The Entrapped

by Chris Bellows

  "How does it feel?"

  The intensity cannot be described, standing in near nakedness, that which is covered in thin pink nylon is perfectly outlined, my nipples coming to points beneath the sheer tight fabric.

  I may as well be enshrouded in Saran wrap.

  "I ... I..." my thoughts cannot be completed.

  Sergeant Kelly smiles.

  "Let's walk. Hold my hand like a good girl."

  The first step sends a brisance of joy to my cerebral cortex. The nerve endings about my impaled squishy backside celebrate the attention... the extended hand and fingers of a woman. The cool evening air rushes up between my thighs to remind that there is little separating me from decency and complete exposure.

  Out the door onto 63rd Street, barefoot. No dog walkers nearby. I breathe a sigh of relief.

  "My car is down the street. There's this nice little avant garde restaurant near Fort Tryon Park. Very much off the beaten path. I think you'll be comfortable there."

  Sergeant Kelly's auto appears as if she purchased it from the police department. A sedan. Plain. Missing are blinking lights and radio communications.

  "I'm Miss Kelly when showing you off, little girl. Drop the Sergeant," she forewarns.

  A long drive for Manhattan, but Riverside Drive moves well as the rush of commuters dwindles. We reach 207th Street in minutes.

  "Now, let's talk about some nice earrings for you... and how you're going to earn such. You can't keep selling your youth for $30 and expect to make yourself comfortable. A girl has to... well a girl has to do what a girl has to do..."

  I'm not picking up on the gist... but then again the deluge of female hormones flooding my male mind... my counselor adequately explained the indeterminable results on the brain when testosterone levels plummet and estrogen levels peak...

  Miss Kelly parks the car in an illegal spot, turning over a placard on the dash to suggest police business. She opens the passenger door and I know to extend my hand... I am to be walked.

  The illegal spot is serendipitous, only steps from the destination restaurant. It is somewhat dilapidated, as with many of the older finer restaurants of New York. When we enter, the Maître, probably the owner, somewhat wizened and speaking with a deep unrecognizable accent, greets Miss Kelly quite warmly. She is known.

  "Mr. Smith's booth, Anwar."

  "Mr. Smith not here, Miss Kelly," the old wretch ogling my near nakedness.

  "He will be. We'll wait in his booth."

  The wretch gathers two menus and leads to the very back of the musty near empty dining area, the atmosphere darkening, becoming darker with every step. My hand in Miss Kelly's, she guides, directing me into the booth first then sitting to the outside. Memories of the odious 'date' in Greenwich Village come to mind.

  "I'll have wine. Nothing for her," Miss Kelly orders, an albescent head nodding understanding.

  He steps away. A controlling hand easily slips under my 'tube' bottom to find my ringed penis and the moisture expected.

  "You're wet, just like an aroused horny little girl," Miss Kelly laughs. "You like being led about barefoot and nearly naked."

  I blush.

  "Well, young lady, you're going to very much enjoy meeting Mr. Smith. Hands high, arms straight up."

  I obey. And just as quickly as my tube top was pulled over my head and shoulders, Miss Kelly removes, sliding it up and away with notable adroitness.

  I am topless... only the relative darkness and the paucity of patrons offering modesty.

  "What's it feel like? Getting your thrill?" Miss Kelly laughing at my blushing reaction of modesty as she stuffs my top into her purse.

  There reappears the old reprobate, ogling more as he plops a glass of wine before Miss Kelly.

  "One of his dates?" he inquires.

  Miss Kelly flashes her badge.

  "You'll not have a problem, Anwar. As you know, Mr. Smith is a gentleman with... shall we say ‘refined tastes’."

  I surmise this Anwar originates from a country where harems, deeply guarded and secretive, have survived the onslaught of moralism and modernity. For he momentarily glares at my prepubescent appearing nipples, seems to nod with approval and once again retreats.

  Miss Kelly next reaches with both hands, grasping the tube 'bottom' at the hips.

  "Scootch, pretty little girl. Lift."

  "Please no, Miss Kelly," fully understanding that I am to slide out of my only remaining garment.

