A Complicated Situation Ch. 02

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Tom continues to be challenged with a new normal.
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Part 2 of the 6 part series

Updated 01/23/2024
Created 12/17/2023
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A complicated situation part 2 - Continued complications

I found myself sitting on my couch, confused, trying to figure out how I wound up sitting here, no orgasm, and still locked in this chastity cage. Amanda was really the only thing on my mind though, how she was dressed, the feelings and sensations from when she pulled me in to hug me against her breasts. I mean, tied up and kneeling on the floor, then being pulled into a hug like that, your face is right in those breasts. You feel the soft hot skin against your cheeks, the intoxicating smells of leather, sweat, and subtle perfumes. I don't remember exactly what I had said to her, but I recall being very passionate and earnest.

When she pushed me away, she told me to calm down for a moment, because she had something to say as well. I was very motivated to be very attentive, convinced that soon this cage would be a memory. I was not even letting the constant painful grip of the cage on my cock distract me.

She sat up straight, took a deep breath to calm herself down, and looked me in the eyes.

"Okay, there are a couple of things," she started, "first, Teresa is dropping by at 7, and she probably wants to ask about our bet. I am leaning towards telling her what I asked of you, and since at this point we really haven't don't anything much more than what neighbours might do..." She paused for a moment and started to blush.

I don't know if she was thinking about how she was dressed, how I was tied up on her floor, or about when she reached out and touched my caged cock on Friday. This did not feel like something I would be doing with just a neighbour. When would you ever have a neighbour knock on your door and tell you she was masturbating, and could she borrow a cup of caged cocks so she could get over the finish line? I blushed just thinking about the situation.

"Well, like I said, I am thinking about it and we don't have too much time before she comes over." She refocused, took another delightful, deep breath, and continued. "The second thing I wanted to say is, I am not sure we are on the same page here, so I want to paraphrase what I think you might be thinking of, and see if I am right."

My heart started sinking when I heard what she said. How could we be on different pages on this? Was I too horny to think straight at the moment? We had a clear path to fix all that right in front of us, and I thought that was what she was looking for as well.

She put her finger across my mouth. I guess I must have looked like I was about to say something. "Let me continue," she said, and after I nodded, she went on, "I am thinking that what you envision is something like we work ourselves up a bit more until we end up in the bedroom, pinching and pulling and sucking and fucking like manic banshees, until we both collapse in complete exhaustions, quite thoroughly satisfied and drift off to sleep in each others arms."

"Tomorrow we wake up, smiles on our faces, both feeling a bit awkward, both eager to take the next steps in building a relationship. A year from now, we are a comfortable couple, we have regular sex, and every once in a while we pick something kinky to do, like bondage, power-exchange, pegging, figging, etc.., but basically planning a future together in relationship bliss. Just nod or shake you head to let me know if I have that right!"

She had kept her finger on my lips, and in that moment it went from feeling somewhat erotic, to feeling, i don't know, controlling? It was still erotic, but it also seemed like if I wanted to respond in a way other than she had requested it would all but impossible.

I took a moment to think over what she had said. The only thing on that list that I had understood was bondage, though I could imagine what power-exchange was. I really did need to broaden my horizons a bit more. Thinking it through though, that would have been the dream. I would leap into that idea in a heartbeat with only a wistful glance back at Teresa's ass. Maybe I could add a three-some to that list of hers? I flinched a bit as my cock responded to the image of Teresa, Amanda and I together, and as the cage forcefully reminded me it was there. I hoped I could get this cage off soon, to pursue that thought a bit more.

I looked back up at Amanda as I finished my thought process, and nodded to her, trying to convey that her description was pretty much where my head is at.

Her smile was a little self-satisfied, probably for guessing right. but it had a tinge of sad or wistful to it as well. She took her finger off my lips, and sat up straight. I took a moment to sit back on my heels, as she looked about to speak again.

