To New Beginnings Ch. 02

I recently decided to get back into writing. This is the first story I have done in a long time. I hope you enjoy this first chapter and I have more to come. CW - This part of the story contains forced feminization.

As always, all participants are of an appropriate age for the activities in which they engage and please leave me a comment when you're done.

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That morning I awoke, almost forgetting that I was wearing nothing but Jennifer's panties. I was woken up by the smell of bacon. She smiled and said

"a little treat after how wonderful you were last night."

I asked what I should wear for a shirt as it felt weird to be walking around in panties and sure that my work polo wouldn't cut it. She handed me one of her tank tops. It was a little tight fitting, but I was impressed that I was almost as small as her after the last 4 months of hard work, within a couple more months I might be skinnier than her... Although she would have more muscle mass than me if I continued working out the way we had been. We sat down to have breakfast and I ate it so quickly. I had hoped that this would help cure the hang over that was blasting my head.

My mind started to wander, wondering if she had gotten me drunk to take advantage of me, or maybe it was my comment about wanting to put on muscle that had spurred her into action.

She looked at me, "a lot on your mind?"

"Well yeah, I can say for sure, that last night was the first night I had been fingered and worn panties" I laughed a bit.

She smiled and wanted to confirm that I was still under her spell, "you still on for going to the mall today?"

"I mean if it's the only way I am going to be able to continue to be with you, I guess I have no other choice."

"Okay then! Well today I want you to continue to follow instructions, you are so very good at that Stephanie!"

I shuddered at the sound of my name feminized but I knew that this was how it was going to be if I wanted to continue to sleep with her.

She sat me down in front of her makeup mirror. The set up reminded me of my 'Battle station' at home but instead of a PC, this is where she went to war with the world. Putting on makeup every day was something society expected even from someone like her, and she clearly had some enjoyment for the process, why else create a shrine to it?

I didn't even offer any objections as she began to do my makeup, applying foundation first and then contouring my face with various shades. She then pulled out a pair of tweezers and shaped my eyebrows with a very prominent arch and cleaned up around them. After further outlining them with an eyebrow pencil, she moved on to my eyes, applying a light line of eye linger, some eye shadow and then the mascara. She instructed me to purse my lips like I was about to kiss, she applied something that stung on them, she told me not to worry that it was temporary limp plumper and finally applying a light coat of pink lip stain. She then sprayed my face and hair with hair spray, going through my hair making it messy like she had suggested the night before.

She told me to open my eyes and when I did, I couldn't believe who was looking back to me. It was still me, but I was much more a feminine version of myself, I am not sure if my own parents would recognize me at a pacing glance. I liked the way it looked, I couldn't lie when she asked.

"Most of my clothes are gym clothes but I do have something that I would like you to wear" she smiled with a most devilish grin.

She handed me a very short pleated red tartan skirt, a black very light partly see through sweater crop, a pair of black lacy thong and matching bra.

I looked at them inquisitively, "umm Jennifer, are you sure I can pull this off? Wont I be really exposed."

She replied with a smile, "you can absolutely pull it off!"

Well, I reasoned I guess its sink or swim. I pulled off the tank top she had lent me and the panties from the evening before. I pulled the new thong up my bare legs and knew instinctively to put my cock down this time, I didn't want her mangling it down again. She walked over and helped me put on the bra and stuffed it with some socks. I pulled the skirt up and put the sweater on over my head. I stood up, there was a gap between the top of the skirt and the bottom of the sweater, showing a couple inches of skin, thankfully the skirt was high waisted and did a good job at hiding my not completely flat yet stomach. She cheered, handed me a pair of ballet flats and told me to do a twirl, which I did. Next, I was not expecting she came and gave my ass a grab from under my skirt,

"there is my good girl. You look amazing Stephanie."

It didn't take her long to get ready. She clearly had this whole thing down to a science and was ready to go in her usual Lululemon pants and tank top within 15 minutes. With that we went down to the underground parking of the building, in her BMW and off to the mall. We arrived, shit of course it's going to be busy today, it's a Sunday, and we missed being here early enough for people to still be in church or working off hangovers like me.

