The Beginning of Womanhood by Barbara Montana I awoke that morning as I had during the previous three months clad in a nightgown and my hair in curlers. This would not seem so strange to the average person except for the fact that people of my sex (male) don't usually wear nightgowns. My wife Carol had gotten me started on the wearing of nightgowns and other assorted pieces of female finery. I was somewhat shocked when she first suggested it but I knew that she meant business when she would only have sex if I were dressed as a vixen. She started one night shortly after we were wed by leaving a long red floor length nightgown on my side of the bed before we retired for the evening. We had been out partying all night and I had a few drinks in me. Carol had already changed into a long silky black low cut nightgown and was laying on top of the covers while I was taking off my cothes and getting ready for bed. I looked at her and my side of the bed (with only my bikini briefs on) and asked her why she had the red nightgown on the bed when she already had one on. She stated that the red nightgown was for me. I looked at her in disbelief. "For me?", I said. "Yes" Bob, she replied and stated that I looked a bit horney and the only way I would get near her was to wear the nightgown. I figured "what the heck" and put it on. "Are you ready for me now?", I asked. "Not yet" she stated "You're not going to leave that underwear on under that beautiful nightgown are you?" I looked down and pulled my gown up. Maybe the underwear didn't go with it. She went to her bureau and pulled out a pair of red tap pants and instructed me to put them on. I immediately put them on and asked Carol if that was all. She said it was for now except that I had to go downstairs for a candle. She said she felt romantic and that would fit her mood. "By the way, what did your sister Jill call you?... Barbara? I blushed.. I complied with her wishes and went downstairs in my new clothes and rummaged through drawers for a candle. While walking around I felt the silkiness of the long red nightgown on my body and the weight of the straps on my shoulders. I enjoyed the swishing of the tap pants on my crotch and thought back to my younger days when my sisters dressed me up when my mother was out. I had been raised as the youngest of five with four sisters who were older. I was somewhat a toy to them, something to dress up and play with. My thoughts went to a little yellow party dress that they had me wear one day. I resisted but without avail and thay finally got it on me. When they got me into it, my resistance stopped. I knew I had been beaten and just took a breather. My oldest sister, Jill, looked at me and said, "Bobby, I think you look more like a Barbara." Being twelve, I couldn't think of anything else to do so I stuck my tongue out at her. She and my other sisters laughed and said that I looked like a little sissy with my yellow dress on and my tongue out. I was humiliated. They comforted me after I started crying and told me they wouldn't bother me any more if I completed my outfit. I agreed and put on white anklet socks with turned down fringe and black patent leather pumps that had belonged to Jill. Jill also handed me a pair of panties that had tiers of ruffles on them and told me to put them on. I was totally embarrassed but did so after shedding my male undershorts from under my frilly party dress. My sisters were all giggling at this point and I was ready to break down and cry. Jill noticed my predicament and gave me a hug. She told me I looked pretty and not to get so upset. My other sisters were saying, "What's wrong Barbara?" (in a mocking tone) as Jill was consoling me. Jill took me into another room and told me that I really was pretty in my dress and asked me to turn around in front of her. I did it and then she asked me to put my arms out as I did my swirl. I did that for her too. She held me by the arms and said that I was as pretty, if not prettier, than my other sisters. I came back to reality and realized that my yellow dress had been replaced by a red nightgown. Carol was yelling from upstairs. Where is the candle? I want to have a soft mood here in the bedroom. "Bring it up here and light it," she dem- anded. I pulled the nightgown up to my knees with one hand, rushed up the stairs and complied with her wishes. "You know Bob," she said "I was talking to Jill the other night and she told me stories about when you were young and your sisters used to dress you up." She said that you didn't like it at first but after a while you really didn't need any encouragement. As she spoke on about my experiences with my sisters, I wondered how much Jill had actually told her. It seemed as she went on that there was very little she didn't know. I admitted that I had learned to enjoy wearing girl's clothes and playing little girl's games including dolls and jump rope. My sisters had conditioned me at a very young age and it was a matter of survival in that household. Carol said that she liked the idea