"A week ago, if we had gone out on a date, we might have ended up just like that if things had gone right," she said. "Today, after the last couple of days, after what you have given me?" she paused and took a breath. "I want so much more! More, more, more! It's not 'relationship' I want, it is 'experiment', experience, trying all these things that have been compressed inside my imagination for..." She was looking up, over my head, but probably only seeing what she had imagined for so long. Her eyes moving back and forth, lingering and blinking between each move. I could imagine that each blink, each change of direction for her eyes, was her visiting a different idea she had read, or had, or lusted after. As she did this she started to look more radiant, thirsty, ravenous. It was a bit overwhelming just watching her and I was wondering if I could escape what might come next, and how could I possibly let go and not be here for this journey.

It felt like she had been doing this for a long time, but it was probably only a minute or so of silence. Her eyes snapped back to mine, and she collected her thoughts.

"A month from now I may feel different, but I am not looking for a relationship now. I am looking for a play partner. A kinky, experimental, scary, exciting, surprising, frustrating, type of play, just to be clear. I want to put nipple clamps on you to watch you react, to slap your balls and find what is too hard and what is too soft, to tease you, to edge you, to make you eat my pussy for hours, then lock you back up unsatisfied, and make you spoon me all night so I can feel your caged cock twitching against my ass when I wake up in the night. There are so many things that I want to feel and do, and none of them would ever be called vanilla. There will be times when I just want a good, old fashioned fucking too, but that is not the normal I am looking for." She paused to let that sink in to my hormone filled brain. How could I possibly think straight when she keeps bringing up fucking her. Her words seem to connect directly to my cock's reactions, and my cock just keeps bashing against her steel cage!

Her next words changed gears a bit, "Tom, I am telling you this because you need to know what I am looking for. I have had my choice, and you have given me a wonderful gift. You have opened my mind and heart, and I know the direction I want to go in right now. I don't think you could understand how much what you have done means to me, or how much I want you to come on this journey with me. I know you have not given much thought to anything kinky, at least that is how it seemed to me. You showed so much courage and generosity towards me by letting me hold the key to your chastity cage. I could not imagine anyone else being introduced to the idea and going along like you have, and we have gotten to know each other so well. You have been open and honest, you have listened and shared. I really think you are a great person."

She started untying me at this point. "Look we need to get a move on here. I know there is a lot more to say, but I need to change, and do something about how I smell before Teresa gets here!" I wanted to argue that there was absolutely nothing wrong with hot, sweaty, sexy, very horny woman smell, but I suppose that was the point, since she had Theresa was coming over.

We both stood up, and I was thinking that this is where I get the key and go take this thing off, but she put her hand on my arm and said, "Look I need you to make a choice and I want you to think about it for a bit. You can unlock the cage, and we can go back to being neighbours, and I can go looking for that kinky play partner I was talking about. I would still owe you a few booty calls for the last couple of days and I might just come knocking with some booty calls of my own." There was a mischievous twinkle in her eyes as she said this that reflected just how horny this had made her.

"Or," she continued, "you could choose to be that play partner! I can promise you it won't be all orgasm denial and chastity. I am pretty sure I can make you cum more often that you really want at times. It would be an adventure, and you would experience things you have never even thought of." As she was saying this her hands had moved to my chest, caressing up and down, finding and rubbing my nipples under my shirt, until they finally moved up and to the back of my neck, so her thumbs were close to my earlobes and her fingers were caressing the back of my head. "I have only ever thought about kinky things, and the fact that you have not even done that means I would get to experience things for the first time while I watch you discover there are new things for the very first time. This would be so much better than finding someone who had been there and done all that before." She flexed her fingers and pulled my head down towards hers, and kissed me. I got lost in that kiss. Her tongue probing, mine responding, both of us leaning in, touching, playing for so long, I had forgotten when it started, and I was startled when she ended it.

She held my eyes for a moment and then said, "Okay, you go back to your place and think about what choice you want to make. I will text you when Teresa is done here and you can come over, get unlocked and tell me your choice. How does that sound?"

