An adult stories – Femdom Flatshare Pt. 04 by WritingSub,WritingSub The evening felt like it lasted for an eternity. I was so excited for the night with Anna that everything seemed to drag along endlessly. After my encounter with her in the kitchen I went to Hailey to tell her that I had finished my chores. If I had expected even the slightest form of thankfulness or appreciation I would have been disappointed. She barely even acknowledged me. But the excitement for the upcoming night prevented me from having any negative feelings at all.
Fortunately for me Hailey did not have any other tasks for me and the others seemed to have other obligations as well. So I had time for myself for a while. There were a lot of things I could have tried to wrap my head around after an eventful couple of days. Alternatively I could have simply relaxed, played some video games or watch some Netflix or whatever….but I couldn’t do any of that. I could not wait for the night to begin so I walked around in my room restlessly, only taking a small break to grab myself some dinner. Until finally the moment had come.
Everyone had already retreated to their rooms so I felt like it was finally time. With the memories of my first night with Anna in my mind I slowly made my way to her room. My heart was pounding and although I was really excited ever since she ordered me to come by, nervousness was taking the hold of me now.
I took a deep breath and then hesitantly knocked on her door. A few agonizingly long seconds later Anna opened it. Her head was looking around the door that she had only opened slightly. Her body was still hiding behind it and she grinned at me with anticipation.
“Looks like you were quite eager to come here after all.” she said.
“Of course I am.” I responded eagerly.
She smiled but when I wanted to enter she stopped me.
“Not so fast.” she teased and held a blindfold in front of the door.
Her arm that was holding the blindfold was not covered by a shirt and I couldn’t even see any sign of a bra or anything like that. Was she really already naked behind that door? I could feel my cock trying to get hard in its cage just from the thought of it.
She didn’t seem to notice my brief dream of her naked body or at least she didn’t care. Once I snapped back to reality I looked at her and the blindfold, that I only now noticed, slightly confused.
“Well, put it on already.” Anna requested.
“But….I….Why?…I want to..” I stuttered frustrated.
“Shhhhh….I know you want to. But you gotta earn that privilege. So…” she shook the blindfold in my face. “Neither touching nor watching for you yet.” she explained.
Reluctantly I grabbed the blindfold and put it on while my mind drifted back to my imagination of her naked body.
Anna dragged me into her room and lead me through it once I couldn’t see anything. We stopped after a couple of steps and she undressed me. Unfortunately she was very careful when she pulled my shirt over my head to not move the blindfold. So I couldn’t even get a small glimpse of her potentially nude body. It didn’t take long until she had removed all my clothes except for the cage around my cock of course. She grabbed it with her hand.
“It looks so cute all locked up…” she said teasingly.
I didn’t think it would have been possible after all my imagination but my cock tried even harder to break out. As Anna noticed she giggled and then pushed me back without any warning. Since I couldn’t see anything I panicked for a second but my fall was stopped quickly as I landed with my back on her bed.
Before I could even protest and tell her to not do stuff like that when I cant see, she had already placed her ass on my face.
“So, let’s see if you have gotten any better since last time.” she said as she wiggled around a bit to find a more comfortable position.
My shock from the push she gave me immediately subsided as I felt her clean shaven pussy on my face. Without hesitation I started to run my tongue over her private parts and taste her again. I felt like she tasted even better than the last time and I could tell she was turned on already. Although she was not as wet as she was last time, after playing with my cock.
Since I didn’t really know what I did do wrong the last time I just tried to follow my gut again. I tried to find her clit with my tongue. To get a bit more control and maybe get my tongue deeper inside of her I tried to grab onto her ass. My hands were moving towards it without thinking about it.
But as my hands only just reached the lower part of Anna’s legs she took a hold of them.
“Didn’t I say no touching?” she scolded me in a stern voice.
I wanted to excuse myself and also explain to her that I think I could do a better job pleasuring her that way. However, since her ass was still placed tightly on my face the only thing that came out of my mouth were muffled mumbling.
Anna didn’t care though.
“Right now the only part I want from you is your tongue….so better get back to licking or you will never get good at it.” she explained her expectations.
I reluctantly gave up my pleas and let my hands rest on the bed again as I kept going as I did before.
My tongue went on like this for a couple of minutes but once again I did not seem to have too much effect on her.
I was starting to feel embarrassed when I heard her yawn. It seemed she was even playing with her phone while I was desperately trying to make her cum. I could not let myself fail again so I tried to gather my focus and really pay attention to any small reactions I managed to get from her. Every little twitch and gasp whenever I circled around her clit or got deep into her pussy with my tongue.
Thankfully it payed off. Slowly I could feel her getting wetter and every now and again, when my tongue luckily found her clit, I felt like I could even hear the slightest of moans.
Her excitement was rising noticeably and it was the best feeling ever for me. My mind suppressed everything else. The sole focus of me was my tongue and her reactions to it. I found a good rhythm and I was certain that I was going to make her cum this time. But then a short clicking noise pulled me out of my trance….
She had tried out her key…I was so busy focusing on her pussy that I didn’t realize that she was playing around with my cage…but she had tried out her key….and it worked. The lock sprung open. My mind was racing. All the build up frustration from the day came back to me and I could only think about one thing…fucking Anna.
Anna obviously noticed that I had stopped licking.
“What’s wrong? Anything happen?” she asked innocently.
I couldn’t have said anything even if my face was not buried under her thick ass.
“You were doing such a good job….I thought you might deserve a bit of a reward.” she continued while stroking over the cage that was still sitting on my cock loosely.
It was dying to get out of there, it tried to get hard and although it had a bit more room than when the lock was on, it was still not enough to get fully erect. I squirmed thinking about her finally touching it and even sucking it.
“But since you stopped licking, I guess you don’t deserve it after all….” she said trying to sound disappointed.
I panicked and immediately started pleasuring her again. There was no way to get back in the state of mind I was in earlier. I just had to hope that my body would remember what I did before. Anna giggled when she noticed how I eagerly started licking again. And after a few moments she was back to moaning and she didn’t hold back either.
“mhhh..that’s better” she gasped as she pulled off the cage and watched as my cock sprung to full attention immediately.
Her fingers just slightly slid across my shaft and it already caused me to moan. A shock of pleasure ran through my entire body. I tried to banish the thought of it from my mind, tried to regain the control and concentration that I had earlier. I couldn’t afford to fail this time. My cock needed to cum, I needed to fuck her.
But right at the moment when I started to reenter a good rhythm, Anna let out a loud, long moan as she wrapped her hand around my cock and started stroking. She went agonizingly slow which drove me even madder. Soon after that I was only able to give her the occasional lick in between groans since she had made me a moaning mess within a couple of seconds. Every muscle in my body was tensing as she stroked me.
“Ahh you must be so desperate to cum….aren’t you?” Anna asked teasingly.
Every time I was feeling like I could maybe go for it again she switched up her stroking. Sometimes she sped up, then slowed down again. She added a little twist to her stroke or just caressed the sensitive head. It was driving me crazy. Anna was doing a better job pleasuring me than I could have done myself. Not only did it feel incredible, somehow she had mastered it to edge me. As the girls had already demonstrated to me in a very embarrassing manner, I didn’t have the most endurance. But somehow she managed to always keep me right there on the edge without giving me that orgasm I so desperately craved. I could feel the precum dripping down my cock. My body was tensing and I was squirming under her ass. But every time right before I would shoot my load Anna stopped and refused to give me any stimulation whatsoever.
“Wow it really looks desperate, I am not sure if I have ever seen that much precum.” Anna laughed.
Whenever she had to stop she giggled at my frustrating moans, the tensing of my body and then she started to rub her pussy over my face. I didn’t manage to properly lick her anymore. Ever since she had me on the edge for the first time I was just a frustrated, squirming mess. But it seemed like she was turned on enough by my frustration as I could feel her pussy juices flooding my face.
As she started stroking me at a medium pace after a small break she had to take, she asked:
“So do you think you deserve to cum now?”
