Training Little Abby (A Dark Age Play Romance) (My Little World Book 5)

by Becca Little

  “So, do you want to have a little pleasure for this accomplishment?” His lips drifted to my ear.

  “I want you to take me out.” I replied. “I want to have a night out with you.”

  “That can be arranged.” He placed my report card on the mantle. “Go get ready and we’ll go anywhere you want.”

  I went upstairs and found the finest dress I could—one that accentuated all my generous curves. I styled my hair and put on my makeup, trying to make myself look perfect. I knew what I wanted and I hoped I knew how to get it. The end of the semester was a big deal for me, and I had fallen head over heels in love with the man who provided me with such an amazing opportunity. When I walked down the stairs to greet him, I saw a shock of disbelief on his face.

  “You clean up well.” He took me by the arm.

  “Why thank you.” I smiled as we walked out the door.

  ***

  The restaurant he chose was one that I would have never been able to afford on my own. All I asked for was somewhere nice, and it fit the description perfectly. Despite doing my best to dress up, I still felt like a peasant when we walked through the sea of wealthy people waiting for their tables. We eventually made our way to the table he had reserved and I sat down with his assistance. The waiter came and I stared at Mr. Addison while he ordered. Even the way he asked for food was sexy and alluring.

  “So why did you want me to take you to dinner? I would have bought you something nice for doing so well this semester, or pleasured you in any way you wanted.” He dug his fork into his salad and looked up at me.

  “I needed a reminder that I’m still a woman. I’m happy to be your Little Abby, but there are times when I still need to know I’m more than that.” I admitted and shrugged.

  My hand went to my glass of wine and lifted it to my lips. I took care not to smear my lipstick as I took a drink.

  “I know I can be a little hard on you at times, but that is just my way. I am just trying to make sure you understand the importance of the things ahead of you. You have an opportunity to be somebody. It is what your father would have wanted.” He pushed his salad away and looked towards the waiter. I was certain he wanted his steak.

  “How did you know him?” I had been curious about that since the day I met Mr. Addison.

  “He helped me out of a jam once long ago. I had an accountant stealing money from me, and I needed someone to audit him in secret. Your father was just getting started; he was young and ambitious. I liked that about him. He saved me millions of dollars, and in return, I invested in his firm.” He shrugged and smiled as the steak arrived.

  “Wait a second. You’re the mysterious investor… The one my mother always talked about. You bought my father’s firm when he died!” Things started to click together.

  “I am, indeed. Bought might be a bit of a loose term. It was in dire straits. I donated some money to your mother, and took care of liquidating it. I made sure your mother wouldn’t have to work again, basically.” He took a knife to the steak and when he cut it, blood spilled onto his plate. I had never been one for raw steaks before, and was quite content with my well-cooked chicken.

  “She always said the money came from his life insurance policy…” I popped a piece of chicken in my mouth and it was like divinity, roasted to perfection.

  “Some of it was, I’m sure. She respected my privacy, but I have checked in on her from time to time, although it was never as often as it should have been. She told me about you, and the trouble you were having. She feels like she didn’t do a very good job with you after your father died.” He picked up his glass and washed his side of mashed potato down with wine.

  “She just couldn’t handle things after he died. I don’t blame her at all. I made my own choices…” I had to stop talking before I started crying at the thought of my mother and the struggles she had after my father passed.

  “That you did. It is good to hear you taking some responsibility for your actions. You’ve been making some interesting choices lately.” He narrowed his gaze on me.

  “What do you mean?” I had no idea what he was referencing.

  “I might a little bit older than you, but I’m not dead. I certainly notice when you wear the shortest dress in the closet…” He left his eyes on mine and I had to look downward to avoid letting my face show my surprise. “I’ve enjoyed pleasuring you, but I think you want more than just my finger.”

  “You noticed…” I felt myself blushing. “Maybe I was just hoping for one of your pleasurable treats.”

  “I noticed, Walter noticed, even my driver noticed.” He shook his head with a slight smile. “I think you are ready to permanently become my Little Abby, and you know what I get in return.”

  “I don’t know…” I really didn’t feel comfortable being confronted.

  “Oh, I think you do. You already know I’m a rather peculiar man and my tastes are a little different.” He picked his glass and took another drink.

  “I like peculiar things…” I finally raised my eyes to meet his.

  The conversation continued with him insinuating I was going to be his when the night was over and we were home. I wanted it, but I also didn’t want to just be another collection in his trophy like Walter had seemed to become. I liked the idea of being his Little Abby, but I wanted to know it was going to be forever if I committed to him. As the night wore on, my inhibitions started getting lowered with the wine and his insistence that I was going to be claimed by him made me burn with desire.

  When we crawled back into his car, he sat really close to me and rubbed his finger along the interior of my leg. I pushed it open, begging for him to pull my dress up, but he kept it below the hemline. I was ready to be his. I wanted it more than anything I had ever wanted in the world. I fidgeted with his hand for a bit and I couldn’t help but be annoyed that he wasn’t taking it further when I was already turned on. I reached for his leg and started to rub up the crease of his pants, but he pushed my hand away.

