Lucy's New Toy

--Writer's note: This story started off as one idea of organizing a fantasy and its variations into a coherent narrative, and turned into much more. The story itself pushes through some personal boundaries of safety and ethics for the sake of the storyline and pace, but who wants to read about pre-negotiated scenes...it's fantasy. What happened in the end was an exploration of desires, and discoveries about my own boundaries, identity, and attractions I had yet to fully realize. It's my first attempt at erotic writing so I'd love your feedback! 😅--

--Warning: contains content that may not be your cup of tea including: Coercion, some physical aggression, cunnilingus, analingus, anal sex, biting, public play, threesome, light choking, sex with a stranger, and transgender sex.--

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-Lucy's New Toy-

I'd been aching to go out all dolled up and feeling sexy. It's not something I do often, and never in public places or alone. But I'd heard about a local bar that was friendly and some other queer folks visited, so I resolved to try and meet people. I've been told I'm fairly passable when fully dressed as a woman, and definitely not recognizable to someone who doesn't really know me. But my voice is a dead giveaway and I have unfortunate broad shoulders...nervous was an understatement. But I glided in anyway and found a seat at the bar.

It wasn't too crowded and I opted to go with wine tonight, feeling it was somehow more "ladylike" than my usual beer (I do like a good red zin). The bartender smiled and served me promptly making me feel a little more at ease, not seeing any negative reaction to my looks or voice. And so I settled in and resolved to pace myself so I could drive home alone as planned, after getting used to the new place and just "people watch". I wanted to know if there were people my age that visited. Were there those who were friendly to trans/enby folk? Would any be a bit kinky? How do you even strike up a conversation about these things? The nerves hit again and I took a long pull from my glass and took a deep breath. 'None of that matters. Just relax and let things happen. Watch, smile, be friendly, and don't forget to tip the bartender well.' I told myself. It was then I saw her.

A lovely woman was sitting alone at a small, round bar table not too far away. She appeared a bit too young to consider sending her a drink, maybe in her mid 20's; myself being middle aged. And besides, she was WAY out of my league even in my prime. Her long, wavy, dark hair flowed down her back and parted over a bare shoulder which peeked out from a form fitting, but classy black dress. Her porcelain skin set in contrast to the dark dress and hair, and the flawless dark eye makeup that I took special note of in hopes I could improve on my own more. Her elegant cheekbones perfectly accented with a little pink, and a red lipstick were the only color on an otherwise black and white goddess. Not so red it clashed, but just enough to seem to be making a statement, leaving imprints on the rim as she quietly sipped a pale red cocktail from a martini glass. Her feminine curves and movement made me feel at once out of place, but I reminded myself not to compare, and if anything, to use the inspiration.

When she raised her glass, she brushed her hair back slightly to reveal a choker. It was hard to see detail from my angle, but it wasn't uncommon as a fashion choice nowadays though it did make me wonder a little. I pried my gaze away not wanting to linger too long in case anyone noticed, especially her, and continued checking out the other people meandering in and out ordering drinks and meeting friends.

I sat and sipped my wine slowly as the time went by, and felt more comfortable. At this point I was just keeping an eye out for others that might be queer to see how they were treated by the rest of the crowd. But it's not like most people are wearing a big sign. It's the little things to notice; body language, casual touches, and I'm always looking for a rainbow keychain or pin, or other small visual cue. For the most part all I could do was guess, but there was a couple of college aged guys holding hands as they came in to sit with friends. One was rather cute in his way, though not typically in my wheelhouse of attraction. But they were obviously a couple out having fun together and it made me wish I had been a bit more open to exploring when I was that young. No one stared or gave dirty looks that I saw, and everyone was enjoying the evening making me feel more like this was a place I could get used to.

I noticed the young woman again, just turning down at least the second guy I'd seen come to her table. I couldn't hear them, but I could tell she was a practiced hand at politely dismissing unwanted attention. I watched him walk away as he made an "oh well" gesture to his friends across the room. As I was turning the young woman met my eyes for a moment and smiled. Taken aback, I felt myself flush as I sheepishly returned the smile, turning away quickly and attending my dwindling glass of wine sitting on the bar. I finished the last of it and tried to make sense of what just happened. "Surely she was just being polite" I told myself, and I tried to push it from my mind as I considered a second glass or perhaps just water.

