Authors note: This is a constant fantasy of mine I thought I would share with you all. While I have never had the pleasure of engaging with a transgender woman its on my bucket list. I hope you enjoy and do not hesitate to drop a line if you do. Also smoking is bad for you!
I didn’t want to be here in the first place. I hate clubs, loud music, dudes fighting over the chance to get laid, and overpriced booze. However, I was a good wingman so I came, my buddy, Chris was going through a “dry spell” that he was determined to break. I never understood why he thought that way, I never went out of my way to get laid and felt like I got laid fairly often. For Chris it was all about the chase, this was an Olympic sport to him and I was just a trusty sidekick.
I tapped him on the shoulder, yelling in his ear that I was going outside to smoke. He nodded casually, too wrapped in the conversation he was having with a seemingly uninterested brunette. She looked up at me, I winked, she smiled, I walked away, see simple. When I made it outside past the bouncer whom I made sure to make eye contact with so he would let me back in, it was cool out. I loved a crisp evening. I wandered around the corner so as not to disturb people since smoking was frowned upon in the world these days.
I walked into an alley and pulled out my smokes, I chuckled to myself popping a cig in my youth and flicking a lighter. It was funny how all of a sudden it became the “hipster” thing to do to still smoke real cigs instead of sucking down e-dicks. I inhaled and looked up into the night still hearing the pulsing vibrations from the club. I wondered when we could just leave. I heard the click of heels on the sidewalk heading in my direction. I sidestepped deeper into the alleyway to avoid blowing smoke directly in her path when it stopped.
I tilted my head and saw a tall blonde standing there taking a good look at me.
“Wow, it’s been a while since I saw a cigarette. Do you mind sharing one with a stranger?” She said stepping into the alley slowly putting a lot of sway into her hips so I could see her curves and how her party dress hugged them.
“Sure, why not. It would be nice to have company in this exile.” I pulled out my smokes, handed her one and held out the lighter. She leaned forward so I lit it for her. Her lips around the end of the smoke were a deep red and the glow of the flame gave her face a beautiful allure.
She inhaled, pulling the cig from her mouth in between two-finger and blowing out the smoke while catching me look her body up and down.
“I suppose exile is about right, can’t smoke these unless you hang out in shady alleyways.” She quipped.
“Exactly, sometimes I ask the local muggers for a light. They get it, being a part of the criminal underworld means we gotta look out for each other.” I took a pull and let my crap joke land.
She laughed a bit amused but real enough not to overdo it. I liked her already.
“Well since we now belong to the criminal underworld do we share real names or the aliases we came up with to sound cool?” She took a step closer looking at me through the hair that had fallen to cover her face.
I stuck out my hand, “My mother named me Diego but in these streets, I am known as Heavy D.”
She giggled, reaching for my hand giving it a casual shake.
“Nice to meet you Heavy D, some call me Tina but when I decided to become a real criminal I changed my name to Uhm…Lady Larceny!”
I let out a full laugh at her attempt to come up with something and land on “Lady Larceny”.
“Well, Miss Larceny, what brings you to this particular hotbed of criminal activity this evening?”
“I am here with some girlfriends, I am the designated sober person this evening and needed a break.” She smiled taking another drag, soon I would either need to offer her another or let the conversation go.
“Same, I have a very thirsty friend inside looking to get a drink tonight.” I stepped forward, popping one more smoke out of my pack holding it by the end filter towards her mouth.
She smiled, pulled the short one from her lips and dropped it, taking a moment to step on it with her heel, letting me enjoy the definition of her leg. She leaned forward and took the smoke from my hand with her mouth. I flicked the lighter, and got it going.
“Well hopefully he gets a drink then, and how are you this evening? Hydrated?”
I smiled, lighting my smoke.
“Come to think of it, I am beginning to get a little parched. What do you say Lady Larceny, you up for some illicit activities tonight?”
“Oof Heavy D! While I appreciate you holding onto the bit you gotta commit some misdemeanors before you ask for a felony.”
And that’s how it went, she was smart, she was funny and was gorgeous. We spent the rest of the night dancing in between check-ins with our respective crews. It didn’t take long for us to simply introduce her friends to mine, it gave Chris three more chances to strike out but her girls were wasted thus increasing his chances.
Tina and I flirted on the dance floor whispering into each other’s ears crimes we would commit together until she breached the one I wanted to hear.
“Indecent exposure.” She breathed heavily in my ear.
I could feel the sweat our proximity was generating. I nibbled her ear and whispered.
