young shemale

I live in the mellow town of Olympia, Washington. A nice place, though quite rainy, with lots of places to hike, kayak, and backpack. Bicycle too if you don’t mind getting soaked. I’m an average, middle-aged guy, in pretty good shape, and I love the tight, fit women that seem to be everywhere around here. After getting divorced a few years ago, I found myself alone in a small house on a one block long cul-de-sac. The house isn’t spectacular but it’s clean and well maintained and has a large yard. I grow a lot of my own food, and what I can’t eat I give to neighbors or one of the local food banks. Lord knows there’s plenty of hungry people out there.



About a year ago, a new family moved in next door. I met them a couple of times—a pretty single mom and her smokin’ hot daughter, Stephanie. The girl was in high school but I didn’t know her age and we barely said two words to each other. The mom, however, was a lot more interesting and I made a point to chat with her if the opportunity presented itself. Eventually she accepted my invitation for coffee once but made sure to mention she was seeing someone. All very friendly but it was clear she wasn’t available. Oh well, I had to try, right?



So a few months rolled past. We waved at each other or made small talk if we were out working in the yard or checking our mailboxes at the same time, but that’s about it. Stephanie rarely had friends over, which I thought was odd. Don’t young girls have millions of friends? In fact, the only time I saw anyone her age over there was when they had a party. Based on the giant “Happy 18th Birthday” banner strung up in the living room, at least I knew how old she was. But the party was quiet and her few friends soon drifted away. It seemed to me that she was kind of unhappy- she always seemed to be moping around, never listening to music or jabbering on her cell phone the way other kids do. I don’t have any children but a few other families live on my street and I see kids walking by all the time, so I have an idea what “normal” teens do these days. Stephanie seemed like a bit of an outcast, but it was really none of my concern and I didn’t give it much thought.



I work weekends and have Monday and Tuesday off, and I often saw Stephanie walking home from the bus stop on the afternoons when I was home. Last week I was pruning the bushes in my front yard when she walked by. I was shirtless and caught her looking at me. I’m a reasonably good-looking guy in my 40s, muscular, with a hairy chest and, I’ve been told, a cute round ass. I’ve been ogled by women before but I figured with the age difference Stephanie wouldn’t even notice me. What high school chick looks at guys that are older than her dad, right? But her head turned as she passed, and she even gave me a shy smile.



I felt my dick get hard just looking at her. I mean, this girl was hot. She reminded me of the actress from Pirates of the Caribbean, Keira something-or-other. She had one of those perfect oval faces with naturally plump lips, a button nose, and wide, innocent blue eyes. Slender but not skinny. Her tummy was flat, her tits were perky little torpedoes, and her lean legs led up to the ass of a lingerie model. Long, light-brown hair framed her lovely face. Oh yes, she was quite a package.



It was September here in Olympia and quite warm, so she wore shorts that showed off her legs and a scoop-neck sleeveless t-shirt that clung to her small, jutting breasts. And of course she had a backpack slung over one shoulder. My cock kept swelling and I had to fight the urge to rearrange myself. What would she think if I started grabbing my crotch when she walks by?



“Hi Steph,” I said, and waved. I made sure to tense my abs and stand up straight so I’d look my best.



“Hi,” she replied. Her eyes never left me and she gave a little half-smile and a wiggly finger wave.



Since she was staring at me I thought it was only fair to stare back. I just turned my head to watch her exquisite eighteen-year-old body glide by, and she didn’t seem to mind. Most of her long, straight hair hung down her back but two tiny braids were pulled back from her temples and clipped in a silver barrette at the back of her head. All too soon she was gone and I returned to my yard work. At least I had the chance to push my dick into a more comfortable position. I figured I’d be jacking off tonight, but what else could I do? No way was I going to put the moves on her. Legal or not, it would be scandalous if the neighbors found out, and her mother would probably kill me. At the very least it would make for a tense and awkward situation, and I didn’t need any more stress in my life.



After finishing the pruning, I hauled the cuttings to the compost pile in the back yard. I figured I would clean the gutters and then call it a day. Taking the big ladder off its hooks on the side of the shed, I leaned it against the gutter and climbed up. I sat on the edge of the roof and started scooping out the leaves and branches that had blown in from a big storm a few weeks earlier. Oh, the joy of home ownership. I worked my way around the roof until I was on the side facing Stephanie’s house.



