1 comments/ 24041 views/ 6 favorites My Fiancée's Weight Loss Program By: PDeanMurphy This is a copyrighted original work by the author. All rights reserved. All characters featured herein are at least eighteen years of age, even if not expressly stated. Any resemblance between actual persons, living or dead is entirely coincidental. Thanks, Dean ***** I was sitting in my fiancés apartment waiting for her to finish dressing so we could head to a movie and I heard, "Oh my God I can't believe it, not again." "Are you okay in there sweetheart?" "Oh I am fine, just pissed off but fine." "What's the problem then?" "I don't want to talk about it." "Okay then why did you scream about something you don't want to talk about?" "Fine, if I tell you will you leave me alone about it?" "I don't know since I don't know what you are talking about." "I am talking about my weight. I am tired of fighting to keep it off and I can't find a diet that works." I almost opened my mouth and said something that I would regret but thankfully my shut-up filter worked for once in its life and I kept my mouth shut. I don't know why Jenny is so worried about her weight. It is not like she is extremely overweight. Let me help give you a picture of her in your mind. She is 5'6"tall and weighs in at about 150 lbs. She would much rather be about 130 lbs. I have heard her talk about this all winter and now summer was approaching and she is going off the deep end again about her weight. She has a great figure even with a few extra pounds. Jenny has a 34 C chest and her hips are about 36 inches. She is about 29 inches around the waist and she wants that to go down some according to her. She has an adorable ass that I never complain about. As a matter of fact it was what drew me to her in the first place but I would never tell her that. We have been dating for about four years and engaged for two of those. She has beautiful long brown hair and when it comes to sex she is what I would call a dynamo. She is willing to try about anything at least once and keeps herself shaved or waxed baby smooth. Some men may not like their women that way but I do. Jenny walked out of the bathroom with only a towel wrapped around her using another towel to dry her hair. "I don't really want to bring this up but if you don't hurry up sweetheart we aren't going to make it. If you don't want to go out I can go get us a movie and snacks and come back." "Would you be really upset if we just stayed in?" "If I was I wouldn't have offered. Do you want me to go get a movie so you can just put on PJ's and sit around and be comfortable?" "I would really appreciate it. I am so tired of trying to lose weight and never getting anywhere. It really bums me out and I don't know what to do." "I will run and get some stuff for us and be right back. If you are having that much trouble I could just paddle your cute little ass if you don't lose the weight." I said as a joke as I was walking out the door. "Thanks you're a lot of help." I ran to the local movie shop and grabbed three movies for her to pick from and some snacks. I also ran through the local convenience store and got some drinks for us as well as fried chicken and salads since I was hungry. I arrived back at the apartment about 20 minutes later and she was sitting on the couch obviously depressed over this weight loss thing. "Here sweetheart I got us some snacks and fried chicken and salads to go with these movies." I handed her the movies to pick which one she wanted to watch. "I tell you that I am having trouble losing weight and you get us fried chicken!" She said almost yelling at me. "I got us something to eat because I am hungry and you can eat the salads if that is what is eating at you thanks." I said back almost in a snotty manner. Jenny started to cry and I felt like a heel even though I didn't really think I had done anything wrong. I loved this woman to death and I would not do anything to hurt her knowingly. She looked up at me and I sat the food on the coffee table and held her in my arms. I told her I was sorry and I did not mean anything by what I got for us to eat, I was just hungry. She looked at me and replied, "I am the one who should be sorry. You put up with my constant complaining about my weight, and then I jump down your throat when you do something nice for me." "Don't worry about it I know you don't mean anything about it you are just upset." "I am so tired of this. I have tried every diet that comes down the pipe and I can't seem to lose weight." "Have you just simply tried good old fashioned diet and exercise?" "I have tried everything." "Sweetheart I don't want to get into an argument with you but you haven't tried them the way they are supposed to be used. You try a few days and then look for a different one because you can't see any results." "I don't do that I try them for at least a week and then I..." She suddenly got very quiet. "What's the matter sweetheart what were you going to say?" "I just realized you were right. I need to find a way to motivate me into finishing what I start." "Tell you what you just sit here and relax and watch the movie and think about what you need to do to make this work and I will support you in whatever you choose to do it...okay?" We sat and watched the movie and I laughed all the way through it. I had seen it about a hundred times but I never get tired of it. I was watching 'Down Periscope', and I love that movie. I don't think Jenny paid any attention to it. Her mind was off in never-never-land probably thinking about her weight problem again. She did eat a salad while I ate chicken and junk food. "I wish I had your body metabolism." She said as the movie ended. "You can eat anything you want and never gain an ounce." I couldn't argue with her on that because it was true. I do however get a great deal of exercise every day and that does make a difference. We were sitting there waiting for the credits to end on the movie when she looked up and said, "Were you serious about what you said earlier?" I may be male, and I may act like a male, but there was no way I was answering that question without knowing what I said. I have made that mistake before and I was not going to dig myself a hole I could never get out of. "Just what did I say sweetheart?" "You said that you would just paddle my cute little ass if I didn't lose weight." "Sweetheart I love you to death and there is nothing I would rather do than look at your cute little ass, but it was a joke." "Does it have to be?" "Okay, you have me intrigued but what are you actually asking me to do?" "I want you to help me lose weight. I want you to spank me if I don't lose it and if I don't I want to be punished for it." "I don't think that is a good idea sweetheart." "Tell me one good reason why it's not a good idea then." "If you don't lose weight, or gain weight for some unseen reason, and I have to punish you with a spanking you will be mad at me." "I had not thought about the gaining weight part but I guess that is also a possibility." "Good, glad you changed your mind, let's just watch the next movie." I said hoping the matter was closed. "I just have to come up with a plan that works for both of us, that's all." She was not going to leave this alone. I put on another movie and in the middle of it she got up and went and got a pad of paper and started to write something. If I looked over to see what she was doing she