TITLE    : Covid Changed My Life
STORYID  : covid-changed-my-life
SUMMARY  : A new BBC roommate makes me a sissy.
AUTHOR   : sissyashley4bbc@lit
DATE     : 2022-09-14
CATEGORY : transgender-crossdressers
FLAGS    : h
TAGS     : |sissy|bbc|interracial|feminized|black cock|black dick|big black cock|black man|white sissy|huge cock|


Covid and layoffs at my company couldn't have come at a worse time.

My name is Ashton, and I'm 23 years old, a year out of college, and just signed a 2 year, $2300 a month lease on an awesome 2 bedroom apartment with the intention of using the small 2nd bedroom as an office.

There was no chance I could make ends meet now, I needed to find a roommate and a new job ASAP!

Not knowing many people in the city, I posted an ad on craigslist for a roommate. The only hit I got was from a guy named Mike. After exchanging emails, he said that he was very busy but would come by to check out the apartment and make sure I wasn't crazy tomorrow at 4pm.

While I was free, I was a little bit annoyed that he didn't ask me if that time worked for me too.

The next day, Mike showed up right at 4pm. I'm not sure why I was surprised, but I was surprised to learn that Mike was a 6'5", black, former college football player.

Me being 5'7", I felt so small having to look up at him as we made small talk. And when we shook hands, his hands completely enveloped mine.

As I showed him around the apartment, Mike commented how much he liked my style and how I had decorated the place. I was flattered.

"Ok," Mike said, "here's the deal. The place is great, but there is no way I can fit in the small 2nd bedroom. There wouldn't be room for my king bed. Also, that closet is way to small, my size 15 shoes would take up all the space. Also, I am going to be working from home for a while and will need office space in my room. Given that you don't have a job, you aren't going to need the space. How much is your entire rent?"

"$2300 a month," I replied.

"How about this Ash? I'll pay $1300, so you only have to cover $1000 a month, but you have to move out of the master suite into the 2nd bedroom," Mike proposed.

I really didn't want to so that, but I didn't have another choice.

"I'll do it if you pay $1500," I negotiated.

"You drive a hard bargain," Mike winked, "but deal!" He said as he extended his hand to shake on it.

I once again marveled at the size of his hands as we shook on the deal. Only having to pay $800 a month was going to buy me some time, but I still needed to find a job.

5 months went by and I still didn't have a job. Unemployment helped, but I was down to the last bit of my savings.

As for living with Mike, it was mostly good. Pretty crazy going from strangers to spending quarantine together though. His work was going great, and he was always very generous, sometimes picking up the tab on groceries and sharing his beer, wine, and weed with me.

There really were only two things that bothered me about him.

First, he was extremely arrogant and frequently made comments about our difference in stature. He wasn't wrong, but he also didn't need to do it so often. When doing that, he also would make comments about how nice my legs and butt were. Saying I more resembled a sexy girl than a man.

The other thing he did that annoyed me was that he always liked to put on porn if we smoked weed late at night. However, it wasn't just that he would put on porn (because I always found myself getting really horny when we smoked), but it was always interracial porn.

Mike has a subscription to "Blacked" so we are always watching movies of white girls getting fucked by the biggest black cocks.

Once I asked him if we could watch a video with a white guy in it, he told me we could if I paid for it, knowing full well I was broke.

After these nights of smoking weed and watching big black cock porn, I would lay in my room, close my eyes, and stroke my penis. Given that all we would watch was big black cock porn, I couldn't fight the images burned into my brain of big black cocks slamming into white girls, giving them immense amounts of pleasure. Sometimes, I would even start thinking about whether Mike's black cock was as big as the guys in the movies.

Regardless of what I thought about, I always came.

By the 6th month of quarantine, I was broke. I couldn't afford to make rent. So I mustered up the courage and went to talk to Mike.

I nervously walked upstairs into his master suite.

"Hey Mike, do you have a minute?" I said, wondering if he could hear the nervousness in my voice.

"Sure Ash, whatsup?"

He always called me Ash now, which I didn't like, it sounded feminine and demeaning to me.

"So, I hate to do this, and I am very embarrassed, but I cant make rent this month. You know I have been trying, but even with unemployment, I can't cover my share of rent and utilities and still afford groceries," I said, starting to tear up.

"Hey Ash, it's ok, tell me how I can help," he responded.

"I can contribute my $600 from unemployment, but that's all I have. Can you cover the rest?" I asked.

"That's close to $1,000 between rent, utilities, and food Ash," he stated matter of factly.

"I know I am asking a lot, but please Mike? I'll do whatever I can to make it up to you."

"I can definitely cover it," Mike said, "in fact, work has never been better so it will really be easy for me financially."

"Oh my god, thank you so much Mike...," I started.

"I wasn't done," he said sternly. "Now I don't believe in free handouts, I think it sets a bad precedent, so you will need to work off this debt throughout the month to me. I will have a contract for you to review tonight. Now get out, I have a meeting."

I nodded and walked back downstairs. I felt a weight lifted off my shoulder, but I also felt belittled from him telling me how well off he is and also a bit nervous by his change in tone and that there was going to be a contract for me to sign.

The next few hours went slowly. It was just about 5pm when Mike yelled for me to come upstairs.

"Yes, you called Mike?" I asked once I got to his door.

"Come sit next to me Ash," Mike said, patting the seat he had pulled up next to him at his desk.

"So Ash, I thought about your situation, and I have a proposal for you right here," he said tapping the piece of paper in front of him.

He continued, "This is a contract for the remaining 16 months of the lease. If you agree, I will cover the entirety of your portion of lease, utilities, and groceries. Additionally, I will give you a $750 uniform stipend to get started and $200 a month for flexible spending. However, all purchases must be approved."

"Uniform?" I interrupted.

"Don't interrupt me Ash," he said directly. "What I am proposing is that you will become my live in maid. However, you will have to be fully dressed as a female whenever you are in the apartment. Since I know you can't afford the proper clothes, I have some things to get you started being delivered shortly, and then you will have to submit your proposal clothes order for your stipend by the end of the day."

"I'm not dressing in drag Mike," I said.

"Unfortunately, that is a deal breaker Ash," he quickly responded. "I am willing to negotiate on payment terms, but not the actual job description. Let me continue. If you agree, not only will I cover your expenses, but you will get to keep your monthly unemployment check, which will go into a savings account under my name, which I will transfer back to you at the end of this contract. If you get a job and can cover your costs, then the contract can be void."

He noticed me trying to do the math.

"Don't hurt yourself sweetie, numbers aren't your strong suit or else you wouldn't be broke. While you will be 100% dependent on me financially for the next 16 months, you will complete the term of this contract with $9,600 in savings from unemployment and the ability to earn additional deposits from me and agreed upon amounts. With what I have in mind, I wouldn't be surprised if you came out of the other side of this with $20,000 in your savings account.

I sat there thinking about it, dressing in drag for 16 months seemed insane. But it would keep me living a good lifestyle in this apartment, and I would come out or the other side with a solid financial cushion.

Also, it could all go back to normal as soon as I find a job, and I have a couple of good leads as is. Worst case scenario, it will be a month or two.

"Well you kind of have me up against the wall, but I'll do it, I'm hoping to have a new job in a month or two anyways. I figured I was going to be your live in maid, I just wasn't expecting having to wear women's clothes. Where should I sign?" I agreed

"I would advise you to read the rules of the contract before signing," he laughed, "signing a dumb contract is what got you into this mess in the first place."

I blushed in embarrassment and took the paper from him. I skimmed over the first paragraph which was everything he just went over regarding the duration of the contract and financial aspect of it.

Then it got to the rules:

"1. From hereon out, Mike will always be referred to as Sir

2. From hereon out, Ashton will always be referred to as Ash, Ashley, Baby, Sissy, or Sissy White Boi

3. Breakfast must be served at 7am on weekdays, at request on weekends

4. Lunch must be served at noon

5. Dinner must be served at 7pm

6. Laundry must be done at minimum once a week

7. Floors must be mopped/vacuumed once a week

8. Upon signing of the contract, Ashley must turn over all male clothes to Sir

9. Ashley must be completely hairless besides her the hair on top of her head, eyebrows, and eyelashes

10. Ashley must wear approved uniform including matching bra at all times, unless told otherwise by sir. No pants or shorts longer than 8 inches.

11. Ashley must wear supplied jewelry at all times

12. Ashley's nails must be painted at all times, approved colors are pink, purple, red, or white. All other colors must be approved by Sir.

13. Ashley's room must be painted purple or pink

14. Ashley will follow a strict diet plan, except for Friday, which will be cheat day

Failure to follow these simple rules is punishable at the discretion if Sir."

This seemed ridiculous but I had no choice. Anyways, we were in quarantine, no one would see me.

I picked up the pen and signed next to his name.

