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I don't know how long I had been driving. It had to be at least 4 or 5 hours. I had taken two weeks off from work and decided to take a road trip. I didn't know where I was going. I would just drive until I found somewhere interesting to stop at.
I knew I was somewhere on Route 3 in the Adirondack State Park. I loved being out in the middle of nowhere. It was getting late. Eight o'clock at night in November and it was getting really cold outside. I figure it was time to start looking for a hotel.
As I drove in the darkness I noticed something on the side of the road just ahead. I figured it was a deer or a coyote. As I got closer I realized it was a woman. A good looking woman. She was waving for me to stop. She carried two bags of luggage as if she just just checked out of a hotel. My heart was racing. What do I do. I was always told never to pick up strangers. But none of them ever looked like this. I kept asking myself "What would a woman be doing hitchhiking on such a desolate road". Could it be she just got away from an abusive husband or boyfriend? It was such a turn on I figured what the hell. As I pulled over to pick her up I noticed she was dressed very nice. She was wearing really tight jeans and a sweater that gripped her body. She had a great body for a woman I thought had to be in her early 40's.
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"Ma'am can I offer you a ride somewhere?" I said as I rolled down the passenger window.
"If you could please. You are the first car to go by in the past hour and it is getting really cold out here. My name is Michelle. You could drop me off at the next town if that is no trouble." she replied as she put her two suitcases in the back seat.
"No problem at all. Glad I came along before you froze to death out here."
Michelle hopped in the front seat carrying her purse and thanked me for giving her a lift. I told her my name is Mark and that I was on a road trip somewhere just to get away for a few weeks. She explained to me that she was trying to get home to Vermont and the last person who picked her up suddenly had to turn around and dropped her there in the middle of nowhere.
As I drove down the dark highway I couldn't help but get turned on thinking about this gorgeous middle aged woman with one hell of a body sitting next to me. I was rock hard and I think she noticed it whenever we passed under a highway light. She fiddled around in her purse for what seemed like ten minutes. I wondered what she was looking for. Michelle had one of those purses that you could fit everything into. Before I knew what happened I felt something sticking into my side. I looked down to see Michelle holding a gun to the side of my stomach.
"Keep both hands on the wheel and your eyes on the road. I don't want to hurt you so do everything I say and you will be just fine. Do you understand me Mark?"
"Very good. About fifteen minutes from now we will turning left off the highway onto a dirt road. Do not talk unless I ask you a question. I have killed before so don't tempt me. I need a hostage until I can get into Canada. Obey me and you will be home safe and sound before you know it. Disobey me and we will have problems. Do you understand?"
"Yes ma'am." I said as I realized I had never been so scared in my life.
"I am going to insure you don't try anything so keep looking straight and both hands on the wheel." she said as she reached in her purse again and pulled out thick 2 inch wide leather collar with a D ring on it.
Michelle place the collar around my neck and padlocked it shut. She then ran a short chain through the D ring and wrapped it around the headrest and locked it shut with another padlock. I was locked to the seat of the car even though it didn't interrupt my driving. She then pulled out a penis gag and told me to open my mouth. Since I was scared of what she could do to me I willingly opened my mouth as she shoved it into my mouth and strapped it securely behind my neck.
"Very good. You took that cock in your mouth so smoothly. I bet you like that huh? See that wasn't so bad. Once we get back to the farmhouse I need to get you tied up nice and tight. You'll like that I bet."
Actually I do like bondage but I never thought that my first time trying it with a woman would be a situation like this. I was being kidnapped by a woman. She had done it so easy. I was now chained to my seat with a cock gag silencing me. When we came to the dirt road Michelle showed me where to turn off the main highway, if you could call it that. In the past fifteen minutes only 1 car had gone the other way by us but it was so dark no one could see me gagged and chained. We drove down the dirt for 2.6 miles. I kept an eye on the odometer just in case I could escape I knew how far it was back to the main road.
We pulled up to the farmhouse and I turned the car off. We were definitely in the middle of nowhere. The closest neighbor had to be over four miles away. I just figured I would just do what she said and hopefully she would stick to her word. Michelle got out of the passenger seat and walked around to my side of the car. She handcuffed my hands in front of me and used ankle cuffs on my legs. She unchained my neck from the seat but left the collar on. She led me into the house and directed me to the basement. She led me to a corner of the basement where she ran a chain through the D ring on my collar and chained to a bolt in the floor. Michelle rehandcuffed my wrist behind my back.
