At my mother's suggestion, I enrolled in an art class at the local community college. She always felt I didn't pursue my artistic talents strongly enough. For my part, I was just hoping to meet new friends, as my old ones were becoming somewhat stale. What I mean is, they didn't understand my lifestyle.
You see, I like dressing as a woman as often as possible. I'm only 21, yet skilled enough to pass easily in public. The reason for this is, once again, my mother. My father died right after I was born, and since my mother really wanted a girl, she raised me as one until I was about 12. With the onset of puberty she was forced to let go, and allow me to be a boy.
But, I didn't want to let go, and continued to dress as a girl at home. My mother really loved that, and would often take me shopping with her. It was her guidance and coaching that taught me how to pass in public. And it was her credit cards that allowed me to acquire a large wardrobe of women's clothes.
I'm really fortunate, too, that my body type, 5'6" tall, very slender, and long blond hair worn in a pony tail, allows me to do this whenever I want. Further, my mother has been sharing her Estrogen with me since I was 14, so I have nice breasts and a shapely figure. At her urging I had my ears pierced when I was 15, and I started wearing earrings. After I finished high school I began spending most of my free time dressed as a woman, which my friends didn't like at all.
Anyway, let's get back to the art class. The first day of class I was dressed in guy mode, in jeans and a loose fitting sweat shirt to conceal my breasts. I was assigned to share a table with a good-looking guy, 6'2" and about 30, named Rod. When I sat down he smiled and introduced himself. I smiled back, saying. "Hi Rod, I'm Sandy. Nice to meet you." Rod just looked at me, like he was mentally undressing me. It gave me goose bumps, as I had never had a guy come on to me like that before.
I was, however, more than a bit interested in Rod. If he was going to flirt with me, I'd have a little fun of my own. After the first week of classes, Rod asked if I'd like to join him for coffee when class ended. "I'd love to Rod," I said, in a soft and feminine voice. "Where's the coffee shop?" Rod gave me a quizzical glance, surprised by my voice.
"Just across campus," he said, "so we can walk there in less than 5 minutes." His gaze never left my eyes as he spoke, which was a big turn on for me. I blushed a little and turned away.
Well, we had coffee, talked and laughed for about an hour, and then I went home. My mother greeted me at the door, asking if I'd met any new friends yet. "Just one, Mom," I said over my shoulder. " A really cute guy named Rod. We had coffee after class today."
"Sandy," my mother said, smiling, "are you finally taking an interest in men? Well, I'm not at all surprised, since you love being a woman. I'm so happy for you dear."
"Well, I'm really intrigued with Rod. He's sweet and good- looking, and I like being with him. I hope he asks me for a date."
"Oh my," she said, startled a bit, "it's that serious already. Well, I hope you really know what you want Sandy, and just be careful." She smiled and gave me a hug.
"I know what I want Mom," I replied, "I want to be a woman with a man in my life." I was hoping Rod would be the one. I just needed to find a way to get him interested.
For the next class I wore a very feminine blouse along with perfume, bracelet and a women's watch. The blouse was low cut, allowing my cleavage to show. Rod loved my perfume, and noticed, I think, that I wasn't wearing a bra. I began acting and talking like a woman, and he was getting intrigued. The following week I added lipstick, mascara and eyeliner, clear nail polish, and a necklace and matching earrings. Again I wore a low cut knit blouse, and added women's slacks, stockings and 1" heels. He was fascinated at my apparent transformation, and commented about how nice I looked and smelled.
We went for coffee after every class, talking, laughing and flirting. After three weeks of flirting, and me becoming completely feminine, he started to really open up. He told me that he had been married, but it ended in a bitter divorce. He also said he was finding himself attracted to men, although he hadn't acted on it. He couldn't see himself, he said, being in the gay scene. I took his hand and held it, thanking him for being so honest. My heart was jumping, just thinking of the possibilities.
"You know Sandy," he said as he gazed into my eyes. "I can't quite figure you out. When we first met I was sure you were a guy, but now I'm not sure what sex you are." He paused, blushing. "That came out kind of awkward, sorry. I'm just confused."
"What would you like me to be?" I responded, smiling at him, a slight giggle in my voice. I had thrown him for a loop, just as I intended, and I had also gotten him very interested.
Rod looked at me for the longest time, and then said, "I want you to be just as you are, a mystery." He leaned over the table, giving me a light kiss on the cheek. I squeezed his hand in response. I was falling for him in a big way, and really wanted him to ask me for a date.
I had been wearing my shoulder length blond hair in a ponytail that was vaguely feminine, but now was the time to pull out all the stops. My mother helped me curl and set my hair the night before the next class, after which I shaved everywhere. The next morning she got me up early, asking if I was going to go through with my plan. "Yes Mom, I really want to do this," I said. She gave me a big smile, and a pat on the arm, as if to say she understood everything.
