I'd like to start off by mentioning that Jenni The Clown Stories inspired me to actually start writing stuff lol. Thanks Jenni <3
Señora Rosario was by everyone's opinion a very serious regional prosecutor in Puerto Rico. The Legal system and the courts only ever saw her in power suits and very serious attire. Like any other self respecting Boricua she was very much proud and traditionally Latina. Her skin was slightly tan due to the sun, she had semi-long black hair and Sabache (black) eyes. After some time in the juvenile correctional facility and public defense she established her own private services, kept to herself and lived a very private life... there was a reason for it...
Lorena Rosario had a hobby, one she was very skilled at keeping under wraps. In Puerto Rico there was a wing in juvenile detention for those above the age of eighteen that were in the process of transferring to adult prison in Bayamon or Ponce, she was tasked in running that entire department. Rosario was the one who decided if and when an inmate could transfer and even could commute sentence into probation with only her packet.
What no one would have possibly imagined is that she abused her power to have something she wanted.
It was very simple, she would find out if the convict was ticklish, would offer a plea and a guarantee of probation and since they were, before, minors, none of this would even appear on the permanent record.
Damn good deal.... There was a catch.
They would have scheduled reviews with their social worker, who was Her, where she would collect her part of the bargain....
Gabriel was about to turn nineteen, had been in Detention the entire time because of a technicality. Depending on the report of the Juvie Social Worker, he would either be moved to Adults or be given probation of nine months with conditional release. He was of average height, dirty blonde hair, on the skinny side, huge lips, dark eyes and average looking to most.
He was moved to the office of Mrs. Rosario with those classic Kung Fu slippers from prison. He seemed aloof when he sat down, daydreaming almost, Lawyer had told him that he would most likely be moving to adult prison and after a year he would be done....
Rosario had Official Barbara as her assistant basically, she specifically requested her for one reason. Barbara patted down every single inmate before and after coming into her office incredibly thoroughly, when she did she did so in a way that would definitely tickle those who were ticklish.
She patted their sides deep, made them take off their shoes and patted their soles, if an inmate was ticklish at all when Barbara patted them down they would most certainly laugh or giggle.
Gabriel could be heard giggling twice and even one slightly too loud squirm right outside her door....
She did her job, filled out all the questions, nothing out of the ordinary for the entire interview... At the end, making sure that the wing was empty, timing when Barbara went for her coffee... She made Gabriel a Proposal.
"Gabriel eres cosquilloso?" She asked, straight to the point. As she did, she leaned back on her chair and observed how he snapped out of his daydream, cocked his head and looked at her with a very slight look of confusion.
"I think so yeah, why do you ask Ma'am?" He answered, it was clear that he didn't think anything of it. She moved her chair to the side, got a little closer and very seriously gestured to his feet and to to her lap.
"Tus pies porfavor, quitate las medias y los zapatos" She commanded, calmly but very much like it was procedure. Gabriel shrugged, thinking this just part of his medical records, removed his slippers and socks and placed both his feet on her lap.
Lorena took her pen, a very expensive looking thing and traced the tip from his heel to his big toe on just one foot. The Young Man reacted by giggling and snorting, taking his foot off her lap before it could touch his big toe and blushed in embarrassment. She smiled, took a packet from her desk and regarded the young man kindly.
"I'm going to recommend you for conditional release, I'll be your social worker on the outside, You will meet with me monthly and, provided you behave accordingly, don't do drugs and don't get in trouble, you'll be free in nine months"
His face contorted in a mix of surprise and confusion but quickly turned into excitement. He would be going home, today! He thanked her profusely, signed all the papers and got ready to shower and head to the outside... but before he left, His new social worker gave him a reminder... and a little reminder....
"You come to all my appointments, you behave, you follow my program or you're back here... in the adult prison Gabriel." She told him seriously and she meant it, but Gabriel would do anything to get out of there and this was better than anything he could have hoped for!
Two Months Later....
Today was the first appointment with Mrs. Rosario, He didn't think much of it, didn't even think twice that instead of scheduling him at the courthouse she brought him to her personal office in Mayaguez. It was a pretty basic lawyer office, fancy sofa, secretary, the works. He came dressed formally, dress shoes, tie and all, He didn't suspect a thing when he stepped inside her office to find something more akin to a psychologists office.
She looked far more welcoming here, gesturing for him to lay on the leaning chair that psykes had.
"All good Mr. Rivera? Staying out of trouble?" He said, pulling out some papers, filling them out and waiting for him to sit and lay down. "Quitate los zapatos en mi officina Gabriel"
He didn't think anything of it when she requested him to remove his shoes at the door, sat down, laid in the therapy sofa thing and nodded back with a smile. "Absolutely Missus Rosario, been taking it easy and staying at home"
She nodded, stayed silent for a while, finished up her papers and finally turned to him while he had his feet kicked up on the chair.
"You were supposed to go straight to La Cuchara, Because of my packet Mr. Rivera you get to not only have a clean record but, not be in prison or detention anymore..."
She rolled her chair to the foot of the sofa where both of his socked feet were placed. He looked at her with a curious look that turned into a smile and then a loud giggle when her nails touched his soles. "Te acuerdas cuando te pregunte si eras cosquilloso Gabriel?"
The young man recoiled his feet, smiled, blushed and turned to answer her question, still not fully knowing what she was planning. "Yeah... I do, I am, why?"
She didn't respond, instead, gestured back to the edge of the sofa and his feet, until he placed them gingerly back next to her nails.
"Our appointments Gabriel will be from four to five, every month you complete I have to send this packet saying your progress is to my liking." She smiled, slowly poking his toes before continuing.
