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Tony's Companion All week I tried to come up with ways of getting out of this date with Tony. I cried, begged, and pleaded with Grace to come up with another date for Tony, and to convince him to let me out of being his date to the Charity Ball. She would have no part of it and engaged my mother to take me shopping for an evening gown suitable for the event, and something to compliment Tony who will be in a tuxedo. "Amy, you have to stop begging. Tony is excited about Friday and has mentioned it several times so there is no way out. He has been a gentleman about all of this, and even asked for my permission to take you out, while knowing you really are my husband. Tony wanted to ensure that this was going to be OK with everyone. I explained that now that I have seen your true inner girl, that you are more of a girlfriend to me and that I want nothing more than the two of you happy." "What? Why did you say I'm more of a girlfriend, not your husband?" I asked. "Well, to be honest Amy ever since I've seen you in dresses and make-up, I have not been able to think of you as my husband. I do love you, and want you in my life, but right now I think of you more as a woman or my girlfriend, and I'm not sure I can ever think of you as my husband again. I'm sure you understand, because you know how feminine you have become, you can't think of yourself as a man, or in that case my husband, can you?" She asked gently. I could tell she wasn't being mean or trying to hurt my feelings, but she made it clear that our relationship has definitely changed. "I guess I can understand what you're saying, and I don't blame you, but I can't lose you, I love you too much," I said. "Oh sweetheart, I love you even more now, and I have no intention of letting you go. Let's just see where this goes, but in the meantime, I suggest you enjoy the ride, and live out your dreams of living as a woman. Not many people in your position would ever have this opportunity, or an understanding wife to help, so please just try to enjoy the things you cannot control. I promise that you are going to have fun and you will be safe because your Tony, your Mother, and I will be making sure everything goes well. Now, tomorrow afternoon your mom is picking you up at 2pm and taking you to Nordstrom's, where I'll meet up with you after my meetings. She is going to help you shop for an outfit for Friday. Since I'll also be at the event, I'll need a new outfit as well, so we can just have fun shopping together, as girlfriends," Grace added. I was horrified. "You really told my mother that I'm going to be going on a date? How could you?" "Amy relax, your mom was so happy for you and wants to be part of your new life as a woman. She was so excited and said she always wanted a daughter to go shopping with, and now she finally has the chance. You're really making her happy and I'll expect you to go along with this, be her daughter, and let her enjoy the experience. She knows all about the affair, and exactly what you will need for Friday." After cleaning up the house the next morning, I took a warm scented bath and tried to relax before getting ready for an afternoon of shopping with Grace and mom. I picked out a flowery sun dress, that would be easy to change in and out of as I would be trying on outfits all afternoon. I wore my black heels that I knew would be helpful for the outfits they would be selecting for me to try on. After putting on my makeup and fixing my hair, I put on my jewelry and perfume, and grabbed my purse just in time, as mom pulled into the driveway. I was walking up to the front door and let mom into the house when she looked me over and smiled. "You look lovely today Amy, and I love what you've done with your hair, it really fits your facial features well. Are you ready to go?" We sopped in several stores but finally found some nice outfits at Nordstrom's, her favorite store. Mother picked out several outfits and had me carry them into the fitting room as she followed. I was a little taken back when she explained she was going to help me dress. Mom giggled. "Don't be silly Amy, us girls do this all the time and besides, I'm your mother, now step out of that dress and let's try this on," as she held up the first of many silky black cocktail dress. I took off my dress and stood in front of my mom in my push up bra, sheer pantyhose, and heels. She looked me up and down and smiled. "You have such a nice figure, I'm sure we'll find the perfect dress for you, honey." There are no words to explain how I felt standing there in my lingerie and heels in front of my mother as I watched her examine the figure of her new daughter, me. For years I wished for this when I was young but now, I didn't know how to respond and covered my breast with my hands. I saw that amused mother, as she just smiled. She took the dress off the hanger and held it open as I stepped into it and slid it up into place. Mom zipped me up, and I put my heels back on and turned to the mirror. "Mom, this is beautiful I love it," I said as I saw the pretty girl in the mirror. The lace top covered my breast and the short dress came to mid-thigh. Sexy and elegant, was how mom described it as I enjoyed the image in the mirror. "Ok, that's enough we have several more to try on, let's try this one," she said as she unzipped the dress and hung it up as I slipped into the next dress just as Grace showed up. They had me try on several different styles until they decided on the first one that mom picked out, a short silky black cocktail dress that worked will with my body and not too revealing up top. It really fit perfectly, and the silky material felt heavenly as it moved across my body and nylons. Grace brought back several dresses to try on for herself, and the one the both liked was also a black cocktail dress but hers was very low cut, which put her large breast clearly on display. I didn't like her wearing something that sexy and suggested other dresses that had weren't as revealing, but my own mother gave her opinion and encouraged Grace to go with the low cut dress. "Oh Grace, that looks spectacular on you and shows off your wonderful figure, you just have to buy that dress. You will have every head turning, I'm sure," Mom said. "It's a little over the top, but I will be the hostess with all the Professional Athletes, it can only help my position and popularity, so yes I agree. Besides, I have to look as good as Amy will look in her dress." It made me uneasy to imagine my wife dressed in a sexy dress, with her breast on display with all those jocks for the evening. I wasn't sure if I could handle watching her with other men, but realized I had lost control of the situation and just sighed to myself. The rest of the day was fun as we shopped for some accessories and picked up some makeup. Shopping for all these feminine items with my wife and mother was fun. As Friday approached, I continued to try to get out of my date with Tony and kept asking Grace to help. She listened to my pleas, but said we really had no choice and finally on Thursday night she told me that Tony had come into her office that morning. "Honey, I spoke with Tony today when he came into my office. I was going to see if he would reconsider, but before I could discuss it, he explained how excited he was about tomorrow night, and promised that he will keep everything a secret. He said, "I've given this a lot of thought this week and I promise nobody will find out about your husband, but that depends on his performance. I'll expect Amy to be attentive, as any girl would be with her date. My image is important, and I need you to make sure she understands that she needs to pass as Amy, not only for herself but for you and me, as it will ruin both of us if she lets us down. What I'm saying here is she needs to remember that she's my date, and girlfriend, which means that she will need to react correctly, if I give her a hug or a kiss and not pull back or make a scene. It would be helpful if she would reach out and touch my arm or hold my hand. You know exactly what girlfriends do on dates, and I want to ensure she is not going to embarrass us tomorrow night. I think it will be fine if she has a good attitude about this, so please prepare her for tomorrow. "What about your marriage? Clearly, you can't consider Amy as your husband any longer. Are you going to divorce him?" Amy looked shocked as I repeated what Tony had said and asked me, "What did you tell him?" "Well, once he made it clear that you were still going on the date and how important it was for you to behave, I told him not to worry and I'll prepare you for tomorrow. I also told him that I had no intention of divorcing you, however, I didn't believe that I could think of you my husband anymore. I told him that I loved you, and that you would stay with me as my girlfriend until we figured things out. "Now more important, let's talk about tomorrow night. As you know I'll be the main host at the charity event, which means I won't have much time to be with you or keep an eye on you. For the most part, you will be on your own and Tony's date. You understand that as his date you will have to act a certain way. I know you don't have the experience so let me help you understand what's expected. "HolMYou will be his eye candy, his girl, and you will need to act as any girlfriend would with their guy. He will kiss you and hug you in front of people, and it's important you respond like his girlfriend and welcome his attention and act happy to be with him. When you stand next to him, be sure to hold his arm or his hand, and show everyone that he is yours because, everyone will notice. "You will always have to mentally be in your girl mode, which you should be comfortable with by now. I'm sure you'll be dancing with him, so just always follow his lead and look thankful and happy. You need to pull this off for both of us tomorrow night. The good news is that the event will only last about three hours, so I'm sure you can pull it off without any problems. Make us proud, Amy." "Oh my god, I'll have to kiss him and hold his hand?" "Well, of course. You are his date and his girlfriend, and that's what girls do. Don't act surprised we both know what will happen. What's important is that you stay in character, and don't show your male side at any time. He expects you to be a woman, all night, and if you don't accept his advances it will be trouble for both of us," Grace said. "Grace, what if he wants something else?" "Well, then you'll understand what being a girl is all about. Come on, you have played with all those toys and you know exactly what to expect. I suggest if things get a little hot that you either jerk him off, or give him a blow job, no big deal. Remember, It's only sex and we're both adults so it's really no big deal." I looked at her in shock and said, "No big deal? A blow