Escorted

by Claire Kent

  Ander slowed his thrusts, pushing deliciously against her contractions until her body had ridden out the pleasure. Then he asked, “You ready for me to come too?”

  “Yeah,” she gasped, flushed and sated by her hard climax. “Yeah.”

  Her channel felt incredibly tight as he pumped into her with a fast, choppy rhythm. She squeezed around his cock as best she could and dug her fingers into his shoulders.

  It didn’t take him nearly as long to come this time, and she watched as the tension cracked on his face and a blaze of pleasure flared up in his eyes. He let out a choked sound and then a thick exhale as his body finally let go.

  There was something deliciously hot and soft about his body after he came. Lori felt it under her hands and between her legs. She only had a few seconds to enjoy it, however, because he pulled off and out of her almost immediately.

  When he got up to dispose of the condom, she pulled down her now wrinkled chemise. She felt kind of weird. Warm, relaxed and pleased with herself but at the same time wanting even more. She was a little sore, but not as much as last time. In an hour or so, she might be up for another round.

  It was just after nine o’clock. They still had a lot of time before midnight.

  When Ander returned, he pulled on his silk boxers and stretched out beside her, obviously realizing she wasn’t through with him yet.

  He turned his head and smiled at her. It wasn’t a broad or uninhibited smile, but it was much better than the one he’d used earlier. “How was it?”

  “Good,” she admitted. “Really good. The best one yet. And I didn’t need all the detailed instructions, so that has to be progress.”

  “How do you feel?”

  “Not bad. Just a little sore. But I think maybe later, we could...” She trailed off, annoyed with herself for feeling a little surge of self-consciousness at her obvious eagerness to have sex with him again.

  “We have plenty of time.”

  They lay in silence for a while, both of them lost in their own thoughts. After a while, Lori turned her head to look at Ander beside her.

  Tonight, she couldn’t tell if he was posing or not. He lay on his back with his hands twined behind his head. His body was relaxed, but his position highlighted the muscles development in his arms and abs.

  She let her eyes linger on his fine chest, his tight belly, and then his long legs and bare feet. When her eyes returned to his bald head, she felt a familiar question prod her unmercifully.

  As if he’d somehow been able to tell the difference between her leisurely leer and her intense curiosity, he glanced over at her. “What is it?”

  “I’m sure you get asked this all the time, but I’m dying to know.”

  His mouth quirked up slightly. “The no hair thing?”

  She nodded sheepishly. “I can’t even tell if you shave it. I’ve never felt any bristles.”

  “I don’t shave it. I started going bald when I was seventeen. I was completely bald by the time I was twenty-three. It’s a hereditary thing. Ran in my mother’s family.”

  Lori was uncharacteristically silent, watching his face, trying to figure out if it was a sensitive subject for him.

  Finally, she asked, “Weren’t there any treatments or whatever you could have tried?” He looked calm and natural, and so she hoped she wasn’t being unforgivably rude.

  Not that it necessarily would have stopped her.

  “Yes. There were. Medical treatments or cosmetic remedies. I was…encouraged to try them.” The brief falter in his reply surprised her, as she’d never heard him stumble over his words before.

  “You didn’t want to try them?”

  He hesitated and met her eyes. And something in her expression must have encouraged him to continue, “No. My father wanted me to do something about it, and I wasn’t inclined to do what he said.”

  “A teenage rebellion thing?”

  Ander gave a half-shrug. “Maybe. There’s a long history, and it’s not a pretty one. Maybe it was just a way to rebel, but my mother died when I was very young and the hair loss came from her family, so it seemed important that I…”

  When he didn’t finish, Lori said softly, “That you affirm her memory that way?”

  “Yeah. My father wasn’t always kind to her.” He cut a quick glance over to her, as if he didn’t intend to say as much as he had.

  She didn’t speak for a minute, not wanting to come off as too nosy and have him close up. Then, “Was he mad about it? About your not treating the hair loss like he wanted?”