The doorbell rang. Go get the door Sissy, your things are here.

"Ok, thanks M...Sir," I said meekly.

"Good catch Ashley, don't worry, you will get used to it," he said, turning back to his work, "and remember, dinner is at 7!"

I looked at my phone, I have about an hour and a half to get dinner ready.

I got to the door and the delivery person and left 3 big shopping bags at the door. I picked them up and took them into my room, setting them on my bed.

The first bag was full of shower needs. Female shaving cream, a pink razor, a brush, a straightening iron, a curling iron, some hair spray, and a blow dryer.

I always kept my long hair in a man bun, but I guess that wasn't going to be enough.

I then opened the next bag, it was full of underwear. I pulled out probably 10 pairs of panties, with matching bras. I sifted through the panties quickly, they were all different cuts, colors, and fabrics. There were also 2 pairs of thigh high stockings, black and white. At the bottom of the bag there were a pair of 4" black high heels.

In the third bag, there was a box with the approved nail polish colors. There was also a black choker necklace with a charm on it that said "sissy". Lastly, there was a big black dildo on the bottom.

I picked it up and marveled at the size. Not sure why this is in here though, there was nothing in the contract about big black dildos. I am sure of that.

I looked at my clock, shit only an hour left until dinner. I ran into the shower and started shaving my legs and arms, luckily I'm not naturally very hairy. Lastly, I shaved my crotch and rinsed off.

As I got dried off, it was strange seeing myself completely hairless. I brushed my hair down and blow dried it, styling it quickly as a woman would.

I hurried into my bedroom and stared at my bed which was littered with panties, bras, and stockings.

I spent 5 minutes looking through the panties, trying to find the least embarrassing ones to wear. Unfortunately, the only plain black pair was a thong, no way I was wearing that. Any pair that was cut more conservatively were also the girliest.

Eventually, I landed on a pair or purple boy shorts with two little white flowers, one on each hip. I slid them up my legs. Maybe it was due to being completely shaved, but I felt my penis jump to life as I felt the tight material hug my ass and penis.

I looked at the clock. 30 minutes until I needed to have dinner ready for Sir.

Remembering that the contract specifically noted "matching bra", I grabbed the purple bra, noticing how elaborate it was. I should have looked at the bras when making my decisions. The matching bra had elaborate stitching with white flowers and stems made of lace on each cup. It felt silly wearing a bra, but they were tiny cups, so its not like it didn't fit.

I stepped into my heels and turned to look at myself in the mirror. I couldn't help but notice two things. First, I didn't look silly at all. I actually looked pretty hot. Everything fit perfect and my ass looked amazing in the panties. If I was a girl, I would definitely stare at my ass. Also, my penis was rock hard. Luckily, I was pretty small, so even when hard I fit snugly in my panties.

I only had 15 minutes left to paint my nails and get dinner together, no chance I could get it done. I needed to get some additional time from Sir.

I walked out of my door and realized that this was going to be the first time he saw me in lingerie. I got very self conscious walking up the stairs, hearing my heels click on the wood floor.

I took a deep breath as I got to the top of the stairs, I knocked on wall, "excuse me, Sir?"

He spun around in his chair, "wow Ashley, you look amazing. Purple might be your color. Turn around, let me see that ass of yours."

I looked at the floor, I didn't want to turn around. I was his maid and cook, not his sexual object.

He sensed my hesitation, "c'mon now Ashley, I'm going to see your perky ass sooner or later. You'll be living like this for at least 16 months."

"Not 16 months, maybe a month or two, I'm going to get a job and pay my fair share," I argued, starting to get emotional.

I felt like I was going to cry. I wiped the corner of my eye.

He walked over to me and pulled me close, giving me a hug. I felt so small as he wrapped himself around me. For a moment, I even forgot that I was being hugged my a huge black man as I stood there in lingerie.

He broke the silence, "hey there Ashley, you are right, I'm sure you will be back on your feet in no time. I know you don't want to be doing this, but I really do think this suits you in the meantime. Now what did you come up for? Just to show me how hot you look in lingerie?"

"No, Sir, I just wanted to see if we can push dinner back tonight, I ran out of time getting ready," I asked.

"No problem at all Ashley, I'll tell you what, since this is your first night, I'll order us delivery from your favorite sushi place, and you just worry about picking out what nail polish you think matches the best. Does that sound good?"

"Yes, thank you," I said, wiping the last of the tears from my face as we broke the hug.

"Thank you...who?" He said.

"Thank you Sir," I said as I turned around and headed down the stairs.

"I told you I would get to see that perky ass of yours! Even better than I imagined!" He yelled down the stairs after me. "Also, dinner will be here in 30 min. Finish your uniform and have a bottle of red wine open by the time I come down."

I walked into my room and looked at myself in the mirror. I couldn't help but notice my penis was still hard. I hope he didn't feel that during our hug. Also, there was a little dark purple spot where the head of my penis was pressed against my panties. I pulled the waistband out to look at my penis and was mortified by the pre-cum that was there. Why was my penis leaking pre-cum? Sometimes I would have some pre-cum in my boxer briefs after we smoked and watched a bunch of porn, but that was on rare occasions.

Oh well, and opened the box of nail polish, I decided just to go with a simple white. I painted my fingers and toes.

I got off my bed and walked out the door before remembering the necklace. As I looked for that box buried in panties and bras, I first found the big black dildo.

I picked it up. It was so heavy. It looked jusy like the the big black cocks from the movies. Thick. Veiny. Intimidating. How would anyone be able to fit this inside of them?

I put it back down and found the choker. I put it on. It felt tight, but kind of sexy.

I walked out to our wine rack and picked out a bottle of red that I know is one of his favorites. Popped it open to breath and set it on the table along with two wine glasses. I then set the rest of the table as I waited for the food.

I put on some music and then sat at the table waiting for either Sir to come downstairs or the delivery.

The doorbell rang and I stood up, walking to the door. Thank god for contactless delivery right now so no one would see me like this.

I opened the door and pale as a ghost.

"Sorry to scare you, uh, m'am, but your order requested signature upon delivery," the delivery man said.

I silently took then pen and receipt, signed it, and handed it back to him. I took the food from him and quickly closes the door.

Embarrassed, I turned around and saw Sir sitting at the table, laughing hysterically.

"Well that was worth the cost of the sushi alone!" He said, still laughing.

"Not funny!" I sarcastically pouted walking over to the table and pulling the sushi out.

"Just a bit of fun! But lets eat," he said, pouring us each a glass of wine.

My white nails caught me off guard when I picked up my chopsticks.

"So how do you like your clothes?" He asked, breaking the silence.

I took a sip of my wine, thinking through my reply.

"I'm surprised you knew my size," I responded.

"Yea, most of the girls I have been with are about your size and always wear smalls. I was most worried about your bubble butt squeezing into a small. But if that is an issue you can always just wear thongs."

"I'm not sure if I am going to wear a thong," I said.

"You never know, you might find out prefer certain benefits of thongs. The other piece I was worried about was your penis. I always assumed you were small given how easily you could hide your erection when we watch interracial porn together, but I didn't think you would be so small that you fit in your panties even when you are erect."

"I'm not erect," I said, "and I'm a grower not a shower."

He laughed, "grower not a shower! Love it. That's just some dumb shit guys with little penises say."

"Its true!" I argued.

"All I know is that when you came up to my master suite earlier, you were hard as a rock and everything you have was well contained. Even soft, I would be falling out of panties," he said sternly.

"I didn't think you noticed," I said, staring down at my plate in embarrassment.

"Why didn't you think I would notice Ashley?" He said taking a sip of wine. "Is it because you have a little white penis that you didn't think I would notice?" He prodded.

"I...I...I guess when you put it that way," I gave in.

He reached across the table and put two fingers under my chin. He lifted my head so I was looking at him in the eyes, "and like I said earlier, you might find that this suits you. Now, lets have some fun, you look sexy as hell, cheers to our new lifestyle!"

I couldn't help but crack a smile.

"There she is!" He laughed, taking a sip of wine.

I took a sip too, letting out a giggle.

"So what did you think of the toy I got you?" He asked, once again breaking the silence and taking control of the conversation.
<hr pg="2" />"By toy do you mean big black dildo?" I responded.

"That's the one," he said, "I'm sure you are still figuring out the new you, but I have heard that many sissies are size queens at heart so you might enjoy taking it for a spin."

"I have no interest of putting that big black dildo, or anything else in my ass," I laughed, taking a sip of wine.

"We'll see!" he said. "As I have been saying, you might find that it suits you."

The rest of dinner was more of the same. He prodded with questions asking me about how my panties fit, bra felt, why I picked the sexy purple set. Anything to get me thinking and talking about my current outfit.

Eventually, we finished the last of the wine and last of the sushi.

