Josie's First Date

Hi. My name is Josephine, but everyone just calls me Josie, and I want to tell you about my first date... with a boy.

This may not seem strange or problematic, but I should mention, I am a transwoman. But I don't like to boil myself down to one specific thing about me. Being a MTF is just something that is just part of who I am: like wearing glasses, or being a bit too tall at 5'10, or having burgundy, chin length hair cut into a cute bob, or having naturally kissable puffy lips, or having a nose that is slightly too large for my liking, or having an inordinate amount of love for art nouveau. Heh, sorry, I also have a bizarre sense of humor, but you get the picture.

Still, why would me being trans affect my impending date, you might ask?

Well it all started while I was at work. I work as a nurse at a local doctor's office. I had just clocked in for my shift, when the Director of Nursing, Dawn, approached me followed by a guy dressed in scrubs that I had never met. He looked to be about 30, with a broad chest, smooth face and with his brown hair close cropped on the sides and combed back on the top. He seemed tall, even to me, as I guessed him to be at least 6'2". But, here's the part where things got complicated: he was handsome. When he flashed a smile of white teeth with prominent upper canines, I actually felt my legs get weak and my hands shook a little.

So far, the headline reads: "Trans-girl falls for cute boy". No big deal, right? Except for me it was. I had been in two relationships so far in my adult life; both were longer term and both were with women. I had basically thought I was a lesbian up to this point. It's not like I had never admired a man's looks before, but whenever I considered a relationship with a boy, it just didn't appeal to me.

"Hey Josie", Dawn's voice broke through the churning ruminations that had torn through my mind brought on by the new guy's smile. I realized that I had sat down owing to the sudden onset of weakness in my lower limbs. Well at least two of my lower limbs, anyways. I was surprised to find my clit stiffening, much to my dismay. I awkwardly stood up, trying to hide my shame by holding it tightly between my thighs. Thankfully, neither my manager nor the mystery man gave any indication that they noticed anything.

"I'd like you to meet Brayden Morris", Dawn continued. I took his outstretched hand in mine, and was pleased to find it warm and a little rough to the touch. Then I said "I'm Josie Clark, nice to meet you" in my voice that always belies any passability my appearance might have earned. He gave me a questioning look, which came as no surprise.

"This is Brayden's first day and, as the "new guy", he gets the pleasure of following you", said Dawn more cheerfully than anyone should at 6 am.

I was, of course, freaked. I hated training, and now I had this drop-dead gorgeous guy, about whom I have all these mixed-up feelings, following me around all day.

"Ok, Dawn, just give me a sec to grab some coffee", I said in a voice I hope didn't sound too dismissive.

"Sure, Josie, why don't you take Brayden with you?"

"Oh, I don't drink coffee", said Brayden, turning a little pink in the cheeks, "its against my religion".

Dawn and I both chuckled simultaneously, before realizing he was serious. "Oh, but if its ok, I will follow you Josie", Brayden quickly added, "maybe you can give me a brief tour on the way". He smiled again, and I had to look away before my painfully throbbing shaft got any bigger.

"Sure, it's this way, 'new guy'", I said, as little smile defiantly crept across my lips.

The rest of the morning went pretty smooth. Brayden was an attentive student, who kept things professional while still cracking a harmless lame joke at the appropriate times to keep the mood light. By the time lunch rolled around, I found myself crushing on him fairly hard. I was looking forward to the solitude lunchtime would offer, as a chance to recenter myself after the morning's whirlwind of emotions. That was, until Brayden said:

"Hey, Josie, where are you eating lunch today?"

"I brought my lunch, so I was just going to eat in the breakroom." I felt a tautness in my throat as I said it, fearing what was coming next.

"Would you like some company?", Brayden asked. His tone was jovial, but his cheeks flushed as he no doubt made not of my hesitancy.

"Sure", I mumbled nervously. Still, I smiled again, unable to help myself.

The breakroom was mercifully empty. I was relieved to see that none of my other coworkers would be able to watch me crash and burn as I attempted to make conversation with the hot new guy. Thankfully, my fears never came to fruition. Brayden was insanely easy to talk to. We mostly talked about work, but no matter the subject, his responses were always kind and encouraging. Just like the morning, lunchtime flew by. Our half hour was almost up when he finally stopped the conversation and stared at me intently, while he seemed to be working up the courage to ask what I knew was coming next:

"You're transgender, aren't you?"

