From the Bedroom to the Subway

She then snatched the blanket that I was using for coverage off me and wolf-whistled before winking "Oh but I'll be nice!" She reached down to her drawer before pulling out a very cheeky black lace pair of panties.

"Put these on, so you have some coverage." My eyes bugged out of my head, she wants me to wear women's panties! I took them from her hand and looked at them. If I adjust them they MIGHT work as a speedo at the beach... but to be caught in women's panties and nothing else other than my sneakers in NYC. I don't know if it's worth it...

Diane pipped in "you know I might have clothes that are a lil big for me in my car... but I can't guarantee they're better than those." I decided to reject the offer and take the gamble on the car clothes.

For a split second, my mind wavered over the thought of being outside but it was too embarrassing. "I think I'll wait until we get to the car."

"You sure?" She asked, smiling seemingly happy with my answer.

I quickly grabbed the blanket and threw it around my waist like a towel. "yeah... I'll just keep the blanket around me until we get to the car."

She looked surprised "the blanket? No honey that's staying here... You don't get any other options but the panties."

"But I need options! You can't expect me to go outside." Suddenly there was a glint of something in her eyes but she nodded "fine... Go near the closet door I have to get a few things together." I did walk over and covered myself as I heard some rustling from the other room and some drawers opening and closing.

She came out and she was zipping closed a small handbag with some clothes in her hands before I got my hopes up. She smiled and took the panties out of my hand and put them on herself. She turned and gave her ass a lil shake as the panties slid right up her crack fitting snugly, then got dressed in a long black sleeve summer dress that came down to mid-thigh. It was a simple, sexy, and beautiful outfit but she showed me something in her hands... fishnets? She gestured for me to walk over to her and she pointed at the floor. I immediately got on my knees and helped put them on. Any excuse to touch her beautiful legs was worth it. I slowly did it and realized that these only went up to mid-thigh. Usually, she has them wrapped around her entire leg,... and no garter belt... strange.

I was taken from the thoughts with a jolt of pleasure as I felt her smooth foot gently drag against my newfound growth between my legs. "You know Kitten if I didn't know any better I'd say you have a foot fetish." she continued to drag her foot along my length and teased me until I was actively trying not to hump her leg. I dropped the blanket

I shook my head running my fingers along her legs trying not to tremble from the touch "I have a You fetish. Anything that you do makes me want you." She leaned down and stroked my cheek "great answer Mikey." I suddenly smelled something sweet and familiar.

She brought her hand just under my nose and it smelled like something sweet and very citrusy. "It's the sensual oils I used on you earlier. I love the smell" and I nodded in agreement. She smiled Kissing my forehead before gesturing for me to stand up fully nude and fully erect.

I walked to the closet nearest the door and she smiled. She walked up opening the door to my immediate left which caused me to bump back and only then did I realize that the item behind me was the door to outside her apartment, she quickly opened the door just as I was falling back and I found myself not so gracefully tumbling out of her apartment with a loud bang of the door hitting the wall. I fell hard on my butt and the feeling of cold tile hitting my ass caused me to freeze as I looked up quickly to see Diane stepping out of the apartment with an evil smile and locking the door behind her!

I quickly got up and tried to open the door but to no avail. "You need to let me in there!"

She smirked as she saw me desperately shaking the door nob. "Need?.... No, I don't." She said flatly, seemingly unconvinced.

I reached down and covered myself just to feel a firm pinch on my naked ass causing me to jump. "No covering... that includes out here."

I opened up my mouth to speak but she quickly pushed me against the locked door, squeezing my shaft just below the point of pain, "You could have had the undies but you chose not to. Consequences of your actions." I moaned out loud and she smirked at me.

She pulled me forward by my dick which caused my dick to still throb in her Vice like grip. "Now you will hold my hand and not cover an inch of you.... Or else..." she unzipped the bag on her shoulder to reveal in her hand a very short rope, probably only 18 inches but that would be more than enough to tie my hands together.

I quickly nodded and reached my hand out before I felt a hard pinch on the head of my dick causing me to gasp and fight back a cry of pain. "I need an answer." "Yes, Mistress! I promise I won't cover myself." She nodded before releasing my head.

