tagTransgender & CrossdressersSweet, Young Stephanie

Sweet, Young Stephanie


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.

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byRegularGuyinOly© 33 comments/ 181347 views/ 318 favorites

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