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In Chapter 1, I discovered the Crossdresser that had been lurking deep within me, in Chapter 2, I expanded the use of my dildo, as well as my small collection of lingerie.
And now, Chapter 3..
I was in a good place, I was having quite a bit of naughty fun, my body had quickly adapted to my dildo, and it had become the focus of my playtime. I’d bought some additional lingerie, including better-fitting bras and panties, but didn’t feel the need to purchase any actual outfits. The truth is, I had no desire to go dressed in public.
At this point, I’d been curious about what it would be like to get dressed up for a guy and let him rail me all night long, but was also really nervous about all of that, so I kept playing it safe, locked in my room at night and fucked myself with ‘Max’ my dildo. I would occasionally go for a couple of weeks at a time without getting off, finally having incredible orgasms, but even during these periods of denial, I could never get off solely through anal stimulation. I really wanted that to happen, I felt like that would be a significant milestone. However, if it didn’t happen, I could easily fall back to stroking myself in my typical way. I just wanted to have as close to a female orgasm as possible, one based entirely on penetration. I just hadn’t been able to at that point. As I said, I was in a good place, I think the only thing that could have been a better place would have been a steady source of pussy, but that just seemed like it’d be a lot of work, with no guarantees. So I didn’t put any effort into it.
I was sitting at my computer one evening browsing Cervin’s site and drooling over their Charleston silk-seamed stockings, one of the product photos showed a model’s legs ending in some extremely sexy high heels.
I didn’t own any shoes to wear with my many sets of stockings.
I thought about it a bit and while I couldn’t deny that slipping into a pair of 6-inch platform sandals would kick the sexy up, I reasoned that I wasn’t leaving my room, so I didn’t need the heels, and besides, I could never walk in those anyway.
Besides, I didn’t have any clothes I could wear with them, even if I did decide to go out in public.
So anyway..
Except that these thoughts kept sneaking into my head, especially after I’d applied my makeup, had my long blonde wig on, and stood in front of the full-length mirror in my room. I looked like a woman. I really did, this wasn’t me convincing myself that I looked good in the mirror. If the reflection in the mirror swayed her way up to me and whispered an invitation for sex into my ear, I wouldn’t have believed my luck.
If I bought just one outfit, and if I could stay honest with myself, if I looked good in that outfit, then who knows.. maybe I could reconsider.
A week later, I sat on the edge of my bed, softly running my hands up and down the length of the charcoal-grey pencil skirt that hugged my thighs. I slid the skirt upwards until the top of my black stockings crept into view, and I arranged the clasp of my garter belt to keep the stocking in place. I slid the skirt back down, grinning for all the gooseflesh I was covered in. I stood and admired the white long-sleeved blouse I wore to complete my outfit.
I’d decided to go with B-cups on the bras I had bought, I thought they looked a bit more natural on me, and while the blouse fit well, it wasn’t too tight. To be fair, I looked a bit like a businesswoman, a shoeless businesswoman, but still. I couldn’t wait for the shoes to arrive and had to see what I’d look like the day the skirt and blouse were delivered. Standing now in front of the mirror, turning this way and that, I wished I had the shoes to complete the outfit, I was so horny there’d be no possible way I could wait another five days till the shoes would arrive.
But if I could. If I could wait that long. I could make a special night of dressing up extra sexy for Max, and the evening would end with wild, passionate sex.
I could wait five days. I could try at least.
The Pleaser Bordello Pumps have just over a five-inch heel, I had purchased the black-glitter color, and they fit my feet well, but I sighed at having not purchased an open-toe design so I could admire my painted toes. I couldn’t quite get over how these shoes transformed my legs. Walking in them however was not easy, it was really a bit spooky, but I wobbled over to the mirror, dressed in my outfit, all dolled up for Max, and struck a few poses that kept my feet on the ground, as firmly as I could manage. How do women walk in shoes like this?
