Double Trouble (F/f, F/m, FF/m)

This story is the winner of the 2002 Golden Feather Award for best nonfiction story of the year.

All three characters in this story are over 21 years old.

This story contains extreme F/m tickle torture, foot worship, and some adult material. If that will offend you, then don't read it.

"Double Trouble"
by Milagros

Part One
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I am waiting, naked, on my hands and knees, for Mistress Zara to enter the room. This is a special day that we have been keenly anticipating--a joint session with her friend, Mistress Kassandra. Mistress Zara and I have worked on a script for this role play, and Mistress Kassandra has read it. I will play the role of a boy, and Mistress Kassandra will play the role of my older sister. Mistress Zara will play the role of our babysitter, hired by our parents to take care of us on a holiday weekend. In the role play, she has been our babysitter before, and has had trouble with us misbehaving.

Mistress Zara enters the room, looking quite young in a cheerleader's skirt and sweater, with her lovely feet hidden in knee-high white socks and sneakers. (Actually, she is in her mid 20's. I am quite a bit older.)

"Are you ready, slave?"

"Yes, Mistress Zara," I answer from the floor.

"I'll go out, and Mistress Kassandra will come in, as your sister. When I return, it will be as your babysitter. You may get up, and sit on the couch."

I obey. The room has a large couch, a padded bondage table, a chair, and a cabinet with supplies. Kassandra enters, also looking young in a cheerleader's sweater, with a short skirt, and white socks and sneakers. (Actually, she is in her early 20's.)

"Yuck!" says Kassandra. "You're disgusting, as usual. How can you go running around in the middle of the day with no clothes on?"

"Who cares what you think, sis! If you don't like it, get out of my room. Nobody invited you in here, anyway. You're a pest!"

As we trade insults and pokes, Zara enters the room.

"Are you two fighting again? After the trouble I had with you last time, I didn't want to take this job. But your parents promised me that you two would behave, and I asked for _complete_ _authority_ to do anything necessary to keep you on good behavior. Your parents gave me a free hand. I can punish either one of you, or both of you, as I see fit."

As Zara glares at us, we look down in shame, and await her judgement. She reminds us that the last time she told our parents about our bad behavior, we were both grounded for a month.

"So you have to do what I say. If you obey me, then I won't tell them. Get up on that bed, back-to-back," she adds, pointing to the bondage table.

Kassandra and I obey, climbing up onto the bondage table, and lying on our sides, back-to-back.

Zara removes many lengths of rope from the supply cabinet, and begins by tying us together at shoulder level. My wrists are then tied behind my back, and the same is done to Kassandra. Then Zara ties all four wrists together inbetween our backs. She takes more rope, and moves down to our feet.

"You should know better than to wear shoes in bed!" she scolds Kassandra.

She unlaces Kassandra's sneakers and pulls them off. She pulls off her white socks, also. Kassandra squeals with laughter; Zara has taken the opportunity to tickle her lovely, now bare, feet. It's too bad that I can not see them, tied back-to-back with her.

Zara has a pleased smirk on her face, as she ties Kassandra's ankles together, and then ties mine together. She completes her work by tying all four ankles together, with yet another rope. I can feel Kassandra's bare feet against mine, which excites me.

"I'm now going to have a contest," announces Zara. "I'm going to find out which one of you is more ticklish. The one who is more ticklish will be the loser."

She begins by holding back Kassandra's toes, and tickling her sole with her fingernails. Zara's nails are medium length and strong, and make excellent tickling implements. Kassandra laughs, shrieks, kicks, and shakes, trying to evade the torment. I am shaking along with her, tied to her at the shoulders, wrists, and ankles.

Zara is ruthless, scratching at Kassandra's soles with no mercy, until Kassandra is laughing uncontrollably. Moving up to her calves gives her a little rest, but when Zara's fingernails get behind her knees, Kassandra goes berserk, frantically trying to get away. We are tied too tightly, and she can not escape the ever moving fingers.

After a light tickling on the thighs, Zara digs into Kassandra's lower ribs with both thumbs, causing her to howl like a mad woman, and beg for mercy.

"Oh, no, young lady, you'll get no mercy until I'm good and finished with you," Zara replies.

