Cruised for Awhile

After laying low due to the cold this week, I ventured out Friday night for a couple of hours. All that I spotted was a guy I sucked off last spring when he was stumbling home from a bar. This time, he was stumbling to the same bar with a friend. I tapped the horn and he waved, but I can't be sure he recognized me. He looked very doable again in his blue jeans.
Headed out of the area, I saw a European-looking stud at a bus stop. I signaled that he could have a ride in the direction I was going to get out of the cold. He shook his head 'no'. So, a cold, cockless night it was. Maybe tomorrow night...

Don't Tell the Wife

Last time I saw this guy was just before Christmas about a month ago. Tonight, he caught my eye again. He was sporting a fresh, clean, cute haircut, new hott white sneakers and an awesome big belt buckle that his wife brought him from Mexico during her holiday visit there. He was looking fine - and, again, all mine. I pulled over and he immediately got in my vehicle and wanted to get away from the main strip. Not comfortable anywhere I drove to, he suggested we go back to his place because his wife and baby wouldn't be a problem at this hour. And, they weren't. He talks about fucking my ass some night but always ends up being very content with a warm, wet, tight-mouthed blow job to get him off. He's a very good-looking, satisfying date for me. Last time I pictured his cock on here was when I wrote "Short Ride - Long Dick" which has the URL: http://cruisingchicago.blogspot.com/2009/07/short-ride-but-long-dick.html

You've Been Where?

There's a guy who's been walking around with a lady for a couple of months now. He's caught my eye over and over again because he's cute as suck. Hanging around with the same woman, I knew he was straight - and something told me that I shouldn't mess with him.
Tonight, he was alone, standing in front of a fence along a busy street where he's usually walking around with the lady. Unlike most times I see him, he looked fresh tonight with clean cream-colored slacks that looked so good with his hott white sneakers. When he saw my driving by, he raised his forearm up to his waist and waved his hand in the 'hello' motion. I instinctively gave him a thumbs up.
Naturally, wondering what's up with him, I circled back around and he wasn't even looking this time. But, I didn't give up. I circled back again and he saw me, and we just looked at each other for a few seconds while he raised his eyebrows as to ask, "What's up?"
This time, I went around the block and waited at the corner until he saw me. He did. He looked in my direction for a while until a car pulled up behind me and I had to move. I slowly passed him to go around the block again, and this time he was leaning against the fence with his legs crossed - looking as seductive as suck - and my cock got hard as a rock and started pounding for those cream-colored slacks and what he has in them.
This time, when I got to the main street, he was gone. I figured he headed down the nearest side street to see if I'd pick him up there since I wasn't picking him up on the main strip. He was right. I was willing to pick him up on a side street.
When he got in my vehicle, he said he remembered me from a few years ago. I looked at him closer and though - possibly, as he's really cute! He's the type of guy I'd pick up. When I asked him to refresh my memory, he said that - first of all - he was walking with his girlfriend a couple months ago and snuck over to have a word with me and I quickly drove off. I told him I vaguely remembered a situation where I had stopped near him and drove off. I explained that that's definitely what I would have done if he was with any friend - let alone a girlfriend.
Then he really surprised me when he said, "And you picked me up about 3 years ago before I went to prison." We talked about why he went to prison and what we did before he got locked up. He said I sucked his dick one night. He gave me details of our oral encounter, but it didn't help me remember. I had no reason to not believe him.
Then, as I hoped he would, he told me he really needed a good blowjob. He asked me to stop for him to take a piss. The strong stream of piss was all I could see from the angle I had, and I knew he had a nice piece of meat to hose that flow of piss out. He got back in the vehicle, spread his legs, and pulled his pants up for the material to hug his package tight. My hand was on his upper leg and package immediately. He said he'd give me a better feel and unzipped his pants so I could feel him through his boxers. From this non-spoken agreement to suck his dick, he gave me directions to his nearby place. I sucked his dick for about 15 minutes, then gave him a ride to a bar. During the ride to the bar, he said he needs to be discreet as he has that girlfriend that I've seen him with - who doesn't blow him enough but does fuck once in a while. He also said that he has 3 kids in the neighborhood with the mother of those kids - so he really needs to be discreet. He said that a couple other guys sucked him before he went to prison but I'm the first since he got out. I was hoping to hear some hott prison stories about him getting sucked off there - but the stories didn't come.
He was sincerely grateful for the blowjob tonight - almost as grateful as I was for getting to give him one.

