Sasha's Portrait

by B J Wane

  Sasha had enjoyed their time with Daniel and Melanie, especially her introduction to lesbian sex. She never would have imagined making love with another woman was so enjoyable, but she had, and she wanted to do it again. But the thought of embracing just any woman wasn’t nearly as appealing as succumbing to Melanie again. She had a fondness for the other woman who had shared so much with her, including herself and her husband. If submitting fully to Derrick meant more encounters with the other couple, she couldn’t wait.

  Of course, she knew enough that agreeing to complete submission meant the pleasant, enjoyable encounters were interspersed with catering solely to Derrick’s pleasures, more often than not at the expense of her own. She thought she was ready to take that step, wanted to steep herself into the sensual depravity of submitting to his every whim, a submission that, thus far, had brought her nothing but satisfaction.

  They arrived in Jacksonville a short time later and stopped at a small outdoor café for lunch. “I want to visit a printer before we find a place for the night,” Derrick said as he paid their tab. “He was referred to me by a photographer and reportedly does an exceptional job making prints. You might want to consider getting prints done of some of your scenes. Prints are cheaper and sell well with the general public.”

  “I bet yours don’t sell to the general public,” Sasha returned teasingly.

  “No, but, I can charge more for mine due to my selectiveness.”

  Derrick found the small shop easily and escorted Sasha inside with his hand at her elbow. They were greeted warmly by a short, older gentleman with a receding hairline, wire rimmed glasses, and a small potbelly. “You must be Mr. Matthews. It’s nice to meet you. I’m Ben Wilkes. I’ve admired your work for years.”

  After Derrick introduced her, he pulled out a portfolio of pictures for him and Ben to look over. Sasha left them alone to do business, walking slowly around the large one room store to view the prints hanging everywhere. She didn’t notice the lull in their conversation until Derrick said her name quietly.

  “Sasha.”

  Sasha turned to face him and swallowed over a throat gone suddenly dry. Derrick’s hands were loosening his belt; and, by the look on his face, she deemed it was time for another lesson.

  “Bend over the desk, bare assed, hands behind you.” Derrick removed his belt and doubled it over as she moved to obey him without question.

  Conscious of Ben’s eyes on her, she crossed to the desk set in the far corner of the room, reached beneath her skirt and lowered her thong to mid thigh. Leaning over the desk, her buttocks exposed and vulnerable, she clasped her hands tightly behind her. Derrick wasted no time applying his belt across her ass, each stroke sure and hard, eliciting small cries from her which he ignored. Sasha tried to stay still; but, by the fifteenth lash, she was wiggling in pain, her entire backside a flaming inferno. The last five were always the hardest, and she had to clench her hands tightly to keep from trying to cover herself. She breathed a sigh of relief when he returned his belt to his waist, but it was short lived when he simply turned from her without giving her permission to rise.

  Derrick returned to the large table where his pictures were strewn, several of them of Sasha. The two of them continued where they had left off, but it soon became obvious that Ben’s attention was more on Sasha’s beautiful, reddened ass than on his pictures. This scene was working out better than he had hoped, and Derrick was encouraged by Sasha’s cooperation thus far that she was going to pass this final test with no problem. He hoped so, because it was a crucial one, a lesson in abject subjugation, ceding to his demands without qualm or question, solely to please him.

  When Derrick noticed Ben’s hand straying to his crotch, his hard-on impossible to ignore as it tented his loose, suspender held slacks, he knew the temptation of Sasha’s ass was too much.

  Looking pointedly at Ben’s crotch, Derrick said, “You’re more than welcome to relieve that in her ass. I can wait.”

  Ben gulped loudly, his eyes widening in surprise and hopeful lust. “Oh, I couldn’t. I mean, I’ve never done it in a woman’s….you know. There.”

  Derrick grinned encouragingly. “Well, then I suggest it’s way past time that you indulged in that pleasure. Trust me, you’ll love it. Sasha’s ass hasn’t been used much and is still exceptionally tight.”

  “And, she won’t mind?” he asked, encouraged.

  Derrick shrugged indifferently. “She does what she’s told.”

