The Slave and the Sissy

Pepper and I knelt on the silky sheets of the bed and studied each-other in disbelief; our cocks rigid and ready for relief. I took her sweet sissy cock in hand as I sniffed and licked at her face and neck; her skin as white and silky as the sheets.  She thrust her slippery little sissy cock back and forth between my fingers as I teased her glistening little pink bell-end.  Pepper panted with anticipation as she unhitched her crop top; her sweet little breasts stood firm and inviting, my cock throbbed as I licked and sucked at her stiff little nipples.  She quivered and let out a little moan as I slid my hand down her feminine back and slid it over her soft bottom, my middle finger straight into the hot cleft of her buttocks and into the hotter inviting tightness of her anus.  She looked me deep in the eyes and whimpered as I probed deep with the one hand and ringed her little cock with the other, fingering her little ball-sac gently as I stroked her back and forth.  She was good enough to eat and I was so impatient; I so wanted my cock to be where my finger was.  Pepper did not keep me waiting; she wailed with pleasure as I curled my finger deep in her anus and I felt her thrust and convulse sweetly; her hot cream exploded from her little cock, splattering on my thigh and dribbling down my knuckles.  I kissed her softly as she spent again and again, moaning sweetly in ecstasy.  We kissed and then she took my hand, watching me with soft eyes as she licked her sticky gift from my fingers.  She bent down and licked my thigh clean, then looked up at me again as she took my stiff cock in her hand and licked my sticky bell-end, making me jerk uncontrollably.  She let go, turned, lay on the bed and lifted her sweet bottom. Now it was my turn.

I knelt between those beautiful white legs and felt the softness of her buttocks with my hands, as Pepper lay there submissively, waiting to be fucked.  I licked the back of her thighs making her shudder and whimper all the more, her sweet anus pulsing in and out expectantly; she had had her orgasm and now yearned to feel my cock inside her.  I licked up the curve of her thigh, and then licked her sweet little scrotum; I felt her tense as my tongue glided up to her hot little anus. Her aroma was as sweet as any female I’d licked, and I teased her tangy little anus, probing deep with my tongue, ensuring she was nicely lubricated. I moved forward and licked the small of her back as I prepared to have her for the first time.  Pepper gripped my hand and squeezed tight as I moved my stiff and wanting cock into the soft cleft of her delicious cheeks.  Gently I eased my engorged bell end into the tightness of her anus for the first time; it was so tight and warm, I was close to coming already, such was the exquisite feel of my sweet little sissy’s pussy. Pepper moaned and cried out softly, making me halt; I did not want to hurt her; she pulled my arm, urging me on.  I stiffened my back and pressed the length of my stiff cock home into the inviting tight warmth of her boy-pussy.  The sensation was absolute heaven as I pushed right to the hilt.  Pepper moved back and forth, slowly at first, making my cock spasm and pulse deliciously; she was enjoying her submission to the full.  The animal in me took over and I released her hand, gripping her soft torso with both mine as I now glided in and out of her gorgeous bottom, my balls slapping hers as I thrusted in ecstasy. Pepper laid face down, arms stretched back, in complete sissy submission; she moaned with pleasure as she was fucked mercilessly. My whole body went into spasm and I nearly passed out, such was the exquisitely strong and ecstatic strength of my orgasm. Pepper cried out in sweet submission, clenching and releasing her anus around my stiff cock as I erupted with a roar into her sweet haven.

I seemed to come for an eternity, spurting again and again into my sweet Pepper; she was mine and I was in complete ecstasy as I viewed the red haired sissy beauty, enjoying being fucked, lying prostrate in submission as I emptied my aching balls into her. She whimpered sweetly as my cock caused her exquisite pain which she thoroughly enjoyed.  At last, panting and completely sated, I released my sissy, pulled my dripping cock clear and we entwined in a loving embrace.  Tears of joy crept out from Pepper’s sweet blue eyes as she held me so tight, as to never let go. I licked them away and kissed my sissy long and hard.  Once again, unknown to us, smiling eyes looked upon us from a hidden vantage point. A dildo dropped to the floor, having worked a third orgasm from a moist pussy. Someone else was pleased with their work; the tease had been worthwhile.  She would keep this vision in her head when the slave next serviced her, and she would have his sissy watch, but before that, she would have them watch the sale of Pepper’s friend, Honey.

