OTK4

You may recall I'd put a listing in the local version of Craigslist , and had gotten a couple of replies. Two dead ends, one live lead. I'll call her Dee. We messaged back and forth, spoke on the phone. She'd never been spanked; she'd never hooked up with someone from online. Which I kind of liked. We arranged to meet up for a drink last night near where I live.

I was at the bar a little before 8. It's quite a nice grown-up place, piano music, cocktails and whatnot. I was wearing a suit. I look good in a suit, also, I thought, she was clearly very interested in the idea of being spanked by an older man (she's 29, I'm somewhere in my 40s) so I thought that a suit would, well, suit. I fended off the waitresses (slow Tuesday night) and waited for her.

She showed up. Looking quite presentable, but nervous. We chatted a bit, I ordered drinks. She apologised for talking too much and said she was very nervous, which I said was understandable. As I pointed out, she was meeting a strange man who liked to spank younger women. She asked me if I was an ax-murderer, and I assured her that I wasn't.. but couldn't help adding that that was exactly what a real ax-murderer would say.

We chatted a bit more. She relaxed. Then, as we finished our second round of drinks (mocktail for me, I'm a real lightweight these days) she leaned forward..

"What now?", she asked

"Well, now that you're relaxed and comfortable with me, I think next time we meet I should spank you".

She looked a bit perplexed "What about right now..? You live near here, don't you?"

I wasn't bargaining on this. My apartment was in a real state. But a half-second's worth of analysis convinced me. She was up for it right there and then. If I let her go, she might go off the idea. So I took her back to my place. I asked her to sit down for a couple of minutes while I made a perfunctory effort to tidy up.

"What do we do now", she asked.

"Whatever we like", I answered, "but given how we met, we should start by me spanking you."

She seemed very agreeable to that idea. I sat down on the couch, got her across my knee, raised her skirt and gave her a few exploratory slaps on the asscheeks. She liked it, so I hiked her panties up a bit to bare her cheeks and gave her a few more. Then, of course, gently running my finger tips over her thighs and butt, spanking her again. She raised her butt, spread her legs a little. She was, I soon found out, nice and wet.

Later, in the bedroom.. she's naked, lying facedown on the bed. I'm sitting next to her, with one hand spanking her bare butt, with the other teasing her pussy. She came. She asked to be spanking again. How could I refuse?

Afterwards, we lay on the bed talking. She's surprisingly literary and we discussed our favorite words. I told her mine was 'feckless'. We nearly fell asleep, then, about midnight I walked her downstairs and got her a cab. Partly because I'm such a considerate host, but also because I was very much in the mood for a post-coital snack. She wants to do it again.

Perfect vs Good

You may recall that this time last week I was due to meet a woman in the bar of a nice hotel. The deal was that we weren't going to say anything. No drink, no chit-chat, no getting to know one another. We were just going to look at each other briefly, then I was going to give her a blindfold, she was going to give me a roomkey. She was to go upstairs, get into whatever state of dress or undress she liked, put on the blindfold and I would come up a few minutes later. I know you've been losing sleep all week wondering how it turned out.

It was strangely unfulfilling. That's the short answer. It didn't go completely to plan, for a start. I wandered around the bar looking for her, trying not to look too much like a weirdo (and fairly conscious of the fact that I had a bag with me that had rope, cuffs, blindfold, toys, condoms, lube - everything I could think of except wet celery and eggbeaters). I didn't see her sitting down, then, as I retraced my steps, I spotted an attractive blonde woman standing at the bar grinning at me. I stopped, kissed her, we had a bit of a laugh. Then I gave her the blindfold, she gave me the room card and whispered the room number in my ear. She walked off to the elevators and I watched her from behind. Nice....

I gave her a few minutes and went up to her room. I did have a bit of a panic trying to remember the room number she'd whispered to me, and I wasn't 100% sure that in all the excitement I'd nailed it. I knew which floor it was on so I figured worst case I could just slide my card into every lock on the floor until I found the right door. Two problems here:

1) hotel security - and what about the bag full of ropes and cuffs?
2) it would have been a crushingly obvious metaphor

I found the room easily. I walked in. She was sitting on the edge of the bed. Wearing a sheer black negliee and stockings. Blindfolded. I got her to stand up and I played with her a little and kissed her. She started playing with my nipples. I told her not to. She kept doing it, so I asked her nicely to bend over and I helped her hands find the edge of the desk. I raised her negligee and spanked her. Not too hard. Played with her some more, spanked her again. We were talking all the time; I was using the low, calm voice I use in these situations. And then, I started losing interest.