  His eyes glued longingly on her ass, Ben lowered his suspenders and started undoing his slacks as he walked over to her. “Well, if you’re sure.”

  “Here.” Derrick handed him a tube of lubricant. “You’ll need this.”

  “Oh, yes, of course,” Ben floundered, embarrassed by his ignorance.

  Sasha had heard every word of their exchange, and she didn’t have to consider whether she wanted to do this or not. She knew this was a test, a crucial one in blind obedience; and, regardless of the humiliation of having her ass offered to a complete stranger, her first priority was pleasing Derrick. At that moment, that was all that mattered. As Ben spread her buttocks and slowly inched his greased cock in her anus, her eyes were on Derrick, wanting to witness the pleasure he received from her degradation.

  “Oh, dear. She’s so tight and this feels too good. Oh, I’m sorry,” Ben moaned when after only three short thrusts, he was spewing his seed deep inside her.

  The whole thing was over so quickly that Sasha barely had time to register the fact that he was in her before he was pulling out with a red face brought on by his orgasm and his embarrassment.

  “Well, that was awkward,” he said to Derrick while pulling up his pants. “My wife’s been dead for five years, you see, and I’ve never done this…”

  “Relax,” Derrick said easily. “It happens to all of us. Let’s finish pricing these.”

  “Huh, Mr. Matthews, she’s not moving.”

  “Because I haven’t given her permission to.”

  “Oh, I see,” Ben answered even though it was clear he didn’t.

  Thirty minutes later they had finished their selection and pricing of the paintings Ben would be making prints of for Derrick. As Derrick was gathering up the rest, he noticed Ben was sporting another hard on and eyeing Sasha’s exposed ass longingly. Smiling, he said, “We don’t have to leave quite yet. Why don’t you give it another try?”

  “Oh, could I?” Ben didn’t wait for an answer as he strode over to Sasha and wasted no time dropping his pants and thrusting into her. His thumbs digging into her cheeks; he spread her wide; his eyes glued to his cock pummeling her puckered, tight hole. “Oh, yes, this is going much better,” he sighed as he pumped slowly, burying his cock fully before pulling back and repeating the movement over and over.

  This time, when Sasha watched Derrick, he watched her also; his eyes lit with pleasure as she docilely lay there for Ben’s use. He lasted a good fifteen minutes this time; and, while Sasha found no pleasure in this ass fucking, she found a great deal of pleasure in the way Derrick proudly helped her up and led her out to their SUV. Later that night, his cock filled her pussy, stretching her completely as he rode her long and hard and allowed her the freedom to come as often as she wished.

  It was almost two o’clock the following afternoon when Derrick pulled into his drive. Sasha could only gape at the beautiful two story ocean front home. She knew he was wealthy being the sole heir to a large pharmaceutical company founded by his father, and his home was a testament to that wealth. The front lawn was a plush green veranda, landscaped beautifully. The back led down to his private beach where she could see a boat moored at the dock. A porch that wrapped around the second story of the house made it easy to view the property from the front or the back.

  “I take it you like it?” Derrick asked, smiling at her gawking expression.

  “Who wouldn’t? I can’t wait for a tour. You must’ve been climbing the walls that week in my small cottage.”

  Derrick reca
lled vividly Sasha standing naked the first time before him in her home. No, he hadn’t felt confined at all that week. Quite possibly, that could turn out to be the most memorable week of his life. Derrick grabbed her bags and led her inside where he set them in the marble tiled foyer.

  “Derrick, it’s beautiful. I’m already wishing I didn’t have to leave on Monday.” Since it was Friday afternoon, she felt the end of their journey looming in front of her, and it wasn’t leaving his home that was bothering her, although she couldn’t tell him that. Her hands automatically went to the zipper at back of her skirt as she asked, “Are you going to show me around?”

  Derrick laid a hand on hers, stopping her from undressing. She had gotten so used to stripping whenever they entered their lodging, it had become second nature to her. “No, Sasha, I’m leaving.”

  “What?! Where are you going?”

