Emily and I stepped out into the street, into the cool air, and looked at each other, exhausted. We had been finishing a major paper for school for almost the entire day, stuck inside the library. Emily had snuck in a bottle of wine and pulled it out as we were finishing the revisions, and soon we were flirting with each other, relieved from completing the assignment.
“Why don’t you come back to my place? Engage in some stress relief?”
She grinned. “What exactly do you have in mind by that?”
I took a step closer, gently putting my hands on her waist and forcing her to look up, our difference in height more pronounced than ever. I felt more confident with her allowing me to hold her like this.
“We could start with a glass of wine, some music… Perhaps a massage.” I brought my lips closer to her ear. “Then I’d kiss you, starting with your lips and down your neck until my head is in between your legs.” She stiffened slightly as she felt my lips touch her skin gently along her neck. “And we could just stay there until you forget about everything else.” I continued kissing her neck, running down to her collarbone as she tilted her head to give me access. Her hands were now gripping my triceps, almost holding on to me to stay balanced as she leaned forward.
A few moments went by as I began my ascent from her chest to her lips. She brought her hands up to my cheeks and brought me in for a kiss.
“Okay,” she breathed out, “let’s do that.”
I gave her one kiss then abruptly pulled away, grabbing her by the hand and pulling her forward. I was already hard and wanted to have her that second, tasting her cum and feeling her thighs against my head. The silky feeling of her dress was still on my hands. I wanted to see it pulled up to her waist, the sleek fabric crumpled up, and the top folded over and tucked under her breasts. I wanted to feel how it felt on my chest as I slid down to her pussy. And most of all, I imagined myself in her position: on my back, legs spread, encased in the silky thin material that only served to remind me of my girlishness, while she pressed herself into me.
I knew, already, that I would cum right on the front of her dress when I fuck her, leaving a big stain and forcing her to throw it away into the trash. I’d promise to buy her a new one – not only would I get to wear a pretty dress once she’d left, but I could go dress shopping with her, watching her go in and out of dressing rooms while I spent time among the racks of dresses in the store – and when she had it, I’d fuck her in that one too. I’d down this with a previous girlfriend, and the dress I’d recommended was more for me than for her, at that point, pink, shiny, and short. The epitome of sexy girlishness, and I remember cumming hard as I filmed myself from behind wearing it, my pantied ass wiggling just like a porn star.
The elevator doors closed, and Emily immediately came into my arms and slipped her hand into my pants, gripping my hard-on.
“Oh, fuck, I am going to enjoy you.” While I was around the average size, her hands were so small that she could grip it with both hands and still not reach my tip. She tried to rub herself against me and kept rapidly kissing my neck and I pulled her in closer. I was a bit surprised – I didn’t realize how horny she was, or that she was this willing to start in the elevator. As we reached my floor, she kept one hand firmly gripped around my cock, pulling me forward without any regard to whether anyone else was in the hallway.
“What way?” She demanded.
“Second one on the left,” trying to keep up with her pace. I was liking this more and more – she was acting dominant and eager, two traits that are the most attractive for me in any woman. It always feels the best when girls acted like they were just using me for my body, getting whatever pleasure they could, rather than trying to please me and act submissive. I quickly unlocked the door and we practically tumbled inside, still frantically kissing, and fell onto the couch. She quickly twisted herself to be sitting on top of me and started unbuttoning my shirt, still grinding on my waist.
“Fuck, Emily, that feels good.” She was pressed up against me. I pulled her dress up and felt her panties and thighs, running my hands to her pussy. She moaned into my neck.
“I want you to fuck me from behind,” she whispered to me. I obliged, pushing her off me and rotating her so her knees fell to the ground and her face was in the couch cushions. Unbuttoning my pants, I pulled her panties aside and quickly pushed my dick in between her thighs to feel her wetness. I felt her hand, wet from playing with herself, grab my dick and guide it into her.
“Ooh!” I went quickly in, pushing and pulling out rapidly. I couldn’t wait. The sight of her, with her dress pulled up, looking so feminine, was already nearly too much for me to hold my cum back. I looked away, slowing down, and allowed her to start pushing her ass against my konya escort waist, taking as much cock as she could.
