My First Time as a Lady

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My First Time as a LadyI was at my thinnest and finally took some time to try shaving my legs and arms, bikini zone, anyplace on me that had hair. I had been applying generous lotion to my skin on a nightly basis and tweezing my eyebrows. People took notice but said nothing. I still wasn’t ‘out’ but I wasn’t worried about being obvious. It had been a few years since my last cock fix and my wild inner woman needed to play again. I had gone in drag for Halloween that year to work, wearing gogo boots with three inch block heels the entirety of my shift. I had tiny little shorts and striped Wicked Witch of the East leggings. My top came with a padded insert so it gave the illusion of breasts. I rocked a hot Gaga wig, orange with blonde bangs. The first customer of the day had asked what I was doing after work. I laughed it off. He let me know he was serious. He was a cute old man and I was now nearing my thirties so it wasn’t all that wild a concept. I just wasn’t ready to make a date in front of my coworkers. I knew it was working after that, my illusion. I started to wonder which of me was the actual illusion however. I felt high and not just from the heels. I was on my own d**gs. I used what I already had and managed to buy some panties from Walmart in the self checkout lane. I bought other stuff and scanned them quickly. I was still nervous. Even just grabbing them as I passed by the ladies’ clothing section had earned me a few scowls. What a great town! Oh well. I met a guy on Craigslist and had been talking to him via text messages for a couple of weeks. I sent pictures of me on that Halloween and he was very into it. We spoke on the phone and he told me how amazing my voice was. I was so worried about the voice. I know I was an alto all the way through my sophomore year in chorus but I could go quite deep. I tuned my range up and did my best. It felt natural. I didn’t hate hearing myself speak. He finally told me his name was Greg and he was straight but he’d always loved looking at sissies like me in porn or online in chat rooms and personals. He complimented my makeup skills and naturally feminine facial features. He talked to me like a lady and I swooned hard.I packed a bag with my change of persona and headed down the street to his apartment complex. He was only five minutes from me. I loved staying close to my comfort zone. I went in as a boy and he greeted me with a loving hug. “It’s so nice to finally meet you.” He looked me over and smiled. He wasn’t conventionally attractive but I’d never worried too much about that. He was older as usual, in his forties with a gut and a hairy little body. Something about being taller than a man always made me happy. When I was back in my womanizing youth I always went for leggy females. I didn’t realize until later that I was looking for my own qualities in women. I hate saying that like I was using them or something because I never did. It hurt each time I went through a breakup but I was constantly fighting my own duality. The pull to the estrogen side was strong and Obi Wan had trained me well. I guess now is when I mention I’m also a huge nerd (sorry).“I can go ahead and get ready bahis firmaları if you don’t mind waiting.” I looked around at his place and took notice of the aluminum foil covering his windows. He sighed.“I work nights. I do that so I can sleep during the day.”“That’s cool.” I nodded. He’d already told me about his security guard job. I’d offered to bring smoke but he couldn’t so he had some beers waiting in his fridge. “I just had one request.” He grabbed a thong from his bedroom and handed it to me. “I picked that out for you. You can keep it. I just thought your ass would look amazing exposed. I like the ones you had in your pics but I just really love seeing those cute cheeks.” “That’s super thoughtful.” I blushed and accepted the gift. “I got you a nightie too.” Now he blushed. His face was really growing on me. I was starting to understand my own rules of attraction. If I like the guy inside, the outside becomes sexy no matter what. I’d have even gone out with him to places and been proud to be on his arm but he was one of those ’discretion is a must’ straight guys. Craigslist was loaded with them. He handed the thin pink thing to me. “It’s your size.”“That’s why you asked.” I giggled.“I’m going to grab a beer if you want one.” He went into his kitchen. The apartment was small so we were nearly in the same room regardless of how far he wandered.“After I get my makeup done.” I didn’t want to get sloppy and I was a true lightweight. This was important to me. I wanted to look perfect for him and for myself.“Sounds good.” He cracked his Bush open and I went into his bathroom to do my thing. I took my time but not too much of it as it was now his time I was using as well. I did my makeup and lipstick all up, slipped the thong on over my soft cock, and slid into the nightie which fit perfectly. Once I had my wig on I stepped into a pair of regular black heels and emerged as myself.“What do you think?” I asked as I walked into the bedroom and spun around like a model on the runway. He handed me a beer with the cap still on. I appreciated that. I’m sure you understand the caution. He even had lube and condoms on the bed. He was prepared for me and my demands. He raised his bottle and toasted me. The clink sealed his approval and my celebration of a new awakening.