"What do you think about ending the night with a bowl of weed and a movie?" He asked.

"On a weeknight?" I asked.

"I have a pretty light day tomorrow, and all you have to do is make sure my breakfast is ready at 7 unless I am mistaken," he said.

"Ok well then sure!"

After all, I was pretty horny already, some weed and porn to put me over the top sounded good.

"Why don't you get the movie set up, I'll go grab my bowl," he said.

I walked over to the couch and picked up the tablet that was hooked up to the TV. He has never let me pick out what we watched before. I went to blacked.com and scrolled through my options.

I landed on one we had watched before but was one of my favorites, it starred a tiny cute blonde, Elsa Jean and Jason Luv, a huge black guy with an enormous black cock. He's working on the house and she stumbled across him in the shower. It's totally cliche, but also hot.

Sir came downstairs wearing a tank top and athletic shorts. "Oh good choice Ashley! This is a great one, and I don't think we have watched it in a while. What's his name again?"

"Jason Luv," I said.

"That's right, great memory. He must have really made an impression on you."

Was he just trying to get me to admit out loud that I knew his name? Did I fall into his trap?

He took a hit and passed the bowl to me. I took a big hit and sunk back into the couch, letting the weed wash over me. I picked up the iPad and pushed play, the movie started on our enormous 70 inch TV.

"Get the lights Sissy," Sir instructed.

I stood up and walked over to the light switch.

"Hard already?" He asked.

Embarrassed, I sat back down on the couch and crossed my legs like a girl, hiding my boner.

I picked up the bowl and took another hit. That might have been a little bit too much, I thought to myself as I felt it tingle throughout my body.

"Good girl," he said from the other end of the couch, "why don't you come sit next to me?"

"No way, I'm not sitting right next to you while we watch porn," I said.

"$100," he said.

"$100?" I asked.

"Correct," he said, "remember how I said that you would have opportunities to make additional money that would be deposited into your account? Well this is one of those."

$100 to sit next to him for 30 min? Easiest money I've ever made.

I got up and walked over to where he was sitting and sat next to him, on his right side. He put his arm around me and pulled me in so that I was leaning into his side. Instinctively, I crossed my right leg over my left to help balance myself, which made me snuggle into him.

He was so much bigger than me.

We were at the scene where Elsa was standing in front of Jason, holding his big black cock as she looked up into his eyes.

"They kind of look like us don't they?" Sir asked.

"How so?" I said.

"Well I'm about a foot taller than you, black, you are a little white sissy. I'll leave my big black cock up to your imagination though," he said.

"Your shorts don't leave much up to the imagination," I joked, trying to be light hearted about the situation.

"Ha, I guess you are right," he said, grabbing what appeared to be an incredibly thick cock through his shorts. "How about this, another $100 if you watch the rest of the movie with your hand on my big black cock."

"$500, and outside of your shorts," I said, assuming that was an absurd enough price to get him to stop.

"Deal," he said.

I turned and looked at him in amazement. I was going to make $600 in 30 minutes. How much money does he make?

He looked down at me, took my left hand, and placed it on his big black cock, outside of his shorts.

I continued to look at him in awe as my hand came to rest on his big black cock. He had it all, the height, the money, the cock. Not fair.

I turned back to watch the movie. Elsa was now on her knees sucking Jason's big black cock. I couldn't help but wonder if Sir's cock was a similar size.

I tried to mentally compare my hand size to Elsa's to gauge Sir's size. I even tried to subtly squeeze his cock to see how far my fingers would wrap around him.

"I think you would be an amazing blonde," he whispered into my ear, breaking the silence.

"Like Elsa's?" I asked.

"Yea Baby, imagine how sexy you would look with that long hair of yours, dyed platinum blonde like a real slut. I'm not sure I could contain myself around you. I tell you what, $1,000 to dye your hair for a month."

"$5,000," I said.

"Deal," he said, "I'll have my friend come over tomorrow to do it for you."

I giggled, "I'm going to make so much money these next 16 months off of you."

"I told you it wasn't going to be only a month or two like you said earlier," he responded.

Shit, he was right. But at the same time, $5,600 in a month is more than I could make with a real job, and who knows what else he will pay for.

Eventually the movie ended and another picked right up. Before I knew it, that one was over too and I had kept my hand on his cock the entire time.

"Do I get another $500 for the second movie?" I asked.

"No, you were the one who kept it there," he said. "Well it's getting late, time for me to go to bed."

Sir stood up, my hand fell off of his cock as he did so. I was now eye level with his hard big black cock as it stretched the limits of his basketball shorts.

He grabbed me by the hand and stood me up, giving me a hug. I could feel the entire length of his big black cock press against my stomach.

"Just so you know, there is one thing that I won't pay you for," he said.

"What's that?" I asked, looking up into his eyes.

"I won't pay to fuck you. You have to beg me for that."

He kissed me on my forehead and turned to walk upstairs. I stood there in silence, in shock. In what world would I beg him to fuck me with his big black cock?

I went into my room and got ready for bed. I kept my bra and panties on. As I lay there thinking about the night, I couldn't stop imagining what Sir's big black cock must look like.

My imagination was running wild. I reached for the big black dildo. Could it be this big?

My hand rested on the dildo. It felt like my fingers wrapped further around the dildo than it did his big black cock. Could he be even bigger?

I pulled my little penis out of my panties and rubbed out a quick orgasm with my right hand, keeping my left hand on the dildo. I came so hard I shot cum all over my bra.

I remembered to set my alarm for 6:15 before falling asleep in my lingerie, with my big black dildo beside me.

The next morning I woke up early with an unfamiliar sensation of sensitive morning wood in my panties. I thought back to my dreams from last night, which were full of big black cock. I moaned and reached down to play with myself.

I closed my eyes and rubbed my aching penis through my panties. All I could see were images of Jason Luv's big black cock sawing in and out of Elsa Jean's mouth and pussy.

Then, I remembered resting my hand on Sir's big black cock for 45 minutes. I picked up my pace.

Then, I remembered that I had agreed to dye my hair platinum blonde today, just like Elsa, who loves big black cock

It was too much, I came from rubbing myself in my panties.

I looked at the clock, 6:15, I had 45 minutes to get ready and make breakfast.

From last night and this morning, my lingerie was covered in cum, I needed to get cleaned up.

I took a quick shower, keeping my hair dry so I didn't have to dry it. Then picked out my lingerie for the day. I decided on lacy blue set of boy shorts and a bra. If I didn't do laundry today, I would have to wear a thong tomorrow.

I looked at myself in the mirror, my penis was already hard again from getting dressed.

I shook my head and walked to the kitchen to start making breakfast smoothies and oatmeal.

When Sir came downstairs at 7, I was sitting at the table waiting for him with breakfast on the table.

"Good morning Baby!" He said.

"Good morning Sir, how did you sleep?"

"I slept well, how about you?"

"Same here," I responded.

"Did you try to squeeze that big black dildo into your ass last night or just jack off thinking about your hand on my big black cock?" He casually asked as if that was normal conversation.

"Ummm..." I didn't know how to respond.

"Wow, the dildo on night one?" He said.

"No, that thing is huge," I defended myself.

"Ah so you just played with yourself thinking of my big black cock?" He asked confidently.

"Yes," I mumbled, playing with my oatmeal.

"Don't be embarrassed Ashley, I was thinking of how sexy you are going to look with platinum blonde hair last night when I was jerking off."

I didn't respond, I just ate my oatmeal.

"Alright I just worked out, need to go take a shower before my first meeting. Your hair appointment is at 9 by the way," he said before getting up from the table and going upstairs.

I cleared the table and did the dishes. It was only 8, so I decided to get some sweeping done. Next think I knew, it was 9 and the doorbell rang.

I was embarrassed to answer the door, but it turned out the lady was trans and was a total pro. She showered me with compliments about my hair, my body, and my lingerie the entire time.

Before leaving she gave me her card and said not to hesitate should I ever want a tutorial for makeup.

The whole process took about 2 hours, and since we did it in the kitchen, I haven't seen what it looked like. I walked into the bathroom to see myself in the mirror.

Staring back at me was a sexy girl with platinum blonde hair. I really liked how it laid flat when she ironed it too. I giggled at how much of a bimbo it made me look like.

I did look good though!

I went back to the kitchen and started making lunch, grilled chicken caesar salads. At noon, I was sitting at the table waiting for Sir with lunch on the table.

"Damn!!!!!" I heard Sir say coming down the stairs, "is that Elsa Jean at my table?"

"Thanks Sir, you like it?"

"Like it, I love it baby!"

I blushed. I was happy he liked it. We started eating.

"Two things I was thinking about," Sir starting talking, "after lunch you need to take all of your old clothes and put them in the trunk in my closet. There is a lock on it, so just close it when you are done. Also, you need to order clothes with your $750 stipend. I would like you to take the afternoon to get your order together and I'll review it after dinner."

