Disclaimer: All characters appearing in this work are fictitious. Any resemblance to real persons, living or dead, is purely coincidental. All characters portrayed are consenting adults - so, please be one yourself and don't read this if you're under the age of majority or consent in wherever it is you live or happen to be reading this. If you like it, the author welcomes feedback. If you don't like it, at least send helpful feedback.
After my wonderful lunch with Alan, I hurried back upstairs and got back to my desk. Not more than 5 minutes later, I got a text from Alan: "Given that lunch was good, how about dinner?"
"Tonight?" Was my response - I hope I didn't misunderstand his intentions, but instantly I had butterflies in my stomach (and lusty thoughts in my head).
My phone rang. "Tonight." He responded. "I was thinking Italian - would that suit you? I know a great little place that's totally out of the way"
I wasn't sure how to play this one. Every naughty bone (err, hem... part) of my body wanted to say "YES!" but I knew I wouldn't have time to go home and I wasn't really dressed for a nice date....
"How about tomorrow? I really want to, but I'm afraid tonight just doesn't work for me - I need to stay a little later at work tonight", I lied.
"Well, how about just a drink then, after work? I can't quite get you out of my head" he persisted.
"Okay, I guess I could do a drink. Meet me in the lobby at 7:30?", I offered.
"It's a date". I almost giggled when he said that.
I was on pins and needles - but then panic set in... it was a date. A real date, with a tall, dark-haired, handsome man... the same man I'd been fantasizing about for the last month! A date and I didn't quite look as hot as I wanted to... thankfully, I had my favorite bra and matching thong on - not so much so that Alan would see it (not tonight, at least) - but because I know they're there. They did make me feel sexy - but to complete it, I'd need some stockings.
I told my boss I had to take care of something and slipped out for a quick trip to Victoria's Secret - thank goodness our office was just two blocks away from one of their flagship stores. I found a sexy pair of lace-top thigh-highs. Enough to tease him and make me feel just a bit more risque.
I was back at my desk by 2:30 and I struggled to keep my mind on work until it was time to meet Alan downstairs. Just before 7:30, I went to the restroom and slipped on my stockings, pulling them up under the edge of my business-appropriate, but sexy black skirt... which I hiked up just a bit so that the lace edges might peek out just a little bit. God, I was so turned on...
I rushed to the elevator and right as I stepped into the lobby, Alan came in through the revolving doors. When we met, he took my hand in his and raised it up as he bent to gently kiss it. /swoon/.
Alan led me out of the building and a few blocks over to one of the bars that had become really popular in the last few months. Walking in, past the line, Alan greeted the hostess by name and with a smile, she led us to a private booth towards the back of a smaller room off of the loud main bar area - I was glad because wanted some privacy but I really wanted to be able to actually hear Alan without shouting.
I may be a beautiful woman through and through, but I still have a man's taste in liquor. I love a good glass of scotch. I surprised Alan by ordering a Glenlivet Nadurra. Complex, strong, yet smooth and a little sweet - much like my date. He took it in stride and I think it was a bit of a turn on for him. Still, one drink - and that was it. I wanted to keep my wits about me...
But one thing led to another and Alan talked me into a glass of wine and then another. And before I knew it, I was somewhere between tipsy and drunk... but more importantly, our hands were all over each other - somewhere in the middle of the first glass of wine, Alan's hand found its way to my leg, and slowly it worked its way up my to the top of my stocking. Each inch was electric. I had to stop him before he discovered my secret - I certainly didn't want to have to tell him about that in some bar - but I knew we had to talk about it soon. To get his mind elsewhere, I began to stroke his leg with my hand, eventually brushing against what started to feel like quite a wonderful cock in his slacks. Each time I let my hand linger a little longer, teasing him with my fingertips... we were both torturing each other, yet pretending like nothing was going on, trying not to miss a beat in conversation.
Eventually, I couldn't take it. I had to ask Alan to take me home. Ever the gentleman, he obliged. As I stood up from the table, the alcohol hit me and I slipped just a bit. I ended up right in Alan's arms - and it was a bit of heaven.
We made our way to a cab, Alan holding my hand the whole way to make sure I didn't slip again. I insisted that I was fine - really, I felt okay. Alan insisted that I hold his hand, nevertheless and he asked if he could walk me to my door when the cab pulled up to my place. I knew I should tell him I was okay... but something in me blurted out "yes" before I could convince myself that I was getting myself into trouble.
Alan walked me to the door as I found my keys in my purse. Alan leaned in for a kiss. I kissed him - and told him to give me just a second, but that I didn't want the night to end.
With a loud "click", the deadbolt snapped open and the heavy wood door swung into my apartment. I put my keys down on the table in the entryway, slipped off my heels and tried not to slip as my stocking covered feet carried me across the gleaming hardwood floors. I almost floated down the hall while Alan waited in the entryway. I rushed around my bedroom, trying to make it presentable. After a quick clean-up, I floated back to Alan, still standing in the entryway.
Upon my return, he pulled me close to him and I kissed him even more passionately than our elevator adventure earlier that day. When we both broke off for a little bit of air, I was still buzzing - the alcohol was still hitting me and the making out had really done something as well.
I took Alan by the hand and pulled him through the doorway into my living room - no bedroom just yet. First, we needed to talk. I was scared, but I knew if this was real, I had to be my real self to him.
I sat Alan down on the couch and asked him if he trusted me.
"Of course I do", he answered, "maybe you've missed it, but I think we have an amazing connection, mental and physical and of course, I trust you".
"Can I trust you with a secret?" Was I really about to out myself as transgendered to this amazing man?