I took off her blindfold, we kissed. We lay on the bed for half an hour or so, chatting. She was quite funny, and very attractive and married. And I was starting to panic.

You see, this situation should have been super-charged with unbearable erotic tension; it had all the right ingredients for me. But it just didn't feel quite right. Partly, I think, because I found it hard to get a really solid sense for what turned her on. Everything, it appeared. Top, bottom, domme, sub. Kink. Bondage. Leather. And she'd done it all. I like doing this sort of thing with people who've been imagining it for years but have not - until that moment - tried it; I love it when they lose themselves in the scene. She didn't (although that did happen a bit later on, which cheered me up a bit).

We played a bit more, and then we lay in bed again, talking for an hour or so, cuddling, drifting off to sleep. Then another play, then more lying together talking.

I have a strong homing instinct; I sleep much better if I'm by myself and I hate being tired the next day. I figured she wanted me to sleep there, but I also figured that as we were unlikely to see each other again I had nothing to lose. I told her I had to go home to sleep. I got out of bed, got dressed.. she was very quiet. I kissed her and left.

I walked home feeling strangely disconsolate. What had happened? It was a great setup. She was funny, hot and up for just about anything, and she liked me. Was there something wrong with me? This was as close to a perfect scenario as I could imagine, but I was left cold by it. Was I spending too much time chasing the perfect sexual encounter? (The perfect is the enemy of the good, that sort of thing.) What was wrong with the playmates I already had? Should I find another hobby?

I woke up the next morning, still tired and vaguely unsettled. For the first time ever I didn't even send a nice thank-you email or text. I felt bad about that too.

Sugasm #141

July 21st, 2008 by Vixen | Updated: July 21st, 2008

Tara Tainton courtesy of Porn Saints.

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 #142? 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
Comedy vs. Tragedy
“Are you on your period? What? Did he just say…”

Ian, or, Sometimes Sex is Hilarious
“In short, it isn’t sex blogger sex.”

A Wish
“I wish that you could know the indescribable pleasure of being enfolded in your warm, gentle wetness.”

Mr. Sugasm Himself
Sugar Bank

Editor’s Choice
Road Rage

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
Forgetting
How Do You Flirt With Milk?
The Hunt
I Don’t Usually Date, but…
I have huge tits.
Men on Pointe
My Femme Cock
Nibbles and Bits: Vegetarian? Really? Doh!
Present and first love making

Sex Advice
How to Make Her Want Anal Sex
Play Safe
The Power of Suggestion- And How It Helps You Meet Women

NSFW Pics, Videos & Audio
Gisele Bundchen Topless and Nipple Slip Pictures
HNT - Purple Lace Part Two
Lady Sascha Does HHNT
Marta - Professional
Once upon a time HNT
Pornsaint Tara Tainton
A rose by any other name would smell as sweet -HNT
Sam Bound

Sex Humor
It did not work
When your mother has more sex than you do…

Erotic Writing and Experiences
Can’t Get Enough
Fiction - The Wrong Smith Girl
Getting to fuck the neighbor 15
Harder…
In any language,…
Le Cadeaux
Nine: of nasty names
Oh Honey, Make Yourself Cum for Me
The Parking Garage
Pointless
The Ride.
Rub a Dub Dub
The Second Time Around
Slow.Soft.Hot.Perfect
Spin the bottle-the conclusion
Tits~n~Teets 2
TNT - Part 2
The Wanting
Writhe

Sex News, Reviews & Interviews
Can A Film Prostitute In 1930’s Shanghai Fare Any Better Than One Of The 100,000 Prostitutes Working The Streets In The City?
Donate To Satine Phoenix’s Tantric Exploration
Escort X: Find great escorts
Spanking erotica interview with Alison Tyler
The value of erotic blogging
Wanted: Your Orgasms Caught on Tape

BDSM & Fetish
Auction of a Slave
Changing Cravings For Pain: A Survey
A Beautifully Cruel Predicament Bondage Scene
Cuntwriting
Fitting Punishment
The house in Vienna
July MVK: Play piercing
Leather Retreat 2008 – The Toll Booth
Mz Berlin Gets The Bastinado And Rack Torture On Hogtied
Necessary Roughness
Routine Maintenance, pt. 2
A Scene in Three Parts … (part III)
Taken and Collared as a Sex Slave while her husband sleeps
Telegraph
Trying on new shoes, Friday night edition

OTK3

I chatted with responder number2 on msn last night, she seems ok. I'm rating her about a 30% chance to end up in the situation pictured to your right ---->

Then today I got this from someone else...

i would like a spanking but don't trust some guys.

As you can imagine, I was all over that like a cheap suit. Let's see....