"What type if clothes am I supposed to order?" I asked.

"Whatever you want baby, you have a sexy style. Only rule, no pants. he responded calmly.

I thought of picking out sexy lingerie, dresses and skirts. I felt my penis twitch to life.

After lunch I cleared the table and started doing the dishes. After completing those chores, I went to my room and gathered up all my guy clothes from my closet and took them upstairs.

It felt weird dumping them all in a chest and locking it. Oh well, it was only temporary.

I walked back to Sir's bedroom.

"Sir, may I please use your tablet downstairs to pick out my new clothes? My laptop is broken and I don't have the money to fix it."

"Did you lock the chest?" He asked.

"Yes, Sir. As you asked," I responded.

"Good girl. Yes, you may use my tablet. Have fun!"

"Thanks Sir."

I turned to walk back downstairs.

"Actually one more thing baby. You have been very obedient through this initial transition. I just wanted to say good job. I rolled this joint for you as a reward. Why don't you smoke it while shopping to get your creative juices flowing," he said.

"Thanks Sir!" I said with a smile, taking the joint from him and turning around to walk back downstairs.

"Damn that is one fine ass baby. Remember, just let me know when you want me to fuck it," he laughed.

"You wish!" I hollered back playfully.

I sat down on the couch and lit the joint, taking a long, slow hit. Damn this was good weed. I felt the high wash over me and my senses heighten. The first thing I felt was my lacy panties pressed against my penis, which was betraying me again, twitching back to life.

Something about the combination of weed and panties, it got me going.

I picked up the tablet and turned it on. I was greeted with the last thing the tablet was used for, Blacked.com.

I moaned as I scrolled through images of scenes where tiny white girls were introduced to big black cocks.

After a few minutes, my penis was now rock hard in my panties and I was incredibly horny. I guess I could watch one of these in the background while I shopped. Sir would never would know.

I put on a new one, 3 white girls, including Elsa Jean, and 3 black guys. I couldn't help but rub my penis through my panties while I watched.

Before I knew it, I had accidentally cum in my panties.

I hated how quick I always was, but this was like embarrassingly quick, like 30 seconds. The girls in the video had barely even dropped to their knees and I had already cum in my panties.

I looked down, cum was leaking through the lace, I had to change before Sir saw me like this.

I got up and started walking to my bedroom. Before I made it into my bedroom, Sir came downstairs.

I ran into my room and shut the door. I wasn't sure if he saw me.

Knock knock knock, "are you alright in there?" I heard him ask.

"Yes, I am fine, I just...I just..." I stuttered.

He opened the door, "you just need to change because you came in your panties as soon as the guys in your little movie pulled out their big black cocks?"

I blushed, "yes," I admitted staring at the floor.

"It's ok baby, this is all new to you. I'm glad you are enjoying it. The best part of your job as my sissy maid is that besides meal time, you will have plenty of time to explore. This is exactly what you should be doing," he said.

"Ok, but can you let me change now?" I asked.

"Of course! Maybe something with stockings this time? For me?" He playfully pleaded before walking into the kitchen.

I shut the door and looked through my options. I forgot that all I had left were thongs. I landed on a black thong with an embroidered black rose on the front and the matching bra. Since the embroidery was in black, it felt like the least girly option.

I slid them up, the thong felt strange nestling in my butt cheeks. But it did feel kind of good too. It felt tight. The front cupped my penis so well.

I looked at the stockings, why not? I rolled up a the thigh highs and stepped into my heels. I'm not sure why, but while I wasn't wearing heels in my purple lingerie this morning, it seemed silly to wear stockings without heels.

I walked looked at myself in the mirror to make sure I looked good and walked out of my room.

"Wow, there she is!" I heard Sir say from the kitchen.

"I didn't think you would be down here still," I said.

"And miss seeing your debut in a thong and stockings? Not a chance. Good call on the heels too. So what do you think about the thong?"

"I...um...I kind of like it," I said.

"I told you! I thought you might!" He said, "I was worried about the front not being able to hold you since it is even smaller, but you are just so tiny down there."

"Well I'm not hard right now," I said.

"To be fair, you did just cum in your panties," he said, "come here."

He held out his hand.

I walked over to him and took it. He pulled me close. Looking down and staring into my eyes, he took my hand and placed it on the outside of his pants, over his big black cock.

I felt the familiar and unthinkable girth from last night.

"Do you think my big black cock could fit in a thong like you are wearing baby?" He asked.

"No, Sir, you are much to big. I'm not saying that you could fit. I'm just saying that this thong might not fit as well when I'm hard and my penis is bigger."

"Bigger is relative, wouldn't you say," he responded, "you at your biggest is still significantly smaller than my smallest, right?"

"Yes, you are right," I agreed.

"Now," he said, "lets take a look at you."

He pushed me back a step and looked down at my crotch. I followed his gaze and looked down.

To my dismay I was hard as a rock again and my erection was pointing straight up. However, me penis was not big enough to make it above the elastic of the panties.

"See, even at your biggest," he said using air quotes when he said the word biggest, "you are still small enough to fit neatly into a thong. Now I have to get back to work. Have fun watching big black cocks and shopping all afternoon."

I wasn't going to do that. I said to myself. Well maybe just for a little bit.

I walked back over to the couch and picked up the tablet. I stared at the giant TV. Three cute white girls kneeling together, with 3 black men with big black cocks looming over them. How could I not watch?

I pushed play and my penis immediately twitched in my panties.

Alright, well I cant just watch this all afternoon, I need to at least be productive and order some clothes.

I googled "sexy lingerie" and came across a site called Wicked Temptations.

I took a hit of weed. Why did I google "sexy lingerie"? I thought to myself. Why didn't I just google "women's clothes"?

I guess it was fun. Lingerie felt taboo and kinky. Women's clothes might just be awkward.

Also, Sir clearly liked me in lingerie and he was being really nice to me.

I started looking through all of my options. There were whole categories that I had never heard of before, chemises, camisoles, bustiers, the list went on. I spent the next hour going between the movie I had on the TV and my options.

Whenever I found something I really liked I would add it to my cart. Every time I did, I could feel my penis twitch. I marveled at the options women had.

When I finally came up for air I had over $900 in my cart. I guess there was a lot I liked.

I looked at the clock, I needed to start working on dinner.

When 7pm hit, I was sitting at the table with dinner ready and a bottle if wine, waiting for Sir.

He came down carrying a small box, complimenting how good dinner smelled.

We ate and made small talk for a bit, but then he took control of the conversation.

"Did you pick out some clothes?" He asked.

"Yes I did, I'll get the tablet for your approval."

I got the tablet and handed it to him.

"This is $150 over your stipend," he said.

"I know, but I couldn't help myself. And 16 months is a long time, I want to have different options," I said.

"I tell you what, we will just take the $150 out of the $500 you made from touching my big black cock last night," he said before pushing order.

I'm not sure I would have agreed to that, but it was too late.

"You seem so excited," he said, "I paid extra for overnight shipping, on me."

He winked at me.

"Thanks Sir. what's in that box?" I asked, nodding my glass of wine at the box sitting next to him.

"An opportunity for you to make some money," he said.

"Oh yea, I would like that!" I responded eagerly.

He slid the box over to me, and I quickly opened it.

"What are they?" I asked, staring at 3 silver objects that had different color jewels on the flat end. One pink, one purple, one white.
<hr pg="3" />"They are butt plugs," he said calmly.

"Butt plugs?"

"Correct. I am offering you $250 a day to wear them all day and night for the next month," he said.

He could see me trying to do the math. He laughed.

"That's $7500 baby," he said.

"That's a lot of money. But I've never had anything in my ass before. Well once my ex put her finger in there when she gave me head," I said.

"And what happened when she did?"

"I came, but that was from the head."

"Sure it was baby. The only other part of the deal is that I get to put it in the first time," he said.

"$7,500 is a lot of money, and they are pretty small," I said, thinking out loud, "ok deal."

"I figured as much, what color do you want to wear first?" He asked.

"Ummm...I guess all of them go with black...how about the purple one?" I decided finally.

"I thought you would choose that one, now bring it over to me baby," Sir demanded.

I picked up the purple one, it was surprisingly heavy, and took it to him.

"Why don't you suck on it so its wet," he said.

I stood in front of him and opened my mouth to get it wet. It felt bigger than it looked now that it was in my mouth. I started to get nervous. Why did I agree to this? Oh yea...$7,500.

I took it out of my mouth and handed it to Sir.

I was standing in front of him in my lingerie, while he sat. He took my hand in his and ushered me to lay across his lap.

I felt my soft penis press against the bulge of his big black cock. My penis twitched.