The two continued to grip each other tightly, soft and secure together, bound by Ella’s chain under the silken sheets as they drifted off to sleep, both entirely satisfied with their first encounter.

…

Ella took the chain from their collars when they reported to her, together for the first time, in the morning.  Pepper’s eyes were exceptionally bright this morning, and slave looked full of vigour and ready to carry out any command that befell him without the slightest hesitation.  Pepper gripped his hand tightly, lest she should suddenly wake from this beautiful dream; she smiled to herself, the tenderness she felt in her bottom could not be down to any dream, she had been well and truly fucked and wanted the day over quickly, so as she could entertain her slave once more. There was a slight tinge of sadness to the morning’s events though; Pepper’s friend Honey appeared in the charge of a large harem mistress with wicked whip in hand.  Ella smiled.

“Say goodbye to Honey Pepper.  We have found a suitable buyer for her and she is to be despatched today when he arrives for her.  I know the two of you used to discuss your fantasies; you are beginning to realise yours, and Honey will be very pleased I’m sure, when she meets her buyer.”

Pepper embraced Honey and the two shed a tear as they hugged.  Honey, a sissy of equally effeminate proportions as Pepper, had soft blonde hair in a long pony-tail and deep brown eyes. She eyed slave enviously as Pepper smirked with pride.

“Are you his? He looks like the sort you were always milking yourself over on ‘relief’ days. He’s very handsome.”  Pepper went her customary pink as she gripped slaves hand and looked up at his muscular body with submissive puppy-dog eyes. Slave could not help but smile with pride too, as his cock swelled at the thought of last night, and of what was to come that evening when duties were over.  His mind was already halfway up that pretty bottom already.  Pepper and Honey cried a little more as they said their goodbyes; slave then took her at Ella’s command and they knelt together in a corner as the buyer’s arrival was announced.  Honey was striped completely naked, her cage removed and her hands were bound behind her back.  My cock rose at her sweet vulnerability; pepper took my hand and placed it on her bottom as we watched.   I whispered to Pepper.

“What was her fantasy?”  Peppers bottom squirmed on my hand as she enjoyed being fondled.

“She likes big black men.”  She giggled softly as right on cue, Ella welcomed in a huge black man, dressed in Arabic style robes, loosely hanging.  The robes showed a prominent bulge at the front, indicating that the man had been savouring this moment. He put his hand under Honey’s soft little chin and smiled as he surveyed her.  He smiled all the more as her little cock stiffened and erected on realisation she was to be owned by a huge black man.  He swept the robes to one side with his free hand, and little Honey gasped as he revealed a huge black cock.  The massive velvety black phallus stiffened as he looked at his prize; he poked the bulbous greyish-purple bell-end under her nose and Honey sniffed excitedly at it, taking in his masculine scent.  Without command she licked enthusiastically at the underside of his massive bell-end, sampling the salty taste of his sticky pre-cum which now oozed freely from his huge organ.  He chuckled with satisfaction and at the delightful sensation of the petit sissy’s little tongue.  Honey’s cock stiffened at the thought of the exquisite pain her little bottom would feel when this huge cock stretched her tight little anus to the limit. The man pulled hi cock away, lest he should go too far. He nodded at Ella who came over and sat behind the sissy, holding her firmly.

The large African knelt in front of honey and gently grasped her sissy cock.  Honey eyed the huge phallus which was still on display and eagerly bucked in the man’s grasp; oh how she wanted to come. The man and Ella both laughed at her submissive impudence.  He began to stroke the sissy’s eager little cock as he spoke.

