The Sheriff : Part 2

(Part 1 from 1)

I had trouble sleeping that night because every time I closed my eyes I had visions of me on my knees sucking The Sheriffs cock. When my wife Sarah and I got up at around 9 am she told me that she had to go shopping items for the vacation. Sarah took measurements of my body from head to toe. I asked Sarah what she needed measurement to buy but she told me that The Sheriff told her she could not tell me what she was buying.

Sarah returned from shopping at around 8 pm. I asked her where all the stuff that she bought was and she told me that The Sheriff made her drop it off at his house. The next two weeks went by excruciatingly slow because I had to wear the chastity device the entire time. Once every two days we would have to go to The Sheriffs house so that my cock could be washed. When we would enter The Sheriffs house he would make us strip to the nude. He would then have us go to the bathroom where he had Sarah put hand cuffs on me behind my back. He would then allow her to take the chastity device off. Sarah would then give me a shower and wash my cock but she had to make sure that I did not cum. Sarah would then have to put the chastity device back on and put the lock back on it.

The Sheriff would make my wife go to bed in the nude every night and I would have to go down on her until she orgasmed. The Sheriff watched this on web cam every time. This made me very horny but of course I could do nothing about it.

The day before our vacation began The Sheriff summoned Sarah to his house. Sarah was at his house for a couple hours. When Sarah returned she did not have a disheveled look at all. I asked Sarah if they had any type of sexual activity when she was over at The Sheriffs house. Sarah told me that The Sheriff had given her instructions for the next day. Finally the Friday of our vacation arrived and we got home from work at 6 pm.

When we got home Sarah handed me a bottle of hair remover. Sarah told me that I had to take a shower and use the hair remover from my neck down and I had to shave my face as close as possible. While I was in the shower Sarah took a shower as well. I was unable to get all of my pubic hair because of the chastity device. We got dressed in jeans and t-shirts. When we left she said that The Sheriff had given her instructions for use to stop and eat somewhere. I said that I could not eat because I was extremely nervous. Sarah said she was nervous to but we had to. Sarah said that The Sheriff had given instruction for me to drink the largest drink with no ice. So we tried to eat and I drank my drink. We left the restaurant at 8 pm.

We arrived at The Sheriffs house at 8:30 pm. As we walked through the front door The Sheriff made us strip to the nude. The Sheriff then inspected us. The Sheriff noticed that I could not get all of the pubic hair. The Sheriff told me that I would be punished. I tried to explain but he told me to shut up and I would get additional punishment for back talking. The Sheriff told me to stand in front of a chair put my palms flat on the chair looking straight ahead. The Sheriff then had Sarah stand directly in front of the chair which put her pussy directly in front of my face. The Sheriff then gave me 40 spanking with a wooden paddle. I had to could every spanking aloud. The Sheriff told me that was the standard way of receiving punishment and I would be in that position unless he changed it.

The Sheriff then sent us to the bath room and had me hand cuffed behind my back so the chastity device could be taken off and the rest of the pubic hair removed. Sarah then put the chastity device back on me and gave the key back to The Sheriff. The Sheriff then left the room and Sarah told me that she would get me ready for the trip. I asked Sarah to let me use the bath room first because I had to pee. Sarah told me that she was not allowed to let me pee. I didn’t argue with her because I didn’t want to receive any more punishment from The Sheriff.

Sarah then had me sit down. Sarah pulled out some a cup breast with adhesive backing on them. Sarah then placed them onto my chest. Sarah then affixes a blonde wig to my head. Sarah gives it a few tugs to make sure it does not come off. Sarah then tells me to lay face up on the bed. Sarah pulls a package out from under the bed. The package is pink adult diapers. At this point I tell her that I don’t think that I can go through with it. Sarah reminds me that if I don’t we would go to prison. I then give in. Sarah has me lift my but up so that she can put the diaper on me. I am getting extremely embarrassed now that I’m wearing a diaper in front of Sarah. Sarah then hands me a pink diaper cover with white lace.

Sarah then fondles the a cup breast to make sure that they are attached well. Sarah then helps me put a pink bra with white lace trim on. The bra also has a pink bow in the middle. Sarah helps me sit down and helps me put white stay up stockings on my legs. Sarah then gives me a white paper nylon pinafore to put on. The pinafore makes a loud rustling noise when I move.


Sarah then goes to the closet and pulls out a dress. The dress is a pink dress that has white ruffles on the sides. It has a pink bow in the center of the breast and white ruffles around the arms. Sarah helps me get into the dress. After the dress is on she puts a lock on the back. Sarah then has me sit down so she can do my makeup. Sarah does my makeup in pink tones. Sarah does my fingernails with French tips. Sarah then gets a pair of white five inch heels out for me to put on. After I get the heels on she puts a lock on each to keep me from getting out. Sarah gets a collar out. The collar is a black posture collar with metal rings on the outside. Sarah puts the collar on my neck and locks it with a lock. The collar does not allow me to bow my head at all. Sarah then fixes my hair. Sarah puts a pink bow in my hair. Sarah helps me stand up which is hard because I have never worn heels before. Sarah lets me see myself in the mirror and I get even more embarrassed. Sarah tells me not to feel bad because we don’t have a choice.

