Part 3
I was alone in the apartment for the first time since Derek had left me tied up and helpless the night he discovered me dressed up as – as he dubbed me – Brandy. However, this time I wasn't dreading his return but anxiously waiting for him to come home. I had spent the past few hours scurrying about the apartment cleaning up and organizing the mess we had built up. Old fashioned though it may seem, the idea of being Derek's maid (among other things) had me moving like the Energizer Bunny and before long our place looked as good as when we'd moved in. I had washed dishes, tossed out garbage and beer cans, vacuumed the carpets, and even daringly made a run to the building's laundry room with a load of his dirty clothes and bedsheets. I say daringly because last time I saw Derek he had just covered my face with his thick cum and told me to leave it there until he got back. My heart was beating as quickly as my feet were moving as I raced through the hallways but my want to make him happy outweighed any fear I had.
Finally feeling a little worn out from my frantic cleaning, I collapsed onto the couch to catch my breath. As I looked around the room, it hit me that even though Derek had instructed me not to clean his load off my face, he hadn't given me any instruction beyond taking care of the apartment and I had spent the past couple hours alone and completely in "character" as Brandy. Probably feeling more graceful and feminine than I looked, I had only covered my skimpy lingerie to make the laundry run but immediately shed my male clothes upon re-entering the apartment. I hadn't stopped to get myself off at any point which only a couple days ago would have been inevitable the second I slipped into the soft leggings or the felt the silky panties hugging my ass. This afternoon had simply been me experiencing Brandy take over my male self and it was all just a subconscious instinct, at no point do I remember "having" to strip down – I just did so reflexively and that thought filled me with warmth and comfort.
I was still in a bit of a daze on the couch when Derek returned home. He looked around the apartment and I bit my lip anticipating his reaction. He gave me a satisfied, but not overly emotive, smile as if he was happy with what I'd done but only because it was just what he'd expected.
"Wow, this place looks great Brandy. Looks like you got just about everything cleaned up besides your face. I really didn't expect you to take to this so quickly but you were always good with instruction." he says to me with a bit of a chuckle, looking me in the eyes as I sat there only able to maintain eye contact with him for a second or two at a time. "Let me take a shower and then I have an idea for you."
Derek turned towards his room and once again left me alone where I sat on the couch as he showered. When he had finished he came back to the living room to tell me what he had in store for me today. He walked up beside me and stood over me, cradling my chin in his big, strong hand so this time there was nothing I could do to avoid looking him in the face.
"If only you could see your face right now, covered in my dried up cum. How does it feel?" He spoke to me in a gentle voice and with his free hand he grabbed my own as I reached up to touch my face and held it in place, clearly wanting an answer.
"I guess I like it, it was kind of cold after a while but I don't even notice it now."
"Hmm, so you're a natural cum slut aren't you? Well like I'd said before, this is the only makeup you have right now so I'll let you keep this on while we go pick something up for you. But I don't want a mindless whore – I know enough of those – so, after today, you are going to need proper makeup whenever you go out with me. Make yourself as decent as you can with that facial, I'm bringing you shopping." He lifted on my chin until I was standing and slapped my ass, pushing me towards my own room.
With nothing more than a shocked gasp as I felt the sharp pain when he spanked me, I quickly ran to my room and grabbed some jeans and a hoodie. Although I had sped through the apartment building earlier, going out in public and, I assumed, to the mall gave me a bit of a fright so I pulled a baseball cap low on my head in hopes that the shadow might mask my, well, mask of cum. Derek clearly knew my motivations with the cap as when I met him near the front door he smirked and flicked the bill of the hat higher up on my head and gave me a shake of his head that forbid me from fixing it.
I was right about our destination. We drove to the mall and despite a few moments of nervousness when I noticed strangers giving me sidelong glances and dirty looks, I actually had a lot of fun. Derek was no trust fund baby or snobby rich kid but his parents were very well off and were paying for his school and credit cards so he told me we didn't really have a limit and to buy whatever I needed. Even though I knew next to nothing about women's beauty or makeup I merely grabbed anything I thought I should have or was excited by. Before long I had a basket full of different coloured nail polish, lip stick, mascara, eye shadow and liner, blush, and a few shades of foundation. While I'd been like a kid in a candy store in the makeup aisle, Derek had ducked off and came back to me with a few packs of cotton panties. They weren't as sexy as the lingerie I had on underneath my clothes but still cute and definitely more for everyday use than the ones I'd had. He'd also found a few pairs of colourful sundresses which he folded up and set on top in the basket.
