The Walk Home

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A crossdresser's walk home after a night out.
2k words
4.64
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Part 1 of the 2 part series

Updated 06/16/2023
Created 03/30/2023
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Lucy_CD86
Lucy_CD86
17 Followers

The taxi pulled up outside the high street shops close to home.

"£10.60 please," the driver says as he steals another look at me through his rear view mirror. Who can blame him? He's just given a ride to a confident crossdresser who's still the right side of 40. I reach into my purse and pull out the cash before zipping up my leather biker jacket, giving him a lustful smile and exiting the car.

He drives away, no doubt with thoughts of me running through his head. He's not the first guy I've teased tonight, there's been dozens of others while I was out drinking in the city centre. I stand under a street light to help adjust my makeup and hair. The short black bob wig has done well tonight and after reapplying some black lippy, I look the perfect goth biker chick.

Whenever I go out, I always get a taxi home to the local high street and walk the final 10 minutes home. I always savour the last few moments of being outside alone. I notice the pub across the road is emptying out, people are going about their own way home and not paying me any attention. One guy stands alone and lights up a cigarette, probably waiting for his friends.

I begin to walk over to a nearby cash machine, readjusting my leather trousers as I go so they're perfectly placed over my generous backside. I've always been of a slim frame but have a nice curvy bum to go with it.

I quickly withdraw some cash and slip it into my purse, turning around, I get the fright of my life. "Jesus, you scared me." The guy who was smoking a cigarette before is waiting behind me at the cash machine.

"Sorry, I err, didnt mean to. Just needed to use the machine. Plus, I wanted to get a closer look at the sexy looking woman I saw. But you're err..." he trailed off.

"Not exactly the woman you were hoping for?" I finished. "Sorry about that."

"It's ok, you looked so hot from across the street. You still look hot now even though I know..." He turns away to use the cash machine.

"Aww, thanks hun. That's lovely to hear." He seems interested and he's cute. He's younger than me, late 20s I'd say with a gorgeous arse squuezed into his jeans and a perfect mop of mousy brown hair. "I'm Lucy by the way."

He finishes at cash machine and says "I'm Rich. So umm, do you live around here?"

Definitely interested! "Not far, just down the hill. You?"

"I'm heading in the same direction." He smiles as he says this.

"Well, in that case you can walk me home. It's the least you can do after scaring me earlier! Plus, every woman needs a strapping young man to escort her home." I place a hand on his firm chest as I say this, hoping it doesn't put him off.

"Ok Lucy. I can't argue with that." We begin walking towards home together. The oub crowd have cleared out and we seem to have the streets to ourselves. "So what's a... a girl like you been up to tonight?"

"Oh you know, just been into town and a few drinks with a few girls. Danced with a few guys..."

"So you're gay then? Or are you a trans... are you transgender?"

Bless him, he's trying hard not to offend. "I prefer not to label myself. 90% of the time I'm a guy. I'm engaged to a woman who accepts this side of me and allows me to have the odd girly night out. I also like the attention of men, as I'm sure you've noticed." The night is cool and dry, but I take this opportunity to fake shiver and slip my arm through Rich's.

"I've got a girlfriend. I've never thought of doing anything sexual with a man. When I saw you, I thought you were a sexy older woman all in leather. Now, I don't know what to think. It does feel nice walking with you." Rich nervously breaks our arm lock and reaches a hand around my waist at this point. I follow suit and snuggle in closer to him as I let my hand graze his backside on the way to his waist. This seems to emolden my handsome new friend and he lets his hand slip down from my waist to my leather clad arse. I notice his fingertips lightly massaging the leather.

"Mmmm, that feels nice. I love a firm hand on my bum like that." I'm glad this is going the way I hoped and he's falling under my spell. All of a sudden, I'm aware of just how close to home I am and want to prolong this feeling. "So, you like walking with me. Would you like to sit with me? I usually spend a few minutes on the bench over by the pond before I head home. It's a nice way to end the night, let's me clear my head and reflect on everything undsr the still moonlight by the water."

Rich smiles and says "Please lead the way" as we head past my street and over the bridge to the pond. "So do you dress all gothic like this when you're, you know, a guy?"

I laugh as we turn into the small park that houses the pond. "Actually, day to day I dress simliar to you. In fact I think I have that same shirt. It's Topman isn't it?" He laughs in acknowledgement as we make it to the bench. "You'd walk by me without a second thought if you saw me tomorrow."

"But you'd be able to recognise me..." Shit, I can hear the cogs turning in his mind as he thinks this over. I need to do something to win him back. I slide closer to him on the bench and slip my arm around him. He responds by doing the same and begins to lightly stroke my thigh, caressing the smooth leather. "You know, it's nice here. I can see why you like spending time here on your own."

