The best job I had in collage

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IzameYouno

Male · 58 · United States of America

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2 Years Ago

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Category: Crossdressers

The best job I had in collage

MY NEW SIDE JOb
Being a Sissy Maid at a party to earn money.

I work at a convenience store while going to college making minimum wage.

Nobody understands how much I have to work to keep up with my bills. Christmas is coming up and I have been working all the hours I can so I can Have some extra cash for the holidays.

Working all these hours my friends stop in from time to time so they can see me. One of our regular customers is a gay couple, one is definitely the man and the other is more feminine, often wearing more girly and pink clothes.

In fact one time he came in wearing a tiny pair of hot pink shorts and when he got out of the car I caught a glimpse of everything. They are super nice people and always joking when they come in.

One time at work my buddy Tim and I weres standing by the register and we were talking while the more feminine, which I later learned name is Terry, was checking out.

I was telling him about how it seems no matter how many hours I work I just can't seem to save up enough to buy a car. He suggested I sell something or try to borrow the money. I know they won't lend me any money do to poor credit. Terry smiled and said good luck as he walked out.

About an hour later I was by myself the store was real slow and I noticed Terry pulling in. I said forgot something? as he walked in. No but I may have a solution for your problem. Oh really, what's your idea? He looked around the store to make sure we were alone, now I was getting nervous about what he was going to say when he did that.

From time to time Bruce and I have house parties with some friends and we hire young men to serve drinks to our guests. It's about 5 hours of work and it pays $500 for the night plus you may get tips. Wow I thought that would give me enough money to buy a car once I add it to what I have saved. I think he knew he had my interest.

Here's the deal all the guest will be men and they most likely be hooking up with each other. You will not be expected to participate or doing anything unless you want too as he winks and laughs just kidding.

Terry then says but you will be wearing a kind of revealing uniform.

But the most important thing is privacy you can not tell anyone about who comes and nobody will say anything about you.

He hands me his number and says I need to know in a couple of days.

I was hanging out with my friend's the next day, they started talking about how little we see each other. I said I am working on something special and after Christmas I will cut back I promise.

The next day I called Terry and we talked. He said the party is next Saturday, he gave me there address and said be there by 4 so we can get ready before the guess arrive. That was perfect my parents were going out of town for the weekend.He asked me for my measurements. I thought it was weird but the I remembered my uniform.

For the next few days I started imagining what I got my self into all I could picture was me in tiny tight shorts serving drinks while men were having sex with each other. I started to get hard thinking abut it and began jerking off to the idea.

It was finally Saturday night I got to Terry's house around 3:45 and he answered the door, good I like that your early. Terry looked like he had a little makeup on but it did not surprise me. He grabbed my hand welcomed me with a hug and asked me to set up some tables which I did.

Terry grabs my hand and takes me to a bedroom, the room was all pink with a canopy bed just as he was about to open the closet to get my uniform the door bells rings. He says sit down that must be the other sissy and he runs out of the room.

Sissy?? What sissy? other sissy? who is the sissy?

Terry walks in holding hands with Steve a guy I knew from school. Holy crap what are you doing here? I said. He says I work here. My face was bright red he said don't worry nobody will know, you'll have fun and the tips are great, besides they like fresh sissies.

What is this sissy stuff? Just then Terry opens the closet and pulls out these two short lace french maid uniforms. These are the uniforms?? Yes sweetie, I told you they were revealing. Um I am not sure about this. Just as I said that Steve lowering his jeans revealing the lace thong he was wearing and started to get dressed.

Come on pal get ready the guest will be here soon. I took a deep breath and said remember it's one night and why your doing this.

I get undressed I can feel Terry and Steve checking me out, Terry hands me these black lace thong panties and looks a my hard cock and says, see this is fun and besides with a cock like that you'll do OK tonight.

I slip the panties on and I have to admit they felt so good I started to reach down to rub them and Steve say no no no don't do that you want to stay as hard as you can.

We put on our maid outfits, they barely reached our bums and just reached the top of our panties. Terry gave Steve and me some high heels. You need learn to walk in heels honey. I said I already can remember last Holloween I dressed up as a girl and wore high heels all night.

Terry then gave us a touch of make up he stood up and said OK sissies we have a few minutes wait in the living room while I get ready.

While standing in the living room Bruce walks in, my my these are some pretty sissies, let look at what we have here. He tells us to lift up our skirts, turn around and bend over. As we are bent over I hear Terry say Bruce stop that, Terry is standing there in a long lace pink dress pink lace panties and Bruce is stroking his cock to us. Bruce, Honey put it away it will get plenty of use soon.

The door bells rings and Terry says go ahead welcome our guest while I go in the kitchen and start making drinks.

Steve, now Stephanie and I open the door and let the men in. They are all greeting each other with hugs, kisses and touching each other.

Stephanie and I go in the kitchen and get trays, we go out to the living room and start asking the men what they would like to drink. as we bring the drinks out the men are getting a little friskier with each other. Pretty soon a number of them are on their knees sucking cock and fucking each other.

One gentleman is getting a blow job and he signals me over, he starts rubbing my bum and gently tugging on my thong, be a good sissy and get me a rum and coke. Yes sir. I go into the kitchen and get the drink from Terry. Terry says your doing a good job, he's getting a lot of compliments on me. I smile and leave to go back.

I deliver the drink while he is still being blown, he reaches in my panties and puts a tip against my cock, pulls his hand out and rubs the front of my panties, I thought I was going to loose it.

Walking away I hear excuse me sissy, before I could turn around he was right behind me. I could feel his bare cock rubbing against my thong and bum, he whispers in my ear as he reaches around rubbing the front of my panties. He asks for a drink and if I was doing anything later. As he is rubbing me I let out a sigh and leak out some per-cum on his finger, he lifts his finger and slides it in my mouth. I took it and licked his finger without a second thought.

The guest leave and we clean up. We are going back to the bedroom to change back. Terry walk in and gives us our money. Holy crap I made almost $700 with tips.

As I start to get undressed Terry points to my cock and says you going to be alright going home like that, do you want me to take care of it for you? Shocked I said I'll be alright. I look over at Steve and is changing but putting on a new thong, a school girl skirt, a lace bra and a top. What are you doing I asked. I have got to pay my rent somehow.

Besides doing the parties, Steve was being a sissy whore. Oh my, are you serious? I'll make another $500 tonight.

Terry says oh honey you can make some money, you know the man who asked you out? He said he would pay $1,000 to break you in.

He could see my mind was wandering but it was not the part of my body I was thinking with. Before I knew it Terry was on his knees sucking my cock and Steve was rubbing my shoulders with his hard cock rubbing against my back. I came in seconds Terry got up and kissed me sapping my own cum in my mouth saying swallow it sweetie and I did.

Steve I have to go you sluts I have some cock of my own I need to take care of.

I get dressed up in something really slutty, Terry walks me to the door gives me that guy's name address and phone number and says, Let me know if you want to work another party sissy and giggles. I replied you can count on it and winked as I walked away.