"And if you are a good and ticklish boy, I'll gladly do that for you... after I've tickled you to my leasiure... Ese es mi trato... Si no estas de acuerdo... facilmente vuelves a la correcional..."
Gabriel blinked, her words being the most unexpected thing he had ever heard. This Woman had freed him, after finding out he was ticklish, for the specific purpose of tickling him in exchange for his freedom. He thought about it, almost blank in his mind, after a while he stammered.
"Cosquillas?... Me quieres hacer Cosquillas?... Nada mas?..." He said sheepishly, a little afraid there was something hidden she wasn't telling him.
She smiled, shook her head and went back to her desk.
"That's it. Is it a deal Mr. Rivera...?"
Not that he had much of a choice... It was much better than prison, The Idea itself so random and out of this world that he shrugged, nodded and blushed. "Ok but I'm really ticklish I, I might kick you or something by accide-"
Rosario held up her hand, having heard all she needed to hear and calmly stood up. "Don't worry about that, take off your socks and place them over here..."
Rosario opened her Cabinet and pulled out a medium size stock, wooden, fancy looking, moved it to the center of her office in front of Gabriel. Now, finally, he knew what he was going to go through, he had never actually been tickled for more than a second and couldn't imagine what that was even like...
For the next few minutes Mrs Rosario took his feet and placed them on the stocks, cuffed his hands behind his back making him unable to reach or move his lower body. His soles were pale, soft, large and very well shaped, on the top of these medieval stocks were rings with thin strings, Mrs. Rosario began to lop those strings across each one of his toes.
Gabriel had never felt anything quite like that, it tickled, it tickled a lot, even just her lightly tying around his toes made him giggle at first, then squeal and finally laugh out loud. He was far more sensitive than he thought, even those light grazes were making him laugh and writhe, trying to pull away by instinct but no luck.
When she was done he realized what those strings were for, to keep his feet from being able to scrunch at all. When she was done, she glared at her handiwork, gave him a look of malice and smiled.
"Eres cosquilloso?" She said, sliding one nail from his heel to his big toe. It was like electric dynamite, it send him in a giggling, laughing mess almost instantly. The first session Gabriel endured lasted only a few more minutes, was entierly too much for him and put into perspective just how ticklish he was...
"Esto es solo una pequeña demostración y hoy te dejare ir más temprano y sin sudar... El próximo Mes, es tu primer día como mi cosquilloso..."
Her warning, ominous as it was... Was Fair...
One Month Later, Gabriel was scheduled to meet her in Isla Icacos, a lone Island off the coast of Culebra, where she had set up a small bungalo, a tent, one lancha and the entire Island, as it usually is, bereft of people.
The Luxurious Boat, several drinks, new clothes and pockets money had Gabriel in a much better mood, for the entire day she just let him have as much booze and fun as he wanted. From Jetskis, to Waveboarding... just as planned...Gabriel had forgotten why he was here....
"Gabriel, whenever you are ready I will be in the big tent" Mrs. Rosario said, serious but with a friendly smile. It took him a while, a good while, but his smile turned to dread when he remembered what she truly had him here for... Why she had him get pedicured, manicured and all kinds of spas... but.... she was fair... It was a deal... and not yet in any kind too much for the Young Man.
Out of sight of the shore, Mrs Rosario had a arabia like tent that was at least fifty meters on all sides and looked rather cool. Golden silk, white floor, torches with anti mosquito oil... The Song of Storms from the Legend of Zelda playing from inside but by some sort of musical orchestra...
"Nice Taste in Music Mrs. Rosario!" Gabby said, smiling and taking a step into her massive tent.
"Take off your shoeware inside please, oh, and Call me Lorena" She spoke very aloof, laying in her absolutely massive pile of pillows and cushions she called a bed. The inside was quite arabian, with all kinds of fancy drapes, rugged and smelling of very cool insence.
Gabriel did as he was told, removed his shoes and walked in. To his right was a very exotic looking Tiki statue and next to that were feathers, brushes and all kinds of ropes and tickling tools. He swallowed hard. "You're going to tickle me Lorena?" He stammered, his nervousness clear and palpable.
She Rose from her decadent throne, long feather in hand and chuckled very softly. "And nothing on earth can stop me!" She said both matter of factly and playfully. "Today is your first actual tickling by me, Today you learn what being my little cosquilloso is... I do really like you... and I want to be a little nice... so...'
She stood, naked from the waist down, wearing nothing by ancient traditional Puerto Rican red dress and sported a red flower on her left ear. The Flower of Puerto Rico, la flor de maga. Her toes were painted black, she had a necklace made of the bark of flamboyanes and had a bracelet and anklet of pure gold. Her tan skin made all of this look like she was pulled out of Puerto Rican Folklore.
"I'll let you chose this one time... I will only tickle one spot... Your feet or anywhere above your waist... You decide..."
She walked around him, eyeing him from head to toe and sat down beside the Tiki, flaunting the large feather around like a wand, teasing the young man.
Gabby was not expecting a woman this flawless even In her age and be treated so... nice, the choice however was obvious. Being tickled one place versus many others seemed a no brainer but he had never before been actually tickled, in her office it was simply a quick tease and preveiw of this one moment...
"I... My Feet Mrs. Ro-... Lorena..." He said, blushing, nervous, a bit scared and very attracted by Lorena herself. She smiled back and despite herself, she too blushed at the attraction of someone much Younger than her. She slapped her cushion/arabic/Pillow bed and kelt down.
When Gabby sat down She was kneeling by his feet and calmly began tying a golden strings around his ankles. While she did that, either on accident or on purpouse, she tickled the arch and tippy toes of his feet and made him squeal and giggle at the lightest touch. Gabby was more sensitive on his soles than any man,.macho or effeminate she had ever seen... This was too good.