“MMMMMMMMM” I responded. Well I tried to respond with a pleading YES PLEASE but her pussy was still grinding on my face.
“Sorry I couldn’t understand you. What did you say?” she asked teasingly as she increased the pace.
Another try of me pleading but ending with muffled sounds followed.
“Did I get that right? You want an orgasm just like last time?” she asked with a big smile on her face.
Last time she ruined my orgasm and it was already incredibly frustrating. But now after this teasing and what happened during the day I could not endure that again….not now….I needed that orgasm.
She was going faster, my body tensed up and I pleaded and begged her to not ruin it again. She was clearly enjoying it.
“Well you didn’t make ME cum so I don’t think YOU deserve a proper orgasm either. That wouldn’t be fair would it?” she added teasingly.
I was almost crying, I needed to convince her somehow. My mind was at another place apparently since I did not realize my mistake as my hands were moving on their own. They wanted to lift her ass out of my face so I could beg her to let me cum. But once I touched her perfect thick ass cheeks she immediately stopped touching my cock.
She smacked my hands and jumped off of me.
“Have you still not learned the rules….” she complained very much annoyed, although the smile on her face, if I could have seen it, would have given away that she got me exactly where she wanted me.
“I…I am sorry…..please…Anna…I need to cum…..please……” I sobbed.
“No, no no! Bad boys like you don’t get to cum.” she said strictly as she grabbed my hands and tied them above my head to the bed with a rope.
“Please Anna,I beg you….” I pleaded.
But she remained strict.
“No! You need to learn to obey rules. And now I don’t want to hear anything from you anymore.” she demanded.
I sobbed while my cock was still throbbing. I heard her walk around in the room. She was grabbing something from a drawer. Then she sat down next to me on the bed.
Seconds after that I heard her moaning right next to me.
“Disappointing….that I…..have to do it……myself once…..agai….AAAAAAAAAAAAAAH” she gasped as she came hard.
My body was still tensing up from frustration and desperation but I didn’t dare to speak anymore. Staying quiet might still leave me with a small chance to redeem myself,or so I hoped.
She kept going with her dildo though.
“Ahhh…at least….a dildo does…..what I expect of it…..AAAAAAAAAH FUUUUCK” she moaned loudly while cumming a second time.
“Please Anna…I am sorry…..let me” I tried once again since her moaning and teasing drove me crazy.
“No!” she interrupted me annoyed, “you have done enough for the night. You will sit there and listen to how it sounds when I am actually satisfied.”
She brought herself to two more orgasms after that before finally collapsing onto the bed exhausted and with a big smile on her face as she watched my still rock hard cock bounce around and desperately seeking some attention.
Anna lay there for a while catching her breath and teasingly running her fingers over my body.
“I guess I won’t be able to lock that thing back up in this condition” she said while gently caressing my cock.
I couldn’t help but groan just from these light touches.
“You could just……let me cum real quick” I suggested carefully.
She got up from the bed and walked around the room while laughing wholeheartedly as if I made the funniest joke ever.
“You must be either really forgetful or really desperate….You messed up your chance silly. But I am too tired to take care of this,”, she flicked my cock, “problem right now.” she continued as she pulled off the blindfold.
Anna had dressed again, apparently wearing a shirt that was long enough to cover everything up.
Although she still looked beautiful I was a bit disappointed I didn’t get to see more.
“So….what are we doing” I asked unsure of what she was aiming at.
“Well I can’t let you leave. You would jerk off immediately you little pervert.” she thought out loud.
“So I guess you will have to stay here for tonight.” she added with a smirk on her face.
For a second I thought she was saying I was gonna sleep with her…fuck her after all, but that was not what she meant.
“Obviously I can’t supervise you while I am asleep so your hands will have to stay tied for the night.” she continued while laying down next to me.
“I hope it won’t be too uncomfortable for you.” she yawned.
I looked at her in disbelief thinking that she couldn’t be serious right now. But Anna just turned on her side and as she pressed her thick ass against my body added an innocent “Good night”.
When I finally had found my ability to speak again she was already fast asleep. And if my hands being tied above my head wasn’t enough to prevent me from sleeping her ass pressing against my groin definitely sealed the deal. It was going to be a rough night. When I finally dropped into an uneasy sleep the sun was already rising. Of course Anna was shuffling around during her sleep but somehow, as if she could control it, there was always her ass or her tits pressing against me. Sometimes she even had her leg wrapped around me. It drove me mad and it followed me into my dreams where I fucked the shit out of her but somehow even there I never got to cum.
I was violently pulled out of my scarce sleep by a bag of ice that Anna pressed against my cock.
The surprise and shock when I felt it had me screaming and sitting straight up in bed immediately.
Anna however was just laughing at me.
“Sorry for the rude awakening. But damn…you might not have the control to restrain from cumming for long but your cock can sure as hell stay hard for long.” she laughed.
I still needed a moment to catch my breath. Waking up like this felt like jumping under an ice cold shower.
“The…..hell….are….you…doing” I grumbled.
“Oh come on don’t be so grumpy…its a beautiful day…..and I even have been so kind to untie your hands beforehand.”, she said as if it was the most generous thing anybody has ever done.
“I just have to leave in a second, so I need to lock you back up and you were still hard sooooo….” she looked down at the bag of ice instead of finishing her explanation.
“You can’t be serious…” I realized in disbelief.
“Of course I am…after all that is how we got you into this thing the first time.” she explained.
Now that she said it I briefly remembered it from that night. The laughing and joking while someone was sitting on my face. Whoever it was still had their pants on though. And then there was this icy sensation just like now before they locked me up…These girls were crazy…
As I escaped my returning memories of that night my cock had gone numb and limb and Anna quickly grabbed the cage and locked me back up. While I was staring at her apathetically she put the key back on her necklace and let it dangle between her tits again. I stared at it as if I was hypnotized by it and she smiled as she noticed.
“Maybe next time you will have more luck. But for now I got to go….have a nice day…” she announced happily as she walked out of the room leaving me alone with my constantly building up frustration.
I tried to go back to sleep without any success. As I got up later that day I walked into the living room and saw Hailey sitting there reading a book. I still have not managed to figure her out at all. It feels like there are different personalities inside of her.
At times there were days going by where I did not talk to Hailey at all. Sometimes because she spent most of her time in her room, probably reading or studying which supported my initial impression of her being introverted and maybe a bit nerdy. At the same time she was out quite regularly. In the beginning I thought she would just spent a lot of time at the university, maybe in the library or something like that. But after a while I learned from the other girls that Hailey actually had a boyfriend.
I mean she was an attractive woman and very intelligent. It didn’t surprise me that a guy would be interested in her but somehow it still did not fit at all to the picture I had of her. She seemed to make quite a mystery out of the guy though. I had never hear her talk about him and even the girls said they had only seen him like twice. It only underlined this whole confused, mysterious picture of her in my mind.
But then there also was the dominant Hailey. She was always present in my mind since that moment she had sent me to the ground and as I walked into the living room that was the Hailey I was about to meet. I just didn’t know it yet as I carefully greeted her and said:
“Hey, Hailey.”
She stared at me with a look like she wanted me dead.
“What? Is there a problem? Did I do something wrong? I didn’t want to disturb you, I am sorry.” I stuttered scared.
“I liked you better when you were down on your knees yesterday.” she said sternly.
“I….what do you…” I stumbled over my words.
“KNEEL” she ordered.
I went down to my knees immediately. Partly because I was scared of the pain but also because I found it incredibly arousing to see that introverted, shy girl act so dominant with me.
“Good, now crawl over here.” she continued.
Embarrassed but also aroused I crawled my way through the room until I knelt right next to her on the ground. Scared I looked at her feet but she pulled up my chin and looked me deep in the eyes.
“That looks like a way more natural place for you don’t you think?” she asked.
“Y…Yes, Hailey.” I responded.
Immediately she slapped me hard on my right cheek.
