Monday, March 29, 2010

I think I met my match, part 2

This is a little long for a part two but I met up with Greg again, literally, one year later, same day (http://windycityboisex.blogspot.com/2009/03/i-think-i-met-my-match.html).  I don't think he remembered hooking up with me.  He was really hung over and stoned off his ass last time.  I get there and he gives me the same line about his place being trashed from the weekend.  Oddly enough, it looks exactly like it did before.  We go into the bedroom and he pulls down his track pants and starts jacking his big cock.  I start taking mine off when he pushes my head down on his cock.  I start sucking his good and fast.  He slows me down and says he's going to cum if I keep at it.  I take it down a notch and lick the head, jamming my tongue into his slit.  I inhale the smell of his pubes, licking around his nuts.  He then shoves his cock in my mouth making me gag.  He repeats this two or three times before I stop his raise his legs and start eating his ass out.  He just showered so it's nice and clean, perfect. He jacks his cock as I eat his ass and dry hump the bed.  He gets close and wants me to swallow, but I stay at his ass.  He shoots his load all over his leg while I blow my load in my underwear eating his ass out.  I go to his bathroom, clean myself up and walk out with my cum-filled briefs in my hand.  I guess I'm going commando today.

Thursday, March 25, 2010

Role Play: Interview

I put out an ad for some role play.  The scene is that it is either a job interview or you are my assistant.  This guy in his mid-40's with a rocking hot body, ok face answers.  His choice was for a job interview.  I 'm sitting behind my desk asking about his previous job.  The code we had set up was that I would say that is not consistent with your resume and head over to him, "accidentally" rubbing my cock into him.  At that point, he pushes into me, grabs my leg and says, "I'll do anything for the job."  I grab his head and push it into my pants.  He gasps and undoes my pants.  He takes out my cock and starts sucking it.  I let him get used to it before I start fucking his mouth.  He tries to take it deep and hold it in his throat.  Fuck that, I decide to jam it all the way down.  He gags and blow it out.  I take his head and start roughly fucking his mouth and this scene continues for a bit.  He stops for a second and take his pants off and shows off a nice thick cock which he starts jacking too.  We pretty much continue on with me fucking his mouth while he jacks his cock until I unload my batter down his throat.  He continues to lick it up and I shiver as it sends shock waves though my body.  He eventually blows his load and asks if he has the job.  I tell him maybe but I have to make sure there isn't a candidate with better skills. 

Monday, March 22, 2010

Rough fucking one of my favorite little sluts

I was online and  saw my bud Erick was online (http://windycityboisex.blogspot.com/2009/02/erick-jockstrap-twink.html).  I hadn't chatted with him in awhile or seen him online, figured he dropped off the face of the earth.  It happens.  We had some chit chat about what we'd been up to when I hit him up and asked him if he was free.  He tells me to come over and resends his phone and asks me to text him when I'm close.  I get to his building and text him.  He says the door is open and he's in the bedroom.  I find him like I have in the past, lying in bed, jock strap on and ass waiting for me.  I love that quality about him, he wants it and he doesn't play games.  I take off my suit and get naked.  I rub my cock up against his tiny little ass.  It's nice.  Small, round and white with a pink hole.  I spit lube my cock and enter him.  He's tight. Tighter than I remember and I let him know.  He tells me he hasn't been fucked in about 5 weeks.  Nice.  I like it when a sluts ass becomes tight again.  I start fucking him nice and slow.  I move down and stick my tongue in his ear and this gets him wild, he starts bucking back.  I'm not sure how this started but I put my hand around his neck and gain control.  He about loses and loves it that I could choke him. So I continue to pound my cock in his hole while I choke him easing up and then taking a firm hold.  He's going completely nuts and my cock is loving every second of it.  Every time he flinches, he grabs a hold of my cock and eventually lose it, blowing my load deep in his ass as I fall on him.  I ask him if I was too rough with him and he says hell no that was hot and he's going to beat off thinking about after I leave.  I cleaned up and went to a work event.  This time, I am not losing his number cause I really liked being rough with him.  I guess there is always new ground being broken.

It's been awhile...

Hey guys,  I took the vow with good intentions and the idea that it would give me some clarity.  Not exactly.  The vow has been broke, (big surprise there) but the time away has been a nice little break.  It's time to get back in the saddle, so to speak and update you on my adventures. 

Friday, March 5, 2010

The first 18 hours - hotel sex



I fell off the wagon pretty quickly.  It wasn't even 18 hours into the vow.  This guy I had been chatting with from out-of-town hit me up.  These things are usually hit or miss.  He was literally 4 blocks away from my office in a hotel.  I guess I had to. 

I meet him in the lobby and we head to the room.  He looks like his pics, a little geeky but for some reason it turns me on.  He's about 29, 5'10, 150, brown, blue, glasses.   We get in the room and I notice his pants are unzipped.  He's kinda embarrassed and he goes to zip them up and I stop him.  Quit wasting time.  We unzip and get into down to our underwear.  We head to the bed where we start kissing.  I pull his underwear off and he has a super rock hard dick.  About six inches.  I suck him for a bit and stop.  He changes places with me and starts blowing me.  We switch up again and I start blowing him  but this time I start finger fucking him.  He's moaning like a little bitch.  I know this is going exactly where I want it.  I start rubbing my cock against his hole and he nods over to the table which has a condom on it.  I grab it and put it on and push in.  I'm not too happy about the condom but I want his ass.  I don't go slowly, I'm just all in and he is very vocal and can see his face wince.  Too bad buddy.  It's time to get pounded and I do for a bit.  He's really vocal.  Eventually he comes and can't take it any longer.  He starts giving me head.  I get aggressive and really fuck his mouth.  He stops me and tells me to come on his chest.  Fuck that.   He made me wear a condom and couldn't fuck after he came, now more demands. I pound away at his mouth and start blowing my load and let him know I'm coming.  It ended up in his mouth, on his face, in his eye.  I cleaned up and left.