OTK2

Those of you with long memories will recall the ad I put in the local equivalent of Craigslist, where I wrote:

Ever fantasised about being over a guy's knee, skirt up, being spanked? Not so hard that it really hurts, just hard enough for it to be fun?
Handsome and basically normal single guy in mid40s, Eastern suburbs, looking for adventurous and naughty younger woman for fun. Spanking, maybe roleplay. I'm literate, imaginative. Limits very much respected.

So far, 2 replies. First one was a week ago. She wrote...

Fantasised and had it done to me, not nearly enough. 24 year old girl in eastern suburbs too

Which I thought was a great start. So I emailed her.. and nothing. In my limited experience with this sort of stuff, women in their 20s are much less likely to follow through than women in their 30s or 40s. I'm starting to form a hypothesis about this, which I'll elaborate on at some point.

Then yesterday, I got this....

Hey, saw your msg on [craigslist]. I'm a 29yo inner city gal, just looking to meet new &
fun people. I am about 5'7", curvy [some detail here I'll omit]. I must admit I have always wondered what it would be like to be spanked but too scared to find out! Would like to hear more about you and possibly meet so email me or msg me if you're interested :)

This is a bit more promising. And I do rather like the bit about always wondered and too scared to find out. I emailed her. Let's see....

Being Prepared.

I visited Judith on Thursday night. We went out for dinner (which is unusual), then back to her place. I've always had in the back of my mind that anal sex is a possibility with her. She'd never done it before, but quite liked having a finger in there when she was nicely aroused (and sometimes requested it), and I'd made no secret all along of the fact that it was on my agenda.

So Thursday night, we had sex. Vanilla, but as always with Judith, very satisfying. Afterwards we were lying in her bed, cuddling, she facing away, me behind her. I love that. I find women's backs very erotic (actually, I find pretty much everything about women erotic, now that I think about it.)

"Kiss my back", she said, and I did. I started kissing her on her upper back, her shoulder blades. She was still pretty excited from the fucking, and I noticed that kissing her back seemed to really turn her on. I continued, naturally, and I started getting more and more aroused. I moved down, kissing and teasing her flanks and lower back... same effect, but more. By this stage, as you can probably guess, I was starting to form a plan.

I ran my tongue down between her buttocks and she made a sound that I hadn't heard before from her; lower, more intense. I kept going.. I rimmed her (which we'd already established she loves) and played with her pussy, and then she said:

"I've never felt like this before..."

I stopped what I was doing for a moment, put my head next to hers and whispered in her ear "I'd really like to fuck you there...". She said "I've never done that before..?", which of course I knew, but said it in a way that suggested that she thought this condition of never-having-doneness was looking a bit shaky.

I thought for a second, sat up and asked her "do you have any lube?". She shook her head.

I did. In my jacket (as I've recreated in the pic above, for dramatic effect). And for a split-second I was torn. What sort of message did it send, that I had secretly brought a tube of lube with me? Would she be angry or upset? But if I didn't get that lube right then and there, I might never have an opportunity this good.. if I chickened out now, would I always remember this as The One That Got Away?

I said "hang on a sec.." and went to rummage around on the floor, looking for my coat. I got the tube of lube out and went back to the bed. Then, while I was playing with her pussy with one hand, I somehow managed (and it's amazing what you can do when you really have to) to open the tube of lube, realise the safety seal was still on it, unscrew the cap, remove the seal and then screw the cap back on all with one hand. And in near-darkness. She knew I was up to something. "what have you got there?". I squeezed some lube on my finger, "this might be a bit cold", I said.

So I fucked her in the ass. I was, as always, very gentle (I didn't remind her, although I could have, that in my former life as a gay man I've been fucked many many times, so I do know what I'm doing).

Afterwards she asked me about the lube. Had I just brought it this time, or did I have it in my jacket all the other times I'd been over to her place? Good question, I thought. I told her I had always had it with me, just in case..

She called me yesterday to see if I wanted to hook up again last night. I like that - it means I must be doing something right.

Hotel

I've been corresponding with a woman I'll Donna. We started chatting on a vanilla site, but I noticed that she had put 'domination/submission' as something she was interested in. I was hoping, as always, that she was going to be someone who'd been thinking about it for ages and was looking to be taken by the hand and led astray, but it turned out she'd done just about everything imaginable. She lived far enough from me that it was going to be difficult, but then she told me she was going to be staying in a fancy hotel near where I live on Saturday night - she's there for some dinner things - and wanted to know if I was going to be free around 10pm.

