A Complicated Situation Ch. 04

A complicated situation part 4 -- Choices

I booted up my laptop and sent off a note to my boss telling him I needed a personal day after all. Then I sat for a while and thought about what Teresa had said. Of course, my mind drifted a lot to what Teresa had been doing. Why did I tell her to stop? I know I was aching and I know it would have just added to my frustration, but watching her cum, watching that orgasm would have been something I could dream about for a long time. Now if I asked her some other time she might not do it, but if I had let her cum, she would have probably done it again for me. Though I will admit that there was a thrill in stopping her, and that she followed my instructions.

I thought about Teresa and why she had been here, why she was teasing me and why she felt safe doing so. If Amanda had not asked me to wear this chastity cage, the last 4 days would have been completely different. I would have jerked off Friday, woken up the next morning and Amanda's request would have been something lame like take her to breakfast. We would have chatted about normal things and gone on with our day. If we had crossed paths in the hallway, we would have been friendlier, talked about a euchre rematch. Then a few weeks or months from now, we might be closer, or I would see strange guys going in and out of her apartment and be somewhat jealous.

As for Theresa, she would not have come over Sunday, there would have been no Monday night dinner, no Tuesday work from my place, nothing. On the plus side I would have had a half a dozen orgasms, played a lot more of my computer games, and otherwise continue a lackluster existence.

I thought about that last statement a lot. Did I really think I was pathetic? No, but I was not out there pursuing babes like Amanda and Teresa, I was hiding in my apartment, going to work, and otherwise simply avoiding what had so excited me these last 4 days. Don't get me wrong, I did not really like chastity, but I did love these horny feelings, always engaged with a sexy thought, and sexy girls. I was not bored.

I know this was not the playboy fantasy of getting blowjobs all the time, willing and giggling bimbos on my arms and living a 'perfect' life. But then that was not a reality. In my reality, I had not had a blowjob since the second year of college, when I broke up with my last girlfriend. My god, over two years of being single and only jerking off to talk about. I had been busy, so finding a girlfriend had not really been a priority of mine, but others had gone through the same and come out in relationships. I had gotten used to being single I suppose, staying in and avoiding social situations, compensating with gaming or work, and when I needed relief, I would think of the girls I had seen, and have a wonderful fantasy and jerk off. Just like I had last Thursday. Just like I would have done on Friday if Amanda had not highjacked my life.

Okay, so I had no regrets over how things had gone the last 4 days.

Now that I understood where I was coming from, how do I choose? I did a long, drawn-out description of my thought process on this, and it is around here somewhere, but I will summarize it now.

I felt a strong connection to both these women. With Amanda it was stronger, but with Teresa it was more visceral. They were very different from each other. Teresa, I think, had been very right in pointing out that I was lonely. I could change how horny I was in just a few minutes, but the only way I would change how lonely I was had to include other people.

It all came down to the fact that Amanda had asked me to choose, and one choice meant I would go back to a lonely, empty life. The other choice meant accepting who-knows-what but being a part of something that would change how I lived my life. I agreed with Teresa that Amanda had a lot of control freak in her, so I don't know just how much change. Also, Teresa had not asked me to choose, or offered an alternative, though I did appreciate how she jumped on board the opportunity that Amanda created. Maybe choosing Amanda did not mean that Teresa would go away?

It was almost 2AM when I had got to that point. I had spent a lot of time thinking things through, and was close to where I needed to be to make the choice for Amanda. I got up, had some leftover pizza, a beer, and watched some TV in the hopes it would help me sleep. I then went to bed and collapsed into sleep, and for a change I actually stayed asleep for quite a while before the cage woke me up. I suppose my subconscious worked on the decision I was contemplating before it got back to images of a gasping and shuddering Teresa.

It was almost 8AM when I got up and showered, made coffee and had some breakfast. I did check work, and my boss confirmed my personal day. So now I had three or more hours to wait for Amanda. Teresa had probably gone off to work. No knock at the door, no note to read. I did re-read the note from yesterday and put it someplace safe. Games? First, I decided to do laundry. The least I could do was clean Teresa's clothes from yesterday. I also tidied up, remembering Saturday with Amanda, and thinking she would probably expect it of me.

