Surprised by the Delivery Man

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Caught crossdressed by delivery driver.
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My wife was away for a few days, giving me a chance to enjoy some crossdressing.

I have been a closet dresser since a teenager, enjoying many private times experimenting with girly clothes and lingerie, along with trying make up and wearing wigs.

Whilst I'm a fit, slim chap, I am rather hairy, so I started my day by shaving wherever I could reach, but especially around my balls and bum!

Nicely smooth I then put on some new black silky stockings, held up by a PVC basque. The basque was very sexy, with buckles at the front allowing me to pull in my waist a little. The suspender clips were nicely finished in the same shiny effect which I admired as I clasped them onto my stockings.

Some nice French knickers went well with the basque, hipster style, covering my cute bum and enclosing my growing cock. "Keep down" I joked with myself.

Then it was time to put on a dress. I have this stretchy lacey dress that covers my upper body and arms as well as pulls down tight to just above the knee,

I slipped on the dress and adjusted it so it clung nicely to my body.

Next was my attempt at make-up which I'm not very good at, but the effect of the foundation, blusher, blue eye shadow, false lashes and sexy red lipstick was very horny.

The foundation was a creamy type that I smoothed all over my face, softly spreading evenly.

Using a cotton bud, I applied the sexy blue eye shadow over both sides, again making sure it was even and not too overpowering. The eye pencil closed the blue and increased its effect allowing me to then glue on the false lashes. These were not too big, just long enough to make the eyes stand out more. Some blusher then produced a nice glow to my cheeks making my face ready for my favourite make up item, red lipstick!

I applied a first coat of the sexy red lippie base, pursing my lips to even it out. Then I used the paired applicator with the glosser. I was getting very exciting as my lips started to shine with the sexy red gloss, causing another adjustment inside my Knickers!

A pair of dangling earrings were then clipped in place and hung nicely ready for my brunette 'bob' wig. I brushed the wig into shape before lifting up and over my head then pulling down into place. The mirror showed me a sexy smiling womanly face, to which I blew a kiss.

I slipped on some black patent heels. Never easy to walk in heels, but these 3 inch stilettos were manageable and added to that lovely sexy feeling I get when dressed.

My final addition, was a pair of long PVC gloves that I slid onto my arms and tightly stretched over my fingers.

Wow, I thought as I again looked in the mirror, what a sexy girl!

As my normal routine, I started walking around the house feeling really horny. With no one at home, it was so sexy to be able to wander around acting feminine.

Strangely, when I'm dressed I like to smoke sexily, but never as a man! So I nipped into the back garden to get myself even hornier! I opened a new pack of Berkley Superkings, which are a long all white cigarette. I placed one in between my lips and lit the cigarette, blowing a sexy plume of bluey smoke.

As I walked around the garden, I could see myself in the window reflection from our glass patio doors. I held the cigarette in my hand with my arm bent upwards to make a pose and it was so sexy that I didn't notice the rear gate open.

A DPD delivery driver suddenly appeared in the reflection.

As I saw his reflection, I screamed of fright or maybe embarrassment or both!

He was smiling as he handed me a parcel, addressed in my wife's name.

Then, in his European accent, he asked me to sign, which was not easy with the PVC gloves on.

As I signed his hand-held gadget, he said "You look very nice today".

I didn't need the blusher to make my cheeks go red this time.

I looked at him as he spoke, noticing his blue eyes and full lips on a slightly tanned face and brown hair neatly layered from a side parting. He was taller than my 5'7'' by a couple of inches and his DPD polo shirt exposed his strong looking arms. I couldn't help looking him over, seeing he was slim and smart looking.

He then surprised me by asking if he could use the toilet. Nervously I said sure and showed him into the house.

When inside, he said he could wait to go, but would like to take a picture of me ''For later'' he said.

I asked him what he meant and he smiled showing his even white teeth and said, ''Something to wank over'', which again shocked me, but also turned me on.

A guy wanking over my picture, wow!

I was now in unchartered territory, but couldn't help but be excited.

"Ok" I nervously replied. As he got out his mobile to take the picture, I posed with one hand on hips and a fresh cigarette held higher in the other, with my elbow bent (my favourite sexy pose as you will already know!).

I moved into some different poses, turning a few times and as he took more pictures, I couldn't help but notice a bulge in his jeans as my eyes were drawn down to admire this sexy delivery driver.

He saw me looking and smiled again. "You are such a tart, aren't you?" he said.

Again, I felt myself blushing as becoming a tart is all part of my fantasy.

"Come over here" he then demanded.

I walked on my heels towards him. I was trembling as he pulled me close and suddenly kissed me! I hadn't ever been kissed by a man before. It was like electric as he darted his tongue to part my red lips, sucking a little as his moist mouth closed over mine and our tongues entwined. It was so erotic, that as I was so close I could feel his growing bulge press against my thigh and thought I could try cock for the first time!

I pulled away from his kiss and dropped to my knees. I caressed his chest as I moved down, gradually letting my hands reach the bulge in his Levi's.

I reached inside the waistband to unclip the button, and I saw his bulge strain against the jeans. I then slowly unzipped his jeans, enjoying the anticipation.

I pulled them down exposing his white boxers. He removed his polo shirt and gently placed his hand on my head.

He was a really fit lad with smooth thighs and a nice slim waist. I couldn't help but caress his toned stomach.

He cock was looking so big in his boxers as I stared with excitement at it.

