My Stepbrother, My Lover: The Prequel

by Alice Ward

  “Jackson doesn’t like a lot of makeup,” I told her. “He says that I look better without it.”

  “You’re obviously going somewhere fancy tonight Kennedy, you have to let me put a little bit of color on your face. Jackson may like the natural look, but everyone at the restaurant will be wondering why you left the house half-ready.”

  We compromised. I let her brush a soft brown mascara over my eyelashes and a hint of bronzer to my cheeks. She finished the look with a soft pink lip gloss and I had to admit, I looked beautiful. It was an incredible thing to admit. Lauren moved on to my hair and had just finished curling the last section into a perfect ringlet when Jackson arrived to pick me up.

  “I’ll get the door, you get your shoes on,” Lauren insisted after we heard the knock. I did as she instructed and turned back to the doorway just as Jackson stepped into the room.

  “Kennedy, you look amazing,” he said in awe.

  “You look pretty good yourself,” I smiled. He did. He wore a tailored black suit, a starched white dress shirt, and polished leather shoes. His hair was gelled to messy perfection and he had a hint of stubble on his strong chin.

  “Are you ready to go? Our reservations are in twenty minutes.”

  “Let’s head that way,” I smiled and grabbed the black satin handbag I’d borrowed from my mother. Lauren beamed at me as we passed and I whispered “Don’t wait up.”

  Jackson and I drew a lot of stares as we left Lowell House. “Everyone’s staring at us,” I whispered as we stepped through the front door.

  “Everyone’s staring at you,” he told me affectionately. “You really do look amazing tonight Kennedy. I was hoping you’d skip the makeup, but now I think this subtle look is my favorite. It highlights your beauty instead of masking it.”

  “I’ll let Lauren know that you approve,” I said as he opened the passenger door of his black BMW.

  “I like your car,” I told him as he slid behind the driver’s seat.

  “Thanks, it used to be my dad’s. The man gives millions of dollars away every month, but I have to drive a hand me down.”

  I couldn’t believe what I was hearing. “Is that really something to complain about?” I asked, unable to keep the criticism in my voice at bay.

  Jackson laughed. “Kennedy, I was joking. You seem tense, I was trying to lighten the mood.”

  I made myself relax. “I’m nervous,” I confessed. “I’d feel better if I knew where we were going.”

  “Fair enough. We’re having dinner at La Belle Notte. After that, we’re going to see the opening of a new show at the Institute of Contemporary Art. I thought we’d play it by ear from there.”

  “That sounds amazing,” I told him. “Jackson, I’ve never been on a date like this before. I’m not sure I’ll know how to act.”

  He reached over and took my hand. “Just be yourself, Kennedy. There’s no certain way you’re supposed to act. Relax and let me spoil you for the night. You deserve it.”

  He pulled into the parking lot of Boston’s most popular and expensive Italian restaurant and drove to the valet parking stand. An attendant opened my door and I waited by the entrance while Jackson gave another attendant his keys. I saw him slip the man a twenty and felt like I was in a movie.

  Jackson wrapped an arm around my waist and we walked into the restaurant together. The ambiance was rich and inviting, with dark mahogany floors and beige walls bearing guilt framed paintings. The lighting was dim and a string quartet played in the middle of the main dining room.

  “Montgomery, table for two,” Jackson told the hostess.

  “Of course Mr. Montgomery, it’s nice to see you again. Right this way,” the plump brunette replied. We followed her away from the main dining room and through a short hallway. We turned to the right and I spotted a small table set up in front of a large bay window.

  “Our best private table, as requested,” the hostess announced. “Paula will be your server, she’ll be in directly. May I take your drink order, or would you like to look at the wine list?”

  “Do you mind if I order for both of us?” Jackson asked.

  “Be my guest.”

  “We’ll have two ice waters and a bottle of your house chardonnay.”

  “Of course, I’ll get them right away.”

  She left and I smiled at Jackson. “They know you here.”

  “This is my grandfather’s favorite restaurant. Don’t hold that against them. He may not be the friendliest man, but he has impeccable taste.”

