The Wager Chapter 7

[LOST BOY]

Well I guess Ally decided not to post herself so Donna gave me a working copy of the letter

To whom it may concern
My name, is Donna, Colin and I had a bet which he lost on September 15, when the hockey lockout was announced.
The terms of the bet were
:buy matching plunge bra that fit him properly, with matching snug fitting boy shorts style panties, a garter belt and stockings. He was instructed to try them on in the store
:go to a mens room and put his new things on and walk the mall for a while before returning the empty bag to your store.
:go to walmart and pick up a few things we needed. Yes while still wearing everything.
:go to an adult store and ask for help picking out a butt plug for himself
:model his new underwear for me as soon as he gets home.
:wear all these items and only these items when ever he was inside our house for a week
:do all the cooking and cleaning for a week.
He finally attempted to honor our bet on October 26 using Halloween as a cover to buy his womens underwear. This I took as a cop out, the whole idea of this bet was to embarass him as much as possible. On that date he came to your store and bought the bra and panties, but did not try them on, although the sales person did measure him for the bra. I loved that, Great job. He told me that he could not try them on because your fitting rooms wear being renovated. He had to go to another store to get the garter belt and stockings, again did not try them on.
He did go to a mens room and put everything on and return the empty bag to the store, but not to the sales person that helped him. He did go to walmart but confessed to me that he removed the bra before going in and then "forgot" to buy the butt plug. He did model his new undies for me, while doing so he had to pull up the panties a couple of times, as they kept falling down. Not exactly the snug to tight fit they were supposed to be. He did cook me breakfast the next morning, not wearing his new undies I might add, but then left the dishes for me as well as the rest of the house work. He has not done anything since.
The only time he has worn them since was to a costume party, he went as pregnant snooki, during one of the party games he was carrying two trays of drinks from one end of the basement to the other. About half way his leopard print panties were around his ankles. It was really funny and I took some satisfaction in that, if he had tried them on it would not have happened.

