[Reposting since I used the wrong tags]
I’ve been meaning to write up some of my personal experiences both for posterity as well as to see if other people enjoy them. This happened earlier this year before FOSTA shut down Craigslist casual encounters in the US.
I’ve used Craigslist over the years as an outlet for my sexual desires without fear of my coworkers, friends, or family discovering my deviant side. It also cuts through societal niceties by targeting a community of people who were also open to something carnal. Normally at a bar I play it safe and am very polite unless I meet a woman who is more forward about her intentions, which is rare. On Craigslist these clean separations allowed me to feel more confident and unencumbered by societal expectations and gave me permission to be direct and sexual since it was implicit. It’s also let me take a shortcut to a few of my sexual bucket list items though I still have many more still to go.
I’ve lost my original posting but there were a few things I tried to do (and often failed) to make my posts stand out in a sea of mostly unintelligent, out of touch, porn addicted, gameless, desperate dick pic postings that are the norm.
1. Post at peak traffic hours.
2. Use a catchy subject.
3. State that I’m selective and want the same (STDs? No, thanks)
4. Describe myself aesthetically (white, 6+ feet, athletic body, average but thick cock, etc), my behavior (polite, patient, etc.) and my sexual preferences (dominant but giving).
5. Describe what I’m looking to show that I am selective (shapely, non smoker, no kids, etc.) but without being too specific to avoid coming off as an asshole.
6. Avoid spelling and grammar mistakes.
7. Request their first message change the subject to something like their favorite color to prove they’re not a bot and that they read my post.
8. Include a photo showing off my physique without showing my face or exposing myself.
I’m not going to pretend like posting to Craigslist was a magical place where you can find whatever you want. It was a slog. Most of the time you’d get a message a minute from spam bots which are easy to dodge thanks to point 7 above. The next most common message was from other men who were either pretending to be women, were “straight” but wanting to mess around with guys, were offering gay for pay, or were honest and offered a discreet hookup. Then finally, there were the occasional responses from women but most of these I found to be unattractive (too big, too old, not feminine enough). Lastly, for the few women I thought were attractive, they might disappear after losing their nerve, deciding I wasn’t their type, falling into their spam folder, or I said something they didn’t like. You have to walk a line of coming off as confident and sexual without being needy or arrogant and responding quickly but not so quickly to come off as desperate.
Post title: No names.
The gist was simple: I wanted to meet someone for a casual one-time fling where we know next to nothing about each other, not even our names. I think I had reposted over a few nights until finally I got a reply from ‘Girly Girl’:
>Hey there,
>
>I will be in LA on business later this month and looking for something casual and uncomplicated. And well a hook up without exchanging names is about as uncomplicated as it gets….not to mention really hot.
>
>I’m 38, blonde, fit, sexy, sassy, kind-hearted, educated, submissive in the bedroom, sexually open minded, disease free, 100% real and 100% female:)
>
>Here are a few pics of me….hope to hear back.
She included a few faceless photos, one of her in a bikini. She was fuller-figured than I usually go for but she was shapely with a nice chest and feminine style and I really liked her enthusiasm in her first message, not to mention that she was visiting which meant she would probably have a hotel room. She was also a little older than me but I was also intrigued by the idea of being with an experienced and confident woman.
>That’s probably the most perfect scenario we can have. I assume you’ll be staying in a hotel downtown? How long will you be here?
>
>I’m over in [location] in LA, so depending on where you are we will have to work out logistics but it shouldn’t get in the way.
>
>You have a sexy body… I’d love to see more. A face pic helps too. I’ll reply in kind. I do want to know — have you had kids? I’m assuming not. Also, how tall are you?
From Girly Girl:
>I will be in town for two weeks and actually staying in Beverly Hills and Santa Monica.
>
>And thank you. No, I have not had any kids and am 5’6”. Can we trade face pics over Kik or Wickr? I’m super cautious about disclosing my identity given that this is CL.
>
>My screen name for both is [name] (and no that is in no way close to my real name ?)
For the uninitiated Wickr is like Snapchat for messaging. You can set a time-span for the messages to expire and they disappear. For this reason, I don’t have the transcript of messages we had together leading up to her visit but in short we very quickly got to talking about our sexual fantasies, past experiences, likes and dislikes, limits and more. She quickly fell into the role of my submissive and was regularly addressing me as Sir and we both addressed her in the third person as my cum slut, cock whore, fuck toy and every other degrading name you can think of. This isn’t something I personally seek out, but I can read people well and I could tell this was the sort of thing she might like and I take pleasure in giving others pleasure. It was for sure her preference and she gave her consent and I’ll admit that there was something hot about a woman older than me addressing me as Sir.
