I have a fuck buddy

I had sex tonight and I have to admit it was pretty great for being a casual encounter.  The older I get the more I crave some kind of attraction beyond merely the physical.  I do like this person even though it doesn’t seem like we have much in common other than both being horny at the same time.

My friend with benefits is of east Indian descent and she pretty much overweight.  I’m not usually into heavy women but I have to admit that she has a certain sensuality that I am attracted to.  She has very large breasts  – I much prefer small breasts with large nipples – -and a nice, shapely ass.

We took our time, watching some [bad] porn on TV.  After a while I began to eat her pussy which was extremely wet.  Soon she nudged my mouth off of her and guided my fingers into her pussy.  Five minutes later she squirted heavily onto the bed, cumming 2 or 3 times.

Then she fell asleep.  Hey!  I was still horny so I woke her up by caressing her ass with my hard cock.  That woke her up and she began to guide my cock inside of her.  I said, “we should play safe,” but she seemed unconcerned, saying that she had an IUD and that she trusted me since she kind of knows me now.  I still felt uncomfortable, even though I have had a vasectomy.  So I got a condom and began fucking her from behind.  But…it’s hard for me to cum with a condom so I removed it.  We were fucking side to side and I leaned over to kiss her.  She is such a passionate kisser that I became ultra-aroused and soon could feel my cock about to explode.  I pulled out and came over her ass.

I have to admit it was a pretty intense orgasm.  Afterwards she took a shower and we spent another half hour watching Netflix before I drove home.

This is a nice person who I pretty much trust.  We’ve been together four times now over a three year period.  It’s nice to see her once every few months.  I don’t think that we can ever be boyfriend-girlfriend since there’s not enough in common between us outside of the bedroom.  But tonight was as good as a casual encounter can be.





My threesome

Believe it or not I have actually taken part in a threesome and it’s actually in the recent past as opposed to the way-back. Here’s what happened:

On a lark I threw up a post on craigslist saying I was a single middle aged man in search of my first threesome.  It was basically a hail mary and I didn’t expect to get any responses.  Lo and behold, out of the blue I received a response from a woman saying that her and her man were rolling and were looking for a third person to play with them.

Naive me didn’t know what ‘rolling’ meant.  When I called up to talk to them, John, explained to me that they were inhaling some kind of vapor similar to what you would get at a dentist.  I think it was similar to what the  Dennis Hopper character did in Blue Velvet.

I was nervous about meeting these strangers at John’s auto body garage in a sketchy part of Oakland, but they sounded nice on the phone and I figured this might be my only chance.  John owned a garage and since he’s married he has his playtime sessions in the upstairs office.

I arrived and Alexa greeted me at the downstairs entrance.  She was wearing fishnets and a blouse – a 40-something woman who, though attractive, looked like she had inhaled a little too much vapor in her life.  John was a nice guy with a stocky build, and a little overweight.  Sitting on the couch naked was a second woman – Pam – who was naked. Pam was the most attractive of the three — a thrity-something with brown hair, a skinny build with pert breasts and shaven pussy.

I took off my clothes and Alexa guided me down onto the carpeted floor.  Alexa has medium sized,  breasts and an almost clean-shaven pussy.  (I prefer hairy pussies as documented in earlier posts) She turned around in a 69 position and began giving me head.  Her pussy was airy and light and clean-tasting and she had a large clit.  She was fabulous at giving head and I could feel myself getting ready to cum.  I didn’t want to cum so soon so I withdrew and began to play with her pussy with my hand.  She grew increasingly aroused and soon she came, squirting over the towels that had been laid down.

We took a break and went to the couch.  John suggested that I give Pam head while he played with her tits.  I began to give her head but Pam had over-vaped and she was barely conscious.  That felt weird to be giving head to a corpse-like body so after a while I took a break.

A little while later John, Alexa and I began playing again.  I put on a rubber and took Alexa from behind while she sucked Jack’s cock.  I probably could have cum this way but I knew how I wanted to cum that night.  After a time I withdrew from Alexa and she began to give me head again.  A couple of minutes later I exploded.  She was that incredible.

And that was my first threesome experience.  It was kind of weird but also kind of good.  Not bad if I do say so myself.  Now if any of you find yourselves in the Bay Area you know you can call on me for a threesome.  I’ve got experience!



A dream threesome gone wrong

It’s been a while since I’ve last posted. During that time I got back with my old girlfriend, Mina, and things were looking good for us.  I should say we were never officially back, but we were seeing each other once or twice a month (we live 50 miles apart) and texting every night.

She was coming to visit me last week for an extended stay as she has done every summer when her daughter stays with her father.  Somehow we got into a big fight via text the very day she was supposed to have come over and we haven’t spoken or texted since.  The fight was trivial but the larger issue is that neither one of us really wants to commit. I love being with her — the sex is better than it’s been with anyone I’ve ever known – we laugh a lot and have similar interests.