I was contemplating leaving soon, but I had to admit I was feeling more comfortable than I expected and thought I may stay a bit longer. It was still early for me, being a night owl, and I had only planned to 'just dip my toes in a bit'. But the water was warm, and I decided to wade in just a bit further. I sat for a bit thinking to catch the bartender's eye and the next opportunity and have just one more glass of wine before calling it a good night's experience. He was at the other end of the bar filling several pints and talking to a waiter, so I glanced around a bit more and waited. After a few minutes he looked my way and I gestured. He came over and began pouring another glass and said, "This one's on the lady."

Confused, I asked "What lady?" No one had ever got me a drink before. I was stunned, and a bit surprised I even got the words out.

With a huge smile he nodded towards the beauty at the round table sitting alone and as I looked, she raised her glass and smiled again holding a hand out indicating the chair opposite her.

"Good luck," he whispered as he turned and walked away. I'm sure he was laughing himself silly at the look on my face, or the sound my jaw made when it fell open and hit the bar. My night had just taken a VERY unexpected turn.

I took a moment to make my legs move, but I managed to slide off the stool. I straightened my skirt and took a step before remembering to take my glass of wine and purse off the bar. I tried to take a deep breath and calm myself as I walked towards her, but I was suddenly aware of every step, feeling very self conscious as she watched me. She gave me a warm smile as I approached, making me feel slightly better.

"Thank you so much for the wine." I squeaked out as I got to the table side.

"Sure! You looked like you needed some company and I could use some myself. I'm Lucy." She had a voice to match her face; beautiful and elegant. She had golden brown eyes that were warm and inviting, making it hard to look away. I could clearly see the collar now and my thoughts lingered for a moment on it. It wasn't a cheap plastic style one often worn as a fashion accessory. I know leather, and this was hand made and well finished with subtle tooling around the edges. But best not to assume.

"I'm Emily. I love your collar." SHIT! Did I just say that out loud?! Being off guard does nothing for my brain/mouth filter. I must have been reaching for any topic I knew something about. Maybe I could play it off if she didn't notice.

"Thank you! This is one of my favorites to wear out. I'm happy you noticed it. It makes me think I sent a drink to just the right girl."

"Oh, I didn't mean to...uhh...what?"

"Shy and sweet?" She lightly touched my hand as she leaned in, smiling wider. "You noticed...and you understand. You do understand?"

"Yes, I...I think so. I think maybe I should have permission to be here talking to you actually."

She sat back laughing a bit and flashed a knowing grin. "Sir and I have an arrangement. I am His, but I also need to have my own." she said leaning back in. "And I like going out and toying with the 'unworthy' trying to buy me drinks and take me home. I like seeing them sag as they walk away. But you wouldn't walk away would you?"

"No Mist...err...sorry, no ma'am? Not unless you asked me." I could feel myself blushing.

I wondered how badly it would show through my makeup. I couldn't help myself. Something about her gave me such a "subby" feeling like I had never felt before. Only a couple of minutes of talking and I WANTED to please this woman...this goddess.

"Oh, I see you'll need a little training, but you're on the right track. My favorite; raw and uncut, in need of polishing. You'll do nicely I think. But why don't we get to know each other a bit better now that we have an understanding." She said, pausing to take a sip from her drink as if she expected me to start.

"Sure." I managed, before slipping into small talk. It seemed odd to move to such a vanilla subject after starting with such "taboo". But we did skip over it, and there's a lot to cover when meeting someone new, however superficial it sometimes seems. We talked for nearly an hour finding out little details. Laughing sometimes and serious at others, but I was feeling very comfortable as I neared the bottom of my wine. She seemed interested in my leather working and crafting, and I really connected to her work as a graphic designer and love of art in general. The time went by quickly and I suddenly realized both our glasses were empty.

"I think I'd really like you to walk me to my car now." Lucy slyly said as she winked and put her purse over her shoulder.