I decide to take advantage of this moment by resting my head on his shoulder and beginning to feel his thigh. "Oooh, I love how you're stroking my leg, Rich. It's the nicest touch I've had so far tonight." He begins to stroke my leg more firmly at this, really pressing into the leather. He's really beginning to turn me on. "Mmm, that feels so good. Thank you baby." He lets out a little groan as I call him baby and a quick glance at his crotch shows quite a substantial bulge forming. I make sure to brush it lightly as I shift my hand along his thigh. He notices and moans a little. I figure it's now or never. "Thank you for walking me home tonight." I kiss him lightly on the cheek. He turns to look at me, with big hungry eyes. I move my hand up his body until I'm holding the back of his head and pull him close for a proper kiss.

He doesn't pull away as I begin running my hand through his hair. I gently push my toungue between his lips and he responds in kind. This is perfect, I haven't had this with a random guy in so long. He reaches his left hand up to my chest and squeezes my breastforms through the leather while his right one goes straight to my bum. Oh god! his hand grabbing my arse feels so good. I slide my free right hand between his legs and make a direct grab fir his crotch. Christ he feels good, at least 7 inches to play with and quite thick too! His tongue is now wrestling with my own as we eagerly explore each other's mouths.

I break off our kiss, a string of saliva keeping us joined. "Fuck, that was so good. You're an amazing kisser, Rich." We're both panting, his hand is still groping my backside while I'm in no hurry to relinquish his cock. "I should reward you for walking me home and making sure no strange men take advantage of me..." I give him my sexiest look as I squeeze his hard cock. He moans with pleasure. "How about we free this thing and I show you my appreciation?"

I begin to unzip him as he says "Yes please, I'd like that very much, Lucy." His cock is impresive, not the biggest but certainly enough to be enjoyed thoroughly. And I certainly intend to enjoy it. "I've never done this before. I'm so turned on." I start to slowly wank his shaft.

"Mmm, good. I can't believe you kept this from me for so long. You've been really well behaved. And now a good boy gets his reward..." He's leaking precum and letting out groans of pleasure while my own cock is straining against my leather trousers. "Would you like me to suck it? Would that be a fitting reward for a handsome stranger like you?" He can only nod in agreement as I bring my lips to his manhood. His scent hits me in the best possible way as I swallow his head, my tongue darting underneath. He moans again. I pull back and flick my tongue against his throbbing cock head.

I return my lips to his cock and begin to go further down his shaft. He's big and thick and I'm out of practice but I'm determined to deep throat him. I stroke his balls with my hand as I begin to gag on his length. This seems to spur him on and he begins lightly thrusting along with my movements. FUCK! I am so horny, this guy has such a good dick. I manage to get down to the bottom of his shaft, it's the thickness more than anything that's making my jaw hurt. I gag some more and come up for air. My eyes are watering and I know my make up is a mess without looking. "Fuck you look hot like that, babe. I need your mouth on my cock." Well, who am I to disappoint? I return my lips to his shaft once more, caressing him with them. I kiss up and down the whole length before wrapping my lips around his cock. I'm going to suck the life out of him and give him a night he'll never forget.

I pick up the pace and start massaging his balls. I can feel his breathing getting heavier. I'm in my element, a leather clad whore on my knees between the legs of a stranger with his dick in my mouth. This turns me on so much and I feel close to coming myself, my cock painfully hard in my pants. I keep sucking his dick and fondling his balls, waiting for the prize to emerge. He tastes anazing, musky man scent mixed with precum and lipstick. I pop the collar on my leather jacket so I can add that scent to the mix. I'm in heaven, I go to town on Rich's cock, bobbing up and down, alteenating between deep throat and licking the head. His moans are getting louder. "I'm going to cum," he declares.

I increase my pace and suddenly I feel him pulsate in my mouth. The first bolt hits the back of my throat and I swallow it down. The second lands on my chin while the third adorns my leather jacket. Just when I think he's stopped, a fourth glob drops onto my trousers. I return my mouth to him, making sure I suck him clean. I look up at him, catching his eye as we both say thank you at the sane time. I scoop up the spunk on my chin and swallow it while maintaining eye contact. I can tell he loves it, even if he needs time to recover and find his words. I scoop up and swallow the remaining cum, it tastes so good. I wish there were more. I tuck Rich's softening cock away and zip him back up. "That was amazing, lover," I say as I kiss him on the lips. "But now I have to say goodbye." I give him a cheeky wave and begin to walk away as he's still gathering his thoughts and reflecting on what's just happened.

Lucy_CD86
Lucy_CD86
17 Followers
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4 Comments
AnonymousAnonymousabout 1 year ago

great story, love it more please of lucy in leather xxx

Monalott69Monalott69about 1 year ago

Beautiful story, hope to hear more of the adventures of Lucy and her journey on becoming a woman

AnonymousAnonymousabout 1 year ago

Excellent story and so erotic

SamanthaSatineSamanthaSatineabout 1 year ago

Brief encounter but a very sexy encounter, thanks for writing and sharing it here xxx

Stay safe out there all sexy lovers xxx

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