of me having an obvious feminine side. She said she wanted to explore it more with me and that she would very much like me to dress up for her and to let her guide me into the ways of womanhood. "I'm kind of excited about this Carol," I said nervously "but I'm kind of scared too." "What are you suggesting?" I asked. She said that since I had such a slight body and such fine features that I would have no trouble passing. She also said that she would like to have a girlfriend to shop and gab with and that I would be perfect. She also humiliated me when she said that I was obviously effeminate and her friends had noticed that and commented to her about it. She said that some were actually jealous of her because she was always able to talk to me about clothes and other feminine things in front of them. I was encouraged by Carole to participate in conversations with her girlfriends when they came over. They were a bit guarded at first when the talk inevitably turned to men, but after a while they discussed their periods, affairs, fantasies and other juicy tidbits in front of me and let me participate fully in the conversation. When the conversation got around to men I usually clammed up but every once in a while I would join in on the commentary about how attractive some male movie or soap star was and the many romantic rumors that surrounded them. After a while I was totally accepted in their gossip and they often substituted me for Carol when they called for her and got me instead. These gossip calls came especially from two of our friends, Peggy and Susan. I became as caddy as any of them and freely talked about the bitches of the neighborhood, gaudy outfits that were being worn by those women we didn't like and other fun topics. Carol said it would be logical for me to express my feminine side and to dress the part occasionally. She then dropped a bomb on me. She told me that she had spoken to Peggy about it and that she had agreed that it would be a good idea. I was flabbergasted. "How could you embarrass me like this, Carol," I said, "oh, how am I ever to face her again?" I held my head in my hands and sobbed. Carol put her hand on my shoulder and told me not to get so upset because Peggy was a friend and should be trusted as such. "Sure," I said, "and the next one she'll tell is Susan." I was filled with a sense of sorrow that my fond relationship with Peggy and Susan was now touched by my secret desires and would never be the same again. I felt like I had lost my best friends in a matter of minutes. Just then the phone rang. I thought it was odd since it was almost eleven o'clock and we usually didn't get calls this late. Carol picked up the receiver, "Oh hi, Peg," she said. I almost died. There I was sitting on the bed with my nightgown and panties on, slobbering and Peggy had to call right at this very moment. I wanted to crawl under the covers and hide. Peggy obviously had a problem with her car and needed a ride to work in the morning. Carol told her not to worry that "Bobby would give her a ride." I held my hands over my mouth and wanted to scream. It got worse. I heard Carol say "wait a sec" and then handed the phone to me. I was in a cold sweat at this point. "How could you do this?" I whispered to Carol. She handed me the phone and I squeaked a hello to Peggy. She said "Hi, hon. I got a problem. My car broke down and Carol said that you can give me a ride to work tomorrow. Is that okay?" I said sure (my voice was cracking by this time). She then continued and said that she had a long talk with Carol about me and that she didn't want me to be embarrassed. I responded that I was and couldn't help it. She said that I was one of her sweetest and best friends and that she wanted me to know that if anything, my desires to dress as a woman could help our friendship grow. I cried and she tried in vain to console me. I finished the conversation by saying that I would pick her up in the morning at eight. She then asked me to put Carol back on. Carol spoke briefly to her and then hung up the phone. She disappeared downstairs. I laid on the bed thinking and worrying about what was next for me. Could things ever be the same with my good friend Peggy? Or would she look at me as a freak; someone who should be on the Phil Donahue show? I went into the bathroom and splashed some water on my face. My long hair was at my shoulders and contrasted quite a bit differently with the red nightgown than with my regular attire. I took a brush and brushed it out so that it fell evenly on my shoulders. I liked the image that stared back at me and I smiled. The breast of the nightgown was cut tightly on the bottom and gave the impression that I had small breasts behind the blousy top. I stroked the fabric and my nipples hardened and felt like small pegs. I have large nipples (about the size of half dolars, quite unmasculine and very sensitive. Carol commented on this feature when we were dating and compared them to her nipples which are just a bit larger. She liked and still likes