Sasha's Portrait Read online

  “Almost done, sir. Ten minutes or so.”

  “Perfect. That’s just enough time to teach my girl a lesson.” He lifted his hand and brought it down hard on her buttock, leaving a bright red imprint. Sasha gasped but kept still. Derrick swatted her again before ordering her to lift her face from her arms. “Turn towards them and see how they watch your punishment with envy.” His hand landed again, and she obeyed him.

  He continued to belabor her ass; his hand falling steadily; his smacks hard and sure as they covered her whole backside. Sasha stayed still as long as possible but was soon wiggling against his hard thigh as much from pain as from excitement. Tears seeped from her eyes as she clenched them tightly, bracing for more blows. With each one, she got wetter and wetter, another orgasm sneaking up on her without pity.

  Derrick noticed her movements, the ways her buttocks clenched as she rubbed against his thigh, and knew she wasn’t going to hold back, again. “Sasha,” he warned, landing a hard blow to the middle of her crack. “Try harder.”

  Sasha was crying openly now, both from pain and despair over knowing she was going to disappoint him again. The orgasm burst upon her with the next swat and continued until he finally quit smacking her and she lay quietly over his lap.

  “Stand up facing me and pull up your pants. I don’t want them seeing your pussy.”

  Sasha did as instructed, pulling her jeans over her reddened ass with difficulty then hooking her bra and buttoning her top. She didn’t know why he kept her pussy from their eyes when he had no problem exposing her breasts and ass, but she was sure he had his reasons.

  “I’m sorry, Derrick…”

  Derrick held up his hand to forestall her apology. “We’ll work on it together. You will, of course, be punished again for disobeying; but, right now, we need to get going.”

  They conversed little over the next hour. Derrick’s curt answers followed by silence told her exactly how disappointed he was in her. It hurt. She was rapidly discovering that pleasing Derrick was growing as important to her as experiencing more orgasmic bliss at his hands. Not even the gorgeous countryside rife with the onset of fall foliage could lift her melancholy. When he pulled off the road into one of the rest areas, she was relieved. Maybe now, he would talk to her.

  “This should do,” he said as he opened his door.

  “For what?” Sasha got out and eyed him uncertainly. He didn’t look like he was in the mood to converse.

  “For your second punishment.” Pointing to the picnic table nestled under some trees, he ordered curtly, “Pants down, hands braced on the bench.”

  Sasha walked slowly to the table more than aware that they were in plain sight of the road. Though the back roads were less traveled than the highways, they had encountered continuous traffic since starting out. The thought of strangers passing by, glimpsing her naked buttocks getting whipped excited her; she just hoped one of her witnesses wasn’t a cop. She had to trust Derrick knew what he was doing.

  Without a word, her hands undid her jeans and pushed them, along with her panties, to her knees. Bending, she braced her hands on the picnic bench and waited breathlessly for the first blow to land.

  Derrick was pleased with her easy acquiescence. She had a ways to go, but he was growing more confident in gaining her total surrender. Removing his belt, he doubled it over, lifted it high, and brought it down forcibly across the middle of her ass. “Twenty, Sasha, since this is your second infraction today.”

  Sasha winced as another blow landed, jerking against the pain. “Yes, Derrick.”

  Derrick continued to talk to her as his arm lifted and fell in evenly paced strokes. “You deserve to be treated this way, don’t you?”

  “Yes,” she gasped as he landed the next stroke right on top of the previous one.

  “You let your body rule you instead of you ruling it. That won’t be tolerated.”

  “I know.” She whimpered with the next strike, tears falling freely.

  “You can’t turn control over to me until you have it yourself, then it will be mine to take from you. Understand?”

  “Yes. I promise, I’ll work harder.”

  By the time he landed the final blow, Sasha was crying openly. She felt completely chastised and ashamed that she couldn’t be who he wanted her to be. She hadn’t realized how badly she wanted these few weeks with him until she thought he might send her home. Rising she turned to face him. His demeanor hadn’t softened any with her spanking.

  “Do you want me to turn back?”