“What did you say?” she asked angrily.
“I….I said….Yes, Hailey.” I repeated confused about what I possibly could have done wrong now.
Again she slapped me, this time on the other side.
“You will call me Goddess Hailey….and nothing else. UNDERSTOOD?!” she demanded.
“Yes….Yes…Goddess Hailey.” I responded.
“Good, now get your goddess something to eat, would you?” she asked.
I got up without saying a word and was about to walk to the kitchen when she intervened.
“STOP…..turn around….” she said somewhat disappointed.
I turned back to face her and immediately without further notice I had her foot between my legs again. I was left gasping for air but at least this time I still managed to keep standing.
“You will thank your goddess for the opportunity to do something for her.” she stated.
I nodded and responded dejectedly:
“Yes…I am sorry…..thank you Goddess Hailey.”
But right when I finished the second kick hit me and this time it did sent me back on the ground.
“Also, I did not allow you to stand up….you will be on your knees when we are alone….is that clear?!”
It took me at least a minute until I was able to respond to her question.
“Yes more than clear….Goddess Hailey.” I said as I was still gasping for air.
“Now kiss my feet.” she instructed.
I followed without hesitation and couldn’t help but let out a small moan as I was executing her instructions. Content she sat back down and I crawled out of the room to get her something to eat.
As I reentered the room with her food she didn’t even cast a glance on me.
“Here is your food, Goddess Hailey.” I declared but she still didn’t react.
She began eating without a comment as I was kneeling at her feet.
“M….May I leave now….Goddess Hailey?” I carefully inquired after a few minutes.
“No.” she responded in short without even looking at me.
She waved me closer to her however and as I was still crawling towards her she placed her feet on my back.
I didn’t dare to ask why or what else I could do so I just sat there for a long time while she was reading, using me as a footrest and otherwise completely ignoring me.
It took at least an hour until Hailey got up and walked towards her room.
“You are free, slave.” she said bored as she walked out of the room.
It sent a shiver down my spine but it also excited me indescribably to hear her call me that.
“Thank you, Goddess Hailey.” I reacted immediately.
Occasionally there were moments where I could have a mostly normal conversation with Hailey. Often about the university and topics related to courses or a possible career later on. We had two courses together that semester so we always had something to talk about. Sometimes we even studied together. I was not as intelligent as her and the content of the courses didn’t come as easy to me as it did to her. Nevertheless it felt like she valued my intellect and my opinion on those topics. However after that encounter she did never let me forget how our relationship was structured. That I was not simply a fellow student or her roommate, not even a man but simply a slave to her.
When she was stressed or annoyed by something she did not hesitate to let that out on me. Most of the time my balls or my ass sometimes even my nipples had to suffer in those cases. Additionally to those moments, which happened probably once a week on average, she found the need to punish me every now and then. When I didn’t do my chores to her satisfaction or when I didn’t address her correctly. In those cases she really put everything into it and sometimes I could feel the pain linger around until the next day. But even with all the pain she inflicted on me it always gave me a rush to kneel in front of her and being completely under the control of a petite, introverted girl like her.
Over the course of the next couple of days and weeks after that encounter my life thankfully became a little less eventful. After all, luckily for me everybody still had a life apart from teasing me. The intensity didn’t really subside however and usually at least once a day someone found some time to have their way with me one way or another. So my frustration was constantly building. However I started to get into a bit of a rhythm and started to feel like I had really adjusted to my new situation. Although it was far away from anything I had expected when I first visited this apartment with Anna, I somehow still started to enjoy the situation…well at least most of the time. I could have done very well without the agony and constant arousal but something about it was also intriguing.
The only really annoying part of this whole thing however wasn’t all the sexual stuff. Once they knew I was enjoying the situation too and was not about to run away, they deemed themselves free to use their position and control to make clear that basically every household task was my duty from now on. From cleaning to washing clothes….even cooking was my responsibility most of the time. It was annoying and in a household of five more exhausting than I would have expected as well. But I felt like it wouldn’t hurt to get on their good side for starters and push through it. If it would really become too much to handle for me I could still ask them to help me at some point in time. Honestly, despite all of it, it didn’t feel like they would be too harsh about it, except for Hailey maybe…
In the beginning I hoped when the semester finally would start and everybody would be more occupied with studying everything would cool down even further. The girls would have other priorities than to drive me mad all the time and I would have something to focus on and take my mind off of things.
However this hope of mine didn’t really come to fruition. The girls didn’t seem too occupied at all with studying, not even Hailey, I guess she was smart enough to not even have to study too much to pass the courses. And for me, I was quite excited for the first couple of days, maybe the first two weeks or something like that. Everything was new and I was looking forward to experience the university life. But the excitement quickly cooled down. Everyday life commenced, the courses were actually way less interesting and at the same time a lot harder than I expected. So it did not take long until I was even somewhat happy when one of them wanted to have some fun with me just so I could get away from studying for a while.
I tried my best to keep up with their demands. I don’t know if I really messed up something all the time or if they just enjoyed my frustration and rising desperation so much. In any way I was not allowed an orgasm for weeks. On very rare occasions I was at least let out of the cage but even then they seemed to do it just to mess with my head even more and then finally lock me back up.
Every time I thought it couldn’t get any harder and more frustrating one of them found their own way of stepping it up and letting my desperation grow even further.
In the beginning my hope rested on Lynn. She had already said that she wanted to fuck me and immediately tried out her key. So I suspected once she gets the right key I would get to fuck her for the whole week. It was random who would have the correct key so on average every four weeks I would get out to fuck Lynn. Maybe now and then I might even be able to convince one of the others. So I was confident that I could live with the arrangement quite well after all.
However I don’t know if she played me from the beginning or if her lust was genuine, but after that one time in the shower with Lynn she changed her attitude. She was fucking around a lot. There was rarely a day where she wasn’t either out to meet up with some guy or I had to hear her moans from her room, sometimes for hours. But that wasn’t something special as I suspected and the girls confirmed. At the start I didn’t really care about it either. I wasn’t looking to date her, I just wanted to fuck her and honestly I didn’t care if I was just one of many to do that. When she had a guy over it was sometimes a bit annoying to hear them…and additionally problematic because it turned me on a lot to listen to her moans, but I could deal with that.
On the rare occasions when she didn’t have a guy to fuck her or if she got turned on while waiting for her dates she had found a new entertainment though. And that was watching me squirm and beg while I had to watch her playing with herself. She did let me touch her and kiss her, even lick her occasionally, but my cock never came out. After the first two key switches they had made, she at least tried it out. However luck wasn’t with me these two times and afterwards she didn’t care about it anymore. It seemed like in her mind watching me suffer while she pleasured herself seemed to give her more than sex with me ever could have. For some reason it seemed to turn her on incredibly hard watching me squirm. Apparently after a while even that was not enough for her anymore though.
The university I went too was reasonably big so there were a lot of students living in and around the city. That meant there was always, and I mean always, a party going on somewhere. I didn’t really have any intentions to go to those often though. Although I was starting to loosen up a little bit with those 4 girls around me all the time I was still more or less the introverted, socially awkward guy I had been for my whole life. So I went to one or two parties in the beginning to try to connect to some people that started studying with me. Since this however resulted only in mediocre success at best, I stopped bothering and focused on my studies. Lynn however was quite the opposite of that. She was down to party whenever someone hit her up.
One weekend came however where apparently no one wanted to go with her. So in the afternoon she burst into my room while I was trying to study and asked me if I would go with her to a party.
I was hesitant and wasn’t really keen on going.
“Oh come on please…it will be fun I promise.” Lynn tried to convince me.
“I don’t know Lynn, I am not really the guy for parties. Can’t any of the girls go with you?” I responded.
“No….Hailey and Anna aren’t home and Sarah will go to the gym later…” she explained annoyed.
She walked towards me and sat on my lap without asking.
“Come on its gonna be fun…we have some drinks, maybe dance a bit and I could even introduce you to some people.” she tried to win me over further.
