Sam's Dressing Up Encounter

SAM.

The door slammed shut, echoing through the house. I smiled to myself as I lay on my bed, already excited, there wasn't many opportunities to fulfil my needs, so I savoured them when they arrived.

I rearranged the excited cock in my boxers and went to the window to check they had gone. I watched as the car pulled away, my mum driving with my twin sister in the passenger seat.

As soon as they were out of sight I hurried to my sisters room, opened the door and walked to her chest of drawers. I opened the top drawer, brushing my long blond hair out the way as it fell over my eyes, without thinking I grabbed a scrunchy and put my hair into a ponytail.

I looked through the top drawer deciding on what panties to pick, I ignored the g-strings, not wanting to garrote my ball bag again, and choose a nice pair of light blue lace panties. I found the matching bra and chucked both on the bed.

I searched through the next draw for my favourite skirt, my heart skipping when I found it, it was a short white pleated skirt, I threw it on Beth's bed. The next draw down had a perfect yellow vest top which went on the pile, a few other tops for padding.

I went to the bed and stripped off my shorts, t-shirt, and boxer shorts, standing completely naked in my sisters room, my 5 inch cock standing to attention in excitement.

The bra was next to go on and stuffed the other tops in to make a nice pair of breasts, I pulled the vest top on, fitting my slim frame perfectly, my flat toned stomach underneath.

I pulled the panties on, tucking in my hard cock, it strained hard against the fabric. I stepped into the skirt, pulling it up to my waist, glad my sister was the right size for me, it rode high on my legs, showing a nice bit of thigh.

Looking down at my legs I knew I needed something else so I went back to the draws, I rummaged around and found a gorgeous pair of plaid knee length socks, I slipped them on and went over to the dressing table.

The next 20 minutes were spent applying some make up, I was getting quite good at it, having watched numerous YouTube videos, but I had to be careful not to use too much of anything, not wanting Beth to realise, so managed to give myself a natural pretty look.

I got up and went over to Beth's full size mirror to admire my handy work. I took the scrunchie out of my hair and threw it on the bed, letting my long blond hair flow over my naked shoulders. I loved my hair, the only part complete in my step to being female, I should of been Beth's sister, I knew it, but had somehow been cursed to have a cock and balls. I was so like her, just a male version, but I wanted to change that, I just needed the confidence to tell someone.

I loved this skirt, high on my thighs and low on my hips, it looked feminine and sexy, showing off my skinny waist. I kept my body free of hair just for these moments, so I could show of my stomach and legs.

I squeezed my fake breasts and ran my hands over my flat stomach and ribs, caressing my narrow hips, venturing down to my thighs, touching the top of the knee length socks, and up my skirt, squeezing my solid cock in my little panties.

I went over to Beth's bedside cabinet and reached to the back, pulling out Beth's dildo, a fantastic surprise I found a few months back. I went back to the mirror and put the dildo to my mouth, pushing the head in and forcing it back my throat, taking in the full 6 inches, my practice paying off. I spat on the end, covering it in my saliva, forcing it back down my throat, giving it a practice sucking.

I reached down with my free hand and pulled my panties down a bit, my cock flopping out and tenting my skirt. I brought my hand back up and spat on my fingers, quickly returning them to under my skirt. I rubbed the spit onto my eager asshole, lubricating my opening, pushing a finger in to get some inside me.

My finger felt around inside me, preparing my hole for the dildo. I popped the spit covered fake cock out of my mouth and moved it down under my skirt, pressing the head against my anus, I pressed it into me, my hole widening around the sex toy. I felt it slip inside me, grimacing slightly at the stab of pain on my ring, but once inside me it felt good, the tip imbeded in my anal passage.

I tried to push it in further but my stance was wrong, I couldn't take any more, and I needed more. I pulled the panties down, stepping out of them, I squatted down and placed the base of the hard dildo on the floor, holding it in place with my hand. I pushed down on it, forcing the dildo in further, enjoying the sensation of it filling me up.

My cock was rock hard, I pushed it down between my legs, rubbing it with my fingers, pretending it was my clit. I forced more of the fake cock into my ass, as far as I could take it, and started slowly bouncing up and down on it, it felt so good inside me, I wished desperately that it was a real cock, ready to fill my ass with cum.

