College Prep Ch 01 1

It was the summer after I graduated from St. John's Prep, had just turned 19 in July and I was both excited and nervous to attend Nazareth College in the fall. My step-sister Bailey had just graduated with her Bachelor's in marketing and was about to start on her graduate degree. We had both attended St. John's for high school so we were used to being away from home. Getting into Nazareth was fairly easy considering that many of the administrators had attended St. John's themselves and Bailey's academic reputation gave me a good name. Even though it was a boarding school, St. John's did a good job of keeping students separated after hours so I never had a chance to date much less do anything else with a girl. I knew college would be different, that not everyone went to a boarding school and that many people had more experience in bed than me, and if I wanted a shot with anyone, I knew I was going to have to figure out what I was doing.

When we were home from school, we lived with our parents at our house in Long Island. My dad had married Bailey's mom when we were 2 and 6, so I never really saw her as my "step" sister. My parents had made their money as financial managers, they stayed away from Wall Street but were sure to hit up every broker who didn't have someone taking care of their money for them. Ironic, but it worked. When they weren't at work, they were usually traveling or attending some event. So this summer, I had access to a house bigger than I could possibly have a use for.

I hear Bailey come home from her shopping trip and come upstairs. She stops by my door.

"Hey Will, what're you up to?"

In my hands I had the Nazareth College Student Handbook. Like I said before, I was nervous, so I wanted to learn anything I could about the school before I went.

"Oh my goodness, you're still reading that? This must be your 3rd time."

"Fifth actually."

"Wow. Believe it or not I was just like you when I was getting ready to go. I was worried about if the classes were going to be harder, what would the professors be like, would I have time to make new friends, not to mention I had no idea about boys."

"That's pretty much how I feel right now... Except for the boys of course. Obviously girls."

She chuckled, "Sounds like you need to find someone to spend time with this summer."

"I guess so."

"Oh, I just remembered. Wait right here, I want to know how this new top looks."

Taking her shopping bags with her, she came back wearing jean shorts and a flowing white blouse that exposed her shoulders and her cleavage in the front. Her shorts came up high on her ass, enough that the bottom of her cheeks were visible.

"It looks..um..it looks good." I tripped over my words

"Not used to checking out your sister?" She laughed.

I chuckled, "no, not really."

"Well you better get used to complimenting girls if you want to have a shot with anyone next year."

"But you know I'm not comfortable with girls"

"You better get comfortable," she walked towards my bed.

"Um..how?" She leaned over to get at my eye level and I could see her large breasts down the front of her shirt. I diverted my eyes, hoping she wouldn't see me trying to catch a glimpse.

"Will! Were you trying to look down my shirt?!" She chuckled.

"What?! Never," I tried to play it off. "Sorry, did it seem like it?"

"I know when someone's checking me out. Don't worry I'm not mad. It's ok. We're not related by blood, remember? I think I have an idea to help you out this summer. Come up to my room in 5 minutes, 'kay?" She leaned in and gave me a peck on the cheek, and then got up and started to leave.

"Umm, o-okay." I wasn't sure if I should be scared or excited. I scrolled through Facebook for 5 minutes and then headed upstairs to her room. I knocked lightly. Bailey opened the door wearing an oversized t-shirt and pajama shorts.

"Hey you," she smiled, then went and sat on her bed. She patted the spot next to her, telling me to come and sit. I nervously complied. She took my hand in hers.

"Will, you trust me right?"

"Of course."

"Ok good. I was so busy with school last semester that it's been a while since I've spent time with anyone, so I think you can help me while I help you learn some stuff. So I just need you to tell me if you aren't comfortable with anything. And also, try not to be too weird about it." She put her hand on my leg and I began to understand what she was getting at.

"Alright. Let's do this I guess." I nervously smirked at her, she smirked back and pulled me in close.

"Let's see what it takes to get you hard," she said slyly. She began to kiss me while she ran her hand through my hair with the other one on the back of my neck. I placed my hands on her waist, unsure of what else to do.