job is no big deal, are you serious?" She looked at me with a smile. "Come on honey, we aren't teenagers anymore. Sex is just sex, nothing more. It's not like you love the other person, it's just sex nothing more. It doesn't mean you don't love me anymore it's just a physical release between two people so don't make it such a big deal." I felt a wave of panic come over me as I wondered if that's how she felt about other guys, and if she was having sex. A wave of jealousy came over me and I had to ask, "Does that mean you are having sex with other guys?" She laughed. "So that's what concerns you? Me having sex with other guys not the thought of putting Tony's cock in your mouth, and giving him a blow job? You're more concerned about me being with a man, then you are about sucking another guy's cock? That's priceless, Amy." That brought the main problem back in focus and I started thinking about having to do that and all types of new feelings were coming over me all at once. I sat there silent as she continued. "For your for your information, I have not had sex with other guys, but if I did it would not mean that I didn't love you because I do, more then you know. On the other hand, I do have sexual needs, and you must know I haven't been sexually satisfied for quite some time. To be honest, I do think about it often, however, I've never acted on all the offers I'm constantly bombarded with, but ever since I saw how happy you living as Amy, I realize that sex between us will probably never satisfy me again. I am not into sex with another woman, so being with Amy is not appealing. For the last year I have considered having sex, just to relieve my own needs and to be honest. after I met Amy, I've been thinking about it much more often. But if I did have sex with some guy, I would just consider it just sex, not a relationship or anything like that, which is why I consider a blow job just sex, nothing else. No emotional involvement but just a natural human event. Society places all these thoughts and meanings to sex, but if you think about it carefully, it is only twenty minutes of getting off with another person. The reason I'm telling you this is because guys have expectations after they treat you to a fun night or give you a nice gift, which is the position you will be in, so you need to be prepared. When you're with Tony and things get to that point, you just need to let yourself go and do what all girls do for their boyfriend. Just remember, it's just sex and all part of being a girl. I know you've fantasized about it, so just like everything you've done recently, it's just another step of becoming a complete woman. It is what you've wanted all along, isn't it Amy?" "Not for real, only in my fantasies," I explained. "Well, just like everything else in your fantasies, this might become a reality as well. You are now living as a woman, and if it happens just accept it and try to be happy that you are getting to live out your inner desires and appreciate the chance to live as Amy. Most girls like you would kill to be in your position and be able to live out their inner desires and live as a woman full time, have an accepting wife, and a date with an alpha male that finds you beautiful and desirable. You do realize that you are a lucky girl, Amy Rose, don't you? You know, as I sit here, I realize how selfish you sound. From now on I want you to be more appreciative of your position, and what your Mother and I have given you. I want to see more enthusiasm and hear you say Thank You more often to me and your mother. It's time you started to show us how thankful you are for all we've done for you! Do you understand?" I sat there stunned. My wife just told me that Amy won't be having sex with her anymore and that she is thinking about having sex with other men. That I must accept having sex with Tony if he wants it. That I must be thankful to her and my mother about being allowed to live as Amy full time. My world has turned upside down, and I felt as if I was falling into a dark hole with no way out. I sat there quietly, feeling worried about what I just heard and didn't realize that she was waiting for an answer. "Well?" "Grace, I understand, and I am thankful for what you and mother have done for me. I know I'm very lucky that you haven't kicked me out after you found me dressed up in a dress and heels, and I'm thankful you've accepted me for who I am, and I really do appreciate everything you have done for me. I'm sorry I haven't been able to satisfy you in bed, but the thought of you with other men is something I never thought about. When I think about you with other men, it makes me jealous and I know I have no right to feel that way anymore." "That's more like it, Amy. I expect you to remember that and show us your appreciation for not kicking you out on the street, and thankful for letting Amy live here and free to become a complete woman. We are still married, and I do love you, and I want you to be happy. If you love me, I would think you want me to be happy as well, whatever it is that makes me happy. Whether it's just sex or something else, I would expect you to encourage me to live my desires, just as I've stood by your side and helped you live your desires. I want to stay married to you baby, but if we can't support each other, then I will reconsider our current arrangements. "You should spend some time and think things over and see if you can live this way, and if not, I will understand but there is not going to be any negotiations. You will live here as Amy from now on and appreciate your place in our relationship. If you can't, then I expect you to be honest and tell me, and then you can move out and live your life without me, but that is not what I want." "You expect me to continue to live as a woman? For how long?" I asked. "Well, for now I expect you to live as Amy, full time. You became Amy in my eyes the minute I saw you all dressed up as a passable woman. I'll help you become all the woman you can be, but for the foreseeable future, you will live here as Amy, my girlfriend and legal husband. "You can continue to work from home or quit your job. Either way, I'll expect you to be the lady of the house, because we both know that I'm the real breadwinner in this family. I guess keeping your job will give you some feeling of your old life, but if you consider quitting your job you will have lots of time to focus on yourself. You can spend time at the gym and get a better female shape, getting a weekly manicure and salon treatment, shopping and being all the woman, you can become. But, as the lady of the house, I'll expect you to clean the house and keep it spotless, do the laundry, food shopping, cooking, and any requested errands. "In fact, I wish you would just quit and live as Amy, because it would make things much easier and help you focus on your transformation. I mean, you are passable as a woman right now, but just think how much better you could become with more time to practice and focus on yourself, as I take care of everything else, you can become the perfect little housewife." Since she explained my situation like she did, I realized that just living as Amy wasn't a bad thing, and if I was forced to admit the truth, it was what I wanted. She was also right about the job, but if I did quit, I was in effect giving up my past life and any means to make a living, and fully dependent on Grace. The more I thought about living as Amy and being a housewife, having free time to develop Amy and not having to work, sounded pretty good. "You might be right, maybe I should give up my job and just stay home and become your housewife, at least for the near future," I said thinking about the possibilities. "That's perfect, I call and take care of everything this week. This will be fantastic, and just last week your mother even offered to help teach you how to keep up the house and do laundry, she'll be happy to hear about your decision. For this to work we will need to get you a complete wardrobe and everything else you will need. But we can worry about that next week, we need to focus on your debut with Tony tomorrow. I'll be home early tomorrow, because I must get ready as well. My limo is picking me up early because I'm the co-host, and I have to make sure things are in order. That means you'll be getting dressed all by yourself tomorrow, and with your hair and makeup already done you should be fine. I've given the girls at the salon detailed instructions again, so all you have to do is show up on time. I'm sure you'll be nervous, but I have some good news. Tony said he got out of his afternoon engagement and will be in the Limo to pick you up, which means you won't have to ride over to the event all alone. You just need to be ready by 7pm." That night I didn't sleep well, as I went over our conversation in my head many times. The realization hit me that I had basically given up my position as husband in the relationship to live as Amy, gave up my job and became a housewife to Grace. I would become dependent on her and truly understand what it means to live as a woman. Eventually I fell asleep and woke up late morning, cleaned the house, and tried not to think about the evening ahead. Wearing a loose summer dress and wedge heels I put on a little lipstick and blush, brushed my hair and went to the Salon for my afternoon appointment. The girls greeted me enthusiastically and told me they were so excited for me and my first date. They wanted me to tell them all about him as they brought me to the back. "Grace said he's tall, dark, and handsome, you must be excited. Don't worry; we're going turn you into a very sexy princess tonight." I told them he's a friend of Grace that came over for dinner, and I was extremely nervous. They tried to make me relax, told me jokes, and not to give him too much on the first date. They were having fun as they worked on me and I had to admit, I enjoyed being treated like any other girl, getting ready for her date. My extensions were adjusted, and my hair was washed and brushed out into a wonderful style, pinned and sprayed into place. They worked on my nails and gave me a new coat of deep shiny red color on my toenails, and my extended fingernails. I had my long eye lash extensions filled in, and given a coat of waterproof, long lasting mascara, after my evening wear makeup was completed. They were very busy completing Grace's list and they finished with a leg waxing before they said they were done. They finally allowed me to look at their work in the mirror, and I stood there with my mouth open. Looking back was a beautiful girl dressed up for a special occasion. The girl was clearly going to be eye candy for her date, and any other guy that saw her tonight. There was no way I was going unnoticed, especially being Tony's date. I felt butterflies in my stomach, as the girls were so excited on how I turned out. "Your date is not