"It would be my pleasure to walk you." I blurted out as I grabbed my own and started for the bar to close my tab. After getting my credit card I turned and took a step for the front door expecting her to be waiting ahead of me, but she wasn't there. I looked and saw her standing a little off to the side.

"I'm parked out back and down a little. We can use the back door." Her eyes lit up a bit and something flashed across her face for a split second as she turned. I went out with the idea of just getting comfortable in hopes one day I might be able to meet someone and actually "pick up" a date. Suddenly I felt like the prey. Did I just get picked up? What was going on? Why do I suddenly feel like I'm the one on the menu?

While she didn't hurry off, seeing I was starting her direction she did not wait and I had to take a few hurried steps to catch up to her. Upon reaching her side I saw what looked like satisfaction in her eyes as she took up my arm and we matched pace. Her walk was graceful and confident, and she was nearly as tall as I was even with my heeled boots. She too was wearing heels, but I estimated I was only an inch or so taller barefoot. We walked through the bar to a single back door at the end of a hallway with a waiters service station, and she stopped expectantly. I was already moving forward and opened the door for her. I stepped out first holding the door and looked around and then back to her as she emerged.

"Well done. It was very thoughtful for you to clear the alley for me." She said as she glided past and veered left. "I'm this way."

"Of course Miss..."

"That will do for tonight. Just 'Miss' from now on." She interrupted before I could correct myself. "Or Miss Lucy if appropriate."

"Yes, Miss Lucy." I breathed feeling relieved to have a proper way to address her.

Her smile widened. "I assume you're interested then?"

"Interested in you? Of course, who wouldn't be Miss?"

"Mmm, yes, but I mean interested in...how you could please me." She said with some thought.

"Oh yes Miss, your pleasure would be mine." My face heated again at being suddenly so forward and I was very glad to have chosen a skirt tonight. As feminine as the woman made me feel, this was not the first time tonight I felt myself "stir" in her presence.

"Good," She said "Then I will lay out some things for you. I would require obedience to me alone when we're together, but I require Sir's approval for all my playthings. Would that be acceptable?"

"You mean Sir would want to meet me?" I asked.

"You will not address Him as Sir. In fact, you will not address him at all; only me. Sir will be present, yes. But you will not address Him or look Him in the eye. I will interact with Him but you will only address me, as you are not worthy to engage. You would be MINE as I am His. Can you agree to this point?"

I thought for a moment. I didn't know for sure about this "Sir" and her reverence of Him made me a little uneasy. But something deep inside her seemed comfortable and inspired trust. Or perhaps, looking back, it was a longing to please her. But at last I answered "Yes Miss, I accept these terms and wish only to please you."

"Excellent. A well stated answer pleases me greatly." she said as her pace picked back up. We had slowed slightly for this part of the conversation and now she seemed satisfied as we came to the end of the alley and rounded the corner.

We stepped into a small parking lot with room for maybe a dozen cars and only a few were taken. Not what I thought of as well lit, but there were a couple of lights; and I could see well enough but for a couple of darker areas. There was a small red car parked next to a white van at one side, but most of the cars were well spaced and the lot seemed disused after hours.

She suddenly stopped as she looked up and her eyes got wide. It may have been the lot's flood light directly on her face, but she seemed to lose a little color making me uneasy again.

"What is it?" I asked, seeing her face and then looking in the same direction as she.

"Sir." she gasped as a shadowy figure shifted and leaned against the white van.

I felt a shiver at her alarm and froze not knowing what to do. All I could muster was, "Miss?"

Lucy straightened and turned to me. All her composure and grace magically returned and she smiled and she placed a hand on my face "My sweet, things have moved more quickly than I planned and I've not properly prepared you. So I will give you this chance to walk away. But I see in you an instinct, and though you are not yet trained, I know you can do this even if you are unsure. I cannot promise you will fully enjoy all that comes next, but I can promise reward and comfort if you give yourself over completely. And perhaps even bliss if you so desire. Now you must choose: Remember what I've told you and follow me to ruin and pleasure on a new level, or leave now and return to your comfortable life."