He said it so earnestly, I nervously laughed a little before responding with an "affirmative." "What gave me away", I asked in a joking tone to cover the terror over what I was sure was going to be a confidence shattering response.

"Oh, believe me, it wasn't obvious", he spluttered nervously," I mean, don't get me wrong, you are very beautiful..." He stopped suddenly at the word, realizing what he had done.

There was an inordinately long awkward pause, before he finally spat out, "Hey, do you want to go out sometime?"

I was so utterly mollified, it took almost a full 30 seconds before I could reply, "Yes! I mean sure, if you want to?"

"I'd love it if you would try this all-night breakfast joint I just heard about with me?" he offered.

"Oh my god, I love breakfast for supper!" I practically shouted at him.

He laughed and we made a date for that night, 8 pm. While the morning flew by, the second half of my shift dragged. The more I thought about it, the more excited I got, and the slower time seemed to move. By the time I finally got to my car after my shift ended at 6 pm, my nether regions had been so swollen for so long that I was in sheer agony. If I was going to get through this date, I needed to calm down. I needed a hot shower. I needed a drink. And I desperately needed orgasmic release from the chains which desire had tightly wrapped around my smooth tan scrotum.

As soon as I got through the door I quickly took care of the drink. I gulped the shot of tequila in one burning swallow and felt its warmth spread from my lower abdomen outwards. I slipped out of my scrubs, and stripped my pink thong and bra from my smooth body. By the time I got into the shower, I desperately wanted to masturbate. My hand kept gliding down my wet, slippery belly and resting on my smooth, shaved boy-clit. But, I resisted with all my will power, ignoring my carnal desires until I finally found myself standing in front of my overstuffed closet. I slid on my black, lacy thong, relishing the feeling as it strung between my soft ass cheeks, and came to rest snugly against my tight little hole. I strapped its matching black bra around my chest. It lifted my barely b-cup breasts upwards and inwards so much that I smiled as I admired the effect in the mirror.

"Hopefully, Brayden isn't a breast man" I sighed out loud and then laughed like a dork at my own joke.

I pulled my black thigh-highs up my shapely, freshly shaved legs, and stepped into my cutest and most favorite strappy black dress. It fell mid-thigh, and billowed outwards at the hips, accentuating the more feminine aspects of my features. As I reapplied my smoky eyeshadow and red wine shade of lipstick I noted the time: 7:42 pm.

"Shit!" I said out loud. "Time to go."

I ran two stop signs as I drove across town to the designated meeting place. It was 8:12 pm by the time I pulled up to the spot: Over Easy, the red neon sign read. It was one of those casual, sit down places. As I admired the building's restored brick facade, I was surprised to see Brayden waiting by the front door. He was dressed in a black slacks and sportscoat combo, looking even more handsome than I remembered. He waved at me when he saw me pull up and I felt a small electric shock run from the top of my head to my pelvic floor. I wanted to touch myself so bad at that moment, but once again I resisted.

When I finally reached him, after parking my car, he said, "Hey, you!" and grabbed me into a deep hug. He smelled like amber and cloves. His arms easily encircled me, and in their strength, I felt comfort, warmth and safety. I was not prepared for this and felt my girl-cock fight against the constraints of my panties. No doubt it was pushing into Brayden's upper thigh as well, but he considerately said nothing to spare me any embarrassment. For a moment, I thought I felt something hard pressing into my lower abdomen. Then he turned sideways to me and held out his arm.

"Shall we, then?" he inquired.

I smiled a big, probably goofy, smile at him and took his arm. The restaurant was fairly empty, and we were seated quickly. Dinner went exceptionally well. Better than I could have ever hoped for. We bantered back and forth easily for almost an hour. By the time our plates had been cleared away from the table we had found common interests in gaming, anime, hiking, and comedies. I was starting to feel like I never wanted this night to come to an end. I guess we had that in common too, because Brayden stood up asked, "Hey, Josie, would you like to come over to my place for a bit? I would love to show you that "When They Cry" anime series I was talking about."

It was all too much. My chest tightened, and I wanted to cry, laugh, and run away all at the same time. But I wanted this, wanted him so very much at this moment. I swallowed hard, and managed to respond with a small, "Yes. Please."