“Public indecency.” My hands traveled down to her ass.
The room ignored us but I was hyper-aware of the number of people grinding around us. I glanced over at Chris, he was lost in a burst of obnoxious laughter with one of Tina’s friends. I was clear, I kissed her neck and slid my hands up her hips enjoying her ass in my lap. I pointed us towards the bathroom, I grabbed my keys from my pocket and whispered again.
“Bathroom,” I said pointing in the direction. “Or, I can take you home and show Lady Larceny how many misdemeanors I can commit before I get to the felony.” I jingled my keys in front of her.
She turned to plant a kiss on my lips. “And what happens to the goof troops over there when you take me home for that…Heavy D?”
I squeezed her ass “are we criminals or are we law-abiding citizens Lady Larceny?”
She laughed. “What happened to stick together? Help me get them home safe and I’m all ours tonight if you will have me.”
“You have yourself a deal.”
I let her go and took her hand bringing her to the table.
“Chris, come over here.”
I watched him get up on wobbly legs, and half dance his way to me looking back at Tina’s friend before turning to me.
“In. The. Bag. The drought is over, big guy!”
“Yeah, yeah, yeah, look I am in need of a wingman myself so I can secure my bag, we need to get these ladies out of here.”
“Ok, let me seeaaaaal the deeeeaaaaal.”
His words were accompanied by what looked like a hand motion for sliding your fingers across the top of a Ziploc bag, I rolled my eyes. It took almost an hour to play the shuffle that was her driving people home, my dropping off Chris and the unlucky lady who chose him, and getting back to Tina.
I had just enough time to run around my place and clean things up before the doorbell chimed. I took a second to not look out of breath and answered, she had an oversized purse with her and still wore her party dress.
“Lady Larceny, you got your girls home. Chris is probably already in love with your friend and now I get you all to myself.”
She laughed while coming in kissing me.
“Time for a drink maybe?” She asked.
I took her by the hand and guided her to my kitchen. We both took a glass of whiskey and went to the porch for a last taste of the night air and nicotine.
“You mind if I lose the heels, cute as hell but my poor feet are killing me.”
I laughed.
“Sure, make yourself comfortable.”
I watched her step from her heels and down to the floor with her bare feet. I took another drag and drank her in leaning against the railing of my balcony. She was stunning, I couldn’t believe my luck.
“You are beautiful, you know that.”
“Stop, you are going to make me blush, don’t oversell I am here with my overnight bag you are already getting laid mister.”
“Aww c’mon, I am not running some game to get into your very sexy dress I mean it. You are beautiful, and funny despite me getting laid tonight.”
She took a drag and closed the gap between us putting her hand on my chest and exhaling to the side.
“If I left now would you still want me in the morning?”
“If you left now I would be upset if you didn’t agree to breakfast.”
She bit her lip, thoughts passed her mind I wish I could have captured. The moonlight illuminated her eyes looking into mine and I could hear my heart pounding.
“Breakfast in the morning. You, me, pancakes, and coffee. What do you say?
“Waffles and coffee, the obviously superior breakfast and you can take me thereafter we wake up.”
I feigned offense to her breakfast jab and planted a light kiss on her forehead.
“You are too pretty to be so uneducated about what makes a good breakfast but I will look past it and agree. First thing in the morning.”
She laughed. “You are a charming man but bound to have flaws, I appreciate that you are bringing them to the table now.”
We kissed, our hands explored each other as half-lit cigarettes fell from hands as we kissed sharing the taste of smoke and whiskey. She moaned into my mouth running her nails down my back under my shirt. I pulled her close so she would feel how hard I was for her. I ran my fingers at the hem of her dress where it met the back of her thighs aching to feel her skin when she broke the kiss.
“I have a confession to make.”
“Oh, squealing before you even get arrested is bad form. I am disappointed Lady Larceny!”
At some point, I needed to let this whole thing go but I will admit I was having fun with it.
“Hopefully my confession won’t be disappointing. I am done with this dress. Would you mind if I put on something else?”
“How about we just get you out of the dress, why bother putting on more clothes?”
I kissed her and both of our cups went ignored. I guided her to my room where she didn’t hesitate to push me down on it. I immediately went for my shirt, pulling it over my head and tossing it aside. Bending at the waist she kissed me as I sat in the bed fumbling with my belt.
“Let me.” She whispered slowly, dropping to her knees.
My belt came on in a smooth motion sliding through the loops before being placed on the bed next to me. She unbuttoned my jeans and I got up slightly so she could slide them and my boxers off in one smooth action springing my cock free.