Last night I had a vivid dream about Mina and her mother.  I should say that her mother does not approve of me.  I’m a jazz musician and although I work and teach nearly every day/night of the week she looks at me as a ne’er do well — someone who would not provide.

In the dream I was sleeping over at Mina’s and her mother was flirting with me.  In real life we’re talking about an elderly Chinese woman, but in the dream, I have to admit, she looked kind of hot!

It was time to turn in and for some reason we were all sleeping in the same bed. So I’m thinking, ‘This is great, I’m going to have my first threesome!‘ Mina turned off the lights and I get right to work — I was passionately kissing Mina when I reaching across her and fondled her mother’s breasts.

You would think that in a dream I might be able to get away with this, but no!  The mother immediately screamed at the top of her lungs and Mina stopped kissing me and turned on the lights.  The Mother proceeded to explain how she had always known that I was no good. “HOW COULD MY DAUGHTER BE WITH SUCH A MONSTROSITY?!”

I guess her Mom was right.  What kind of a sicko dreams of an incestuous threesome? Don’t answer that!


Snowflakes and vaginas: No two are alike

Well you guys really liked yesterday’s vagina post so I figured I’d write some more about the big V.  Now that I’ve had the epiphany that they’re all different I wish I had kept a vagina journal.  At this point I can only really remember the last two.

The trouble is that when I was young and first having sex I would come so fast that I didn’t have time to fully internalize the experience.  All I knew that it was the most magical place I ever knew — the feeling of being inside a pussy was exponentially better than anything I had previously felt.

I got a little older but by then I was mostly using condoms so I really couldn’t feel much.  In my 30s I got married and I really liked my wife’s vagina.  It seemed to fit my cock just right and I think we had good sexual chemistry.  Once we had kids, however, sex became more and more infrequent and we gradually grew apart.

Now that I’m middle aged and single I savor sex in a way I didn’t when I was younger.  Sometimes I just want to stare at the vagina, committing it to memory.  I love hairy pussies which appear so much more womanly and sensual than their shaven pre-pubescent counterparts.  I like large labias that protrude and that are so lovely to roll against my tongue.

There’s nothing quite like a vagina.  Mysterious, heavenly, and the answer to all life’s stress.

In search of the perfect vagina

A thought occurred to me:  Why is so much emphasis put onto penis size but not vagina size?  We know that not all penises are created equal so shouldn’t the same be said of vaginas?  It’s unfair to us guys top bear the lion’s share of the genitalia burden.

It struck me that I have rarely heard an individual vagina described in print, or verbally by a friend.  Just because they’re concave doesn’t necessarily mean they defy description.  They are the greatest feeling organ ever known to man, you’d think someone – a poet or an writer – would have written about them.   What feels as good?   The mouth comes close, but not that close.

I have to say that I didn’t care for Careen’s vagina.  Sorry, not sorry, but it didn’t feel as good as most other vaginas I’ve experienced.  I actually think it was too small.   That’s not bad for my ego, actually.  How many chances do I get to say that my cock was too big?  There was something about the angle or the shape of it that made it feel shallow to me.  It wasn’t that she was dry — she was very wet and I would eat her pussy for long stretches.  I really enjoyed that — she had a great tasting pussy with  a beautiful labia and clit. But the actually sex was not great, especially compared to Mina.

It will be interesting to see how I perceive my next partner, assuming Mina and I do not reunite.  I’ll be keeping a look out for the perfect pussy.


The curse of the jackhammer

I read a blog post recently by a woman who was [metaphorically] destroyed by a well endowed man who pummeled her with his jackhammer love-making technique.  Yet she continues to see him even though she’s unable to have vaginal sex in the wake of his coital maiming.

That just shows you how much less effort goes into dating and love-making when you’re reasonably attractive and in possession of a schlong the size of Cincinnati.  Guys like me, who are smaller (5’8″) and have an average sized cock have to work so much harder on all fronts. We have to go into overdrive on the first impression, turning on the charm and especially the humor.  Then we have to appear sensitive, YET MANLY.

It’s not easy.

I shouldn’t complain.  I’ve had my fair share of lovers, probably more than I deserved.  For me the equalizer was [is] that I’m a jazz musician.  Being an artist comes with a certain cache and the fact that I’m a little out of the mainstream gives me a slight edge. But I still have to work my ass off to get laid!

Fuck these mongoloid, arrogant, narcissistic, cockee-doodie motherfuckers!

That’s all.

Fantasy and reality

Some years ago, when I was still married, my wife and I were friends with a single mom (who would later become our accountant) whose daughter was friends with our daughter.  Every once in a while we’d have them spend a weekend with us at our country home in upstate New York.  Ellie was a sultry, extroverted, free-spirited Italian American woman. She was an olive skinned, raven-haired – petite but not skinny.  She had full breasts and a curvy ass.  Her entire being exuded sex.  She would often wear low cut jeans exposing a bit of her ass to me.  She was flirtatious and playful.

