Lucy's First Blowjob

It was late 2018 and around six months after splitting up with my ex-girlfriend. I'd been taking my new found freedom as a sign to dress up as much as possible. I'd come home from work and immediately get changed into something sexy, I'd spend time browsing online for new outfits and had started experimenting with sex toys.

I'd been getting back into the idea of dating and as well as looking at straight dating sites, I'd also downloaded a couple of apps where I could let Lucy out for attention. I'd had a fair bit of attention but never got close to meeting up with anyone. Either they'd be too pushy, something would come up that I wasn't particularly interested in or I'd get so horny from the chat that I'd end up wanking myself silly and then have no desire to carry on the conversation after I'd cum. Plus, I wasn't quite ready to meet a blokey bloke, I was focussing more on finding a girl like me. All these things I'm sure are fairly common occurrences for closeted crossdressers, I've certainly read of a few similar experiences.

One Sunday I woke up early and decided I was going to have a day fully dressed. I went into the bathroom and covered my body in hair removal cream and then washed it all off in the shower. I dried myself off and went and admired myself in the full length mirror in the bedroom. I loved how feminine my slight frame looked now it was devoid of all its hair, my long legs looking particularly appealing.

I slid on a black thong and carefully hid my cock and balls away, grabbing a matching bra and slipping a couple of breast forms in, I could see the feminine illusion begin to take shape. I slipped on a pair of tights and selected a red leather mini skirt to go with them. Slowly, I pulled the tights up over my smooth legs, savouring the wonderful feeling as they encased my legs. I pulled the skirt up over my bum and zipped it up at the back, admiring the curve of my behind as I did. Next I grabbed a white blouse and threw that on top.

I sat in front of the mirror and began to apply my make up, smoothing the foundation over my skin. I applied a grey smoky eyeshadow and a small wing with my eyeliner. Lastly, I picked out my reddest, sluttiest lipstick and applied it heavily to my lips. This wasn't enough, I needed to look sexier and dirtier today. I scrambled around my makeup supplies, looking for my liquid lip gloss. Found it! I applied it liberally until my beatiful red lips looked soaking wet. Looking at myself in the mirror, I was already fully aroused at the sight before me and I hadn't even chosen a wig yet! I picked out a long dusty grey coloured wig and attached it in front of the mirror. Almost perfect! Still need shoes and accessories! I put in my biggest silver hooped earrings, matching nose ring and a couple of bracelets. Around my neck, I wore my silver gothic crucifix. I finished off my look with a pair of red patent stilettos.

I couldn't believe how good I looked! I was making myself so horny, I quickly snapped a couple of pictures and uploaded them to the dating app. Almost immediately I got a message of approval from another crossdresser and an accompanying dick pic in a cute pink thong. Their cock wasn't that impressive but I was in full horny mode now and had to get back on my bed and pull some toys out.

I got out my purple six inch dildo and pulled down my tights before slowly inserting it in my ass. It felt so good as I rubbed my hard cock through my leather skirt. As I lay there, rubbing my cock with a dildo inside me, I snapped a quick pic and sent it to the crossdresser who had messaged me. They were very appreciative and asked me to meet. I asked where they were and was gutted to find they were over 2 hours away. I let the conversation die and focussed on myself. By now, I'd taken my cock out of my thong and was gently stroking it, feeling so turned on and ready to burst. I kept thinking of the other crossdresser's dick and how I'd have loved to suck it dry if only she'd been closer. This sent me over the edge and I exploded in an intense orgasm, my cum shooting onto my blouse and the feeling of my muscles contracting against the dildo inside me feeling heavenly.

Laying there in post-orgasmic bliss, I was determined that today I would remain dressed up and that I would, at some point, meet someone. Determined not to let that post-orgasm guilt set in, I got up and cleaned myself up. I took off my blouse, tights and skirt and had a quick outfit change. I put on a leather halter neck top and a pair of black PVC trousers and matching biker jacket. I decided to pop on my leather ankle boots too. Looking at myself in the mirror, I was so turned on again but I was determined not to just sit back and masturbate again. I did miss the feeling of having something in my bum though, so I quickly pulled my trousers and underwear down and slipped in my small metal butt plug. It felt divine as my hole swallowed it up. I pulled up my trousers, checked my makeup in the mirror and headed downstairs.

The sound of my PVC creaking as I walked and the plug in my arsehole were keeping me on edge. Today was going to be one horny day! I made myself some lunch and sat down to eat in front of the TV. I was just finishing up when there was a knock at the door. Shit! I'd completely forgot about the delivery! I wasn't ready for anyone to see me like this! Reality set in and I was panicking as the knock repeated. Ok, calm down, it's just a delivery. They don't know you, they'll be out of your life in seconds. Nervously, I got up and walked towards the back door of the house. What if the neighbours see? Too late now, the delivery guy has seen me through the kitchen window, I've got to go through with it. As I approached the door handle, my brain suddenly kicked back into gear and I seemed to remember how sexy and empowered I usually felt dressed in PVC. Reaching out for the handle with my left hand, my right dropped to my plastic encased thigh and caressed the smooth shiny material. "Parcel for you si... err miss," the delivery driver said as I opened the door. I could see a little smile forming on his face as he handed me the package. I chose to believe this was because he liked what he saw and not because he found the idea of a crossdresser ridiculous. Thanking him, I closed the door and began opening the box. I'd completely forgotten I'd ordered a mains powered wand the other night while I was up late feeling horny! I could feel my dick beginning to strain again against the tight PVC, I absolutely have to try this new toy out!

