Transforming Bobby By Paula Thomas
Busted, I thought to myself, totally busted, as my stepmother angrily picked up the phone and keyed in a number. "Hello, John?" she said into the phone. "It's Martha. I finally caught him wearing my lingerie, just like I told you I would. What?" she exclaimed, somewhat exasperated. "Oh, well let's see, my garter, stockings, panties, bra, slip and high heels." She paused briefly, listening. "Yes, of course they were all in black," she replied to an unheard question. "And no, this time he didn't put on one of my dresses, at least not when I caught him."
I squirmed uncomfortably, my world crumbling, as my secret life was being exposed to a stranger on the phone. I wondered who this John guy was. I started to leave the room when she turned and said angrily, "Stay right here young man! You're not going anywhere just now." Resigned to my fate, I slowly slumped down in the corner, trying to block out her voice. I was 17, and nearly finished with high school. Another couple of months I'll be 18 and I can move out on my own. Oh, why did this have to happen?
"Look John, I just can't cope with him anymore," she said into the phone. "Bobby really needs to be around a man like you at this point. Ever since his father was killed in that awful war he's been acting strange, and it's a lot more than just teenage angst. I think proper guidance from you would be just the ticket."
Strange might not be the right word, I thought. Conflicted maybe, about my sexuality. I was really attracted to women's clothes, especially black satin panties, slips and black patent high heels. I had an almost uncontrollable urge to wear them whenever I was alone in the house. I'd started when I was 12, right after my dad was killed. I was wearing her underwear almost every day after school. I guess she must have known, because she appeared out of nowhere and ambushed me after I started getting dressed up today. Boy, did she chew me out.
"I was hoping he could live with you John," she said, "at least until he turns 18 in two months. Oh, that would be wonderful. I'll drop him off tonight. Thanks so much." As she hung up the phone she turned to me, with a look of sadness in her eyes. "You're going to live with my friend John until you turn 18," she said sternly. "And you're going to finish school too. Do you understand me?"
I nodded sullenly, with my head down, avoiding her glare. My life was ruined, I thought, just ruined. Now I had to go live with some guy named John for two months. It'll be agony, I figured. No friends around, in a strange place, and worst of all, no women's clothes to wear. I felt like dying.
My stepmother started boxing up my motley assortment of clothes, lecturing me the entire time about starting to act more like a grownup. She said that she had known I was wearing her things for several years, but figured I'd outgrow it, like so many other boys. But I didn't outgrow it, instead I continued right up until today. I even made several attempts at makeup, and tried on some of her dresses. I really like wearing makeup and dresses, and I dreamed of becoming a young woman. I have long blond hair, a slender frame and stand about 5'7". If I styled my hair a little, I thought, maybe I could pass as a woman, but I never got up the courage to go out in public. Oh, how I longed to do that.
Later that night she drove me to John's house, a big brick house with a circular driveway, in a very exclusive part of town. Oh great, I thought, I'll be living with some old rich dude. Resigned to my fate, I hauled my boxes up to the porch, rang the bell and waited. A light came on, then suddenly the door opened and a slender, athletic man of about 40 appeared. "Hi Bobby," he said, shaking my hand. "I'm John. Please, come in. Let me help you with those boxes." He grabbed a box and started into the house. I followed reluctantly, in a really sullen and angry mood.
John showed me to my room upstairs, and we set the boxes down so I could unpack. He said he'd make sure I was awake in the morning, and he'd take me to school. "Whatever," I said sarcastically, as he left the room. I looked around at a very large bedroom, with a king size bed, dressers, a desk, a bathroom, and a sliding door that led to an outdoor balcony. Nice, I thought, really nice. I guess if I have to be here at least I can be comfortable.
The next day John dropped me off at school, and said he'd pick me up at 3:30. That was cool, since my stepmother always made me wait until at least 4:30. When school finished for the day I walked outside and there was John, waiting for me. I hopped in his car and noticed the smell of Chinese food. "I picked up some food on the way Bobby," he said as he started the car. "Let's go home and eat, then I have a surprise for you."
"A surprise," I said warily as I glared at him. "What surprise?"
