Wow – I started the below LONG after I wrote a note to the group about feelings of humiliation linked with masturbatory habits, and I never finished it as I kept jacking off too much.  Finally, here you go…the first sentence below picks up from where I left off a couple weeks ago or whenever, it won’t make much sense now but anyway just read on…

So after what I described before, I went into a foot fantasy as the video I earlier mentioned went on.  Fused a bit of loser-ness but actually not really as this fantasy has virtually no self-deprecating stuff and no demeaning insults, it’s just being blackmailed by the possibility of shame is
 all.

Okay, so there’s a woman I know in real life, and she does turn me on, she’s a powerful woman and I do find her attractive.

So I imagined the below…as you can imagine no real names are used…but everything else below is true in terms of the setup of the fantasy in that the starting stuff is real and so forth.  Will probably put this up on a site somewhere, it’s turning out good even if I do say so myself…

Kathleen and I were hanging out after the larger group of us had broken up, “us” being a bunch of colleagues from a professional association (I’m being deliberately vague of course). 

We’re having a kind of “business-geek” talk, both techy and re business itself, both pretty versed in our respective fields. She’s a pretty well known speaker among a small but notable circle is probably the best way to say it, and she’s both a great public speaker and great private speaker.  She’s funny and powerful. 

We’re talking and laughing.  And we’re quite tipsy, both of us.  Okay, probably more than that, at least on my side, though she seems equally “happy.”  Franky, I’m thinking I’m grateful I’ve called home before the group went out as my wife wouldn’t like hearing me this obviously drunk.

And as I once in a great while do, being clumsy, I flip a glass of wine over.  It flies, spilling all over her dress.  I feel terrible!  There’s hasty napkin action, the request for club soda, and so forth. 

The worst of it dealt with for the moment, she says, “Well, the night is young.  But if I go upstairs and change, I know I’m not gonna feel like going out.”

I say, “Oh, I forgot, you’re staying at this hotel.  Ah well, sorry about that, I know it’s uncomfortable, I’m such a klutz!”

She laughed, “No, no, I do the same thing all the time!  Hey, there’s that complementary bottle of wine in my room, I’m not tired.  If you’re not, we could split it.”

Sorry, but let me pause the action here.  For what happens after this, you must frame in the right context to believe how it happens.

I think it’s fair to say “in real life” she finds my company enjoyable, whether it’s as much I do hers I wouldn’t be so bold as to say.  To put this in context, she’s one of those rare people I like so much that I know I don’t want to show it as that’s not acceptable to people, scares people off, that kind of thing, if you follow me, you know, where you don’t want to be socially awkward in showing that child-like “wow, you’re cool!” kind of thing (isn’t it a shame we lose that from childhood?).  And it’s especially so of course between married people, especially where their genders or preferences may make people whisper, unfortunately. 

While I might fantasize about her, it’s quite infrequent, most likely not even exhausting the digits of one hand (take that as you will), perhaps not more than once or twice.  And to be fair, I fantasize about all sorts of people I know from casual acquaintances to best friends, on some occasion, so that’s not much of a measure I’d say that way. 

So I do think twice, as we’re each married to others and there’s propriety and all, but she’s offering and I don’t think she means anything by  it beyond a friendly drink and continuation of the topic we were so intensely on.  I even know her husband, we met at a conference.  I’m sure there’s nothing wrong with it.  She’s a very liberated woman and can stand up for herself, and I’m no cad. 

So I say, “If you really want, I mean I don’t want to impose.”  I better leave an out for her, and I don’t want to seem over-enthusiastic.  Maybe she’s just being polite. 

“No, not at all, let’s go.”

We gather our things and in no time, chatting as we go about some character in our association, diverted from our original topic, we’re in her room.  It’s large, having a little anteroom with a couch. 

She says, “I have lots of points with the hotel, they seem to treat me nice, I didn’t even ask for this.”

She collapses on the couch, upright of course, feigning exhaustion.  “Well, it’ll be nice to get out of these shoes.  I have to admit I chose them more for the cute and didn’t realize they weren’t so comfortable.  I wasn’t going to wear them anyway, they’re really more if we had to go somewhere dressy, but I didn’t pack right and didn’t have others.”

