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

by Piper Sullivan

  “Damn, you’re tight as fuck,” he grunted, as he buried his face in the crook of my neck.

  I wrapped my arms around his neck as I felt him pushing deep into me with long hard strokes. His sheer size stretching me beyond anything I had experienced before. But instead of pain, I felt immense pleasure as I felt my walls clench his hard shaft.

  This wasn’t the lovemaking fantasies I had envisioned as a teenager. This was carnal and savage, almost primal and it didn’t take long for my body to start tingling from the base of my skull down my spine to my toes. Each relentless thrust pushing me closer to the edge, and from the way Jason had dug his fingers into my ass cheeks, he wasn’t far from his release either. Whether it was the long dry spell of having no sex, or the fact that it was Jason, was yet to be determined. All I knew was that I was done for, and so was he. We both clung to each other as shockwaves of pleasure rippled through our bodies, as if our bodies served as conduits. As his breathing slowed and I finally felt my limbs relax, he released my legs slowly, and I slid down the length of him. He didn’t let me go straight away, his hands were resting on my hips and I was leaning with my forehead against his chest, unable to string together coherent thought.

  That was until the sound of Jaime’s door broke the silence. Instinctively we both held our breaths, and waited. Jason held up a finger in front of his own mouth and I nodded. The rustling sound of dragging slippers passed Jason’s door, and then we heard the light thudding of footsteps going down the stairs. Only then did we both let out a sigh of relief.

  Oddly the heightened sexual tension was replaced by an awkward silence, neither of us daring to say what was really on our minds.

  I placed my hands on his chest and pushed gently, “I should go.”

  He dropped his hands from where they rested on my waist but didn’t step back. “Ally…” his expression troubled.

  I held up one hand and just shook my head, I had to be realistic. He didn’t want strings, and he was practically sex starved. I was just an outlet. Don’t get me wrong, it was probably the best sex I’ve had in years, but it was just sex.

  “Jason, I… I’m glad you’re back, but this can’t happen again.”

  His face instantly dropped and a curtain of anger masked his earlier expression. He stepped back and deftly gestured towards the door, without any objection. I knew I should have said more, but somehow I didn’t think that anything I said at this point would change the way he felt about me. I tiptoed down the hallway, but when I heard the toilet flush, I knew Jaime had come back upstairs. Hoping the sound of the water flushing masked my steps I ran down the hall as quickly disappeared into my room.

  It was only a few seconds, but it felt like hours before I heard the sound of her door click. Climbing into bed, I pressed my fingers to my swollen lips. Running my tongue over my top lip, I could still taste the hint of root beer that had lingered on his tongue. I knew this could never happen again, and that it was the right thing to do. But how could something so wrong, feel so right?

  Jason

  After the incident last night with Ally and my sister’s untimely interruption, it had taken me several hours to fall back asleep. Even when I did manage to fall asleep it was restlessly. I spent all night tossing and turning, and when I finally woke up and rolled over to see the clock on my nightstand it was already after 10 am, I wasn’t all that surprised. I hadn’t meant to sleep that long, but I also hadn’t planned on a midnight rendezvous with Ally.

  Nevertheless, I didn’t have time to dwell on the whole debacle. Even though I had been released, I was still required to report to a parole officer. My original sentence had been 15 years; however, I had the option of being paroled after eight for good behavior, so my time spent in solitary and staying out of trouble paid off. Once released, I would be on probation for a year. Any violation and I would be sent back to prison for the remainder of my sentence. I didn’t want that. I couldn’t go back there. I would do whatever it took to keep from going back there.

  I grabbed a quick shower and then headed downstairs. I was surprised to find Jaime at the kitchen table, text books spread out and huddled over a legal pad. She looked up from her books and smiled sheepishly.

  “I wasn’t sure if I was supposed to let you sleep in or not, but I figured you needed it.”

  I just shrugged, “it's fine, I just have to call my parole officer by 11.”

