Sweet, Young Stephanie

Her perfect oval face gazed up at me expectantly, both excited and nervous. Her big, innocent eyes looked at me, then drifted to my lips. I'm sure I looked like a mess: mouth covered with saliva, cum trickling down my chin, hair a tangled mess. But I could sense her excitement as I bent closer. I brushed my lips against hers and felt them part. Her tongue probed my lips tentatively, then with more force. She totally wanted my mouthful of cum.

Reaching up, she caressed the back of my head and pulled me closer. Her tongue pushed more forcefully between my lips as she pulled me down, kissing me with more passion than I expected.

I locked my lips to hers and opened my mouth. Her tongue slid inside, probing between my teeth and stroking my tongue as the cum drained from my mouth to hers. Moaning again, she held me close and kissed me, savoring the warm liquid that filled her mouth. I placed two fingers on her throat and felt her Adam's apple bobbing as she swallowed it down. After searching my mouth with her tongue one last time she released me.

"Hee hee," she giggled. "That was naughty."

"Oh yeah," I agreed. Without being asked I came the rest of the way in, climbing over her and sitting on the edge of the bed. My cock was so hard I thought I might cum right then. I took a few deep breaths to calm myself. It was really happening—I was actually in bed with a gorgeous, naked teenage girl. Well, not quite a girl, but she was better looking than a lot of the real women I've dated.

Looking over, my eyes roamed her tight, young body. Her nipples poked up like pencil erasers and her cock had only deflated half way. She stared back with those big blue eyes and I knew I couldn't hold back any more.

In a flash my shoes, jeans, and underwear lay on the floor and I stood beside the bed in only my socks. I guess we matched because socks were all she had on too. My cock poked out at full hardness, bouncing in time with my pulse. Pre-cum smeared over half my length and a thick rope of it dripped slowly from the tip. I watched her look at my dick, her eyes opening wide with excitement as she reach for it tentatively.

"First time?" I asked.

She glanced away and nodded, as if she were embarrassed. It must be weird to be a high school girl but really be a guy. She'd probably been through all kinds of teasing, or worse. Maybe I was the first man to accept her as she is, to be genuinely turned on by her. All of her. I said, "You don't have to do anything you don't want to, but I'd really like to feel your mouth on my cock."

She rolled onto her side, looked up at me with that sweet, innocent face and said, "Really?"

"Oh yes. You are so beautiful, I probably won't last long before I cum."

"You want to cum for me?" she asked coyly. I half expected her to bat her eyes.

"Mm-hmm," I replied as I crawled onto the bed. On my knees, I brought my throbbing dick within inches of her mouth. "You want a mouthful of cum?" I asked.

She giggled. "Another one? I don't know..."

What a tease. Well, I was gonna cum even if I had to stroke it myself. But she reached out again, taking my cock by the base and gripping it lightly. Her hand moved up and down and her gaze dropped lower to watch herself work. I scooted forward, practically sticking my dick in her mouth. Her hand kept stroking as my cock got closer and closer to her shiny tongue.

"Mmmm," she said, and opened her sweet, plump lips.

At last her warm mouth slid over the head of my cock and I almost shot it right then. She removed her hand and her moist mouth glided all the way down my shaft until her nose was in my pubes. Her tongue swirled around my head as she slowly pulled away.

Reaching up to massage my balls, she moaned again. "Mmmmm, yeah," she mumbled around the head of my dick and started back down for another long, slow slurp.

I knew this was going to be tough so I started imagining gross stuff, like the muck I cleaned out of the gutters and the dead mouse I found that morning. Not very exciting but it did keep me from blowing my load after five seconds. I tried to relax and let my dick soften. I stayed really hard but at least I didn't cum. After a few slow breaths I took a chance and looked down at her.

That angel face looked up at me, as innocent as a baby. But the twinkle in her eyes told me she was really enjoying herself. I think she'd been fantasizing about something like this for a long time, and I was happy to help her fantasy come true. I reached down and stroked her silky hair, gently thrusting into her young mouth.

I still thought she was pretty inexperienced because she was doing the same things to me that I had done to her. Flattering I suppose, and it left lots of room to show her new stuff. She squeezed the sweet O of her lips around the base of my cock and sucked. Pulling her head back, she maintained the suction and worshipped my throbbing dick with her warm, slippery tongue.

"Oh shit, that's good," I said, feeling myself start to tremble. "I can't take much more of this."

"Mmmm, mmmm," she mumbled, and picked up the pace.