Over the following days I had her performing slutty assignments in preparation for her visit, including modeling outfits that I would choose from to fuck her in, getting her nails done, masturbating silently at work in the bathroom and walking around in her soaked panties all day, and meeting a nightly orgasm quota. When she failed to complete her assignments she was punished with even sluttier assignments. One night when she failed to model one of her outfits for me from the night before I had her write the word SLUT across her ass and CUNT above her pussy in lipstick, then shove the lipstick tube inside her pussy and send me photos as proof. She complied and enjoyed herself a little too much. The night before we met she had another punishment to masturbate to orgasm in front of open hotel windows or her open hotel door. I knew she would pick the windows but wanted to test her anyway.
It was through these chores I learned a few more basics about her: she’s a well paid executive at a large company with all male peers, she lives on the east coast, she’s single… all still very generic but helpful to me to get an idea of her personality.
I had concocted a plan of how our night would go in great detail and told her all about it to get her excited. I deliberately left out some details until the last second to keep things interesting and left plenty of room for things to deviate if needed. I had her scout some private areas of the hotel lounge for us to first meet but be secluded from others. I also had her investigate some of the hotel’s facilities to see if there was anywhere I could fuck her in public without being caught as that was a turn on for both of us. There weren’t any but I think the chores were a hot distraction for her to fantasize about.
Finally the day had come. She was going to meet me in her hotel lounge on Friday after work and have a cocktail with me to assess if we were both willing to go through with it. We had discussed many of the details in advance but I drafted much of my instructions to her on my phone so that I could easily copy/paste them to Wickr without having to think too much in real-time. Here are those notes — each paragraph represents a single message I would send to her. Keep in mind that she would respond and some time would pass between each message.
>Are you ready to be my obedient slut today?
>
>I want to remind you both of us reserve the right to stop and walk away from things at any point. We are both consenting adults participating in an atypical situation but that does not make it an obligation. As your Sir I will be assuming you agree implicitly unless you explicitly disagree with your words or actions. Please explicitly state that you accept this now and state any firm things you do not want in advance.
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>You must also assume that this may be the only time you get to see your Sir so you should savor every moment. Once he leaves you will not message him again unless he messages you first.
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>I am preparing to head to the hotel now. I’m going to need some time to get myself a cocktail and get comfortable. In the meantime here are your tasks:
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>1. Get your toys and blindfold and lay them on the desk.
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>2. Get your candles and lighter and arrange them but do not light them (she ultimately forgot to pack the candles).
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>3. Get two bottles of water or two cups of water and place them on the stand next to the bed.
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>4. Freshen up your perfume and touch up your make-up.
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>5. Put on your stockings and pumps.
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>6. Turn off any overhead lights but turn on all lamps and ambient lighting.
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>7. Open the blinds or curtains to your windows.
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>8. Turn on quiet background music.
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>9. Get a piece of hotel note paper, preferably with the hotel’s logo on it. On this paper write the following:- Today’s date.
– Three or more things you’ve enjoyed the most talking with your Sir.
– Three or more things you’re excited about for today.
– Sign it with your favorite dirty name for yourself.
– Place a lipstick kiss next to your signed dirty name.
– Add “PS. Sir gave me _____ orgasms today”. You will fill in this blank with your official count of orgasms before I leave.
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>10. Fold the note up like a sleeve around your room key and write your room number on it.
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>11. Send me a message when your tasks are completed and you’re waiting for your Sir.
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>12. Sit quietly and gently pet your pussy through your underwear while you wait for further instructions.
After I had arrived I let her know I was in the lounge but had her wait in her room. I eyed the perfect spot but had to wait for a couple to finish their drinks and vacate. It was in the back of the room; a couch across from another couch with a glass coffee table in between. I sat on the couch facing the room, leaving her to sit on the opposite couch with her back to the room. I got myself a glass of whiskey and sat down on the couch.
>You will not speak unless asked a question with the following exceptions:
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>1. To voice disagreement, discomfort or that she needs a moment to rest.
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>2. To communicate pleasure and optionally describe what is currently happening.
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>3. To communicate her orgasm count has just increased.
