Babysitter Takes My Virginity

³"A babysitter! I'm 18, I don't need a babysitter!" I screamed.

"Now John, lower your voice." Mom said. "It's more like someone to keep you company and help you watch the house. I know you still talk to Sandy once in a while, it should be fun."

"Yeah, I talk with her, she USED to be my babysitter.

"Besides Son," Dad added, "we need someone to make sure you don't have a steady stream of girls coming and going out of here."

I know he was trying to lighten the situation, but I just rolled my eyes, stormed off to my room and slammed the door, throwing myself on my bed.

"Have a great vacation!" I yelled sarcastically through the door.

Just then the doorbell rang. I heard Sandy's voice although I couldn't make out what she was saying.

"Bye honey." My mom said, My only answer was to flip off the door.

About 15 minutes went by and I heard a light rap on my door.

"John? I know this sucks for you, can I come in or you come out? Let's talk about how we can make this bearable for you."

"Doors open." I mumbled, sitting up on the side of my bed.

She opened the door and stepped inside. The only good thing about having her here was she was drop dead gorgeous. She was about 5' 6" with shoulder length blonde hair, deep brown eyes, with lips just full enough to make you want to kiss them. She had on a vee neck t-shirt that showed a nice amount of cleavage and denim shorts.

She sat next to me and started talking.

"I knew you would hate this and I almost told your parents no, but the money was decent and they said they would find someone else if I didn't do it. I figured it would be better to have a friend here than a stranger. My thought is to take care of the house and as long as you don't plan on doing anything really stupid, I'll leave you alone. Who knows, we might even have some fun along the way."

"I guess when you put it that way, it's not so bad. Will I need to tuck you in at night, because I heard you old people go to bed early."

"Old? You little punk! You know damn well I'm only five years older than you."

She playfully punched me in the arm, so I hit her with my pillow. She then pushed me down and started tickling me. I slid out from under her and stood up. She got up as well and I couldn't help but notice her nipples pushing out against her shirt. She noticed me looking and looked down at herself.

"These things have a mind of their own." She giggled.

I felt my cock swelling and grabbed a pillow to hide myself. Sandy noticed before I could completely cover up.

"Oh shit! I'm sorry, I didn't mean to...I'll give you a minute. Come on out to the living room when you're ready and we'll watch a movie or something."

She walked out, closing the door behind her. I thought about jerking off real quick but I knew if I took a few minutes, she would know what I was doing. I was slowly deflating, so I rearranged myself and walked out.

"I'm really sorry Sandy, I didn't mean for that to happen." I did notice she had put a light jacket on.

"No, it's cool. We can't control what our bodies want to do. Let's make a deal, if our bodies do things without our consent we don't make a big deal out of it, or worry about hiding it."

"Deal, then why are you wearing that jacket?"

Sandy smiled as she unzipped her jacket.

"Until we made the deal, I wanted to save you any embarrassment. Oh, and just so you know, it doesn't bother me if you look at my body. I've worked hard to look like this, and I'm proud of it."

We sat and watched TV for a little while in relative silence.

"John, can I ask you a personal question? You can ask me anything after."

"Sure, I guess."

"I know you went to an all boys high school, how much experience do you have with girls?"

"Not a whole lot."

"Have you ever had a date?"

"I had a date for the prom."

"How did you find her?"

"The other half of the campus is all girls. We were kind of assigned dates."

"Wow, how romantic." She said sarcastically.

"So, you've never even really kissed a girl?"

I felt myself turning red. "We were allowed to kiss her cheek at the end of the evening, so I guess the answer is no."

"Don't be ashamed, you can't help how you were raised. Do you know anything about sex?"

"Just from what I've seen on my computer."

"So jerking off to porn. It's all good, I do it too."

Thinking about her masturbating make my cock begin to stiffen.

"How about you?" I asked. "What have you done with a guy?"

"Fair question. Well, I've certainly done more than kissing. I started with hand jobs, moved on to sucking dick, then full on fucking, and finally letting a guy cum in my mouth. I haven't given anyone my ass yet because I want to give my ass to someone very special, someone I trust to take their time and to stop if I don't like it. I've poked around back there myself a little. I think I will like it. I'm sure I'll find out someday."

By now my cock was rock hard and making quite the tent in my jogging shorts. Sandy's nipples were hard again and she was absently running a finger over one.

