Nanny with Benefits

by Amy Brent

  I stepped forward and rubbed my cock up the length of her pussy. She was wet and swollen. I slipped the tip of my dick inside her. She flinched as I stretched her out. She was tight—tighter than she had been. She must not have been fucking much for the last few months.

  I pushed my cock deep inside her. She moaned and clutched her sheets. She hung her head but kept her back arched for me. I put my hand on the small of her back and screwed her, hard and deep, until I was about to explode.

  I pulled out just in time. I wasn’t ready to stop. Not yet.

  She gasped when I slipped a finger into her. I didn’t let her recover. I slid another finger in and pushed down, right against the spot I knew she liked. Her back hunched for the briefest moment. I knew I could make her orgasm in seconds.

  I fucked her hard with my fingers. The only thing stopping me from going deeper was my own knuckles.

  “Come on baby,” I said to her, flicking my fingers in her juicy pussy. “Let it happen.”

  She did. She threw her head back to the ceiling and let out a whimpering cry of pleasure. As her pussy filled with her own juices, I pulled my fingers out. She squirted, spraying my thighs and her sheets. As she quivered on the bed, I stepped forward again. I slicked my cock with the juices on my fingers and then proceeded to thrust myself deep inside her.

  She cried out again and collapsed forward. I grabbed the back of her shirt and pulled her up, holding her as close to the edge of the bed as I could get her. I wanted to be deeper. Always deeper.

  She came again. I felt her walls constrict around me as I mounted my own orgasm. I bucked against her, and she went wild. Her thighs shook, and she buried her face in her mattress to muffle her scream.

  When I was done, I gave her a couple slow thrusts, enjoying the way my cum felt inside her. Then I pulled out. She dripped on the bed. I slapped her ass lightly.

  She rolled over and lay on her back, looking at me. “That was better than all the ones I imagined,” she said breathlessly.

  “Damn straight. That little pussy of yours deserves to be fucked like that,” I said, making my way to the bathroom. I left the door open while I cleaned myself off.

  “Do you want to stay for a while? Watch a movie? Spend the night?” Allie called from the bedroom.

  I pumped some of her hand soap into my palm and paused. The offer was tempting, but things were moving quickly. I didn’t want to throw myself in too deep again. Friends was a safe place to be. Friends who fucked was a great place to be—especially with Allie. That body and that pussy of hers were too good to pass up.

  “Allie,” I said, leaning back to look at her through the open door. “I don’t think that’s a good idea. Maybe another night?”

  “Oh,” she said, sitting up and pulling the blankets over her still naked lower half. “Yeah, that’s fine. I have an early morning tomorrow anyway. I’m sure you do, too.”

  “Yeah, I do,” I lied.

  The only thing I would be waking up to do was jerking off while thinking about the session she and I had just had.

  Chapter 18

  Allie

  My pussy was wet when I woke up the next morning. It was early, only quarter to six, and my alarm wasn’t set to go off for another half-hour. My dreams of Steven had woken me, and now I was horny as hell, and my pussy was aching for something—anything. I wanted Steven’s cock again. I wanted him in my mouth, down my throat, and in my tight little hole.

  I wanted to feel his body grinding against mine. Thinking about his tender kiss, and how it had become something feral and savage made me wetter. I wished he was there to fill me up.

  I settled for my own fingers, running them down my belly and over my clit. I wandered down the length of my slit, easing my folds to the side like petals. All the while I thought about how Steven had fucked me the night before.

  When he had bent me over and shoved his cock into me, I thought I might scream. I hadn’t had sex in over three months, and his dick felt bigger than I remembered. He hadn’t warmed me up, either, like he usually did. He had gone right for it, thrusting deep inside me and not holding back.

  Then, right in the middle of it all, when he had used his fingers, I lost it. It had felt so damn good.

  I slipped a finger into my pussy and pretended it was Steven’s. I wanted him to do that to me again.

  I used my other hand to caress my bud. My orgasm was close. I was so wet. I was ready to be fucked again. I wished Steven had stayed the night. We could have woken up together—or he could have woken me like he did that one time by pressing his erection up against my back. What a delightful way to wake up.

  I sucked in a breath and held it while my pussy tightened. My toes curled. I held my breath as my orgasm shook me. I let it consume me and didn’t gasp for air until I was done.

  I stared at the ceiling for a while afterward, catching my breath, enjoying the ticklish sort of feeling as I ran my fingers over my pussy until my alarm went off.

  There was no better way to start the day.

  At work, I couldn’t shake the nagging feeling that had settled in my belly since my morning session. I was worried that Steven wouldn’t reach out again. Maybe he had got what he wanted. The way he had left the night before kept replaying over and over in my mind, and the anxiety over losing him reached an all new high.

  “I don’t think that’s a good idea,” he had said. What did that mean? We had enjoyed our meal and laughed as freely as we used to. He hadn’t hesitated to carry me to the bedroom, where he proceeded to screw me like he never had before. I had been sure that he had wanted to fuck me as badly as I wanted to fuck him.