I felt his big fingers slip inside the back of my thong and he moved it to the side so the thong was resting on my right butt cheek, giving him full exposure to my asshole.

"Suck on my finger," he said, presenting his finger to my lips.

Without hesitation I sucked on his finger. Once it was nice and wet, he took his finger out of my mouth and rubbed it on my asshole, making it wet.

"Damn, I can't wait to fuck you baby," he said.

I moaned as he pressed the butt plug into my ass.

"Ugh, it feels bigger than I expected," I said.

Once he popped it all the way in, he moved my thong back into place and gave my a light spank.

"All done!" He said, "you took it like a champ. Can I show you something quickly?"

"Yes Sir," I said, standing up in front of him.

He grabbed the waistband of my thong and pulled it down. My tiny, but hard, penis sprang to life.

"Three things I want you to observe. First, your penis wasn't hard before this plug went into you. Second, you called the plug small, but it is thicker than your own little white penis," he said holding one of the other plugs next to it, "and third, my finger that you sucked on is the exact same size as your little white penis. Imagine what it will be like to suck my big black cock."

I moaned. My penis twitched right in front of him. There was no hiding that my body reacted to the idea of my lips wrapped around his big black cock.

I stared at the floor, which meant I stared at my little, but painfully hard penis as he held his index finger next to it.

He was right.

"Want to see a fun trick?" He asked.

"Sure," i said hoping for the embarrassment to end.

"Now this apparently only works with really hungry sissies, but lets give it a try."

He reached behind me and grabbed the base of my butt plug with his right hand, and held my hip with his left hand to steady me.

"Now, watch your little white penis," he directed before moving my plug in a circular motion.

I moaned as I felt the part of the plug that was inside of me rotate inside of my ass. He pushed the outside of the plug towards the ceiling which put pressure against my prostate.

I moaned again.

"There it is!" He said, "your little white penis is leaking from just your plug. It worked!"

I moaned in embarrassment. My little white penis betrayed me.

Instinctively, my hands went up and covered my mouth as I felt another involuntary moan coming on.

My knees went week, but Sir let go of the plug and steadied me with both hands.

"Easy Baby," he said, "you are clearly very thirsty."

"What do you mean by thirsty?" I asked.

"It just means you are an extremely sexual person and your pleasure spots are very heightened. This plug is just the tip of the iceberg for you baby," he said before pulling my thong back up over my little white penis and putting the back of my thong back over my ass.

"I'm not thirsty," I pouted.

"Baby, your little white penis is leaking like a faucet from your pretty plug. Now clear the table, do the dishes, and lets smoke a bowl. You can pick out the movie again tonight," he directed.

I wanted to cry. This was a lot for me. I stood at the sink, doing the dishes, and tried not to cry. How had a gotten myself here? Did I enjoy it? Was I just trying to get money? Why was I was so unfortunate to have such a small penis? Why was my little penis always so hard in my panties?

I thought through it. Maybe I did like it, and maybe that was OK. Maybe this was unlocking something that I wasn't aware of. Maybe I should just enjoy it and see where this goes, I was at least making money.

I walked back into the TV room confident. I needed that internal pep talk.

"I love the way that plug makes your ass sway when you walk. Come sit next to me baby," Sir said.

"$10," I said.

"You drive a hard bargain, but deal," he laughed.

I sat down next to him. On impact, my plug was forced deeper into me than it was previously.

I moaned.

"I bet that made you leak a little cum, didn't it sissy?"

I touched the tip of my penis through my panties, it was wet.

"I think so, or that might have been from earlier. It's hard to tell," I giggled.

He handed me the tablet while he started to pack a bowl.

"Also Sir, I was hoping we could set up my savings account so I can track the money going in."

"Absolutely Baby, go get your phone and I'll give you access to it."

I got up and walked into my bedroom. My little penis twitched at the sight of the dildo on my bed from last night. I grabbed my phone and walked back to him.

I couldn't help but moan as I sat down, more gingerly this time.

He took my phone and handed me the tablet. I scrolled through the Blacked library and landed on one of Elsa Jean where she was going to fuck her friends brother. From the preview it looked like he had a torpedo of a black cock.

"I'm ready when you are Sir," I said.

"Perfect, here you go," he said handing me my phone.

True enough there it was, a savings account with cash already in it. He even already had the $250 from today's wearing of the plug there.

"Want to see how it works?" He said.

"Yes, of course," I responded.

"OK then, sit on my lap for this movie," he said.

"$100?" I asked.

"Deal," he said, reaching for his phone.

I stood up and backed up into him. I put my hands on his knees and slowly sat myself down on his lap.

Oh my god, I was sitting on his big black cock. I felt it start to harden. His big black cock was forcing the plug deeper in me.

"Ding" my phone beeped. I opened my app, $100 had been added.

I smiled. As long as he kept finding me sexy I was going to make some really good money. I leaned back into Sir's big body. Even when I leaned all the way back while sitting on his lap, I still didn't make it to the top of his shoulder.

I felt his big black cock harden more. It was so powerful that it lifted me up slightly as blood rushed to it.

He grabbed my hips and grinded my butt onto his big black cock.

"Look at what you are doing to me baby," he whispered into my ear.

Playfully, I pulled my the elastic of my thong forward. A string of pre-cum went from the tip of my penis to the material of my thong.

"And you me," I said.

"So thirsty," he laughed.

Once the movie ended, my butt had started to go numb. Without thinking I leaned forward and reached behind me to rub my butt. However, when I did that I accidentally rubbed his big black cock with the back of my hand.

I stopped once I realized what I was doing.

"You don't need to stop baby, I don't mind," he whispered in my ear.

"I wasn't trying to rub your big black cock, my butt just hurts," I said.

"Well if your sexy ass hurts, why don't you sit next to me and keep rubbing my big black cock," he suggested.

"How much?" I said.

"I'll give you 3 options, $10 for sitting next to me and resting your hand on my big black cock over my shorts, $50 for putting your hand down my shorts and holding my big black cock, $200 for taking my shorts off, sitting on my lap, and holding my big black cock in front of you."

I bit my lip and thought. $10 didn't seem worth it. Really, what was the difference between holding his big black cock in his shorts and doing it while sitting on his lap. My butt won't hurt anymore if I'm not sitting on his big black cock.

"Ill go with the $200 option," I said.

"Great, now take my shorts off," he directed.

I heard the ding of another deposit being made as I got down on my knees in front of him, tugging on the end of his shorts. He wasn't lifting his butt to help me.

"Try taking then off from the top," he said.

I scooted closer to him and reached up to grab the waistband. I pulled them down around his ass. I leaned back and slowly pulled them the rest of the way down.

I couldn't help but to watch in awe as inch by inch of his big black cock was revealed to me.

Instinctively, my jaw kept dropping further and further as each inch of his big black cock was revealed.

Once I got the waistband of this shorts to almost his knees, I could tell that the head of his big black cock was the last bit still in his shorts.

His big black cock had to be over a foot long.

I gave one final tug and his big black cock was freed from the confines of his shorts. Since he was hard, his big black cock sprang upwards and slapped me under my chin, closing my jaw that was open in amazement.

He laughed.

I reached up and rubbed the side of my jaw. It kind of hurt!

"Sorry about that baby, you can see it is pretty strong, sorry you felt it's wrath!" He laughed.

"Your big black cock is...is...something else," I said, staring at it intently.

I knelt there in front of him, mesmerized by the big black cock that stood at attention, inches from my face.

"I just didn't know they could be this big," I said.

"I know you have seen plenty of big black cocks in porn, but I'm sure seeing it in the flesh is a whole different experience," he said calmly, reached forward and brushing my hair out of my eyes, tucking it behind my ear.

A minute or so passed.

"Don't worry baby, take as much time as you need. I can imagine how this changes things for you. You aren't the man you thought you were. How could you be a man when there are black men like me with big black cocks that dwarf you? How could you ever truly pleasure a woman with that little penis of yours? Not only that, but how can you call yourself a man when you are kneeling in lingerie before a black man?"

I couldn't take my eyes off of his big black cock. It towered over me. Not only was it long, but it was incredibly thick. It had big thick veins running up the shaft like a powerful muscle. Every part of it was powerful.

"Well either suck it or sit on my lap sissy," he said, breaking the silence, snapping me out of my trance.

I blinked and shook my head. What just happened to me?

He reached down, putting his hand on my cheek. With his thumb, he wipes a string of drool from the side of my mouth.

"Like I said, you are one thirsty sissy."

"No I'm not sir, it was just, your big black cock hit me on my chin and knocked some saliva out," I protested.

"Sure, just come sit on my lap," he said, if ignoring my protest.

I swung my leg over his big black cock and sat down on his stomach. It was much more comfortable as I sat up straight, his big black cock sticking straight up, obscenely, in between my legs.

