Cassie's Black Glove

"I don't know...I mean, I'll be honest Jake, I don't usually date straight guys. I've been hurt before" Cassie says looking slightly embarrassed. I look into her beautiful deep brown eyes, already lost in them. Her smooth, almost elfin face has a perfect complexion, though slightly blushing at this point. She tilts her head down and a cascade of dark brown wavy hair partially obscured her face.

"I'm sorry if I made you uncomfortable, Cassie. I just...I figured I would give it a shot. I have to admit I've been crushing on you for a while. Even before I heard you were..." my voice trails off, not wanting to say it out loud in the busy hospital cafeteria. The last thing I want to do is make this more awkward for her.

She smiles as she tucks her hair behind a perfectly kissable ear.

"Trans. You can say it you know. I don't exactly hide it." She says looking at me expectantly.

"Well, you don't exactly advertise it either. I had no idea until Katie mentioned it one day. I was crushing on you the day you started here, and was clueless. To be honest, when Katie said you were trans it all kinda clicked in my head."

Cassie rolls her eyes dramatically, "Fucking Katie! I love that bitch, but she has a big mouth!"

I laugh, knowing that Katie is the source of all gossip on the unit.

"Still...there is a reason I usually don't date straight guys. Like I said, I've been hurt before. Some guys think this is what they want, until they are face to face with it, and then they freak out. It hurts when a guy you like suddenly runs off like he made a mistake." As Cassie says this, I hear the hurt in her voice. Without even thinking about it, I reach out to hold her hands on the table.

"Hey, Cassie, I promise you I'm ok with it. You being trans doesn't change that I've been dying to take you out since the day I met you. I think you are absolutely beautiful, and the fact that you are packing doesn't change that for me." Cassie snorts laughter at my use of "packing" and pulls her hands free.

Cassie smiles, and then looks at her watch "Oh Shit! I gotta go back to the floor. Look, I'll text you my address. Tomorrow at six? Just a date?"

"Just a date! Absolutely!"

"Don't fuck this up..."

"I'm a perpetual fuck-up. But I promise I won't fuck this up the way you think I will."

She gives my hand a final squeeze and stands to leave. As she stands I take in her full figure, the hospital scrubs tight and hugging her curves. Five and half feet tall, maybe 130 lbs, but in all the right places. Her breasts aren't huge, but look to be a comfortable hand holding size, perky and round. Flat stomach and slender waist that round out to wide hips that scream to be gripped and held. As she turns to go, her best asset comes into view. Her scrubs tight against her round strong ass, shifting rolling as she walks away on firm smoothly muscled legs.

As she goes she looks over her shoulder, hair bouncing, and I know she knows I'm very intently checking her out. She rolls her eyes, and mouths "Dork" as she leaves.

Our first date went much the same as many first dates: dinner, a movie, laughs and stories shared. At the door to her apartment, there was the awkward first date end of the night nerves.

"Soo, you want to come in?" She asked.

Looking at how her skirt and low cut blouse hugged her body, I definitely wanted to take her up on the offer, but I was determined to not fuck this up.

"Maybe another time...taking this slow right?" I leaned in and kissed her full lips, and after a moment of indecision she kissed me back, our lips parted and for a brief moment our tongues touched. We made hasty plans to see each other again and I left before the bulge in my pants became too evident.

The third date was much more relaxed, we had started growing into each other and this night we just went to a local pub to hang out. She was wearing a pair of tight jeans and an off the shoulder top that looked to be two sizes too small, but in the best ways possible. After a few drinks and chatting, we found our way into her apartment. Sitting on her couch, we kiss lightly as first and she eventually sits on my lap, straddling me. Hands running up and down her back, sucking her ear lobes, kissing her neck, my hands slide over to cup her firm breasts, massaging and then pulling her top off.

As she grinds against me, I play with her beautiful tits, rubbing my thumbs over her erect nipples, then sucking on them, lightly biting. I feel my cock getting hard, but also feel something hard rubbing against me. For the first time I feel her girlcock pressing against mine, and the feeling makes my whole body shiver in anticipation.

Cassie looks at me with her sparkling brown eyes and bites her lip lightly. "I think it's time for this to come out..." and she reaches down to undo my pants.

Soon we are both naked, I gaze up at her perfect body, everything I had imagined now on full display. Entranced by her wonderful curves, she sat again on my lap, our hard cocks rubbing against each other.

