He's moaning and groaning. We keep moving around on the carpet so much that he hits his head on the wall and we have to move back. I keep going at it, fucking his nice tight boy twat. We keep it up and I eventually lose it, breeding his ass. We get up and start to dress when I move in and we start kissing. He looks at me and starts to unbutton his jeans. I go down oh nim and take his dick and start sucking. He's pretty worked up about the whole scene, probably thinking about my hot jizz in his ass and he starts to cum. I don't ever swallow but he kinda snuck up on me and he starts shooting in my mouth. I was so into the whole scene and him that I didn't push him off. Plus, he already sent the first two shots down my throat and I did just knock him up with my sweet cum, so why not. Plus we would have fucking hot kids. As he's getting ready to leave, he looks up at my wall and starts laughing. He says we have the same last name. He must have seen the look on my face of complete horror as I have a distant cousin with his first name but it dawns on me that he would be in his 30's not 24. We laugh about it and talk about our backgrounds for a bit and make out a bit longer. It was a very hot Sunday afternoon with a hot dude.

The 40 year old virgin returns

We all know that he isn't a virgin anymore thanks to me. That's his story and I probed him on it and he stuck to it claiming I was the first dude to fuck him which also makes me the first dude to breed him. He also lets me know his ass was sore for a week and I'm surprised since I took it easy on him. Oh well no one said bottoming was easy. Now it's happened a second time and I know he was sore. I met up with him again after a meeting I had by his house. I get there and much like the last time except he's really happy to see me. We don't waste much time, he takes off his clothes, I get out of my suit, he grabs some lame lotion like Jergens or Suave, lubes his ass and my cock and sits on me. I let him get comfortable and I start aggressively fucking him from underneath. After a few minutes, I reposition him on his back and just start an aggressive all out assault on his ass. I bang him so hard he's hitting his head against the wood bed frame but I won't let him move. I just keep pounding my raw dick in his tight ass until I shoot my load deep in his Latin daddy ass. We clean up and I leave. No BS, no kissing, just two mutually satisfied guys. I might have to make find a reason to have a meeting out this way again.

The return of the space cowboy

About a year and a half ago, I met this twink, I'll call him, space cowboy, cause he kinda reminds me of the Jamiroquai lead singer, a younger Jay Kay without the drug problem. Nice kid, at the time was 21, now, 22, about 6 feet tall and 145 pounds. One of the types I really like, skinny twinks. He has a total daddy complex due to his real dad not wanting anything to do with him and his step dad physically abusing him. Throw in some low self confidence, growing up without a lot money and being picked on for being gay, you can kinda get the picture. We fucked a bunch until June 08 when I rough fucked him bb on my desk at work (I may need to tell that story sometime, it was hot). After that he had a blow out with his roommate, who smacked him over the head with a beer bottle and decided to go back home, out-of-state. He moved back early this year and we chatted on line for a bit but never met up. Last week he texts me and says hi and asks me to hang out. The bb fuck came up and I told him I wanted to do him bb again. We talked about it for a L-O-N-G time cause he wanted to use a condom but I told him the truth, once you have bb sex with someone, using condoms loses the intimacy and somehow it's not the same. He agreed to bb for me after he felt sure I was clean (even tho the first time we didn't discuss it, I just did it). We make plans to meet up the next day.

I get to his place early in the morning about 8:30, before work. He answers wearing a tight t-shirt and small Papi briefs. I'm totally aroused already. We catch up and chat about things. He tells me about what he did back home and how he met this guy and they are kinda dating still dating but long distance. It's hard for me to resist but after a bit I move in and kiss him. We're making out, kinda softly until I pull him over and have him sit on my lap and we really start making out, grinding into each other. All the while we are making out, I am feeling his smooth, Lily white body. I can see his hard on in his little briefs and need to get out of my suit. We head to the bedroom. We undress and I lay back on his bed. He start sucking my cock while I am feeling up his body. He's really good at giving head. He really knows how to suck cock and use his hands to get you going. I have to stop him cause it feels so good and I don't want just a blow job. I go back and get on top of him and start kissing him again. Slowly sucking down his body until I get to his cock which I take into my mouth for a bit. While I suck his dick giving him a sloppy blow job getting it nice and wet as I am fingering his ass. He tells me he wants my cock. He wants to ride me so he quickly puts my cock in his mouth to get it wet and then gets on top of me and lowers himself on to my bare cock. He controls the pace, placing his hand on my chest to leverage himself. Once I know he's comfortable, I pick up the pace and we really start to fuck. While he is bobbing up and down on me, I notice that I've marked up his neck and chest so he's going to have hickeys. After about 10 minutes I tell him I want to change positions, that it's hard for me to cum this way. He gets on his back and I line up my cock and going all the way in to him. I start pounding my cock hard in him. He's totally getting off, jacking his cock while I pound away. I can feel him edging up but he stops jacking. I tell him its OK to cum first and he goes back at it. I start can to feel myself getting closer and I shoot my load deep in him and continue to fuck. He tells me he's close, I pull out and watch him cum. He grabs a towel and wipes the cum up as we kiss and talk. Finally, it's 10:30 and I have to head to work as I have a noon meeting. Nice start to a Friday.