  She made a face at the mention of the parole officer but I just ignored it. Instead I focused on the books at the table. “What are studying?”

  “I’ve got a chem lab quiz this afternoon. Just trying to make some quick notes I can study from. I should actually be heading out to meet up with my study group, but I wanted to see you before I left.”

  My sister really made me proud, with everything she had to go through, she still found the drive to study. She wrote down couple more sentences and then began to pack up her books while I rummaged around in the fridge for stuff to make a sandwich. Pleased by the fact that the content in the fridge didn’t consist solely of diet food, I grinned, it was really good to be back home.

  “I have classes all afternoon and then a shift at the bookstore so I won’t be home until 10. You’ll be okay by yourself right?” she asked her brow furrowing with concern.

  I lifted my head up out of the fridge and just smiled as she came over.

  “Yes, I think I can manage to occupy myself,” I said as I kissed her on the nose.

  She crinkled her nose and rolled her eyes just like I thought she would.

  “Fine, I won’t worry. See you later bro,” she hollered over her shoulder as she headed out the door.

  I smiled to myself, enjoying the feeling of someone watching my back. It had been a long time since I had felt that. I quickly fixed two beefy sandwiches and poured a big glass of milk before grabbing the cordless phone. I was thankful that Jaime had kept the house phone, otherwise I would have had to find a payphone to make the call to my officer. I took the piece of paper out with his number and dialed. It rang three times before a woman’s voice answered.

  “Malcolm Dunlevy’s office, how can I direct your call?”

  “Um, yes hi, this is Jason Armstrong, I was told I needed to check in with Mr. Dunlevy within 24 hours of my release.”

  I felt a little uneasy about how she might treat me but was pleasantly surprised when she maintained the polite and homey tone.

  “Of course, one moment Mr. Armstrong and I will see if he is available.”

  I was a bit taken back at being addressed as Mr. Armstrong. In prison I was referred to only as prisoner 57124, or monikers too vile to repeat. I was on hold for maybe 30 seconds before her voice came back on the line to let me know she was transferring me to him.

  “Malcom Dunlevy,” answered a deep baritone voice.

  “Yes sir, this is Jason Armstrong. I was released from Kenworth Prison yesterday and was told I needed to check in with you this morning.”

  “Armstrong…. Armstrong…Arm,” he muttered more to himself. It sounded like he was shuffling papers on his desk looking for something. “Ah, yes here we are. Jason Armstrong. Voluntary manslaughter, sentenced to 15 years, paroled after eight.”

  It was ugly to hear him rattle off the details so casually and not sure how else to respond, I replied with another, “Yes sir.”

  “According to your parole requirements you are to check in with me within 24 hours, which you’ve already done. You are to continue to check in with me twice a month for the duration of your probationary period which is 12 months.”

  Most of what he was telling was not news to me. The day of my parole hearing, after it had been granted, the warden had gone over the details of my probation. But I let him list the details and acknowledged each one of them as he went.

  “The final requirement is to be gainfully employed within two weeks’ time.”

  This last one was news to me.

  “Excuse me sir,” I interrupted. “Did you say two weeks’ time?


  “Yes, that’s correct.”

  “Um, is that a new requirement, because the warden didn’t say anything to me about it after my parole hearing?”

  I hated the uncertainty in my voice, but I had no idea how I was going to find a job in such a short amount of time. Not with my record and with Gladys Walters still a very prominent figure in the community even at her age.

  “No, it’s a standard probationary requirement,” he answered curtly. “Is there a problem Mr. Armstrong?”

  “No sir, it just caught me off guard. I am just not sure that I can find anyone in this town to hire me with my record sir.” I hated to admit it, but it was the truth, “It’s uh, complicated.”

  His tone softened a bit, “I am aware of your situation and the prominence of the Walters family. I have spoken with several of the city councilors and they assured me that you wouldn’t receive any prejudice.”