I hurried upstairs and took the wand out of its box, plugging it into the socket next to my bed. Flicking the power on, I was immediately amazed at how much more powerful the vibration seemed compared to my battery powered toys. I laid back on my bed and placed the vibrating head against the crotch of my trousers. Even through the thick PVC on this low setting, I was finding it hard to resist. I began bucking my hips slightly and let out a small moan. I began feeling my breastforms with my free hand as I slowly moved the wand up and down my still covered cock. I slipped the wand's power up higher and felt the immediate effects! I was in ecstacy, holding it directly to the underside of my cock head was sending waves of pleasure through me like I'd never felt before.

Suddenly my mind wandered back to the delivery guy. I imagined inviting him in with my parcel, placing it on the side while I dropped to my knees in the kitchen and pull his hard member out of his trousers, I rub it against my PVC clad breasts before taking him in my mouth. Working my tongue under his head while I fondle his balls between my fingers, he holds my head firm to make sure I keep him all inside me. I keep sucking as he moans deeper, my tongue frantically swirling around his shaft. In my mind I feel his cock begin to pulse as he shoots his seed doen my throat.

Back in the real world, my legs begin shaking uncontrollably as I feel my own orgasm begin to take hold. The feeling from this wand is so intense, the pleasure waves moving through my entire body. My balls feel like they're about to shoot off into space! My dick begins to convulse under my PVC trousers as I unload for the second time today. Fucking hell, was this toy ever a good purchase! My whole body feels like it's glowing and my cock and balls feel so sensitive but in the best possible way! I slowly unizip my trousers and lay my just spent cock out in the open. I turn the wand down a little and just rest it under the head of my penis. I'm too exhausted to move, but this feels great. To my surprise, it's not long until I feel another orgasm building and I ejaculate again, this time splashing my PVC jacket. I lie there and scoop up my cum from my jacket and bring it to my lips. Mmmm, it tastes so good. I swallow every drop and finally turn off the toy.

I lie there on the bed, spent. I'm not sure how long it's been or if I had a nap. Eventually, I get up and take off my dirty clothes, remove my make up and run myself a bath. While my body is submerged in the bath, a worrying thought hits me. I came while fantasising about a man! Not a crossdresser or trans woman, an honest to God man. The delivery guy, an actual real man that I met. But why? I'm not gay, I like women. I'm not attracted to the masculine form. But it was a sexy fantasy and I'm getting hard again. It's so confusing!

I got out of the bath and dried myself off. I'm not done dressing up today! I redo my makeup in a heavy goth style. Foundation a shade lighter than usual, black eyeshadow, eyeliner and lipstick. Nails too, can't forget those. I slip on my red lacy thong and matching bra and suspender belt. Next, I slide my fishnet stockings up my legs and attach them to the belt. I grab my sheer top from my drawer and throw it on. Turning to my wardrobe, I know exactly what I want; my PVC dungaree style minidress that's actually two sizes too small and so absolutely clings to me. I slide it over my head and zip it up, the zip just about fastening all the way. I grab my leather knee boots with a chunky heel and slip my feet into them. Next, I slip on my black bob wig and adjust it so it sits perfectly on my head. Completing my look, I grab my leather spiked collar with o-ring and put it on just one notch too tight so I feel a little lightheaded. Bliss. I look in the mirror and admire myself in my 3rd outfit of the day. I snap a few pictures and upload them. I hope I get more attention now it's evening time.

I sent a few flirty messages back and forth with a couple of crossdressers but nothing came of it. I was just about to log off when I received a message from someone whose profile was named after the local shopping centre, a well known hook up spot. Opening the message I'm disappointed to see it's a picture of a guy's abs. I was hoping for a sexy CD! But he does have a nice body. But I'm not into men, I prefer the feminine form! Another picture comes through, this time it's his cock. His gorgeous, long hard cock! Fuck it, I'm so horny and I was determined I was going to have an experience today. I messaged a quick 'Hello'.

The reply comes back:

'Hi. You look sexy. What are you looking for?'

I reply:

'I want to suck my first dick. I can accom.'

'That's cool. I love being fucked.'

'I don't want to go that far yet, I just want to suck someone's cock tonight.'

He didn't push the point and politely asked when we could meet. I told him right now if he wanted. He did. I gave him my postcode and told him to message me when he was on my street. Fuck, it hit me. I've just arranged to meet a man for sex and to top it off, I don't even know what he looks like. Well, too late to back out now! I sat in front of my mirror and touched up my makeup, making sure my wig was set perfectly. It wasn't long before I got a message saying he'd arrived on my street. I sent a message back with my house number and instructions to come to the back door as the front door was blocked. I threw on my black PVC trench coat with the floral embroidery on the sleeves, I wanted to gvive him a bit more to unwrap! Suddenly, there was a knock on my front door. I looked out of the window as my nerves took over to see the guy I'd been texting standing there. I motioned through the window to go around the side of the house but he just stood there. Nervously, I stepped out of my back door and walked around to the front of the house, thank God I'd worn my coat! It was a lot colder than it looked.

