Part 6: Cheryl

About a week later I heard that Bruce Johnson had broken up with his long-time girlfriend Cheryl Albright a few weeks earlier. I knew Cheryl a little from English class. She had a nice personality and sense of humor. Cheryl was about 5'-7" with short black hair. She was a little overweight, but not too big. I hadn't been with a girl in five weeks. I was getting desperate. I decided to ask Cheryl to pizza and a movie on Friday night.

After English class I walked with Cheryl as we left the room. "Cheryl, um... would you like to, uh... to go out for pizza and a movie with me on Friday night?"

"Sure Will, that sounds like fun." My heart skipped a beat. A date! I finally had a date.

"Uhh... OK." I was mentally off balance. 'Pull it together!' "I'll pick you up about 5:30 pm."

"I'm looking forward to it Will."

I floated to my next class on a cloud. My badly bruised confidence was recovering. The rest of the school week flew by. I couldn't wait for Friday night.

My mom drove me over to Cheryl's house on Friday night. I went inside and met her parents. They talked with me for a few minutes. They reminded Cheryl and I that Cheryl had to be home by 10:30 tonight. Mom welcomed Cheryl. Mom and Cheryl kept a conversation going the whole way through Lancaster to the mall on the other side of town. Mom dropped us off at the pizza place near the movie theater. She said she would pick us up around 10 pm.

We ordered our pizza and sat down at a table. Cheryl was a great conversationalist. Talking with her was easy. She asked the right questions to keep the conversation going. After we finished the pizza, we walked over to the movie theater. We picked Adam Sandler's latest movie.

We took seats in the middle of the theater. After a few minutes of the movie, I stretched and put my arm around Cheryl. Cheryl immediately snuggled up against me. She put her hand on my knee and rubbed it. We watched the movie for awhile touching and holding each other. Cheryl laid her head on my shoulder.

"Cheryl can I kiss you?"

"I thought you'd never ask, Will."

I kissed Cheryl on her soft lips. Her tongue came snaking into my mouth immediately. My tongue met hers. We opened our mouths wider. Our tongues probed each other and slid back and forth between our mouths.

Cheryl reached for my arm that was across her shoulders. She took that hand and placed it on her breast. She held her hand over mine and pressed. I had forgotten how much easier this was with a girl who was experienced. Cheryl obviously knew what she wanted. I would be happy to help her out. I squeezed and rubbed her breast. Cheryl rubbed her hand up and down my right thigh.

Cheryl and I made out during most of the movie. Near the end of the movie, she started to stroke my cock through my pants. I had to stop her so I wouldn't cum in my pants. That would have been really embarrassing. When the movie was over I used my coat to hide my erection. I didn't think it was going to go down until I got home and could jerk off. We sat on a bench outside the theater while we waited for my mom.

"Will, I had a really good time. Can we get together again?"

"I did too. I'd really like to do that. Are you busy tomorrow afternoon?"

"No."

"I have the house to myself. My little brother has a hockey game at 1 pm. The rest of the family will be at the game until 4 pm. Why don't you come over?"

"That would be great. I haven't had quality time with a guy I like in too long a time. When to you want me to arrive?"

"Why don't I call you when the rest of the family leaves?"

Mom pulled up in front of us just as we finalized arrangements for tomorrow. We hopped in the back of the car. My mom drove us to Cheryl's house. I gave Cheryl a fairly discrete kiss good bye.

When we pulled away from Cheryl's house my mom asked, "You like her don't you?"

"I do. It's only the first date, but I had a really good time. Cheryl's fun to be with. She's easy to talk to. I'm going to ask her to go to the spring dance in two weeks."

"I like her too. She seems like a very sweet girl."

I cleaned up my room on Saturday morning. I wanted it to look nice for Cheryl. Also mom had been bugging me for two weeks to clean it. I thought that Cheryl was after sex just like me. Even if she wasn't, I was confident that I could convince her to have sex after I gave her an orgasm or two. It always worked before. My horniness didn't let me stay still. I paced. I went for a bike ride. I shot some baskets out in the driveway. Anticipation was driving me crazy.

