Caught

by Lorraine Simmons

 

My wife Diana found out that I was a cross dresser two years ago when she indivertibly found my secret wardrobe of female clothing hidden in our attic. I tried to explain my feelings but without any acceptance for over a year, during this period our sex life eroded to almost nothing and I felt truly worthless. The only relief for me was the rare opportunities to cross dress when she was away on business. I always wondered what Diana was getting from our marriage and I was left to be lonely and frustrated. Diana never explained where she would go or for what reason she poured everything into her work. Our marriage in my opinion was falling apart and there was nothing I could do to improved the situation. Diana was a very successful attorney and a beautiful woman and I was very lucky to be married to her. I envied her feminine good looks and business success. She never approved of my dressing but would say, "as long as you keep it private and contained to the home she would tolerate my problem because she refused to even think of getting a divorce."

There started my real problems. I recently lost my job and I rarely had contact with anyone. I began to search out some form of companionship. I should have known better but I searched the Internet for another cross dresser, like myself who wanted to share our interests. I found another T-girl named, Paula. She and I e-mailed each other for several months. The day final came that I wanted to meet face to face. Diana was to be away for a week and I made an appointment to meet Paula. That was mistake number 2; I would be leaving the sanctity of our home for the first time fully dressed as a woman. This is something I had never done and would violate the rules directed by my wife. I got up in the morning alone and wanted our meeting to be perfect. I took a long hot, perfumed bath and shaved my whole body to further pursue my image of a totally feminine body. I put on my silk robe and sat to do my nails. I shaped and painted my fingernails a rich red color and then my toenails. I knew that no one but me would see my toenails since I planned on wearing pumps but I wanted to feel as feminine as possible. I then did my makeup but felt disappointed when I saw that my eyebrows looked too full. I was too scared to pluck them into thin, highly arched feminine eyebrows because I knew Diana would surely see them when she got home. The crowning touch was my long blond wig I placed upon my own rather long hair. I always wanted my own long hair, but it was another point of argument between by wife and myself. She never said a word but I could tell she was annoyed that I let it grow as long as I did. I looked into the mirror and my most feminize self-looked back. The final addition was clip on hoop earrings, I always wanted to use pierced earrings but again was afraid to anger my wife with holes in my ear lobes. A long final look in the mirror and a feminine flip of my head and I felt just perfect.

Once made up I started the process of getting dressed. I first slipped into a black thong panty, which always make me feel more womanly and then put on a black long line bra and filled the cups out with old stockings. I have looked into buying breast forms but didn't want to further enflame my wife's anger. I then pulled on some sheer black pantyhose. The final addition is a firm black panty girdle, which holds me in very securely. I then put on a lacey full slip and have selected one on my wife's good business suits. She and I are almost the same size and I wanted to present the image of a successful businesswoman, very much life my own wife, at the initial meeting with Paula. That was mistake number 3, borrowing my wife's clothing. At this point I could only think about the meeting with another T-girl. Not once thinking how my wife would feel, with me her husband wearing her very expensive clothing. I put on a pair of black 3" heels and filled one of Diana's expensive purses with my money, ID and keys. I looked one last time in the mirror and was very pleased with my transformation. I just realized that I should spray myself with some of Diana's perfume before I leave the house. After using one of her most alluring fragrances, now not only did I look like a woman I even smelled like one too. At the time I did not realize I was remaking myself into a rendition of my own wife.

My stomach felt like it was going to get sick from all the excitement and nervousness. My hands were shaking as I grabbed the car keys and walked to the front door. The moment of truth had arrived and I was going out as Lorraine for the very first time. I opened the door and stepped out into the daylight as a beautiful woman, just as though I did this every day of my life. It felt great. I walked to the parked car my heels clicking on the pavement and opened the car door. I seated myself first as any natural woman would; swinging my legs into the car in the same manner I have watched my wife elegantly enter a car. I closed the door and placed the key, gripped by my own luxurious manicured fingers, into the ignition and started the car. My senses were heightening and the feel of my own high heels on the car pedals and very feminine fingers gripping the steering wheel were unique experiences. I drove to the restaurant and spent the next hours being excepted as Lorraine Simmons, successful businesswoman. Paula and I spent a wonderful time comparing stories and dreams of feminine situations. We then did some shopping and made plans to meet again tomorrow night. I felt so special once I got home. I planned to sleep that night in one of my wife's long, sensual, frilly nightgowns. I did all the nightly beauty preparations I have witnessed by wife perform and after putting on her most feminine nightgown I entered our bed as she would each night. I dreamt about the plans for the next night on the town and how I would feel as the lovely Lorraine Simmons and what I could do to make myself even more feminine. The experiences reacted like a drug and I wanted more.