turned the paper so that I could not see what she was doing. By the end of the movie she was smiling to herself and looking at me with the cat got the canary smile. When the movie was over she looked at me and said, "Rob we need to talk." I was not sure what she had come up with but I knew that I was going to be involved one way or another. "Would you really help me lose weight if I asked you to?" "If there was something I could do like counting calories or something like that I would." "That is not what I asked you. Will you help me lose weight if I came up with a plan that I think will work?" "I guess if you put it that way and you really are sincere about losing weight I would be glad to help you." "Okay I have a plan that I believe will work. You simply have to agree to do what is required of you if I don't follow through with the weight loss plan." "What do I have to do?" "Let's talk about this for a minute sweetheart," she said batting her eyes at me. "Okay." "Here is what we are going to do. I must lose weight each day for 30 days. I haven't figured out what I am going to do for the exercise part of it yet but that is the plan." "What's the catch?" I said knowing she wasn't finished yet. "I will weigh in each evening. When I weigh in if I have not lost weight I want to be punished for it." I started to say something and she told me I had to wait until she was finished giving me the entire plan and then we would discuss it. I thought at least she had thought the plan through that far. She went on to say, "If I don't lose weight you are going to spank me. If I gain weight then the punishment gets more severe. At the end of the week if I have not lost weight then I get paddled as well as suffering something that I have never allowed you to do before. The idea is that I want this to work and I had to come up with something that I feel is a punishment." "Just what are you having me do that you have never allowed me to do before?" "If I get paddled I need something else to help me to learn that I was serious about this. You get to put a plug in my ass." I think my heart did a flip flop. I have always been excited to play with her ass and she just was not into it. I tried putting a finger in her ass and she just plain said, "No." "I don't think you know what you're saying." I told her not believing that she really thought this through. "I have thought this through. If I don't lose weight I get spanked and if I gain weight I get a paddling and a plug." She said as a matter of fact. "Okay if that is what you want and you think it will work then I will agree to it." "Rob, that's not all." "What else are you making me do?" "I think I should get a reward if I lose weight don't you?" "I suppose you should so what do you have in mind?" "If I lose weight then I get to spank you." "I don't think I like this idea anymore." "You said you would support me, and besides it might be fun." She had me and I did not want to admit it. If I didn't go along with her plan it looked like I wasn't supporting her. I was doomed and I knew it. "Okay I will agree with whatever plan you put together." "Rob, if I lose enough weight I will be really grateful and I might just have a special gift for you when we are finished." "What's the gift?" "If I lose the amount of weight I want to lose then you get the gift, but I am not telling you what it is until after the 30 days of weight loss is over." "Okay, how are we going to do this?" "I don't have any idea I just know I want to lose the weight." "I have an idea. Can I think about it and tell you tomorrow if I think it will work?" "I guess that will be okay." We kissed each other and I headed home trying to come up with a plan to help her lose the weight. I had a great idea I just had to see if it would work and I wanted to sleep on it. I used the information she had given me and told her I had a plan that I thought would work, if she was sincere in wanting to lose the weight. She told me that she did and I told her I would be over at her house that evening to talk about it. When I arrived she gave me a kiss and we talked about her plan. We decided that she would be spanked if she didn't lose weight and paddled if she gained weight. She also kept with the plan of using a plug as punishment as well. I tried to talk her out of that because I did not want her to think of anything anal as a bad thing. She already would not let me touch her there and now she wanted me to punish her, using her anus as part of the punishment. She said she was sure that I would agree and she had gone out and bought some things for us to use as well. I asked her to show them to me and she said that when she had to be punished I would see them. She did show me a leather paddle she had purchased and I told her I hoped she knew what she was doing. I also told her that she should weigh herself in the morning because that is normally the best time. She said she knew that but hoped that weighing at night would also help to keep her from overeating or eating things she shouldn't during the day. I wasn't going to argue with her so I left it the way she wanted. "Okay sweetheart, when do you plan to start this diet?" "I am going to weigh myself at 9'oclock tonight and then at the same time every day or as close as I can." "Why so late in the evening?" I asked wondering what she was up to. "I don't plan to have to take the plug for gaining weight but if I do I want to wait until it's almost time for bed before you put it in, since I have to keep it in until morning." "You did not say anything about keeping it in until morning." "I realize that but it is supposed to be a punishment and I hope it keeps me from gaining weight." "I hope you didn't buy one that's too big then." "Oh I bought several and I am also going to make you increase the size each time I mess up as part of the punishment as well." "You really are serious about this aren't you?" "Yes I am and you better follow through on your part as well." "I told you I would." She also realized that while we were discussing this we were supposed to be gone on vacation for two weeks during that time. "What are we going to do about vacation?" she asked wondering if it would affect our vacation. We had planned on doing some hiking along a route I found through North East Iowa. I had heard the trout fishing was good there and there are several places we could camp on the way. With the weight thing thrown in that was going to be a bit of an issue since I was not packing a scale. We talked about it at length and then she asked, "Can't we just pick a place to camp that is out of the way and drive out to different places to fish and hike each day?" "I guess I don't see any problem with that." We sat and looked at maps and decided that the best place for us to stay was in Decorah. It had a great campground that had firewood, showers, etc. that would make it a little less rough but still allow us to go out and enjoy nature. "The only problem with this plan sweetheart is that giving you a spanking in the middle of a campground is going to draw attention that we really don't need." "Can't we just find a place once we get there out away from everyone if I get a spanking or perhaps if you do?" she said with a grin. I had hoped she forgot that part but she hadn't so I agreed with her on that part. "We can look for a place after we get there, perhaps at one of the streams. We are going to change your weigh