  “Yes,” Ander admitted softly, his eyes shifting to stare up at the ceiling. “He was mad. That was the turning point.”

  There was something here. Something Lori desperately wanted to know. A story. A history. The shadows of Ander’s background. She was dying to ask him, to give him a whole inquisition—despite the guarded look in his eyes and the slight tension on his face.

  But she had grown up a lot since she was a child and blurted out any question on her mind. Now, occasionally, she could manage to keep her mouth shut.

  So she didn’t push him, realizing it might bother him or hurt his feelings. Instead, she just said, “I’m sure you know you’re absolutely gorgeous and the baldness just makes you look more fascinating, so I think you made the right decision.”

  Ander’s expression relaxed and he turned back to her with a slight twitch of his lips. “I appreciate your affirmation, but where were you when I was seventeen years old and all the kids thought I was a freak?”

  She laughed softly at his dry question and responded in kind. “I was probably still playing jump-rope, don’t you think? I’m twenty-six.”

  His smiled widened briefly. “Yeah. That’s about right. I probably wouldn’t have thought much of the admiration of a ten-year-old. Besides, when you were teenager, you were probably crazy about some big, strapping jock with a full head of hair.”

  To Lori’s absolutely annoyance, she blushed.

  Chuckling, Ander said, “Thought so.”

  She made a face at him, but she answered willingly enough. “I was in love with my best friend—who was definitely jock material. He, of course, never thought about me that way. But I was in love with him all through high school and college.”

  “That’s a long time to be in love with someone who doesn’t love you back.”

  “Yeah,” she said with a sigh. “Sometimes you hold onto something—just because.”

  Ander met her eyes. “In my experience, it’s rarely just because.”

  Lori was silent for a long time, thinking about that. Thinking about her hopeless yearning after her friend. So many years of her life.

  No wonder she was a failure at love.

  Eventually, she let the questions and insecurities dissolve into her memories and she turned back to look at Ander. His eyes were closed, and she didn’t know if he was dozing or if he was just giving her some privacy for her thoughts.

  Gazing at his smooth bald head—which she now found infinitely attractive—she thought about how he must have felt at seventeen.

  “You must have been so lonely,” she blurted out.

  Ander’s eyes flew open and he turned toward her with a little jerk of surprise. “Excuse me?”

  “As a teenager,” she explained, feeling silly at her lack of segue. “I was just thinking you must have been so lonely. Kids can be cruel about things like that.”

  He gave a half-shrug. “I’ve grown accustomed to not having any hair.”

  “Of course. In fact, I’m sure it’s been an advantage in your profession, since it makes you look so cool and interesting. But I meant as a teenager. Even though you had your reasons for not doing anything about it, it still must have been…hard.”

  Ander swallowed and gave another half-shrug.

  Obviously, this wasn’t something he wanted to talk about. So Lori changed the subject by saying, “Can I feel it?”

  He blinked at her.

  “Your head.” She waved in the direction o
f his scalp, suddenly wishing she hadn't asked. “It’s fine if you don’t want me to—”

  “Of course, you can,” Ander said. He adjusted so that his head was within arms' length of her.

  She gently, almost delicately, stroked his smooth head with her fingertips. It really did feel delicious—the skin stretched tight over the rippling curves and ridges of his skull.

  She let out a breath as she caressed him and ridiculously felt her own body respond.

  She really wasn’t very sore anymore.

  When she brushed against a spot on the side of his skull, she heard Ander’s breath hitch very slightly. Whether or not it was in response to her touch, the sound made her inner muscles clench in excitement

  Without her volition, her hands trailed down his head and neck to gently caress his chest. Ander lay still and perfectly silent as she rubbed the smooth planes there. Then her hands lowered and lingered on the rippling muscles of his flat abdomen.

  She felt the sensations under her fingertips deepened in her growing arousal.