In a daze, I just nodded and turned around. She took that opportunity to give me a hard slap on my left butt cheek. I turned my head to look at her as I made for the door. She was grinning, in her irresistible Domme outfit, waving her fingers from the hand she had just used to smack my ass. I could not help but smile back at her as I went back to my apartment, still feeling the tingling imprint of her hand on my ass.

I am not sure when I got back to this couch. I did go plug my phone in before sitting down, thinking I did not want to miss her text because my phone died, then I just sat here, thinking. I think I recall hearing a knock on Amanda's door from the hallway at one point, that must have meant Teresa had shown up. Other than that, I sat there numb. My cock was finally calming down, with only momentary reactions as I thought through the last couple of days. This was so completely different than I had expected. I had not even known that feeling this way, obsessing over an entire set of experiences that had only lasted 2 days, could happen this quickly. I know Amanda had asked me to make a choice, but what was I choosing? Right now, I wasn't unhappy, I was just really horny, I wanted get my cock free and to cum, more than that, I wanted to bury my free cock deep in her hot pussy and just explode. Beyond that I couldn't manage to care right now, I was so horny. I know she was asking me to choose, but I couldn't even understand that there was a decision here. There was just a desperate want, which I either solve with a lonely, and pathetic jerking off, which honestly would be a sad way to end this two days of crazy, or I stay in a state of uncertainty with someone else deciding when I can cum, if I am locked of free, how I am to feel tormented...

My dazed musings were interrupted by a knock at the door. Amanda must have decided to come over instead of texting. I checked the clock on my way to the door and saw that somehow it was almost 9PM. They must have been doing a lot of talking, but I wondered more about how time could have passed so fast.

I opened the door, still not sure what choice I was making. On the other side was a very blonde, grinning face, almost bursting with excitement.

"Hi Tom!" Teresa said enthusiastically. "Mind if I come in?" she asked, as she step in close, moved my hand from the door, and rubbing up against me as she turned to push the door closed behind her. She then backed up to lean against it. Her eyes were on me, and she bit her lower lip for a moment.

I stammered "I... Teresa, hi, look this is not the best..."

She stepped forward, put a hand on my chest and said, "Stop!" and I did. She then continued, "Look, Amanda told me everything. Well probably not everything, but I understand the situation. I told her I would drop by on my way out, so she even knows I am here. I always think that who-knows-what-about-whom is always a thing that everyone involved knows about."

"Okay, but..." was all I managed to get out before she move her hand from my chest to my lips.

"SHHHH!" she said, managing to make it sound very emphatic, and accompanied it with a steely look. "I am here because I want to see!" Her voice had that insistent, spoiled princess tone, that is annoying as hell but is really kryptonite to very, very horny men! Her hand moved back to my chest and using both, she pushed me gently back from the door and properly into my apartment.

She started to explain, "You see, in a few minutes you and Amanda will talk and you will tell her your choice. If you choose to take the cage off and escape Amanda clutches. then i have no idea if I would be able to get you wearing one ever again, so would never be able to see you locked up in chastity." She paused, and I was feeling a little scared of the lust that she seemed to be experiencing for that idea.

"Your other choice," she continued," is to let Amanda sink her claws in deep and leave her in control of everything, and in that case I would need to go through her if I wanted to see, and I really don't know what that would cost me."

"But for right now, you are free, just a poor boy with no owner and his cock locked in a cage. One thing I know is that straight, horny, cock locked boys need do as they are told by pretty little things like me, so follow me!" With that she grabbed my right wrist and pulled me along. She went to one of my dinning table chairs, turned it around and sat down facing me.

I had started moving from confusion to embarrassment as I let her pull me along. First that I was letting her just pull me along, and secondly, she had called herself pretty, but that was an understatement. She was toned, athletic and gorgeous, though that bias might come from being this close to her perfect ass and being so horny. She wore a lot of loose clothing around the building, probably to minimize the attention she got, but she always seemed to know how to get my attention. When she sat down facing me, my distracted mind was on her hot little body and I started blushing furiously, which I am sure amused her.