She gripped me again, stroking my cock in rhythm with her bobbing head. Twisting her hand around my shaft, she sucked harder and went just a bit faster. It felt like heaven and I knew I couldn't last much longer.

"Oh god, baby, you're gonna make me cum real soon," I said, feeling the delicious warmth of her young mouth sucking enthusiastically on my engorged cock. Given her inexperience, I thought I should point out an important issue. "When I cum, it's up to you," I gasped. "Swallow it down, take it in your mouth and spit it out, or back off and let me shoot all over. But whatever you do, keep pumping your hand, okay?"

"Mmmm-mmm," she mumbled and nodded.

I thought about mouth-fucking her the way she did me but I figured she might like to bring me off entirely on her own. It was her first time, after all. On my knees, I leaned back onto my elbows and waited for the inevitable. My cock pointed straight up as this delicious teen bobbed her head up and down, stoking and sucking for all she was worth. Her moans got louder and so did mine. Tongue swirling, sucking harder now, her lips and fist pounded up and down my throbbing dick like a piston. I felt the tingling in my balls that told me a huge orgasm was on the way.

"Ah! Oh yeah!" I shouted. "Fuck! Here it comes!"

If it was possible, she sucked even harder, moaning like a slut from a porn video. She was enjoying this as much as me. My balls got tight and I knew this was it.

With a groan I ejaculated into her willing mouth. I moaned and bucked my hips as blast after blast fired from my rock-hard cock. She was moaning too, slurping and stroking and bobbing away. I looked down but her eyes were closed as she worked my spurting dick. Cum dribbled from the corners of her pretty mouth as she struggled to swallow my huge load.

"Oh God, that's good!" I shouted. "Keep going, keep going! I'm still cumming..."

Another hot squirt blasted from my dick, and then another. God, this chick was draining my balls like I haven't been drained in years.

"Uhhh!" I said, shooting another red-hot blast of sperm into her mouth. Her head bounced up and down and she kept moaning like she was being tortured. Fuck, I didn't care. Another thick shot of cum blasted out and I could just imagine her bobbing Adam's apple as she gulped it down.

"Oh shit," I moaned, finally nearing the end of my orgasm. "Oh God baby, slow down a little."

I felt her suction let up a bit and she slowed her demanding rhythm. Still, her moist tongue spiraled around my shaft and her warm mouth coaxed me to keep going. If I could cum for an hour, she would slurp it up without protest.

Eventually my dick quit spurting, but she didn't give up. Now I knew for sure that she'd never sucked a cock before. I'd just dumped a cumload that would choke Linda Lovelace but she wanted more. I could tell by the low, throaty groans that this chick would gulp anything I could give her. Didn't she know my balls were empty? For a chick with a dick, she sure had a lot to learn. If she kept sucking she'd pull my bladder out through my pee-hole.

"Slow down, honey," I said. "You got it all. There's nothing left."

Oh shit, I thought. What a fucking awesome blowjob. I hadn't been sucked like that since I was in college. And still her angelic face worked my shaft, staring up at me like she was looking for approval. Oh yeah, I approved all right.

"Fuck, baby, that was great," I said honestly. "You have the mouth of the gods."

I had no idea what that meant but it sounded good. And she could suck better than most of the women I've known. Holy shit, I thought. If I can just keep this sweet little cupcake, even for a few months, I'll go to my grave a happy man.

I felt her lips clamp the base of my softening cock and then pull upwards, squeezing the last dribbles of cum out. This hot, slutty muffin wanted every drop of sperm she could get.

"Oh shit," I said. "That was spectacular."

At last she let my half-hard cock slip out of her mouth. She smiled at me but it seemed uncomfortable somehow. Like she was embarrassed. I don't know why, since she just gave me the cock-sucking of a lifetime. But maybe that was the issue.

"That was great, honey," I said.

She looked at me, a young, delicious girl wracked with guilt.

Her lips curved into a taunting smile. She was trying to be innocent but she knew that after today, that part of her life was over. How much cum can you gulp before you realize you aren't a virgin anymore?

I suddenly felt a little guilty. Have I just taken advantage of a young girl who's only trying to find her place in this world? Didn't seem likely, given how much she enjoyed gulping down my hot load. Still, something was going on that I didn't know about. Her angelic face, so full of hope, told me that she needed the same thing everyone does: acceptance.

