The Babysitter

I didn't want to break it to her, but that was about as hard as I could possibly fuck anyone. My dick was still hard, of course, but once I had shot my load into the condom, it wouldn't be getting any harder. When she was finally done, she climbed off me, and quickly removed the condom from my semi-hard dick. I wasn't sure what she was going to do, and I nearly broke out laughing when she held it up and squeezed the contents out into her mouth and swallowed it.

"Told you I would give you a blowjob," she said, laughing. Then she leaned over and cleaned the last drops of semen from my dick with her tongue. Even though I had just finished coming, the feeling of her warm lips wrapped around my cock created a little twitch.

Claire giggled again and started teasing my dick with her fingers. "If you can get it up again that fast, then I can get it back down."

"I don't think I can," I replied. "Even when I was young and dinosaurs roamed the earth, I needed longer than that to recover."

Claire seemed to be thinking about timing. "Let's go back to your place anyway. It is early, and I need to do a science experiment."

She seemed to have forgotten that her car was already at my place, but I was not about to argue with an offer like that. The sex had been amazing, and if given an hour or so, I thought I might be able to recover.

On the way back to my house, she resumed talking, and in fact, talked about sex almost non-stop.

"Wes can come six or seven times a day. It is fine with me because I dig lots of sex, but sometimes I wish I could just kiss him without him pulling his dick out."

"I bet that makes for an awkward trip to Starbucks." I laughed.

"If you only knew," she smiled. "I gave him a blowjob once in the library in between classes."

"I used to actually dig stuff like that," I replied. "My old girlfriend once gave me a blowjob at the lake, just standing out behind my truck."

We compared sex stories on the way back to my house, and sure enough, by the time we got to my house, I had a pretty good erection again. It helped that Claire had hiked up her dress and was fingering herself as she told me about all the guys she had fucked.

Unless I was counting wrong, or she was lying, she was up to about ten different guys. It could be that she was fucking other guys for money, but if it was, she didn't say so. In fact, she enjoyed talking about it so much, that it seemed like she might be making up stories just to get off. Even though my experience was somewhat limited, I didn't think that girls who are hookers would enjoy sex that much. And Claire obviously enjoyed the hell out of it.

My total number was higher than the number of her stories, but only because my wife used to recruit women for the two of us to share. When I started telling Claire stories of one of the threesomes, Claire told me to take the long way home, and actually had another orgasm in the car just from masturbating herself.

When we got back to my place, as soon as she got inside the door Claire practically ripped my clothes off, and got down on her knees to take my dick in her mouth. She sucked me for just a few minutes while she fingered herself, but I could tell she wanted more.

I didn't want to break the rules, so I let her take the lead, and didn't touch her. I waited for her to instruct me, and it didn't take long. When she finally stood up, I could tell that she was frustrated, and I knew what she was about to do. When she turned and bent over the couch, I immediately grabbed her hips, and plunged my dick into her tight pussy as far as it would go.

My dick is about eight inches long (if you measure it just right), and I sometimes feel it "hit bottom" when I fuck a girl this tiny, but I didn't feel that with Claire at all. So maybe she was telling the truth and she had been with more than a handful of guys. She didn't seem bothered by how rough I was being, and even asked for it "harder."

By that time, I was fucking her as hard and fast as a jackhammer, and she was matching my pace, pushing back against me with each stroke.

"Did you bring the condoms in?" she whispered, almost gasping. "I don't want to get pregnant."

I was actually settling into a pretty good pace, and felt like I could keep it up for a while. So even though I could promise not to come inside her, I went ahead and told her that I had gotten a vasectomy many years earlier.

This seemed like it really excited her, but all she said was "Oh, Oh, Oh..." She continued bucking against me, and when she finally started coming, she started moving her ass up and down to increase the friction even more. Her orgasm seemed to get stronger and stronger, until finally her legs started to get weak. When she slowed, I held her hips up to my dick, and continued pounding her. She was so small that I could hold her up easily, and I was basically moving her up and down on my shaft at will.

The feel of having complete control over her was amazing, and the view of her ass was enough to send me over the edge.

"I am about to come." I warned her.

I assumed she would move away, but she didn't. "Do it," she moaned. "I want to feel you cum inside me."

When I finally started pumping deep inside her, I paused my motion for a moment so she could feel my dick jerking. When I did, she had another orgasm, and nearly collapsed. If I had not still been holding her up by the hips, she would have crumpled.

As my dick pumped its load deep inside her, she confessed with a smile: "This is my first time without a condom, it feels fantastic."

After she finally pulled away, I thought she might snuggle on the sofa for a bit, but she didn't. Instead, she headed upstairs, dumped her remaining clothes on the floor, and jumped into my shower. I figured the rules were pretty much shot to hell at that point, so I joined her in the shower.