Well, I have a dinner on too, but I'm notorious among my friends for leaving things around 10 or 1030 because I get tired and grumpy. So yes, I could make it to her hotel. But what to do? I send her this...

-----------------------------------------------------------------------
[Donna ]
Nice talking to you today, it's always good to hear someone's voice. I will be free tomorrow night from about 10pm, as it happens. I'm going to dinner, but I can always excuse myself...

As I see it, there are three options:
1) we meet up and have a drink and chat. then play another time.
2) we meet up and have a drink, then if we like each other, we go up to your room to play
3) we meet very briefly, we don't have a drink or a chat. we play.

Here's how I see option 3. You're in the bar. I come in. We see each other. If I look ok, you come over and give me a spare key to your room, and I give you a blindfold. You go up to your room, put the blindfold on. I'll come up in a minute or two. We start playing...
What I like with this setup, if you can get comfortable with it, is that it's like we're complete strangers. Whereas if we have a chat and a drink I'll start to be too nice. Sometimes I'm too much of a gentlemen, and we probably don't want that.
I'd need to know what do you do and don't like. I like blindfolds, teasing, mild spanking, bondage (but I'm not sure I'll be able to bring anything with me), toys, anal, watersports.. always safe. I like being in charge, but I'm fairly calm when I'm doing it. I don't like shouting, and I'm not at all into anything too painful.

Any thoughts?

------------------------------------------------------------------
She loved it!

Faking it

I thought only women faked orgasms, until I started doing it myself. As you can imagine, it's more difficult for a man to fake an orgasm (there's come, after all) but the reality is that if you're fucking someone and you have a condom on, they're not going to pick up the discarded condom and look for evidence of actual come in it. So in that situation it's quite do-able. But why? This is something I never imagined wanting to do. To be fucking someone and not wanting to come - surely that's the whole point?

Yes and no. I can think of three reasons why you'd want to fake coming.

First, you might be fucking someone and you're just not into it. Now if you're 25 that's not a problem, but if you're in your 40s and you don't fancy someone it's going to take a lot more work for you to come, and as you run it through the cost-benefit analysis (this all in real-time, as you're fucking), you realise that getting it over with is more important to you than coming. So you fake it....

Second, and this is the most surprising - sometimes you're fucking someone, and you've been playing for a while and it's all been great and you're totally into it.. and you realise that the overall quality of this particular sexual encounter is going to be great whether you end up coming or not. (Hard to explain to a 25yo, I know.) Sometimes the journey's more fun than the destination, or something like that. And the extra effort involved in coming - that mad dash to the finishing line - seems not to add anything. (One of my women friends told me this happens to her quite often. She says that she can have incredibly satisfying sexual experiences that don't neccesarily end in her coming. Or maybe she's just saying that to humor me...) So you fake it..

Third is due to overscheduling. You may be fucking someone at midnight and be aware that you have another assignation the next day at, say, lunchtime (this happened to me. today). For some guys this wouldn't be too challenging, but I'm always worried that going again too soon I'll lose wood. And there really is nothing quite like being really horned up. So you fake it..

Sometimes there's an unexpected bonus. Last night, I had very nice sex with Judith. And for reason number 3 I faked coming (and a bit of reason number 2 too). But after I'd 'come', we started playing again.. and lo and behold, I was just as horny as I'd been before I 'came'. She thinks I'm a truly legendary swordsman.

Arms

My friend Judith came over tonight, and after we'd had fun we were lying in my bed, cuddling, me behind her with my arm around her. She was stroking my arm and shoulder and she said - and please bear in mind this was totally unsolicited - "that gym works' really paying off". I murmured an embarassed thank you, and she kept going "I have an arm fetish", she said.

Gym boy

I was at a party earlier this evening, and as I was getting dressed and leaving one of the other guests said to me "so you're a gym-boy?" in a fairly pleasant and conversational sort of way. I froze. I was, of course, dying to hear what was going to come next but at the same time horrified that this sort of thing means so much to me. He went on "you have a very muscular butt...". Butt? I was hoping for shoulders, again.

Telegraph

I was talking to a friend the other day about fetishes, and about how some of them can get quite specific, and I remembered a guy I'd run across when I lived in London (notice I didn't say come across.) I never met him but I must have read his profile a dozen times. He had a thing for being beaten on the buttocks with a rolled-up newspaper by an older man wearing a suit. He was quite specific, and there's something a bit magical in the details.

First, it had to be a broadsheet newspaper, which (and this was a couple of years ago) narrowed it down to four. He wasn't going to be beaten with a rolled-up copy of the Currant Bun, or the Daily Mail. And among the broadsheets, he didn't want the Guardian. Too soft-left, one assumes; it's the newspaper for social workers. The Indy and the Times were barely acceptable. What he really wanted, it turned out, was to be beaten with a rolled-up copy of the Telegraph. And in a horrible way that does make a lot of sense.