“They’re very nice,” I offer.  I’m trying to balance that I should be polite and that I love them, they expose the top of her feet, black straps cross-crossing across the tops on a modest heel (just 2″), a few simple but effective lines, the back held by a bold red strap across the ankle. 

There’s a problem now.  I’m drunk, but damn if I am not getting hard!  I’m standing.  I don’t wear underwear, and the position is awkward, my shirt is not covering the area.  Damn!

She says, “Take off my shoe.”

I laugh. 

She says, “No, take it off,” holding up her left shoe. 

I’m trying not to let my hard, nervous breathing show.  I laugh more.  “Yes, ma’am,” I exclaim but don’t move, like I’m kidding around, too, but we both know this is fake. 

“Seriously, William, I’m just tired and these are a bit tight, do you mind?”

I say, “no,” and I realize I’m somehow both disappointed and relieved.  I just want to get them off and be done with it, and while it seems a bit odd, I realize I have a foot thing so it is surely me being over-sensitive.  I do so, I do not linger, whatsoever, except she’s right, the simple design has the back holding her firmly in place, and I’m thinking she probably has a tiny bit of padding (being a cross-dresser I know how you sometimes can shape the inside of the heel) on the inside of the back of the foot to further press but with comfort.  So I struggle briefly, and I pause and it’s killing me as I have to really hold her foot now to get her shoe off.

My right hand is pressed on top of her foot, the very bottom of the hand above the toes as my thumb and index finger embrace her ankle.  I pull the shoe a bit more firmly with the left hand.  I am trying not to think about it but damn I am getting harder.  At least I am crouched over now and she can’t see.  But how can I stand up?  I try to carefully position myself so my shirt will cover.

But the problem is my right hand is shaking!  I am looking down, afraid to look up, pursing my lips. 

But I have to be normal, I say, “Ha, it’s tight,” weakly. 

She isn’t laughing.  She isn’t saying anything.  I don’t want my breathing to get worse. 

But the shoe is off, of course, in less time than it feels, than the eternity.  Quickly my hands are off and her right foot is up.  I repeat as quickly as I can, having learned now how to get through it. 

I stand up carefully. Shit shit shit, I am getting so stiff why why why!!!!!

Now, after all this, she speaks up, “What’s wrong?”

I say, “What?”  Quickly, too quickly I know.

She giggles a little, “Look at you.  You’re making a tent!”

FUCK FUCK FUCK it’s worse than I thought.  I have to look down, what can I do!?

“Take it out.”  She says. Flatly.  Not really exactly commanding, but like I’m supposed to just do it.

I am struck dumb.  I nervously laugh, “What?”

She repeats, “take it out.”

She crosses her leg and her stockinged (just beige but on the very sheer side) right foot bounces, expectantly. 

I just stammer, “umm, um…”

She says, “Why not?  You’ve been looking at my feet all night.”

I gulp.  Really, was I that bad?  I couldn’t help it, but I had really tried not to, and at the bar I know I didn’t, except for when we got up, as it was under the table.  That’s why I sat that way, as we did, so I wouldn’t look.

She says, “Right?”

I say, “Yeah, I’m sorry, look, Kathleen, I’m really sorry, I’m so sorry, it’s not, I’m not, like, meaning to, um, you know, I just, they’re nice shoes, that’s all, I like them, and your feet look nice in them, I’m sorry, I just didn’t mean anything, you see, I haven’t, um, I’ve been traveling, I haven’t, um, and, my, um, I can’t help, and I really didn’t think – “

She interrupts me finally, “It’s okay.  Show me.”

Defeated, I don’t know what to do.  But really?  I have had a problem with compulsive sex.  I can’t afford to blow it.  But this is a dream come true.  I love my wife…

She says, “You wouldn’t like me calling Ann and telling her you were all over me, would you?”

I gasp, “What?  Kathleen!”

She says, “Get over it.  You know you want to.”

I’m REALLY defeated.  My wife won’t believe me when I say otherwise. She even knows I like this woman a lot, I’ve gushed over her, sort of.  DAMN!

