A Legacy of Shadows

"You assumed correctly."

Walking down the street of a major city with a woman like this on my arm was a feeling of freedom that I'd never experienced before. I smiled, and soon Rachel broke the amicable silence.

"Penny for your thoughts?" she asked. "You look delighted."

"I am. Can I confess something to me?"

"Oh, please do. I'm dressed for all kinds of confessions."

"Um. I fantasized about this a lot. Taking you out somewhere. On a date, just the two of us. Is that weird?"

"No. It's flattering if you think about it."

"How so?"

"That's what I lo...like about you," Rachel said softly. "You're humble. I think you're a bit innocent, too, but you never think of yourself as better than anyone. You're confident and handsome, but you don't use it as a weapon, or expect people to bow down to you because of your family."

I was glad for the shadows of night covering my intense blushing.

"I don't know how much of that is really virtue, though. I guess I've just never seen myself as anything beyond what I am."

"What are you, though?" Rachel asked. We both stopped, apparently at the restaurant. Belatedly I opened the door for her. The building was very humble from the outside, a simple brownstone-lined up with others between more significant structures. The entry read 'Pulaski's Fine Dining.' We walked through a small foyer to another door, which was opened for us this time. The doorman and maitre d' were in tuxes, and the waitstaff were all in smart black outfits. The bar was filled with well-dressed high-end professionals, flirting, and chatting. The walls had oak paneling, and the elegant red tablecloths combined with the candle and gas-light to make the place exude class. We were recognized immediately and led to the very back, where a small alcove awaited us. Soon we were seated and alone again for a moment.

"I guess I'm just a regular person in irregular circumstances," I said, after a moment, belatedly answering her question.

"No," Rachel said, "that's not true. You're more than that. Like it or not, you've got some of your dad in you. And you've had experiences and exposure to things that a lot of people, even wealthy people, don't even know exists. You should, by all reason, be a bit more arrogant and cruel. It would make sense. But you're not. I guess I'm just wondering what keeps you grounded."

"You do," I said. "So does Isa. And Dad's better advice. And Mom. And Earl's Diner in Capuchin. And knowing that whatever else I might do, I don't truly deserve this wealth and power. I have to earn it, in a way, by being more than it. Or at least not being awful."

Rachel sighed and reached her hand across the table. I took it eagerly.

"That's what surprised me most about you," she said. "At first, I wondered if you would be a great deal like your father. Not that there would be anything wrong with that, but I was pleasantly surprised. It was easy to see by how well you responded to my instructions when I was teaching you, or how you treated your sister, that you were your own person."

"If I'm honest, what surprised me most about you was your appearance. When Father said we'd be learning self-defense, I imagined a veteran. And then you show up, just three years older than me, and beautiful. I had a tough time, not staring at you. I still do."

"So," Rachel said with a wry grin, "am I just a hot body with some surprising skills?"

"No," I answered immediately. Her tone had been joking, but I suddenly felt very serious, as though I needed to express what I felt right then. I felt an opportunity coming, and even in my naive state, I knew that some doors open briefly and may never open again. "You're my friend, and I trust you. I don't trust many people. I rely on you, yeah, but I don't think of you as a teacher or a bodyguard or a driver. I...honestly I really care about you. Maybe I haven't done a good job of showing it, but I do. Beautiful women have always worked at the house, and most of them are smart and skilled, but you're special. I don't know what I'd do if you left."

"Reuben," she said, and while I couldn't see very well in the dim candlelight, I knew that her eyes were misting over a bit. The table was too wide for it, but I felt a sudden urge to pull her body against mine and kiss her. I settled for squeezing her hand instead. The waitress politely interrupted us then, but we were both famished, so we welcomed the intrusion.

Soon we were drinking wine and flirting and eating the best steak I'd ever had. I gathered later that this place was a hidden gem in Chicago, expensive and generally with a long waiting list, but open to us that night. Rachel was hemming and hawing over dessert, so I stepped up and ordered cannoli, splitting it with her.

I paid, which made me feel important. It was a silly thing, but I think Rachel understood it to be a compliment to me. She could take care of herself. I realized as she waited to take my arm that she had only really behaved in a submissive fashion to two men: my father and myself. I couldn't put that out of my mind.

