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Ass-pirations: The Boss’ Daughter


I pulled up to the large Victorian house where my boss Fred lived. I had to drop off some paperwork he would need for a meeting the next day. Chrissy, Fred’s daughter answered the door. Her long blonde hair was pulled back and she was wearing a black knit dress that was very low cut, showing off her young pert breasts, and very short, barely covering her ass.

I had known Chrissy since she was 10 years old. I had been about 20 years old when I’d started working with her father. Chrissie had always been pretty and had a lot of potential, but my thoughts never went further than that. I hadn’t seen her in several years and she was definitely not a little girl anymore. I could feel a stirring in my pants.

With a devilish sparkle in her blue eyes, she invited me into the house and led me to the living room. “My parents are at a concert but should be home soon if you want to wait,” she explained. Who was I to say no to spending time with a pretty young thing?

“Yeah, sure,” I replied trying to sound nonchalant.

“Can I get you a beer?”

“That’d be great.” While she was in the kitchen, I moved around the room, trying to distract myself from the hard-on I was getting.

I was sitting in her father’s favorite chair when Chrissy handed me the beer, leaning forward so that her dress fell away from her slim body and I could see that she was wearing nothing underneath the dress. I think I whimpered aloud. She giggled.

“Do you like what you see?” I was unable to speak so I just nodded my head. I wasn’t even sure she was legal, but my head started getting fuzzy as the blood rushed to my groin. “It’s okay,” she whispered. “I’m 18. You can undress me if you want.”

I set the beer on the table next to me then reached up and slid the dress over her head. I groaned as her body was unveiled. I dropped the dress on the floor then took her small nipple between my dry lips. I sucked gently on it, running the tip of my tongue over it.

She moaned softly, and I felt her hand reaching between us to play with herself. I glanced down just in time to see her hand disappear between her legs and into the soft down covering her pussy.

I pulled back and she pouted at me. “Don’t you want to touch me?”

“Oh god. Yes!”

“Do you want to do more?” I looked into her eyes. The thought of actually fucking her hadn’t crossed my mind. My cock was rock hard and started to ooze when she suggested that I could do more than just touch her.

“More than anything else,” I answered.

“I’d like that, too.” I didn’t need to be told twice. I stood up, scooped her into my arms and carried her upstairs.

“My room is on the left after the bathroom,” she directed.

I laid her naked body down on the baby-pink, lacy bedspread then trailed my finger along her breasts and down over her stomach, stopping just above her pussy. “You’re so sexy,” I murmured then quickly undressed. I laid next to her on the small, twin-sized bed, caressing her soft, young body. My pale office-worker skin contrasted with her youthful tanned skin.

I kissed her softly, my hand playing with her breasts again, moving back and forth between them. I lightly caressed and tugged on the nipples, loving the sound of her moan as she responded to my touch.

“Can I touch your cock?” she asked. Her voice was soft and vulnerable. I nearly came at the thought of her hand touching me. I wordlessly guided her hand to my cock and closed my eyes, thinking about anything but what she was doing to keep myself from coming before I had a chance to fill her.

Her fingers slid up and down the shaft as she lightly gripped it—like a pro. If it wasn’t for her age, I would have thought she had been playing with cocks for many years. She moved her hand faster and I had to bite my lip to keep from coming. “If you do that much more, I won’t be able to fill you,” I warned. She grinned at me.

“So it feels good?”

“Too good, I nearly came on your hand.”

“We don’t want that!” She giggled and pulled her hand away. She rolled over and looked into my eyes. “I’m not on birth control. Do you have a condom?”

My cheeks flushed. “I haven’t carried a condom in years,” I replied.

“Oh.” She frowned. “What can we do? I … I want to feel you inside me.”

My cock limped in disappointment. There was no way I was going to fuck her without protection, I wasn’t interested in becoming her baby daddy or losing my girlfriend.

“Could you fuck my ass?” she asked suddenly. My cock perked up at the thought of using her back door. That would be more than acceptable.

“Are you sure? It could hurt,” I warned. I hadn’t had my cock in an ass in more than two years and I had missed it. She nodded her head slowly, like she wasn’t completely sure. “You don’t have to do it.”

“I want to,” she said. “Please?”

How could I say no to that? “Get on your hands and knees,” I directed. I was happy that my cock had been oozing precum. I moved behind her and spit on her ass hole a few times to lube it up then pressed my index finger slowly into the hole. I could hear her hold her breath as it moved into her then a soft moan as my finger gently moved back and forth. “Is that okay?”

“Yes, it feels weird but good.”

“Are you ready for my cock?”

“Yes!” I pulled the finger out and spread the precum down over my shaft then spit on the hole again. I pressed the tip of my cock against the entrance and very slowly pushed it in. She gasped a few times but was a trooper as I filled her.
Her ass felt so amazing, even with only three inches of my cock inside her. I thrusted in and out of her carefully, not wanting to hurt her or to end things quickly. As her muscles loosened, I pushed more of my cock into her and moved faster. It wasn’t long before I had all eight inches buried inside her.

I reached around her hip and found her clit, rubbing the nub as I fucked her harder and faster. “Oh god,” she whimpered. I could feel her orgasm approaching and braced myself. When her muscles started tightening around my cock, I couldn’t stop it and I filled her ass with what felt like a pint of cum.

I fell against her back and rested there, trying to catch my breath then pulled out of her carefully.

“Are you okay?” I asked. She nodded her head and smiled.

“It was better than Susie described it.”

I tried to hide the surprise on my face but failed miserably. I couldn’t believe that she and her friends talked about anal sex. “I’m glad I could help answer your question,” I replied.

She looked at the clock. “Oh shit, my parents will be home any minute.”

I jumped out of bed and picked up my clothes. I closed the bathroom door and quickly washed my cock then got dressed. Chrissie was standing outside the door when I finished. She was in the dress again.

She led me back downstairs and I remember the paperwork I’d brought over. “Can you make sure your dad gets the stuff I left in the living room?” I knew I wasn’t going to be able to look my boss in the eye after having just fucked his daughter in the ass.

“Sure, it is the least I could do to thank you for popping my anal cherry,” she replied. “And, don’t worry, I won’t ever tell Daddy about it. Pinky swear.”

“Thanks, I appreciate it.” I said. “Have a good night.”

I emailed my resignation when I got home. I never heard from Chrissie or her father again but there was no regret. Taking Chrissie’s anal cherry was definitely worth having to find a new job.

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