Babysitters Grow Up

I am an early thirties single dad, divorced after just 4 years of marriage. I don't trust my son with just anyone so I use the same babysitter from when my wife and I were married. She still babysits for me even though she is in college. She says she loves my son and would not trust him with anyone else either. She is very protective of him.

Allie, the 19 year old babysitter, is a very cute, curly haired brunette with a very nice body. She is 5'5" and weighs 123 pounds. She has a nice hour glass shape, elegant shoulders, and small breasts, wearing a B cup to cover them up. She has a wide smile with perfect teeth, thanks to the braces she was in for 14 months, bright green eyes, and a nice sloped nose. She stands straight as a board and her ass sticks out like it wants to be noticed. She plays tennis and is on the track team at the junior college she attends and whatever she has in small breasts are more than made up for in her legs and ass shape.

Friday night, I had a date so I called Allie earlier in the week to set everything up. She agreed but came over a little earlier than I was expecting. As a matter of fact, I was still in the shower. She had let herself in the back since she knows where the hidden keys are at and was sitting on the corner of my bed waiting for me.

I had just finished drying my hair, put on some cologne, and walked into the bedroom naked.

"What are you doing here already?" I asked as I ran back into the bathroom.

"I was bored," she laughed.

"How about a head's up next time," I said as I shook my head. I was flush and turning red. I had known this girl since she was 14 or so and now she had seen me in the flesh!

She said sarcastically, "I've seen a naked man before, don't worry."

I suddenly realized her voice was that of a woman. It sounded like a confident, mature woman now. It was deeper, the words were much less awkward, and the tone was matter of fact. It was actually somewhat comforting, but I was still embarrassed!

I wrapped a towel around my waist and walked into the bedroom to get my clothes. She stared at me the whole time with her legs crossed above the knees and a semi short black clothe skirt showing me a lot of leg that I tried not to look at. I did not see the line of her panties anywhere but I did not gawk like I really wanted to.

She said, "I'm going to go check on little man," and walked out as I continued to get dressed.

In a few minutes, I exited the bedroom and found her playing with him and his trains on the floor in the living room. She was sitting Indian style on the floor and I shamefully tried to sneak a peek under her dress but it was not quite that short.

"I'll be home around 10 or so. You have my number just in case," I said.

"No worries. Everything will be fine," she said back. "Take your time; I don't have a curfew anymore."

The date was not what I expected. The girl I asked out from work really did nothing for me. She wanted to talk about everyone at work that gets on her nerves for whatever reason, and was real pushy about marriage. At one point she asked me when I was thinking about getting married again. I have no intention of that any time soon and I made that clear. I kissed her when I dropped her off and felt nothing. I then headed home kind of bummed. It had been a few months since I had gone out with anyone. I enjoyed being single in some ways, and in other ways, I really wanted some affection.

The closer I got to the house, the more I thought about those legs sitting on my bed and wish I could have seen whether or not Allie was wearing panties. Then my mind wandered off, "Does she shave or wax? Does she suck? Does she do anal?" I was getting worked up at this point. I had to settle down before I got home and walked through the door with a big bulge in my pants.

I ended up pulling in the drive at 9:30. My boy was already in bed, probably 2 hours ago. I opened the door and Allie was sitting on the couch watching a movie.

"Hey sweetheart, I'm back."

"How did it go?"

"Well, I won't be going out with her again," I replied. "She just wasn't my type."

"Too bad," she said and stuck her bottom lip out while she made a pouty face. It was so sexy the way she did it looking over her shoulder at me while she stayed planted on the couch. "You know," she continued, "there's always tomorrow." She winked at me and smiled seductively.

I got a strange feeling she was hinting at something. Maybe she wants a date. What would my ex think about that? I'd get the third degree for sure then. Besides, I need to quit fantasizing about the babysitter anyway. She's way too young and I have a great relationship with her as is.

As we talked, the subject of my ex came up. I was a little uneasy talking to Allie about it since she knew us when things were going good just two years ago.

All of a sudden, Allie said, "You deserve better."

I replied, "It's more complicated than that. You wouldn't understand."

Allie then said, "I understand she hurt you bad and I heard you cry behind your bedroom door. Do you know how bad I wanted to come in there and hold you?"

I did not know she heard me. I tried to keep it quiet.

I then said, "It wasn't all her fault, you know. Things happen."

Allie replied, "Why do you always take up for her? She messed around on you because of convenience, and you are okay with that?"

Allie had an affair when she went on business trips with a guy from work. I kind of understand. It was a stressful year, but Allie is right. I do feel it was circumstance. However, I never cheated.