  “Not in car… Wait until we get home. We have place to ourselves tonight. There’s no reason to rush things.” He gave me a smile and I felt my heart leap up on my chest.

  “Okay.” I pulled my hand away.

  I could barely wait until we got inside, but out of respect for his privacy, I waited until the driver was out the driveway. He kissed me on the front steps of the house and after my head was spinning from our first kiss, he finally opened the door. He stepped behind me and rubbed his hands up and down my arms. Just feeling the sensation of his touch made my hairs stand on end... A grin crossed my face as he brought both of his powerful hands down onto the back of mine and squeezed.

  I could feel his breath on my neck and the slight tickle of his kiss, which caused me to giggle a little. He kissed my shoulder several times and then turned me around. I wrapped my arms around his muscular shoulders as he kissed me on the lips. His kiss was light and tender at first, and then it got more forceful. My brain instantly flooded with endorphins as his tongue entered my mouth and wrapped around mine. His hands went around my waist and he pulled me close. I could feel his cock already beginning to bulge in his pants as he lightly pushed it against me. My fantasy was going to come true—finally.

  “After tonight, everything changes.” He said with a tense whisper. “I am a very possessive man.”

  “I want to be your Little Abby in every way, and I want to be the only woman you love.” I whispered back and he kissed me again. “I want you to be the first man to have me.”

  The feeling of my lipstick being passionately smeared from my lips made me smile as he furiously kissed me and pulled my body as close as it could get to him. Each time my body rocked against his as our lips formed a hungry seal, I felt his cock getting harder and harder. It felt so good to be wanted. He brought his hands down and rubbed my ass through my dress as he kept kissing me and he pushed me back towards the dining room table.

  The sturdy wood would easily support our weight. He turned me as soon as we
got to it, and placed both hands on my ass. He started kissing my neck as he slowly pulled my dress up to expose my panties. His hands on my body felt amazing, like silk mixed with callouses and lust. His hands continued to massage my ass as he rolled it in his fingers and kissed my neck and ears with a little more force. I sighed deeply, loving every second of the incredible moment.

  “Tonight, you’re not only going to be my Little Abby.” He said with a kiss. “I’m going to make you a woman.”

  “I’m ready for that...” I felt myself getting wet as he talked to me with such furious passion. I certainly didn’t want to be his little girl in that moment.

  “I’m going to claim you as my own.” He said as he continued to squeeze and caress me.

  “I know what I want.” I smiled, even though I was quite nervous.

  After a few passionate kisses against my neck, he let the lobe of my ear sink into his mouth and he gently sucked it. I giggled once more as the ticklish sensation sent chills down my body. He turned me around, moving his hands up and down my back as he did, finally resting them on my ass. With a strong heave, he brought his hands behind my thighs and pulled me up onto the table. My ass pressed against the cold mahogany and he pushed my knees apart. He stepped in between them and started kissing me again, holding my back and my ass in his hand as he did. I wrapped my hands around his neck, fingers going across tough muscles, larger than I had ever felt in my life. His mouth sank back into mine and we kissed with my body grinding against him.

  I pushed against him so much that I began to slip off the table. He caught me in his arms as my feet gently touched the floor. He turned me around and bent me over the table slightly, bringing my dress all the way up until it was around my hips. His hand came down with a playful smack and the flesh jiggled. He massaged my bottom and spanked me a few times, with me moaning with pleasure after each one. He pulled my panties up into the center of my ass, effectively turning them into a thong that totally exposed every bit of it. He brought his hand down on the exposed flesh a few more times, and then his finger drifted down the line of my panties, rubbing the edge of my pussy. His finger moved hard and fast, with some of it touching the exposed flesh, but the majority rubbing across the fabric of my panties.

  “You spank your women too?” I asked playfully.

  “I spank whoever I want to spank.” He slapped my bottom one time hard and I moaned.

  He grabbed my ass and once again put me on the table, this time with enough force that the table created a thud. He grabbed my head with a passionate, hard kiss and I grinned. My heart started beating in my ears as his touches and his kisses got more forceful. He pulled my dress off my shoulders and straight down until my bra was exposed. He quickly unsnapped it and threw it on the floor, massaging my naked breasts.

  He leaned down and kissed the right one, taking the nipple into his mouth and rolling around on his tongue before giving it a slight nibble. The sensation shocked me, but it felt great. He moved across my chest to the other exposed breast and squeezed it until the hard nipple poked straight out. He took it in his teeth and rapidly licked the tip with the edge of his tongue. I rolled my head back and locked my fingers around the back of his neck as electric sparks shot through my entire body from the slight pain and intense pleasure.

  “I like that.” I said with a long sigh.

  I wrapped my legs around his waist as he continued to suck on my breasts. My fingers tore at his shirt, peeling off each button one by one. Once I it open, I ran my fingers across the outline of his abdominal muscles and ribs. I tugged until the undershirt was free and I could sink my fingers into his rock-hard muscles. His lips came up to my neck and he kissed me and his excited breaths felt warm and tingly on my lips. I brought my hand down to his pants and found his cock still hard and waiting. I gripped it through is pants and stroked it the best I could. Even after having it in my mouth most of the weekend I was punished, I was still amazed at the size. I couldn’t wait to find out how it felt inside my pussy, even if it hurt.