“Lynn…dancing and meeting new people…really not my strong suit.” I tried to stay hard although her ass on my leg and her perfume were already weakening my resolve.
She put her arm around me coming even closer.
“Come on….maybe when we come back I might even try my key…..I am sure that could be your strong suit…” she said seductively as she slowly stroked the cage over my pants.
I already hadn’t cum for a couple of weeks or so. Therefore I was really desperate. Because of that my resolve melted away at the thought of a night with Lynn.
“argh….Fine I’ll come….when do we leave?” I gave in.
“Yay…we leave in an hour…” she said enthusiastically while jumping up and walking out of the room happily.
I tried to focus on studying but since the thought of potentially having a night with Lynn today was set in my mind I couldn’t really be productive at all. So after a while I gave in and just got myself ready for the party.
About an hour later Lynn and I were ready to depart. She was wearing extremely short, jeans hot pants and a black top that I am pretty sure was actually just a bikini and left very little to the imagination. You could even catch a significant amount of sideboob but knowing Lynn that was exactly what she was going for with that outfit. It was warm outside so I couldn’t blame her for the amount of clothes..but jesus……even for her that felt a bit more sluttier than normal.
After I had to listen to Sarah joking about how this would be the hottest “date” I would ever have and I would never get to go on a real date with a girl like Lynn let alone get to fuck her, we finally were on our way. The party was somewhere in a park near our home so we walked their. I couldn’t stop myself from looking at her tits or her ass in this outfit every so often. It was not surprising that her supply of guys willing for a quick fuck was never running out.
After a couple of minutes we arrived. There were already quite a lot of people there, Lynn had told me on the way that the party was organized by some people from her study program. It made me wonder why the hell she dragged me with her. Surely she must know someone who is studying with her, even though passing or even visiting courses hasn’t been her priority lately. It was already too late to back out for me now though.
After we grabbed some drinks it only took a minute or so until Lynn had found people she knew. It was a group of three guys and two girls. I learned later that it was two couples and one single guy.
“No way!!! Lynn going to a party with a guy?!…Damn man you must be quite something if that girl settles for someone” one of the girls joked as Lynn dragged me towards them.
“Don’t kid yourself” Lynn laughed and greeted all of them, “This is Nick, our new roommate.” she introduced me.
“Oh you had me shook there for a second girl.” the girl who apparently was named Emma joked acting relieved. They all greeted me and they seemed like nice guys all together. They welcomed me very nicely. We sat and talked with them for some time and of course had a few drinks together. It was honestly way more relaxed than I expected it to be.
The sun had already set when Lynn tried to get me to dance with her but I told her that not even all the alcohol in this town would suffice to convince me to do that. So she and the two girls went on their own while I stayed with the guys. I was a bit nervous being left alone with some random people that I had only known for an hour or so and was afraid it might get awkward but everything went smoothly. They just kept talking like they did before. One of them was actually studying in the same field as me. He was just a year ahead of me and told me about some of the courses, which ones were easy, which ones were hard. He even offered to help if I need anything. I really started to calm down and enjoy the evening. The amount of drinks was also helping my introverted self to become more relaxed but I sincerely enjoyed the company of these guys.
After a while the girls came back. The third guy, his name was Oliver and he was the single guy, looked at them.
“How do you manage to dance while keeping those tits in a tiny bikini like that Lynn?” he asked blatantly. He had been staring at her every now and then while they were dancing. It felt a bit weird but honestly I couldn’t blame him for it. It was quite the view.
Lynn laughed at him and playfully punched him.
“Its a secret….Why do you ask….would you like to see them?” she teased.
He grinned at her greedily.
“They must be quite the view.” he said.
“Well maybe you just might get lucky tonight…” Lynn responded as she bit her lip.
I was caught off guard by that. I mean it was no real surprise that Lynn was flirting with some guy, not even with a guy she had just met. But that blatantly and right in front of friends of hers….and me. It caught me off guard. When she looked at me and saw my confusion and surprise the grin on her face grew even bigger and their was lust in her eyes. The same lust I did see when she had been pleasuring herself in front of me.
They kept on flirting with each other for the whole evening. It did make me a bit uncomfortable at the beginning but the others seemed to be used to that type of behavior when Lynn was around. So I tried to just not bother.
At some point the inevitable happened and Lynn and Oliver went to grab drinks….although everybody knew that was not what they intended to do. It felt weird seeing her walk away with a random guy even though I had heard her fuck a lot of times already at home. I caught myself wondering what that would mean for my chances for tonight. As I realized that I seemed to be desperate enough to be down to fuck her even after I knew some random dude was inside her a little earlier that day, I felt embarrassed and quickly gulped down another drink.
The conversation returned to normal for a while, not caring about Lynn and Oliver. It was still fine although I did feel a little left out now that I was alone with the two couples. So I was just considering to leave the party early. I grabbed my phone to write Lynn that I would leave just in case she would be wondering where I am once (or if) she came back from her adventures with Oliver. But just as I had pulled out my phone I received a message from her. As I opened it up I nearly spat out my drink. I was looking at a picture of Lynn with a big cock in her hands and her lips wrapped around its head.
“Such a nice cock
I could feel the cage getting tighter in my pants. Listening to her fucking made me horny all the time but this was on another level.
The others looked at me and asked me if I was alright. I must have looked a bit shocked and probably made some suppressed moaning noises as well due to my cock desperately seeking attention.
“Y…Yeah….Sorry….I was…..It’s all good” I stuttered. I excused myself as my face turned bright red and quickly walked away from the group.
I walked around the park trying to sort out my thoughts and calm down. Though just a few minutes later my phone vibrated as I got another picture from Lynn.
This time his cock was placed between her big tits and she looked as happy as she could be.
“Sorry, can’t let a cock like that go. He will take me home with him. The key thing must wait for another time. Maybe I send you some more pictures though, would you like that?” she asked.
As my cock was pressing so hard against its cage that it nearly drove tears to my eyes I couldn’t stop my hands from typing: “Yes please.”.
“What a greedy cuck you are.” she responded.
I walked home waiting for another message but unfortunately for me Lynn only sent one more picture later that night. She was on her knees, her tits covered in cum and it said:
“Sorry, was a little busy 😉 Next time I’ll sent more”
I was a bit disappointed that I didn’t get to see more. However from that day on I was regularly getting photos from her hookups. Sometimes she even told me about them in detail when we were sitting together in the living room….And I loved every second of it. When I listened to her moans before, my imagination would go crazy and it turned me on a lot. However seeing what she was doing with all these guys….every imaginable position….her telling me and seeing her being turned on by reliving these moments in her head….FUCK it was hot. With every picture and every story Lynn told me I knew more and more that I needed her…I needed to fuck her. When she was out on a date I caught myself often just staring at my phone waiting for a picture of her with a cock in her mouth or up her ass.
The only problem was that she never did deliver on her promise to try out the key. Once while we were sitting in the living room and I had eagerly listened to a story of hers where she got spit roasted by two guys I asked her about it. I was a horny mess after that story and I begged and pleaded her to let me fuck her just once, told her that I needed it more than anything.
Lynn grabbed my face, kissed me and moaned into my mouth but then she pulled away, laughed and explained:
“No honey, you’re my cuck now….Cucks don’t get to fuck….they watch.”
I cried out of frustration as it hit me that Lynn, the girl that basically went to bed with every cock in this town, wasn’t going to fuck me. I still eagerly awaited every picture and story of her fucking around and although I was still craving to fuck the shit out of her, I had to admit to myself that my hopes of ever getting out of that cage had to be redirected to someone else for now….
My training sessions with Sarah had continued on in the mean time. It kept feeling really good to finally get my body back in shape a bit. I could feel the improvements every single time we went to the gym.
During these sessions Sarah continued to be a completely different person. She took her workout very serious and she was very ambitious. You could tell she always wanted to get the maximum out of herself and she wanted the same for me as well. It felt like she really wanted me to improve. She kept motivating me to push further without being harsh. My improvements were noted by her and she was genuinely happy for me. At times I even caught myself thinking about the possibility to get…closer…to her.
