Trolling Craigslist


Wanted: SWM for one night out on the town. If we hit it off we’ll end the night at my place. You must have an open mind and be well groomed. Call me and it will be my treat.

Her picture was attached to the “no strings attached” add and I was intrigued. She was beautiful. Her long red hair and easy smile dominated the picture despite the fact that she wore little more than a bra and panties.

I was a little afraid someone would beat me to the punch, so I called the number right away. “Hello, this is Tammy,” she said in a sweetly breathy voice.

“Hi, my name is Ed,” I said. I took a deep breath and continued. “I saw your ad on Craigslist and wanted to know if you had found a date yet.”

“Not yet,” she said, “but I’ve had a lot of calls on it.” I could imagine her twirling a finger through her hair as she continued. “Why don’t you tell me why I should pick you.”

Shit. I had not considered that there would be an interview. I looked at her ad once more and said, “I’m clean shaven and well groomed. I am good looking, but not so much that I think it is all about me. I am open minded politically, spiritually an sexually, not because I don’t have opinions, but I think that we can’t learn and take the most from this world if we close our minds. I think you are beautiful and I would be honored to be your date for the night.”

I stopped talking and held my breath. There was nothing but silence on the other end of the phone and I knew I was going to be spending the night alone.

“Do you know Gustav’s on Third?” she asked.

It was a nice little restaurant with a modest bar attached. I had been there a couple times for dinner, but never on a date. “I know the place.”

“I will meet you there at eight,” she said and hung up the phone.

“Yes!” I put away my phone and hopped in the shower. I took my time and gave myself a fresh shave below the waist even though I had already done so that morning. A quick shave and slight splash of cologne and I was ready to get dressed.

Gustav’s was nice, but casual, so I threw on a pair of khaki’s and a short-sleeved, button-down blue shirt. I gave myself a quick once over in the mirror and walked out the door.

I got to the restaurant a few minutes before eight and went in through the bar entrance. I looked around, but did not see her there, so I sat at the bar and ordered a glass of merlot from the tired looking bartender.

With wine in hand I turned and surveyed the bar. It was just bright enough inside to make it easy to see everyone within, but not so much that privacy couldn’t be found. The booths that ringed the room were bastions of shadow that would only be penetrated by eyes standing at their edges. There were a couple of dozen people sitting at the tables throughout the room, and I imagined they were all regulars except for the couple of individuals sitting at the bar.

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A short blonde woman walked up to me and asked if I would buy her a drink. She was attractive, with large breasts that her too small shirt fought to contain. Any other night I would have ordered that drink without a moment’s hesitation, but I politely told her that I was meeting someone. She smiled and told me to come see her if I changed my mind. I said I would and happily watched her well-rounded ass as she walked away.

I turned back toward the door and Tammy was standing there watching me. She was wearing a tight green dress that stopped just above her knees and showed just enough cleavage to attract the eye of any man looking her way. She walked through the bar like she owned the place and for all the attention she was receiving from the other patrons she may well have. When she stopped in front of me the other men went back to their wives and dates.

“You must be Ed,” she said as she held out her hand to me.

I stood up, took her hand in mine, and kissed the back of it. I felt a little ridiculous, but it seemed like the right thing to do at the moment. “It’s nice to meet you,” I said.

“Bring your wine,” she said as she turned and headed toward an empty booth in the corner. I watched her go and was pleased to see that her ass was even more impressive than the blonde’s. I followed and slipped into the booth across from her.

“How did you know it was me?” I asked.

“I saw you turn down the blonde,” she said, “and I figured that anyone who would reject a fine piece of ass like that must be waiting for something better, so you had to be the guy I was looking for.”

I smiled and laughed. “I’m glad to see I made the right choice.”

“That you did,” she said. “Would you mind scooching over a bit and meeting me half way?” She slid around the table and I did the same until we were sitting close enough together that our knees were touching. “Sitting across from each other feels so formal, doesn’t it?”

“Yes it does,” I said with a smile.

Tammy waved to one of the waiters and said to me, “Well so far your description has been pretty accurate, except you cut yourself short on the good looks.”

