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My First Cross dressing ExperienceMy first crossdressing experience.I don’t remember exactly how we got to it. But I remember the conversation word for word.I was talking to my girlfriend about different outfits she would look good in. I said”I want to fuck you in those heels” She just grinned a little and raised an eyebrow at me.I said “You’d be wearing the heels obviously.””You sure you don’t want to wear them?” She quickly replied and giggled.”Not really, but at least my ass would look great in them””Prove it” She snapped.”They wouldn’t even fit me” I replied”Fair enough. If they did though we could get you a little pink dress and some stockings”I just looked at her a little worried, but slightly amused. I was actually incredibly turned on which was actually what worried me more.She stood up from the bed and put her arms around me and grabbed my ass and pulled me close. She definitely knew it turned me on as my cock was rock hard and there was no way she didn’t feel it.She ran one hand up my side and then flipped my hair as she moaned in to my ear “Mmmm and we can get you a pretty pink bow for your hair. We don’t even need to get you a wig!” I have long hair almost down to mybutt.She kissed me, laughed, and let go of me and carried on playing a game on her phone. I just stoodthere for a second, thinking to myself “Well that was weird. Why did that turn me on so much?”I didn’t think about it too much and the conversation never came up again.That was until about a month later.I go to her house and she calls to me “Hey I’m in my room can you come help me with something?”She probably needs me to move her drawers or something I thought as I went up the stairs, I open her door expecting something to be moved half way across the room. It wasn’t. Room looked exactly the sameas it usually does. She’s there lying on the bed smiling. “So what did you need help with?”She giggles and shuffles across the bed and reaches down the opposite side where I can’t see and bringsback up a shoe box.It was a vans shoe box or something so I just assumed it was a gift (It was, just not the kind I wasexpecting)She hands it to me and I open it up.Theres a pair of black heels in there. In my size. “Prove it” She says.”Are you serious?””Yeah. Put them on” She giggles.She was enjoying this a little too much. “You really want me to put them on?””Yeah. I bought them just for you””Alright, whatever” I was so excited, I have no idea why. Maybe the taboo of crossressing? Evenif it was just a pair of shoe’s it was still something I’d never done. I did my best to hide my excitement. I think I did a good job.I awkwardly put them on and just stand there “Happy now?””Turn around let me see that ass” She said whilst biting her lip and looking me up and down.I stumble just trying to turn around and she laughs. “Aww can you not walk in heels?””Of course I can’t” I say whilst grinning. I manage to turn around.”Mmm I think you were right baby. But I can’t really see your ass properly in those pants. I think youshould take them off. The shirt too” I take the heels off, slowly take off my shirt and pants while looking her in the eyes, her looking backat me biting her lip. She gets up onto her knees as I move towards her thinking that was it and I was going to get laid.”Nah uh. Put the heels back on and show me that sexy ass”I stop in my tracks. “uhm. What?””Did I stutter? Put the heels on” giggling the whole time.”Put the heels back on” I mockingly mumble to myself as I do it whilst trying not to laugh.I put them on and turn around. Now just in my boxers and a pair of black heels.”For fuck sake baby!””What? I put them on!””Your ass looks better than mine” She growled as she got up from the bed and put her arms around me frombehind.She bursa escort grabbed my cock through my boxers “Why are you so hard?””C-coz I thought we were going to fuck” I was so nervous all of a sudden. I don’t even know why. It wasn’t like I was worried about how she would react to it turning me on. It was her idea.”Why would you think that?” She whispers to me and softly kisses my neck”You told me to get undressed””You got hard in the half a second it took to take your pants off? You were alreadyhard when you turned around to take them off””Yeah, sure” I say whilst trying not to laugh.”Your ass does look fucking good in those heels though” she says as she smacked my ass.I jumped a little, it caught me completely off guard.”Wait before you take them off” she squeals as she jumps onto the bed and falls onto her stomache to reach down the other side of the bed again.I just stand there, so many thoughts running through my head, wondering what was coming next.I remembered the conversation about the bow. Holy shit. I was so turned on remembering it but thought tomyself “No. It won’t be that. I hope it is? I think. Does she even remember that? Obviously she does dumbass she bought the heels.”I hear her slide a box or something out from under the bed.”Uugh, there we go” She dramatically