The clock finally ticked by enough that there was finally a knock at my door. I opened it and found Amanda on the other side. She looked good. She was dressed for work, her rolling suitcase and a garment bag beside her, she was taking a long look at me, and said "Hi."

I was enjoying looking at her and was very eloquent with a reply of "Hi."

"I could use a hug." She then said. There was a tone in her voice that almost made it a question, and I realized we had never hugged before and she was probably wondering if it would be okay with me if we did. I just nodded. She moved in for a hug, and I wrapped my arms around her. She held the hug for what seemed a really long time, but I did not mind. It was a very nice hug.

"Thank you, I needed that!" She said as she let go and stepped back.

She held out her hand, holding a small key between thumb and forefinger. I looked at it and reached for it.

"Ah!" She said, and I stopped. "Unlock only. Well, you should probably clean too, but no orgasm yet. I need to go shower, unpack and then make myself a coffee. I should be about an hour, but will text you when I am ready and you can come over and have that talk." With that, she let me take the key, smiled up at me, patted me on the chest, then turned to grab her stuff and head into her apartment.

I watched her go, sad that her coat did not let me see her cute ass. As soon as her door closed, I looked at the key for a moment, then rushed back into my apartment to get this cage off!

I had a stray thought that perhaps she had given me the wrong key, but it was the correct one! I was free. It took a bit to get the cage off, but I did, and then hopped in a quick shower to properly clean my cock. If felt amazing to have my hard cock back in my hand, to be able to stroke it. I almost got carried away, before remembering what Amanda had said. Then I thought of how much better it would be for my hard cock to be in her hand, or mouth, or pussy, rather than in my hand. I turned the water to cold to shock myself away from doing something I would regret. I got out of the shower and got dressed again.

I cleaned and dried the chastity device. I put the lock back on it, just so it would all stay together rather than be in 3 pieces, then I waited for Amanda's text. It was closer to an hour and a half, but the text finally came.

It said "Come on over, door is unlocked so you can walk right in."

Heart racing, I put the chastity device in my pocket, made sure I had the key to my apartment, and went over to Amanda's place. I did knock as I opened the door, as it felt very weird just walking in.

She was sitting on her couch in a big fluffy, white bathrobe. As I came in, she put down her cup, got up and came over and gave me another hug.

"I like this hugging thing." She said, smiling. "Can I get you something to drink?" she then asked. I replied that I was good for now, so she invited me to join her on the couch.

As I sat down, I took the chastity cage out, and put it on the coffee table.

She glanced at it and said "Oh, I think you should keep that as a souvenir. You can keep the key too. I don't think I could put that one on anyone else." She smiled, and continued "Anyhow, that is not what we should really talk about first." She reached over and put her hand on my wrist and said, "Before you start in on what your choice will be, you need to tell me about what happened from the moment Teresa knocked on your door on Sunday until you last saw or communicated with her." I started to worry. How would she take it if I told her everything?

I looked at her, and she shifted to sit cross legged on the couch facing me. In a bathrobe that is bold. I could not quite see anything, but I almost could, and I was getting very distracted again. Her face looked happy and eager to hear the story, so I resolved to tell her everything as honestly and openly as I could remember.

I described the scene from Sunday where Teresa came bursting in, and aggressively handled my balls. I told her about the letter the next morning, my thought process, the messages I had sent. I even showed her my texts. I went on to describe the dinner we had, and all the details from a very overwhelming Tuesday, including the part where I had stopped Teresa from having an orgasm. I even shared the observations that she had just before she had left for the night.

Amanda seemed to love the story. She was hanging on every word, she asked me to elaborate on details, on how I had felt, how horny I was and what it felt like going through this locked in chastity. As I had done on the weekend, I was completely open with her, saying far more than I ever thought I would to anyone. She was a great listener and made me feel safe expressing things that I usually keep to myself.