My heart thudded like a hammer in my chest. The fear inside screaming for me to leave; just walk away. I felt my pulse pounding in my ears as I pondered what she had just said. 'leave now and return to your comfortable life?' She knew somehow. Many times I thought of how my vanilla comfort had badly become uncomfortable, and resolved that pushing my boundaries, though painful, was necessary for my happiness. How could this woman have instilled such trust and longing in such a short time? How could I disappoint her? In the second it took to consider all this, I made a decision. I took the uneasy feeling in the pit of my stomach and set it free to wash over me. I cloaked myself in it. I relished it. I resolved this new feeling was a boundary of comfort, and experiencing it was a sign to push through to new levels of growth and pleasure and life beyond. I fell to one knee.

"Please Miss Lucy, ruin me...I wish only to serve."

She placed a finger under my chin and turned up my face to meet her eyes. That deep gaze I could not ignore as it searched out my inner most desires and secrets said it all.

"Come now my little toy. It's time to play." she whispered.

I stood and fell in a little behind her as she started walking toward the van and car parked together. The man had stood, back straight with arms crossed over his chest. I couldn't quite make out details as he was in the shadow of the van, but he was taller than us both and seemed to have an athletic but not bulky build. Suddenly he pointed at the space between the vehicles and a firm gesture. Lucy picked up her pace at seeing this and I followed suit. Seeing her speed up, he moved between the cars and waited.

As we reached the back of the cars I heard a calm yet firm voice, "Well my dear, it looks like you've found a new toy." It was not overly deep or cruel, but it somehow commanded respect. "Let's see it then."

"Yes Sir." she said as she turned to me and commanded "Stand here, toy." pointing at her side.

"Yes Miss." I glanced up as I stepped forward but didn't let my eyes linger, remembering what Lucy had said about looking Him in the eye or engaging directly. I could see he was clean shaven with dark hair that seemed very business-like to me. He wore a black button up shirt and slacks. Classy but not flashy. He was not someone who made me suddenly decide I was actually attracted to men after all, but he was not unattractive in his way.

His voice hardened a bit, "I said, let me see it."

She addressed me again. "Turn around slowly so He may assess you, toy."

My cloak of discomfort billowed and I gripped it tighter in my mind as I slowly turned for their amusement.

"Oh my, this is a lovely toy. And its limits?" He said more smoothly, seeming to have been appeased as I finished my display and turned back to them.

"Acceptable my love." Lucy replied.

"And does it please you?" He asked her.

"I believe it will, Sir, but it is not yet tested," she replied, then addressing me, "Remove your panties, toy."

Startled, I looked at Lucy, "Miss?"

She slapped me. Not overly hard, but enough to get my total and undivided attention. "When I give a command, you may either ask for clarification in a complete thought, or you may comply. I detest ambiguity."

"Yes Miss Lucy." I said as I quickly removed my panties from underneath my skirt working them over my healed boots and letting them fall to the ground. Removing my panties in the parking lot, however secluded, was unnerving but exciting. Again I felt myself stirring at the prospect.

Wasting no time Lucy stepped forward and pushed me against the van, sliding one hand up under my skirt and gripping me, feeling all around and getting a sense of what I had hidden. She smiled deviously and turned to Him still holding my growth firmly, "Yes, I believe this will do nicely."

Stepping in himself, he also reached under my skirt taking my member from her grasp. I had NOT expected this and gasped in surprise. Fear began tearing at my shroud of discomfort and I felt panic rise up. I tried gripping my cloak tighter but I was unsure I could keep it under control in the gust of uncertainty.

"SHHH" came from Lucy's lips as she stared into my eyes. The command was firm, but her eyes showed understanding and compassion. I remembered what she said and understood. I decided then to fully give over trust and control to Her. I let Her take all my fear and let go of my grip on discomfort. I realized it was not a cloak at all, and I had simply been wrapping a curtain around me; a veil marking a barrier. A covering I no longer needed. I pulled apart the curtain in my mind and stepped through into the unknown, wholly engulfed in its vastness.

"Hmmm, " He murmured. "It seems you've found a perfect little toy for your ass."

She quickly looked at Him but was quiet for a moment before she replied, "If that is your wish Sir."