  I gave a derisive snort before I could stop myself. Quickly apologizing, “I’m sorry sir. I just hope you are right.”

  “I’m confident there are people in this town who are willing to give you the benefit of the doubt.”

  After a few more instructions, we agreed for me to contact him again in two weeks. I hung up, feeling far from confident. I knew it was going to be an uphill battle, and by no means did I expect life outside prison to be a walk in the park, but two weeks was ridiculous. If anything, the department could have assigned me to some sort of community service. But since my instructions were loud and clear, I had no choice. I was willing to do what it takes to stay out of prison and be there for Jamie. If I was honest with myself, I didn’t want to leave Ally either, but I tucked that thought away as soon as it came up.

  Just after midday, I got the newspaper, and worked my way down the list of possible vacancies advertised in the job section. To my dismay there were no real jobs that would suit me right away, most of them wanted credentials, experience, degrees, the list was simply endless. Considering my rep, I stood no chance to get a decent job. My next step was to walk door to door hoping that somewhere, someone would offer me a chance at making something of my life. Luckily our town was relatively small, and the business district was only about a mile and a half away. I wish I could have had my parole officer’s optimism, I thought as I made my way there.

  But once I started knocking on doors, reality set in. No one was interested in employing me. It was like a penguin caught in oil slick and then being held in captivity for years until it could be rehabilitated enough to be released back into the ocean. In the case of humans however, there was no such thing as a slow fade back into a world that you had no part of for most part of your adult life. While life inside the prison pretty much stagnated, life on the outside progressed at a much faster pace.

  After being turned down by more than a dozen places, some of them even displaying Help Wanted signs in the window, I suspected that either the councilors had lied to Mr. Dunlevy or Gladys had gotten to them already. Some made the excuse that they already filled a position; while some blatantly admitted that having a staff member with a criminal record was bad for business. That much I could still handle, but then there were the ones who were downright assholes, not bothering to hide their hostility.

  After being berated by an elderly lady at the fabric store and called a murderer to my face, I had all but accepted my fate and that I would be heading back to prison in next to no time. For a moment, I wondered if that wouldn’t be better, I would be no burden to Jaime, Ally wouldn’t have to put up with me again, and they could both carry on with life in the fast lane. I continued walking, not really paying attention to where I was headed. I eventually arrived at a bar on the outskirts of town called Hennigan’s. So much had changed over the years, new buildings had been erected, some of the older places I did recognize had been completely restored and revamped, and this bar was one of those. From what I could remember it was a downright shady bar, but standing in front of it, it looked like it had been completely transformed.

  I had no idea what to expect when I first entered, but I was pleasantly surprised. The ambience was dark without being dingy; the mahogany wood of the bar was polished to sheen, so much so you could probably lick a spilled drink off the counter. And even at 4pm in the afternoon, the bar had a decent crowd. I hesitated at the door, not sure if I would end up running into one of the many enemies, known and unknown, who would want to have a piece of me. I scanned the crowd and then I casually headed up to the bar and ordered a whiskey on the rocks. I pulled a bowl of peanuts closer and grabbed a handful, anything to look preoccupied and not like some shady stranger about to start trouble. The bartender placed the glass in front of me and casually moved on to the next customer. She was a fetching woman in her late thirties or early forties by my guess. She didn’t take much care to get all dressed up and the minimal makeup showed that she wasn’t the type to hide behind a fake face. What you saw was what you got. Although she was a small woman, she looked like she could handle herself; she radiated an air of confidence that could quite easily intimidate.

  After a couple of drinks, I ordered an appetizer to soak up the alcohol I have been indulging in, then a second and a third. I must have looked rather pathetic because by the third one, she came over and asked, “Okay, so who pissed in your cheerios?”

  “What?” I looked up in surprise.

  I guess I had been wallowing in my own self-pity, or she knew who I was and that was her point of entry.