says as if its super heavy, as she puts it on the bed””Whats that?”She opens the box with the lid to ward me so I can’t see what’s in it. Slowly lifts up a pair of pantiesabove it and smirks. “Here”. She throws them to, I catch them and hold them up. Theyre bight pink, lacey,with a little ribbon on the front.I stand here holding them, almost shaking I was so nervous. We just look at eachother for a few seconds.She smiles at me and gives a little nod.I bend over and put one foot in and hesitated a little, I put the other foot in and I slowly pull them upI get them up to my thighs and I start thinking to myself “Oh shit they’re not going to fit” (I work out a bit so I have fairly big thighs for my height)I pull them all the way up and the back gets caught on my butt, before I can even adjust my hands to theback so I can pull them over my bum she jumps up so she’s kneeling on the bed.”Wait wait wait. Stop!” I start to panic at this point thinking she had changed her mind or this was a joke or something and thisis where she tells me.She starts laughing “Are they caught on your ass!? Oh my god show me!” I sheepishly turn around with my hands still hooked into the panties at my waist”Holy shit that’s so fuckin hot” I feel her hands on mine as she slowly runs them around to the back,hooks her things into back of them and slowly pulls them up over my ass whilst moaning.She smacks my ass again and reaches around, grabbing my cock, still rock hard.I feel her breath on my neck as she squeezes my tighter.”You’re throbbing” She whispers quitly into my head.She pulls me against here saying “We’re not done yet baby”I can’t even believe what’s happening at this point. I’m standing here wearing a pair of black heelsand these lacey pink panties, dick harder than I can remember off the top of my head.She let’s go of me, I turn around to see her leaning over to pick up the box.I still can’t see what’s in it. I don’t even really care at this point. I’m so turned on and all I canthink about is the way the lace feels against my cock. I always liked the feeling. But it was always a girl wearing them. It was somehow completely different now I had them on.She hands me a pair of long socks. White with pink bows on the front at the top Which I also love. On a woman. I don’t hesitate this time and I take the heels off to put them on.Last time I had to wear any “long” socks was when I was a teenager and had to wear them for football(Real bursa escort bayan football, not American)I fumble around for a second trying to get the first one on. I manage to get my foot all the way in andI put my foot up on the bed infront of her and slowly pull it up whilst looking at her. I wasn’t so nervous at this point. I could tell she was enjoying it was much as I was so I started to have some fun with it.I get it all the way up. They reached up to a little above my knee, maybe 4 or 5 inches.”Jesus Christ. Even your fucking legs look good!” I laugh and turn around so she can see my ass in the panties. I run my hands down my other leg as Ibend down to put the other sock on. I jump as she grabs my ass and I hear her giggle. If I’d had the heels on I probably would have fallen over.”You’re gonna make a sexy fuckin’ girl oh my god I can’t wait!” She squeals as I hear her rummage aroundthe box.I turn around to see her holding up this little outfit. Its pink pleated skirt, with a t-white shirt (Or so I thought)with the little thing over the shoulders that those japanese school girl outfits have. I don’t know thename of them. But it had a big pink bow tying the corners together to hold it up.She hands it to me “Now put it on. Slowly” she giggles while excitedly looking me up and down.I lay it on the bed and unbutton the skirt. At this point I realised it wasn’t a t-shirt. It was a onesie,like a swimsuit type thing.I wrap the skirt around me and button it up. I hear her laughing and I look up.”What?””It’s on back to front baby.””What? I don’t know I’ve never worn one! Do they even have a back?”I turn it around so the buttons are now at the back. I’d been paying attention to the buttons this whole time. I suddenly realise its pretty short. I’m thinking “Does this even cover my ass?” it was so short. I lean over to pick up the onesie thing and I feel it. I was right. It doesn’t cover my ass. the second I start to lean forward I feel the fabric brushing over my butt. I pause as I put my hands on the onesieIt probably barely reached to the bottom of my butt or it was just above. I felt so dirty but the fabric of the skirt and the lace felt amazing.”What?” I hear my girlfriend say.I look up at her “This skirt is really short.””I know, that’s why I picked it”I stand up holding the onesie by the shoulders with it facing me. I couldn’t wait to get it on.But having never worn one. I literally had no idea. I didn’t even know where to start. Blood was being diverted away from my brain.”You don’t know how to put it on do you””No…”She stands up and takes it from me. “Turn around”I hear a pop which I now know was the buttons at the