What she did next surprised me even more. She pulled out a sharp knife and began cutting all my clothes off me leaving me completely naked. Michelle brought out this metal tube with a single handcuff attatched to it. She put my penis through the tube and locked the handcuff around the base of my penis and balls. I was locked into a penis chastity. If she needed a hostage then why did she need to do this?
"There that should hold you." Michelle replied. "Even if you were to get loose you are naked and your penis is all locked up and I have the only key. Now one last thing before I leave you for the night. I want you hogtied."
Michelle took a short chain and ran it through my handcuffs and ankle cuffs and locked it with another padlock. She went upstairs as I lay there on the basement floor hogtied, gagged, and locked up in a chastity device. As scared as I was I was still turned on by how gorgeous she was. I could hear her footsteps upstairs walking around. I wondered how long she would keep me like this.
Three hour later I heard Michelle coming down the stairs. When she came around the corner I noticed she had changed. She was wearing a short black skirt with a white silk blouse. She had black stockings on and 5 inch high heels. She walked over to me and made a cliched type of remark that I had not left.
"I see you like what I am wearing. You would probably be hard if your cock wasn't all locked up. It is time for Part 2 of my plan so I need you asleep."
I watched as she took a rag out and poured something onto it. I realized it had to be chloroform. Chained up as I was I could not fight. Before I knew it I was drifting off to sleep.
When I came to I felt different. I quicky realized that the penis chastity had been taken off. I was laying face down on a bed. I was no longer chained up but I was tied up with rope. My wrists had been behind my back. A rope had been wrapped around my wrists and pulled them up to my neck. That piece of rope was tied to my collar. Each of my ankles had been tied to the posts of the bed leave me spread open. I was also dressed, but I was dressed as a woman. I could tell by the feeling of the stocking on my legs. I could feel the garters pulling on the stockings holding them up. I was also dressed in a bra, panties, and high heels. I also had been place in a black dress that was tight on me and made me feel like a slut.
"I see you are awake finally my litttle whore." Michelle said. "I figured before I left we could have some fun."
I tried to answer but the penis gag was still in place. I turned my head to see she was still dressed sexy. If I was going to get sex from her then why was I tied down on my stomach. How was she going to get under me? She wasn't. I could see her putting on a strapon dildo. She was going to rape me before leaving.
"Before leaving I am going to fuck your ass. I always wanted to do this to a guy but never had the chance. Sorry about this but it's not like you can do anything about it." she said as she poured some type of lube on it.
Michelle climbed on the back of me and slid the dildo right in my ass. I screamed into my gag. She laughed as she fucked me as hard as she could. I never felt so violated in my entire life. Dressed as a woman, tied down cruelly, and raped in the ass. As Michelle raped me she pulled my penis out of my panties and stroked my cock. After about five minutes I exploded into her hand. That was the most incredible orgasm I have ever had. Michelle then removed my gag and forced me to lick all my semen off her hand. Michelle then put the penis gag back into my mouth and secured it once again.
"Well you lived up to your end of the deal so I am going to let you live." she said
"But my ride is waiting for me outside and I have to go. The woman that lives here should be home tonight. You can explain your situation to her. Maybe she won't call the police. Maybe she'll like you like this as much as I did."
As Michelle was about to leave she turned around. She walked back over to me with her strapon in her hand. She forced it back up my ass secured the straps around my waist holding it in my butt.
"That should keep you occupied until she comes tonight." Michelle said as she left.
I spent the next eight hours tied face down in woman's clothing with a dildo shoved up my ass. Eventually I heard someone coming up the stairs. I could tell it was a woman because she had been talking to herself not realizing someone was tied up in her bedroom. I figure she would flip out and call the police but at least I would be free and could explain my predicament to the police. The lady walked into the bedroom and saw me in my predicament and her face lit up in shock.
"Jesus Christ! Those are my clothes you are wearing" the lady screamed. "Damnit Michelle I told you not to use my clothes. You are in trouble boy!"
What? Oh my God! What is going on I thought to myself.