My sister's flatmate - Chapter 08 - Liz's first anal experience

I woke up on a sunny Saturday morning to the smell of coffee. I opened my eyes and looked at the naked Liz kneeling on the ground right in front of my face. Her hands held a cup of coffee in front of her breasts.

"Good morning" she said and held the cup in my direction.

I moved myself up in the bed until I sat and was leaning against the headboard. I grabbed the cup from Liz and took a big sip.

"Good morning Liz." I smiled at her and she smiled back, "how did you sleep and how did you wake up?"

"I slept very well. When I woke up I was really confused at first. Being naked and woken up by a vibrator was something new for me. But then I remembered my task and slowly got up and into the kitchen. When I was waiting for the coffee I noticed that I was really wet already."

"Sounds very good. I'm also having a giant morning wood. Get up here and start working on it." I pulled down my shorts, spread my legs and padded to the space between my legs. Liz immediately did as I asked and kneeled between my legs. She started by running her hand up and down my shaft and giving me a few slow strokes. Then she leaned forward and let my cock slide between her tits up to her face. She opened her mouth and started to suck at my tip. That made me moan out loud and heavy. I took a few sips of my coffee and enjoyed the feeling of her mouth that moved down further and further. Once she had nearly my whole cock in her mouth I made her gag by pressing down her head even more. My cock was slipping in her throat and I enjoyed the pressure around my cockhead. When she gagged I released her head and pulled her off my cock. She inhaled sharply to get some air in her empty lungs.

"Good job, my little subbie. But don't make me cum yet. It felt really good when my cock was resting between your tits. Try to pleasure me with them."

"As you wish. But I never did this before. I don't know what feels good for you."

"You will notice." I said and grabbed my phone. I turned off the vibrator and waited for Liz to start. She positioned my cock between her breasts and moved up and down with her body. I slightly increased the vibrator intensity.

"Press them together with your hands."

"Like this?" She said while pressing her tits together. I increased the intensity again. She bounced up and down my cock. Her eyes traveled between my face and the tip of my cock which poked out from in-between her breasts.

"Lick my tip my little subbie" I ordered her. Her eyes were now glued to her breasts. Whenever she saw my dickhead she either made an o-face and let it slide in her mouth or her tongue darted out and gave it a quick lick. I increased the intensity of her vibrator again and got a little moan as a response. I finished my coffee while I watched Liz working my cock. It felt really good and I needed to concentrate to not cum right away. I played a little bit with the vibrator from time to time and saw that she also was getting closer and closer to an orgasm. I didn't really want to do it, but I turned off the vibrator.

"Oooh fuck Liz. It's enough please stop. I don't want to cum yet." She gave me one final lick and released my cock from in-between her tits.

"I hope I did okay."

"Yes you did really well my little subbie. I'm proud of you. But there is one more thing I want to try together with you." I reached into a different drawer of my nightstand and pulled out latex gloves and lube. I handed it over to Liz who looked at me very confused. She was still kneeling between my wide spread legs. I moved a little bit further down and reached for a pillow which I placed under my lower back.

"You are allowed to use the gloves whenever you like. Now lube my cock up and give me a nice sloppy handjob my little subbie."

"No problemo" Liz said with a smile and reached for the lube. She put a good amount in her palm and waited a moment to warm it up a bit. Then she reached for my dick and started to let her hand run up and down my throbbing dick. I let her continue like this for a while and played with her vibrator from time to time.

"Move one hand further down below my balls."

"Here?" She asked while her hand was placed exactly where I wanted it to be.

"Oh fuck yes perfect. Try to press slightly.... Oh yes exactly like that." I enjoyed Liz's touches for a few moments. I played with her vibrator and really got her excited as well.

"Move it further down my little subbie." Liz was hesitating for a moment. When I saw her eyes wandering towards the gloves I rapidly increased the speed of her vibrator. She moaned out loud and moved her hand to my anus.

"May I cum please? I can't hold it anymore!" Liz suddenly asked.

"Only if you put your finger inside first." Without any hesitation Liz increased the pressure until her finger slid inside of me. It was the first time that I felt another person's fingers in my ass and it felt amazing. It felt so good that I came right away and unloaded myself onto Liz's hand and my lower stomach. Liz pulled her finger out of me, threw herself on her back, spread her legs and used both her hands to rub her pussy. It took her only a couple of seconds before she came. I think her orgasm might have been even bigger than my own one. She came and came and came. It took her minutes to come down from it. She looked very sweaty and used even tho I didn't fuck her.

"Thank you for the orgasm" Liz said and smiled at me.

"You earned it. You did good. And both of us have earned a shower. Get up and move your ass to the bathroom."

"That's a very good idea" Liz laughed and got up.

I cleaned the cum from my belly and searched for some clothes before I also went to the bathroom. When I reached the door I had to notice that Liz closed and locked it. I heard the shower running on the inside.

"Open the damn door Liz. I never told you to lock it." I said while hammering against the door.

I walked back into my room and grabbed a few items. This was maybe the right moment to teach Liz a little lesson. When I came back to the bathroom the door was still closed but not locked anymore. I entered the bathroom and saw a smiling Liz in the shower.

"Hey, sorry I didn't..."

"Shut up and get out of the shower." I interrupted her. I was playing a little angrier than I really was but I think she got my mood. She walked out of the shower with her head down. I pointed to a place on the ground and ordered Liz to kneel down. I laid the three items on the ground in front of her.

"It's time for a little punishment Liz. You need to understand that you have to listen and do exactly as you are asked to. But I'm not the devil. You can still decide your own punishment. You have three options Liz. The first one is this flogger. It will be painful but it will be over in a couple of minutes. The next ones are these nipple clamps. The pain is less, but they will stay on longer. Your third option is this small anal plug. It will stay in the longest but there is no pain. Think about it, but think quick. I want an answer before I'm nude."

While Liz's eyes traveled between the three items I started to remove my clothes. However it only took Liz a couple of seconds before she decided.

"I would like to be punished by the clamps."

"What a good decision." I answered. I had been pretty sure beforehand that Liz would decide for those. I finished undressing and ordered Liz to stand up again. I picked up the clamps and checked the adjustment. I didn't want to make them too strong for her first time. Then I gently rubbed at her nipple to make them a little bit stiffer. I brought the clamp around her now stiff nipple and closed it gently.

"Ouch"

While ignoring her for the moment my hands travel towards the chain, which is attached to the clamp, and pulled at it. Liz made some weird looking faces but kept silent. I reached for the clamp at other end of the chain and placed it at her other nipple.

"Ouch"

"Better get used to the feeling. You will be wearing those for some time." I grabbed for the chain and started to walk towards the shower. Liz quickly followed to keep the tension low. When we reached the shower I turned on the water and pointed at the sponge and the soap.

"You are gonna wash me my little subbie"

Moments later I was able to feel the soapie sponge on my skin. Liz started with my upper body, shoulders and my arms. But a few moments later she was kneeling in front of me and cleaned my legs. As you might imagine the view was quite stunning and I had a hard one since we entered the shower. As soon as she was done cleaning most parts of my body I put my hand behind her head and slowly pulled her towards my waiting dick. She obviously understood the hint and opened her sweet mouth. It already was the second blowjob of the day but I enjoyed it nonetheless. After she had pleasured me for some time I reached down and pulled at the chain connecting the clamps.

"Get up and turn around."

"Ouch ouch ouch" was all she was saying while she tried to get up fast. I pressed against her shoulders and she leaned forward as intended. Her hands are placed at both sides of the shower head and a big part of the water stream landed on her lower back. I grabbed my cock and pointed it at her entry. I wasn't sure what had made her more wet. The shower or her hornyness? I however was super horny and slowly pushed my cock into her cunt. She was way tighter than the night before because she didn't have a dildo in her for the last hour. I fucked her merciless and slapped her beautiful butt from time to time. She moaned every now and then. My hands ran over her butt cheeks until I found her butt crack. I explored it with my fingertips and added some soap to make it more slippery. I stopped when my fingers reached her anus. I felt the muscle under my fingertips and slightly pressed my middle finger against her tight closed hole. All the time I was moving relentlessly in and out of her cunt. My other hand traveled along her hip towards her left breast. It rested around her breast and I pressed the tit every now and then. I reached for the chain which connected her nipples and pulled on it. Liz moaned from the pain and tried to remove the pressure from the chain. I released it and pulled it again a few moments later. This time I was also increasing the pressure on her anus. My plan worked well. Distracted by the pain in her nipples Liz was not paying attention and my finger slipped into her anus. I kept my finger still and released the pressure on her nipples. Since Liz wasn't reacting at all I slowly retracted my finger from her anus again. I haven't had lube, I didn't want to overdo it and I was close to cumming anyways. However her ass has been tighter than I had imagined it and definitely way tighter than my own. This definitely increased my urge to fuck her ass even further.