  Surprise widened his grey eyes as he just looked at her for a moment. Her face was streaked with tears, her eyes filled with worry. “Sasha, this is only our first day and your first lesson. As long as you’re willing to take your punishments for your lapses, you’re staying with me as you promised all the way to Florida.”

  Relief flooded her and dried up her tears. “I’m willing.”

  “Good. Now, I didn’t give you permission to rise. Bend back over.”

  Sasha quickly complied, eager to redeem herself. She heard his zipper being lowered and felt him behind her as he grabbed her hips and thrust into her wet pussy.

  “Just as I thought,” he said with humor. “You’re so wet you’re soaking my cock.” He pulled back and then pushed slowly in again and again before pulling completely out of her clinging dampness. “Now you may get up and kneel.”

  Sasha rose unsteadily. Her buttocks throbbed painfully; her pussy felt swollen and empty, in need of more fucking. Kneeling before him, his cock thickly coated with her juices thrust in front of her, she was acutely conscious of her naked reddened ass facing the road.

  “Lick me clean.” Crossing his arms over his chest, he stared down at her, waiting.

  Sasha licked down and then up his hard length, tasting herself as she cleaned him. She knew there was a reason behind this maneuver, just as she knew he’d let her know what it was in his own good time. When she had completely cleaned his cock of her juices, he instructed her to bend over the bench again. Again, he coated his stiff penis with her abundant cream and ordered her to lick it off.

  “Do you like the taste of your feminine cream?” he asked when she had licked him clean a second time.

  Sasha looked up at him and nodded, smiling. “Yes.”

  “Good. Now suck me until I come down your throat. Make it quick. We’re pushing our luck out here as it is. Only a few cars have gone by since we stopped.”

  Fearful of recriminations, Sasha quickly took him in her mouth, sucking hard. His hands went to her head, guiding her movements as she reached behind him and grasped his buttocks to pull him closer to her face. It took him only minutes to come, his salty-sweet come spewing down her throat. She loved the taste of him, the hot hard length of his cock, the way he jerked as he came in her mouth. A car went by, honking, but she didn’t care what they saw. She had pleased him; and, at that moment, that was all that mattered.

  Chapter Eight

  It was late afternoon when Derrick pulled up in front of a posh downtown hotel. A bellman rushed to open the doors for them as they got out. “Nice to see you again, Mr. Matthews. Your usual suite is all ready for you. Would you like your luggage brought up?”

  “Yes, Tim. Thank you. There’s not much.” Derrick took Sasha’s elbow and escorted her into the plush lobby, signed in, spoke a few words to the desk clerk, and then led her to the elevators. Her eyes were wide with wondering awe as she took in the elegance of the four star hotel.

  “The one and only time I was in New York was right after my high school graduation, right before I left for college. My parents and I stayed at the Holiday Inn.”

  “Holiday Inns are nice.” Derrick punched the top floor button, smiling down at her.

  “But not the best, right?”

  “Right.”

  Derrick’s two large suitcases and her small bag were already sitting by their door when they got off the elevator. The suite was just as beautiful as the rest of the hotel with white carpet, a large,
four poster king sized bed, separate sitting area with a big screen television, a small, stocked bar and refrigerator, and the largest, most elegant bathroom Sasha had ever seen. Done in white and gold, it boasted a huge, walk-in shower, Jacuzzi tub and double sinks. The commode was conveniently nestled behind a short tiled wall.

  “Wow.” Turning mischievous blue eyes towards him, Sasha said, “I hope you don’t expect me to make myself ready on short notice the next few days. It could take me hours to prepare before going out.”

  “Giving me another reason to punish you already, Sasha?”

  “I don’t think you need a reason. You would punish me no matter what.”

  “True. But, right now, you’re giving me an excellent reason to give you a third whipping today. Our hotel rooms will have the same rules as your home did.”

  Understanding dawned quickly. Sasha didn’t hesitate as her hands went to her sweater and slowly unbuttoned it. She liked getting naked for him, especially when he remained clothed. She dropped her sweater and bra on a chair and then unsnapped her jeans. When she made to push them down along with her panties, he held a hand up to stop her.

