A Complicated Situation Ch. 01

** Author's note: This story came out of a challenge to write a story about a picture. The picture was a drawing that had a Domme sitting in an easy chair, high boots, a collar on a man who was kneeling, gagged, and bound who had turned around to find a butter knife on the floor behind him. This is a story that lead to that scene.**

My name is Tom and how I got into this situation is complicated.

I moved into this building a couple of months ago. I don't really know many people in town as I got this job out of college and had to move. My neighbours all seemed nice, but most were too busy with their lives to socialize. There were a couple of women on the floor who were single, and with whom I flirted a bit in the hallway when we crossed paths. There was Amanda, across the hall from me, and Teresa who lived down the hall with her brother Mike. I ran into Amanda more than Teresa, but I really had the hots for Teresa. Amanda always seemed a bit too unavailable, but she was a lawyer and always had those power suits on, so it was hard to tell.

One day  just after I got home from work there was a knock at the door. My eyes lit up when I found Teresa on the other side. She was wondering if I played a card game called Euchre. She and Mike wanted to have a Euchre night-in on Friday and wondered if I was available. I did indeed, and more than that, it was a perpetual lunch time game that I played through high school and college. I was a terror at the Euchre table and always enjoyed a good game.

As we were chatting Amanda was getting home, and Teresa asked her if she would be our fourth. They would have food, if we just wanted to bring our own drinks. An excited Teresa left us, already planning the night in her head. My eyes may have just lingered a bit long on her cute ass bouncing down the hall back to her apartment.

When I turned back Amanda was watching me, amused. I cleared my throat, but before I could say anything she said, "She does have a nice ass. You don't need to be embarrassed."

I coughed and said "So you play Euchre much?", just to change the subject.

Somehow this got us both to bragging about how good we were at the game, and ended up making a bet. She never bet money, so we talked about various other things: Cleaning the winner's apartment, but her place was spotless, cooking a meal for the winner, but I had trouble boiling water. We realized that we had different needs and abilities and somehow landed on the winner gets to choose the reward they want.

That night I fantasized about her cleaning my apartment in a slutty maid outfit. It was a very revealing slutty maid outfit, and I had a lot of fun jerking off to the images wandering through my head. She had a very nice ass too!

Over the next couple of days there were a lot more smiles and flirting with both Amanda and Teresa when we passed in the hallway. I was really looking forward to Friday, and was jerking off a lot.

On game night we told Teresa and Mike that Amanda and I could not be partners because we had a side bet going, so I ended up with Teresa as a partner. Both women had chosen shirts that were a bit low cut, and their cleavage was a constant, arousing distraction for the evening, only interrupted by visions of their asses in tight pants when they got up to get something. Mike seemed to be having a lot of trouble with Amanda's outfit, but I was having trouble with both of them.

I won't relate the game play, since I don't know if you know the game, but at the end of the night we were tied, and playing the rubber match with Teresa and I ahead 9 to 4. I was feeling good about French maid outfits, when in two hands we lost, and now I had Amanda gloating and Teresa disappointed in me.

We wrapped up our night, and as Amanda and I walked back to our apartments, I asked her what she was going to choose. She said she had a couple of ideas, but had not quite made up her mind yet, but would let me know soon. With a last, lustful, lingering look, I turned into my apartment and started getting ready for bed, thinking through all the wonderful things I had seen this evening. Yes, I was going to really enjoy jerking off tonight.

Just as I turned off the light in the bathroom, I heard a knock at the door. I was surprised, and then hopeful. Maybe Teresa or Amanda were coming for a booty call? I checked the peephole, because you do that at 1AM, and Amanda was out there. She had not changed yet and my heart beat a little faster. I opened the door.

"Hi!" I said.

She was blushing a bit, "Hi!", she replied. "I decided what I want as my choice!", and she held out a small box to me. As I took it, she said, "Can I come in?".

"Oh, yes, yes!" and I moved out of the way, she came in and I closed the door behind her.