  After several minutes, during which her breathing accelerated audibly, Ander murmured, “Again?”

  She nodded. She’d been noticing some progress in his boxers, but she didn’t know if it was from her touch and because of the mental thing he did to prepare himself. “Is it all right if we try another position this time?”

  “Of course. It’s always your choice.”

  Feeling very brave, she swung her leg over his hips and straddled his prone body. “Like this?”

  “Of course.”

  Ander raised his hands and stroked her upper body over her satin chemise, his skillful touch triggering nerve endings and pleasure receptors and causing Lori to drop her head back for a moment. Then he eased her upper body down so he could take one of her breasts in his mouth, stroking her hard nipple with his tongue through the thin lace and slippery fabric.

  He suckled and kissed her breast for a few minutes while his hands slipped under the chemise to caress and fondle her back, thighs, and bottom.

  She’d thought being on top was supposed to make one feel more in control, but she felt helpless and overwhelmed by the growing sensations as she sprawled on top of him and panted hotly into the pillow.

  She gasped when she felt one of his hands at the hot, swollen flesh between her thighs. Then he nipped her over-sensitized nipple and slipped two fingers into her wet, clinging channel.

  She bit down into the pillow as a jolt of intense pleasure shot through her.

  “Do you like that?” Ander asked, his voice once more sounding just a little hoarse. His mouth was still against her breast, and the vibrations traveled through the wet fabric to stimulate her even further.

  “Mm-hmm,” she whimpered, her voice muffled by the pillow. “Mm-hmm.” She had to hold herself back from humping his belly, since her clit was getting some delicious, indirect stimulation on his torso. She managed her turn her head and gasp out, “More.”

  Ander nipped at her nipple again and started to pump his fingers inside her. She buried her face in the thick pillow again, desperately glad Ander was lying far enough down on the bed for the pillow to be in her reach. She let his mouth and fingers build her up toward climax.

  She’d been gasping and grunting softly into the pillow, but after a few minutes of ever-increasing urgency she turned her head and begged, “Ander, please make me come.”

  “I will,” he murmured, the rhythm of his fingers accelerating even more. He twirled her nipple with his tongue with agonizing skill and added, “You’re close now. I can feel it.”

  So some reason, his words made Lori want to whimper so she hid her face in the pillow again. His fingers were curling against her g-spot, applying hard, steady pressure exactly where she needed to feel it. He hadn’t touched her clit at all, and the bit of flesh was pulsing and swollen.

  Lori’s body tightened. She suddenly realized she was going to come without any stimulation on her clit. She shook desperately. Then felt Ander’s teeth on the soft flesh of her breast.

  She came, biting down on the pillow and trying shamelessly to ride his fingers to draw out the sensations.

  When her body had softened, she was able to summon up enough to energy to pull herself up. “Wow.”

  Ander’s face was slightly flushed, probably because she’d been nearly smothering him by pushing her breasts into his face.

  “Am I going to be too tight now?” she asked, scooting down his body until she was straddling his thighs. She could see that he was fully erect beneath the thin fabric of his boxers.

  “I think you’ll be all right.”

  She pulled down his shorts while Ander reached over to grab the condom packet and lube from the nightstand. Then she waited while he rolled on the condom and slicked his cock up with lubricant.

  “All right,” Ander said, holding his cock upright with one hand. “You still want to do it this way?” She nodded, mesmerized by the sight of his waiting erection. “Lift up and we’ll get ourselves lined up. It takes a little practice.”

  Lori raised herself with her thighs and scooted forward until she was poised above his cock. Then she lowered herself slowly and, with Ander’s help in alignment, was able to slide her channel down over the substance of his erection.

  It was tight, and it took a minute to adjust and catch her breath. Then Ander helped her ride him, guiding her motion with his hands on her hips.

  She rocked over him, trying to build a steady, pleasing rhythm the way Ander always did when he moved above her. She wasn’t sure she did it very well, but finally she found an angle and speed that seemed to bring the most pleasure.