I do it.  I just do it, but now I am deflated. 

She bounces her foot.  She keeps doing it. 

I am coming back to life. 

She says, “Go ahead.”

Hesitantly, I start to touch it. I then go ahead, stroking quickly in front of her.  I can’t talk.

She says, “Kind of below average.”  Just matter of factly.  She pulls her white iPhone out of her purse from next to her and speaks into it, “File height under adequate.  File width under tolerable.”

I grimace, I know, but I can’t  help it, I furrow my brows, and I try to straighten my face but close my eyes as I jack faster and faster.  It’s getting me off and anyway I have to get this over.  But…cum in front of her?  What does she want?

She says, “Back.  File height under tolerable.  File width under subpar.  File performance under interesting.  File fetish under humiliation.  File fetish under feet.”

I jack faster and I go “uh.” I think, “Fuck, she’s got me, goddamn goddamn god\damn.”

She says, putting down her iPhone, “You’re into being belittled.  Into my feet.”

I just say, “Yes.”  Now I calm down to a fast but regular stroke, but a lot of cum is ready and I back off, and I instinctively, because I’m so used to it, reach out to pick up a bunch of precum, taking my right hand off my dick to capture it while playing with my left to ride the edge. 

I now have it, and I eat it, because it’s just what I do. As said, I am drunk.  And then I realize how stupid this is. 

She says, “Wow, that’s odd!”

I’m like, “oh shit.”

My cock is not fully hard now but certainly more than half hard. I just stand there, having edged. 

She picks up her iPhone and points it at me and says, “Go ahead, go back to what you were doing.”

I say, “oh, no, and I start to put it in my pants.

She says, “Stop.  Remember, I can just make an accusation behind the scenes and your life is hell.”

I say, frozen, hands on pants but dick still out, “Uh…no, wait, you wouldn’t, and now, this, this is going to – “

She said, “Yes, this is going to seal the deal.  We both know you want this.  You wouldn’t be acting this way in front of me if you didn’t.”

I give up.  I stroke, and she takes pictures. 

She puts the phone away and asks, “What do you want to do?”

I said, “What do you mean?”

She says, “I want a foot rub.  But I want you to get off first so that it’s good and thorough.  Then maybe I’ll let you cum again if you do a good job.  So how do you want to get off?”

So I reply, having nothing left to lose and everything to gain by that, “I want to kiss your feet and cum.  To be honest, I won’t last because I haven’t cum in so long and – “

She says, “Fine,” cutting me off.  “Get down there.”

I do.  She puts her feet into my face as I’m on my knees, jerking with one hand, steadying myself with the other.  I am kissing her feet, at first so lightly.  on the bottoms.  On the sole.  On the arch. I kiss downward to her heel, move to the other one.  I start to nibble, I am allowed, I kiss open-mouth, I suck on her heels one by one back and forth. 

I look up and she’s watching intently.  She doesn’t seem aroused, but she doesn’t seem either disgusted or amused.  She’s just looking at me do this. 

I move my mouth quickly to the toes of one of her feet, kissing then sucking the big toe. 

She says, “Hold my foot up.”

I reach with my non-jerking hand and hold her just on the backside of her leg just above the ankle.  She is firmly seated and I realize I can pull a bit so that I can continue to balance while I jerk with the other hand.  I continue sucking her big toe then move my tongue between her big toe and the next one. 

She says, “Hurry up.”

Instinctively I say, “Yes, Kathleen.”  I look up and see she is now laying back and still looking at me but I think her chest is heaving with heavy breathing. 

I suck her toes and jack quickly.  I realize if I cum it will go all over the floor.  I ask, “Where should I cum?”

She says, “Oh, yes, we don’t want a mess.  Put your pants back on and just jerk into them.”

I look up and freeze only for a moment, then I simply get up and put my pants on.  I walk back and sit crouching, feet on the floor, holding her foot up again and going right back to sucking the toes while I reach down with my other hand into my pants and jerk off fast.  I start moaning and start to lose myself, not caring anymore about appearances at all. 

I start moaning, “Oh yeah, thank you Kathleen, thank you,” and look up to see she has her iPhone out again and is taking pictures again.  I couldn’t care less.