Sitting in this position, my hard little white penis, encased in my panties, pressed against his big black cock. I couldn't believe how much bigger he was than me.

"Don't forget you have to hold my big black cock to get the money," he whispered into my ear.

I reached down with both hands, I felt like a pilot holding a joystick. Even with both hands around it, I could barely reach around it.

The next movie had started, but I kept trying to sneak glimpses of my soft white hands around his big black cock. My painted nails looked so sexy and feminine around him.

"It's OK, you don't have to watch the movie, your hands feel really nice," he said as he lightly thrusted his hips up, essentially simulating me jacking him off.

"I...I...I..."

"It's OK Ash, a sissy like you is understandably overwhelmed in situations like this," he said, commenting on my inability to form sentences because of the power his big black cock had over my mental state.

He kept thrusting up and down. I didn't care. It was hot. My little white hands, painted nails and all, holding onto his big black cock.

I'm not sure when, but eventually he stopped thrusting, but I kept going. I worked my hands up and down, exploring the length of his big black cock.

As I slowly jerked him off, Sir reached around me and out a bowl of weed up to my mouth and sparked his lighter. I inhaled as I continued to rub my hands up and down.

I was in my own world. Everything around me disappeared. Well, everything except for his big black cock.

I was so horny. I pulled his big black cock against me and thrusted my panty covered, little white penis, against his big black cock.

I shivered, almost cumming right then. Oh my god, that was incredible. I went to do it again, but Sir broke my trance.

"Alright well I need to go to bed," he said giving my ass a slap, "do you want to take my tablet into your room so you can keep watching?" He asked.

"What? I thought we were..." I pouted.

"Thought we were what?" he said. "Thought I was going to let you hump your little white penis against my big black cock until you came in your panties?"

I blushed. It sounded so ridiculous when he put it like that.

"No sir, I was going to keep jacking off your big black cock too," I protested.

"I don't want a handjob, we aren't high schoolers," he stated, before standing up, forcing me to my feet too.

I turned around so I faced him. I reached out, grabbing ahold of his big black cock. I stroked him back and forth, looking up into his eyes.

"Please, let's keep messing around, I need to get off," I said.

"Then beg me to fuck you in the ass," he said matter of factly.

My ass quivered at the thought.

"No, I'm not gay," I said.

He laughed, "you are standing in lingerie, soaked in precum, jerking off my big black cock. You are one thirsty and confused sissy. To be continued..."

He leaned down, giving me a deep kiss. I moaned as his tongue swirled around in my mouth.

I melted into him. But Eventually he, broke the kiss, "good night!" He said, pulling away and heading upstairs.

Frustrated, I headed to my room with his tablet In hand.

Looking in the mirror, I noticed how wet my panties were. I needed some dry underwear, I picked out a light purple lacy thong, then changed my bra to match. My penis twitched at the feeling of a new thong. I was so excited for the rest of my clothes to get here.

I climbed into bed and put on yet another Blacked video. I couldn't get enough.

After a few minutes, I felt myself getting really horny again, and with it came an itch in my ass.

I reached down to scratch it and felt the plug. I wiggled the plug around, it wasn't deep enough to scratch it. I tried to push it in deeper, but I didn't want the whole plug to get sucked into my ass, so I took it out and replaced it with 2 fingers.

As deep as I could go, the itch always felt like it was just a centimeter deeper. I moaned in frustration and lust as I looked down to see dark purple spot on the front or my panties.

I was leaking pre-cum again.

I pulled my fingers out and tried to pleasure myself by rubbing my penis. However, that seemed to only make the itch get stronger.

I was writhing and moaning in sexual frustration on my bed.

How could I scratch this itch? It kept getting stronger and stronger as I watched the little blonde on screen get completely owned by a black man on my TV.

I turned my head, closed my eyes, and rubbed my penis feverishly, but it kept getting worse. No relief.

I opened my eyes and saw the big black dildo sitting on my night stand.

I picked it up, maybe this would help? No one would need to know.

I licked it before positioning it at my asshole. I felt the tip rest against my tight hole. The itching feeling got worse. In a mixture of arousal, frustration, and embarrassment, I closed my eyes and pushed. My ass was so tight it wasn't allowing the foreign intruder.

I moaned and pushed harder on the base.

POP. I gasped as the bulbous head slid in. If took my breath away. I laid there, motionless, as I adjusted to the big black dildo.

My ass felt numb from the initial pain of entry, but as I caught my breath, the pain subsided and I began to feel that itch in my ass, which was just slightly deeper than where the dildo laid rest inside of me.

I closes my eyes and moaned as I pushed the dildo in further, determined to reach the itch. However, it proved to be out of reach, the deeper the big black dildo went, the deeper the itch moved.

Before I knew it, I was bottomed out on the big black dildo. I moaned. I felt so full as I laid there, marveling at my achievement. At that moment, I felt the itch again, but it was no longer deep inside me, but rather on my stretched asshole. I pulled the dildo out slowly, the itch subsided as the veiny dildo rubbed against my asshole. But this satisfaction was fleeting. As soon as I got to the head, the itch went deeper, forcing me to slide the big black dildo back in.

In and out I went, chasing the itch. I increased the speed, but to no avail. The faster I slammed it in or ripped it out, the itch always seemed one step ahead. I switched positions, kneeling on my bed, bouncing up and down.

This helped. I started to catch up. I anticipated the itch. I took control of this feeling and rode the big black dildo harder and faster. I arched my back to hit new places, the itch couldn't hide. I rode and rode until BAM! I closed my eyes and squealed in delight as cum shot through the lace of my thong.

I covered my mouth, hoping that Sir didn't hear what just transpired as I rested, catching my breath, fully impaled on the dildo, catching my breath.

I reached down, admiring the large pool of cum that my little white penis shot through my lacy panties.

Was that my best orgasm ever? I hadn't even touched me little penis, but the result was hardly debatable. I don't ever remember producing that much cum.

I wonder how cum Sir shoots out of his big black cock. His balls are enormous as well. I assume it would be a ton of cum.

My little white penis started to twitch back to life as I imagined myself gulping down stream after stream of cum from his big black cock.

Wanting round 2, I moaned and lifted my ass up on my big black dildo before sliding back down. My ass was sore. I rode slowly, enjoying the pain and pleasure. Somehow the pleasure outweighed how sore my poor little ass was though.

What else would bring me pleasure? I thought as I slowly rode up and down on my favorite new toy. I closed my eyes and reached for my breasts, giving them a squeeze as I had seen girls do in porn.

I'm not sure if it gave me pleasure, but I moaned, feeling my sexy lace bra.

I kept riding, kneading my bra covered tits until I came again. Hardly any cum this time, but that is to be expected given how small my balls are and how much cum I already expelled.

I leaned forward, resting my head onto my pillow. Next thing I knew, my alarm was going off.
<hr pg="4" />As I woke up, I felt my big black dildo still lodged inside my ass.

I moaned, reaching down to remove the intruder. I gasped as the last bit of the head popped out of my ass.

Oh my god. I felt empty. Thinking about the feeling of emptiness made my little penis twitch to life. I wanted to cum, but I knew I had to get breakfast ready.

I got out of bed and started walking to the bathroom, still in my lingerie and heels from the night before.

My ass was so sore. I could feel the aftermath of last night with every step I took.

I showered, spending extra time to clean my ass and penis from the lube and cum.

Once I felt like I was all cleaned up, I wrapped a towel around me and walked back to my room.

"Good morning Ash," Sir said, already sitting at the table.

"What time is it, Sir?" I said, worried it was 7 already.

"Don't worry baby, its 645, you have plenty of time," he said, not even looking up from his phone.

I hurried back to my room and grabbed a fuchsia thong, matching bra, and white thigh highs.

I looked at myself in the mirror to make sure I looked good. I looked hot, but got embarrassed seeing the absurd dildo on my bed. I didn't want Sir to see it, so I quickly pulled my blankets over it before running to the kitchen and making him an egg and coffee.

Once ready, I hurried it over to him, setting it down at 659.

"Cutting it close sissy," he said.

"Plenty of time, Sir," I responded, giving him a smile before sitting down across from him.

"Do you have one of your plugs in?" He asked.

"Shoot, no, I totally forgot. I'm sorry, is it too late to put one in?" I pleaded.

"Well when did you take it out? Just to shower?" He asked.

I thought back to last night. How I removed my jeweled butt plug and replaced it with my big black dildo.

"Umm...yea...I just..."

"Dont lie to me Ash. Why are you looking at the table, look me in the eyes," he interrupted.

I raised my head and looked across the table into his eyes. He would know if I lied.

"I took it out last night," I said, telling him the truth.

His eyes looked angry, "that wasn't the deal, Ash. You owe me $250 for not leaving it in all night."

"I'm sorry Sir, I didn't think it would be a problem. I was just so horny. I had to take it out."

