Becoming Chloe

Our hostess came over to tell us our table was ready. We had the bill transferred to our table and got up to follow her into the dining room. I followed Kate and the hostess and as we were leaving the bar I noticed a very handsome man staring and waving at Kate. My heart stopped and I felt fear race through my body. I was worried this was someone she knew and that I might be discovered. She immediately saw him and turned her head to me and said, "Go to the table and I'll be there in a few minutes."

I watched as he took her hand and gave her a kiss on the lips as I followed the hostess out of the bar. I didn't want to look back or stare because I was afraid he would want an introduction, so I kept up with the hostess and sat at the table.

"It looks like we lost your friend. I'll let her know where you are and I'll have them bring you another drink."

"Thank you," was all I could say as I tried to look and see what was happening with Kate. I sat there alone for about five minutes worried and concerned about Kate as well as being alone and what was happening in the bar with that guy. She finally turned the corner and sat down with me at our table.

"Who was that, Kate?"

"Do you remember when I told you about the guy I dated in college, Ricky Carter?"

"Yes, you dated him for 3 years and almost married him, as I recall. Was that him?"

"That's him. He just moved here a month ago and lives just a few miles from us. I haven't seen him in years and now, just like that he lives right nearby."

"Well you seem very happy to see him again."

"He's a great guy and I always enjoyed spending time with him. Are you a little jealous baby? Don't be, remember you're Chloe my girlfriend. Girlfriends support each other. Don't worry, I'm sure we can find a guy for you too baby." she said giggling.

"Not funny, Kate."

"Oh just relax, its part of being a woman. Men will always be involved at some point and the sooner you realize that the quicker you'll understand what really being a girl is all about."

"I'm not sure I'm ready for that, Kate. Do you want to be with him?

"I understand that you're scared but if you really want to be like me, a woman, then you will have to face the fact that at some point there will be a guy hitting on you or wanting to date you, Chloe. You already admitted that you like it when they find you attractive and it makes you feel warm and tingly all over. It will take time and I'll be there to help you and yes, I think it would be fun to spend some time with him again. He asked me out for drinks sometime and I gave him my number so I might see him again, yes. You can understand my needs to be with man, can't you honey? You do know I have needs too and you can't be selfish with me, honey. Let's change the topic. How long have you had your little cage on now?"

It took a great deal of effort to change my thoughts about Kate and Ricky but I did and said, "It's been 4 days now, can we take it off tonight? I really need some relief. Every time I start to get hard the intense pain stops the erection and my balls are so ready to come. Can we, please?" I pleaded as I saw her smile.

"Well to tell you the truth, you're begging, it's making me wet. No, I think after you complained about Ricky hitting on me tonight that you will need to keep it locked for until next week. If you're a good girl I'll release you next Friday night. Now you have a little incentive to make sure I'm happy. If you please me this week then yes, next Friday will be your release date. In the meantime I think I want you in my bed tonight and between my legs. Between you dressed up like this and Ricky, I'm really horny tonight!"

Oh my god! Another week locked up like this? And what happens if I don't please her or do something wrong? Does my date change? I'm not sure I like this, I said to myself.

We both had salads and finished our drinks as the topic turned back to fashion, hairstyles, makeup, movies, and gossip. Sitting there in my wonderful dress and feeling so feminine was beyond description. I was living a dream and was thankful for Kate and her encouragement. Without her I never would have had the courage to dress up daily, practice my feminine movements that she taught me, or even have the nerve to leave the house in my heels and this complete transformation.

"Are you having fun on your first girls excursion, baby?"

"I was just thinking how thankful I was to you for helping me become so feminine and how you gave me the courage to go out dressed like this. I love how it feels being out in a dress like this and how people are reacting to me, just like I was another girl. I love it. Thank you, Kate. I really mean it, you are really a special person."

"Oh baby, you're welcome. I'm happy I could help and bring out the girl you've kept hidden all these years. To be honest, I really enjoyed tonight and we will be doing much more of this, I promise. I want you to be completely comfortable as Chloe so that we can do all the girly things girls do and I mean everything, baby."

The drinks had me giggling and smiling as I laughed and said, "I can't wait, honey."