These thoughts were cut short though since outside of that training it was still the same old thing with her. Jokes on my expense about anything she could find. She didn’t seem to care who was around to hear them either. Didn’t matter if we were alone at home, if the other girls were with us or we were outside walking home from the gym or someplace else. So yeah the theory that she would get nicer once you get to know her, as Anna had claimed at our first meeting didn’t really seem to be true, at least not for me. On the contrary, Sarah seemed to really enjoy making fun of me. Comments about my dick size or how I would stay a virgin were things I had to endure on the daily. However stuff like that was pretty much the only thing remotely sexual between us if you could call it that.
She made fun of the cage but never even seemed to consider taking it off or playing with it. In the beginning I said to myself that she wasn’t even my type anyways but with time and the growing sexual frustration I couldn’t help myself. Especially seeing her in her tight gym clothes was turning me on quite a lot. I never really dared to ask her about the key though. It was very likely that the only thing I would get in return was a laughing fit and some humiliating jokes.
To my (pleasant) surprise however after a couple of weeks had passed, maybe it had already been one or two months, out of nowhere she walked into my room ordered me to get my pants off and checked if her key was working. And when it didn’t she would just walk out without another word. I was left really confused after the first time but she continued doing this every single time on the day they switched around the keys. She seemed to be very unlucky though since the cage never came off.
Over the next couple of weeks her attitude in the gym slowly changed as well. At first the supportive, encouraging, motivating Sarah slowly disappeared. At the time I just thought she might have just had a rough couple of days or maybe she had some competition coming up and wanted to focus on herself or something like that. But it did not stop.
When I had a rough day a few weeks later and did not manage to keep up with the training at all she snapped. It seemed like she had turned into a drill sergeant all of a sudden. She yelled at me to stop whining and being a bitch. She started to use her usual insults like “pathetic little virgin” and so on during the training.
It was probably heard by nearly everyone in the gym given how loud she was yelling and I could have sworn I saw a smirk on pretty much every guy that was walking by.
I figured that something was clearly going wrong since that wasn’t normal even for Sarah. However I figured it would be better to talk to her when she calmed down at least a little bit. So I endured the humiliation for that one day. We walked to the locker room without saying a word once we had finished the workout.
As I entered the locker room there was another guy in there. He was very muscular, clearly way stronger and better trained than me. The guy was completely naked and his body was still wet. He must have had just finished his shower. So far I had managed to miraculously dodge any weird encounters in the locker room but it looked like my luck had finally run out. And as if things wouldn’t get awkward enough in the following moments I couldn’t help but look at his cock for a second because it was massive. Even completely soft it was way bigger than mine was fully erect.
The guy just glanced at me when I entered.
“Whats up man.” he said and turned back to drying himself up without paying too much attention to me.
“Uhh…Hi” I said as I managed to take my gaze off of his cock and walked over to my locker.
It was right next to him and I noticed that the guy was towering over me. I tried to grab my stuff as slowly as possible, trying to figure out how I would manage to change without him realizing the cage on my cock.
As he finished drying off he looked at me again.
“Hey…you are the ‘pathetic little virgin'” he laughed.
My face turned bright red. I faked a laugh trying to appear as if I was taking it with a sense of humor although I was dying on the inside.
“Bro, what did you do to your girl that she is so harsh on you?” he asked.
“Uhhh…I….” I stuttered trying to figure out what to say.
“Did you cheat on her or something?…How do you even get a girl like that. I mean no offense but….you don’t seem like the workout type.” he continued as he put his hand on my shoulder.
“I…um….she is not….my girlfriend. We are just roommates.” I explained.
“Oh is that so?” he said intrigued.
“Well in that case…..” he grabbed some paper from his bag and wrote something down.
“Why don’t you go ahead and give her my number.” he said with a sly grin on his face as he held the paper towards me. I looked down at it wondering if he was serious right now. As I looked down my eyes were drawn to his cock again. I prayed he didn’t notice as I quickly took the paper to avoid even more awkwardness.
“ehm…sure.” I said as my face turned bright red once again.
“Thanks man, you are a good pathetic little virgin” he laughed as he patted my back.
He finished putting his clothes on and left.
“See you around man.” he said as he walked out of the locker room.
I was unsure about what just happened and very much embarrassed. Even at the welcoming party with the girls I hadn’t felt an urge that big to just disappear to anywhere else but here. I desperately hoped that I would never have to see that guy again.
As I walked out of the locker room Sarah was already waiting for me.
“Finally…what the fuck are you doing in there?” she asked. I didn’t respond but as she smelled me still sweaty after the workout she continued:
“You still don’t have the balls to take a shower in there….What the fuck takes you so long?”
“I…nothing….let’s just go….” I tried to avoid this talk.
We headed outside but she was not going to let this go.
“You are even more pale than usual. Whats wrong? You are not seriously a bitch about me yelling at you, are you?” she asked annoyed.
“No…but what the hell is going on with that anyways, Sarah?” I used my chance to change the topic instead.
“What do you mean? Haven’t you understood by now how pathetic you are?” she asked rhetorically.
“I…..” I wanted to protest but I felt like that wouldn’t get me anywhere so I calmed myself down, took a deep breath and changed strategy.
“Are you alright? You act very different during our workouts the last couple of weeks.” I inquired.
Sarah didn’t respond though.
“You can talk to me you know?” I continued but still got no response from her.
She just looked at me for a minute up and down as if she was searching for something.
“I don’t get it…” she said more to herself than to me as she took her gaze off of me.
“You don’t get what?” I questioned.
“Whatever….Now tell me why the fuck did you take so long. You didn’t find a way to get out of the cage did you. Did you jerk off you horny little bitch?” she interrogated sternly.
“N…no I didn’t.” I replied.
“I don’t believe you.” she grabbed the cage through my pants and dragged on it right on the fucking street and I groaned in pain.
“There…was a guy in there….we…..talked.” I gasped.
“You talked?….That doesn’t sound convincing…” she continued to keep a hold of my cage.
“We did….he….he heard how you talked to me….” I explained.
“So what? Was he offended….another wimp like you….” she said annoyed.
“No…quite the contrary.” I panted without thinking.
She finally let go of my cage.
“What do you mean, the contrary?” she said curious.
I realized I shouldn’t have let that slip.
“He…he was curious why my girlfriend would call me stuff like that.” I continued.
“Your what?” she said in a high pitched voice sounding actually disgusted by the thought.
“It’s what he thought….I corrected him” I hastily explained.
“You better, bitch.” she threatened, “but how do I know your not just talking yourself out of punishment for jerking off.” she grabbed the cage again.
A guy drove by on his bike and nearly crashed because he couldn’t take his eyes off of that scene.
My face turned bright red. I saw no other way out of this than to give her that fucking number.
“He….he wanted me to….give you his number.” I admitted as I handed her the piece of paper dejected and humiliated.
She looked at it for a second and then started laughing.
“You are such a wimp….But I guess you are good for something after all”
She continued laughing the whole way back home.
Two weeks after this incident she once again barged into my room after she had received the new key. I undressed as I knew the procedure by now although I still didn’t know what was going on with her. She inserted the key but still had no luck.
Annoyed she walked out of the room again as always as if nothing happened. I was still confused about her behavior but at this point I had given up trying to understand it.
The next night Sarah woke me up. The sun had not risen yet but Sarah was standing next to my bed shaking me until I was awake.
“What the hell is going on?” I asked barely able to keep my eyes open.
“Get up you lazy bitch we are going to the gym now.” she ordered.
“What?” I asked confused. We had not been to the gym together since that day. It was somewhat unfortunate in theory but based on how those workouts developed the last couple of weeks it was probably for the best. Additionally even when we were going back then, we were never up that early.
I had a bad feeling about this.
“Just go by yourself…What time is it anyways…” I said as I turned to the other side and tried to continue sleeping.