It took her a good time but his ankles werent moving anywhere, his toes were not scrunching or doing much of wiggling at all. She came up to him, noticing his very nervous expresión and calmed it by playing with his hair. She gestured to get his hands above his head, he did so, but when she reached for his wrists he reflexivley pulled it down expecting tickling somewhere in his sides.
Lorena smiled genuinely, shook her head and couldn't help but to laugh. "Ay no te preocupes mi cosquilloso, no te haré daño, pero si te voy a hacer cosquillas hasta que pienses que no puedes más... si es que eres tan cosquilloso como aparenta ser el caso..." She teased, cooing him while tying his hands above his head and securing them above his head and into the base of a large wooden pillar that held the tent in place.
"How many cosquillosos do you have or am I just that special?" He said, nervous but much less, enough to sound like he was charming... even hitting on her... a slight sense of romance and class... smoother even.
"Oh you are special, quite so Gabrielito... You'll meet my others eventually... maybe tomorrow... maybe tonight, im sure you will like my cosquilloso... but for now... You're going to be my ticklee... that's what you call the ticklish victim of the tickler." She smiled, devilishly, sitting by Him and admiring his upper body which was bare...
Gabriel had his swimming trunks, unusually short ones and nothing else. Her black, medium nails seemed to have been trimmed to have pointy ends, and they were head right for his exposed belly. Gabriel, former convict, not the toughest or the bravest but certainly no push over, couldn't help but to giggle and snort... even before her nails even touched him at all...
"Oh I haven't even touched you... besides... I promise I would only tickle your feet remember?"
Lorena pulled both his legs into her lap, his feet dangling slightly off her knees. They looked glossy, shiny, felt soft and looked absolutely amazing.
"Mrs. Ro-... Lorena, I am much more ticklish than you th- hahahahahahha!!!" Gabby instantly broke into childish, loud, screaming, high pitch laughter as Mrs. Rosario began tickling his feet wildly. No man no matter how gentle had ever had this ticklish feet... he bucked wildly, kicked and squirmed quite a bit, his feet were quite fiesty! She did have a solution...
She stopped after a few moments into her ticklish assault and already he was giggling, panting, gasping and seemingly ready to pop. She had barely tickled me for a few seconds and I don't think I can handle a lot! Why did I chose my feet!? I have to switch! Anything is better! Gabriel thought to himself....through giggles... after he caught his breath...
"Wait... Mrs. Rosario can you tickle my upper body please? Is it too late to change my mind? Please... I don't think I can handle my feet being tickled..." He asked, she was seemingly in a good mood... she had asked him, it should go his way.
Lorena, shook her head, tied the bottom of the linen on his ankles tight below her bed, making both his feet immobile, his toes pulled back... he could only slightly wiggle them from side to side. "Im a woman of my word, I expect the same courtesy my cosquilloso..."
Without warning Lorena began to tickle his heels, the calloused spot still sending him into a fit of giggles and yelps. I'm between each one he baerly managed a 'Please!' And 'Not the Feet!' In both Spanish and English... which was wonderful to hear. She let him feel the tickling In his heels before moving to the outside arch and the edges of his feet, both of them, at the same time.
The volume was raised almost double, the begging was at least tripled and the gigglesnorts began. "Oh you are a sensitive boy aren't you? Are you my Cosquilloso En Los Pies? Si?"
The teasing was quite effective but her relentless tickling of his outside arches was slowly making him squeal quite girlishly, something he was not happy about. He refused to say anything she wanted, his pride being tested, it was the sound of his own girly voice that made him stubborn! It did not last however... it did not last a single minute.
Lorena kept going, around the edges of his soles, pricking, tracing, poking and just outright tickling the very edge of his feet. "Ok! Ok!! Soy Tu Cosquilloso en los pies! Ya!!! Enouhuhuhahahah!!!"
As soon as she said what Lorena wanted she went straight into the arch of his foot, going around the center, above the heels and then back down. This made the young man explode in desperate loud laughter. She wasnt tickling him hard or digging in rather tracing her fingers softly but firmly up and down his arches. She sometimes poke him, sometimes trace and scratch a spot that had a good reaction... mainly the very middle and then, nonchalantly keep going, almost aloof.
"Do you know another language mi cosquilloso? If you tell me You like tickling in any other language... You'll. get a break and a prize..." She cooed, he probably, most definitely, did not know a third language, so, she kept going and going. She never stopped, never showed down, simply traced his helpless arches over and over.
At first he tried to beg but his ticklishness kept him from Even forming complete sentences. Just being lightly tickled like this was enough to break him? He could't really grasp it, but he would do or say anything for even the slightest repreive... When the chance came, when she tickled his heels, giving him the faintest moment, he shouted in clear italian. "mi piace essere solleticato!!!"
His efforrt granted him sudden reprieve from the tickling torture. His size ten soles were quivering, their soles tight and red, nothing on them as they hadn't been scratched or roughly tickled at all. Lorena actually had her jaw slightly open... He knew Italian...
How absolutely perfect. "meraviglioso, esaudirò il tuo desiderio ma a una condizione." She smiled, sat back and took out a large, Crystal vase filled with a nice smelling oil.
"I will grant your feet a nice long rest, I won't tickle them while I massage them. But..." She smiled, massaging his bare soles with this oil that smelled of guayaba or tamarindo, or both. "Someone else will tickle you... not in your feet as you requested.... Trato? Mi cosquilloso?"
She massaged me so good, so skillfully and with something that felt so good I would have said yes to anything she said... except my feet being tickled again. I nodded and relaxed, wiggling my toes in her fingers while she catered my soles.
