Daddy's Best Friend: An Older Man Younger Woman Box Set

by Charlize Starr

  She was here now, and the blood went rushing to my groin as I tugged my tie loose.

  I greeted her, hoping that I sounded sane as she responded. I knew that she lived in La Jolla near my younger sister, so I brought that up, adding in that I visited her a lot. I didn’t work as much as Brad did, insisting on vacations and time to decompress. I told her that we should have dinner sometimes when I was there, something that she agreed to as I hardened under my slacks. Jesus, Alyssa was hot. I saw the way that she was looking at me as well and wondered if she felt this too. Brad came back into the room, and I watched as his chef spooned something into bowls that she and Alyssa carried into the formal dining room. There was also a plate of bread and a salad there, filled with vegetables and making my stomach growl. I didn’t eat well as a bachelor, though that was probably the only thing that I missed about Linda. I’d considered hiring my own chef for some time now, but it was easier to grab something on the way home from work at this point.

  One bite of this stew made me reconsider my choices as Brad went right back into the new malpractice suit we had going on now. It was big news in the office. I looked at him as he spoke, wondering why he hadn’t hugged his daughter yet or greeted her at all. I offered suggestions and felt Alyssa’s big eyes on me as we talked. I’d draped my tie over the chair, needing to breathe as the room heated up around me, feeling the electricity between her and I. What the fuck was happening? I was no angel since my divorce, but I’d never felt this way before. I allowed my gaze to rest on her from time to time, feeling my own blue eyes darken with need as she stared back at me. Somehow, I managed to eat and keep up with the conversation, enjoying every bite of the meal even through my distraction. I knew we were in for a long night, so I devoured everything on my plate and promised myself a long workout in my home gym in the morning.

  I noticed as Alyssa nervously left the table with her dishes and felt everything good in the room leave with her. Brad pushed away his half-eaten plate and mumbled something about getting to work as I tried to find a reason to go talk to her in the kitchen. “Go ahead and call Michael. I’ll make some coffee and meet you in the office.”

  I stood with my own dishes and went in, clearing my throat when I passed through the door so I wouldn’t scare her. Alyssa dropped something on the counter and turned to see me as she pressed a hand to her chest and took a deep breath. I explained that I was going to make coffee as I walked over to the sink, seeing her nod and go to the coffee maker as she stared at it blankly for a moment. She seemed to move past whatever was troubling her, filled the reservoir with water and opened a drawer located nearby as she asked me what I liked.

  I moved closer to her and told her that I wanted something strong. Alyssa shivered, pulled out a pod and inserted it into the machine with shaking hands. “You feel it as well, don’t you?” I asked her as I watched her carefully. She grabbed a mug from the cabinet and placed it into the machine before pushing a blinking red button.

  “Feel what?” Her voice was soft, almost a breath as she pulled out a pod and set it on the counter.

  “This heat, this attraction,” I replied as I moved my hand to rest it on her lower back, above the soft sweater. I longed to pull her closer to me, but I resisted, reminding myself that she was young and likely feeling uncomfortable by this. She arched her back, jutting her full breasts out towards me as her body moved closer to mine.

  “Nathan,” she whispered with her eyes wide as she stared at the entrance to the dining room.

  “He’s on the phone in his office,” I assured Alyssa as she pressed her lips together. I wanted to add that I doubted he noticed her at all, but I bit my tongue. “I am not going to push this with you, Alyssa. I just know that I want you and I can see in those scared brown eyes of yours that you want me as well.” I remembered something else and stroked her back. “I am divorced now and available. Linda left two years ago, looking for something else.” Alyssa expressed her remorse, and I shook my head as she pressed her enticing lips together. “Don’t be. It was time.” I watched as she pulled out the coffee and asked if I wanted cream and sugar, making me shake my head as she remained close to me. She made another cup, presumably for her father before she stared up helplessly at me.

