Saturday, August 30, 2008

Let's go commercial.

Of course sometimes it actually works. A few months ago there was a young woman on the same site (same as Miss Runaround, as below). She said she was interested in roleplay, being dominated and in hotel rooms. I can well understand this last one, I love hotel room sex.

I lived in Singapore for a while when I was married and one day I accidentally let slip something about how the rooms in the Four Seasons were very cold, and it was hard to adjust the air-con. My wife gave me a very strange look. But I digress.... Where were we? Oh yes. I sent her a message:
Nice hotel room, as you suggest. But we play it like this: I'm a hotel guest, I come back to my room and find you (stranger? hotel worker? doesn't matter) rifling through my papers. I'm furious, my first thought is to call the cops but then I decide that what you really need is to be taught a lesson. You resist; I keep going.

At first I have to tie you and spank you (hands, belt, anything else i can find), maybe also clamps and pegs, to see if a little pain makes you smarter, then when I've calmed you down a bit I start to explore your body. You say you'll do anything ... "anything?", I ask?

On it goes. You're mistreated, and ideally at one point I have you in the bathroom for some watersports fun (fun for me, that is). You can also look forward to a great deal of anal attention.
Just an idea. And despite all this I'm actually pretty normal. This would be fun as a one-off or - better yet - whenever we felt like it. I have other ideas too...

Let me know. I expect you get hundreds of messages.
Now, just to set the record straight, I'm not quite as into rough sex as this message makes out. But in her profile she'd seemed very keen on it, so I figured I'd skew the message a bit. She liked it. And she did, in fact, get hundreds of messages. We chatted back and forth a bit on msn over the intervening four months, she had a few adventures, some satisfactory, most not. We spoke on the phone a couple of times - she seemed refreshingly normal. I figured there was a decent chance we'd meet up sometime.

Last week we got chatting again on msn, and she said she had an idea and wanted to meet me for a drink to discuss it. We couldn't meet for a drink that week (my schedule - you'll be surprised to hear that I have a busy professional life), but she told me her idea anyway on the phone. She's a graduate student. No money. She likes roleplay. She wanted to know whether I thought it would a good idea for her to charge for sex.

For a start, I don't have any moral or political qualms about this. I did point out to her, though, that if she were proposing this as a business plan then it sounded a bit foolish. However, if she were just figuring on a way to monetize her hobby, it might work.

I guess that like most guys I've paid for sex a couple of times (not including getting married, that's the most expensive sex I ever had and it wasn't that great). I didn't like it. Once was in Germany, once in Taiwan. Both times it was with women who looked bored and a little ashamed (or was that me?). I know some guys get off on the idea of having sex with someone who'd really rather be doing something else, but for me it was a turn-off. It didn't surprise me. But I felt I should try.

But would it be different with someone who you knew was really up for it? If there was ever a situation where paying for it wouldn't be an issue for me, this would be exactly it. I told her all this as I was thinking out loud. Then I realised that having a commercial transaction would also give it a nice and nasty roleplay element. I'd be the customer, and I reminded her that the customer's always right.

So we met for lunch. She seemed very nervous, and she confessed later that she very nearly chickened out at the last minute. But she didn't. She was lovely. Articulate, nervous, attractive. We discussed the commercial terms over a light lunch, and I was very business-like about it. I could tell she liked that, being a commodity.

Then back to my place. As we walked in the door of my apartment I handed her some cash, and to her credit, she blushed. I didn't tie her up but I did play with her a lot, and I did something to her she'd never had done before and which she really liked. It was extremely good fun, but I still feel a little uneasy about the whole thing. Had this been her agenda all along? I suspect not. But if it was, she went to a lot of trouble to set it up. No, I think it was all exactly as it seemed.

Afterwards we had dinner. She offered to pay, which was nice. She did, after all, have money.

Thursday, August 28, 2008

The Runaround.

About a month ago I stumbled on a profile on a BDSM-ish site, from a young woman who sounded interesting. So I sent her this...
Nice profile. You like the idea of being blindfolded and having your pussy and ass probed and explored by one or more imaginative older men? Objects, food..?

I like all this, and more. Happy to chat.. also to meet up. Otherwise, I'm pretty normal. Mid40s, [location]. Interested?
I sent this off into the ether, figuring there's about a 15% chance of getting a response. To my surprise and delight, within a couple of hours I got this:
Hi, I thought your profile interesting too. It seems we're in synch on a number of levels not least of which was the scenario you opened your email with. Bingo, that's one of my favourites. Blindfolded and restrained, stretched wide open for any of the older men to intefere with. I am genuinely curious, with a wild imagination and love erotic chat and dirty talk. These are tentative steps i'm taking and will need plenty of encouragement and guidance. I'm not for the impatient.
Great. She can spell, and she can write coherent sentences (I'd quibble about the 'h' in synch, but that's just me being picky). So I went back with this:
Nice to hear back, and nice to get a positive response. That general scenario is a real favorite and I'm pleased it struck a chord.