in time to 6 pm when we are camping though." "Why do we have to change to time?" "It gets dark around nine and we are not going to rummage around in the dark." "Okay, that makes sense." "I am going to go and weigh myself right now and use that as my benchmark for tomorrow's weigh in." She said as she headed for the bathroom. "Bring the scale out here or I am coming in there." "Why, do you need to be in there?" "I want to see the numbers not have you tell me the numbers. You are not going to have a chance to cheat on this since it was your idea." "Fine, I will be back in a sec with the scale." She walked in and put the scale down on the floor and stood on it. The scale read 151 and she was not happy about it. "I told you I need to lose weight." "I know you did and now you are going to or you will have a very sore ass in more ways than one." I told her I would get everything ready for the trip and then asked her if she wanted me to take my camper instead of the tent since we are staying at a campground and she said, "Yes please." We had a week before we were to leave and she would have to lose weight during that time as well so this could get interesting. What I did not know at the time was how interesting she was going to make it where I was concerned. She had left out a few little details about what she was going to do to me. I told her that I was heading home and that I would see her tomorrow for her 'weigh-in'. She gave me a kiss and told me that she would not be home until about 8 since she had told some of her girlfriends that they would go out for a drink after work. I knew this was not a good idea but I guess she will learn in more ways than one. Besides this whole thing was her plan, not mine. I got home from work and started to clean up the camper and pack things away that we would need for our vacation. I still think doing this weight loss thing during vacation is a mistake. I put away some food items into the camper that I like to eat and some nutritional and low calorie things that she could eat as well. Around 7:30 I headed over towards her house and she pulled in the driveway just ahead of me. We hugged in the driveway and then went into the house. I could tell that she had been drinking by the way she talked. After she has one drink she starts talking faster and I was having trouble trying to keep up with her. We sat on the couch and talked about our trip. She had got onto the computer at work over lunch and found some places she wanted to visit while we were in that area. They weren't necessarily where I wanted to go but it is a vacation for the both of us so I figured that I could suck it up and go where she wanted to go as well. About ten minutes to 9 she said, "Oh it's almost time to weigh in and I am so excited. I am sure that I haven't gained any weight today since I only had a salad for dinner." Jenny went into the bathroom to get the scale and then sat it down on the floor. She got out a tablet that she had written her weight down on and then stepped on the scale. "That is not possible, it just can't be!" Jenny almost shrieked as she looked at the scale. "It says that I weigh 152, and that means I gained weight." She just stared at it in disbelief. Then she looked at the clock and said, "Wait, I have three minutes till it's 9 o'clock, I will be right back." Jenny ran to the bathroom and when she came back she got back on the scale. This time it read 151. "Whew that was close, but I don't get it I only ate a salad." "How many drinks did you have?" "Well only three but that shouldn't make a big difference." "If they were 8 ounce drinks and you had three that is 1.5 pounds sweetheart, and how much exercise did you get today? "Are you going to do this every time I weigh in?" She asked as if irritated. "That is what you told me you wanted me to do and I told you this was not a good idea remember?" "Yes I remember." "Well get over here and let's get your spanking over with then before I go home." "I don't get a spanking to day I have the exact same weight that I had when I weighed last night, or is your memory that bad?" "My memory is perfect. You told me if you didn't lose weight you were to be spanked and if you gained weight you were to be spanked and then plugged, correct." "Yeah but I didn't gain any weight." "You didn't lose any either." "Fine, if you want to spank me that bad then here." Jenny walked over and laid herself over my lap and said, "Go ahead and beat my ass then." I took her by the arm and sat her in my lap, looked her in the eyes, and said, "From the beginning I said this was a bad idea and you wouldn't listen. Now when you don't finish what you say you are going to do you get mad at me? I am going home and you can go to bed and figure out a different method to lose weight." I picked her from my lap, kissed her on the forehead and walked out the door. My Fiancée's Weight Loss Program Thankfully the next day was Saturday and I had the entire day to work on getting ready for the trip, if we were still going. I probably should not have walked out the way I did but I needed to prove a point. I am sure I made it but at what cost. I did not want to lose my fiancée but I also did not plan to keep playing this stupid weight loss game of hers either. I was working away and had my head inside the closet when she walked up to the camper door. "Can we go inside and talk for a minute?" She asked rather timidly. "I don't see any reason why not sweetheart." We went in the house and stopped in the living room. She looked at me and she had tears starting to form in the corners of her eyes. I grabbed her and told her that I loved her and just held her till she looked up at me and said, "I'm sorry." I looked at her and smiled and said, "Why don't we just forget that it happened and move on baby, will that work for you?" "Yes and no." "What do you mean by yes and no?" "Yes we can move on but no we have to finish what I started, because I need you to help me and I was wrong." "Okay, we will just use your weight from last night and start today then will that work for you?" I asked her with a smile. "I wish I could say yes but for this to work I need to actually follow through and I didn't last night so can we just take care of it now please." "I guess we can do that but we never really decided how much you were to be spanked." She looked at me and said, "I don't want to put a number on it, and I trust you to give me what you think I need each time. I don't want the punishments to be easy slaps; I want to know that I did not follow through." "If that is what you want sweetheart then that is what I will give you." I said as I sat on the chair across the room. "I motioned for her to come over and she stood to my right and just as she was about to lean over I looked at her and said, "This is to be a punishment sweetheart and part of that is the embarrassment of being spanked correct?" "Yes, I suppose so." "Then you are to take your pants down to your ankles as well as your panties and then lay your cute little ass over my knee." Jenny began to unbutton her pants and then pulled the zipper down before pushing them down towards her ankles. One they were there she hooked her fingers into her panties and lowered them in much the same manner. She was now standing to my right giving me a full view of her clean shaven pussy. She stood there for a minute and then looked at me and said, "Don't tell me that you are not