A Complicated Situation Ch. 05

A complicated situation part 5 -- Learning

There I was standing in the hall with Teresa, exhausted and ready to collapse. Teresa looked at me and said. "I could use a beer if you have one?" and the next thing I know I am inviting her into my apartment.

I told her to sit on the couch while I went to get a couple of beer. I put some pretzels in a bowl too, so we could nibble on something.

I noticed that she had sat in what I am starting to think of her spot on the couch, and that she had taken her top off! I tried not to stare at her breasts, as I gave her a beer and put the pretzels on the table, but I was not very successful.

She was looking at me grinning and said, "I hope you don't mind that I got comfortable?" She had an innocent look on her face.

I cleared my throat a couple of times and said, "Honestly, I love it when you are naked, or part naked. You are sexy and beautiful. My only problem right now is I have never gone this long without an orgasm, I am locked in a tiny tube that gets very tight and uncomfortable. My balls ache, and judging from the location of other aching my prostate is getting to the point where they don't like me being this horny without getting relief."

"Oh, sorry." She started reaching for her shirt, " I did not realize that. I can behave."

I stopped her and said, "No, no, don't do that on my account." She paused and looked at me, so I continued, "I am just sharing, so you know what effect you are having. You have my permission to tease me like this as much you want. I am pretty sure that Amanda would be okay with it too, since she seems happy about the last few days, as long as neither of us cum without permission. I am okay with you doing what you want to do. If I start to feel it is too much I will say so." At that she smiled and put down her shirt and took a sip of beer.

"So how is the new cage?" She asked. "I was really very surprised to find out you were back in a chastity device. When I said yes to her, I thought I would be tormented with having to watch her fuck you, while I just got teased!"

I started by answering her question, "The cage is much lighter, does not pull as much, and so far I have hopes that it is more comfortable to sleep in. The pressure when I try to get erect is even, and there is no pinching from the gaps that the metal cage had between rings." I figure it was my turn to ask a question and said, "So if you don't mind me asking, I have a couple of questions for you. First what made you say yes to Amanda, and secondly, were you... have you...?" I did not really know how to ask her is she went down on women often, but Teresa just sat there smiling at me, watching me struggle to get it out, "How surprised and ready were you to be the one giving her oral tonight?" is what finally came out of my mouth.

I won't go into the details of what she told me, but it turns out that a lot of her decision to accept is that she has been very lonely too. She is in a new city, living with her brother and working in a family business. She plays on an all-women sports team and the guys she can meet are either at the bar, or at the office, neither of which appealed to her. Most other men in the building were in relationships, which did not stop them from hitting on her. She had been surprised that I had not been more aggressive, but actually liked that. If I had, I would have triggered her defenses and she would have kept me at arms length.

The euchre game the previous week was the best social activity that she had had in a long time, and the fun since then had been perfect. She had been very depressed at the prospect of going back to being lonely. She was not sure what being controlled would be like, but it was giving her a thrill even if it had gone in a very different direction than she had imagined.

She asked me how I was feeling being kept in a chastity device, and we had a good conversation about it. She told me it was giving her a thrill just knowing I was wearing one, and she really enjoyed teasing me when I was. The biggest thrill she had had earlier was knowing I was watching her ass and desperate for relief in so many ways.

Even though she was still teasing me, it felt like we were connecting on more than just an 'I-really-like-your-boobs' kind of way. We talked, and sipped beer for a while, then she left giving me a nice, passionate, touching, lingering kiss on her way out the door. I did check to see if she had stolen the lockbox that Amanda had given me, but luckily that was still here.

I set my alarm for 5:30, double checked it then went to sleep. There were still some periods overnight where I woke because of the cage, but they were not nearly as bad as with the other cage. Oddly enough I was already up because of it when the alarm went off. I got up and made a coffee and sat to wait for 5:45AM. Right on time I used the app on my phone to open the lock, and it went click! I got the key out and was about to get out of this cage when a message dinged on my phone.

It was Amanda, and she sent, "Good morning. My, someone is eager!"