After breakfast, I did a very light job with my makeup, as I was going to get a complete makeover at a beauty salon. I did add a lavish amount of perfume though.
I put on my lingerie, starting with a lacy ivory pushup bra and garter belt. The bra created several inches of cleavage, which looked really sexy. Nude stockings came next, along with ivory tap panties and a half slip. Finally, I slipped on a pair of 3" black heels. I added a necklace and earrings, bracelet and watch, and slipped on an ivory silk blouse and black knee length skirt with a black belt. I left the top two buttons of the blouse undone, so my cleavage would show. With my newly styled hair I looked better than I ever had before. My mother smiled when she saw me, and said, "Oh Sandy, you look lovely this morning. Have fun, and I'll see you when you get home."
"Thanks Mom, I will," I said, as I picked up my purse, fumbling for my car keys. "See you after class."
At the salon the beautician did a fabulous job with my makeup. I went there as a feminine looking woman, and came away a stunningly gorgeous blond. This will get Rod's attention, I thought.
I entered the classroom by the rear door, and Rod didn't notice me, but the instructor did. He stared at me, surprised at my appearance. I just smiled at him. I approached our table from the rear, and as I passed behind Rod I placed my hand on the back of his neck briefly. "Hi Rod," I said in a very seductive feminine voice, as I sat down. I turned and looked him in the eye, and smiled. "Do you like the way I look today?"
Rod just stared in stunned silence for a minute or so, his eyes wandering over every bit of me. He lingered just a bit on my cleavage. "Wow Sandy, you look fantastic today," he said as he stared at me. "I think you're the most beautiful woman I've ever seen." He was a bit flushed with excitement, and obviously taken by my very feminine appearance. I was pretty sure I had him hooked.
We went for coffee after class, and as we walked across the campus Rod gently took my hand. I moved closer, so we were just touching as we walked. At the coffee shop he sipped his coffee in silence for a few minutes, and finally turned to me, nervously clearing his throat. "Sandy, I've never been with such a beautiful woman. I'm really nervous and afraid I'll be rejected, but would you like to go out for dinner this evening?" His eyes told me he really wanted me to say yes.
"Dinner tonight? I'd love to Rod," I said, smiling happily. "I thought you'd never ask." I was excited beyond words at the prospect of my first date as a woman, and with a hunk like Rod to boot. I wrote down my address for him, and he said he'd pick me up at 7:30. When we got up to leave the coffee shop he took me in his arms and kissed me passionately, drawing applause from the other patrons.
When I got home I was bursting with excitement. "Mom," I said breathlessly, "He asked me to go to dinner tonight. I'm so happy right now. He kissed me today."
"Oh that's wonderful news," she said, smiling. "And he kissed you? That's great. I'll help you get ready, so we can pick out just the right outfit for you to wear. I love seeing you so happy." She was beaming with delight.
We rummaged through my large walk-in closet for a bit, selecting a black long sleeve slinky knit dress, very low cut, that fell just below the knees with black beaded fringe on the hem. It would be perfect for an elegant dinner with him. I went through all my jewelry, finding just the right necklace and earrings combination, a bracelet that matched, and two rings.
After bathing, being careful not to mess up my makeup and hair, I got dressed. Black lingerie came first, starting with an uplift bra, lacy garter and black mist stockings, and panties. I added a black half slip and 4" black patent high heels. I applied a generous amount of Emeraude by Coty, a scent no man could resist.
Finally, just before he was due to arrive I slipped on my dress, admiring my large amount of cleavage, with the necklace calling attention to it. I touched up my makeup and hair, picked up my black patent purse, and I was ready to go. "Here," my mother said, "Have a glass of wine to calm you down. You're much too excited right now."
"Thanks Mom, you're right," I said, as I sipped the wine. "I'm just tingling with nerves. Do I look okay?"
"You look beautiful Sandy," she said, as she looked me over approvingly. "You'll have a wonderful time tonight. Why don't the two of you come back here after dinner, and spend a little time together alone. I think that would be the best thing to do on your first date."
Wow, I thought, she knows I want to be alone with him. Well, okay, so she knows. She would have found out soon enough, I guess, and it doesn't sound like she minds a bit. "That's a good idea Mom," I said as I finished the wine. "We can snuggle on the couch or something." I smiled at her, letting her know I appreciated her support. Just then, the doorbell rang. It was Rod, right on time. As I stepped out the door, he nodded approvingly at my appearance, and we left.
Dinner with Rod was wonderful, not only because it was a very good restaurant, but also because I was a woman with my first date. He fawned over my every need, as we laughed and flirted the whole time. We arrived back at my house about 10, and my mother met us at the door. I introduced Rod to her as we entered.