  “I have a few things to do, like return that rental, and then I’m going to my club for the weekend.” He placed his fingers across her mouth as she started to reply. “Just listen, don’t say anything. I want you to join me, but Sasha, only if you’re willing to submit to me completely. I want you and complete control of you.”

  Sasha knew this moment was what he had been leading her up to and her first inclination was to say yes. She wanted to be his, to belong to him in everyway. But, she refrained, listening as he asked.

  “If you agree, the weekend won’t be easy for you. You’ll receive little pleasure and be subjected to public discipline, as I deem fit. Two days of catering to my pleasures only, Sasha, so think carefully before deciding.” Reaching into his back pocket, he withdrew a one-way ticket back to Nantucket. “I told you when we set out that you were free to return home at any time. Take this.” He laid the ticket in her hand. “You have two choices. Spend the weekend with me as my sub, or spend it here, in my house, and return home Monday morning. You’re free to help yourself to my home and anything in it. If you’re not at my club by six this evening, I’ll know you chose the latter. No matter which way you choose, I want you to know I’ll have no regrets.” Going to a small writing table, he wrote something down and handed it to her. “That’s the address of the club. There’s money in with the ticket for a cab.”

  Before Sasha could say anything, he kissed her fast and hard and then left without another word or look. Sasha had to physically quell the urge to run after him, beg him to take her with him now. She didn’t need to think about it, it’s what she’s wanted all along, what he had prepared her for. She spent the next two hours poking around his home, walking on the beach, killing time before calling the cab.

  At five o’clock, with fingers shaking, she phoned for her ride. Slipping the plane ticket in her purse, she left everything else behind when she left a few minutes later. Handing the paper with the address to the driver, she settled back and tried to stem her nervous excitement. She was more afraid of the unknown rather than of Derrick demanding anything of her she couldn’t handle.

  When the cab pulled in front of a building that would pass as a very plush resort surrounded by a six foot stone wall, she ignored his knowing grin, paid him, and took the final steps on her journey of self discovery. A young woman dressed in a short black dress was standing behind a tall counter as Sasha entered the dim interior.

  “May I help you?” she asked politely, her warm smile putting Sasha at ease.

  “I’m here to meet Derrick Matthews.”

  “You’re Sasha! We’ve been expecting you. Let me ring Lana. She’ll prepare you to meet Master Derrick.”

  A few minutes later, a tall, slender woman dressed in skin tight black leather pants and a black leather semi-bra which barely held her ample breasts, her nipples bare and pointed, strode up to her. “I’m Lana, and I’ll be preparing you for your Master. Follow me. I’m glad you’re early as I’ve got a busy evening ahead of me.”

  Sasha meekly followed the other woman down a corridor and into a sparsely furnished room. She saw nothing of the club other than several other closed doors in that same hall. Lana shut the door behind them and then turned her sharp gaze to Sasha.

  “Strip, down to your thong.” Expecting to be obeyed, Lana simply stood there, arms crossed under her breasts.

  Sasha did as ordered, trying to be quick and efficient, but her hands were a bit clumsy due to nervousness, and it took her several attempts to get her back zipper lowered and to slip out of the rest of her clothes.

  “I need to emphasize a few club rules,” Lana said as she walked slowly around Sasha. “You will refer to your Dom as Master, or, in your case, Master Derrick, at all times. When standing in his presence, you’re to stand with feet spread, hands behind your back, if they’re not cuffed, and head bowed.” She stopped in front of her, her eyes staring with intimidation. “When your Master commands you to do something, you do it, no questions asked. When outside your room, you’re not to speak unless spoken to or given permission. Assume the position means on your knees, face to the floor, and hands behind your back. Are you clear on these?”

  “Yes,” Sasha replied, not sure how to address her.

  “Good.” She nodded brusquely. “Up on the table, face down.”

  Sasha climbed onto the massage table and lay with her face down in the hole at the head. Lana gave her a very thorough, very intimate head to toe body massage, checking to make sure she was smooth between her legs as well as everywhere else. Twenty minutes later, her body oiled, rubbed, and completely relaxed, Lana ordered her up.

  “When was the last time you used an anal douche?” she asked.