going to be able to keep his hands off you tonight, Amy. We're so excited for you, please come back and tell us all about your date!" the girls said as we all smiled and giggled. I got home around 5 o'clock and Grace was gone but left a note for me on the table. The note read, 'Amy, I had to get to the event, so I'll see you later tonight. I left a few things I want you to wear with your outfit tonight in your room. Please be sure to wear them, because I'll be checking later tonight. Tony called and told me how excited he was for his date, I hope you're ready for your first date, it will be fun watching you all night. See you later, Love Grace.' When I got to the bedroom, I saw what Grace left out of me to wear with my outfit. Some new hoop earrings, some rings, a necklace, several bracelets, and a garter belt with a new pair of seamed stockings. There was another note pinned to the garter belt. This note said, 'I know you always wear pantyhose but tonight I want you wearing stockings. I want you to feel the tugging of the garters all night long, the fear of your nylon's tops being exposed to everyone, and how it feels to be vulnerable. It will make you feel much more feminine and remember, if Tony gets a peak it will certainly excite him, so be careful honey. If you feel nervous and overwhelmed, I left a pill on the nightstand that you should take to calm you down. It's a low dose sedative that will take the edge off and help you relax and survive the evening. Put it in your purse and take it if you feel like things are getting out of control, this will help you. See you soon.' When the Tony rang the bell, I felt my heart race and knew it was my moment of truth, and things would never be the same. I wanted to run out the back door and hide, but I knew there was no choice but to go through with this and get it over with. My legs were shaking as he greeted with a quick kiss hello when I opened the door, and then let me to the limo after I locked up the house. The limo driver held the door for Tony and I as we entered the stretch limo, which is when I had my first experience wearing stockings. As I entered the limo, my dress slid up giving both Tony and limo driver a clear view of the tops of my stockings, and the garters holding them up. I quickly slid in and pulled the dress down, over the stockings which unfortunately gave the impression that I was flirting. I now realized what Grace meant when she told me to be careful wearing stockings because unlike pantyhose, they will be visible whenever you aren't careful. I realized I would need to pay more attention to that, as the night continued. I saw both men smile and watched Tony slide next to me in the back seat. Fortunately, he didn't say anything about the incident. I had never been in a stretch limo before and was impressed with the experience. Tony sat next to me and offered a glass of champagne, as we started on our thirty minute journey to the hotel. "You look amazing Amy, and I love what you've done to your hair, you look very elegant." "Thank you, I'm glad you like it," I said trying to hold the champagne flute, but my nerves made my hands shake and almost spill the drink. I took a few sips and tried to relax. "You look a little nervous Amy, are you OK? I know this is your first time out and I will help make you comfortable tonight. Grace told me about the sedative in your purse and maybe you should take it now before we get there. It might relax you a little when we get there because there will be a lot of people and activity, I want you to be relaxed. Hand me your purse," he said forcefully. I handed him my purse and he found the pill and held it out in front of me. I saw my long red nails carefully take it from his massive hand and put it to my lips. "Good girl, go ahead and swallow and soon you will feel much better." _______________________________________________ I felt small as I sat beside Tony, which made me even more insecure and submissive. I was quiet as I sat there still frightened about what was to come and tried to drink out of glass without spilling anything. After a few minutes I felt a warmth wash over my entire body and it felt like a huge weight was taken off my shoulders, I relaxed and allowed myself to sit back and lean against Tony. Whatever was in that pill worked it's magic, and I was now completely relaxed. Tony saw my compliance and put his arm around my shoulder and pulled me close, as I just enjoyed all these new feelings. Between the drinks and the pill, I was not only relaxed, but I became ultra-aware as Tony held me. Everything was now moving slower and more peaceful, as the sensations of the garters pulling on my nylons created a wonderful sensation. I noticed my long eyelashes as I blinked, the creamy feel of my lip gloss, and the smell of my floral perfume. I was awash in a wonderful world of feminine feelings and felt safe with Tony's strong arm as he held me close. I found myself enjoying the attention and that safe feeling as we sat there and smiled at each other. "I can tell that the little pill you took has started working, and it should help you get through the evening. Grace explained it should last about 6 hours, which is how long this night should last. I'll keep an eye on you and make sure that you're OK, but you need to remember what Grace told you about tonight. It's important that everyone believes you're a woman and my girlfriend," Tony said softly into my ear as I just sat there listening and smiling. "Yes, I understand and I'm sure you will be proud of me tonight," I said as I wondered why I said that out loud. When we arrived, the driver opened the door, Tony helped me exit the limo, which was not easy due to the two glasses of champagne and the sedative. I giggled as I pulled the bottom of my dress down and took Tony's hand, as he led me into the venue. I asked Tony to slow down, as I tried to keep up with him in my high heels. He was gentle and understanding and led me into the ballroom where we were seated at the front table near the podium, where Grace was standing with someone having a discussion, most likely about the event. She saw me, smiled and waved, and a few minutes later came over to say hello. "Amy, you look amazing in that dress and you two make a cute couple," She said smiling. That would have bothered me except for the drinks and the pill, but now all I could do was just smile back at her. Grace continued, "You look very relaxed for a girl on her first date. You took the pill already, didn't you?" I nodded and smiled back at her. "I suggest you don't have too much to drink tonight or you will lose all your inhibitions, and possibly become an embarrassment. Be careful and remember what I told you about how to act tonight, people will be watching." Grace gave the welcome speech and joined us at the table with Jared, the CEO and President of the company. I had never seen Grace in a work environment and was impressed on how professional she acted, and how attentive she was to her boss. Tony kept me busy with conversation and I enjoyed how he treated me as an authentic female, and his girlfriend. Remembering what Grace had told me how to act, I paid close attention to him, touched his arm and held his hand or arm all evening. I was hanging on to him and from anyone looking at us they would only see a couple enjoying each other's company. He even commented later in the evening as we sat there together. "Amy I wasn't sure how things would go tonight but you've really gone out of the way to make me feel special, and I am impressed how attentive you've been. Every other girl I've taken out has always been self-absorbed, but you make me feel special. That first night I saw you I felt an attraction right away, and I'm thankful that things have worked out as they have," he said right before he leaned in and gave me a gentle long kiss, which I found myself allowing and returning. When we broke the kiss, we smiled at each other and sat back in my chair only to see Grace looking at me with a shocked expression and mouthing the word. WOW! That sobered me up as I had the feeling of being caught again but this time I it was kissing another man. I can only imagine what she was thinking and feeling. I didn't have time to think about it because Tony took my hand, and led me out to the dance floor, where we spent the next twenty minutes dancing together. He held me tightly as I had my hands around his neck and my head on his shoulder, as he led me around the dance floor. I felt his strong arms and massive chest hold me safe and tightly, as we danced. I felt his big strong hand wander down my back and rub my bra strap and then my garter belt. It was at that moment that I felt his large cock start to press against my stomach, as we continued to dance. I was not sure what to do and just kept dancing and allowed him to rub my back, and eventuality my ass in the dark recesses of the dance floor. Without the sedative I'm sure I would have reacted much differently, but I was so relaxed that I just went along and tried to enjoy the evening. We kissed a few more times during the dance and when we broke the last kiss, I saw Grace dancing closely with Reggie, a former NFL running back. She saw us kiss again and gave me a wink, as we both danced with these large muscular men. I should have been jealous, but Tony's hand was now rubbing my bun so hard it was hurting. I looked up to tell him to go easier, but when I started to speak, he gave me a deep long kiss as we stood in the middle of the dance floor. We were still kissing when the music stopped and when Grace passed by, she said, "The music stopped, you two should just get a room." We went back to the table and I could see Tony's hard-on pushing out of his pants and smiled to myself, thinking that I had done that to him and for some reason, it felt kind of good. Grace was now talking with a few of the players and having a good time, laughing and teasing the men. It was getting near the end of the night and I was getting sleepy from the sedative and drinks and ready to leave. We ended up sitting and talking for another thirty minutes before then Tony said it was time to meet our limo outside. Grace saw us getting ready to leave and just waved, as she was now alone with Reggie in a deep conversation. I wanted to know what they were talking about and if she was going to come home alone or break our vows and be with Reggie. I didn't have too much time to think about it as Tony grabbed my hand and led me out to the car. The drive home was much different than the ride to the event. Tony closed the partition to the driver and wanted privacy. Tony now felt he could just kiss me at will, and freely made out with me on the drive home. He took my hand and placed it on his enlarged cock as we kissed. "Amy, you are a sexy and exciting girl, and I want to be with you again," He took my hand and moved it over his cock and said, "Look what