"So...are you ok?" Cassie asks nervously. The small tremble in her voice makes me feel so protective of her. In response, I reach down and wrap my hand around her, slowly stroking, loving how soft her skin felt in my hand. She lets out a low moan and smiles at me, running her hands up and down my chest.

Reaching behind her to the table, she produces a bottle of massage oil, and squirtes some into her hands. Sliding up closer to me, she wraps her hands around both our cocks, slowly stroking us together.

"Oh, Cassie...yes..." I moan, leaning back, enjoying the feel of our shafts rubbing together between her hands.

"Let me take care of you baby..." Cassie says as she works us both.

I continue to divide my time between playing with her breasts, running my hands over her delicious curvy hips, and squeezing her tight ass. As the feeling builds in my balls, I let out a moan, breathing faster. Cassie squeezes us tighter, stroking faster.

"Cassie...baby...god I'm close..."

She locks eyes with me, and leans forward to kiss my lips, the kiss turns into a bite, my lower lip lightly between her teeth, then she leans closer to lick my earlobe, I feel her hot breath on me, "Cum for me baby...please...cum for me Jake..."

My body tenses and I surrender to a massive orgasm, my cum spurting up over her hands, leaking down over her own throbbing cock. Cassie let's out a squeal and cum erupts from her cock as well...I feel her body trembling on my lap as her orgasm takes her, I wrap my arms around her, holding her close until her shaking stops.

I push her back and kiss her lightly on the lips.

"Thank you, Jake" she says.

"For what?" I say laughing.

"For not fucking this up."

———————-

Cassie and I meet again a few days later. We make plans for me to go to her place after my shift. As I knock on her door, I'm full of nervous anticipation, not sure what to expect, and still riding that high from going so far outside my safety zone.

As Cassie opens the door, I'm again stunned by her sheer beauty. Her smile feels like it is just for me alone, and I feel a flutter within me. I close the door behind me and she surprised me by pushing me up against it, smothering me with a kiss full of desire and unspoken promises of more to come. I return her kiss, nervousness replaced by a surge of lust, my cock hardening, and hands reaching for her body.

Cassie breaks off the kiss and pushed her self just out of reach laughing.

"You just got off shift and smell like hospital. Come on, let's shower."

Without looking back, she turns and starts an exaggerated (though appreciated) seductive walk to the bathroom, stripping her shirt off and tossing it aside as she goes. I hurry after her, scrubs and underwear hastily becoming a pile on the floor.

I step into the steaming wall in shower, and she immediately puts her arms around me. We kiss as the hot water cascades over our entwined bodies, her firm breasts pressing against me, and our cocks rubbing together, both slowly hardening. She begins to soap me down, slapping my hands out of the way when my breast fondling gets in the way.

"Jesus Jake...how about not be a 12 year old boy for a minute."

"I'm pretty sure 12 year old me would be confused as fuck right now." I said pointedly staring at her pretty girlcock.

"Asshole!" She says with a smile and a light slap to my half erect penis.

As her soapy fingers caress my body, I relax in the hot water, all of the day's stress gone, and I feel her finger slowly rubbing against my asshole, gently probing and circling.

Her free hand gently cups my balls, and the up my shaft, soaping and cleaning as she strokes.

Her finger eases into my ass, as she continues slowly stroking me with her soapy hand. "Oh, Cassie...who's the...ah...fuck never mind." As she finishes, I pull her in front of me, her ass grinding against my now rock hard cock, my hands sliding up and down her firm tummy, lathering her perfect breasts, and down to her beautiful cock, stroking slowly. I pull her earlobe into my mouth, sucking and gently nibbling. As my teeth close on her delicate ear, she lets out a sharp moan.

"Baby...I love that"

Eventually the water starts to chill and we hastily get out and dry off. She takes my hand and leads me to her bedroom, where a large towel has been folded in half on the middle of the bed. A black bag sits next to the towel, and I can see on it an array of toys and bottles of various shapes and colors. Cassie sees the look on my face and giggles, rubbing my ass.

"Relax baby...I promise we will take it slow. We have to get you eased into it. Are you nervous?" Fuck yeah I am I think.

"Fuck yeah," I say.

She laughs again, and leans over to kiss me gently. I'm once again lost in her brown eyes, my head going in too many directions like usual.

"It's ok baby...I got you. How about something to help you out a little? Want to try some Molly?"

"Sure...been a long time since I did that."

We both take a pill, and wash them down.

