The Age of Madeline

by Tasty Little Pop Tart

Copyright© 2015 by Tasty Little Pop Tart

Romantic Sex Story: Madeline has been in hiding for years. Her desire for companionship finally wins out over caution. The only problem is she is disguised as a boy, and needs to prove the boy she likes is trustworthy to keep her identity secret. Her plan to find out nearly backfires.

Caution: This Romantic Sex Story contains strong sexual content, including mt/ft   Consensual   Romantic   Reluctant   Heterosexual   Fiction   Humor   First   Oral Sex   Transformation   .

Note: This story is dedicated to my friend Bill, who convinced me to keep writing.

I never expected to kiss a boy again, much less suck his cock. But I did, the night of my sixteenth birthday.

I sucked two, actually, my two best friends, Michael and David. They were sixteen also. We were in my basement, trying out my new Xbox 360. It was an awesome machine.

About ten o'clock, right out of the blue, David asked if I would suck his cock. "Sure," I said blithely. "Whip it out, dude!" I couldn't believe when he did.

"What are you doing?" I croaked, horrified. He wasn't just out, but fully erect. I realized he--they--had planned this. I began to laugh.

"You are out of your mind! What makes you think I would even want to?"

David shrugged. "We were hoping you would. Both of us, you know?"

"You're out of your mind!" I repeated.

To my horror, I wanted to see his cock, see what it looked like erect, how big it was. I kept my eyes right on his.

"I'll give you ten bucks," he said.

"Fuck you!" I shot back, laughing.

A glance at Michael showed he looked embarrassed. David was embarrassed too, red faced with anxiety. Peripherally, I could see him losing hardness. Thank God. I was so not ready for this yet.

No one said anything for a time. Then I said, "I don't want to suck you. Put it away, David."

He did, humiliated. I could tell he planned to go. To ease the tension, I asked, "Has anyone ever sucked it before?" I meant a girl, of course.

He zipped up, shaking his head.

"Why did you think I would!" I asked, honestly curious.

His face got redder. He muttered, "Because of those stories you write."


"What stories?" I croaked.

"The ones on the flash drive you left in my bedroom."

Oh, fuck, I thought. The flash drive. When was the last time I saw it, I wondered. I hadn't written anything lately. I was so not ready for this.

I sighed. "You got it all wrong, David."

He blinked at me, confused.

"It's his cock I want to suck," I lied, nodding at Michael.

Wordlessly, I unzipped Michael's shorts, freed his penis and put it in my mouth.

It wasn't much, as blow jobs go, but I tried my best. They were both over anxious and I was butterflied and intimidated. Neither one came, although both leaked in my mouth. I was pretty sure about that.

David was significantly bigger than Michael or me. I stroked myself while I sucked, my first time doing either as a boy. I didn't come, and wouldn't know how to do it anyway, in disguise. I had never occasion to experiment.

"How long have you wanted to do this?" Michael asked. He was bigger than me too, about five inches long. David was six inches plus, and much thicker. He had a man's cock.

Rather than answer, I let David transfer my mouth to his cock, while I awkwardly stroked Michael.

"Do you like it?" David asked.

I nodded. It was embarrassing.

"Have you always wanted to do it?" he asked.

I shook my head.

"You know, in those stories you wrote, you asked me to come in your mouth. Michael too. And you swallowed us."

How humiliating to be reminded of that. I nodded acquiescence. I would let them come in my mouth. If they wanted to. Turned out neither wanted that. It was too new.

You can imagine how I slept that night. Or didn't. It was misery in school the next day, but neither of my friends said anything, though both were obviously disturbed. After school, Michael whispered that they wanted to play the Xbox again. It took less than a minute for David to bring it up.

"Can we do it again?"

I have to admit he was neither overeager or demanding. Both he and Michael were shamefaced and anxious about this. Michael's face was on fire.

"We'd also like ... you know ... if you would... ?"