She moves up the rib cage very slowly, as Kassandra laughs and laughs, unable to speak. When she reaches the armpits, she pokes under both arms at the same time. Kassandra howls again, like an insane woman, and Zara is gleeful.

"I've found your best spot! Right under the arms. Now you're in for it, young lady. This is quite a lot of fun. And this is going to go on for quite some time."

She keeps digging into Kassandra's armpits for a good five minutes, until Kassandra is too weak to laugh very loudly, until she is truly desparate for air, until she would promise anything to Zara in exchange for a break from the tickling, but she has no breath, and can not speak.

Finally, Zara stops. Kassandra is now panting and gasping, and still can not speak. Zara walks around to my side of the table, and looks deep into my eyes.

"Your sister is quite ticklish, about 8 on a scale of 0 to 10. But now it's your turn, young man, and I don't believe that you are going to enjoy this."

Zara begins by digging into my collarbones, which she knows are very ticklish. I begin to laugh hard, and shake, dragging Kassandra with me as I struggle.

"No way you can escape my magic fingers," says Zara, moving down to my armpits. I go berserk, as she pokes and pokes under my arms. I am laughing so hard that I can't breathe well, and the bondage table is shaking, even with my weight and Kassandra's on it. Zara never lets up, and I am hardly able to make a sound, as she keeps tickling and tickling under my arms.

It seems like an eternity, but is probably only five minutes, when she moves down to my ribs. She plays them like a piano, one hand on each side, as I laugh and laugh. My armpits still ache, as she gives my ribs a real going over.

In between my bursts of laughter, I manage to get out two words, "please, mercy."

"No mercy for naughty boys!" says Zara. "Not now, not ever. Tickle, tickle, tickle, baby boy. That's what you'll get--endless tickling. Tickle, tickle, tickle. Do you like it? Because I haven't even begun to tickle you, really."

It is not so bad when she goes down to my thighs. They are ticklish, but not nearly as much as other places. Behhind my knees causes me to thrash and howl again, much to Zara's amusement. She digs her nails behind my knees for a few minutes, and grins at my frantic reaction.

She stops, goes to my feet, holds the toes back on my right foot, and pauses. She lets me tremble in anticipation for ten full seconds. Then it starts--the deadly scrabbling of her fingernails on my taut sole. I go mad. I kick and thrash so much that she climbs up on the bondage table, and sits over our four legs to keep me still. I am laughing so hard that I can't breathe at all, and I am desparate. But she keeps it up, switching to my left foot, until I think that I will pass out. I am in tickle hell, suffering and suffering, unable to do anything about it. Zara revels in my helpless ticklish vulnerability, and tickles me without a pause. She tickles and tickles, and I can do nothing but endure it.

At long last she stops. I just tremble and gasp, and Kassandra speaks.

"He's more ticklish, isn't he? Don't I win?"

It is obvious to all three of us that I am indeed more ticklish than Kassandra, but Zara says, "I'm not sure. So I'll just have to continue the contest."

She climbs down from the bondage table, and picks up two toothbrushes from the supplies. With a look of delight, she pokes them into Kassandra's armpits. Kassandra shrieks, and laughs, and struggles. Zara keeps this up for only about two minutes.

"Still an 8," says Zara.

She comes over to me, and holds the toothbrushes in front of my face, and grins. Again, she lets me tremble in anticipation for about ten seconds, before poking them under my arms. I howl, and the whole table shakes, as I laugh and laugh. She keeps it up for five full minutes, until I'm too exhausted to struggle, and just lie there, enduring unbearable tickle torture.

She stops, and drops the brushes to the floor. She looks at me with pity. My armpits are aching worse than ever, and I am panting.

"You're a 9 at least, maybe 9 and a half. You lose the contest."

"Yippee! I win, I win, I win!!" exults Kassandra.

Zara unties all the ropes that hold us together, and then unties Kassandra's ankles and wrists. As Kassandra gets down from the bondage table, rubbing her wrists to restore full circulation, Zara tightens the ropes holding my ankles together, and also tightens the ropes holding my wrists together behind my back. This does not bode well for me, I think.

[to be continued in this thread]

Part Two

Part Two
--------

"Help me get your brother onto the floor," says Zara.

The two of them soon have me on my belly on the rug. Zara ties my ankles to my wrists, very securely, completing a classic hogtie. She smiles, and pulls over the chair, near to me, and sits down. She takes off her sneakers and socks, and wriggles her bare toes, knowing that I am twisting my head to see her perfect bare feet.