you've done to me, Amy. Other girls never get me this hard, but you have really proved yourself to me tonight. Unzip my pants and hold it, please." How did I get here? A few weeks ago, I was only dressing in woman's clothes but now, I'm not only dressing but living the life of the girl I've kept hidden. Not only that, but I'm with a very handsome man who thinks I'm sexy and wants me to rub his cock. My desire to just dress and act like a woman has suddenly changed, and now I have this desire to make this man happy and if that meant holding his cock, why not? After all, tonight I was Amy Rose his girlfriend. I watched my long red nails fumbling with his zipper as he moved to allow me access. I unbuttoned his pants and put my hand under his underwear. At that moment I wrapped my hand around his pulsating, warm, nine inch cock. It felt strong and alive as I held it in my hand. Tony moaned, as I moved my hand on his shaft and that gave me the encouragement to continue. The power I felt from holding his large cock was exciting, and I watched him sit back in the seat with his head leaning back. As I stroked his shaft, he closed his eyes and smiled. He was extremely excited and getting even bigger as I continued to stroke him. At this point he moved his hand up my dress. and was now playing with the top of my stockings and rubbing my exposed thigh. We were both turned on at this point as he said, "Amy, I love when girls wear stockings like this because it is so sexy, and you have such sexy legs, don't stop stroking me baby. Just like that, yes keep it up just like that. You really know how to get me going baby, we have to do this again." I felt the car stop and realized that we were now in front of our house, but Tony wasn't done and said, "Don't worry about the car, he will wait for us so just keep that up and kiss me, Amy." I moved forward and continued to stroke him, as we kissed. He was now rubbing my ass under my dress and freely exploring my body as I felt him get very hard and then he broke our kiss. He rolled his eyes back and stiffened up as he shot his load all over the car. His hot stream of cum hit the top of the car, my face, the seat and splattered everywhere. I kept stroking him until he was completely relaxed and sat there smiling and satisfied. I grabbed some paper towels and tried to clean everything up including Tony and my face. I couldn't believe I just gave a guy a hand job and removed his cum from my own face. What have I become? After a few minutes Tony pulled his pants back up and I straightened my dress before he opened the door. The limo drive was there waiting and smiling. I was embarrassed as I realized that he knew exactly what we were doing back there, and just walked to the front door as Tony followed. He thanked me for a wonderful evening, kissed me good night, and told me he would call me this week. I went in the house and collapsed on the couch and thought about the entire evening. I woke up on the couch at around 3 o'clock as I heard Grace coming in the door. "You're still up?" "Yes, I was waiting for you to come home. I've been home for hours, what took you so long?" I asked. "Well, Reggie and I stayed for a few drinks and closed the bar down. He wanted me to go up to his room like he always does, but I told him no and that I was married and came home. You, on the other hand, were all over Tony tonight. You really played the part of his girlfriend well, but I didn't expect you to be kissing him all evening, I heard several girls asking who you were and how lucky you were. You passed Amy, everyone believes you are Tony's girl. You really are amazing and I'm so happy for you, but I need some sleep. We can talk in the morning. Oh, I invited your mom over for lunch so be sure you're up and dressed by eleven. She wants to hear all about your date tonight, so I told her to come over and we can chat, like all girls do after their dates. I went to Amy's bedroom, washed off my makeup, put on a nightgown and fell asleep in record time. Between the sedative and the late night, I slept soundly and woke up to the sunlight shining through the window. The clock said nine o'clock as I laid there slowly waking up. Remembering that mother was coming over for lunch I got up, showered and put on my make-up. I knew that Grace would expect me to have lunch ready, so I hurried up and got dressed and put on a pot of coffee, as I tried to figure out what to serve for our luncheon and decided on a Mushroom Asparagus Quiche, some fruit, juice, and coffee. As Grace slept, I set the table on the patio for three place settings, prepared the food, and had a cup of coffee ready for Grace when she finally came down around eleven o'clock. "Thank you, sweetie," she said as I handed her the coffee cup. "Looks like you have everything read for our brunch, very nice. You really do make a good housewife, Amy," she said with a giggle. I didn't pay attention and continued to start to make the Quiche, knowing that our mother would arrive shortly. "Did you sleep well, Grace?" "Oh yes, I was exhausted from having to work that event all night. I didn't get to play and relax like you did all night. It sure looked like you had a good time with Tony." "It was all right, from what I remember. That pill you gave me really helped my nerves and allowed me to get through the night. Without it, I'm not sure I could have pulled it off," I said. "Well you did because I heard many people make comments about the pretty girl that was with Tony, and how close they were. They were all wondering where he had been hiding you because with all your loving touches and kisses, everyone believed you two have been a couple for quite some time. I bet Tony was happy with the outcome and your performance." Mother arrived and we all sat on the patio as the food was cooking, and we enjoyed several mimosas, that I had prepared. It was a pleasant day, with a nice breeze and blue sky as we just sat there, enjoying each other's company. I served the food and refilled the drinks as Mom and Grace just relaxed outside. We talked about going shopping next week and picking up a few things together as girlfriends do. At this point, I accepted things and started liking our outings together. After we finished eating, I cleared the table, put things in the dishwasher as Mom and Grace chatted alone. I tried to hurry up so I could hear what Grace was telling her in private. With a pitcher full of lemonade and clean glasses, I came back outside and served more drinks to the girls and sat down. Mom smiled and said, "Grace is right, you really are becoming a perfect housewife. Are you enjoying your new role as the lady of the house, Amy dear?" "Yes mother, I do like taking care of Grace and she has been so kind to me that I want to make her happy." "Well enough small talk, I want to hear all about last night, after all that's the reason I came over. Your first date and the first time Grace got to see you out with a man. Did you think he was as handsome as Grace said he was?" Embarrassed and humiliated I just sat there as Grace and Mother waited for an answer. "Amy, answer your mother. If you're going to be my girlfriend you will need to get used to girl talk, it's what we do, and we expect you to be one of the girls." "Yes mother, he is very handsome, tall and well-built." "Well, you're a lucky girl. Grace showed me some photos of you from last night and I must say the dress we picked out looked lovely on you," mom said. "What pictures? I don't remember taking any photos." Grace turned her phone and displayed several pictures of me dancing with Tony and one of us kissing. "Was that your first kiss as a woman, dear?" mother asked. I knew I had to answer and said, "Yes, I never kissed a guy before." "Did you enjoy kissing him," she asked as she casually drank her lemonade. "I was sedated, and I don't remember much but from what I recall it wasn't horrible." Grace turned to mom and said, "I had Amy wear nylon stockings with her outfit, no pantyhose last night. I wanted her to feel vulnerable and know what we girls go through," She turned to me and asked, "Did Tony like your stockings, dear?" "He saw them by accident when I got out of the limo, and he said he thought they were sexy." "Did you like wearing them?" mom asked. "I did, yes. The tugging on the nylons reminded me why I love dressing as much as I do, and it felt utterly feminine. I love wearing pantyhose, but I can see where stockings have an advantage." "Did Tony get to feel your stocking tops, Amy?" Grace asked. I blushed and tried not to answer but they waited for an answer. I told them all about the ride home and how he felt me under the dress and played with the stocking tops. I also had to give them details about our kisses, how many, how long, if we French kissed, and if I did anything else. Finally, I told them how he asked me to touch him down there and asked me to take it out of his pants. "So, you touched his cock! Did you give him a blow job as well?" mom asked as I sat there stunned by her words. "No way. I just kind of stroked him there the limo," I said. Grace smiled and said, "So no blow job on the first date, but you did give him a hand job. Did he come for you?" "Yes, and it was gusher. He came all over the place and I had to clean everything up off the seats and the car ceiling," I said realizing I just confessed to touching a man's cock and bring him to climax while we kissed in the back seat of a limo. "Oh, you little slut, and you did all that on the first date. I'll bet Tony will be coming around for more of that Amy," mom said giggling. "It was the sedative, I'm sure. I never would have done that if I was sober." Mother looked at Grace and said, "How does that make you feel, Grace. I mean, your husband or should I say girlfriend having sex and you all alone. That doesn't seem fair at all. Do you have someone to date? Because it doesn't seem fair that Amy gets to have fun while you just sit home alone. It's not healthy for pretty girl like you, to be alone, honey." Grace looked at me and then lowered her head. I could tell her mood had instantly changed and I saw a tear in her eye and then she just stood up and said, 'Excuse me, I'll be back in a few minutes." "Mother why did you say that, it clearly upset her," I asked feeling helpless. "How could you encourage her to find another man to be with? What were you thinking?" "Amy, even though you make a very passable and pretty female, you don't have a clue about our emotions. That would change if you decided to start taking some estrogen but, in the meantime, you need to consider the feelings of others and stop being so narcissistic. Yes, Grace and I have accepted your desire to dress and live as a woman but where does that leave Grace? Have you considered her feelings? Her husband is now living with her as a beautiful woman and has already been out and sexual with a man. If you can put yourself in her