One Sunday evening found both of with our two daughters spending the night in that house. (My wife had to leave early to go to work Monday morning)  Of course I had fantasies about the kids going to sleep leaving Ellie and I alone by a roaring fire.  Perhaps she would have complained of a bad back, asking me to massage her.  Or maybe we would have simply looked into each other’s eyes and began kissing.

Nothing happened. We played a board game with our kids and retired to our separate rooms.

Looking back on that time I can fantasize about how great it would have been to have sex with her, but now I can do it without the baggage of how messy things would have been afterwards.  What if I had acted on my fantasy only to have been rebuffed?  Awkward!  Sometimes people flirt and they don’t realize they’re flirting.  Or they’re not flirting at all and people like me misconstrue.

Now I still have my fantasies as well as a good accountant.

There ought to be a rule


I saw someone on Twitter complaining that films often depict ugly guys with smoking hot women.  The person’t outrage stemmed from the fact that this devise objectified women –  as if even ugly guys are entitled to hot women.

I’m more outraged that normal looking women aren’t cast in films. To me a tall women with large breasts is a boring look.  I’m tired of bulbous boobies.  Why?  Because we see it all the time.  I want to see normal looking people with normal breasts that sometimes sag, and penises that are average in length, have sex.  Now *that* would be hot.

That’s why porn is so unsexy.  It’s cookie cutter people with enhanced bodies, whether it be cosmetically or chemically, pretending to enjoy having sex. Who can fantasize about that?  I would rather see someone with unusual looks have sex, but more than that I want to see arousal.  I want to *be* aroused.


The strangest breakup ever

So it’s been three months.  Things have been crazy busy on this end with wall to wall gigs and students so there’s not much time to update.  In this interim I have been ping ponging back and forth between Careen and my longtime girlfriend, Mina.  I think that Mina and I may be back together now but it’s complicated and I’ll need to flesh out the details in a future post.

In the meantime Careen and I got back together about a month ago.  The thaw started on Facebook and spilled over into an actual date in late January.  We had a great night and I ended up going back to her apartment and staying the night.

Careen and I just didn’t work as a couple.  She’s an incredibly nice, warm, socially conscious, caring person.  And she’s beautiful.  She has the kind of looks that I’m usually attracted to.  She’s a petite Filipina with a lovely, easy smile, small breasts with pert nipples that respond instantly to the touch, and a great ass.

We got along well personally and our banter was always easy and fun.  She loved sex, and as recounted in an earlier post, was almost always the one to initiate.  The trouble was that sexually we weren’t compatible.  Don’t get me wrong, I was very attracted to her but for some reason the actual act never felt as good as with Mina, my previous girlfriend.

Careen was into pain.  She wanted rough sex and she wanted me to spank her and slap her face.  I’ve never been into pain, either giving or receiving,  but I can get into a little spanking once in a while.  The face-slapping, however, was too weird for me and frankly felt a little like a line could too easily be crossed.  She said we needed a safe word but that never seemed like a viable option to me.  Plus, how do you find a safe word that doesn’t make you laugh?

Careen was always calling me ‘Daddy; and ‘Papa’ during sex and this too made me a little queezy, as if she was living out an incest fantasy.  I’m not a prude and I’m all for fantasies but the incest fantasy had the effect of removing arousal rather than causing it.  And its a sick act — I can’t go there in any way.

So the break up:  On what would be our last morning together she woke me up at 6AM to have sex. I was half asleep and tired from the previous night’s marathon sex romp (I am middle-aged man, after all) but there I was, happily thrusting away in the missionary position when she said, “Say my name…”

What is she, Heisenberg?  I’m trying to wake up and perform to my usual standard of excellence and now I have to vocalize as well?!  OK, it’s not that hard to do.  Why not?


A few seconds later she pushed me off of her asking, “What did you say?”

“What do you mean, ‘what did I say?’ Careen.”

“No you didn’t, you said another name!  Is that your old girlfriend’s name?!”

Folks, I did not say another name.  I was tired and I wasn’t speaking in my full voice so it came out in a whisper.  No matter how much I protested she refused to believe me, saying that she suspected I had feelings for my old girlfriend.

Here’s where things start to get Freudian.  I’m 99% sure I said Careen’s name, but she happens to be right.  I do have feelings for Mina and I think I will always have feelings for her. So whereas I thought Careen wrongly accused me, her larger point was something I couldn’t refute.

We met three nights later at a local bar and amicably agreed that it was best to go our separate ways.  As far as I could tell there is little animosity between us.  Still..what a nutty way to break up!