We kept going for awhile, until I flipped her over onto the floor and sat on her chest, bringing my dick up to her face. I put one of her hands on her pussy, encouraging her to play with herself. Pushing my cock to her lips, we locked eyes as she slowly opened her mouth to take the head of my cock in. Her tongue came out, washing over the head and stretching along the underside of my girth. It felt amazing as I kept pushing, leaning over her, and sliding my cock in and out of her lips. As I heard her start to moan around my cock, her hand furiously rubbing her pussy to cum, I pulled out.
“Fuck yeah, cum on me, please!” I shot the first load directly into her open mouth, then pulling back, I made sure the rest landed in a line straight down her dress, over her covered breasts and down to her stomach. I rolled over and we laid there for a moment, both panting.
“Damn it, I think you ruined this dress – I meant to cum in my mouth, silly.” I turned over and smiled.
“Sorry, my bad – here.” I took to fingers and started to pick up the strings of cum along her body, and brought as much I could to her mouth. She smiled coyly, less willing to act slutty after finishing, but opened her mouth as I pressed my fingers up to her lips, licking the cum off.
“This is a good look for you Emily,” I smiled, as I scooped up the rest of the cum and fed it to her. Once I finished, she pushed me away, laughing.
“I need to go clean up. Can I wash this in your sink?”
“Sure,” I responded.
I went and put on pajamas while she did her best to clean her dress, now just wearing panties as she stood over the sink. I laid down and waited for her to finish up and join me.
She came over in a few minutes.
“Okay, so I couldn’t clean it all off, but I hung it up in the bathroom.” She slipped under the covers.
“Alright. Sorry, didn’t mean to ruin it.”
“It should be fine, it was worth it.” She kissed me. “I do need to sleep though, so good night.”
I kissed her back. “Good night Em.”
A few minutes passed and I laid there, pretending to go to sleep, even as all I could think about was her dress hanging up in the bathroom, waiting for me. After some time my cock started to grow again, and I thought about what it would be like. After awhile, I felt Emily drift off, and I quietly removed myself from the bed, grabbing an inconspicuous bag from my closet on my way to the bathroom.
Emily’s dress, now hanging on the back of the door, was cute. As I stared at it, I opened the bag and pulled out a few items. My girly bag, I called it, with all of the femme items I owned – toys, a few slutty Halloween costumes, panties, a few dresses. I started to put on what I needed and looked back at the dress.
Made of a sleek black fabric, maybe velvet, it was soft to the touch and almost shimmery. It was trimmed with an adorable white collar, and had matching white bands where the puffy sleeves ended, just over the shoulder. Around the waist was a big floppy bow, wrapped like a present, and the ribbons hung down to the end of the thigh-length dress.
It would match the ruffled white panties I had slipped into, caressing my hard cock. Not too sexy, but the perfect amount of girlish innocence that was appropriate for a virgin like me. I bit down on my index finger slightly and wiggled my hips in the mirror, watching my perky butt shake each frill. My other hand was stroking my cock outside of my panties.
Emily was asleep, but in my imagination she was behind me, a hard strap-on pressed up against my panties and lining up with my ass. Her hand rubbed my breasts, pinching my nipples, and she pressed my finger deeper into my mouth, making my suck on it before pulling it out. I had done this so many times to girls before, pulling up their dresses and bending them over so they could take my cock in their pussies. I loved fucking women while they was still wearing their clothes, feeling the textures of the skirts and lingerie and blouses against my skin.
In my mind she murmured softly into my ear, her hair brushing up against my bare shoulder.
“Do you want me to put you in my pretty dress sweetie? You’d look so cute in it, sexier than me. Of course, you’d need the matching thigh-high stockings and bow in your hair, maybe some makeup and cute shiny high heels. You probably don’t need a bra with those adorable little titties of yours, but I think I’d give you one anyway. I’m sure we can find a frilly white training bra at Victoria’s Secret for you. Model it for the salesgirls, maybe. It would complement your panties perfectly.”
I moaned to myself as my hand stroked faster. I needed to put the dress on now, otherwise I wouldn’t last. I yanked it off the hanger, gathering it above my head and pulling it down, twisting my arms to squeeze through the escort konya tight bodice. It was slim throughout the chest, the puffy sleeves nearly filled by my shoulders, the neckline almost digging into my skin, reminding me of its presence. I sat on the edge of the bath, pulling up my stockings, a pale white lace design with tiny bows on the edges, up along my legs. I stood back up and grabbed my hair bow, adjusting it behind my ears and ruffling it slightly to stand out more.
