The Daddy Box Set

by Claire Adams

  She was right. I knew she just wanted to hear what he would say and how he would react. Ally loved playing matchmaker, especially for me. I didn’t know whether to be thankful or disgusted.

  “Fine,” I said. I put down the slice of pizza I was eating. I was only three bites in, and it was so good, but this was Justin we were talking about. I had to scroll through my contacts to find his number. I was so nervous when I pushed dial. I felt like a high school girl calling her boyfriend for the first time.

  It only rang twice before he picked up. “Hello, Anna,” he said. He sounded like he was happy to hear from me, which helped me relax a little bit.

  “Hi, Justin. I hope I’m not interrupting anything.”

  Ally held up a thumbs-up sign.

  “No, no. Not at all. What’s going on?”

  “This is going to sound a little random because I know you don’t want to come by anymore, but do you think maybe you can stop by my studio tomorrow?”

  “Yeah, sure. Is everything okay?” he asked.

  “Yeah. I just have something I wanted to discuss with you.”

  He laughed, “It can’t be over the phone?”

  “No. I’d rather do it in person. If you’re free. I mean, if not, it’s okay. We can figure out another time or something.”

  “Anna,” he said with another laugh, I assumed to stop my rambling. “It’s fine. Tomorrow works out great for me.”

  I smiled. “Okay, good. Thank you.”

  “What time?”

  “Whatever time works for you?”

  “Is ten okay?” he asked.

  I smiled because that was his normal appointment time.

  “Ten is perfect,” I said.

  “Alright, I’ll see you then.

  “Okay, bye,” I said and hung up the phone as soon as he said bye.

  Ally laughed. “See, that wasn’t so bad, was it?”

  I laughed and shook my head at her. “Just eat your pizza.”

  I was glad it had been so easy to ask him. I was starting to feel better after everything that happened on Monday, but I couldn’t help how nervous I was already beginning to feel. I still had almost a full day to get through.

  I only had one client the next day, and I figured I would just cancel with her. She had been a regular for quite some time and wasn’t going to miss a session. I’d give her a discount to make up for it.

  Ally looked at me like she was waiting for something.

  “What?” I asked her.

  “Shouldn’t you be thanking me? I told you he had a thing for you. My signs are never wrong, sis. When are you going to realize that?” she said.

  “Thanks. But um. No. Nothing has happened yet. What if he thinks I’m crazy?”

  Ally rolled her eyes. “He isn’t going to. He’s going to agree to it because he can’t stand to be away from you, and this is a chance to be your fake boyfriend, which will possibly turn into a chance to be your real boyfriend.”

  She sounded sure of herself, but I didn’t want to jump in and believe her again. I didn’t want to be let down if he didn’t really feel that way.

  After I took Ally back to her car by my studio and went home, I couldn’t help but think about what might come of this arrangement. I didn’t really think we would start dating for real, but I did let my fantasies run wild when I took my shower.

  I pictured us kissing. We would realize instantly that there was an undeniable connection between us. I pictured my parents leaving and him ripping my clothes off and ravaging my body in ways I never thought possible. I went to bed with my vibrator in hand and slept peacefully through the night.

  Chapter Seven

  Justin

  I had mixed emotions the next morning when I woke up. I took Margie to preschool and went back home to get ready for my meeting with Anna. She called me the night before asking if I wanted to come see her at her studio because she had something she wanted to ask me. My mind was racing all night with the possibilities. I was a little nervous about what exactly it might be. I had to admit I was really excited to see Anna. I couldn’t stop thinking about it.

  She didn’t explain what she wanted to talk about; she was being pretty cryptic. I was curious. Intrigued. And nervous. After the way I left on Monday, I didn’t think I would ever hear from her again. And now I was going to see her.

  She picked the perfect time. Margie was in preschool and would be there for a few more hours. I would have to pick her up later in the afternoon, but at least I could have a conversation with Anna without worrying about Margie running all over the place. I didn’t mind her tagging along with me, but sometimes it was just easier to go to places alone.