Too Long Since Getting Anything New

Last night, I ran into a date who's been very regular this winter. Though I planned on finding something new, I was quickly approached by this guy when I first headed out around 10:00 o'clock. He was hanging around on a street near a doughnut shop when he got in my vehicle and started playing with his cock through his dark blue gym pants. He said he'd been working all day and could use some head.
Getting the idea I better take him now rather than stall or I might not get anything off the quiet streets, I followed his instructions as he gave me the quickest directions to his house.
Once there, he took me in his living room, laid down on his back on the couch and arched his back as he pulled his gym pants and underpants down to his knees and then spread his knees to give me ample room to get between his legs. He grabbed the back of my neck and pulled me down to his cock which he was holding up with his fingers. I took it all in my mouth and sucked it up until it was plump, long, and hard. Then I took my mouth off to have a look at my expert work and he arched his back again and put his cock down my throat. He needed a blow job - and he needed it now!
I bounced my head up and down on his shaft with his hand still holding the back of my neck firmly until he took it out and stroked it a few times. Then he force-fed me his tool again. When getting close, he held my head on his cock head and started breathing sooo heavily. I clamped firmly on his cock head and worked my tongue on it and the slit on top. He loved it! In no time, he let out a grunt of delight and the strong hott shots of his manhood hit the roof of my mouth. It was soooo hott getting the load this way. I held the cock's head without tongue motion for about ten seconds before starting to move my tongue over the slit of the cock's head again. This made him laugh, squeal, and pull his cock out of my hold as his cock's head is very sensitive after he nuts for me. He could see I was ready to go for another taste when he quickly pulled his pants and underwear up to block me from messing with him more.
Here's one of our past dates from two months ago. (URL: http://cruisingchicago.blogspot.com/2009/11/cruising-same-area-as-last-night-was.html)

After leaving his place, I saw a former date leaving a bar that I've written about in the past. He's an older guy who likes having his dick tasted once in a while. After what I'd just gotten down my throat, I didn't stop for this guy even though he was trying to wave me down. He's reluctant to take me back to his place and wants carsucks - which I don't care for. Were he more apt to take me to his place for the quickie, I probably would have done him last night, too, as I haven't had him since last summer.
Still headed out of the area, I saw another former date on the street walking with two other guys in the direction of his place. I discreetly made myself known, but, as suspected, he didn't make any sign of recognizing me with his straight friends around. As good as he looked in his red baseball cap, blue and yellow jacket, hott blue jeans and white sneakers, I wanted to suck this cutie. I thought I discreetly parked in front of his place so he could sneak away from his friends, but one of his friends was aware of me following. He came to the sidewalk and checked out what I was up to. I ignored the friend and drove off. So I'll have to keep hoping to find the cutie I've sucked twice now walking alone before I'll get him for the third time. At that, I called it a night - a good night for available cock!

Surprised to See Him

I had just got to a street I cruised often in the past but not lately. I've been avoiding that area because it's been a while since I've seen anybody 'interesting' on that street. Yet, tonight, I was driving along and saw a guy I've been meeting up with regularly. He said he had car trouble and needed to walk. Well, he got a ride and more!

Usually, I meet up with this guy after he gets off work late at night, but today he wasn't working and looked fine as fine can be when I spotted him around 10 o'clock in the evening. Sporting a new crewcut haircut, awesomely trimmed goatee, hott new blue jeans with an inviting wide black belt to be unbuckled, sports shirt opened to show a blue T-shirt, hott-as-hell white hightop sneakers and white socks (so I'd find out when I was before him on my knees massaging his legs as I did my duty on him). He also had a huge hicky on his jaw which I asked about. The ripe bruise was from his girlfriend who gave it too him earlier in the day. I asked him if she got his load or if he fucked her, and he said they only made out by kissing. That's when I knew his balls would be extra full and ready to be drained - and they were! After dropping him off at his friend's house, I headed home with his hott-tasting creamy load's after-taste still lingering in my cocksucking throat. Loved it!

To see one of my dates with this hott stud from last month, go to this URL: http://cruisingchicago.blogspot.com/2009/12/hott-gangbanger-unzips-again.html

Cruising

Cold as it's been, I went cruising a bit tonight and saw a couple of former dates. The last guy I sucked was walking down the street with another guy towards the bar I picked him up at the first time I got to know him. I never approach when a guy is with a friend. He looked my way and quickly looked away which means he didn't want to be acknowledged or acknowledge me while he was with a straight friend going to a straight bar.
Next, I saw a former date that I'd been with a good number of times last spring and summer until he started having cleanliness problems. Though he's been looking better lately, I still haven't dated him since I don't know what his current condition is and don't want to have to turn him down like the last two times we spoke.
Finally, I saw the guy with the big teardrop tattoo looking so fine on the street corner. I pulled up in hopes of him needing a ride again so I could continue to get to know him better, but he said he was waiting for a relative to pick him up. I pulled over and looked him over for a while anyway. Nice jeans, cute gangbanger's face, hott white sneakers all added up to this cocksucker drooling for a while. Then I called it a night.
When it's cold like this, lots of former dates contact me but at bad times for me. Over this weekend, at least four calls from guys I know by their phone numbers and several unknown numbers which are probably guys who have changed location and phones since I first met them. Just too cold to make plans and drive long distances this weekend. Hopefully it will warm up soon.