I rode with him in his car, giving me more time to learn about this fascinating, magnificent creature I had met only hours ago. He explained his history: He was religious but not active in his religion. He told me how he had gone on a mission to Thailand for his church. There he was introduced to kathoey, or ladyboys as they are known in the U.S. He was able to strike up relationships with these Thai trans-girls and found them to be intriguing and attractive. Yet he claimed to have never fucked a single one.

"And I have only been with cis-born women ever since I got back from the mission", He concluded.

"You are honestly telling me you have never been with a trans-girl?" I asked with mock suspicion.

"It's true!", he insisted, "but ever since my mission, I have desperately wanted to."

It took everything I had to not snake my hand between his legs, pull out his cock and give him the greatest blow job of his life. Yet my feelings betrayed me once again: What if I wasn't what he was hoping for? What if he gets me naked and doesn't like what he sees? What if we go all the way and it's just terrible? I mentally snarled as I swept these thoughts from my mind. Then we pulled up to a red light and he said,

"You're amazing." I felt his large warm hand slide into mine. His fingers interlocked with mine. My palms immediately began to sweat.

"What?!", I choked, as I fought back the tears. I turned my head to see him looking at me. "Had he just read my thoughts?", I wondered. It was now or never, I had to be honest. I didn't know where this was going, but if it was going anywhere, I couldn't leave this for later.

"Brayden, I think you are amazing too...", I began. He looked slightly crestfallen as if he was anticipating bad news to follow. "I have to confess, I have never been with a man before", I quickly blurted it out to soften the blow.

He sat silent in thought for a moment, before asking, "well...do you still want to come over?" I took my hand from his and touched his cheek, enjoying the roughness of his five o'clock shadow. Then before even I knew what was happening, I was kissing him hard. He responded by sliding his hand around behind my head and shoving his tongue into my mouth. I was practically over the center console and in his lap making out with him, before we realized the light had changed and people had started honking at us.

By the time we got to his place, we were all over each other. He grabbed me by my hand and practically ran us to the door of his apartment. We had barely closed it behind us and we were already stripping out of our clothes. He grabbed me under my thighs and lifted me against the wall of the hallway. I made no mistake this time; I felt his massive, pulsing dick pressed against my thong-clad boy-pussy. I slid my hand across his solid, shaved pecs. This made my own clitty swell so bad I thought it might explode. I knew if I looked at it at that moment it would have been purple. He kissed me hard, and ground his cock against my hole. I let out an involuntary cry. He laughed and threw me over his shoulder before throwing me onto his bed.

I sat up laughing and saw him standing a foot in front of me. The bulge in his pants was at eye level. I let my hand move up to his waistline. I looked him in the eyes as I slowly unbuttoned his slacks and unzipped his zipper. The pants fell free to the floor. I looked down to see his blue boxer-briefs stretched almost comically at his crotch, as if it were going to tear free at any moment. I tortured him a little more by gently stroking his steel-like shaft through the thin cotton fabric. He let out an expletive. I couldn't take it anymore!

I grabbed the elastic band of his underwear in both hands and pulled downward. Once freed it swung upwards, nearly hitting me in the face. It was probably 9 inches in length and at least 2 in girth. And, OH MY GOD, it was sexy! Smooth and brown in color, it was as if I were in a trance. I reached up and wrapped my hand around it gently squeezing while I pulled the foreskin back. He moaned and ran his fingers through my hair. I slowly let my tongue curl around the head of the monster. Already I could taste salty pre-cum dribbling from its tip. I took the head into my mouth, feeling my tongue massaging the underside of it. It was so slippery and soft in my mouth. I felt it slide down past my soft palate to the back of my throat. It was so big, I had only about half of it in my mouth.

"Ohhh, Josie!", he gasped. I kept my hand around the base of his cock and stroked it as I began to rhythmically slide the rest in and out of my mouth. After a minute of this he pulled his dick from my mouth.

"Okay, baby, we are going to have to stop that! I have been saving this orgasm for you and I want to unload all of it inside you."

I almost melted. I laid back on the bed wearing only my panties, bra and stockings. He reached down and slid the black thong from my waist. I straightened my legs and raised my feet upwards to make it easier for him. I reveled in the feeling of the string being pulled from between my cheeks, and the feeling of the cool air on my ass. My cut, 6-inch girl-cock was so hard that it sprung backwards and slapped audibly against my tummy. He smiled at this and took my cock in his warm, rough hands. He squeezed gently as he slowly stroked it. Letting his thumb come to rest on the bottom side of the head with each stroke. I moaned each time it happened feeling the impending orgasm closing in. He put a hand behind each of my knees and rolled me backwards orienting my tight little butthole upwards.