  “I’m sure he has all sorts of good qualities,” I offered kindly. “He’s been a big influence in your life and you’ve turned out pretty well.”

  “Thank you for saying that, Kennedy. I hope you’ll keep an open mind when you meet him. Most of what you’ve read about him is true, but that’s not all he is.”

  “I understand,” I assured him, trying not to panic at the idea of meeting his grandfather.

  Paula arrived with our drinks. She introduced herself as she set our water glasses in front of us and then uncorked the wine and offered Jackson a sample.

  “Perfect,” he said after taking a sip.

  “Would you like to order or do you need a few more minutes to look at the menu?”

  Jackson looked at me.

  “Go ahead,” I told him.

  “We’ll start with Cesar salads and the roasted tomato soup. After that, we’ll have the stuffed tenderloin and the seafood primavera.”

  “Would you like the entrees served family style?”

  “That would be great.”

  Paula left to put in our order and Jackson poured us each a glass of wine. Our appetizers arrived in less than five minutes and I marveled at the attentive service money could buy. We finished the chardonnay with our first course and Jackson ordered a bottle of Merlot to go with our entrees. When we finally left the restaurant two hours later, we were both drunk and happy.

  “We can’t go to the museum Jackson, neither one of us can drive,” I told him as we stepped out onto the sidewalk.

  “I’ve already got that taken care of,” he told me with a sly grin. He approached the valet attendant he’d given his keys to.

  “Are we on schedule?” he asked.

  “Yes, Mr. Montgomery.”

  “Jackson, what’s going on?” I asked.

  “Our ride is here,” he explained, nodding to the driveway. A long black limousine was parked by the curb. He waved at it and the driver pulled up to the valet station and got out of the car.

  “Hello, Mr. Montgomery, my name is John and I’ll be your driver this evening. Are you ready to go to the museum?”

  “Yes, John, thank you,” Jackson replied as John opened the back door. Jackson turned back to the valet attendant. “My friends David Foster and Mark Buchanan will be picking up my car.”

  “Of course, Mr. Montgomery. I’ll check their IDs and make sure they get it back to your home safely. “

  Jackson passed him another twenty and we slid into the limo. The leather seats were soft and spacious and I was pleasantly surprised to see a bottle of sparkling water chilling in an ice bucket.

  “Are you cutting me off?” I teased, lifted the bottle.

  “Not at all,” he smiled. “I just thought that we should sober up a little before we get to the museum. Plus, we’ll feel better tomorrow if we stay hydrated tonight.”

  “You should have been a pre-med major,” I teased again.

  “You’re certainly in a playful mood,” Jackson observed happily. “I take it that you’ve finally relaxed.”

  I nodded. “I’m having such a good time, Jackson. And not just because you’re taking me to fancy places and spending a bunch of money. I love being with you, I don’t care what we’re doing.”

  He put his arm around me and looked deep into my eyes. “You have no idea how happy I am to hear you say that. I love being with you too, Kennedy.”

  I put a hand on his prickly jaw and pulled his face to mine. We kissed softly, hesitant
ly at first, until Jackson finally parted his lips and our tongues found each other. He pulled me closer and our breathing synchronized as we lost ourselves in the moment. When the limo stopped in front of the museum, I was disappointed that we had to leave the car.

  “Let’s go somewhere else, somewhere private,” I suggested. Now that I’d decided to be with him, the need was urgent.

  Jackson shook his head, smiling down at me and rubbed his thumb across my bottom lip. “There will be plenty of time for that later tonight. I’m really excited to see the new exhibits with you.”

  “I’ll be back at eleven o’clock,” John told us, holding the door open again. “If you decide to leave earlier than that, give me a call.” He passed Jackson a business card; we thanked him and then walked hand in hand to the museum entrance. A flyer about the new show was posted on the front door.

  “Jackson, I think you’ve made a mistake,” I told him. “This says that the show doesn’t open until Sunday.”

  “That’s not a mistake,” he replied with a mischievous grin. He opened the door with no further explanation. We stepped inside and were greeted by a middle aged woman dressed in a black pinstriped pantsuit.