Cute Guy Gives It Up for a Second Time

The successful pick-up and date I wrote about in the post called "Rough Week" on 12/24/2009 (URL: http://cruisingchicago.blogspot.com/2009/12/rough-week.html) was walking home tonight with groceries when I spotted him in a hott red baseball cap, light blue and yellow jacket, awesome bluejeans and white gym shoes. I pulled over to give him a ride in the bitter cold, and he was anxious to get more than a ride again. With his hat off, he has the hottest clean haircut, and with pants open, he has the biggest - 9 inch - cock to suck, to get a face-fucking by, and to make oral love with. He loves a good blow job. He can tell that I want to kiss his cute face and allowed it. When I brought his head down so I could kiss his cute haircut, he got nervous and protested as he thought I was trying to lower his head to my crotch; I reassured him that I wouldn't do that as I know he's into big tits and tasty pussies as he told me the night we met. Yet, he wants a smaller hole than my warm wet tight lips some night, which is causing disagreement between us. He says he'll only put the head of his cock in my arse; but the way he bangs my throat with his thick 9" tool, I don't trust him to not 'go ape' on my virgin butt. When he reaches for my ass, I stop sucking until he quits reaching. Awkward, but it works - he stops going for it when I refuse to suck. I've managed to stall him twice now by saying I'll try it at my place with him putting on a condom only. He says he's got the condom on him to go back to my place, but I claim I don't have the time to take him back to my place - whether I do or not. I'm not sure I will let him fuck me anally, but I'm thinking about it since I've met several hott guys lately who want to fuck other holes besides my suck-hole.
Again, I gave him my phone number in hopes he'll call rather than wait for me to just spot him on the street walking home again. Very nice date with this incredibly delicious and cute guy.

Thrills but No Date

Sitting along the street in my vehicle, the hott gangbanger I saw a few nights ago walked up on me and wanted a ride. I gave it to him. I told him I didn't recognize him the other night because of the huge teardrop tattoo which I didn't remember seeing on anyone before. He explained that he hasn't had it that long. We talked about where we first met - in front of a restaurant - and then I remembered the first night I went out of my way to show my interest in him. He looks too tough to be too forward with or to mess with - until I get to know him better. And I definitely want to get to know him better. He's suckin' sweet looking, has a girlfriend, and is quite friendly with me. Maybe one night...

Warmed Up a Frigid Date

In near-zero temps in Chicago, there was surprisingly quite a bit of pedestrian traffic out around 10 o'clock in the evening last night. So, I took a look around and discovered a former date freezing at a bus stop. He spotted me before I spotted him and he darted to my vehicle. He needed a ride about a mile away - and needed to get out of the cold, too, I'm sure. His little bit of a sexy goatee had frozen spots from the cold which meant he was out there a while. When I touched his hand and uncovered ears, however, they didn't feel all that cold. Yet, he said he was out there waiting for a bus for about 20 minutes. Shortly after he got in the vehicle and we were on the way, he was playing with his dick in his black sweats and I sensed he was wanting me to take over - but I didn't just yet. When we got to his destination, he asked if I could wait a few minutes so he could get a ride back to his place in this unbearably cold weather. I said I could and questioned whether his wife and baby were home. He smiled and said, "No problem." On the way back to his place, he was anxious to be touched and I played with his sweats - and what was in them - on the way back to his place which got me excited and ready to suck his cock. When we got back to his place which was about a block away from the bus stop where I found him, he had me take him down the alley behind his house and he ran in to see if everything was good for me to enter. He came back in less than a minute and said all was well. I parked on the street and hurried in the back door, freezing. He got me into a quiet room and he immediately pulled his black sweats and his hott horizontally multi-colored striped briefs down to just above his knees, and I sucked on his cock until it got hard which didn't take long. Then he stroked it a very short while and signaled me to go for the big finish. He held the back of my head demanding that I engulf the entire shaft as his cock pulsated in a way that showed me how bad he needed his cock sucked tonight. Bolt after bolt of jizz hit the back of my throat from his canon-like release. As I took my mouth off his cock's head and started to wipe my lips off, he pointed to his cock and said, "More." I saw that I'd taken my mouth off a little too soon and a glob of thick stringy ivory-colored cum landed on the top of his nice-sized, plump cock's head and dangled down nearly the entire length of his cock's shaft. I went for the last of my reward and he squealed from the sensation caused by me going down the length of his spent-cock's shaft and ate the last of his awesome-tasting cum. We exchanged thanks and I was gone.