enjoying this because I know you are. I picked this punishment because I know you have always wanted to spank me and play with my ass and I have always turned you away. I had to do this for the both of us and I hope that by the time I have lost weight I can either accept the fact that I enjoy this or you can accept the fact that I can't. Now please spank my ass so we can go get the camper ready." Jenny laid herself over my lap and I began to slap her ass like she was being punished. I did not give her slaps to warm her up because this was not a game to her. She wanted it to be a punishment for not following through with her plan. I gave her probably 15 good shots to her ass covering it entirely and then I stopped and told her that I was finished. Jenny stood up and rubbed her ass and then pulled up her panties and pants and turned to go towards the camper. We worked the rest of the day getting the camper ready and making sure that we had everything we needed. We finished early enough that we had time to go get another movie and she made us taco salads for supper that evening. We sat and watched the movie and just enjoyed being with each other. She was very careful what she ate and drank all day and made sure not to grab a snack even when she wanted one. We only had 5 days until we left for our vacation and I wished we could have left right then. Around 9 she went and got the scale and sat it on the floor. She looked at me and smiled and then said, "It looks like it's your ass tonight buster because I only weigh 149." I knew I was going to get it but she had lost weight and that was the deal. She didn't tell me any more than that however. "Let's go, get those pants off and across my lap. I can't wait to see your ass with a nice red tinge to it." "You are starting to enjoy this a little too much I think." I said to her laughing. "Oh I am just starting to enjoy it. This is only the beginning honey. You told me that you would do whatever it took to help me get through this and tonight I am going to begin to show you what I am going to do to you every time I lose weight." "I agreed to let you spank me." I protested. "You agreed to and I quote 'and I will support you in whatever you choose to do it...okay?' does that ring a bell for you honey?" I was in trouble because I had said that. "Don't you think it would be fair if I only got punished in the same fashion you would get punished for not following what we agreed to?" "That works for me sweetheart. So if I gain weight I get a paddle and a plug correct?" "I believe that is what you wanted me to do." "So if that is the case you should get the paddle and a plug if I lose weight then." She said with a huge smile on her face. "Didn't we forget a step in there somewhere? You know where you only get spanked for losing weight and the paddle if you gain. How do I go directly to the paddle?" I asked before this got any farther out of hand. "Yeah I realized that when I thought about it but I then realized that since you agreed to support me in any way that I chose I was good with it...how about you?" My goose was cooked or in this case my ass was. I dropped my trousers to the floor and then pulled my briefs down to join them. I was standing right in front of her and my cock was getting stiffer the longer I stood there. She looked at me and said, "Why don't you just go ahead and remove your shirt as well sweetheart, it's only going to get in the way." I peeled off my shirt and then stepped out of my clothes so I was standing stark naked in front of her with my cock acting like a divining rod. She reached out and grabbed my cock and pulled it toward her. She placed it between her thighs as I went down over her lap and then closed her legs together trapping my cock between them. She then told me to spread my legs apart as far as I could get them so that she had access to my entire ass. It was not long and she started to spank my ass with her hand. She must have spanked me about 20 times with her hand and then she reached over and picked up the leather paddle. "You mean I get both?" I asked hoping for a reprieve. "You sure do and I appreciate your support in me losing weight. I hope I lose at least a pound a day for the next 30 days." As soon as she said it she started to hit me with the paddle. She could have hit me much harder but she didn't. I think this was more of a power thing to her at this point and she wanted to see if I was willing to allow her to do this to me. She probably gave me about 15 swats with the paddle and then she sat it down and started to rub my ass. During this whole time my cock had been trapped between her thighs and cum was dripping from the end. I could feel it leaking out and she had to feel it between her thighs. While she was rubbing my ass she told me that she knew I was enjoying this even if I was not the one doing the spanking. "I hope you like the rest of it since you will be doing the same thing to me if I mess up." I was not sure exactly what she had in mind yet but when she told me to reach back and spread the cheeks of my ass apart I knew what was coming. "She reached over and grabbed a bottle and I heard the sound of the cap being taken off. She squeezed it and allowed some lube to land right on my asshole. The cold from the lube told me what was coming and then she said, "You better pull them apart farther than that or I am going to get a plug to use on your ass." It is amazing what a person will do to get there ass spread farther when you get threatened in that way. I really did not want the plug in my ass. I wanted to put the plug in her ass. She rubbed her finger around my anus for a minute or so and then she shoved slowly into my ass until it would not go in any farther. I started to hump into her thighs with each stroke she made with her finger. Her finger went out and my ass followed. When she shoved the finger in I pushed my cock forward and down between her thighs. She knew exactly what she was doing. She was using her thighs to milk my cock. She could feel me getting close because I suddenly picked up speed and was trying to get myself to climax between her legs. She suddenly pulled her finger out and shoved two fingers into my ass and opened her thighs at the same time. I let out an audible gasp when she did it causing her to laugh. "Remember sweetheart it is supposed to be a punishment for me so I guess in some way it is going to be one for you as well." She then pulled her fingers from my ass and added a third finger. She continued to pump her fingers into my ass until she knew I was beyond frustrated and then pulled them out and told me I could get up now. I got up from her lap with my cock still hard and wanting and she said, "Remember if things go well you will get a present at the end of this, one that you have never had before. I know I left you frustrated and I expect the same when you punish me. It is a punishment for me and I am going to make it one for you as well." I pulled up my briefs and my pants and put on my shirt. She looked at me and said, "I hope I get to do this every night just so you know." "I looked at her and said, "Don't take this wrong but I hope you gain weight a few days so I can return the favor." "You are supposed to help me lose weight." "Yes I will. I am going to spank it right off your ass the next time you mess up." "Is that a promise?" "Yes it is my dear, yes it is." I kissed her on the lips and she