  I walked into Anna’s studio, and she was standing at her white checkout counter. She was on the phone looking at an open appointment book, so I figured she was making an appointment. She looked at me and held up her pointer finger to tell me she would be with me in just a minute.

  I nodded my head and sat in one of the waiting chairs. There were a few magazines on the table. I picked up a “People” magazine just for shits and giggles. I wasn’t the kind to care about celebrities, but I needed something to do while I waited.

  “Okay, Becca. Sounds good. I’ll see you Monday at three,” I heard Anna say before she hung up the phone.

  “Hey. Thank you for coming,” she said as she walked over to me. She seemed nervous, and it made her even more adorable. I loved when she got nervous around me. It made me think there was a chance for us, that maybe she had feelings for me too.

  “You’re welcome. Is everything okay?” I asked.

  She laughed, and I realized how much I missed her laugh. From the time we met, it was my favorite thing about her.

  “Yeah. Now, please hear me out before you freak out. This is going to sound super weird.”

  “Okay,” I said slowly. Now I was even more intrigued than before.

  She sat down in the chair next to me. It seemed like she was getting more and more nervous. She took a breath and said, “So, I just found out my parents are coming to town.”

  “That’s cool.” I didn’t know if this had to do with what she wanted to talk to me about or if she was trying to make small talk.

  “Yeah, I guess,” she said. Her leg bounced as she spoke.

  “Something tells me you aren’t happy about this news,” I said.

  She shook her head and grimaced, “So, they have this thing. Well, it’s mostly my mother. She has this thing she does… where she bugs me about why I’m not settled down yet.” Anna looked at me nervously. “I’m sorry this is so weird.”

  I placed my hand on her leg to let her know that I wasn’t bothered. I smiled and said, “It’s okay. Just tell me.”

  She closed her eyes as she said, “Will you pretend to be my boyfriend while they are in town?” Then she opened her eyes again and continued, “I was thinking in return, I could give you free massages. As many as you want, each week.”

  “You don’t look like the type of girl that would have to pretend to have a boyfriend,” I said.

  She blushed. “I know this is really awkward, and I’m sorry for springing this on you like this.”

  “Don’t be sorry. I’ll do it. I was just making an observation,” I said with a smile. I wanted her to be less nervous.

  A big smile spread across her face. “Really?” she asked with excitement in her eyes.

  “Yeah, it sounds like it could be fun,” I said with a wink.

  “Thank you, Justin. You won’t regret saying yes. I promise.”

  She looked so gorgeous when she got excited. It reminded me of the way she looked at me before my fight last weekend. When I looked up in the stands and made eye contact with her, she was just as excited. She really was an amazing woman. I was excited to help her with her parents. Pretending to be her boyfriend would allow me to spend more time with her. Plus, I couldn’t help but think something more might come of it.

  “And I promise you won’t regret asking me. I feel pretty
honored actually,” I said with a laugh.

  “Well good because I don’t ask just anyone to play my fake boyfriend,” she said.

  We sat quietly for a moment. It didn’t feel awkward. It was a comfortable silence before she asked, “How was your fight?”

  I took a deep breath. “I lost.” I wasn’t about to go into detail with her about the bet I made, especially not after the favor she just asked me. I didn’t want to ruin anything that might happen between us.

  “You look tense,” she said. “Do you want a massage now? I don’t have any more clients today. I cleared my schedule so I could talk to you.” Her smile was a little shy, yet I could sense her confidence.

  “That would be amazing,” I said as I followed her into the massage room.

  I couldn’t help the excitement that was flooding through my body. After my big loss the other night, I needed a massage. I couldn’t wait to feel Anna’s hands against my skin again.

  I stripped down to my boxers. I did it every time in front of her. For some reason, it never made me nervous. Maybe it was because I was sexually attracted to her, and it just added to the atmosphere.