  “Hello, Mr. Montgomery, I’m Rebecca Nolan. We spoke on the phone. I’m so happy you’re interested in our new show, everything’s set up for you in the east wing. We’re still setting up some of the final touches on the exhibits so please excuse our mess.”

  We’re getting a private viewing. I realized in shock.

  We followed Rebecca through the corridor and stopped in front of a large set of double doors.

  “If you need anything, I’ll be at the lobby desk. When you’re ready to go to the roof, you can use the elevator down the hall.”

  “Thank you for everything, Rebecca,” Jackson told her. “I appreciate you giving us a sneak peek.”

  “It’s my pleasure,” Rebecca gushed. “The Montgomery Foundation has been very generous with the Institute. The least I can do is give you a private showing. Please give your father my regards next time you speak with him.”

  “I will,” Jackson promised and looked pleased at his father’s generosity.

  Rebecca turned back down the corridor while Jackson and I entered the east wing. A small table just inside the door held booklets about the new show. We each took one and started down the massive room.

  The new show was comprised of several collections of Contemporary American art. One exhibit held sculptures by William King, Duane Hanson, and Rudy Autio. The next was filled with photographs by Ralph Eugene Meatyard. There were more paintings on display than anything else, and Jackson and I spent over an hour comparing the merits of James Bama, Kenneth Davies, John Altoon, and Sylvia Sleigh. The final exhibit held a massive installation piece by Edward Kienholz.

  “Jackson, this has been amazing,” I told him as we made our way back to the double doors. “I’ve always loved going to museums, but to be able to see everything on our own… this has been the best night of my life.”

  “It’s not over yet,” he said with a smile. We left the east wing and walked towards the elevator.

  “What’s on the roof?” I asked. I couldn’t imagine what Jackson had planned next.

  “Just a little nightcap,” he replied.

  The car carried us to the top of the building and the doors opened into the clear night air. There was a soft breeze and it blew my hair gently across my face. The roof had been decorated in small, twinkling white lights and a small café table was set up close enough to the edge that we had an amazing view of the city. The streets buzzed below us with traffic, but from where we sat, it felt like Jackson and I were the only two people on the planet.

  A bottle of champagne chilled in a standing ice bucket and a large covered platter sat in the middle of the table. Jackson popped the cork out of the bottle while I uncovered the dish to find strawberries, whipped cream, and pound cake.

  “Alright,” I said suspiciously. “Who did you talk to?”

  “What do you mean?” Jackson asked innocently.

  “First you take me for Italian food, which is my favorite. Then you bring me to a private showing at my favorite art gallery. And now, I’m looking at everything we need for strawberry shortcake, which is my favorite dessert. Those can’t all be coincidences Jackson. Who gave you advice?”

  He had the grace to look embarrassed. “Lauren,” he confessed. “I wanted to make sure you enjoyed yourself. And I thought, who’d know you better than your best friend? I hope you’re not upset. I’ll be more original next time we go out. I promise.”

  “I’m not upset at all,” I assured him. “I’m flattered that you went to so much trouble. But next time, I want to see all of your favorite things.”

  “Even if it means getting on a plane?” he asked with a grin.

  Plane? I took a deep breath, trying to remember how much bigger his world was than mine. “I’ll try to get used to the idea,” I replied. I still wasn’t sure that I’d ever feel completely at ease in Jackson’s world, but after the night he’d given me, I was open to giving it a try. We sat on the roof, drank champagne, and fed each other strawberry shortcake. We talked about what we wanted for our futures and I was pleasantly surprised to hear that Jackson wanted to settle down and start a family young.

  “Not while I’m still in school, of course,” he said quickly. “But I want to be young enough to be active with my kids. I want to be a hands-on dad, to give them the kind of family I wish I’d had.”

  “I feel the same way,” I confessed. I still hadn’t told Jackson the story of my conception or explained that I had a donor instead of a father, but I knew it wasn’t the time to get into complicated family history. I was having too much fun to bring up such a serious subject. I had something much more enjoyable in mind. I pulled my phone from my purse and saw that it was thirty minutes to eleven.

