It’s complicated

I had no idea how to respond to stephanie. Her words and proposal shocked me to my core. Once more my perception of her as just a cold bitch has been turned on its head. She was giving me an out of this ridiculous situation and I sensed no deceit from her. More than that, I could hear the care in her voice as she pleaded with me to trust her and try this out. The rational part of me was screaming to take her up on this offer and get out of dodge. But my mouth wouldn’t form the words.

I felt the dampness of my panties, undeniable proof that at least a part of me was enjoying what was going on. I felt the plug in my ass, keeping me feeling pleasantly full. And I couldn’t truthfully deny that I had enjoyed the way people had stared admiringly at me as we walked in. My whole life I felt like I was irrelevant. Not ugly enough to be picked, not handsome enough to be noticed, not smart or dumb, not anything of note, just average. Then there was Stephanie, who lit up any room she entered. Always the center of attention and the focus of their desires and admiration. Maybe that was part of the reason for my hate of her over the years, I wanted so desperately to be like her, but I couldn’t.

But maybe I could? I got more attention in the brief walk through this mall than I had my entire life combined. People thought I looked good and wanted me, that felt really good. But wasn’t this wrong? And was I ready to commit to this fully? I was frozen in indecision and felt my breath grow shallow as my brain short circuited.

Seeing my struggle, stephanie pulled me into her arms and hugged me tight. “Shhh Jenny, it’s ok, this isn’t something that needs to be sorted out in one day. If sexuality and gender were that simple, life would be a lot easier for a lot of people.”

My voice shook as I spoke through my emotion, grateful for stephanie’s reassurance but still scared and overwhelmed. “I don’t know what to do Steph. Part of me wants to try, but isn’t it wrong? And I’m not sure this is who I am.”

She tilted my head up and gave me a kiss, swallowing part of my insecurities as she said softly, “is it wrong for me to like women? Do you think there is something wrong with me?”

“Of course not Steph, you’re amazing, it’s just-“

“Then why can’t you give yourself the same acceptance you give me? And like I said, just cause we go to the salon and you dress up and be a gorgeous girl for a few days, doesn’t mean that’s your life. You’re young and curious, now I’d the time to experiment.”

I blushed and looked away as I nestled deeper into her arms. “You really thing in gorgeous?” I whispered, needing to hear her say it again.

She laughed gently as she said, “of course silly! Why do you think I keep jumping you? You’re just so sexy.” She winked at me and I laughed, feeling much of my anxiety disappear as she let me go.

I grabbed her hand and gave it a grateful squeeze, telling her confidently, “then let’s go to the salon.”

I nearly fell multiple times as she excitedly dragged me to her salon. She moved so fast as if scared I would change my mind, but at least I got a nice view of her plump ass swaying as we moved. Before long we reached our destination, new you salon. The hostess, I fit woman seemingly in her early twenties greeted stephanie by name and brought us to two chairs next to each other without delay.

Someone to do each of our hair and another each for our nails came up quickly and asked what we wanted done. Before I could reply, stephanie declared she would just be getting a blow out and her usual nails. I on the other hand would need hair extensions, fake nails until mine grew out and white polish on both my fingers and toes. No one waited for my say on the matter and they got to work.

In all my life I had never quite experienced this. I was used to a barber shop, quick and efficient. But this was something else entirely. Before they started really doing my hair, they brought me to the sinks and started washing my hair. Their delicate yet powerful fingers helping release all my stress away. I was floating as the started working on my extensions and working on my nails. Living my life until now as a man, I never knew what it was to be pampered and sat there contentedly as they worked on me. I couldn’t say how long we sat there or what they did, just that when we stood to leave, I was sad to do so. The only saving grace was stephanie’s hand in mine, giving me another squeeze of support as our eyes met.

Stephanie had left her card number with the people over the phone so we walked right out of there hand in hand. Taking our time as we walked towards the car. I took the time to savor the stares and felt something stirring within me. Soon enough it became agonizing to walk this leisurely pace and I started walking faster, dragging stephanie along until she took the hint, and thankfully we made it to the car quickly after that. She looked at me confused as we reached the car, but without a word, I pulled her in for a kiss.

Before I knew it, I was pinned against the car, one leg wrapped around her waist as her tongue invaded my mouth once again. I felt the plug get pushed deeper as I was pressed against the car and grabbed Steph’s hand, dragging it towards my ass so I could feel what I did before. To my dismay, she pulled away and said between pants, “Jenny, not here. We are going home, now.”

Her eyes were filled with lustful fire and I nodded obediently to her command, hopping in the front seat after she opened the door for me once more. I ground my ass against the seat, not happy to have to wait, and bouncing impatiently as we made our way home. It felt like we hit every single light on the way, but finally, we made it home and I sprinted inside.

Stephanie quickly followed and the moment the door shut, she picked me up and pressed me against the door. My legs wrapped around her and she kissed me hard. I felt so dainty in her strong arms, it felt effortless for her to hold me up as I submissively let her control the tempo of our make out session. I moaned into her mouth as her hand found my plug once more and I gasped as she pressed it in deeper.

With a grunt of satisfaction, stephanie pulled away and stared at me with lust, still holding me aloft. Without breaking eye contact, she carried me over to and tossed me onto the couch. I sat there panting as she reach into her pocket and took out her phone, sternly, she asked me, “would you like your plug turned on Jenny?”

“Yes, turn it on stephnie!” I begged. Each time we did this, I got more and more frustrated and the need to cum increased to new heights. I feared for my sanity if I didn’t cum soon.

With a sigh, she looked down at me and said disapprovingly, “yes what Jenny? Only good girls get their plug turned on.”

I didn’t care, that was the thing that had gotten me closest to cumming and I needed it. “Yes please babe, please turn on the plug so I can cum! Please I’ll be a good girl!” I was near tears as I begged. I didn’t care anymore if I was a man or a girl or weird or whatever, I just wanted release!

Thankfully, this seemed to satisfy stephanie, and with a grin, she hit the button. Immediately I felt the device close to that secret spot I couldn’t identify and started gyrating in the couch, trying to get it deeper than it seemed possible to get it. It felt good, hitting spots that sent jolts of pleasure surging through me, but it just didn’t quite reach where I needed it.

As if reading my mind, stephanie stepped forward and leaned down towards me, mouth inches from my own. “Not quite deep enough is it Jenny?” She whispered.

There was no use denying it as I sat there, wilding humping the couch and panting like a slut all the while, “no babe it’s not. Please help me! Please help me cum!” I begged her. I linger forward to kiss her again, but she stepped back at the last moment, leaving me whining from my seat.

“Jenny we will make you cum, but first, you have to show me how much of a good girl you are.” Before I could ask what she meant, she slowly started unbuttoning her shorts. I stared at her, feeling my caged cock jump as more and more precum soaked my panties. Finally, I would get to her sexy body. Slowly, she started moving them lower down her body, and just as it was about over the promised land, she turned around. She looked over her should at me as her shorts and panties hit the ground, revealing her perfect ass. I barely was able to contain my drool as I felt my cock painfully press into its cage. Hoarsely, she asked , “are you ready for this Jenny? Are you ready to show me how much of a good girl you are?”

“Yes sweetie I am!” I begged/screamed at her, even more turned on than I already was. With a chuckle she turned around and I stopped working my plug into me as my mouth opened in shock.

“Well Jenny, come show me what a good girl you are.” She demanded while her hand stroked her cock.