I would accept this chick 'til the ends of the earth. That heavenly mouth? Those firm, perfect tits? I didn't care that she was really a guy, at least biologically. My hard cock needed a place to unload and I found it. Just like she needed hard, throbbing proof that she was desirable. We all have our needs.

She collapsed on her back, wiping the trickles of sperm off her cheeks.

"Did you like that?" she asked.

Either she was the world's greatest tease or she was really, really insecure. I didn't care which.

"Honey, that was great," I assured her. "You have the sweetest mouth I've ever felt."

It was true, and I think she understood that. Nodding, she stroked my dick and said, "God, that was amazing. I've never..."

Again with the innocence. Maybe my cock was the first one she'd ever sucked, but I'm sure she'd thought about it many, many times. I was laying in the bedroom of this saucy high school girl, and her mom would be home in less than an hour. Could it get more dangerous than this? Maybe, but I didn't care.

Her rosy, sperm-slathered lips gave a shy smile. She looked at me like a wide-eyed virgin licking her way through a butter pecan ice cream cone. Whitish-clear liquid coated her lips and dribbled down her chin. Her innocent gaze seemed to ask, "did I do something wrong?"

I like to think that I'm a decent guy. I really hadn't planned to spy on her, suck her sweet young cock, and then crawl through the window and force-feed her my dick. But that's just the way it turned out. It wouldn't take long for my cock to get hard again, but in the mean time we chatted. She was actually a very articulate girl. We talked about her daily routine. Frankly, I was curious what her life was like. Did anyone know her secret? Was she getting hassled at school?

Turns out that she was bullied a lot the last place they lived. That's why they moved. Her dad, unable to accept her seemingly strange behavior, had just left, and it went downhill from there. Everyone at her school knew her as Steven, at least before she started living as a girl, and the harassment got worse with each passing year. It culminated when a group of boys cornered her behind the gym one day. Seems that they alternated between smacking her around and trying to get blowjobs before one of the teachers showed up and put an end to it. But it was obvious that it really hurt her.

It's tough to be who you really are, and stand by it no matter what. In the end, Stephanie and her mom had moved halfway across the country so she could have a chance to start over. Here, she was just Stephanie and no one knew any different. No one even suspected, or that's what she said. I sure never did.

She rolled on her back again, stretching languidly, for all the world like a delicious eighteen year old girl wiggling on her bed. Her nipples still stuck up, and with her cock tucked between her smooth thighs there was nothing to even hint at her secret.

I knew her mom would be home before too much longer, so I had to decide what to do. We'd talked for maybe ten minutes but that was plenty of time for my cock to start inflating again. My eyes roamed her taut body, drifting from the striped socks that bunched at her narrow ankles, up her smooth, lean thighs, past the patch of hair at her crotch flecked with stray blobs of cum, over her flat belly to those small, pointy tits. She watched me admiring her young body and gave shy smile. Her full lips curved up almost unwillingly and her luminous blue eyes were both alluring and somehow hesitant. With that perfect oval face she could easily be one of those teen models, showing off her trim young body in department store ads. In spite of her luscious curves she seemed insecure. Given the reality of what dangled between her slim thighs, I guess I could understand why.

For all I knew this would be the only chance I had with her before guilt or fear made her refuse to see me again. I leaned over and kissed those plump, fashion model lips, licking up the traces of cum as my hand drifted to her tits. We made out for a couple of minutes and then I lowered my mouth to her nipples. I sucked and licked them, squeezing them gently and getting soft moans of approval from Stephanie. She opened her thighs and her rock-hard cock sprang out and smacked against her firm belly.

I reached for the cock and began stroking it. My mouth drifted south and slowly engulfed the head and she moaned again. I gently bobbed up and down, giving long, slow sucks with almost no suction.

"Mmmm, yes," she said. "Keep going, I like that."

I moved down so I was now between her slender thighs. Bobbing my head I massaged her balls, and then let my fingers slip down into the crack of her ass. I poked gently at her asshole and she gave another long, "Mmmmmmm." After slathering my finger with a thick coating of spit I again pushed at her little pink button. My middle finger slipped in and she groaned.

Sucking a bit faster, I slipped my finger all the way in and then pulled it back almost all the way out. I slurped her knob and finger-fucked her tight teen ass as she started gyrating, bucking her hips up and down and groaning in ecstasy. I knew exactly what she needed.

"You want me to fuck you?" I asked.

She lifted her head and looked at me with those wide young eyes. "You really want to?"

"Mmm-hmm," I assured her, nodding. "You'll love it."

