"What do you get for the woman who has everything?" Jack asked himself. His wife Carol was easily as successful in business as he was in his law practice. Neither of them wanted for much materially and after ten years gifts of extravagant jewelry or even sojourns in exotic locations seemed almost anti-climactic. This year he would give Carol something he knew she'd been dreaming of for the last few years. He would give her an indulgence she hadn't thought she would actually be able to have. The "what" determined the how became his mind's task.
Jack began interviewing candidates discretely. The pretext was that Jack was looking for an eighteen year old senior to be an intern "gofer" with his law practice. The clever attorney made arrangements to interview seniors from St. John's. Jack had no doubt he would find the perfect gift for Carol among the student body. Jack wanted a candidate from the local parochial school for the simple reason that he knew that what Carol craved above all else was a boy's innocence.
After interviewing several eager workers; all of whom were too short, spotty or chubby, Marcus walked in. After a quick interview with innocuous seeming leading questions it seemed that Jack had found his man. Slender, dark haired and olive skinned with deep brown eyes, the boy was exactly Carol's type.
"So tell me Mr. Cicero; you ARE eighteen, correct?"
"Yes Mr. Carson, I am," Marcus replied.
"This job might cut into your free time, are you sure your girlfriend won't mind?" Jack asked slyly.
"I...I don't have a girlfriend, Sir."
"A strapping young man like you, well, I am sure you have had plenty of girls."
"Um...no Sir, I haven't met the right girl yet."
Was this kid perfect or was this kid perfect? Feckless, definitely a virgin, fresh faced and fit. All that was left was to make the boy burn for Carol. This would be easy enough, as the intern was given free time on an office computer that Jack "carelessly" loaded with several videos of his stunning wife in action with several of her lovers. The boy surely would get an eyeful of Carol's full breasts with their long, chubby pink nipples as well as her lustrous auburn hair, flashing green eyes, and long, elegant legs. At thirty-five Carol Carson was the kind of older woman every young boy spent countless hours daydreaming about; powerful yet feminine, sensuous yet nurturing.
Jack finally caught Marcus watching a video of Carol. This was one of Jack's favorite home videos; where Carol took on three black soldiers home on leave from Afghanistan. The sultry Carol did her patriotic duty, satisfying their massive young cocks with her well-seasoned holes. Jack remembered how they had left her filled with hot cum and savored the memory of getting "sloppy seconds". Marcus was masturbating furiously watching the orgy on the computer screen.
"You like my wife's body?" the lawyer asked.
"Errrrrrmmmm," the boy was caught. He had no idea how to react.
"My wife likes younger men, Marcus. It is a fact I have come to terms with and have come to enjoy. I get quite an eyeful and when she's done enjoying her stallions she satisfies my every need. It's an arrangement we are both quite happy with. So my question to you, Marcus, is would you like to fuck my wife?"
"Mr. Carson," Marcus stammered nervously "I...I'm a...v...v....v...."
"A virgin, Marcus? I already knew that. It's why I hired you. I decided this year I would give my wife a virgin to have any way she wants. Would you be willing to be my wife's Christmas present, Marcus?"
Marcus only had to think about it for about thirty seconds. Here was a chance to become sexually experienced without the pressures of an ongoing relationship and it was certainly less tawdry than losing it with a prostitute. He heartily agreed and terms were discussed. Marcus would be presented to Mrs. Carson nude under the Christmas tree with his hands tied behind his back and would obey her every command knowing that at the end of the evening he would have spent his virginity in the velvety warmth of the statuesque goddess' caress.
In the weeks leading up to Christmas Marcus fantasized constantly about Mrs. Carson; her voluptuous body and outsized sexuality. He'd seen so many scenes of her on Mr. Carson's computer, mostly with younger men and in some cases orgies involving groups of men and women who seemed to be married couples of the Carson's acquaintance. He was certain his initiation into the mysteries of sex would be much more...interesting...than most young men's. His mind kept returning to a video he'd seen where Mrs. Carson used a strap on dildo to anally violate a younger guy and felt anxious, yet aroused. As directed by Mr. Carson Marcus refrained from masturbating at all on Christmas Eve. He couldn't sleep from the anticipation of what he would soon experience.