I had agreed to our deal so I didn't try to hide it. I think I actually wanted her to see it.

Suddenly Sandy realized what she was doing and pulled her hand away from her nipple.

She looked at me and noticed my state of arousal.

"Thank you for not trying to hide that from me. I guess we both got turned on by my sexcapades. Have you ever measured your cock? It looks pretty big from what I can see."

"Just about seven inches. Is that big?"

"Not huge, but bigger than average."

I was just about to excuse myself to knock it down.

"Do you need to take care of that, and can I watch?"

"You want me to jerk off in front of you?" I said in astonishment.

"Yeah, it would be hot! I really want to see your cock. At least show it to me and then you can go off in private if you want to. I'm really horny, so I'll do it with you if you want. Pull your clothes off and I'll get naked too. You'll finally get to see a naked girl in person."

I hesitated for a second, but the thought of seeing Sandy naked pushed me on. I stood and peeled my shirt off. I was in good shape due to playing sports all through high school. I could tell Sandy liked what she saw by the way her eyes widened when she saw me shirtless.

"Keep going." She urged me on. "I promise I'll get naked after you."

I pulled my shorts down and my cock sprang straight out. As I stepped out of my shorts she slid closer to me on the couch to get a better look. Her face was only inches away. I was hoping she would grab my cock or even put it in her mouth, Luck was not with me at that moment.

"You have a beautiful cock! Some girl is going to be very happy someday. Now I have to keep my promise."

She stood up and pulled her shirt off over her head, revealing her awesome tits. Her nipples were erect like two pencil erasers.

"Look all you want before I take my shorts off, then you can stare at the rest of me."

I kept looking back and forth between them, studying every little bump. I so badly wanted to touch them, but that was not part of the arrangement.

"Before I lose my pants, I'll be right back."

She ran off to the bathroom and returned with two towels. I was mesmerized watching her boobs sway as she walked. She threw one towel on the couch.

"John, drag that chair over here right in front of the couch."

I did as I was told and she tossed the other towel on it.

"Now for the big reveal!"

She pushed her pants to the floor and stepped out. She raised her arms above her head and slowly rotated around, bending over to give me a good look at her ass.

"So, am I worth jerking off over?"

"You're prettier than all the girls I've seen on the internet!"

Sandy smiled and bent over to spread the towel over the couch. I realized what she was doing and spread the towel over my chair.

"Hey John, that ass is almost as nice as your cock!"

Sandy sat on the couch and slid her ass almost to the end. I slid my chair as close as I could. Sandy put her feet on my armrests, opening her pussy up for me to view.

"See how wet my pussy is? I told you I'm horny."

She opened her lips so I could peer directly into her. She ran her fingers around her lips, then slid a finger deep in.

"Don't be shy, grab that cock!"

"I'm just afraid I won't last very long."

"I don't care if you cum in five seconds. I want to see your cock fire it's load. We can always do this again."

I wrapped my hand around my cock and slowly slid my hand up and down. Sandy had two fingers buried deep in her pussy and was sliding them in and out. Her other hand was pawing at her tits, twisting one nipple then the other. Just watching her made me want to cum.

Sandy's eyes tried to stay glued to my crotch but she couldn't help but close them occasionally because of the pleasure she was giving herself. I was doing the same, trying to see as much as I could.

She released her tits and brought her hand down and began rubbing her clit.

"John, I'm going to cum for you! I need you to cum for me!"

My hand started flying up and down my shaft. I knew I would cum in seconds. Sandy started moaning and her body was shaking.

"Oh fuck, I'm cumming!" Sandy screamed as her body went rigid.

This was more than I could handle and my cock erupted. Streams of cum shot out of me. I didn't think I would ever stop. When I did I was covered in a white mess from my chest to my knees.

Sandy chuckled, "Well, thanks for sharing."

She leaned toward me and scooped up a glob of cum with her finger that had landed on her leg. I almost came again when she brought her finger to her lips and sucked her finger clean.

Mmm, tasty. I guess I should offer you a taste of me."

She took the two wet fingers that were in her pussy and leaned forward and extended her arm. I leaned in and took her fingers into my mouth, I cleaned up every bit of her flavor that I could.

Sandy took the towel from the couch and tossed it to me.

"Here get cleaned up, you made quite the mess."