She said, "I was thinking about this, and realized I really want this, but if I wait until I sober up in the morning I will probably just pick something different. Go ahead and open it up."

I opened the box, and in it was a metal chastity device. I looked at it, then at her, then back to the box. "You can't be serious!" I said.

She was still blushing a bit, but looking me straight in the eyes, "I bought this ages ago when I was in college, and hoped my boyfriend at the time would play with me. He didn't, and we broke up shortly after that. He was the last person I dated, as school and then work have been my priority. I just want to have the experience of having someone locked in chastity. I need to know what it feels like. I don't plan to pull you into a relationship or anything, but I do want this as my choice. Are you going to welch on the bet, or let me have my choice?"

I thought about it. and to be clear, I thought about doing as I was asked, allowing Amanda to have her choice. I had honestly never thought about chastity before. It was currently having a very non-arousing effect on me. On the one hand, I don't think it is reasonable to expect something this personal, this intimate, out of a bet between neighbours. On the other hand, if I refused all those fantasies about Amanda, and probably Teresa could just be thrown away, and I was probably too horny to let that happen just now.

She watched me as I thought this through, and finally I said, "I have always been a man of my word, and if this is your choice, I will accept it. How do you want to do this?" 

She told me to go to my bedroom or bathroom and put it on and she would wait here, and she would ask to see it locked on when I came back. 

I went into the bathroom, and opened the box. It took me a while to figure it out, and it only took two "Do you need some help in there?" giggling enquiries for me to get it on and locked. I noticed that there were no keys to the lock, and locking it was a tough decision, but I did it and went out to my living room. 

Amanda looked very eager and excited as I came out. She stood as I came to the couch, and said "Show me." Embarrassed, I pulled down my pajama bottoms to show her. She made a sound that was hard to describe, something between a sigh, a meep and a moan might be the best way to say it. She reached out and grabbed my caged cock and balls in her right hand, and that had an electric effect on my cock, it jumped and twitched. 

Realizing she had reached out without thinking, she started blushing furiously. "Sorry, I didn't mean to....", she cleared her throat and backed up. "Anyhow, I was thinking we could meet for breakfast tomorrow morning and you can describe everything to me about how the cage is feeling. Say, meet in the hallway around 10?" 

I think I went into shock at that point. "But I thought you just wanted to see it on then take it off? I can't just have my cock locked up like this!" 

I was watching her face, and I could tell there was a lot going on in her mind just then. She had probably been working on this fantasy of hers for a while, and wanted to push through with it, but we also did not know each other too well and she did not know how hard to push. What she finally said was, "Well first, I don't have the key here so I have to go anyhow, and second my choice was to have you put it on, and while I was not thinking this was some backing into a D/s relationship, I do want to get the full experience out of my choice! We can discuss how and when it comes off at breakfast tomorrow!" With that, she turned and headed for the door, and was gone before I could process what she had said. 

My night after that was the most troubled, frustrating night of my life. I was so bloody horny, It was bad enough before Amanda came over, but from the moment she touched my caged cock it went up to an insane level. I was also angry at being locked and left. Also, oddly, the fact that Amanda had this interest in me felt intimate and arousing. Needless to say, getting to sleep was difficult. Then I was surprised to wake up with a great deal of discomfort from my cock and balls. It took a moment to realize I was getting an erection in my sleep and the cage was crushing it. This happened several times overnight, and finally around 7AM I got up and showered. As I was getting dressed it occurred to me that I was going to have to go outside with this cage on. I wanted to change the plan. I didn't even want to go into the hallway like this to knock on Amanda's door to discuss this. We hadn't even exchanged phone numbers so I could not even text her. 

I got ready, resigned and feeling so embarrassed, I headed out the door at 10, to wait for Amanda in the hallway. While I waited, I heard a door open down the hall and turned to see Teresa coming down the hall with a garbage bag, heading to the garbage chute, which meant she would walk right past me.  She was not really dressed, she was just wearing an extra long shirt, and did not have a bra on, her breast moving with every step, and nipples clearly visible. It made me so much more aware of the cage, aware of her. 