Anyone have any other ones? It's the specificity I like. Don't be shy, leave a comment.

OTK

For the last few days I've been seized by the urge to spank someone, and as noone I currently see is really into it, I put an ad up on the local equivalent of Craigslist:

Ever fantasised about being over a guy's knee, skirt up, being spanked? Not so hard that it really hurts, just hard enough for it to be fun?
Handsome and basically normal single guy in mid40s, Eastern suburbs, looking for adventurous and naughty younger woman for fun. Spanking, maybe roleplay. I'm literate, imaginative. Limits very much respected.

What I'm hoping (and I know this is very much a longshot) is that someone will stumble across it and it'll trigger something - one of those moments where our hypothetical reader smacks her forehead with her open palm and says to herself "Yes, that's exactly what I've been wanting for ages...."

Quiet

Why, I can hear you asking, this sudden quiet patch? I'm in a different city this week and I'm looking after my kids while my ex-wife has a well-earned rest.

The family nextdoor have an 18yo daughter who's a university student. And one sure sign of the way that parental responsibilites have changed my life is that when I realised this, the first thing that came into my head was "I wonder if she babysits?". The answer, as it turns out, is yes.

I did manage to sneak out the other night for dinner with my ex. He asked me about my various love interests, especially my friend who runs a gallery (see a post a week or so ago). I told him that she was fine, and I'd been to her opening a week ago. He nearly lost a mouthful of food - the word 'opening' set him off, as I knew it would.

Sugasm 139

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 #140? 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
Flunking A Call
“I fell silent again and tried to think. What did he want?”

Revision
“He seemed… perfect. ”

Shaving, revisted.
“I don’t do it for society, for anyone who will or will not be seeing it. I do it for me.”

Mr. Sugasm Himself
Sugar Bank

Editor’s Choice
Exploitation, objectification and breaking the law…

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.)

The best sex I've had this year was with my friend Tina. We've known each other for a year or so and had sex once or twice, fairly vanilla stuff. We then discovered during a lengthy msn chat one evening that we were both a bit more adventurous than we'd let on, and we hatched a plan.

She's in the habit of having a afternoon nap on the weekends, and when she does, she wears an eyeshade (like the ones on airplanes). Or, in other words, a blindfold.

So the plan was this. I'd come by while she was asleep (or maybe just pretending to be asleep.. works either way). I'd let myself in.

On the day in question, I had to go to a christening that morning, my best friend from high school, then after that a post-christening lunch. I was on fire... chatting with my friend, his father (who I hadn't seen since I was a skinny surly teen), his brother, flirting with his wife's friends. Then, after a while, I excused myself and left.

I got a cab to Tina's place, found the key she'd hidden outside, let myself in very quietly (just in case she really was asleep). I stood in her living room, took my shoes off, my shirt and pants and then quietly went into her bedroom and stood at the foot of her bed.

She looked to be fast asleep. I watched for a moment or two, then gently sat down at the bottom of her bed. I picked up the cover and slowly raised it. She was naked (as instructed), and lying on her side, facing away from me. Her top leg raised. I couldn't see her pussy but I could see her ass and her inner thigh. I moved the covers aside and watched her, then very gently ran my hands over her. She was, I knew, awake, but didn't acknowledge anything. I moved her legs further apart and touched her... she was very aroused.

She kept the blindfold on and pretended to still be half-asleep.. we didn't say anything. I ended up fucking her from behind and it had a real intensity to it that quite shocked me. I left her to sleep and let myself out. We later compared notes: we'd both been very agreeably surprised at how primal it had been.

Course

I was at a work offsite for the last two days, learning all about Leadership. Why am I sharing this with you? By lunchtime on the first day we'd already been blindfolded, and the word 'roleplay' had already been used. You can imagine how excited I was. But I was ultimately a little disappointed; it wasn't like that all.

Gallery

I have a friend who owns a small gallery. She invites me along whenever she's having an opening, which is what happened tonight. I go straight from work; I wear a suit. The crowd is typically:

50% women
20% gay men
10% straight men who are starving artists
15% straight men who are partners of the women
5% single straight men who have a real job

I'm most of that last 5% (although 'straight' is probably stretching the definition a bit far, given that I've had sex with like a thousand men....). My function is to flirt with her friends and clients, she sometimes calls me 'the bait', or once, memorably, 'the tethered goat'. I was secretly in love with her for months last year but I've gotten over it.