We left arm in arm, but it was chilly out, and soon Rachel was leaning into me. When we reached the club that she'd picked out, I opened the door with one hand and put the other on the small of her back, gently guiding her. I felt her tense for just a moment and worried that I'd misread her, but when we got inside, under the dim light, I could see the flush on her cheeks. Something about what I had done had gotten to her, and in the way, I wanted it to.

The club was too loud to hear each other properly, so we didn't speak. I got Rachel and myself each a whiskey on ice, which we drank quickly. The flashing lights did nothing to tame the heat that was growing between us. We met eyes, then I stood up and took her hand, going to the dance floor.

I can't dance for shit, or at least I don't think I can, but I can let loose, and that's what was important in the moment. I'm coordinated enough to move with a partner, and Rachel is a hell of a partner. She moved and shifted like a serpent, and her dress showed off her tight body when she did it. I could tell that others were enjoying the show. Men and even women shouted vulgar encouragements. She wasn't looking at them, however. The entire time she shifted and gyrated, just a few feet from me, her eyes were on mine. Two college girls came over and danced with her, grinding on each other and her. Rachel looked at me, cocking her head slightly. She was asking for permission, and I gave it. The three really tuned up the crowd, and their dates, as they moved and shifted. One went to kiss Rachel, but she just shook her head, so the two college girls kissed instead. The crowd went wild.

It became too much, and I moved to her. The display had aroused me but also angered me just a bit. I knew it was a display, and I knew it was for my benefit, but I was still jealous. I knew that I should feel bad, but I didn't. Instead, almost instinctively, I did what I needed to. I pulled up close to her, put my arm around her waist, and pulled her into me. She whimpered, a noise that only I was close enough to hear, but did not resist. As I crushed her to my chest, I kissed her for the first time.

I'd never kissed anyone like this. It started out strong, her arms around my neck and mine around her waist, her body melting into mine, our lips colliding and tongues dancing. Then it intensified. She ground against me, and I moved my hand up under her skirt to grab her ass. She gasped, then reached down and took hold of my cock through my pants. I grunted, and she moaned. We stopped for a moment and looked at each other.

We'd only been there for a half-hour, maybe forty-five minutes, but some hidden communication moved between us. As one, we turned and left the dance floor. Perhaps someone noticed our urgency and laughed, knowing what we were going to do, but we didn't care. We walked at a fast pace back to the hotel, my arm casually around her bare shoulders. We didn't speak, but we both knew what was going to happen. Our breathing was a little faster than it should have been, our faces a bit more flushed.

We passed through the lobby at light speed, ignoring the doorman's smirk. As soon as the elevator closed behind us, we were making out again. I moved into Rachel and pushed her into the wall. She breathed hard and started unbuttoning my shirt. I noticed with a little bit of satisfaction that her hands were trembling with excitement. She wanted me, really and honestly.

When the elevator door opened, Rachel danced out of my grip, giggling and practically running to our room. I followed at a slow step, partially out of a need to draw things out but also because I was a little tipsy and didn't want to fall down and embarrass myself. As we neared the door, Rachel turned around and faced me. I pushed her into the door, harder this time than at the elevator. I half-expected her to ask me to slow down or be more gentle, but she just wrapped her arms around me and kissed me again. Somehow, I fumbled the card key out and got the lock open. As the door swung open, Rachel almost fell backward, but I steadied her, with my hands under her ass.

Rachel made a small noise of shock as I lifted her up. I worked out then, and I do now, and while she was in good shape, she was rather small. As I pulled her up, her hemline lifted to her waist, and she wrapped her legs around my waist. Anyone watching us could have seen her lacy red panties. Neither of us cared. I kicked the door closed behind me then carried her to my bed, throwing her down upon it. She giggled and looked up at me, then stopped smiling, sitting up. The mood hadn't soured, but it had changed.

"What is it?" I asked.

"Do you really want me?"

"Jesus, Rachel, if you can't tell by now..."

"You're a healthy eighteen-year-old man, and I'm a girl. You'd want to get in my pants regardless. But do you wantme? I need to know, Reuben. I need to hear it."

