Fun With Friends


This story is a work of fiction, although some of the facts within it are true!

Thanks to kjplotts for helping with the structure of the story.

I am a 28 year old single heterosexual male who happens to enjoy cross-dressing. It started with the desire to wear high heels and after that developed into pvc, leather, latex...anything slutty to be honest. The thought of being caught while dressed as a woman gives me an equal measure of excitement and fear! This is the story of what happened when my secret was discovered.

A friend of mine, Greg, started seeing a girl called Becca and they moved in together. This meant that I spent a lot of time with them both, including many drunken nights out. It was on one of those nights in Portsmouth that my secret came out.

Greg was at the bar getting drinks when Becca pointed to a girl's shoes and said how sexy they were. I agreed and she said that it was a shame that they hurt your feet so much.

I replied, "Yes but it is worth it".

To this she said, "Yeah, but you don't wear them do you?"

I had had a few drinks by then and I responded with," that's what you think."

We looked at each other, both a little shocked, but stopped as Greg was coming back with the drinks and Becca could see that I had gone a little red. Throughout the night, Becca kept asking me what I had meant and since the drinks were still flowing eventually, when Greg was away again, I confessed to her that I enjoyed dressing up like a slut and especially loved wearing 'skyscraper' heels.

Over the next few weeks, Becca kept asking about my little fetish and even came round to my house to check out some of my outfits. She was amazed by the slutty quality of my clothes and that I was able to walk in some of the shoes that I had. Through this time, though, there was no hint of anything sexual between us as she was living with a good friend of mine. This was soon to change.

One Saturday, Becca called me to say that Greg was going to football and that she wanted me to be round at their flat in an hour wearing my most slutty outfit and my dark wavy wig. I protested and suggested that she come to mine; she said that she wanted to put me through the humiliation of walking up to her front door dressed like a whore and that's why I had to go to her. She said that if I didn't, she would tell everyone we knew about my little secret...and that even if 99 people out of one hundred didn't believe it, there might be one who would. I had told Becca about my fantasy of being dominated when dressed so I guess she wanted to make my fantasy come true.

I took a shower and shaved off all of my body hair apart from a small strip above my cock. I picked out my most slutty dress and started to get ready.

Now this dress should not be worn outside of the bedroom never mind the house! From the front it's a short black pvc, halter neck dress but the back is another story. Basically, it has no back apart from the necktie and a thin strip of pvc that sits below the ass designed to hold the bottom of the dress in place. My ass is therefore out there for all to see.

I slipped on a black thong, the dress, and a pair of 6" black patent high heels with a 1" platform. By this point, I was rock hard so I slipped my cock from under the dress and stroked myself off into my other hand.

I have read about guys who would then lick their hands clean but I only fantasized about being a slut and did not actually want to suck a cock, taste cum, or get fucked by a guy so I cleaned myself up and then put on the brown wig and some makeup. While no expert, I could do enough to make myself look a little less manly so I went for dark eyes to match my outfit but then hot pink, wet look lipstick to give some contrast.

As I was checking myself in the mirror a text came through from Becca telling me that I had better be on my way because I only have ten minutes left to get there.

My house has an internal garage so I jumped in the car and made the short drive easily enough. Once at the flat I knew the problems would start. Their flat is about 100 yards from the car park but luckily is on the ground floor with its own door so there would be no buzzers or stairs to navigate. I saw that Greg's car was not in the car park as I pulled in and parked up and after a second or so stepped from my car and started making the walk to the front door.

Now there I was, walking to their flat in 6" heels dressed like that, with my ass on show to the whole world and it was only four in the afternoon, who knows what anyone who saw me like this would be thinking.

I would soon find out as in front of me I saw a girl of about 23 come from around a corner walking towards me. She looked me up and down and as we passed she said "Fucking slut."

I wonder what she would have called me if she had seen me from behind!

I got to the front door and knocked loudly as I didn't want to be on show for very long. Becca opened the door and I went in, glad to be inside. I saw that she was wearing a black leather cat suit with a built in boned corset as well as some stunning thigh high boots. She told me to close my eyes for a second and as I did so I could feel her place something around my neck and fasten it. She told me to open my eyes and I could see in the mirror behind her that she has placed on me a pvc collar with the words CUM SLUT spelled out in fake diamonds.

She whispered in my ear, "We both know it's true".