“God…listening to your whining in the morning is even more annoying. GET UP! I am not asking.” Sarah commanded.
I turned on my back annoyed and looked at her.
“So..what if I don’t do it…will you insult me again….” I asked sarcastically.
She looked at me with anger, an intensity of anger I had never seen before in her.
“Are you sure you want to find out?” she questioned devilishly.
In my groggy state my mind placed some flames in her eyes as I was looking straight into the devil’s eyes. She scared me and I was scared for her as well. I was certain something was bothering her and based on her reaction it must have been something serious.
“Ok, ok fine. I will come…just give me a few minutes.” I said dejectedly as I dragged myself out of bed.
We made our way to the gym without talking but she seemed to become a bit more relaxed with time. I went to the locker room to change and then headed out to meet Sarah. We started the workout as usual although it still felt weird after what had happened the last time.
After a couple of minutes I heard a voice saying:
“Mind if I join you guys?”
We both turned around and looked at the guy from the locker room the other day. I was surprised but Sarah got up and hugged him.
“Not at all.” she responded in the most friendly way I had ever hear her talk as I watched the guy grabbing her ass. I found it hard to believe that Sarah would let that slide and as she turned back to me I could have sworn she seemed annoyed for just a millisecond.
“I believe you have already met, so there is no need for introduction?” Sarah stated seemingly not caring about his hand on her ass after all.
I didn’t know the name of the guy and I knew something awkward was about to happen but I still had the hope to maybe salvage this and make everybody forget about the last time.
“Yeah, we did….But I didn’t quite catch your name last time.” I said as I offered him my hand.
“I am Jake.” he responded as he shook my hand although it felt like he wanted to crush it instead.
“Nice to meet you I am…” I started to introduce myself.
“A pathetic little virgin, I know.” he said without letting me finish with a sly grin on his face.
Sarah burst out laughing.
“Indeed he is.” she gasped while catching her breath and looking at me with a triumphant smile as if she had just won a gold medal at the Olympic games. My face turned bright red as I stared down on the floor realizing that there would be no way to salvage this situation.
The workout went on and they both were mocking me whenever I failed at an exercise. Sarah didn’t have the anger in her voice she had the last time but she didn’t go any softer on the insults. They were simply having fun and although I really wanted to disappear, in some weird way I was happy to see Sarah having fun. I thought maybe this would help her finally relax and even open up about what was going on. I thought I could endure one more gym session of pure humiliation if this helps us get back to normality.
However the looks she gave Jake every now then confused me. There was some genuine admiration for his body in there and I am gonna be honest it made me feel a bit insecure about my body since she would definitely never look at me like that. But there was something else in her looks as well…it seemed like she…detested him….but she obviously had invited him there so I must have imagined that I guess.
After we had finally finished we headed to the locker rooms together. Jake and I were about to take the turn towards the men’s locker room when Sarah grabbed my arm and pulled me towards her.
“I expect you to take a shower this time…” she whispered.
“But I…” I wanted to protest.
“You understand me?!” she said more sternly and the anger was back. Her hand was grabbing my arm painfully hard.
I nodded and she finally let go of me.
I hesitantly got out of my clothes when I was in the locker room. Our lockers this time around were on opposite sites so he didn’t see it immediately. My face had already turned bright red though.
“Dude I just wanna…” he started to say as he turned around and wanted to walk over to the showers.
I didn’t look at him but it was obvious why he stopped talking.
“Bro what the FUCK is this?” he asked pointing at the cage.
“A chastity cage…” I whispered more than anything and let out a big sigh.
“A chas….Wait she isn’t kidding is she? You are actually a virgin? What, are you doing some kind of chaste till marriage thing?” he asked confused. Apparently Sarah had not told him about our relationship at all. That probably was my chance to get out of this smoothly but the embarrassment and the fear of what Sarah would think of next stopped me from thinking clearly.
“N..No it’s….they locked it onto me….” I explained reluctantly.
“Who?” he was still endlessly confused and couldn’t take his eyes off of it.
“……My roommates…..” I sighed.
He kept on asking questions until he figured out the whole situation, it was mortifying but so far he seemed just interested, curious and he had stopped making fun of me. That was a good sign in my books. His last question caught me off guard though.
“Sooo…I mean I get it they got the keys and all but….Bro, you do realize there are other ways out of this thing right? Its just plastic man…:” he said.
I wanted to respond immediately but I hesitated. I mean I wasn’t stupid I knew if I really wanted it I could have been out of that thing a long time ago. So why? Why didn’t I do it? Yes if they found out that I had gotten out they probably wouldn’t allow me to live there anymore. But was that room really worth all of this. No…if I was being honest with me…fully honest, that was not the reason I endured this. I didn’t even think about looking for a new place to stay all that time. Slowly I had to come to terms with the fact that I…..I liked it…..I really did…..not just in a horny moment after I got teased into a total mess….but all the time.
Jake had this sly grin on his face again as I snapped out of my thoughts. I hadn’t responded for way too long.
“Wanna know what I think?” he said and put his arm around my shoulder as he lead me to the shower. I couldn’t have cared less about what he thought at that moment but I still didn’t manage to say anything.
“I think you truly are a pathetic little virgin…..and I think you like…..no you LOVE it, man” he continued his observations.
I knew he was right but I couldn’t admit it, I wasn’t ready to admit it to myself but definitely not to this random guy in a gym locker room.
“No I….I just need the place to stay man” I responded finally hanging on to the one saving grace I managed to come up with.
He laughed and began to take a shower in silence.
As he was ready to leave he turned to me once again.
“Well buddy, I am gonna go and have fun with one of your mistresses now. You have a great day man….and I will talk to Sarah, who knows maybe next time we are in here……you’re gonna be my bitch too.” he teased me and laughed as he wiggled his massive dick around.
I walked home alone that day but it was probably for the best. I really needed some space after that humiliating morning. I walked straight to my room and laid in bed. I was lost in my thoughts and drifted off to sleep for a while. It was already afternoon when I woke up. My thoughts were still going crazy and I didn’t feel too much better. I had received a couple of pictures of Lynn where she was blowing a guy and then later on was riding one…I was pretty sure they were with two different guys. Two different hookups in one day and it was only afternoon that was impressive even for Lynn. But at the moment even these pictures couldn’t lift my mood. They didn’t even arouse me as much as they usually did. I couldn’t stand laying in bed and staring at the wall any longer, so I got up.
As I walked into the living room Anna was sitting there.
“Hey, wanna watch something together?” she asked as she noticed me. She was going through Netflix right now searching for something to watch.
“Nah…I don’t feel like it.” I responded.
It had caught me off guard a little bit when I found out that she was an integral part of how my whole situation developed. But Anna had a way of winning me over. She had me wrapped around her finger in no time whenever I was questioning her intentions.
So usually I was always down to spend some time with Anna. Over time I had spent some time with every single one of the girls under more normal circumstances and it was nice and enjoyable most of the time. But with Anna it felt different, we laughed a lot whenever we were together and I really felt like I was starting to develop feelings for her. She probably was aware of that too, although I never had told her about it myself.
What she definitely knew without a doubt though was that I was always eager to spend some time together. So she was rightfully surprised when I rejected her offer.
“Is something wrong?” she asked seriously concerned.
“No…it’s just….I don’t know….” I asked not sure how to explain it to her.
She looked genuinely concerned realizing something was bothering me.
“Ok…then we are going out.” she said cheerfully and determined.
“What? I really…”I wanted to protest.
“Nope, no discussions. Go on get ready you have 5 minutes.” she stated as she smiled at me.
I couldn’t resist her smile…her cute freckled face…god she was so beautiful…and maybe it would be good to be distracted for a while anyways.
“Fine.” I agreed and walked to my room to get ready.