She gets up and holds one sock in front of my face. Its sole is stained with sweat, and covered with grime.

"Open wide," she says, and then stuffs the sock in my mouth, making sure that the entire soiled sole is inside, with the upper portion, that had covered her calf, sticking out. She ties a length of rope between my teeth and around my head to hold the sock in securely. The taste is acidic, quite sour, but I relish it. It is the taste of sweat from the sacred foot of my beloved Mistress Zara.

Zara sits back in the chair, and pokes my ribs with her toes. I giggle, but it can not be heard through my gag.

"Here's what you won," says Zara to Kassandra, pointing to me.

"As the winner of the contest, he's all yours. To tickle, and tickle, and tickle some more. Tickle him to your heart's content. Tickle him as much as you want to, as long as you want to, as ruthlessly as you want to. I'll just sit here and use him as my footstool as you tickle him insane. He's well gagged, so don't worry about the neighbors hearing him. Tickle him until he goes mad. Go to it! Get him good! Drive him senseless. Tickle him insane!!"

With joy in her eyes, Kassandra hugs Zara, and kisses her on the cheek.

"Oh, thank you! Thank you so much," she says, as she sits beside me on the rug, picks up both toothbrushes, and digs into both of my armpits.

The hogtie offers no protection; although my arms are pulled behind me and tied to my ankles, Kassandra is able to get the toothbrushes well lodged into my armpits, and she tickles relentlessly, with no pause and no mercy. I am laughing hysterically into my gag, and Kassandra taunts me as she tickles.

"You are _so_ _helpless_! Tickle, tickle, tickle. So utterly helpless and defenseless. Tickle, tickle, tickle. Utterly at my mercy, little brother. Tickle, tickle, tickle. And I'll have no mercy, none. Tickle, tickle, tickle, tickle. Zara has rendered you into my living tickle toy, much more fun than the Tickle-Me Elmo that I used to have. Tickle, tickle, tickle. So I'm going to tickle you forever--I may never stop. Tickle, tickle, tickle. The more that I tickle you, the more that I want to tickle you! Every squirm and wriggle that I see incites me to tickle you more! Tickle, tickle, tickle. I just can't get enough of this--I really will never stop. Tickle, tickle, tickle. I'm going to tickle you _insane_! Tickle, tickle, tickle. And there's not a thing that you can do about it. Tickle, tickle, tickle, tickle, tickle."

As Kassandra taunts me and tickles my armpits, Zara digs her bare toes into my ribs again. I am in agony, laughing uncontrollably into my gag, unable to catch my breath, and wishing that I could faint. It goes on and on.

Finally Kassandra takes a break, and I take big breaths through my nose.

"Don't let up!" says Zara. "Don't stop! Tickle him more, keep at it, don't give him a rest, get him good!"

Kassandra is just moving her attentions to my feet; she had no intention of stopping. She scratches both of my soles with her nails, and I waggle my feet to try to get away from it.

"Oh, you'll never escape," says Kassandra, firmly grabbing my toes with one hand, and bending them back, to keep that foot still, as she scratches its sole with her other hand. She tickles and tickles my vulnerable sole.

"You're all mine, little brother. Tickle, tickle, tickle. All mine, to tickle and tickle, and then tickle even more. Tickle, tickle, tickle, tickle. Endless tickle torture, from your big sister, who has put up with more than enough crap from you. Tickle, tickle, tickle. I'm going to tickle you into madness. I'm never going to stop tickling! Never! Tickle, tickle, tickle, tickle, tickle."

No longer willing to just watch, or just use her toes, Zara now sits on the rug beside me also, and digs into my ribs with both hands. The two women smile at each other, and they both keep tickling and tickling. They are enjoying my helpless agony, as they just tickle and tickle. My armpits still ache, my diaphragm now hurts, and I laugh and laugh into my gag.

They seem to know that I'm about to faint, and let up just enough to keep me conscious. Every minute seems like an eternity to me, an eternity of ticklish agony. The sock gag is sodden with my saliva, and I am covered with sweat. They tickle and tickle, keeping me on the edge, keeping me in tickle torture hell.