I had never had never been eaten out before by either of my exes. Blow jobs? Of Course. But neither of them dared to go where Brayden was about to go now. Because of this, there was no way I could be prepared for the amount of pleasure that was about to come my way. The moment his tongue traced the outer edges of my fuckhole, I felt my eyes go wide. I let out a loud gasp and squirmed with delight.

"Hold still", he said. His voice was muffled by my ass, but I could tell he was smiling. He grabbed by hips and drove his tongue in deeper. This time I gave out a little scream. My hand flew to my stiff cock, but he slapped it away. I so desperately wanted release! It was pleasure and torture all at once, the feeling was indescribable.

"Please...", I begged, "I can't take it anymore. I need you inside me!"

"I couldn't agree more, baby", he said grinning as he grabbed his dick and began rubbing the head against my wet boy-pussy. I felt the tip push inside me. "You said you have never been with a man before. Are you sure you're ready for this?"

Such a sweetheart, thinking of my comfort. My last girlfriend was very adept with a strap-on, but I didn't want to go into details right now: I just needed him, all of him, inside me. I nodded my head, and closed my eyes. Then he pushed the head of his cock into my puckering hole.

"Ooooohhhhhhh!", was all I could manage. I felt him inch by inch slide into me. My eyes rolled back into my head. I bit my lip. His pelvis slapped against my ass. The head of his cock hit my p-spot. That was all it took. All of the slow burn, the growing pressure that had consumed me to this point gave way and the dam broke. My cock jerked once and my jizz shot along my abdomen and tits. With the orgasm came a flood of relief. Relief so powerful, the likes of which I had never known before. I felt tears gather along the edges of my lower eyelids. "No!", I thought wryly, "I am not screwing up my makeup tonight!".

"Oh Baby, Yes!", Brayden exclaimed, evidently pleased with what he had done. He grabbed my dick and rapidly stroked it, milking the cum from my now softening cock. The orgasm began to fade to afterglow. My eyes returned to center and I saw him smiling down at me. I felt my face flush. I grabbed both hands behind his neck and pulled his head down and kissed him softly. He let go of my now limp clit, and caressed my cheek.

"I hope you aren't mad that I came so quickly", I said.

To this he just laughed and replied "My dearest, Josie. I...so enjoyed that. I hope I get to see that again very soon. But we're not done yet!"

I giggled when he flipped me over. "No, now I want to watch that sexy ass bounce on my dick, until I blow my load deep inside you." His hands slid along my torso and came to rest on my breasts. His fingers nimbly plucked at my hard nipples. His lips brushed the length of my spine. I already felt blood rushing back to my girl-cock. Without a word, his hands slid to my hips and pulled my ass onto his still very firm dick. He pushed in easier this time. Again and again, I felt his thick shaft slide out of my ass until the head tugged delightfully at the edges of my hole, before sliding forcefully back in. Each time his head slammed home I felt my clitty swell a little more.

The dull throbbing returned deep inside me, growing at pace with my pleasure. Exclamations mixed with expletives spilled from his lips: "Josie! Damn, Baby! Yes! Oh Fuck!"

I felt Brayden's cock engorge and stretch me a little more with each passing second. He was about to cum. "Oh, yes, yes!" I cooed over and over again. I heard the tone of my voice go higher with each thrust as I rapidly approached my second orgasm.

Brayden suddenly picked up the pace. I felt my ass jiggling with each collision. He slapped my right ass cheek and yelled, "FUCK!" I felt the warmth as Brayden unleashed his full load inside me.

I was so close! Just. One. More. Good..."Ahhhhhhh..YES! Oh Fuck, Oh fuck, Oh fuck", I screamed as my rigid little cock shot what was left in my balls onto Brayden's bed spread.

Brayden collapsed on top of me and we layed there for a few seconds trying to catch our respective breaths. It felt so good, so right having his strong sweaty body pressing against me. Feeling the rhythmic motion as chest rose and fell. His lips grazed my ear and I shuddered as goosebumps broke out all over my body.