Housesitter

To say the least, this has become an interesting summer. My name is Mike. I travel a lot for business. Usually I'm away just a few days at a time, sometimes for a week or more. In the past, I've hired lawn service and gardeners for the yard, pet-sitters for my dog and cat and whoever I could find to come in every few days to water the plants. Expensive, and the service was poor. This year I hired Melissa, a young college student from the neighborhood. Over the years I've watched her mature from a gangly kid into a beautifully poised young woman. My business is doing well, so I pay her well, at least as much as she'd earn from any other summer job in the area.

I guess her official title would be "housesitter," but she is really much, much more. Despite the difference in our ages, we have become enthusiastic sex partners. No, actually we've become more than that, we've become friends. We especially enjoy playing our "daddy games." Here's a little glimpse into our time spent together:

* * * * *

"Spread your ass-cheeks for me, Kitten," I said.

"Yes, Daddy," she said as she reached behind her with both hands and gently parted those smooth reddened globes, exposing her small, perfect, virgin anus.

I let my fingertips gently graze over her butt-crack from her open pussy to the base of her spine and then gently back. Each time my finger touched her brown, puckered opening I could see and feel her wrinkled aperture open and close slightly to my touch. I knew at that point that I needed to feel those tight muscles milking the swollen head of my cock.

"What should I do now, Daddy?" she said.

"Nothing, baby," I said. "Just let Daddy play with your sweet little butt-hole for a while and then Daddy will show you how to make my cock feel real good with that tight little ass of yours. Now get the bottle of massage oil, warm it up a little in the microwave and wait for me in the bedroom."

"Will it hurt, Daddy?" she asked as she looked over her shoulder on the way to the kitchen.

"We'll make sure it doesn't, baby," I said as I watched her worried look change back into the sweet smile I was accustomed to seeing.

I love to watch her walk around the house naked. She is naturally graceful as she moves and totally without a hint of self-consciousness. Quite different from when she first arrived. But I can always tell when she is aware of me watching her. Her movements remain ever graceful, but she seems to add a bit of flirtation to her walk, sometimes pausing to bend over affording me a fleeting view of her perfect ass and bald pussy, or at other times, pausing momentarily, turning sideways to offer me a silhouette view of her beautiful profile--slightly protruding butt and small perfect breasts with hard, erect nipples.

As I watched her walk from the kitchen to the bedroom, I had only one thing on my mind--her shapely ass and that brown, wrinkled butt-hole that I only minutes ago felt open and close to my gentle touch. Just imagining the feel and the sight of the head of my cock parting her crack and slowly pushing into that hot, tight canal was starting to get me very hard. I left the last of my clothes on the couch and followed her into the bedroom.

Missy was sitting on the bed when I walked in, rolling the warmed bottle of massage oil back and forth over her pointed red-brown nipples. "How do you want me, Daddy?" she asked.

"Get on all fours in the middle of the bed and spread your knees apart so I can feel your pussy. Now put your head on the pillow and get comfortable," I said as I knelt behind her and gently pushed her shoulders down with one hand while cupping the other against her smooth, shaved pussy.

"That's nice, Daddy," she cooed as I gently pressed my fingers against her puffy lips.

I then opened the bottle of sweet oil and poured a generous amount into my hands. The cheeks of her perfect young ass were still red from the spanking and in need of some soothing from my well-oiled hands. Missy moaned softly as I started the light massage of her reddened globes. The sight of her brown, puckered hole winking and peering at me as I spread her cheeks was definitely having its effect as my cock swelled and bobbed only inches from its target. I paused for a second to reach down with my oiled hands and give my cock a few slick strokes, reaching further back to gently touch my own butt-hole for a second and oiling my shaved balls in the process.

Returning to the easy massage of my little girl's ass-cheeks, I moved my face as close as possible to her wrinkled hole without actually touching it. I wanted her to be able to feel my breath on her asshole and pussy. Several times I let my warm breath bathe her and each time as I inhaled I was treated to the delightful musky scent of her pussy, ass and the sweet massage oil. It was intoxicating!

As I reached down to stroke my cock to full hardness I noticed that its slit was already oozing pre-cum so I moved forward and pressed the tip against her tight anus, lubricating her sphincter with the slippery juice.

"Oh!" she said when she felt the head of my cock pressing against her virgin hole. "I'm scared, Daddy! Maybe I'm not big enough back there. Please be slow and gentle."