Christmas morning at 6:00 am Marcus arrived as directed and was prepared by the maid for his role under the tree. Irena undressed the youth and directed him to a tub filled with warm water infused with rose petals. After his fragrant bath, his hands were bound with red cord and a red ribbon was tied around his erect member. A collar was buckled around his neck with a cheerful tag affixed reading "To Carol, Love Jack".
Marcus was directed to stand at parade rest in front of the tree and to wait for the Carsons to make their way downstairs. Around 9:00 am the wealthy couple descended the staircase. Wearing full makeup and a sheer purple negligee, Carol caught a glimpse of her present and squealed. She ran to the tree and clutched Marcus' stiff penis in her delicate hand "Oh Jack, he's perfect...please tell me you are a virgin, boy." Marcus nodded as his cock dripped pre-orgasmic nectar into Carols hand. Carol licked up the sticky sweet pre-cum and smiled wickedly.
"You are going to be a good boy and serve drinks to my guests and watch me with them and then....just wait cutie!" the decadent older woman's voice was like hot cinnamon and orange blossom honey pouring all over the lad's soul.
The first guests to arrive were a party of young men introduced as a street dance troupe. There were five of them and they all were young; three cut black dancers, one Latino and one very tall blond boy with a crew cut. Marcus was teased mercilessly as he brought the dancers bottles of beer which they quickly downed. It was not long before Carol had unzipped the Latin dancer's pants and was sucking his fat cock. Seeing an opportunity one of the black boys positioned his pole beneath the ravishing cougar's wet vagina as one of his compatriots pressed his massive erection into the married woman's asshole. Carol took the other two young men's large cocks in her hands and gave them pleasure as her holes were filled deeply with their buddies' cocks.
Marcus had no relief. Once the orgy commenced his hands were bound again and he was made to sit in a simple chair placed next to Mr. Carson's comfortable leather recliner as they watched the insatiable Mrs. Carson take several loads of hot cum in each of her willing holes. Her studs drained, Marcus brought the young men more beverages and then was he was commanded to lie down and open his mouth. Carol crouched over Marcus, showing him her freshly fucked cunt.
"Do you want this pussy, boy?" she sneered.
"Yes I do." Marcus answered with a croak.
"Call me Mistress Carol."
"Yes Mistress Carol, I want your pussy."
"Lick it clean boy!"
With that command, Carol Carson forced her cum filled slit over the boy's mouth; draining every drop of the goo inside her birth canal into his pretty mouth. To her delight his tongue coiled deeply into her hole and his lips made love to her vulva and clit. The kid was a natural at cunnilingus. He would make some woman very happy one day. The brilliant businesswoman knew only too well hard cocks were a dime a dozen, but a man with an open mind and a talented tongue was worth marrying. His future wife would one day thank her for training this pup.
After allowing herself several Earth shattering climaxes over the sweet boy's mouth, Carol turned her attention to his stiff, dripping member. He clearly needed relief, but she wasn't ready to complete the boy's sexual education. Instead she went upstairs with the boy, leading him into the bathroom. He was told to face away from his Mistress. Carol discretely donned her harness with her ten inch flesh colored dildo and coated the artificial phallus with lube.
"Bend over boy!"
Marcus whimpered in anticipation, but complied with the sultry auburn tressed woman's request. First she invaded the boy's body with her long, slender fingers with plenty of lubricant. Marcus moaned deeply as his hole relaxed and the awkwardness gave over to pure pleasure. Carol drove the proxy cock slowly into the young man's virgin anus. Once she felt her hips touch his cheeks she pulled back much more quickly than she drove in. She slowly guided it back in, withdrawing quickly once more. After a few more of these loving strokes the wicked lady began pumping the youth's hole as if the dildo were a real cock with needs of its own.
As she plowed Marcus tender young hole, Carol spoke her mind about her boy toy. "You are nothing but a bitch boy! Just a bitch for a strong woman and her studs to use. I'm breaking you in, but sooner or later you'll need a real cock up this fuckhole of yours. Yeah, that's good. Take it boy!"
Carol rode Marcus' ass hard and deep for what felt to him like at least an hour. Finally he felt his balls pull close to his body, his cock twitch and then the explosion. With Carol's toy buried deep in his bowels Marcus cock spurted several thick arcs of hot cum all over the bathroom tile.
"Lick it up bitch boy!"
"Yes Mistress Carol," the boy complied.
To his own surprise, Marcus found himself savoring the sweetness of his own jizz on his tongue. Serving a strong woman felt natural to him. Was this his lot in life? He hoped it would be.