"Oh, you'll see after dinner," he replied, smiling. "I think it's just what the doctor ordered for you." So, we rode home in silence, with me not at all interested in talking to an adult. I was intrigued by the idea of a surprise though. The Chinese food was okay, and he offered me a glass of wine, something my stepmother would never have done. The wine helped my mood a lot, and I finally opened up a bit. We talked about my school, my plans for the future, and general small talk. After dinner John said there was a package waiting for me in my room, and I could go up and see what it was if I wanted to. In a flash I bounded up the stairs and down the hall to my room, where I found a large department store shopping bag on my bed. Looking in the bag, I saw something in black satin, so I quickly unloaded the contents. There was a pair of lacy black panties, a black bra, a slip, garter, black mist stockings, black patent 3" high heel shoes, and a beautiful black satin robe with acres of lace. I gasped, stunned by what I'd found. Wow! I couldn't believe my good luck. Just then, the door opened, and from behind me John said, "Go ahead and put them on Bobby. They're all yours and you can wear them whenever you feel like it."
My sullen mood changed in an instant as I held the satin garments up to me. "These are beautiful! Are they the right size?" I said excitedly as I turned toward him, my eyes gleaming with delight.
"They are Bobby," he replied, smiling. "I had a long talk with your stepmother today about this, and she told me what size you wore. I had my secretary go to the mall and pick them out. Do you like them?"
"Like them," I exclaimed, "I love them! Thanks so much John. Oh wow, you made my day, no, my whole year with this."
"Well, go ahead and get dressed up. Come downstairs if you want to. I'd love to see how you look in that outfit," he said as he closed the door.
After getting over my shock and surprise, I got undressed and showered, excited and happy with the unexpected turn of events. Once I dried off I slipped on my new lingerie, trembling with excitement. As soon as I pulled on the panties I got an erection, which always happens. Everything fit perfectly, including the high heels, which were obviously expensive and much better than my stepmother's heels. And the satin robe was wonderful, flowing over me like water. I was in heaven. Fortunately the robe concealed my aroused cock.
After admiring myself in the full length mirror on the wall I figured I should go downstairs. After all, John had bought this outfit, so I guess I should wear it for him. I descended the stairs and made a cautious entrance into the den where John was watching TV. I had never been dressed like this in front of anyone before, so I was really nervous, almost trembling. I was also very aroused by the feel of the fabric, the smoothness of my stockings, high heels and, well, you know, the whole ensemble.
"You look wonderful Bobby," John said, beaming with delight. "Come in and sit down. How do you feel?"
"I feel wonderful John. I really can't thank you enough for this," I said as I sat in a chair, crossing my legs in a feminine manner. My stocking covered legs protruded out of my robe, looking really sexy. And those black patent high heels looked so good. I just shivered with excitement and sheer pleasure.
John was relaxing on the couch, with his feet up on the coffee table, not really paying attention to the TV. He just smiled at me as I spoke. "I really feel completely relaxed when I'm dressed like this," I said. "It's as if this is the way I'm supposed to dress. You know what I mean?" I didn't want to tell him how aroused I was, or that I had a rapidly awakening interest in men.
John offered me a glass of wine, which I readily accepted. "Yes, I know exactly what you mean. I'll tell you what Bobby," he said as he sat back down on the couch. "Let's complete the outfit tomorrow. We can go to the mall after school and find you a really nice dress to wear. Maybe a few other things as well. Would you like that?"
"Yes!" I replied quickly. "Maybe I could try some makeup too. And maybe even curl my hair or something," I continued, almost breathless with excitement.
"Well, sure Bobby," he said as he sipped his wine. "In fact, I have an idea about that. Let me work on it tomorrow. You know, I think you need to explore your feminine side a little, find out what it's all about, what it really means for you." We had a bit more wine, watched some TV, and said goodnight early.
After school the next day we went to the mall, and entered a large department store, riding the escalator up to the women's clothing floor. Before us was a vast array of dresses, skirts, blouses and other things. John took the lead and quickly found a knit dress in black with red and gold accents, long sleeves and knee length. Guessing at the size, he selected one and steered me to the nearest fitting room. I quickly tried it on, and it seemed to fit perfectly, so John bought it. I shivered with excitement at the thought of having my own dress.