We eventually found a place to park and got out. It was a decently warm July summer day. I felt the air hit the bare skin of my legs and then up my skirt. I was so thankful that in addition to it being warm, it was also a calm day, with no wind to speak of. Had there been even the slightest of breezes, everyone in the parking lot would be seeing all of my ass. I felt like all the eyes were burning on me but in truth it was mostly families, parents paying attention to their kids.

We walked inside the mall, Jenn holding my hand, she had a plan and knew where she wanted to go. First, we hit up a jewelry store that also did ear piercings, I was sure going to an actual piercing shop would have been better, but Jenn had her mind made up and I knew better than to argue with her. She bought me a really cute pair of cubic zirconia earrings, they looked like a million bucks but cost much less. I didn't really care about real diamonds anyways being dug out of the ground, likely by some poor kid in Botswana. I was pretty easily able to move on from my ears being pierced, with my longer hair, earrings could look cool, like a rockstar once all this feminine stuff was done with.

From there we headed up an escalator, I could hear some 20 something guys from behind us talking amongst themselves, one getting a little too loud saying "dude you can totally see all of her ass from our view and it's a nice one too."

I felt a small bit of pride in the compliment but also part of me hated Jenn for turning me into such a slut. At least it was just for the day. We moved on to Victoria Secret, Jenn had told me that it wasn't the highest quality lately but since I was currently losing weight, it was a good middle ground between the really expensive lingerie like the pair she had given me in the morning and the Walmart bargin bin. We picked out 10 different pairs of panties and thongs of various different colours. She told me that I could wear her bras since she only wore sports bras these days. We also picked out a pink negligée that she said she couldn't wait to put on me and then take off.

As we were headed back to the car, we ran into the same group of guys again, the one who had talked loudly before made a bee line straight towards me,

"Hi there!" he said excitedly, "my name is Tom, and I just have to say that you are smoking hot." Looking straight into my eyes, he turned his attention over to Jenn

"my other friend over there is really into athletic chicks and thinks that you are the hottest one he's seen... like ever"

I was dumb founded and was not sure what to say so I just looked back over at Jenn who replied curtly,

"that's nice, thank you."

He replied without a moment's hesitation, "my friends and I were planning to go out for lunch, how do you ladies feel about some good sushi and some drinks. My friend is totally loaded, so it would all be covered."

I looked back to Jenn trying to beg her with my eyes to say no. I already felt completely exposed, this guy had seen my full ass and now was wanting to get even closer.

"Sure! That sounds great, who am I to turn down a free meal and drinks."

I could feel the burning rage inside me, I was already here at the mall under Jenn's direction and now I was going to be forced to go to lunch with these fuck boys. What if he reaches under my skirt and discovers me? Is he going to attack me? All the thoughts ran through my mind, I pleaded with Jenn as we followed the guys down to the Japanese restaurant in the mall,

"Pleassseee Jenn, don't make me do this."

"Do what?" she quipped, "it's just a free lunch and couple of drinks."

As we walked, I tried to reason with her over and over that I just wanted to go home and spend time with her. I told her I would do anything if we could not do this... But she wasn't having any of it.

We just pressed on to the restaurant as we entered and we were seated at our table, Jenn had me sit right next to Tom and then her right next to him and his loaded friend who was into her on the other side of her. I did my best female voice impersonation, thinking back to the high pitch I was able to achieve last night and introduced myself to Tom as Stephanie. I had to be polite, try not be flirty but also do not be rude. I just have to get through this meal and then I will be free to go home with Jenn.

Tom and I chatted, he actually turned out to be a really nice guy, he was 25, in great shape, short brown hair, worked for his dad at a place that sold super and hyper cars. I was happy to have something to talk to him about that wasn't sexual. Asking him all kinds of questions about the kinds of cars he's gotten to drive and what was his favourite. He said that if he could have any car in the world, it would be a Countach, I had said that since I was a few years younger that my dream was the Diablo. We both agreed that the Mclaren F1 was an amazing car but valued at well over a million dollars, it would be terrifying to drive.

