Serving My Roommate and Her Friend Ch. 04

Author's note: Thank you all for your kind comments on the first three chapters of this series, it means a lot that people are enjoying it. I'm sorry this chapter took so long. Rest assured that more chapters are on their way. Another series will be coming as well.

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For the second night in a row I couldn't get any sleep. But instead of having trouble due to a dick that wouldn't calm down this time my issue was basically the opposite. Miss Caroline had been very clear that I was not allowed to come until at least the next day when she arrived. But the footjob Miss Katie gave me earlier felt so damn great no matter how hard I tried I couldn't hold back.

I had been so pent up that I came in a torrent. Cum ended up everywhere, including on my lap and on Miss Katie's feet. Once my head cleared from the afterglow of the orgasm I was so ashamed by what I had done that my first instinct was to clean it up as fast as possible. I grabbed some tissues and wiped up the mess from Miss Katie's feet and around my cock.

"Bad pet!" Miss Katie kicked my thigh, "you were not supposed to come."

"I know Miss Katie, I'm so sorry, I tried to hold back, you wouldn't stop."

"Don't blame this on me. That thing between your legs is your responsibility. Miss Caroline is not going to be pleased. I wonder what punishment she'll have for you."

The feeling of having disappointed Miss Caroline felt like punishment enough but I knew there would be more. Miss Katie's had an excited look in her eyes, I could only assume she was looking forward to seeing that punishment.

"I hope it was worth it, pet. Did you at least enjoy your orgasm?"

"It was amazing, Miss Katie, your feet are so soft and sexy. Thank you. And I'm sorry." I hung my head low.

"Yes, you are." Miss Katie got up from the couch and went upstairs to bed.

I sat there for a moment, pitying myself for my failure, before getting up to clean the cum I had shot around the room. Making the evidence go away made it feel like it hadn't happened. Though my soft dick seemed like pretty clear proof.

As I laid in bed, tossing and turning, I thought about the devilish smile on Miss Katie's face as my orgasm was building. And how she seemed to ignore my pleas to stop. Maybe she was too focused on making herself come to hear me. Or maybe she ignored me on purpose.

After finally getting a few hours of sleep I got up to start the day. I started with a shower. I quickly realized after that I would have to talk to Miss Katie about the clothing rules since I certainly couldn't go to the office naked.

She was still sleeping so like the previous day I went to the kitchen to have breakfast waiting for her. Nothing as elaborate this time, just a cup of coffee the way she likes and a quick batch of scrambled eggs.

She eventually came downstairs fully dressed for work. The smell of breakfast made her smile but the sight of me and memory of how I failed last night switched her into stern mode.

"Good morning, pet. Trying to assuage your guilt for failing last night?" She sat down and began eating.

"No Miss Katie, you just deserve a nice breakfast."

"You're right about that. Maybe you should start bringing it to my room in the future."

"Whatever you want, Miss Katie. Uh, I have a question."

"Yes?"

Looking down at myself, "how does the no clothes rule work in cases where I have to leave the house, like for work today?"

Miss Katie laughed, "yeah, that would be awkward, wouldn't it? You can wear your normal work clothes but I don't want you to put them on until right before you walk out the door. When you get home you'll remove them immediately. And as I mentioned yesterday you don't get to wear your underwear. You can, however, wear these."

Miss Katie pulled another pair of her painties out of her pocket and tossed them to me. Unlike yesterday's basic cotton pair these were a shear, lace, thong. I lifted them up and stared at them.

"Why don't you put them on now. It's not like they're going to cover muchanyway," Katie laughed.

I stepped into them and slid them up. The front was so small there was no way my cock would stay inside, the fabric just went around one side leaving my cock sticking out. The thong, however, did its job getting right up between my cheeks.

Miss Katie gave my cock a few strokes. "Looking good, pet," she laughed, "but maybe you'll need some in your own size. She finished eating and stood to leave. "Remember, Miss Caroline will be here after work so get home as fast as possible. And if I were you I'd be on my best behavior after what you did last night." She once again flashed me a devilish smile. "Hurry up, can't be late for work," she smacked me on the ass.

I quickly cleaned up breakfast and ran up to my room to get my clothes and bag. Miss Katie was waiting by the front door when I came back down.

"May I get dressed for work, Miss Kaite?"

"Yes you may, pet."

After I put on my work clothes Miss Katie rubbed my cock through my pants and gave me a light kiss on the lips, "have a good day, pet, I'll see you this evening."

"Thank you, Miss Katie. You too."

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Work was nearly impossible. Mondays are never fun but between the panties Miss Katie had forced me to wear and the thought of seeing Miss Caroline my dick was excited and it was impossible to focus. I was excited to see Miss Caroline even knowing that punishment wouldn't be too far behind. Or maybe I was excited in part because of the idea of punishment? Either way I knew I missed her, it had only been a couple of days but she was always in my thoughts. Her sexy toes, her shapely legs, her round ass, her heavy breasts, and that smile. I so looked forward to being in her service again.

Somehow I muddled through the work day. The seconds seemed to last forever and I'm not sure I got any actual work done but it didn't matter now that I was on my way back home. I was lucky not to get pulled over as I sped through the streets as fast as I could.

I was the first one back to the house. As soon as I walked through the door I dropped my bag, stripped off all of my clothes, and carried them up to my room. I went to the bathroom and washed up before hearing a car pull up to the house. I rushed back down to the front door to great whomever it was.

The door opened as I was walking up to it. It was Miss Katie, it looked like she had a long day as well. I reached out offering to take her bag from her.

"Well hello, pet, this is a nice way to be greeted."

"Hard day, Miss Katie?"

"Just long and busy. And of course my thoughts kept going back to..." she drifted off as she looked around.

"Miss Caroline isn't here yet, Miss Katie."

"Ah, good, I'm going to take a shower before she arrives. Why don't you wait right here." Miss Katie pushed me down by my shoulders until I was kneeling a few feet from the door.

"Of course, Miss Kaite."

She continued upstairs and a minute later I heard the shower start.

I knelt there considering the pleasure and pain I was likely to experience tonight. Every thought filled me with nervous excitement.

I didn't have to wait long before I heard a car pull into our driveway. I tried to calm myself down, to tell myself not to overdo it as soon as I saw her. It didn't work.

Miss Caroline opened the door and stepped into the apartment. I immediately looked at her with puppy dog eyes but when she met my gaze I looked down embarrassed that I'd failed her last night.

She walked over to where I was kneeling sure to get close enough that all I could see before me were her chunky boots. I knew what she wanted without having to be asked. I bent down and kissed each boot once.

"Well hello there pet."

I lifted my head, slowly taking in her beauty. In addition to her shiny black boots she wore a long, tight black skirt with slits all the way up both legs and a simple tight t-shirt that accentuated her large tits. Her dark outfit contrasted wonderfully against her creamy white skin.

Finally looking her in the eyes again I couldn't help but smile. She looked down on me with a smile of her own, though hers was more playful. She could see my cock was already getting hard. She lightly tapped it with one of her boots.

"It's nice to see you too, pet," she said with a smirk.

She slid one boot closer to me and I knew what she wanted. I focused my attention back down as I untied her laces and gently removed the first boot from her foot. I put the boot aside and bent my head low to kiss the top of her sock-covered foot. After a few kisses she pulled it from me and presented the other boot. I removed it and added some kisses to that foot as well.

I took her sock in my mouth and tried to work it off of her foot. Miss Caroline helped by lifting first one foot off the ground and then the other as she chuckled at my struggle. When both of her feet were naked she stood tall in front of me with both feet together. On all fours I bent my head down to her lovely toes and pushed my ass into the air. They were still painted in a glossy black

I took a deep breath of these sexy feet I had been dreaming about for days. They smelled of leather and sweat, I never before would have imagined I would have enjoyed such a combination but I couldn't get enough.

I kissed each toe once starting at her left pinky toe and moving across all 10 to the right pinky. I then moved slightly up her foot and kissed my way back across. I repeated this back-and-forth, making small kisses along the top of her feet moving slightly higher each time.

When I reached her ankles, Miss Caroline stopped me, "this feels wonderful pet but do you think I could make my way inside?" she laughed.

"Oh of course. I'm so sorry, Miss Caroline."

"Your enthusiasm is appreciated, pet, I'd just like to sit down."

"Please do, Miss Caroline. You left so abruptly the other day and I've really been looking forward to seeing you again.

I moved out of her way and she patted me on the head as she moved passed me to the living room.

"Oh yeah, I had to get to that date. Well it was supposed to be more of a date but I was so horny when I left here I just went straight to his place and fucked his brains out."

Miss Caroline made her way to the couch and sat down, leaving her bag on the floor next to her.

"Lucky guy," I said full of jealousy.

She crossed her legs leaving one foot in the air near my face.

"And you're a lucky pet. How lucky depends entirely on you."

She rotated her ankle and flexed her foot. I sat there transfixed by the movement.

"You may continue, pet..." she said slightly annoyed.

I took her foot in my hands and began licking the sole. I worked my way up from the heel, lavishing every inch with my tongue. When I reached her toes I took the big one in my mouth and sucked on it.

"So I guess you missed me?"

I removed her toe from my mouth long enough to answer, "I've thought about you with my every free moment. And even some of the time I was focused on Miss Katie."

"Where is my baby girl?"

"She went up to take a shower shortly before you arrived."

Miss Caroline switched her legs and presented her other foot to me. I repeated my worship on this one as she continued talking.

"I hope she's as excited to see me as you are, pet."

"I'm sure she's excited, though I'm not sure anybody could be as excited as me, Miss Caroline," I said with a laugh. "I think she really enjoyed being in charge the last couple of days."

"Mmm, I bet she did..."

I continued sucking on her toes, taking each into my mouth and swirling my tongue around it.

"What was my baby girl like as 'Miss Katie'?"

"She was demanding but fair. She kept me on edge as much as possible. It was a pleasure to give her pleasure."

"I'm sure it was. She is very beautiful and we know how much you like to give pleasure. What did she have you do?"

"I toweled her dry after a shower. I massaged her whole body for hours, licking up any of my drippings that landed on her, of course."

"Of course."

"I licked her dildo to get it wet for her use and then licked it clean after."

"What a delicious idea."

"Mmmm, it was delicious," I licked Miss Caroline's feet some more, "the next morning I made her a big breakfast and stood by her side hard at the ready while she ate. My meal started with toes dipped in maple syrup."

Miss Caroline laughed, "I know you love that real maple syrup."

"Now more than ever," I chuckled, "later when Miss Katie returned from the gym I undressed her and worshiped her sweaty feet. She 'rewarded' me by stroking me to the edge multiple times."

"But didn't make you come, right pet?"

Miss Caroline stared directly at me, interrogating me with her eyes. She could tell, I just knew it. Why didn't I tell her the truth right away?

"No, Miss Caroline, I didn't come then..." oops.

"'Then'?" Miss Caroline raised an eyebrow and her voice.

I considered lying further but I knew I wouldn't get away with it. Not only was Miss Katie there but I had no doubt Miss Caroline could read me like a book. I also just didn't want to keep something like this from her. I broke down.

"Oh god, I'm so sorry, Miss Caroline, I failed you, I tried to hold back but I couldn't. I came last night." I lowered my head to the floor in shame.

"You horny little slut," Miss Caroline snapped as she grabbed my hair and pulled me back up to look her in the eyes.

I braced for more anger but instead I felt her disappointment.

"Oh my dear pet. You couldn't even last a couple of days. And then you tried to hide it from me. I expected better from you."

"I'm so sorry Miss Caroline. Please, how can I make this up to do? I'll do whatever you want."

"You already will do whatever I want. I think you know what this will require."

"Punishment," I said softly.

"Punishment. But first, tell me what happened."

"Well as I said Miss Katie kept me on edge as much as she could with multiple worship sessions and teasing me often."

"Yes, I would hope so, I told her to test you."

"Last night we were here on the couch and she was rubbing her feet on my dick, I of course couldn't touch her. She started playing with herself and when she came her feet went wild and I couldn't hold back."

"You're not trying to blame her are you?"

"No, of course not, it's my cock it's my fault," even though I had a feeling Miss Katie made me come on purpose to see me punished I knew it would only be worse to blame her.

"Why didn't you tell me as soon as I arrived?"

"I was so nervous about how you'd react and then when I saw you I was distracted by excitement and lust. Please forgive me."

"We'll see, pet, forgiveness has to be earned. Now get over here and give me a place to rest my legs," Miss Caroline commanded with a snap of her fingers as she stretched her legs out straight

I moved closer to her and got on all fours under her feet and she let them drop on my back with a thud. She leaned forward to smack my ass. She rubbed her hand over my stinging ass cheek and smacked it again. This may have been the start of a punishment but I think she just wanted to play with her pet. She even slipped her hand between my cheeks letting her finger graze my hole. After another smack she leaned back and pulled out her phone. She wanted me to know that I was just a piece of furniture for her at the moment.

About five minutes later we finally heard Miss Katie coming down the stairs. She joined us in the living room wearing a silk robe. She walked to us trying to project confidence but we could both tell she was a little apprehensive. After the last couple of days it was a little odd for her to not be the most commanding presence in the room. She stopped a few steps away from the couch.

"Caroline! It's so great to see you again," she said with a nervous smile.

"It's nice to see you too, baby girl..."

Miss Caroline rose from the couch. She nudged me with her shin to get me to move out of her way so she could close the short distance to Katie. Despite being a couple inches shorter there was no doubt that Miss Caroline was the more confident and powerful one here. But would Miss Katie give in to that power so easily? Without warning, Miss Caroline grabbed Katie and pulled her close. She kissed her deeply, pushing her tongue in Katie's mouth. Katie moaned as she kissed Miss Caroline back. Katie tried to assert herself as they battled for dominance with their tongues. She used her extra height to her advantage, getting right on top of Miss Caroline. Katie slid her hand up Miss Caroline's back and ran her hands through her hair. Miss Caroline playfully smacked Katie's ass with both hands causing Katie to jump and nervously giggle.

"...yes, very nice to see you, indeed. But we have a few problems."

Katie's eyes widened in worry as Miss Caroline moved her hands inside Katie's robe. She caressed Katie's tits and moved her mouth to nibble on one ear. Katie moaned some more as her defense weakened.

Miss Caroline whispered, "first, it's 'Miss Caroline', and second..." She pushed Katie's robe off, letting it pool around her feet, "...I didn't say you could wear any clothes."

Miss Caroline kissed her again and playfully but forcefully squeezed her nipples. Katie softly yelped into Miss Caroline's mouth.

Katie kept her eyes closed, perhaps she knew she was too weak to look Miss Caroline in the eyes. She spoke softly, "Caroline, I'm not so sure about all this anymore. We had some fun the other day but I don't think this is really me."

"Ha! Not really you? And when did you decide that? Was it before you came downstairs in a sexy robe or after we made out for five minutes?"

Katie lowered her head.

"My dear old friend," Miss Caroline continued, "this is more you than you can possibly imagine. And I'll prove it to you before the night's out."

Miss Caroline lifted Katie's head to look her in the eyes.

"But we need to get one thing straight first. 'Miss Caroline'. Say it."

Katie hesitated.

"Just be my good baby girl and say it. I promise it will come with great pleasure and a better understanding of yourself."

She was getting close but Katie still hesitated.

"I know you really want to say it. And you want everything else too."

Katie's resolve was weakening.

"You're just nervous. But we're going to do this. Together. Just say it.

"Yes... Miss Caroline."

"That's a good girl. Thank you."

Miss Caroline kissed Katie again and rubbed her tits.

"And don't forget it again. You may be above the pet but never forget that you're my little one." Miss Caroline traced her fingers around Katie's body, "I must be shown the proper respect and I must have easy access to your beautiful body, your sexy supple skin"

Miss Caroline lovingly kissed Katie's upper chest and lightly ran her hand across her pussy causing Katie to moan.

"I gather you enjoyed your time alone with the pet"

Miss Katie relaxed. "I sure did," she looked at me with glee in her eye, "it was thrilling to tease and deny him. Not to mention having him worship me."

"It would be nice to have him worship more of you wouldn't it?"

"I can't wait until he's allowed to, Miss Caroline."

"Are you as eager to do what is required to earn that privilege?"

Miss Caroline had previously made it clear that Miss Katie can only have me worship the parts of her that she has also worshiped on Miss Caroline.

"Of course, Miss Caroline," Miss Katie said unconvincingly. Miss Caroline just stared into Katie's eyes. "To be honest I'm nervous."

"I can imagine. This is all very new for you. But you'll do what you're told, right, little one?"

Miss Katie bowed her head, "um, of course, Miss Caroline."

"Good girl." Miss Caroline lifted Katie's head with a finger on her chin and kissed her once more. "The pet here was telling me about the last couple of days. Massages, edging, maple syrup," they both laughed, "any highlights for you?"