She walked towards the door to the lounge telling me to spin for her. I did so and she whistled saying that she would make so much money if I was to be put to work on the streets. My cock was rock hard at this point and the front of my dress certainly showed it. It was then that I noticed that Becca was holding a camera and had been taking photos of me as I did my spin. A look of horror must have been on my face but she simply told me to go through to the lounge but to make sure that I don't look her in the eyes as I do so.

I walked past her and passed from the carpeted hallway to the wooden floor of the lounge with my head down, the sexy sound of my heels clicking filled the air as I did so. As I looked up I saw that my friend Greg was sitting in front of me on the sofa, naked, blindfolded with his arms out at the sides and tied at the wrist. He obviously heard the clicking as I noticed that his cock had started to harden.

I turned around but Becca was right behind me with a finger to her lips telling me to be quiet. She said quietly that if I did not go along with this then she would show the photos she has just taken to everyone we know.

She then said loudly, "So Greg, you have always been keen on me to get my stripper friend Davina to come back with us for a's your lucky day."

She then followed by saying, "Davina is going to give you a lap dance to start with and then we will see what happens. For the time being though, you are going to remain tied so that Davina can do her thing."

She grabbed a remote and the Britney track 'Piece of Me' started to play.

I had 2 choices: 1) Go along with one of my fantasies and have some fun or 2) Get shown up to be a cross-dressing slut to all of my friends and family. I noticed that Greg's cock was now rock hard and must be at least 9" long and quite thick too. My mouth opened as I stared at it and Becca must have noticed as she laughed and lightly pushed me forward while saying for Greg's benefit, "Hell you go girl...your man is waiting."

I strutted over and turned my back to him positioning myself over one of his thighs before I started to grind down on it. Greg started to moan and so after a bit, I swapped sides and did the same to the other. I could tell from his moans that he was enjoying it and letting myself go I slipped off his leg and started to rub my ass against his crotch and huge cock. I could feel it between my ass cheeks as I rubbed myself up and down on him and knew that Greg wanted to fuck the dirty slut that was giving him a lap dance, unaware of who it really was!

Taken over by the moment I turned around and straddled him putting my lips against his. I was shocked by this myself until I felt his lips part and his tongue enter my mouth. We French kissed for 30 seconds or so until I remembered that we were not alone in the room.

I turned around and started to grind against Greg's cock again and could see that Becca was sat opposite us with her cat suit unzipped at the crotch and the fingers of her left hand buried inside herself as she flicked her clit with those of her right.

She looked at me and mouthed the words, "Do whatever comes naturally."

Just after she said this, the song Man Eater by Nelly Furtado started and so I took this as a hint! I pushed myself up off Greg and turned, lowering myself between his legs. His huge cock was now just inches from my face and, as my life so far flashed before my eyes, I thought screw it and reached for his huge piece of meat. As I took hold of it, Greg moaned again and a drop of precum appeared at the tip which I licked away. I circled my tongue around the top of his cock licking and spitting on it to get it nice and wet before taking the first few inches into my mouth. After a minute or so, I was bobbing up and down on it like my life depended on it.

This was all too much for Greg as he started to call me a dirty slut and telling me how after cumming in my mouth he was going to fuck me like the bitch that I am.

At this point, I could hear Becca walking across the room and looked up to see that she was now standing behind Greg. She removed his blindfold and I gagged on the cock in my mouth thinking that he would recognise me. He immediately looked down and we made eye contact, but with my wig and the angle I was at I realised that he did not know that it was me sucking him off. This turned me on even more and so I went further down his cock whilst also working it with my hand. Greg started to moan and I knew what was about to happen. Becca did too and so walked behind me and pulled the wig from my head so that he could see that it was one of his best friends giving him a blowjob.

As she did this she shouted at him, "Yes Greg! Yes! Cum in your friend's mouth! Treat him like the slut that he is! Show him how a real man acts."

His eyes went wide for a second as he realised what was happening before going skywards as he started to erupt into my mouth. This was my first time sucking a cock or tasting cum and as the first stream hit my throat, I instinctively pulled away which caused the next couple of thick spurts to hit me in the face. I took him again in my mouth and licked and sucked until there is no cum left.

I eventually allowed his shrinking cock to drop from my mouth and looked up, at which point Becca took another photo of me, this time with my cum-covered face and Greg's cock both in the shot.

She smiled and simply said, "So, what do we do now?"

Report Story

byHighHeeledHoney© 11 comments/ 99170 views/ 45 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartPikafan, AngieGurl and 43 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous02/22/18


Would love more

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 11 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: