The Surprise Transgender Crush |

I’ve lived in a small town for just over five years, where being transgender isn’t exactly an everyday topic. I was sure that plenty of such individuals were just living their lives around me. But it wasn’t something I personally heard about all that much. Of course, as a closeted biual male who was married to a cisgender female for most of those five years, how would I?

But that was before I met Joanna.

Joanna worked in the coffee shop just around the corner from my office. I stopped in nearly every morning to grab my usual, and sometimes, to have a bite of breakfast. Joanna was almost always there, and we eventually built up a healthy rapport.

She would ask about my work as a software dev, and after boring her to tears, I’d ask about her mastery of the coffee arts.

“It’s the best kind of witchcraft,” she’d always say.

But despite being friendly for several months, things never got personal. That’s not to say I wasn’t attracted to her, however. She was tall, with long blonde hair and beautiful blue eyes. She had a curvy figure that wasn’t too thick, and her cleavage often peaked out from the top of her apron.

She usually wore a flowing skirt that came just above her knee, and sometimes, much higher. Her legs were tanned and smooth. I often found myself noticing those legs as she’d walk away from my table. Yes, I was definitely attracted to her.

As time went on, our interactions grew more flirtatious, and we became more comfortable with each other. I wasn’t sure how she felt about it, but I was ready for it. I’d been divorced for just over a year, and was honest with her about it. She was “happily unattached,” as she put it, and was always quick to remind me.

She had gone from being just the friendly girl who served my coffee, to being the friendly girl I’d find myself thinking about the rest of the day. I thought about her so much that I’d swing by to grab an afternoon cup, just to see her again.

It was during one such afternoon trip that I found out more about Joanna than I expected. First I was disappointed. Then I was relieved. Then I was excited. But it all happened within the span of a few minutes.

I sat at my usual table, and saw Joanna smiling as she approached me. “Back again, I see.”

I returned her smile. “Guilty,” I said.

She sat the cup down on my table, and bopped her head to a song that wasn’t playing. “My French Roast brings all the boys to the yard,” she sang.

I sat back and extended my hands toward her. “Hey, not bad! I think you missed your calling, working here.” I motioned to the empty chair across from me, and she sat down, shaking her head.

“Ha, nooo,” she said, “not me. I love to sing, but it’s only for fun, or when I’m with somebody I like.”

I sat forward and put a hand to my heart. “I’m flattered,” I said.

“You should be,” she said with a wink.

I took a sip, and set my cup down next to her left hand. That’s when I noticed her ring finger. I felt my expression drop, and she must’ve noticed it. She held her hand up to me, and pointed to the diamond. “Saw that, did ya?”

I forced a smile, and nodded. “I did,” I managed. “Congratulations.” What had happened to her status as ‘happily unattached?’ Should I ask? Was it any of my business? I was upset, and I was sure she could see it.

She stared at me for a moment, frowning as she did. “It’s not what you think,” she said.

I attempted an innocent look, though I wasn’t sure how convincing it was. “No?”

“No, no,” she said with a wave of her hands. Finally she stopped and sat forward, coming nearly nose to nose with me.

“It’s not real, it’s just for protection,” she said softly. “I’m sick of assholes hitting on me.”

I exhaled a bit louder than I meant to, and my smile returned. “Ohh,” I said with relief, “okay, okay.” Then I thought about it, and pointed to my chest. “Wait, so, I’m–”

“No! No!” She grabbed my hand and pulled it down to the table, layering it with her other hand. “Not you, I swear.”

“Oh man. Okay, good, good.”

She shot me a curious look. “You seem totally relieved.”

“I totally am,” I answered.

She eased back in her chair, but kept hold of my hand. “Good,” she said. After a quiet moment, she continued. Only, this time, her smile was gone and she looked more serious than I’d ever seen her look.

“I also put it on because if I can weed out the assholes, then I won’t have to worry about anyone changing their mind about me once they find out.”

I stared at her. “Find out?”

She spoke quietly, as if each word was a serious effort. “Find out that I’m transgender. Because for some guys, that’s a problem. Which is fine, I get it.” She locked eyes with me. “Is that a problem for you?”

When I didn’t immediately answer, she pulled her hand back. But I quickly took hold of it again. “No,” I said, “not at all. I’m just surprised, I mean, I didn’t know.”

“Right,” she answered. “That’s fair.” She hesitated. “Good surprise?”

