My First Time as Sara... Pt. 01

I changed names only to protect them. These stories represent a fully non-fictional account of how I became me. All stories and people are real. Enjoy them.

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I only knew Steve as my landlord. To be exact, Steve was the only son of the two people that owned the small apartment complex I am currently living in as of right now.

My reason for moving here was out of necessity than anything else. Three months prior to moving in the 20 unit complex I lived on the other side of town with my then fiancé Sara. We're both late 20 something kids that moved in together after collage and while the first couple of years seemed grand, it was bad things that were under brewing in the relationship. After months of bickering and arguing, the decision made by her was that I wasn't man enough to take care of her and in that blink of an eye she left.

I moved because I didn't want to live there anymore. I was devastated. I lacked any real self worth and felt as if I was not lovable. Not lovable by any person.

After she packed her things and she left, I found the apartment complex and moved in. I moved there because the folks that owned it lived there as well and their son was hands on in getting all issues resolved ultra quick.

It took me about two weeks after I moved in before I finally started to unpack my things. Mostly I laid around on my couch and watched TV. As I opened box after box I came across some of the clothes I packed into boxes from my dressers. In the pile of my clothes I found a few of Sara's things. Specifically a couple of pairs of her panties, a nude pair of pantyhose, pair of black opaque tights and a bra.

At first I was devastated and couldn't stop crying. I touched them, holding them in my hands and brought them to my face. I could still smell her perfume on it. It lingered. It also got me a little excited.

Actually very excited.

I wasn't the usual guy in terms of how I looked. I was about 5'8", slim in build with what both my mother and former fiancé said was very girlie hips and as one guy said to me drunk at a bar, the finest girls ass on a guy. Despite my girlish figure, a few guys have confused me as a woman with my shoulder length blonde hair and very sharp, angular features of my face.

I also dabbled in my own sexuality. I've been with one guy, about a year into my college time and a year before I met Sara. He lived on my floor in the dorm and we became quick friends. We'd study together and play video games or just crack open a few beers and chill in his or my room. Then there were the times I would let him give me the most incredible blowjobs and I would jerk him off.

I also tried crossdressing a couple of times when I lived at home. In my early teen years I was extremely confused as to who I was in this world. I would swipe a pair of either my sisters panties or my mothers pantyhose and lay them on the bed or slide them on and try it out. Try to figure out why girls wore them other than to turn guys on.

So here I am in my apartment with her stuff and I'm completely flooded with grief and all these emotions. The breakup was still raw. All her words about my manhood, how my penis was too small to satisfy her, let alone any other woman. She was vicious and venomous in her words. I should hate her but it wouldn't be anytime soon.

After a few weeks I finally got into a routine. A routine to finally build up my life again, to feel normal and to finally get back to becoming just me.

My routine essentially became going to work, come home, grab either something from the store or cook up a frozen pizza or something, watch some TV, load up some porn on my laptop and then jerk off, cum and go to bed. Almost every single day this is what I did. There would be times I'd go have dinner or hang out with close friends or visit my family, but I always ended up doing my routine.

One night I decided to do something different. After I ate my dinner I turned on the TV and then decided to grab her things she left behind. I took her panties and rubbed them over my hard cock. I'd put my hand in her pantyhose and stroke myself off. Sometimes I would slide either her tights or panties on and stroke my hard cock over her tights and panties. Then I would cum. I'd cum like I never have before and then I would sleep the best I ever have.

Soon my routine was dressing her her stuff. I'd put on her panties, slide on the pantyhose and lay in my bed, the cold sheets meeting the nylon and giving me the hardest erection I ever had, and then I would explode.

As time moved on and I would dress in her things and saw how I looked. I saw a girl in her things. I saw what she saw. I wasn't a man. I was a woman in this pitiful guys body. Soon I couldn't go a day without dressing and stroking my pathetic excuse for a cock.

Soon the decision had to be made. It was time to go further. To take my persona even further than I ever thought I would. I had an early work day so I went to the mall. I decided that I needed to further craft this new person I became in the privacy of my new home. I bought all kinds of things a girl would need. I bought a couple of panties, one cute and the other this sexy lace and mesh one, bra to match them. I got a garter for my stockings and a pair of nude pantyhose. I even bought a nice slip because doesn't every woman need one.