place for a minute, how do you think it makes her feel? You have so much to learn, and both Grace and I will help you, but you really must start thinking about others more than yourself. Don't misunderstand me, I've accepted your desire to become Amy, and it seems as if Grace is giving you the opportunity to live out your dreams, however, you must realize that by doing so you give up your role as a husband and accept your new role as her girlfriend. And just so you understand, real girlfriends encourage and help each other, and want the best for their friends. You do want to the best for Grace, don't you sweetie?" "Of course, I do, but..." She cut me off, "Stop. You said want the best for her and that's a good start. Now, do you enjoy sitting here in that cute dress, your hair looking so feminine, nice make-up, as you move and act like a perfect woman? Do you want that to continue or are you prepared to give it all up forever, and return to being a man? Think about that, because your answer will certainly create changes in all of our relationships. Do you want to continue to live as Amy? Simple question," she asked. "Yes," I answered. "Then you need to tell Grace and let her know that you will live as her girlfriend and will not stop her from living a full life. When she comes back you will tell her you want what's best for her, and if that means seeing other men, then you understand, and that it's completely natural. You'll tell her you're giving up your status as a husband and will be there to support her as her best friend, her girlfriend." Mother encouraged me to find the strength to let her be free, find happiness, and understand that my decision to live as Amy should not stop Grace from being happy because, all woman need the strength and love of a man. Mother explained that it's a choice I've already made, and once I give her permission to be happy, my own concerns and worries will be over. She explained that it was time to show some love and understanding, and how thankful you are to have such a loving partner that will support your own desires. "Whatever happens, I'll be there for you sweetheart and I feel closer to you, more than I have ever felt before. Having you as my daughter is a dream come true and I want to help you in any way I can, so please don't shut me out. Allow me to teach you the things every mother teaches their daughter," she said. Grace came back and I excused myself and said I was going to refill the glasses. I gave her a few minutes to settle back and chat with mother before I came back with another pitcher of lemonade and poured the drinks. "Thank you, Amy. This is so refreshing," Grace said trying to show that she was relaxed and over her emotional outbreak. I leaned forward and touched her knee and said, "Grace, mother and I have been talking and she made me understand some things. Since I've been living as Amy, I have only been thinking about myself and was inconsiderate to your feelings. I want to fix that and tell you that I love you, and I am grateful to you for staying with me during this time and allowing me to live out my own desires. I know realize that it would be unfair of me to think you still belong to me as my wife, and fully understand that I gave up being a husband the moment I agreed to live with you as Amy. It's clear that living as Amy means that I am your girlfriend, and that I do not have any restraints on you. In fact, I want to encourage you to be happy. By that I mean, whatever you want and whatever makes you happy is my dream for you, and if that includes being with another man, I understand. Please know that I want to encourage you to follow your own feelings and desires, just like you've done for me." I saw mother tear up and watched as Grace smiled and looked deep into my eyes. "Oh Amy, thank you so much for understanding. It has been so hard for me since I learned about Amy. I wanted to help you because I really do love you but, I have also lost my husband and that's been hard for me. Thank you for understanding, and not trying to control me or tell me how to live my life, and yes, I will love having you as my girlfriend, but this won't get you out of your housewife duties. Afterall, you are now a stay at home girl, and I am the money maker," she said smiling. We hugged and I told her I would love to be her homemaker, and that I will make her very happy. Thanks to my mother, that afternoon was a healing experience for both of us as I admitted that I was committed to living as a female and housewife. Grace accepted my desire and I accepted her living her life as she sees fit, including any male relationships. Everyone was happy and we spent the rest of the afternoon making plans for shopping and dinner for the following week. As mom was getting ready to leave Grace's phone rang and she turned it towards us showing that the Caller ID displayed that it was none other than Tony. "Hi Tony," she said as mother watched on very interested. Grace listened and said, "That's great, she told me she had a really good time as well. Of course, I don't mind, and I think she would love that. Why don't you give her a call later tonight and tell her yourself? I think that's a great idea, Tony. OK, see you on Monday." Grace looked at mother and said, "That was Tony, Amy's boyfriend," She then looked at me and said, "He really enjoyed your company and called me to make sure I was going to be OK, if he asked you out for date. You heard me tell him that it was fine and to call you tonight. He wants to take you to his beach condo for the weekend, and I told him that would be a great idea." Mom sat there in shock. Grace smiled at mother and said, "Well, it looks like our little girl is a hit with the boys. I hope you told her all about the bird and bees," she said giggling. They both had a good laugh as I sat there in shock. This was all moving so fast and I was losing control as Grace and mother were navigating my new life as Amy. Next Chapter The following Monday I sent in my resignation letter, effective immediately and at that moment, I became fully dependent on Grace and agreed to remain as Amy and become her housewife. That decision came with expectations that Grace outlined, and I had to agree without objection. Mother did stop by each day and helped me set up a housekeeping plan, taught me some laundry tricks, and how to iron correctly. I learned how to hand wash our lingerie and special items, and how to fold them and put them away properly. She gave me her favorite receipts, taught me how to shop for the correct items, and how to cook and prepare meals. The correct way to set the table and how to clean up the kitchen efficiently. Every morning I got up early and got dressed in an outfit appropriate for the day's activity, that mother had mapped out for the week. One day I dressed for some heavy house cleaning in a smart dress, one inch heels. Another day I dressed for a day out of shopping, manicure with mom, and lunch. Mother always treated me as her daughter, and not once did she refer to me as her son or a man. In her eyes I was now Amy, the daughter she always wanted, and I could tell she was enjoying our time together. I could tell how much she enjoyed teaching me things or correcting some of my movements and even what topics we discussed. She directed our conversations to fashion, decorating, and things for the home, cooking and gossip magazines. I was now fully immersed in the female world, and I had never been happier. Mother was fast correcting me on my posture, how I carried myself and my casual movements. She pointed out how I needed to use and bend my wrist more often, keeping my elbows closer to my side as I walked, even how to be more convincing when I walked in heels. It was embarrassing at first as she had me walk back and forth in my living room as she perfected my walk and movements. That caused me to move a little differently and after several days, I was used to the new walk which gave me much more confidence. This new movement also made my hips sway from side to side as I walked which I knew would draw more attention to my legs and bum. At lunch we often talked about my figure, some new hairstyles, and that we need to pick up a couple of bathing suits for my weekend with Tony. As I was eating my small salad, she looked at me, with what I can only describe as a motherly look and finally asked me about Tony. I could tell she had been wanting to bring it up and this was her opportunity. "Honey, do you like being with Tony? How does he make you feel?" I almost choked and quickly looked up. "Mother! I don't want to talk about that." "Oh Amy, come now I'm your mother and you can tell me anything. It's natural for you to be interested in men, and from the photos I saw he is very handsome and besides, we all know what happened in the limo last week. We're both adults, and I want you to confide in me as my daughter. It's what girls do, honey." Her smile was comforting, and I felt like I owed it to her, for how she's helped me and accepted me as a woman. I took a deep breath and decided to open up to her. "He treats me very respectful and special. It's hard to explain but I really like how he does things for me like open doors, holds my chair for me, takes my hand when we walk, or when he puts his strong arm around my shoulder. Even though I feel like an object sometimes, I like how he makes me feel safe and protected." Mom smiled. "That's how men treat the woman they like and want to be with, and feeling that way is how we girls should feel. You're experiencing feminine feelings, and exactly how they should be felt. Women desire men to take charge, make us feel safe, and treat us special, just like you described." "But mom, I feel like I shouldn't have those feelings. I never thought I would want to feel that way around a man, I never thought of myself as being gay." "Amy, you're not gay or anything like that and you know it. When you're putting on your make-up, doing your nails or hair, stepping into your dress and heels, or putting on your lipstick, do you feel anything other than being female?" "Well no Mom, but." "No buts, Amy. You're a woman and having those feelings towards a man is natural. Those feelings are completely normal, and as I've been telling you all week, you need to embrace your deep feminine feelings and understand that even though you may not have every part in the right place, you are living as a woman and should act, and feel that way without thinking about it. So, from now on, I want you to watch what you think about and don't allow any negative thoughts to enter your mind. You are to think of only feminine things from now on, nothing else. Do you understand?" "Yes, mother. I understand and I'll do as you say. Thank you again for all your help." "Amy, you're very sweet, and I love you and I'm so happy we can spend time together like this. Now, this weekend you're going to spend two