The good news if that I'm not impatient, and so long as I feel like we have similar-ish ideas I'm very happy to chat or talk for as long as is takes for us both to get comfortable with each other. (More so you with me, given the situation..)

I love the idea of guiding, teaching, persuading someone like you to realise their fantasies. It can be a lot of fun.

Any other things in particular you like? I did a thing not long ago, a woman I'd chatted with and spoken to on the phone for a few weeks. She was comfortable with me. She was staying in a hotel here in [ ] (visiting). I met her in the bar of her hotel. We didn't speak, just looked at each other. Then I handed her a blindfold, she gave me a key to her room. She went upstairs, put on the blindfold.. I followed a few minutes later.

I love that sort of setup
It's very hard to know what to write. I don't want to seem too pushy, but then again, I do want to advance the agenda a bit. And given the nature of the site, there's not much point sending a nice message about the weather or politics. She came back with:
Another gem... the hotel scenaio, not a word said, it struck a chord that caught in my throat before it shot to my crotch. I'm turned on and terrified in equal propotions, and I like the way that sit's. A favourite fantasy of mine is Dr/Patient. After some mild sedation, I'm restrained, inspected, and tested on.
Bullseye! (Apart from sit's) She responded to the hotel thing, and she's mentioned a real favorite of mine. The Doctor is IN! As keen readers will know, I have done this a bit lately. Here, here and here. Bizarrely enough, if you google doctor/patient sex roleplay you end up on this blog. I sent her my email address (msn too) and this:
I did a doctor/patient thing recently, with someone from [this site]. A respectable married woman (which I loved!). She came to my place one lunchtime, she made sure she called me 'doctor' the while time. I examined her, undressed her, examined her more.. very thoroughly. Took some pictures. I suggested to her that it would be even more fun (and more thorough) if there was another doctor with me as well. She LOVED that idea.. How are you doing? Fancy chatting? I'm very curious to talk to you, it sounds as though we have similar ideas
Then this:
Hi, I like the sound of one of those appointments. Though,I seem to have gone all coy. Quite uncharacteristic. We should chat soon, I think we ARE on a similar wavelength...
Where did coy come from? She's sent me a couple of pictures of her pussy (or, quite possibly someone else's), she's described in a bit of detail some fairly interesting fantasies. All we're doing is exchanging emails every couple of days. That's fine, maybe she want to slow things down (but why? either you want to do it or you don't, surely. See Rule #3).

But I appreciate she probably wants to do this slowly, she's waging some inner battle. The good angel on one shoulder telling her not to, the bad angel on the other telling to meet the weird middle-aged pervert who seems to know which buttons to push. I do notice that she logs into this website just about every day, so it's not like she's completely lost interest.

What troubled me was that she says "We should chat soon". By this stage we'd been emailing for about 2 weeks. She had my contact details. My email, my msn, my phone number. She had pictures of me, and not my wedding tackle either, I mean my face. Given how interested she'd been in what I'd been emailing her (" struck a chord that caught in my throat before it shot to my crotch...") I would have expected some attempt to engage in actual conversation. Not phone, I can understand. But msn, or yahoo or something.

What can "We should chat soon" mean, apart from "I'm not going to chat now"? I left her for a couple of days, then messaged her again on the site, saying that she had all my contact details and that if she wanted to chat I was happy to as well.

And then... nothing. I couldn't help myself. After a few more days I messaged her again (which I know I shouldn't) and said something like "you've gone very quiet... still interested in chatting?", to which I predictably got no response. I tell myself to move on, to forget it, but then I found myself messaging her again a couple of days ago (about a month after our first emails) with "What happened? You said you were interested in chatting, but I guess you're not", which sounds, I know, petulant and desperate.

Of course, it was never going to happen. At some level I realised this very early on. In my experience (and despite what you think, I really don't do this very much) people who want to establish contact usually do, and a useful rule of thumb is that if someone hasn't made a serious effort to contact or be contacted within two weeks - even if it's just a phone call - then the chances are it's never going to happen.

This happens quite often. I think it's rude. I would have settled for one of the following, just for closure:

1) I'm sorry, I'm just not ready for this right now
2) I've met someone
3) I'm actually a 50yo fat man and I've been getting off on these email exchanges

I suspect 3) is the right one here. But I'm not a woman, and while I think I have a much better idea of how women think than I used to, I maybe have completely misjudged this.