I wiped myself off then went into the bathroom to properly clean up. I came out with my cock bobbing out in front of me.

"You're still hard?" Sandy asked.

"Well, that was the most incredible thing that has ever happened to me, so yeah I'm still turned on."

"Okay, then come sit down and we'll let things relax and take it from there."

I sat in the recliner and Sandy reclined me back.

"Close your eyes and chill for a bit, if you still need to, you can jerk off again."

I closed my eyes, but images of what we did was still running through my brain. I could feel my cock still throbbing. I knew there was no way I was going down soon.

Suddenly, I felt something warm and soft pushing against my lips. I opened my eyes and saw blonde hair hanging over me. I realized that Sandy was kissing me.

She stood up and asked, "how was your first kiss?"

"Amazing! I'm not complaining but I thought we were only going to get ourselves off."

"I changed my mind. I thought you could use some basic skills for when you get a girlfriend. If that's alright with you."

"I'm all yours! Teach away."

"So because your parents are going to be gone for about a week, I'm going to be your mock girlfriend. I'll show you some pointers and take it from there. I was going to show you how to kiss a girl goodnight, but I think it would be better to do that clothed That would be difficult with this guy showing no signs of going down, so..."

Sandy reached out and grabbed my cock. I couldn't believe my cock was in this beautiful girl's hand.

She whispered into my ear. "Relax and enjoy."

She ran her fingers all over feeling every bump and vein. She reached over from the top, hooked her fingers lightly under the head and gently pulled up.

"Sandy, that feels awesome!"

"I'm glad you like it. I can't wait to feel your hot cum all over my hand."

She started pumping my cock, alternating the speed from barely moving to making her hand a blur. This being the first time someone besides me had touched my cock, I could feel my orgasm coming quickly.

"Sorry, I'm gonna cum soon." I gasped.

She slid her other hand under my balls and gently rolled them around.

She leaned in real close and whispered. "Good, I want to make you cum. Blow that cum high in the air. Cover my hand."

That pushed me over the edge. I shot my cum straight up. I felt it falling back onto me as I continued to blast into the air. Sandy kept slowly stroking my cock even after the last drops oozed out.

Her hand was totally covered in a layer of cum. She managed to squeeze a few more drops out of me.

Then to my surprise, she brought her hand to her mouth and licked and sucked her hand clean.

"I hope you don't think this is gross, but I actually kind of like the taste of cum. I know a lot of girls won't touch the stuff, but I don't mind at all."

"I think it's awesome! I thought only the girls in porn videos pretended to like it."

"You mean like this?"

She scooped my cum from my belly and opened her mouth and stuck her tongue out. She let the cum dribble onto her tongue and turned to me as if facing a camera. She made a big swallowing motion then showed me her tongue again to prove it was gone.

"Yeah, just like that. If you ever decide to go into porn, I'll be your biggest fan!"

"Thanks, but that's not going to happen. Now let's go get cleaned up again and get dressed. Then I'll teach you some dating etiquette."

We met back in the living room. Sandy told me it was time to learn.

"Okay, so this is a very important rule. If you go to pick your date up at your house, never ever sit in your car and toot the horn. Always go to the door, otherwise you will piss off her parents. There could be some exceptions to this rule, but you're smart enough to figure it out."

"Next lesson is kissing. You bring a girl home and walk her to the door, how do you know if you should kiss her?"

"Um, ask her?"

"You could, and some girls would think that is sweet, but if you're interested in kissing, and you may not want to if it was a shitty date, but lean in and see where it goes. You might have her turn away and shake your hand to a full blown make out session, or anything in between. So want to practice?"

I jumped at the chance!

Sandy took my hand and we walked to an inside doorway.

"So this is me." She said, "I had a really nice time."

"I did too." I replied as I leaned in.

Sandy turned her head, patted my shoulder with her left hand and shook my hand.

"Okay, we'll like I said I had a good time. Can I call you again?"

"Now don't ask that if you don't mean it." Sandy warned.

"No, if I actually had a good time, I can try for a kiss the next time."

"Nice! Now let's try again. Come in for a kiss."

I leaned in and this time our lips connected.

She backed away and said to me, "You need to relax your lips. You're keeping them all stiff. They need to feel softer. Put your finger on my lips."

I did as I was told.