Almost afraid to ask I sheepishly query. "Si tu no me vas... a hacer las cosquillas... quien vas a dejar que me Haga Cosquillas...? Mrs. Ro-..." He smiled, fighting back a giggle as she went between his toes with her oily fingers. She did that on purpouse...
"Lorena... soy demasiado... I'm too ticklish and I don't think I can take much... ahhhh.... That Feels... what is that?" He could't see her put her toes in his mouth while she deeply massaged him. It felt good, really good, whatever it was, Loreena was very aroused while she did this to ticklish men with cute feet and soles.
"I know you are, which is why I'll let you go back to your feet and chose your tickle spot for today... As for who te viene a hacer cosquillas?" On cue, someone entered the tent, then another person entered the tent. He couldn't see them until they started mumbling something, they sounded like males.
"Yo te dije de mis cosquillosos, creo que los vas a conocer. De Arecibo Vasco y de Ciales Cofresi. These two will take over while I sit and enjoy... please do tell me if you miss me Gabby..."
The massage stopped, I felt two figured approach me, to my sides. One was tall, blonde and very physically fit, not large but tones and fit. The other was an average, skinny, Black haired boy no way older than I was. They were talking another language, not italian or Spanish or English and they seemed to be pointing at several of my body parts, smiling to each other as they did.
"Wait, guys, Vasco? Cofresi? I don't like men ok? I would much prefer Mrs. Rosario and also I am way to sensitive. You might hurt me or, I have no idea, I'm not conf-WHAHAHAHAHAHHA!!!!"
Vasco went under my shirt, squeezing the little bone at the edge of my hips, Cofresi did the same. I don't remember being ticklish there, I never knew how bad it truly was, they were both giggling at my screams of ticklish agony. After a few seconds they let go, I caught my breath, began to form a sentence to beg when they did it again, making me scream and squeal like I was being murdered.
"You ticklish here little guy?" The blonde one said while gently tracing his hands beneath my shirt and tickled my chest and sides.
"Y en el ombligo papi? Te da risa? Cual es peor?"
The Black haired one began tracing his hands around my bellybutton and under, then around my belly.
I nodded, screaming, laughing, tears flowing down my face as they just played with my upper body. I couldn't beg, I had no air! It was quickly when I got a breather, to my despair, they came close to my ears, both of them, and whispered a bunch of questions. It tickled... quite a bit... giggling and blushing as these two guys were teasing and basically emasculating me. I felt... So Humiliated by them, as they made of me say or do whatever they pleased! And what they pleased was to see me literally tickle tortured into oblivion!!! Surely it would end!! Perhaps... if I asked for my feet being tickled?
"Donde te da más cosquillas papito? En Los Pies? En el obligo?"
"Where are you most ticklish? Where does it tickle most? Is it your feet? Your belly button? You can tell me Babe.."
While they whispered they graced and traced one hand across my bound body and they tickled and teased everywhere that made me giggle, then they would leave and go somewhere else. I was too ticklish, even for all of this light grazing...
"Plehehease!!! Ill do anything! Please!! Stop! I cahahahant tahahahake it!!!"
It was one of the many begs I had done today, but it worked... they did indeed stop... They giggled in satisfacción as they got up and sat on either side of my feet.
"Ya casi se acaba mi cosquilloso Gabrielito, pero, debes escojer una cosa. Piensalo como un juego..." Came the seductive voice of Mrs. Lorena Rosario.
"Pick a Color of one of my feathers... red, blue or green... and it will decide who and where your tickles will end... sound fair?"
I nodded. But I couldn't take much more... surely she had to see that, surely she cared.... "Red... please... I can't take more, I need a break...."
I couldn't see her smile, but Loreena did smile and nodded to her two men, then she left. They sat back down next to me and slowly began to comfort me, playing with my hair, patting me and otherwise making it feel like everything was fine now.
"It's all over, it's all downhill from here. My name is Vasco, I won't tickle torture you anymore." His smile was devilishly geniune.
"Yo si te voy hacer cosquillas, y no voy a parar hasta que te vengas Papi. Así que, vamos a ver cuanto duras... te da cosquillas en las bolas? O en el bicho?"
I tried to protest but the blonde, caring, very strong one put a single finger on my lips. The good con bad con routine was working and my parts were unbuttoned and my member was exposed. I was not gay, nor was I ticklish in my balls or dick like Cofresi asked, so I felt uncomfortable and weird being fondled by two men... still... better than being tickle tortured once again.
"I'm not gay guys, with all respect you won't get what you're after so- HAHAHAH! WHAT was THAT!?"
I had never actually been tickled in my balls or shaft by a feather but that came from my ass! They had a small little feather in between my butt cheeks and it was tickling my ass so, so much.
"That's a shame cause red feather means tickled until you orgasm, or faint. So..." Vasco said, cradling my head and moving his hands into my parts.
"Yo apuesto a que eres cosquilloso en el Nie" Cofresi said as he moved the tiny feather to that spot between your dick and your ass, the Nie. It was instant, like a Bolt of lighting, I tried to move but they spread me and pinned me to really zero in to that spot.
No one had ever touched me there, much less tickled me, I begged and pleaded and screamed for a while but they kept tickling this one spot like actual torture. I'm not entirely sure why but after what must have been ten minutes of relentless tickling in that área I did get an erection.
I did not want to let two men make me orgasm... but I had no idea that when erect my balls were ticklish. While Vasco held me down Cofresi cradled my balls and lightly grazed them with the tip of his manicured hands. I broke long ago, I couldn't orgasm on command with that, so I just had to beg, plead and scream until finally... mercifully, I orgasmed.