  I couldn’t help myself as I leaned down and kissed her, barely brushing my lips against hers to test this chemistry. I tingled from the contact and heard her suck in her breath before I forced myself to pull away. I knew that I’d rather keep this going, ending the night with her in her bed as I took her hard and fast.

  I carried my coffee into the office, and she followed with her father’s, looking visibly shaken up. Brad finally hugged her, and she smiled before she looked at me and told us to let her know if we needed more coffee before she left the room. I had to excuse myself to use the restroom so I could jerk off after that brief encounter before I settled into work for the night. I dropped my pants and took my hard cock in my hand, aiming at the toilet as I replayed the feeling of her lips against mine. I wanted Alyssa badly, and I felt my orgasm coming on as I told myself to shut up. Just let it go.

  I shot forward with a jerk of my hips, mostly making it into the toilet. I cleaned myself up and wiped down the floor and toilet seat before I decided it looked like I’d never been in here. I looked into the mirror, seeing my flushed face as I analyzed myself. I was forty-eight though most women thought that I was only in my thirties. I knew that Alyssa was twenty-three now, which was young but she was an adult. I made my way back into the office, just settling in when there was a tap at the door, and she came back in with two plates. She set them down on the desk as she shot me a nervous look and reminded us to let her know if we needed more coffee.

  Fuck if I wasn’t hard all over again.

  Chapter Four - Alyssa

  I took my plate to the sink and washed everything before I made my own cup of coffee before wandering into the big den to find something on television. I wasn’t used to a lot of idle time since my work habits mirrored my dad’s. I told myself that down time was healthy and that it was good to just sit and watch television as I searched through the extensive channel list. I found a holiday film that Mom and I used to love and settled back as my thoughts drifted back to the kiss. It was nothing compared to ones in the past, not as aggressive. But while those were aggressive, they were also clumsy and without any of the feelings that Nathan gave me. Just a brush of his soft lips, hardly anything - and I was so turned on that I couldn’t stand it. I hated it when he pulled away and wondered if I wanted it to go further.

  No, it couldn’t. Nathan was older, a lot older even if he still looked at least ten years younger than his actual age. That was wrong, or was it?

  I imagined his mouth claiming mine in a harder kiss as I squeezed my legs together with a sigh. I wanted his tongue against mine, stroking it as he gave fuel to the fire that was growing inside of me. I wanted his hands on me, stripping me and touching me as his lips moved down my skin. I let out a moan, feeling the need inside of me as I blinked and looked around.

  The television was playing infomercials, and I realized that I must’ve fallen asleep. I stretched and saw a piece of paper flutter to the floor in the dim light. I reached down for it, finding a note from Nathan including his number. I stared at it before shoving it into my pocket. I stood up and shut off the television before walking upstairs to my room, taking note of how quiet the house was. Dad must be asleep, and Nathan likely went home.

  Once there, I locked my door and changed into a pair of pajama pants and t-shirt before I dropped on the bed. I saw that it was past one in the morning and I stretched as I played back the erotic dream that I was having when I woke up. I remembered a kiss that felt real, and I pressed my fingers against my mouth, wondering if that’s what woke me up.

  I waited for a moment before I slipped off my pants and got under my covers. I looked at my locked door and at the moonlight shining through the window before I moved my hand down my stomach and into my underwear, finding my fo
lds slick and hot. “Oh, God,” I murmured as I stroked myself, finding the sensitive nub that I was seeking as I arched my back. I knew how close I already was to coming as I slipped two fingers inside and pressed my palm against my clit as I let my mouth drop open. It was intense, building up inside of me from within as I fucked myself harder and finally shot up to the ceiling.

  The release pulsed through me as I rocked against my hand. I recovered slowly and stared at my walls as I wondered if that was what sex felt like. I didn’t know. More to the point, I wondered if that’s what sex with Nathan would feel like.

  When I felt like I could walk, I made my way to the bathroom that was attached to my room and cleaned up. I looked into the mirror to see the dewy look to my skin and the wonder in my eyes. I washed the day off of my face before dabbing it dry with a towel and walked back to bed to try and get some more sleep. I had made plans with some high school friends to go to lunch and shopping, which wasn’t a great day for me. It sounded better than staying home and staring at the walls, though.

