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?

Michael reached for the waist band of my shorts. I popped my hips up and let him lower the shorts. I don't know if he expected it or not, but my shorts were lined. I had nothing on beneath my shorts. I plopped my bare butt on the bed and lifted my feet up so Michael could remove the shorts. There I was in all my skinny, pale, white glory.

"Too skinny," I remarked as Michael stared at me. "I know. Everyone says it."

"You look hot," Michael answered. "I want to make love to you so much."

"That is what we are here for," I said. "If you still want me."

"I most definitely want you, Rosie," Michael declared as he clambered onto my body again. His hard, 185 pound body pressed against my body as we returned to kissing. He rubbed his hard, cloth encased package against my naked crotch as we continued making out. Hot? God, this boy was making me hot.

Michael switched to kissing my cheeks, nibbling on my ear lobes and then kissing down my neck. He continued down across my chest until he hit one of my sensitive spots, my hard nipples. Michael knew it. He lavished attention to kissing, suckling, nipping and biting my sensitive brown swirls of flesh.

This was mind blowing already. Taylor and I enjoyed our sexual exploration together but it had never, ever been this intense for me. Michael continued sawing his hard, cloth-covered erection against my naked groin. I was afraid I would come just from Michael's dry humping.

I managed to squeak out, "You still have clothes on," between moans as Michael blew my brain's circuitry. He stopped his assault on my nipples momentarily and hopped out of my bed. He smiled before slowly pulling his boxer-briefs down.

The sight confirmed all my hunches about Michael's endowment. This boy was big! I stared at his cock. It was a brown, quite a few shades darker than the rest of his body. It had a light band of skin just below the big, purplish-brown head. I shuddered as I stared at the mesmerizing organ. It had to be eight inches long and a couple inches across. That was going in my body!?!?

"Are you ready for this, Rosie?" Michael asked as he gestured towards his cock.

"Soon, but not yet," I answered. "Come up on the bed. You went down on me last Wednesday. I want to return the favor."

"You know you don't need to," Michael responded. "We can hump some more or get down to the main event – whichever you want."

I patted the bed. "You went down on me," I explained. "I want to return the favor."

"I won't turn down a blow job if one is offered," Michael answered. "Just remember, it isn't necessary, if it grosses you out or anything."

"I've never done it before, but I am willing to try."

Michael climbed into my bed and lay down beside me. I scooted around cross-ways on the bed and lowered my head towards Michael's groin. This cock was impossibly big.

I had no experience giving blow jobs but had read up on the techniques on-line since Wednesday. I knew I needed to share everything if I was to develop a relationship with Michael. If it turned out that I was willing to have a relationship with this boy.

I swallowed hard and engulfed his big cockhead with my mouth. "Teeth!" Michael hissed.

"Ssoorrwwy," I mumbled with a mouth full of cockhead. I tightened the seal with my lips and made sure my teeth didn't touch Michael's sensitive cockhead. I swirled my tongue around the big invader. I could hear Michael moan as I sucked him. I wrapped one hand around his cock shaft. Damn! This boy was big. My thumb and forefinger couldn't touch as I encircled the engorged phallus. I stroked the big boy as I suckled and teased the head.

I must have been doing OK. Michael was moaning and squirming as I blew him. I pulled off his engorged head. Michael moaned an "ahhhh..." I licked around his head for a moment and then licked down the big vein on the underside of his cock, until I reached his balls. I licked around his hair-covered balls. I tried to suck one of the balls into my mouth. It barely fit. Michael's balls were proportional to his big cock. I licked my way back up his cock again before engulfing his head with my mouth.

I sucked and stroked, stroked and sucked. It didn't take very many minutes before I noticed Michael tense up. I knew the meaning of this. I sucked extra hard and swirled my tongue around his cockhead while I stroked his shaft. Michael moaned and squirmed from my efforts. He tensed and growled, "Oooohhhh ... Shit! I'm ... gonna ... FUCKING ... come..."

I could feel his cockhead swell in preparation for firing. I was OK with giving head but I wasn't ready to swallow, at least not yet. I gave Michael one more suckle before pulling my mouth away. I felt his cock pulse as I pulled off. The first spurt of semen spurted against my cheek. I pulled further away. The rest splattered across his chest and stomach, pooling in his belly button.

Michael gasped and panted. I sat on my haunches and looked down at the boy. He just glowed from his orgasm.

"That was fucking awesome, Rosie," Michael finally panted, as he recovered his wits. I wallowed in the boy's praise as he recovered. I grabbed some tissues from my nightstand. I wiped the come off my cheek before cleaning up Michael's belly.

"You ready for the main event?" I asked. Michael was fisting his tumescent cock.

"I'm almost ready but you're not," Michael answered. He motioned for me to lay down on my bed again. "You need to try some fingers before you get this." He waved his rapidly hardening rod towards me. "This might be a bit much for the first thing in your hole."

"You know better than me," I admitted.

"Where's the lube?" Michael asked. I pointed towards my dresser. Michael hopped out of bed and retrieved the squeeze bottle. Michael pushed my legs apart and climbed into bed between them. He pushed them up so my knees were practically up to my shoulders. He squirted the cool lube onto his fingers and then probed down below for my hole. He let his thumb strum across the sensitive area above my opening.

