Caught again

So I’m finding it hard to get privacy to dress up of late. So I decide to go down the country and rent out a holiday home for a weekend. I brought all my gear including make-up,and wig. When i arrived at the holiday park I entered the reception area. Behind the counter was a pretty women named Jill. I introduced myself and filled out the required forms.

“You be staying in trailer 9, my husband will show the way……Mike!!!!. She yelled.

Mike walked in to room, introduced him self and took my bags. Little did he know one bag was full of lingerie and dildos. Mike was medium build and around 5,9, couldn’t be more than 35 years of age. He gave me the grand tour of a nice cosy trailer. We made small talk for few minutes then he told me to enjoy my stay and left.

At last, Time to get naughty. I had planned to wait tell after dark till I got dressed but I couldn’t wait. First I put on my makeup. My dick was already hard. I then choose a purple nightie, with matching panties, black stockings and sexy high heels. To complete the illusion I put on a black wig. One look in the mirror makes me shiver with excitement. I put some porn on the t.v, sat on couch and proceeded to fuck my ass with varying size dildos. I decided to get comfortable and lied down on the couch facing the tv. I rammed a large dildo in & out. I moaned with pleasure. I looked at the porno and fantasised that I was the girl been fucked in the ass. I was really getting in to it when suddenly.

“ Um Sorry”

I quickly twisted my head around to see Mike standing there. “I knocked but……Im so sorry but im looking for Mr Jones”. He obviously hadn’t recognised me. For some reason I decided to just come clean. “I am Mr Jones” I replied.
“What……. Oh I see, you’re a……..cross-dresser. You certainly scrub up well”
“ Ah… thanks”

“So how’d you get into that? “ he said. “Into what?” I replied.


This question leads to us talking about my cross-dressing history for a few minutes. I suddenly realise I sitting in lingerie talking to a man I don’t even know.

“Anyway I better get dressed”. I started to get up off the couch. Suddenly he puts his hand on my leg. “No wait”. Before I had time to react he leant in to kiss me. I was surprised so i pushed him away. He tries again this time I kiss him back. He suddenly leap’s on top of me, pushing me down on my back. I could feel his dick harden as we dry hump and kiss. I pushed his trousers down and squeezed his ass cheeks.

“I want you inside me” I said

He jumps up, pulls off his jeans and his top. I reached over for the lube. I rubbed it on my ass hole. With his dick hard as a rock he practically jumped on me. He struggled to put his dick in so I reach down and guided it to the entrance. “ OK push it in” . He began to put his firm dick in my ass.

“Ah fuck yea” he whispered. “You like that” I said.

He didn’t answer. He just keep moaning as he firmly trusted his dick in and out ass fast as he could. Every so often he would kiss me for long periods.

“My wife never let me have anal sex” he whispered

“Well I’m not your fucking wife. Now fuck me” I shouted back.



As he pounded away, I wrapped my legs around his waist to encourage him to get as deep as possible.

After a few minutes I pushed him off. “What’s wrong?” he protested.

I reached for his dick and began to suck him off. “Oh god, this unbelievable”.

I could feel him getting close so I stopped and jumped off the suite. I put my hands on the kitchen counter which over looked the sitting area. I bent down and invited Mike to take me from behind. Surprisingly he bent down and began licking my ass-hole. I didn’t expect this. It felt so good. He then spit on my asshole and rubbed it with his hands.

He quickly guided his dick in to my ass once more. This time his big dick slipped in with ease. He began to fuck me. “Hold my hips….that’s it. Now ram it in as hard as you can. That’s it” I shouted. After five minutes of this I nearly feinted with pleasure.

Then out of the corner of my eye I saw what I taught was a human figure standing in the darkest only 10 feet away beside the exit. Oh shit its Mikes wife, Jill. What was she doing? Shes just standing there.

I should have stopped Mike from fucking me but I didn’t. I let him continue. I looked towards Jill’s eyes and shouted “ yea Mike fuck me…..come inside me Mike”. She never moved. Mike seemed too preoccupied to see her.

“Oh I am cumming” Mike shouted

I could feel his cum spill into my ass. I then came really hard. Cum sprayed on to the floor. I looked at Jill again and smiled. I wasn’t sure if she was horrified or enjoying the show. But my god did he feel to be watched. As Mike pulled his dick out I turned around and kissed him. I turned around to see Jill reaction, she was gone.

Anyway the next day I decided it would be best to leave a day early. I entered the reception hoping Jill wouldn’t be there. “Good morning mister Jones” Its Jill.

“Hi I want to check out” I replied. “So soon, your not embarrassed about yesterday evening are you” She said with a smile. I wasn’t sure what to say.

“Truth is Mike loves his cross-dressers, Can’t keep his hands off them.

“What?” I replied feeling confused

“Yea, we get guys like you up here all the time”

“Son of bitch” I whispered

“Let me guess he seduced you, right” she said as she laughed

" If it makes you feel any better, he said you were the best yet"

I left in a daze. I couldn’t help but feel tricked. The more I thought about it on the way home the more I felt I wanted to do it again. :)

97% (42/1)
Categories: AnalGay MaleShemales
Posted by monkeynuts0
3 years ago    Views: 1,793
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1 month ago
yes, liked the end with Mike's wife
1 year ago
As Celine stated I'd make it a point to visit more often and ask the wife to join in on the fun.
2 years ago
2 years ago
wow need to have a threesome soon
3 years ago
Have to go back and include the wife she would probily love to get fucked by a crossdresser
3 years ago
That was so hot voyuerism is so fantastic please write more stories like thisone thanks
3 years ago
Very good story, You should have stayed for an extra day.
3 years ago
I'd make that place my regular stop over!
3 years ago
NICE story! thanks for posting