"See how tight my lips feel? That's how you're kissing. Now touch them again."

Once again I touched them, it felt as if my finger was sinking into them.

"Let's try again."

Again our lips came together, this time she didn't pull back. We kissed for several seconds.

"Wow, you're a fast learner! I think it's time to add some tongue. Leave your mouth slightly open and follow my lead."

Again our lip touched and after a couple seconds I felt her tongue pushing into my mouth. I pushed mine into hers and soon our tongues were dancing with each other.

I'm my opinion, this was going beyond learning to kiss and into making out. She pulled me closer and I wrapped my arms around her drawing her in tighter.

I felt my cock growing again. She must have felt it as she started grinding her hips against me. I was hoping maybe she would jerk me off again. I didn't dare to hope for more.

Her lips left my mouth and she began kissing my neck. I never thought that it would feel so good! She unbuttoned my shirt and started sucking on my collar bone near my shoulder. She leaned back to look at me.

"There, you have your first hickey. I put it there in case it doesn't fade by the time your parents get home."

Doing what she asked, I followed her lead and began kissing my way down her neck. She pulled her head back, giving me full access to her neck.

"Do it! Right there, give me a hickey. I don't care if anyone sees it."

I sucked on her neck for several seconds then looked at my handiwork. I have to say I thought I did pretty well for my first time.

Sandy pushed me back.

"Wow! I think you've got kissing down! Now I'm going to teach you patience. Even though I could feel your hardon, sometimes you have to end a date without getting off. So, for the rest of the evening we can snuggle up on the couch, make out a little and watch TV. Okay?"

"Yeah, that works, I mean I can't help it if I stay hard."

"That's okay, I like knowing I make you hard."

The rest of the evening was spent watching movies, with a little making out mixed in. I had a feeling that she would notice when I would start to soften and make out more with me.

After a while, she reached over her head, stretching.

"I'm off to bed." She announced. "Thank you for not pushing to get what you wanted. More lessons tomorrow."

She hugged and kissed me with my cock poking at her belly. She went to the guest room and I went to my room. I told myself I wasn't going to masturbate, but after fifteen minutes of my cock refusing to go down, I grabbed ahold jerked it with visions of Sandy's hand wrapped around my cock and covered in my cum.

Next morning, wearing just my boxers I made my way to the kitchen, following the scent of bacon. Sandy was in front of the stove wearing only a t-shirt and panties.

"Good morning John. I hope you slept well. Did you masturbate last night? I did. Are you ready for more lessons today?"

"Um, yes to both."

"I see you're ready to get started, judging by the tent you've got going."

"Well I'm eager to learn and I have to admit, I've got a bit of a crush on the teacher. What are you teaching me today?"

She just smiled and dropped a plate of food in front of me.

"I jumped the gun yesterday when I jerked you off, but we'll be going to second base. Yes, that means you get to touch these today."

She pulled up her shirt and flashed her tits at me. I damn near spit my food back out. I felt my cock pulse and thought I might cum right there. I suddenly lost my appetite and wanted to get straight to my lessons.

"Eat!" She ordered. "You're going to need your energy. I have plans for you!"

I ate as fast as I could without choking. I quickly ran to brush my teeth and found Sandy on the couch. She patted the seat next to her so I sat. She lifted my arm and slid under so my arm was around her.

"Just start by doing what seems natural, and tearing my shirt off isn't it."

I started stroking her hair then kissed her on top of her head.

"Mmm, nice." She purred.

I sat her up and brought my lips to hers. She eagerly opened her mouth and our tongues snaked around together. My hand slid lower and brushed past the side of her tit. I kept going and slid my hand up under her shirt and rubbed her tight stomach.

Her hand dropped to my thigh and slid up just under my balls. I so wanted her to touch them!

I slid my hand up further and stopped when I hit the bottom of her boob. She didn't stop me so I slid up and cupped her tit. I squeezed a little, feeling her nipple harden under my palms.

I felt her hand rest on my balls through my underwear. She then squeezed my cock and I thought I was going to cum in my shorts.

I started lifting her shirt, she raised her arms allowing me to pull it over her head.

"Hey, stand up for a second John."

We both stood up and she pulled my underwear down leaving me naked. I reached out and pulled on her panties. I knelt in front of her and pulled them to the floor, leaving me with an incredible view of her naked pussy.