The one thing I wasn't expecting was when Derek handed me his credit card and told me it was time to pay. I glanced over to the cash registers with a lump in my throat and slowly made my way over, deciding who might be my best bet to get through this quickly and easily. Eventually I decided on a middle aged woman with a very motherly aura about her and felt good in my choice until, as she scanned the last of the makeup and panties and took the credit card, she spoke to me.
"Here's your card back, honey. Looks like you're going to have some fun with this. It's all going to look great on you!"
"Um, it's for.... uh... thanks." I squeaked out, my eyes looking up briefly to see here staring at me with a wide and warm smile, holding the card out in her hand which I quickly took and hurried from the store.
Derek was waiting for me outside the entrance with his own trademark smile, at once putting back at ease the closer I got to him. I held out his credit card which he accepted with a wink and once again gave me a quick slap on the ass before we headed to the car.
Getting home, I finally had a chance to calm down. For the last month or two I had fantasized incessantly about being a woman – Derek's woman to be precise – and having him on top of me and inside me in a myriad of positions as he made me his but I'd never expected to be out in public with his cum on my face while buying girl's clothes and makeup. Kicking his shoes off, Derek turned to me and perked his eyebrows as he grabbed the bag from my hand and looked inside.
"Nice haul, Brandy. This should do you well for a while. I think you owe me a thank-you, don't you?"
"Thanks Derek, that was kind of fun. I'm actually looking forward to playing around with some of this." I meekly responded.
"You say that as if there was ever any chance you wouldn't enjoy this." he said after a bark of laughter. "I think we both know this is just what you want. So grab me a beer and go make yourself pretty."
I obediently fetched him a cold beer from the fridge and took my shopping bag of new treasures into the bathroom. Derek was right, this is something I wanted and I quickly got lost in the moment as I began a new ritual. I showered, shaved my face and body from the neck down, and set to experimenting with applying makeup to my face for the first time ever. I don't know what I expected but it was harder than I thought. The nail polish wasn't too difficult, but I felt clumsy and awkward with most of the rest of it and had to wash down and start over more than once. After a few attempts I no longer looked like I'd been hit with a makeup shotgun and was feeling proud of my nearly-competent job when Derek startled me by knocking loudly on the door and asking if I was done yet. I quickly put everything away and opened the door hoping he would be as happy with the results as I was. I stood in front of him, naked but for the makeup on my face and nervously twirled a lock of hair around my fingers waiting for his judgment.
"You're going to take some time to get the hang of this, but you almost look better than you did with my cum all over you this morning. Why don't you get dressed? I'll wait on the couch."
As I entered my room I could tell something was different and it didn't take me too long to discover that my dresser and closet were almost completely empty. No clothing was left except for the lingerie set and the new panties and dresses Derek had just bought me. He must have cleared out my male clothes while I was in the bathroom. Deciding to mix it up, I grabbed a basic pair of white cotton panties which weren't as thrilling to look at as my hot pink crotchless panties but I found just as exciting to wear I suppose because wearing everyday women's underwear was almost more of a signal to my femininity than simply jerking off in lingerie. Not to mention the way they hugged my little bum as I walked around just felt amazing. I had always been a fan of seeing ladies in sundresses before all this and when I pulled a soft yellow dress from the closet and slipped it on, I understood that it was more than a one-sided appreciation. I felt free and open as I twirled the dress about my knees, smiling to myself in the mirror and taking a few laps around my bedroom. I never wanted to take it off, this simply garment made me feel so cute and right that I practically ran out to seek Derek's approval.
He was sitting on the couch with a fresh beer watching something on the TV. I was only focused on him and he seemed to ignore me as I stood before him until he finally turned his head to take in my transformation. From what I'd seen in the mirror, I thought I looked pretty damn sexy and while you could easily tell I was not a real girl, it almost seemed in reach with a few more items and some work on my part. Derek clearly agreed, taking me in with some slow nods as I repeated my twirls and spins for him to show off.
"Shit, you actually look pretty good, Brandy. Keep growing your hair out and with some practice at the makeup you are going to be one hell of a sexy little slut for me!" Derek's words melted me and I wanted him to just jump my bones then and there
Thankfully, he had something similar in mind.
"I can tell just by looking at you that you're having the time of your life. And I have to say that I'm surprisingly happy with this too, but I think a little thank you is in order, don't you? I mean, I did just pay for everything you have on right now." Derek grabbed my hand and gently but assertively pulled me to the floor in front of him.
