Prince Daddy's Nanny: An Older Man & A Virgin Romance

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by Piper Sullivan


  “You thought it wouldn’t matter?” The expression on her face quickly changed. Playfulness was replaced by hurt, “Of course it mattered. You’re my brother.”

  She looked away and sighed, “I’m sorry. I know things were…difficult and strained when mom died. I didn’t handle it very well.”

  I put my hands on her shoulders, forcing her to look at me, “James,” I started using my old pet name for her, “I should be the one apologizing, not you. You were barely 19, and you were left alone to deal with her death and all the arrangements by yourself.”

  Regret washed over me. I had missed so much in the years spent in jail that I never once thought about how much she would have to do all on her own. The only thing that mattered to me at the time was what I had saved her from. Never once giving thought to everything else she would have had to endure once the dust had settled.

  A small smile tugged at the corner of her mouth, flashing one dimple, “It’s not your fault Jason. And besides, I got through it; at least it made me grow up faster. I had no choice really, I only had Ally, and I couldn’t depend on her forever.”

  At the mention of Ally’s name, my mind drifted to earlier memories. Immediately, I could feel the blood rush below and my groin tighten uncomfortably. Now was NOT the time for this.

  Abruptly changing the conversation back to my initial question, I asked, “But that still does not explain how you’re here, how did you find out I was being released early?” I tugged on a lock of hair affectionately, “Don’t get me wrong I’m glad you are I am just curious how you found out.”

  “Oh, well, a little birdie in town told me.”

  I could always tell when my sister was lying. She would never look me in the eye, her eyes darting anywhere but my face, while tucking her bottom lip under her teeth.

  I chuckled and crossed my arms cocking a suspicious brow. She shuffled her feet, still refusing to make eye contact. But, I knew how to wait her out.

  With a huff, she finally blurted it out, “Okay fine! I found out from the old bitch Gladys.”

  Gladys. A name I had tried to burn from my memory. I could feel the familiar burn of rage simmering just below the surface of my skin. After all the pain and hurt her and her family had put us through, it killed me to hear that she had any part in my sister life or our blissful reunion. Refusing to let it mar this occasion, I suppressed my anger and kept my tone blank,

  “What do you mean you found out from her?”

  “Well, I know she didn’t mean for me to find out, that much was clear.” Jaime began to pace back and forth, gesturing wildly with her hands.

  “I had been in the county office, paying the back taxes on the house…”

  My teeth inadvertently clenched and my jaw tightened at the mention of her having to handle back taxes, but I remained silent, allowing her to continue uninterrupted.

  Eyeing me warily, she continued, “The clerk at the county took me around back to her desk to verify the amounts owed. So, I was half-hidden behind her cubicle wall when I heard her voice, you know, Gladys’s? She was obviously irritated about something because she wasn’t even trying to keep her voice down. I was trying my best to ignore her until I heard you name.”

  I loved my sister, but she tended to be long-winded. I tried not to show my impatience as I willed her to get to the point. She must have sensed my agitation because she rushed through the rest of her story.

  “Anyways, she was talking with the Sheriff about your release. She was trying to get it denied and threatening the Sheriff’s job and throwing around her family name and so on.” Jaimie rambled on, getting all worked up again, hands waving around as she explained what happened, “So I stood up and made my presence known. Gladys immediately turned red and accused me of spying on her. I don’t know what came over me, but I was tired of being bullied by that woman and her family. So I blatantly told her that if she hadn’t wanted the whole world to know, she shouldn’t be shouting it from the rooftops, like a banshee.”

  Jaime managed to look both proud and a little sheepish at the same time, “I may have also mentioned that she may have been able to buy the judge and jury of this little town, but that her influence stopped there.”

  I hated that I hadn’t been there to protect her from Gladys’s sharp tongue, but I couldn’t help but admire the fierce young woman she had become. I smiled at her proudly as I put my arm around her.

  “I’m proud of you. You’ve managed to rise above everything and thrive despite that family, and what they did to us.”