While we showered, she talked casually about how great the sex was, and I stood behind her, and felt up her tits while I soaped her whole body. Her tits were smaller than average, but had a good shape, and were young and firm. I even reached my hands down while soaping her up and rubbed her pussy for a minute or two. She leaned back against me and put her hands over mine. "Thanks," she said. "I had a great night."

When she got out, I finished my shower, and was surprised how quickly she was dried and dressed. With her complexion, she didn't need any makeup, and there was none left in the house anyway. By the time I was out of the shower and getting dressed, she was getting ready to head out the door.

"I left some babysitting money on the counter." I said. I had taken out $200, because I didn't want to seem cheap, and she actually tried to give me $100 back again.

"No, I meant to do that," I assured her. The dates and the money had actually messed up my budget that week, but I had made up my mind that it was totally worth it. I was pretty sure it wouldn't last, and I wanted her to look at me like a great guy, instead of someone who would try to save money on a full-service escort.

She seemed genuinely happy at the big "tip", and she came over and stood on her toes to give me a quick kiss.

"OK, then, the next one might be on the house."

She had driven her car, even though I lived only a block away from her house, so I just walked her to the car and thanked her for the babysitting.

She smiled and looked up at me in the darkness, standing slightly closer than a babysitter would. "My pleasure," she replied.

In fact, she did come over a few times at random just to fuck, so maybe the investment paid off. Susan maybe sensed that I was getting some action, because she stopped offering to give me blowjobs during our occasional visits. She didn't ask me though, and so the rest of our relationship continued as if things were completely normal.

Claire continued to "babysit" for me for free several times that Summer and Fall, but I had told her that I didn't want to interfere with her life. If I called her for babysitting, it was always just babysitting, and anything that she did over and above that was up to her.

By the time Winter rolled around, I assumed she had either grown tired of the business, or met a new boyfriend or something, but she had mostly stopped returning my text messages. She hardly had time to even babysit, but I had promised that there would be no emotions, and I kept to my promise.

Claire seemed to know whenever Susan came by, and I was slightly worried that they might be talking. By winter, Susan had resumed giving me blowjobs whenever she came over, and even had anal sex one time "just for fun."

One night near Christmas, Claire came over late at night, snuck into bed with me.

Johnny was asleep, and I was not even sure how Claire had gotten in, but near midnight, I saw her familiar thin form taking her clothes off in the darkness of my bedroom.

"Hey," I said, trying to sound casual.

"Hey," she replied, as she climbed into bed with me and snuggled close.

I tried to think of something else to say, but it was clearly going to wait. Without saying another word, Claire had pulled my boxer shorts down, climbed on top of me face-to-face, straddled my hips, and started grinding her pussy lightly on my dick.

As soon as I became hard, she inserted my dick using her hands, and made love to me slowly and tenderly. She might have had a small orgasm, or she might have been faking it, but she pushed herself down hard but slowly on my dick until she felt it pumping deep inside her.

While I came, I left my hands wonder over her small body. Her shoulders were thin and strong, and I could feel the outline of her breasts pressed against my chest. My dick gradually got soft inside her, but it didn't fall out. She was clearly not sleeping, and neither was I, but she seemed to be working up the courage to say something.

I could tell something was bothering her, so I just held her for a long time, and waited for her to speak. She giggled slightly when my dick fell from her pussy. I had pumped a huge load inside her, and neither of us had made any move to clean it up in any way. I could feel my semen running down my leg, but it didn't matter. I could tell it was not the right time to start worrying about cleaning up.

When she was ready, she told me "This might be our last time."

"Is something wrong?" I asked.

"Not really," she said. "I just wanted a sugar-daddy type relationship, but I am having real feelings for you and another guy at the same time."

"I understand," I said.

"I am not sure you do," she said. "You would be my first choice by a mile, but we are really at very different points in our lives. I haven't even been giving Brad a fair shot because there is always you in the back of my mind."

I wanted to continue the conversation, and I told her so. "Listen, there is no one else in my life right now. And I have thought many times how great it would be if you wanted a real relationship."

She seemed a little sad, but she was firm. "No, I made up my mind a long time ago. You are going to go back to dating women that want to be a mom, and I am going to grad school." Then she laughed and continued: "... and start fucking students instead of professors."

She laughed a little, but it was more of a forced laugh than her usual.

And that was it. I tried to get her to continue the conversation, but she was already up and getting dressed. She left just as quietly as she had come in, and left a spare key on the dresser that I had forgotten she even had.

After that, I literally never saw her again. But I still remember her as the best babysitter ever.