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>You will always address me as Sir and yourself by your favorite dirty name or any other dirty name of your choosing.
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>Do you understand?
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>I’m ready. You will find me down in the lounge area in the back. There is currently a live jazz band playing although they may be done and packing when you arrive. Sit down across from me on the red couch. Do not say a word. If anyone approaches you will speak to them only if absolutely necessary, otherwise I will answer for us. If you need to communicate with your Sir you will use your phone to send a message. Do not speak.
It was at this point that she made her way down to the lounge. She texted me how she suddenly got very nervous and it showed in the way she carried herself as she walked in.
I had decided that she would wear a professional looking dress she liked. It was black with pin striping and some white details, modest around the collar but with a flared skirt with black pumps. I wanted her to remember getting fucked in it the next time she was in an important meeting at work in it. I was wearing a dark gray suit with a black button down shirt and tie. She nervously sat across from me, holding eye contact with a naughty smile, then started texting me to ask if I liked what I saw. I did.
We chatted over text in silence across from each other, each with slight smiles on our faces and frequently looking up to hold eye contact, all the while others in lounge chatted away and moved around us unaware of the circumstances of our rendezvous. She said her coworkers were also staying at the hotel and was afraid one of them might see her but it was also part of the thrill. She said she thinks she needs a drink to calm her nerves and asked if I wanted one, then went off to fetch two whiskeys on the rocks.
After she returned and a few more messages back and forth to nervously delay, I sent her this:
>When you feel comfortable, part your legs, lift your dress, show me your panties and gently pet your pussy through them. Continue to do so until you see me signal you that you can head to the restroom. Remove your panties in the restroom, wrap them as best you can around the room key and note and return. Place the card underneath my drink and sit.
She messaged me that I needed to alert her if anyone was coming over to our table. I nodded. She nervously looked over her shoulders to survey the room, then cautiously placed her drink down in front of her. She cautiously parted her legs and began to pet herself over her panties — I quietly gestured that her dress was obstructing my view for her to lift it and she did.
It was just then that an older group of people sat down at the couches behind her. While their view was obstructed by the back of the couch she sat in, the sudden proximity of other people upped the intensity of the situation. She briefly paused and then continued to pet herself. I nodded again and pointed my finger in the direction of the restrooms and she excused herself.
She returned, slightly more anxious than before. She cautiously placed the card underneath my glass like a coaster. I fired off my next message:
>When you feel comfortable, part your legs, lift your dress, show me your pussy as you gently trace it and finger yourself for me. Continue to do so until you see me signal you, then take the fingers from inside your pussy and use them to stir my cocktail, take a sip, then slide it towards me. You will then leave to head to your room and wait for further instructions.
After a brief delay she parted her legs again and carefully touched herself. Her dress was again in the way, so I made the same gesture. She lowered herself on the couch, sliding her hips forward, lifting her skirt and rubbing her clit, all while staring at me to watch my response. I smiled, alternating my gaze between her pussy and her eyes. Reality sets in. Here I was, sitting in a hotel with a room full of people, having a cute girl *who I have never even said a word to* expose her pussy to me and play with it. Life can be wild if you make it happen.
I gestured for her to move on to the next step. She slipped her finger inside of herself, again a second time, then sat up and picked up my whiskey, stirring it with her wetted finger. She took a sip and placed it back down on the card and slid it back to me. I picked it up and took a sip. I sent her a message telling her that the Whiskey was good but it was time for her to go up to her room. Once she’s there:
>Take a chair and center it in the space on the floor by the windows. Take the blindfold from off the desk and seat yourself facing the windows. Put on the blindfold and begin to touch yourself but do not cum. Edging only. Continue until your Sir arrives but do not stop unless commanded to.
When she left, I inspected the coaster she left behind. I unwrapped her panties from it, smiling to myself and placed them in my pocket. I then unfolded the small note and read:
>[Date sometime in Mar ’18]
>
>I have very much enjoyed talking to my Sir about what turns him on, all of our past experiences, what Sir will do to me tonight and his views on facials =)
>
>Tonight I am most excited about tasting Sir’s cock, being blindfolded while Sir has his way with me and having Sir’s cock fucking my pussy until I can’t cum one more time.
>
>- Your Cum Slut
>
>P.S. Sir gave me __ orgasms today.