What a pain in the As*ian this guy was

I was up real early last week and put up this ad for an early morning fuck. This cute Filipino guy responds and we make plans to meet up. He makes me promise that this will not be a blow and go situ, he is looking for a longer encounter. Sure, I have some time so sounds OK. I get there and he's just like his pic, mid 20's, I believe 25 or 26, 5'6, 145, smooth. We start undressing and we get into bed. He starts kissing me and I start moving down his bod. As soon as I get to his nips, he starts complaining that I can only lick them, no sucking, biting or twisting. Whatever dude, let's take all the fun out of nipple play. I comply and eventually start going down and start sucking on his cock. It's small, probably about 5 inches. As a top, a big dick doesn't do much for me but it's nice to look down at a big one when you are fucking ass. He asks me to eat him out. After all of his rules, I was waiting for something goofy. I start eating his ass and he's getting into. He asks if he can sit on my face. Not the way I usually do it but I'm game. Plus, I want to fuck that ass so, if this gets him going, it's all good. He sits on me and I get in his ass pretty deep with my tongue and tongue fuck him. He's getting off on it and his man pussy is getting nice and wet. I lift him off and go behind him, starting to rub my cock on his ass. He asks if I have any condoms. I tell him no and can feel the air leave the room cause as fussy as this bitch is I know he's not going to let me fuck him raw. To my surprise he leaves his ass out and not needing an invitation, I put my cock deep in this little slut's hole. I'm fucking him for about a minute when he pipes up..."I don't fuck bareback". I'm thinking guess, what bitch, you are today. I keep at it and about 2 or 3 minutes later he pulls a move which makes me come out of him. At this point, he clenches his ass up and is going to make it hard for me to get back in. Never one to give up or not like a challenge, he's either going to let up and just let me finish, he's going to get a serious ass wall breach or I'm just going to have to quit. He ended up with a serious ass wall breach. Then he starts complaining about how it hurt and I was not in the mood to hear any more of his shit, so I told him to shut the fuck up. He kinda listened as I was on top of his grinding my dick deep in his tight little ass and not stopping and he ultimately said just don't cum inside me. Fine, I'll give him that. I keep pounding for a little bit and pull out and blow my load up his back. He immediately starts questioning about where I came and goes on for a bit. I'm kinda exasperated with this guy but want him to cum too so I tell him to jack and I start licking his nipples. He blows fairly quickly and starts to hold me trying to cuddle. I'm so not feeling this right now but I did kinda rough fuck him plus I promised a longer encounter. So I wait for a few minutes organizing my schedule for the day as he is talking about some nonsense that I'm trying to block out. Eventually I tell him I had to go, wash up and hit the road. Even though I got what I wanted, I think I would have been better off beating my meat at home. I hate prissy boys. He was such a cunt.

Cold Outside Fuck w/ 19 year old

I answered this ad from this 19 year old kid. He's Italian and has a cute face, a bit of a cub. I'm pretty horny so I figure why not. I'm supposed to meet him at his sister's place. As I'm on my way, he lets me know his sister is going to be home but to come over and we'll find a place in her building. We're looking around and there are not any spots to play. We walk outside by the outdoor garage and there are some dark corners but not where you can't be scene. Then I notice that part of wooden privacy fence is knocked down. We go over to the building next door and the back is pretty private. The buildings around can't see and there's only a back door. So we both nod to try it. It's about 42 degrees outside so this is going to be a clothing on and try to finish off asap. We start kissing and rubbing each others crotches. I unzip my pants and pull my cock out of my boxers but leave the pants belted and on. He drops his pants a bit and I turn him around. I spit on my cock and push it in his hole. He asks me to be gentle that he is really inexperienced. I will but it being dry isn't going to help. He was super tight but I get my cock in him. I ease slowly further in. I'm taking nice slow, long stokes. He's moaning like a little girl. I smacked upside his head and told him to shut the fuck up. I start fucking faster cause it's too cold to be fucking outside and he's going to get us caught. As I getting ready to blow, we hear some noises so I cum everywhere. In him. On his crack. On his underwear. I get some on his jacket. He's a mess. False alarm. I zip up and we walk back into the building and I leave. He emails me later saying that he found a room we could of used. I love breaking in new ground as I've never fucked outdoors before.