  I slept fitfully before I heard my alarm and rolled over to shut it off. I dreamed about Nathan all night and got myself off again, though with slightly less intensity. The girls were going to come and pick me up in a couple of hours, so I went to make some coffee while I took a shower. Sherry was the only one home, and she greeted me as I pressed the button for my drink. I took my time showering and got out as I wrapped a robe around my body and dried my hair. I reached for my pants that were on the floor, digging into the pocket for the note as I glanced at my phone charging on the nightstand. I brushed my hair as I read Nathan’s suggestive invitation to contact him anytime, nibbling on my lip as I reached for my phone. I sent him a simple good morning text and went to brush my hair as I waited for a response.

  I giggled as he responded and asked how I slept. I told him well as I walked down to the kitchen to get my coffee and reheat it. The phone was in my pocket, and I made some toast as Sherry worked on meals for the week, since I was here. I nibbled on it at the bistro table as I sent texts back and forth to Nathan, smiling with each one. “Who is that?”

  “Just a friend from home,” I responded as she looked curiously at me. “I swear.”

  “You’re smiling so much that I thought it might be a boyfriend of sorts.” I blushed and shook my head with a laugh, assuring her that I worked too much for that.

  I hurried upstairs and dressed as he asked me if I’d like to stay in the city tonight and have dinner with him. It seemed so sudden, but it felt right as I pulled on jeans and another cashmere sweater, this time in a dark plum. I slid some cute boots over my thick calves and applied a little makeup as I kept glancing at his texts and the time on my phone.

  I was outside waiting when my friends pulled up, and I gave them an awkward group hug before I climbed into the back of the Escalade. We talked about life after graduation, jobs and boys as we drove and laughed, most of which was fake on my part. I wanted to get to our destination and text Nathan back more than anything else. We parked near Bloomingdales and walked down the street as I looked around with the same wide eyes that I always had in the city. As much as I didn’t want to live here, it still took my breath away during visits.

  We wandered around the store and looked at clothes as we kept chatting, all the while with my mind wandered to later. What was going to happen? Could it just be a dinner and nothing more? “You seem distracted today,” Melissa told me as I glanced at her with an apologetic smile.

  “I’m so sorry. I’m used to working nearly all of the time, and this is strange. I need to learn to enjoy it.” Some of the girls didn’t have jobs and probably did every day. I was never that kind of person, but I could fake it for the next couple of weeks.

  They wanted to go to Bosie Tea for lunch, and I thanked God that I was having dinner later today. I liked food a lot, which was evident and small bites of this and that didn’t do it for me. The other girls were all smaller, some too skinny for my taste but I followed them in and chatted through the appetizers that were served to us. We went to one of the malls for a few hours and shopped as I grabbed a few things for Dad and Sherry for Christmas. I would make a private trip for the family later, and I grabbed a few shirts and pants off of the rack to try on.

  I ended up with some beautiful things, particularly a shirt that I would wear later. I had my green pea jacket on that I could wear over it since it was thinner than a sweater and sexy with its dip in the front and dark red color.

  The girls headed back to Long Island for family stuff about an hour before I was supposed to meet Nathan, and I gave them all hugs. It seemed like we had a lot more in common before, which made me wonder if I was them before. I waved as they walked back to the car and turned to do a little window shopping. I was meeting Nathan at the Empire Diner, which I loved and I had a little time before I had to change.

  I stepped into a bathroom as an art store, switching out my shirts and adding some matte red lipstick to my lips before I ruffled my loose curls. I headed out with my bags and my purse slung over my shoulder to the diner. I walked inside and looked around as my skin warmed up, meeting Nathan’s eyes as I watched him look me over hungrily.