nights with Tony, are you prepared for that? Have you thought about what might happen this weekend?" "Well Mom, to tell you the truth, I've tried not to think about it too much. I'm very nervous about going with him, and would rather stay home, but Grace has insisted, and I really have no choice. What did you mean when you said, did I think about what might happen?" "You need to think about it because men like Tony have expectations and will get what he wants. You need to mentally prepare for anything while you're with him this weekend. Have you considered that he will expect you to be sleeping with him in the same bed? You have already touched him down there and relieved his male urges, so you realize you'll be doing that again, right? He will be buying you dinner, taking you out, and treating you like a special lady, and for that he will expect you to do things for him, I'm sure of that." "I haven't given that much thought, but I guess I should. What should I do, mom?" "Well, if you want to see him again you will have to give him what he wants and I'm sure that will mean lots of kisses, letting him hold you close, and probably oral sex. Even your mother knows that men expect that on dates, baby. I know you haven't had that experience yet, but you should prepare yourself for that with Tony. If things go well, he will probably want to make love to you by the end of the weekend, and that will seal your fate. Have you given much thought about my conversation about encouraging Grace to live her life without feeling guilty? You know, she needs the touch and love of a man just as much as you, Amy. She has been so understanding with you and for that you owe her a great deal. You must have that conversation with her before you leave for the weekend otherwise risk her continued support and understanding. I suggest you have a nice conversation over dinner and thank her again for allowing you to flourish into this beautiful woman, and how important it is to you for her to be happy again. Tell her to follow her desires where ever that leads, and that you will be one hundred percent supportive. You need to remove any guilt she might have, about being with another man and that you love her, no matter what." "Mom, I know you're right but it's so hard to give her up to another man. I mean, I love her dearly and I'm not sure I can see her with someone else." "Sweetheart you need to realize that Grace is not bi-sexual and being with Amy is not going to satisfy her needs. If you want to remain in this new role as my daughter and Grace's housewife, then you have to make concessions. Is it worth living as a woman and giving up your hold on Grace? Can you stop being Amy or more important, do you want to stop living as a woman?" "That's not fair, mother. You know the answer already. Amy is here to stay and that just means I will have to understand her needs and be supportive, as you've already explained. It will be difficult for me to tell Grace to date other men, and that it's important to me that she is happy, and that as her housewife I realize that I can't satisfy her needs. I'll be officially giving up my role as husband, forever. I know it is the right thing to do mother, but you do understand how hard this is going to be." "Amy dear, we all make sacrifices and right now it appears that you're getting the better part of the bargain. You have your wife and mother helping you transition, a handsome boyfriend that wants to take you away for the weekend, a loving and understanding wife that is encouraging you to be happy. You already know what you have to do, so stop your complaining and tell her before the weekend." Tony and Grace spoke a few times that week, about the plans for the weekend. They seemed to enjoy making plans for me without my involvement, but Grace realized that I wasn't ready to be making these types of plans just yet and was protecting me and helping me along the way. "You'll need to be ready by 3pm on Friday so I've made a salon appointment for the morning which will give you lots of time to pack and get ready. You'll be spending the weekend in his beach condo in Palm Beach, you lucky girl. Your mother showed me the outfits you purchased, and I think you'll look lovely in them but, Tony was a little concerned about the bathing suits and we discussed some options that he believes will solve any potential problems. Even though his beach area is quiet, there will be other people there that know Tony and he can't risk anyone finding out that you have a little extra in your panties. We both agree that you look, sound, and act like any other women but he can't take a chance of an unexpected bump in your bathing suit bottom. Tony said he had a solution that worked in past with other girls and sent a package over for you to use this weekend. I did some research and I think it will prevent any problems," Grace explained. "What is it, what did he send over?" I asked. Grace picked up a small box off her lap and handed it to me, smiling and said, "Open it and find out." I recognized the small metal device right away and just stared at it in shock. "You both expect me to wear this under my clothes? The tight panties and have kept things hidden to everyone, why this." "Amy, this is a chastity device or just a little clitty cage, and that's what Tony likes to call it. It will prevent your little boy bits, from getting excited and keeping things under control and out of sight, in case something happens. That means, the bathing suits you'll be wearing will not give any secrets away. Tony said that he had some close calls with previous girlfriends and can't take any chances and until you start taking T Blockers, he wants you to wear this for both of your sake. At first, I thought it was odd but the more I thought about how it works, the more it makes complete sense. It's really no big deal, and you said that you don't get turned on by men, so you shouldn't have any objections. Let's see how it fits." She had me pull up my skirt and remove my panties and for the first time in weeks, Grace touched me but, it was all clinical, nothing sexual in how she worked the device into place, and clicked it closed. I felt humiliated as I held up my skirt and allowed her to put my only male vestige into that device. Surprisingly it wasn't horrible since it was so small. The shape of the device kept my boy bits tight against my body, and presented a noticeably smooth front in my panties, after I pulled them up back into place. "Looks like Tony was right and the size he picked was perfect. No matter what happens or how excited you get now, there will not be any accidents and you'll now be able to wear some of those sexy tight dresses. You can even wear your bathing suits without worrying about showing everyone our little secret. Wear it for the rest of the night and try to get used to it because, you'll be wearing it all weekend." Knowing I had agreed to obey her wishes, I wore it to bed and the next day after my shower. It wasn't uncomfortable and it did give me extra protection and a much flatter figure. However, I was a little shocked, and even more humiliated when my mother came over for coffee the next morning, I wanted to run and hide when she asked me how I liked wearing it and if it was very uncomfortable. Grace must have told her about it and now she was asking me how I liked wearing this device. I realized at that moment that nothing was private between Grace and my Mother. It was difficult to get used to, but I knew I had no choice in my new position as a daughter and housewife. I didn't want to discuss it, but I knew she expected me to say something, so I said, "It's OK and I'm already used to wearing it." "Well, it will be worth it when you slip on those sexy bathing suits and wear those tight dresses. Now more importantly, did you discuss what we talked about with Grace? Did you encourage her and tell her it was OK for her to be happy and that she needed to live her life however she desired?" "Yes mother, we talked about its last night. I took some time and told her how much I loved and cared for her and wanted the best for her. I thanked her for helping me and staying with me through all this new stage in our lives. I apologized for not letting her know about my feminine desires sooner, and I also told her I was sorry about the way she found out. She thanked me and said she only wants the best for me as well, and she can tell that letting Amy live her life was the right thing to do because, she hasn't seen me this happy in a very long time. She said she loves me and now feels much closer. "Did you tell her it would be OK for her to have other male friends, if she ever needed their company?" Mom asked. I lowered my head and said, "Telling the love of my life that it would be OK to date or be with other guys, was one of the hardest things I've ever had to do, mother. She was shocked at my honesty but was also grateful and thanked me for my understanding." "What did she say, tell me everything Amy." "I told her that I have been so wrapped up in my new life that I was not really thinking about her feelings and needs. Living my new life as Amy, going out with Tony, and living as the girl I've kept inside me, was overwhelming. After I found out I was going out again with Tony and leaving you alone while I'm out with some guy, has given me a tremendous amount of guilt. I said, Grace you're a sexy woman, and I know guys are constantly hitting on you, and that you've been nothing but faithful to me, and now that isn't fair. Since I'm going to be living with you as your girlfriend, I realize that I've given up my position as husband. With that in mind, I want you to be happy and if that means having friends that are men, is understandable and only natural, and something I want if it is what you want." Mom was pleased with my comments. "Wow, good for you Amy. That took a lot of courage to do that, but I'm proud of you, and I know you it was the right thing to do. What did she say to that?" "Mother, she had such a big smile on her face when I said that. She finally stopped smiling and said, 'Thank You, Amy! I didn't know how to bring it up and you made it easier for me because you're right, I do need male friendship and the more I'm around you as Amy, the more I realize how alone in this relationship. I don't have anyone in mind but just knowing that you understand what it must be like for me, is amazing. I'm so happy for you and I'll be there all the way to help you with anything you need, and I expect that same from my girlfriend. Let's make a promise to tell each other everything, just like all girlfriends do because, that will make us so much closer as girlfriends. I know this is all new for you but, I'm here to help you with anything you need or any questions you have.' Date Night Ever since my conversation with Grace about our relationship, she was now so much more friendly and giggly as she