I had spent the day fully dressed as a businesswoman and made plans to dress even more daring for our next adventures. I selected a silk cocktail dress from my wife's side of the closet. I did not know at the time how each encroachment into her things would increase her anger and resolve to make me pay for those foolish mistakes. I dressed more sexually this time and wondered how others would receive my appearance as a woman. I never had any homosexual thoughts and never realized how a man might come on to me while dressed. Paula came and picked me up and we two "hot" looking women went to a lively nightspot. We found a corner booth and Paula order some wine and we chatted "girl" talk between ourselves. The waitress brought us two fresh drinks and told us it was from two very handsome businessmen at the bar. We smiled at them and waved. The men came over and asked to join us, Paula, who had more experience being in public said yes. Each of the men slid into the booth, shutting off the means to escape. Bob, the guy seated next to me caught sight of my long exposed legs I had foolishly displayed with me being so new to public dressing as a female. I felt very self-conscious and tried to cover my thigh with my clearly feminine hand and Bob instantly rubbed my nylon-covered leg. They became more forward and we said we had to go home. As I stood up to leave Bob kissed me before I could react. He also placed his hand on my ass and gave it a rub at the same time. Paula and I laughed all the way home. If only those guys knew who we really were under the carefully applied make up and feminine clothing, they would have died. Before leaving me at my home, Paula and I made plans for tomorrow I was having so much fun I didn't want it to end.

I was getting more confident as Lorraine and for the next day I planned to wear Diana's favorite outfit. This was my worst idea and I had no idea what was going to happen to me for that error in judgment. It was a very sexy black lace dress with lots of lace and a very short skirt. It fit perfectly and I loved how it made me look. New smoky hose and matching lingerie came next and sleek spike heels matched the outfit. I put on my make up and loved the attention Paula and I was getting and wanted to look even more desirable today.

I teased the hair on my wig and decided I looked hot enough. I got my purse and keys and headed to the car to pick up Paula for lunch. As I was between the car and the house I froze in my heels when I heard Diana's voice. "Well, well, well!! What do we have here?" Diana taunted as I stood in shock in the driveway. "Very pretty, lets see.. What was your name? Oh yes, Lorraine, Lorraine Simmons, wasn't it? Oh, I see you are now even wearing my very best clothing, we will have to see about that!" she continued. I gasped as she told me to go back to the house and kept calling me Lorraine. I knew I was in trouble.

Once in the house she handed me a thick envelope. I think you will find this very amusing. I opened it and was stunned as she had over 100 pictures of Paula and me fully dressed as women all over town, shopping, having lunch and even the little episode with the men. There was even a photo of when Bob kissed me and felt my ass. I had you followed, you know I am an attorney and need to keep my private life spotlessly clean. "You know how I felt about your dressing and you going out flaunting it in public. We are going to have some changes starting right now. For starters, Lorraine, we are going out to dinner tonight and that outfit is not special enough for your new adventures I have planned. There are two gorgeous men who are taking us to a very exclusive restaurant in the evening. Since you enjoy men so much and being such a feminine girl I know you will have as much fun with me as you did with Paula," explained Diana.

I protested but she slapped me and told me to shut up. Just like a woman, talking too much. She told me if I disobeyed anything she tells me to do that I will be exposed to all my friends as the faggot, who dressed up in his wife's clothing and pretended to be a girl. That was her initial means of control and I could not then foresee to what lengths she would go to in the future to further enslave me. At this point all I wanted to do is keep my cross dressing our secret. She had a wild look in her eye and I knew better than to object. First get out of my best outfit and put on something else till we get you your own clothing. As I removed her dress she saw the cups of my bra. "You need something more pliable and realistic than old stockings that you use to fill out the cups of your bra. I brought you some very realistic breast forms. I need you to remove your bra so I can attach them to you properly" she orders. She cleans my chest and applies the adhesive to the forms and holds them in place till the glue dries. She applies more glue and blends the seams with a special make up. I can hardly tell where the forms end and I begin." We don't want your date ripping them off! Lean forward and enjoy the womanly weight of your new breasts as she reinstalls my bra to contain the massive breast forms I now have securely bonded to my skin. She laughs at me. Now that I given you a very womanly chest and think you need to know what it's really like being a woman. I think you need to feel ultra feminine and I know of no other womanly event then having your period." She makes me lower my girdle and hose and then forces a super size tampon into my anus. "Now you know how you fucked me pretending at being a woman, you wanted to do girly things, now you can suffer just like a real woman. She hands me a sanitary pad and demands I place it in my panties before I pull them up. From now on you will have to sit on the toilet just as any other woman and pee just like one of us. I put on another of her conservative business suit and Diana redoes my makeup. I look into the mirror and look just any other business woman dressed to go to work, but now feel the very real weight of my new bust and the tampon now lodged deep within me.