"Now come here, let me take care of you baby," she says softly, as she pushes me down on the bed. Cassie climbs on top of me, her breasts lightly trailing over my chest as she moves to kiss me. She traces her tongue down to my nipple, sucking and the lightly biting. She kisses her way down my stomach, her hair tickling me as she goes. I finally feel her breath on my cock, and then a tongue gently licking at the head, down one side of my shaft, and up the other. I harden in her hands as she kisses me.

Cassie reaches into the black bag and pulls out s single black latex glove, and a bottle of coconut oil.

"Coconut oil?" I question, doubtfully.

"Good for your skin, and lasts longer. Trust me," she says as the black glove snaps over her wrist, her eyes not leaving mine as she generously rubs the oil over her index and middle fingers. Oh, fuck....

Cassie laughs again, and smacks my leg.

"Big tough ex-Army Ranger scared of the little trans girl and her black glove?"

"Usually the black gloves weren't lubed and headed for my virgin asshole..." I say with a smirk that did a poor job of covering my nervousness.

"Relax baby...maybe I'll be gentle..." she says. Any quip I have in response is lost in a groan as she wraps her lips around the head of my cock, gently sucking, taking me in her mouth. I feel her slick oiled finger tracing a lazy circle around my asshole, massaging in and down my taint, slipping back to gently probe me. As her mouth engulfs my cock and her expert tongue caresses me, her finger pushes slowly but inexorably into my ass.

Working in and out, she steadily pushes her finger deeper inside, twisting her hand palm up, stroking my prostate.

Her mouth stops its wonderful work long enough for her to look up at me. "You OK baby? Tell me if you need me to slow down."

I reach down to gently stroke her cheek, loving the vision of her beautiful face next to my throbbing and wet cock.

"No baby...keep going" I manage to get out through a suddenly awkward mouth.

Cassie giggles again, and her head drops back down, lips once again wrapped around me. I groan again as I feel her middle finger easing in to join the first. Cassie slips her black glove clad fingers in and out of me as she sucks, then stops to lick and kiss. She uses her free hand to lightly slap my wet cock against her cheek.

She slides her fingers out of me, and I am surprised to already miss the tantalizing feeling of her in me.

" Let's try something else?" She asks as she reaches into the bad and withdraws a slim black vibrator, only as big around as her two fingers together, but ridges along its length.

" Scarier than it looks baby. This is one of my favorites. Hits all the right spots."

Cassie quickly lubes the toy, and I feel the cold silicone pushing into my ass. I give a little jolt as she turns it on, feeling the vibration spreading through me. She alternated between sucking and licking, keeping me constantly hard and stimulated, but taking her time. When her mouth isn't busy on my cock, she whispers soothing words of encouragement, or just kisses my thigh, or stomach.

Her tongue traces over a scar picked up in a place of sand and fire and pain. She kisses the scar, and while her kiss doesn't heal, it does push away the pain.

"Cassie...I want your fingers again," I mumble to her.

"You don't like the vibrator?" She asks.

"No, it's just not you," I say with my eyes closed.

Cassie pauses as she looks at me, contemplating for a moment, then without a word she slips the vibrator out and replaces it with her black glove clad fingers.

I moan as I feel her milking me, her mouth once again engulfing my cock. The tension builds within by balls, at the base of my cock.

"Cassie...slow down baby...I'm close...not yet.." I moan, twittering on the edge of orgasm.

"It's OK baby, we have all night...cum for me...please baby...I want to make you cum for me, don't hold back any more...let it happen," she says just before once again taking me in her mouth. My whole world collapses down to her fingers stroking my ass on the inside, and her mouth sloppily stroking my cock. I gasp out a cry as my orgasm hits, cum spurting out in wave after wave, the feeling rippling through my body.

Cassie continues to suck greedily, even after my orgasm passes and my cock slowly softens in her mouth.

As she raises her head, a single drop of my cum is there on the corner of her mouth. She uses one perfect finger to wipe this drop off, and the reaches up and slips it into my open mouth. The taste of my cum, her finger, and traces of coconut oil mix in my mouth as I revel in my post nut clarity.

——————————————————

Cassie kisses her way back up my body, and when she is face to face with me again, we kiss deeply. Petting each other, nuzzling against each other, we relax in each others arms.

She looks over at me, "Ready for round two there big guy?"

"Fuck, Cassie...I might need a few before I can get it back up again..." I stutter, "The spirit is willing, but the flesh is spongy and bruised."