Ugh. I looked exactly like a boy in a dress, but I felt so girlish that I loved it. The hemline ended right above the stockings, showing a sliver of my thighs. The outline of my cock pressed through the dress, a noticeable bulge. My boobs were nonexistent and I pouted, crossing my arms to my shoulders covering my chest, and shaking side-to-side in what I imagined to be sexy, baby disappointing-like. My thumb crept into my mouth and I bent at the waist, sticking my butt out from under the dress. Reaching under the counter, I grabbed the small pink dildo hidden behind the shampoo and popped the tip of it in my mouth. I swirled my tongue around it, imagining Emily behind my as I looked into the mirror.
“Aww, good girl. Make sure your lips are nice and tight around the head of the cock. Firm suction, baby girl, just like when you suck on my clit in bed. Pout your lips out – look a bit more excited, dear. Boys like it when us girls want their cocks in our mouths. And you do! Make sure he knows how eager you are darling – go a bit deeper down. Put your hand on the base and tickle his balls a little bit – those are going in your mouth next.”
I had the dildo nearly all the way in as I pulled the dress up over my cock and pulled it out. I still wanted to see my cute ruffled panties around my waist, even with my ass popped out slightly, still pretending it was rubbing up against Emily’s strap-on. I was bobbing up and down, my knees together, and my head still moving back and forth with as much dildo in my mouth as I could manage. My moans were muffled as I kept watching myself, focusing on the dress and panties and cock and hair bow until I only saw a sexy girl in the mirror pretending she was cock slut for her boyfriend.
“Uh!” The dildo popped from my lips as I emitted a high-pitched girly moan and my cock started to cum. I kept rubbing as I sprayed into the panties, trying to get one last suck of the dildo until the impulse faded. “Fuck,” I breathed out, slowing my movements and leaning against the counter, the hair bow askew.
I checked the door – still closed, good. I returned the sex toy to its hiding spot and started undressing, smoothing out the wrinkles and wiping out as much girl cum as I could from the panties, throwing the tissues into the trash can. I hug the dress back up and returned the stockings, panties, and bow to my secret bag of girl clothes, putting my pajamas back on. After washing my hands, I left the bathroom and slipped quietly back into bed with Emily, still lying there asleep. I snuggled up close to her, and she rolled into my arms, pulling one in between her breasts. I smiled – I had gotten away with it once again, and closed my eyes, now satisfied.
I woke up uncomfortably.
“Erhm,” I moaned. Something was in my mouth. I tried to reach up, but my hands were somehow tied behind my back, I realized. Still groggy, I tried kicking, but my legs too had been crossed over one another and tied. I couldn’t get the covers off me to see what had happened.
“Uegh!” I tried again. I looked around – Emily was gone. The room was empty. Fuck – what had happened? Did someone try to rob my apartment? I kept shaking, trying to get out of bed. Despite the circumstances, I could feel my hard cock, just woken up from sleep. Finally, I had shifted enough to the edge of the bed. I took a quick breath, and rolled over, falling to the floor.
“Oof!” Free from the bed, but now I was lying on the floor. I rolled over on my stomach and looked down, promptly surprised.
This had to be a dream. Had to be. My pajamas were gone, replaced with bright pink leggings. My cock was pushed over to one side. My toes were painted a bright red. On top, I was wearing some sort of black crop top with something written on it in sparkly pink letters. The short sleeves were pushed down over my shoulders, creating a strapless look while still covering my pecs. I could feel a thong riding up my butt. As I noticed this, I could feel a necklace lying on my collarbone.
What had happened? When I dream about dressing up, I feel like I’m almost watching myself – here, I was definitely in my head. In a crop top and leggings. Tied up. What the fuck happened? I struggled a bit more. Ribbons had bound my tightly bound my ankles together, and I couldn’t shift either of my feet. My hands, too, were too constrained to reach the ribbons binding them. I rolled back over on my tummy, and started inching across my floor to the doorway. konya escort bayan It was slightly open, so I thought I could slip through and find a knife or something.
Right as I was getting close, the door swung open. I squeaked into my gag in surprise and yanked my head out of the way, falling back on my knees with my head in the carpet.
