Mistress Elaine Ch. 08-10

The chatter increased as his position became clear: an older man, with his legs in heels and dark stockings, with his legs in a wide V and his body leaning forward. The black thong barely contained his erection and the green satin basque pushed his breasts so that they hung down with pointed nipples. Someone slapped him hard on his ass, and a smooth feminine hand cupped a breast. Then the group moved away, and he was left waiting. He then felt a tug on his leash as Jennifer was quick to remind him that she was still by his side. She leaned closer to whisper in his ear.

"Still feeling manly, Boxwood? Just focus on giving, not taking."

As Jennifer stood close by, holding his leash, a blindfolded Boxwood heard the voices and chatter as more women joined the party. Some looked and then laughed at the ridiculous way he was displayed in heels and green satin. Others explored him, with their hands running up his stockinged legs, patting and probing his exposed ass, and slapping and pulling at his hard cock in the tiny thong.

Others found his exposed nipples and his breasts lifted high amusing, rolling the nipples or snapping them sharply to watch his reactions. A few put fingers or thumbs to his lips, where he sucked and licked them. If he hesitated to respond, Jennifer gave a hard tug on the leash and slapped his thigh with the riding crop. He kept his mind on giving his body and offering pleasure. He tried to ignore his hard penis and his ever present need.

There was a ringing, as Mistress Elaine chimed a glass for attention.

"Ladies, I'm so glad you could make it here this evening. I see many of you have met Boxwood, a new possibility for my stable. He's working on learning to give up his misguided idea of himself as James Bond, seducing beautiful exotic foreign girls, and learning to accept his true role as a giver not a taker. He needs to get away from a focus only on his own feelings."

Mistress Elaine nodded to Jennifer, who put down the leash to move closer to him. He felt her cool hand on him, pulling down the thong to cup his balls and stroke his hard shaft. His shame and his excitement rose and as he braced his arms on the chair his hips rocked and he was thrusting in her hands. Just as he began to cum he felt numerous pinprick stings on his ass as Mistress Elaine hit him firmly with her flogger. He felt the rim of a glass against his cockhead and as Jennifer continued to stroke him the combination of the pleasure of Jennifer's touch and the pain from his Mistress's flogger caused him to spurt copious amounts of cum into the glass. Jennifer held up the wineglass, now painted with Boxwood's cum, for the audience to see. The laughter was mixed with some applause.

Mistress Elaine gave him three more strokes of her flogger across his already reddened ass causing Boxwood to jerk against his bonds with each successive hit. She then slipped off the blindfold. He was still stretched out and exposed, dripping, and now in considerable pain as he looked around the circle of women. "Pleasure only gets you pain and defeat, Boxwood. Drink up, and we can get on with my party."

He tilted his head back and Jennifer held the wine glass to his lips as he swallowed the milky liquid and licked the inside of the glass clean.

Chapter Ten

Mistress Elaine had not allowed him to clean up after the embarrassing display so his lips were still coated in his own dried cum. Jennifer had stuffed his soft cock back into the thong and unchained him. Now he worked the room with her, offering around silver trays of the party snacks Jennifer had made. As he offered his tray, some women touched him, laughing with each other as they handled his exposed breasts, cock and ass, or smiled at his difficulty walking in the high heels. Now he was the cocktail waitress, pawed by the customers, and he had to take it silently and with a pasted on smile.

Jennifer caught his eye and glared at him. They were not in this together; she clearly felt superior to him was highly annoyed at sharing the limelight of the party and the attention of Mistress Elaine with him.

He held still as a tall blonde woman put his hand inside her dress to fondle her voluptuous breasts and whispered in his ear that she would like nothing more than for him to fuck her on the coffee table with everyone at the party cheering them on. His cock pulsed when he heard her lewd suggestion but then suppressed the idea of actually doing it. Instead, he began to wonder about Mistress Elaine's stable of submissives and Jennifer's place in it. He also wondered about his role as well.

Mistress Elaine regaled the partiers with stories of the submissives she had in her stable over time and ended with the story of Boxwood having to clean the guest bathroom with his undergarments and his tongue and then to wear his soiled undergarments after he was done. The guests were howling with laughter as Mistress Elaine embellished on the tale and most stole a glance at Boxwood, who was standing in the corner in his frilly outfit. He was humiliated to be the butt of the party jokes, yet his cock remained erect, to the delight of the partygoers.

At the close of the party Mistress Elaine announced that she would conduct a contest. Two female volunteers would be given oral sex by Jennifer and Boxwood. The winning team would be the one where the guest had her orgasm first. The winning guest would be rewarded with a bottle of wine of her choice from Mistress Elaine's cellar. The winning sub would be directed to treat the losing sub as his or her slave for a full day and would be able to exclusively service Mistress Elaine for one day. Of the dozen or so females in the audience all but one raised their hands to volunteer. Mistress Elaine selected Reagan, one of her college roommates, to pair with Jennifer. Mistress Elaine had spent many hours making love with Reagan and knew what to do to make her cum quickly.

Mistress Elaine approached the one woman, Gloria, who didn't volunteer. "May I ask you why you didn't volunteer?"

"Of course," said Gloria. "I'm not a big fan of oral sex. I prefer vaginal or anal intercourse. I can't remember the last time I had an orgasm through oral sex."

"I think Boxwood has potential in this area. Would it be all right if I paired him with you?"

"Sure, I'm always willing to try and since you're asking how can I refuse?"