As he saw me coming around the house, he began to walk towards me. My nerves were reaching new heights, matched only by my horniness and desire to suck my first man. He said I looked sexy and held me around my waist as we walked toward the door. Instantly, my nerves vanished at the feel of his arm around me and I turned and kissed him on his lips! I couldn't believe it, my first time kissing a man and I'm doing it outside, dressed up where all my neighbours could see! I felt like such a slut as I broke the kiss off and led him inside.

Getting him inside, I took my first proper lookk at him. His face was handsome, very manly and rugged looking in the best possible way. He was dressed in sweatpants and a zip-up hoodie. Standing in my front room, I took off my coat and then ran my hand along his chest as we kissed again. This was different than kissing a woman, not as soft and without that sweet feminine smell but it felt great as he eagerly probed my mouth with his tongue. I unzipped his hoodie and dropped to my knees as he took it off and removed his t-shirt. Wow, I was face to face with those magnificent abs, I don't know what came over me but I leaned forward and kissed them softly. I could see a hard bulge in his joggers and knew now was the time. I reached into his waistband and under his boxers to claim my prize.

Here I was, on my knees dressed in PVC and holding another man's dick in my hand for the first time! No, not another man's dick, just A man's dick as I was wholly in the feminine role right now. I pulled it fully out of his clothes as he pulled them down and stepped out of them. Such a lovely cock, nice and thick with a good length. Must be easily 7 inches. I began stroking him with my hand as I would normally do myself, he let out a little moan and I found myself getting so turned on at this. I slowly moved my fave infront of his engorged head, gingerly flicking my tongue out and making contact for the first time. He moaned again and I gave a more prolonged lick as I continued to wank his shaft. I slowly opened my mouth and began to place his head inside, this was it, I was finally sucking my first dick! It was warmer than I'd expected and tasted quite musky but in a way I liked. I licked underneath his cockhead while I sucked and pulled back. I moved my head forward again, this time taking part of his shaft into my mouth too. He moaned louder and I could feel my own excitement growing. I leant back a little so I could feel my butt plug pressing against me, I was in heaven!

Feeling a mixture of brave and horny, I tried to take his whole length into my mouth. I got about three quarters down before I started gagging, but I could hear his groans becoming louder. I pulled my head back, took a breath and tried again. This time, I got all the way down and could feel my face buried into his crotch. I pulled back, still gagging slightly and went back to sucking his head. I began to play with his balls in my right hand while I worked his shaft with my left. After a couple of minutes, he gently pushed me back.

"Lie down on the sofa babe." I complied and withon seconds he was on top of me in the 69 position. As his dick hung before my face, I could feel him freeing mine from my lace thong. I began to lick his cock while he started stroking me. I have to admit, it wasn't easy for me to suck his dick in this position but Lord, was I going to try! By now he'd begun to suck me too and it was the best feeling I'd ever had, no woman had ever come close to having this sort of control over my pleasure! I become lost in my own feelings and let him slide from my mouth, this feels fucking heavenly! Fuck, he could fuck my arsehole right now if he asked. I'm so close and if I hadn't already cum today, I know I would have blown a huge load in his mouth right now!

Suddenly he stops and starts to scoot down my body, positing himself over my cock. I'm pulled out of my haze and brought back to reality. "I said didn't want to do that tonight. I don't even have any condoms!" He aplogises, climbs off me and kisses me gently on the cheek. My mood softens and I beckon him to climb back on me so we can resume sucking each other. Soon, I have those heavenly lips wrapped around my cock again and can feel my climax building, only to have him edge me expertly and cool off until my writhing subsides. He definitely knows his stuff! I get extremely brave and begin licking his butthole, it doesn't taste great but he definitely enjoys my tongue darting between his cheeks! I begin wanking him hard and fast as I lap at his hole. We're both moaning pretty badly while pleasuring each other and I feel like I'm finally going to cum when he stops.

Before I can react, he's on my floor on all fours, furiously wanking his own cock. This is weird, but I'll go with it! Staring at his hole while he's on his hands and knees, I go back to licking him. I'm so turned on and so close to cumming that my earlier reservations go away and I decide I want to fuck his arse after all. I slap my cock against his cheeks and spit down his crack for lube, preparing to enter him. Just as I begin to line myself up between his cheeks, he cums loudly all over my carpet. Quick as a flash, he stands up and apologies, throws his clothes on and leaves. I'm left there, horny and speechless with a strangers huge load on my carpet to clean up. I can't believe the bizarre turn of events that have just taken place.

I clean the mess up and go upstairs, hopping back online and hoping that someone, anyone at all, wants to come over and have a normal sexual encounter. Alas, it's late and I end up wanking myself off again to the thought of what could have been. I got a message from the guy the next day asking if I wanted to meet again. I never responded, but all these years later, I wish I had. He had the nicest cock I've ever played with.