to play with mine during our lovemaking sessions and takes great pleasure in making them stick out when I get aroused. I lowered the spaghetti strap on one side of my nightgown and played with my now naked breast. I looked at the image before me in the mirror. There I was with my long blone hair, parted in the middle (I usually keep it in a ponytail), flowing around my shoulders. One side of my nightgown was down with my nipple exposed and my hand was carressing it. My appearance was quite feminine although I didn't have a great deal of mass in my chest area. I cupped my breast from underneath and pushed it up so that it would give the appearance of a more feminine form. I touched and stroked it with the other hand. I was feeling a tingle in my crotch and lowered my hand to massage it when I was shocked back to my senses by Carol's voice. She was talking to someone right outside! I then heard Peggy's voice. Carol knocked on the door and asked if I was inside. I said I was after getting over the initial shock. She asked me to come out. I pulled my nightgown back up and was completely confused as to what to do next. I looked around for something other than the nightgown to put on. I had left the bath towels in the bedroom after an earlier shower. There were no clothes in the hamper. I had done a wash this morning. There were nothing but face towels on the shelf and I was in trouble. There was no way out and I knew it. I was trapped. I decided to come out and face the music. I brushed my hair again, fixed the straps on my nightgown and walked into the bedroom. I saw Peggy and Carol sitting on the bed talking. They looked over to me as I entered the room and Peggy said, "Hi, hon. (her usual greeting to me) I had to come over after my call. I couldn't think of sleeping after I knew you were so upset." She then got up from the bed and came over and gave me a hug. I almost melted. She kissed me on the cheek and said that she wanted me to know that she was and would always be my best friend. She wanted me to be happy and that she didn't want to lose me. She said that she understood and appreciated my situation and that she and Carol wanted me to give in to it and that as wife and friend they would support me in any way possible. A tear came down her face as she talked to me. I looked into her eyes and took both of her hands into mine. I told her that I loved her and that she was indeed my best friend. I looked at Carol and told her I loved her too. She got up from the bed and we all hugged, kissed and cried together. Peggy held my hand and gave me a small package. I accepted it and opened it. It was a thin gold chain with a gold heart. On the back of the heart Peggy's name was inscribed. She told me to turn around and she fixed the clasp, securing the necklace. She asked me to turn around so she could see it. I saw Carol looking on with a teary smile and I walked to the mirror to admire my friendship pendant. It was pretty and I loved it. "You really didn't have to do this Peggy," I said. "No, I wanted to" was her reply. "You are a dear friend and I wanted to show my feelings toward you. You are going through changes and I want you to know that you can depend on me if you ever need me. I want you to be the happiest girl in the world." She said "girl." I walked over to he and gave her a big hug. I kissed her on the cheek and thanked her again. She said that she had to be going and I said that I would pick her up at eight. She asked if I minded driving her home also. I said I didn't and then she asked if I wanted to go shopping with her. She would be getting out early and she was going to buy some clothes with a recent bonus she had gotten. Carol was smiling and I said "Sure, that would be fun." Peggy gave Carol and I a kiss goodnight and gave me a pat on the butt. "You're going to be fighting the guys off soon, hon. Maybe we should get you some conservative clothes so you won't be mauled. That nightgown makes you look delicious." I blushed and waved her off with a limp wrist. "See you tomorrow" she said. I went to bed that night happy with myself, my wife, Carol and the world. Carol and I hugged each other and fell asleep in each other's arms, two feminine forms resting before a new beginning which would be coming soon. Womanly Part 2 "Coming Out" By Barbara Montana Well, six-thirty came around pretty quickly and I was bushed. Carol patted my rear end and said, "Wake up sleepy-head." "Let me sleep," I cried. She said I couldn't, I promised to drive Peggy to work and I had to keep my promise. Carol pulled me out of bed, helped me off with my nightgown and pushed me into the bathroom with only my panties on. I looked in the mirror. What a mess. My eyes were still puffy from crying and my hair was in knots. I searched for some cream rinse for my hair. Ah, yes, here it is. I pulled off my panties, jumped in the shower, shaved real close, and washed and rinsed my hair (and of course my other parts). I was starting to come alive again. I finished up, wrapped myself in a towel and