  We almost kissed on Monday. I had wanted to kiss her for quite some time. I wanted to kiss her last Saturday night after my fight, but I had to fight the urge. Then, on Monday, it took all my strength not to lean in and press my lips against hers. It wouldn’t have felt right to kiss her and then say, “Oh, by the way, I can’t come back.”

  I laid on the table. First on my stomach, and as per usual, she went slow and hard. It felt so good. I tried to close my eyes and enjoy the relaxing feeling that came with getting a massage, but for some reason, it was hard today. I couldn’t block out how much Anna was turning me on.

  I moaned. I didn’t mean for it to sound so sexual, but I couldn’t help it. The way she touched me was so sensual, and it just felt so good. “I knew I kept coming back to you for a reason.”

  I heard her laugh. “Good to know I’m good at this. It is my career after all.”

  She moved her hands down to my lower back and moved her thumbs in a circular motion on each side of my spine. I felt all my problems from the last week just melt away. At that moment, it was just her and I. Everything else melted away.

  I laughed. “You really are though. I’ve missed this a lot.”

  “I thought maybe you found a new massage therapist.” She sounded like she was messing around, but I could sense that the thought had crossed her mind.

  “Never. There’s no one better than Anna Winters,” I said.

  She laughed again. “Oh please, how would you know? Have you been to other massage places?” I loved the playfulness in her voice, but it wasn’t helping the sexual tension between us.

  “No. But I already know there is no one out there like you.” I was flirting hard, but so was she, so I didn’t bother trying to stop.

  After ten minutes on my stomach, she asked, “Want me to do the front again?”

  “That’s my favorite part.” I was so turned on. I couldn’t hide it.

  I rolled onto my back and watched as she got the hot oil and poured some onto my chest. She started massaging my arms, and then my chest going in slow movements. It was this moment that I wished I would have kissed her the other day.

  “Mmm. That feels so fucking good,” I said, my voice was full of lust. I hoped it wasn’t scaring her off. When I opened my eyes, she looked at me and bit her lip. It made the whole thing even hotter.

  “You like?” she said. I could sense that she was getting turned on as well.

  I nodded my head, “So much.” She moved down my abs and then back up. Her movements were torturously slow. I was looking forward to getting massages from her on a regular basis again. I had only missed a few at this point, but until today, I didn’t think I was going to get anymore again.

  I tried not to let my sexual thoughts get the better of me, but it was hard. She was so good with her hands. There had only been one time that I only partially got turned on, and that was on Monday. I was turned on then, but not as bad as other times because I knew I had to tell her I wouldn’t be coming back. It kind of put a damper on the whole thing.

  Even just looking at her turned me on. It caused me to have a massive hard-on. She didn’t even have to touch me for my body to ignite with desire.

  “You’re so hard,” she said as she massaged my tense arm muscles. She had turned it into a double entendre, and it was so fucking hot.

  “That’s why I come here,” I said with a wink.

  She blushed and bit her lip again. I wanted to be the one to bite that lip.

  I wondered if Anna had ever been turned on by me. I had to assume that she had, especially the way she was massaging me on Monday. But I couldn’t be sure.

  She moved down to my abs and the way she was touching me this time was completely different from the times before this. I could tell it was meant to be sensual, sexual. She was naughty, and it made me wonder if sex might be included in this new arrangement of ours.

  At this point, it was taking everything in me not to start touching her. I didn’t want to push my luck even though I had a feeling her panties were probably a little wet already.

  “You’re so hot,” I said, testing the waters.

  “Thank you, Justin. You’re hot too,” she said and moved her hands onto my thighs. She started massaging my legs moving up and down. She usually did this, but this time was a little different. She was moving slower, and every time she would massage my thigh muscles, her fingers would brush my dick. This had never happened before, so I could only assume she was feeling the sexual tension in the air.

  I had to say something again. I needed to know how she felt. I needed to be sure that she wanted this just as much as I did.