“Now little Honey, I am going to make you come.  If you make any noise whatsoever when you squirt, you shall have a whipping before my entire household staff, as soon as you arrive at your new home.”  He stroked her vigorously making her pant with pleasure.  He and Ella smiled at each-other, knowing exactly what the totally submissive sissy would do.  Honey tried her hardest at first, to make it look like she wanted to comply.  She watched his large black hand move rhythmically up and down her little white cock, teasing her oozing pink bell-end remorselessly , she eyed that huge cock, still on display; oh how that would hurt her bottom, she looked at his large features and imagined him brandishing a whip; oh how she would love to be whipped before an audience.  It was all too much.  Honey let out a high pitched squeal with gusto as she spurted in heavenly ecstasy.  Ella and Honey’s new, huge black owner, laughed as she did so; she had certainly earned a whipping.  The black man watched with pleasure as his hand teased the last spurts of cream from his new sissy.  Hot white jizz dripped down his black knuckles.  He held his hand to Honey’s mouth and she lapped his fingers clean without being asked; she knew her place.

The black man then bound his sissy ready for the journey; ankles bound, and a ball gag strapped in place, Honey’s little cock was erect again as the black man took a little something from his pocket.

“A gift for my new sissy; this will please you at all times and remind you that you are mine.”  It was a vicious looking ebony butt-plug, shaped like an aerodynamic phallus with balls below, designed to tickle the wearer’s prostate. He grinned with satisfaction as Honey’s little bottom accepted the plug, the sissy making a muffled cry as her little bottom clenched around the intruder.  Her little cock stiffened and pulsed as he produced a huge black silk sack; Honey was lifted to her feet and glanced lovingly at her new owner as he shut her out from the daylight, ready for her journey.  The sack went right down to her ankles; straps were applied around her knees, waist, arms and neck.  Honey made muffled whimpers as she enjoyed full bondage, her little cock stroked at the silk; how she wanted a whipping now.

The huge man deftly picked up his prize and casually put her over his shoulder.  The party followed him down to the outer courtyard where a donkey awaited him.  The sissy was laid carefully across in front of the small saddle.  The huge African making sure his sissy’s cock was erect up against her belly.  Honey moaned as she squirmed in the darkness of the silk, her little cock teased against the leather clad back of the donkey.  A tie then went under the donkey, from ankles to collar strap.  Honey now felt completely bound and helpless; her cock pulsed with pleasure as the plug teased her anus and she squirmed in erotic heaven against the delicious bonds which held her.  Before they departed the African spoke again.

“You will now begin your journey to another life.  If you mess on my silk during the journey, you shall have a further whipping.” He smiled as he urged the donkey forward; the movement making Honey‘s erect cock squirm continually, a huge hand on her bottom to let her know she was owned, which deftly fingered the plug in her bottom.  He knew she would come and earn the extra lashes.

…

After watching the African depart with his new sissy, Ella turned to Slave.

“On the subject of Africans, you have an appointment to honour with Mistress Ayesha the day after tomorrow; make the most of your sissy tonight, I shall cage your manhood again in the morning in preparation for your visit.  Pepper will manicure her when she arrives this evening to take you tomorrow, she will be my guest tonight as we have business to discuss; I’ll let her know of your fondness for each-other, I’m sure she’ll enjoy teasing you both about it, in one way or another.”  Pepper gripped slave’s arm tightly; she wanted him all to herself now, but knew this not possible.  Ella smiled as slave reacted by kissing Pepper softly.  Pepper smiled through the concern on her face; she was resigned to the fact that at least she’d be able to share him.