With that in mind I emptied my balls deep in her pussy. After groaning out loud I slapped her butt again, pulled her upper body back to its normal position and turned her around.

"You did good my little subbie" I said and kissed her deep.

"Can your little subbie also cum?" She asked when we parted from the kiss. Hearing her call herself my sub let my blood flush into my cock again. After a few seconds of thinking I shook my head.

"No not now. You barely made up for locking the door. I don't think that you have earned it yet."

"I'm very sorry. It was out of reflex. I wasn't thinking."

"Don't worry Liz. You are being punished and by that it's forgiven and forgotten."

"But I really want to cum." She insisted.

"I said no Liz!" I answered a little bit pissed "I wasn't aware that touching your ass makes you so horny. You can cum if you put that plug in your ass first."

Liz's eyes followed my pointing finger and she was actually thinking about it for a moment. Then she shook her head.

"Then I would prefer to not cum." she finally said with a little bit of sadness in her voice.

"Good. Now let's get out of the shower."

After Liz had tried me with my towel I chose some clothes for myself and waited for Liz to finish her bathroom routine. Once she joined me in the bedroom I told her to get her one allowed outfit. Once she had spread it out on the bed I took the bra and the panties away from it.

"Okay put those on Liz"

"Finally some clothes again." She replied while putting on the garter belt. While watching her pulling up the black stockings I expected a question regarding the nipple clamps. But to my surprise she just pulled the pullover over her head.

"Done" she said and smiled at me "It feels good to have something on the skin again." She said with a big grin.

"And you look stunning. Even with clothes on." I joked. "Put on your shoes, we are leaving in a minute."

I saw how Liz hesitates.

"It's super cold and windy outside. I think this skirt with no panties under it might be a little bit too fresh." She finally said.

"Come here Liz" I ordered and added "Put your arms behind your head" when she stood in front of me. I reached under her skirt and touched her pussy. It was as wet as I expected it to be.

"Maybe you shouldn't be so wet. That would make it warmer." I said while playing with her clit "And just to make it clear: it's not your job to think. You do as I tell you to do." With that being said I removed my hand from her pussy and reached under her pullover. I pulled it up until her breasts and the nipple clamps were exposed. While holding the pullover up I tightened both clamps.

"Oughm" Liz muffled due to the increased pressure on her nipples.

"Now that I think about it I have a better idea. Drop your skirt subbie." I said while walking to one of my closets. With a rope in my hand I came back to Liz.

"Open your legs a little" I commander her "I will try a tie I never tried to anyone before. You are allowed to feel special Liz."

I spun the rope around her hip once slightly above her garter belt. I then went from her front under the garter belt and through her crotch to her back. I readjusted the rope multiple times and added a few extra knots. When I was done I looked at my work of art. The three knots were pressing against her clit, her pussy and her asshole.

"Walk a little bit for me. Does it hurt anywhere?"

"No. It feels weird but it doesn't hurt."

"Good. Get back in your skirt and put on some shoes. The next time you disobey I will secure a dildo with the rope."

A few minutes later we were walking through a nearby park. The weather wasn't super nice so I aimed for a cafe at the end of the park. Once we arrived in the cafe we sat down and ordered a coffee. Liz was making a weird face when she sat down. I could only guess that the knots were doing their job. While we waited for our coffee I took the opportunity to write Liz a quick text.

"I have tortured you long enough. Move one hand at a time under your pullover and open the clamps."