The walk was humiliating. We only walked by one elderly woman who appeared to be blind until I heard her say "if only I was younger" with a cackle. But there was also no urgency to her walk. Every time I tried to pick up the pace, she would stop and say I wasn't going to rush her. The worst part was that no matter what went through my mind my dick was permanently erect.

The idea of being so vulnerable outside under her guidance...made it so hot. Finally, we made it to the parking lot. She kissed my hand which did cause my stomach to flutter, then a blast of cold air hit my entire body as we stepped into the parking lot and I immediately clung to her out of embarrassment and partially out of warmth. she immediately shoved her ass against my dick and caused me to start growing again despite the cold air. "Mmmmm does a shy kitten not like being out in the cold, or is that you don't wanna shrink?" Realizing that the cold air can impact me like this brought another level of embarrassment. Though I would never consider myself small, normally, frigid cold air can impact that! It was October after all and you never realize how cold it is until you're butt naked and not allowed to even cover yourself!

After an eternity of walking across the parking lot and one car honking at us, we made it to her car. "Oh dear I forgot my keys!" she said with animated shock.

The idea of having to walk back and have more people see me was horrifying "What?!?" I'll have to relive this.

She stuck her tongue out playfully "Just kidding my lil streaker!" And the car chirped.

I was about to jump in for modesty but was firmly swatted on the ass. "No, change out here!"

"Mistress I wanna change in the car! There are people!" She grabbed me by the face and spoke softly but firmly "change out here.... Or be tied to the front of my car... And be spanked for the next hour while people watch. Do you think I won't?"

I gulped when I realized how serious she was and immediately opened the bag and my jaw dropped. Inside was a pair of men's... Shorts? They looked like running shorts but were altered to what appeared to be booty short length. And the tank top very much looked cropped to be at my navel. And on top of these was a bright electric blue thong "Mistress! These are so tiny! You said they were better than the black ones!"

"No, I didn't." She said with a tinge of humor in her voice "I said I have clothes... but I can't guarantee they're better." I say you got off lucky cuz those shorts and thong have more coverage than the ones I'm wearing."

"I can't wear a thong! I'm a boy! You need to go and get-" and was promptly cut off when I felt a hard smack to the full length of my dick and was then forcibly turned around to a barrage of spankings to my ass.

"Wrong." She said harshly "I don't NEED to do anything you say. Watch that word... You know... No driving anymore... we take the subway." My ass was now fully red and stinging, and both sets of cheeks I have now bright red.

I tried to object but she took out her phone "You have 30 seconds to get dressed before I start taking clothes in that bag away." She said before showing me an alarm on her phone already ticking down.

I quickly grabbed the bag again and as I turned to start getting dressed I felt another gentle smack to my ass this one feeling like it was making my entire butt jiggle. I saw the thong and with only a second of hesitation, I grabbed it and quickly stepped into and slipped it up my legs before I felt it ride up my ass, and although it did feel foreign... It didn't necessarily feel bad. And when I turned around to see Diane staring at me with this gaze I definitely felt a bit more sure. She looked like she wanted me in just the thong so I figured it would be better to speed through the rest. The white shirt was small for me... It was taught against my entire body and seemed sheer, like it would be transparent if too much light was on it. The shorts were light blue and looked like they were men's shorts. As I stepped into them and slid them up my thighs I definitely felt a difference. Most shorts that are a few inches above the knee have a lining. These felt much thinner and much shorter. The majority of my thighs are being shown and I could feel the faintest feeling of air going against the bottom of my ass cheeks.

But it was clothing and I felt better. I turned around just as the timer went off and she had a smile on her face. She reached up and cupped my face very softly. "I am very happy, and proud of you for trying. I wanna check in and make sure I haven't pushed too hard."

I took a breath and nodded, smiling. "I'm good... my heart is through the roof but... this feels strange... and good. Am I really making you happy?" She smiled at my question before leaning up and kissing me and gently grazed her tongue against my lip and I couldn't help but moan slightly.

"Yes... ready for the subway?" I looked down feeling the blushing go darker before I realized that my cock was almost starting to poke out of the shorts so I quickly tugged them down but in doing so part of my butt started peaking out.