"Light another cigarette, I like it" he said.

Dutifully I lit another long white cigarette, looking up to his smiling face, blowing smoke up to him. He leant over and kissed me again, slowly but wetly, as I felt his spit across my lips, still red from my super lip pencil.

I couldn't wait anymore, so I then pulled his boxers down allowing his beautiful cock to spring out.

It was about 7 or 8 inches erect and quite thick, slightly veined with nice foreskin still partially covering he head as it lifted to an upward angle.

This lovely cock, my first, was dripping already. I blew smoke over it, wanting to take my time on my first blow job (other than dildos!).

I licked at the base of the head, where the foreskin pulls away, flicking my tongue, then around the deep pink helmet tasting his delicious pre-cum, next up and down his long shaft as he started to moan gently. My mouth enclosed over his long cock and I slid my mouth down a couple of inches, closed my lipstick covered lips around his shaft, sucked a little and slid my mouth back off his cock. Then again, but deeper in my mouth this time, sucking a little harder and again and again.

It was wonderful, sucking this young guys big cock and by the sound of his moaning, he was enjoying it. Just what a slut like me wanted.

He suddenly pulled my head off him and pushed me back onto the sofa. I lay on my back, exposing my stocking tops. Roughly he pulled my lacey dress up where he could see my hard cock struggling to contain itself inside by French knickers.

He pulled my knickers down, smiling (or was he laughing) at my 5-inch cock and my smooth balls drooping below.

He pushed me further onto my back and laid over me lifting my legs up so his cock was close to my little bum hole. I took a drag of my cigarette as he slowly started to slide his cock into me, he laid further over me and kissed me again as he slid into me...oohh it was so good to feel a real cock in me. He started to move his hips and slowly fuck me as he kissed me, then started to get faster and he sat up a little, but fucked me harder and faster.

"You dirty slut" he shouted "I'm going fuck you hard you tart".

I loved it as I whispered, "Please please fuck me" to which he really started banging his full length in each time.

A few minutes later, he pulled his cock out of my ass, only to notice that I wasn't 'clean'.

I hadn't expected to be fucked after all!

"You dirty bitch, look at your shit on my cock!" he shouted.

"Clean me up!" he said, but as I went to get up for a towel, he said "No clean it with your mouth bitch."

I was shocked. Both at how this sexy lad had become more aggressive, and at what he told me to do, I never played those sorts of games.

I stared at his cock with a brownish coating over it, but also a thickening of brown caught under the helmet.

He grabbed my head, pulling me closer and pushed his cock on my face, then in my mouth. I tried to pull away, but he held a firm grip.

I had no choice, so I started licking and sucking, tasting the dirt. Strangely It was disgustingly sexy! This nice young man making me do something I've never done, but his cock was so sexy I couldn't resist but do what he wanted.

I cleaned him nicely but his hard cock wanted more action. I turned on all fours and offered him my ass again. I always wanted to be fucked in this position, submissive under a thrusting man.

He spat on my asshole, then rubbed his cock head along my crack, before sliding back in and fucked hard and fast.

He spanked me hard on my bum cheeks making me squeal with slight pain but lots of pleasure!

I could feel his big cock start to throb as he said "I'm cumming".

Then I felt a stream of his hot spunk shoot into me. It was so horny that my cock also throbbed with joy and a little drop of my cum dripped onto the sofa below me.

He kept fucking and emptied into me. Moaning as he slowed his movements, leaving his big cock to start to reduce inside of me.

I put my hand under my bum to feel his cum as it dripped out when he pulled out of me.

"That was good" he said as I turned and saw his softening cock covered in his cum.

I looked into his eyes as I licked his cum from my hand and said I can clean him again if he wanted me to?

He smiled an approval. So obediently, I sucked his cock clean of his cum as well as wiping up more of his dripping cum from my ass and smearing it on my own face. He sure was a big cummer! There was loads of it, so tasty, salty yet creamy and still warm.

I looked up at him with my cum covered face and cum dribbling lips as he said, "My turn to clean you"

"Oh, ok" I replied.

I was expecting he meant he was going to suck me which would surprise me after he had already cum! But then I realised he didn't meant that, as I felt a sudden gush of his hot pale coloured piss strike my face.

He now needed his pee and continued to use my face as his urinal, washing away the cum, but also pissing into my mouth, I gurgled his sweet tasting pee and put my mouth over his cock until he stopped, swallowing as much as I could as I didn't want the mess over the sofa!

Satisfied, he then put his boxers and jeans back on and shouted, "Thanks babe, see you next week, same time" and waved goodbye.

I sat back shocked at what had just happened, but smiled as I thought of his big cock in me.

I lit a final cigarette and stoked myself to a lovely cum!

I can't wait until next week!

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AnonymousAnonymousabout 5 years ago
Air Conditioner Guy

Had something similar, AC guy came unexpected while I was dressed. After he finished he asked me if I was a fag. I told him I was, he asked if I would suck his cock and I did. After I swallowed his load he said he needed to piss, I told him the urinal was my mouth and he used me.

AnonymousAnonymousabout 5 years ago
Cum in me

Loved this story would loved to been me in that position. Loved every thing he he did to you . My fantasy from the start keep writing x

AnonymousAnonymousabout 5 years ago
Great story

Loved it...I want to be fucked...cummed on and pissed on whilst dressed in sexy underwater...by more than one guy...

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