Of course I had to finish my first purchase with a basic white blouse, a simple black skirt that came to mid thigh and modest heels. I looked like a cute secretary. Then I bought some mascara, lipstick and other things to finish the job.

Over the next month I would lay out my clothes in the morning. I would carefully put the blouse and skirt, my panties, bra and either the stockings or pantyhose on the bed and get dressed for work. All day I would think of it as a date of sorts. I would go to work and my mind would drift to when I would get off and go home to become my female self.

Today wasn't any different. At least I wasn't expecting it to be.

I decided to drop by the liquor store and grabbed a bottle of wine. I ordered candles online that were delivered yesterday and bought some pasta at the grocery for dinner.

Before the final steps up my stairway to my apartment I stopped by the apartments office to check on a request to have them fix the slow leak in my kitchen sink and also to drop off my rent.

Steve was late thirties I think and nothing out of the ordinary about him. He was a regular guy. Cute in that normal way. Average height. Average weight. Always wore jeans and a t-shirt whenever I saw him. He was the only one in the office when I stopped by to drop off my rent.

I handed him the check and he had this rather queer smile on his face as he looked at me in the eyes, never leaving my face. I give him the same quirky smile I always did for anyone I met. He took the check and smiled, quickly licking his lips as he said thank you and put the check in the desk drawer.

As I was leaving I stopped at the door. He was staring, almost like he was looking me up and down. I caught him just before he quickly pretended he was doing something on the computer.

"Any news on my kitchen sink?" I asked.

"Just waiting for a part. Probably tomorrow morning," he said, still with that smile on his face.

I opened the door and he quickly asked a question.

"I thought you lived alone?"

I stopped and got extremely nervous. "I do. Why?"

"I went to your apartment to look at the sink and also decided to check on your filters," he said, now his smile going to almost a smirk. "I saw some girls clothes on your bed."

Now my heart dropped. Whenever I go to work and leave my sexy clothes on the bed all laid out, I close my door. Did he open my door? I mean the little closet where the AC unit is is across from my bedroom but did he open the door?

"You know if you have someone else living there you have to let us know," he said. Now all he had on his face was a smirk.

I had to lie. "It's a friend. She came over last night and forgot her clothes."

"As soon as I have the part I'll come over to fix the sink," he said as I walked out and to my apartment.

I walked in and saw the door was open a crack. My heart was racing. My mind was flooded. I kept asking... Did I leave the door open a crack? Did he open it? Did he buy into my lie or did he think those were mine?

All the worrying kind of ruined my whole evening I had planned. The constant fear that he might think these were mine, which they were made my stomach upset. This was my secret and if I did leave the door open a crack then I did it to myself. I wasn't careful.

Even my newest purchase, a powder blue and white lace silk nightie didn't make my night any better. I opened it and took it to my bedroom, laying it on the bed.

The rest of the night I spent on my couch, tears in my eyes and heartbreak in my mind. As the night wore on I realized that my sadness was not possibly having my secret discovered, although that was not ideal but that I might not have the privacy to do this. That I would be looking over my shoulder and wondering if anyone else knew that these pretty things were mine. Then the depression that I was not really a man, not able to further my transformation into becoming the women that gave me great comfort.

As midnight approached I stepped outside of my apartment and onto the balcony and surveyed the complex. Most lights were out, residents sleeping without the worked that I currently had. Even Steve's apartment was pitch black. Perhaps he was sleeping... Dreaming of discovering my secret.

I couldn't sleep and since I was lucky and didn't have to work tomorrow, I didn't feel the need to worry about a lack of sleep. Eventually I went into my bedroom and saw the pretty clothes laying on the bed. They were feminine and pretty. They laid on the bed and looked unloved. Unappreciated. They needed me as much as I needed them.

I slept that night in my new nightie with panties underneath. I haven't slept that well in years and drifted to dreams of becoming this female while wrapped in the feel of silk and lace, linen bedsheets and cotton panties.