Diane quickly slid her hands down to grab both my cheeks and pulled me towards her for another kiss, this one a lot more aggressive. Her hands wandering and kneading the flesh of my ass caused an immediate effect between my legs and she quickly broke the kiss and looked down "oh kitten that is going to be a problem." I looked down and with my cock at full length, a part of my head was sticking out.

She snaked her hand down the back of my shorts and started rhythmically tugging the string of the thong causing friction. The friction against my backside and the rubbing of my cock was a strange and pleasurable experience. My cock slowly started bobbing up and down matching the pace and she nodded seemingly satisfied. "High or low?" She asked me with a mischievous smirk.

"What's it about?" I questioned, confused. She raised her eyebrows and shook her head disregarding the question.

Not knowing what it pertained to I guessed "um... high?" She smiled nodding before releasing the string between my cheeks and then pulling the thong up to show a whale tale an inch out of my shorts.

"What if I said low?" adjusting to the new sensation of the wedgie digging into my ass.

"I would have pulled the shorts down until the upper part of your ass was more exposed than it already was. I think you made the right call for overall modesty." I nodded, smiling and she grabbed my hand.

Walking was a strange experience. It wasn't outright scandalous other than my shorts being short and with the cold feeling in the air, my crotch wasn't in jeopardy of being exposed at the moment. But if anyone stared at me for longer than a few seconds then there would be the sheerness of my shirt and noticeable thong from the back. Diane stood in front of me as there was some blockage at the turnstiles so there was a slow-moving crowd. I found myself pressed behind her and she didn't seem to mind. Every step she took though she would take half a step back. And just for a second grind against me. It wasn't dramatic. Anybody watching might even think it's an innocent bump. However, the fact it was every step and her ass would only grind against my crotch for a half second was a clear sign.

The attention was causing some growth, but it wasn't officially dangerous territory. All I know is that I couldn't focus on her... If I just didn't focus on her beautiful ass, covered in those sexy cheeky panties... with those slender legs encompassed by fishnets. I felt my cock start growing even more when I realized that I was turning myself on and immediately stepped forward so that she was covering my front. She looked a bit surprised but noticed the poking and she smiled. We made our way to the escalator and she shifted us so we were facing each other with me on the lower stairs. So I was looking up just slightly.

She slowly started kissing the top of my head and ran her fingers through my hair. "She smiled and gave me a gentle kiss on the lips before whispering, "I think you finally calmed down enough." I looked down to see the tent drastically reduced. I turned just as I stepped off and felt a firm pull on my thong which caused me to muffle a squeal. I turned to see her winking.

She pulled me away from the escalator to the bathrooms. I briefly thought about her taking me in there and allowing me to cum but I quickly shut down the idea. She wouldn't let me get off that easily. "I have to pee. You wait here." And she walked in LEAVING ME ALONE. I suddenly felt a lot less sure of anything. It felt like every pair of eyes was on me. I was dressed like a lil deviant and no one was there.

I sat down on a nearby bench and cringed from the feeling of my mostly naked cheeks on the cold metal. I looked over to see 2 women staring at me. They were whispering and laughing and I couldn't help but think. Why would I do this? I've never done anything like this and now I'm probably going to be laughed at by everyone. Maybe she left, and this was her plan all along. My mind continued to race for what felt like a lifetime until I heard her voice "Mikey look at me." I looked up and Diane was staring down at me concerned, I glanced at the two women and apparently, she sent them a look that had the two ladies stop laughing and walk away quickly.

I looked down again ashamed and without a word, she sat me up and straddled me right there on the bench putting my head in the crook of her neck and she started shushing me. I just had to handle something in the bathroom, next time I'll make sure it's a gender-neutral one so you can come in."

I nodded before confusion set in "what did you have to handle?" I looked at her and she felt very warm, almost hot, and her skin, which is usually pale, had a slight pink hue around her cheeks.

She gave a slightly embarrassed and mischievous smile. "You wanna see?" She took out small headphones and stuck them in my ear. She connected them to her phone and she turned the screen towards me.