  “Eh, I did what I had to,” she said and shrugged, “Come on, let’s get you home.”

  As we pulled away from the desolate bus stop, I forced myself not to look back at the prison. For the first time in years, I felt light. I felt hope.

  Ally

  I finally managed to get a moment to just catch a breath, happy hour was over and most of the patrons were heading home. Te, and although the place was still reasonably packed with a few stumbling die-hards, who insisted on having just one more drink for the umpteenth time. My toes were numb from standing so long, and the fact that I was so distracted didn’t help at all. By now Jamie would be on her way back from prison, a bombshell she decided to drop on me just this morning and boy was I gobsmacked. It’s been years since I last saw Jason, and to be honest I never thought I would see him again, but that never stopped me from reminiscing about him.

  I pushed myself away from the wall and placed my hands on my hips, stretching and arching my back to get some relief from the stiffness. So my weight wasn’t really ideal, but then again I was never one to bother with diet plans and boot camps to become the perfect size six. As long as I didn’t cringe when I looked in the mirror, I didn’t care what people thought, besides if Kelly Clarkson can get someone like Brandon Blackstock to fall head over heels with her, there was hope for me right? I rolled my eyes to the heavens and blew a stray strand of hair that fell over my eyes out of the way. Who was I kidding, Jason branded me for life, after him, every date I went on ended up being a science experiment or a chemistry lesson, and the chemicals never mixed. Every relationship I ever attempted fizzled to nothing within the second week. I sunk down on plastic beer crate outside the door and leaned my head back against the wall, letting the memories swamp me.

  ***

  I had been staying at Jaime’s house while her parents were out with friends that weekend and of course we had done exactly what most teenage girls with freedom would have done, smoke, drink and watch R-Rated movies for shits and giggles… I had conveniently forgotten to mention to my mom and dad that Jamie’s parents were out of town when I asked them to let me sleep over.

  “Jamie, if we get caught we’re going to be in so much crap!” I said as Jamie snuck the bottle of whiskey from the drinking cabinet.

  We were only fifteen and I guess it was the excitement of being so recklessly naughty that inspired the whole thing.

  “They’re away for the weekend, relax!” she said.

  “What about Jason?”

  “He’s too preoccupied shagging Sonia’s brains out, he won’t even notice us,” she giggled and took a swig from the bottle. Of course she broke out in a fit of coughs, and then burst out laughing and handed it to me.

  That was how that night started, and a night that would be tattooed into my mind forever. Unlike Jamie and I, who always stood on the side lines and sat at the furthest corner of the cafeteria in school, her brother Jason was the popular playboy every girl tried to dig their nails into. Jason had been eighteen then, a senior, and I was the nerdy, chubby fangirl who shamelessly swooned over my best friend’s brother. What made it even worse was, whenever he had taken a girl to his room, Jamie and I would sit and eavesdrop, and then mimic their moans and groans. But what started as a complete mockery eventually became the very thing my fantasies were based on. Not quite appropriate for a girl my age, but either way, I was fifteen going sixteen, hormones had taken my body hostage, and I was just an innocent bystander.r />
  I remember it as if it was yesterday, I had gone upstairs to Jamie’s room to crawl into bed. The world had started to spin out of control, Jamie was passed out like a sailor on the living room floor, and I simply needed to sleep.

  I passed by Jason’s room, tempted to knock and make up some excuse to bother him if he was in there, but I resisted. He probably wasn’t even home anyways. He was always out on a date with a different girl. He didn’t have time to notice me.

  Turning away from his door, I forced myself to walk the rest of the way to Jaime’s room and closed the door behind me. Leaning against the door, I expelled a small sigh. Why couldn’t I get over this crush? I didn’t quite understand why I reacted to him the way that I did.

  Shaking my head, I pushed off the door and headed for my overnight bag. It was definitely time to get some sleep. I stripped out of my clothes, down to just my panties. Even though my breasts were quite large now, I hated sleeping in a bra. Since I hadn’t planned on leaving Jaime’s room again, I took my bra off and tossed it on the floor.