"Rachel, I want you. I've wanted you since you first showed up at our house. The first time you put your arms around me to help adjust my shooting stance is a memory that I can't forget. I dream about you, Rachel. About your body, about your lips on mine, about...god. I care about you, but yeah, Rachel, I want to fuck you. I want to fuck you so bad it hurts."

"Oh god, Reuben," Rachel said, standing up, "That's what I needed to hear. I need to know that I'm...important to you. You'll have so many women, and so few of them will end up mattering to you. I need to matter to you. Even if this is our only night together."

"It won't be," I said with confidence that shocked me. "I won't be able to keep my hands off of you. Not after tonight."

Rachel smiled but didn't answer. Instead, she took me over to the window. We had a balcony with a beautiful view of the lake. We could see the lights of boats on the water and airplanes coming into land. She slid the door open, and a breeze came in, crisp and refreshing.

"I've wanted to do this as soon as you turned eighteen. Let me prove too you how much I want you. Let me show you how I...how I love you."

The word shook me. I didn't let it show, although I probably should have. I didn't expect it. I cared deeply for Rachel, and yeah, I'd even call it the beginnings of love, but it was far from my mind. How long had she felt this for me? She was older than me, although admittedly only a few years. Had she wanted me for a long time? Even when I was underage? I had difficulty focussing and just nodded in response. Rachel smiled and turned around.

"Help me get out of this. I want you to see me," she said.

I found the well-hidden zipper and pulled it all the way down. Then I pushed it down off of one shoulder and then the other. Rachel let gravity take it the rest of the way, shimmying her hips slightly to get it to fall all the way to the floor. She wore no bra, and I saw gooseflesh break out on her back in the cool breeze. She kept her red panties, thigh-highs, and heels on, and somehow that was far more arousing than pure nudity. She turned around to face me. She was a vision. Her pale skin glowed in the night. She bit her lip and dropped to her knees.

Rachel fumbled with my belt and zipper, more eager than I'd ever seen her. She fished my cock out, and it looked large in her smaller hand. She made a hum of satisfaction and leaned into its hardness, rubbing her cheek on it, affectionately. I placed my hand in her hair and stroked her head. She rewarded my touch by licking me once from the base of my cock to the head. I groaned loudly, and she giggled.

"I'm going to make you cum in my mouth," she said. "I don't want you to hold back. I know you've got more than just one time in there for me. I want to make you feel good and then...then we can get to fucking. Don't worry if it doesn't take you long. That's fine, I want to take the edge off for you. Oh, and when you get going, don't be gentle. Just put your hands in my hair and fuck my mouth. I...I love that. I'm going to take care of you, Reuben. I'll always take care of you."

I nodded, and she took me in her mouth. I knew then that she had a lot of practice, and it didn't bother me. Mainly because her technique made me forget about anything other than what she was doing. Her left hand played with my balls gently while her right moved at the base of my shaft. Her mouth moved quickly up and down, and her tongue stimulated me in ways that my naive mind had never imagined it could. Over and over, she moved, her mouth making the lewdest slurping and sucking noises. Now and again, she would make eye contact with me, and she would look at me with such pleading, such complete devotion that even in the midst of that much excitement and pleasure, it took me aback.

I put my hands in her hair and groaned as I felt her tongue twist and turn. I let my hips move naturally, and soon I as plunging into her mouth. I had to go deeper. I needed it. I pushed hard, and she released my shaft, but she never fought me, never resisted. I heard her gag and choke, but I didn't stop. As I built up speed, I looked down and caught a glimpse of what she was doing. One hand braced herself on my thigh, but her other was clearly down her panties. She was so excited that she was touching herself while I fucked her mouth. I remember thinking how amazing she was as I slammed into her once more and let go.

Rachel moaned as I filled her throat and mouth with my cum. I pulled back slightly, letting her recover and giving her a chance to release me, but she didn't. Instead, she kept up the suction, gulping my cum down eagerly. She kept it up until my pulses of sperm slowed and then stopped. She let me out with a slight pop and then looked up at me. A tiny trickle of cum had escaped her mouth and dripped down her chin. As she looked at me, she wiped it up with her finger and then licked it clean.

