Spending time at the club as a girl did wonders for my confidence. Guys were checking me out, dancing with me, buying me drinks, and giving me their phone numbers. I was never very popular as a boy, but as a girl, I was the center of attention! I liked the feeling. As Stacy and I left the club, I put a little extra swish in my walk. The doorman, the one who had let me in without an ID, extended an arm as I walked out and wrapped it around my waist, pulling me toward him. Instead of feeling panicked, it was fun! I laughed and looked into his eyes as he put his arms around me and said, "You come back real soon, Sugar!" Without thinking, I raised my face toward his and gave him a quick kiss. It felt natural. I was a girl, and he was a nice man, so I kissed him. He was still undressing me with his eyes as we walked to the car.
Stacy said that we had one more stop before the night was over. Before long, she pulled the car into the parking lot of the restaurant where we both worked! This was too much. It was one thing to go to a club where no one knew me, but she wanted me to go into my workplace, among people that I knew, dressed up completely as a girl! What would people think?
"We have to go in. Marco is working tonight," she said, and I remembered that Marco hadn't seen me fully feminized yet. We walked in the front door, and everyone said hi to Stacy. No one recognized me, and she introduced me as her friend Joanne from school. Our manager, Helen, was a nice woman in her mid-thirties, and her eyes lingered on me for a few moments before Stacy asked if we could go back into the kitchen. Helen said that non-employees couldn't go into the back, but she let Stacy go. The next thing I knew, Stacy had left and I was standing there alone in front of my boss, dressed like a girl!
"That's a lovely outfit, Joanne," said Helen, and I thanked her.
"Where do you know Stacy from?" she asked, and I stammered that we had a couple of classes together. Suddenly, Helen broke into a smile and said, "It's okay, Joe, no one except your close friends would ever know." For a moment, all the confidence that I had gained at the club vanished and I felt silly standing there in front of my boss. I figured she would be angry, maybe even fire me, but instead, she gave me a hug!
"You really do look pretty! Don't take this the wrong way, but you make a much more attractive girl than a boy." That took me aback for a moment, but I realized that it was a compliment, and I had been trying very hard to look pretty. I smiled and thanked her.
"You obviously do this very well. Do you plan to dress this way all the time?" Dressing as a woman full time was the farthest thing from my mind and I told her so. "That's a shame," she said. "I just had two of my waitresses quit and I could use some experienced help. You know, with tips, working as a waitress would pay a lot more than you're making now."
Things were turning upside down again. I had only just begun to experience presenting myself to the world as a female, and now my boss was actually offering me the opportunity to dress like a girl every day, and getting a raise in the bargain! How would I work it? I would have to go to class, come home and transform myself, then go to work. As exciting as the idea was, it just seemed like too much and I told her so.
"I understand. Well, as good as you look, you should dress up more often. It will get easier for you as time goes on. If you're ever interested, let me know and we'll see what we can work out." She gave me another hug, and I suddenly felt a huge sense of relief that Helen, who I liked and respected (and who I depended on for a paycheck,) was so completely accepting of my dressing up. That little pang of male guilt that had been kicking around in the back of my mind got much smaller. Helen left, and I turned toward the kitchen to see if I could find Stacy and ran right into the big chest of...well...I guess I could say it now...the big chest of my boyfriend, Marco.
"Damn, girl. You could cause a riot," he said. "You are smokin' hot! Turn around and let me look at you!" I gave him a slow, smooth, twirl, giving him an extra long look at my backside. As I turned back to face him, he was right there close in front of me, and he bent down, put his hands under my buttcheeks, and lifted me up until we were face to face. My arms went around his neck, and we shared a long, lingering kiss, I could feel his stiffness as he held me against him, and it wasn't until we heard Helen clear her throat that we realized what we were doing in a public place. Not very professional...
"I'm off in an hour," he said, and I told him that I would wait for him at home. As Stacy dove me back over to my place, my mind was a whirl of thoughts and sensations. I had passed myself off as a girl, and with only one exception, no one could tell the difference. And the one person who did figure it out had just offered me a job as a girl! I had felt what it was like to go outside in public wearing panties, stockings, a slip, bra, and a dress, with my face made up and my hair styled femininely. And I had succeeded! I was much more popular as a girl. Part of me still felt guilty, but I knew this wouldn't be the last time I went out as a girl. Oh, and there was one more thing on my mind...my 6 foot 4 inch black boyfriend was coming over to my place in an hour to have sex with me.