I knew what he wanted and I wanted the same thing. On my knees between his legs as he sat on the couch, I slid a shaky hand up his thigh to unbuckle his belt as I stared up at him, transfixed by the way he was smiling down at me. I eagerly unzipped his pants and sunk my hand in to feel his semi-hard cock waiting for me. It still felt so big in my hand that even touching it over his boxers felt electric to me and I was at once upset and excited when he pushed me back for a second to slide his pants to the floor for easier access. He sat back down and I resumed my exploration of his cock. Only the second time I had truly been able to experience it at my own will and pace. It was twitching at an increasingly fast rate, tenting his boxer shorts more and more with each pulse as I slid my hands up and down, around and around the beautiful dick I knew was waiting beneath the flimsy layer of fabric. The thought that this dick was getting hard because of me was exhilarating and I had to have it right away.
I pulled at the top of his boxers and he stood once again, letting me pull them to the floor. This time he remained standing as his now full erection stood at full mast, staring me in the face. He placed a hand on my head but I didn't need any motivation as I leaned in a took his mushroom head in mouth, reaching a hand to roll his balls around in my palm as I started sucking and tonguing the head of his cock. I was rewarded with a stream of pre-cum, and he produced a lot of it, that only made me go crazier. I loved the taste of him and wanted more. My free hand latched on to the base of his shaft and began jerking him off slowly while I went to town suckling the head for more of his juices.
He could sense my eagerness and removed his hand, leaning his head back and letting out an animal groan of pleasure to tell me I was doing a good job.
"Fuck yeah, suck it just like that." he said as if I needed any more encouragement.
I always felt like time slowed when I had a dick in my mouth, and after what felt like an hour to me, Derek pulled himself out from between my lips and told me to get him another beer. Not wanting to leave his cock but knowing that the faster I did as he said the sooner I would have it back in my mouth I raced to the fridge and back to find that the commercial break that had started as I'd first entered the room was just ending meaning I'd only been sucking him off for a couple minutes at most. I handed him Derek the beer and resumed my rightful place on my knees before him. The hand not occupied by his beer was holding his cock near the base and waving it in my face so I waited for him to shove it back at my wanting mouth and felt that switch flick in my head once more that stopped time and let me focus purely on the task at hand, or perhaps at mouth.
I could have spent all day sucking pre-cum from the tip of his dick but I knew Derek would want more and started pushing myself deeper onto him. I had practiced with my dildo countless times and so I wasn't worried about my now abolished gag reflex, but this was still only the third time I had had a real flesh and blood dick in my mouth and took my time so as not to scrape him with my teeth. I was about halfway down his 7" length when he grabbed my hair and decided to speed up the pace. Pushing me further until my nose was squished against his pelvis and the only air I could breathe was musky with the manly scent of his pubic hair which only drove me more wild for him.
He held my head in place for a few seconds before pulling me off and then slowly fucking my mouth with his hand controlling my head. I closed my eyes and devoted myself to feeling and tasting him with my mouth as he had his way with me. I had a hand braced on his muscular thigh and the other was back playing with his balls when he pulled me off completely, a stringy bead of saliva and pre-cum keeping me attached to his dick as I looked up at him like a dog begging it's owner for a treat.
"That was a good start, but I spent a lot of money today, I think a proper thank you is in order." he flopped back down on the couch and patted his thigh a few times, making it clear what he wanted.
I stood up and sat myself on his lap facing him. He slid a hand all the way up my freshly shaved leg and began tickling my inner thigh with his fingers and watched my reaction with obvious contentment as I shuddered at his touch.
"You want to get fucked again, Brandy?" he asked as his hand was sliding under my thigh and past my panties to tease around my asshole.
"Mmm, Derek I want you to fuck me so bad, yes please!" I didn't even think as the words spilled out of me.
He smiled, pushed my chest down, and repositioned me with ease so that I was lying across his lap like I was about to get spanked. And I did. He lifted my dress up and continued rubbing the back of my thighs which was driving me crazy. Suddenly the soft caress turned into a sharp and yet not overwhelming pain as he spanked my cheeks quickly.
"I can't believe you have had such a nice girly butt this whole time and I never noticed." he kept spanking me, but slower and with varying strength. I had always thought I had a nice ass and I could tell Derek was enjoying playing with it himself.
