The Babysitter

The tension at dinner the previous night was palpable with both boys looking at me, still in my sexy pajamas. It wasn’t uncomfortable, but more like a thick, sexual tension. After dinner, I had gone upstairs, closed and locked the door and masturbated like there was no tomorrow. I must have given myself six or seven orgasms with my face buried in a pillow and my fingers buried in my pussy. I hadn’t been that horny in a long time. After I finished, I was exhausted and basically passed out.

I woke up Saturday morning and cracked an eye. Sunlight was streaming in through the partially open drapes, motes of dust hanging in the air. I had no idea what today was going to hold, but I was sure it would be interesting. My shorts from yesterday had dried from the big wet spot and I put those on without panties and pulled my shirt on. I realized I forgot to bring a bra and I didn’t even have a substitute. I looked through Sarah’s drawers and found her bras. She was probably a cup smaller than I was and it was a bit tight so I went sans bra. I decided that I definitely needed to go home and get some more clothes before tonight.

I came downstairs and called out, “Good morning, guys.” After yesterday, I couldn’t think of them as boys anymore.

They both responded, “Good morning, Jennifer.”

“What are you planning on doing today?”

John spoke up first, “I’m heading over to a buddy’s house to do some gaming today. There are some COD matches that we want to play.”

“Alright, have fun with that. Will you be home for dinner?”

“I don’t know, but I’ll give you a call. I’m going to take mom’s car. Is that okay with you Steven?”

“Yeah, I don’t have anything going on today at all, so I’ll be here.”

“No girlfriend or friends to go out and do things with?”

“Not really, but because this week is a holiday week, most of my friends are gone. Parents would have taken us, but we only have a week and they wanted to take two weeks off.”

“Oh, right. I forgot. School and Spring Break. No such thing in the working world unfortunately. Alright, well, I’ll be around if you need anything. I was just going to relax around the house and read or something. Maybe you can help me grab some things from my house that I realized I didn’t have for the rest of the week?”

“Sure, just let me know.”

John picked up the car keys and turned to leave. “Bye, see you tonight.”

“Okay, if you want to stay out tonight, give me a call, I need to know where you’re going to be.”

“Aren’t you being a little overprotective,” John said.

“Hell no. Your parents trust me to look out for you and I adore your parents so I’m going to do everything I can to make sure you’re safe.”

“Okay. Bye.” And he walked out the door.

“Steven, it’s just you and I today. Is there anything special you want to do?” I looked at him suggestively, more to see what he would do. John’s confidence was a little unsettling, but Steven’s innocence was a straight turn on. When he didn’t respond I turned back to him.

“Steven, are you okay? What’s wrong?”

“Um, was what happened yesterday a one-time thing?”

“Did you want it to be a one-time thing?”

“No. I, uh, that was really hot, and you’re really beautiful.”

“Then it won’t be a one-time thing.” I leaned in and kissed him on the lips. Then it dawned on me. “You haven’t been with a woman before?”

“Uh-uh.”

“Was that your first blowjob?” He nodded, too embarrassed to speak.

“Steven, it’s nothing to be embarrassed about. There has to be a first time for everything. But you’re a young, good-looking man, you haven’t had any girlfriends?”

“I’m a little awkward when it comes to talking to girls. They want someone who knows what they’re doing and who’s confident. Like John. He’s confident. He’s always got a girlfriend. He’s probably had sex before and I can’t even get a date.” He looked like he might start shedding tears. I went up to him and put my arms around him and hugged him.

“Steven, it’s okay. It will happen at some point, and you’ll find the right woman for you.” I felt him start to harden against my hip. “And you have a great gift to give any woman,” as I pressed against his cock. I hugged him one more time and then stepped away. “How about we have some breakfast and then you can help me get some things from the house to bring back over here.

“Yeah, sure,” he said with a not quite cheery demeanor. Well, I would change that soon enough.

I made us some quick omelets and served us some orange juice and we ate in uncomfortable silence. When we finished I said, “Steven, could you clean up the kitchen while I grab some things from upstairs and then we’ll head over?”

“Sure.”

I headed upstairs, grabbed my pajamas and bikini, and headed back downstairs. “Okay, let’s go!”

We walked down the street; the only sound was our footsteps on the asphalt. Steven didn’t look up or look at me, he walked with his head down, looking at each step and nothing else. There was a slight rustle of leaves as the wind blew and the only thing I could think of was, what am I going to do to cheer him up? Well, that was easy, and I didn’t even need much of a plan. We reached my house and I unlocked the door and we went in.

“Come on up to the bedroom. I need to get clothes for the week.” Steven followed me upstairs and we went into my bedroom. “The closets in here, come on in and I’ll hand you some clothes. You can just put them on the bed and then we’ll get a bag.”