  She smiles, nonchalantly... flippantly. I begin to realize how quickly and easily me and my new garb can part.

  Powerful hands tug. I feel the tight stretchy garment slide away reversing the earlier effort... over the hips... down the thighs... knees... calves to my ankles.

  "You excited?" she asks in leaning to pull the taut garment from beneath my feet.

  I am. I am quivering... and not due to cold. I can feel my drool on the hard wooden bench of the restaurant booth. The scene and the anal plug have me secreting.

  Then she stands, taking the time to gather the potential covering of napkins and toss to a nearby table, and steps away, leaving me completely nude in the booth. Though somewhat dark... a passing patron will have no doubt about my lack of attire.

  ***

  In the gloaming of a May evening, Miss Kelly pauses as we step from the restaurant, grasping the bottom hem of the tube bottom, pulling to turn it up over my belly and lower back. She once again demonstrates how quickly and facilely she can bring exposure. This leaves me naked from the waist down and I feel this added urge to get to her car.

  “So you enjoyed being with Mr. Smith?” taking my hand for the short walk.

  I remain silent. The man was old... and creepy... with hands exploring everywhere. Not an inch of flesh escaped his examination. I never before felt so violated. There was no gender subterfuge, his fingers quickly finding my trapped penis. He smiled wickedly and still referred to me as ‘little girl’.

  Then came the six sordid words. Yes, he later had me fellate him, slowly, casually eating a meal as I knelt under the table partaking otherwise.

  “Well, it’s better than three ‘Hamilton’s’,” Miss Kelly lectures, referencing my impromptu demand for $30 cash in the park. “Mr. Smith paid a rather heavy ‘fine’ for his exploits... Benjamin’s,” Miss Kelly patting her purse.

  She tightens her grip and walks slowly, building the trepidation of discovery. I attempt to increase the pace, spying local dwellers exiting Fort Tryon Park as the sun has set. She resists... the power of her badge will extract her from difficulty... but not me from the intense humiliation offered by onlookers.

  “Yes, we’ll be getting you some nice earrings. One benefit of being in Vice, Renee, we know who can pay... and who must instead go to prison. Manhattan is chock full of Mr. Smiths.”

  Reaching the car she pauses, surveying my nakedness with a gloating smile similar to Nurse Sueann. Then she again demonstrates both her power and my obeisance, tucking fingers under the tube top and turning it down to join the bottom at my belly.

  “Ready to ride?” playfully flicking my nipples as I squeal in delight.

  I certainly am.

  ***

  I am to learn that Sergeant Kelly is correct concerning the plurality of ‘Mr. Smiths’. Meetings are thereafter arranged Thursday and Friday evenings. Different men... different places... larger anal inserts... similar results... with Sergeant Kelly keeping my interest piqued utilizing varying levels of undress, mentally tormenting me with possible exposure to the unwary, offering vague reports as to how close I am coming to owning diamond pendants.

  Saturday she demands my attention for the entire afternoon.

  ‘Have copies of your apartment keys made for me,’ she more than suggests on the phone. ‘Tired of ringing that buzzer. Leave them in your mailbox.’

  Yes, it is an appropriate step. Who am I to have the ability to deny her access to me at any time?

  And so I am frolicking about in nakedness on late Saturday morning. C
atching the reflection of my glabrous, soft and rounded flesh brings an inward smile.

  I hear the scratch of metal at my door. A key inserts and before I can hide or find covering, Sergeant Kelly enters unannounced. I am most chagrined to see that another woman joins her and I make a dash for my bedroom and the covering of a robe.

  “Stop, Renee. You know you are to greet me in the nude. Where are you going?”

  I indeed stop... feeling that twinge as, without benefit of covering, I must confront the unknown woman.

  “This is Candace, Renee... Miss Candace. She’s going to teach you a few things... expand your repertoire,” Sergeant Kelly seeming to find delight in using the word.

  This Miss Candace is in black leather and carries a matching black leather brief case. Tall with short black hair, combed as would a man, she appears quite masculine – I am to learn how masculine.

  “Cute,” uttering the word I hear so often, her voice deep and husky.

