Chapter 1

My name is Sharon, but all my friends call me Cher. I was something of a party girl in high school, and had a reputation as a fun person to be around.

I’m 5’4”, naturally light blond, in great shape with 32C breasts and a pretty face, so I’ve never had a problem getting dates. The problem was I would go out with guys, and even make out with them, but I didn’t let them in. At 19, the biggest thing I had ever had inside me was my own fingers.

My brother is 3 years older than me, and a couple of years earlier when the high school guys began to pass me by for girls who would put out, I went to him for advice.

“Look Cher,” Brian had told me, “You can’t get a guy all hot and bothered and then just leave him cold. We need some relief when we get all worked up. If you’re just calling it off at that point then that’s why the guys are avoiding you now.”

“So what do I do? Use my hand on a guy? Do I just stroke up and down until he squirts? How long will it take?” All the questions came out in an embarrassed rush.

“You can, and the guys will like that, but they’ll like you more if you use your mouth.”

I just sat looking at him, waiting for more. Some sort of explanation. I was really pretty clueless at that point. Brian just looked at me.

“Oh hell,” he sighed, “you don’t have a clue what I mean, do you?”

I blushed fiercely as I shook my head slightly and tears vegan to well up in my eyes.

Just then Mom shouted from the kitchen, “I’m going to Sam’s. I’ll be back in a couple of hours. Either of you need anything?”

“No thanks!” Brian replied.

“Dr Pepper!” I yelled down the hallway.

“Oh sure. Never have too much of that! Unload the dishwasher before I get back. And feed the dog.”

“Ok Mom! Will do! Be safe!”

Brian and I just looked at each other as we heard the door close and then Mom’s car start up and drive away.

“How do I do that?” I asked, after the sound faded.

“Go in Mom and Dad’s room, look in the second drawer under the shirts and bring the toy back in here.”

“Toy?” I said hesitantly.

“You’ll know it when you see it. Go.”

I walked down the hall into Mom and Dad’s room and over to the chest of drawers in front of the bed. I didn’t go in there often, and certainly didn’t go thru their stuff. I quietly opened the second drawer and gingerly lifted the T Shirts, as if I was afraid they would somehow magically know. I still didn’t really know what I was looking for, but my eyes fell on a very lifelike dildo as I moved the shirts out of the way. I swallowed hard and reached in with one hand to pick it up. It had an interesting feel in my hand, and I turned it over and examined it.

“Today would be a bonus, unless you want mom to catch you with it,” Brian called from the other room, breaking my reverie. I put the shirts back and took the rather lifelike, to me anyway, rubber cock to Brian’s room.

“There’s a pretty big gap from kissing and letting a guy feel my boobs to this,” I said, holding the dildo in front of me. “How do I bridge that gap?”

“I can’t believe I’m doing this,” Brian muttered. “Give it here. Now sit down next to me, like I’m your guy and you’re sitting center in my truck.”

I sat on the side of the bed next to him, feeling kind of weird. He put his arm around my shoulders and turned me slightly to him.

“Ok, so we’re parked and making out.” He laughed at the look on my face then.

“Pretend, silly girl! Pretend. You really are blond.” I giggled and relaxed some. It was his standard joke for whenever I showed my naivety.

“So you already said you’ve let them feel your boobs. You ever feel them up in return?”

“A couple of times, on the outside of their jeans.”

“Ok. So you have a little experience. Give me that towel.” He pointed to his shower towel from the night before, hanging on the bed post. I took it and handed it to him.

“So, these are my jeans,” Brian said. He put the dildo on top of his crotch and covered it with the towel. “Get the point? This is so you can pretend and practice.”

I nodded. “Ok.”

“So I’m your guy, and we’re making out. Turn this way. So I’m copping a feel on a boob.” He held his hand up in front of me.

“So now you start to explore more downward.” He took my hand and put it on his stomach. I noticed he was holding the towel and dildo with his other hand. He pushed my hand downward slowly, over the towel, until I reached the bulge of the dildo underneath it and he let go of my hand.

“Keep going.” Brian said simply. He turned my head so I was facing him, rather than looking down where my hand was.

“Remember, we’re making out, so you can’t see. Move your hand by feel. And close your eyes, unless you’re that rare girl who kisses with her eyes open.”

I shook my head and closed my eyes, then swallowed hard as I let my hand side down over the dildo. I was relieved when I felt Brian’s hand on mine, guiding my movements.

“Move up and down slowly, like this,” he said, moving my hand up and down the towel covered dildo.

“Your guy is going to be responding now, maybe moaning or moving his hips. Oh yeah, baby. That sort of thing. That’s how you know it’s time for the zipper. Course, this towel doesn’t have a button and zipper, so pretend.”

He moved my hand up above the dildo. “Here’s the button. Undo it.” I worked my fingers like I was unbuttoning my own jeans. It seemed pretty natural. I reached down and held a piece of the towel, then slid my fingers down, like I was pulling down a zipper.

“Now you’re getting it,” he said. “Now you’ll probably find his undies still covering it up. Start stroking him up and down again.” I moved my hand up and down the dildo, outside the towel again.

“They’ll be elastic, so you’ll have to work your fingers under the band.” I noticed Brian was holding the edge of the towel. When did he move his hand off of my shoulder? I slid one hand under the edge of the towel and felt the head of the dildo.

“Keep going,” Brian said. I didn’t realize I had stopped. I slid my hand down the length of it and back up again.

“Ok, you can look now. I’m going to show you some things.”

I nodded. Brian moved the towel away. He held the dildo by the base, in about the same spot as his cock.

“So move up and down with your fingers wrapped lightly around it. Pause a little around the head, right below where it meets the shaft.” I did as he said, and he continued to guide me for a few minutes.

“After a bit, you break the kiss, and kiss his neck and down his chest now.” He gently pushed my head down as he said this. I turned my head toward him and put my hand on his chest, moving it down in place of my lips.

“He’ll know what you’re doing now, and he’s getting excited. You’ll probably be able to tell. He might flex his hips.” He did then, pushing the dildo up in my hand. “At some point he’ll encourage you.”. I felt his hand on the back of my head then, gently pushing me down until my lips bumped the tip of the dildo.