Señora Rosario was by everyone's opinion a very serious regional prosecutor in Puerto Rico. The Legal system and the courts only ever saw her in power suits and very serious attire. Like any other self respecting Boricua she was very much proud and traditionally Latina. Her skin was slightly tan due to the sun, she had semi-long black hair and Sabache (black) eyes. After some time in the juvenile correctional facility and public defense she established her own private services, kept to herself and lived a very private life... there was a reason for it...
Lorena Rosario had a hobby, one she was very skilled at keeping under wraps. In Puerto Rico there was a wing in juvenile detention for those above the age of eighteen that were in the process of transferring to adult prison in Bayamon or Ponce, she was tasked in running that entire department. Rosario was the one who decided if and when an inmate could transfer and even could commute sentence into probation with only her packet.
What no one would have possibly imagined is that she abused her power to have something she wanted.
It was very simple, she would find out if the convict was ticklish, would offer a plea and a guarantee of probation and since they were, before, minors, none of this would even appear on the permanent record.
Damn good deal.... There was a catch.
They would have scheduled reviews with their social worker, who was Her, where she would collect her part of the bargain....
Gabriel was about to turn nineteen, had been in Detention the entire time because of a technicality. Depending on the report of the Juvie Social Worker, he would either be moved to Adults or be given probation of nine months with conditional release. He was of average height, dirty blonde hair, on the skinny side, huge lips, dark eyes and average looking to most.
He was moved to the office of Mrs. Rosario with those classic Kung Fu slippers from prison. He seemed aloof when he sat down, daydreaming almost, Lawyer had told him that he would most likely be moving to adult prison and after a year he would be done....
Rosario had Official Barbara as her assistant basically, she specifically requested her for one reason. Barbara patted down every single inmate before and after coming into her office incredibly thoroughly, when she did she did so in a way that would definitely tickle those who were ticklish.
She patted their sides deep, made them take off their shoes and patted their soles, if an inmate was ticklish at all when Barbara patted them down they would most certainly laugh or giggle.
Gabriel could be heard giggling twice and even one slightly too loud squirm right outside her door....
She did her job, filled out all the questions, nothing out of the ordinary for the entire interview... At the end, making sure that the wing was empty, timing when Barbara went for her coffee... She made Gabriel a Proposal.
"Gabriel eres cosquilloso?" She asked, straight to the point. As she did, she leaned back on her chair and observed how he snapped out of his daydream, cocked his head and looked at her with a very slight look of confusion.
"I think so yeah, why do you ask Ma'am?" He answered, it was clear that he didn't think anything of it. She moved her chair to the side, got a little closer and very seriously gestured to his feet and to to her lap.
"Tus pies porfavor, quitate las medias y los zapatos" She commanded, calmly but very much like it was procedure. Gabriel shrugged, thinking this just part of his medical records, removed his slippers and socks and placed both his feet on her lap.
Lorena took her pen, a very expensive looking thing and traced the tip from his heel to his big toe on just one foot. The Young Man reacted by giggling and snorting, taking his foot off her lap before it could touch his big toe and blushed in embarrassment. She smiled, took a packet from her desk and regarded the young man kindly.
"I'm going to recommend you for conditional release, I'll be your social worker on the outside, You will meet with me monthly and, provided you behave accordingly, don't do drugs and don't get in trouble, you'll be free in nine months"
His face contorted in a mix of surprise and confusion but quickly turned into excitement. He would be going home, today! He thanked her profusely, signed all the papers and got ready to shower and head to the outside... but before he left, His new social worker gave him a reminder... and a little reminder....
"You come to all my appointments, you behave, you follow my program or you're back here... in the adult prison Gabriel." She told him seriously and she meant it, but Gabriel would do anything to get out of there and this was better than anything he could have hoped for!
Two Months Later....
Today was the first appointment with Mrs. Rosario, He didn't think much of it, didn't even think twice that instead of scheduling him at the courthouse she brought him to her personal office in Mayaguez. It was a pretty basic lawyer office, fancy sofa, secretary, the works. He came dressed formally, dress shoes, tie and all, He didn't suspect a thing when he stepped inside her office to find something more akin to a psychologists office.
She looked far more welcoming here, gesturing for him to lay on the leaning chair that psykes had.
"All good Mr. Rivera? Staying out of trouble?" He said, pulling out some papers, filling them out and waiting for him to sit and lay down. "Quitate los zapatos en mi officina Gabriel"
He didn't think anything of it when she requested him to remove his shoes at the door, sat down, laid in the therapy sofa thing and nodded back with a smile. "Absolutely Missus Rosario, been taking it easy and staying at home"
She nodded, stayed silent for a while, finished up her papers and finally turned to him while he had his feet kicked up on the chair.
"You were supposed to go straight to La Cuchara, Because of my packet Mr. Rivera you get to not only have a clean record but, not be in prison or detention anymore..."
She rolled her chair to the foot of the sofa where both of his socked feet were placed. He looked at her with a curious look that turned into a smile and then a loud giggle when her nails touched his soles. "Te acuerdas cuando te pregunte si eras cosquilloso Gabriel?"
The young man recoiled his feet, smiled, blushed and turned to answer her question, still not fully knowing what she was planning. "Yeah... I do, I am, why?"
She didn't respond, instead, gestured back to the edge of the sofa and his feet, until he placed them gingerly back next to her nails.
"Our appointments Gabriel will be from four to five, every month you complete I have to send this packet saying your progress is to my liking." She smiled, slowly poking his toes before continuing.