“Let me see that ass.” He lifted the back of my nightie. I bent over slightly and pushed my ass out. “Mm hmm.” He sipped his Bush while admiring my lack of one. “You’re fucking gorgeous.”I sipped my beer then set it down on his nightstand. He was sitting on the edge of his bed. I took his beer and set it next to mine. He scooted back as I climbed onto his lap, straddling him. The feel of his bulging crotch against my delicate thong nearly made me orgasm right away. This was everything I’d been waiting for. I felt his chest up as I lifted his shirt and tossed it aside. He looked a bit nervous now, but happy. His eyes were not intense like the last guy. I was in control this time. I tickled his bare chest with my wig and leaned in for a kiss. He was gentle and sensual. I caressed his stubbly cheek and licked his lips. He closed his eyes and purred for me. I could feel his kaçak iddaa cock growing through his zipper and wanted it. I took my time. I turned and sat on his lap, rubbing and grinding against his bulge. He slid his fingers over my hips and down to my exposed ass cheeks. Now I was the one purring. I felt the resistance of the thong as my own cock grew. I started to think of it as my clitty instead. My pussy twitched as I went on with the tease, giving him a private lap dance right there on his own bed. “Do you like that?” I asked in a soft girly whisper, twisting my head back to look at him. “Oh yes.” He slid his hands up my tummy and groped my tits. I moaned and gyrated against him faster. I started to slide down his lap onto the floor. I turned on all fours and crawled up to his zipper. My fingers gently took it down and reached inside of his jeans. His cock was about the same size as my clitty. It was so perfect. I enjoyed size but I didn’t mind him being a bit smaller than the last guy. I stroked him slowly and looked up into his eyes. His face told me how happy he was for all of this to be transpiring. At that moment, I licked the precum off of his tip and he twitched wildly. “Fuck yes, baby.”I took my time sucking him slowly. I teased and savored him. I rubbed his balls gently and pushed them into him a bit. I followed his responses and did everything he liked, backing off from whatever he didn’t seem to. I sucked his cock, licked it, and kissed all around his thighs. I worked down, licking his balls and even gave his ass a kiss. “Oh yeah.” He rolled back to lift his ass up for me and I licked his hole. He was loving it. Another first for me. I spread his cheeks and snaked my tongue deep into him. He tasted like paradise. I pushed one finger in slightly and teased his anus. I licked his balls, then returned to sucking his cock. I took it to the balls and felt it throb in my throat. I’m not even sure I ever had a gag reflex. “You’re so fucking amazing, Princess.” “You saw my bracelet?” I laughed and stroked his wet cock for him.“It was in your pictures.” He giggled.“So observant.” I stood up. “You should lay down.” “Yes ma’am.” He scooted up onto his pillows after I helped him out of his jeans and boxers. I straddled him on the bed and started grinding my clitty against his wet cock. It felt so good. I moved up and felt it teasing my ass. “You should come up here.” He was waving me toward his face. I slid myself up and he pulled my panties aside, kissing my clitty and sucking on it. I was moaning and swaying my hips slightly as he took me into his own throat. I grabbed the back of his head and pulled on his unkempt hair.“You’d better slow down unless…” He didn’t. He sped up and grabbed my ass, sucking every last drop out of me as I screamed and squirted into his throat. “Holy fuck!” I think I nearly blacked out. He grabbed my hips and flipped me so I was the one now laying down on my back, my head sinking into his fluffy pillows. He hovered over me and fed me his cock. I sucked hungrily and massaged his ass, fingering him a bit more. The hair all over it turned me on. Everything about him turned me on so immensely. “I really kaçak bahis want to be inside of you now.” He told me as he pulled out of my mouth. He dismounted and flipped me onto my tummy. My face was buried into his soft pillows, right between both of them. I felt him spank me and pull my hips back, yanking my thong out of his thirsty way. He licked my pussy deep and spread my ass as I had done for him. I clawed at his comforter beneath the pillows and sang in soprano lust. I was on all fours and ready for him.“Oh my fucking God yeah, baby!” I’d never been vocal like that in my life. He licked all over my cheeks and ran his fingers between them, pushing one inside of me. He grabbed a condom and put it on, coating his gloved cock in lube. I felt his hands on my shoulders and reached back to help guide him into me. He fucked me gently. Slowly. It was the very opposite of the rough first time I’d had as boy me. This was a true gentleman. I loved his touch and his cock. I loved hearing him breathing and even snorting. Manly sounds make my ears and mind wet.“You’re so tight. You’re so soft.” He pulled my hips back and went deep inside of me. He thrust quickly but barely came out or went in. He was simply there inside of my pussy, filling it. “It takes me forever and sometimes I don’t even cum.” He told me. “I drink a lot I guess.” I could feel his sweat splashing onto my back and my ass. He placed one firm hand right above my ass and rode me. It went on for probably ten minutes before I fell flat and he followed, hooking his arms under mine. He kept fucking me. “Just tell me if you start to hurt.”“Don’t stop.” I replied without hesitation. Compared to the last guy, this was easy. It was fantastic. I was tingling all throughout my pussy and up my spine. My legs were weak. I came again into his comforter. He heard me orgasm and reached down, grabbing my flat tummy after feeling the juices all over my thong. “That’s fucking hot.” He grunted. He pulled out and snapped the condom off. He was tired. He was coated in alcoholic sweat. He collapsed on the foot of his bed, panting. “I’m so sorry.” He covered his face in shame. I felt so bad for him. I crawled over and sucked him a bit but he stopped me. “You okay?” I felt the most feminine I’d ever felt in that moment. I didn’t care about anything. I just didn’t want him to feel ashamed or inadequate. “Yeah it just sucks.” He chuckled.“You made me cum twice.” I smiled wide. “I think that’s an accomplishment in itself.”“Yeah.” He smirked. “I’d like to see you again if I can.”“Sure.” I nodded. I got up and pulled my wig off. “Does this freak you out?” I asked with my exposed boy hair and messy makeup, still in my nightie and thong.“You look beautiful.” He sat up and kissed me.“You’re a really great guy, Greg.” I assured him before heading back into the bathroom. I washed my face and changed back into my tight guy jeans and shirt. We talked a while and finished our beers. He hugged me tight before I left. I saw Greg a few more times before he moved out of state. I still miss him but life moves on. He unlocked that moment for me. I never was the same again. I knew the true me was that woman who he’d finally shot ropes of cum onto the second time we got together. Not saying he calmed his drinking down for me, but maybe he did. Either way I will always be grateful and feel a tiny swell of love in my heart for him.

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