Wednesday, August 27, 2008

Booty call!

I've been a bit out of sorts this week, for various reasons. 'Joan' came over on Monday night but even that didn't cheer me up. She was pleased though when I told her that the video I'd posted on xtube of me fisting her had gotten almost 30,000 views. She's an exhibitionist, and quite likes being talked into doing stuff. The other thing I like about her is that when fully-clothed she's quite a senior executive with a large and very well-known consumer goods multinational. We're both so very respectable.

But then today I got not one but two - yes count'em, two! - text messages from women asking about my availability for tomorrow. First one was Dee, who as I'm sure you recall is keen on being spanked and fucked by two men, but she just wanted to see if I was around for a bit of one-on-one.

And then at lunchtime, I got a text from Sarah!

Hello, any chance of slipping away from work tomorrow? I have an 11am meeting near your place and could meet you afterwards.

Sadly, I had to decline both. But it did make my day. I love the thought that these two women (one of them, as you may recall, is married) were having lustful thoughts about me.

Saturday, August 16, 2008


I was chatting online again last night with Dee, who is ,as I'm sure you'll recall, a young woman (late20s) who responded to a listing I placed in a Craigslist equivalent where I was looking for someone who wanted to be spanked.

She' s started opening up to me a lot more since we played that one time, and I suspect part of it is that we're fellow language pedants. I love that. She's the sort of person who's troubled by the use of the word 'enormity' to refer to size. As I am.

She told me she'd love to be spanked and fucked by 2 or 3 guys. No face-slapping, no hair-pulling. All done reasonably nicely. I will organize this when I get back....

Friday, August 15, 2008


Interesting thing in the NYT about how advertisers are very keen on sites that appeal to women (based on the premise that women buy more stuff than men).

It says, among other things, "Although men are heavy users of the Web, they tend not to visit sites explicitly aimed at them." Except for all those 5 trillion porn sites, of course. D'oh!

Cylindric Pleasure

My friend Becky (not her real name) sends me from time to time the highlights of the messages she gets sent on an adult personals site. She knows that I'm exquisitely sensitive to language, and that I love prurient detail. She got this one recently, it's a classic of the genre.

hello precious
When I dreamt of you, I lay down on the bed and you crawled over me on your hands and knees...I was below you and your tits bounced over my face as you took your position...your chichi just dripping on my face...the lips slightly parted and you lowered it a little so i could begin licking and softly slurping the tender pink meat..It wet my cheeks and my toungue gently paintbrushed your insides...I parted your lips with my hands and used chin, nose and tongue to plasure you, while slowly but surely taking in your flavour and my lips went in your chichi like a painter soaking his brush on his pallette...over and over again, I softly bit your pussy inside with my lips and gently brushing my teeth onto it to stimulate you, which you seem to immensely cock was fully aroused, its head taking the full tension and red crimson in colour.

Then you shifted and took your position in the driving seat and I felt sliding into your sanctuary, the cylindric pleasure almost unbearable and you rode me and shook me and we both wriggled in joy and my tongue kissed yours while you rotated and jumped on me as I thrusted and felt like almost touching your ovaries...

a sweet kiss from me and I look forward to your comunication, my precious lady

There are so many things about this I love. Which things, I can hear you cry. How about " toungue gently paintbrushed your insides", or "like a painter soaking his brush on his pallette".

Then, in the next paragraph there's a passage that has "sliding into your sanctuary" and "cylindric pleasure". It's probably mean of me to quote it all here but I couldn't resist sharing. I do like that he's gone to such a lot of trouble and I wish him well.

Does anyone else have any they can share?

Monday, August 11, 2008

Naked Yoga

I was reading something on another blog which mentioned naked yoga, and I just had to leave a comment. And because I don't have much else to write about (been quiet for a week, had a cold) I figured I'd just do a blog post about it too.

Yoga was one of those things that'd been on my list for years, and, like a lot of things on that list, it was destined to stay there. Then I heard about Naked Yoga. Now, before you get all excited, I have to point out that, at least in the city I live in, naked yoga's an all-male thing. And while it's very open to all sexual orientation, in practice it's only gay guys. I think straight men would find it a bit confronting. Naked men in a room. Cocks. Asses. That sort of thing.

I wanted to do it precisely because it was a bit confronting. I've always been very self-conscious about being naked, and I thought (correctly, as it turned out) that this would be a good way to get over it.

