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  1. #1
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    Hanging out with the bad boy

    I was relaxing at home two nights ago enjoying a few days off before an upcoming Monday surgery and got an email from a week or two old craigslist ad I had posted looking to give head to someone on a semi-regular basis. I checked the email and it said the guy was 33 and had a phone number to text him for a pic and to work things out.

    The email arrived through gmail, and I immediately recognized the name. I work in the field of law enforcement (not a cop) and knew the name, and knew he was kind of a bad boy and had spent some time in jail a few times. It was very possible there was more then one person with the same name, and I knew he did not know me so I texted the guy to see. Sure enough, the pic he sends back was who I thought it was. He is married, 3 kids and lives 2 towns over. It was like 130 in the morning and he said his wife was sleeping and he was curious about trying something with a guy. I said I would be willing to give him head and see if he likes it if he came to my place. He said he did not have a license and asked if I would go to him.

    I was so nervous, but for some reason the whole things excited me. I told him I would be out, that I just needed to shower first. He said he would do the same. 20 minutes later while Im on my way he tells me where to park and says he will be out when he sees me arrive. I pull in, kill the lights, and get out of my car, It was a cool, breezy night and he came walking up the yard in shorts and a hooded sweatshirt just like I had on. He started to walk towards my car and I told him I did not want to do it there and asked if he had any other ideas. He said we could go to the back deck. We went out back and there was a small deck right connected to the house. I glanced over and saw an outside shed not far away and asked if we could go in there and he agreed.

    We went inside, cleared some space on the ground and found something to sit on and then closed the door behind us. It was dark but also lit by the moon a bit through the windows. He then said something that shocked me. He said, before you suck me off I want to try sucking you. I wasnt expecting that, was nervous and told him well im pretty soft right now, not sure I can get hard. He said that he could help with that. I sat down, slid my shorts down and he got on his knees and took my cock into his mouth. He was able to get me hard pretty quick, but my thoughts kept going from surprised to it feeling good to me just sitting there quiet. I started grabbing his head and guiding him a bit, and making his get it all in his mouth. Im not that large so it wasnt a huge feat. He sucked for between 5-10 minutes at a pretty awkward angle while I played with his head, rubbed his back and slid my hands up his shorts playing with his hardon. He stopped saying that his jaw was starting to hurt a bit.

    I told him it was ok and asked him to stand up. As soon as he stood up I pulled him close to me, yanked down his shorts and took his hard cock in my mouth. He was also just an average size so I was able to go balls deep whenever I want and he was loving it. He was thrusting his hips and holding my head and basically face fucking me doing most of the work himself while I just sat there. It allowed me to let my hands roam up his legs, hold his ass and reach up under his sweatshirt. Every few minutes I would stop him, take his nuts in my mouth and suck on them and then go back down on his cock and he would take over from there. He warned me when he was about to cum and I did not pull off, instead letting him dump it down my throat. I kept sucking when he was done to clean up every drop. He was moaning and loving it and whispering that it was sensitive but I made it clear that I would decide when I was done by holding his ass and pushing his body into my mouth. I finished up my last few strokes and released him from my mouth. The first thing he said after was "damn, I should have brought a cigarette out with me"

    He gave me a hand off the floor and we got dressed. He said his jaw was still hurting and he doesnt know how I did it all the way. I just told him I have had more practice. He said, well keep my number, Ill be in touch.

    I texted him last night asking if he enjoyed what we did and he said absolutely, and said next time I go out he wants me to try fucking his ass. Im not sure im comfortable with that or not, but we will see when the time comes. It was a hell of a night, and the first time I ever did something outdoors or partially in public. I usually stay right in my house. Its a night I wont forget for awhile.

  2. #2
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    Re: Hanging out with the bad boy

    Wow, good story. It was getting me hard just reading it.

  3. #3
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    Re: Hanging out with the bad boy

    Here are some updates with this guy. So I had my surgery and did meet up with him 2 more times just for head out at his place in a vehicle, which was fun. Nothing out of the ordinary to talk about though. However, the other night I was going through my phone and saw his number and decided what the hell, Ill see if he is up since it was the middle of the night. He was, and this is what followed.

    ME-Hey you awake
    HIM-Yeah
    ME-You want a blowjob
    HIM-Yeah, that and more, but I moved and am further away, but please come.

    He gave me his new location, and I was in the car and on the way. When I picked him up he said he needed to stop at a friends house real quick so I brought him there. He was telling me he had not had sex in awhile, that he and his wife were having issues and that is why he was staying with family. After we stopped at his friends house we were back in the car and we needed a place to play. I thought of a place off the main drag behind an old abandoned building. We stopped, I started to give him head but every time headlights would come down the road he would get weirded out. Well, I had driven to far for this not to happen, so I said listen, why don't we go back down to my house and finish what we started. He was like, ok, we could do that.

    We got to the house, went inside and right to the bedroom. I realized as he began kicking off his shoes and pants that I have never seen his chest, which is one of my favorite parts of a male's body so I reached out and started lifting his shirt off. He started to stop me, but I said, no, I want to see you naked. He said ok and off It came. He laid back on my bed, head up on the pillows and I got down between his legs. I started by taking each one of his nuts into my mouth one at a time and sucking on them. After a little of that I took his semi hard cock in my mouth and started working it up to fully hard. I was letting my hands roam all over his sexy beefy body from his hairy legs to his hairy chest and nipples. I had never done anything more then head with him, so I was not sure how far to push his limits. I decided to try anyway. I stopped sucking on his cock and moved up to his nipples and started sucking on one and then the other, working it with my tongue and biting with my teeth. His breaths picked up a bit and it was clear he was enjoying it. I then kissed my way down his stomach until I had his cock in my mouth again. I began playing with his balls in my hand and some of the saliva was running down his cock and balls. I spread his legs a bit, took some of the saliva on my finger and began playing with his hole. He closed his eyes, relaxed a bit and seem to open himself even more to me as if to say to keep going. I found more saliva, and again started just playing with the entry way of his ass as I continued to suck him. A few minutes more of this and then I decided it was now or never. I took my pointer finger and ever so carefully pushed it in. He immediately began moaning but allowed it to go in. I worked him a bit with that finger and then took it out and put in my middle finger instead as it is a bit longer. I started really massaging his prostate while sucking him, and he was moving around on the bed, moaning out loud and it only took about 90 seconds and he was spilling all of his seed down my throat. He said he really enjoyed the finger and that got him off so much quicker. I decided it was time for one more first, I got up on the bed further and straddled him so I was sitting over his legs and began massaging his stomach and chest, leaned down to once again suck each nipple, then went to his neck and started kissing there and then moved towards his lips. He said, no man, Ive never kissed a guy. I said, just one? He said ok. I told him to close his eyes, it was just lips and it would feel the same. I leaned down, our lips touched and he actually reciprocated and we kissed for about 20-30 seconds. After that I just collapsed beside him and cuddled him for awhile until it was time to bring him home so he could be there for when his son left for school. It was a fun encounter and I hope he is back again soon.

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