“Aww, baby, that’s not how sissies get out of bed in the morning! If you were so eager to say good morning to Mommy, you could have just given me one of those pretty moans louder!”
I froze. It was Emily’s voice. I tried to lift my head up to see her, but I felt her foot drive down straight into my back, forcing me to lie back down.
“Isn’t that better? You don’t need to get up just yet. This is a good position for you.” I felt her sit down on my lower back, painfully pushing my hands out of the way. I moaned into the gag again as she pushed them to the side.
“Yummy, babe, I didn’t know you liked this. Don’t worry, we can do it again later. But for now I have a few questions for my little darling.”
I felt her reach behind her and pull the leggings down slightly, exposing my butt. She pulled up on the thong slightly, and it squeezed my balls.
“Nice ass, sweetheart.” She grabbed my head, pulling it up, and making me look out into the corner of the room. My chin was now resting on the floor, and she kept me looking forward, not letting my head go to the side. I felt her undo something at the back of my neck, and I could feel the gag in my mouth loosen. I tried to spit it out, but she snapped it back sharply.
“Yikes! Getting ahead of ourselves aren’t we?” Her weight shifted on my back as she reached to the left near my desk.
“Now, don’t close your mouth baby. Nice and wide.” Her hand went to the gag and started pulling it out. I watched her wrist and felt my sore jaw close thankfully. Right as it came out, her right hand came into view and shoved something else in my mouth. I squirmed for a second, then realized I recognized this feeling. Oh, fuck. It was my pink dildo from the bathroom. My thoughts raced – how did she find it? What happened – how could she know about this? It was her first time here. Sure, it wasn’t hidden incredibly well, but there was no reason that she would normally come across it, and how would she even know it was meant for me?
I tried shifting my head as she shoved more of the length into my throat.
“C’mon babe, I know you can take more of this. That’s not even half!” She giggled. “But I guess it’s enough for now – in this position, I doubt it will be comfortable to take any more than that.” She bounced happily up and down on my back, forcing my body to grind itself into the floor. My cock, more than ever, was massively hard and hurting from repeatedly hitting the floor. She pinched my ass as she spoke.
“So, we’re going to play a fun game. I’m going to ask you questions, and you’re going to answer them. For every right answer, I give you a little treat. For every wrong answer, that dildo is going an inch deeper in between those pretty lips of yours. Ready?” She had adopted the tone of a sexy schoolteacher admonishing her pupil in class in perky baby talk, just playing with me.
I tried to shake my head and plead with her to stop.
“This’ll be fun sweetie! Don’t worry, you’ll like this game. Now, did you play dress-up last night?”
Fuck. How could she know? The door was closed. There’s no way. She grabbed my hair, pulling my mouth open and removing the dildo. I gasped for air.
“No! What is this-?!” She reinserted the dildo, silencing my begging and rotating it around in my mouth, pushing my tongue around.
“Wrong answer, silly. One more inch!” She cried gleefully out as she pushed in in further. I nearly choked, and tears started to come to my eyes. I still hadn’t even seen her except for her hands.
“Let’s try again. Did you act naughty after we fucked and play dress-up in my clothes last night?” With every syllable she pulled on my hair left and right, forcing me to tug on the dildo as my head shifted. She pulled it out again. I gave up – she clearly know somehow. I had to come clean – from this, perhaps, maybe she didn’t mind.
“Yes!”
“Well, no, that wasn’t so hard was it darling! But I still have to put your toy back in because you lied first.” She shoved the dildo back in my mouth.
“However, you did tell the truth now, so you get a treat!” I felt her shift around on my back. She grabbed both my butt checks and spread them apart. Damn – I was not ready for this. I started shaking and moaning as best I could.
“Shh, baby, the neighbors will hear. You can say thank you later.” She slapped me on the bottom, then pulled my cheeks apart again. She made a small noise, and I felt what must be lube on my asshole, cold and wet. Releasing her grip, I felt her pinky finger, slippery with lube, slip down and toy with my opening. I kept showing resistance.
“Baby, you can’t keep taking it in the mouth – sooner or later, boys want pussy.” With that, she pressed the tip of her finger in, slowing pressing down and coming back up.
“Yikes, somebody has a tight pussy. Good thing we started with just one finger.” It already felt painful, but she kept going deeper with each push.
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