reached around and grabbed my sore ass and squeezed it. "That was so you don't forget me tonight." She said with a laugh. I shook my head and headed toward the front door to go home as my cell phone rang. I thought it was odd that I was getting a call from the office on Saturday night but I answered it anyway. After taking the call I looked at her and told her that I had to go to St. Louis on business but I would be back in time to leave on Friday so we could go on vacation. "Great, just great," she said acting disgusted. "What's the matter sweetheart?" "I finally get a program that I think will work and you have to leave now what am I going to do?" "It's simple, each night at 9 o'clock you get on the scale and take a picture of the dial so I can see it. We will settle up when I get home." I told her realizing her disappointment. "Well someone is going to have a very sore ass if that's the case." "There might be two people with a sore ass if things go the wrong way you know." I said laughing. I told her I would look for her text with the picture in it tomorrow night and then after she sent it we could talk just like normal. "I am only gone four days and then we get to leave. I will be home on Thursday evening and I get Friday off because of the short notice." I kissed her again and headed home to pack and then I was off to the airport to catch my plane for St. Louis. The plane ride to St. Louis was okay but I was already missing her and was wishing we were on vacation. It is amazing how the days drag getting to vacation and how they fly once you are on vacation. Oh well I guess I will just have to wait for her text tonight to see which one of us is in trouble. At almost 9 o'clock on the dot my phone sent me a text showing the scale and it showed 148 lbs. Great I knew she would be calling very soon and then my phone rang. "Your ass is mine again; your ass is mine again." She said in a sing song voice. "I love you too sweetheart and I see you lost another pound. That is great to hear." "Do you really mean that or are you saying it so I will go lightly on your ass when you get back?" "Both." "At least you were honest about it." She said, as I could almost hear her smile into the phone. "It's okay sweetheart I am sure you will continue to lose weight if you don't want me to get to your cute little ass." "I don't mind you getting to my cute little ass but I hate losing. Besides I already know how I am going to spank you the next time and it is going to be so much fun." "Oh really, and how is it that I am going to be spanked?" "I am going to bend you over the back of the couch this time so that I can watch your ass as I spank it, and with you bent over like that your ass cheeks will spread open for the plug I am putting in there this time." "For someone who didn't want to be spanked or have their ass played with you sure do seem pre-occupied with mine." "Yeah I have started to like this a little bit, but right now it's your ass getting into trouble and not mine." "We will see how you do when you are bent over that couch with my finger in your ass lady." "Promises promises promises." She said, laughing at me. She told me goodnight and I went to bed knowing I had an early day tomorrow. The following evening the phone did not ring at 9 o'clock like it did the night before. I finally called her to see what was going on and she didn't answer. I texted her saying, "I don't know why you didn't call me or send a pic. I don't know why you didn't answer my call. If this has anything to do with you gaining weight and you are ignoring me, the last thing you will have to worry about is the punishment you will get for gaining weight. That spanking will be minor to the one you will get for ignoring me." I hit the send key and in a flash my phone rang. "Why there you are sweetheart and why haven't you called me?" "I don't want to talk about it." "What don't you want to talk about?" "You already know why and I am pissed that I gained a pound." "So you were ignoring me because you gained weight." "I guess I was and I am sorry." "Your ass is going to be sorry." "Please don't be mean." "You call me up in a sing song voice when you lose weight knowing you get to have fun with my ass but on the day you gain weight you ignore me." I say with a bit of irritation. "You are right and I should have just called and told you and sent the pic. I guess I can't blame you for being upset with me." "I am more upset that I thought something was wrong when it clearly wasn't." "I guess I hadn't thought of that." "I needed to tell you that I am going to be flying to California tomorrow to check on a project there and then I will be flying home from there." "How am I supposed to keep track of what time zone you are in?" "That is why I called. Just text me your pic's each night and we will talk by text till I get home. I love you and can't wait to see you." "You mean you are all cheery now that you get to paddle my ass." "I would be lying if I said that I wasn't looking forward to that." "I know I just don't want to gain weight." "Sweetheart as much as I love you, I know you will lose the weight you want and my ass is going to be very sore before vacation is over." "How do you know that?" "Because if this is that important to you I intend to make you lose weight while we are gone." "You can't starve me to death." "I don't intend to but I do intend to walk you to death hiking and fishing." "Hey that is a great idea." "I know, glad I thought of it. You do realize though that you will have days that you won't lose any weight, its normal." "I know and I love you. I will text you tomorrow with the pic either way." "Okay talk to you tomorrow and I love you." Tuesday morning I hopped my flight to California knowing that the next few days would be difficult due to the fact that text messaging would be about the best I could do given the time differences and my schedule. I got into San Francisco and headed for my hotel to get settled in and then called the office there to see when it would be best to come in to look at the issues they were having. They asked if I could come in right away and I told them I would be there within the hour. We worked up until my phone went off signaling a picture had arrived and I took the time to look at it and saw a message saying, "pay up buster." She had lost three pounds and was down to 146. I sent one back that said, "Don't count your chickens too soon lady. Score your ass 1, my ass 2." She texted me back with an, "I love you, are you at work?" "Unfortunately yes and I love you too. Don't know when I will get out of here." "Okay, ttyl, Love you." I went back to work knowing that I was probably going to have a sore ass but if it helped her with the weight issue I was okay with that. We worked up until 11 o'clock pm and I went back to my hotel knowing it was after 1 a.m. back home. I didn't bother Jenny since I knew she would be sleeping. I went to bed and got up at 7 and went back to the office. We worked through lunch but had some brought in to try and speed things up. It was Wednesday and I was leaving the following day. We worked on finalizing what I was working on at that time when another problem came up that also needed my attention. Working into the night was our best option since everyone else was out of the building and you can get more done without people bothering you asking what you are working on. At 9 o'clock my phone went