I thought about that. “Is it weird if I say ‘best surprise ever?’”

I watched as she thought about that one. “No,” she said cautiously, “no? I mean, as long as you’re sure it’s not a problem. Because I really, really don’t want it to be.”

I took her other hand, and motioned her forward with my head. She came close to me again. “Not a problem for me. Besides, I’m biual. Is that a problem for you?”

She let out a sharp breath, as if she’d been holding it for hours. Her expression softened as she spoke. “Not a problem at all.”

She looked over my shoulder, and slid her chair back to get up. “Somebody just walked up,” she sighed, “duty calls. Are you headed back to your office?”

I nodded. “I am, yeah. But I’ll be here in the morning, bright and early. I want to get here before your French Roast fills up the yard.”

……

I drove back to the office, but it was a struggle to focus on work. Every time I got started, I thought about Joanna, and her surprise revelation. I never saw it coming, and the more I thought about it, the more I couldn’t stop thinking about it.

I had never been with a transgender person before, but was always curious. So to find out that the girl I’d been crushing on was one? It was almost too much to comprehend. I eventually had to get up from my desk and move around, just to try and regain focus. To say that I was turned on was an understatement.

I finally managed to finish up, and after leaving for home that night, I wondered why I didn’t get her number. I didn’t want to be pushy, or risk the fun connection we’d built, but I did want more. We had a moment together, there was no doubt about it. After I showered and laid down for the night, I decided that tomorrow would be the day. Transgender or cisgender, I wanted Joanna. That was it.

I arrived at the coffee shop around nine, and was greeted by an older brunette. She recognized me, and pleasantly took my order. I sat at my table, and laid my phone down. I took a sip of my coffee, burning my tongue a little. I waited, and glanced around. But there was no sign of Joanna. When the bagel I ordered was delivered to my table, she wasn’t the one to do it.

I took a bite, and wondered if maybe I’d been wrong about our “moment” from the day before. That’s when the sudden sound of Joanna’s voice over my shoulder caused me to jump.

“How’s that bagel?”

“Jesus,” I said, “scare the hell out of me, why don’t you.”

She plopped down in the chair opposite of me. “You love it, you know it.” She locked eyes with me. “Hi,” she said with a smile. “How are you?”

“Hi yourself,” I answered. “I’m good. But I thought for a minute you weren’t here.”

She shook her head. “Me? No way. I have to be here, so I can talk to you. It’s not like you have my number or anything.”

“Yeah,” I said with a laugh, “that’s on me. I should’ve asked for it yesterday.”

“Yep,” she agreed, “you should have.”

I sipped my coffee, and slid my bagel in her direction. “So, what time do you get off today? Are you busy tonight?”

She quickly grabbed the bagel, and greedily took a bite. “Well,” she said as she chewed, “that depends.”

“On what,” I asked.

She slowly inched her hand toward my cup, and I nodded with a grin. She took a sip. “On how busy you are in an hour or so. She rested her elbows on the table and laced her fingers together. “I’m thinking of blowing off today.”

“Meaning?”

“Meaning, getting out of here and not working anymore.”

“You can just do that?”

She waved off my question with a flick of her hand. “Are you kidding? Of course I can. I’m kind of a big deal around here.”

I smiled. “Is that so?”

“Yep. Actually, Britt just came in. She missed a day this week and wanted to make up her time. So, I think I’ll split.”

“Well,” I said, “I don’t have that much going on today. But I do need to go by the office for a few. We could meet there, if you like.”

She raised an eyebrow at this. “You mean the office you don’t share with anyone? The one with no windows, where no one can see you or hear you scream?”

“That’s the one. You’re not scared, are you?”

“Should I be?” she asked with a wink.

I put my hands up in a playful protest. “Hey, it’s cool if you don’t want to. Chicks are lining up to hang out with me, just so you know.”

She tilted her head to one side as she spoke. “Chicks?”

“Yeah. Chicks. Dames. Broads.”

“So, your office is in the 1940’s. Good to know.”

……

By the time Joanna arrived and I pulled the door closed behind her, we were all over each other. The kiss that had been hanging in the air between us finally happened, and so did everything else. Before I knew it, my hands were up her skirt, clutching her ass, and inside her thong.

She was unbuttoning my jeans, and pulling them down just enough that my hard cock jumped out. She took it and began stroking me, as I slipped her shirt off over her head. She unhooked her bra as I removed my own shirt, and I watched as her tits fell out one by one. They were perfect, and I quickly grabbed them, gently pinching each nipple in my fingertips.

