Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click hereI'd completely forgotten that the repair man was coming round to fix the coffee machine. My wife had arranged it. I was at home alone and had jumped at the chance to be fully dressed. I was wearing a cute green flowery mini dress with white kitten heels. I was fully made up and had even painted my nails and toenails a lovely shade of pink.
When the doorbell rang I just assumed it was an Amazon delivery. They normally ring the bell, put the parcel on the doorstep and leave.
I didn't even think about it. I opened the door and there was a guy standing there. "Hi I'm Simon " he said. "I've come to fix your coffee machine."
I was in a state of panic but what could I do. I told him to come in and he followed me in to the kitchen. He was right behind me and I was trying to walk as a girl should and just be feminine. My imagination was telling me that Simon must have been wondering what he had walked in to.
"Here's the machine," I said.
I turned round to look at Simon for the first time. Simon was black, not too darked skin, about 5'11" and definitely handsome.
He was chattering away and I began to relax. He seemed very friendly and I forgot all about being a crossdresser. His whole demeanor was very nice. I felt very feminine in his presence.
I got him a drink of water. He didn't want anything else and then left him to it.
My brain was working overtime. He was taking all of this so well. Did he realise that I was a crossdresser? I began to fantasise a bit but knew that I wasn't brave enough to go in the kitchen and flirt with him.
I was suddenly brought back to reality when I heard him calling me.
I went back in to the kitchen and he started to explain that he needed to wait for 40mins while he checked the machine was pressurizing to make sure it wasn't leaking or at least something like that. I wasn't really listening to the detail. I made him a hot drink. We were having social chit chat when suddenly he says "do your neighbours and wife know you crossdress It would be a shame for you if they found out." Before I could answer he told me how pretty I looked and he took some photos on his phone. It was like I was being hypnotised. Give me a twirl came next. I did as I was told. Lift your dress up let's see what you're wearing underneath.
I just obeyed. Half of me felt embarrassed but the other half was totally exhilerated and loving it. I'd never done anything like this with a man before.
It was like I was rooted to the spot. He came up to me and put his arms around me pulling me in to him. He started to kiss me forcing his tongue in to my mouth. Initially I resisted but soon found myself responding. He dropped one arm and I felt his left hand go up under my dress stroking my thigh getting higher and higher until I felt his hand on my panties. He pulled me even closer to him with his other hand and I couldn't help but feel the lump in his joggers pressing into me.
It was like being in a dream or was it a nightmare. No definitely a lovely dream and it was happening for real
He started kissing me again, his tongue exploring my whole mouth. This time I responded immediately which seemed to make him kiss me even more passionately. His hands were suddenly on my shoulders pushing me down on to my knees. I didn't resist. I didn't want to resist.
My face was staring at the bulge in his crutch. He pushed down his joggers and boxers revealing a gorgeous stiff uncut cock. It was about 7" long and not too thick. "Be a good girl You know what to do," he told me. I'd never sucked a real cock before but yes I definitely knew what to do but I'll cover that later.
I started to lick the tip and then slowly took him in my mouth working his cock with my tongue just like I'd been taught. With one of my hands I started to rub his big tight balls squeezing them slightly but being careful not to hurt him. I looked up to his eyes. He was taking photos with his phone. Later I discovered that he'd taken a video too.
He put his phone down grapped my head and started to fuck my mouth. Apparently I have a small mouth. His whole shaft was in my mouth and I felt like I was going to choke gagging as he continued to use my mouth like a girl's pussy. This carried on for what seemed an eternity until suddenly he shouted, yes shouted, "I'm coming baby."
His cock seemed to stiffen even more then I felt his seed gush in my mouth hitting the back of my throat. I instinctively swallowed savouring the taste of his cum. It made me gag a bit but the taste wasn't horrible at all. "Good girl. Swallow every last drop," he told me.
He took his cock out of my mouth. "Now lick me clean." I did as I was told licking his cock all over until he told me to stop.
He pulled up his joggers and boxers. I stood up. He made me pull my dress up revealing my panties. There was a huge damp patch where my precum had ouzed into them. He smiled. "You enjoyed that didn't you!" He was right I really had. "Now you've had black cock you won't want anything else," he told me.
He started to get his tools together.
"Don't you need to check the coffee machine?" I asked.
"No it's all fixed," he replied grinning at me. He obviously knew what he wanted when he told me he had to wait to check the machine was ok.
His car was round the back of the house. He got me to go outside with him and help him put everything in his car. Some of my neighbours could easily have seen me but I really didn't care. It was quite breezy and I felt the breeze catch my dress making it blow up. My hands were full so I couldn't do anything about it. He came behind me and stroked my backside giving it a squeeze.
He got in his car. "I'll send your wife the bill. Can't wait to see you again. I think we're going to have fun. Bye for now."
With that he started the engine and was gone.
I went back inside, locked the door and went in to the bathroom. My makeup looked a mess, my lipstick totally smudged and I could still taste his cum in my mouth.
I couldn't believe what had happened since the doorbell rang. I felt exhilerated and knew I wanted more.
My wife would be home in an hour or so. What would I tell her? I started to remove my makeup and nail polish before having a shower. Should I tell her that Simon had discovered me dressed?What did he mean"we're going to have fun." I had to come up with a story...
To be continued
Damn. Why do do many people think that cross dressers are all gay?
Clearly the repair man is.
Great, Hot short story! ⭐⭐⭐⭐⭐ Being a closeted CD of sorts myself, I'd be very afraid of someone finding this part of me out and picking on me. Instead, in this story, Simon didn't seem fazed by it, which would have helped ME relax about it too. Then when Simon blackmailed him, this story got even hotter. Personally, it would have made me scared.
Being grabbed and kissed, like Simon did to him, my resistance would wane too. Then a man putting ME on my knees, and telling me to be a "good girl," would make me feel nervous all over again. The pictures Simon took of the mc was a shock to read about! I'd be so scared if someone took pictures of me in that situation! This is SO HOT to read about though!!!