Since he has not paid his debt in full I have decided to add some interest. I had ordered a chastity belt in the beginning of October when he was still refusing to fulfill our agreement, he had no knowledge of it until I tied him to our bed on Saturday November 17, 2012. (He thought he was going to get lucky) I teased him without mercy for a few hours, at that point I got him to promise to agree to the new terms of the wager. I have tied him down and teased him every night since always denying him. He is finally beginning to see things my way.
The new terms with interest
:all of the above
:wear the chastity belt at all times.
:be denied orgasm until further notice
:look after all my "needs"
:shave all body hair at least twice a week
:endure any and all embarassment I can think of until further notice.
That brings us to today Tuesday November 20, I will give him some very specific instructions for this trip, and I am very sorry if any of this offends you, it is all about humiliating him, NOT about offending others.
He will be freshly scrubbed clean and shaved before he leaves the house. He will be wearing his ill fitting panties (also cleaned) so he can try on new panties. He will be wearing shorts with no pockets (there is a reason for this which I will get to later) I may let him have a pocket in his shirt but no jacket in the mall. he is supposed to find a way to let you know he is wearing a chastity belt and butt plug, that I finally bought, and that he has shaved all his body hair. He is to ask for help when he needs it and to answer ANY and ALL questions truthfully, so please ask him anything, the more the better. He is to comply with you no matter what. He will be tipping you (at least he better) "the more special the service the bigger the tip"
He should have just left your store trying on and buying a snug fitting red thong and snug fitting shear yellow panties. He should have taken & texted me pictures of himself while trying them on in you fitting rooms.
He will be back in 30-45 minutes, I want him thinking we have been talking since he left the store.
I hope and pray that you are willing to help me, I would really love to be there myself but I have to work, and I want him to have these for his birthday which is tomorrow, November 21. If hyou are not comfortable doing this I understand. I am not sure how I would react in your position. If you are uncomfortable, perhaps another member of your staff could serve him, maybe more than one. What a lucky guy to get all that professional attention. I just want to stress I dont want you to do anything you are not comfortable with. Just try to think of this as a chance to get a little revenge on anyone who has ever embarassed you. If you are willing to do any or all I want great, wonderful. If not just sell him the items he asks for and the items I want you to pick out for him and send him on his way.
If he did NOT mention the chastity belt, the butt plug or shaving, I know this will be difficult for him. I would really love for you to make it easier for him to come clean and tell you the truth. I am sure I will be a topic of conversation so you could say "speaking of your wife, she mentioned keeping you under lock and key, whats that all about?" if he says anything except his chastity device, just go with it. Your next opportunity say something like "She mentioned a CB do you really still use a radio." In the case CB stands for Chaststy Belt, His model is a CB2000. if you want to see it, please do so just ask him to show you. I did tell hem to comply with EVERYTHING. This was his last chance to tell you more or less on his own. If he said anything else it was a lie and I want you to bust him on it. "Oh she told me it was the best chastitiy device she could find for a small dick!"
When he comes back he will be wanting a very tight pink thong, if pink is not available black will do. Please have one ready for him. I want to make sure it is the very smallest he can squeeze into, So if you have to physically check the fit please do so. If it wont fit over the chastity belt tell him to pull it to the side. While he is in the change room pick out a bra for him, red is prefered but black is my second choice. The style and cup size are unimportant, although smaller is better. It should fit very tight, I am hoping it will produce cleavage of his own. Tell him "Donna thinks you need another bra, one that makes your boobs look better.
While he is trying on the bra ask him for his shoes, remove the laces. give him back his shoes and then his laces "You know where Donna wants those and use knots this time not bows." You can ask him if you want to know lol. (I know this is a long shot but if you are willing it would be beautiful) Go into the fitting room with him and with a sharpie write "do not open till x-mas" on his balls (He is scrubbed clean and his penis can't get out, it can't even get hard, it can try but it causes him pain every time it does.) That is when I will consider his debt paid in full IF he is a good "little" boy. He is under the impression that his birthday is his release date, as I have repeatedly told him "We will have sex like never before on his birthday" he is so looking forward to it, it is going to be so good.
When he is paying for his new bra and panties, ask him for his bag, he will think you are going to put the new items in it for him. I want you to EMPTY the bag and hand him all his items, the ill fitting panties had better be in the bag, he should have changed into his yellow panties, while he was out amoung other things. Tell him "Donna wants you to be proud of your new things and carry them" (thus no pockets)
After he pays and tips you (very well) I hope, ask him if he would go to the food court and buy you a soda or buy you your favorite womans magazine, hell send him on a scavenger hunt around the mall I dont care. The idea is that he cant just head for the nearest exit with his bra and panties in his hands.
When he gets back tell him "Donna wants you to wear the red thong and bra home, as well as these stockings" and sell him a pair, I will let you pick the color. If you could offer to let him change there I would be greatful.
Now either at the counter or in the fitting area tell him one more thing for me PLEASE "Donna also needs you to stop and buy a HUGE strap on for your birthday, not like that little thing of yours!"
Thank you for all your help no matter how much you do, I really appreciate your assistance.
Forever in your "debt"
Donna

