Two days later I received another letter from William.
James,
I am happy you have accepted my invitation. Since this is a Halloween party I want you to come in costumes I want you dressed like a girl. I remember that those pictures of shemales turned you on so I thought you might enjoy playing that role for one night. The day of the party I will send my assistant Ana to your place with what I want you to wear. She will be of great help to get you ready. You might remember her. She was the blonde that turned you on in the group of women.
I was curious as to why I would need help in getting ready. The party was over a week away so I focused on school work and try to find a job after graduation. The time passed quickly.
The knock on the door to my apartment started another memorable weekend. The beautiful blonde at the door was the one I had seen in the video at William’s home. She was prettier in person than in the video. The only difference was that she was wearing clothes. She was carrying a suitcase.
“Hi, my name is Ana and I am a friend of William. He asked me to help you get ready for tonight’s Halloween party. ”
“HI Ana, my name is James. I am not certain how you will get me ready for this party, but I am open to you.”
Smiling Ana replied, “William tells me that you have an interest in shemales and that I have an interest in making men sissies. We are going to this party as a couple. You as a sissy/shemale and I as your Mistress. I have both our costumes and we are to get dressed together.”
“This sounds strange but I know William always knows how to get people excited.”
Ana said, “Let’s get started. I need you to get naked. The first thing we have to do is shave your body. No hair. You are to become smooth like a girl. Have you ever shaved your pubic hair?”
Shocked I said, “No”
“Don’t worry I have done it dozens of time. Let’s go into the bathroom and get started. Since I am going to be your Mistress tonight and William warned me that you are very easily aroused, I am going to put this chastity device on your cock as soon as I shave you. That way you won’t get out of control until tonight. So let’s get on with it. Take your clothes off and let’s start getting you ready.”
While I was reluctant to start, I obeyed. It was one time to be naked with guys quite another to be naked and alone with a beautiful woman. As soon as my pants were off, my cock got rock hard. Ana was turning me on.
“Okay big guy, put that monster of yours away. ” Pulling an ice pack from her bag, my cock soon felt cold which caused it to shrink. At that point she slipped the pink chastity device over my limp cock.
She said, “that will keep that monster caged until tonight. Don’t worry your Mistress has the key.”
I immediately felt the constraints on my cock which started to respond.
It was strange to see my pubic hair gone. I hadn’t seen a bare cock and balls since I was 10 years old. Having Ana shave me was a turn on. As she continued to remove my body hair, the logic verses sexual emotion arguments raged. Why am I letting a woman do this to me? The thought of me giving up my manhood to please some guy hold a party made no sense. This entire thing was crazy.”
Once Ana was finished, she told me to take a shower. To my pleasant surprise she stripped and got into the shower with me. But with my cock caged, the only pleasure I could receive was washing her back.
My clothes for the party included thigh high nylons, bikini panties, bra, and a party dress usually worn by little girls. A pair of white flats and a blonde wig completed the costume. Ana would apply makeup just before we left for William’s home.
Ana was wearing black leather pants that had no back; black booths; and a black leather vest. She wore no underwear or bra. In order to get to the party she had a black skirt to cover her backside. She look fantastic. The question was why was I going to a party dressed like this with a woman dressed like Ana with a damn chastity device on.”
As we left my apartment, I could only hope no one would see me. The trip to William’s home took approximately 20 minutes. During that time my cock strained in the chastity device as I sat next to Ana. She was beautiful.
To this point Ana and I had not really had a chance to talk. Our focus was getting ready. So now was my chance.
“Ana, how did you meet William?” I didn’t know what to expect except that she didn’t meet him at an X-rated movie theater.
After a few moments of silence, she started to share. “My former husband owes a friend of William a great deal of money. Unfortunately, my name is on the note and so I am also liable. At age 23 I owe over $500,000. I have become in effect an indentured servant.”
I responded, “That’s against the law.”
With tears in her eyes, “Perhaps but my former was involved with illegal activities and William has friends who could put me in jail. William saved me and I am now one of people he uses when he needs sexual activities.
“How long will you be forced into this situation?”
Ana hesitated then said, “Until either my husband pays off the obligation or William is tired of me. I wish I could start a new life, but I owe him for saving me from jail or being sent off to some foreign country as a sex slave.”
“That could really have happened?”
“Yes, when you cross the Russian mob you either pay up or they find a way. I am not worth $500,000 to them but I could bring them at least $50,000. A small amount but the revenge Is the key.”
Shaking my head as we pulled onto to William’s street, “I can’t believe you are mixed up in this and I can’t believe I am involved.”
Ana said, “James, you are lucky. You are involved because you became sexually excited. You receive pleasure. I receive nothing except being effectively held as collateral for a debt.
Parking the car, Ana removed the skirt that provided to modesty protection. Her ass was now bare and exposed to whomever wanted to touch it. I walked behind her in an attempt to provide some cover.
Once inside the Victorian mansion, William greeted us.
“I am happy you are here. Your guests are in bedroom 3. They are interested in a number of things so please keep them happy. Ana, I hope you are still on the pill. I instructed them to bring condoms but these are special friends who do what they want. Just obey and everything will be alright.”
With that warning Ana and I moved to bedroom three. It was a large room with a full bath, a bar, bed, and some sex furniture. A man and woman were waiting.
To be continued . . .