She quickly checked if someone was watching her, reached inside her pullover and opened the clamp. Her facial expression quickly turned from happiness towards pain when the blood started to flow back in her nipple. It was clear that she didn't expect it to be so painful. A lot less energized she moved her other hand to her other tit and released the clamp as well.

"Ouch" she said silently and placed her closed hand on the table. I took the clamps from here and let them slide in my pocket. Shortly after we received our coffee. It was delicious and came with a little cookie that was delicious as well. We talked a little bit about this and that was afterwards. Liz looked like she was enjoying the normality of the situation.

"I will quickly go to the bathroom." She said and left. I was wondering how she would pee with the crotch rope. I made an interesting looking face when Liz walked back to the table. She blushed slightly, knowing exactly what I would ask.

"I pulled it to the side. Like a bathing suit." I had to laugh and Liz somehow had to join me laughing.

We paid shortly after and went back walking in the park.

"How is the rope Liz? Is it painful? Does it give you pleasure?"

"It feels weird. It's not really giving me a lot of pleasure and it's also not painful. When sitting it was uncomfortable to have the knots pressing against me."

"But is it giving you some pleasure?"

"Yes that is for sure."

We were in a less crowded part of the park. The main part of the park was shielded by a hedge. I quickly looked around but I couldn't spot anyone in this small area. So I asked Liz to lift her skirt.

"Show me how wet you are."

I saw the panic in Liz's eyes. She looked around and her eyes searched for other people. I gave her a second or two to lift her skirt before I got mad again

"I asked you to lift your skirt Liz. What is taking you so long?" Slowly she started to lift it until I was able to see the rope between her glistening pussy lips.

"You look very wet Liz." I said while stepping a bit closer. My hand moved towards her waiting pussy and carefully touched her down there. I ran them along the rope and pressed the knot against her clit.

"You also feel very wet Liz. Why are you lying to me? You said it's not arousing you but it clearly is. And why are you not doing as you are told? When I say you lift your skirt you are gonna lift your skirt. Understood?"

"Yes, I understand. I just wanted to make sure that nobody sees us."

"You don't need to make anything sure. You only do as I tell you. Drop the skirt and expose your tits."

This time Liz reacted a little bit faster. She quickly looked left and right before she lifted her pullover. I really liked how she was standing there. On this small path, with trees and grass behind her. Really a nice view. I pulled the nipple clamps out of my pocket and readjusted them. I ignored the two "Ouch" when I placed the tighter clamps on her nipples.

"Drop your pullover." she did as I asked her and I continued "That was one punishment but you misbehaved twice. Until we are home you can think about your second punishment. You remember your choices, right?"

"Yes I do remember them." Liz said frustrated. I took her hand and walked her through the park. We continued to chat and slowly made our way home. As soon as we entered my flat I turned around and asked Liz what her punishment should be.

"The flogger please."

"As you wish. I need to go to the bathroom. We meet in the bedroom in 10 minutes."

When I entered the bedroom Liz was sitting on the bed.

"Liz, why are you doing this? The first rule I gave you was, that you always have to be naked in the flat. Why do you still have your clothes on?" Liz jumped up and started to strip.

"I'm sorry, I didn't realize that I should strip already. I didn't know it, I'm sorry."

After waiting patiently for Liz to strip I ordered her to get in the bed.

"Place yourself in the middle of the bed, head down and ass up."

Liz presented me her bald pussy, which was split in two by the rope running through her slit. Two knots were visible for me which pressed against her two holes. After enjoying the view for a view moments I moved her legs a bit further apart.

"Stay like this." I ordered her while I moved towards my wardrobe. I grabbed a few ropes and tied her ankles to the sides of my bed. That way she couldn't close her legs.

"Grab your ankles with your hands"

As soon as her fingers closed around her ankles I tied her wrists to her ankles. Liz was now fixated in the head down ass up position. With another short rope I tied the chain connecting her nipples to the crotch rope. I made sure that the chain was tight and pulled at her nipples.

I ignored Liz's protesting sounds for now and grabbed the flogger.

"Soooo how many slaps did you earn Liz? Maybe 10? 20? Let's meet in the middle. 15 it is."