After some more talk, she decided it was time to go. I walked her to her car and she still acted as if she either wanted to tell me something or she wanted me to say something to her. I was puzzled at the games but it was some exciting flirting at the same time and the adult conversation we had shared. Before she got in the car, she bent over into it to put her purse on the passenger seat and I got the shot I had been hoping for. She was wearing no panties and I thought I could tell she was shaved. It was a very brief peak, but enough to make me very excited. I couldn't wait to get inside and think about that shot as I pleased my own body. I kind of thought the show of flesh might have been deliberate at that point.

I checked on my son and placed his favorite dinosaur in his arms as I gave him a kiss on his forehead.

I Went to my room and pulled my cock out of my boxer briefs and had just started to stroke a bit when I got a text message on my phone from Allie. It read, "go check ur pillow."

I was already laying in my bad so I grabbed my pillow. It was damp. I had no idea what had happened.

The next text read, "r u awake?"

I responded, "yes."

She text back, "smell the pillow."

I stuck my nose close to the pillow and it smelled like pussy! What had she done? Did she have some guy over and they screwed in my bed? I was not happy at all.

Then she text, "my pussy juice 4 u."

I text back, "Wtf?"

She text back to me, "I watched one of ur pornos and fucked myself with ur pillow. i wanted it 2 b u."

I sat there and didn't know what to do. I text back, "that's hot." I didn't know what else to say.

The next text I got had a video attached. "Watch this and see what you missed out on," the text read.

I started playing the video and it was Allie, in my bedroom. She had her phone sitting on my night stand videoing the scene. She was rubbing her legs and knees up and down. She eventually started rubbing under her skirt, then pulled it up to reveal her shaved pussy. After some rubbing, she took her skirt off and moved her pussy closer to the camera for a moment or two. She was facing the phone cam with her pussy in plain view while she kept looking at the TV to her left. She kept looking at the TV, then the camera, then closing her eyes. Her hands were working her shaved pussy, rubbing up and down with a finger disappearing every few strokes, digging into her sweetness. My pillow was between her legs as she continued to rub herself into ecstasy.

She was licking her lips and brought her hand up from her pussy to taste her own juices. She leaned down into the camera view and whispered, "mmm, it tastes so good. You want to taste it, too, don't you? You wanna fuck me, don't you?"

She stuck her hand in front of the camera for a moment and I could see how wet her hand was. Her hand then returned to her mound. She was riding my pillow and rubbing her pussy with her right hand and her belly with her left. Her left hand then disappeared up into her blouse as she rubbed her breasts. She threw her body back in a spasm and ground her pussy into the pillow even harder.

I was rock hard by this point, watching her, while I am sitting in the very spot she had just cum a couple of hours ago. I began stroking my cock again as my eyes stayed fixed on that little screen of my phone. I was lost in a lustful buzz as all of my attention was on this beautiful woman pleasing herself.

Her back began to arch and both hands now worked her pussy. One hand rubbed her clit and the other fucked her at a quick pace. I could hear the smacking of her juices as she punished her lovely sweetness. I knew she was cumming and I wanted to cum, too, but was not yet there. I watched her orgasm until the end and at the end she whispered something else before reaching for the phone and turning it off. I replayed it with the phone to my ear and fast forwarded to the end to hear it better and she had said, "This could be with you any time."

I text her back, "right now?"

About two minutes went by and no reply. Had I missed the opportunity to fuck this little college girl?

Then a text came back through, "I am on my way over."

I quickly took a shower to wash my lower body and put on a t-shirt. I tried to let my penis relax as much as I could, and then waited for her arrival.

When Allie arrived, I was waiting at the door. I opened it and turned off the outside light as she entered the house. Without so much as a word, she grabbed my face with both hands and began to kiss me passionately. I was half hard while waiting for her arrival but that kiss sent my cock into full attention. She continued to kiss me as I rubbed her back and shoulders.

I picked her up by her waist and carried her to the bedroom. We began kissing again, this time with our hands free. I began pulling her blouse up and over her head. I then unfastened her bra and let her breasts free. Her nipples were dark brown and nickel size, but were hard in the middle from all of the stimulation.

Allie whispered in my ear in a sex crazed voice, "I want to taste your cum."

She got down on her knees and pulled me sweatpants down. My cock sprang right into her face and without even taking my pants off of my legs, engulfed me into her mouth. I grabbed her hair and massaged her scalp as she sucked my cock. Her pace was fast but not so fast that I couldn't feel each stroke. Her tongue pressed hard against the bottom of my shaft and she rammed my cock into her mouth. I knew my release was near now.

She continued to suck in even steady strokes and within a minute or two, I could not hold back any more. I announced to her in case she wanted to withdraw before I shot my cum into her mouth, "I'm going to cum!"