The morning came as quick as the night did and I woke up in complete and utter content, dressed in my new nightie and these cute black cotton panties. I woke up for the first time with a smile on my face and the pain was not that bad.

I had the day off and all to myself. Although last night was rough, worried that my secret was discovered with by my landlord Steve snooping around, or by my own doing by leaving the door to my bedroom opened a crack, I decided when I woke up that I would enjoy the day by working on my newly discovered female persona.

I showered and shaved. While at times I cursed it, I didn't have a lot of hair on my body and never was able to grow any facial hair. Shaving was done quickly and I even bought some shower gel that smelled of grapefruit. All in the name of becoming this woman I knew was inside me.

As I was prepared to leave and run some errands, I decided to wear my cotton panties under my shorts and again, left the rest of my clothes on the bed. I did this because that was how my mother prepared to get ready for the day. She would lay her clothes out on the bed before getting dressed. I like that I picked up that from her.

I made sure that my door was closed this time. I assumed that Steve would be by sometime today to fix my sink and didn't want him to see my clothes again. I closed it and pulled on the doorknob a couple of times to make sure that the door was closed.

I ran my errands. Went to the mall and did some window shopping at the department store. While I bought my initial clothes at the big store mart, I knew that as I grew in this I would want maybe sexier and better quality dresses and lingerie.

Some of the associates at the department store gave me looks as I held up this black dress. It had sequins and would fall to about my knees with a slit up the side to about mid-thigh. It was an amazing cocktail dress and it was my goal to become female enough to wear it.

I ended up buying another pair of stockings, black with a red seam up the back. They were so pretty and the girl inside of me giggled at getting the chance to wear them.

I ended up going into the bath store and buying what she called a bath bomb that smelled like lilacs for my "girlfriend". I went to a restaurant to eat and then headed home in the late afternoon.

Steve was at the apartment, I assume finishing up the last of the repairs on my sink when I walked in. I had the bath bomb and my new stockings in my bag from the store. Steve stopped for a second and gave me that same smile as before. I looked down the hall quickly to make sure my bedroom door was still closed.

It was. I silently sighed relief.

"Thought you'd be at work," he said.

"Actually had the day off," I responded.

"Do some shopping?" He asked.

I looked at my bag and gave him a smile for some weird reason. "Had to get some new golf shirts for work." It made sense as I worked in an office and dressed business casual.

"Well I'm finished with the sink, so I'll get out of your way," he said.

"Thanks."

He left and now I had time to enjoy my afternoon. Really enjoy it.

I stripped and took the bath bomb out and dropped it in the water. The smell of lilacs filled my bathroom as I sat in the bath. I escaped my life and my world and could only think of myself as this beautiful woman, soaking in her bath before she got dressed. Dressed for a hot date or a day of shopping. A girls day.

I toweled off and went to my bedroom. The afternoon light spilled into it and it gave it an aura of relaxation. I lit one of the candles in my bedroom, dropped the towel to the ground and took the deepest of breaths.

I slid on my mesh and lace black g-string panties and then I took out my new stockings and slid them up my legs, taking the extra care to make sure the seam was straight. I slid on my garter and attached them. At this point my cock was hard, throbbing and filling the black panties that covered my cock. I put on the bra and put in the silicon breasts I bought online.

I stood in the mirror and smiled. It was all coming together. Slowly I was shedding this make skin like a snake and becoming this woman I see in my mirror. I slowly pulled up my skirt and buttoned my blouse, sprayed the perfume I bought online and applied my new lipstick.

I was more than this woman I've created. I was a sensual woman and was becoming more aroused by the minute. I stood in front of the mirror and smoothed out my skirt, fixed my blouse and then tried to style my hair. While it was already long and full, I brushed it like a woman should.

I decided I wanted to grab a quick glass of wine and get up the nerve to take pictures of myself. I have never felt as sexy or as alluring as I did right at this minute. I wanted to capture this moment so if for any reason I couldn't dress that I would have proof I was really this woman that I not only felt but looked as well.