  Chapter Five - Nathan

  I watched her walk over with that red lipstick, more taken aback than I was the night before. She was beautiful and looked older than she was right now, a fact that I found reassuring. When she reached the table, I observed her as she dropped her coat to reveal a clingy red shirt that made me shift in my seat. Part of Alyssa’s gorgeous curves were her heavy breasts that strained against the material in the best way possible, even offering a hint of her cleavage.

  Alyssa looked at me as she slid in across from me after getting her bags settled. “Is Dad going home tonight?” She asked as he frowned and ran a hand through his tousled dark hair.

  “Your dad has been seeing a woman here in the city for the past six months or so.” I felt bad telling her, but she didn’t seem sad about it as she smiled. “He stays in between places.”

  “That’s good. Dad needs more in his life than just work,” Alyssa said as she sipped the water on the table. A waitress came by and we ordered some wine and looked over the menus. I decided to go with the bacon cheeseburger, planning a longer time in the gym silently and Alyssa chose the lobster macaroni and cheese. She looked at me as the wine was set in front of us and a nervous expression crossed her face. “So, what is this?”

  “Dinner,” I replied as she nodded and looked around the restaurant.

  “Is that it?” She sipped the wine and watched me as I felt the energy fill the air again, making me wonder if I’d be over Alyssa if I just slept with her one time. I pushed the idea away as I let the guilt wash over me. This was Alyssa, not some woman to toss aside. “Why did you leave me the note?”

  I stared at her for a moment before responding. “I wanted to give you a kiss good night, and I slipped it in as a bonus.” I saw her panicked look and smiled. “He was in his office, and I was on my way out, Alyssa. I didn’t stay.”

  “I wish you had,” she murmured as I leaned closer and looked at her. Alyssa blushed, and she realized that she’d spoken out loud and shook her head. “Sorry.”

  “Do you, though?” I asked as she nodded. “Same.”

  “I…” She looked around the room before leaning over, just as the waitress stopped by again. Alyssa blushed, and I ordered for both of us before leaning forward again. She seemed to reconsider what she was going to say and pressed her lips together. “I went upstairs after I woke up and touched myself,” I told my cock to calm down and watched as her face softened. “It’s never felt like that before, and I think that it was the dream that I was having about you.” There was a soft smile on her face, and I stared at her as she looked at me. “I think I felt your kiss last night.”

  “There’s a lot more where that came from,” I told her as she sipped from her wine glass again. “What dreams?”

  “Oh, there were several. They were craz
y,” Alyssa said to me vaguely as she shook her head. “I’m a virgin, though not because I’m some religious nut or anything. I just haven’t wanted anybody before now, not like this.” She gave me a fearful look as if she thought that I was going to get up and leave the table.

  “Do you want that with me?” I asked her as she nodded and gave me a nervous smile. “I just wonder if it’s wrong.”

  “I’d never force you to do something that you didn’t want to do.” I looked into her eyes as I spoke, knowing it was the truth. I didn’t want to hurt Alyssa or traumatize her for later in life since this would be just a fling. “I’ve done the same thing remembering our kiss, more than once. I don’t know what it is about you, but you’re beautiful. You always were, but you’ve grown up now. We’re both adults, Alyssa. We can agree to this, and nobody has to know.”

  “I don’t want Dad to find out,” she said as the waitress swung by to set our plates down in front of us.

  “He has nothing to say about it. You’re an adult, but I respect your wishes.” I watched her nod as she picked at her meal with a fork, knowing that she was scared to disappoint him. I could see in her face that she thought she already was and it angered me since Alyssa did nothing wrong. She was just a girl that lost her mother and father in the same time frame and missed them. Part of me wished that I didn’t want her physically, that I could just comfort her and be a friend. I could make it worse bringing this to a sexual level, but my body wanted her, and I could see that she felt the same as she stared at me across the table.

  The meal was relatively quiet, both of us aware of the sexual tension rising in the air around us. I finished my burger and pushed the plate away as I licked my lips. Alyssa was eating slowly, looking at me with those eyes and making me ache under the table. “I have an apartment here in the city, for the incredibly late nights and early mornings. Will you come there with me?”