"Good morning." she said, as I struggled to look her in the eyes. I must have been blushing quite a bit, and she must have noticed, but just kept smiling a sweet, endearing and intimate smile. "Last night was a lot of fun, thank you for coming over!" 

"Hi," I replied, "it was, and thank you for organizing it!. We should do it again soon, and next time we win!" I meant that, I wanted an opportunity to get even with Amanda! 

She laughed, "There is always winning and there is always losing when playing cards. It is fun winning, but it is more fun playing and having company than anything else. Mike and I decided to have a side bet too, after hearing what you and Amanda were doing, which is why I get to take the garbage out all weekend! You and Amanda never did tell us what you bet was about. How did that go?" 

Embarrassed, and clearing my throat, I said, "Well we're heading off to breakfast to discuss that." 

"Now you just have me more curious!" she said, then "Excuse me, I need to get this to the chute." and she proceeded to walk down the hall, as my eyes followed her. 

Amanda's door opened at this point, startling me a bit. I made a note to myself about updating my life lessons, the hypnotic power of a woman's ass grows exponentially when you are really horny and locked in a chastity cage! 

"H!" I said, blushing again. She was dressed nicely, but the only thing that stuck in my mind is that I could see her nipples poking through her top and would have to really struggle to keep my eyes focused on her face. 

She smiled. "Good morning! I heard voices out here?" 

I pointed down the hall and said "Teresa was taking the trash to the chute, and stopped to chat with me on her way by."  

By this point in time, Teresa had deposited her trash and was walking back our way looking just as distracting as she had on the way from her apartment. I was feeling like I was going to explode at this point. It was embarrassing enough being here with them, while locked in a cage, when one of them knew, and the other did not, but being so horny, I wanted to look everywhere all at the same time. I just hoped I did not say or do anything to make this more embarrassing. Hoping it would be over soon, but only really hating that I could not just leer!

Amanda and I started walking towards the elevator, which was towards Teresa. 

"Thank you so much for last night Teresa." Amanda said as we came together. "It was so much fun, and I have not done that sort of thing in ages. Next time maybe we will do it at my apartment?" 

"That sounds like a great idea. I will talk to Mike. We don't go out much, so most weekends work for us." she said smiling. She looked at me, then back at Amada, "I hear you two are off to have breakfast and talk about your side bet? I would invite myself along otherwise. Tom wouldn't tell me about it, but he was blushing a bit when I asked." 

"We are, and I think he is just embarrassed at losing a bet. Especially after his bragging about his Euchre skills yesterday." Amanda replied. "Anyhow, we are going to get going. Talk to you later." 

"Enjoy! Bye" Teresa said as she continued back towards her apartment. It took a great deal of willpower to keep my eyes forwards towards the elevators rather than watching her as she went. 

We were quiet for the walk to the diner a couple of blocks away. An awkward, but very intimate silence. I had done this type of walk with a one night stand before, and it was similar but very, very different. 

At the diner, in a corner booth, we finally got our coffees and someone had to break the silence. I started with an "... Ummmm." 

Amanda put her hand on my arm and said, "Please let me talk first?"

Making sure I was looking her in the eyes, I nodded, and she continued. "I really want to thank you so much! I have been thinking about this for so long! I was around 15  years old when I first started fantasizing about having a boy in chastity, and I only ever talked about it with that one boyfriend, and that conversation ended our relationship. I have been terrified of bringing it up ever since!  If I had not had that whole bottle of wine last night, I would not have even brought it up. It's what gave me the courage to try. Last night felt liberating, it felt like the most exciting and arousing thing ever. I went back to my place and masturbated so much. More than I ever had before. I had some of the best orgasms of my life last night, just because you did this for me. So thank you!"  She was still holding my forearm, looking at her, she looked so happy, so grateful and so genuine, I started to feel that it was worth a bit of discomfort for a night. Listening to her talk about her arousal, her orgasms, and her sexuality however was also just pushing more of those horny buttons I had. I was about to respond, when she said,  "Okay, so tell me everything! Tell me how it felt, how your night went, how your morning went, how you are feeling now, everything!" 