helped me pack for my weekend. She picked out all my outfits, told me what to wear for dinner, what cover-ups to bring down to the beach, and what sandals to wear, what to wear to bed, and encouraged me to remember that I'm Amy, a girl and on a date with a real man. She even said, "Be Amy, and do things Amy would do with her boyfriend, and remember I love you no matter what you do, I just want you to be happy, and discover how great it is being a female in today's world." Going to the salon now was no longer a big deal because, I knew what to expect and the girls were always nice and supportive. That day they added some highlights to my hair, worked on my extensions, had a body wax, got a new manicure and pedicure with coral pink polish, for a nice beach look. They replaced and added some extended eyelashes, cleaned up my eyebrows, and after my facial they did my makeup, as they explained the process with each step. They enjoyed teaching me all their techniques and encouraged me to practice them often. The results were more amazing than ever as the girl in the mirror was stunning, and with the new highlights in my hair and amazing make-up, that girl in the mirror was, sexy. I smiled in amazement at how my life had changed so fast, and how great it made me feel to be living as Amy. As I pulled up to the house, I was surprised to see mother's car in the driveway and even more shocked to see Grace home from work when I entered the house. When they saw me, they both gushed, "Oh my, look at you, my sexy girl. They really went all out today on you, didn't they?" Grace and Mom gushed. Mom spoke up and added, "Yes they did, my little girl is all grown up." Having my mother and wife fussing over how good I looked as a woman, was a new feeling which made me smile. "Why are you two here?" I asked. "Well your mother wanted to meet Tony, and I wanted to be here to make sure my girlfriend is ready for her big weekend. It's your first time spending the night with a man, and I want to make sure you're ready. Mother and Grace sat on the couch in the living room as they had me model my outfit for them. They both liked the pink sundress and wedge sandals and said it would be perfect for the dinner on the beach, which apparently is what Tony had planned. "With all that exercise combined with that diet you have been on, is certainly paying off. Your figure is getting slimmer and more girlish every week. Those tight outfits and bathing suits, will look much better on you now," Grace said with a happy expression. Grace and mother helped me dress for dinner as they handed me on piece of clothing after another. Grace helped put the silicone inserts into the new bra as I was pulling up my panty girdle over my caged boy parts. It worked as I was completely flat in front with no chance of anything popping up, so to speak. I saw mother watch as I expertly slid on a new pair pantyhose and finally stood before both. "Very nice figure, and lovely lingerie you picked out for her, Grace. I stepped into the silky black dress that fell to mid-thigh. Mother zipped me up as Grace adjusted my breast in the dress. Without being told I walked over to the closet, picked up my heels, and as if I'd been doing it all my life, easily stepped into the four inch heels. I stepped in front of the mirror and took in the pretty girl that was looking back at me, as Grace and Mother adjusted my outfit to insure it was perfect. I put on all the jewelry along with the new chandelier earrings, we purchased this week. I touched up my makeup, and hair, and applied some fresh lipstick and was ready for my weekend. While I was dressing, my mother and Grace finished packing my things. When I was ready, I turned and took a deep breath. "I'm as ready as I'll ever be." Grace handed me a gift wrapped bag, which contained an expensive purse and card. The card said it was from Grace and my mother. Inside the purse was my makeup, several packages of condoms, and 5 tampons, and nothing else. They giggled as I held the condoms in my hand and said, "This isn't funny. I'm not ready for anything like that." "Well ready or not, you might not have a choice sweetheart, and you need to be careful," mother said as they both giggled. "That's not funny, mother. Where is my phone and wallet? I will need them," I said. Grace whispered and said, "No sweetheart, you won't need them. This weekend you will have no money, ID, or phone, which will make you completely dependent on Tony. Your mother and I discussed this and, we think it's best for you to fully understand what it means to feel dependent on a man, and completely vulnerable. Trust us, it is for the best. There is another item we put into the side zipper pocket. You will find 3 sedatives you can take if you find things are making you too anxious. This time you should only take half a pill, in order to be more alert and remember everything. Only take them if you really need them because, it's best for you to be fully awake so that you can remember everything this weekend." I stood there in shock with my mouth open as Grace told me that last detail. That's when the doorbell rang and I quickly put the condoms I was still holding back in the bag and answered the door, as Grace instructed. Mother and Grace remained on the couch as I led Tony into the living room. "Hi Tony" Grace said. Grace smiled and said hi to Tony and then said, "Amy, aren't you going to introduce Tony to your mother?" "Tony I'd like you to meet Carol, my mother. Mother, this is Tony." "Hello Tony, lovely to meet you. My daughter has told me so much about you and it's a pleasure to meet you." I stood there feeling humiliated, scared, and shocked as I listened to my mother and my date discuss me as her daughter, and how I told my mother things about him. It was like an out-of-body experience as they spoke. "It's nice to meet you as well, Carol. Your daughter is quite lovely and special, as I'm sure you know," Tony said shaking mothers' hand as they met. Grace took the opportunity to speak and said, "Oh yes, Amy is very special and has been talking about this weekend all week-long. She is so excited, aren't you Amy?" Feeling trapped and not knowing what to do or say I just smiled and shyly nodded my head. "Well that's good to hear because I have a fun weekend planned, and your little girl will have a great time, I'm sure," Tony said. "That's wonderful, she deserves someone nice like you Tony. Please take good care of her," mother said. "Yes, we want our little girl to have a good time and experience all types of new things," Grace said, giving me a hug around the waist. Mother held up her phone and said, "You two make such a cute couple, can I please get a few photos of the two of you?" Tony and I stood for several photos of us and then mother took a few of just Grace and I as well as the three of us together. Embarrassing me even more, mother asked Tony to take a few of her and her daughter and then a few more of mother, Grace and I together. "We have dinner planned and we should get going. Do you have some bags I can bring out to the car?" Tony asked. Grace pointed to the 3 bags and Tony brought them out to the car as I stayed behind with my Grace and mother. "Just have fun, baby and do not hold back. Enjoy yourself and remember if anything happens, it's just sex, nothing else. Unless you start having feelings for him in a special way, whatever happens is just physical, nothing more. Let yourself go and enjoy everything. Your mother and I know what it's like, and as woman we can enjoy sex without emotional feelings, so enjoy yourself and remember that our feelings will not change if anything happens, as we are sure it will. Do you understand, honey?" Half in shock I looked at both of them standing in front of me smiling and I said, "Yes, I understand. But this is all new to me, and I'm not sure how to feel." "Don't think or feel, just go along with whatever happens and live in the moment. Don't think, just do. You'll understand and I'm sure it will be fun. Now here comes Tony, kiss us goodbye and enjoy this new experience and the weekend." As I left with Tony, I looked back at Grace and Mother and felt as if I was being led away from the woman I loved, to a new experience that was out of my control. I saw them chatting as the door closed. "Poor dear, she looks so frightened," mother said to Grace. "Yes, but after this weekend she will have a much better idea what living as a woman is really all about. I guess we will have to wait until Monday to see if Amy is really here to stay," Grace said. "With a man like Tony, I would agree. You do not get much more manly, that's for sure. He is quite handsome and so muscular. I have to admit, they do make a cute couple." "Yes, they did. Please have Tony take some pictures and send me a copy of those photos, I'd love to see them tonight," Mother said as they saw us drive away. In the car Tony started the conversation. "I have to say that Grace has been very supportive of us, and your mother is very nice. I think it's wonderful how much they love you." "Yes, they are very special." "I think you're going to have a fun weekend, baby. I have some fun things for us to do and we start with dinner on the beach at sunset, at a very romantic spot I picked out for us tonight." As he spoke, I noticed how my legs were crossed and my skirt was half- way up my freshly waxed, smooth feminine legs, and the new purse on my lap, which made me feel weak and submissive next to his big muscular man. I was quiet and didn't say much feeling scared, and nervous about being alone with him all weekend. "Amy, I can tell you're nervous, but I want you to relax and just enjoy the weekend. Grace told me you enjoyed our last date, and were looking forward to seeing me again, so there is no use in being shy with me, OK?" What had Grace told him? He was under the impression I was looking forward to being alone with him, but the truth was that I was petrified, and this really was Grace's doing, not mine, but I couldn't say that to Tony because of what Grace had told him, and besides I know he wouldn't believe me anyway. He was very attentive and a perfect gentleman as he took my hand and led me to the restaurant. I noticed several men turn their heads as I walked by, which gave me a little more confidence, as I tried to keep up with Tony's long strides. He held my chair as I sat down and then he leaned over and kissed me sweetly on my glossy pink lips. "I wanted to get that out of the way, to break the ice. It will make things easier for both of us as the night progresses." He ordered us some Cosmopolitan's and they went down easily. After a couple more I was much more relaxed and started to enjoy the surroundings as we sat in the only a few yards dimly lighted restaurant, which was only a few yards from the ocean. The view of the city and ocean was exciting as we both watched several expensive boats sailing in clear view. It