The spanking stopped as quickly as it began and his fingers forcefully tugged at my white panties, sliding them down my now-tender ass. It was only as he pulled them down to my knees that I felt the wetness and realized just how much of my own pre-cum had been released and drenched my panties from just sucking him off, I hadn't even touched my own dick at that point. Derek must have noticed this and scooped his fingers into the crotch of the panties, smearing my own pre-cum around my asshole with two strong fingers. I let my head hang down and reached back with my hands to spread my cheeks and give him better access to my vulnerable hole which he took as a sign to plunge the first finger into me. The now familiar pleasure of being penetrated took over my senses. Combining spit with more pre-cum, Derek worked my hole with his fingers and quickly picked up on the fact that hitting my prostate sent me to the moon with pleasure. The deeper he went the more my dick streamed slippery pre-cum which he then applied to my asshole and continued the circle of pure ecstasy for me.
I couldn't say how long he had been playing with and stretching my hole but I felt a swelling feeling in my stomach and just HAD to have his dick inside me again.
"Der, please, fuck me now!" I yelled breathlessly to him.
He didn't say anything but merely hummed and stood me up once more. He pulled my panties completely off and tossed them to the side, grabbing his dick and holding it straight in the air from his seated position on the couch. I took the hint and did my best to take him all the way into my throat one last time before he pulled me off and grabbed my hips to spin me around. My ass was facing him and he pulled me down, controlling the whole situation. I didn't resist his guiding hand as he pulled me lower towards his cock and when I finally felt the head poking at my hole I began to push out and readied myself. Unlike the first and last time he had fucked me, I'd only had a minor warm up and no lube besides spit and pre-cum so as he pressed the tip of his cock into me I felt more pain than before. I tried to grit my teeth and take it, undeterred by the discomfort and anticipating the pleasure that was surely coming. The head popped in and Derek kept pulling me down until his bristly pubes were tickling my wet ass cheeks and his hard cock was totally filling me. I used one hand to bunch the skirt of my dress in front of me and out of the way, the other hand reaching back to rest against Derek's leg as I sat still and got accustomed to his cock inside me.
He now had both hands at my hips and started lifting me slowly and then pulling me back down. First going no more than an inch or two and gradually increasing the depth and speed of my bouncing on his dick. It was still painful for me and at this point I preferred just sitting with him filling me up, I would have exploded if so much as a breeze had touched my dick but Derek was clearly the one in charge here and he was controlling the pace. For several minutes he worked me up and down the length of his cock and was obviously enjoying this more than I was. Every once in a while his cock would hit the right spot and I would involuntarily moan in pleasure but his constant grunts made it clear this was more for him than for me.
After some time he seemed to tire of doing all the work and without pulling himself from me he lifted me up and spun us around so that I was on my knees leaning over the back of the couch and he was standing behind me. In this position he was able to really start pumping at my ass and did so without holding back. It was all I could do not to burst out in tears from the pain I was feeling and I think Derek could tell I wasn't enjoying this as much as the previous time. He slowed down and leaned forward to gently coo and whisper in my ear to try and calm me.
"Derek your cock is so big, I need more lube." I told him in a pained voice and immediately betrayed myself as he hit my prostate and loosed a scream from my lungs that was undoubtedly pleasure.
"Sounds like you're enjoying it to me. Just relax and get used to it." was all he replied as he gently brushed my face with a couple fingers and kept feeding his cock into me.
While the pain was constant, I had to admit that as far in between as they were, the bursts of pleasure I felt when he touched the right spot inside me more than made up for any discomfort and I surrendered myself to his thrusting, thinking to myself that this is what I had dreamed of for so long. Before much longer, I felt him slow his pace and grab my cheeks, pulling them apart. He pulled completely out of me, then thrust in balls deep and gave a few quick, short pumps before groaning loudly and I suddenly felt a tide of warmth filling me which told me he had just filled me with his hot cum. He sit still for a minute and then pulled out, keeping my cheeks spread and holding me down over the back of the couch.
"Brandy your hole looks so sexy and used up with my cum leaking out of it. I think I like this even more than wasting it on your face." Derek poked and prodded at my gaping hole and I felt the gooey cum dripping out of me and down my thighs. "Good girl." he said as he gave me a final light spank and pushed himself away.
Any pain I'd felt earlier was erased from my mind after hearing his words and I laid on the couch in a glow, feeling at ease in my new dress and with Derek's cum filling me up. I knew I never wanted to go back to how things were before if this was what life could be like for me as Brandy. I heard Derek turn on the shower to cleanse himself of what we'd just done whereas I felt the complete opposite way in that I never wanted to wash his cum from me, I wanted to be covered in his essence and knew I truly was Derek's girl.
So sorry it took me so long to get this part online. It took me a little while to put together and recently have just had too much going on to put much effort into writing it. I won't make you wait this long again, promise. Thanks for reading and as always any feedback/criticism is appreciated so don't be shy :)