"Thank you for telling me all that. It feels really nice that you trust me enough to open up like that, even when I don't have you locked in chastity." She was smiling and seemed genuinely content.

"So," she said after a moment, "I asked you to make a choice. You could choose to be my play partner in a kinky adventure I want to embark on, or you could choose to not be my play partner for that adventure and I would need to go find someone who would say yes." Then she paused.

"Sorry, I think this will be easier if I am sitting properly and facing you." She said and got up to go sit in the easy chair facing the couch. She sat forward elbows on her knees, I shifted to be facing her too, she took a deep breath and then continued "These last 5 days have been a roller coaster for me. I am sure for you too, but for different reasons. The feelings you get from fantasies are very different from those when you actually take action, like locking someone in chastity. That has made me think a lot about what I want, what I am hoping for, and what I am scared of hearing. I had some twinges of jealousy as Teresa kept me up to date on what she has been doing to you, partly because I wanted to be first doing some things, and partly because I wish I could react the way she does, dive into her passion, just do, and apologize afterwards if necessary. I really appreciate her telling me everything, and it was amazing hearing the experience from your side."

She took a breath and admitted "It has made feel really horny and really needy right about now."

Another breath, and she continued, "Anyhow, I was actually very happy to hear about the restraint you showed in light of Teresa's teasing. If you two had gone too far before you gave me your choice, I am not sure how I would have felt if you then chose to be my play partner." A brief pause, and questioning look, "Is it strange that I want to say playmate, but that brings up too many images of Playboy bunnies? Anyway, back on point here!"

She paused again for another breath, looked me in the eye and said, "One of the things I have realized is where I want to start playing, so here is what it will mean if you choose to be my playmate. First, I am in control, I like it and get off on it. It will be up to me if and when you cum, what we do will be my choice too and a lot of that will be kinky, sexy fun you have probably not thought about yet. Also, I will tell you what to do, I like the idea of making you adopt good habits, like cleaning, cooking meals, etc..."

"You are allowed to make suggestions, but I will decide. You are allowed to tell me no, and I will listen. I may decide your reluctance is reasonable. For instance, if I want to have 'Property of Amanda' tattooed on your ass, and you say no, that is reasonable. I may decide that you need a period to adjust to new ideas, for instance when I want to peg you, you may... Yes?" I had raised my hand at that to interrupt her.

"What do you mean by 'peg'?" I asked her.

Her lips tightened in a smirk like smile as she realized just how little I knew about the kinks that she had been thinking about for a decade. With an amused look on her face she explained, "Well, you might really need an adjustment period for this one, but 'peg' or 'pegging' is when a woman puts a harness around her hips and ass that can hold dildo, and with a lot of lube, patience and glee proceeds to penetrate, or 'peg' your ass. Basically, you get fucked up the ass with a strap-on. In men it massages the prostate apparently and can even give you an orgasm." She was looking me in the eyes as she said this, and I am not sure what was making me most uncomfortable, what she had just described, or the determination and eagerness that seemed to be hiding behind her shy smile as she told me.

She gave me a couple of moments to digest this before asking, "Can I continue?" I swallowed and nodded, not trusting myself to speak right then. "So, adjustment periods might be necessary, but I will want my way in the end. I reserve the right to come up with consequences to act as motivation if the adjustment period is taking too long to my mind." After hearing about 'pegging' I did not think I was ready to hear about consequences, so I did not ask at that point.

"Secondly," She continued, "safety and health are a priority, and sometimes play might go a bit too far. We both need to be aware of, and willing to say stop if something is wrong. As an example, when Teresa was squeezing your balls on Sunday, you did not try stopping her. There is a strong connection between pleasure and pain at times, but it does not take a lot to push that over into a complete turnoff, just pain and maybe injury. So we both have the right to say stop."