  He brought his hand down around my ass and squeezed as I continued to stroke him through his pants. His lips found mine again and started to kiss and suck gently on my bottom one. I let go of his cock and pushed his shirt off his body. He brought the tip of it against the edge of my panties and he started to slowly grind against my clitoris. I knew it was only a matter of time before I had him inside me. I peeled his undershirt off and started to unfasten his belt. Once it was undone, I pulled it from his pants and went for the button. I opened them with trembling fingers and started to massage his cock through his pants again. After a few strokes, his breathing intensified until I could feel his heart beating against mine. He pushed my hair off of my neck and kept kissing me as I pushed his pants to the floor.

  “I didn’t get to really feel it before… It’s so big…” I had to struggle to wrap my whole hand around it.

  “I bet you can’t wait to taste it again.” He flexed it in my hands a couple of times and I nodded.

  I pushed him back a little and slipped off the table, dropping to my knees. I pulled his underwear down until his cock was exposed and took it in my hand. I moved my hand up and down the length, feeling it get bigger and harder with each stroke. I brought my hand to the tip and opened my mouth, bringing my tongue and lightly touching the head. It was a lot different to be in control, without the ring in my mouth. His fingers moved through my hair and he sighed with pleasure. I put my mouth on the tip and stroked up and down, bringing his cock further and further into my mouth. It was the first cock to ever pass my lips, and they felt stretched as they tried to take him. It took a little bit of effort to open my mouth wide enough for him to easily slip inside, and once he was inside, the task of getting him into my throat seemed impossible without him forcing it.

  “This is so much better than taking you through the ring.” He let out a loud moan of pleasure.

  His hands continued to stroke my head and my scalp as my lips went up and down his shaft. I ran my fingers down to his balls and started to massage them as I sucked the massive cock, and he seemed to get even more excited from the dual stimulation. Once he was well lubricated, I could move my mouth up and down the cock with relative ease, but I still couldn’t get him all the way in. He pressed his hands to the back of my scalp and assisted, pushing his cock the rest of the way into my throat. Feeling him so deep without gagging gave me a huge sense of accomplishment. If it would have been possible to smile, I would have. I finally had him in the right spot, so I started to move up and down the length of his cock and I could feel his throb and his lips pursed into deep relaxed smile.

  “So much better…” He moaned again.

  The feeling of his cock going from the edge of my lips, all the way to the back of my throat was incredible. Each time I reached the bottom of his massive member, I felt my lips brush against his balls. I continued to massage and stroke them with my fingers while my mouth slithered up and down his cock. My saliva mixed with my lipstick, and the pre-cum forming on his tip creating a quick and easy slide. I felt him continue to tense and throb while his hands moved through my hair again. A few times, when I got near the end, he would grab my head and forcibly shove his cock the rest of the way. It was harder and faster than I could manage on my own and each time the head of his cock hit he back of my throat I felt him pulse and swell with the excited pleasure.

  I sucked him until I felt him pull his cock from my mouth. The sudden sensation of no longer having him in my throat left my mouth tingling. He reached under my arms and pulled me back up to the table. He pushed me over it and landed a few hard smacks on my bottom and I wiggled it at him. His finger drifted down to my pussy again and he stroked it through my panties as I felt myself getting wetter and wetter. He finally sank his fingers into my pussy and pushed my dress all the way up near my breasts. He dropped to the floor as my panties came down and pushed my legs apart. I leaned over to give him full access for what I hoped was about to happen. I felt his finger poke and pro
d around exterior of my labia and my clitoris.

  “I can’t wait to taste you.” I felt his breath on my pussy and I gasped.

  “Yes, please…” I begged. I was beyond ready.

  His fingers pushed apart the thick flap of skin protecting my most sensitive area and then his tongue lifted. The touch of his tongue was something so marvelous and perfect that I pushed against it, begging for more. He slowly licked around the exterior, then down to my clitoris. His tongue touched and rolled around it and I felt his getting hard and tight. He brought a finger into my pussy and slowly pushed it in while his tongue flicked my clitoris. I had lost my hymen with my own explorations, so the only barrier was my tightness. The sensation was so intense I had to grab the edge of the table and bend forward. My mouth opened and formed a perfect shocked O of pleasure as I leaned against the mahogany surface. He ran his tongue down the slit, then back to the clitoris as he pushed his finger in. His pace was slow and steady but his fingers were thick and meaty, so they sent waves of pleasure through me as he explored.

  “That feels really, really good.” I sighed and started to breathe heavy, long sighs.

  I could feel myself getting wetter as he pushed in and out, each time going deeper. His tongue stayed focused on my clitoris while he picked up the pace. He started furiously licking me with his tongue and picking up the pace and the intensity with his finger, which was pushing against my hymen. I had no idea oral sex could be so intense. It was so much better than the first time and it seemed the passion of knowing he was going to have my pussy soon made him more focused than when he rewarded me. I thought my whole body was going to go weak and fall onto his finger as he kept pushing and prodding.