Her house is right next door, separated by a six-foot wooden privacy fence. There are no windows on the side of my house facing hers, and both back yards are blocked from the street by another fence. Several huge rhododendrons and laurels grew along the property line. Stephanie’s bedroom was on this side of the house too—I’d seen it when I cleaned out the gutters last time. In fact, the only way to see into her room was from the exact spot where I now sat. Looking down from my high angle all I could see was part of the bed and floor.



Then Stephanie walked in and flopped down on the bed.



Talk about feeling torn! Part of me was hoping she’d strip but I knew if she spotted me spying on her I’d be in big trouble. But she was so fucking hot, surely it wouldn’t hurt to watch for just a second. And I did have a legitimate reason to be up there. One glance and she’ll know I’m not a voyeur, just some old dude cleaning out the gutters. My throbbing dick convinced me not to rush off just yet.



From my vantage point I could see her luscious body from tits to toes. Her head and shoulders were outside my view, which was good because it meant she couldn’t see me either. I waited, not knowing what to expect. I am not a peeping Tom and would never have gone out of my way to spy on a young girl, or anyone else for that matter. However, I found myself with a great view of a delicious eighteen year old and just couldn’t bring myself to move. I knew her mom worked days and would not be home for a few hours, and no one could see me up there unless they were on their roof too, so I felt relatively safe.



She was laying on her back and I figured she would start reading or maybe watch TV. Nothing would happen and I’d get bored, finish my work, and go jerk off in the shower. But as I watched, I saw her hands drift up and start caressing her nipples. She kneaded them gently, then began massaging her small breasts. My dick sprang to attention and it took all my willpower not to start stroking myself right there on the roof.



Soon her hands slipped under her T-shirt and the massaging seemed to get more forceful. I wondered if she was one of those girls who can orgasm just from tit-play. She started grinding her hips a bit and I began to hope I’d see a full-blown teen orgasm soon. The cock swelled so much it almost hurt. I should probably leave. But I didn’t.



Suddenly she tugged at the hem of her shirt and yanked it up over her head. One hand worked a breast while the other slipped under the waistband of her skirt. Oh man, this was really getting hot. She rubbed her crotch for a minute or two, her hip gyrations getting more pronounced. Then she withdrew the hand, reached behind her back, and undid her bra. With a couple of wiggles and a shrug, the bra ended up on the floor and I got my first look at her tits.



They were on the small side, but firm and perky. The areolas were about the size of quarters and a blush-rose color. Her nipples looked like pinky-tips. The breasts were slightly up-swept and I was sure if she stood up they would not droop but would point proudly skyward. Tiny torpedo tits. And her skin was flawless—not a blemish to be seen, smooth and pale, and absolutely hairless. A wonderful example of an eighteen-year-old girl. I would definitely need to get of the roof before I fell off or my dick exploded.



Then she unzipped her shorts and wiggled out of them too. I admired her tight teen body, now clad only in red cotton panties and cute, striped, teeny-bopper socks. Her hands again drifted to her tits and crotch, massaging and rubbing as her hips moved left and right. Then she tucked her thumbs into the waistband of her panties and slipped them off too. She kept her legs clamped together and slid a couple of fingers down into the patch of brown hair at her crotch. I figured she was working her clit, and based on her gyrations it seemed like an orgasm could come at any minute. Then I got the shock of my life.



She spread her legs and a rock-hard cock sprang out and slapped against her flat belly!



What the hell?



This teen fashion model is really a guy? Oh man, I never saw that coming.



I consider myself straight. Yeah, I’ve been blown by a man a few times and sucked cock a couple of times too, but I’ve never done anal and I’m sure not into kissing or body contact or any of that stuff. I had a gay roommate years ago and he would give me “mercy sucks” when I struck out with the ladies. That guy could really suck cock too, but it was strictly for release, I never considered it a relationship or anything. So maybe I’m Bi, I don’t know.



I thought I was watching a hot teenage girl rubbing herself but it turns out to be a hot teenage girl with a dick, and if anything that made it even hotter. I’ve seen some tranny porn and gotten turned on by the thought of sucking a dick that happened to be attached to a woman, but I’ve never done it.