Swallow them, I know. "Yes," I agreed on both counts.

David requested I leave my cock in my pants this time. It really bothered them, he said, seeing me stroke it off. It bothered me too, for exactly the same reason.

"Whatever you want," I told him. I prayed neither would ask me to take off my shorts. In some of those stories I had anal sex with them. I wasn't ready for that dream come true yet.

They stood side by side and I dropped to my knees. David freed himself while I unzipped Michael and took him out. Same as last night, I made Michael hard with my mouth. David had no such problem.

To his surprise, I said I wanted to measure him fully erect. I ran to Mom's bedroom and found the cloth measuring tape in her emergency sewing kit. On the way back, I considered how crazy this was, a day after my sixteenth birthday, sucking my two best friends. No girl should do that.

"You won't tell anybody about this will you?"

They both looked sheepishly stunned. David croaked, "Are you nuts? Tell someone I let you suck my cock? No way!"

"Don't want to be thought of as gay," I said dryly. The stab further reddened his face;, Michael looked like he wanted to leave. I said to relax, and thanked them for letting me do this. Writing about it only frustrated me.

"How long have you wanted to do this?" Michael asked again. This time I answered.

"The website I post those stories to doesn't allow any sexual activity or relationships of any characters before the age of sixteen, so let's say I wanted to as soon as I woke up yesterday morning."

"But--?" Michael started to object. I held up my hand.

"Stop. I want to write about this and post it on that website. I can't do that if we talk about anything prior to my sixteenth birthday. So shut up, Michael..."

I wouldn't have told David to shut up. Though not much of one yet, he was the Alpha male of our trio. I was the Beta, despite being on my knees with my mouth open, and not a boy.

David was 6-1/2" long, and 5" around, which translates to 1.6" in diameter. Michael measured 5-1/2" long, which surprised me, because he seemed so much shorter than David. I managed a puny 4-3/4" long and 1.25" diameter, not bad, I thought, for only my second try. I'd have to stay that length, for some time to come.

David asked the loaded question. "Did you ... you know ... want to have, um... ?" He glanced anxiously at Michael, who colored a dark red.

"I'm not ready for that yet," I assured him. "This is all I can handle at the moment. When did I leave my flash drive at your house?" I asked suddenly. I hadn't looked for it in my backpack yet.

"Last week. It was under my desk. It must have fallen out when you were looking for something." He glanced away, embarrassed. "I shouldn't have looked, but I was curious."

"So am I," I teased. I put him back in my mouth and proved how curious I was.

It lasted an hour and twenty minutes with me spending an equal time on each cock. Michael finally loosened up and began to enjoy himself. After a while, they sat down side by side on my bed, but David stood again to try fucking my mouth.

"This is okay?" he said, anxiously. "You don't mind me doing this?" It was one of the things I had written about in the stories.

"Uh-uh," I said, shaking my head. He had a hand on the side of it and one behind, holding it steady.

After a minute or so he began running my mouth up and down his cock, as well as fucking it. I fought not to gag. Mouth-fucking and giving a blow-job are nothing alike.

He reached orgasm suddenly, yanking himself free and beating off violently while shooting cum in my mouth, and all around it. I coughed and gagged and struggled ineffectively, not trying to get free, only shocked. I tried to swallow, but that wasn't happening. I was totally grossed out. I should never have written that part.

"Excuse me!" I croaked, struggling up and running for the bathroom. I was gagging and about to throw up. I spit the stuff into the toilet and scrubbed my face with tissue paper, so grossed out. I cleaned it off my hands, the smell sickening me again, and scrubbed my lower face with soap and water. It was on my neck, and the top of my t-shirt. I yanked it off over my head, made sure I had nothing to see, and then went back.

In the bedroom, I muttered an apology and put on a fresh t-shirt. This session was done; Michael had no interest in doing anything else, including Xbox. They left with my best wishes and I immediately jumped in the shower and scrubbed myself clean. That afternoon nearly ended my excursion into gay sex. I changed, and nasty-bated as God had intended me to, with my middle finger.