I continued riding the cock for a bit as I built myself up to climax, the cock slick with lube sliding slickly in and out.

My pretend fingering wasn't working, I needed to wank properly so I let my cock spring up and lifted the hem of my skirt over it, grasping it in my hand.

I heard a large gasp behind me, making me jump, then it turned to a yell, my head spinning to catch the top of a head fall out of sight below the window frame.

"What the fuck," I said, then yelped as my feet slipped out from under me and I fell on my ass, ramming the dildo inside further. I squealed in pleasure and shock, falling onto my side, the cock slid out of me, covered in my spit.

I quickly sprang up and ran to the window to see our window cleaner, Darren, clutching his knee on the ground below, his ladder still propped on the window sill. I turned and ran downstairs.

DARREN - 20 minutes earlier.

My favourite house, hope she's in, I thought, as I pulled up to No 72. Mr and Mrs Simpson had the most gorgeous daughter, Beth, pretty, petite, blonde, and a fucking stunning body. Easily the hottest girl I knew.

Liked to flirt too, often hanging around whilst I worked, chatting to me. If only I had the nerve to ask her out for a drink. I was only 22, she was 18, perfect.

Nice sunny day too, good opportunity to take off my t-shirt, show off the muscles.

The daughter normally wore sexy outfits, showing off her body, and leaving little to the imagination, but just enough to get you hooked on finding out what the rest was like.

I knew she was a twin and I had sometimes bumped into her brother, who strangely looked like a male version of her, he even had long blond hair too, which struck me as a bit weird, but each to their own right, it was a free country.

I pulled into the empty drive, concerned they were all out, parked the van and got all the tools out, I set up my ladder and got to work on the front, taking my shirt off half way through, not to show off, as it looked like no one was here, but because it was too hot.

I finished the front and set my ladder up to a window on the side, this was Beth's window, I climbed the ladder praying that she would be in there masterbating wildly on the bed.

"Thank you God," I whispered as I looked in the window. It was better than I could have dreamed, there she was squatting, playing with herself, and riding a dildo.

She looked fucking amazing, I couldn't quite see her face, her long blond hair over the side of her cheek, but I could make out her slim body, the smooth small of her back, the dildo just under her tiny skirt, her legs wide as she bounced up and down on it.

Her hand was down between her legs, again I couldn't quite see, but her arm was jiggling. My cock instantly started straining in my shorts as I watched for a bit. After a while of perving I decided to knock on the window, see if she needed help, then I saw her lift her skirt, leaning forward eagerly, she had something in her hand, was that a.........

I gasped at the sight of the cock as it caught me completely off guard, I took a step back forgetting I was on a ladder, one storey up. In slow motion I started falling backwards, my hands flew out to grab the ladder, they grasped at the metal rungs and missed, I tried again desperately and caught hold, starting to steady myself until my other foot slipped.

I slid down the ladder, banging my chin and hitting the ground hard, a pain shooting through my left knee, I grabbed it groaning, drawing it up to my chest and holding it. I lay there in pain, my hard cock wilting to Its flaccid state.

"I'm so sorry," came a voice, as someone hurried out around the side of the house.

SAM.

I apologised continuously as I ran up to Darren, looking around frantically to make sure no one else was around, I had never been outside dressed as a girl, and the moment was slightly thrilling, it was just a shame it was for this incident.

"I'm so sorry," I apologised again, "is it bad?"

"It's okay, it's okay," he said, grimacing, "it was my fault, I shouldn't have been watching."

Watching! How long had he been there? My mind whirled, had he been enjoying it and then slipped at the sight of my cock.

"Can you stand?" I asked, "I think you're supposed to put some peas on it or something, sure we've got some."

"Can you help me up?" Darren asked.

"Of course, come on." I said, helping him up.

I helped Darren up, my hands under his thick bicep, as he pushed himself up onto his good leg, he put his arm over my shoulder, and I acted as a crutch as he hopped around to the front of the house. I helped him in the front door, his taut muscular body pressed against me, I felt small in his arms, but safe and warm, a good place to be.

We maneuvered till he was sitting on the stairs, still clutching his knee, I stood back. His eyes wandered over my body and I felt a twinge of excitement, a shiver passing through me.

"I'll get some peas," I said, looking down and blushing. "I'm Sam by the way."