bottom.”Arms up!”I hold my arms in the air and I hear her laugh as she realises she can’t reach that high. “Arms down!”She holds it infront of my “Arms in!”We’re both giggling at this point. I slip my arms into it and she lifts it up over my head again and pulls it down.It was tight. Not like it was too small. It fitted very well. I was quite surprised she got it in sucha perfect size.I felt her reach between my legs to grab the bottom part. She pulls it between my legs and up nice and tight then buttons it up at the back. I feel her lift my skirt up at the back and over dramaticallygasp. “Oh my god” *Smack* she smacks my ass again. Hard this time. “Your panties are showing you naughty girl!”I pull the skirt down and step away from her and turn around and in my best girl voice say “Stop looking up my skirt you perv!” I adjust my skirt trying to get it to actually cover my bum.She looks down at my feet and slowly looks me up. Then back down. “Wait, there’s one more thing””Is it the bow?” “Oh, so you do remember? I really thought maybe you didn’t”She takes a pink bow escort bursa out of the box and hands it to me like I’m supposed to know what to do with it.I just hold it. Look at her, look down at the bow, back at her and just raise an eyebrow.”Oh right!” She takes it off of me and starts tying it into my hair. She kisses me and steps back “All done!””Finally!” I sayI see her expression change as a look of disappointment comes over it briefly.”I thought you were having fun?””I am.” I put my arms around her and lean in to kiss her “I’m just so fucking horny.”She kisses me back and then pulls away “Hold on.” She covers my eyes with her hand and leads me acrossthe room. “You need to see how hot you look. Oh my god. I think you look better than I would in it.”I hadn’t even really thought about how I looked in it. I was just going along with it and enjoying it.”I probably look ridiculous.””Oh no no no. She takes her hand away.I see myself in the mirror. I didn’t even recognize my self. I honestly wasn’t even sure it was me atfirst. I’m probably biased but I think I looked pretty good. my shoulders are a little wide for a girl but I think I could probably pass. As long as I don’t talk”Pick your tongue up off the floor” She giggles.She’s standing behind me at this point with her arms around me. She suddenly pushes me forward towards the mirror with one arm around my waist she pushes against the middle of my upper back to lean forward.I bend over a little. I feel the skirt going up just from me moving. I put my hands up against the wall either side of the mirror. I’m usually pretty dominant when it comes to sex so this was completely new to me. I didn’t know what was happening. I feel her run her hand down my back and grab me by my hips.She starts kissing down my back as she starts to rub my cock through the onesie and the panties.”God you’re so hard!””Mhmm” I moaned softly and started to move my hands.”Yeah that’s it baby!” She grabs my cock and I feel her lift the back of my skirt all the way upwith the other hand.”Your panties are showing again!” She smacks my ass again. I jump again. She smacks my ass harder and I let out a moan “Oh you naughty little girl” *Smack!*”You pulled my skirt up its not my fault!”She puts her hand through the back of my panties and the onesie and pulls them up as tight as she couldagainst my cock while she keeps a hold of it.I’m looking at myself in the mirror. Pink bow in my hair. This short pink skirt with long white socks onand these blacks heels. Exactly the kind of outfit I love seeing on a woman. I felt like such a little slut.I realise she’s watching me in the mirror over my shoulder. She knows how much I’m enjoying it.She starts kissing my neck while holding eye contact with me in the mirror. I feel her start to rub my cock throught the clothes. But not while holding my cock, the way you would a girl.She has the palm of her hand flat on my stomache and is just teasing the head of my cock with her fingers.”You like that baby?””Mhmm””Moan for me like a good little girl”I start to moan in my girliest voice.”Mmm good girl” she says as she smacks my ass.I feel her push me forward with her hips so I’m just a few inches away from the mirror, just leaned over slightly. She pulls the panties to the side and takes my cock out, she grabs so hard and starts jerkingme off. I moaned out loud again. I could feel the orgasmbuilding. She knew I was close and started going faster.”You gonna come for me baby? Be a good girl and come for mummy”She spanks me again right as I cum. I feel my cock twitching in her hand as I shoot all over the mirror. My legs even got week, luckily she realised and held me and stopped me from falling over. She’s leaningon me and kissing my neck and shoulders, gently rubbing my still dripping cock. She squeezes out every last drop. Licks up what’s on her hands and pulls the panties back over my cockbefore pulling my backwards ontop of her on the bed and just lay there.

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