We found a costume jewelry display where John selected a gold necklace and a matching pair of clip on earrings, telling me that I should consider getting my ears pierced. I asked about makeup, but John said he had a surprise that would take care of it. Leaving the mall we stopped and ordered a pizza for dinner, which we ate at home. "Ah, it's almost 7 o'clock Bobby," he said as he looked at his watch. "Better get a move on, because Carol will be here in half an hour."
"Carol?" I replied, looking at him. "Who's Carol?"
"Oh, you'll see, but now you need to take a shower," he said, "and be sure to wash your hair." He handed me a small plastic bottle of hair remover, telling me to apply it to my legs, chest, arms and arm pits, and wait 5 minutes before getting in the shower. It would remove all my unwanted hair. After my shower I applied a moisturizing lotion all over, which made my skin feel nice and soft. As I was applying the moisturizer John called through the door. "Bobby," he said after knocking on the door. "Just put on your lingerie and robe for now. The dress will come later."
I sat on the end of the bed and slipped on stockings and garter, panties, bra and slip, and finally my high heels. The stockings really felt nice on my smooth legs. As I was putting on my robe there was a knock at the door. "Bobby," John said, "are you ready yet?" I said yes, so the door opened and in walked John with a very attractive young woman named Carol.
Carol was a beautician and carried several items which she placed on the desk. After smiling and saying hello to me she turned to John, nodded and said, "I can do a lot with him, he's perfect." John just smiled and left the room.
First, she had me sit while she applied hot curlers to my hair. Then, she tweezed my eyebrows into a feminine shape. It didn't take long, which was good, because it hurt like crazy. To define my eyebrows she applied a very light coat of brown mascara to them. She explained that a proper eyebrow shape was essential for a feminine face. Then, she sat in front of me, applying a small amount of foundation, mascara to my eyelashes, a bit of eyeliner, powder, and a touch of rouge to my cheeks. She carefully explained everything she did, and said she'd leave all the makeup she was using so I could duplicate it on my own later. She also told me how to remove it at bedtime. The final touch she added was lipstick, followed by a spurt or two of perfume.
Finally, she removed the curlers and brushed and styled my hair. Satisfied, she stepped back and invited me to look in the mirror. I couldn't believe what I was seeing. I was a gorgeous young woman now! Oh wow, I thought, I didn't know I could look that good. Carol said I could go ahead and put my dress on now, and join John downstairs. With that she smiled, said goodbye and left.
I really was anxious to put on my new dress. I stepped into it, and reached around to zip it up in back. I added my gold necklace and earrings and I was ready. I took a long look in the full length mirror, hardly believing it was me. Boy, was I excited and aroused as I made my way downstairs to the den.
I entered the den, very nervous about being with someone while dressed like this. John was relaxing in his bath robe, his feet up on the coffee table, a glass of wine in his hand. Soft jazz played on the stereo. He dropped the book he was reading and just stared at me, his eyes wide open. "Wow! Bobby, you look incredible! What a beautiful young woman you are. Come, sit beside me tonight," he said as he motioned for me to join him. I slid down on the couch, crossed my legs and tried to look ladylike. His hand rested lightly on my knee as he turned to me. "Do you like being a woman Bobby?" he asked softly, his eyes roaming over me.
"Yes," I replied, "it's what I've dreamed of for years. This is what I've always wanted to be, a beautiful woman. Now I am one, and I'm so excited about it. Could you pour me a glass of wine?" My hand brushed across his leg as our eyes met. I sensed a spark of sexual energy between us just then.
John got up and went into the kitchen, returning with a glass and the wine bottle. He poured one for me, then refreshed his own, before turning toward me. "Bobby," he said, "I want you to feel like a woman tonight, like the woman you're meant to be. I want you to express yourself fully to me as a woman. Do you know what I mean?"