I walked out of the bedroom and into the gawking face of Steve, who apparently knocked on the door a couple of times and when no one answered, came in to retrieve a wrench and screwdriver he left in my apartment.

I froze. I literally couldn't move. My heart was beating faster than it ever has and I struggled to make even the slightest of sounds. I was in essence a statue of a man dressed as a woman.

Steve didn't move as well and just stared at me. Time stopped. It was just Steve and myself in my living room. Steve in his shorts and dirty t-shirt and myself in my skirt, blouse and sexy lingerie.

"What the fuck?" he uttered, finally.

I was flustered. How do I explain this to him? What excuse do I come up with? Do I just tell him a lie and play it off as a joke. 'Hey Steve. Was dressing up as a joke. Ha ha.' Maybe something else? Maybe he doesn't even recognize its me?

Except that he knows it's me. It's the same clothes that were on my bed the other day. Same skirt. Same blouse. Same heels.

"Listen. I can explain," I finally get out of my mouth. It was hard as my mouth was dry with nervousness.

"So those were your clothes on the bed then," he said as his eyes fixated right on mine.

"No. See..." I try to say the words stumble coming out of my red lipstick painted lips.

"You dress up like a girl?" He asked.

He looses his lock on my eyes and starts to look up and down my entire body, taking in my outfit.

"This isn't what you think it is," I mutter out.

He walks up to me and in seconds, which feels like forever, he's only a couple of feet away from me. I imagine the intoxicating smell of my perfume combined with the lilac bath bomb fills his nose.

"Then tell me what it is," he says.

I can feel his eyes piercing my soul. I almost feel his breath. I decide at this point it's far better to go for broke. For the first time I take a big chance.

"Ever since my fiancé broke up with me, I've been lost. I've felt like a loser. I found some of her things in my boxes and when I wore them it made me feel better."

He looks at me strangely. "These are her clothes?"

I swallow and take another breath. "Actually I bought these myself."

His face breaks and he gives me a cocked smile. "So you bought this skirt and shirt?" he asks.

"Actually it's a blouse," I correct him. He doesn't look amused.

"Do you wear girls underwear?" He asks me.

My heart beats hard again. "Yes."

"Show me."

"What?" I stammer out of my mouth.

"I said show me. I don't believe you," he says, his cockiness and confidence flowing.

I lift up my skirt just a few inches.

"Higher. I want to see if you're wearing panties."

I try to lift it higher but in bunches around my hips and because I'm already nervous and flustered, I begin to struggle.

"Just take the skirt off," he says, or actually commands.

I pull the zipper down slightly before he interrupts me. "Actually take off your blouse too."

I try stalling but the look on his face tells me I better listen. I unbutton my white blouse and drop it to the ground. Then I follow his other request and slowly unzip my skirt and let it fall around my ankles. As i do this, he gives me that same smile as last time. He knew those were mine.

I stood in front of him in my new lingerie and his eyes focus on my hard cock, stuffed in my black panties. His eyes move back up to my face. I'm even more nervous than I was seconds ago.

"So you dress as a girl. Is that all you do as a girl?" He asks, the question dripping with attitude.

"Yes."

He takes a step closer. "So you don't kiss like a girl then?" He asks.

I'm flabbergasted. I'm lost for words. In my mind I dress as a woman because not only does it make me feel better as a person but it also felt right. Felt that who I am right at this moment, dressed in these beautiful clothes and lingerie is who I am.

"I don't think so," is all I can muster.

He leans in and kisses me. Not a gentle peck neither but a strong, hard and passionate kiss. He slides his tongue with force, playing and trading mine and I just stand still. I don't know what to do at this point. I never considered myself gay or anything else but I have jerked off another man, so maybe I am. Maybe I was. All I knew is that I feel like a real woman.

He pulls back and a little of my lipstick is on his lips as he smiles. "I think you kiss like a girl."

Before I can say anything else he kisses me again, but this time it's with an embrace. A hard and manly embrace. He wraps his arms around me and the kiss is just as hard as before but this time I reciprocate and kiss him back. I however kiss softly and let his tongue go into my mouth and caress it with mine. Our breaths mesh and I put my arms around his body and we pull closer.