I emailed the guy who runs it, then spoke to him on the phone. He sounded pleasant and not at all creepy, and he said that it didn't matter that I'd never done yoga, there were all sorts of people there. I didn't even need a mat! He always brought a few spares.

So one Sunday evening I showed up. It's a very nondescript building, on a major road, opposite a gas station. It's used sometimes as a theater rehearsal space. I went over to the gas station to buy a bottle of water and watched guys going in, they looked pretty normal. And importantly, they weren't all 25yo gym-bunnies. I gathered all my reserves of courage and walked over the road, then in the door and up the stairs.

In the room were a dozen or so men, all still clothed. At the front of the room was Steve, the guy who runs it. I introduced myself to Steve, he gave me a mat and I found a space. Then I sat and waited. Eventually Steve closed the door, and that, I realised, was the signal for everyone to get undressed and start having sex. No, I'm kidding about the having sex. We all got undressed.

Like a lot of people (I've checked) I have dreams about being naked in places where I'm not supposed to be naked. At work. Going through customs and immigration at LAX. At the supermarket. That sort of thing. And I found that no matter how many times I went to naked yoga, I still had this delicious frisson of doubt as I started taking my clothes off. I'd have to remind myself that everyone else in the room was also taking their clothes off, and that it was ok.

Then, naked, we'd stand on our mats. The front of the room was a floor-to-ceiling mirror running nearly the whole length of the room. So you'd see yourself. You'd also see the other guys, and without making it too obvious you'd check everyone out. I assume we were all doing this, not just me. I may be wrong.

Then the yoga started. I liked it, as it turned out. It was physically quite challenging, lots of balance and strength work. Once in a while someone would get a hardon, usually someone new. We'd always pretend not to notice. I was too busy being serene and blissful, but if I did notice someone enjoying the class too much I couldn't help feeling just a little bit smug. Having a hardon in naked yoga would be a real bitch.. there's nowhere to hide, and once you were aware of it you'd never get rid of it. Never happened to me (except once or twice in the meditation bit, but the lights were out).

Then, after about half an hour, Steve said it was time for 'partner work', and we each had to find a partner.

When you're doing naked yoga with someone, you get a bit fussy. You don't want the fat hairy guy. You don't want the creepy guy either. I worked out pretty quickly that there's a lot of strategizing around where you put your mat. You especially don't want someone who sweats a lot. Not so much because it's icky (which it is) but more because you fall off them.

After partner work, more yoga. Then meditation.

I found the best thing about going to naked yoga was that it meant I could tell people that I went to naked yoga. They always looked at me a little differently after that, especially women. And that's the way I like it.

Friday, August 8, 2008

Sugasm 143

Sugasm #143

HNT courtesy of No need to be coy.

The best of this week’s blogs by the bloggers who blog them. Highlighting the top 3 posts as chosen by Sugasm participants. Want in Sugasm #144? Submit a link to your best post of the week using this form. Participants, repost the link list within a week and you’re all set.

This Week’s Picks
Anti-Porn Protest Gets Weird
“People get very excited about their causes and lack the sense to see if the information backs them up. ”

The Come Shot
“You don’t see their bodies going blotchily red and hear them howling like a banshee.”

Third Time’s a Charm
“If I lift my kilt on Bourbon Street I’m much more likely to get arrested than if Elizabeth takes off her top.”

Mr. Sugasm Himself
Sugar Bank

Editor’s Choice
In My Office

More Sugasm
Join the Sugasm

See also: Fleshbot’s Sex Blog Roundup each Tuesday and Friday.

(Sugasm participants should re-post all the links above within a week. The following links may be excluded as long as you include all the above links.)

Thoughts on Sex and Relationships
The game is afoot!!
I Look Good Naked
It is a Journey that Defies Labels
My Doppelgänger Wrote About Me!
My First Peeping Tom
Perfect vs Good
Why I hate threesomes
You Say Po-tay-to, I Say Po-tah-to

Sex & Politics
Musings on Masculinity: Gabe
Prostitution: To Legalize Or Not?

NSFW Pics, Videos & Audio
Blonde whore sex video with blowjob
Cam Lover is addicted to CamWithHer clips
Femdom Mz Berlin Double Fists Audrey Hollander’s Ass In Lesbian Bondage Scene On Chanta’s Bitches
First post, first HNT!
Fuck me like your bitch boy (pic)
Girls and computers
Half-Nekkid with a New Toy
Jodie Marsh in Hot Party Dress Spilling Out her Boobs
Ms. Elle with Lash
Phone Sex Grandma
Satine Phoenix Forced To Cum On Fucking Machines
Tits for Troops
Where are the women?
X Marks The Spot