was a romantic setting and I found myself enjoying myself. I finally had the courage to start a conversation and said, "This is a lovely restaurant, do you come her often." "Not too often, only when I'm with a sexy girl like you that wants to spend time with me," he said as he ran his foot up my leg under the table. "Well, I love the view and these drinks have helped me relax. To be honest, I was very nervous about all this, but now it feels much better, in fact I'm enjoying myself," I said. He smiled. "That's perfect, this is just the beginning, and by the end of the weekend I'm hoping you will feel much more comfortable being around me. And I'm also hoping that after this weekend, you will want to spend even more time with me. To be honest with you, since our last date you're all I've been thinking about, and when Grace told me you felt the same way I was so excited. I could not wait for this weekend to get here. I'm hoping you enjoy the rest of the weekend as much as I am. Whatever you want this weekend is yours. It's my way of thanking you for going to dinner with me last week, it really was fun," he said smiling. I smiled and felt warm and tingly as he said all those sweet words. I never dreamed I'd hear those words from a man let alone a hunk like Tony. I had a small salad and some grilled fish with another drink, and after sunset he paid the bill and helped me walk back to his car, where I carefully got in feeling quite tipsy, no kind of drunk. He drove us to his condo and took me up to his condo on the 19th floor, which had a wonderful view of the ocean. After he brought my bags into the bedroom, he led me out to the large outdoor deck, onto a double wide lounge chair where I laid down and enjoyed the view. "I'll be right back, just relax and enjoy the view," he said. I was so relaxed and enjoying myself and forgot about all the things that I was worried about. I heard Tony open the door and saw him carrying a bottle of wine and two glasses. He poured two glasses and handed me one, as he snuggled next to me on the lounge chair. He maneuvered his arm around my shoulder as I leaned into him which gave me another warm feeling. I felt safe and protected at that moment, and I to my surprise I really enjoyed how that felt. I smiled to myself and took a sip of wine. We lay there quiet as he stroked my arm with his strong hand, and I continued to lean into his muscular body. I realized, that there were a thousand girls that would love to be in my place at that moment. After a while I moved a little and turned my head to look up at Tony, who took that opportunity to pull me into him for another kiss, but time it was much stronger and much more passionate. At first, I resisted, but only for a few seconds until I gave in and kissed him back. Yes, I kissed him back, and I was enjoying how he was making me feel and I didn't want it to end! Before I knew what was happening, Tony led me to our bedroom while we continued to kiss and feel each other's body. His strong hands on my body was amazing, and feeling wanted and desired like that, was a big turn. When we broke our kiss, I realized we were now sitting on the edge of his bed, when he stood up and took off his shirt revealing his muscular chest. I gasped as he unbuckled his pants and they fell to the floor. Before I had the chance to sober up, he took off his underwear, revealing that massive cock. I just stared in wonder, comparing it to my little appendage now locked away. With an excerpt ease, Tony laid on the bed and pulled me next to him and started to kiss me again. The room was dark except for the moon light, coming from the wall of windows in front of the bed. We kissed and hugged each other as I laid next to this gorgeous naked man. Tony moved back, and with his arm bent and his head on his hand, looked at me and smiled. "Amy, you are amazing, and really turn me on more than any other girl I've ever been with. Besides being so pretty and feminine I really enjoy being with you, and our chemistry is obviously strong. I've been with lots of girls, but you are so much different. The feminine way you move and that sexy voice, drives me crazy. I also loved it tonight, when all those guys were checking you out at the restaurant. I was proud to be with you as your date, and the fact that nobody had a clue what's hidden under your panties." Tony looked deeply into my eyes as he continued to tell me how pretty I was and quickly unzipped my dress, and was now pulling it off me, as I moved to help him. I was now laying there in my matching yellow bra and pantie brief. I moved my hands up to cover my bra, because I felt self- conscious as he stared at my body. His touched the lace of my bra and to my utter dismay, his other hand touched my panty, where my clity cage was hidden. He smiled and said, "Thank you for wearing my gift. I should explain why I sent it over for you to wear," he said as he pulled down my panties exposing the pink cage. As he touched the device through the nylon he said, "I guessed at the size and picked the smallest one I could find, and it looks like I got you the right size, as it really conceals your clit. There was a couple of reasons for this and the obvious one is it conceals things and prevents any accidents that I cannot afford. But the main reason I like you wearing it is because, even though I love girls like you, I don't really enjoy seeing your clit. I just enjoy knowing it's there, but what turns me on is your presenting as beautiful woman and knowing you have no control of things. When you are like this, I see you as a complete woman, and will treat you accordingly. When you look as sexy as you do it just drives me wild, and when I hear that sexy voice, I'm in heaven. I really want to keep you like this and spoil you, if you'll let me." He didn't give me a chance to answer as he leaned over and kissed me hard and played with my bra and panties and nylons. I enjoyed the kisses and his attention, and I didn't even mind his demand of me wearing the clity cage. I didn't realize it until my hand was now touching his large cock, Tony had expertly moved my hand there while we were kissing without my knowledge. "Play with it Amy, please," he said as I took it in my hand. It was so hard, hot, and big, like nothing I had ever felt before. In comparison, mine was just a clit and nothing like his massive tool. For some reason, I wasn't grossed out and allowed myself to be in the moment as remembered what Mom and Grace told me, that I was Amy this weekend and to act as Amy would behave with her date. I did. I held him as we kissed and slowly found myself stroking him, as he got hotter and harder. I liked it. I liked the control I had over this huge man and let myself just enjoy the moment. We continued to kiss, and he continued to rub my bra as I stoked him for a long time, until Tony could not take anymore and gently pushed me down onto the bed. He placed a pillow under my head and straddled me as I looked up at this massive man now on top of me. "Amy you really got me excited and I want you," he said as me positioned himself so that my head was propped up and he towered over me with his hard cock in front of my face. I knew what he wanted and realized that if I didn't stop things at that second, that from that moment forward my life would change. If I let him put that in my mouth, I knew I would forever become a cocksucker, and something I can never take back. I was apprehensive and trying to avoid the inevitable until Tony's testosterone took over. He could not wait any longer and moved himself up on the bed until the tip of his cock was sitting on my bottom lip. He leaned forward and I felt his very hard cock start to spread my lips. The pressure forced me to give in, and his weight forced my mouth opened just a little, but enough to encourage him to push forward. Almost instantly the head of his cock was now inside my mouth resting on my tongue and I realized I had just past the point of no return. I felt my mouth open a little more and Tony took over and did the rest. I looked up into his eyes as he started to move his cock in and out of my mouth. He was fucking my mouth and I was giving him a blowjob, I had become a cock sucker and something I could never take back. I tried to relax as he looked into my eyes and continued to move his cock in and out of my mouth. "Oh, that's it Amy. Just like that, don't stop," he said as he let out a small moan. I felt my boy bits start to get excited, but the cage instantly sent a pain signal to my brain and my clity instantly stopped getting hard. I put all my concentration to the cock in my mouth and tried to focus on everything that was happening. My tongue now ran up and down his cock as I explored every nook and cranny and became very familiar with Tony's cock. This went on for well over five minutes when he looked down at me again and said, "I'm close Amy, get ready baby I'm about to come in your beautiful mouth. I want you to swallow me baby, take all of me," he said as I felt him grow and start to pulse inside my mouth. The first squirt of cum hit the back of my throat, and I had to either swallow or choke. I swallowed the first load, and the next seven, that he shot into my mouth. He came so much that his cum quickly filled my mouth and poured out over my lips and face. He finally stopped shooting his come, but he continued to fuck my mouth for several more minutes, as he let out cry after cry of satisfaction until he finally stopped and let it rest inside my mouth. I looked up at him and wondered if he would ever take it out of my mouth. He had such a satisfied look on his face and smiled, as he looked down at me and said, "Wow, that was the best blowjob I have ever had. Amy, you're amazing, thank you." He finally removed his cock and laid down next to me on the bed and continued to look into my eyes. He took his two fingers and scooped up the come on my face that I wasn't able to swallow and fed it to me as he continued to look deeply into my eyes. "That is so sexy, Amy. I can tell you enjoyed that darling, and I'm so happy you like my cum, and I want to give you so much more," He leaned over and kissed me deeply, and once again he played with my padded bra as I enjoyed all of his admiration and affection. Yes, he was right, I did enjoy it and wanted more, but part of me questioned what I was doing and what I had become. I realized there was no going back, and I had to accept the way things were, and try to accept and enjoy the moment. I wondered what Grace would think of me, and realized that at this point, after telling her she could see other guys, it probably would not matter anymore. He held me as we lay there and we both drifted off to sleep in each other arms. We were exhausted and I slept soundly safely wrapped in his strong arms and would stay that way for many years to follow, as husband and wife... ...but that story has yet to be written