  Sergeant Kelly beckons me to approach then points to the knee high boots of her cohort. I know to kneel and kiss. Then in not being excused I know to begin to lick as well.

  “Nice touch,” Candace suggests, not at all surprised by my truckling greeting. “You’ve been opening her?”

  “Slowly. Progressively larger anal plugs.”

  “Good. Girly boys like this really learn to enjoy it. In time they even beg.”

  Miss Candace speaks without vocal inflection, a woman with apparent experience as I note Sergeant Kelly nods in agreement.

  “Yes, Renee has not overly resisted yet... once I have her plugged all protest ends,” her smile somewhat knowing.

  “The coffee table is too low. Perhaps the kitchen?” Candace suggests as she opens the black brief case and places it on the coffee table.

  Why should I be surprised to spy a vast array of dildos with accompanying straps and other paraphernalia?

  To the kitchen, Sergeant Kelly lifts me like a child to seat me on the Formica table.

  “Let’s start supine. Many will enjoy playing with his nipples... and also enjoy the look of distress as he must accept something larger than he’d like,” Miss Candace lectures as a dildo harness is removed from her briefcase.

  The woman is adroit, buckling the many connecting straps of leather about her waist and thighs as nimbly as one would don shoes. Meanwhile Sergeant Kelly bids me to lie back.

  “Knees to your chest, little girl,” Miss Candace firmly advises. “And it’s also best to convey some expression of fear... a little play acting... guys like that,” more lecture.

  There is no need to act, as Miss Candace selects a sizable dildo. My concern is genuine and palpable. The black rubber is longer than any of the anal plugs... and seems stouter. Yet without the bumps and ridges it may glide easier.

  “Now some guys will like to play here a bit... heightening the sense of power and subjugation... others will just plunge,” her fingers toying about my anus.

  I am chagrined to find enjoyment, and that such will soon end.

  “For today we’ll lube you up, pretty little girl. But when with a man, you best do it beforehand. Most will not care whether you’ve taken the time to protect yourself against tearing... some will even revel in splitting you open. So be clean... be well greased.”

  Spoken as a handy jar of KY jelly is found in her black leather brief case. The fingers return, more pleasure as I am indeed thoroughly lubricated.

  The dildo tip is aligned. Her hips roll effortlessly. My sphincter yields. I whimper. The women laugh.

  “And in we go... for now nice and slow. Always look into the eyes of your sodomizer, Renee. A meek fawn-like look. He’s mastering you... taking your sphincter...and your pride. He’s big and strong and you are just a soft and warm lump of putty to have his way with... a tight place for his penis...”

  The words are even toned, forthright. As stated... it is a lecture on the art of submitting to anal sodomy. Thrust, withdraw, thrust, withdraw... it hurts. The dildo is large. But more than the physical is the emotional... the psychological... submitting to a woman... with another looking on... it’s a three point attack on the psyche.

  Plus I am to time the tightening and relaxing of my sphincter, concentrating on maximizing male pleasure.

  “Squeeze the very tip when you feel it withdraw. Challenge reentry, be a little minx. First defy the penetrating virility then whimper when your man forces you to take it... again... and again... and again. He’s besting you. Forcing you to offer pleasure. It so much builds his ecstasy.”

  Gloved hands begin to toy with my secured penis, positioning it such that some of the friction of each thrust abrades the tip. Her fingers toy with the loose flesh of my empty scrotum... adding a tinge of delight. This brings a smile, spurring some endorphins, loosening my sphincter.

  The experienced Candace knows. In feeling my reaction, she also smiles... for the first time.

  How many... how often has she taken? And how deeply?

  “See how quickly they learn to enjoy,” she notes... the gloved hands rising to my nipples to tweak and broaden both my smile and my delight.

  Sergeant Kelly nods, equally joyful... but hers is so differently derived.

  “He’s drooling... the little whore,” her comment drawing all eyes to my penis tip.

  I am.

  ***

  Sunday I find myself sore. It is understandable. Miss Candace had fucked me smoothly and consistently, her stamina unending. Tiring of the supine position, I was placed tummy down. A larger implement was deemed appropriate... having been ‘properly opened’. Then the sodomy resumed.