“Heavy D…..I didn’t know you were into concealing weapons.”
I loved that she was still into this little game. I was already leaking pre-cum.
“Never know when you may need it, better to have it I say.”
She gripped reached behind her, unzipping the dress letting it expose her breasts before grabbing the base of my cock and kissed the tip letting it press against her full lips.
“I would agree with you there, I am glad you have it. I need it to steal something from you, I hope you don’t mind I am after your jewels Heavy D.”
Her hand massaged my balls as she said the word jewels. My head was swimming watching her kiss the tip of my cock and rolling my balls with her fingertips. I was running out of clever things to say.
“Exactly what I expected Lady Larceny, you are going to have to work pretty hard to get them though.”
She giggled her beautiful laugh with her lips against my cock planting little kisses. She was thinking of a comeback, I was thinking about shoving her face down my cock but I chose to enjoy her taking her time. Something about her made me want to take this slower than usual. After a few moments, she stopped thinking and opened her mouth taking the head of my cock in and sucking it gently, running her tongue over my hole collecting what had already escaped before letting it go.
“I needed this, you taste so good. It’s been a while, do you mind if I take my time?”
My ego inflated along with her cute factor at that moment. I was so glad I was sober enough to appreciate it.
“Take all the time you need,” I whispered.
I watched her slowly start to suck me, giving me the most intimate blow job I had ever received. She worshiped my cock planting kisses along the shaft and sucking the tip for a while before descending to suck my balls. I moaned, leaning my head back, closing my eyes, hearing the very subtle sounds of her taking my full length in her mouth and gagging slightly. She tested her throat several times before being able to push through and place her lips against my pelvis introducing my cock to her tonsils.
“Good lord you are amazing.” I groaned.
She didn’t bother responding, simply kept going as I gripped my sheets anxious to have more of her but unwilling to press her to stop what she was doing. She didn’t pick up the pace, she didn’t make explicit sucking or slurping noises and she didn’t start gagging profusely, all the things I thought I liked. She slowly and methodically sucked, coaxing my cum to the surface. I knew I would have to stop her so I wouldn’t finish in her mouth.
“I am getting close, let me take care of you,” I begged.
“Or you finish and see how long it takes me to get you ready again.” She whispered leaving my cock for only a second.
It wasn’t a request, she simply stated what was about to happen and I surrendered control. I allowed myself to lay back and let her work. It took moments, not minutes for my body to tighten and release my pent-up need into her mouth. She didn’t stop, she took me at my most sensitive moment and continued sucking slowly drawing out every bit of cum I could muster. I exhaled sharply only then realizing I had been holding my breath and let myself sink into the bed as she kissed my balls.
“That was….amazing.”
“I am glad you liked it.” She said planting one last kiss before getting up and letting her dress fall to the floor.
I looked up just in time to see her climbing on the bed next to me, her curves on display as she placed a hand on my chest and went in for a kiss but in the corner of my eye, I noticed something that shouldn’t be there.
I scrambled up and off the bed.
“What the fuck you have a dick!”
Her face showed as much alarm as mine did but it was there plain as day a small cock laying exposed between her thighs.
“Oh my god, I thought you knew! My friends said your friend knew so I assumed you did as well, Oh my god I am so sorry this is… Oh god!”
She covered herself hopping off the bed and out of my room slamming my bathroom door. Suddenly I felt like shit, I could hear her crying in the bathroom and I was confused. I liked her, that blowjob was amazing but she has a dick? Am I gay? What the fuck just happened? I took a few deep breaths and composed myself. I needed to relax to think straight, the first thing that came to mind was I needed to apologize.
I grabbed some shorts out of my drawer and went to knock on the door. I hesitated for a moment hearing sniffles and dropped my head. I had been an ass, but damn that was alarming. I knocked.
“Hey, I am sorry I freaked out like that. I didn’t mean to hurt you, I just…I just didn’t know.”
I waited for a moment and she didn’t respond.
“Look, can you come out so we can talk about this?”
“It’s not your fault I am sorry, I should have been clear about this. I just thought you knew.”
“Can you come out, please? Please?”
I waited for what seemed like an hour before the doorknob turned and she came out wearing a towel trying to cover herself. I had to admit she was still beautiful, I just didn’t know why I wanted to admit that to myself.
“Can you grab my bag please?”
“Yeah, it’s over here but can we talk about this?”
I walked the distance to get it and came back holding it out in front of me hoping she wasn’t trying to leave.
Why do I want her to stay?