"Good, because I'm quite certain that things will change for us. After tonight I'm even more sure of that."

The waiter came over with a desert menu, "Would you girls like to order some coffee or desert tonight?"

Kate spoke up, "Thank you Sweetheart but we need to watch our weight, so not tonight."

He flirted a little and said, "Oh you girls don't need to worry about that, you both look gorgeous and don't need to watch your weight at all."

I blushed as he was looking at me and said, "Thank you, but we'll pass tonight honey."

He left and Kate giggled, "Honey? You handled that perfectly, just like one of us, Chloe. I think you're going to well around men, sweetie."

That night Kate had me between her legs and she had multiple orgasms as I strained in my cage begging her to relieve my swollen balls. I was in need of relief but Kate was starting to enjoy the power of being the key holder and explained that when I am finally allowed to have sex again, the experience will be heightened and better than ever. She said that it was only a week of waiting and that right now her happiness was all I should focus on.

My instructions for the week was to keep myself hair free, live as Chloe and dress full time. I was to please Kate whenever she demanded and if I lived up to her expectations come Friday night I would be released and I would finally be able to have sex and relieve all of my frustrations.

The following week I worked at home like I do every day but this week I was dressed perfectly all week. I remained on edge all week and didn't want to displease Kate and jeopardize my release. So all week I took care of all the house chores, made dinner, kept myself looking perfect, and pleased Kate in bed each night. She would tease me and play with my cage and balls then watch me suffer as my cock tried to grow inside the chastity cage. She enjoyed the situation and laughed each time she saw my discomfort.

"Oh honey, I'm really enjoying this. Who would have imagined that such a small device could give us such pleasure and pain? I glad you agreed to this honey because in the end I believe you'll be happy with the results.

Well tomorrow night is your release date and you've been such a good girl all week that it looks like you've earned your freedom. I have a project for you tomorrow and unfortunately it will involve you dressing back in your male clothes and being my husband again for a few hours. You have an appointment at the bank tomorrow afternoon to sign some papers regarding our Mortgage and Insurance. You are to meet with Jean Conner at 3:30 pm. After you finish the paperwork I will meet you at Clovers for some drinks and afterward I'll take you home and release you from your cage.

I considered having you dress as Chloe for the appointment but realized that it would be too cruel but I still want you dressed. What I want you to do is wear your bra and panties along with your pantyhose under your man clothes. If you wear a suit jacket nobody should be able to see your padded bra pushing out from under your shirt. I want you as horny as possible all day and I think this will help enhance your night in bed. No arguments, so if you want your release tomorrow night you will do exactly as I've instructed. Do you understand exactly what you are to do?"

With my mouth wide open in shock, I nodded and said, "Yes."

The next day I begrudgingly showered and put on a pair of dress pants along with my Oxford dress shirt over my lingerie. The pantyhose under my pants made my legs tingle and feel sexy but the padded bra was clearly visible in my dress shirt which made me very self-conscious but I did as Kate suggested and wore one of my sports jackets If I held it a certain way the padded bra wasn't that visible. It would be a test of my will as I knew I had no choice but to as Kate instructed if I wanted to finally get my release tonight.

The paperwork signing and meeting went without a hitch and Kate was right, nobody noticed or cared that I was wearing a full set of women's lingerie under my clothes. I drove over to the bar and got there at 5pm and waited for Kate at the bar and ordered both of us martinis as I knew she would be arriving shortly. I felt very self-conscious as I sat there with my padded bra pushing out my shirt under my sports jacket but nobody seemed to notice and once I started drinking my martini my confidence grew and I relaxed a little more.

Kate was right on time and I watched as she crossed the bar as every guy watched her glide in her high heels exposing her long legs under her short skirt.

"You look sexy today, honey. Every guy at the bar was watching you just now. You sure know how to turn heads and that you make that outfit look very sexy."

"Thanks sweetie, and you look very sexy with your little padded bra," she said as she reached under my jacket and fondled my right bra pad.

"Stop that, honey. Someone will see that and get suspicious."