---------------------------------------------------

When they finally stop, remove my gag, and untie me, I just lie on the rug, senseless. I have been tickled to exhaustion, too weak to move, tickled senseless.

"How long?" I manage to ask.

Kassandra glances down at her watch. "It was 45 minutes, but we're _not_ done with you."

"Oh no," says Zara, "and you were able to wriggle too much in the hogtie. So now we'll stretch you out."

I make no effort to resist as they tie my wrists together again, turn me over onto my back, pull my wrists high over my head, and tie them to a metal ring in the floor. They now tie my legs together at the knees and at the ankles, stretch me out tautly, and tie my ankles to another ring in the floor.

They both grin at me. Zara, with her gorgeous red hair, has her green eyes gleaming with tickle lust. Kassandra, with her lovely,long, dark brown hair, has a similar gleam in her brown eyes. They are both happy to be in total control of a helpless, ticklish male, and they intend to take full advantage of it. They say as much.

"You're even more helpless than before, baby brother, and I'm going to tickle you even more than before!" says Kassandra, as she tickles me under the chin.

"We're going to tickle you senseless again," says Zara, as she tickles my collarbones, "we're going to tickle you insane!"

Zara picks up an electric toothbrush, and turns it on. She straddles my chest, and works the brush first in one armpit, then in the other, then on collarbones, and then back to the first armpit.

As Zara drives me mad with that infernal electric brush, rotating her attentions, Kassandra sits on my legs and tickles my feet endlessly. I laugh out loud at first, but my laughter becomes weaker and weaker as they continue. My struggles become feeble. But they just keep on tickling me, and tickling me, and tickling me.

Zara looks into my eyes, silently, as she tickles and tickles. It is a look of pure joy, reveling in her power over me. Kassandra begins to taunt me again.

"It's just too much fun to stop, baby brother. Tickle, tickle, tickle. This is more fun that I can tell you. Tickle, tickle, tickle. So much fun to watch you squirm. Tickle, tickle, tickle. So much fun to watch your toes wriggle. Tickle, tickle, tickle. Knowing that you can't get away, knowing that you desparately want us to stop, knowing that we _won't_ stop, not for a long, _long_, LONG time. Tickle, tickle, tickle, tickle, tickle. You are utterly helpless, and totally under our control. And it's going to stay that way, forever. Tickle, tickle, tickle. We're going to tickle you, forever. Tickle, tickle, tickle."

"Or at least until your parents return, on Monday night," says Zara. "Tickle, tickle, tickle. No hope for you, no escape, no rest. Tickle, tickle, tickle. Maybe I'll call five or six of my girlfriends to come over, and we'll gang tickle you all night! Tickle, tickle, tickle."

They both laugh at that idea, and keep on tickling me. I am now too weak to struggle at all, and just lie there. My mouth makes laughing motions, but I don't have enough breath to make a sound. I spend what seems like another eternity in tickle torture hell, suffering endlessly. It goes on and on, as they tickle me ruthlessly, endlessly.

-----------------------------------------------------

At long last they do stop. I am utterly exhausted again, and too weak to move or speak, barely noticing as they untie me.

"We'll give you a break from the tickling," says Zara, "but only if you make yourself useful. My socks were so dirty because I did a five mile jog in them this morning. I want a foot massage. So does your sister. Will you agree to massage our feet?"

I have gotten some breath back, and manage to answer.

"Yes," I say, sincerely, "I'll be glad to."

[to be continued in this thread]

Part Three

Part Three
-----------

The women sit on the couch, their lovely feet on the rug. I take a position sitting at their feet, and Zara extends her left foot to me. Her feet are size 7, with high arches, short cute toes, and smooth heels. She has had a pedicure the day before, leaving the soles soft and ever so beautiful. Her nails are painted dark crimson, and perfectly shaped.

Mistress Zara has had me read about reflexology and learn to be competent at foot massage. I balance her foot in my lap, and use both hands, as I concentrate on massaging her. I do most of the work with my thumbs, as the books recommend, working slowly up her sole, from the heel to the base of the toes. I then pull and roll each toe separately. I concentrate some extra effort on the ball of her foot, as she sighs with pleasure. Then I go back to her heel and start over. I am in heaven, serving at the lovely sacred feet of my Mistress, my Goddess.