She increased her pace just a bit and I felt my cock reach its full size as I started my release into her throat and onto her tongue. I could feel the slippery cum in her mouth as it continued to ejaculate from me. After I shot enough, she paused just a moment to swallow, and then continued.

When I finished, I noticed my legs were shaking. I was light headed and Allie asked, "Do you need to sit down?"

I said, "I think so. Wow that was awesome!"

I sat down on the bed and Allie took my pants the rest of the way off and then my shirt. She then took her skirt off and sat in my lap facing me, both of us completely naked now. Her hot pussy was right against my cock as it continued to throb a bit from the orgasm I had just had.

I took one of her breasts into my mouth and began to suck the nipple. I then licked underneath of it and kissed her all over her chest and shoulders. I pushed her hair back on her left and kissed her neck and earlobe. I couldn't wait until I was hard again. I wanted inside of her pussy this time.

I laid back on the bed and said, "Sit on my face."

She said, "Call me a slut!"

I said, "I said sit on my face, you fucking slut, now!"

She moved her mound up to my face. She leaned over my head so I could access her clit and folds. My first lick started at the bottom of her folds and worked its way in between them. I pierced her pussy as deep as I could with my tongue. She had a musky smell, probably from all of the masturbation earlier. I dug deep into her pussy with my tongue and she moaned.

I pulled my tongue out and said, "you like that, you slut?"

She said, "Yes, fuck my slutty pussy with your tongue. Fuck it good!"

I dug deep into her again. I moved to her clit and began to suck her mound while my tongue rubbed her clit. Her pussy was so wet it was nearly pouring its excitement into my mouth at this point.

I continued to suck and wrestle her clit with my tongue until she began grinding her pussy into my face. She grabbed my head like she had grabbed that pillow earlier. She was pulling my hair and rubbing her mound all over my face as I fought to stay glued to her clit.

I felt juice run over my cheeks as she came all over my face. When she settled down a bit I said, "I'm going to fuck you like the slut you are!"

She got up and started to lay in front of me with her legs open. I said, "No, like this."

I repositioned her facing the headboard with her hands on it. I got behind her and put my shiny bell at her entrance. I pushed slightly and opened her folds up enough to see my bell disappear. She took a deep breath and arched her head back a bit.

Then with one smooth stroke, I buried my shaft all the way into her. She let out a muffled scream, knowing my son was down the hallway asleep. I pulled out slowly where only the bell was in her, and then rammed her again.

She demanded, "Fuck my pussy like it's the last one you'll ever have. I am a woman now so fuck me like one!"

I started with a slow, deep pace giving her all of my 7 inches each time. I had my hands on her ass as I slid in and out of her. Her pussy felt so hot and so good as it took me on.

I leaned over her back and grabbed her hands, holding them captive as I shoved everything I could into her pussy. Her body began to tense up again as she said, "I'm going to cum! Oh my God!"

Her breathes became deeper and her pussy released more juices as she tightened onto my shaft. I could feel it pulsing and releasing.

I released her hands and put my hands back on her ass. Then I took my right hand and reached down to get some lube on it from her juices. I get the middle finger pretty well lubed and started massaging her anus. I rubbed the outer areas of it and then reached down to get more juices. This time, I rubbed a little, and then stuck a finger into her ass. Her body language responded with pleasure. I pulled my finger out and soaked it in a little more lube and sank it into her up to the second knuckle, then the third.

I continued to fuck her as I worked the finger in and out of her ass. Her ass was so tight I really wanted to test my luck and try to fuck her there, but for now, I was too close to coming again to worry about trying that. I didn't want to break the good rhythm we had going either. I could feel her getting close again.

My head started to get light again and I felt myself ready to cum. As my cock grew, Allie began to cum again, too. Her back arched and she said, "Harder! Fuck me harder!"

I pulled my finger out of her ass and grabbed onto her hips. I rammed my cock into her so hard I nearly picked her up off the bed. I was cumming myself so hard it almost hurt. Her pussy tightened up and my shaft grew inside of her. It was so tight.

"Fuck!" I said as I clenched my teeth.

I released everything I had inside of her as her pussy released back and when she finished, she collapsed onto the bed as I collapsed on top of her with my cock still in her tight pussy.

We laid there panting in a pool of sweat and cum. She said in a worn out and relaxed voice, "See, I am a woman every bit as much as any other."

I replied, "Yes, and you are a beautiful woman as well. I consider myself the luckiest man on earth tonight."

"Thanks, "she said, "but the pleasure is just as much mine."

We actually fell asleep for a half hour or so until I woke up and rolled off of her. I woke her and asked if she wanted to go home but she said no and went back to sleep. I went back to sleep as well.