We sat at the bar and finished our second martini as she talked about her day and how different it was to see me a pair of pants for a change. We were both feeling the drinks and giggling as we sat there.

"I definitely like you better in skirts, Chloe. I can't wait to release you tonight and see what a week in chastity has done for your sex drive."

"Oh Kate, I'm so frustrated. Getting that cage unlocked is all I can think about."

During our third drink, Kate giggled and said she thought of a new game to play. I said I wasn't sure and said the drinks are making me a little tipsy and we might need to take a taxi home if we kept drinking. "Let's just go home now. No games, let's just go home so you can unlock me."

"Not so fast. I'm having fun here and I'm really enjoying the power I seem to have over you and the night isn't over. I want to play a game and you have to play. If you choose to not play or if you lose the game I will keep you locked up for another week. How does that sound?"

"That's not fair. You promised to let me out tonight."

"Relax. The game is simple and you can't possibly lose, unless you don't want to play. Besides, I promised to let you out if you were a good girl and obeyed my wishes all week. The week isn't over yet, honey. So you will play the game."

"Since I don't seem to have a choice, Yes. What's the game?"

"It's called the Yes game. For the rest of the evening both of us have to answer yes, to any yes or no question that anyone asks either of us. It's very simple. Just say yes for the rest of the evening and we're on our way home for your release and the best sex of your life!"

"That doesn't sound too difficult. OK, I'm in."

"Wonderful, this should be fun. Do you want another drink, honey?"

I didn't want one and almost said no but replied, Yes. It was going to be my fourth martini and I would definitely be over the limit and I knew that I now had to pace myself.

"So Chloe, do you want to stay dressed as my girlfriend full time?"

"Yes, that's an easy question."

"OK, let's try this. Chloe, do you dream about men when you're dressed up? Remember, a no answer and you lose the game and no release. Isn't this fun?"

"OK, Yes."

"I thought so. Do you dream of being their girlfriend?"

Just a game, I was going to go along because I wasn't going to jeopardize anything tonight

"Yes."

"I'm so glad you're being honest tonight, Chloe. Would you like me to set up a date for you and maybe even a double date for both of us? Wouldn't that be fun?"

I look at her with my pouty lips and said softly, "Yes, very funny."

"Oh Chloe, I just love this game. I'd love to go on a double date with you and make all your dreams come true. Would you like to see me with another man and be happy as well?"

"Come on, this isn't funny. You can't expect me to answer yes to that. Let's stop the game, Kate."

"The nights almost over baby, answer the question. Would you like to see me with another man and happy again?"

"Yes, OK? Yes!"

She giggled and finished her drink as she grabbed my leg. Come on, smile baby. We're just having fun," she said touching my cage and rubbing my balls. I smiled and said, "I can't wait until we get home."

As we sat there I noticed a large man walk up to the bar, very close to Kate and order a drink. Suddenly, my heart stopped as I recognized him as Ricky, her ex-boyfriend that we met a week ago. He hadn't noticed Kate yet and I hoped he would just take his drink and go away but my hopes were dashed when Kate turned to see who was leaning against her at the bar.

"Excuse me, you're pushing me off my chair," she said to him as he turned and faced her.

"Oh I'm so sorry. Kate? Is that you? Oh my god, I'm so sorry but I'm really happy to run into you again."

"You can lean on me anytime, Ricky. No worries. How have you been?"

I sat there holding my jacket closed as they chatted for several minutes laughing, having a good time, and ignoring me. Finally after several minutes he realized that I was with Kate before he arrived. "Are you with someone, Kate? I don't want to interrupt."

She looked at me and emphasized the answer, "Yes! Yes, I'm with my husband, but he doesn't mind if I spend time talking to you at all. Honey is it OK if I talk to my ex-boyfriend while you sit here alone?" She said winking to me and mouthing the answer, YES"

I knew if I objected I'd be locked up for another week and I knew nothing was going to happen with them so I just said, "Yes."

"That's very nice of you, buddy. Can I take her over to my table with my friends?"

I could tell she wanted to break out laughing and watched me as I looked into her eyes and said, "Yes."

"Honey, are you really going to let me spend the rest of the night with Ricky and his friends?