I loved how the shoes really made my outfit complete, but the unsteadiness had quite an effect on me. I just didn’t feel as sexy as I wanted to, I had these plans for tonight, I’d prance around the room, teasing Max until he’d bend me over the bed, spread my legs, then force himself deep inside me for being such a Tease. Except I constantly felt like I was going to break an ankle moving in these shoes.
Doubt began to creep in, as it had the day I ‘met’ Max, but with patience, and practice I could take him fully now, almost easily. I just needed to practice, I just needed to stick with it, and make a little progress to maintain motivation. I could do this, it just wasn’t going to happen overnight. I decided no playtime with Max until I could move around like a big girl in my new shoes. That should keep me on task.
It took more time than I expected, I watched many videos on how to walk in heels, and I wanted to just stop on more than one occasion, but as I squatted in front of the mirror, perched confidently on the heels, I grinned and stood, and moved slowly away from the mirror, swaying my hips as I did. I spun around, posing, steady, confidently, and walked to the mirror, stopping and placing my hands on my hips for a moment before assuming the squatting position once again. I was 90% to where I wanted to be on these shoes, and the practice had paid off. I felt like I could walk out of the house, and check the mail without a single Onlooker ever having a clue I wasn’t a woman.
I wanted to go out now. I wanted to show the world ‘Nina’. I also felt that if I did go out, it would inevitably lead to me eventually having sex with a guy. This was a fairly big point of confusion for me, as I said previously, I considered myself straight. To be clear, when I wasn’t dressed, I was not at all attracted to guys. Like nearly every other guy, all I thought about was pussy. I wasn’t getting any, and so my other-self developed as someone that the ‘straight’ me would want to fuck, but ‘Nina’ had developed beyond that now. When dressed, I felt good, I wanted to see if others viewed Nina the way I viewed her, as a beautiful, sexy woman.
I was able to arrange a short weekend trip, a four-hour drive that would give me the opportunity to go through with venturing out into the world as Nina. I was excited right up until that Saturday morning when I started getting cold feet. I managed to make a nervous wreck of myself and nearly called to cancel the hotel but decided that at the very least I could go, check out the local area, grab a meal, and drive back the following day. If things felt right, then maybe Nina would be checking out the local area and grabbing a bite to eat.
I checked in and knew immediately that I needed to shower and let Nina decide what was next. After getting dressed, I paced back and forth in the hotel room. I reasoned that nobody at the front desk would have any idea what room I just left, it wasn’t like they checked me in and then waited patiently for the guy that just arrived to change into women’s clothes so they could laugh and make fun. I was making a bigger deal about this than I needed to, I checked myself out in the mirror once again, exhaled, then turned on my feels and walked out into the hallway. I immediately saw a woman walking down the hall with an ice bucket, talking on her cellphone.
Well, I’m out here, so let’s do this.
I turned towards the elevator, and as we closed to pass each other I smiled and said ‘Hi’ and she smiled back and said ‘Hello’.
That small thing is something I won’t ever forget, the whole interaction took maybe three seconds from the time I stepped into the hallway. The very first person to see me was a woman, and women have a radar that immediately alerts them anytime they come into contact with a guy wearing women’s clothes right? Well, this woman either didn’t have her radar turned on, or she just didn’t know. The one thing that happened though, is it gave me an incredible confidence boost, I added just a bit more sway in my hips as I left the elevator and headed out into the parking lot, standing there for a moment before decided which direction I wanted to go.
I sat in the car and realized there is no way to drive when you have 5″ heels on. So I slipped off my heels and admired my shiny red toenails that very closely matched the press-on nails decorating my fingers, I started the car and checked myself in the rear-view mirror before heading out onto the road. As I didn’t know the area, I just wandered around and figured that if I saw something interesting I could stop. Pretty quickly I wondered if there were any sex-toy shops in the area and entertained wicked visions of myself squatted down in front of a group of guys as I jerked a few off while they watched me hungrily sucking the cock of another, breaking off for a moment and spitting on it like some of the porn Actresses do.