"Thirdly, this is play I am proposing. I am proposing it because I like you, and what I know of you I think you and I will be very compatible. I am not proposing a relationship in a traditional sense. This is not based on emotional bonding, it will be based on kink and exploration. I don't think we can avoid bonding, and I would not want to avoid it, but that is not the primary focus to start. Having said that, I know we both have lives, we both have work, family, obligations, so I am not expecting us to disappear into an unrealistic fantasy. We will talk and plan things appropriately in our lives and make time for play." She concluded.

After a dramatic pause, she spoke about the other option, "if you say you don't want to my playmate, well, I have not thought too much about that, but I have worried. I would need some time to digest that I think. So, can you now tell me your choice?"

My turn. My heart was hammering again. I felt like I did in school when I had to stand up and do a presentation in front of everyone. I nodded and collected my thoughts for a moment. Setting aside all the scary things she had just said, I focused on all the appealing ones. I started talking, telling her about my thoughts from last night and this morning. I expressed myself and how conflicted I was in some ways, and all because of Teresa. I finally covered my conclusion, and my hope that this choice did not completely exclude Teresa, but that I would love to be her playmate and see where this adventure took us.

"YES!" she said enthusiastically, "I was so hoping you would say that. I was so scared of any other answer!" she had stood up and did a bit of excited dancing around at that point. I was watching, noticing the tie on her bathrobe had slipped a bit, and was really hoping it would fly open any moment. But she had noticed the same thing and pulled it tight. "Okay, we have some things to do, but first, I need another hug." I stood up as she came close, and she hugged me very tight. She was bouncing a little as she did so, because she could not contain her excitement.

"Okay, you need to strip down right now, and I will be right back." She said.

I got very excited at this point. Going straight to naked was always a good thing. She went off to her bedroom while I took my clothes off and tossed them on the couch beside me. By the time I was done, she was back, holding two small boxes. She looked at my pile of clothes and said, "You need to fold those neatly and then make a neat stack on the couch. I don't like sloppiness!"

That deflated me a little bit, but I did understand that she felt there was a right way to do things, and I had agreed to abide by her wishes. Standing there naked as she watched me, I took my clothes, folded them neatly and stacked them pants first, then underwear, then shirt and socks on top. She seemed to think that was good enough, nodded, and handed me one of the boxes. "Open this and put it on."

Wondering what it was, I opened it. It was a smart watch. I gave her a questioning look, and she answered by saying, "Like I said, I like control. This watch will track your heart rate, blood pressure and activity. You will always wear it, even in the shower, as it is water resistant. You will let me know when you take it off and why. I will have access to all the data from the watch and over the next while I will figure out from the data how to tell your moods and level of arousal. I will also figure out what an orgasm will do to you, so I will always know when you have had one. It might take a lot of experimenting with that to make sure I have a good understanding of it." That last she said with a grin. Being promised a lot of orgasms sounded really good to me. I put the watch on my left wrist and checked the display. It was fully charged, and in the box was a cable to recharge it as well as instructions on how to pair it with my phone and access the information from the cloud.

Amanda was watching me waiting for me to be done. I think I blushed a little bit remembering I was naked, but it was a bit of a turn on being the focus of her attention like that.

She then handed me the other box, and watched while I opened it. Inside was another chastity device. A plastic one. Not quite as big and certainly not as heavy as the metal one. I looked over at her and started with, "But I thought " then she interrupted me.

She had a determined look on her face and said, "You are not going to cum today. Soon, but not today. I am in charge, and now you have to accept it and learn what that means. Jerking off is not allowed at all, and unless you have my permission you don't cum. Accidents will have consequences. A cage removes temptation, builds trust, and it gives me that sense of control that I crave. This cage should be better for longer term use. Teresa had mentioned seeing chaffing from the other one and this one being lighter should be better in many ways. It is narrower too and reviews I have read say that it has less problems with waking you up in the middle of the night."

"I would help you put it on, but I think in your state if I am touching you, that cock will never deflate without shooting its load. That will not happen today, so you need to put it on now. Do you want me to get some ice?" she finally asked.