First, I grabbed a handful of panties and bras. Nothing sexy, just normal, everyday underwear. Next, I grabbed some dresses for work, a couple of sweatpants to wear when I got home along with some t-shirts. Finally, some socks and a couple of pairs of shorts. Then I reached in to get some of my sexy underwear. The first item I pulled out was a blue teddy that left absolutely nothing to the imagination. I handed it to Steven whose jaw literally dropped open. “Do you like it?”

When no reply was forthcoming, I poked him in the ribs. “Do. You. Like. It?”

“What, yeah, of course, wait, what did you ask?”

“What are you thinking about right now Steven? Don’t be shy with me, tell me.”

He looked me in the eye and said, “You, in this outfit.”

“Good. How about this one?” I handed him a see-through nightgown. He licked his lips. His cock was clearly outlined through his khaki shorts going down the right leg of his shorts. “I can see how much you like it. How about we just take care of this right now.” I reached my hand out and placed it on his cock and gently squeezed. He snapped out of it.

“Jennifer, I don’t know what to do.”

“I’ll show you.” I leaned in and kissed him on the lips and felt his cock twitch under my hand. His lips responded to mine and he pulled my head closer to his, mashing my lips against his. His other hand dropped my nightgown and latched onto my right breast and started squeezing. “Gently, gently, Steven.” I went back to kissing him. “How about we get out of the closet and into the bedroom?”

He reluctantly let go of me and followed me out of the closet and into the bedroom. “Undress me.” He moved in quickly and gripped my t-shirt to pull it over my head. “Stop. Not that way. You always want to be gentle, and you will get me undressed, I promise. But slowly, sensually. Turn me around, gently but very handsy.” He put his hands on my hips and stomach and slowly turned me around, moving close up behind me. “That’s it. Run your hands up my body and slowly move my shirt up. Touch me, play with me. Run your hands from my thighs up my stomach and then touch my tits.” He followed instructions well and I could feel his hands sliding up my hips, then to my waist and my stomach. He pulled me back into him a bit and I could feel his cock nestled between my ass cheeks. His hands went higher, sliding under my shirt and up my stomach. His lips came down and kissed the back of my neck. He continued up my stomach and cupped my tits, and then he ran his palms over my nipples, and I moaned and lifted my arm to put behind his neck. He kneaded my tits under my shirt more and then slid my shirt up and over my shoulders. “Well done, Steven. Kiss my neck, shoulders, ears but don’t stop touching me. Touch is what turns a woman on, not necessarily pawing her tits or her pussy. In fact, take your shirt off so I can feel your chest against my back.” He kissed me, and he was so sweet and gentle about it. After about ten minutes his hesitancy evaporated, and he became more confident. He spun me around slowly and kissed me full on the lips, his tongue parting my lips and I moaned into his mouth. He pulled me closer and my pussy pressed right up against his cock. I started sliding my pussy up and down his long cock and started moaning harder in his mouth.

I pulled away from him and took a deep breath. “How about we try something different? I’m going to show you how to please a woman. Always remember that a satisfied woman is going to make you a very satisfied man. Pull my shorts down, again, slowly and with a lot of touch.” He unbuttoned my shorts and slid his hands in the top along my hips and slid his hands down, taking my shorts with him until they dropped to the floor. “Run your hands back up my thighs, with one hand between my legs. Gently, gently,” as his hands slid closer to my steaming pussy. “That’s it, now rub the end of your hand against my slit.” I leaned into him as he followed my instructions, my legs involuntarily opening to give him better access as my legs got weak. “Ohhhhh, yeah, oooohhhhh, just like that Steven. Turn your hand so you’re cupping my pussy and slowly move your hand back and, oooooohhhhh, forth. Yes, yes, yes, just like that. Oh god, you are a good student.” I had both my hands around his neck right now, just holding myself up. “That’s it. Do you feel how wet I am? Use two of your fingers to spread my lips and rub your middle finger in the opening. Ooohhhhh, yeah. Oooohhhh, fuck yeah,” I whispered in his ear. My hips started rocking back and forth in time with his hand. “That’s it, now slide your middle finger into my pussy. Oooohhh, fuck me. Do you feel the hard little nub? That’s my clit and that will give a woman an orgasm ever time, if you’re gentle. Keep moving your finger in and out. Oh fuck, oh god, yes, yes, yes, yes, YES!” My whole body shuddered and I pushed my pussy into his hand as Steven kept fingering my clit. “Oh, fuck Steven. That was amazing. How about the next step? He nodded again.

“Lay me down on the bed, again, gently.” He moved me to the edge of the bed and held my elbows as I slowly sank to the bed. I pushed myself back on the bed and Steven moved with me, kissing me the whole time. “Get down between my legs and lick my pussy. Start slowly, kiss it, just like they’re my lips. That’s it. Use your tongue just like you’re French kissing me. Yesss! Oh, fuck, just like that. Uhhhhh, keep moving your tongue in and out. Now start moving it up and down my slit also. Oh my god, that’s so good.” I had both hands on the back of his head and I was pulling him hard against my pussy.

“Hmmmm, hmmmm.” I couldn’t tell what he was doing so I let go of his head and he came up gasping for air.