He put his hand on my thigh and for some reason I didn't smack it away. Maybe it was just nice to have a regular conversation about cars and my mind wasn't in the right place. The sushi and sake kept flowing through the afternoon. I am sure they would have liked to seat another group, but we just kept ordering. It was my first time having sushi before but I instantly loved it. I wasn't sure if this was the best example with us being 1000 KMs from the ocean but we did have a lot of lakes around. The sake I could pass on in the future, but it was helping calm down my nerves and I didn't feel confident enough to order something else myself.

The meal finally ended without much drama, Tom gave me a kiss on the cheek and handed me his number. Said to call him any time. I didn't think I would. Jenn smiled seeing that,

"see that wasn't so bad!"

I shot back quickly, "it could have been a lot worse if his hand went any further up my thigh"

She sighed "you are going to have to learn to be a lot more comfortable around people."

With that I knew she had wanted to keep me dressing this way for as long as our relationship or whatever this was lasted.

We walked back to the car, hanging on to her for dear life, the sake hitting me pretty hard. I had to remember that I had now dropped over 30 pounds and would not be able to drink like I used to. It was one of the few things my dad did that I agreed with, he let me have some coolers around 14 years old, he figured it was better to have me drink at home rather than go out and seek it elsewhere. Little did he know what I was so much of a loser that there was no way I was going out to parties or getting drunk at friend's houses. It taught me how to moderate my alcohol but after seeing everything he put my mom through, there was no way I was going to turn into a drunk like him.

We finally arrived at back at Jenn's car, me plopping down hard into the seat and her throwing our VS spree into the trunk. As we headed down the road, my head with the gentle buzz, the lights of everything on the street. I wasn't used to being a passenger anymore. It was a nice change. We pulled off the road into a strip mall. There was a nondescript store 'Little Shop of Pleasures' written in script above the door. Jenn turned to me,

"I just need to run in and grab a couple of things. You can hang out here. I won't be long"

We arrived back at her apartment. We sat down on the couch and started watching a movie, when out of nowhere, she turned to me and said,

"I think you should move in."

"Wait, what?"

"Yeah, I've been thinking about it, it would be a lot easier for me to train you, we could get you on a diet, really easily... Plus I've enjoyed your company these past 24 hours Stepanie... Also, we would have a lot more time to have some fun," she smiled from ear to ear awaiting my response.

I thought about it in silence for a bit. I didn't have much going for me, it had only been a month out of school, but it had been a month realizing the realities of the world. I knew I didn't want to end up like my dad working an entry level job for the rest of my life... But at the same time, I didn't know what I wanted to do for work. This could be a good hold over period, giving me time to figure things out, while getting to have sex with a girl who I considered way out of my league.

I wasn't bad looking but all the attention I was getting these days was from guys like Tom and that wasn't what I really wanted... was it? Could I live with Jennifer? Could I be her girlfriend because that's what me being here would amount to. How much further was she wanting to push this? Had she been planning this all along. Wait, the supplements she was giving me, the rate my hair was growing, the softer skin, the puffy nipples, even my chest had started to have pain, felt like it was growing even though we hadn't been doing any bench presses, so it shouldn't be. I made a mental note to search to Google those things later on. Made after she fell asleep not to raise any suspicion.

"Okay, let's do it!" I finally made up my mind.

She smiled from ear to ear, cheering and hugging me tightly.

"Yay! I have been looking to have someone clean up around here and to make meals for me. It will be nice knowing that you are here at home all day."

"Wait, all day?" I replied, pushing her back a little, looking at her eye to eye.

"Oh yeah, I guess I forgot to mention that part. It will just be so much easier for both of us if you can take care of both of us. It won't cost me much more to buy food for you, utilities will be a bit and all your new clothes will be costly, but I have a few ideas to help out with that. You will just need to go into work tomorrow and turn in your ID badge. You always talk about how much you hate your job anyways."

