The Tree Man saw me!

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Wife planned a visitor who caught me out as a sissy cuckold.
2.5k words
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I woke early on this Saturday morning without a lot planned other than housework.

My wife, Jackie, had gone away for the weekend with her girlfriends (A booze cruise she called it!) leaving me with some chores.

The first was the weeks washing, so I carried the wash basket to the utility room as usual and started to sort into suitable piles for the wash.

The jeans and towels went together, and the coloureds were placed separately.

I came across a pair of my wife's lace knickers and noticed a stain peering up at me. I couldn't resist but place it to my nose and inhale deeply. The sweet smell of her pussy, the dampness of the patch and the slight but noticeable stain behind. I got hard as I sniffed and then placed my tongue on the damp area, tasting the delights of smelly pussy.

I didn't recall her wearing these panties, but as I was away a couple of nights before, it may have been then? I suspected she may have been seeing another chap and as I tasted the cotton patch, thought it may be cum that was making the creamy stain. Despite the realisation that perhaps she had been shagging someone else, my cock got harder at the thought of this man's cum and me licking it off the knickers.

My resistance was low, so I dropped my pyjama bottoms that I was still wearing and slipped on the knickers, with my hard cock poking out of the top. I knew that I would now have no choice but to go and see her lingerie and have a cross dressing session!

This was a usual event when she was away as I loved to dress feminine and then wank myself stupid!

I ran up the stairs wearing only her knickers to explore her wardrobe and chest of drawers.

I quickly found a suspender belt along with some stockings, a lacey skimpy bra (she had small breasts). I also selected a tight stretchy black dress she wore that showed her figure, but was short to expose her legs.

Before starting to dress, I went into the bathroom so shave the little hair left on my legs as well as trim by pubic hair tight above my still erect cock, although this was drooping a bit now as I concentrated on dressing up.

As I'm slim and trim, my smooth body was ideal for being feminized, although facially I was not convincing!

I try to overcome the more manly face by make up, so now was the time to prepare for this more difficult task, before I dressed.

Again, a nice clean shave always felt good and after moisturising, I applied a light foundation over my face, brushing wherever I could see. A little blusher exaggerated my cheeks a little ready for the eye make-up, the hard bit!

False lashes are great, so after a tricky glue application I managed to fix them reasonably in position as I then placed a blue eye shadow across my eyelids, not realising it would be easier the other way around!

Somehow, I got there and my eyes were starting to look the part, but as I brushed in mascara and pencilled my eyebrows, it all came together, only needing the lipstick.

My favourite part is the lipstick! A brushed on red base was followed by a lipstick pencil to bring out shape in a bright red shade before a gloss pen finished them off nicely.

My tummy was nervously excited as I looked at my feminine self in the mirror.

A pair of dangling silver and pearl clip on earrings added to the image now just needing the final head attire.

My wife likes dressing up, so has a couple of wigs to use when shes in the mood. One is a brunette bob with a slight fringe. I brushed it through before lifting up and over my head, before pulling back into place, trying not to smudge my make up.

Wow, I thought as I looked at my smooth body and feminine face.

I pulled the bra onto my chest clipping it easily into place. The suspender belt equally clipped around my stomach ready to attach the stockings.

The black, silk stockings were so smooth and sexy as I pulled up evenly to the top of my leg before attaching the suspender. I repeated the other leg and then pulled up the original lace panties. I resisted a look in the mirror as I wanted to see the completed package first!

The black stretchy dress was one that I could pull up my body. I stepped into it and slowly pulled up my legs through to my shoulders.

I am able to squeeze into my wife's size 7 shoes, so I selected a sexy pair of black patent stilettos and tightly managed my feet into them.

Now I was ready!

I uneasily walked, trying to be sexy, across to the full length mirror and opened my eyes to see the girl in me!

I blew myself a kiss as I felt so sexy, a bit tarty and very horny!

Well, now I thought I would continue with the chores, but knew I was desperate to have some fun with my sexy body and a couple of toys! What a dilemma!

Suddenly I heard a truck draw up onto the drive. I didn't recall anyone saying they were popping in? I sneaked a peek through the window to see the Tree Surgery lorry and the back of a man at the front door.

The bell rang...I froze.

"Oh Shit" I remembered that the tree company said they would pop in to do the hedges when the weather improved and now, being a nice day, was obviously the day they had planned.

I waited a minute or two without moving.

I heard the lorry door open and then movement around the truck sounding like tools being clattered about.

Then the noise of a chainsaw started. He was clearly going to get on with it anyway, so I was safe! Phew as that would be embarrassing!

I relaxed a little, but was a little curious about the tree man.

I stood back and aside from the window and could just see him working below.

We had taken off his jacket and was in a tight fitting white tee along with jeans and a chainsaw leather coverall on his legs and his working boots. He had longish dark hair and was tanned from his outside work. I noticed his muscly arms and knew he would be in great shape.

I reached down my dress to feel my hardening cock as I watched his swiftly trim the overgrowth. I moved closer to the window so I could see him as he moved around the garden when he suddenly looked up at the window. He smiled and waved!