  “You’ve been sitting here for three hours, nursing my cheapest whisky, snacking on oily fries and looking like someone kicked your puppy. Spill it.”

  I studied her briefly, there was a tenderness behind the cold exterior that reminded me of my own mother, or maybe the whiskey had softened me up and had broken down the walls I had erected around myself. I found myself confiding in her. I told her everything. About being paroled and trying to take care of my sister and how my parole officer had assured me that this town had forgiven me but the harsh reality was that the people here in Galena had the memory of an elephant, and the Walters name still had clout.

  At the mention of Gladys Walters, her face hardened. I thought for sure I’d done it, and that she too was in the pocket of the Walters. She stared at me for a long minute, before asking pointedly, “You Joe Armstrong’s boy, aren’t you?”

  That was not the question I had expected her to ask.

  “Yeah, I am,” I answered hesitantly, unsure of where this was going. She gave me a long measuring glance.

  “My father knew him before he passed. He was a good man.”

  I didn’t quite know what to say, and just swirled the whiskey around in my glass. She uttered the words with such compassion that I felt my heart cramp in my chest.

  It was the great mystery of life that always had my mind boggled. I often wondered exactly what it was that maps out the road ahead for an individual. Circumstance and disaster were the things that shaped the yellow brick road to Oz, it either throws a left turn or gives you up hill, and you have no choice but to follow it diligently and hope that you eventually get to the end.

  “Are you an alcoholic?” she asked out of the blue.

  “No.”

  “You do drugs?”

  “No,” I answered a bit offended, “I’ve never touched drugs and I don’t plan on either.”

  “Good. You can start tomorrow night,” was all she said before walking away.

  “Wait, what?” I said shocked.

  She glanced back over her shoulder and said, “You heard me. Be here at 8pm.” And with that she walked into the back room as another bartender took over.

  Ally

  Yawning sleepily, I took another big sip of my grande Caramel Macchiato as I sat in the back booth at Java Jones. I had been coming here for the past few weeks straight, slipping out of the house at 6am to avoid Jason. Jamie had confronted me a few times, but I told her that I was just trying to get in some extra studying since I had papers to submit. I made up some excuse that I wa
sn’t coping too well with one or two courses, and had to put in extra effort if I was going to pass the mid-terms. In some way, there was some truth to the lie, studying part time and working was a little harder than being in college and running to classes all day. Needless to say, my excuses, albeit valid, still weren’t enough to convince Jaime that everything was okay.

  It didn’t help that two days after we’d had sex; Jason had showed up at Hennigan’s. I had been about to confront him and ask him what the hell he was doing there, when Mac came by and introduced him as the new bouncer.

  And that right there just complicated everything. Jason was flung back into my life, like a comet out of orbit heading straight for impact. He was everywhere, in the house, at my work, in my head, and there was nowhere for me to hide. At home I pussy-footed around him, uttering an occasional hello or good night. Whenever a conversation started, I darted for my room, with the age-old “I have to study” spiel. As for work, I did manage to get Mac to change my schedule Jason’s first week, but then she started giving me a hard time and questioning my motives. So, I had to go back to my normal working schedule since I couldn’t really give her a good reason for not wanting to work during happy hour when it was the busiest time. That, and I really needed the money. Tips at happy hour were the best, but that meant I had to spend close to six hours a day in Jason’s presence. Thankfully, when it was really busy I was distracted and hardly had time to think about him. But it was during those quiet times, when I could feel his eyes on me, that an undeniable flutter would swirl in the pit of my stomach. Of course, when it came to cashing up and so on, I had no choice but to be civil while he hovered around like a drone. We hardly spoke, but considering the tension, words weren’t exactly needed.

  I hadn’t really had time to reconcile what had transpired between us and I had no idea know how I felt about it. Truth be told, I had tried everything to avoid thinking about it. Hoping that ignoring it completely would somehow make it all just go away. But deep down, I knew that it wouldn’t, and that I was nothing but a coward.