went out to the bedroom where Carol was fixing her makeup. I was wrapping my hair in a towel when I looked down at the bed where some clothes were spread out. I looked at Carol and she was already dressed for work. "They're for you" she said. I looked again and saw a white satin bra and matching panties, a pair of tight flowered stirrup pants with a pink, jewel neck, tunic length sweater. On the floor was a pair of red ballerina flats. "I can't wear this out, Carol," I protested. "It's not a question of can't, Barbara, you can and you will," said Carol. She directed me to put the clothing on, and threw me a pair of opaque black pantyhose to wear with the outfit. She said that she had promised Peggy that I would pick her up "enfemme" and that Peggy was quite excited. After drying off I resigned myself to putting on the clothes Carol had laid out for me. I started with the panties. Thet had a ridge of lace on the top and legs and felt cool as I put them on. I then rolled the panty hose on. Carol commented at how well I mastered the task. She said that I do it faster than her. I was not sure what to do with the bra so I put the flowered pants on next and then the red shoes. Carol looked at me and said, "What are you waiting for? Put your bra on." I looked back at her and said, "But there's nothing to put in the cups Carol." She laughed and went to a top drawer in her bureau and pulled out two small forms. She inserted them into the bra after I had fastened the front clasp. I slipped the pink sweater over my head and pulled it down around my hips. Carol motioned me over and put a bit of lipstick on my lips. She also dabbed a bit of blush on my cheeks. "Do you want mascara, Barbara?" she asked. I said why not since I might as well be convincing since I was going out in drag. ««She did my eyes and then proceeded to finish hers. "You're lucky in a way, Barbara, not having to work." "Do you think I wanted to lose my job?" I replied. "No, I'm not saying that. It's just that you have time to explore the far reaches of your personality. You are not hindered by time as I am. You look great, by the way," she said. "Thanks" I replied as I was blow drying my hair.« Carol asked me to stop at a jeweler and get my ears pierced this morning at the mall and to get som small diamond studs. After a look in the mirror and checking out the reflection, I was more than glad to say yes to her and to ask where she suggested I go. She told me of a little shop on the second level of the mall which was run by a girlfriend of hers. She put a pair of clip-ons on and said they were for now and new ones would come tonight. I wasn't sure what she meant and she touched my lips with her finger when I was about to ask. "You'll find out," she said. "Now move the car, I have to get to work. You might as well get Peggy now so I can get out of the driveway." I looked at the clock and it was seven fifteen. I was nervous about going out in my new outfit but Carol grabbed me by the arm and said "Let's go, I'm going to be late." So I went. While walking, I looked down at my "breasts" under my long sweater and got a charge. I loved the way they proudly stood out. I generally liked my look. "Baby, I'm going to be late tonight," said Carol. She explained that she had a client coming in from California who was showing a new line of fashions (Carol is a buyer for a large department store) and had to bring him out to dinner. She told me to have fun with Peggy this afternoon when we went shopping and suggested we go out to dinner ourselves. She offered to let me wear a new dress that she had bought and only worn once. I was a black sleeveless cocktail dress that fell mid thigh and looked great with pumps (the higher the better). I told her that I thought things were going a bit fast and that maybe we should slow it down a bit. She looked at me and said, "Who are you kidding? You were born to be doing this and you know it." I giggled a bit and she laughed. "Go get your girl friend and get her to work Barbara. And behave yourself today." I kissed her, careful not to, mess her makeup or mine and went off to get Peggy. On the way over I got quite scared since I had no wallet, no identification, just the clothes on my back and the car keys. I pulled up in her driveway and got out. I walked up the front stairs and rang the bell. She met me in a bathrobe and curlers. Her eyes lit up when she realized who I was after she gave me a double take. "Bobby?" she said. "Yes," I said, "can I come in?" "Oh, sure,sure, I'm sorry. I just wasn't sure it was you. You look gorgeous. Oh, you're blushing. It's okay, it looks cute on you." I was waiting to come up for air. Peggy was racing around the house screaming about how late she was for work, running and holding her curlers in her hair. She was wearing only a shortie kimono silk bathrobe that kept opening as she ran around exposing various body parts. I was really enjoying the show and she knew it. During a sprint with a comb in one hand and an uncurled curler in the other, she finally