  Sasha couldn’t help the blush that stole across her cheeks. “This morning.”

  “Okay, then you’re ready. I’ll escort you to Master Derrick’s room.”

  Wearing nothing but a black lace thong, Sasha followed Lana out the door and up a wide staircase until she stopped before a large, ornate door, bracing herself to meet Derrick as her Master for the first time.

  Chapter Fourteen

  Derrick flung open his door, impatience shimmering in his grey eyes as he looked at her. “Thank you, Lana. You’re dismissed.”

  “Yes, Master Derrick.” Lana walked away, leaving Sasha alone with her Master.

  As he shut the door behind her, Sasha only captured a brief glimpse of the room before she quickly remembered the rules and bowed her head; her feet braced apart, and her hands clasped tightly behind her. Other than a large four poster bed, the only furniture was a small table and chairs and a dresser which was where Derrick had moved to before returning to stand in front of her.

  “Look at me,” he demanded.

  Sasha raised her eyes past his long, muscled legs clad in black leather. A matching black leather vest was all he wore over his strong chest, and the sight of his hair roughened torso made her pulse leap with excitement as well as the objects he held in his hand.

  Derrick set the flogger, butt plug, cuffs and nipple clamps on the table and held up the collar for her to see. “I had this made especially for you in New York. As long as you wear it, you’re mine. Are we clear on that, Sasha?”

  “Yes, Master.” Made of soft, supple sable leather and studded with sapphires, a silver D ring in the middle, it was a beautiful sign of his ownership, and she never hesitated in accepting it. As Derrick fastened the collar around her neck, she was surprised at how right it felt, how much it emphasized her status.

  Stepping back, he picked up the cuffs and walked behind her where he attached them and then hooked the two together before returning to stand in front of her. “Your coming here and submitting to me means more to me than you’ll ever know, Sasha,” he said as he calmly attached one clamp around her right nipple, ignoring her gasp of pain as he moved to the left. “You look beautiful like that, baby. Your nipples are red and tight, your breasts fill my hands perfectly.” He cupped her flesh and ran his thumbs over her distended tips before stepping back again and looking into her eyes.

  “Assume the position.”

  “Yes, Mast
er.” Sasha knelt and, with his help, lowered her head to the floor, her nipples sore as they rubbed the carpet, her ass high, her knees spread. She felt her pussy swell with need and dampen with desire brought on by the ache in her nipples and her submissive pose. When Derrick spread her buttocks and pushed the greased, large plug up her ass, her hips bucked, and she ached to feel him penetrate her cunt with fast, hard strokes.

  “Look how wet you are,” Derrick observed as he knelt behind her. Running a single finger through her slit, he brought it up to show her how it glistened with her juices. “This is how it should be, your pleasure stemming from mine. Your body mine to do with as I please, whether it’s to cause you pain or pleasure. I will share your mouth and ass, but this,” he said, cupping her pussy, “is mine. A few might get the privilege of seeing your pussy or, maybe even touching it, but no other cock will enter you here.” He inserted three fingers inside her dripping passage. “Your cunt is mine and mine alone while you belong to me. Do you understand, Sasha?” Two fingers pinched her clit and held it while she answered.

  “Yes, Master,” she gasped as the pain filled her pussy. “I want no other to fuck me there.”

  His fingers caressed her clit before he rose and picked up the flogger.

  “That’s good.” Running the flogger over her buttocks and thighs, he asked, “Do you know why I’m going to whip you?”

  “No, Master,” she answered as the braided strands from the flogger caressed her between her thighs, making her shudder.

  “Because I can, and I like seeing your pretty flesh marked by my hand.”

  The first strike of the flogger elicited a cry from her as well as the second and third, cries he didn’t forbid as he striped her flesh from the top of her ass to her thighs, raising light red lines that, along with the way she was trussed up for him, made his cock swell.

  Sasha bore the pain as it quickly gave way to pleasure, intense, body consuming pleasure. She had to force herself to shy away from it, concentrate on her master’s pleasures only and await his permission to indulge her own. A knock on the door put a stop to the lashes after the tenth stroke.