I tensed as I felt his fingers spread the cool lubrication around my opening. I tensed when Michael tried to worm one finger into me. "Relax," my soon-to-be lover commanded. I tried my best. The finger slipped into me. I felt Michael probe my insides for a moment before withdrawing it. The finger returned again, pressing more easily into my hole this time, cool from the additional lube Michael had applied.

I wasn't sure if I would be able to stand something thrust inside my body. I found one finger felt OK. Actually, more than OK. I was getting into his finger fucking. Michael stopped for more lube two more times. I felt stretched a little each time he returned the finger to my insides.

"Does three fingers hurt?" Michael asked soothingly.

"Three?" I gasped. "That's three?"

"It is," Michael confirmed. "Three with lots of lube and plenty of preparation."

"Am I ready for the real thing?" I asked. The moment my cherry disappeared was rapidly approaching. That big, brown, monster was looking huge again. Could I do this?

"Let's try four fingers first," Michael suggested.

"You have the experience," I agreed. Michael pulled his fingers out again for more lube. I knew he had applied a lot. I could feel it running down my bottom and between my butt cheeks. There was a little pressure and a pinch as my soon-to-be lover forced four digits into my poor, stretched hole. Michael finger fucked me for a minute or so. I didn't feel any pain.

"I think you're ready," Michael announced. "Are you sure you want to go all the way, Rosie?"

"Absolutely," I confirmed. "Take my cherry."


"You are going to use protection, right?" I asked.

"I'm not an idiot. It's 2014," Michael responded. "This never goes anywhere without being wrapped." I watched as Michael pulled a condom out of his pants pocket and tore the wrapper open. He carefully unrolled the sheath down over his huge cock. Michael spread lube over his humongous organ as I watched.

'Was I really ready for this?' I wondered. Michael's cock looked much too big to ever, EVER fit inside me. Michael clambered into bed again, between my legs. He pushed my legs back so my knees were pinned against my shoulders again, neatly exposing my hole for his use. Michael gave my hole one more shot of lube before scooting up against me. I stared down at that big, angry looking brown rod. Was I ready for this?

Michael nestled the head again my hole. I involuntarily clenched my muscles. "Don't tense. This will hurt if you do." I willed myself to relax as he stared down at me. I could see the love and concern in his eyes as he prepared to deflower me.

Michael pressed gently, barely perceptibly at first. My lover was patient. He continued the gentle pressure until my hole relaxed more. Suddenly an inch and a half of his big cock slipped through the ring into me. I know it is supposed to hurt, but it didn't.

"Are you OK?" Michael asked. I smiled and nodded yes. He leaned down and kissed me on the lips. Our tongues dueled. I felt him hunch his torso in towards my body as we kissed, burying more of that big, hot invader in me.

The feelings Michael was giving me was unlike anything I'd ever felt before. Michael broke our kiss and pressed further. I loved the feeling of this huge, hot cock burying itself in my body. The friction as it forced its way into me was exquisite.

"God, you're tight," Michael moaned as he bottomed out. I could feel his balls planted against my backside. "Does it hurt?"

"It feels amazing," I responded. "Fucking amazing."

"That's the idea," Michael laughed. "Ready for more?" I nodded my consent. Michael pulled his torso away from me, slowly withdrawing the hot cock from my hole. It felt great sliding out but it left a void. Michael humped forward again filling the gaping hollow in me.

In and out. In and out. Michael varied speed and angle of thrusts for variety. In and out, he continued humping me. I reveled in the feelings he was generating. Being fucked was the best thing that I had ever felt in my sixteen years on this earth!

In and out. I grasped and rubbed his muscular sides as he humped and thrust. Occasionally I would wrap my arms around his neck and pull him onto my chest so we could kiss and allow our tongues to duel again. Michael never let up the assault on my hole. In and out. God, this was wonderful.

I was getting hotter as I was fucked. Michael hunched over as he humped. He licked, kissed and suckled at my left nipple as he used quick, short rabbit thrusts into me. His pubic area bounced against my body. I was going to come! I knew I was going to come! Soon!!

Michael rose up off my body again and stared into my eyes as he slowed his thrusting into my body. "I love you, Rosie," he declared.

"This is amazing," I responded. "You're so special, Michael Murray." Did I love this boy? Maybe. Could I say the words to Michael while I was going steady with Taylor? That didn't seem right. I had so many issues to decide. Loving the way Michael fucked me just complicated my life immensely. It would be so much easier if I had hated this.

My orgasm was approaching and I hadn't even touched myself. I had never experienced anything this intense before. I let Michael fucking sweep me over the edge. As I felt the first contraction of my orgasm, Michael groaned, "Oh ... God! I'm..."

I didn't need him to announce it. Michael burrowed his cock as deep into my hole as it would go and froze, his face a mixture of pain and delight. I could feel the pulse of his contractions as his spurted his seed into the condom protecting the two of us. My brain was fried.

I stared down between us. My balls were laying on either side of my cock. Untouched by man or boy, it twitched and then spit out my load. The first of my come landed halfway up my chest. More spurts landed on my chest and stomach. The final dribbles of my spend pooled just below my belly button.

I collapsed back on my bed to recover. Michael grinned down at me with unfocused eyes. After half a minute he declared, "That was fucking awesome. Hadrian Justinian Rose, I love you!"

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