Stacy dropped me off at my apartment and I went inside. I touched up my makeup, spritzed on a little more perfume, and thought about the night I had just had and the days to come. Maybe Helen was right. I knew that I was going to go clubbing again as a girl, and in time, I would get better at transforming myself into a female. Maybe being a waitress would work. I thought a lot about Marco. There was a lot to like there. He was smart, funny, and gentle. He was a year ahead of me in school, majoring in chemical engineering. He was cute, too...no...handsome. He was tall and well built, with a small waist and a tight little bubble butt. He had strong, sinewy arms and legs, and he had one of those six packs that only black guys seem to be able to get. He had a handsome face, full lips... I was thinking about those lips when the doorbell rang. I opened the door and there he was, looking devastating in tight jeans and a tight white tee shirt that accented his smooth black skin.
"Hey, baby," he said with a smile, and I closed and locked the door behind him and we were alone. He picked me up again, just like he had at the restaurant, cupping his hands under my buttocks. I put my arms around his neck, and he effortlessly lifted me up to his level. I wrapped my nylon covered legs around his torso and we just kissed. His tongue tickled my lips, and I opened up enough to allow him entrance, and our tongues intertwined slowly and passionately. I kissed his neck, his ears, and nibbled on his earlobes. I ran my fingers through his hair. Marco carried me to the couch and sat down, leaving me sitting on his lap facing him. After several minutes of kissing, he asked me to tell him about my night.
I told him everything that had happened. From Stacy bringing a suitcase full of new wardrobe and getting rid of all my boy's underthings, to visiting the salon and getting my hair done and having my ears pierced, to dressing up in nylon and lace, then putting on feminine outerwear, all leading up to going outside into the world as a woman for the first time. I told him everything about the club. I even pulled out all the phone numbers that guys had given me. He laughed good-naturedly about all the phone numbers, and that's when I realized something about why I liked Marco so much. He wasn't jealous at all. It wasn't arrogance on his part, he was just...confident. He knew he looked good. I'm sure he got plenty of offers from all kinds of women. It was funny that out of all those women, I was the one he wanted. Wow, there was a profound thought...the woman that Marco wanted was me. We kissed some more, and I had him pull off his shirt so I could run my manicured hands over his strong, luscious chest. We didn't hurry. We just enjoyed each other's close presence, but eventually, I wanted more. I slid off Marco and got on to my knees on the floor in front of him. I unfastened his jeans, and he lifted up his hips as I slid them down his long legs. He was in front of me in just a pair of boxer briefs, the outline of his huge weapon outlined in his underwear. I gently hooked my fingers around the waistband of his briefs, fascinated by the contrast of my small, delicate hands with red-painted nails against his dark, muscled, ever-so-masculine torso. I pulled down his briefs and his cock sprang into view. That little guilty voice in my head cried out as I realized that I was on my knees in a submissive, absolutely feminine position, about to take a cock into my mouth just like a woman. That guilty voice was still there, but it was overwhelmed by everything that had happened that night. I wanted to be a woman tonight. I wanted to be Marco's woman. I wanted to use my hands, mouth, and bottom to give him pleasure. I wanted him to fill me up with his masculine seed and feel it swimming around inside me. I leaned forward toward his crotch and smelled that familiar musky aroma of maleness. I nuzzled against his ball sack and slowly inhaled the heady essence. Marco's hand gently came to rest on my cheek, stroking me as I licked and nibbled at his manhood. I took took his cock in my hand and licked all the way up the underside, then back down one side, then up the other. Marco was silent, just breathing deeply and stroking me with his big hand. Finally, I was ready to get my mouth full.