“I’m so sorry Steven! You have to be careful when you turn a woman on like that, she might not want to let you up for air. Sometimes you have to force yourself up. When you go back down, spread my lips with your fingers and run the tip of your tongue over my clit. Pull back the skin that’s covering it, that’s it, that’s oooooohhhhhh, yeahhhhhhhhh. Ooohh, ooohhhh, ohhhhh fuck, yes!” I came again and pulled his head down tight to my pussy again. “I need a break. Time to change things up. Lie down on your back.”

I unzipped his pants and pulled them down and his cock sprang up and hit him in the stomach. I got between his legs and licked his cock from balls to head and then lifted it up and put my mouth over his head. My tits dragged against his thighs and my nipples dug into his skin. I lowered my head down over his cock and took as much of him in as I good. I slowly moved up and down. “Does that feel good Steven?”

“Yes Jennifer. It feels as amazing as last time.”

“It gets better,” and I lowered my head back down and took him into my mouth. My hand gently squeezed his balls and then stroked his cock into my waiting mouth. After a few minutes, I swung my leg over his head and lowered my pussy onto his waiting tongue. He didn’t forget his previous lesson penetrated my pussy with his tongue. He raised a hand up and inserted a finger into my pussy. I started to grind my pussy against his mouth while my mouth sucked his cock deep inside. I felt and orgasm building and started moaning around his cock. “Oooh, yeah, Steven, I’m going to cum again, don’t stop.” He grabbed my ass and pulled my pussy down tight against his face and I came again. No screaming, no yelling, just a shudder from the core of my body that shook my whole body. I lifted myself off of Steven to see his face covered with my juices.

“Are you ready?” He looked at me and nodded. I turned around on him again and propped one foot up on the bed and guided his cock to my waiting pussy. I nuzzled his head in between my lips and watched Steven’s face. Then I slowly lowered myself down on him, gently taking more and more of him inside me. Steven’s eyes were practically rolling up in his head as he watched his cock disappear into my pussy. Finally, I had all of him inside of me. “How does that feel.”

“Incredible. It’s the most amazing thing I’ve ever felt. You’re so tight.”

“I’m not that tight, you’ve got a nice size cock. Now, just hold still for a little bit.” I gently started raising and lowering myself on his cock, my hands on his hip to help lever myself up and down. Eventually I leaned forward to rest on my hands and rocked myself back and forth onto his cock. “Grab my ass and help me move back and forth on your cock. And move your head down to suck on my tits. Yes, that’s it. That’s it, just like that, don’t stop.” He kept rocking me back and forth. “How does that feel?”

“Soooo, good Jennifer.”

“Okay, roll me over, but don’t pull out of me.” After he rolled me over I said, “Now put my legs up over your shoulders, this will help you get as deep into a woman as you can possibly get. Gently though. You’re so big you might hurt a girl.” He gently sunk himself all the way into me and I felt his head press up against my cervix. “That’s it, gently. Now start pumping that cock in and out of me. That’s it. That’s it Steven. Oooohhhh, that feels so good. You’re going to make me cum again.”

“Jennifer, I think I’m going to cum.”

“That’s okay baby, just pound my pussy now and fill me up with your cum.” He did just that and started slamming me into the bed as his cock bottomed out in me and then came back up and slammed into me again and again and again and I came. “Oh fuck Steven, that’s it, pound me, pound me, fuck me, fuck me, I’m cumming, yes!!!!” And I felt Steven’s cock stiffen up and start shooting cum deep in my pussy. He stopped pounding me, but his cock kept filling me with more and more cum. I felt it start leaking out of my pussy and running down my ass. I wrapped my legs around him and pulled him into me as I felt his cock deflating.

“You’re not a virgin anymore.”

He lay there, breathing heavily until he caught his breath. “Thank you, Jennifer. That was an amazing gift.” He leaned down and kissed me, slowly and sensually. “What does this mean for us?”

“What do you mean?”

“Can I date you?”

“Oh Steven, this isn’t the time to have this discussion. This was something that I really wanted, but I’m not ready to make a commitment to anyone, not yet. You’re wonderful, but you’re just graduating high school and I’ll be lucky if your parents don’t kill me. You still have so much left to learn about life and love and women. You aren’t in love with me, you’re in lust with me and that’s okay.” He looked terribly disappointed. “Look, how about this, if you ever want to have sex with me, you only have to ask. You are an amazing lover and you’re only going to get better. I had what, six, seven orgasms? I lost count. What girl would say no to that? For right now, let’s just have fun. But Steven, I promise you, when you’re a bit older, if I haven’t found anyone, we can have this conversation again. Okay?”

“I guess I’ll have to live with that.”

“You will, and you’ll be fine with it. Especially when word of your prowess gets out, the girls aren’t going to be able to keep their hands off you.”

After another half an hour of recovery, we got up, took a quick shower, dressed and headed back to Paul and Sarah’s house with my clothes in tow and one newly minted boy who now considered himself a man.