I called Cheryl as soon as my family walked out the door. Cheryl's house was about a half mile away. Cheryl arrived on her bike about five minutes after the call. We went to the family room. I turned on the TV. The movie "Risky Business" was on. Cheryl and I sat down on the couch. I put my arm around her. Cheryl snuggled up to me immediately. Within a couple minutes, Cheryl and I were making out. I fondled Cheryl's tits. They were large, soft and extremely inviting. I started unbuttoning Cheryl's blouse, wondering what her reaction would be. Cheryl smiled and unbuttoned my shirt.

We pressed our bare chests together as we made out. After kissing for awhile, I leaned away and started to play with Cheryl's tits. I squeezed them and rubbed her nipples. Cheryl stroked her hands up and down along my chest and sides. By the time Tom Cruise was losing his cherry on the train in the movie, my hand was down Cheryl's pants stroking her juicy cunt. Cheryl reached over and started rubbing my cock through my pants.

"Cheryl, do you want to go upstairs to my bedroom? I think we would be more comfortable."

"Yes, let's do that. It's been too long for me." Cheryl said as she stood up and waited for me to lead her to my room. We raced upstairs to my room. We kissed and then Cheryl pulled me down on the bed on top of her. I rubbed my crotch against Cheryl as we kissed.

"Cheryl, can I see your pussy?"

"Yes, let's get naked."

I thought, 'Cheryl must be really horny. I'm definitely getting laid today.' We removed the remainder of our clothes and sat back down on the bed. I pressed my body against Cheryl's while we kissed. After a couple minutes, I kissed my way down her body until I reached her pussy.

Cheryl's pussy was crowned with a crown of dark curly hair. I ran my finger down her puffy lips. Then I licked up and down her lips. I worked my tongue over her clitoris.

"Ooohhh... Will what are you doing?"

I paused for a second. "What do you think? I'm licking your clit."

"Bruce never did this. Isn't it nasty tasting?"

"You've never tasted your pussy juice? It's really nice." I rubbed my finger along her pussy lips and collected some of her juices on it. I held it up to her mouth. "Try this."

Cheryl licked my finger. "That doesn't taste too bad."

I went back to work. I licked and sucked her clit while I worked her pussy. Cheryl moaned, squealed and shook as I stimulated her pussy. She screamed when she came the first time.

"My Lord Will. Where did you learn to do that? I didn't know a guy could do that to a girl!"

"I've had a little practice. I like to make sure my girl enjoys sex. Have you had sex before?"

"Yes, Bruce and I did this."

"Shall I eat you out again?"

"God yes. Please."

I rubbed her clitoris this time between my thumb and finger while I tongue fucked Cheryl. It only took a couple minutes to bring Cheryl to another climax.

Cheryl lay on my bed panting while I got ready to fuck. I pulled out a condom and opened the package.

"You don't have to use that Will. I don't mind."

"Are you on the pill?"

"No, but I should be safe this week."

"I'm going to use it anyway. I don't want any surprises in nine months." I rolled a condom down over my cock. "Are you ready Cheryl?" I grabbed a pillow.

"God, yesss... Will. Put it in!"

I lifted Cheryl up by the ankles. I put the pillow under Cheryl's ass. "Will, what are you doing?"

"Be patient. I'll show you. Put your ankles on my shoulders."

I put my cock against the entrance to Cheryl's velvet tunnel. I pushed the tip in slowly. My cock slid in fairly easily. Cheryl wasn't as tight as my last two girlfriends, but her pussy still felt tight around my cock. My cock sank the whole way down until my cock bumped into Cheryl's cervix. My balls were resting against her ass.

"Will, how long is your cock. It feels like it goes the whole way to my belly button. You are much longer than Bruce. He never reached the bottom of my pussy. Fuck me now, I really need it!"

I pulled almost all the way out and pushed in fast. I wanted Cheryl to feel every inch of my cock. I hit bottom on nearly every thrust. I pumped and pumped. Cheryl was so stimulated from her two orgasms that she was going wild. Her pussy quivered and spasmed as I fucked her. After a couple minutes, Cheryl orgasmed again. I wasn't close yet, so I kept thrusting into Cheryl.