  Lori was glad she was still wearing her chemise, even if it was wrinkled and the fabric was wet at the breasts from Ander’s mouth. She felt his eyes on her, scanning her body and motion in what was likely observation designed to give her the best advice about improving her technique. But his hands were firm on her hips, and his face was once again damp with perspiration.

  After several more minutes, Ander moved one of his hands under the fabric of her chemise until he could find her clit. As he started to massage it, Lori’s head fell back and her spine arched.

  “There you go,” Ander murmured. “Can you come again?”

  “Yeah,” she said on a taken breath, feeling like her eyes might roll back in her head from the raw feeling of his cock's penetration from this angle and his firm massage of her clit.

  She rode him until she came, and then her body bounced and jiggled in response to the spasms of release. She kept moving over him, even after she came, because Ander hadn’t yet come himself.

  “You came?” Ander asked thickly.

  She blinked. “Yes. Couldn’t you tell?”

  “Thought so. But you’re always so quiet.” He jerked his head to the side as her inner muscles tightened involuntarily. “Should I—”

  “Yes. That’s all I can handle tonight. You come now.”

  Flushed, sated, and ridiculously proud of herself, she gazed down at him and intensified her motion, trying to squeeze around him as best she could despite the soreness she could already feel.

  Ander began to buck up into her from below—not hard or rough, just little upward pushes of his hips. In less than a minute, his back arched up just a little and his face transformed with his climax.

  Completely exhausted, Lori collapsed on top of him as she felt the pulses of his release. His body was hot beneath her, and it was starting to soften deliciously. She gasped and clung—completely unconscious of doing so.

  “Let me up for a minute,” Ander said, “So I can take care of the condom. I can hold you afterwards, if you want.”

  Lori rolled off him immediately, wincing as she pulled her body off of his cock. She pulled up the covers against the chill of the room, but she shook her head when Ander returned and gave her a questioning look. “No. I don’t want any fake cuddling. Thanks, though.”

  “You’re welcome.”

  “I didn’t kn
ow my body was capable of feeling that way,” she admitted, glad she was already flushed so he wouldn’t see her blushing even more at the memory of her shameless eagerness.

  He gave her a little smile. “You might be surprised by what your body is capable of feeling.”

  That made her blush even more. But, keeping her courage up, she quipped, “We’ll have to test that theory next time.”

  He chuckled as he returned the lube and DVD to his case. “So you want to schedule another engagement?”

  “Definitely. When do you have open?”

  Ander pulled out a smartphone to check his schedule. “My earliest is two weeks from tomorrow.”

  “That will be just fine. Put me down.” She couldn’t remember her schedule but figured there was nothing important enough to keep here from taking his earliest slot.

  “You can book ahead if you want,” Ander offered. “If you want to schedule regular engagements.”

  Lori swallowed. That was exactly what she wanted to do, but she wasn’t sure whether she was emotionally ready yet to schedule weekly or bi-weekly appointments with a male escort. It would mean committing to this lifestyle, and that still made her feel a little weird.

  At least this way, she could decide on the next appointment on a case-by-case basis. And she could change her mind at any time without seriously inconveniencing Ander.

  “I’ll keep that in mind,” she said, smiling at him teasingly. “But why am I not surprised you threw that option out there?”

  He blinked and his face grew strangely still. “What do you mean?”

  A little surprised by his reaction, she explained, “Just that you’re the quintessential businessman, always looking to expand his business.”

  Ander relaxed. “Right.”

  “You can take a shower again, if you want.”

  He thanked her, grabbed his clothes, and then went into the bathroom. Lori stretched out in the bed as he showered, thinking that she was going to really sleep well tonight. She’d spent the night in the hotel room the week before after Ander had left, and she decided to do so again tonight. After three orgasms this evening, she was feeling incredibly relaxed and there was nothing like sleeping late into the morning in a plush hotel room.