A shiver of excitement tingled through me, hoping that he and I wanted the same thing. I wanted to satisfy a man, this man, right now. "John," I said softly, swallowing hard to muster the nerve, not sure what to say, "I want to be your woman tonight." My hand returned to the inside of his leg, as I gently massaged his thigh.
John leaned back and took a long drink of wine, as his eyes roamed over my face. "Bobby," he said, "I was hoping you'd feel that way. Let's enjoy some wine, relax for awhile, and get to know each other a bit. I just really like seeing you as a woman. You're truly beautiful and it's hard to take my eyes off of you."
I smiled at him, grateful for all he's done for me. I slowly drank my wine, then asked for some more, as I relaxed and enjoyed myself as a woman. Finally, I put my arm around his neck and kissed him gently on the check. He responded by kissing me passionately on the lips, then leaned back again and had some more wine. Wow, I thought, I was just kissed by a handsome man. I didn't think that would ever happen to me. He set his wine down and turned toward me, his arm around my shoulder.
"Bobby, untie my robe baby," he said as his breathing became shallow, "and slip your hand inside." The moment of truth for me had arrived at last, and as much as I wanted to I wasn't sure I could go through with it. My hands trembled as I nervously undid the cord and slid my hand under his robe, gently stroking his leg. I really liked my hand on his bare skin. Finally, I gave him a kiss and took a deep breath. I knew now that I really wanted to do this. Slowly I reached over and pulled his robe open. Much to my delight he was completely naked under his robe. His beautiful hard cock, nicely cut but not too big, beckoned to me. I couldn't resist, as my hand found its way to it, gripping his erection gently. "Please, Bobby," he said breathlessly, "kiss it baby. Kiss it just once for me."
"I'm afraid John," I said, swallowing hard again. "I want to, I really do, but I'm afraid." I continued to stroke his erection, which was slowly growing. I really liked the feel of it in my hand, especially the way it responded as I stroked it.
John gently placed his hand on the back of my neck, pushing my face down toward his gorgeous erection. "There's nothing to be afraid of. Just kiss it for me baby," he moaned, "please, I want to feel your lips on my cock, the lips of a beautiful young woman. I want it in your mouth tonight Bobby." I really wanted to suck his cock, just as I had dreamed of doing, but I hesitated for just a bit, apprehensive about having it in my mouth. But, my resistance was rapidly crumbling and I knew I just had to try it. Slowly I slid down on my knees between his legs. I was nervous, not knowing what would happen. Finally, I summoned the courage and gently kissed his wonderful cock as he moaned with pleasure. I was surprised at how smooth and soft it was, and the taste was nice, really nice. I kissed it again and again, my tongue tracing a pattern around his hardening shaft as he exhaled in sheer delight. I could tell he was getting really hot. This was happening so fast my head was spinning, but I was really starting to like the idea of kissing his cock.
"Oh Bobby, take it in your mouth baby, please," he moaned softly, his hand holding my head close to his cock. I felt hot and light headed with desire, my lips on his cock, my tongue sliding down his shaft. I really wanted to please him, so I slowly took it into my mouth. It was wonderful, as I slid my mouth slowly up and down his shaft. I never imagined that having his cock in my mouth would be so pleasant and satisfying. I really loved the feel, the taste, of his hard erection deep in my throat.
His breathing was becoming more rapid now, his hips thrusting his cock into my throat, his hand pressing harder on my neck. "Oh Bobby, oh baby, take it deep in your throat. Baby, please, deeper. I want to come in your mouth baby," he moaned softly. I responded by taking his wonderful cock as deep into me as I could, sucking slowly in and out, my tongue sliding around it, anxious for his sperm to be inside me. The moment seemed to last forever, and I loved it. I knew then that this is what I was meant to do, to suck my lover's cock and take his sperm in my mouth.
Suddenly, crying out with pleasure, he thrust his hips into my face, held my neck tightly, and climaxed in waves, spurt after spurt, deep in my throat. I struggled to keep from gagging, and finally swallowed his sweet, delicious sperm, licking it off his erection. It was wonderful, better than I ever imagined it could be. God, I loved the taste of him in my mouth. Why was I so afraid? Well, now that I knew how much I liked it, I hoped he'd want me to suck his cock every night. Slowly, reluctantly, I withdrew my mouth from his soft member.
