I was on a business trip out of town a few months back, and found myself bored, lonely, and horny sitting in my hotel room. I began searching through Craigslist, and ended up posting a fairly innocuous ad looking for a female in the area. I was pretty vague, but honest, and really said I was looking for a dinner or drinks companion more than anything else.
About half an hour later, I got a response from a woman not too far away. Her name was Carrie, and she described herself as mid 30's, recently divorced, and would be up for meeting somewhere for dinner. We exchanged a few friendly emails, not ever really bringing up anything sexual, and she agreed to meet me in the restaurant in my hotel lobby. She was familiar with the area, had never eaten there, and had heard it was actually pretty good! We set up a time for later than evening. She sent me a photo so that I could recognize her, and I was reasonably happy with what I had seen: she looked to be average height, dark brown shoulder length hair, pretty brown eyes, and a great smile. She looked thin, with probably a B cup from her photo. I sent her a decent shot of me as well, and I showered, shaved, and cleaned up for the evening. I threw on a pair of charcoal dress pants and a dark button down, and headed to the lobby at the appropriate time.
I thought I would be a few minutes early, but I found Carrie already in the bar area. She was wearing a nicely fitting black dress – nothing overly dressy, but very classy and tasteful. I greeted Carrie with a hug, and I sat down in the bar next to her and ordered a drink.
Carrie was very nervous meeting some stranger from Craigslist, but I reassured her that I was a perfectly normal and sane individual. I asked her what led her to respond to my ad, and she confessed that she had been fairly isolated since her recent divorce, and that she was trying to break out of her shell a bit. Carrie was very likable and easy to talk with, and our conversation continued to flow over the next hour or two. We both had several more drinks, neither of us drunk by any stretch, but definitely loosening up a bit.
Eventually, the conversation steered into the sexual realm, and Carrie blushed a bit. She confessed that this was her first "date" since her divorce, and she hadn't even let herself think about sex since their break-up. But she said that she thought enough time had passed, and that she was ready to pursue things again. I made a mental note of this, and my cock jumped a bit and the potential of things to come.
As I paid for the check, I asked Carrie if she was interesting in keeping the night going, maybe find a club or somewhere nearby to head over to. She quickly agreed. I told her I just needed to run up to my room to freshen up and grab a few things, and she offered to ride up the elevator with me and wait in my room. As we entered into the room, Carrie's demeanor changed a bit, and she seemed a little nervous. "Is everything ok?" I asked. She said she was fine, she knew what about to occur, but she was probably a little out of practice. I smiled a bit, grabbed her hand, and leaned in to kiss her. "We can stop whenever you want," I said. I kissed her on the lips, nothing too long, and then pulled away. I leaned in again, and she immediately reciprocated with a long kiss back, and her hands grabbed me around the waist. We fell down on top of the bed, kissing passionately, each of our hands on the other's waist. My cock began to throb inside my pants, and Carrie must have known, as she began to rub it through the outside of my pants. I slowly reached down and began to rub her breast through the outside of her dress, as she moaned softly in between kisses.
Carrie began fumbling with my pants zipper, and I rolled over on to my back to give her better access. She smiled, then shimmied by pants and boxers down in one motion. She began to stroke my cock with one hand, and playing with my balls with the other. "God, it's been awhile," she joked, but the stiffness of my dick showed she still knew what she was doing. Slowly, she began to drop her lips around my cock, licking up and down the shaft a few times, and then pulling away. She was a bit of tease, but she gave a damn good blowjob. I unbuttoned my shirt and took it off while she continued to suck on my dick long and hard. Eventually, she worked herself around on the bed so that I could ease my hand up inside her dress, sliding closer and closer to her pussy. She eventually hiked her dress up over hips, exposing a beautiful ass with a nice pair of black panties underneath. I eased one finger inside her panties, and could tell she was extremely wet. My fingertip just barely entered her, and she let out a loud moan. She stopped sucking my dick for a minute as I began to slide my index finger into her as she sat on the bed on all fours.
She begged me not to stop, so I began to finger fuck her with a constant, steady rhythm. I got off the bed, pulled Carrie to the edge of the mattress, and quickly buried my face between her pussy lips. She began to buck her hips wildly, and it didn't take very long at all before she began to whisper "I'm going to cum, I'm going to cum" over and over. A few more well placed strokes of my tongue on her clit and Carrie let out a loud moan of pleasure as she orgasmed. I let her lay there and catch her breath for minute before crawling into the bed next to her, my dick still hard. I had grabbed a condom and began sliding it over my dick as Carrie sat up and stripped her dress completely off. She gave me that "come fuck me" look as she laid back on the bed, and I slowly slid inside of her. I fucked her hard and steady in missionary for a few minutes, until eventually pulling out so that she could flip over. Carrie leaned over the edge of the bed, and I entered into her from behind. Her pussy was tight, and felt amazing around my dick. Soon after, I could feel my balls beginning to tighten, and I began pounding Carrie's pussy even harder. I came long and hard, and collapsed onto the bed.
After a little while, Carrie and I just laid in the bed and drank a few more things from the in-room bar. Eventually, she said she needed to go, so I put some clothes on and walked her back down to her car. She thanked me for the evening, and told me to call her if my work ever brings me back to town.
Source: reddit.com/r/gonewildstories/comments/3zfylk/out_of_town_craigslist_success_mf_long