The Entrapped

by Chris Bellows

  The warm wet cloth swaths along my inner thighs, right and left. Then she teases, tantalizes where Mr. Depraved entered me. Her touch is divine and with penis secured the tip benefits from her tendance as well.

  Then the covers ruffle, yet for some reason I still cannot shift my head from under the pillow. I remain shaking. Then I feel more warmth. I feel the smoothness of feminine flesh. Sergeant Kelly slips under the covers and presses herself against me. And she is as naked as me!

  My trembling stops. I revel in what I have felt so rarely... the intense desire for which was quashed when my testicles plunked into a waiting metal dish.

  The strong knowing hands begin to push and press at my head and shoulders. I have an inkling of her desires... her wants. I adjust myself accordingly. Head from under the pillow, eyes closed, I slip lower under the covers. And indeed Sergeant Rogers is without a shred of covering. My heart leaps as in moving lower there comes the fragrance of her love nest.

  “I trust you can still please a woman, Renee. The doctor took the time to modify, imbuing you with that which can offer pleasure in place of that tiny organ you prefer to keep hidden.”

  She softly laughs again. I know to begin licking. Thinking of my Greenwich Village episode, I will not need water... I enjoy her taste.

  ***

  I serve naked, as always, Sergeant Kelly finds a robe. It barely fits and her fine breasts challenge the ‘V’ at the neck formed by the lapels.

  It is Sunday morning. The adrenaline of last night’s ordeal finally dissipating... the expenditure of energy and lust in unending cunnilingus... we slept late in exhaustion. I awakened her with my tongue.

  “You have not been entirely truthful with me, Renee,” Sergeant Kelly lectures, taking an offered cup of coffee from the tray.

  I have an inkling of what she references. It required someone with considerable resources and boldness to confront a New York City police officer in such a manner... seizing her on the sidewalk of a busy street.

  Yet she endured.

  “Did they take the money?” I find I must humbly inquire.

  She shakes her head reaching for some toast.

  “Not money they were after. They wanted something... something I promised them.”

  She chews. I remain ashamed in not helping her... coming to her aid. I still harbor fear... yet the dauntless Sergeant Kelly takes breakfast most serenely.

  “You know Pablo Escobar, Renee. And I’m not saying ‘of him’... I am saying that you know him,” her tone most direct.

  I bashfully nod. Weeks ago... during my ‘arrest’... in narrating my life story... my life of transformation... I omitted all reference to Pablo Escobar and the frightening encounters at the Waldorf. Deep within... I know it is he who has for some reason found interest in Sergeant Kelly. But I do not know why. So I can no longer hold within the story. To some degree, I have duped my protector... and last night could have been very dangerous for her. So I break down... slowly and in great detail telling of Miss Ramona... Miss Maria... and the Waldorf affair.

  Sergeant Kelly listens intently, but at the end comes her only comment, “Think I’m going to get you a hood... a cunnilingus hood. Tight rubber... smooth... without sight... without sound... it will help you focus.”

  ***

  New York, New York

  Sergeant Kelly Rogers

  Mid Sunday afternoon I depart Renee’s apartment. I need to think. Though I feigned a degree if indifference, I am somewhat incredulous over the story Renee told.

  Considering what Pablo Escobar is offering me to deliver Renee, these women must have had the cojones to separate him from what is presumably a considerable sum!

  Well... business is business. Escobar’s sealed instructions offer not only the coordinates of the Islas Rosario, but how I am to present Renee... effeminately... in makeup, heels, hair styled... and with a very telling article of apparel.

  For this task I need to review my list of perverts. I need to find more information about Islas Rosario. But most of all, I need to uncover what so much concerns Pablo Escobar... to travel to New York and joust with a police officer in such a brash manner. Do his fears bring irrationality? Or is what he perceives to be on the table worth the risk of capture and incarceration.

  The Waldorf Apartments will be key. What sources have I there? Vice does not get called into such a ritzy environment very often. But I know the security personnel assigned to the hotel operation are wary of extremely high priced call girls. That’s a start.