I took a deep breath and started talking, it came out disorganized and out of sequence, but as I talked I ended up saying everything: How I felt the night before, how close I had come to just saying no, how shocked I was to be left in the chastity cage instead of released, the intolerable night of waking up with every night erection, how it felt leaving the apartment caged, being out in public that way, everything my eyes saw that morning in the hallway or on the way to the diner, or in the diner (our waitress was hot). I continued and told her what I had planned if I had won the bet, what her and Teresa's outfits were doing to me last night, the fact that I had just about been ready to jerk off when she knocked, and what I had hoped for when it was her! I even told that before Friday night I had been jerking off to thoughts of her or Teresa for a long time now.

At the end of my story I was looking down at the table, really not sure why I was so candid or forthcoming about all the things I had said. I was feeling embarrassed in a different way now. She had listened without interrupting me, and I was pretty sure she now thought of me as a pathetic, perverted jerkoff. 

"Thank you!" was all she said. When I looked up, she was smiling, her eyes were happy, her pupils dilated, and yes, I had noticed that her nipples were still straining against the fabric of her shirt. 

There was silence for a bit, but not awkward this time. It felt intimate, and I don't think either of us wanted to break it. 

Finally I said "I am feeling differently than I thought I would, and I am actually happy to have been able to give you this experience, but I would like to get out of this now. When can I get this thing off?" 

She looked a little embarrassed. She said "Well there is a small hitch in that plan that might delay releasing you until tomorrow. You see, somewhere between my first orgasm, and the last one where I passed out, I took the keys to the lock and put them in a safe. I set the combination lock using an app I have, and the timer will give me that combination tomorrow night at 6PM which is when I can unlock you. My mindset last night was that I did not want this feeling to end, even now, I just want to go home and spend the rest of the day masturbating. Instead, though, I think since I have you locked up I should spend the day with you, maybe being your Domme, maybe just being your neighbour or friend. To be clear, what I am proposing is a "neighbour" type situation, not a girlfriend/boyfriend type situation. The only reason for the distinction right now is I feel I have forced you into a situation where you can't really give free consent. How does that sound?"

There was another emotional rollercoaster going on in my head. Locked until tomorrow night? I wanted out now! But then I am thinking of her masturbating, of watching her, of helping her. Then I pull back to think of spending the time with her, of being horny and teased and feeling intimately connected with her, of having her there, those nipples just a glance away, that smile, the bright eyes that are making me want to get hard, that ass when she turns around. I was thinking my balls might just burst there in the diner. Then the crash when I realized this would just be a platonic experience, and though I respected her more for that I was just so horny I really, really wanted to make that deal with the devil. It did make a lot of sense with the way she proposed, when I thought about it. Maybe once I was out of the cage, and had the chance to jerk off 20 times, I could think clearly and then talk to her about moving to the next level?  

I just nodded to her question, not able to explain the ups and downs of my thought process just yet. 

She smiled again, and I realized my heart was starting to beat a little faster every time she did. "I think I am beginning to really, really like you Tom. I  would love to discuss where we go from here after you are unlocked and have a chance to balance out your hormone levels." That last was said with a grin and a wink. "Trust me, if you were my boyfriend I would probably have your face between my legs right here and right now, and shock that pretty young waitress." 

I thought it was amazing that we could be thinking the same thing at the same time. 

So how did we go from here, to that place where I am tied, gagged and turning around to find a butter knife on that carpet? Well let me give you some highlights of the next 30 hours. 

We exchanged phone numbers, just so we could stay in touch, and went back to our apartments. She told me she would be right over. I tidied a bit while I waited, and when she knocked I let her in. She had a long coat on for some reason, and when she took it off. my eyes just about pop out of their socket. She had a black corset like thing on, I'll swear it was just black underwear, and then black boots that went half way up her thighs. I had goosebumps and a great deal of discomfort from the cage. She told me that she figured she should at least look the part of the Domme, if she wanted to get the full experience.