I kept watching, unable to tear my eyes away. Her dick looked to be about seven inches long, straight, and hard as a baseball bat. Pre-cum dribbled from the tip. With one hand she worked her balls while the other slowly stroked the shaft up and down. Her hips arched and she picked up the pace. I knew she was gonna spew soon. Watching that babe work her cock just about made me cum right there.



Then a squirrel came bounding down the fence, running along the tops of the planks, making a lot of scratching noise that sounded like fingernails on a chalkboard in the afternoon silence.



Stephanie sat up and looked out the window, straight at me.



Oh shit.



Now, it was pretty obvious I was on the roof working. I had on leather gloves and had a couple of scrub brushes sitting beside me. But it was also obvious that I had seen everything.



Her eyes got big and round as a terrified expression contorted her pretty face. What should I do?



I gave her the most dazzling and appreciative smile I could, and offered two thumbs-up. Staring right into her eyes I tried to convey how much I enjoyed what I saw, and that her secret would be safe with me. She seemed to relax, then smile a bit. Shifting to a kneeling position on the bed, she made sure I had a good view and began stroking herself again. I just stared, astonished at the sudden change in her attitude. This girl liked me, I thought. Maybe she was even thinking about me as she masturbated. Her smile grew bigger as her hand pumped her hard cock. I couldn’t take any more.



Leaving my gloves and tools on the roof, I scrambled down the ladder and clambered over the privacy fence. Walking up to the window I realized couldn’t even see in. The ground sloped downhill and I looked around frantically for something to give me a boost. I went around the back of her house and found an old six-foot wooden ladder. I carried it back, leaned it against the wall below her window, and climbed up about half way. Once again I could see into her bedroom.



She still knelt on the bed, tugging her hard cock. She gave a lascivious smile stroked a little faster. My cock was about to burst. Why not take this all the way? I reached up and tried to open the window but it was locked. I looked at her, licked my lips, and pointed to the window lock. After a moment’s hesitation she clicked it open. She lifted it enough for me to get my fingers under the pane and push it all the way up.



I couldn’t believe what was happening. I was about to climb in the window of my neighbor’s house to fuck an eighteen year old girl who, despite her luscious female appearance, was actually a boy. First time for everything I guess, I wasn’t going to let this opportunity go to waste.



I climbed up one more rung, which put my face just about level with her cock. She had stopped stroking herself and knelt only a couple of feet away, flat stomach and torpedo tits and rock-hard cock tantalizingly close. I reached out to massage her small breasts. She moaned and pushed forward into my caressing hands. If it wasn’t for the dick I would have sworn she was a girl. But there was no ignoring that cock. It needed attention fast.



Sliding my hands over her taut body, I reached around to squeeze her firm ass. I pulled her toward me. She crawled forward willingly, a look of desperate lust on her fashion-model face. I wondered how much experience she really had. Judging by the almost manic gleam in her sky-blue eyes, this could very well be her first time. I was determined to make it memorable.



She knelt on the bed, dick poking out the window, exactly level with my waiting mouth. I cupped her balls with one hand and held on to the window sill with the other. I didn’t think I’d need much hand work to bring her off. Her breath was coming faster and she thrust her hips forward, anxious for a warm mouth to finish her. I could see her dick jumping slighting in rhythm with her pulse, making the long rope of pre-cum that dangled from it twitch and swing. Yeah, this chick was ready to spew.



Licking my lips to get them nice and wet, I gently took her cock head in my mouth. She moaned louder and I thought she might shoot it right there. Slowly, I slid my mouth the length of the shaft, getting it slippery wet and tasting her pre-cum. I teased her balls and bobbed my head forward and back, forward and back. She was hard as bone and smelled feminine, not masculine at all. I slurped some more, lavishing attention on the head and underside. I knew firsthand how great that felt.



“Oh God,” she whispered. “Oh God, that’s so good.”



I sucked a little harder and took as much of the shaft as I could. I got all but the last inch, and then I squeezed my lips to get a tight seal and gave slow, gentle sucks. Not so hard that it hurt but strong enough so she could feel the suction. Then I backed away, maintaining the suction and slathering her dick with my tongue. I bobbed some more, sucking and licking, working the shaft like a thousand-dollar hooker. It felt so good I started to moan a little too.



“Oh shit, oh shit,” she said, sounding almost panicked. “That is so good. I’m…I’m…”



I sensed she was unsure of the etiquette involved. Should she just fire off in my mouth? Pull out? If this wasn’t her first time it was pretty close.



