No More Cherry

by Douglas Fox

Caution: This Sex Story contains strong sexual content, including mt/ft, mt/mt, Teenagers, First, Safe Sex, .

Desc: Sex Story: Shockingly, Rosie is captivated by hunky football star, Michael. The problem? Rosie is going steady with Taylor. Will Michael and Rosie's Saturday afternoon tryst spell the end of Rosie and Taylor relationship?


Rosie – 16 years old, junior in high school – 6'-2" tall, 138 pounds – member of school volleyball team.

Michael – 17 years old, senior in high school – 6'-2" tall, 185 pounds, football team captain and tight end.

Taylor – 15 years old, junior in high school – 5'-5", 130 pounds, avid Scout and camper. Has been going steady with Rosie for the past four months.

Skinny Rosie unexpectedly falls for hunky, football team captain, Michael. Things escalate. Will Rosie, who is going steady with Taylor, cheat with Michael and allow him to go all the way one weekend when the parents are away. How do they handle the inevitable trouble that results from this hook-up?

'How had this happened?' I wondered. Michael's heavy body pressed against mine as we Frenched. His tongue diddled against mine. Both us were topless. The wisps of hair on his chest tickled me as our bodies rubbed together. His body rubbed against my stiff nipples.

"You make me so fucking hot, Rosie," Michael gasped between kisses.

My parents were away for the weekend. I was alone in my room with the hottest guy in our high school. We had all afternoon alone, with no possibility of being disturbed. Could I go through with this? Could I go all the way with this ... this boy?

Michael and I continued making out. It felt ... amazing. I'm no stranger to first base – or second and beyond either. It was more intense than I'd ever experienced while dating others. The way his body rubbed against my chest and the things his tongue and lips were doing to me ... God, he made me so horny!

I knew I was having the same effect on Michael. His "package" was hard and pressing into my stomach. Would he want to go all the way with me, a tall, skinny volleyball player? He's a senior, a captain and a tight end on our football team. Me? I was, by everyone's agreement, a beanpole and a year behind him in school.

None of my insecurities affected Michael. He continued kissing and dueling his tongue with my tongue. I wrapped my arms around his muscular sides and back as we made out. Michael slipped a hand between our bodies, grasping my chest so my stiff nipple was under his thumb. He rubbed it. Oh ... My ... God!

I thrust my tongue into Michael's mouth. He sucked it in and twirled his tongue against mine. We continued, heedless of anything except lips on lips and tongue on tongue. We made out frantically for ... minutes? Who knows? Finally we had to break our lip-lock momentarily to breathe.

"God, Rosie," Michael gasped between pants. "Why'd we ever stop being friends?"

Michael and I had been had been playmates when we were small, before his family moved to another neighborhood.

"Different elementary schools?" I offered. "Different circles? I don't know."

Five years at different elementary schools had killed whatever connection we once had. By the time I was in the same middle school as Michael, I had my friends. He had his. Anyway, he was a grade ahead of me. We said, "Hi," when saw each other in the hallways. Nothing changed when we moved on to high school – until the school year started a month ago.

Michael and I were signed up for the same Photography class. By chance, our teacher assigned us to sit at the same table. The decade apart just seemed to slip away as we talked, laughed and worked together. Soon Michael was teasing me and calling me Rosie again, like he had years ago. I responded by calling him Mikey, but that didn't last. It didn't fit the football tight end image he cultivated. I settled on calling him Michael.

Our friendship rekindled and then burst into flame two weeks ago. I'm supposed to be in a steady relationship ... well ... I AM in a steady relationship right now. Things escalated beyond friendship two weeks ago when Taylor, my steady, had a Scout camping weekend. Recently broken up with his bitchy, high maintenance girlfriend, Brittany Miller, Michael and I decided to go to the movies on a Friday night – just as friends.

We saw one of Pixar's animated flicks. It was funny. We laughed and had a great time. Things developed further at the end of the movie when Michael drove me home. He pulled over and stopped a block from my house.

"This was a great night, Rosie," Michael. "You have no idea how much I enjoyed this."

"I had a great time too," I agreed.

"I need to admit something, Rosie," Michael said as he stared into my eyes. "You will keep a secret for me, won't you?" I nodded yes. "Maybe I should show you rather than tell you."