Neither suggested anything the next day and then it was the weekend. On Monday, after an uncomfortable ride home on the bus, David apologized for Thursday afternoon

"My fault," I told him. "I wrote about it, you know. Just please, you know, don't do it again, David."

We all laughed, and then went to my house for sex.

This continued the rest of the semester, David and Michael in my bedroom after school a few times a week, sometimes getting together on the weekend and doing it. Both came in my mouth routinely. Michael finally did it that Monday afternoon in September and was comically ebullient and unrestrained when he came. David nearly doubled over laughing.

Neither got tired of having their cocks sucked. I became a real pro: Matthew, the incredible cock sucker. We took a break for the holidays and then started up again in January.

"Do you think anyone's getting suspicious?" Michael asked. It was a Wednesday afternoon, the middle of of the month. It was pretending to snow outside.

I looked up, glancing between the two guys. "Nobody is, right?" I asked.

David shrugged. "Not that I've noticed. Why, you think someone is?" he asked Michael.

Michael shrugged also. "I think some people are beginning to wonder, yeah."

"Who?" I said, alarmed.

David glowered at him, a why'd you bring that up, look if I've ever seen one.

"What's going on?" I demanded. "Does somebody know? Did you tell somebody?" I rocked back on my calves, horrified, knees popping loudly.

"No, no!" David assured me. "I haven't told anyone. I promise you that." He glanced at Michael, who only shrugged. "What?" he demanded. "Did you tell someone, Michael?"

Michael turned brick red and muttered something indecipherable.

"What did you say?" David was furious and alarmed.

"My cousin," he admitted glumly. "I may have mentioned it to him over the holidays."

David punched him hard on the shoulder. "You ass! What did you tell him?"

"Pretty much everything," Michael confessed, rubbing his bruised shoulder. David jumped up to beat the living crap out of him. I motioned him to hold on.

"Does he want a blow-job?" I asked.

"Hey!" David objected angrily. He still wanted to pound Michael's face.

"It's okay. If that's what it takes to defuse this mess--" I almost finished by saying, I'm okay with it, but looked to David, instead.

"There is no way," he said hotly.

"OK. What do we do then?"

"Best the shit out of Michael!"

"Besides that?"

He looked down at me, aggravated. "Excuse the way this comes out, but I am not sharing you with anyone, Matthew."

I glanced at Michael, embarrassed. David glared at him, but was beginning to calm down. The growl in his throat, excepted.

Michael looked emasculated and his erection had totally wilted. He was too embarrassed to put it away, and under the circumstances, it was hands off for me.

Matthew, the voice of reason. "If we can avoid a disaster--"

David cut me off. "No way!"

"David..." I soothed.

"One more word out of you, Kendall, and I will take you over my knee and spank you bare-bottomed!"

He meant it, and I shut up. I ended up sucking Gerry Lyon's cock, anyway.

Gerry wasn't a bad guy. He was eighteen years old and a jock, but a pleasant, jocular one. He played varsity football, basketball and lacrosse. He couldn't believe I agreed to suck his cock. He was embarrassed and uncertain he wanted to do it.

"You won't tell anyone!" he threaten his cousin. That made me laugh and David to bunch his fists. All three of them stared at me.

"I'm the one doing this," I pointed out. "That's my question to ask."

"It wasn't a question," Gerry clarified. "He's got a big mouth."

I thought wryly, no, that was me. I said, "Michael has learned his lesson. No one here will say anything more. Besides," I pointed out, "his need to confess is what brought you here in the first place. He deserves some credit for that, don't you think?"

"He deserves a punch in the mouth," David grumbled.

I was not ready for Gerry Lyon's cock. My stomach lurched and I broke out in gooseflesh and a cold sweat.

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