"A good girl always drinks whatever her man gives her," she said and smiled wickedly up at me. I didn't notice at the time, but later I would think back and wonder if that was something she had memorized, a kind of lesson she had learned before she had met me.

I held my hand out to her, and she took it, and I helped her back up onto her feet, kissing her deeply. I tasted a bit of myself on her lips still, but it didn't bother me. I was falling for Rachel much harder than I had imagined possible. It didn't hurt that she'd just given me my first blowjob, and I wasn't going to waste time returning the favor. I led her to the bed and then took off my shoes, socks, shirt, pants, and boxers in the time it took her to take off her panties. She giggled at my eagerness.

I was already getting hard again, and Rachel looked at my cock with satisfaction.

"Are you ready to fuck me now?" She asked.

"No," I said. "I want to make you feel good first. I've fantasized about it before. What you taste like."

Rachel's expression changed slightly, and she blushed. I was far too driven by hormones to really notice at the time, but later I would wonder. How could a woman like this not have men lining up to go down on her? How was that even possible, given how attractive she was? Did her previous partners not care about her?

Rachel slid up the bed and laid back, parting her legs. I ran my hands up her legs. She'd left her stockings on, and the transition from their slightly rough texture to the smooth warmth of her inner thighs did something to me. I slowly took off each high heel, kissing her on her each calf as I did so. I took my time, enjoying the feel of her firm, athletic body. When I looked back at her, her lips were parted, and she was absently pinching her own nipple. Her pussy was trimmed, but not shaved, and was a slightly darker auburn than her other hair. Her labia was swollen and wet, and I could smell her arousal from where I was. I moved down, kissing her on her inner thigh as I did so, before finally tasting her.

Rachel gasped, and I felt her hands in my hair. Her touch was light, almost tentative and unsure. I looked up at her.

"Tell me what you like...or just move me where you want me, I've...I mean obviously, I've never done this before. I don't want to fuck it up."

"You're off to a great start. Just keep it up, and I'll...oh god...I'll tell you what to change."

I didn't wait for her to finish before I started licking and lapping at her. What I lacked in experience I made up for in enthusiasm. After a bit, I felt a slight pull on my hair, too light to cause pain, but I liked it anyway. I responded by moving up until I was licking around but not directly on her clit. She stroked my head absently as I heard her moan.

"Fuck, Reuben. You're good...at this...at loving me..."

In response, I moved my hand over her taut belly and up to her chest, where I followed her example and pinched her nipple, lightly at first.

"Harder," she said. "Oh fuck, pinch them harder, and move up...just a little. There, oh fuck there..."

Rachel's words degenerated into a stream of noises and exclamations, meaningless but telling me I was doing it right. Her grip in my hair became painful, and her legs locked around my head. I felt her body go rigid, and she cried out, gasped, and then cried out again, her body locking and unlocking as she was taken by orgasms. I wanted to watch her, but I didn't dare stop. I kept it up until she started pushing my head away.

"Oh, god, enough, enough. I can't take any more, baby..."

I looked up and was very pleased with myself. Rachel was panting, her expression one of satisfaction, her whole body flushed with pleasure, her eyes half-lidded. She crooked a single finger at me, and I moved up her body, kissing her, belly, breasts, nipples, neck. I wanted to be inside her then, badly. That's what she wanted, too. As my cock slid along her wet slit, I groaned, unable to control this fire-like need, and kissed her, clumsily but with real affection. After a minute, we paused, and she looked me in the eyes.

"This is your first time, isn't it?"

Rachel asked the question simply, with kindness.

"Yes."

"Good. I want to be your first. I want to be special for you."

I don't know what I expected at that point. I had ideas about the way men and women should fuck, and they were pretty simple and a bit naive. Rachel corrected me. As soon as she stopped speaking, her eyes turned predatory, almost merciless, and she rolled hard. She was strong, at least as strong as I was, from constant exercise and training, and other activities. I found myself on my back, her straddling me, my wrists pinned as she kissed, no, attacked my neck and ears. She bit and nipped, and I cried out more than once. I never asked her to stop.

"Say you want me," she breathed, her voice hard.

"I want you."

"Say you need me."

"I need you, Rachel. Please!"