My name is Sam. I have been a cross dresser just recently. I am currently 16. I have short blond hair,dark brown eyes and I am very slim. I have a older sister who emigrated but I visit her once or twice a year with my mom. My dad passed away a few years ago. Considering my mom had financial problems she works a lot so that gives me time to cross dress.
My mom is very sexy and has great taste in clothes so I borrow her underwear and wear it instead of men's underwear.
The summer began so I rested for a while by staying in bed. It was noon when I woke up, I had a shower put on some sexy,white cotton panties I borrowed from my mom a while back and kept them in my underwear drawer.
Over the panties I had a pair of tracksuit bottoms and a t-shirt. I went downstairs where my mom was reading the paper. I went to reach up for a jam filled dough-nut when my mom grabbed my trousers saying, "What is this"?
I knew exacully what she meant but I said nothing. She continued saying, "Does the man of the house want to be a sissy little girl?"
I felt I could say nothing but, "Yes".
My mom just went silent and left the room. I continued wearing the panties more as the days went by. It was very quiet between me and my mom but a few days later when my mom said, "Get in my car".
Knowing nothing what was happening I just went along with it. It was an awkward and quiet journey until we arrived at a well gated house. When we came up to the front gate but my mom had a clicker to open it.
When we got up to the house the door was open with a note stating to go into the living room. My mom instructed my to go by myself cause she needed to use the toilet. I did as I was told and entered the living room to be greeted by a sexy middle aged woman.
She had long blond hair, huge breasts and sexy smelling perfume. She later told me her name is also Sam. She also told me her and my mom are lesbian lovers. When my mom came in she sat down gave Sam a passionate kiss. After a long kiss they gave me a box containing a pair panties,a bra, above knee stockings, a suspender belt, 5 inch heels, bra stuffer and a black cocktail dress.
They all matched and look rather expensive. She told me they cost $600. She instructed me to put them on and return with them when I had dressed. I did as I was told and I returned to a make over and another car trip. We drove for a while and I was instructed to put on a blindfold. After the blindfold went on we stopped and I was brought to a closet type room by a dull light. It was a while until I knew what I was getting in to. My mom and Sam said I was going to pay Sam for the outfit by making some horny people happy by doing what they wanted for ten minutes and they would pay $50.
The first person was a well build male who was very aggressive. Straight away he pulled down my panties and rode me non-stop until his time was up and then paid again and for a second and third time. He came twice and it filled me.
The second person was a shy rather young male who requested a blow job. I made him cum and I swallowed every drop like a little slut. I actually enjoyed sucking him. I hoped more would request a blow job. Many more men came and most wanted anal but some want a blow job.
It was a long day but I heard Sam shout, 'Here's the last one.'
When the door opened I saw a girl named Chloe from my school and class. I had a huge crush on her but she had a girlfriend. Knowing she paid $50 for sex I told her in a girlie voice that I was really a man. She said she knew then she removed a strap on from her bag. Thinking to myself, I'm not going to be fucking my dream girl, I'm going to be fucked.
And fucked I was.
The dildo was huge bigger than any other man's cock, she rode me hard but I blasted out shouting, 'Fuck me harder!'
After the ten minutes we both left and she walked off but I stayed with my mom and Sam. After a good few steps Chloe turned around and said, 'Pleasure doing business, Sam.'
The only thing that went through my slutty head was which Sam was she talking about?
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