Erick - Jockstrap twink

I've been chatting with this guy Erick for about 6 months but we haven't been able to meet up as it's always been are u free now and the answer has always been no. So yesterday we catch each other online and both are free and horny. He's totally adorable, a little twink (5'8, 130, 23 y/o). He says he's house sitting and if I want to come over. Of course I do. He lets me know this is what he wants: "I like anonymous or walk in type scenes where you just find me on the bed inside and have your way." I'm up for that, so I tell him I'll be there in about 30 minutes. I call before I get there and leaves the door open for me. I walk in and he's in the bedroom wearing a jock strap. He helps me undress, and rubs his ass on me as I am unbuttoning my jeans. He helps and does it again when I am in my boxers. I let him rub on me as I take my t-shirt off. He pulls out my cock and starts sucking it. I'm totally hard. He pulls my boxers down, twirls them around and throws them aside. I ask him if he is going to leave the jock strap on and he says "I love wearing a jock when I get fucked." It is pretty hot so I cool with it. He's now on all fours, with his ass staring at me. There's no lube or rubbers out, so I spit on his hole and rub my cock on it. I spit again and push the head in raw. He goes nuts. Starts moaning and bucking like a little bitch. He's really moving around a lot, throwing me off a bit, so that I keep coming out. He pushes me right back in and continues to buck and groan. I come out again and he turns around on his back, pulls off his jock and raises his legs. I go right back at him and he moans like crazy. He's getting a little loud and he pulls the pillow over his face and starts yelling and groaning into it. I'm getting really turned on. He eventually grabs his ankles and spreads his legs out as far as he can. I continue pounding at his hot little ass until I shoot my load right up it. He knows I did and groans louder. I continue fucking him until I go soft. I get up to clean off and he's prancing about with this big winter jacket on but no clothes. He starts showing off his ass and I tell him his white, creamy ass looks good like this. He comes over and rubs his ass against my crotch. He's a good little bottom bitch and just looking at his ass above makes me want to fuck it again.

Hotel Guy - Jim

I am not quite sure what it is but there is something about hotel sex that gets my juices flowing. It could be the dark room, a great view (usually), the smell of the room or the fact that inhibitions are down as this is usually a one and done and you don't have to worry about running into each other. Whatever the reason, it usually is hot. I was completely horned up yesterday. It felt like I hadn't had sex in a month even though it had only been a few days. I literally had to walk around at work with files and stuff to cover up the stiffy in my suit pants. Was I at work with my co-workers or back in high school. I meet up with Jim who is visiting and has a limited time to meet up before work obligations. He's looking to get fucked on all fours. I can work with that. So I arrive at his hotel and head up to his room. He's wearing mesh shorts and a white-t. Nice. He's ok, nothing special but the room is dark, porn is playing in his lap top and the city lights are shining from the window. We start to undress, he's faster cause he has less on on. He's stroking and hard before I'm completely nude. Once I'm naked I start stroking but not much is happening. He gets down and starts to give some pretty good head. Nice mouth, he obviously knows what he is doing. He gets me good and hard and turns around and gets on all fours. He points to the lube and condom laying on the bed. I grab the lube, squirt some on his ass and my dick and throw it on the bed. I decide that I am not going for the condom, he's going to have to make me put it on. I rub my cock on his ass and quickly ram it in. He knows I didn't get the condom but moans in pleasure. I quickly realize he's not going to fight it plus I was already in and banging his ass. I wasn't planning to stop. He wants a pounding and I do want to pound. We go at it, stretching his ass walls out. He's asking for it harder and for me to cum. I keep plugging away. I can feel my guys edging up from my balls and I tell him I'm going to cum. I don't give him the chance to move and he didn't anyhow. I shoot it deep in him and keep fucking. I don't pull out until its soft. He laughs and says thanks, I shrug, clean up and don't think I even gave him another look. I don't think he intended to take it raw but knew once I started that was the only option. And you wonder why I like hotel sex.