I ran my tongue up the side of his cock, pursed my painted lips into a little cocksucking "o" and slowly went down on him. Marco groaned in pleasure. I went as far as I could, trying to get as much of his cock into my mouth as I could, only getting about halfway down. I knew I would have to work on that. I wanted to be able to take him all the way down my throat. If I was going to be a cocksucker, I wanted to be good at it. Marco didn't have any complaints for now, though, as I bobbed my head up and down, swirling my tongue all around the shaft and head of his cock as I sucked. It felt so nasty to have my lips wrapped around another man's big cock, to feel the delicate velvety skin of the shaft between my lips and the hardness underneath. I could see lipstick on his shaft. My lipstick. On his cock. I was breathing deeply, but not panting. It was all so unhurried. I was just enjoying...sucking Marco's big dick. His big, muscled thighs were on either side of my head as I took him into me. They were warm and firm. It made me feel secure somehow. As I knelt on the floor in front of him, the hem of my dress tickled the back of my nyloned legs. I could feel my lace-trimmed panties gently cupping my bottom and my insignificant, irrelevant little manhood. I ran my hands along Marco's thighs, up his torso, and over his chest. Then he took one of my hands and kissed it all over. I rested my hand on his shoulder and went lower and lower onto his cock, bringing the head all the way to the back of my throat. I wanted it to go all the way in! I wanted my lips to go all the way down his shaft until my lips rested against the pubic hair there at the base of his shaft. After awhile, with practice, I could get a little over half of his cock in my mouth, and I was learning to relax my throat and fight my gag reflex. I knew that if I practiced, I could learn to deepthroat even a big cock like Marco's. I had a feeling Marco was willing to let me practice as much as I wanted. He started rhythmically thrusting his hips upward, and I knew what was coming. I pursed my lips around his shaft and bobbed my head up and down his shaft. Marco's breathing quickened, and his hands went to my shoulders, his fingers twitching. His hips began thrusting harder, and he let out little, "oh...oh's!" as I prepared myself to take him inside me. Suddenly, he stiffened and I felt him swell inside my mouth. The first jet coated the back of my throat and I surprised myself by eagerly swallowing. It tasted salty and musky. I was tasting a man's maleness, just like women had done since the beginning of time. I swallowed the second and third pulses from his cock. They were getting smaller now, and I was getting dizzy from the smell and the taste of him. Marco held tightly onto my head, pressing my face into his crotch. God, I wanted this! I knew that I was going to feel guilty about this tomorrow morning, but right now, all I wanted was to have his cum inside me. Cum that I had gotten from him by using my mouth. Marco's thrusts weakened, slowed, then stopped as I sucked the last drops of cum out of his cock. When I pulled my pursed lips up the last time, his cock was clean as a whistle, except for a few lipstick stains. I had swallowed every drop. Now Marco's sperm was swimming around inside me. Marco let out a long sigh, and chuckled. I smiled up at him and laughed, more in delight that we could bring each other so much pleasure than anything else. I got up and got him a beer, then snuggled up next to him on the couch. I knew he wasn't done for the night yet, but I figured he would need a little time to recover.
We snuggled a little more. Kissed a little more. He told me how cute I was and what a world class cocksucker I was. A couple of weeks ago, that would have been an insult, but now, wearing a dress and lingerie, with a man's sperm irrevocably deposited inside me, it sounded like the highest praise. We talked about all kinds of things, not just my adventures in crossdressing and wanton gay debauchery. After a few more minutes, I told him that I wanted to "slip into something a little more comfortable" (I had always wanted to say that to a man!) and went back into the bedroom to change.
My lipstick was a mess, but otherwise, I was still surprisingly presentable. I slipped out of my beautiful new dress and hung it in the closet next to my pants and shirts. "The first of many?" I thought to myself as I hung it up. Would dresses outnumber the pants before long? I stood in front of the mirror and took off my slip. Standing there in a white bra, garter belt and panties, with beige stockings sheathing my smooth legs, I again marveled at how much the visit to the salon and a little makeup had made me look like a woman. I took everything off except my panties, then went to the dresser to see just what Stacy had left for me. Among the assorted slips, camisoles, panties, and stockings, I found a little sheer black babydoll nightie with lace trim around the bodice and hem. It was apparently part of a set, because I found a matching pair of sheer, black, lace-trimmed brief panties and a pair of black stay up stockings in there, too. Oh well, I had shamelessly flirted with men all night and sucked off my boyfriend; I supposed that black lingerie was appropriate. I went into the bathroom and touched up my makeup. When I fluffed my hair, I was surprised at how naturally it fluffed to become more full, bouncy and curly. They had done a good job at the salon. It was going to take some effort to make my hair look like it was on the "male side of unisex," but I wasn't worried about that right now. I drew a tube of lipstick over my lips and put a dab of perfume on the sides of my neck, on the back of my knees, and just for fun, on the inside of the cheeks of my bottom. Then I picked up those naughty sheer black panties. I never got tired of pointing my toes and inserting them into the leg openings of a pair of panties, then drawing the cool, delicate, slippery fabric up my smooth, hairless legs, the lace tickling as they came up to my waist, the fabric snuggling against my bottom and concealing my insignificant little maleness in a feminine, lacy little cocoon. I rolled the stockings into little donuts and put my painted toes through, pulling them up my legs and feeling the soft, gentle caress of the nylon. The nightie was next. It had a built-in padded bra (Stacy thought of everything!) and frilly little lace ruffles around the shoulders, neckline, and hem. The hem fell about three inches below my waist, so you could easily see the bottom of my panties peeking out. I was ready.