She was right. I did hate my job but at the same time, just dropping everything to move in with the girl I had just met a few months ago. It seemed like all too much. I think she could see the hesitation in my eyes, she leaned in and kissed my lips. Sweetly this time. Not aggressively like last night. She whispered in my ear how excited she was to have me living with her. She did it again, it didn't matter what my objections were. The whisper in my ear and they were gone.

She requested I stand up and smile in front of the bed. She pulled out a really fancy digital camera. I wasn't aware that she was into photography. She took a bunch of pictures of me. She said she loved the way I looked and wanted to keep this day in memory. She instructed me to get on the bed and then walked me through taking a bunch more pictures. A few were a little too risqué for me to keep as a memento but who was I to argue?

After she was done taking pictures, she moved on to the bed herself, kissing my lips passionately again. I had missed this so much, even though it hadn't been long since the last kiss. I could kiss her lips every day for the rest of my life and be happy. She took off my sweater, massaging my pecs over the bra, treating them more like boobs, it felt kind of weird until she pulled the bra down and took my nipple in her mouth, it felt like bliss. I couldn't remember my nipples being this sensitive before but then again, I guess I had never played with my own nipples.

She reached under the skirt, pulling the thong off, my cock at once jumping up upon being freed from its tight home. She pulled off all of her clothes in a moment, not taking much time with it. I would have loved to see her strip a little more slowly but here we were. Kissing again, me returning what she had done with my chest with her perfectly firm and round B cup tits.

She slowly moved herself down, guiding my cock into her wet waiting pussy. It was heaven. I was finally losing my virginity. She was controlling the entire moment, slowly riding up and down on me. I would get close, and she would clinch down on me and stop. Extending out the moment longer and longer. She whispered in my ear that she was on the pill and not to worry about cumming inside of her. Finally, after what seemed like an eternity, she let me cum inside of her. She stopped there for a moment, feeling me get soft and slip out of her.

With that she made a quick move, and her pussy was over my face. My cum now leaking out of her into my mouth, our juices mixing together. The taste was weird, but it wasn't the worst thing I ever had in my mouth. I started licking at her clit, trying to return the favour of bringing her to orgasm. I felt her grab my soft dick and she put my balls through something and then my dick through the same thing, moment later I heard a click. All I could see was her pussy and ass above me.

I kept licking at her clit, hearing her moan, getting close started to get me hard again but my dick was struggling against whatever she had just put on to my dick. I tried to pay no attention to the pain and focus on the job at hand. I felt her reach down and put something cool on my butt hole and then there was her fingers again into my hole. I moan into her clit which got a loud moan response from her.

I could feel her attacking my prostate again but as quickly as I started to enjoy it, her fingers left my hole and I was disappointed, only for her fingers to be replaced by something hard, and then the sounds of the vibration turned on. I quickly realized she had just put a vibrating butt plug inside of me but with the feelings it was giving me, I didn't care. My moans got louder a long side hers. We ended up orgasming at the same time, I felt my cum run down my thighs, at the same time her cumming expelling more of our combined juices into my mouth.

She reached down and turned off the plug. I was happy to finally let my body calm down. She reached down, pulling out the plug, I felt empty, but it was quickly replaced by another one. She patted my ass playfully and hopped off. I looked down finally seeing the pink object that was containing my dick. I looked up at her quizzically,

"it is called a chastity," she said answering the question I hadn't asked yet,

"you are now no longer a virgin, so you don't have to worry about that anymore. I know you have a problem with masturbation, so this will fix that. Also, from now on, if you are going to cum it will be from anal stimulation only, maybe if I am feeling nice, I will let you use my viberator on your clit. I also know giving me pleasure turns you on, so at some point, you might figure out how to use that to bring you to orgasm. Lastly, the butt plug is to never leave your hole except for in the shower to clean out your hole or if I take it out. If I find it out for any other reason, you will be punished."

I could tell from the clear, strong voice she was using, there was no arguing about this. She handed me the lube,