Matt - Southern kept boy

I had a meeting out in the burbs yesterday and figured why not check out the suburban meat. Matt sends me a pic and he reminds me of a younger Ralph Fiennes. Not as hot as Ralph but a resemblance. We make plans to hook up before my meeting. He gives me an address in a real wealthy suburb so I am figuring he is either married or a kept boy. I arrive and I am not easily impressed but this place is huge and impresses me, this is a million and half dollar house. I get there and he looks just like his pic, early 30's, 5'11, 160 pounds, blond, blue, and a southern transplant. He didn't have to state his deal, as long as I was out of there before his sugar daddy came home, all was good. Worked with my schedule. He leads me up the staircase to the master bedroom. He takes off his clothes and is naked in the bed before I even have my suit off. I join him and he starts to kiss me. My cock is already hard and I rub into him as we kiss. I feel him get harder. He kisses down my chest and sucks my dick for bit. He wants to kiss some more and I decide to take some control. I role up on top of him and continue to kiss him. I am rubbing my cock into his big sack. I lift up his legs and throw them back and start rubbing up against his crack. He moans as I push across his ass lips. I spit down for some lube and continue rubbing, intentionally poking my head against the outer lips so that I am not in but he can feel me. I do this for a little bit before I spit some more. He's digging the frottage but I need to fuck him. I push in him and he gasps. He keeps holding tight, switching between grabbing my legs and the side of my chest. I'm giving him a nice slow fuck cause he's kinda tight. I can feel his ass gripping my raw cock. I pick up the pace and he really starts to react. I move him closer to me and take a look at my cock in his ass and this gets me even harder. I start pounding him cause it feels good but I also have a meeting to get to so I can't fuck all day. He's going nuts and pretty soon I blow my nut deep in his ass. I don't pull out when I cum. I continue to fuck him as he strokes his cock, not pulling out until he cums. It was a decent fuck but the thing that really turned me on was that I was fucking this kept boy in his sugar daddies' bed. I guess being a millionaire may get you the boy but won't stop him from get bred in your bed while the daddy works. I found a pic of the house online and the daddy bought it for $1,600,000.00 in 2004.

Snowy day fuck - Artist

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Friday night disappointment - Brandon

Unexpectedly on Friday, late, after 9, I was free. I decided to take advantage of the situation and see what was out there. If I knew, I wouldn't have beat off earlier or drank the wine. So I put up an ad and this young dude, Brandon answers. He's 23, 5'6. 150. From his pics he wasn't fat but solid, muscular. I head over to his place. It's freezing out and I have to wait for him to come down and open the gate. He's totally cuter in person, nice little Irish boy. Auburn hair, nice little body, solid. We get up to his pad and it's sort of a New York style loft - brick walls, bed elevated 8 feet from the ground. We go to the bed and start chatting and kissing. It's almost sweet, like we had been on a date and are messing around after for the first time. He' s totally cock hungry and starts by unbuttoning my jeans and pulling my cock out. He starts sucking it. I eventually take my pants off and start to take my socks off and he says don't I have a sock fetish. That's cool bro but don't ask me to mess with your feet. I get naked and start taking his clothes off and it's all good except for the thong. He's got a nice milky white skin, the type with pink nips and cock. He's also a little hairy but in all the right spots. His cock is nice, bigger than I thought it would be. He's sucking me again, I am kissing his neck, twisting his nips, moving to his cock and start fingering the outside of his ass. He gets up and goes to this box and pulls out some poppers and lube. He lubes my cock and his ass, takes of hit of poppers and sits on my cock, no condom. I'm stoked cause I like to fuck bare and we never talked about it. He rides me and it's good despite the mattress being soft and sinking. He's controlling the fuck while he's sniffing away on the poppers I decide to start thrusting in him to see how he takes it. He's doing OK, so I pick up the speed and starting using my hands to thrust him up and down too. I lift him up and move him to his back with my cock still in him. I hit a couple of soft spots, one in his ass and the other his head on the brick wall. He says he needs a sec and goes to the bathroom. So we stop and I lose my hard on. He gets back and I'm soft and I start rubbing on him, frottage style. No luck. I turn him over and rub on his ass which almost always works, no luck again. We tried for 25 minutes and no go. I take a piss hoping that will help, we're sol. I tell him I don't think I can get it hard. He was really cool about it but not happy. I ask what I can do to get him off. He says keep trying to get hard and asks me to rub my feet and dirty socks on his face while he jerks. I let him suck on my socks and feet and he cums. I try to be cool and feel bad cause I really wanted this boy. By the look on his face, I know I'll never get a second chance and I'm pissed cause he's totally fucking adorable. A lesson learned, when drinking, I may want to keep and ED pill close by.