off again and I didn't even realize it was that late. There was no picture this time it just said, "are you still at work and the score is 2-2. I went off the wagon and went out with the ladies now I am back to 150. Sorry." I typed back, "No need to be sorry. We are even at this point so I guess we both have to pay the piper. I will be home tomorrow night and I miss you terribly. I can't wait to see you and I should be home around 6 p.m." We finished up what we could and then I went back to get some sleep. What I had to finish would take only a couple hours so I knew I could catch a flight to get me back in a reasonable time. I finished the following morning around 11 and got a flight for noon. I arrived back into town at 7:30 p.m. and texted her saying I was home. She immediately texted me back asking if I was coming over or if I was too tired. "I am never too tired to see you sweetheart." All I got in return was "CU in a bitJ" I jumped in the truck and headed to her house. When I got there she was standing on the porch and she ran to the truck to give me a big hug and several kisses. "Wow, a guy likes to know that he has been missed." "Oh I missed you alright. This was hell on my diet. I missed you so much all I wanted to do was snack all the time." I raised an eyebrow and looked at her and she had a little frown on her face. "Are you telling me something that I don't want to hear sweetheart?" "I don't know yet since I haven't weighed today but it probably isn't good." "Well I guess we have this evening to take care of what needs done?" "We can do that at another time. I think we should spend tonight just cuddling and enjoying each other." "We can cuddle and still take care of your issues and mine but we are staying on track with this except for one change if you agree to it." "What's the change?" "I think this weighing in every day is too often. I think we should have you weigh in on Friday and give out whatever punishment is deserved at that time." "I think I like that idea but what about what we were using to decide what we got for punishments?" My Fiancée's Weight Loss Program "Well since we are doing it weekly then I guess the spanking and paddling part wouldn't change much but I guess whoever is in trouble will have to endure several different sizes of plugs on that night, within reason." "What do you mean by within reason?" "I don't want to hurt you so let's just play it by ear and see how it goes, okay?" "That works for me, now we can just cuddle tonight and see what happens tomorrow." Now that we had that all taken care of I was ready for a good meal and I wanted to go out to get one. Jenny wanted to stay in and cook it so I gave in and ran to the grocery store for something to eat. I got some steaks, potatoes, asparagus, and a carton of low-fat Ice cream for dessert. Jenny liked what I picked out and said it was sweet that I got low-fat ice cream. She even ate a little of it but not much. She ate about half what she normally eats and then after we finished eating she wanted to go for a walk. She never wanted to go for a walk. Maybe she was finally figuring out that exercise even a walk was better than being a couch potato. I stayed until about midnight and told her I would be over the following afternoon with the camper to pick her up after work. She gave me a kiss and told me she would see me tomorrow. I picked her up and she was elated to get started on vacation. It took us about two hours to get to Decorah and we did not have a problem getting in since we were there early enough on Friday. We looked at a map of available sites and picked one west of the check-in back on the very far west side. We were next to a small parking lot so we had no one to our south and there was not anyone on the north so far. I did not expect that to continue but we would take it the way it was. I figured after the weekend that our odds of getting more solitude would be higher. Sure enough while we were unpacking a couple with about 4 kids parked to the north. That really did not bother me since the kids were younger and made enough noise that they would drown us out if we got frisky. We had the camper set up and then Jenny wanted to go inside and talk to me. I hate it when people say I need to talk to you. I feel like I am either in trouble or about to be. We went into the camper and she said that while she did agree with the new rules we had made she felt that we should at least square the books from the week before. "Sweetheart if you haven't noticed there are people right next to us and they could hear us and it was 2-2 so why are we going to bother?" "It wasn't 2-2 it was 2-3 and I already knew I had lost the third one before you made your offer." "Why are you doing this?" I asked. "Because I need to and I want you to punish me for not doing what I needed to do. I gained 5 lbs. while you were gone and I feel terrible about it." "I guess I didn't realize that you had gained weight." "Well I did and I need this before we start with the new rules, okay?" "If that is what you want then we will take the truck and go find a secluded place to take care of the penalties." "Thank you, I already put the stuff we need in the truck." "Pretty sure of yourself were you?" "Pretty sure that I could count on you." She said with a smile. We got in the truck and started to drive via a trout map to a stream labeled as North or South Bear. There were two of them that met at one location but that was way to open to others to do what we were going to do. I told her we would just go upstream and cross the streams at each mile and see if we thought it might work. We went up to almost the Minnesota border and crossed but there was a car at that location. We headed back south and found a place to park that there were no cars. "This looks like a place to get out and go for a hike to see if it will work for us." I told her when I parked and shut off the truck. Jenny grabbed the bag and I grabbed the fishing poles. "I don't think we are going to need that sweetheart." "Well it makes a good cover story if we do meet someone, and besides I want to eat fish for supper." "Okay, are we going to fish first or take care of business first?" "If I warm your fanny you can always sit in the cold water to cool it off you know." "Okay we take care of business first and then we can sit in the cold water while we are waiting for the fish to bite." She said laughing. We walked for a distance and then I spotted what I was looking for. I started walking towards it and it was in a great location. We could see or hear anyone coming from upstream or downstream before they got to us. She looked at me and I pointed to an old tree that had fallen down that was about three feet in diameter. "What is so important about that old log?" Jenny asked looking confused. "Well we can see in both directions and you can lay over it putting us at the right height." I answered. "What do you mean by us?" "I lost twice and you lost three times, remember?" "I thought I was the only one getting this." "I keep my promises, we can take turns, and then tonight we can take turns rubbing in lotion as well." "Okay then I get to go first then." She replied. "Why is that?" I asked wondering what her reason was. "It works out better that way if I do, just trust me." She looked me dead in the eye and said, "I expect to be spanked and paddled but we can save the paddle for the last time it's our turn. After