“Thank you,” I said. “You look even better than your pictures.”

“I hope you still think so when you see wearing as little as I was in those pictures.”

“I can’t imagine otherwise.”

“Ahem.” The waiter coughed as he stepped up to our table.

“I’ll have a glass of syrah and a menu, please.” The waiter nodded and walked away. “Now,” Tammy said, “where were we? Oh yes, we were going to get to know each other a little better.”

For the next hour we drank wine and picked at our meals while we talked and flirted. Okay, to be fair we spent much more time flirting than really talking, but we did get to know each other some. By the time our check arrived we were almost sitting in each other’s laps and Tammy’s hand was travelling up and down my thigh.

Once the waiter had taken the check she looked at me and asked, “Do you trust me?”

I looked back, staring into those pretty blue eyes and realized that I did.”Yeah, I do.”

“Okay then here is the deal,” she said. “I’m not looking for a boyfriend. I just want a man I can have some fun with from time to time. If you come home with me tonight I guarantee you will have a night that you will never forget. If you want to do it again then we’ll figure that out later.”

It was an offer I couldn’t pass up, but thoughts of knife play or water sports entered my thoughts, so I said, “What do you have in mind?”

“Nothing painful, filthy, or illegal, but you’ll have to keep that open mind and promise you’ll give it a try.”

I looked at her once more and decided it was just for one night. Even if she strayed into the realm of the truly weird I could always say no. “All right. I’m in.”

Tammy squealed and kissed me. It started simple, our lips pressed together, but she squeezed my thigh and our mouths opened. I am no stranger to kissing, but kissing her was like nothing else. I felt the thrill of it all the way down to my toes while our tongues wrestled between us.

“You two need to take that somewhere else,” the waiter said as he dropped the receipt and credit card on the table. He walked away and Tammy flipped him off. We slid out of the booth and headed outside.

“How do you want to do this?” I asked.

“The better question is, how won’t we do it?” she said with a laugh. “Why don’t we take your car and we can pick mine up in the morning?”

“Sounds good to me,” I said. I opened the door of my pickup and Tammy climbed in. I got behind the steering wheel and after a couple of directions from her, we were off.

We were not a half-mile out of the parking lot when Tammy’s hand was on my leg and moving upward. “I don’t think I can wait to get home before I see what we’re working with,” she said as she rubbed my cock through the fabric of my pant leg. The harder I got the more she rubbed until she finally freed me by unzipping my fly and pulling me out. “Very nice.” She slid her hand up my shaft, squeezing out a clear drop of pre-cum. Tammy wiped it off with her thumb and placed it into her mouth. “Mmm the perfect dessert.” With a slight shift she bent over and sucked the tip of my cock into her mouth. Her tongue flicked about the tip. But her lips never moved from just below the head.

When we pulled into her drive way I was about to grab her by the head and push her down, but she released me at the last second and sat upright. “Inside,” she said. “Let’s get inside.” We both fumbled with our doors and ran for her front door. I had not bothered to put my cock away, so when she fumbled with her keys I pressed against her ass with it. Tammy moaned and squirmed against me until she found the right key and opened the door.

We stumbled through the door, barely closing it behind us, and stopped in the living room. I spun her around, grabbed her by the hips and pulled her against me. We kissed and Tammy took my cock in her hand. She slowly stroked me and I thought I would go mad if I didn’t have her soon.

I don’t know how she did it, but she managed to undo my pants and push them down to the floor without me knowing. She broke our kiss and looked me in the eye. “Just one rule, okay?” she said. I nodded and tried to kiss her, but she held me back. “If I do anything you don’t like you have to tell me right away. ” I nodded again and Tammy smiled.

She unbuttoned my shirt and I pulled it off. She ran her fingers down my chest and across my stomach as she dropped to her knees. I held my breath in anticipation while my cock hovered before her mouth.

3 thoughts on “Trolling Craigslist

    1. Okay, my android ap screwed up the post, but I have fixed it now…I added the end of that sentence back on plus a couple of paragraphs…it will still leave you hanging though…


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