I stepped out of the bathroom and went into the living room to find that Marco wasn't there. Nor in the kitchen. Smiling, I went into the bedroom and found a tall, ebony god laying on my bed completely naked. I sashayed over to the bed but before he let me get in beside him, he made me do another slow turn. (I think he really liked looking at my butt.) I lay down next to him and his arms went around me. His huge chest was against mine, and we kissed again. It was long, slow, and unhurried. His big legs and thighs lay against mine, and I teased him by stroking his calves with my nylon covered feet. He got up a told me to lay on my tummy. I thought I knew what was coming next, but instead of feeling him lay down on top of me, he got onto the bed right beside me and started massaging my legs, bottom, and back. It was heavenly! Big, strong, manly hands, kneaded my muscles and deeply relaxed me. His hands lingered around my bottom, and before too long, he began to pull down my panties. I raised my hips to make it easier, and once they were removed, he spread my legs, knelt between them, and began kneading my buns, drawing them apart, working his thumbs closer and closer to my little pucker. Then I felt him kissing me back there! It was so sensuous! He kneaded and massaged my buns and kissed and nibbled all over my backside until all at once, I felt his breath, then his tongue touch my opening. The feeling was electric! Not like having a finger there, or even a cock. His tongue was wet and slippery, and I gasped as he pushed against me, seeking entrance. At that moment, he could have done anything to me and I would have asked for more. All my masculine pretenses crumbled as I pushed my butt back toward him, wanting more of the feeling of his naughty little tongue inside me.
He chuckled and said, "Well, well, it looks like we found Joanne's 'on switch.' " I was past caring as I thrust myself back toward him, relishing the feel of his tongue invading me. I was gasping for breath, and even my little penis was rock hard. Marco kept at it for several minutes until I couldn't take any more. I wanted his cock inside me! I turned over onto my back and put my legs on his shoulders. He leaned forward, applied some lube to his cock, and brought the tip of his penis to my opening. Slowly, he increased the pressure, seeking entrance. He made short little thrusts, slowly relaxing me until I felt myself yielding, opening up to his manhood. Ever so slowly, he kept a constant, gentle pressure on me and in one agonizingly long, unbearably slow movement, buried his entire length inside of me. With every inch, I felt my masculinity slipping away. There was only a sense of sweet, delicate surrender, of giving myself to this man, allowing him to use me for his pleasure. This was where I wanted to be, on my back, with a big strong man taking his pleasure by using my body. Marco stayed buried to the hilt for a long time, letting me get used to the feeling of him being inside me, then he slowly drew back, and gently, slowly thrust into me again. Each entry of his huge cock battered down what little was left of my manhood. He was passionately taking possession of me, and I wanted to be his! I could feel his strong arms around me, and he leaned down and kissed me, his tongue invading my mouth as his cock was invading my innermost depths. Over and over, he thrust into me, quicker now, and my arms went around his torso, feeling how big and massive his body was. Feeling his strong, manly body that was joined to mine. My legs wrapped around him and I squeezed, trying to work him deeper and deeper into me. I had never been so turned on! His hard abs were rubbing against my little penis, adding to the almost unbearable stimulation I was already feeling. He kept into me for what seemed like forever, and just as I felt like I was about to come, his movements became more jerky and spasmodic. He thrust into me harder and harder, ravishing me, and I could feel myself starting to come. Just as I did, I felt him flooding my bowels. He held himself tight against me, getting the maximum penetration into my body. I could feel the looseness around his cock as he lubricated me from the inside. He held there, tight against me for a few seconds, then relaxed and collapsed on top of me. I lay there completely spent. We were both exhausted. His sweat dripped down from his face, his neck, and his broad shoulders on to me. I held him tight against me, tasting his sweat, and I could feel his masculinity softening, still inside of me. I wanted it to stay there forever, but I knew that it would be back soon enough. We held each other a little while longer, then he withdrew from me and rolled over, completely exhausted, onto the bed. He held my hand to his lips and kissed it. I got up from the bed, went to the bathroom, inserted a tampon into my pussy, and took a long, lingering bath. My persistent guilt was trying hard to make a comeback, but it was hard to pay much attention after all that had just happened. As I lay in the tub, I thought that maybe Helen had the right idea. I'd have to talk to her about being a waitress tomorrow, just to see how it might work. After my bath, I toweled off and looked at myself without makeup. The "boy" version of me was back, barely, but I knew that I could change into Joanne whenever I wanted. I slipped into a pink nightie, climbed into bed, and cuddled up next to Marco. He rolled toward me, put a big arm around me, kissed my neck, and fell back to sleep. Tomorrow was Saturday. I didn't set the alarm.
Thanks to all for the kind comments! More of Joanne's story to come!
copyright 2010 Aunt Joanne