A video started and Mistress was in the frame. It looked like a bathroom stall that looked pristinely clean. The video of her was her making a shushing sound to the camera. She slowly pulled her dress up and my eyebrows raised. I saw her panties and she was speaking quietly, almost mouthing the words "seeing you in your outfit has got me feeling very excited. How excited?" She slowly rubbed her legs, and it went from doing a type of massage to her calves to working over her soft thighs, to gradually sliding upwards to over her panties and I could hear the wetness as her fingers explored her area.

The sadness and insecurity I felt melted away into the sounds and sights of her. Even in the video, I heard the sounds and sights of her excitement and it was the most hypnotic video I've ever seen, all the porn, improper thoughts, and glances from any other person dissolved into thin air. Everything felt like it was happening in slow motion. Every second had me completely absorbed.

Her hand slid across her smooth belly, and over her black sheer lace panties as her hand wandered between her soft thighs. Her dampness was audible. She laid her head back as her breath quickened. Her fingers began moving in a small circular motion and then quickly dragged across the length of her slit, while the other hand held her still-clothed breast. This was the most beautiful thing ever. Suddenly her hand went from outside the panties to seamlessly sliding behind the panties, and I saw her sigh and smile into her fingers. I couldn't help but whimper... I wanted that... I wanted to give her that. She teased herself and saw her other hand unclasp her bra, thrusting her beautiful round tits out, and started harshly teasing her nipples. I know I saw those beautiful breasts less than an hour ago, but seeing her this exposed and raw while comforting was insane. She moaned softly with every stroke in the video. She rubbed her thighs together, resisting the urge to spread her legs. She thrust her hand into her crotch faster and faster. Her ass gyrated in time with her pumping. Her moaning grew louder, as did the slurping sound from her sex. Suddenly she arched her back, her moans becoming breathless squeals. Her body shook madly, but her madly pumping hand kept working. She let loose one final, sustained moan, and collapsed against the seat, her body covered in the beautiful blush I asked about only moments ago.

I saw her look at the camera and wink before she stood up on wobbly legs and re-clasped her bra and adjusted her dress. My jaw was already on the floor, but then it was sinking into the earth. She reached up her skirt and shimmied her hips to see her now-soaked panties around her ankles where she picked them up and put them in her bag. She shifted her hips and I felt the heat radiating off between her thighs as her newly discovered naked sex rested on my thigh. The video cut out and right when it did, I felt her hand on my jaw and open my mouth as she forced something into almost the back of my throat, and I was met with the taste of satin... and something tart... and sweet. The panties taste... omg this was her!

The panties were completely drenched and I tried my best to savor as much as I can before she pulled them out without warning She gave me a surprised look and she looked deep into my eyes. "Mikey... I think we discovered something, didn't we?"

I blushed but nodded "I want... that... I want to do that for you."

She smiled "hm... I can get that arranged... if you do what I say" I nodded. This wasn't a thought, this was a need. "I am yours to command, please... just let me... do that. I need to do that."

She nodded "if you earn it, yes." She stood up and looked down at my full-grown tent. "Calm down." My rigid wood still standing tall didn't budge "you better calm down or else the deal is off." I immediately started thinking of any disgusting thing I can to cause myself to calm down and it finally started going down.

We stood up and waited for the subway. The subway was packed! I found myself with my back to the center handrail that connects from floor to ceiling. She stood in front of me with her back turned. I don't know why but I can tell this is going to be where We were all rubbing shoulder to shoulder. Suddenly the lights flickered off and we were in the dark for a few seconds... Suddenly I felt a very gentle stroke along the full length of my dick.

The lights turned back on and the feeling stopped. "Now it's the time to earn it, and this is also a lesson." The lights went off again and with all the white noise Nobody heard her or the rustling of my shorts and I felt my dick get pulled out of my shorts. I suddenly smelled a sweet citrusy scent that I immediately detected as the sensual oil. I felt a heavy amount of the oil thoroughly lathering my cock. I suddenly felt a snap back of the cock going back into my shorts just for a few seconds later to have the lights flicker on. She was now facing me when the lights turned on and her eyes could have made me cum alone. They were filled with this primal desire I'd never seen before.