Cruising in My In-Laws' Neighborhood

I used to travel for work. Often being gone for weeks at a time and all across the country. I discovered Craigslist and the personal sections for some no strings attached fun. As I settled in at the hotel, I would start scouring the personal ads for some fun. The women were usually all talk, but the men and some of the couples were often up for fun.

One of my most exhilarating adventures was when I was staying in my in-laws city (they lived an hour and a half away) and I started looking. I was staying about 15 minutes away from them and figured the chances of coming across someone who knew them were slim enough.

I saw some ads that caught my eye and replied to a few. One reply came through quickly from a married guy who was at home but could use a trip to the store as an excuse to meet up in the parking lot behind the grocery store for a quick bit of fun. I agreed that we could meet there and use the back of my van - I folded down the middle seats to give some room for gear I needed for work, but that space would also work for some fun. The back row seats were set up and would be better than trying to work around the steering wheel. I gave him the description of my van and agreed to meet him in a section of the lot with less lights. I got into the van and headed right over.

As I was following the directions, I realized that the grocery store was the same one where my mother-in-law worked. We were going to be less than 3 blocks from their house and only a few blocks away from a few of my wife's friends that I knew. Normally there wasn't too much chance of getting caught on the road - usually used the hotel room or their house. In my van, in a public parking lot added some excitement to it. And knowing that my mother in law might be inside working or her parents or one of my wife's friends could be out for a stroll and walk past was exhilarating. More excitement at the possibilities.

I pulled into a spot, careful to park away from a car that looked like my mother in law's. Not too close to a lamp post and hoping for some good shadows, although anyone seeing a guy climb into the back of a van where another man was waiting would look suspicious. I climbed into the back and sat on the back bench, waiting nervously - this was a first to meet up in a van in a public spot. I sat there rubbing my crotch, waiting. Luckily I didn't have to wait long before there was a knock on the window.

I opened the door to a a guy who was average height and weight, clean shaven and short brown hair - it was tough to see a lot more details in the dark parking lot. Like me, he was wearing sweat pants and a t-shirt and I thought I could see the beginning of a bulge.

"Come on in," I said and closed the door behind him. We sat on the back bench and he didn't waste time and leaned in to kiss me and started to rub my cock through my pants. Off to a great start. I took a second to ask what he wanted to do, since his ad had said he was up for whatever. "I can jerk you off, give you a blow job or top or bottom for you. What do you want to do?" he asked.

Part of me wanted to just give each other blowjobs and be done, but I also wanted to fuck and possibly get fucked. In answer to his question, I reached down and slid his pants free from his cock and seeing that he was a decent size, I said I wanted him to fuck my ass and then I would fuck him after.

He was at least 6" but not very thick and and had a big curve to it. I leaned forward and started to lick and suck him, to get him ready, while removing my pants at the same time. After slobbering on his cock for a bit, I turned away from him, and on my hands and knees, presented him my ass. He reached out and kneaded my ass cheeks a bit and moved one finger to my hole, which he wiggled into my ass, before leaning forward and licking my hole. After a bit of play to loosen me up, he positioned himself with his cockhead against my hole and started to push his cock inside me. Slowly my ass spread for his cock and I felt him entering me. As he got himself fully inside me, it felt different. He wasn't as thick as what I had experienced before and I could feel the upwards curve pushing against my insides differently. Slowly he slid his cock in and out of my ass, the curve giving a different sensation.

I had him pull out for a second and got on my back and lifted my knees up and had him enter me that way. Every time he slid in and bottomed out, I felt a wave of pleasure radiate through my body and I would tense up a bit. In and out he pumped, getting faster and harder and I could hear his breathing getting heavier as he was leaning in my ear as he fucked my ass. I turned my face to him and we began kissing deep and forcefully- his thrusting began to match, fast, hard and a bit rough. Faster and harder he fucked my ass, with waves of pleasure ripping through my body as his cock pounded some magic spot. He gave a grunt, tensed up and let out an exclamation. "Oh God, I'm coming," he grunted as he shot jets of hot cum into my ass. His body jerked a few times as he filled me up. He leaned forward again and kissed me gently, before letting his cock fall out of my ass, as he kissed his way down to my cock, kissing and licking the head of my cock. Then he pushed my legs forward and began to lick the cum out of my ass.

Without saying a word, he got onto his hands and knees and stuck his ass towards me. I didnt need an invitation. I got a finger full of cum that he missed and rubbed it into his asshole, working one then two fingers in to get him ready. I set the head of my cock against his asshole and pushed not too gently inside him and he gasped a bit. My cock then slid all the way inside him and another gasp escaped his mouth. He was super tight, wrapped around my cock, his cock hanging down between his legs. I grabbed his hips and started to slide my cock in and out of his ass - never fully coming right out. I fucked him for a bit where just the head came almost out and just back in again - it felt amazing and hopefully for him as well. Then I slid it all the way in again and fucked him with long hard strokes, slamming into his ass cheeks each time, my balls slapping against him. I alternated in a minute of short fast movements, speed fucking his ass.

Occasionally he would clench his ass tight as I was all the way in, not letting me slide out at all. Then he would relax and I would pound his ass for all it was worth. I started fucking him harder and faster, knowing I was getting close.

"Ass or mouth? Where do you want it?" I asked him as I was getting real close.

"Mouth. Come in my mouth," he said, so I pulled out and he knelt in front of me as I jerked my cock, his tongue out and mouth open, waiting for a load.

"Here it comes!" I said as I let loose, cum hitting his tongue, landing in his mouth and onto his face as well. He wiped it all up and made sure to swallow it all.

Without saying anything, he quickly got dressed, opened the door of the van, got out and said, "Thanks. Say hi to Joy for me," as he walked away.

Guess I was too close for comfort. Who was he and how did he know my wife's name?

It wasn't until I got back to the hotel and saw a message from him, saying he was at our engagement party, but he didn't expect me to remember all of Joys friends. And not to worry - our secret is safe and could be something regular anytime I was in the area. His wife could never know and neither could mine.