My only Craigslist encounter [FM]

I like to live life to the fullest but I am not reckless. I value my safety and try not to put myself into dangerous situations but I also don’t want to miss out on the experiences life can provide. I was balancing that thought process when browsing Craigslist personals one night a couple of years ago.

Craigslist has never been the biggest site of its type in the UK. We have Gumtree but that stopped doing personals a few years before Craigslist did so a late-night session of laughing at dreadful ads always sent me in one direction.

I was browsing one night and there was a post near me asking for someone to go for a walk. The poster claimed to be a single man in his early forties who wanted someone to spend an hour or so walking around public, well-lit areas talking, getting to know each other well enough to see if we wanted to spend the rest of the night in private.

I was intrigued by the idea. It seemed either really considerate or quite devious and designed to create a false sense of security. I decided to move on but after a few minutes, I was reading the message again. It was after 10pm and the ad was asking for a meeting that night so there wasn’t much time to decide. In the end my curiosity took over and I fired off a quick reply saying I was 27, female and willing to go for a walk. His reply fell into my inbox within five minutes with a picture, a polite response, a mobile number and a suggestion of where we could meet. I fired off a quick reply to say I would be there in 15 minutes and went to get my coat.

I found a bench with a view of where we had agreed to meet and brought his picture up of my phone. Soon enough a figure matching his description sauntered into view and I made a quick assessment of him. He seemed confident, well-dressed and handsome. He was wearing jeans, a jumper and a jacket and from a distance seemed like he could be interesting. I stood and started to approach him. He turned to face me and a flash of realisation crossed his face. I was wearing skinny jeans, a t shirt and a long jacket that obscured my figure but I could tell he was scanning me to work out as much as he could. We exchanged pleasantries and started to walk.

We walked for about 45 minutes, staying to well-lit and non-threatening areas. Conversation started polite and distant but soon got more adult, but still polite. Having acknowledged why we were meeting, we gently probed each other for details to see whether we were compatible. My early assertion that he was confident only seemed more accurate but he didn’t seem arrogant. We got on well and soon got back to our starting point. Decision time. He asked whether he should call an Uber and take us back to his hotel and I replied that he should. A smile crossed his face and we talked for a few more minutes until our car arrived.

We walked through his hotel room door and he offered to take my coat. I shrugged it off, he hung it on the back of the door and turned to look at me. His eyes roamed over my body and settled more than once on my big boobs. He approached slowly, placed his hands lightly on my hips and leant in for a kiss. I returned the attention and our kiss became more energetic.

We switched from gentle to frantic as hands roamed and clothes were removed. Before long, he was in his boxers and me in bra and knickers. Our tongues were wrestling as my hand landed on the front of his boxers to find a hard, twitching cock. Giving him a dirty smile, I lowered myself to my knees and took his boxers down with me. His cock bounced up in front of me and I guessed it to be about seven inches long. Giving it a couple of strokes, I looked up and our eyes met. He asked me to suck it and I couldn’t resist a little joke about his age as it had been one of our conversation topics earlier in the night. He was fully hard and I asked if he would be able to get it up again if I made him cum. He gave me a smile while calling me a cheeky bitch and pushing my head onto his cock.

The blowjob started with me dictating pace but he soon took over. What started as a soft but energetic blowjob soon evolved into him face-fucking me. Spit was streaming down my chin and my eyes were watering as he thrust in and out of my throat. His hands were on the sides of my face and his fingers laced behind my head as he got closer and closer to his orgasm. He pulled my head closer as he thrust deeper to cum down my throat with a roar. His cock spasmed with every rope of cum he shot. When he was spent he released my head and I sank back to sit on my heels to catch my breath.

He recovered his composure and saw me catching my breath, spit, tears and make-up making a mess of my face. He apologised for going too far but grinned when I asked which bit was too far and that it was my turn now.

Having wiped my face down, I sent him to the bed. He made himself comfortable and I straddled his face. His tongue was willing and fast meaning I was soon grinding my soaking wet cunt onto his face. His stubbled grazed my lips but the sensations only heightened the experience. My hands were braced against the wall to keep my upright as my orgasm inched closer. I could feel it build and gasped that I was going to cum just as my first orgasm hit. I bucked writhed while trying to stay on his tongue, moaning and gasping for air at the same time. His tongue didn’t stop throughout and, as I raised myself to let him breathe, his hands found their way over my thighs and pulled me back down. His tongue went up a gear and it felt like he was trying to lick his way into my soul.

More orgasms followed until even the wall wasn’t enough to keep me upright and I had to get off of his face. I lay next to him on the bed and couldn’t help but giggle at the glistening pussy juices on his face. He was catching his breath too and said that he was going to clean up but he couldn’t let me go without fucking me. As he disappeared into the bathroom I fumbled in my bag for a condom and left it on the bed next to my feet as I got into position for him coming back.

As he came out of the bathroom, he was greeted by the sight of me head down, arse up and back arched on the bed. I was open and exposed but loving it and soon heard him whisper ‘fuck’ and unwrap the condom. He lined up behind me and I felt his hands steady my bum as he began to push in to my pussy.

There was no need for gentle. My pussy was slick, his cock was diamond-hard. Once his head went in, it was all fast and energetic from there. He plunged in and out of me, sawing his whole length from root to tip through my very willing pussy. He fucked hard and our skin slapped together with each thrust. The room suddenly felt hotter, we started sweating but that just made it better. He kept his pace, occasionally slapping one of my bum cheeks and saying how good my pussy felt. I was loving the hard fuck and my fingers instinctively went to my clit. The combination of fingers, cock and the sounds of grunting and skin slapping together brought my next orgasm on fast. I breathlessly said that I was going to cum and he started fucking even faster. I cried out as I came and he gave a guttural grunt as he pushed as deep as he could and came hard. I could feel his cock twitching as he filled the condom with his second load of the night.

As we caught our breath we untangled ourselves and straightened up. He disposed of the condom and we dressed quietly. He thanked me for answering his ad and gave me his number again for if I wanted to do it again. I left and made my way home for a shower, confident that I wouldn’t call him. Some things, no matter how good, should stay in one time and one circumstance. The memory is often better than the second attempt.

Source: reddit.com/r/gonewildstories/comments/ctv879/my_only_craigslist_encounter_fm