  I dug around in my duffle until I found my favorite sleep shirt. It was an old Pink Floyd t-shirt that used to be my dad’s. I had found it in a box of clothes marked for the Goodwill and had taken it for my own. It used to be so big on me, hanging down to my knees like a dress. Over the years, I had finally started to grow into. It now hit me just above mid-thigh. Which wasn’t too bad. It still covered my ass.

  Now my chest was another story. Ever since my breasts decided to double in size over the summer, the t-shirt could barely stretch across them. Already threadbare from the numerous washing over the years, the material was so taut it was almost see through. But again, I didn’t think anything of it because I wasn’t planning on seeing anyone but Jaime.

  I went to go put my retainer in its case. But it wasn’t in my bag. After throwing everything out of it and checking every pocket, I remembered that I had left it in the bathroom. I stood there for a few minutes debating with myself whether to go and get it.

  I couldn’t sleep in it, and I really didn’t want to just leave it lying around. That’s how I had broken the last one and my parents would kill me if I ruined another. They weren’t cheap. I had no choice. I would have to go grab it real quick.

  I hesitated wondering if I should put my clothes back on but that seemed silly. So, I cracked Jaime’s door and stuck my head out. Her brother’s door was still closed, and everything was quiet. Taking a chance, I raced down the hall to the shared bathroom. I shut the door behind me and leaned against the sink to catch my breath.

  I admit, I felt a little silly at my reaction. I placed my retainer in its case and then I splashed a little cold water on my face to calm down. As I turned to wipe my face on the hand towel hanging against the wall, I heard giggling coming from down the hall. Followed by a male voice whispering and another giggle. The giggle was definitely female, but it wasn’t Jaime. Jaime didn’t make high pitched squeals…ever. I knew instantly that the sounds were coming from behind Jason’s door.

  I waited a few moments until I heard the sound of his radio turned down low in his bedroom. Quietly, I opened the bathroom and peeked out. The coast was clear. I would still have to make my way past Jason’s door to get to Jaime’s, but knowing he had a girl with him. I knew he would be …preoccupied for a little while.

  Tiptoeing into the hallway, I made my way as quietly as possible. I didn’t think they could hear me, not with the radio. But I didn’t want to take any chances.

  As I approached his door, I saw that it was now slightly ajar and not as tightly shut as when I first passed. I could hear whispers and the unmistakable sounds of kissing. A pang of jealousy hit me. I wanted to be that girl. I wanted to know what it felt like to have his arms around me.

  Jason never had any trouble getting girls to fall all over him, and it wasn’t any surprise. He was cut from years of playing sports. He was also quite charming and had the same twin dimples that Jaime had. It was an irresistible combination that even I couldn’t resist.

  It’s not like I hadn’t been over when he’d taken a girl up in his room. Jaime and I would usually laugh and joke about it. That was back when we thought it was disgusting. But lately, I hadn’t found it disgusting. In fact, I had found it enticing. I wanted to know what it felt like. I wasn’t very experienced. Sure all of the guys in our class stared at my breasts and made crude jokes about them. But they still all preferred the stick-thin pretty girls. I was what you would call full-figured if you were being generous. Always had been. Though I would never admit it to anyone, not even Jaime, I was very self-conscious about the way I looked. My self-consciousness came across as shyness when around the opposite sex, so I’d never actually had a boyfriend yet.

  Before I realized what I was doing, I was in front of his door and gently nudged it further open. Wide enough to see the mirror over his dresser. Which was positioned directly across from his bed. I had a direct view of Jason and the one and only Sonia.

  I just couldn’t tear my eyes away. Had I been observant enough to know that the mirror also reflected the exact spot where I had been standing, I would have run for cover almost immediately. But I didn’t know that, and I just kept watching.

  Jason took a breath from sucking on the blonde’s neck to yank her blouse open, buttons flying everywhere. The girl admonished him, but he ignored her. My entire body began to tingle and I felt hot as I continued to watch through the crack in his door.

