Chapter 2

“I guess so,” Cindy said softly, “It’s just that I’m ... a little bit nervous.”

I smiled at her and said, “Don’t worry. I’ll take you through every step. We will take it nice and slow, okay?”

Cindy nodded her head yes and gave me a nervous little half-smile.

“Okay now, when you and your boyfriend want to have sex, he will probably want you to get him hard if he isn’t already. You can do this by sucking his cock. Have you ever sucked a guys cock before, Cindy?” I asked.

“No, never. I’ve never even seen a cock in person before. Only through a guy’s pants. Yours is the first I have seen naked like that,” she said, blushing at her innocence.

“Well don’t worry about that. By the time we are finished today that won’t be the case,” I said trying to put her at ease.

“Thank you, Steve, for all of this,” she said.

“Well your mom and I are close friends so that makes you a close friend. And what kind of a friend would I be if I didn’t help my close friends when they need it?”

Cindy smiled at that. I laid down on the bed next to her on my back. My seven inch long, two inch wide cock stood tall and erect pointed at Cindy. I smiled and said, “Okay, Cindy, I want you to start off by just licking on it a little. Lick around the rim and lick up and down the shaft. Lick the whole length and all around it,”

Cindy nodded her head and nervously put her tongue on the tip of my cock. I had a drop of precum sitting there waiting for her and she tasted it.

“Well how does it taste?” I asked.

“A little salty but not bad. Actually pretty good,” she said.

Then she began licking my cock and I showed her the best way to do it the way I liked it, and the way her mother licks me when we have sex. She was pretty good at it and a fast learner. Before long she had me hard as steel and ready for the next step.

“Okay, Cindy, that was great. Now I want you to take me in your mouth and suck it. Remember to not use your teeth because my cock’s really sensitive.”

“Wow, it’s really big Steve,” she said.

“Don’t worry, soon you’ll be taking this way up your pussy. It’s much easier using your mouth.”

Cindy opened her mouth and slowly slid me into her mouth, making sure her teeth did not touch my cock. Then as I directed her, she began to suck it awkwardly.

“Like a popsicle, Cindy,” I said coaching her. She obeyed. “Oh yeah ... that’s better,” I said, encouraging her.

Cindy popped me out of her mouth to smile, then wolfed me back into her mouth again. She took this as her first step in accomplishment. For the rest of the time, she would work hard and try her best to please me.

Cindy slowly bobbed her head up and down and I let out a soft moan as I put my hands on either side of her head, guiding her rhythm until she knew how fast I liked it. I also guided her how deep to take me, pushing her head in a little deeper with every few strokes. She choked once so I quickly made her pull out.

“Ahh ... sorry,” apologized Cindy as she wiped her mouth.

“That’s okay, hon. It takes some practice. Now let have another go at it.”

Cindy dived back onto my cock and sucked more. I slowly began to push her to stuff my cock in his mouth and Cindy tried to resist the choking and gagging, but it was no use as she pulled out again nearly throwing up.

“Sorry,” Cindy said again.

“It’s okay,” I smiled, “You did pretty good for your first time, really.”

I climbed on top of Cindy and propped my upper body up on my forearms so I wouldn’t be too heavy on her. I began kissing her again. She had forgotten all about her worries of her virginity being taken as she moaned and melted into our kiss. After a few moments of tasting her sweet lips, Cindy broke the kiss “Fuck me, Steve, please fuck me now.”

I raised up a bit and took my hard cock in my hand, rubbing the head of it on her wet slit and letting her feel it just push her lips apart.

“Mmm, that feels nice...” she said.

“Okay honey this might hurt a little being your first time. But I will go slow and be as gentle as I can be,” I said. Cindy nodded her head and bit her lip a little, looking worried but not afraid.

“Here we go hon,” I said as I pushed just a little stretching her opening to accommodate the head of my cock.

“Ooooh” she said as she felt her pussy being opened. I watched her intently, judging her reactions to what I was doing to her. I pressed a little deeper and suddenly I felt the head of my cock slip past her lips.

The sudden shrinking of her pussy startled her. “What was that, what happened?” she said, wide eyed.

“It’s okay sweetheart, it’s just the head of my cock slipping into you,” I said softly. My calm manner put her at ease again – I guess she figured if I wasn’t worried about it, things must be going all right!

I stayed there for a moment letting her get used to me inside her. “Oh my God, your cock is so big! But it feels ... wonderful!” she said. Cindy squirmed as my cock prepared to dominate her cherry. I felt my cock poking at her hymen and stopped for a moment. She nervously looked at me.

“Okay, Cindy, I am at your hymen ... your ‘cherry’. Now this is going to hurt a little but I have to get past it to take your virginity. I will be as gentle as I can. Can you be a big girl for me?” I asked her.

“Please Steve, this is what I’ve wanted. I know you don’t mean to hurt me. Please, take my cherry ... make me a woman,” she said. I had to kiss her for that and I kissed her hard and deep – like I kiss a woman.

I gathered myself for this and then I looked at this beautiful creature I was about to claim. “Ready sweetheart?” I asked. Cindy took a deep breath and nodded clinging tightly to me. I pushed forward and felt my cock tear her innocence in two.

She gasped as she felt me enter territory that no man had ever been in before. I slid easily into her the rest of the way until my balls slapped her ass. I was all the way in and pushing on her cervix. I felt Cindy digging her fingernails into my shoulders and I thought to myself, Fair is fair – I hurt her so she can hurt me a little!

I held myself inside her for a little while as I knew she was hurting and I didn’t want to make it any worse. I had never taken a cherry before and this was my girlfriends daughter – I cared about her.

After a couple minutes I looked at her, seeing her cheeks and eyes wet with tears. “You okay Cindy?” I asked.

“Y-yeah...” she said.

“Are you ready to continue?” I asked. I didn’t want to pressure her – I would have been okay with either answer. But she was on a mission and she wanted to keep going.

“Please,” she said.

I started slowly withdrawing until just the head of my cock remained inside her. Then just as slowly I pushed back into her until she had all of me inside her again. I stroked her slowly and fully for a few times, helping her to get used to me.

Cindy, bless her heart, gritted her teeth and powered through the pain and discomfort. Every time my cock bottomed out in her she whimpered and screamed softly in her mouth mixing the pleasure with the pain

“Shift your hips as you need to so I can hit where it feels the best,” I said and Cindy obeyed.

She shifted her body right and then left until I slid straight down into her tight pussy and scratched her g-spot. She moaned and closed her eyes while arching her back and I touched it again.

Her pain and discomfort was beginning to fade away and pleasure was creeping through along her thighs. She had never felt this kind of feeling even while masturbating. She screamed lightly as my cock suddenly pounded at her cervix and her body shivered with excitement.