  Lastly on the kitchen floor.... doggy style. Knees parted, head down, gloved hands grasped my hair. It was disconcerting... knowing where her hands had been.

  After each segment I was instructed to engage in a very polite ritual.

  ‘Thank you, Sir, may I clean your penis for you?’ the words so obeisant... the act of humbly licking that which penetrated my anus so humiliating. Yet, Miss Candace assured that each dildo subsequently gleamed with my saliva. Quite an insistent woman.

  Yes... more acclimatization.

  Yet... the advantage... in so interacting... there would be no need to continue the subterfuge over my birth gender. My assailants will be well aware of the vestigial remnants of maleness. So from what dregs of New York will Sergeant Kelly draw to obtain more ‘Benjamin’s’?

  With Miss Kelly’s eight years on the Vice Squad, I will find out... I am sure.

  The long afternoon ended with Sergeant Kelly snipping my cable tie. I served drinks to them in the living room, Miss Candace finding my floppy little penis to be most amusing.

  ‘Good oral skills you say? I suppose nature must compensate in some manner.’

  ***

  Right hand in Sergeant Kelly’s left, the feel of her power and presence assuages the trepidation of walking Fifth Avenue in nothing more than slinky tube top and bottom and high heels. Full makeup, it cannot be determined whether I am a little girl or an underdeveloped woman. No one would ever begin to guess my birth gender, except she has me donning my special gift from Miss Ramona... my plastinated testicles. And in being anally plugged, my own motion kneads my prostate and brings forth the drool. I hope it does not show... very unladylike.

  “Lots of Benjamin’s, pretty little girl,” Sergeant Kelly patting her purse and building my eagerness.

  I cannot imagine how many after the many weeks of indecent rendezvous. In offering myself anally, I am well opened. I am a neutered guy... and still there is little circumspection among the eager, well paying patrons so desirous of the Greek style. Thankfully, I have not been anally subjected to the penis two nights in a row... Sergeant Kelly well aware of the soreness after fervent plunging... each phallus seeming to become larger and plummeting deeper.

  So I am to offer fellatio on alternating evenings. For those patrons seeking oral gratification the gender ruse continues.

  Where does she find them?

&nbs
p; Most humiliating, the abundant seed, that which I will never again expel in ejaculation, oozes freely down my thighs, no underwear to offer modesty or to absorb the evidence of sodomy. Chocked full of sperm, the cloudy essence is quite evident, much more notable than my clear prostatic fluid. In being walked about after such coupling, Sergeant Kelly seems to be in a nirvanic state... the ultimate in feminine power... control... selling one lowly male beast to another. And I suppose having her bag stuffed with cash does not at all detract from the thrill.

  We reach Tiffany’s. In the window, many diamond pendants. I smile. I blush. My circulation pulsates. I am a little girl at her birthday party.

  “We can buy any pair you want, Renee, but we’ll need to negotiate a deal.”

  Why would I think this would be without emotional trauma?

  We enter. Since it is Tiffany’s attention is immediate and detailed. A man in his fifties introduces himself to Sergeant Kelly. He assumes me to be a minor, thus focusing on the adult. I am given to blurt out that every dime of expended cash will be from my earnings! Yet I know to remain silent. Little girls don’t talk to men in big important stores.

  “Earrings. I’d like to look at the largest, most ostentatious pair you have... for little Renee.”

  The man is not impressed with the choice of words. Nothing offered at Tiffany’s is ‘ostentatious’. He is also not impressed with the manner of my dress. Probably agreeing that any jewelry on such an audaciously attired strumpet would indeed appear unwarranted.

  “If you can join me in a private room, I can show some very favorably priced items...”

  “Price is not a consideration,” Sergeant Kelly understanding that the man does not want me seen in the store. I can assume with reasonable assurance that the wealthy and notable are not invited to a private room... Tiffany’s preferring to have them display themselves to impress the lesser clientele.

  “Of course. Any preferred range?” he inquires as he ignores Sergeant Kelly’s rebuttal and leads to the private room.

  “$10,000 to $15,000. In cash. Plus we’d like to negotiate a trade.”

  Not uncommon in the jewelry business... but what have we to trade?