  His words had left an opening for doubt. Maybe it had just been sex for him. It was more than possible. Had he moved on over the last three months. Maybe he didn’t love me anymore.

  I knew I loved him. I had never stopped. Even though I doubted I would ever see him again, I be forever in love with him. For a fleeting moment, I had thought the feelings were mutual last night. Now, I was back to being completely unsure.

  Now that I thought I had him back, I was terrified of losing him again. My heart wouldn’t be able to handle it.

  I spent the first half of my shift tense, nervous, and checking my phone every fifteen minutes hoping to see a text message or a missed call from Steven.

  That afternoon, I found myself sitting at a new salad bar around the corner from my work. It was a small place with a minimalist feel. The tables were all aluminum with matching chairs and a glass vase with a single daisy in the middle. I was meeting Melissa there, and for the first time in a long time, I had arrived first.

  When Melissa did arrive, I had finished perusing the menu. It had been an adventure. There were over thirty salads to pick from. I stood up, and we hugged. Then we both sat back down. I let Melissa choose her salad, and once we had ordered, she tucked in her chair and blew out an exasperated breath.

  “I’m sorry I had to bail on you so last minute yesterday,” Melissa began. “Everything has been so crazy at work lately. This is the first lunch break I’ve had all week. And I’ve been working until eight every night. This is the worst time of year, you know, and we are totally understaffed and—” she stopped talking and shook her head. “Nevermind. We only have an hour. All I’ve been doing is working. I don’t want to waste this time thinking about that place. How are you? You look good.”

  I smiled and tightened my hands in my lap. Melissa had been worried about me over the last few months. She had told me so many times. Living without Steven had been rough. It had taken a mental and physical toll, and Melissa had seen me at my worst.

  “Things are really good,” I said, waiting for her to ask more questions.

  “Really good?” Melissa said with a tilt of her head and an arched eyebrow. “Care to elaborate?”

  “Well,” I said, leaning forward and not fighting the smile that was stretching my cheeks. “I ran into Steven yesterday on my lunch break. I went to that little diner down the street. He was
sitting at another booth by himself. When he saw me, he got up, and we sat together.”

  “It wasn’t weird?” Melissa asked skeptically.

  “It was a little bit, but it passed. Especially later when I invited him over to my place for dinner,” I said.

  “He came over last night? Really? What did you guys do?” Melissa sipped her glass of water but kept her focus on me.

  “We ate dinner. And we talked. And then, after we talked, and after he forgave me, we went into the bedroom. And you know, one thing kind of led to the other.”

  Melissa put her glass down and shook her head. She was smiling, but it was small. “Good God, the two of you are something else. Does this mean you’re back together, or what?”

  “We were never together in the first place, remember? We were just friends who happened to be attracted to each other.”

  “And who fucked each other’s brains out. Yeah. I remember. I also remember the last three months where you’ve been miserable and, on some days, were incapable of even dragging yourself to work.”

  “Things are looking up,” I said, hoping some of my optimism might rub off on her. “Although, they aren’t what they were before the whole Andrew thing came out in the open. I asked Steven if he wanted to spend the night last night, or even stay and watch a movie. He said no. Which was weird. He never used to turn down movie nights. He said he didn’t think it was a good idea.”

  “Maybe you just need to take baby steps to get back on track,” Melissa suggested.

  “Maybe.”

  “Look, all I know is that you were so happy when things were going well between the two of you, and you were miserable when they weren’t. Don’t let him go this time, Allie. You deserve to be happy. If Steven is the one who can give that to you, you need to pursue that. Don’t you think?”

  “Sure,” I said. “It sounds great when you put it like that, but it isn’t just about me. I don’t know where his head is right now. He said he forgave me, but when he left, I had the impression that he might still need a bit of time. Which is fine. I can give him that. I should give him that, right?”

  Melissa shrugged and sipped on her water again. “I don’t know. You know him better than anyone else. It’s your call. All I know is I’ve thought the two of you should be a couple since the first time I saw you together. Don’t let something come between you again—even if that something is time.”

  I sighed and rested my chin on my hand. I blew a loose strand of hair out of my face and gave Melissa a pouty face. “When did life get so hard?”

  “Oh, I don’t know, Allie. Maybe when you started fucking your best friend?”

  We both burst out laughing. It felt good to laugh again, even though it was at my own expense.

  Our salads arrived, and we chatted a bit about other things. Melissa ended up talking a bit about her work, which I didn’t mind. She needed to rant, and I was more than willing to be her sounding board. After everything she had done for me over the last few months, it was the least I could do. Without her, I knew I wouldn’t have come out the other side still employed.

  After we had paid our bills, Melissa leaned in close. “Okay, I have fifteen minutes left. Spill the dirty details. I want to know everything. How was he?”

  I giggled and rolled my eyes. “He was better than ever. Not to mention, he’s somehow even hotter. He’s got the beginnings of a beard going on. He looks like a rugged businessman now.”

  “Shut up,” Melissa half-squealed half-whispered.