She says, “Cum in your pants, William.  Do it now.”

Obediently I jerk faster and faster, I’m close anyway, and in moments I am cumming in my pants while I’m desperately sucking her smaller toes.  I moan “oh” repeatedly.  I feel the wetness against myself and then dripping down and collecting around my balls and the bottom of the pants below. 

“That’s a good boy,” she says.  “Stand up,” she tells me, and of course I do.  She takes a picture aiming right at my wet spot in my pants.

She says, “Okay, you can give me a proper foot massage now.”

I do.  I’m sighing, from shortness of breath and sexual ecstasy, as I do.  I flex her toes on her left foot, move my knuckles up and down her sole, and rub, squeezing up and down.  I reach back and knead her ankle. 

She says, “More, that’s good,” and she is leaning entirely back now, phone down.  She slightly moans.

I continue, and go back up and down the foot with squeezes and more knuckles up and down the sole.  I go back to her ankle. 

After a short time more she says, “Other foot,” and moves it right in place of her left.

I repeat the procedure.  By the time I’m finishing with the right foot on the ankle, she says, with urgency, “Reach into your pants and play with yourself.  Suck my toes.”  I can hear her breathing heavier, and I glance to realize she’s reaching into her skirt, through the band, not pulling it up so the treasure inside remains hidden to me.  She’s clearly playing with herself now.  She pushes both feet in my face.  I am sucking again and now have one hand playing with her toes and the other in my pants.  She shoves the sole of her right foot into my face while I am sucking her left toes.  I moan and cry out, “oh god.”

Her feet are jerking back and forth into my face and mouth as she’s playing more with herself, causing her lower half to bounce around.  My cock is already fully hard and I’m pulling below and up the head and squeezing it. 

A short time later she says, “William, cum, do it, you fucking … little slave …. uhh… my slave.”

I say, “Yes, yes, I’m your slave,” and I now squeeze my cockhead and twirl and am kissing all over her feet.  Shortly I am cumming as she is moaning and shoving her feet into my face.  She is moaning loudly and saying, “Do it, do it you little…little shit.  Oh fuck!”

We both feed off each other climaxing and start just incoherently half-yelling and moaning.  After she says, “Oh, god,” as I am now just holding my spent penis in my pants and lightly kissing her feet, she gives me a little slap with her right foot across my face, just a gentle push really, and then shoves me back with her left foot.

She gets up and laughs and says, “Mmmm, that was good!  Now, don’t take this personally, but you just need to leave.”

I said, “Wha – I’m sorry, I’m sorry, I didn’t – what – “

She says, “No, William, you’re fine.  I just want you to get out now that I’ve used you.”  She gives me a big smile.  She likes me, but she really is done with me.  She says, “Good night.”

I say, “Oh, okay, uh…” and I look down and around and realize I have everything, my clothes are on…just there’s a huge wet spot on and dripping down my pants.  I say, “Oh, okay…good night!  Thank you, Kathleen – really, thank you.”

She says, “You’re welcome.  I’m sure there’ll be another time you can help me out,” and winks.  She says, “Have a good rest, and a good flight tomorrow.”

I say, “Yes, you, too,” as I open the door and leave. 

I have to go to my room a few stories up.  I look terrible with my cum-soaked pants.  I have no choice but to just go to the elevator.  It’s not that late and sure enough there’s a few people in there when I walk in.  Clearly they can see.  A couple businessmen talking half-freeze and then look at each other and snicker out loud, then try to talk about some business deal as if nothing happened.  A couple is there, coming back from some big night on the town.  I see the woman’s eyes widen then she looks away at her mate and tries to pretend nothing happened.  He, though, is oblivious and says, out loud, “What’s wrong?”  She half-whispers, “NOTHING,” and I can hear her whispering as I am turned around, having whipped around in a rapid 180 as soon as I got on the elevator. 

Worse, I get off the elevator first, the rest going even higher up, and I can actually hear them all laughing as the elevator door just closes!

I spend nearly the whole night masturbating, not really able to cum and not wanting to.  I imagine Kathleen might also be masturbating but have no idea of course.  I keep wondering is was to come…