"Why did you have to take it out Ash," he questioned.

I looked down at the table and blushed. My thong rested against my sore asshole reminded me of my actions.

Too embarrassed to look at him. "I had to take it out to put the dildo in," I answered quietly.

"Speak up sissy," he demanded, growing aggressive.

I looked him in the eyes, "I had to take my butt plug out so I could ride my big black dildo," I said.

"Wow, is that right? I guess that is a fair rule. As long as your plug is replaced by a big black dildo or my big black cock, you can still earn your $250 for the day. Does that sound fair?"

"Yes Sir, that sounds fair," I said, Not believing what I just agreed to.

"Good. Well now thats settled, go get a plug," he instructed before taking a sip of coffee.

I grabbed the pink one as it was closest to my fuchsia lingerie and brought it back to him to put inside me.

He laughed, "sure, I can put it in if my little sissy prefers that."

I blushed. I guess the only rule was that he did it yesterday, not everyday.

He stood up and out one hand on my back, bending me over the table. Instinctively, I laid flat over it and reached out across the table, sticking my ass out with the help of my high heels.

I turned my head and noticed his index finger was at my lips. I opened my mouth and sucked on it, assuming he was going to use it as lube.

I continued sucking his finger as he used his other hand to move my thong to the side.

Once sufficiently wet, he removed his finger and rubbed it on my sore asshole.

He popped the plug in.

"Wow, we might need to get you some bigger plugs, your pussy is already adjusting to accommodate larger things," he said before giving my ass a light tap.

I couldn't argue. My ass was still a sore, but i couldn't tell if I was just still a little numb or if I didn't really feel the small plug.

I sat back down, embarrassed.

"Are you excited for your clothes to show up?" He asked, kindly changing the subject from me riding a big black dildo all night.

"Yes, Sir, thank you for buying them for me," I responded quickly.

"I couldn't help but notice that you only bought lingerie, you really are very thirsty."

I blushed. He was right. Why did I only buy lingerie?

My penis twitched in my panties.

"I'm not thirsty," I protested, "I just thought that's what you wanted."

"I mean it is, I love my sissy in sexy lingerie, I just didn't know you liked lingerie so much too. Which piece are you most excited about?" He asked.

"Probably the dark purple bustier with matching thong and garter," I responded immediately.

"That was quick!" He laughed. "I assume that is what you will want to wear when you beg me to fuck you with my big black cock?"

"I'm not going to beg you," I said quietly.

I could feel my face turn red as I thought through the proposed scenario of not just getting fucked by his big black cock, but the embarrassment of getting on my knees in lingerie and begging him to fuck me. Like I needed his big black cock so bad that I couldn't live one more second without him inside of me.

I bit my lip. I couldn't get his big black cock out of my head and he knew it. Especially once he saw the growing wet spot in my panties.

The door bell rang, breaking the growing sexual tension.

"My clothes!" I squealed, getting up quickly and scurrying to the door:

I was so excited about my package that I forgot about my little boner in my panties giving away how horny I was.

I could hear Sir laughing about my excitement from the other room.

Luckily, the delivery guy was no longer there as I opened the door. Whew, I didn't think that through!

I bent over to pick up the box and Sir let out a cat call.

"I am going to absolutely tear up that tight sissy pussy soon!"

"Yea yea yea," I responded coyly, "maybe I will need your big black cock deep inside of me later today. Or maybe I will never need your big black cock since I have my amazing big black dildo that you so nicely gave me!"

I took my box into my room and started going through it. Everything felt so sexy, I stepped out my panties and slid up a purple lacy though and pulled the matching bustier over my head. The tight hug of the bustier made me feel incredibly feminine. I moaned as i pulled the garter straps tight to snap onto my white stockings. I loved how tight they pulled against my thighs.

I felt sexy, and proud of how I looked in the lingerie. I wanted to show Sir to see what he thought. I bet I would make his big black cock hard just from him looking at me. I realized that I took pride in being able to turn him on.

I walked out to where he was eating breakfast, but he had already gone upstairs to start working. Bummer!

I felt a familiar twinge in my ass. I was already horny from the conversation with Sir earlier, but the outfit really put me over the top. I guess a little ride on my big black dildo is in store!

I moaned, part in anticipation and part in embarrassment as I gave into my urge and crawled onto my bed, picking up the big black dildo with both hands. I stared at it in awe as I squeezed some lube on the tip before jacking it off to even it out.

On my knees, I reached back to move my thong to the side before pulling out my plug and positioning the tip of the big black dildo at the entrance of my ass. I could feel how sore my ass was from the onslaught I gave myself last night as I slowly lowered myself down, one inch at a time.

I noticed how the soreness actually felt good. I thought it would hurt, but in reality it just heightened my senses. It was a good sore. A soreness that not only reminded me of the pleasure from last night but my current state of pleasure. I kept working my way further and further down.

I felt full. I leaned forward, still on my knees, but resting my head on my pillow to catch my breadth and adjust to the size of my big black dildo before I started to ride the big black dildo in search of another sissygasm in my new lingerie.

I moaned into my pillow. My whole body felt so good. I laid there as the pleasure washed over my body. The calm before the sissy storm that I was about to embark on.

I was so caught in the moment that I didn't hear Sir come into my room.

"Damnit Sissy!" I heard him yell, snapping me out of my euphoric state.

"After your comment earlier about not needing the real thing since you have your dildo, I realized it is time to remove that crutch from your sissy journey," he explained as he crawled up on my bed.

He roughly pulled my legs out from under me so I switched from kneeling forward to laying down face first on my bed. He got on top of me, his weight completely immobilizing me.

"Please sir, just let me keep my big black dildo. It's the only way I can have a good orgasm these days," I begged for mercy. "I haven't cum yet, please!"

"Fuck no Sissy," he said before I felt him grab the dildo and in one motion, rip it all the way out. Cold air hit my asshole, I felt so empty.

"Please put it back in Sir, please, I'll do anything! Just let me cum!"

I couldn't see him, but I heard a zipper. Was he pulling his big black cock out?

My question was answered as with one hand he grabbed my ass and with his other hand he slapped his big black cock onto my ass, laying it along my crack.

It felt thick and heavy. And warm! Almost hot. I wondered how different the heat of his big black cock would feel inside of me compared to the room temperature black dildo.

"If you want to cum again sissy, it will be from my big black cock," he said while rubbing his big black cock up and down my ass, holding my hips in place with his strong hands.

I felt so tiny, so vulnerable, so feminine. He could take me right now if he wanted to, but he didn't. He wanted me to beg him.

I lifted my ass to meet him as he continued to tease me by grinding against my ass. I wanted to get off, I wanted him to fuck me. I just couldn't bring myself to beg him, it would be so humiliating. I could never recover from that sort of humiliation, I would always know what a slut I had been for a big black cock. And worse, he would hold it over me forever.

I kept trying to meet his thrusts to tempt him, letting him know he could fuck me, but he wasn't taking the bait.

"You know what you need to do if you want me to fuck you with my big black cock," he said slapping me on my ass with his big black cock as he said big - black - cock.

I moaned. Closing my eyes as my mind raced, weighing my options as I felt Sir on my backside and his big black cock on my ass, hardening by the second, ready to fuck me into a sissygasm.

I wanted to cum. I needed to cum. His big black cock would feel so good.

Fuck it.

"Ok sir," I said meekly.

"Ok sir, what?" He responded.

I took a deep breath. My whole life was about to change. If I go through with this I will forever be the sissy who let a black man fuck him.

"Sir, please f..." I started, about to beg him, but he interrupted me.

"Hold that thought sissy," he said, "lets get you ready."

He leaned back, and pulled my hips up so I was in position for doggy style. His big black cock laid across my lower back as he reached around and set up his phone so it was facing me on selfie mode, recording my face, but so I could see myself.

"Ok its your time to shine sissy," he said, rubbing my back with his strong hands, encouraging me, "beg into the camera."

"Can we please not record this Sir?" I asked.

"Not a chance Sissy. This is important. I can't risk you changing your mind and accusing me of rape or some bullshit. This is irrefutable evidence that you begged me to fuck you into sissy heaven."

I closed my eyes and took a deep breath before lifting my head up to look directly into the camera.

"Please Sir. Please fuck me with your big black cock."

He didn't start fucking me, he just kept rubbing my back. I took that as a sign to continue.

I stared deep into my eyes on the phone.

"Please sir. Make me your big black cock addicted sissy. Since you have moved in, I have dreamt about this moment when I could finally feel your big black cock inside of me. I need your big black cock more than you could ever know. Make me your sissy and I will be yours to do with as you please. Please let me be your sissy. Please fuck me with me with your big black cock. My sissy pussy belongs to you."