"John, that was great," I said, as I slowly got up, straightened my dress, and sat on the couch, "I loved that sweetheart. I hope you'll let me do that again." I smiled at him, and sipped my wine, as he looked into my eyes. I leaned over and kissed him passionately several times.
" Bobby, you did really great," he said between kisses. "If you're going to really explore your feminine side you'll need more than one dress. Tomorrow's Saturday, so let's go to the mall again. I want you to wear your dress and high heels. I think it'll be good for you to be seen in public. Okay?"
"I'd love to John, that's something I've always wanted to do," I replied after kissing him again. "I just hope I can do my hair and makeup on my own."
"Oh, you'll do fine. By the way," he said as he reached behind the couch, "these are for you." He handed me three large shopping bags from the department store. Inside were complete sets of lingerie and high heels in brown, red and ivory. I was absolutely delighted, and I let him know by kissing him passionately. "My secretary picked them out for you. I figure you'll need at least this much," he said as he smiled and kissed me, "and we can get you more anytime you want."
The next day I took all the time I needed to get ready, and finally we went to the mall. I had the time of my life and passed easily, holding John's arm like two lovers as we shopped. Our first stop was to a small shop specializing in earrings, where I got my ears pierced and gold studs installed. I selected a dozen pairs of dangling earrings, but I'd have to wait a couple of weeks before I could wear them. I also picked out several necklaces. In the department store, at John's urging, I picked out ten lovely dresses in different colors, more than a dozen skirts and matching blouses, lingerie in pink and white, new perfume and lipstick, and several pairs of stockings in different shades. This was really fun!
John made us a light dinner while I put away all my new clothes. After dinner I showered and prepared to dress for the evening. I put on my new red lingerie with nude stockings, and my new 4" red patent high heels. Oh boy, did they look sexy! After doing my makeup and styling my hair, I selected a knit dress in red and black. I was ready to put it on when John opened the door slightly. "This is a little gift my secretary just dropped off for you Bobby," he said, handing me a box. Inside were two silicon breast forms with exquisite nipples. "Just what you needed, baby," he said as he left the room.
I couldn't believe all my good luck. The breast forms fit perfectly in my bra, and really gave me a nice figure. After putting on my dress and jewelry I made my way downstairs to the den. John handed me a glass of wine, and we toasted to our new relationship. We kissed over and over as we talked, laughed, and flirted for more than an hour.
"Tonight Bobby," he said finally as he looked at me, "I'm going to make sweet love to you, to complete your transformation. Then you'll be a woman and you'll never look back."
"Oh John," I said, "I was hoping you wanted to do that. I'm virgin, so please be gentle with me, but I want to feel you deep inside me. Let's do it right now, right here on the floor, baby." John stood up and pulled me to my feet, unzipping my dress which fell to the floor. He untied his robe and let it fall as well, standing nude in front of me. He knelt down and slipped my panties off, then pulled me to the floor. I still had my lingerie and heels on, tingling with excitement and desire, as he lowered himself down on top of me. I wrapped my stocking covered legs around his back as he fumbled with a tube of lubricant, applying a generous amount to my pussy, after which he slid two fingers in and out several times to loosen me up a little. God, that felt so good, and I could only imagine what his cock would feel like inside me. I was so excited I could hardly stand to wait. Finally, he applied some to his erection.
"Raise your hips up baby," he said, "and try to relax. This will hurt a little at first, but if you relax it'll feel really good." With that I felt him thrust his cock slowly into my pussy, pausing a short way in to allow me to relax. "You're going to love this baby," he said softly. "Once you learn how to do it you'll be begging for it all the time."
"Oh John, that hurts baby," I cried, my arms wrapped tightly around his neck as I kissed his ear. "Go slow. Not too deep yet. Oh, baby that hurts. Stop please, oh, oh, that hurts, John baby, oh yes, don't stop, oh god that feels so good. Oh, yeah, that's better. Oh, baby, oh, god that feels so good, please fuck me baby. Push into me John, push baby, yes, fuck me harder! Yes!" My legs were wrapped around his back, pulling him into me. John began thrusting deeper into me, as I was finally able to relax. Slowly the pain subsided. The further into me he went the better it felt, until finally he could push in and out with no pain at all, just pure pleasure. I loved getting fucked as a woman more than I ever imagined.