  “Just the jeans for now.”

  She didn’t know why he wanted her panties left on, but she didn’t question him. She had no sooner laid her jeans on the chair and slipped out of her shoes when there was a knock at the door.

  “Stay as you are,” Derrick ordered when she made to go back into the bathroom. Opening the door wide, he ushered a young man in bearing a cart laden with food.

  His eyes widened appreciatively at her nudity, lingering on her nipples, which were stiffening into excited, stiff peaks. Sasha blushed, her excitement at being almost bare in front of this strange man apparent.

  “Huh, enjoy your dinner, Mr. Matthews.”

  “Thank you, we will.” Slipping a large tip into his hand, Derrick led the ogling youth out the door. Turning back to Sasha, he acted as though that was a typical scenario, which, to him, it was. “You may remove your panties now.”

  Sasha slid her panties down and off, slowly coming to the realization that everything Derrick subjected her to was meant to teach her to submit totally to him. So far, she had found his lessons highly stimulating.

  Derrick undid his pants and moved slowly towards her, backing her to the bed. Sasha fell backwards, laughing, as he dropped his jeans and grabbed her knees. Spreading her wide, he pushed her knees to her shoulders as he came down on top of her, his cock impaling her in one smooth stroke.

  “Welcome to New York, Sasha.” He crushed his mouth on hers as he fucked her hard and quick, demanding she come with him as she eagerly lifted for each of his thrusts, grinding her pelvis against his until they exploded together.

  Sasha was rudely awakened the next morning by a hard swat on her naked ass. “Ow! What was that for?” Rolling to her side, she glared at Derrick’s unrepentant, grinning face. He was showered and dressed already.

  “Get up. We’re going to be late.”

  Sasha glanced at the clock. “It’s only seven. I thought we were on a holiday. That means sleeping in.” Plopping back down, she started to grab the sheet to pull back over her when Derrick sat on the bed and unceremoniously hauled her across his lap. He wasted no time raising his hand and smacking her ass hard, raising an instant blush.

  “I told you last night you had a spa appointment this morning,” his hand continued smacking her, making her wiggle in pain and gasp with instant arousal.

  “Derrick, please,” she pleaded as his blows became harder and faster.

  “Are you awake yet?” he asked, moving to the under curve of her buttocks and tops of her thighs.

  “Yes. I’ll get up, I promise.” She could feel her arousal building and knew if she didn’t get off his lap soon, she’d be writhing in the throes of an orgasm within minutes, and she didn’t want to take the risk of disappointing him first thing this morning.

  Derrick stopped smacking her as quickly as he had begun. “Hurry up. You’ve got ten minutes, or you can go without breakfast.”

  Sasha ran into the bathroom, quickly washed up and dressed again in the same clothes she had on yesterday. She would definitely be glad to spend his money on something else to wear. She was starving. Continuous, mind blowing sex tended to do that to her. She made it in time, barely, thank goodness.

  After breakfast, Derrick hailed a cab, explaining it would be suicide to try to drive themselves in downtown New York. As he had explained last night, Sasha would be spending the next three hours being totally pampered at a well known spa.

  When the cab pulled in front of the spa, Derrick instructed him to wait as he escorted her in. “You’ll get a complete wax job as well as a belly button ring. The ring I chose will match my earring.”

  “This doesn’t sound like fun,” she grumbled as he held the door for her. “It sounds like pure torture.”

  Derrick just smiled at her. “You can handle it. I promise the rewards will be worth the pain. Just think of how much pleasure you get from getting your ass whipped.”

  “Not the same and keep your voice down,” she hissed as they were greeted by a tall blonde at the front desk.

  “Mr. Matthews! This must be Sasha.”

  “Debbie, take good care of her. I’ll be back in a few hours. Make sure my instructions are followed to the tee.”

  “Yes, sir. We’ll have her ready for you.”