Both of the women "volunteers" slipped off their panties and laid back in the leather club chairs in the living room. Mistress Elaine whispered into Jennifer's ear. Boxwood and Jennifer then both knelt in front of their teammates and looked to Mistress Elaine to begin. Boxwood was certain he would lose and would be subjected to a full day of pain and humiliation at Jennifer's hands. Jennifer was already thinking about the ways she would make Boxwood's life hell.

Mistress Elaine dropped Reagan's panties on the floor and the contestants began. Jennifer loved pleasuring women. Reagan was an attractive woman in her 40's. She had soft, shapely thighs and a shaved pussy. Jennifer heeded Mistress Elaine's advice and first started licking Reagan's ass. Mistress Elaine told Jennifer that a good ass licking would make Reagan's clit ultra-sensitive. Reagan responded with audible moans as Jennifer swabbed Reagan's puckered hole.

Gloria was one of Mistress Elaine's mentors. She was in her mid-50's. She had gained a bit of weight over the years but was still attractive. She parted her plump thighs and Boxwood could see a thicket of dark curly hair and could smell her earthy aroma. Boxwood reverted to what he knew. He stabbed Gloria's vagina with his tongue and then worked his way around her clit. Gloria was surprised at Boxwood's skill, as the penetration with his tongue was quite pleasurable. She pushed Boxwood's head hard against her crotch as the pleasure from Boxwood's tongue made her tingle.

Reagan was panting heavily as Jennifer was now working diligently on her clit. However Boxwood took Gloria's preferences into account by wetting his middle finger and sliding it into Gloria's ass. "Ahhhhhhhhhh," cried Gloria as she came, to the delight of the guests. Boxwood lifted up his head, soaked with Gloria's juices, in triumph. Gloria thanked him for his service and was delighted that she was able to cum through oral sex.

Mistress Elaine showed the guests that she was pleased, but Boxwood saw her icy stare as she was saying her farewells. Jennifer did everything she could to keep on her happy face, while secretly wanting to throttle Boxwood.

As the last guest left the cottage Mistress Elaine closed the door and faced her charges. Both of them dropped to the floor with their heads down and their hands clasped behind their backs.

"First I want to congratulate both of you on a successful party. The food was fabulous and the service was attentive. Thank you. Second, I will be punishing both of you . . . severely. I will need to think about what punishment is appropriate. Jennifer, you lost. And you lost when I told you what you needed to do to win. Boxwood, you cheated. I saw you slide your finger into Gloria's ass. I told you this was an oral sex competition. The use of your finger was not allowed and you knew it. Now clean up the party mess and then clean up yourselves and present yourselves to me in one hour, naked."

Jennifer was beside herself that she would be punished once again due to Boxwood's actions. Boxwood feared the reprisal from Jennifer would be far worse than that meted out by Mistress Elaine.

Mistress Elaine emerged from her room precisely one hour after she discharged her subs. She went back into the living room and both Boxwood and Jennifer were waiting there kneeling, heads bowed, with their hands clasped behind their backs. She had showered and her long strawberry blonde hair was still damp and hung limply on the front of her robe. The belt of the robe was untied, allowing Boxwood and Jennifer to feast their eyes on Mistress Elaine's exposed breasts and damp cunt.

"Jennifer, as a slut what do you desire above all else?"

Without hesitation she said emphatically, "To worship my Mistress's body."

"And what part of Mistress's body?"

Staring at the object of her affection, Jennifer replied, "Mistress's pussy."

"Precisely. For your punishment I'm going to let Boxwood eat my pussy. You will watch him eat my pussy and while he is doing so you will tell me why his pussy eating skills are superior to yours."

Jennifer blanched at her punishment. She would have rather endured 20 lashes from her Mistress's cat than provide a color commentary on Boxwood's superior pussy eating skills.

"And Boxwood, what would you fear the most right now, and be truthful or I'll double your punishment."

Boxwood did not hesitate to confess his greatest fear. "I'm afraid of what Jennifer will do to me for winning the competition in an underhanded fashion."

"I suspected as much. But I don't want to reward Jennifer by allowing her to punish you. Two of my subs are returning from vacation from Moscow tomorrow. They will undoubtedly be distressed to learn that I am considering adding another to the flock and will want to subject you to a hazing that even I couldn't imagine. It's a married couple, Valentin and Galina. I'll let Jennifer fill them in on the details from these past two days and then they will determine your punishment."

Boxwood was elated that he would be able to worship Mistress Elaine's pussy, but that elation was tempered with the knowledge that he would feel the wrath of a Russian couple that would like nothing more than for Boxwood to go home crying. Then his attention turned again to Mistress Elaine.

Mistress Elaine looked directly at Boxwood and he at her. She shrugged her shoulders and let her robe drop to the floor, puddling at her feet. She stepped over the robe and approached the living room sofa. In her uninhibited nakedness she made a point of casually laying sideways on the sofa, every bit the voluptuous femme fatale that Boxwood would worship in a Rubens painting. He realized now how well Mistress Elaine masterfully exploited his dreams and his fears. Kneeling naked, he was hard and excited to see her sensually exposing her body and to know he would be tasting her soon. At the same time the idea of other subs, especially a couple, filled him with dread but made him hard, too. He would clearly rank below the three he knew of, and there could be others, and he shivered to think about how Mistress Elaine would use Valentin and Galina to humiliate him even more. He knew he would be tasting Valentin's cock and feeling him penetrate his ass, things he had never done nor sought to do. It made him wonder if he should stop this now.

Then Mistress sat up on the living room sofa, opening her legs wide and using her finger to silently beckon him. He saw her smooth slender thighs, framing the strawberry blonde pubic hair damp from the shower, and his choice was made. He was crawling to her, heeding the siren's call, her demanding more and him needing more.