My reaction was one of shock, he saw me! I smiled sort of and waved back.

He carried on working and went out of site.

A few minutes later as the shock had sunk in, the doorbell rang again. It was him.

As he had seen me, I couldn't ignore it, but what do I do?

He called out "Hey, can I get some water please honey?"

I had to go down and answer the door.

"Sure." I said in my best feminine voice as I opened the door and stood behind it in one swift movement, trying to hide myself.

"Hi." he said as he stepped inside.

He bent to take off his boots so I saw his cute bum as he pulled them off before quickly turning and looking straight into my eyes.

"Hey, where's Jackie today." he said through a smile.

"Oh, you know her?" I quizzed.

"Yes, I pop round most weeks to help out, did she not mention me?"

"N..N..No, I stammered." wondering what he was talking about.

"She said she was away this weekend, but that her husband was in and he would pay me."

"Oh, Ok. But I don't have any cash at the moment."

He smiled again, a lovely soft grin from his thick kissable lips.

"Well, when Jackie is out of cash she helps out in other ways."

What was he talking about, I thought.

"Oh, Ok, what do you have in mind." I stuttered now realising what he must have meant.

"Well, Jackie does do a rather good BJ!" he laughed.

"What!" I exclaimed. "My wife sucks your cock?" I shouted. She doesn't suck mine I thought to my annoyance!

"Oh yes, she says its much bigger than her husbands and just loves to suck me as she has a smoke."

"But my wife doesn't smoke?" I said confidently.

"Ah, I get it, you're her husband!" he laughed.

I realised what I had said and felt embarrassed and hurt with jealousy.

"Sorry mate, he said, you look so great that I thought you must be her friend not the husband!"

"Well I am!" I stated.

"Are you jealous?" was his smirk.

"Yes, of course."

"Well, why don't you have a go and then you will be even?" he suggested.

He walked closer and pulled me strongly to him.

His lips brushed mine as he held tight.

I couldn't resist but to respond and pressed my red lipstick covered lips onto his. Our tongues soon entwined and we started a passionate kiss.

He broke away and led my to the front room.

He stood back to admire me and whistled. "Were gonna has some fun babe."

My aroused state took over. I reached into the kitchen draw to pull out the discarded cigarette pack, turned and he lit my cigarette.

As I blew smoke sexily at him, he pulled off his tee to parade his abs and pecs, smooth and tanned, so sexy.

I smiled as I looked at him smoking sexily.

He undone his jeans and slowly dropped then to the floor, standing with just his boxers and a curious bulge.

It was an easy decision to drop to me knees in front of him.

I placed my thumbs in his boxer waist and slowly drew them over his hardening cock, gradually exposing a beautiful 8 inches of man meat.

"Wow!" was all I could say as I looked up at his gorgeous blue eyes watching my every move.

My hand went around the thick shaft and pulled back a little to move his foreskin further down his tool. The bulbous pink helmet expanded as his cock grew hard and erect in front of me.

A drag of my cigarette was followed by a blue smokey haze over his cock as I lent forward and started to lick up his length. Both sides were equally veiny, sexy and taught. I held his massive balls that were swinging below as I then engulfed his hard member with my mouth.

I covered the head before pursing my lips around his cock. A slight suck and hold as I pulled back over the helmet to taste his pre cum. He was leaking lots of juicy fluid which I licked before then sliding my mouth down his shaft and repeating the exercise. I moved my mouth down further then pulled up but leaving a couple of inches in my mouth. I tried to get all of it in, but probably only managed 5 inches before choking a little. He laughed as he started to face fuck me.

I moved my hands to his lovey bum as he thrust forward to force fuck my mouth, slowly at first but then faster. I started to gargle on all his pre cum and pushed him back so I could breathe.

"You wanna be fucked like your slutty wife!" he asked demandingly.

Still in shock that he was fucking my wife, I simply nodded.

"Well she likes it in her ass."

'Not with me he doesn't.' I thought!

"Bend over you slutty bitch."

I did as I was told and turn around.

He lifted the tight dress exposing my wife's lacy knickers that I was still wearing.

"I recognize those." he laughed, "I wiped my cum off in them a couple of days ago."

The sudden realization made me quiver. I had licked his cum earlier today!

"Oh please fuck me!" I now demanded wanting him more and more remembering that creamy taste from a few hours ago.

He pulled the lace to one side as he knelt down, his cock bouncing onto my smooth bum which was raised in the air, waiting for him.

He spat onto my ass and as I felt his spittle run over my hole, his cock suddenly pushed against my initial resistance. He pushed a little more without penetrating, but I moved back promptly making his big cock break my seal as he slid into my desperate hole.

"Mmmm." he muttered as he then slid in deep, making me gasp with pleasure. Slowly at first, he pulled back and again spat now on his cock and spread over his shaft just as he pushed again. In and out so smooth as he got faster. My ass was in ecstasy and my prostrate was receiving its desired attention making me dribble my cum on the tiled floor below.

"Fuck me babe!" I screamed back at him and he quickened his pace and fucked me hard, holding my hips and pushing down on my back as he fucked me.