"Thank you Sam," Darren said, his eyes flicking up and staring into mine. I just managed to break the look and hurried off.

DARREN.

What the fuck, he, I mean she, I think, looked just like her sister. I watched her hurry down the hall, a cute little ass swinging in that short skirt. My mind was telling me I shouldn't be looking, but my cock was getting hard again, I couldn't stop it, even the thought of that cock should of been enough to put me off, but when she was stood in front of me she looked all girl, a tight sexy body.

I had seen enough cock's watching porn to not shy away from the sight of another man's penis, and I had occasionally watched shemale porn, not ashamed to try new things, some of them looking all woman apart from the thing between their legs, and Sam here was definitely in that bracket.

Sam appeared down the hall, I watched her arrive, my head very confused. She knelt down in front of me and put the pack of peas onto my left knee.

"Where does it hurt," she said, looking up at me, her large blue eyes meeting mine. She had a surprisingly feminine voice, I guess she was putting it on, I didn't know.

I took her hand with the peas in them and maneuvered them left a bit. "There thank you," I said, not really wanting to, but letting go of her hand.

"How long have you, um, I mean," I stuttered, Sam saw my discomfort and finished.

"Been dressing as a woman?" Sam said.

"Yeah," I said, looking down at her hand on the peas.

"A little while, but only in secret," she said, "I'd like to do it all the time but I'm too scared to tell anyone, I don't want to be male!" She blurted out the last bit, like it was something she had wanted to get off her chest for ages. A tear ran down her cheek, she wiped it away.

"You should tell your sister, she'll understand, you look just like her you know," I said.

"You think so," she said, smiling, "that's quite a compliment, do you really think I'm that pretty as a girl."

I thought for a second, looked at her, "yeah I really do," and she did, if only it wasn't for that cock, but saying that, even that made her more interesting.

"Maybe I could pretend to be her," she said, blushing, "I'm sure there's ways of doing things that make it look like it's with my sister, so you don't have to see it." Her hand moved off the pea's and up my shorts, I couldn't stop her.

SAM.

"I don't mind if you call me Beth," I added, my hand sliding up his shorts and boxers, my fingers touching his already hardening cock. I couldn't believe I was doing this, but I wasn't sure I'd ever have an opportunity like this again, I had to try and he seemed to be letting me.

I was glad I had put the panties back on before running downstairs, it would be easier to hide my bits from him.

He felt big already as my hand wrapped around his member, peeling the foreskin over the head and pulling it down, he groaned in my hand. I squeezed tighter and started slowly wanking him off in his shorts.

"Oh Beth," he groaned, making me smile.

I knelt higher, reluctantly taking my hand out and tugged at the waistband of his shorts, Darren lifted his hips so I could pull them down, his cock sprung up, hard and throbbing, making me gasp, it was at least 7 inches and beautiful.

I studied it intently as I stroked him, a small glistening blob of precum appearing, I leant forward and licked it up, tasting his salty excretion. I ran my tongue up the shaft, the heat from it intoxicating, I had to feel it in my mouth.

I swallowed him in, stretching my mouth wide and forcing it back my throat like I practiced on Beth's dildo, the tip of his cock making me gag. I came back up for air and spat on his cock, like they do in porn, and took him back in my mouth. I wanked him off with my mouth my left hand wrapped around the base, listening to his groans.

I moved my other hand to between my legs, stroking myself under my skirt, I was so hard in my hand.

Darren took my hair in his hand and started forcing me to go faster and deeper, his cock hitting the back of my throat everytime. He pulled my head down hard, his cock stretching my throat to take the head of his cock, I started gagging and he let me back up gasping, I loved it, the want in his grip.

"Again," I said, breathing heavily, and he pulled me back onto his shaft hard.

"Good girl," he said, my lips touching his balls as I gagged. He let me up, spit stringing out of my mouth. He stood up and still gripping my hair started fucking my face, ramming his cock into my mouth, his balls bouncing off my chin.

After a while he led me up to a standing position by my hair, he kissed me deeply, my mouth and chin covered in my own spit.

"Do you want my cock in your ass Beth," he said, "to feel me stretch that hole of your's?"

"Oh god yes," I begged. "I want you deep inside me."

DARREN.

Oh fuck, what was I doing, she was.just too hot, the way she eagerly took me in her mouth had pushed me over the edge, her lips stretched around my cock. She wanted it bad and I couldn't resist.