I felt my crotch start to tingle. My climax was getting close. I drove my cock in hard and deep. Then I pulled out fast. Finally I drove it in and held it there as my cock spurted my cum into the condom.

I pulled my cock out and fell over on my side on the bed near Cheryl.

"Will, I don't know what to say. I didn't know sex could feel so good. I've never orgasmed with a boy before."

I looked over at Cheryl and said, "I'm glad you enjoyed it. You're very sexy. Have you had sex very often?"

"Bruce and I did it four times in the month before we broke up."

"You said I didn't need a condom even though you aren't on the pill. What did you and Bruce use for birth control?"

"A couple times Bruce pulled out before he shot off. The other times he got too excited and didn't pull out."

"Aren't you afraid he got you pregnant?"

"No. I had a period last week. I'm OK."

I pulled the condom off and dumped it in the waste basket. I rolled onto my stomach and kissed Cheryl deep. "Will, would you like to do that again?"

I glanced at the clock. We only had about twenty minutes. "I'd love to, but I don't think we have enough time. We better get cleaned up and dressed before my family gets home from my brother's hockey game.

We put some of our clothes on upstairs in my bedroom and then we went to the family room to find the rest of the clothes. We sat down on the sofa.

"Will, can we get together again soon? I'd like to do this again."

"I'd love that. I'm busy tomorrow. How about after school on Tuesday?"

"No, I have piano lessons on Tuesday. What about Monday?"

"I have scouts then. Wednesdays?"

"I'm free then. On Thursdays I have Dance. Are you free on Fridays?"

"Most Fridays. So, we'll get together on Wednesdays and Fridays. It sounds great. I've really enjoyed spending time with you Cheryl." I gave Cheryl a kiss. "One more thing. Would you be my date to the Spring Dance at school in two weeks?"

"Yes. Of course."

We were watching TV when my family got home. My brothers Kyle & Andrew went flying by the door. Then my sister Lizzie went by. My mom stuck her head in the door.

"Hi Cheryl, it's nice to see you."

"Hi, Mrs. Henry"

"Actually, it's Mrs. Martin. I'm remarried. What have you guys been doing?"

I answered, "We've been watching TV."

Cheryl continued, "We're just hanging out and getting to know each other."

Mom replied, "That's nice. Don't mind our interruption. Keep doing whatever you were doing." My mom left the room.

I asked, "Just getting to know each other? Maybe you should have just told her, 'I was screwing your son.' I really don't want to tell my parents too much about my sex life."

"Relax Will. It's fine. By the way, what time is it?"

"4:30"

"I've got to get going. My mom gets pissed if I'm late for dinner. I'll see you at school on Monday."

Each school day, Cheryl and I talked between classes and before English class started. We discussed our plans for Wednesday afternoon. Both of us were horny and ready to explore each other more.

Wednesday afternoon, Cheryl arrived at my house about fifteen minutes after me. We went straight to my bedroom. We kissed and made out for fifteen or twenty minutes. We kissed and groped each other, removing one piece of clothing at a time.

I loved Cheryl's breasts. They were almost as large as Megan's. The skin was silky smooth and quite white. I loved the feel of them in my hands as I massaged and caressed them. Cheryl giggled and kissed me as I fondled them.

When Cheryl and I were naked I asked her to lie down on my bed. I got between her legs and licked and lapped her pussy. I pleasured her with my fingers and tongue until she orgasmed.

I asked, "Cheryl, would you be willing to try fellatio?"

"What's that?"

"You lick and suck on my penis. It feels really good. I imagine about the same as when I do that to your clit."

"Oh, you mean a blow job? I've never done that. Bruce wanted me to, but I said no."

"Cheryl, will you try it for me, please? It'll feel as good for me as when I do your clit."

"I guess I can try. You have been really wonderful to me when you eat me out. What do I do?"

I sat on the bed and motioned for her to get up and kneel in front of me. "Hold onto the base of my cock. Now lick the top."

Cheryl licked the drop of precum off the tip of my cock. "Wow, that tastes pretty good."