I guess he felt like I sufficiently begged him. I felt him position the tip of his big black cock at my ass. He held my hips tight so I wouldn't move forward, and he pushed his hips towards me slowly but firmly.

I saw my eyes get huge in the camera as the mushroom head of his big black cock pressed into my tight ass.

"Oh my god," I moaned as he pressed inch after inch of his big black cock into me.

"Your big black cock is so big. It feels so good inside of me Sir."

He knew what he was doing. Not only was he blessed with an amazingly big black cock, but he was a master of his craft.

For every inch he pressed into me, he pulled a half an inch out. Letting my body adjust to his size while working his big black cock further into me.

He wasn't even fucking me yet and I felt like I could explode from pleasure.

I buried my head into the pillow.

"Oh my god, your big black cock, oh my god. Oh my god. Sir. You feel so good. This is incredible."

I was a babbling idiot. His big black cock was taking me to a place I had never been. I felt so good. It felt so natural. Not just his big black cock inside of me, but being in lingerie, dolled up for my man.

I had been a shitty lay as a man. Even just a minute in, I knew that now. I always was extremely sexual, I had just been in the wrong position until now. I was a shitty lay as a man because I wasn't a man. I am a sissy. This is sex for me.

Another inch in, another half an inch out, another inch in. I moaned.

With one hand I reached down to grab my painfully hard little penis and rub it.

Before I could pull my little white penis out of my panties, Sir stopped me. He grabbed my hand firmly and redirected it back above my head.

"You don't touch your little white penis sissy. Not during sex. Never. I will lock your little white penis is a cage if I ever catch you playing with your penis."

"Yes Sir," I moaned, "whatever you say Sir, I am your sissy to do with as you please. I meant what I said. Please just never stop fucking me with your big black cock. It feels so good."

"That's a good sissy," he said as he started rubbing my back.

I noticed he had stopped moving. I felt so full. A sense of pride washed over me as I successfully had the entirety of his big black cock in my sissy ass. I was stretched to my limit. It felt like my asshole was stretched as wide as it possibly could.

We stayed like that as I caught my breadth and adjusted to his size. Like I said earlier, he was a master of his craft. He read me perfectly. He could sense that I needed a minute to prepare for what was coming next.

He wanted to give me time to not only physically adjust, but mentally adjust. Let it sink it to my core memories that I was fully impaled on his big black cock. That he was my master, and I am his sissy.

My senses were so heightened. I felt the cold straps of my garter stretched tightly against my thighs, my incredibly little and hard penis trapped in the confines of my panties, and most importantly, I could feel every ridge and vein of his big black cock stretching me to new capacity.

I was so horny. I'm pretty sure that if a gust of wind hit my little white penis through the lace of my purple panties, I would erupt into the biggest orgasm of my life.

Sir didn't move. He just knelt behind me, fully inside of me. He continued to rub my back with his large hands in encouragement and comfort.

He was going to make me fuck myself on his big black cock. I shifted my weight forward, pulling myself off of a few inches of him before rocking back into him. Slowly of course as my sissy pussy still wasn't used to his size.

Forward, backwards. Forward, backwards. I worked myself on his big black cock with care and intention. I could feel myself inching closer to sissy bliss as the rigid head of his big black cock continued to rub slowly along my prostate.

I moaned and rested my head down on the pillow, continuing to work my ass along his big black cock.

His big black cock was so strong, it felt like it was holding my ass up high in the air in perfect position for him to do with as he please.

"Oh my god. Sir. Your big black cock feels so good," I cooed as I continued to work his big black cock to the best of my ability. "Please fuck me. Fuck me with your big black cock. Make me cum with your big black cock. Please take me. Take me however you want. I am your sissy."

On queue, he reached under me and lifted me up. I was still fully impaled on his big black cock as he spun me around so I was now on my back.

I moaned as I spun around his big black cock.

He laid me gently on my back. Instinctively, I lifted my ass slightly and wrapped my legs around his lower back, insuring his big black cock remained deep inside of me.

He leaned forward and gave me a deep kiss. His tongue dove into my mouth and I did my best to respond, swirling my tongue along with his. Even his tongue was so much larger than mine.

I am no man. I am his sissy. I thought as I moaned into his mouth in a fit of passion. My hips meeting his as I tried to pull his big black cock as far into me as possible.

He grabbed my legs with his strong hands and unwrapped them from around his waist. Keeping one hand on each thigh, he brought them over my shoulders, completely exposing my sissy pussy to him while rendering me completely immobile. I was pinned in this position.

He leaned forward for one more kiss before he started pulling his big black cock out, seemingly taking my insides with him. I moaned at the empty feeling of withdrawal before he unexpectedly slammed his big black cock back into me.

I screamed in pleasure as his big black cock assaulted my prostate. I covered my mouth with one hand in embarrassment. I had never made a noise that loud during sex before. I always thought noises during sex were fake, just part of the act, but in the role of a sissy, his big black cock was forcing noises out of me that were completely involuntary. I loved it.

He growled as he continued to jackhammer my exposed sissy ass. He had me just how he wanted me. I felt my orgasm building with each thrust.

I moaned louder and louder, pinned under this gorgeous black man as his big black cock hammered my sissy pussy. I had lost all control.

I strained to lift my head so I could watch his big black cock assault my pussy. It was so incredibly thick. I loved watching it. I loved seeing the juxtaposition of his thick, veiny black cock going in and out, just inches from my incredibly hard little white penis tucked neatly away in my panties.

How they could both be considered a penis was astounding. They couldn't be less similar.

"Oh my god your big black cock....is....so....fucking....hot!" I squealed in between his thrusts.

My orgasm was building. I was completely lost in sissy la-la-land.

"Make me your sissy. Oh my god. Oh my god. Oh my god I'm about to....your big black cock....oh my god. Your big black cock. Please. Don't stop. Oh my god. Your big black..."

I came. I came harder than I had ever cum in my life. My whole body shook as wave after wave of orgasm left my sissy body from the depths of my pussy out through my little white penis. Cum shot out through the lace of my panties.
<hr pg="5" />I closed my eyes and let the orgasm wash over me. He wasn't done yet, so I had nowhere to be besides under him. Helping him achieve the same bliss that I just felt at the hands of his big black cock. I wanted to bring him the same level of pleasure he had just brought me. Because deep inside of me, I knew I needed him. And if he doesn't feel like he needs me, then he might not continue to fuck me with his big black cock.

Once I regained feeling and control of my legs, I was ready to get started on my mission to make him cum.

"Could I please ride your big black cock, Sir?" I pleaded, looking up at him with my best doe eyes.

"You got it sissy," he said before pulling out of me and laying on his back.

I stepped out my soaked panties leaving me in my bustier, garters and stockings before crawling back on the bed. I looked up at him and reached for his big black cock with both hands before licking his big black cock from the base to his tip. I worked the head for a minute, swirling my tongue around the head as best I could given there wasn't much room in my mouth.

I pumped his big black cock with both hands as I did this. He moaned. I was happy.

Sucking his big black cock felt very natural. And I was good at it based on the reassurances he gave me through his moans and numerous "damn, sissy."

I have never sucked cock before, but I just thought about what I would like if I had a huge cock and did that to him. No one knows their way around a cock better than a sissy who has spent years pleasuring themselves after striking out with women. Sure, I had to get adjusted to the differences in size between his big black cock and my little white penis, but I still knew how to work a cock.

After a few minutes of worshipping his big black cock with my mouth and hands, I kissed his stomach and crawled up on top of him. I never let go of his big black cock as I held it straight up and positioned it at the barrier of my sissy pussy, squatting above him.

He reached for my hips and slowly guided me down. Further and further I sank down his big black cock until I was once again fully impaled on him.

I admired how hard my little white penis was still, standing at attention. No longer in the confines of my panties. Guided by his strong hands, I worked my way up and down his big black cock.

He loved this. Moans and growls escaped his mouth as I rocked my hips to change the angle. Learning what he likes. Learning what I like.

My pace quickened, my little white penis leaked cum onto his stomach. I kept riding.

"Fuck me with your big black cock, I need it so bad," I managed to get out as my orgasm grew closer.

I continued to ride.

"Yea, right there sissy," he said after a new move where I arched by slightly backwards.

That's all I needed to hear. I reached behind me to grab his shins, arching backwards. He grabbed my hips and thrusted into me from below, harder each time.

He pulled me down hard and growled. I felt his big black cock pulse and cum shoot deep inside of me. Rope after rope of his cum painted my insides.

I came. Spilling my sissy cum onto his belly.

"I'm sorry Sir," I said. Assuming he was mad about me cumming on him.

I leaned forward to lick it up before collapsing onto his chest, his big black cock still inside of me.

We breathed deeply together. A black man and his little white sissy.

"I'm your sissy," I whispered into his ear, in between breaths.

"I know," he said before giving my ass a light slap.