After I've been working about 15 minutes, and done each of Zara's feet twice, Kassandra is getting impatient.

"I want my turn," she says sharply.

"Alright," says Zara. Then to me, "Switch to your sister's feet now."

I move over to Kassandra's feet, and she puts her left foot in my lap. Her feet are size 9, with high arches, long elegant toes, smooth heels, and creamy soles. Her nails are painted brick red. I use the same massage technique, working slowly and carefully with both thumbs.

"He's really good at this," she says to Zara, as I finish her right foot for the second time. She withdraws it and presents her left again.

"He'd better be," says Zara, "or I _will_ call half a dozen of my girlfriends to come over and tickle him all night."

They both laugh, as I gently roll the toes of Kassandra's left foot, my armpits and diaphragm still sore from my earlier tickling. I strive to give an excellent massage, and to please her.

Kassandra looks at her watch, withdraws her foot, and speaks to me.

"You're a fine masseur, little brother, but your break is over. Now it's tickle time again, and you're going to get it worse than ever. We're going to tickle you insane, we're going to drive you mad with tickling!"

"Yes," adds Zara, "we'll tickle you non-stop until Monday night. We'll drive you crazy with tickle torture!"

Then she looks at her watch, and her expression changes. She is no longer Zara-the-babysitter; she is again Mistress Zara.

"The role play is over," says Mistress Zara. "We'll resume it the next time we have a joint session. Get the dice, slave."

I go to my bag and bring a small plastic case with six dice. I hand her the case. I wait on my hands and knees.

"First, we'll determine your fate," says Mistress Zara. She takes two dice for herself, and hands one die to Mistress Kassandra. I close my eyes without before she orders it, and I hear dice rolling.

"Open your eyes, slave. You may have the sum of my two dice, or you may have Mistress Kassandra's. I'd advise you against mine."

I can see that both of her fists are closed, as is one of Kassandra's. I decide to trust her advice, and say that I'll choose Mistress Kassandra's. She opens her fist, and shows me a '4'.

"Wise choice," says Mistress Zara, opening her fists and showing me a '1' and a '2'.

"I know what that means," says Mistress Kassandra, grinning.

This is not our first joint session with her, and she knows the meaning of the '4'. Between now and my next session with Mistress Zara, in two weeks, I will be permitted to gratify myself only four times. I must record each such event in writing, and record my thanks to Mistress Zara for the permission.

"Only four times in fourteen days, how will you manage it?" asks Mistress Kassandra, with a smirk on her face.

"I take cold showers when I need to, Mistress Kassandra," I say, "because I would _never_ disobey Mistress Zara by going over my quota. I'm not allowed to go under it, either. It must be exactly four. To show that I belong to Mistress Zara, totally, even when I am not with her. To show that she owns my sexuality."

Mistress Zara nods, with approval. The one time that I did go over my quota, she punished me severely. In a way that I don't even like to think about.

"Any requests, slave?" asks Mistress Zara.

"I most humbly beg for permission to lick your soles, Mistress." I say.

"Well," says Mistress Zara, "we did give you quite a thorough tickling. So I'll be generous to you. You may lick my soles, and Mistress Kassandra's soles also."

Mistress Kassandra nods, and gives me a big smile.

"Oh thank you, Mistress," I say. It is rare that she allows me to lick another woman's soles.

"Roll two dice. Would you rather have the sum, or the product? You must answer _before_ you roll."

"The product," I say, hoping not to roll a '1' on either die.

I am very lucky indeed. I roll a '5' and a '6'.

"Thirty!" I exclaim happily.

"You may begin," says Mistress Zara, putting her left foot in my lap.

I hold the foot in both hands, and give it thirty licks, along the whole length of the sole, from the back of the heel to the tips of the toes, with my tongue fully extended. I count each lick out loud as its done, and end like this:

"29."

"30. Thank you ever so much, Mistress. I most humbly beg your permission to lick your other foot."

"You may," she says, graciously, extending her right foot to me.

I am once again in heaven, as I lick and lick her sole, savoring the flavor and feel of it, as I count off the thirty licks. I thank her again when I am finished.

I move over the Mistress Kassandra's feet, and address her.

"I most humbly beg for permission to lick your soles, Mistress Kassandra."

"You may begin," she says sweetly, putting her right foot near my face.