you spank me there is a bottle of lube in the bag and a set of toys for you and a set for me. Pick a set and use that set for me and I will use the other one on you. We have to keep the last one in until we agree that we have had them in long enough." "What kind of toys are you talking about?" "I told you I went shopping and I bought a set of anal dilators for each of us. You have always wanted my ass and I figured that if I was getting punished I would have to take them and maybe, I said maybe, someday I might let you do what you have always wanted to do. But I am not saying yes yet, okay?" I did not know what to say. I was not expecting this at all. She was so dead set against me playing with her ass. "What made you change your mind all of a sudden?" "Do I have to tell you?" "No, that is your choice; I am not going to push." "Maybe someday I can tell you, for now just be happy that I am willing to explore the possibility, even if I am using it as punishment right now." "Okay, I will leave it alone till you're ready, if and when you're ready." I answered. "I think it's time for us to begin," and she slipped off her shoes and dropped her pants and panties to the ground and stepped out of them. She stepped back into her shoes and then took off her shirt and bra. She was standing stark naked out here in the middle of nowhere. I started to take off my clothes and she looked at me and said, "No, please leave yours on till it's your turn." She then turned and laid her clothes over the log and then lay over the top of the clothes leaving her ass bare and waiting for me to start. Her feet were still on the ground for balance so I told her to move them farther apart and she quickly moved them just beyond shoulder width apart. As soon as she was in place I started to smack her ass with the palm of my hand. I slapped and slapped until her ass had gone from white to pink. Since I knew that we were doing this more than once I did not want to make it totally unbearable for her so after I made sure that her entire ass was the same color I stopped and told her to reach back and pull her cheeks apart and hold them there. I reached for the bag and took out the lube and a set of white dilators. They ranged in size from one inch up to two inches by quarter inch increments. She would be getting the first three today. I lubed up the one inch plug and placed the tip at her asshole and then decided to put some on my finger so make sure she was ready to accept it. I didn't want this to hurt her and I also wanted it to be pleasurable even though she was thinking it was punishment. I circled her little pucker for a minute and then pushed my finger in slowly. "That doesn't feel so bad sweetheart push it in please." She said. I pushed my finger in and left it there for a minute and then moved it in and out to get her used to it. I slowly removed my finger and then picked up the plug again and placed it at her slightly gaping pucker and slowly inserted it. Granted it is not that large but it is larger than my finger and when I pushed it in she groaned. "Did I hurt you?" I asked concerned. "No stupid, I am not a china doll you won't break me." "Pardon me for worrying about you." I smarted back. "Sorry I guess I should thank you for trying to make this easy for me." She said as she started to get up. "Don't you want me to take it out?" "I told you it was punishment and it stays in until we decide to take them out, that means during the spanking as well." I really don't think she thought all of this through but then again maybe she did. Someone had given her some instruction on what to do and I am guessing that is what peaked her curiosity about anal play. But who I wondered?" Once she was ready I also took off my clothes much the same way she did and laid over the log. As soon as I was in position she started to spank me just like I had her. She was not giving me sharp slaps yet. I figured those would be on the next round with the paddle since I only get spanked twice. She told me that my ass was a nice shade of pink and I needed to spread my cheeks and get ready. I reached back and pulled my ass cheeks apart and she placed her lube covered finger into my ass all at once causing me to grunt out loud. "That sounded like an enjoyable grunt to me," She said as she slapped my ass again. She stroked her finger in and out a few times and then reached for the plug. She lubed the tip of it and placed it to my asshole and gave one even thrust pushing it into my ass, which also resulted in a grunt. I got up with the plug in my ass and it was not uncomfortable, it just felt strange. I had never had something in my ass other than her finger. I looked on as she again lay over the log and spread her legs apart. Her asshole was starting to spasm a bit with the plug in it. It was moving in and out slightly I assumed from her anticipation. When I looked again I realized that she was having an orgasm. She had fluid running down the inside of her thighs. To me this was a good sign, a sign of someone who was enjoying anal play. I started to spank her again just like before only this time she was slightly pink when I started and I began to slap her ass harder than I had the time before. I did not want her to think I was going easy on her. She would be disappointed if I was. I slapped her ass for a good ten minutes without stopping and I could just begin to hear the echo of the slaps in the trees. Nothing too loud just enough to know that it was happening. Once her ass was a nice light shade of red I stopped spanking her and turned to tell her to spread her cheeks but she was already grabbing them in anticipation. I lubed up the one and a quarter inch plug and the slowly pulled the one inch plug from her ass. Her ass was gaping a bit more than before so I knew that the next size should not be too much for her to take. I slowly inserted the plug into her and she moaned out loud with a loud, "Oh yes." Her body started to shake and she sort of bounced on her feet up and down as she again made the plug suck in and out a bit while she recovered. I asked her if she was still okay and she replied, "Wow, more than okay so far." She stood up and said, "Okay assume the position buster." I walked over and assumed the position and worried about her hitting the plug. I don't know why I did not think of that when I was spanking her. I guess that I saw it and avoided it without even thinking about it. The first smack to my ass drew out a huge sigh from me and an echo in the trees that I could hear. It sounded like a gun shot off in the distance. She was not hitting me that hard but the sound echoed into the wilderness. I can imagine what the wildlife would say when they got home at night, "You should have seen those stupid humans out in the forest today, standing around stark naked, beating each other on the ass, and sticking some dumb looking thing up each other's ass, and they think we are the wildlife." I laughed to myself as another shot hit my ass. Jenny made sure to cover my ass completely and it almost felt like it was on fire when she finished. It really did not hurt me but it made me realize that my ass had been severely warmed up, and had my cock standing at attention. When she put the paddle down I reached back and waited for the plug that I knew was coming. She looked down at me and said, "Okay I am going to remove your plug and then shove this one straight in, I hope you're