New Year New Dude - Robert

Here's to starting the new year out right. I put an ad on when I got in from NYE. I was horny but really didn't want to head far cause of drinking and couldn't host. I chat up with this mixed 25 year old Asian/black dude and I'm thinking I'm gonna fuck a Tiger Woods type. He seems nice and not too far but it's not happening. He keeps texting me his pic but I don't get it. I end up going to bed. The next day I text him telling him I didn't get it but am interested. He repsonds back. We chat on the phone. He asks me if I fuck safe or bb. Every time I hear that I've fucked the guy raw. I head over to his place in Wicker park and we make plans to watch the Blackhawks play in Wrigley. He's pretty cute, a bit thicker than my general type, 5'10 180, but looks Asian, not black, probably Korean. We start kissing and touching each other all over. He has a muscular ass and strong legs. He gets down on his knees and unbottoms my jeans, starts giving me head. I start fucking his mouth. He handles the aggressive play well. He takes off my pants, I lift his shirt and he has his nipple pierced. I love tugging on a piercing. I pull down his track pants, now I know why he's a bottom. Small dick but it's all good cause I'm going to fuck him not the other way around. We end up on the bed. He's blowing me and I jump on top and start rubbing my cock on his ass. We start kissing again and he asks me if I want to fuck him. Duh...So he grabs some lotion and a condom. He puts it on me and we start to fuck. I start slow cause he's tight. Get him used to it. But it feels good. After a couple minutes he pushes his legs together to make it almost impossible to fuck. I pull out and the condom cums off he's gripping so tight. I ask if he's ok and he's says fuck yeah. I pull the condom out of his ass and let him know it came off and then fuck him bb. It feels so good. He's tight. And then he does the leg together thing again and without warning I blow my load. I'm pissed. I wanted to fuck a lot longer cause it felt good and he was turning me on. So i fuck him a bit longer until I go soft. Now I need to get him off cause I hate selfish tops that don't make sure their partner gets off. I suck his cock a bit but the lotion taste is bad. So I start playing with his balls as I suck his nips. Well he shoots a missle, right past my face. Fucking hot. As I'm leaving he gives me an open invite back. And we didn't see any of the Blackhawks-RedWings game.

A great starting point - Lewis

I ended '08 hooking up with this skinny black thuggy twink (20, 5'8, 140) that I chatted with about 6 months ago. He originally answered my CL ad but was looking for generous. I chatted with him but didn't meet him. He's im'd me a bunch and finally we chatted again. He didn't remember me but knew my sn so we went through the pics and made plans to meet. I love the fact that he is unaware of who I am and what I want but I plan to fuck this vers top. I tell him I am a top and he's open to it, although he claims he hasn't been fucked in over a year. He gets here and he's hot. Skinny, nice little ass, uncut 7 inch cock that is nice but not scarey. We get to things, we start by kissing and rubbing up against each other. He can't wait to start sucking me off. He's blowing me and I spit in my hand and start fingering his ass. He goes nuts. Eventually starts sucking me and puts his ass in my face to eat it and he tastes great. Clean. I get him in missionary position and start rubbing my cock on his ass. He eventually pushes me down and in him raw. I start fucking him and he says to nut on his chest. After about 5 minutes, I nut in him but he does realize it (maybe). I keep it up for a bit longer and suddenly he has to go the bathroom. He goes, cleans himself up again and cums back. He wants me to continue but I need time. So I start blowing him again. After about 20 more minutes I start getting hard again. So I do him doggy cause its easier. I fuck him on the mattress, then him on the bed me on the floor, then both on the floor and lastly, partially on the bed frame, me on the floor. I am super dick now cause I'm hard and came so I'm not cumming again so soon. After 25-30 minutes he can't take the pounding. I pull out and jack on his chest, eventually cumming. I get on top of him as he jacks, his head is brushing against me and he cums a bucket. Later on he IM's me telling me he beat off to me and wants it this weekend. We'll see but he definitely got treated like the slut he is and wanted to be. And the only thing generous was the long fuck. (Not his ass but it looked alot like this pic)