On a hill just a mile or so from Ella’s household, a huge black man on a donkey brought his beast of burden to a halt.  His huge cock stiffened as the trussed silk bundle which lay helplessly before him, squirmed uncontrollably; plaintive sissy whimpers made his huge member pulse and poke upward in his robes.  Honey’s sweet little buttocks were clearly outlined in the silk which held her captive.  A huge black hand fondled her cheeks with delight, pressing firmly home the wicked butt plug. Inside the divinely soft prison, the sweat dribbled off Honey’s fragrant body under the hot sun.  The man had brought the beast to a halt just as she was to come; he had thoroughly enjoyed the tease and knew what his sissy would do now. Now she squirmed for all she was worth without the aid of the donkey’s motion; the hand which now owned her pressed the plug sweetly in time with Honey’s bound thrusts in the silk against the leather padding.  She flexed against the bonds which held her, controlled her; she felt the tightness of her wrists and ankles, the taut rope which went from neck to feet, keeping her in submissive heaven as she thought of that huge black cock stretching and hurting her little anus, writhing in ecstasy all the more against those bonds as she relished a whipping by the huge man, before an audience.  Oh how she’d cry as the cruel whip punished her soft little bottom, oh how that huge black cock would hurt, Oh how the silk felt so exquisite as her stiff little sissy bell-end rubbed in satisfaction against it.  Honey wanted to pee and defecate at the same time, such was her complete submission to the situation; her little balls tingled the sweet alarm of her inevitable orgasm as she squealed into the gag. The huge cock, the whip, the audience, the silk; the black hand pressed hard on the plug as honey clenched in complete and utter ecstatic submission, her whole body was bathed in sensual pleasure as she stiffened and shot her cream,  her little bell sliding sweetly now as she messed.  The full impact of her bondage was realised as she tried to straighten out in full orgasm, only to enjoy the sweet sensation of rope about her neck and ankles, holding her at her master’s pleasure, making her spend all the more as she thought of the extra whipping.  

The black man laughed triumphantly as he cracked his whip for the donkey’s benefit; anxious to get his sissy home and relieve his aching cock.  The sound of the whip added a sweet finale for Honey; her bottom clenching tightly at the plug as she heard its wicked noise. Her little sissy cock dribbling a final sweet tribute at the sound.

Another huge African was now in attendance at Ella’s fortress; Ayesha, no stranger to slave; he knew every nook and cranny of the magnificent woman’s beautiful physique, he had licked her clean before.  The haughty bitch wore only a purple chiffon full length dress and a golden thong which barely covered her sumptuous womanhood; this was there purely as part of her schedule of titillation; she had been key in developing slave’s wanton urge whenever confronted by soiled panties.  As she eyed slave with contempt on arriving, she had made sure he noted her deftly pulling the thong tight into the crack of her glossy black arse and evidently sweaty pussy.  She would enjoy making him beg to sniff and lick the thong clean.  She would make sure to wear the same thong tomorrow, to ensure that it was sweetly scented after the labours of two days, tucked tightly in her magnificent cleft.

Slave and Pepper were made to kneel in opposite corners of the room whilst Ella and Ayesha drank wine and discussed business and the topical fact that slave now belonged to Ella. Ayshea was so pleased that he had been wrested from the fat woman; she loved his services as did Ella and was often at the fortress.  She was most interested at the developing relationship between sweet little Pepper and her favourite tongue. It was time for her manicure.

Slave was called over and made to hold Ayesha’s long, formidable, sleek black legs as Pepper daintily painted her toe-nails gold; the glittering varnish contrasting beautifully with her gorgeous dark brown feet. The black woman sniggered.

“I’ve decided to take both of you on slave’s appointment with me tomorrow; a sweet sissy will see what a male’s true position is amongst women, I may even have you perform before my womenfolk and their canes.”  Pepper quivered as the black woman laughed, she was glad to be going with her love, but her cock and bottom tingled with fear at the prospect.

Honey whimpered as she saw daylight for the first time in an hour.  She was surrounded by a crowd of black males with cocks as huge as her new master’s, sissies and nubile females of all races in various states of bondage, and before her in the middle of a courtyard amongst the smiling faces was her immediate destiny.  A large padded leather pole with shackles which awaited her.

…

Honey was viewed like a new toy by her new master’s people as she was led whimpering to the ominous looking padded pole, the males jostled to fondle her soft white bottom and rubbed their erect cocks against her sweet little body at every opportunity; the womenfolk smiled with eager anticipation at the prospect of seeing a whipping; the sissies looked on with blank faces, having tasted the whip before.  The males at the front howled with wicked derisory laughter as they viewed Honey’s little cock rising to an erection once more; despite having already spent herself generously twice before today, the effect of the thought of a whipping surprised even her; the derision and humiliation only pandered to her sweet submissive nature, her sissy cock was stiff as she reached the pole.