“We don’t need to talk, I won’t tell anyone, we can just pretend this never happened.” She reached for the bag and I forced myself to not hold it hostage. I was getting frustrated.
“We DO need to talk this isn’t about you telling people I don’t give a shit right now! I like you and I don’t know how to feel about this so we need to talk about it, Tina!”
She looked as if I had slapped her in the face, she stood frozen with her bag in hand looking shocked I raised my voice or just shocked in general.
“You don’t want me to leave?” She asked slowly and with a heavy amount of curiosity.
“NO! I want to take you back to bed and this is all new to me and I don’t know what to make of it and I just need to talk this through.”
I realized I was pacing and stopped forcing myself again to calm down taking deep breaths.
“Ok, I’ll stay. Let me put on some clothes and we can talk.”
“Thank you, I’ll be outside.” I huffed giving her more attitude than she deserved.
I located my smokes and my glass downing the two fingers of whisky and lighting up a smoke. It took her a few moments but she came out wearing sweatpants and a hoodie burying her curves outside of the healthy amount of ass.
“I’m not gay.” I blurted.
She looked hurt but let it roll off taking a smoke from the pack and lighting it herself.
“I know.” Is all she said.
“But I like you, we had fun tonight even before you gave me the best blowjob of my life. What does that mean?”
I took a long drag and lit another with the cherry of the first.
“I like you too, and if I am honest I like that you liked me without knowing. Sometimes I worry guys are just out to scratch a kink itch.”
I took a second to take that in and understand how difficult it must be for her to find people that see her for her. I empathize, although I couldn’t truly understand.
“Sorry if I made you feel like shit. I really am.”
I turned to look at her so she could see my face as I apologized again. It hurt to see her upset and it hurt to see how far she was from me. It was like in a moment we went from lovers to strangers. My mind screamed at me to close the gap but my body did not move.
“It’s ok, you have made me feel really good otherwise. Just poor communication on my part.”
She located her cup and downed her whisky just as I had. I put my smoke out and grabbed her glass enjoying the proximity again. My fingers rested on hers as I stared into her eyes.
“I’ll get you another one. If you want.”
Somehow I was nervous around her again like I was just meeting her for the first time. She bit her lip looking at mine before nodding. I took both cups in and poured a heavy glass for both of us. I took a second to get in sync with my inner dialogue.
You are thinking too much just relax, you like her, she is a cool person, just let it ride for now we will sort the rest out later. I agreed with myself and walked back out to the balcony where she was standing in the spot I just left. I handed her a glass and held it up. She touched hers to mine and chanced a small smile.
We each took a sip, the tension was immense and something had to be said but I had no idea what.
“At least my heist was a success, Lady Larceny strikes again.” She offered raising her eyebrows over her glass.
I smiled, I actually laughed, and we both burst into awkward giggles.
“Best heist I have ever been a part of by a long shot.”
“You said that already you are going to make me blush, you can’t just keep congratulating my “heisting” skills like that.”
I shrugged feeling the blood divert its attention to my cock again.
“I mean, I kinda have to give credit where credit is due. You have terrible communication skills and your ideology about breakfast is appalling but you can heist the shit out of some jewels.”
I liked this feeling, the whiskey was taking away the edge off the conversation and we were able to speak frankly about what was going on between us.
“Well…” She paused.
“I promise I will work on my communication skills, I refuse to convert to the blasphemous church of pancakes but if you wanna participate in another heist down the line I would be willing to have you join me.”
The tension thickened again as she casually dropped the real question. Is this over?
I put my glass down and looked at her.
“I can’t promise I will be able to give you what you want, I don’t even know what that is but I’ve never touched another dick before.”
She shot up from the banister and into my space faster than expected, hugging me catching me off guard.
“Thank you, we don’t have to do anything you are not comfortable with and I am willing to wait just thank you for not throwing me away.”
I hugged her tightly, I could feel my cock stirring as I inhaled her scent. She looked up at me and I kissed her. I pushed past the voice in my mind that was still trying to overthink and enjoyed the moment. We broke the kiss and a single tear cascaded down her cheek. I wiped it with my thumb.
“Can I take you back to bed?” I asked.
She smiled and nodded. Again we abandoned unfinished drinks. I closed the door to my bedroom behind us and pulled up on her sweater. She hesitated but let me pull it over her head, we stared at each other for a moment as I got up my nerve to grab the drawstrings of her sweatpants. She put her hands over mine.
“It’s ok, we don’t have to.” She whispered, still smiling.
“I want to.”