stopped short about six feet from me. She turned to me and laughed. Her robe was wide open and she was naked underneath. I could see the tuft of hair between her legs and her well formed breasts. She quickly marched over to where I was on the couch and sat next to me. She kissed me on the cheek and said, "I'm not going to work today, Barbara, we're going to play, okay?" Her breasts were fully exposed now as she sat there next to me and I looked at them, rather than her, and said okay. She took my chin in her fingers and lifted my head up so I was looking her in the eye. "Are you talking to them or me?" she asked. "Oh, you of course," I replied. "Good," she said, "I thought I lost you for a minute." I laughed hard and so did she. She picked up the phone and called into work and told them she was not coming in all the while smiling at me. She explained about her car and how she wasn't feeling well and how she just couldn't do it while she winked at me. She hung it up and put her hand out for me to give her "five" which I did and she said' "let's party." I was game but didn't know what to expect. "First Barbara, we have to get you some clothes and lingerie. We can do that this morning. Then we go out to lunch. We'll stop at the hotel for the four to six crowd and then go bar-hopping. Are you game?" I stood there with my mouth open. "That's a big step for me Peggy," I said. She assured me I looked great and would have no problems. She was really charged up about blowing off some steam and needed an accomplice. I was that accomplice. "Peggy, I don't have my ID or credit cards or anything," I said, "how can I go shopping?" She told me not to worry, that she would charge everything on her cards and I could reimburse her. She started to pull the curlers out and dropped her robe to the floor. She stood in front of a full length mirror and combed her hair our. She turned to look at me and said, "Since you're one of us now, I don't have to worry about walking around in various states of undress with you anymore. Come her and help me get dressed." ««I helped her clasp her black bra and matching garters to a sheer set of sandletoe thigh highs. She pulled up a black string bikini panty and finished with a black leather mini and a white see-through blouse. She put on a wide belt with a gold buckle and a pair of three inch spike pumps. A touch of makeup and she turned around and asked "How do I look, Barb?" I could have dropped to my knees. She looked gorgeous. I stared at the pumps especially. She asked if I wanted to borrow a pair and that she could match the red color of my flats to which I said, "Oh, yes might I?" (I couldn't believe I said it but I was completely spellbound by the figure before me and the costume and aura that surrounded me.) I wanted to go further and further with this and wasn't quite sure when or where to stop. Peggy handed me a pair of red spike pumps. I tried them on and they were a bit tight but they fit and I pranced around the room in them. I swung my butt and hips for Peggy and she laughed. She remarked that I appeared to be getting off on the experience. One look in my starry eyes told the whole story. I was. I loved it. She held a hand out and motioned me to come with her into the bedroom. She held my hand and led me to her large closet. "Is there anything that you want to wear today that's in here, Barbara? I have a lot of things that will fit you. Carol says you're a ten just like me." I gazed in wonder at the many dresses, skirts, blazers and blouses that were hanging in front of me. Peggy told me to remove my sweater and my pants which I did. "You can put the pumps back on if you want," she said. I did. I stood there and tried dress after dress on. I was having a ball and so was Peggy. She and I finally settled on a black mini with a flame red low cut blouse with a black camisole showing underneath. I wore garters and stockings underneath and a pair of four inch patent leather heels finished off the look. Peggy teased and sprayed my hair, used additional eye shadow and mascara and finished me off in a black biker jacket with studs. I looked in the mirror and almost fainted. Between the punk hairdo, the tough looking jacket, the low cut blouse and the "knock me down and fuck me" pumps, I was in a state of shock. "Is that really me?" I sad. "Sure is," replied Peggy. "It's fun being a girl, isn't it?" "Yes," I said, "if I ever live through it. My pulse must be about two hundred right now Peggy." Peggy looked at her watch. It was twelve o'clock. "Time for lunch, hon. Let's go to the Homestead." "But that's a pick up joint," I said. "I know, silly, why do you think I recommended it?" She gave me a shiny black leather pocketbook with a long shoulder strap and put some hankies, makeup and an old wallet in. She then opened a drawer in her night table and took a tampon and a rubber and dropped them into the purse too. "You want to look real don't you?" I laughed and we scurried out to the car and to our lunch date.« >>>>>>>> to be continued (soon) >>>>>>>>>