Backing off, I let her cock pop out of my mouth. I glanced up her tight teen body, past those pointy little tits, and made eye contact. I said, “It’s okay, go ahead and cum whenever you’re ready. You can let me know you’re about to shoot, but don’t hold it back.”



She nodded, her blue eyes locked on mine. Her mouth hung part way open and her breasts heaved with her fast breathing. This chick was ready to explode.



I released her balls and held on to the edges of the window frame with both hands. If she came as hard as I thought she would, I didn’t want to risk falling off the ladder. Licking my lips for the final suck off, I again took her cock in my mouth. I went right for the deep-throat, or as deep as I could manage, burying my nose in her sweet-smelling pubes and getting a good suction. Thrusting my head forward and back, I sucked that cock with everything I had, moaning now almost as much as she was. No way could she last much longer.



“Oh God, oh God!” she moaned. “Oh shit, oh God!”



She grabbed onto the window frame with both hands, her body starting to shake. I reached around with one hand and touched her ass, pushing it forward to suggest that she move her hips. She must have understood because she started thrusting into my mouth, moaning even louder. I hoped nobody walking down the street would hear.



I kept up the suction and she thrust like a maniac. Her legs tensed up and I could feel her whole body tighten. Her rock-hard dick drove in and pulled out, over and over. I knew this was it.



“Oh God,” she said. “Mmmmmm, oh shit! Oh shit!”



She fucked my mouth so hard I was glad I held on with both hands. Grabbing a handful of my hair with one hand, she mouth-fucked me a few more seconds, moaning and making incomprehensible noises. He dick slammed in and out of my clamping lips and it was all I could do to stay on the ladder.



“Ahhhhh!” she cried out. “I’m cumming!”



I felt her hand tighten in my hair, holding me in place as she ejaculated. A huge blast of hot liquid squirted in my mouth. I managed to pull back enough so that only half her cock was in my mouth. I didn’t want her load going down my throat, I wanted to savor it. Hell, it was the first cum I’d tasted in years.



“Oh god!” she yelled. “Oh shit yes!”



Blast after blast of hot cum shot into my mouth. If she hadn’t been holding my head in place I would have enjoyed watching this load shoot out, but she wanted to cum in my mouth and I was happy to oblige. Moaning so intensely that I almost thought she was in pain, she just held onto my head and emptied her balls in my mouth. Thick, warm liquid blasted over my tongue, filling my cheeks until I thought I would either have to swallow or abandon my suction and let it dribble out.



She kept my head right where she wanted it, pulling her dick out only an inch or so and then thrusting it back in with each squirt. It tasted mildly salty, but not bad. Sweet, delicious eighteen-year-old girl cum.



“Mmmmmmm,” she moaned, finally winding down. “Oh God, that was good.”



I released the suction seal, allowing air into my mouth, now full to the brim with hot teenage sperm. All I could do was say “Mm-hmm,” nod my head, and gently work her shaft.



Her cock was bathed in her own cum. I again looked up past her heaving tits and into those blue eyes. She had a dazed expression but also a huge smile. I kept eye contact as I bobbed on her cock, enjoying the warm cum. Slowly I brought her down, feeling her cock soften in my mouth. I’d never swallowed cum before and wasn’t really sure what I was going to do with this mouthful.



As if reading my mind she said, “Do you…still have my cum in your mouth?”



She asked so innocently, I almost creamed my pants. As it was I had so much pre-cum leaking from my dick I was sure it had soaked my underwear and was well on its way to seeping through my jeans. With a few final, gentle sucks I let her half-hard cock drop from my mouth.



“Mm-hmm,” I answered her, nodding in case she didn’t get the idea.



“What are you going to do with it?” she asked.



I gave a little shrug, and then an idea hit me. Since I couldn’t talk I just pointed from my lips to hers and raised my eyebrows in inquiry. Hopefully she would understand that I was asking if she wanted it.



“Oh,” she said, seemingly taken aback. “Well, I never…I mean…”



So she was interested but embarrassed. I patted the bed, indicating that she should lay down. If she had any qualms they quickly disappeared because she lay down on her back with her head just a few inches from the window. I climbed up one more rung and leaned in over her.

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.

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