There was a glittery pink lipstick imprint over the second paragraph because the paper was too small to fit everything in its own space. The room number was written on the opposite side. The P.S. was a fill-in-the-blank for end. Regarding facials: we had discussed them recently. Admittedly, I love giving a woman a cum facial, probably from watching too much porn. Most of the girls I’ve been with aren’t into it for various reasons that are completely understandable: it’s degrading, it’s gross, it irritates their eyes or gets in their hair. She had explained her ex liked to do them with her and he did it in a way that made her feel humiliated. For me, it’s not about degradation. It’s intimate. I love seeing a smiling or laughing girl with my cum sprayed on her lips, teeth, cheeks, nose and forehead. To me it feels like a sense of ownership, like marking my territory, and it turns me on to think of her going about her day and talking to people when she had had my cum on her face. If I’m with them I like to visualize it in my head. She said she had never seen it that way before.
I picked up my whiskey, took a deep breath, and made my way up to her room. I paused briefly outside of the door thumbing the room key to savor the moment, then unlocked the door and set the key on the table. The room was warmly lit, with soft music playing and she sat in a chair in the center of the room with her back to me, blindfolded and masturbating.
I sat my whiskey down next to hers on the desk. I didn’t say a word, leaving her to listen intently and try and figure out what was happening from the sounds she could make out. I stood over her right shoulder, unzipping my pants and then brushed the head of my hard cock across her right cheek. “How does it feel to know that the first time I touched you it was with my cock?” She smiled. “Very good, Sir,” continuing to masturbate more aggressively and leaving her mouth uncontrollably open as an invitation. I continued for a few moments brushing my cock across her cheek, letting her feel its size and contours over sensitive skin that’s not frequently touched.
The precise details of what was said and what happened at this point are fuzzy and to be honest the build up is the more exciting part to read but here are the highlights:
* As I fed her my cock, she reach behind me to grab my ass and pull me into her throat. She only had to do this once before I took over pushing my cock all the way into her mouth with my balls resting against her chin.
* I asked her if she was ready to get fucked, then I removed her blindfold and had her walk out onto the hotel balcony and bend over. The balcony rail was simple metal bars. It was a cool but clear night that night in LA. I picked up my Whiskey, pulled up behind her and lifted her skirt and slowly pushed my hard cock inside of her. We were only a few floors up from the valet and she was doing her best to keep quiet while I fucked her over the railing, casually sipping my whiskey. I remember seeing people walk on the sidewalk and in and out of the hotel, thinking there was a very real chance they saw us because we were in clear sight fucking. After a few minutes, I told her she was my cup holder and to hold my whiskey so I could fuck her harder without spilling. She asked if she could have a sip and I told her no; she has her own whiskey, this one was Sir’s.
* I stopped, had her fetch her own whiskey while I sat in one of the balcony chairs. I told her to sit down on my cock while she enjoys her drink. She hopped on and bounced away, getting progressively louder.
* We stepped back inside the room and I had her bend over doggy on the edge of the couch. I took turns fucking her pussy, then walking around and fucking her mouth, then back to her pussy.
* All throughout this, she was orgasming constantly. I gave her instructions to count them but there were so many I couldn’t keep track to make sure she was accurate.
* Exhausted from cumming she collapsed on her still pristine bed, still in her work dress. I laid next to her, clothes half-on. She stroked my cock as we laid until I got up and fucked her missionary style.
* She let me know she was becoming sore and overstimulated from orgasming too much so I straddled her face and stroked my cock while she sucked my balls (my favorite for some unknown reason) until I gave her a cum facial. She enjoyed it.
We cleaned up and collected ourselves but I didn’t linger. I had her complete the PS of her note, now crumpled in my pocket. I told her that I hoped she had enjoyed herself and let her know that I left the room key on the table. I left her panties on the floor and left. I went downstairs and called an Uber home. It wasn’t even midnight but I was exhausted. I came home, showered and went to bed reviewing the filthy things I had done as I fell asleep.
She had mentioned in our earlier texting that she wouldn’t mind seeing me again since she comes into town from time to time. I figured it was best for both of us to leave things exactly as they were because the more we talk the more we would get to know each other which would remove the mystery of the first situation… I never talked to her again but I hope that I left a smile on her cum covered face. I still have her note…
>P.S. Sir gave me 19 orgasms today.
Source: reddit.com/r/gonewildstories/comments/8tmrhm/fm_one_night_domination_of_a_business_executive
Damn that was hot