Guest Post: The Craiglist Experience

Today’s guest post is a very personal (and hot!) confession from The Silver Salmon @Dr_Allen80


Craiglist may have been a cesspit full of opportunist money grabbers and sex workers, but it did have at its core a group of kinky weirdos that just wanted to enjoy the freedom of indulging their deepest fantasies without any fear of rejection. For those not familiar with the website’s personals section (now sadly closed), it worked the same way as any message board, broken down into sections such as men for women, couples for women and every other possible configuration you could think of. Let’s say it was truly accessible!

I had dabbled on the site previously in a purely dating context, all vanilla and standard: boy messages girl, girl responds to boy, date arranged and so on, and to be fair I had met some lovely people, so I knew how to navigate some of the less-trustworthy clientele that lurked on the site. When I came back to Craigslist following my divorce in my early thirties it was driven by, at first a sense of loneliness, but more and more it opened up my curiosity of what other people were actually engaging with that I had barely, if at all, been aware of during my safe and quite plain married sex life.

There were people willing to kick you in the nuts for a few quid right up to people that wanted full-on baths in the stuff most of us just flush happily away through the U-bend! Some were pretty grim and some could be quite hilarious, but it all certainly opened my eyes to what was potentially happening behind closed doors. My boredom, loneliness and general curiosity lead me to start responding to some of the ads, and in time I did have some interesting conversations and even more interesting liaisons, and I felt like this was my perfect time to experiment and expand my horizons.

There were also quite a few ads for menial tasks to be performed in the nude for the advertiser’s pleasure, which eventually lead me to more specific ads geared towards CFNM (clothed female naked male) scenarios. I guess the kink here for me was very much exploring a submissive side of myself I had never been aware was even there.

I found one such ad, posted by an older woman; I think she was in her late forties. She sounded safe and experienced in the scenario and it seemed like an easy way to dip my toe into this world. She was looking essentially for a naked butler for an evening at her house; and so, totally out of my comfort zone and filled with anxiety about actually going through with it I sent an email saying I was interested. There was a bit of chat about my limited experience, I sent my stats and a picture (just my face at this point), and waited to see what would happen.

I didn’t have to wait too long.

A response dropped into my inbox. She said that my limited experience wasn’t an issue and it was something she had done a few times and had had lots of fun with. She also went into a bit more detail about the sort of things that would form my tasks for the evening, all of which were pretty tame: keep her wine filled up, cook dinner, maintain a fire and potentially provide a massage at the end of the evening. It all sounded easy enough, and we emailed a few times just chatting about when and how it would happen. We also agreed to have a quick chat on the phone to make sure that neither of us was a complete psycho. She seemed nice and we had a bit of a laugh during a short 10-minute conversation in which we arranged to meet up the coming Saturday. I’d drive to her and pick up some wine and she would provide the steak for me to cook.

Barefoot in the Car

I’ve never been hugely confident in my self-image and even less so about my naked body, so for me this felt like a huge deal. It was much less intimidating thanks to her being a bit older than me, and I felt this would make it much less judgmental, but still the intimidation was very real! I was going to be spending an entire evening with someone and I was going to be butt naked! During our conversations I had told her that I had a low self-image of myself and I guess part of this experience for me was to break through that barrier, as well as the huge turn-on I was getting about being someone’s eye candy for a night.

Saturday rolled round and at about 6 o’clock I jumped in my car and headed to Tesco to pick up some wine. I’m not a huge wine drinker so didn’t really know what to get but as soon as I clapped eyes on it, I knew it was the one. A nice bottle of Barefoot white, which seemed quite apt. Feeling thoroughly pleased with myself I got back in the car and headed to East London. Her place was pretty easy to find; it was a nice quiet street which again helped with my nerves. With my perfectly-named bottle of wine in hand I headed to her front door and rang the bell.

She answered and greeted me in a way that made feel in no way awkward, so I instantly started to feel at ease in her presence. Though sadly I didn’t get quite the reaction I had hoped for with my wine choice. We chatted easily and went into the kitchen where she got out two glasses and I poured the wine. We talked about how I was feeling and again just ran over how the evening would go; it was nice and very calming.

But as I finished my glass of wine the time came for me to head upstairs and take off every scrap of clothing I was wearing. My first audience member was the pet cat who sat there quietly judging me as I undressed. After a short pep talk with the Puss, I gingerly started going down the stairs.

The Moment of Truth

It was nerve wracking going down those stairs, I felt so self-conscious but as soon as I walked into the front room there was not even a mention of me being naked, I just was! My hostess asked me to start a fire in her wood burner; no matter how happy I had been with my body, bending over to do that would have been a test for anyone I think, especially as it took me a while to get her fire going (so to speak!).

