The Entrapped

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.”