"Now lick around the head and then up and down the shaft." Cheryl followed my directions exactly. I hadn't had a blow job since I broke up with Michelle a couple months ago. Cheryl was doing great for a beginner.

"When you're ready, put the head of my cock in your mouth. Move up and down on the head." Cheryl followed directions exactly again. Her mouth was so moist and warm.

"Aahhhh... watch out for your teeth, please?" I pleaded.

"MMmmssorrrieeee Mmwilllllllll..." Cheryl tried to say with a large cock stuffed in her mouth. She pushed her mouth down my cock shaft and pulled up again, fucking her mouth with my cock. I moaned and squirmed as she sucked me. Once she gagged when she went down too far. Cheryl was more careful after that.

When I felt the "URGE" coming, I pulled her head off my cock and jerked myself off until my sperm shot out. I made a mess all over my pubic hair.

"Wow, Will. That was cool. Did it feel as good as it sounded?"

"Oh yes. You did great for your first time. It was wonderful."

"Your cock is drooping. Will you be ready for the main event?"

"I will be if you play with it a little. I lay back on the bed and Cheryl lay beside me. She stroked and rubbed my cock. It took about five minutes, but I was ready to go again.

I sat up and picked up the condom I had on the nightstand. I opened the package and started to roll it down over my cock.

"I'm safe this time of month. You really don't need that Will."

"I'd rather use it, OK?"

"If you want."

Cheryl lay down on the bed and spread her legs. I said, "Cheryl, I'd like to try a different position."

"What do you mean? Is there another way than you on top of me?"

"Ah, you poor sheltered girl. There are many, many more ways than missionary position. Let's try another."

"OK, what do I do?"

I lay down on my back in the center of the bed. "Get on top of me and straddle my waist with your legs." She did this.

"Get down on your knees." I held my cock straight up, pointing at her pussy. "Now just sit down on my cock."

"Like this?" Cheryl sat down and sank my whole cock into her pussy.

"Yes, exactly! Now you are in control. Go as fast or as slow as you like. This is called the female superior position."

Cheryl started to hump herself on my cock. Slowly at first as she got used to this position. Then she picked up speed. Her pussy dribbled juice onto the base of my cock. I played with her tits as she fucked herself on my cock. After a few minutes, I switched to playing with her clit. Cheryl and I were both moaning and panting as we brought each other towards climax. I twiddled her clit, trying to send Cheryl over the edge.

"Keep doing that, ooohhh... Wwwwiii... lllll... Ohhhh... Aaaeeiiiiii" Cheryl moaned.

Her pussy squeezed and milked my cock, begging for my sperm. I held out for about ten more seconds as Cheryl rose and crashed down on my cock. My second orgasm drained my sperm, and my energy. I collapsed back onto my bed in a stupor. Cheryl lay on top of me, my cock still embedded in her womanhood.

She kissed me and played with my nipples while I recovered my senses.

"Will, you are amazing. Bruce and I didn't have a clue what sex was." I cringed at the mention of her ex-boyfriend again. I was getting tired of hearing about Bruce. I kept my mouth shut.

"Will, why do you always use a condom? It's safe right now for us to have sex without it. It feels so much better too."

"I know it feels good. I have done it without a condom with girls on the pill. It's just that I have two friends, no actually two couples of friends, who got in trouble. You probably know who they are. They go to our school."

"Who?"

"One couple is Justin Baer and his wife Sherry. Do you know who I mean?"

"Of course, everyone knows who Justin is. He's a football star."

"Well, they have a 2 month old son. The other couple is Jon Miller and his girlfriend Amy Holt. Amy is due in two weeks."

"How do you know them?"

"We all went on a two week camping trip in Canada last summer. John and Amy weren't a couple when we left. But they fell in love on the trip. They lost their virginity on the trip. Sex without protection. The baby is the result. Actually I lost my virginity on that trip too."

"Did you bring condoms on the trip?"

"No. I was just lucky. The girl I was with was on the pill. I could just as easily be in trouble like Jon and Amy. That is why I am so careful about protection. I've watched Justin, Sherry, Jon and Amy. I know I am too young to be a father. Way too young."