Diana takes me to her favorite dress store and I am forced to try on various dresses of her choice. She selects a very tight black sequined dress for me to wear that night. It is a bit tight but Diana says after the pending corset fitting, it will fit perfectly. After buying the dress I am taken to a lingerie store. Diana walks up to the owner and tells her that I need to be fitted in a tight black corset. It is apparent that prior plans had been made for this fitting because the shopkeeper knows all about me. I am led to the rear of the store and told to undress. My bra is removed and I feel very exposed with my newly attached breast forms, but not for long. I stand if front of this woman with my glued on breast forms sagging just as any natural woman. The shopkeeper comments, " I see that your wife has seen to assure you the full reality of being a very fully endowed lady. Your new breasts look very real and I would think you would like them properly supported." The corset Diana has selected has full cups which grasp the breast forms and once the front busk is closed I sense that I will appear very sexy in the new dress. The owner begins to lace me tighter and tighter. My breasts are amply supported and my ribcage is made smaller by the powerful garment. I am allowed to walk about while the new corset adapts to my body. After about a half hour the lacing is retightened and I comment that I think the corset is way too tight. The owner say to me " a woman must suffer to make herself attractive for her man and your wife will need to retighten the corset before you go out on your date. Now let us try on your dress." What was once extremely tight fits my newly formed body like a second skin. I look in the mirror and I have a body to die for.

Our next stop is the nail salon. Here I am seated and the girl is instructed to apply 2" acrylic nails to my fingers. As the girl works on me I wonder how I am going to get these off. The process looks very permanent and I am getting very worried. I ask Diana how am going to return to being a man with these rather permanent looking feminine fingernails and attached breasts. "Just worry about looking and acting as a perfect lady for your date tonight" Diana slyly laughs. Bright red polish is applied and I am slowing being changed into a female. The next stop is the beauty salon and there I begin to wonder if I will ever again be allowed to be a man again. The wig is removed and the beautician informs me Diana has ordered a full and very complete makeover. Firstly hair extensions are securely attached to my own hair. My lengthened hair is washed, cut, bleached a bright blond and then rolled up tightly upon assortment of pink rollers. Once all the rollers are placed a permanent lotion is applied to my newly dyed hair I catch a look in the mirror. My head is covered with a multitude of rollers and I now look like any other woman in the salon. I am placed under a dryer and feel my hair tighten about the curlers. Once my hair is dried the rollers are removed, my hair is then styled into a very feminine hairstyle on long silky blond curly tendrils hanging about by face. All I can do is sit bounded up in the extremely tight corset and look at the very feminine hands I now have thanks to the nail technician. I watch as my attached false breasts rise and fall as I labor for breath and I have no idea how I can remove them, if Diana would allow me to, but that does not appear to be an option. She continues the attack to my remaining masculinity and starts to pluck my eyebrows into two very thin feminine lines more radically shaped than I ever could imagine doing myself. Individual long artificial eyelashes are glued among my own eyelashes and then coated a deep black. I could feel the weight of the new fuller lashes and sensed an increased feminine appearance. The final assault is two permanent holes punched into each of my ear lobes and first long dangle hoops are put through the lower holes and then diamond studs in the upper holes. As she applies my new evening make up she jokes with Diana how I must have been a very bad boy but thanks to her I now appear to be a very good girl. I look in the mirror and I am in shock, no trace of my former male self remains. I now look like a beautiful and very feminine woman. "I hope you are happy with your present appearance, because I plan to keep you looking like that from now on. You will become my new girl friend and live with me in our home, but from now on living in the guest room, since I now look 100% like a woman and not anything like her husband. We will do everything as two women from dating to weekly visits to get our nails and hair done. I will tell everybody you left me for another woman. No one will realize the other woman is in reality you. I will get a permanent identity change for you so I can legally keep you as a woman for the rest of your life."