Almost ashamed to meet my eyes, she glanced away and whispered, "Okay."

That was good enough for me. "Roll over," I said. "Get on your hands and knees."

She did as I said, but reached for a drawer on the nightstand. Pulling open the drawer, she removed a small bottle and set it on the bed within my reach: Astroglide. Oh yes, she'd just been waiting for a day like this. She looked back and gave shy smile. "Take it easy, okay? This is my first time."

Oh lord. A virgin, delicious teen ass just waiting to be plundered. I nodded solemnly but knew that I would pound her as hard as she'd let me get away with. If her previous wild abandon was any guide, she'd soon be begging me to fuck her as hard as I could. I would be happy to oblige.

I had the most exquisite view of her slim, round ass and firm thighs. Her big, hairless balls swung below her pink, puckered asshole, which was already starting to gape. I knew from fucking women in the ass that the hands-and-knees position was great for opening her up and easing my entry. Leaning forward I kissed her round bottom as I worked a lube-dripping finger into her hole. She groaned again and I could see into her butt. This chick was totally ready for my cock.

Getting on my knees behind her I gave my hard cock a good coating of lube and moved the tip the entrance of her sweet hole. "Just relax," I said. "You can set the pace, I'll go along with whatever you want to do, okay?"

I barely heard her say, "Okay."

I pushed forward and the head of my dick popped right past her sphincter. "Oh!" she said.

"You okay?"

"Mmm-hmm," she said. "Feels good. Do more."

No problem, I thought, and pushed in more. She moaned as half my length sank into her slippery hole, then three-quarters. Finally I stuffed my entire cock in, right up to my pubes. I stopped to give her a chance to get used to me.

"You like that?" I asked.

"Oh yes," she said in a throaty whisper. "Oh God, that's good."

I pulled out about half way, very slowly, and then pushed back in. Her groans got louder. My cock felt like it was on fire, this chick's ass felt so good. I'd have to be careful not to pop off too soon. Slowly I fucked her tight hole, then a bit faster, holding onto her smooth hips as I thrust into heaven.

"Oh yes," she moaned. "I like that. Fuck me. Fuck me harder."

I picked up the pace thrusting my shiny cock into her tight, lubed butthole. My balls slapped against hers, which almost hurt, but I kept going. Faster and harder I went, slamming into her like I was fucking a well-worn slut. She groaned louder and pushed back against me.

"Oh shit, oh God," she said. "Yes! Yes! Fuck me!"

The window was still open and I hoped that no one walking by would hear. I rammed her good and hard for a couple of minutes, my heart racing and my dick struggling not to explode. Then I slowed down, dropping the pace and backing off the intense fucking.

"Why are you stopping?" she gasped. "Did I do something wrong?"

"You're doing great, honey," I assured her. "I just want to change positions."

Reluctantly pulling out, I pushed her onto her side. "Roll on your back."

She did as she was told, an expectant, almost scared look on her pretty young face.

"Lift your legs up and hold them," I said, guiding her hands to grasp behind her knees.

Her hard cock was dribbling pre-cum like crazy and a big, shiny slick of it coated her cock and belly. I knew she'd want release soon. Bending over, I sucked her throbbing dick for a minute or two, sliding two well-lubed fingers into her steamy butthole. Her moans got louder again and I figured she'd spew if I kept going. Straightening, I smeared a bit more lube on my engorged cock and again lined up with her pink hole.

With one slow thrust I pushed inside her as far as I could go. She gasped and I felt her butthole clamp down on the base of my cock. "Just relax," I told her. "You're gonna love this."

She nodded but still looked a little scared. Now, I've always been a limber guy. I did martial arts for years, which involved lots of stretching, and stretch regularly to this day. But I think I took her by surprise when I bent forward and took her cock in my mouth even as my dick slid into her ass.

"Oh!" she said. "Oh wow. I never even thought..."

I couldn't take her whole length into my mouth while I fucked her but I could get about half. I thrust into her slippery ass while bobbing her knob and slurping away. She groaned her loudest groan yet and I felt a shudder run through her young body. I knew she couldn't last much longer. I sucked and slathered her trembling dick and rammed her hot, wet ass. If possible her dick got even harder, and she let go of one leg and put her hand on my head, moaning and thrusting. I sucked for another minute or so but the strain of being bent almost double eventually caught up with me and I had to straighten up. But this allowed me to slam her with full-length strokes which set to moaning louder.