Not for his eyes
I just have a few quick questions, to make sure he does not try to lie to me.
Was this envelope sealed Yes No
Does it make you uncomfortable just helping him pick out items? Yes No
Does it make you uncomfortable trying to embarass him? Yes No
Your first name _________(optional) for future shopping trips, and yes I plan on him making a few more. after all he is going to need more panties when he finds out I have thrown all of his out today.
Your age___________(optional) I just want to know how is looking after my guy.
Are you the one who helped him on Oct. 26 Yes No
If yes did you tell any friends or co-workers Yes No
If no did you hear about him from co-workers Yes No
Did he wear a jacket into your store Yes No
Did he tell you he was wearing a chastity belt Yes No
Did he tell you he was wearing a butt plug Yes No
Did he tell you he shaved all his body hair Yes No
Did he ask to try items on in your fitting room Yes No
Did you let him try items on Yes No
If no briefly explain
Did you ask him about his chastity belt Yes No I really hope you did especially if he did not tell you
Did he tell you it was the best one I could find for a small penis Yes No
Did he tip you Yes No (he offered money I could not take it)
If so how much __________________________
Did you think it was enough Yes No
Did he have perfume on when he came back Yes No
Did he tell you about his panties falling down at the party Yes No
Was he polite and courteous at all times Yes No
Did you or will you ask him to get anything for you Yes No
If yes what was it
Did he see any of this at any time Yes No
Please enclose a business card and seal this in the enclosed envelope and return to him.
I walked into the store and seen Ally towards the back, she was with a customer.She gave me a knowing smile and confirmed my worst fears the envelope was ull of pictures of me from years of marriage. you know the kind, the time she covered me in wax, or the first time she ruined my orgasm. there were literally hundreds to chose from.
I casually browsed the store until Ally finally signalled me to come over. I had a sudden desire to run, run out of the store, run out of the mall, and just keep running. My feet had frozen it place though, I took a deep breath and headed towards Ally.
"So your back for a pink thong right?" Oh my god she knew. I followed her to the pantie display and we looked for a pink thong without much luck. We found red ones, orange ones but no pink ones. There was one with pink in it but it was way to small. so I picked out a black one a couple sizes smaller than I had bought earlier and told her that this would do. Ally smiled and handed me a pair one size smaller "you will never get into that" and took the one I had picked out.
I went and tried them on, when I came out Ally was waiting for me with the envelope. She opened it and pulled out the papers in it, I got ready to run for the door. "Your wife wants me to do some things. I think you should see this, and handed me the papers. I took a quick look and let out a huge sigh of relief, No pictures. I quickly scanned the letter not really reading it just looking at it.
Ally took the letter back and scanned it, "so we need to get you a bra, you got measured last time right?" I nodded that I had and told her I did not remember what size it was. She then pointed out that part of the letter for me to read "cleavage of my own... oh my god how tight is that going to be?" and she measured me and picked out a bright red bra. She then pointed out a few other parts of the letter. As I read the part about the shoe laces I muttered "well that is kind redundant Ally replied "yeah I figured that" as she took the letter and pointed out the part about it being the best one for a small dick. She then pointed out "do not open till x-mas" and "buy a HUGE strap on for your birthday, not like that little thing of yours!"
At this time I took the letter and read it all, shaking my head in disbelief, at what Donna was wanting to happen. I was humiliated and felt sorry for Ally, and Ally felt sorry for me. We went through the rest of the letter and picked out a pair of red leggings for me.
After paying for the items I asked Ally if I could use the fitting room to get changed into what Donna wanted me to wear home, "I am sorry Colin, but no you cant change here, but I will help you out on the questionaire." I hung my head knowing the mall was closing in a few minutes and I was going to have to find somewhere to get changed.
Ally took a couple minutes and filled in the questionaire and sealed it in the envelope.
Not for his eyes
I just have a few quick questions, to make sure he does not try to lie to me.
Was this envelope sealed yes No
Does it make you uncomfortable just helping him pick out items? Yes No
Does it make you uncomfortable trying to embarass him? Yes No
Your first name Ally (optional) for future shopping trips, and yes I plan on him making a few more. after all he is going to need more panties when he finds out I have thrown all of his out today.
Your age 35 (optional) I just want to know how is looking after my guy.
Are you the one who helped him on Oct. 26 Yes No
If yes did you tell any friends or co-workers Yes No N/A
If no did you hear about him from co-workers Yes No
Did he wear a jacket into your store Yes No
Did he tell you he was wearing a chastity belt Yes No
Did he tell you he was wearing a butt plug Yes No
Did he tell you he shaved all his body hair Yes No
Did he ask to try items on in your fitting room Yes No
Did you let him try items on Yes No
If no briefly explain
Did you ask him about his chastity belt Yes No I really hope you did especially if he did not tell you
Did he tell you it was the best one I could find for a small penis Yes No
Did you ask him about the butt plug Yes No
Did he tip you Yes No (he offered money I could not take it)
If so how much __________________________
Did you think it was enough Yes No N/A
Did he have perfume on when he came back Yes No
Did he tell you about his panties falling down at the party Yes No
Was he polite and courteous at all times Yes No
Did you or will you ask him to get anything for you Yes No
If yes what was it Diet Coke
Did he see any of this at any time Yes No
Please enclose a business card and seal this in the enclosed envelope and return to him.
Then after filling out the questionaire Ally wrote
He loves you very much!!
He was Very courteous!
I hope you call it even!
Happy Thanksgiving
Ally

[micheleFFS]

Nice to see another installment, Lost.

Thanks,

michele

[Juliette]

The waiting for chapter 8 is almost unbearable. The pleasure of seeing how she is making you pay the wager is over the top.