Sex Advice
Study The Master: How to Flirt, The Dean Martin Way
Thai green curry is the way to a spicy sex life

Sex News, Reviews & Interviews
20 Questions With Tina Tyler
Andrew Blake Thinks He’s Stan Brakhage
Interview with John of Leather Thorn Paddles
Perpetuating Stupid Stereotypes
Review: The Clover Plug
Sextoy Review! The GIGI “Pleasure Object” by LELO
Win A Vollers Corset From Mio Destino Lingerie

Erotic Writing and Experiences
After tapas
Autobiography of a Masturbator: Porn O’Graphicus, Part 3
Can you keep quiet?
Contrast (a love song)
Fiction: Hipster Girl
Hard times, hard-ons, hookers, & strippers
I need to fuck Amanda.
A Little Tingle
Mister McIntyre’s Secret - Part One
Mrs. Kink Gets Kinky Email From D
No reservations. part 6
“Once there was a boy and he was beautiful… “
One Track Mind
She danced into my fairytale-Part Three
She Kissed Me
Slut in the park
Try not to scream…
View From The Balcony

Sex Humor
Taking the Piss Out of the Internet, One Golden Shower at a Time

BDSM & Fetish
Amber’s Wedding Day Confession (Part Three/Continued)
Catalina loves FetLife
Famed Dom Sgt. Major Brings His Slutty Friends To Backdoor Bondage
Fine Art 101
The locks are broken
A Master And Femdom Cane A Slut Who Kneels On Frozen Peas, While In Bondage
Prelude in E (for Embarrassment)
r’s naughty thoughts on a scene with his Mistress and Ms. Nikki Nefarious
Strap On Play Is Not Just A Fetish, It’s Fun!
Sub night
The Tea Party
A virgin does Thunder, part II
Weekend, part two: dancing
A Wicked Tease

Monday, August 4, 2008

A Good Seeing-To

"Why so quiet?", I can almost hear you ask. I have a bit of a cold so I've had to stop the fucking (and the spanking and all the other stuff) for a few days. Normal service will be resumed later this week.

I read a couple of novels (one good, one bad), played a lot of music and caught up with a few friends. My best friend, the woman I'm falling in love with, took me out for a lovely breakfast on Saturday. We've known each other for about a year and a half, and in that time we've slowly gotten closer and closer. We see each other a couple of times a week and the way I can tell that I really like her is that I can spend hours with her without starting to feel antsy - with most other people after about an hour I start wishing I were somewhere else.

When we first met, I was in a relationship with a guy (the only time I've ever been in a relationship with another man), and one of the really neat things about that is that women would really relax around me. They'd tell me things they'd never tell a straight man. I learned a lot, and I started realising that women were more like men than I'd thought. Who knew?

My other insight came, strangely enough, from the world of man-to-man sex. I categorise myself as 'versatile', meaning that when it comes to fucking, sometimes I like give, sometimes I like to take. And if you're interested in what drives that, a lot of it depends on what the other guy's like. If he's more than a few years younger than me, I'm a top. If he's my age or older, and especially if he's very masculine, I'm a bottom.

And if I'm being fucked by a masculine older guy, it turns out that I really like the feeling that he's in charge, that he knows what he's doing. I love that idea that as he looks at me (and right now as I'm writing this, I'm thinking of someone in particular) no matter what he's saying or doing, what he's really thinking is that he wants to stuck his cock in me. And I absolutely love that feeling of almost being objectified, of being just the object of someone's lust.

Then I had my epiphany: what if women feel this? Yes, I know that sometimes they like tender, gentle love-making, but what if sometimes - or maybe most of the time - they really just want to be fucked.

Years ago, when I lived in London there was a quasi-reality TV show where they put cameras into a house and watched a couple for a week. Two 'relationship experts' gave commentary - to the viewing audience, not to the couple. At one point the couple had had a minor fight and were in the middle of making up. The male relationship expert said that the woman probably wanted to be made love to. The female expert interjected - and these are her exact words -
No, she wants to be taken upstairs and given a good seeing-to.

Saturday, August 2, 2008


Many years ago a woman I was going out with confessed to me that she didn't think she'd ever be able to suck cock. This was at a point where our relationship was moving from the just-dating phase to being something a bit more serious, and I was quite impressed with her forthrightness on this. She wanted to let me know, just in case it was a deal-breaker. It wasn't, and she eventually did overcome her reluctance.

She said the reason she didn't think she could was that at some level she couldn't get over the idea that it was 'unladylike'. All I could say to that was "But that's the whole point of it..."

Friday, August 1, 2008

Search me....

I'm delighted to report that someone found this blog by typing into google:
doctor/patient sex role play