  If there is one thing I have learned about the sexually depraved it is they are consistent. There just does not seem to be an effective avenue of reform... assuming any of the perverts would even choose to take a single step down such a thoroughfare. So in my eight years I have kept personal notes... a log... with names, phone numbers and addresses of every deviant encounter... even those I let off with a warning. It is from this log that I pimp out Renee... those I sprung... after negotiating ‘bail’... money for myself. And none of them has been borne again, instead readily agreeing to a tryst with my little tart whose fellatio is becoming renowned and whose cheeks open on command.

  So I review my log... who is wealthy... who has a yacht... who can take the time to cruise the Caribbean and benefit from unending debauchery? The question not needed to be asked... who has the inclination... they all do.

  I search. Locate a candidate. Make a call.

  Next it’s to the Waldorf; I have the name of retired Detective Sergeant Manny Matthews, now on security detail. We meet. I introduce... with the badge. He is uncomfortable knowing I am Vice. The Waldorf? Vice? We speak sub rosa in a secluded corner. I have Renee’s pic remaining on my cell phone. Seen him/her? Yes, he has... but not in the hotel. Went to the apartments. Which one I ask? Number 2207. He’s good, the childlike Renee raising suspicion. He followed up.

  Progress!

  ***

  Monday morning the progress slows. A call to NYC Buildings and Records suggests that Waldorf apartment 2207 is owned by a trust based in the Cook Islands, the level of confidentiality concerning ownership, etc. not to be broken... the paper walls of the trust not to be penetrated.

  Correspondence. Someone pays the bills... monthly maintenance to the Waldorf for heat, power and cleaning. I write a note, to whom it may concern, offer my name and phone number. I return to the hotel and leave it with the Waldorf apartment’s administrative office.

  Of course they explain the high level of confidentiality... everyone anonymous... no assurances offered that my note will go to anyone of responsibility... but it cannot hurt to try and make contact.

  Leaving the Waldorf, I realize that I will need to arrange a vacation for Renee. But when he/she does not return? Too many questions will result. So I call this ‘Mr. Thompson’, he mired with the task of supervising Renee and maintaining sanity in his department. I introduce myself... ‘Sergeant Rogers, NYPD Vice squad’. Some questions concerning a ‘Robert Warren’, all information offered to be kept confidential. He is upset by the call... but not surprised.

  And that is all it requires, a transsexual Renee being on thin ice since his alteration. It will require a couple of days, big companies need the approval of legal counsel, but Renee will be terminated. So from an employment standpoint, my ward will not be missed.

  Ending the conversation with Mr. Thompson, my cell phone rings, my call to Wadsworth Danforth McBride being returned... and promptly.

  “Waddy, so good of you to return my call...” I offer in jest.

  He dares not defy me. Waddy, I caught in flagrante delicto some three years ago, standing in a Times Square alley, receiving oral sex from an underage runaway. Well, one would normally say... ‘a guy’s got to do what a guy’s got to do’. But in Waddy’s case, it wasn’t a situation in which he could not keep it in his pants. Waddy was dressed in drag at the time, the head of the girl bobbing away under a flowing pleated skirt.

  So, what’s a mega wealthy guy like Wadsworth Danforth McBride do
when confronted by such an ignominious situation? Bribe everyone and everybody with a wallet or a pocket book.

  I spared him a trip to the precinct and bought a nice watch.

  I have not yet ‘introduced’ Waddy to Renee, saving the low hanging fruit, not to be puny.

  “Been sailing lately, Waddy?”

  “No Ma’am.”

  “How about a little cruise? Where’s your yacht?”

  Waddy has some sinecure position at his family’s trust company. And yes, he does wear male clothing when tending to business. But among the trust officers and his family his ‘eccentricity’ is known, though not details like the Time Square alley episode, and therefore very little responsibility is delegated to him. Matter of fact, I believe the more accountable employees at the trust company are probably thrilled with every long weekend taken.

  “Fort Lauderdale. New sails. Engine rebuilt.”

  “Excellent. I have a proposition for you. Something a man with your refined tastes will not refuse.”

  “Word is out on that young trollop, Sergeant Rogers. Have you no shame?”