Smiling, she said "Here, maybe this will help!" With that, she reach up and started pulling off her top. My heart skipped a beat as I watched, mesmerized as she revealed her breasts. She was not wearing a bra underneath and my eyes stayed glued to her moving, jiggling breasts as she finished taking off her shirt and putting it on the table and lingered on those beautiful, hard, pink, nipples that seemed to be begging to be sucked. I could not spare a moment to look, but there must have been an evil glint in her eye as she knew what this was doing to me. The crushing and twitching reaction from the cage certainly tried to wake me up from my horny stupor. I would not have called what she dd a 'help', with anything but my compliance.

"Put your hands behind your head, and interlock your fingers nice a tight!" she said, watching the twitching bulge in my shorts. "I would not want you to injure yourself by thoughtlessly starting to fondle my breasts or anything." she added, giggling.

Once she was sure my hands were in place, she changed her focus to my shorts. she leaned forward a bit, put her hands gently on my hips, and caressing up and down as she went, moving her hands down my thighs, until she gripped the bottom of my shorts. Then she started slowly pulling down so she could reveal my caged cock. My cock was trying to get hard, well straight I suppose, it was as hard as it could get and as big as the cage would allow. It was poking straight out and did a big bouncing display as the waistband of the shorts finally let it escape.

Teresa moaned a little bit, as she let my shorts drop to the floor. It also turns out that Teresa is not nearly as shy as Amanda, and she just reached out and with one hand started caressing the cage, and with the other she started fondling my balls.

The feeling on my cock was very strange, with so many sensations at once, the tight, painful grip of the cage, an almost pinching sensation from the gaps in the cage rings that always seemed to move, then her hand, but only on the narrow bits of my cock that bulged through the metal rings of the cage. It became so frustrating to see a woman grasp my cock and only be able for feel a fraction of her hand, her grip. It did not even feel like she was stroking it, but I could see that was what she was doing.

I could feel all of her other hand on my balls though. It felt more intense than it ever had before! Even with my cock screaming at me, I just wanted to keep feeling her hand, her grip on my balls! My balls had never felt so, so, I guess sensuous is the right word?

At this point, I heard my phone buzz behind me. My head turned and I started to move my hands from the back of my head.

"Stop!" Teresa said firmly. "A couple of minutes won't make much difference and I am not done!" Her left hand closed around my balls, her index finger and thumb making a loop around my desperate nuts, under my caged cock, and she pulled gently but steadily. "Clear?" At that she took her eyes off my cage, turned her head rather than raised it, and look up at me but managed to be looking at me sideways. I don't understand how she managed it, but there was so much more 'don't mess with me' in that look, than if she had just raised her head. I looked her in the eyes and nodded, understanding who was in control at the moment, which seemed to make her very happy. She returned her attention to my cage, while I wondered why I was enjoying this scary woman's hands on my balls so much.

"What have you been using as a lubricant here? Lube?" She asked, turning her head to look up at me again. I nodded. "You should find a good moisturizer instead, and apply it as needed. You seem to have some chaffing starting here. I like the look of metal on your cock, but if you ever wear a cage longer term, you should really have a plastic one. We really need to make sure we are taking good care of this cock. " she continued inspecting and caressing my caged cock, and her grip on my balls had not loosened, continuing to drive me crazy, but somewhere in my head there was a moment to digest the words she had used. Longer term? What does that mean? There are plastic cages too? Why is she talking about taking care of my cock as a 'we'?

Those thoughts were interrupted by Teresa's right hand leaving my cock, pushing up under my t-shirt, rubbing and weaving across my abs, until she reached my left nipple, which she started rolling around between her thumb and forefinger. I gasped a bit when she pinched it.

"You know, I was very put out by you and Amanda getting all involved and everything this weekend. I invited you to play euchre hoping I would be jumping your bones all weekend." She pinched my nipple harder as she said that, and the grip on my balls tightened.

My phone buzzed again in the background. I was starting to feel a sense of urgency on getting to it, as Teresa's right hand moved to my right nipple and pinched that one hard, making me groan. I had the feeling that if I wanted to get to my phone, I would have to leave my balls, and maybe one of my nipples behind, so I just stayed put.

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