I use the same technique, with full tongue extention, licking slowly from the back of her heel to the tips of her toes. She giggles a little, she is so ticklish on her feet. Her feet taste a little saltier than Mistress Zara's, and, of course, each lick is longer. I count out loud, and thank her after the thirtieth.

"Thank you so much for allowing me to lick your sole, Mistress Kassandra. I most humbly beg for permission to lick the other sole."

"You may," she says, smiling as she extends her left foot.

After the last thirty long, slow licks I look up and smile at both of them.

"Thank you both, ever so much, for being so kind as to allow me to lick your very lovely soles. I am most grateful to you."

"You're welcome, slave," says Mistress Zara, "and now lie down."

"It was a pleasure," says Mistress Kassandra, "getting a nice tongue bath on my soles."

I lie down, on my back, on the rug. Both of them put their bare feet on me. Mistress Zara has one foot on my forehead, and one foot over my mouth. She orders me to keep my lips shut. Mistress Kassandra has one foot on my chest. With the ball of her other foot, she strokes my genitals, very softly. Within a minute, I have a firm erection. She sees this, and stops. She lets the foot rest on my thigh.

"I've made sure that he'll use up one of his four permissions tonight," she says. Both of them laugh. I am in heaven, with four beautiful bare feet pressing down on me.

Alas, the time has now expired, and I must dress and go home. It will be two weeks until I next see my beloved Mistress Zara.

The End

Mistress Zara has a website, and it can be found here:

http://www.mistresszaranyc.com/

Mistress Kassandra has a website, and it can be found here:

http://mistress_kassandra.tripod.com/

My earlier story about a session with Mistress Zara, entitled "The Session (F/m)", can be found here:

http://www.ticklingforum.com/showthread.php?s=&threadid=12717

Some of my other stories are available here:

"Sisters (F/m)"
http://www.ticklingforum.com/showthread.php?s=&threadid=15910

"Cousin Laura's Revenge (F/m)"
http://www.ticklingforum.com/showthread.php?s=&threadid=13731

"Ted's Big Break (F/m)"
http://www.ticklingforum.com/showthread.php?s=&threadid=15171

"A Great Summer (F/m)"
http://www.ticklingforum.com/showthread.php?s=&threadid=14620

"The Free Ride (F/m)"
http://www.ticklingforum.com/showthread.php?s=&threadid=16965

"Help for Bobby (F/m)"
http://www.ticklingforum.com/showthread.php?s=&threadid=18395

4 hands

Man, that guy had endurance!! I don't go in for the licking part of the soles, but the endless tickling (of course, I don't know how long my version of endless could be) was something to be commended.

My favorite part, too, is the way that they talked to him. Egging someone on in a lee position has got to be one of the best parts of the whole thing.

Kathie

I'm glad that you enjoyed the story, Kathie. 🙂

That guy was me. I was tickled senseless; when they were done with me, I was too weak to stand up, and thoroughly disoriented.

The session took place in The Hidden Chamber, a dungeon here in Manhattan, on August 8, 2002. I have some polaroids to help me remember the wonderful experience.

Both Mistress Zara and Mistress Kassandra know that I love to be taunted while they're tickling me, so they did a lot of it.😀

Endurance to the max

Hi!!🙂

I'm glad that you identified yourself in the story. Sounds like a great experience and I am glad that you lived to tell it.

Madame Z and Madame K sound very sadistic and yet they are giving men what they want. I don't know that I could do that as far as not letting up on someone when I see that they are about to pass out from laughing too hard. Of course, I want to be in your position as far as being the "victim" and yet I don't know if I am totally comfortable with that yet.

Can't wait for a gathering and experience a lot of this first "hand". (No pun intended)😀

Kathie

wow!

I gotta say, that was an amazing story. As an f/m fan, and admirer or those two beauties you enjoyed your time with, I gotta say I'm extremely jealous! LOL, Kassandra and Zara are gorgeous and seem to thoroughly enjoy tickle torturing - I agree with you, the verbal taunting intensifies the experience for sure. Great stuff!

wow did i love how they taunted you milagros. the anticipation beforehand is such a turn on for me. well written as ever and i can see why it won the golden feather. you are one lucky man to have two such beautiful Mistresses. truly a fantasy come true.

isabeau 🙂

only just read this one, Mils--thanks------ great story