  Yes, the depraved talk to each other... really communicate over the internet in squalid secrecy... and in anonymity, of course.

  “Shame that I was not offered first go,” he adds with a snorting laugh.

  So Renee’s exploits have been made known to him. The question... known to him as a purveyor of oral sex or anal... the difference being whether Renee’s birth gender has been divulged to Wadsworth Danforth McBride.

  Yet, with Waddy’s propensity to cross-dress, does it matter?

  So we arrange a little cruise. I tell Waddy the ultimate destination is Cartagena, Colombia, preveniently countering his concern over security by stating that I will be adequately armed. His ketch is roomy but can be sailed by two. And though Wadsworth Danforth McBride’s choice in lifestyle is quirky and peculiar, his seamanship is known to be worthy. I know he’ll plan and chart an appropriate course.

  I patrol the park for the remainder of the day. Nothing exciting... a usual Monday. In finishing my shift, I stop at a sex shop and purchase a hood for Renee. Black latex, very stretchy, it will cover her entire head, one convenient hole for both the nose... in order to breathe... and for the tongue and lips... in order to... well in order for Renee to be Renee.

  I return to Renee’s apartment. My little bundle of joy awaits. Naked, finely made up, nails glossy, earrings ringing, penis clasp chiming as she prances about... offering me a glass of wine then licking my shoes.

  I move to Renee’s computer, my little girl squeezing under the desk to worship my feet. There I log into a website from Germany. Instructions in Escobar’s note... Robert Renee Warren is to be delivered in chastity, secured by the most ineluctable device made... The Neosteel belt. I click and find the model which will cover well the evidence of Renee’s birth gender, but also offer access to his tight little bottom. I read over the measurements to be taken and instruct my little treasure to find a measuring tape.

  The Neosteel is expensive but of noteworthy quality. I measure Renee then order... express shipping.

  I also give thought to my planned Caribbean excursion, then shift to another website to purchase a second device... less expensive... no measurements required.

  ***

  Yes, Mr. Thompson was quite annoyed being contacted by the police... the Vice Squad. End of my shift Tuesday, I enter Renee’s apartment and am greeted with dejection.

  ‘Suspended,’ Renee glumly proclaims.

  To me that means the legal department is weighing the risks of a wrongful termination suit versus the ‘inconvenience’ of an employee whose very presence is disruptive and, with questions coming from the Vice Squad, could become an outright embarrassment. She’ll be fired... it is a fait accompli.

  Renee is not effervescent. Has not spent time looking pretty for me. His naked toes don’t glide and patter about. When she hands me a glass of wine I reach forth to tenderly tweak a nipple. This brings a reluctant smile.

  “Let’s travel. You’ve garnered a pile of cash for me. I’ll spend a little on you.”

  She smiles... wanly... Renee as aware as me that she will probably soon be jobless. I surprise myself in feeling sympathy.

  “Bought something for you, little girl,” I announce with enthusiasm.

  Time for the hood. I display it... dark... foreboding... it will be as tight as a condom when stretched over my little one’s face and head.

  “Take off your earrings.”

  It must be disheartening I am sure, Renee spending so much time trying to look pretty and ending up deaf and sightless, but I need to instill concentration and discipline. So I stuff her ears with thick wads of cotton, slip the hood over her head and pull tightly.

  Snug indeed... denying sight and sound, I lead her to the bedroom. If I cannot cheer her I may as well cheer myself. So I disrobe, push and prod and within a moment have Renee lying prostrate, her hooded head wedged between my thighs.

  Good cunnilingus... yet with much possibility for improvement. The sensory deprivation will heighten her attention to detail... seemingly enhance my taste. And that tongue... so strong... so nimble…

  ***

  Wadsworth Danforth McBride comes through. As expected of the depraved, nothing musters enthusiasm like the semblance of debauchery. He calls to announce his refurbished yacht, ‘The Crosser D’, is ready to sail. We can depart for Fort Lauderdale any time.

  While we speak, I click to my email where there has been sent a web address offering the status of my Neosteel belt. Due to shipped air freight in two days.

  “I’ll make flight reservations, Waddy. Looks like we can leave Sunday.”