  She beckoned him forward slipping the remains of the shirt off her shoulders and tossing it to the floor. He stepped forward closing the distance between them. She went to say something smart, but he silenced her with his lips in a quick devastating kiss before he pushed her back against the bed until her knees hit the edge.

  She fell back on the bed and he covered her body with his. His hands none too gentle has he grabbed her breasts through her lacy pink bra. She squirmed under his attentions and drew her knees up.

  She was wearing a mini skirt so I could see that she was only wearing the tiniest of thongs. Her small rounded cheeks exposed. She gave a startled yelp when his hands slid down to her bare ass, before he slapped one side firmly. Did he just spank her? I was so confused. I had seen sex on tv before, but never like this. But then he was soothing the tender red flesh with slow massaging circles.

  She sat up long enough to release the clasp of her bra, sliding the straps seductively down her arms before tossing it to the side. She had small, perky breasts with tiny, tight pink nipples. He smiled as he leaned over her and took one tiny bud in his mouth.

  I felt my own nipples harden in response. Rubbing against the soft fabric of my t-shirt. It was uncomfortable in a good way. I wondered what it would feel like have his mouth on my breasts. To feel his tongue and lips on my nipples. I could feel myself getting damp between my legs as I fantasized about being the girl in there with him. I shifted my legs uncomfortably, trying to ease the ache.

  I let out a small whimper before I could help myself. Shocked, I clamped a hand over my mouth and that’s when he glanced in the mirror directly at me. My eyes locked with those drop dead gorgeous baby blues, and he smirked at me.

  I had run for the bathroom, frantic and embarrassed for spying on him so openly, hoping that he would simply ignore it and carry on with life as if I didn’t exist. But I would be so lucky.

  He had made his grand appearance behind me in the small, confined space. He asked me if I liked what I saw, and of course I was speechless, or rather brain dead. I stuttered like a fool and the way his lips turned up and his brows had cocked in amusement had me grasping for straws. There had been nothing, not a single excuse I could have thought of quick enough that would save me from utter embarrassment.

  But that was where things got a little interesting. Whether the fact that I, or any other person for that matter, had watched him, had turned him on, or whether he had this secret love for preying on innocent young girls’ emotions was another story altogether. All I knew was that
it was the night that would change my entire outlook on the male gender forever…

  “So,” Jason said with a smirk, “You liked what you just saw?”

  “I…uh, I didn’t see… much,” I lied.

  “Liar, you saw everything, you were spying me and Sonia for almost five minutes,” he smirked.

  “Well… yeah, but… I didn’t see…” I was in the hot seat, caught red handed and there was no way to get myself out of this one, “You could have closed your door!” I retorted instead.

  “It’s my house; I can do what I want.” he chuckled and stepped closer, then sniffed the air, “Were you drinking?”

  Great! I had told Jamie that we were going to get caught.

  “Jamie… well we had some whiskey, just a little.”

  Jason laughed, but his eyes were full of mischief, he came closer until I was caught between him and the towel rail.

  “Have you ever been kissed?” he asked, a smile tugging at the corners of his mouth.

  “Of course…okay no, I haven’t,” I admitted nervously.

  “Do you want to be kissed?”

  “I-um-no,” I lied.

  Jason clearly didn’t fall for it; instead he bent his head and pressed his lips against mine. I froze like a statue, too scared to breathe or move. The persistent movement of his tongue tracing the seam of my lips tore my defenses down and when I finally gave in, I kissed him back. The kiss was clumsy; I had no bloody clue what to do with my tongue, or how to angle my lips. My nose was in the way, but somehow the kiss evolved on its own. Then he stopped, looked at me with another smirk, turned around and sauntered back to his room. And Sonia.

  As soon as his door slammed shut, I quickly ran back to Jaime’s room. I grabbed a hairbrush off her nightstand and pretended to be brushing my hair when she came in just after I did. I feigned being tired and climbed into the top bunk. She turned off the lights and soon I could hear the faint sounds of her snoring as she slept.

 

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