"Yes."

"I mean, you know we were lovers for years and you're still going to let me be alone with him tonight?"

"Yes," I said almost in tears.

"Ricky, he is so understanding and generous with me, it's incredible. Give me a minute, while I talk to him," she said as she turned her back to Ricky and leaned close and spoke quietly as she fondled my balls and played with my cage.

"I'm having so much fun with this baby. I hope you're loving this game as much as I am. Remember, we both have to answer Yes to any questions for the rest of the night. I can't imagine where this will lead but isn't this fun. You need to leave now baby and when I get back home tonight I want you in your prettiest nightgown all made up pretty and waiting for me in bed. You've been such a good girl this week that I am going to release you and give you the best relief you've ever had.

Since you agreed for your wife to spend time with her ex-boyfriend I'll be with Ricky and his friends. I'm not sure where this will end but having to answer yes to every question should be very interesting. Oh, and you had better hope I continue to answer yes because as part of the game if either of us says no, then you have another week locked up."

She stopped speaking softly and move back so Ricky could hear us again.

"Now you do you want me to have a good time with the boys, right baby?"

"Yes!"

"And you will be OK with whatever happens with them, right?"

"Yes"

"Last chance baby. I'm going to be with my ex-boyfriend and lover having drinks and you're OK with anything that goes, right? If he wants to kiss me, you're going to approve?"

"Yes!"

"If he wants to touch my breast or pussy, you won't' mind, right?"

I wanted to scream NO again but I couldn't stay locked up for another week and answered, Yes!"

She came in close one more time and softly said, "You know this makes you my cuckold now, don't you?"

I thought about that for a moment and had to agree, "Yes."

"There is no taking this back, you understand. Once you become my cuckold, you will always be my cuckold. Now I'm going to go off with Ricky and have fun. I want you to imagine all things that might happen with him tonight, especially with me having to say Yes all night. You do want me to say Yes to everything, right darling?"

I gulped, hung my head down and said, "Yes."

She turned so that Ricky could see both of us again and said, "Since Ricky will be taking care of your wife tonight I think you should run a tab for our table before you leave and I'll close it out for you when we leave. Oh, and one last thing. I think you should thank Ricky for taking care of your wife for you tonight. That seems like the right thing to do. Go ahead."

Ricky was clearly confused and my heart was breaking as I looked up at Ricky and said, "Please allow me to buy all your drinks tonight as a thank you for taking care of my wife for me. Please have fun and thank you."

"You're so sweet baby. Now be ready for me when I get home because I know I'll be very horny. I'll see you back home. Take a cab home and be ready."

I watched her look up at Ricky and smile and then walk back to his table and I felt my heart drop when she took his hand as he led her through the crowd. I sat at the bar and watched them for a while as they sat close and looked into each other's eyes and talked. I saw her hands disappear from the table and could only wonder what they were doing under table.

At one point she turned and looked over me and gave me a little wave and a knowing smile. I had no choice, I was trapped but I couldn't take the chance of being locked up for another week, besides I trust her and I know she was just teasing me so I decided to pay the bill and go home.

The waitress came over and said, "I notice you're looking to leave but your wife over there said to just leave the credit card and the tab open because she knows you want to take care of their bill tonight. So if you can leave me your card I'll take care of her guest for the rest of the night, is that OK?"

Kate was enjoying how the evening was turning out and how lucky she was to be able to spend the rest of the evening with Ricky. She couldn't believe how good the Yes game played out and made a mental note to play it again.

I watched as he gave the waitress his credit card and then left the bar holding his jacket closed. The poor dear must be so frustrated right now, I can't imagine what's going through his head and the expression on his face when Ricky asked him if it was OK to take his wife, was priceless. This could not have worked out better.

"Kate, what was that all about with your husband? He sure was quick to let you go off with another guy, is that normal in your relationship?"

I giggled and said, "Yes, it is. We're playing a little game tonight and your timing was just perfect but now that I'm here tell me how things are going for you."

"Now that I'm with you, things are just perfect and I'm happy I could help. I'm sorry but I have to ask because I'd love to spend more time with you again. Do you two have an open marriage?"