  “Since you keep brushing it, why not just massage it?” I said, bracing myself for her to freak out. I waited for her to run out of the room and tell me to never come back. She didn’t.

  “You mean like this?” she asked as she moved her hand onto my hard dick. She ran her hand up and down the length of it. It felt so good the way she was doing it. It almost felt like I could cum just from that.

  I nodded my head. I wanted her more than ever right now and moved my hand out to grab her ass. “What do you want to do to it now?” I asked her.

  She paused what she was doing looked at me with desire in her eyes.

  “Let me go lock the front door,” she said.

  I watched her leave the room and could hardly believe my luck.

  Chapter Eight

  Anna

  I locked the front door quickly so I could get back to Justin. My body was hot with desire, and I definitely did not want to keep him waiting, but I also didn’t want any potential clients walking in and hearing us. I thought for a second about putting up a sign that said I would be back in thirty minutes but decided not to keep Justin waiting any longer.

  I walked back into the room and began removing my shirt and shorts, and then my panties and bra. I had to calm myself down. I couldn’t believe this was actually happening, and for a moment, I almost paused. My insecurities made me hesitate for a fraction of a second, but I knew it would be better to just roll with it.

  “I’m ready,” I said and walked over to where he was lying naked on the table. It was an amazing sight to see. The size of his dick was huge, and I was a little intimidated to feel it.

  I bent over the table and took him in my mouth. He moaned deeply, and the sound of his pleasure made me wet. I slid my mouth to the tip of his dick and started licking it. Then, I moved it back into my mouth slowly. It was so big that I had to stretch my mouth a little bit to fit it in without scraping my teeth, but I didn’t mind. He started rubbing and lightly spanking my ass as I was bent over him. His arms were long, so he didn’t have to struggle to reach me. I was standing there completely naked. Before I knew it, he was sliding a finger inside of me.

  “Mmm,” I moaned with him still in my mouth. I began to suck harder, movin
g up and down on him. He slipped in another finger and began to finger me harder. He moved his fingers in and out so fast that I had to stop sucking on him when the pleasure became too intense. I could feel myself losing control of my body, and I didn’t want to accidentally bite him.

  He pulled his fingers out of me, and a small whimper of protest escaped my lips.

  He grinned at my complaint. “Get on,” he said in a seductive voice.

  I quickly grabbed my purse and pulled a condom out of the secret inside pocket. I tore it open, using my teeth, and then pulled the condom out and slowly rolled it onto him. He let out a small moan, and it was almost too much for me to handle.

  “You’re so sexy,” he said as he moved his hand up and down his long shaft.

  It was hot the way he was looking at me while he played with himself, and I wondered if he had ever masturbated to the thought of me.

  I climbed onto the massage chair and lowered myself into a straddle position. I leaned forward a bit so our chests were touching, and I began to feel him enter me. He was so hard, and I was so wet that he slid right inside.

  “Mmmm, your pussy is so tight,” he whispered as his eyes fluttered closed. Chills shot up and down my back.

  I didn’t respond. Instead, I focused on feeling him move in and out of me. I could feel each and every time he hit my special spot. It was driving me wild and starting to get me closer to an orgasm, but I wasn’t ready for the fun to end. I didn’t want to come too quickly. So, I sat up.

  “What are you doing?” he asked.

  I put a finger to his lips to tell him not to talk. He nodded his head. I carefully moved my body around so I was facing away from him, and once again I lowered myself onto his erection. This time though, it felt different. He was deeper inside of me, and it hurt a little bit, but the pain was a good pain. I could handle this because it just meant he was big enough to get all the way up there.

  “Oh, fuck,” I said as I began to move my body up and down on top of him. I started going slowly, but quickly picked up the pace.

  This was everything I had imagined it would be and more. His body was perfect, and I was loving that I got to touch him the way I had always wanted to. This was everything that I had wanted to do on Monday, and the waiting had only made it that much more intense.