"Hi Rod," she said, taking his hand. "So nice to meet you. Why don't the two of you make yourselves at home on the couch, and I'll pour some wine for you." Rod took my hand and we walked into the living room and sat down on the couch. I slid close to him, and he slipped his arm around my shoulder. I allowed myself to melt into his arms. "Here, you two, have some wine," my mother said, as she handed us each a glass. "I'm just going to bed."
With that she turned to go upstairs. Thankfully, her bedroom was upstairs, while mine was downstairs, and at the opposite end of the house. At the foot of the stairs, she turned and said, "I hope you're still here in the morning Rod, as I'd like to fix breakfast for both of you. That way I can get to know you a little better." She smiled at both of us and turned and went upstairs.
"Oh god," I said to Rod. "I'm so embarrassed. I had no idea she would say something like that."
"It's okay Sandy," he replied, chuckling a bit. "The thought of spending the night with you is exciting. If it's okay with your mom, it's okay with me." With that, he reached over and pulled me toward him, kissing me passionately. I more than returned the passion, kissing him over and over. He ran his hands over my body as we kissed, making me hot with desire. My hand instinctively slid from his knee to the inside of his leg, almost touching his erection. He let out a little moan.
After several more kisses I sat up and said "I'd like to slip into something a little more comfortable. Why don't I get you some more wine, then go change. It'll just take a minute." I got up and poured Rod another glass of wine, handing it to him as I made my way to my bedroom. After closing the door I quickly slipped off my dress, bra, panties and slip, but left my garter, stockings and black patent heels on, as I thought they made me look sexy.
Then I put on a black satin and lace negligee and matching robe, tying the cord loosely around my waist. The negligee was mostly lace, and almost sheer, and when I sat down my legs protruded out in a very sexy way, showing the tops of my stockings. Because I tied it loosely a lot of me showed, including my bare breasts. I tingled with excitement at the thought of what was about to happen. All of my practice dressing as a woman had been for this moment, when I was going to make love to a man for the first time. I just needed to make sure Rod knew what I wanted.
Gliding silently back to the living room, I bent down to retrieve my wine glass, allowing Rod to get a glimpse of my breasts. I smiled at him, and said, "I'll be right back lover. I just want to get some more wine." He had a look of pure lust on his face.
When I returned to the couch I sat down beside him, took a sip of wine, and leaned over and kissed him passionately. He slid his hand inside my negligee, fondling my breasts softly. "Hmmm, nice baby," he said as he kissed me again and again. I tingled with passion, as his hand glided softly over my bare breasts. My nipples were really sensitive, and I gasped as he touched them.
"Oh Rod, I want you so badly," I whispered in his ear, kissing him on the neck and cheek. My hand moved from his knee up the inside of his leg, brushing lightly over his erection. Feeling his enormous, throbbing member through the light fabric of his pants, I started breathing more rapidly. As I stroked his cock it became harder and longer. I wanted desperately to slide my hand inside his pants and feel this wonderful erection.
Sensing my desire, Rod began unbuckling his belt. I fumbled with his zipper, getting it down just as he rose up a bit, and slid his pants and briefs off down to his ankles. He gazed at me and said "Go ahead, I know you want to kiss it baby." He lightly pushed me toward his now bare erection, so I slid down on my knees, taking his cock in my hand.
It felt strange, holding another man's cock like that. I'd never done that before. Slowly, I started to stroke it, as it became harder and bigger. I really liked the way it felt, and the way it responded to my touch. "Just lean down and kiss it Sandy. You'll love it, I promise." With that he applied the lightest pressure on the back of my head, signaling he wanted me to kiss it.
I couldn't resist any longer, so I lowered my head and lightly kissed it. It tasted wonderful, so smooth and soft, so I kissed it again and again, my tongue flicking along the shaft, moistening it. "Take it in your mouth baby, all the way in," Rod moaned softly, his desire and passion boiling. "I've been dreaming for weeks about this. Hurry baby."
Eager to please him, I lowered my head down, sliding my mouth down his cock. I took it deep into my throat, my tongue caressing it. I loved the taste of him, as I slowly moved my mouth up and down his shaft, sucking voraciously. I tried to take him all the way into my throat, as his manly scent filled my senses. His cock grew larger as I sucked it, his passion building. This was heaven, I thought, having my lover's cock in my mouth, about to explode deep in my throat.
Rod started pumping his hips in time with my movement, as we worked together to bring his magnificent erection to climax. "Oh baby," he cried, "that feels so good. Deeper baby, take it all the way in. Oh yeah," he moaned passionately, his hands clasping the back of my head.
I loved every minute of it, as I sucked as hard and deep as I could. His hips began moving more rapidly, his breathing grew shallow and fast. I sensed he was about to come, so I took a deep breath and took his cock all the way in. Just then he cried out, "Oh yes! Yes! Baby yes!" as he shot his climax deep into my throat. Wave after wave exploded into my mouth. It was delicious.