I untied the drawstrings, hooked my thumbs in the band, and kissed her while I pushed down. I felt the pants hit the floor at my feet. Her hands went to my shorts and dropped them. I pulled her close, kissing her deeply, I could feel her arousal poking me, I didn’t mind it.
We stood there just embracing the moment of our brazen nudity. I made the move to lay her down and she slowly made her way to her back scooting up the bed. I looked at her, a sliver of moonlight cut across the room and over her stomach. She was nervous still feeling exposed like she was but I could see the lust in her eyes. She wanted this as bad as I did.
I crawled on the bed stopping at her nipples for a quick kiss, enjoying her moan, I kissed up her neck to her ear and whispered.
“How do I make you cum?”
I felt her smile as she turned her head and met my lips.
“Fuck me, I’ll cum for you..”
We kissed passionately until she rolled over pushing her ass up into my lap. I watched her lick her hand before using it to lube herself and offer herself initial penetration. I followed suit, spitting in my hand and rubbing it on the head of my cock. I was hard as I had ever been. I could feel my cock straining to find more room to expand. I was so turned on by her.
She turned her head looking over her shoulder. “I’m ready, just..take your time it’s been a while.”
“Of course, You got to show me your heisting skills. Now it’s time to show you why they call me Heavy D.”
We both laughed, more out of nervousness on my part, maybe hers but it felt good to giggle before I pressed the head of my cock against her asshole. True to my word I pressed slowly, she grunted into a moan as soon as my head pushed through. I held her waist pushing in with a controlled measure offering a half-inch at a time. I was nervous and turned on, her tight ass was amazing and I didn’t want to ruin this. She moaned under me with a little labor like she was in pain.
“You ok?”
“Yes-.” She gave me a short exhale.
I stopped a moment trying to help her relax.
“No, don’t stop. I am fine you are just so big. Takes a bit to get used to.”
I said ok and kept going slowly until I had finally sunk completely inside of her. She moaned into the mattress as I pulled out to my head and sunk back in slowly. I wanted to fuck her hard, I wanted to work out this confusion, I wanted to punish us both for liking this so much but her moans, the arch of her back, the smell of her was enough to make me slowly work her. Just as she did me I would take my time with her.
With each stroke came a sense of ease, she was relaxing, her moans went from labored to silky as she looked back at me throwing her hair out of her face. I loved the eye contact we made as she allowed me to see her face full of pleasure.
“You like this baby?”
“Yes Daddy, just like this.” She moaned tickling the hairs on the back of my neck with the term “Daddy”
I mixed up my strokes from full deep strokes to half strokes reading her body as she moaned for me. She liked when I squeezed her ass so I took it a step further raising my hand and slapping it hard.
“Oooh yes, slap it!” She cooed encouraging me further.
Her hips began to keep up with my strokes as she brought herself back against me. I slapped her ass again. She pushed her ass back harder, rolling her hips, taking control of the strokes, and taking in what she wanted. Now I was the one groaning watching her work. I slapped her ass switching sides enjoying her squeals with each one.
I grabbed her waist and pushed in offering her deep strokes over and over until she moaned deeply.
“I’m going to cum Daddy don’t stop.”
I followed instructions and I felt her body tense, heard her staccato breaths and quick jerks of her body. Her hands gripped the sheets as I stroked every last drop out of her.
“Wait, wait, hold on.”
I slowly pulled out and lay down next to her enjoying her post-orgasmic bliss through strands of hair covering her face.
“Can I get a washcloth or something Daddy? I made a mess on your bed.”
I laughed and got up to get one, she wiped up as much as she could and I settled for just pulling the blanket off the bed. I laid back down next to her, rubbing her back as she lay on her stomach.
“Time to finish you off Daddy.”
She climbed on top of me straddling my waist and lining up to sit on my cock. She was beyond feeling self-conscious and slowly sat down. I held her waist and watched her run her fingers through her hair giving her breasts a nice bounce to them with each stroke. Her flaccid cock bounced on my stomach and I couldn’t help but watch it still drip. She placed her hands on my chest staring down at me with fierce intensity bouncing harder.
“Cum for me Daddy make me your good little slut.”
I groaned as her explicit verbiage took me over the edge and she rode me through my second load for the evening. We kissed as I caught my breath and came down off the intense high I was feeling. I was in a half-daze as she cleaned me up and cuddled next to me. I held her and kissed the back of her neck.
“Still want breakfast?” I asked.
“After that and what you are going to get when you wake up, hell yes, I’ll even have pancakes Heavy D.”
xx
Belle