I was shocked when he put his hand around my neck and pulled my head closer to his. He leaned in and kissed me. On the lips! I was flustered and startled but my body responded when he slipped his tongue into my mouth. My eyes glazed over and I saw stars as this ... this boy kissed me like I'd never been kissed in my life.

We necked for probably five minutes. It was nothing like when I necked with Taylor. Taylor and I had gone much further sexually in the four months we'd gone steady but the feelings then were nothing like these now. I finally realized the time as Michael and I made out.

"I've got, like, three minutes to get home," I protested as I broke away from his kiss.

"Are you all right with this?" Michael asked. "I didn't freak you out with the kiss?"

"I don't know," I admitted. "I never expected ... I ... I'm just confused."

"This is our secret?" Michael asked.

"Yes, totally," I agreed. "How could I tell?"

"I want to be more than friends, Rosie," Michael responded. "Can you feel that way ... about me?"

"I don't know," I answered. "I just don't know. This is all so unexpected. I never suspected you ... I have Taylor."

"Do you love, Taylor?" Michael asked.

"Love?" I remarked. Taylor and I had fun together. We explored each other's bodies as we learned about what teenaged hormones could do. It was fun but ... was it love? "I'm confused. I need time."

"Fair enough," Michael said. He planted one more, less intense kiss on my lips. "Let's get you home before you turn into a pumpkin."

Michael and I surreptitiously hooked up half a dozen times after that movie. Mostly they were make-out sessions except for last Wednesday after school. Michael had given me an oral quickie. It blew my mind. Taylor had tried before, without nearly as much success. The feelings were so much more intense with Michael. Wednesday's quickie, and Taylor's announcement that the family was heading to the west end of the state this weekend to visit the grandparents, led directly to Michael being alone with me this afternoon in my bedroom. We would explore whether I was ready for a serious relationship with Michael.

"Rosie, I am falling in love with you," Michael declared, as he sprawled on top of me, chest to chest in my bed.

"Is that a good thing?" I responded. "What are people going to say?" Michael laughed.

"It's a black-white thing, isn't it?" he asked.

"No, it's not," I declared. Michael always joked about being a black man. I guess to some he would be considered black, no matter what he looked like. His dad is a red-haired Irishman with skin paler than mine. Granted, his mom is considered African-American, albeit, a very light skinned African-American. Michael had straight red hair that looked nothing like what you would expect for a black person. His skin color was slightly darker than my Caucasian skin, but only to a slight degree. He certainly wasn't black. Not even brown or beige. Michael's skin color could best be described as matching my coffee, on the few occasions I drank coffee – lots of milk and sugar with a touch of coffee for flavor.

"What then?" Michael asked rhetorically. "I don't give a rat's ass what people say. I am falling for you and I don't care who knows."

"It isn't that simple and you know it," I insisted. "People WILL talk."

"Fuck 'em!" Michael answered.

"That wasn't the idea for this afternoon," I said. "I wanted you to do that to me, not everyone else."

"Are you sure, Rosie?" Michael asked. His face went serious as he stared into my eyes. "We don't have to if you don't want to."

"I need ... no, we need to explore what this is between us," I responded. "I need you to take my cherry this afternoon. I need to understand this."

"It may hurt," Michael said. I could feel that big, steely bar in his pants, pressed into my abdomen. I knew he wasn't going to be small. This would be a hell of a first time for me.

"I'm sure," I answered, laughing and pointing to the bottle on my dresser. "I bought lots of lube. I hear that is important for the first time."

"Lube is always important," Michael agreed. "If it isn't sloppy it isn't good."

"Let's do this," I declared. "Kiss me again." We swapped tongues for a minute or two. Michael sat up, straddling my torso.

"We've got too many clothes on," Michael remarked. That was only partly true. Michael and I took full advantage of this late September, Indian summer weekend to dress in T-shirts and sport shorts today. This weather was simply not normal for late September in Connecticut. I pulled his shorts down to reveal a pair of gray Under Armour boxer-briefs. Michael hopped out of bed and shucked the shorts but kept the briefs on.

I eyed the bulge in Michael's briefs. I don't know if the stereotype of all black men having big cocks was true or not. I did know Michael was well endowed. I gulped as I thought about that big thing going inside my body. Would it fit?

.... There is more of this story ...

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Story tagged with:
mt/ft / mt/mt / Teenagers / First / Safe Sex /