I stood up, and spun her around, the peas falling to the floor, my sore knee forgotten, bending her over, she put her arms on the stairs to steady herself. Her small tight ass stuck in the air, the short skirt riding up and showing her panties. I knelt down, taking her thin thighs in my hands and pulled her towards me slightly. I moved a hand over and pulled the crotch of her panties over, revealing her puckered asshole, glistening with lube.

I leant forward and brushed it with the tip of my tongue making her groan, I then pushed my tongue in, entering her slightly, the tight ring fighting back against it. I spent the next few minutes lapping at it, spitting on it and getting it ready for what was next.

I stood up and covered my own cock in spit and then positioned the tip against her asshole.

"Put it in," she said, "please put it in me."

"I'm going to fuck this tight asshole so hard," I said. With one hand on her boney hip and then other holding my cock in place, I pulled her onto me whilst pushing my own hips forward. The tip of my cock stretched her open, her asshole widening around me as I slowly slid in.

SAM.

"Fuck, yes," I screamed, as Darren cock entered me, a mixture of pleasure and pain as he stretched me open.

I felt his head sliding in, the thickness almost too much as it reached its widest point, I was no stranger to things up my ass though and well lubed from earlier, so only felt a bit of pain for a second before his shaft slid all the way in, making me groan loudly.

It felt amazing inside me, filling me up, the hot throbbing cock pressing against my inside walls. He wrapped his hands around my waist and started slowly thrusting in and out of me. His cock hitting the back of my anal cavity. I started groaning with every thrust.

He sped up, thrusting hard, nearly knocking me over onto the stairs in surprise, but I regained my balance, just, with the help of his tight grip.

I hoped he didn't see, but I gripped my cock and started wanking, stroking it frantically, I needed to cum desperately.

"Yes, Yes, Yes," I screamed with every thrust.

DARREN.

Fuck, she was so hot, I had almost forgot she had a cock as I was banging away, my hands wrapped around her tiny waist, the toned small of her back, slender shoulders and long blond hair. I looked down at my shaft sliding in and out of her tight asshole, reaching the brink.

"Fuck, so tight," I groaned. "I'm going to cum."

"Cum inside me," she groaned, between screams.

SAM.

The thought of him cumming inside me sent me over the edge, my hand still pumping away on my cock, I let out a long groan and ejaculated into my sisters skirt, my body shaking in ecstasy as jet after jet of cum squirted into the fabric.

"I'm cumming," Darren groaned, my asshole contracting and squeezing his cock, sending him over the edge. I felt his cum fill my asshole.

Then he pulled out, leaving me empty. I looked back, still shaking from my own orgasm, as he continued to come over my asshole, and Beth's skirt that was up round my hips, his cum still erupting in long streams, and then finally subsiding.

"Wow," Darren said, "that was awesome," he was still stood there stroking himself slowly, still hard, cum dripping out the end.

I turned round, sat on the stairs and took his cock in my mouth, sucking and milking the last of his cum out, tasting his salty thick sperm.

"Good girl," he said.

I stopped sucking, flopping back onto the stairs, exhausted.

"That was fun,' I said.

"Yeah," he replied, his eyes wandered down to my lap, my cock was still hard, tenting my skirt, a look of discomfort crossed his face. "I better get on, I've still got other jobs to do."

"Yeah, no problem," I said, sadly, not really sure what I was expecting.

Darren pulled his pants and shorts up, straightened himself out and limped out the front door, leaving me sitting on the stairs.

I could feel the cum dribbling out of me into Beth's already cum stained skirt, my asshole slightly sore from it's pounding.

I was fine with Darren's reaction, I had got a fuck out of a fit guy, I couldn't of asked for much better out of this morning. I better get changed I thought, I had a bit of time before my mum and Beth got back, but it was getting close.

I ran upstairs taking off Beth's clothes and the make up off, putting my own clothes back on. I put her clothes back in the drawers, apart from the skirt, I stared at it, covered in cum, Darren's stains on the back and mine on the inside, I had no option but to throw it in Beth's washing basket, doing the laundry now would make my mum highly suspicious, I just had to hope Beth wouldn't notice.

I went downstairs and sat in front of the TV watching netflix. Half an hour later Beth and my mum came through the door.