  “I think that you should call John,” I announced.

  “Are you ready to leave?” he asked, the smile fading from his lips.

  I shook my head, stood up, and settled down in Jackson’s lap. “No, I think you should call and tell him to make it eleven-thirty,” I said, then leaned closer and whispered. “Or midnight.” I couldn’t believe I was being so brazen.

  Jackson retrieved his phone and John’s business card from his jacket pocket and made the call, his hand tracing up and down my back. As he spoke to the driver, I stood again, unbuttoned his slacks, and slid my hand over his smooth, stiff cock. Jackson gasped as I touched him, but managed to keep an even voice as he finished talking to John. He ended the call and let his phone fall to the floor.

  “What’s gotten in to you, Kennedy?” he asked, his smile a mix of bewildered and pleased.

  I was breathing heavy, from desire and nerves as I continued stroking his long, thick shaft. I wasn’t exactly sure what had gotten in to me. Maybe it was the champagne, or maybe it was the way Jackson had looked at me all night, but I suddenly understood what my mother and Lauren had been talking about when they encouraged me to let loose and enjoy myself.

  “I was hoping you’d be getting in to me,” I answered with a smile I hoped was sultry. I wrapped my hand around his throbbing member and gave him a light squeeze.

  Jackson groaned in pleasure. “Are you sure…? Here? Kennedy, I hope you know that I didn’t do any of this to get you in to bed tonight.”

  “I know that,” I replied. “And I don’t see a bed anywhere.”

  I bent over him and pressed my lips to his. We kissed passionately, our tongues dancing with each other. We parted so Jackson could slide my dress over my head. He kissed my skin as it was exposed. My belly, the tops of my breasts, my neck. I stood before him in my black lace panties and bra and I’d never felt so beautiful as he took me in. When his blue eyes were looking at me, our lips crashed into each other again.

  Jackson gently pushed my panties down to my ankles and I kicked them away as I stepped out of them. Feeling brave, I pulled him to his feet, pushed his pant
s down his legs, and pushed him back into the chair. I retrieved a condom from my purse and made a mental note to thank Lauren for insisting I be prepared. I rolled the rubber over Jackson’s already dripping prick and then straddled him, taking in the entire length of his shaft. I settled into his lap and remained still for a moment while my body stretched to accommodate Jackson’s enormous girth.

  “You feel so amazing,” he told me as he traced soft kisses across my collarbone. “So hot and tight. Perfect.”

  “So do you,” I whispered, my teeth biting his ear. I moved my hips in slow, clockwise circles and Jackson’s cock stirred within me as I ground down. I gradually increased my speed and he grasped my hips, his fingers sinking into my flesh and gently bounced me up and down in his lap.

  It was heaven. His cock filling me, the tip of ramming against my deepest, most sensitive spot. Over and over again, we drew together and then apart. My insides tightened and I knew my orgasm was approaching.

  “Oh Jackson,” I sighed, holding on to him tighter. “I’m going to come.”

  “Yeah, baby?” he whispered, thrusting harder, sending me to the edge.

  “Yes,” I cried to the stars above me.

  “Wrap your arms around my neck,” he instructed. I did as he said and he stood from his seat. I wrapped my legs around his waist and he held me so tight. As he lifted me up and down on his cock, I opened my eyes and took in the view around me. The museum was surrounded by much taller buildings and I wondered if anyone was watching us from the darkened windows. The thought sent a surge of erotic excitement through my body and I bucked harder against Jackson. Gravity helped him push even further inside of me and I exploded in the most powerful orgasm I’ve ever had. As the waves of pleasure overtook my body, Jackson cried out in his own release. He collapsed back into the chair and I fell against his chest, our breaths warring with each other.

  Jackson slid out of me, removed the condom and then we held each other for what seemed like hours. Finally, Jackson’s phone chimed with a message from John. He was downstairs waiting for us.

  “I guess it’s time to go,” he announced reluctantly, kissing me again. “I wish that we could go home together tonight.”