Headed back through the strip where the pedestrians had been just an hour before, the crowds had thinned to almost nothing except for someone all bundled up waiting for someone in front of a restaurant - or maybe he was panhandling. I pulled over for a couple minutes to see if it was someone who would recognize me and come over - but he never approached in the very short time I was there. Therefore, he likely wasn't a panhandler as they will often approach a parked car for change, too, and not just hit on the people walking in and out of the restaurant. I found myself checking out his hott sneakers to see if I recognized them because in the winter when guys are bundled up from head to toe, one has to try to recognize a guy any way he can. Naturally, I know the shoes and boots of the guys I blow, as well as the type of pants they usually wear because I spend lots of time down there when I'm with them.

My last date with the Papa that I sucked last night was December 5th, about a month ago, as detailed in "Cold Night - Hot Date" which has the following link: http://cruisingchicago.blogspot.com/2009/12/cold-night-hott-date.html

Zero Degrees Out, But Found One

Early in the frigid evening, I was driving and saw a regular who was quick to get in my vehicle out of the car. He needed a ride. When we got the short distance to his destination, he asked me if I could wait a couple minutes and give him a ride back. As soon as he got in for the ride back, he started playing with his dick through his black sweats and asked me to come back to his place. I asked if he didn't fuck his wife today or what. He said he's been getting nothing. Well, he got a blow job to completion tonight. He's a below-average sized cutie who always busts a nut to satisfy my appetite for cum.!

New Year - So Far So Great!

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New Years

After the New Years celebration died down, I took off to cruise. Due to the single-digit temperature in Chicago, there weren't all that many people out on the streets where one usually finds a lot of pedestrian traffic on a weekend or holiday night - especially a New Year's night. Yet, one guy I'd been with a few times in the past approached my vehicle very abruptly at an intersection and reached for the locked door. Since I immediately remembered he made me uncomfortable last time we were together by pressuring me for beer money I didn't have, I just opened the window a little and shouted, "No money for beer tonight," and drove off.
Just a few blocks further, there was a guy stumbling down the sidewalk past a parked car with a man in the car. The man in the car got the stumbler who was tall, olive-complected, and had black curly hair to walk over to his car. The guy in the car struck out - the guy didn't get in his car. I circled back around and took my turn. Telling him that it was cold and I'd give him a ride, he loudly said, "No. I'm not going far." As I took off, an SUV pulled up and tried his luck. I watched to see if this guy had any luck, and he didn't. Guess there were lots of cocksuckers out looking for cock last night - and very few good-looking guys headed home. For New Year's Eve, it was early though - not even one o'clock in the morning yet. I can't imagine how many guys tried to pick this cute guy up before he finally walked all the way home.
In another area, a guy walked up to my vehicle at an intersection. He wanted a ride but I didn't trust his approach. I told him that I didn't remember him, and he said that we didn't know each other but he's seen me around - which is very possible since it's an area I've cruised before many times.
Finally, I saw a cute guy outside a bar where I picked up a guy a week or so ago and had great suck-cess. The guy last night was skeptical of me, but eventually walked over to see why I was just hanging around like he was. When he approached, I'd remembered his handsome face - a very good looking guy. He got in my vehicle and warmed up. Surprisingly, he wasn't drinking at all even though it was New Year's Eve night. He swore we'd never seen each other before, but I told him I'm positive I've seen him around before because of his strikingly good looks. Soon, he got out of my vehicle and walked. Then, a former 'date' walked up and got in to warm up. He wanted a blow job, but he was drunk and appeared dirty. So, I said I didn't have time. When the cute guy outside the bar saw that I knew this guy - a friend of his - he was more comfortable and came back and got in again. He wanted a ride home. I ended up giving him a ride to his place on my way home and made my totally honest "interest" in him very clear by the time we got to his place. He said that sucking his dick wasn't a possibility, but a good massage was quite possible. At that, I was massaging his muscularly rock-hard leg - in hopes of getting him hot for a mouth on his cock. The massage must have felt good because he allowed my hands on his muscular legs for a good while. The one time I moved up his leg towards his crotch, however, he stopped me cold. I gave him my phone number to call when he needs a ride - and a massage. Rock hard, I drove home and took care of my own just thinking about that cuter than cute guy.