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My first time crossdressing
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Hi so this story is about my first bi experience and the start of my journey into crossdressing, enjoy x
So I was in college and had been with my then gf since highschool. She had always been quite dom and open sexually. We usually fooled around at hers when her parents were out (friday evenings usually) and had experimented with a few things. She loved the feeling of kissing me while we were both wearing lip gloss, she'd fingered me a few times and she would always get me to cum on myself (at first I was reluctant but over time started to enjoy it). This friday evening was a little different. When I arrived she had was in a silky dressing gown with her make-up bags ready and told me she wanted to do my make-up. I was a little taken back but also very curious/excited so I agreed to do whatever she wanted (as usual) She put on some music and got to work. As soon as she started I was instantly hard. I look quite fem anyways and have long hair so it wouldn't take much to have me looking convincing but she always did heavy slutty make-up on herself and thats exactly how she did me. Plenty of foundation and blush, smokey eyes with thick liner and bright red lips with a gloss coat. She showed me and I was surprised how good I looked  "Put these on and come with me" she said as she passed me a thong. I go to strip off and she says "no leave your top and and take everything else off" so there I am in her living room in a baggy t-shirt and thong with a face of make-up hard as a rock wondering how I ended up like this but feeling very comfortable. She made me walk first up to her room spanking me and telling me how much of a slut I am. We got into her room and embraced, kissing passionatly and groping each other. She pushed my head down and I slowly kissed down her body until I got to her pussy. Her underwear basically wet through I kissed her through her thong until she couldn't take me teasing anymore and demanded I "stop playing and get to work". I could tell how horny she was by grinding up my face as I was eating her out. It wasn't long before she started to shudder holding up back of my head as she came hard. She then gestures me to stand as she got on her knees and slid my cock out of the thong and took it straight to the back of her throat. She was always great at giving head and had huge lips which felt amazing against mine or around my cock. After a short while she started to spank me again and probe my ass, she took my cock out of her mouth and spat on her hand and started to enter a finger into my ass. My cock twitched to which she laughed as said "you like that don't you slut" partly embarrassed I muttered "yes". "Of course you do now bend over for me" I got on all 4s on her bed and after a short time I felt something warm on my ass, she spat on me and started working a small vibrator into me. Within a minute she was slamming my ass as hard as she could telling me I was a whore and I should be taking real cock. I agreed and said I wish I was taking a real cock. She turned me on my back and started wanking me as hard as she was fucking me. I knew I was getting close and so did she, "open your mouth" I did as instructed and within seconds I sprayed my biggest load all over myself, covering up top neck and had some around/in my mouth. She collected some from my top on her finger tips and told me to suck it, still horny was fuck I did as instructed and sucked my fresh cum off of her fingers feeling used and very conflicted. She smiles and tells me to put my jeans on and leave as her parents wouldn't be too long. "Can you atleast get this off of me, I have to catch a bus home!" I protested but she just giggled and said I'll have to wash it off when I get home.... So there I am, in heavy make-up, covered in my own cum and still wearing her thong. The thought of being out in public this is was starting to make me hard again I think to myself I'll have another wank before taking this off and getting cleaned up when I get home. It's only a short walk to the bus stop and its dark so I shouldn't have anything to worry about. The stop is empty and the bus is due in about 20 minutes so I put my headphones in and listen to some music to pass the time, which is when I feel a hand starting to caress my butt..... |
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By *usie pTV/TS
over a year ago
taunton |
Oh yes lovely, please don't keep us in suspense too long. It reminds me a little of the time another gurl did my make up for me she was very skilful I always wish I had taken some pics I could not even recognise myself in the mirror. |
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A little startled I take a step away and turn around. Standing there is a tanned guy 6ft quite stocky smiling at me.
"Hey beautiful" he says in a thick eastern european accent.
"You okay there mate?" I reply
He steps toward me and asks if I want a smoke, I decline politely.
"So what have you been up to tonight?" He asks, looking me up and down
"I've been to see my girlfriend, just catching the bus home"
He looks me up and down focusing on the obvious cum stains all over my top and smiles.
"Sure you don't want a smoke?" He asks again
"Sure why not then, thanks"
He hands one over and holds a light for me. As I lean over he squeezes my as while staring me in the eye.
"I have a girlfriend and I'm not into guys" I say
He chuckles and says sorry.
He fixates on my lips as I'm smoking and says I look cute.
I awkwardly say "Thanks" and give him a little smile. I had never considered myself attracted to guys but the whole situation was getting me super horny.
I think he notices after a short while as he steps toward me again feeling my ass "You have a cute butt" I don't pull away this time as I feel a warm rush through my body and my cock twitches. "Thanks hun" I respond taking a large drag of the cigarette.
I turn away and slightly brush against his cock and I walk towards a bin to put the nub in. I don't know what has come over me (other than myself) and I drop it just before the bin on purpose, knowing this guy was watching me I bend over to pick it up showing him my ass and giving it a little spank before standing up.