"I will, Kitten," I assured her as I poured a stream of warm oil from the top of her ass crack, watching it flow down over my cock head, coating it and her smooth pussy lips below. After setting the bottle on the nightstand I moved up tightly behind her, adjusting my cock so that the sensitive underside could slide easily up and down between her slippery cheeks. I reached one hand under her belly to spread the dripping oil completely over her pussy lips and forward to her hardening clit. I love the way my fingers can move so gently over her clit when it is slippery with oil, tracing the outline of the shaft, lightly around the hood and back up the shaft to the point where it disappears.

Missy's breathing is getting heavier now as my fingers move over her wet slit and slippery clit and I can hear her whisper "Oh, Daddy. Yes! Yes! That's it. Mmmmm...., Don't stop. Unhh, Unhh!" between her ragged breaths. And I don't want to stop either. I would love for us to cum just like this, with Missy's pussy grinding against the palm of my hand and my cock sliding between her perfect ass-cheeks, the ridge pressing tightly against her sphincter as I shoot a pool of cum on the small of her back.

"No, wait, Baby. Daddy's cock is going to have your sweet ass tonight. Remember?" I said as I released my hold on her pussy and backed away from her butt.

"Yes, Daddy," she pouted. "But it was starting to feel really good!"

"This will feel good, too. You'll see," I whispered as I moved forward, guiding the head of my cock towards Missy's waiting virgin back door. I held my cock firmly against her puckered hole and with the other hand on Missy's hip guided her gently back. "You do it, baby," I said. "I won't push. I'll just hold steady. You push back and let your asshole open to the head of Daddy's cock."

"I don't know, Daddy," she whimpered. "It's just too big!"

"Relax, baby," I whispered as I lightly rubbed her back.

Missy pushed back and groaned slightly as I looked down to see the swollen head of my well-oiled cock disappear inside her dark, virgin hole. The pleasure from her tight grip was exquisite, but I had to keep up a steady pressure against her hole as I felt her muscles trying to push me out. Eventually she relaxed enough so that the head of my cock felt securely lodged in her tiny butt.

"Is it in, Daddy?" she asked?

"Yes, baby, Daddy's cockhead is in your sweet butt-hole," I reassured her as I softly touched her face and hair. "But now you have to relax your inner muscles so Daddy can slide in and out."

I kept a steady pressure against Missy's back door and looked down to see my cock slowly sliding in. I could feel her inner sphincter spasm around my cock as it disappeared inside. When I was about three quarters in Missy gasped, "Daddy, stop!" So I did.

I held steady as I felt Missy's inner muscles grip my cock and then begin to relax. If I moved only a fraction of an inch, her sphincter would grab me again and then relax, tighten, and then relax again. After a few minutes I felt a loosening around my cock and Missy said, "OK, daddy, give it to me now! Shove that big cock all the way up my ass! Now, daddy, now!"

I slid all the way, deep into Missy's dark tunnel. She grunted as I felt her clamp down on my cock one more time. The pressure felt exquisite! As Missy's muscles began to relax I started fucking her sweet tight asshole. Slowly at first and then longer strokes, deeper strokes until I was fucking her virgin ass in earnest, my balls slapping against her smooth, oiled pussy lips. The heat and tightness around my hard, swollen cock was incredible.

"Yes, daddy, fuck my ass! Give it to me! Shove that cock deep in my ass! Yes! Yes! All of it! Take your little slut-girls ass. It's so dirty! Yes! Oh, god, yes! Make it yours, daddy! Make my slutty little asshole yours, daddy!" she screamed as I reached my hand under her belly to play with her pussy.

What I felt was not her pussy, but her own fingers furiously flicking back and forth over her hard, slippery clit. So I just rested my hand gently over hers, enjoying her desperate attempt to bring herself to orgasm.

That was it for me! There was nothing more that I wanted than to fill Missy's tight asshole with a load of hot, thick cum when I felt it start. A pulsing deep in my body, somewhere between my own butthole and my heavy, swinging balls. As I felt the cum begin to race through the core of my veined shaft, I pulled out so that only the head of my throbbing cock remained inside Missy's tight, pulsing asshole, and I filled her smooth, hot tunnel with shot after shot of milky cum.

Missy was still feverishly working her fingers over her throbbing clit and soaking pussy when I pulled my cock slowly out. I watched her puckered hole open and close, and then open again, expelling part of the load of hot, sticky cum.

At that point Missy gasped, "Oh, daddy! Oh, god! I'm cumming now! So nice!" as she shoved her fingers in and out of her dripping cunt and I slammed my still hard cock back into her slick, cum lubricated tunnel.

We collapsed onto the bed gasping and I whispered in Missy's ear, "Did you like that, Kitten?"

Missy whispered back, "Can we do this again, daddy? Soon?"