"Touch me," she moaned quietly. She removed her hand from my neck and grabbed my wrist. She placed my hand back on her waist, but this time under her shirt and began moving it up to her breast. I cupped her large, soft breast as my cock grew harder. She pulled away suddenly and removed her shirt completely, revealing her two large tits. They were pale with hard, red nipples. Bailey went back to kissing me and started to remove my shirt. I pulled away and took it off. She looked at my torso. I had kept in good shape, especially leading up to summer. She bit her lip as she studied my body. She put her hand on my leg and slowly moved it up to my crotch. She groped my now fully erect cock.

"Oh my God," she said with surprise. "I thought you'd be big but not that big. Take off your clothes. I got up and took of my shorts and boxers allowing her to see all of me.

"Come closer." I did. My dick rested just in front of her face. She teased me by lightly scratching her French nails down my stomach. Her small, pale hand wrapped around my shaft and began to stroke. Her soft skin was the best thing I had ever felt. She looked up at me.

"Do you want more?" I nodded.

"From now on I want you to be shaved when I see you. Go clean up and come back." She stood up and whispered in my ear.

"And don't you dare touch yourself." She pecked me on the cheek and gently pushed me to the door. I quickly went to my bathroom, turned on the shower and grabbed a new razor. I shaved everything smooth and grabbed a towel. Surprisingly I was still halfway hard. I hurried back to Bailey's room and stood in her doorway. She yanked my towel off.

"I never told you that you could cover up again." She took my hand and led me to her bed and pushed me onto my back. Her assertiveness turned me on and my erection grew again. Her hand stroked my member until I was hard again. She then leaned over and put her mouth around my cock and began to move her head up and down. I could feel my head enter her throat again and again. My body began to tense up and I gripped at the sheets. My back arched and I was able to barely get any words out.

"I'm gonna cum." She removed herself just in time and pointed my cock at her breasts. The biggest load of cum I had ever shot exploded onto her and dripped down my shaft.

"Did you like that?" I nodded in agreeance.

"What do you say?" She chuckled.

"Than-thank you." I was still out of breath.

"I'll be right back." She went to her bathroom and came back with a hand towel. She had already cleaned the cum off of herself. Using the towel she wiped me clean and then threw it aside. I sat up on the bed and she sat across from me with her legs at my sides and we began to make out again, and again, she took my hand and placed it on her smooth, flat stomach. She pushed my hand down to her waistband. I continued on my own, I felt my way through her short pubic hair until I felt her slit. My middle finger reached her clit and I began to massage her slowly. She moaned.

"Go farther." Finally, my finger went inside her and she gasped. I moved inside and out of her as she continued to get wet.

"Is this your first pussy?"

"Yeah, it is."

"You're doing so good, I want to show you something more though." I pulled my finger out of her as she moved away. She took off her shorts and laid back on her bed. I could feel myself getting hard again just by seeing her fully naked. Her pussy was topped by blonde pubic hair that was trimmed into a short triangle.

"Lick my pussy, Will." I complied and moved my head to her crotch. I cautiously licked at her slit. I tasted her and licked harder. Knowing I was pleasing her turned me on and I wanted more. I licked at her clit as she began to moan. She placed her legs on my back and pulled me in. My youngest entered her vagina and she arched her back. She ran her fingers through my hair and pushed me farther into her. Her juices and moans encouraged me. She moaned one loud final moan as she climaxed. I came up and she smiled at me.

"That was really good for a first time. And I see you're hard again."

"It was really hot seeing you orgasm from me like that." She chuckled.

"Maybe I'll let you try again sometime. But for now, go get cleaned up for dinner. And don't you dare masturbate. You can put your boxers on." The last sentences sounded firmer than I was used to, but I complied. After I showered we had dinner and we went to bed. I struggled to fall asleep because of the days events. I wanted to pleasure myself but I didn't want to disappoint Bailey. Eventually I fell asleep thinking about what tomorrow held.