"And if you are a good and ticklish boy, I'll gladly do that for you... after I've tickled you to my leasiure... Ese es mi trato... Si no estas de acuerdo... facilmente vuelves a la correcional..."
Gabriel blinked, her words being the most unexpected thing he had ever heard. This Woman had freed him, after finding out he was ticklish, for the specific purpose of tickling him in exchange for his freedom. He thought about it, almost blank in his mind, after a while he stammered.
"Cosquillas?... Me quieres hacer Cosquillas?... Nada mas?..." He said sheepishly, a little afraid there was something hidden she wasn't telling him.
She smiled, shook her head and went back to her desk.
"That's it. Is it a deal Mr. Rivera...?"
Not that he had much of a choice... It was much better than prison, The Idea itself so random and out of this world that he shrugged, nodded and blushed. "Ok but I'm really ticklish I, I might kick you or something by accide-"
Rosario held up her hand, having heard all she needed to hear and calmly stood up. "Don't worry about that, take off your socks and place them over here..."
Rosario opened her Cabinet and pulled out a medium size stock, wooden, fancy looking, moved it to the center of her office in front of Gabriel. Now, finally, he knew what he was going to go through, he had never actually been tickled for more than a second and couldn't imagine what that was even like...
For the next few minutes Mrs Rosario took his feet and placed them on the stocks, cuffed his hands behind his back making him unable to reach or move his lower body. His soles were pale, soft, large and very well shaped, on the top of these medieval stocks were rings with thin strings, Mrs. Rosario began to lop those strings across each one of his toes.
Gabriel had never felt anything quite like that, it tickled, it tickled a lot, even just her lightly tying around his toes made him giggle at first, then squeal and finally laugh out loud. He was far more sensitive than he thought, even those light grazes were making him laugh and writhe, trying to pull away by instinct but no luck.
When she was done he realized what those strings were for, to keep his feet from being able to scrunch at all. When she was done, she glared at her handiwork, gave him a look of malice and smiled.
"Eres cosquilloso?" She said, sliding one nail from his heel to his big toe. It was like electric dynamite, it send him in a giggling, laughing mess almost instantly. The first session Gabriel endured lasted only a few more minutes, was entierly too much for him and put into perspective just how ticklish he was...
"Esto es solo una pequeña demostración y hoy te dejare ir más temprano y sin sudar... El próximo Mes, es tu primer día como mi cosquilloso..."
Her warning, ominous as it was... Was Fair...
One Month Later, Gabriel was scheduled to meet her in Isla Icacos, a lone Island off the coast of Culebra, where she had set up a small bungalo, a tent, one lancha and the entire Island, as it usually is, bereft of people.
The Luxurious Boat, several drinks, new clothes and pockets money had Gabriel in a much better mood, for the entire day she just let him have as much booze and fun as he wanted. From Jetskis, to Waveboarding... just as planned...Gabriel had forgotten why he was here....
"Gabriel, whenever you are ready I will be in the big tent" Mrs. Rosario said, serious but with a friendly smile. It took him a while, a good while, but his smile turned to dread when he remembered what she truly had him here for... Why she had him get pedicured, manicured and all kinds of spas... but.... she was fair... It was a deal... and not yet in any kind too much for the Young Man.
Out of sight of the shore, Mrs Rosario had a arabia like tent that was at least fifty meters on all sides and looked rather cool. Golden silk, white floor, torches with anti mosquito oil... The Song of Storms from the Legend of Zelda playing from inside but by some sort of musical orchestra...
"Nice Taste in Music Mrs. Rosario!" Gabby said, smiling and taking a step into her massive tent.
"Take off your shoeware inside please, oh, and Call me Lorena" She spoke very aloof, laying in her absolutely massive pile of pillows and cushions she called a bed. The inside was quite arabian, with all kinds of fancy drapes, rugged and smelling of very cool insence.
Gabriel did as he was told, removed his shoes and walked in. To his right was a very exotic looking Tiki statue and next to that were feathers, brushes and all kinds of ropes and tickling tools. He swallowed hard. "You're going to tickle me Lorena?" He stammered, his nervousness clear and palpable.
She Rose from her decadent throne, long feather in hand and chuckled very softly. "And nothing on earth can stop me!" She said both matter of factly and playfully. "Today is your first actual tickling by me, Today you learn what being my little cosquilloso is... I do really like you... and I want to be a little nice... so...'
She stood, naked from the waist down, wearing nothing by ancient traditional Puerto Rican red dress and sported a red flower on her left ear. The Flower of Puerto Rico, la flor de maga. Her toes were painted black, she had a necklace made of the bark of flamboyanes and had a bracelet and anklet of pure gold. Her tan skin made all of this look like she was pulled out of Puerto Rican Folklore.
"I'll let you chose this one time... I will only tickle one spot... Your feet or anywhere above your waist... You decide..."
She walked around him, eyeing him from head to toe and sat down beside the Tiki, flaunting the large feather around like a wand, teasing the young man.
Gabby was not expecting a woman this flawless even In her age and be treated so... nice, the choice however was obvious. Being tickled one place versus many others seemed a no brainer but he had never before been actually tickled, in her office it was simply a quick tease and preveiw of this one moment...
"I... My Feet Mrs. Ro-... Lorena..." He said, blushing, nervous, a bit scared and very attracted by Lorena herself. She smiled back and despite herself, she too blushed at the attraction of someone much Younger than her. She slapped her cushion/arabic/Pillow bed and kelt down.
When Gabby sat down She was kneeling by his feet and calmly began tying a golden strings around his ankles. While she did that, either on accident or on purpouse, she tickled the arch and tippy toes of his feet and made him squeal and giggle at the lightest touch. Gabby was more sensitive on his soles than any man,.macho or effeminate she had ever seen... This was too good.