I beg her to stop before it's to late. "It is already too late. Just look at yourself, do you think anyone would know it's really you looking at the woman you appear to be now. I think you make a far better girlfriend than a husband. I have spent so much time and effort on creating your appearance you better just get use to being a woman" I plead with Diana that I don't want to be a woman, but she just laughs at me and says "You should have thought about that before wearing my clothing and pretending to be a girl. You just need to sample your new reality because you don't have any choices" We got home and await our date's arrival. I am given black silky seamed stockings to put on and I am instructed that my seams must be absolutely straight since men like the provocative look. Next black paten leather pumps with slim ankle straps are tossed at me; I sit on the bed and secure the ankle straps with great difficulty due to my new extended feminine fingernails and my newly lengthen hair falling over my face. I slowly stand and Diana retightens lacing of the corset before helping me into my new dress. She forcefully rises and secures the rear zipper encasing me into what I know is a very sensual feminine dress. She next attaches to me a shiny diamond bracelet and necklace. The gold hoop earrings are replaced with long dangle diamond earrings Diana hooks and locks into the lower holes in my earlobes to complete my look. Diana next removes her own diamond engagement and wedding rings from her left hand and hands them to me. "I think you should be the one wearing these from now on to further enhance your new position in our relationship as the woman with a married past, since you no longer look anything like my own husband and now you can play the part of the suffering wife." I reluctantly put them both on my left hand as would a woman and feel that another critical step in my feminization has occurred. Diana forces me to stand in front of the full length mirrors and berates me "You wanted to dress and pretend to be a woman, well now we are no longer pretending and I have even more womanly adventures in store for you! I believe I have made you into much more of a woman than any of your fantasies and I have no plans of ending your feminization." I have to slowly descended the stairs due to the confinement of the dress and my extremely high heels to open the door and greet the two men, who are taking us out tonight. I bring them in and walk ahead of them to our living room. I know there eyes are on my butt and I know that is due to the tightness of the dress and the dark seams on my black hose tightly attached to my garters and the fine silky curly blond hair swaying as I walk. I am giving a great show and helpless to stop what Diana has planned for my humiliation. The two men are named Jim and Brad, and Brad will be my date for tonight. Diana calls me to come to her. She sprays me with some more perfume and tells me she expects me to act very nice to my date. She say "I doesn't expect you to go all the way tonight due to my having my period, but other than that I better act as the very seductive woman she has transformed me into and give your date a very pleasant time". I now totally trapped and horrified at the instructions Diana wants me to follow. I stand teetering in my high heels my body encased within an extremely tight corset and dressed to kill in a very tight sexy dress; my hair and makeup reflex the image of a very sexy desirable woman and my wife demanding I now live the part with no hope of returning to being a man. I look just like my dream image but I am horrified at the same time. She hands me a silk evening bag and all that is in it is a replacement tampon, a small perfume spray and lip stick which matches the shade I have on. There is no money, ID or credit cards so I will totally dependent on Diana or my date tonight. Lastly her own silver fox jacket is given to me to wear and I remember how seductative and vulnerable she look wearing it and now I would be seen as the woman seen wearing it. This further heightens my fears. She escorts me back to our dates and introduces me as Lorraine Simmons, an old girlfriend of hers and that I am now separated from "my husband" and will be living with her till I get re-established as a single woman after a very demeaning marriage. She makes me show that I am still wearing my rings but that I really know that the marriage is over and that I will be starting a new phase in my life and just needs a little time and tenderness from the right man before I become comfortable being a single woman again. She further embarrasses me by telling that unfortunately for me it's "my time of the month" and hopes I will good company tonight. I am on the verge of tears totally embarrassed by the new position my wife has forced upon me. Brad reaches around my waist and gently kisses me on the cheek as he brushes my hair from my face and I feel his other hand lower to grasp my behind. Jim greets my wife, Diana, with a very passionate embrace and kiss all I can do is stand and watch as she emits very womanly moan to further emasculate me. I am instructed to bring our dates a glass of wine to start our evening. I begin to open a bottle of wine, but Brad rushes over and surrounds me and opens it for me. He is eyeing me up and I don't know how to respond since I have never been in this womanly position before. Diana tells me to start flirting with my date and act as she does with Jim or she will make tonight a living hell for me. Diana promises to give me an advance degree in the arts of being a woman. Brad offers a toast and says how lovely I look and how he plans to show me a great time and treat me with a great degree of physical interaction. After empting his glass he embraces me and gives me a passionate kiss. I feel his full mouth on my lips and then the thrust of his tongue into my mouth and due to his firm embrace must endure the attack as would a natural woman might under similar conditions.

My first date will be a series of new experiences and hopefully for me I van completed my first night as a "real" woman without any further problems arising. I had forgotten that my wife moves in an elite circle and I will in public with a man whom is expected to treat a lady with respect. Since I now looked the part of a natural woman I should be accorded that honor. Before leaving I was helped into my sensual silver fox fur coat and at this moment I knew my life was now alternated and I was helpless to steer the direction my life would take in the future. Diana, my wife, had complete control and I had better do everything she planned for me and that included being a woman for the balance of my life. I walked out the door and I knew that I was Lorraine Simmons and that a whole new life was starting.

  

  

  

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