I grabbed the crotch rope and pulled it slightly to get a moan and an ouch from Liz. On one hand the third knot pressed against her clit on the other hand this also means that the chain pulled on her nipples.

I placed a first light slap on her ass with the flogger.

"Ouch" Liz screamed. If she only knew that I would increase the power of the slaps.

I alternated the slaps between both her cheeks and caressed her butt in between slaps. From time to time I was pulling at the crotch rope to give her some pleasure.

The fifth and sixth slap was already really hard and Liz started to not only"ouch" but to actually scream. I was starting to feel bad for her but I also knew that it's important to finish her punishment. I slapped even harder the ninth and tenth time and Liz added a sobbing sound in between the screams. I acknowledge the reddish color that formed on her cheeks and I could feel the heat that was radiant from her skin.

"This is the last one." I announced before I gave Liz one final slap. I made sure that it's a little harder than the previous ones. Liz screamed one final time and continued sobbing afterwards. I let my fingers run over her glowing ass and applied a cooling lotion onto her skin. Then I opened the knot holding the crotch rope and let it fall on the mattress between her legs. I was greeted with a wet glistening pussy right in front of my eyes. As soon as my fingers touched her Liz shivered. My fingers traveled through her slit and slid into her waiting wet hole. While I was playing with her she calmed down a little bit. Her hands and legs were still tied so she had no real chance to move. Her head was pressed into the mattress. She turned it to the right side. I kneeled on that side next to her and looked into her tear covered face.

"It's over my little subbie. You did good. I'm proud of you." I said while cleaning her face. When I was done I reached under her upper body and opened the clamp around her right nipple. She inhaled deeply when the blood came back into her tortured nipple. We repeated this on the other nipple as well.

"Good little subbie." I patted her head and leaned back. "I really don't want to punish you. Please stick to the rules in future. Do you understand?"

"Yes, I will try my best."

"Good, there is one punishment left." I said while pulling the plug out of my shorts. "It's for not getting naked as soon as we entered the flat. Are you ready Liz."

Liz gulped once and then nodded slightly. "Yes I am ready."

I moved out of her field of view and dropped my shorts. I obviously had a hard one. I was staring at a beautiful, naked, tied girl for some time now. How couldn't I have a hard one. After moving behind her I dropped some lube on her ass and watched it running down her butt crack. I also coated my dick in some lube and pressed it against her waiting cunt. I slipped into her right away and enjoyed her tightness once more. While my cock was sliding in and out of her cunt my hands traveled along her ass until I found her anus.

"Relax" I said while pressing my pinkie against it. "Try not to think about it Liz. Focus your mind on this." I reached between her legs and touched her clit. Liz moaned out loud and I used the distraction to push my pinkie into her butt.

"Well done." I complimented her while fucking her with my finger. After a few moments I pulled it out and started the game with my next bigger finger. I really took some time to prepare her. I want her to enjoy it.

"Next will be my thumb, are you ready?"

"Yes I am." She answered with a little bit more confidence in her voice. While touching her clit again I moved my thumb into her butt more or less effortlessly. Again I moved my finger a few times until I pulled it out. All the time I was fucking her relentlessly. I was getting closer to an orgasm but didn't want to cum yet so I pulled out of her.

"It's time for the plug now. I really want to let you cum Liz. But not as part of a punishment."

The plug was rather small. When I use it for myself I don't need any stretching and can just push it in. However for Liz I coated it with lots of lube before putting the tip against her slightly opened anus. The silicone of the plug made it's way into Liz until only the blue diamond was visible. I enjoyed the view of her glistening cunt below the diamond for a moment. But I couldn't last long, I just had to fuck her. I pushed myself into her again and enjoyed the feeling. I don't know if she really became tighter or if it was just my imagination. However it felt really really good and it didn't take me very long to orgasm for the third time this day.

When I came down from my orgasm I untied Liz and she immediately collapsed onto the bed and rolled herself up. I laid myself next to her and assured her how good she took it and that I'm really proud of her. We just chilled for a while. I caressed her hair a bit and slowly made her feel better again. It has been a hard day for her already. But it was only 2pm. It wasn't over for her yet.