As I turn around I notice a large buldge in his joggers and a grin across his face.... |
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"I thought you didn't like men" he says with a smirk on his face
"Maybe I just need convincing" Before I even finish saying that he leans in and kisses me hard, squeezing my ass and exploring my mouth with his tongue. I was a little nervous but I didn't even flinch, kissed him back and started to rub his bulge through his joggers.
Until now I hadn't even entertained the thought of doing anything with a guy but now here I am, dolled up a few minutes away from my girlfriends house making out with a random guy in a bus stop while stroking his hard cock.
"Shall we go back to mine?" He suggests
"I'm not sure, I kinda need to get back home and there aren't many buses left" I reluctantly reply. It was getting close to 11pm and I didn't want to walk back looking like this.
"Come with me and I can get you a taxi back" He says
"Still I don't even know you or where you live..."
"I'm Lukasz and I live a minute away, satisfied?"
Fuck it, why not I think "Sure"
He spanks me and takes my hand. Engaging in some small talk along the way as he feels me up telling me how much he likes my ass and how much fun we're going to have. I start to get nervous as the way we're walking I will be going straight past my gfs house as we get close I see her bedroom light on and try not to look over. We get a few doors past when he says "here we are".... opposite side of the road but I can still see it 
He presses me against his front door asking "Are you sure you want to come?"
I debate leaving for a second before committing and kissing him while feeling his cock.
He chuckles and says "Just the answer I was looking for" opening the door. I was lead into the kitchen where I was seated while he made us both a drink. He hands me a glass (vodka redbull) and puts an ashtray next to me.
"Another smoke?" As he hands me a cigarette.
"Thanks hun" I feel myself becoming more relaxed and increasingly horny. Again he holds a light for me, this time feeling my legs and hips. "Your lips look and feel incredible, I want them around my cock" I cough nervously and giggle to myself. I take a swig of drink and start to touch his cock again.
"As soon as I'm done smoking you'll get to find out" I can't believe what I'm saying or doing but it all feels natural. At this point it feels as though his cock is about to burst through his trousers and so does mine!
He pulls down his joggers and boxers and a hard thick 8" cock drippinh with precum is just inches from my face |
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I feel that familar warm rush as I stare at it, curiosity and pure lust. I take another large swing of drink and another drag of my cigarette and put it in the ashtray. I cup his balls with one hand and start to rub my tongue across his bell end. I see strings of pre cum from his cock to my mouth and lap it up as I slide his hard member into my mouth. It tastes salty and a little slimey but I love it. (Kinda used to the taste and feel of cum as my gf likes to male me taste my own)
He lets out a moan and says "good girl"
This gets my cock harder than before and I start to try my best to please him. Massaging his balls as I take him as deep as I can.
Which is when he firmly hold the back of my head and starts to fuck my face. I try not to struggle but every now and heave a little as he goes all the way down my throat. After a little while I relax and he can tell I'm enjoying it so he fucks my throat harder and deeper, calling me a whore.
"You ready for my cum slut?" He asks while still fucking my mouth. I can barely make a sound before I feel his cock start to pulse and line my throat with a massive thick load. I start to cough but he says "Swallow all of it" It feels like its gonna start coming out of my nose at this point but I start to gulp it down as his cock gets softer. "Good girl, now take those jeans off" I look up at him a bit nervous.
"You didn't think we were done did you?"
I stand up and take my jeans off revealing my thong tented as I'm still hard as a rock "it looks like you're not done either" he remarks. He feels my cock and guides me to his sofa. "Bend over the back" he demands and I assume possition. He reaches round and starts to wank me, I feel as though I could burst any second and I think he can tell as he stops and I feeling a searing pain as he spanks me hard saying "not yet slut". Another few spanks and I feel something warm on my ass, he's spitting on my hole and starting to probe it with a finger. I shudder a little but don't move away and for the first time I'm getting my ass played with by another guy.
"You like that don't you slut?"
"Yes" I whimper
"Yes sir, slut!" He says
"Yes.. yes sir, please carry on"
I feel like I'm getting stretched as he enters another and starts to pick up the pace as he fingers my ass. He reaches round again to find my hard cock coated in precum. "My little slut is enjoying this a lot" he remarks.
He removes his fingers and I feel empty, but only briefly as I again feel something warm enter my ass... It's his tongue... rimming me and tongue fucking my ass as he wanks my cock. I feel myself getting close again before he turns me over and I see him at full mast again! I instinctively lean forward to take him in my mouth again but only for a few seconds as he says "not yet" and smirks at me. He pushes me back down as puts two fingers in me and starts to wank and fuck my roughly. I feel like a slut and I'm loving every second.
"Tell me when you're ready whore" he says
"I'm close... sir"
He starts to rub my cock on his as he's finger fucking me and I cum hard all over his cock and stomach.
Just as he says "good girl" post nut clarity hits and I realise what I'm doing and what situation I'm in. A million thoughts running through my mind and I want the world to swallow me up.
He notices and says "you can leave now if you want but you'll have to walk.... and it would be a shame for all this lube to go to waste"
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