“Mmm,” she said with a smile. “Do you like them?”

I answered by kissing her nipples, and then sucking them, first the left, then the right. She pushed my jeans down to my knees, and I wiggled my way out of them. I took her face into my hands and kissed her again, my cock pressing against the lump in her skirt. I reached down and unbuttoned it, then watched as it fell to the floor.

Her hard cock was pushing to escape from her pink lace thong, and I gently pulled it free, stroking it with my right hand. She was big, and it suddenly hit me why she always wore skirts. She stroked my cock, and we kissed, pressing our flesh together as we stood there.

My heart was racing, and as our tongues danced, I thought about moving us to the bed in the backroom. As soon as I had the thought, she pulled back. “Too bad you don’t have a bed.”

“I do, actually.”

Her eyes were wide, but I interrupted before she could speak. “No, no,” I laughed, “it’s not like that. Sometimes I just crash here.”

“Why not go home?” she asked.

“I work late. Plus, the internet sucks at home.”

She stared at me for a moment. “Hmm. Okay, good enough.”

She stuck her tongue back into my mouth, and we continued stroking each other. She dropped down and began sucking my cock. She slurped it loudly, back and forth, working it with her left hand as she did it.

“Jesus, hell,” I whispered.

She took it out long enough to ask, “So, where is this bed?”

……

After fishing a small bottle of lube out of her purse, Joanna followed me into the backroom, where we stood at the foot of the bed. I glanced at the bottle as I clutched her ass with my hands and kissed her neck. “That’s handy,” I whispered.

She tossed it onto the bed and lifted her left tit, then guided my mouth to it. “Maybe I was hoping you’d want to hang out with me today,” she said in a nearwhisper.

I licked her hard nipple and sucked it like I was working for milk. I stopped long enough to say “Okay, good enough.”

She responded by digging her nails into my ass and biting my shoulder. I sat down on the bed, and she straddled me, kissing me and running her hands through my hair. We stayed there for a while, just enjoying the moment. I finally pushed myself backwards until I was fully on the bed. She remained on top of me, our hard cocks rubbing together as we moved.

She turned around, putting her cock near my mouth, and I eagerly took it. She tasted so good, and her skin was so soft. She moaned as I sucked her, and she was propped onto her left knee to watch me.

“Fuck baby,” she moaned, “fuck yes.” She took my cock into her right hand, and went down on me, taking it all into her mouth. I moaned in response, and we began matching rhythm as we ’ed. Then I slowed down, and so did she.

I took her cock out, licking the shaft up and down, and she mimicked the move. Her choice to mirror me was such a turn on, and I let her know by gently running my fingertips up and down her spine.

“Mmm, so good,” she said.

I put her cock back into my mouth and kept both hands on her back, sliding them to her ass. She planted her left leg down, fully on top of me as she sucked me. We maintained our shared rhythm, both of us softly moaning as we did.

Finally, she broke rhythm to run her tongue down to my balls, and further. I held her, and shifted, moving us on our sides. She moved her right leg, and I tucked it under my right arm, aiming my mouth straight at her asshole. She made the same move as well, and felt her tongue begin to lick my hole.

“Fuck yeah,” I moaned, and then began working on her opening too. She tasted sweet, and I pulled back a couple of times to admire how perfect her hole was. Her balls were warm on my chin, and I stroked her with my right hand as I ate her ass. The sensation of her tongue inside me was nearly overwhelming, and I had to stop a few times, just to exhale.

I heard the cap pop open on the bottle as she began sucking my cock again. I shifted slightly, and started sucking her again as well. I felt her take my cock out and start lubing it up. It was a little cold, but I didn’t care. As she continued prepping my cock, I started deepthroating hers. I grabbed her ass and pulled her back on top of me.

“Oh my god,” she said, as her cock hit the back of my throat. I moved back to her hole, and she sat up on her knees, riding my mouth. My tongue was sloshing in and out of her ass, as I kept soaking her from the top of her split to the bottom of her balls.

“Jesus fuck,” she nearly screamed and lay down on me again, shoving my lubed cock deep into her mouth. She took it out and spit on it, then spun around to mount me. Her mouth hung open as she looked down at me, and I reached up to squeeze her tits as she began working the head into her ass.