It took her a good time but his ankles werent moving anywhere, his toes were not scrunching or doing much of wiggling at all. She came up to him, noticing his very nervous expresión and calmed it by playing with his hair. She gestured to get his hands above his head, he did so, but when she reached for his wrists he reflexivley pulled it down expecting tickling somewhere in his sides.
Lorena smiled genuinely, shook her head and couldn't help but to laugh. "Ay no te preocupes mi cosquilloso, no te haré daño, pero si te voy a hacer cosquillas hasta que pienses que no puedes más... si es que eres tan cosquilloso como aparenta ser el caso..." She teased, cooing him while tying his hands above his head and securing them above his head and into the base of a large wooden pillar that held the tent in place.
"How many cosquillosos do you have or am I just that special?" He said, nervous but much less, enough to sound like he was charming... even hitting on her... a slight sense of romance and class... smoother even.
"Oh you are special, quite so Gabrielito... You'll meet my others eventually... maybe tomorrow... maybe tonight, im sure you will like my cosquilloso... but for now... You're going to be my ticklee... that's what you call the ticklish victim of the tickler." She smiled, devilishly, sitting by Him and admiring his upper body which was bare...
Gabriel had his swimming trunks, unusually short ones and nothing else. Her black, medium nails seemed to have been trimmed to have pointy ends, and they were head right for his exposed belly. Gabriel, former convict, not the toughest or the bravest but certainly no push over, couldn't help but to giggle and snort... even before her nails even touched him at all...
"Oh I haven't even touched you... besides... I promise I would only tickle your feet remember?"
Lorena pulled both his legs into her lap, his feet dangling slightly off her knees. They looked glossy, shiny, felt soft and looked absolutely amazing.
"Mrs. Ro-... Lorena, I am much more ticklish than you th- hahahahahahha!!!" Gabby instantly broke into childish, loud, screaming, high pitch laughter as Mrs. Rosario began tickling his feet wildly. No man no matter how gentle had ever had this ticklish feet... he bucked wildly, kicked and squirmed quite a bit, his feet were quite fiesty! She did have a solution...
She stopped after a few moments into her ticklish assault and already he was giggling, panting, gasping and seemingly ready to pop. She had barely tickled me for a few seconds and I don't think I can handle a lot! Why did I chose my feet!? I have to switch! Anything is better! Gabriel thought to himself....through giggles... after he caught his breath...
"Wait... Mrs. Rosario can you tickle my upper body please? Is it too late to change my mind? Please... I don't think I can handle my feet being tickled..." He asked, she was seemingly in a good mood... she had asked him, it should go his way.
Lorena, shook her head, tied the bottom of the linen on his ankles tight below her bed, making both his feet immobile, his toes pulled back... he could only slightly wiggle them from side to side. "Im a woman of my word, I expect the same courtesy my cosquilloso..."
Without warning Lorena began to tickle his heels, the calloused spot still sending him into a fit of giggles and yelps. I'm between each one he baerly managed a 'Please!' And 'Not the Feet!' In both Spanish and English... which was wonderful to hear. She let him feel the tickling In his heels before moving to the outside arch and the edges of his feet, both of them, at the same time.
The volume was raised almost double, the begging was at least tripled and the gigglesnorts began. "Oh you are a sensitive boy aren't you? Are you my Cosquilloso En Los Pies? Si?"
The teasing was quite effective but her relentless tickling of his outside arches was slowly making him squeal quite girlishly, something he was not happy about. He refused to say anything she wanted, his pride being tested, it was the sound of his own girly voice that made him stubborn! It did not last however... it did not last a single minute.
Lorena kept going, around the edges of his soles, pricking, tracing, poking and just outright tickling the very edge of his feet. "Ok! Ok!! Soy Tu Cosquilloso en los pies! Ya!!! Enouhuhuhahahah!!!"
As soon as she said what Lorena wanted she went straight into the arch of his foot, going around the center, above the heels and then back down. This made the young man explode in desperate loud laughter. She wasnt tickling him hard or digging in rather tracing her fingers softly but firmly up and down his arches. She sometimes poke him, sometimes trace and scratch a spot that had a good reaction... mainly the very middle and then, nonchalantly keep going, almost aloof.
"Do you know another language mi cosquilloso? If you tell me You like tickling in any other language... You'll. get a break and a prize..." She cooed, he probably, most definitely, did not know a third language, so, she kept going and going. She never stopped, never showed down, simply traced his helpless arches over and over.
At first he tried to beg but his ticklishness kept him from Even forming complete sentences. Just being lightly tickled like this was enough to break him? He could't really grasp it, but he would do or say anything for even the slightest repreive... When the chance came, when she tickled his heels, giving him the faintest moment, he shouted in clear italian. "mi piace essere solleticato!!!"
His efforrt granted him sudden reprieve from the tickling torture. His size ten soles were quivering, their soles tight and red, nothing on them as they hadn't been scratched or roughly tickled at all. Lorena actually had her jaw slightly open... He knew Italian...
How absolutely perfect. "meraviglioso, esaudirò il tuo desiderio ma a una condizione." She smiled, sat back and took out a large, Crystal vase filled with a nice smelling oil.
"I will grant your feet a nice long rest, I won't tickle them while I massage them. But..." She smiled, massaging his bare soles with this oil that smelled of guayaba or tamarindo, or both. "Someone else will tickle you... not in your feet as you requested.... Trato? Mi cosquilloso?"
She massaged me so good, so skillfully and with something that felt so good I would have said yes to anything she said... except my feet being tickled again. I nodded and relaxed, wiggling my toes in her fingers while she catered my soles.