The males now openly played with their huge cocks as the soft and delicate sissy was strapped to the pole; her master making sure her erect little member went up tight against her sweet little belly as Honey was stood on a small platform to lift her to the desired height on the pole; allowing the smiling crowd a full view.  Then the leather straps were tightened around her ankles, thighs, and shoulders; her forehead rested on a pad which kept her face from the pole, and one of the women took great delight in stepping up on the platform to secure Honey’s head to the pad with a pink silk ribbon.  Her soft little bottom was puffed up by the tight thigh strap, making an inviting target; her new master stepped up to her and gently eased his finger into her tight little anus; he then showed her the vicious leather plaited whip, and felt the sissy clench her sweet bottom on his finger with fear. He smiled with satisfaction; how tight that delicious pussy would be, when he forced his huge cock in there later.

Her master was an expert with the whip; he would not damage his latest asset, but he would ensure the sissy knew pain; his audience and his bulging impatient cock demanded that the sissy suffered.  He cracked the whip in the air, and Honey yelped through fear alone, making the crowd of leering males and women laugh at her all the more.  Honey’s cock stiffened and rubbed the leather padding as she squirmed; her little balls and anus tingled as she viewed some of the males to the side of her, stroking large erect cocks; they would enjoy her whipping, and honey rubbed her stiff cock on the now slippery leather and her soft belly as she now relished the cruel kiss of the whip.  She was not sure if she heard the crack or felt the pain first, but she was sure of the pain that stung her soft cheeks.  The men stroked their cocks vigorously as the sissy squealed and wept as the lash bit home, Honey did not hear a crack with the next delivery, just a swirling noise as her master expertly made the whip coil about her middle, causing her exquisite pain; the crowd jeered and applauded as a sweet red line was left upon her cheeks.  Through her tears, Honey was now enjoying the pain; she saw some of the men shoot wads of cum, the spectacle so sweet they were unable to hold on till the end; Honey’s little cock pulsed and buzzed as she squirmed against the pole and flexed her tightly bound body, each exquisite bite of the whip brought her closer to yet another orgasm.  Her master’s cock stood fully erect now, tucked under his belly strap as he brandished the whip; he could see the urgency of his sissy as her little bottom gyrated sweetly against her restraints and knew she was ready to disgrace herself once more; he smiled as he raised the whip for a final salvo, he would fuck an utterly defeated and drained sissy.

Honey was now in sweet trance-like state as her little bell-end squeezed and pulsed between the pole and her belly; she felt the whip bite again and again in quick succession now, saw huge black velvety cocks with dripping shiny bell-ends, thought of how her new master’s cock would hurt her bottom more than any whip, heard the women laughing at her pain… she squealed in a different tone now; the lash bit home yet again as she trembled all over in sweet ecstasy and complete submission, hot cum squirted lavishly up her belly and the luxurious feel of the leather pole.  Though she had already cum twice before, her orgasm in the face of an audience of wickedness was as though she had not cum for a month; she squirmed in heavenly submission and felt the last lashes as she messed like never before, and watched to her side as those males who had managed to hold on, now shot their hot tributes to the suffering sissy.

Honey sagged against the pole, spent and punished, her little cock dribbling gratefully as the crowd applauded and cheered their appreciation of the show, but the show was not quite over yet.  The womenfolk released her from the pole and rubbed a balm into her soft white flesh, soothing her wounds which were superficial.  They smiled gleefully as she had been lain across a beam to allow access to her sweet cheeks; her hands were harnessed and her master, who was rampant, wasted no time on ceremony.  Honey, exhausted and spent, whimpered pitifully as she felt the large African part her cheeks, her little cock did its best to erect and her anus tingled as she awaited the pain.  Her master stood with huge stiff cock, arched his pelvis and eased his huge black cock into the tight warmth of Honey’s anus. She squealed feebly, thinking he might split her; such was the pain, as her anus became her pussy for the first time.  Her master grunted with pleasure as he pushed home to the hilt, making Honey weep again bittersweet tears as she tingled at the thought of being owned.  Honey’s whimpering’s helped her huge master quickly to his goal; in no time at all he moaned in heavenly ecstasy as his huge cock jetted a generous load into his new sissy; Honey now pursed her lips contentedly as she felt the hot surge within her, and felt cum trickle down her legs.  She was mastered now, and in submissive heaven.