I gently pushed up as she started sliding up and down. Her ass was so wet and so tight, it felt amazing. I watched her face as she eased all the way down, her mouth opening wider, and her eyes squinting. I grabbed her face, pulling her down to kiss me. “Goddamn,” I whispered, “you’re so perfect.”

Her tits smushing onto my chest and her hard cock rubbing on my stomach, she moved back and forth as I fucked her ass. She stuck her tongue into my left ear and began whispering quietly to me.

“I’ve never wanted someone so bad in my life. You feel so good.”

I kissed her again and grabbed her ass with my hands. I held her still and started pushing my cock up, going deeper than before. She lost her breath and let out a loud gasp.

“Are you okay?” I asked.

“Fuck yes,” she moaned.

I kept a steady rhythm, not wanting to go too fast. I didn’t want to cum yet, and I knew if I started moving faster, that’s exactly what would happen. She licked my neck and whispered in my ear again.

“Are you close?”

“Trying not to be.”

“Your cock feels so good,” she said.

“I want to feel yours.”

“Yeah?”

“Yeah.”

She kissed me, maybe more intensely than she had so far. She sat up, found the lube resting against my leg, and slowly began to lift herself off my cock. She popped open the lid again, but I stopped her before she could use it. “Come here,” I whispered.

She slid up my chest as I slid down in the bed. She was on all fours, lifting her cock up just enough so I wouldn’t choke on it. She slowly started my mouth, moaning as she moved. “Mmm,” I moaned as I fingered her ass with my right hand.

I could hear her breathing harder as she began to move faster. I took her cock deeper than before, and by the time she pulled out, it was dripping wet. She smiled down at me. “Fuck, gotta stop that or I’ll cum first.”

I sat up and kissed her before getting on all fours myself. She positioned behind me, and I felt her tongue lapping at my asshole. I rested on my elbows and laid my head onto the bed. She rubbed my hole with some lube and slowly slid one finger in, then another.

“Are you okay?” she asked.

“Fuck yes,” I said.

She laughed a little and kissed my balls before moving up and teasing my hole with her cock. She moved slowly, working the head in. I took a deep breath and exhaled, opening up for her and she slid her cock in even more. I felt her hands on my hips as she gently fucked me. I closed my eyes as she moved, enjoying every inch of her hardness.

I reached down with my right hand and stroked my cock, as she began to go a little faster. She rubbed my ass with her hands, and then laid down on my back. I could feel her tits on me, and she kissed my neck, running her hands over my shoulders.

“I can’t wait much longer,” she whispered.

“That good, huh?”

She giggled as she spoke. “Sooo good, baby.”

She moved back up and slowly pulled out. I rolled onto my back, lifted my legs, and she slid back inside of me. She grabbed my stilllubed hard cock, and began jerking it as she fucked me. I reached up and she leaned over so I could grab her tits.

“Fuck me,” I said, “do it.”

Her mouth opened as she smiled, and she began moving faster. It didn’t take long until she was slamming into me, her hand jerking me faster and faster. My eyes watered as her cock was all the way inside, me hard. I dropped my arms to the bed and laid there, enjoying every moment of it.

I thought it would never end, and I didn’t want it to. But I was so close, so I grabbed my cock, taking it from her hand, and as I did, she suddenly pulled out and exploded all over me. Thick ropes of hot cum shot up my chest, onto my cheek, and splattered all over my hand as I jerked off.

“Ohhh, ohhh fuck,” she screamed, “Oh Jesus, oh fuck!” She kept jerking, cum continuing to shoot out, and as I felt my own cock beginning to twitch, I dug my left hand into her leg.

“I’m cumming,” I gasped. “Oh baby, I’m cumming!”

She quickly grabbed my cock, shoving it into her mouth as cum began to pump out of me. I grabbed her head and started ramming my cock deeper, hitting the back of her throat.

“Mmm mmm mmm,” she moaned deeply, as my cock emptied down her throat. She kept swallowing as I came, and I finally loosened my grip on her head. She waited until I was finished and sucked my cock dry, taking it out to kiss the head. I shivered in response and sat up to kiss her.

I gently pulled her down onto me and wrapped my arms around her. We were both out of breath and trying to get it back when she licked the cum from my cheek. “At least no one heard me scream,” she laughed.

We spent the rest of the day together, followed by that weekend, and nearly every night afterward. I didn’t expect to fall that hard for Joanna, and I also never thought I’d be that happy. It surprised me. But it was the best surprise ever.