Nope, I’m just driving around, there isn’t going to be any sextoy shop romancing on this trip. I came to a stop at a traffic light and was looking at the shops near the intersection when my gaze crossed the occupants of the car next to me, a couple of guys in their early 20’s both were looking directly at me, and I just smiled at them, which caused them to get bright-eyed and smile back. The light changed and off we went.
That felt -good-
I decided to find a place to eat that would be low-key, with little chance of too much interaction. Yes, I’ll admit it, I really liked those guys checking me out, well, checking out what little they could see of me in the car, but I wanted to avoid anything more than a quick pass by, or greeting. I didn’t want to get involved in conversations or offers of drinks, etc. I may have been overthinking things, but this was the first time Nina was out in public, and I didn’t yet know what to expect.
I saw a sign for a Sushi place and decided to go there. As I walked in, I found only one table with customers (a couple) and another table that had an employee eating. So far, so good! A beautiful Asian woman approached me asking ‘Just one?’ I nodded and smiled at her, and she beckoned me to follow her. She brought me to a booth and said someone would be by soon for my order. At this point, my confidence was quite high. I’d had multiple interactions, all went well, there wasn’t a crowd in the restaurant, and I was quite enjoying myself. As I pondered things, my Server arrived, and she asked if I had any questions, I smiled and let her know I was ready to order, and soon enough I was enjoying a delicious meal. A thought came to me, and while I didn’t have to relieve myself, I felt like I should freshen up my makeup before leaving, and naturally, I’d have to use the Ladies’ room. my Server stopped by and asked if I would like a refill of my water and I shook my head but asked where the restrooms were, she pointed to the hallway. I thanked her and made my way into the Ladies’ room.
That felt sexual.
I entered the stall, and as I sat on the toilet, with my panties pulled down, I immediately became hard and started softly stroking myself. I knew that I had to get off right then, right there. A soft, girlish moan escaped my lips as I continued stroking, and less than a minute later I shot an explosive load into the palm of my hand, which I eagerly lapped up and swallowed like a good gurl. I took a bit of toilet paper off the roll and cleaned off any remaining cream before standing, tucking my softening cock back once more, and pulling my panties into place. I flushed the toilet and cleaned up at the sink before freshening up my lipstick in the mirror.
God, I felt so good.
I confidently walked back out to the booth and sat, with the Server bringing the check soon afterward, I smiled and thanked her and as she turned and left, I realized that I’d be paying with a credit card that did not have a Female name on it. I felt a lump in my throat for a moment but reasoned that it could be thought of as my Husbands card, however, I wore no wedding ring, I started thinking too much into all of this, and simply placed the card with the check and the Server quickly retrieved both, a few minutes later she returned with my receipt, which I added a tip and signed before getting up and leaving. As I walked to my car, I wondered if the Server had any clue, and as I opened the door to my car, and sat on the seat with my legs still out of the car, pulling my heels off, I glanced back towards the restaurant. Both the Hostess and the Server were in the window staring at me, the Hostess had a bit of a surprised look on her face, but the Server had a big, possibly knowing grin. Both of their expressions immediately excited me, and as I tossed my heels into the passenger seat, I took a moment to slowly rub my calves and looked back to where the women were, and still were, I grinned wickedly at them, then raised my hand to my mouth and blew them a kiss before turning and closing the door, then driving off.
Once again, my cock was at full attention. that was not the reaction I thought I would have if someone determined I was a guy, but somehow it just felt so extremely naughty, I don’t know if they had decided I was a guy based on the name stamped on my credit card, but something caused those two women to watch after me as I left, with two very different expressions. It was so exciting thinking that they figured me out, I was shaking I was so excited. I drove back towards the hotel, and licked my lips, I knew Max would be there waiting for me, and I’d have to tell him what a naughty girl I’d been today.