"Of course."
"Alan - I know this is quick, but I feel myself so amazingly attracted to you... but you need to know something about my past", I continued... this was really hard, but I trusted him to at least not hurt me, even if he completely lost interest in me.
"Alan, I was born as 'Adam', but I'd always known I was really a woman. Ever since I was a little kid, I knew I was a girl." The words just kind of hung there, in the air.
Alan took a second and said "Maddie - I've had my suspicions for a while. Don't take that the wrong way - you're amazing and totally feminine to me, but when we kissed earlier today, I felt something press against my leg. That, along with your bashfulness under the table made me wonder."
I think I turned a few shades of red.
"It's really okay - kind of hot, actually", he said, as he gently took my hand.
My heart was still beating quickly - a mix of passion and fear - an elixir like no other... but before I knew it, I was crying just a little bit - the tension of it all, mixed with fear and yet, somehow relief.. and a bit of alcohol just made me cry a bit... "Are you sure?", I asked, trying to hide the tears.
"Yes, I'm sure", he said, putting his arm around me and lifting my chin with the other hand.
I could see that he meant it as he looked me straight in the eyes. Nervously, I reached out and gently kissed his beautifully lips. He kissed me back. Gently at first, but soon it was passionate once again. His hands were all over my body - one around my back, keeping me close, the other gently caressing my breast. I could feel my nipple getting hard under his expert teasing.
Somehow in all of this, I decided that we needed to move to the bedroom. I slowly pulled myself back from his embrace and took him by the hand, leading him down the hall to my bedroom.
Was I really doing this? The bedroom, on the first date?
Yes. Yes I was. I wanted him - and I was starting, just maybe, to fall for him... but if nothing else, I wanted him to be my first, just like I'd been fantasizing about.
We quickly made our way to the bed and fell into it as I pulled him down on top of me. Finding ourselves on the bed, Alan had one of his arms around me, holding me tight while the other hand found its way to my skirt and grabbed a handful of my ass, all while he proceeded to kiss me like no other man had before. The passion was overwhelming. Carnal. I pressed myself against Alan's beautiful body as his hand found its way lower. As we continued to make out, Alan's hand found its way under my skirt, caressing my thigh through the black lace of my stockings. Slowly, expertly, he worked his way up the back of my leg until he had my skirt pulled up enough to expose my toned, petite ass, covered only slightly by my gray lace and satin thong.
With every inch that his hand went higher, my breathing grew heavier - more excited - and Alan knew exactly what he was doing to me as he continued to kiss and caress me.
I wanted him. I couldn't take it any longer - I started moving my hand to unbutton my shirt and Alan got the clue. I started and the bottom and he took it down from the top. My bra covered breasts eagerly greeted Alan's exploring hands. I pushed him back, however, telling him I wanted his shirt AND pants off, in trade.
My hands found their way to his belt, unbuckling it and moving to the button and zipper just behind it. Once he had his shirt off, Alan helped me with his pants, pulling them off and revealing a pair of boxers, nicely tented, all for me. I reached out and put my hand on Alan's crotch, amazed by how natural it felt to have his cock in my hand.
Staring into his eyes I said, "Alan, I want you to make love to me. I want you to fuck me. I want to be your little girl tonight"
Alan grinned and pulled me onto my side so that he could unzip my skirt and pull it off, one handed, all while kissing my neck and making me wet, wanting him so. Once he had my skirt off, Alan let me back down and his hands found their way around my back to my bra. He unhooked it and pulled it off of me. Almost instantly, he tried pulling me on top of him.
I had to stop him, for a moment, so that I could pull a condom and some lube out of the nightstand - I kept a few there to use with my toys and I'm glad I had one that night. Pulled Alan's boxers off and his cock sprang up to meet me - it was a thick, un-cut 8 or 9 inch beast. I wanted it in my mouth so badly - but I wanted it in me even more. I unwrapped the condom and slowly unrolled it down Alan's shaft. Once covered, I ran my hand along his length, spreading a bit more lube on him, saving just a bit for my waiting, wanting, aching hole. After I slipped my lube covered fingers past my thong, I quickly fingered my tight hole - getting myself slick and ready for my new lover to have his way with me. Not wasting any time, I asked Alan how he wanted to take me.
"Let's start with you on top - I want to watch you bounce as I fuck you" he responded.
I quickly straddled him and helped his rock hard cock find my waiting pussy. I held my ass so that the tip of his cock just barely pressed against my opening. I took a breath and started to impale myself on his pole. I pushed out as he pushed up and he slid into me faster than I would have expected. It hurt a bit, but I loved it.
I breathlessly told Alan that he'd just taken my cherry. That set something off in him. I felt him get even harder in me, filling my ass even deeper. I began to pull out of me and then push back in, slowly at first, guiding my hips with his strong, manly hands. Soon he was moving quickly and I was matching his pace - we were a well oiled machine and his piston was pounding into me, working me, deeper and fuller than I'd ever known before.
I was delirious with pleasure, and I started to moan, saying all sorts of dirty things to my new lover as he drove himself into me from below. After a few minutes, I couldn't take it any longer - I was in a frenzy, pushing myself up and down, riding Alan's beautiful cock for all I was worth. Alan was starting to moan as well and soon he arched his back and I could feel the warm flood as he came deep within me.
That set me off too, and I came just after he did, covering my slate grey thong with a sticky white mess. I felt Alan grow soft within me and he slipped gently out of me as I collapsed in his arms, spent... and no longer a virgin.
Want to hear more? I'd love to get hear your suggestions for where the story should go next: ams.dca@gmail.com