It was a nice sunny day. Anna was wearing a sundress with a lot of cleavage showing as always. But for some reason she seemed even more beautiful to me than usual with her long red hair falling down over her shoulders. We walked around for a while just enjoying the sun, we talked and laughed. It was nice and it allowed me to rest my mind for a while. We came along the coffee shop we had met for the first time.
“I gotta go and grab a coffee real quick. Should I get you one as well?” Anna asked.
“Uhm…sure, thanks.” I said and watched her swaying ass as she walked into the cafe.
When she came back we walked a little further and sat down at a lake to drink our coffee.
“So wanna tell me what bothers you?” Anna asked carefully.
“Uhh…I don’t….know…” I responded.
“You know you can talk to me right?” Anna said.
“Yes….I know…..it’s…..So I went to the gym with Sarah this morning….” I started to explain hesitantly.
“Oh, did she overdo it?” Anna questioned immediately.
“I don’t know….no I don’t think so….” I continued unsure of what to say.
“You know you can always tell us to stop right? I know we might be rough on you sometimes….some more than others…” she said as she stroked my leg, “but even Sarah or your ‘goddess'”, she laughed saying that word, obviously talking about Hailey, “they will respect it if you say something is too much. You belong to us, don’t forget that”, she warned me, “but we all want to keep it that way, you know what I mean.” she finished calmly and smiled at me.
“That’s good to hear, Anna. Thanks…But I think I was aware of that already…more or less.” I said as it was indeed really reassuring to hear that.
“Ok good, then what’s the problem, what did she do?” she inquired.
I explained to her what happened. Anna did listen to me carefully although I felt like just for an instant I might have seen her smirk now and then.
I wasn’t sure what to do when I finished my report about this morning and the past weeks with Sarah so I looked at her and then shyly onto the ground. Anna giggled in response to that.
“You are cute when you are embarrassed, so I can’t blame her for wanting to see you like that…But the attitude seems honestly weird, you are right. I will talk to her and see what’s going on. Maybe she opens up to me a little more. But as I said if you are uncomfortable with what she expects from you then you gotta tell her yourself.” she repeated.
“It’s….It’s not that I don’t….I am afraid…” I whispered.
“Oh don’t worry sweetie, Sarah just acts tough…she will respect your boundaries trust me, she wouldn’t have taken you to the gym if she wouldn’t like you.” Anna reassured me.
“No, not afraid of Sarah…scared that I…..really……like….this” I stuttered.
“ohhhhh,” Anna exclaimed as she understood, “right…must be quite a wild ride if you have no experience at all.” she giggled.
She pulled me in for a hug and stroked my back.
“Don’t worry about it, there’s no shame in liking stuff like that. I mean we are all into it too, just from the other side. I wouldn’t have chosen you if I wouldn’t have thought you would be submissive and into this stuff…Although I must admit…you did turn out way better than I expected.” she laughed as she let go of me.
“And you can always talk to me…about anything, ok?” Anna eased my mind further.
That talk with her made me feel way better. My mind had finally stopped racing and calmed down. Although a different feeling returned at the same time. I looked at her with her friendly, reassuring eyes, staring right into mine and I could feel the butterflies in my stomach.
“Yes, thank you Anna I…….I….ahem…thank you….” I couldn’t do it. I wanted to tell her how I feel about her but I couldn’t. I was afraid of the response. We had a nice relationship so far and this conversation made me feel even closer to her. I just couldn’t risk losing this so I held myself back.
After we continued walking around for a while we were on our way back when Anna remembered that she still wanted to go buy some drinks and snacks for Hailey’s birthday.
“Hailey’s birthday? I didn’t know there was a party…I didn’t even know that her birthday is around the corner.” I realized.
“Oh don’t worry about it, Hailey never celebrates it…she doesn’t really like her birthday for whatever reason.” Anna explained.
“Oh okay….wait why do you need to buy stuff then?” I asked even more confused than before.
“Well, since SHE won’t celebrate, but WE deemed it necessary….and let’s say she made it very clear that she doesn’t want any surprise parties or anything alike going on….we made it a tradition that at least all of us would have a nice evening together.” Anna explained.
“Ah, ok good to know.” I understood.
“Sorry I didn’t think about it. I probably should have told you earlier. I don’t need to buy much though so you can go ahead and head home already if you want.” Anna apologized.
“Oh no, its all good I come with you, help you carry the stuff. No problem.” I responded. I didn’t have anything else to do anyways. So we headed to the next grocery store.
We were standing in front of the liquor shelf in the store when some guy came up to us.
“Who do we have here? Long time no see.” he said while he slung his arm around Anna’s waist.
I was surprised by how forward that guy was and was nearly expecting Anna to punch him in the face.
“Hey, Henry.” she said and smiled at him instead.
“So what have you been up to? You haven’t texted me in quite some time.” he asked Anna while his hand was suspiciously close to Anna’s ass.
“I am sorry, Henry. I was quite busy in recent weeks.” Anna reported.
“I see…and who is that? You got a boyfriend I don’t know of?” he joked while looking at me.
I could feel my hate for that guy growing with every second. I didn’t know how they knew each other or what their relationship was. But seeing how he touched her without hesitation and how he talked…it was enough to know I hated him. Well realistically it was probably mostly the jealousy talking but he most definitely appeared to be an asshole nonetheless.
Based on the mix of a content grin and a scolding impression on the face of Anna my feelings were probably shown on my face more than I would have liked. Henry didn’t seem to notice or care though.
“No, to be my boyfriend he would need to have the courage to ask me out….” she said looking at me and taking a small break as if waiting for me to say something but I was to absorbed in my jealousy at that moment to realize this. Anna let out a barely audible sigh and continued:
“Henry, this is Nick our new roommate. And Nick this is Henry a…..friend of mine.” she introduced us to each other. We shook hands but the suspense was tangible.
“Nice to meet you man, hope you stay longer than the last guy.” he said and then immediately turned his attention back to Anna.
“So, you wanna meet up sometime, or are you still too busy?” he asked as his hand was groping Anna’s ass.
“Sure why don’t you come by…tomorrow?” Anna responded while trying to catch glances of my reaction to see what was going on inside of me.
I felt my stomach twisting and turning hearing these words but I didn’t dare to say anything. I didn’t want to give Anna the wrong impression. She wasn’t supposed to know what I felt for her.
“Great, I will text you.” Henry said as he gave her a small clap on her ass and turned to leave.
I looked at Anna skeptically now that Henry was gone.
“What?” she asked.
“Who was that guy?” I responded with a question myself.
“A friend.” she answered.
“Really?….A….friend?” I remained skeptically.
“Yes…with certain benefits” she explained. I felt a pain in my heart hearing this.
“Seriously?….That guy?….He seems like…..an asshole.” I said hesitantly. Anna just grinned at me knowingly.
“What? Are you jealous?” she asked teasingly.
“What? Jealous….N…No…why would I be? He just….doesn’t seem like your type.” I tried to dodge that accusation with limited success as her smile showed me. However she did let it go….more or less.
“Well…..his benefits are quite…big…” she whispered in my ear and I could feel myself blush.
“Besides it’s not like any nice guy is asking me out….or have I missed something?” she asked. I did not respond however. Her insinuation about his dick size had me still flustered.
We finished the shopping and headed home but in my mind the events of that day were playing on repeat over and over. The morning would have been crazy enough to have my mind racing for a week and the talk with Anna had given me a lot to think about as well but all of that did not really matter. What I was wondering about were all these dating hints Anna had dropped the whole time in the grocery store. I didn’t really notice them in the moment but while I was reliving the day in my mind, they became clear to me. Maybe even clearer than they actually were but I couldn’t help it.
Was she dropping signs? Did she want me to ask her out? Those feelings that I had…were they actually mutual? I was doubting it in the beginning, convincing myself that I was just imagining things. But with every time I remembered the conversation I started to believe I might have a chance with her after all.
For her “date” with Henry the next day I left the house. I couldn’t stand it to know that this asshole was in the other room fucking her while I was sitting in my room figuring out if she liked me or not.