We then walked into the living room where The Sheriff is waiting. The Sheriff makes us stand in the center of the room. The Sheriff makes my wife stand with feet shoulder width apart with hands behind her back. The Sheriff inspects my costume. The Sheriff takes a lot of pictures of me. The Sheriff then tells me to go stand in the corner while Sarah gets dressed. I then wonder what my wife will be wearing. I hear Sarah come back into the room and The Sheriff has her stand for inspection. I hear her gasp and start to moan. I hear Sarah then orgasm. The Sheriff orders me out of the corner. I see what my wife is wearing. She is wearing a pair of skin tight jeans no bra and a white t-shirt. The shirt has MY HUSBANDS SUCKS COCK on the front in black letters. She is also wearing vibrating panties.

The Sheriff tells us that all the needed items are in the truck. The Sheriff then has us go to the truck. The Sheriff has me get in the back seat of the truck on the passenger side. The Sheriff tells me to spread my legs. The Sheriff then puts a spreader bar between my legs at my ankles and another above my knees. Sarah then puts leather cuffs on my wrist and locks them. The Sheriff tells me to lean back and place my hands behind my head. The Sheriff then laces the cuffs through the collar ring and the head rest and then locks me into place. I now cannot move my head forward at all. Sarah seatbelts me in. The spreader bar at my ankles is attached to the front seat preventing me from moving my legs at all. The Sheriff then tells me to open my mouth. As I do he gets a cock gag and places it into my mouth and locks it into place. They then get into the truck and we begin the trip.

The Sheriff tells me not to move and that I cannot use the bath room until we get to where we are going. I am so uncomfortable in the back seat. I try to move to get a little comfort but I am unable to but the pinafore makes a rustling sound. The Sheriff then tells me that I will be punished for trying to get out of the restraints. I have to pee badly but don’t want to pee in my diaper.

We get about two hours down the road and pull up to a stop light. The Sheriff turns on the vibrating panties and rolls down the passenger window. He makes my wife get the driver of the vehicle next to us attention and show them her shirt. The Sheriff then makes her tell them that I suck the drivers cock and do it better than her. About 30 minutes later we pull into a crowded gas station for gas. The Sheriff ask me if I want to get out and I nod no because I don’t want anyone to see me. I do have to pee badly but am too embarrassed to get out.

We continue on the road. About 15 minutes after I can’t hold it anymore and begin urinating into the diaper. The Sheriff hears me moving while I trying to stop wetting myself. The Sheriff asks me if I just wet myself and I nod yes. He tells me that I will receive punishment for the offense. I then wish that I had not stopped myself because I still had to go bad. Another 15 minutes go by and I can’t hold it and wet myself for the second time. The Sheriff notices again and tells me that I will receive more punishment for not following orders. This is the most embarrassing thing ever wetting yourself with your wife sitting in front of you.

A little while later we turn onto a deserted road when the sun starts to come up. The Sheriff stops the truck on the side of the road and comes to my door. The Sheriff then uncuffs my hands and unbuckles me. The Sheriff undoes the two spreader bars and has me get out of the truck. The Sheriff takes the penis gag out of my mouth. The Sheriff has Sarah put the spreader bar back on my ankles. The Sheriff tells me that the cabin is the last on by the lake and I will walk the rest of the way. The Sheriff says it is 1 mile down the road and there are only a couple other cabins on the road. The Sheriff and Sarah get into the truck and drive away. I start walking hoping no one will pass. About halfway a woman about 35 and nice looking pulls up beside me and starts to try to help me because she thinks that someone has played a prank on me. I tell her not to help me because I have to walk to the cabin like this. She then drives off. I then start to see the cabin and realize I need to pee again. I let myself wet my diaper again and walk to the house.

As I come up The Sheriff is waiting on me. The Sheriff tells me that he saw me wet myself again and would be receiving 60 spankings at a later time. My wife is standing on the porch in only a bra and vibrating panties. The Sheriff has me stand in front of Sarah. The Sheriff has Sarah put pink lip gloss on my lips and take the spreader bar off. The Sheriff then has me turn to the side. The Sheriff then stands in front of me. The Sheriff then puts his hand on my shoulder and pushes down and I go to my knees. Sarah then steps up to us and pulls his cock out of his pants. Sarah then holds it to my lips and tells me show her how to suck cock.

I then open my mouth and let his cock slid in. The Sheriff lets out a sigh and says he has been waiting two weeks to have my mouth on his cock. The Sheriff says he’s going to have a nice load for me because he hasn’t masturbated at all. I start moving my head back and forth on his black cock. I hear Sarah’s panties start to vibrate. I can tell The Sheriff is getting close and I speed up. The vibrating panties stop and he stops me from sucking on his cock. The Sheriff tells my wife to keep watching the sissy suck his cock and stop closing her eyes. The Sheriff turns the panties back on and start to face fuck me. Sarah starts to pant as she nears orgasm. The Sheriff then fucks my face harder.

As Sarah starts to climax I feel The Sheriff start releasing his cum into my mouth. I can’t catch all of it in my mouth and move back. The Sheriff keeps stroking his cock shooting it all over my face. I can’t believe in the span of two weeks I have sucked his black cock twice and I am made up like a sissy. The Sheriff makes me stand and face my wife to show her my face.

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