  Sasha was led away feeling like a cow being led to the slaughter. Three hours later, she had a change of heart. The pain and humiliation of having every scrap of hair removed from her pussy all the way up her crack was made bearable by the full treatment that followed. She had been massaged from head to toe, front and back, warmed in a hot tub, dipped in a mud bath, steamed in a sauna, her whole body lotioned, creamed or oiled, her nails manicured, her hair washed and styled, and her belly button adorned with a beautiful sterling silver loop with a matching chain around her waist. Except for the still slight soreness from her waxing, she felt wonderful.

  “How did it go?” Derrick asked after helping her into the cab.

  “Other than the waxing and piercing, it was wonderful.”

  “The stinging won’t last much longer,” he replied confidently.

  “What do you know about it? You have all of your hair. And, these jeans are killing me.” Her euphoria from being pampered was slowly being over shadowed by the constant stinging of her most private parts.

  “My, someone’s testy. You must be hungry. We’ll stop for lunch and then shopping. That should make you feel better.”

  Sasha looked up at him, a calculating gleam in her eyes. “I’m going to find lots of things to buy.”

  “No doubt,” he returned dryly. “Which is fine, but I get final approval on all purchases. No pants. Dresses and skirts. Thongs, no panties. And, no bras.”

  Sasha rolled her eyes. “Why don’t I just go naked?”

  “You will, when I tell you to. Now, behave.”

  They ate salads at a small Italian Bistro and then walked hand in hand to the exclusive shop Derrick had chosen for her wardrobe. She liked the way he held her hand or elbow as he escorted her around in public. For her, it was a very personal gesture that said he liked keeping in close contact with her, and maybe, just maybe, she was more than just a temporary sex partner. Foolish thinking, she knew, but then she had always been one to live in a fantasy world.

  Apparently, Derrick often made trips to New York and knew everybody. The owner of the clothier greeted him by name and, having been apprised of their arrival beforehand, made arrangements for private consulting.

  “I’ve stacked a pile of dresses, skirts and tops near the dressing room, all in size six as you requested, Mr. Matthews. I’m sure the styles will be to your liking.”

  Sasha didn’t protest at his high handedness and presumption. On the contrary, she found she liked being catered to, liked having him make these decisions for her, which made her wonder if she was as opposed to submitting to him as she c
onstantly claimed. Besides, the sheer magnitude of clothing articles in the two story store was enough to boggle the mind. She would have spent hours combing the racks if they hadn’t thought ahead.

  Derrick handed her several outfits and held the curtain to the dressing room aside. “Try on the ones you like and show me. I’ll be right out here.”

  Sasha closed the curtain and slipped off her jeans and sweater. Picking up the first dress, she slipped it over her head, and it fell just scant inches below her buttocks. If she happened to bend even the slightest, the under curve of her ass would be exposed. She was disappointed because she loved the dress. Made of light blue knit, it clung to her body softly. Picking up a skirt, she pulled it up over her hips only to discover it was even shorter than the dress. Holding up several other garments, she found they were all too short.

  Dressed in nothing but her panties and bra, she peeked around the curtain for Derrick. “Derrick, please find some other things. These are all too short.”

  Derrick grabbed a halter dress from the remaining clothes piled next to the dressing room. Holding it up, Sasha eyed it longingly. She had never worn such sexy clothing, dresses made to show off her slender figure and catch a man’s eye. “How about this one?”

  “It’s the same as the others.”

  “Then they will all be fine. Madame Rousse knows what I like. She wouldn’t have picked wrong.”

  “Derrick! I can’t go out in public unable to move because my ass will show. Are you trying to get me arrested?”

  “That’s enough, Sasha,” his tone brooked no argument and showed his displeasure with her arguing.

  “Well, I’m not getting any of these…” she squealed in surprise as he jerked the curtain aside and crowded her inside.

  Grabbing her arm, he sat on the padded seat and abruptly pulled her over his lap. Jerking her panties to her knees, he swatted her bare ass hard, the crack of his hand on her naked flesh echoing loudly. “I think you’re goading me on purpose, Sasha, and I don’t like it.” His hand fell rapidly five more times before Sasha’s surprise wore off and she started wiggling.