ready for it." She did as she promised as she shoved the new plug straight in listening to me moan as she did it. She reached around and grabbed my hardened cock and stroked it a few times and then said, "That ought to hold you for a little while." As I groaned needing her to finish what she started. While I was trying to recover and was standing up she walked back over into place and waited for me to begin. I grabbed the paddle and began to paddle her ass just like she had done to me. I could also hear the echo's more distinctly in the distance and wondered if I was hitting her too hard. When she started to moan I knew that I wasn't and I could watch that plug move in and out again and her legs shake as she was beginning to orgasm again. I waited for a second or so and let her relax and started again. I did not want her to achieve her orgasm yet. I wanted her to have that last plug in her ass before that happened. Her ass had turned a nice shade of red by this point so I dropped the paddle and grabbed the one and a half inch plug and lubed it up. "Okay sweetheart do you want me to put this in the same way you put mine in or do you want it slow and steady." "Please just shove it in." I wasn't going to just shove it in since I didn't want to hurt her so I pulled the other plug out and as I started to shove the larger plug in I slapped her on the ass fairly hard with my hand and started it into her. That took her mind off how fast it went in and she started to shake again like she had before. Once it was seated she reached down and put her fingers to her clit and started to rub. Then I heard, "Just don't stand there staring at my ass put your cock in me and fuck me." I had never heard her say anything like that before but it was a turn-on to say the least. I placed my cock at her dripping pussy and shoved it in with no effort at all. She was more than ready for me to begin so I grabbed her hips and set a very faced pace fuck until I came a few minutes later. She had fluid running down the insides of both thighs and when I pulled my cock out she just stayed there allowing my come to run from her pussy. I reached into the bag a got some of the towels that we carry and began to gently wipe the sweat from her neck and back until I worked my way down to her pussy and thighs. I made sure to wipe her clean and then she stood up with the plug in her ass and turned to me and gave me a hug and kissed me on the lips and said, "Thank you." "I don't know what you're thanking me for that was the most amazing thing we have ever done!" "Yeah, it was pretty good for me too." She said with an impish smile. We got dressed and started back toward the pickup with our plugs up our asses reminding us of what we had just done. When we got almost to the truck I remembered that I wanted to catch some fish and she asked me if I could just catch them back at the campground. I told her that wasn't a problem unless she wanted to give me ten minutes to see if they would bite here. "Okay you have ten minutes and then we will see." Ten minutes later I had two very nice trout and I cleaned them and we got in the truck and sat very gingerly on our sore asses making sure that the plug was situated just right. We got back to camp and decided that it was time for the plugs to come out so we went into the camper and removed each other's and then kissed some more before we started supper for the evening. We ate our supper listening to the kids next door fight and bicker amongst themselves and their parents telling them if they didn't behave they were going to get a spanking. We were both drinking a beer when that happened and we almost spit it out when we heard it, as we laughed to ourselves. If that lady only knew. The next two weeks at camp went almost the same except that we had managed to only get us both to the next to last plug. We made a couple of bets during the week where she lost one and I lost two. That made us even up in the plug category but we still had this Friday to have her final weigh in. She had lost 23 pounds while we were out here mainly due to eating only what we cooked at camp and from walking everyday fishing. We walked about five or six miles each day through some pretty heavy timber and you burn some calories doing that. Tomorrow night was the weigh in and I figured that I was going to get the largest plug. I knew she had to lose some weight so I was doomed. We headed out to fish for the final time and she said, "Wait I want to weigh myself before we go." Oh great I thought to myself and she ran in and looked at the scale. She came out the door beaming. "I only weigh 133 pounds and I owe it all to you." "You are welcome sweetheart but you have to give yourself credit as well." "Well we are going to take the bag with us and we are going back to that fallen tree like we did the first night. I liked that spot and I think you will too. We drove to our spot and I was surprised that there was not anyone there. It was just after lunch on a Friday though so people were still at work. We walked back to our log and she looked at me as we both began to undress each other this time. It had gone from a punishment at this point to two people who loved each other wanting to give the most pleasure to the other they possibly could. Anyone who is not into spanking would not understand that, but the high that we get from it is something that we share. I honestly thought that Jenny had been turned on by using the plugs as well and I hoped that maybe someday we could continue to share that as well. Once we were undressed she said, "Today we have a new set of rules and I will go first. We are going to only use the paddle and we are to give each other only ten slaps with it and then we put in the plug." I looked at her confused I guess because she then said, "We are going to use all five of the plugs, not just the little ones." "Are you sure about that sweetheart I don't want to hurt you." "You won't hurt me and I need you to do this for me okay?" She walked over and laid some of our clothes over the log and then lay across it and spread her legs wide waiting for me to begin. I laid ten rapid slaps across her ass as she grunted with each one. I didn't go real easy on her and I know she did not expect me too. She reached back after the tenth slap and grabbed that beautiful ass of hers and spread her cheeks apart waiting for the plug to be inserted. I lubed it up and placed the tip at her pucker and slowly inserted it. She moaned with its insertion and shook slightly even though it was the smaller plug. I chose not to lube her with my finger since we had been doing this for the last two weeks and we were past the need of someone getting us ready. We were both primed and ready for this before we got here. After the plug was seated she stood up and motioned for me to lie over the log. I took my position and she began to slap me with the paddle much as I did to her. She did not go easy on me either since she also knew we would only be getting 50 slaps by the time we finished. I reached back and spread my cheeks and she lubed up the first plug and inserted it straight into my ass without slowing down. I moaned in delight as she inserted it. By this point it was not so much about the plug it was more about the trust between us and the pleasure that we had from being together doing something that others might think was kinky or weird. To us it was normal I guess.