"Bobby," he moaned breathlessly, "I want to make love to you every night. You feel so good baby." His thrusts became more rapid while my hips moved in and out in time with him, making love, sweet love to this man, like the woman I am. Waves of multiple orgasms washed over me. I was in heaven. Finally, he pushed deep into me, cried out in passion, and climaxed, his warm seed flowing into me like a waterfall. God, I loved it so much. John was right, I'll never look back now.
We lay there in a passionate embrace for a long time, his slowly shrinking member still inside me. It felt so good I wanted it to stay. "John," I whispered, "that was wonderful baby, just wonderful. I hope we can do this every night. I can't get enough of you."
Slowly he rolled off and sat up, reaching for his robe. "Well, Bobby," he whispered softly, "you've become a woman, my woman, so I'll be on top of you most every night from now on." He smiled, and reached for his wine glass, while I just curled up on the floor in my slip, stockings and heels, happier than I'd ever been before.
"I wonder what my stepmother would think if she knew what's happened here?" I said, looking at John as I giggled a bit.
"Oh, she knows what's going on Bobby," he replied, chuckling a little himself. "The only reason she was mad was because you were wearing her underwear instead of your own. She sent you here so you could become a woman. She correctly figured out that you were a lot more than just a cross dresser, you're genuinely transgendered. What we've done, what you've done, is exactly what you were supposed to do, and exactly what she wanted for you. Like I told you, we had a long talk the day after you came here, and we also talked at length before you got here, and she told me she wanted you to become a woman. My assignment was to turn you into that beautiful young woman, and I've done that for the most part."
I was stunned at this latest revelation. He took a long drink of wine and just looked at me, smiling, then reached for my glass and handed it to me. "I will say though," he added, "that it's certainly been my pleasure. You've turned into a gorgeous and sexy young woman, and I've really fallen for you Bobby." He smiled, leaned over and kissed me gently, his lips lingering on mine.
"Now you've been fucked like a woman, and you responded like a woman," he continued, as I sipped my wine. "Even though you were a virgin you performed really well, and you've got me wanting to come back for more. You have one more week of school, then you graduate. After that we're throwing all your male clothes out."
"I want you to live with me full time as a woman," he said, "day and night, with your body smooth and your hair styled. I want to see you in skirts or dresses and high heels all the time, completely feminine. You'll sleep in my bed and I want to feel your satin lingerie and smell your perfume when I wake up in the morning and when I go to sleep at night. You're going to suck my cock every morning and I'm going to fuck you every night sweetheart." I just sat there listening, a broad smile on my face. I was deliriously happy. "I want you to start taking female hormones next week," he continued, "and in a few months you won't need those breast forms. I think you'll really like the effect hormones will have on your body."
He paused briefly and smiled as he took another drink. "The hormones will change your figure for the better over the summer," he continued, "so if you need new clothes we'll get them, as many as you want. Money is no object. I'll get you a driver's license with your female picture, and a credit card in your name so you can go shopping on your own. In fact, I would really encourage you to learn how to act on your own in public. The more feminine you become the better I'll like it. That reminds me, there's a BMW in the garage that you're free to use. In short, baby, once school is done you'll be a woman, my woman, full time, living with me as my wife. Does that sound good?"
I just looked at him, studying his face as he spoke, as I tried to process everything he said. My mind was racing, this was happening so fast, and I felt like I was in a fog. Finally, I said "It's like a dream come true John. It's what I've always wanted, and I'd love to suck your cock every morning, having the taste of you in my mouth. Could I start tomorrow morning?" I sat up next to him and smiled, put my arms around him and kissed him passionately.
Maybe he had fallen for me, at least I hope so, but I can tell you, I have really fallen for him.
Paula paulabthomas@yahoo.com.au