Irena returned, and was asked to clean Marcus up for the next round of visitors. He was showered by the rotund maid then dressed in fishnet stockings and suspenders. His face was painted and his cock placed in a restraining cage. Finally, Irena put a frilly yellow frock on the boy and led him downstairs.
Marcus was introduced to Carol's boyfriend Tyrone. Tyrone was tall, at least six foot five, and built like a linebacker. He was standing nude with Carol. Flaccid, his deep ebony cock had to be at least nine inches long and was as thick as Marcus' wrist. Tyrone was looking contemptuously at Marcus and Carol was cackling at his appearance and drinking a dry martini.
"Suck my dick, bitch!" Tyrone snarled.
Marcus looked questioningly at Carol, fear and excitement warring behind his deep brown eyes.
"You heard him, bitch boy. Suck his cock. Get him good and hard so he'll fuck the shit out of me!"
Marcus wrapped his pink painted lips around the massive black member. Fear gave over to lust at first taste. The sweetness of the taste and the strength of the musk seduced Marcus brain. He fell in love with the symphony of experience as the hot black cock found the back of his throat. Marcus gag reflex tried to assert itself as the stiffening cock inched down his gullet, but with Carol's sweet yet firm guidance Marcus managed to deep throat Tyrone. When the cock was removed from his mouth the boy sighed in disappointment.
Marcus was soon treated to a sight that took his mind off the emptiness of his mouth. Tyrone and Carol began to fuck standing up. On Carol's command Marcus happily licked them where they met, getting a taste of cock and pussy all at the same time. Tyrone ordered Marcus to suck his balls and Marcus gladly took the dark globes in his mouth. The taste of the bigger man's balls drove Marcus mad. The boy would have surely been masturbating were it not for the restraining cage on his raging cock.
At last, Tyrone's massive cock spewed its load deep into Carol's quivering quim, spilling out and covering Marcus painted face with hot semen. The pretty boy licked every drop gladly from his Mistress' cunt and off of Tyrone's massive cock. This resulted in a second erection from the black stud.
"Bend over, bitch," Carol sneered.
Marcus complied and Tyrone embuggered him without any pretense of gentleness. Marcus spewed cum as his ass made room for the monster cock invading him. Tyrone's massive balls beat Marcus much smaller nuts as the bigger man used Marcus like a whore. Twenty minutes of hard pounding and Tyrone erupted inside the boy whose cock twitched and shot a small squirt as he had one more climax.
Carol kissed Tyrone deeply, helped him get dressed and saw him out tenderly. Marcus was hopeful to finally have his Mistress' undivided attention. He hoped he would finally be allowed to feel her warm folds embrace his virgin cock. His hopes were to be further delayed. A group of Carol's lady friends and their husbands were coming over. Marcus would be providing oral favors to all of these guests but first he was again cleaned and his makeup was refreshed. Much to the young man's delight several of the husbands had massive members and two of them chose to enjoy him anally.
Next would be Christmas Dinner. Marcus role was as centerpiece; a large candle in his asshole providing light and a conversation piece. After dessert Marcus was allowed a repast of leftovers before being prepared for his final duties of the evening.
Marcus was cleaned up and brought into Carol's bedchambers. The stunning woman was clad in a black leather bustier and matching thigh high boots. She was holding a riding crop. She ordered Marcus to lie down in the bed. She lovingly stroked his body all over with her crop. Light swats to his tender nipples left him fearful yet excited by the leather tip, but she refrained from striking his stiff cock.
After what seemed like an eternity of teasing, Carol decided the boy had waited long enough. She descended onto him, absorbing his long skinny penis in her warm wet folds. The tormented young man's blood caught fire and he climaxed immediately. Carol laughed and kissed him.
"It's ok baby boy. That happens to most boys their first time. Now lick it up and you can go home and think about what has happened today."
"Yes, I got what I wanted Marcus; your virginity. Now clean me out like a nice boy and go home so I can satisfy my husband."
Resigned to his fate, Marcus eagerly licked every drop from his Mistress snatch. Dressed and at the door he asked with deep hope, "Will I see you again Mistress Carol?"
"Yes Marcus, if you will do as I say and wear this at all times," Carol presented the young male with what she explained was a chastity belt to which she would hold the key.
Marcus thought about it long and hard...