I met him briefly when he was heading out as I just came back home. While looking at him all the jealousy came up again and I realized I needed certainty.
A couple of days later Anna had ordered me into her room for the evening. It was a regular thing now that she would invite me to her room so I would perform oral on her. She called it training sessions. I still had never been allowed to see her naked or touch her which was incredibly frustrating but nonetheless I enjoyed these nights a lot to be honest.
I had been getting good at understanding her body and understanding what she likes and what not but somehow she always managed to distract me just enough with her teasing so that I couldn’t focus enough to get her over the edge.
I was standing in front of her door, feeling as nervous as I could be. My hands were shaking as I took a deep breath and knocked on her door. As always she opened the door just a little to hand me the blindfold but this time I did not take it immediately.
I stared at her for a few seconds nervously.
“Is something wrong?” she asked confused. I took another deep breath.
“I….ehm…would you…..I was won…..Would you go on a date with me?” I stuttered and finally blurted out. She looked at me but I wasn’t sure what it was I saw in her eyes: surprise, happiness, confusion, intrigue, disgust? I didn’t know, I wasn’t able to read it.
However she didn’t say anything. She just smiled at me and put the blindfold in my hands and nodded invitingly. I didn’t know what to say. To ask the question itself had me exhausted and stressed out already. I was prepared for a lot of different scenarios but I wasn’t able to wrap my head around this sort of response. So I resorted to the routine and proceeded as usual. Taking the blindfold, getting naked and preparing myself to pleasure her.
I could feel her being unusually wet this time and although my head was still trying to figure out what this reaction to my request meant I had her moaning like crazy after just a couple minutes. I realized this might be my chance to lighten her mood and maybe afterwards I could go for another shot. Anna was trying her usual whims at trying to tease me and make me lose focus by playing with the cage and my balls but she was way too into it this time. I could feel her getting close and it was different from the other times. I had gotten her close before, she had admitted it herself even, but it always felt like she still had full control. This time though she was lost in her lust. I could tell by her loud, heavy moans and the way she was starting to grind on my face.
“Oooooohhhh fuuuuck……Yeeeeees……Fuck you have gotten so good with your tongue.” Anna moaned and finally broke the silence.
“You……ohhhhhhh fuuuuuck.” she tried to start saying something. However this time she was the one that couldn’t focus anymore. She ground faster on my face as my tongue was running over her clit over and over. Her breath got shallower and shallower and then with a loud:
“YEEEEEEEEEEEEEEEEEEEEEEEEEEEEES” that was probably heard by everyone in the house she came. She came hard right on my face. It was incredible, like I was in heaven. I was in trance and just kept on going, mesmerized by her taste, her smell and her moans until she finally sat up. I still had a hard time believing that I finally did manage to make her cum.
Anna glided down, her pussy placed right on top of the cage her breast pressed against my stomach and her head rested on my breast as she was catching her breath.
“Wow…..you have really come along way since that first time…..” she said still breathing heavily.
“Ehm…thanks….” I still didn’t know what to say. I could hear the grin on her face thanks to my flustered response when she continued talking.
“You know….I think you deserve a reward for that….” she whispered.
I got excited at the sound of that and my cock was pressing against the cage even harder than before.
“Unfortunately I don’t have the key…….” Anna continued after a moment of silence.
The disappointment hit me hard. Although I knew she probably didn’t have it currently I had not thought about it in this moment and had already mapped out scenarios of finally having a relieving orgasm while fucking Anna all night long.
“So I am gonna give you a choice….” Anna said as she had finally regained her breath but it seemed like her lust was not fully satisfied as her pussy started to grind on my cage.
“Option 1….” she started to explain as she got up and put the cage between her massive tits, “is I let you touch me….all of me….these gorgeous tits….my nice thick ass you have been staring at for so long….I even allow you to finger me to one or two more orgasms right now….” she said while still mercilessly teasing my cock in its cage and giving it a titjob.
I was going nuts. It felt like she had me on edge just like that without even needing to unlock me. Precum was dripping out of the cage and on to her tits. I was about to agree to this no matter what the other option was.
“Or Option 2….” she continued and licked the precum off of the cage, “I agree to…..” she made an agonizingly long break while she laid back down next to me and whispered: “go on a date with you.”
I was dumbfounded. Was that a trick? Or was that really happening? Would I really go on a date with her?
“Before you decide though…this is a one time offer…” she explained, “If you decide to touch me, give me pleasure that I….oh desperately need right now…there will never be a date.” she grabbed my cage again.
“I will even give you the promise to give you the pleasure you so desperately need….when I get the key the next time….How long has it been since you last came? You must be going crazy right about now.” she added teasingly while caressing my whole body. I could basically hear my cock yelling at me to not choose the date as it was throbbing in its cage.
“But if you decide otherwise….I consider us dating….so these nights….won’t be happening anytime soon….I am a decent woman after all I don’t jump into bed with every guy.” she whispered in my ear with a big grin on her face, seemingly happy with seeing my brain work hard on a decision.
My mind was racing. I wanted to date her, I wanted her more than anything but what if I mess up? I might ruin all of this, the friendship I had with her….these nights….I wouldn’t even get to pleasure her anymore…and by god I really needed that orgasm….I mean I made her cum once I could do it again and then get other rewards…even better rewards. I was fantasizing about just taking her right now kissing every part of her body, massaging these massive tits she has been teasing me with since day one…
“So….what will it be Nick?” she whispered in my ear while playing with my balls. I gulped hard….
“I…..I want…..to date you, Anna.” I said hesitantly while my body was cursing me for it. She immediately took her hands away from my balls.
“Ohhh, you are so sweet.” she claimed and kissed me on the cheek. I could have cried as I thought about what I might have given up. But once the immediate sensation of her hands on my balls had subsided just a little bit I could feel the excitement. I was going to go on a date with Anna……I would have never imagined that when I met her a couple of months ago….not in my wildest dreams.
While I was still trying to order my thoughts Anna pulled the blindfold off of me. I looked at her confused and a bit disappointed as I saw she had put on a shirt that was reaching down below her ass and covering all the important parts that I was not allowed to see…yet. She giggled as she saw the disappointment in my eyes.
“What? I told you I am a decent woman.” she joked with a sly grin on her face.
“Right….so that means we are dating now?” I responded carefully.
“It appears so….” she said happily, “However there is one condition beforehand…” she continued.
“What? What condition?” I asked while panicking, afraid of losing the chance to date her after all.
“You do realize that this can’t affect your relationship with the other three girls right?” she asked.
I looked at her confused. She wanted to date me but expected me to still do whatever the others say? I mean I didn’t really think that far since I never assumed to get to this point. But nevertheless it felt weird that I would still serve the three other girls while potentially getting into a relationship with Anna. Or was that just a game for her after all?
“Ehm…okayyy” I said hesitantly. I guess after all the other three didn’t really do anything too intimate with me so far. Whatever….I definitely wasn’t about to give up my chance with Anna for this.
“Good I am glad you see it the same way….so I need you to make sure the others are ok with us dating.” she explained.
“What? So you expect me to ask them for permission to date you? What are they your parents or something?” I joked but Anna looked at me seriously.
“I mean it Nick…I don’t want to endanger our dynamic….” she stated sternly.
“Okay…Okay…I will ask all of them.” I assured quickly before she would take back her offer. I couldn’t really see why anybody would have a problem with us dating anyway. The only potential problem could have been Sarah in my mind. But knowing her she would probably believe I would mess up my chance with Anna anyways. And I was confident that Sarah would enjoy watching that way more than denying me the opportunity in general.
“Great then you can leave now.” Anna said.
“Leave? Why? I have always slept here in these nights.” I reacted confused.
“Well I told you sweetie…these nights are over now…so go on back to your own bed.” she chased me out of her bed.
“Alright…Alright I am going…” I said laughing, “and I am looking very much forward to our date.” I told her looking deep in her beautiful eyes.
“Me too…so you better hurry to get your permission, mister.” she said jokingly with a smile on her face….