  “Serious,” I said. “And he does this new thing with his hair. It’s shorter on the sides and slicked back on top. It’s so sexy.”

  “Right, right,” Melissa said, rolling her hand in the air between us to encourage me to skip ahead to the good parts. “And in bed?”

  So I gave her the details. She listened in electrified silence, her mouth falling open when I revealed the juicy parts. When I was done, she sighed wistfully and poked at her empty plate. “I need a man who will do that to me,” she said.

  “Well, I’m sure one will come along,” I said with a small shrug.

  “I don’t know. Steven isn’t exactly representative of the male population. He’s kind of a rare find, you know? Good looking. Successful. Hot as hell. Good in bed. A trustworthy friend. It’s not fair to roll all those qualities up in one person.”

  “No, it’s not,” I agreed with a nod. “It’s kryptonite.”

  Chapter 19

  Steven

  Dante’s would be crowded and busy within the next couple hours. For now, it was humming with that “before the party starts” energy. People were clustered at tables sipping on martinis while the DJ was readying his line-up for the night. The lights were on but dim, and the steady hum of conversation was heavy in the air.

  Chance and I were sitting at the bar in our usual spot. We were sipping on cold beers and snacking on peanuts, and I was deliberating whether I should mention my run in with Allie the previous day.

  “So,” Chance said, interrupting my thoughts. “What’s going on with you, man? You’ve barely said a word all night.”

  I twisted a shell to get to the peanuts inside. I popped them in my mouth, washed it down with a mouthful of beer, and shrugged. “I’ve been thinking, I guess.”

  “Thinking about what?” Chance pried.

  “Whether or not I should tell you that I saw Allie yesterday.”

  Chance arched an eyebrow and put his beer down. “Oh really? Did you finally get the balls to call her?”

  “No,” I said. “I saw her at a diner. She was on her lunch break. I sat with her. Then she invited me back to her place for dinner. We talked, and things felt almost the same as they used to. It was good. I told her I forgave her.”

  “Just dinner and talking then?” Chance asked. He had always been able to see right through me. Before even asking a question, he knew the answer. He just wanted to hear me say it out loud.

  “Dinner led to other things,” I admitted.

  “Right. So you guys fucked again, hey?”

  “Yeah,” I said, draining the bottom of my beer glass and catching the bartender’s eye. I pointed at our beer glasses to order Chance and I another round. When the bartender gave me a thumbs up to acknowledge he understood, I looked back at my friend. “She asked me to spend the night after. I should have seen it coming, but it threw me off a bit. I didn’t know what to say. Staying felt like a dumb move.”

  “So you blew her off?”

  “Sort of. I told her it wasn’t a good idea, and I left. It was kind of awkward. It surprised her, I think. But she handled it well.” I thought of the way Allie had pulled the covers over her naked lower half. “At least, I think she did. I don’t know.”

  “Dude,” Chance said, almost scoffing. “Why would she handle that well? She invited you to dinner, and you agreed to come over. Then you talked and got everything out in the open. You forgave her. Then you fucked her.”

  “Yeah,” I said hesitantly, already suspecting the direction Chance was taking the conversation.

  “What impression was she supposed to have after that? Of course, she asked you to stay. If I know Allie, which I do, she would have been as bent out of shape as you were the last three months. You were a fucking mess, man. Don’t even try to deny it,” he added when I opened my mouth to object. “You drank more in three months than you’ve consumed in your entire life. I would know, I dragged your ass home four nights a week for the first month. Allie would have been just as devastated. And then, all at once, she thinks those ninety days are behind her. When she lets herself be vulnerable, you shut her down again. Man, sometimes you can be so thick-headed.”

  The bartender passed us two full glasses of beer. I stared down at mine as guilt tickled my gut. “Shit,” I said.

  “Yeah. Shit,” Chance agreed, polishing off his old beer and reaching for his new one. “Listen. You can do what you want to do. If you don’t want to go all in with Allie, that’s your call. But let’s be real for a m
inute here. You can’t be friends and fuck her. It’s not going to work. You want more than that, and so does she. And you both deserve more than that. Tonight is the first time in months that you’ve seemed like your old self. Do you think that’s a coincidence?”

  “No,” I admitted. “But Andrew—”

  “Man, forget Andrew. She buried that for a reason. She obviously doesn’t want him. She was sixteen for fuck’s sake. It was a mistake. You know, a mistake? The thing people make all the time and should be able to put in their rearview mirror? Let her move on. She’s a good person. Correction, she’s an amazing person. She doesn’t need you holding this over her head. Right?”

  “Right,” I said, meaning it for the first time since I found out about Andrew and Allie.

  “Exactly. Steven, you’ve loved the girl for years. Stop sidelining yourself. Don’t lose her again. You might not get another chance.” He lifted his glass and nodded down at mine, encouraging me to follow suit. I lifted mine, and we tapped them together. “To putting the last three months behind you and getting your head out of your ass,” Chance said.

  “Nice toast,” I said, a smile tugging my lips.