Almost afraid to ask I sheepishly query. "Si tu no me vas... a hacer las cosquillas... quien vas a dejar que me Haga Cosquillas...? Mrs. Ro-..." He smiled, fighting back a giggle as she went between his toes with her oily fingers. She did that on purpouse...
"Lorena... soy demasiado... I'm too ticklish and I don't think I can take much... ahhhh.... That Feels... what is that?" He could't see her put her toes in his mouth while she deeply massaged him. It felt good, really good, whatever it was, Loreena was very aroused while she did this to ticklish men with cute feet and soles.
"I know you are, which is why I'll let you go back to your feet and chose your tickle spot for today... As for who te viene a hacer cosquillas?" On cue, someone entered the tent, then another person entered the tent. He couldn't see them until they started mumbling something, they sounded like males.
"Yo te dije de mis cosquillosos, creo que los vas a conocer. De Arecibo Vasco y de Ciales Cofresi. These two will take over while I sit and enjoy... please do tell me if you miss me Gabby..."
The massage stopped, I felt two figured approach me, to my sides. One was tall, blonde and very physically fit, not large but tones and fit. The other was an average, skinny, Black haired boy no way older than I was. They were talking another language, not italian or Spanish or English and they seemed to be pointing at several of my body parts, smiling to each other as they did.
"Wait, guys, Vasco? Cofresi? I don't like men ok? I would much prefer Mrs. Rosario and also I am way to sensitive. You might hurt me or, I have no idea, I'm not conf-WHAHAHAHAHAHHA!!!!"
Vasco went under my shirt, squeezing the little bone at the edge of my hips, Cofresi did the same. I don't remember being ticklish there, I never knew how bad it truly was, they were both giggling at my screams of ticklish agony. After a few seconds they let go, I caught my breath, began to form a sentence to beg when they did it again, making me scream and squeal like I was being murdered.
"You ticklish here little guy?" The blonde one said while gently tracing his hands beneath my shirt and tickled my chest and sides.
"Y en el ombligo papi? Te da risa? Cual es peor?"
The Black haired one began tracing his hands around my bellybutton and under, then around my belly.
I nodded, screaming, laughing, tears flowing down my face as they just played with my upper body. I couldn't beg, I had no air! It was quickly when I got a breather, to my despair, they came close to my ears, both of them, and whispered a bunch of questions. It tickled... quite a bit... giggling and blushing as these two guys were teasing and basically emasculating me. I felt... So Humiliated by them, as they made of me say or do whatever they pleased! And what they pleased was to see me literally tickle tortured into oblivion!!! Surely it would end!! Perhaps... if I asked for my feet being tickled?
"Donde te da más cosquillas papito? En Los Pies? En el obligo?"
"Where are you most ticklish? Where does it tickle most? Is it your feet? Your belly button? You can tell me Babe.."
While they whispered they graced and traced one hand across my bound body and they tickled and teased everywhere that made me giggle, then they would leave and go somewhere else. I was too ticklish, even for all of this light grazing...
"Plehehease!!! Ill do anything! Please!! Stop! I cahahahant tahahahake it!!!"
It was one of the many begs I had done today, but it worked... they did indeed stop... They giggled in satisfacción as they got up and sat on either side of my feet.
"Ya casi se acaba mi cosquilloso Gabrielito, pero, debes escojer una cosa. Piensalo como un juego..." Came the seductive voice of Mrs. Lorena Rosario.
"Pick a Color of one of my feathers... red, blue or green... and it will decide who and where your tickles will end... sound fair?"
I nodded. But I couldn't take much more... surely she had to see that, surely she cared.... "Red... please... I can't take more, I need a break...."
I couldn't see her smile, but Loreena did smile and nodded to her two men, then she left. They sat back down next to me and slowly began to comfort me, playing with my hair, patting me and otherwise making it feel like everything was fine now.
"It's all over, it's all downhill from here. My name is Vasco, I won't tickle torture you anymore." His smile was devilishly geniune.
"Yo si te voy hacer cosquillas, y no voy a parar hasta que te vengas Papi. Así que, vamos a ver cuanto duras... te da cosquillas en las bolas? O en el bicho?"
I tried to protest but the blonde, caring, very strong one put a single finger on my lips. The good con bad con routine was working and my parts were unbuttoned and my member was exposed. I was not gay, nor was I ticklish in my balls or dick like Cofresi asked, so I felt uncomfortable and weird being fondled by two men... still... better than being tickle tortured once again.
"I'm not gay guys, with all respect you won't get what you're after so- HAHAHAH! WHAT was THAT!?"
I had never actually been tickled in my balls or shaft by a feather but that came from my ass! They had a small little feather in between my butt cheeks and it was tickling my ass so, so much.
"That's a shame cause red feather means tickled until you orgasm, or faint. So..." Vasco said, cradling my head and moving his hands into my parts.
"Yo apuesto a que eres cosquilloso en el Nie" Cofresi said as he moved the tiny feather to that spot between your dick and your ass, the Nie. It was instant, like a Bolt of lighting, I tried to move but they spread me and pinned me to really zero in to that spot.
No one had ever touched me there, much less tickled me, I begged and pleaded and screamed for a while but they kept tickling this one spot like actual torture. I'm not entirely sure why but after what must have been ten minutes of relentless tickling in that área I did get an erection.
I did not want to let two men make me orgasm... but I had no idea that when erect my balls were ticklish. While Vasco held me down Cofresi cradled my balls and lightly grazed them with the tip of his manicured hands. I broke long ago, I couldn't orgasm on command with that, so I just had to beg, plead and scream until finally... mercifully, I orgasmed.