I topped up her wine and poured myself some more too, she then asked me to sit on the sofa beside her and we chatted about how I was feeling about it again. It was clear that at least some part of me was enjoying being naked as there really is no way to hide that when you’re left with everything hanging out. It became easy. We were watching a bit of TV, just having a laugh and drinking some wine, me naked, her fully clothed. It got to the point where it just wasn’t really a thing anymore.

I cooked the steaks, making sure to be careful that I didn’t get fat on my exposed skin and most importantly didn’t burn my very own exposed piece of meat. We had a nice dinner and again it was as if I wasn’t even naked at all! Strange how you acclimatise to situations so quickly. She was an easy companion and the fact that it wasn’t referred to much obviously helped.

The Massage

With dinner done, the wine flowing, and the fire in full blaze, we sat and let the food go down for a while whilst chatting about various things. A little bit about the situation obviously, some about her previous experiences from Craigslist and some just general getting to know you chat about life and work. After a while she suggested that she would like a full body massage.

It turned out that she was well equipped for this, having her very own massage table. I was instructed to go and fetch it so I took my naked body back up the stairs (the cat was still hiding in the bedroom possibly scarred by what she had seen earlier), to fetch the table from the spare room. Back in the living room I moved the dining table out of the way and set the massage table up ready.

My host came back into the room now wearing a robe and climbed onto the table before taking the robe off to leave us as just two naked people in a front room. She lay on her front and using oil that she had supplied I started working her body starting with her feet and ensuring that I spent sufficient time on every area as I went from foot to calf to bum and all the way to the shoulders and neck. It was not a short massage and I probably spent about half an hour with her that way, wine was topped up throughout, before she rolled onto her back and once again I proceeded to work her body from the bottom up.

I was intimate but not too intimate as I worked her inner thighs – limits hadn’t been discussed – so I was just testing and reacting to her. From her thighs I moved over her hips and up the side of her body again to her shoulders and neck. I then began to work her breasts. I was enjoying the feeling of her oiled nipples slipping under my hands as I caressed her entire upper body, again watching and reacting to her and letting her stay in control of how far I went. The response was very encouraging and I was becoming more and more aroused. I had positioned myself at the head of the table and was having to lean over her to massage her breasts and the side of her torso, this way my penis was very much in her eyesight.

I then moved back down her body so I was working her inner thighs again, this time I pushed the limits a little more until I was solely focused on massaging her outer lips. My hands were absolutely covered in the oil I was using, but it was clear she was enjoying it just as much as me as I slipped my fingers inside her, gently running them from the front of her pussy before fully exposing her wetness. I could hear her breath catch as I ran my finger back up to her clitoris and circled it, softly flicking across it at the end of each circular motion.

Whilst I continued to explore and excite her with one hand I used the other to gently massage her breasts until she came hard with my fingers inside her, feeling every pulse of her body. I think with the build up of the massage the whole thing lasted around an hour, which really helped build the tension in her. Without a word and almost as soon as the convulsions began to subside, she rolled onto her side and took my penis into her mouth.

This is what I had been hoping for and she certainly didn’t disappoint. She was extremely good at her craft and using her tongue and lips to full effect, had me pumping the contents of my balls into her mouth in no time at all. As my penis began to soften she didn’t stop but just kept on sucking me hard, she clearly enjoyed what she was doing and so did I – after a while I began to get semi-erect once more. This surprised me, and even more surprising was that she managed to make me come again so quickly after the first orgasm! It really was one of the absolute best blowjob experiences of my life.

The Short Goodbye

After the massage and both of our huge orgasms we had a short chat about how much we had enjoyed it before I went back upstairs to get back into my clothes and wash the oil from my hands. When I came back down she was back in her robe. We discussed doing it again which I was happily open to; she even told me that she sometimes had friends over and that a naked butler would be most welcome at such an event.

I said I’d think about that as it may be a step too far for me, but the idea drove me crazy at the same time. I had told her about my body hang-ups previously and she reassured me as we said our goodbyes. I left her and was buzzing as I walked back to my car. It had been a very liberating experience – obviously the happy ending was a great treat, but it was the whole experience of being naked and being ok with it that stayed with me.

I never saw her again. We did talk from time to time, but unfortunately the bigger group session never materialised, and I still believe it may have been one step too far. It might have ultimately led me to a full blown life as a stripper!

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2 Comments

  1. deelightdee
    23rd November 2019 / 10:14 am

    Unusual with a very erotic element 👍

  2. Nick
    24th November 2019 / 7:49 pm

    I would love to say “you bastard” but will just say you lucky sod. This is one of all time favourite fantasies, particularly the group thing. Not been able to engineer it yet but would love to one day.
    Well written and very erotic. Thanks!

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Names and some minor details have been changed to protect the innocent. And sometimes the guilty.
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