Finally, he relaxed a little, as I continued sucking him for a bit. I was rewarded with one final spasm of climax, and then he was completely spent. "Sandy, baby," he said softly, as he stroked my hair, "that was just the best ever. I hope you want to do that again."
I got up from my knees and sat down beside him, putting my arms around him. I reached for my wine and took a long drink, washing his climax from my mouth. "Rod," I said, "I loved it, and I hope we do it again, as often as you like. I wanted to be your woman from the first day we met. I've dreamed of being with you, having sex with you. Tonight you made me very happy."
He took a drink from his glass, set it down, and reached over, fumbling with my robe and negligee. "You are my woman Sandy," he said as he kissed me. He slid his hand inside my robe, feeling my stocking-covered legs, then moved his hand up toward my aroused cock. The moment of truth had finally arrived, as I waited nervously for his reaction to what he was about to find.
His hand found my stiff cock, and he began stroking it. Softly, he said, "Just what I was hoping to find. You're the perfect woman for me Sandy." He kissed me several times, then asked me to stand and remove my robe and negligee. I stood before him, completely nude except for the stockings and garter, and my 4" heels, as he gazed appreciatively over my body. "Nice, really nice," he said as his hands stroked my legs, "just what I've dreamed of. I was hoping all along that you'd be like this. It just took me forever to work up the nerve to ask for a date."
As he said that he lowered himself down on his knees, and kissed my erection several times. "This is the first time for me too," he said as he took my cock into his mouth. It felt wonderful. Slowly I moved my hips in time with his sucking, as my raging erection slid in and out of his mouth.
I clasped my hands around his head, moving my hips in and out. "Oh Rod, that feels so good. Keep going baby, more." I was really getting excited now, my hips frantically moving in and out, my hands tightly clenched behind his head. Finally, I climaxed in a passionate frenzy, deep in his throat. "Oh, oh, oh, god, that feels so good," I moaned, holding onto his head. "Oh Rod, that was wonderful."
Rod kissed my cock several times, then got up and returned to the couch. I slipped my robe back on and joined him, melting in his arms. "Let's go snuggle in bed," I said softly, as I kissed his ear, "where we can curl up nude under the covers."
He nodded and got up, pulling his pants up. We closed the bedroom door, and I helped him get undressed, then we got into bed and pulled the covers up around us. Rod took me into his arms, kissing me softly, stroking my breasts and cock. I turned my back to him and snuggled up tight. I could feel his growing erection against my rear, so I lifted my leg, allowing it to slide between my cheeks. It felt wonderful there.
Slowly, Rod started moving his erection in and out, massaging it between my cheeks. I loved it, and responded by moving with him. I could feel his erection growing with each thrust. He kissed me softly on the neck, and said, "Do you have any KY lubricant?" I tingled with excitement, knowing what was coming next.
"Yes," I whispered, "in the nightstand." I had been using KY and a dildo for several years for pleasure, so I was ready. He began applying it to my opening, rubbing it deep inside, which felt wonderful. Finally, he applied a large amount to his erection. "Hurry Rod," I said breathlessly, "I want you so bad." I got up on all fours, spreading my cheeks for him.
Before I knew it he was inside me, plunging his rock hard cock deeper and deeper. I gasped with delight at the feel of his huge erection deep inside me. I had never felt such pleasure before. I tried to move in time with him, to help him get as deep as he could. In and out he kept thrusting, bringing me to a level of passion I didn't know existed.
"Oh Rod, more baby, more, faster baby. I love it so much," I moaned passionately. Rod was moving in and out more rapidly now, and I could sense he was near his climax. He reached around and grasped my stiff cock, stroking it in time with his movement. "Push baby, come on, push," I urged him. "I want you to come deep inside me baby, please. It feels so good, you feel so good. Hurry baby." I was white hot with passion by this point, with the pure pleasure of having him so deep inside me. I felt like I would climax with him, as he continued stroking my cock.
Then, Rod pulled my hips tightly to his groin, and climaxed deep inside me. As he did, I came on the sheet in a moment of passionate frenzy. He stayed inside me for a bit, then collapsed on the bed, exhausted. I rolled over and snuggled up to him, stroking his head. "Baby, that was great. The best. I hope you want to be my girl," he said softly as he put his arm around me.
"Of course I want to be your girl, silly," I said as I kissed him. "I want to be your girl forever." I snuggled next to him, happier than I had ever been. We both were completely spent, and drifted off to sleep. My last thought was that I was going to throw away all my men's clothes.
Suddenly, out of our sleepy haze, there was a knock on the bedroom door. "Sandy honey, it's time for you and Rod to get up." It was my mother. "I hope you had a nice time last night. Anyway, it's time for breakfast, so why don't you two get up and I'll fix you something. Then you can tell me all about it, okay?"
Paula paulabthomas@yahoo.com.au