"Smoke you tart." he said quickly. Clearly his fetish was smoking, which turned me on even more.

I reach aside and pulled a fresh long cigarette from the packet, then lit it with one hand whilst I held myself on all fours bouncing against his continuing thrusts.

As I held the cigarette and looked back at him, his eyes were shut and I saw his face tighten as he screamed "I'm coming, honey".

The first shot made me also dribble more cum on the floor, then his second and ongoing thrusting produced more and yet more of his hot creamy spunk.

A final push and he held himself deep in me, his balls bouncing against mine.

"Wow, that was better than fucking your Mrs you tarty bitch!"

"Mmm thank you babe that was great." I replied, just as the door slung open and Jackie appeared, looking tipsy with a glass of wine in one hand a cigarette in the other.

"Better than me hey?" she said as she smirked at me.

She knelt aside him and kissed him passionately on his mouth. "I told you he would be a good fuck didn't!" she said to him.

"What, you planned this?"

"Oh yes, I knew you were sissy fucker, so thought I would treat you!" she laughed.

She pulled his softening cock from my gaping hole and wiped his cum off his cock and pushed her fingers back in my hole. "Here, you can taste some of his fresh cum rather than off my stale knickers!" as she held her wet hand in front of me. I looked at her twinkling eye as I licked her hands clean. "Mmm tasty!" I smiled.

"Right, now I'm going to let him fuck me hard when he gets it up again, then you are going to lick me clean, ok?"

"Yes Please." was all I could say.

This was the start of me dressing for him on a regular basis, so as well as keeping Jackie satisfied, he also kept me suitably filled with cum in both holes!


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AnonymousAnonymousover 1 year ago

That's when he had the treeman arrested for sodomy and his wife for pimping. Then he divorced her. Got to be consequences

AnonymousAnonymousalmost 4 years ago
Fantasy realized

I am long time cross dresser and always get a good hard on dressing up usual in PVc, short tight mini skirts tight top and thigh boots prancing around then inserting a vibrator up my arse and wanking my self silly. One evening I decided to go for a drive I dressed in a tight red pvc pencil skirt a black silk blouse and a laced front bodice. I alway wear undies a lace trimmed black bra, matching waspie tightly laced, panties and suspenders with black silk stockings full make up and a shoulder length black wig. Teetering on a pair of 4" stilleto heeled booties I slipped out of the house and drove round a while then it happened a puncture I pul over, it was quiet country road. I got out lifted the boot bent in to retrieve the spare tyre when a car came pulling in behind me. I was scared as a tall man got out smiled at me saying "Hi you got a problem" I swallowed nervously and said "Yes a puncture" he stared then said "here let me help you". He changed the tyre as I stood watching feeling a rising excitement inside me. He finished put the spare in the boot saying "there all done". I smiled at him and said "what can I do for you you were so kind"

He just stared at me I ran my hands over my body "Maybe you would like some fun with me" His hand slid down to his crotch and unzipped his flies pulling out a stiff cock, Hopw about you suck my cock" I'd never done this before but watched plenty of porn movies so dropping to my knees on the grass I cautiously took his cock in my hand then licked the tip before sliding into my mouth. He muttered "fuck suck it go on" I was soon sucking and licking him as he began to fuck my mouth panting and gasping "youre a fucking slut ooh you fucker" and my mouth was filled with warm sticky sperm. I swallowed as fast as I could but he was pumping sperm out hard I gasped his cock slipped out and my face was covered in a jet of his sperm.

I sat back my own cock rock hard under my skirt, he looked down at me the pulled me up spinning me round pushing onto the car bonnet.

I gasped "No don't please" as he pulled up my skirt over my hips, he pushed my legs apart holding me down. I felt him yank my pantes aside then finger my anus before he pushed is cock against it. Several thrust and some pain his cock slid inside me. I gasped "oh please no" then he began fucking I was held firm and my body began shivering with uncontroled extascy my cock twitiching then I came in the biggest come I'd ever had as I was fucked hard. He grabbed my hips rammed his cock hard into me gasped "you fucking kinky slut oh my" he was pumping his spuck into me by the bucket load. He sagged over me panting the pulled put his cock I felt his sperm oozing from my anus. I pushed myself up as he stood back my legs were shaking, he smiled "see you around slut maybe I'll fuck you again" I replied" I look forward to that any time you want to" He left after I'd given my phone number I stood watching his car leave my cock stiffened and I wanked my self coming all over the car bonnet feeling his sperm oozing down my legs.

Two weeks later we met again and his cock was up my anus in two minutes then I was taken by his friends but thats another story.

AnonymousAnonymousabout 4 years ago
I loved it, was well written

I really enjoyed it, it was very well written and got me hot, after all the years of dressing i need a man like this to own me and make me his bitch in all ways, thank dianefritz8395@yahoo.com

Old GreeboOld Greeboabout 4 years ago
Unconvincing

Some sissy stories read as though the writer is mature enough to be writing from experience - both of the fetish he's describing, and of life in general. This one doesn't convince me in either respect. Also, it needed editing, or at least a re-read before publishing.

petey377petey377about 4 years ago
nice

lucky sissy will it continue

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