"Futurama? Dork!" Cassie slaps my chest as she snorts out laughter. "Besides this is just a quickie, and then we can grab a snack."

"Lead on then, my master," I say with a flourish of my hand.

"Careful with that 'master' stuff, you may bite off more than you can chew," Cassie says as she again reaches into her black bag.

I'm her hands are two butt plugs, one made of shiny metal with a long fox tail attached to it, the other a modest black silicone.

"Oh please tell me I get the fox tale!" I say giddily.

"Nope! I'm the foxy one. Yours has a surprise. Come here, I just need you to pull your knees up."

Cassie pushed my legs up and kneels between them. Once again, coconut oil is slathered over a toy, and Cassie gently begins easing the plug in and out of my ass, while slowly fondling my balls and, surprisingly, slowly hardened cock.

"Just relax baby...I've got you. It may be a little tight and uncomfortable at first, but that won't last." She applies gentle pressure, and I grunt as I feel the thickest part of the plug pass inside of me. Gone is the stretching feeling, and instead I feel a pleasant full feeling. She continues to play with my penis while gently pushing and twisting the plug, eliciting little moans of pleasure.

"My turn now," she says as she gets on all fours in front of me.

I gaze at her beautiful round ass, firm and muscular in front of me, perfect little puckered asshole staring at me, and her sack and semi erect cock hanging below.

"You just going to stare? Play with me, put the plug in, do something! I'm thirsty!"

I run my hands over her firm ass, feeling the smooth warm skin, down her strong thighs, and back up to cup her sack and stroke her to full erectness.

I reach into her bag and grab one of the black latex gloves, and after a quick lube with coconut oil, I run the tip of my finger up and down her ass, and then gently push a finger inside her.

"Like this, Cassie?"

"Oh baby...yes...one more finger babe...oh yes...just like that, now turn your hand...oh! Just like that...mmmm now make a come here motion...ahh...yes...yess"

As Cassie coaches me in the best way to finger her ass, my free hand strokes her cock, squeezing and sliding. I lean forward and kiss her round butt, licking her cheeks, and giving her a little bite, making her yelp.

"Asshole...you'll pay for that..ohhhh" she moans as I find her spot, and focus on it.

"Ok...stop, stop! I don't want to cum yet."

"What happened to 'we have all night?'"

"That was for you. I'm waiting for something else," she looked over her shoulder at me, hair spilling over, almost covering her face, "Now give this foxy bitch her tail."

I work the fox tail plug gently in and out of her ass, finally pushing it fully in.

Cassie gets up and starts walking around the room, beautiful ass shaking, and long fox tail twitching with every step.

"Fuck you are beautiful Cassie," I say with reverence in my voice.

"You don't need to sweet talk me, you already got me in bed. Come on! Snacks!"

We walk into the kitchen, her with sensual grace, and me walking with a slight limp, still getting used to the feeling of the butt plug riding in me.

I gingerly sit on one of the chairs, feeling the plug go in a bit deeper, but not uncomfortably so. I shift my weight back and forth a bit, experimenting with the sensation.

Cassie brings a plate of fruit and cheese and bottle of beer for me and a Truly for herself.

"Truly? What a girl..." I say with a smile.

Cassie sticks her tongue out and slaps my leg. "Asshole!" Comes her predicted response.

As we sit and chat, the Molly starts to hit, and I just drift for a while. Cassie touches my hand, "You ok there?"

"Yeah babe...just vibing. I've got a butt plug in, while I sit naked at a sexy trans girl's table eating grapes and talking about work."

"Pretty wild huh?" She smiles radiantly. "Speaking of vibing..."

Cassie pulls out her phone, and pops open an app, I jerk in my chair as the plug in my ass begins vibrating. The sensation rocks through my body, I let out a slow moan.

"Ohhhhh shit Cassie...little warning next time? Fuck that feel amazing."

She laughs as she flicks her finger up and down and the pitch of the vibrations change.

"Looks like I'm in control. You like that baby?"

"Goddamn Cassie, just leave it!"

She giggles and then hits another app, from the Bose speakers in the apartment the heavy beat of a Sleep Token song begins to play.

"Ahh I love this band! Play the Summoning"

Cassie looks at me, then hits another button on her phone. Now the vibrations from the plug are in synch with the song. I sit there, hearing and feeling the song, my vision gone past high def, fully in the grasp of the Molly. I look at this beautiful girl, so perfect, looking at me.