  And while we wait, I can set up more ‘dates’ for Renee. A girl can never have too much cash. And now that Renee is unemployed, the otherwise debasing fellatio is the only thing that separates her from loneliness... that and lapping away at my quim.

  ***

  Fort Lauderdale, Florida

  Renee/Robert Warren

  An uneventful flight, though airport security gave great pause when comparing my photo driver’s license to my pretty effeminate looks. Sergeant Kelly interceded, badge in hand, explaining that I was undergoing therapy, a ‘very delicate matter’, and offering assurances that this blonde girl... well made up... nails polished... in heels with frilly blouse and short skirt... was indeed Robert Warren.

  Curious, but after finally passing through, Sergeant Kelly relieved me of my purse... all identification included.

  At the airport we meet this Wadsworth Danforth McBride character. He looks at me as if I am a cupcake to be devoured, stepping forth to closely examine my attire and complimenting with gusto. Handsome, six foot, dark hair, there is masculinity, but also something foppish about him.

  Sergeant Kelly introduces him as an old friend. I refrain from offering the six words I am ingrained to utter whenever Sergeant introduces me of late. After all we are in an airport... with much security.

  Before departing, Sergeant Kelly suggests a visit to the lady’s room, always a mental challenge. For the flight, in order to breeze through the metal detector, my penis clasp and attached chimes were stowed in Sergeant Kelly’s purse, inspected, but not confiscated as a potential weapon.

  But the three hours of airport waiting time and flight time were all the time she is going to allow my penis to be freed.

  To the ladies room... to a stall... I know to bend. She flips up my pleated skirt at the back, left hand pulls back my tiny appendage, and right hand clasps the penis ring to the guiche. I once again chime with every step. And perhaps it is imaginary, but I do believe the hollow tubes dangling between my thighs extend below the hem of my skirt.

  The ringing attracts much attention. It is what Sergeant Kelly desires for me. The humiliation intense, I feel the twinge. I begin to ooze... I know the drool will follow.

  Please, I need to exit the airport quickly.

  To the claim area, our luggage comes. Very li
ttle for me. A heavy suitcase for Sergeant Kelly. I am to later learn of the contents. She has used her credentials and specially arranged to check through some weapons.

  ***

  The yacht of this Wadsworth Danforth McBride proves to be ideally suited for a very private voyage in the idyllic sunny waters of the West Indies – large but capable of being sailed with two... plus a cabin girl... me.

  Within minutes of exiting Fort Lauderdale harbor a smiling Sergeant Kelly steps proximate and unhitches my skirt. Accustomed to being naked in her company... but not outdoors... and not with ‘Waddy’... there comes concern. Of more dismay, she tosses the garment overboard. Waddy turns and observes from the cockpit as next my blouse is removed... then my shoes... leaving me completely exposed. There also come splashes as my cheap platform shoes are tossed. My blouse is launched skyward, fluttering about in the ocean breezes to settle into the wake of the Crosser D.

  “I suspect you’ll not be feeling the luxury of clothing again, my little one,” Sergeant Kelly ominously proclaims, tweaking a nipple.

  I smile and blush... at first. Then I recall the limited packing done on my behalf. It would seem my only covering is now among the fishes. How will I return to New York?

  Then my purse is tossed as well, all identification within bobs then sinks. It seems I shall not be returning anywhere.

  Well out of the busy port, Waddy also disrobes. I am shocked though, when he playfully dons a grass hula skirt.

  Sergeant Kelly disappears into the cabin then returns within moments.

  “Time for my crew to be properly outfitted.”

  As Waddy navigates, Sergeant Kelly lifts the front of the grass skirt. I now note that Waddy keeps himself neat down below, his pubes shorn. I recall from college days some of the more lecherous guys so shaving... claiming it facilitated more oral attention from otherwise squeamish and reluctant girls.

  “What are you doing, Sarge?” Waddy having to keep his eyes and hands tending to navigation.

  “Just a little something to enforce discipline amongst the crew.”

  It is apparent that though this Waddy owns the craft, Sergeant Kelly is assuming control. For he docilely lets her have her way, as her hands rummage about under his skirt.