I replied back "Good morning! Oh my, yes!"

She sent back " Well remember, though I am letting you out to go to work, you are not to cum, and maybe best if you avoid playing with your cock entirely. Lock back up when you get home! Dinner over here tonight. I will let you know timing."

I sent her back a scrunched-up-face emoji and "Yes Amanda! I will do as you say. Dinner sounds great."

My day was eventful in a work kind of way, with only one thing to note here. I was regretting my original choice of hotelling stations. I had picked this one because it was close to our director's admin assistant. She was a bit younger than I, she was cute and perky, and in my current state, she was very distracting. We called her Miss Perkins, because that was what our director called her. Everyone else on our floor was on a first name basis. When I asked her why this was, she said he liked the name from an old movie or show and made sure to point out that it was not the reference to the John Wick franchise that he was thinking about. Anyhow, she made the day more pleasant in a very distracting way.

When I got home after work, I put the cage back on, and the key went back into the lock box. If I didn't need the key to lock this thing on, I would have just needed to open the lockbox once, use the key and put it back in. Anyhow, this gave Amanda an opportunity to know when I was doing this, and she sent me a big grinning face. I had periodically been chatting with both Amanda and Teresa throughout the day, so I knew Teresa was going off to play volleyball, I was to shower and head over to Amanda's and she was going to make me help her make the dinner we were going to eat.

Amada had gotten home before me, so she was ready for me to come over whenever I was ready, which ended up being at about quarter to five.

When I got there she, of course, had me get naked. She seemed to enjoy watching me do that. At the end of the kitchen counter she had a collar, the smooth one which got me thinking, and the cuffs. As she locked these in place she pointed out that locking my hands to the collar with the chain would be counterproductive to cooking, so that would not happen yet. She then gave me an apron to put on, saying with a grin that you should not cook naked. It was a yellow apron that said 'Kitchen Minion' across the front. I guess I knew my place.

We made burgers. She said it was simple, and I guess pressing ground meat together with some spices was easy enough, but she had me cutting and chopping for the toppings and salad. I had never used a large knife before, or properly learned to slice onions and tomatoes. Now that she had taught me how, I was apparently just going to need a lot of practice, which gave me a hint at her future plans. It did not help my state of mind that she would frequently slapped my ass, and at least as frequently would rub and caress it. It made getting the job done right longer and more difficult.

When the meal was over Amanda told me there was something else she wanted me to learn and to practice, but we would have to take the cage off. She then brought me to her bedroom. At this I got very excited. Finally, after a whole week, I was going to get to cum!

In her bedroom I saw that she still had the chair at the foot of her bed, and she directed me to sit in it. She then pulled out her necklace that had the second key to my chastity device and handed it to me.

"Here, you better take that thing off." She said. She was probably worried that if she did it, I would not be able to relax my cock enough and we would never get the damn thing off. She was probably right. But she made it difficult anyhow, as she started to do a slow striptease while I tried to unlock the cage. She was done stripping, and she was naked sitting cross legged in front of me on the bed, just watching me work and I was still trying. I finally got it off by completely shutting her out of my field of vision, and once off, I looked around to appreciate what she looked like naked. She had really nice breasts. They were bigger than Teresa's with bigger nipples, maybe a shade darker. She had a very nice belly that I spent time appreciating, then my eyes traveled further down. I could see the hood of clitoris poking out from the small amount of pubic hair she had, the tops of the crease where her pussy lips started. The view was fantastic, the reaction from my cock was enthusiastic and I was eager.

Amanda waited until I raised my eyes to look at her face. She was smiling and asked, "Have you ever heard of 'Edging'?"

I got very confused as this is not anywhere near what I had expected. I did not think she was talking about lawn maintenance with my dad, so I frowned and said "No..." It was very uncertain no with some questioning elements to it, mostly because I had no context for what she was asking.

Her smile just got bigger. "Okay. Well I have faith in you that you will learn this faster than the knife work from earlier." She said. "Now I want you to start stroking your cock. Start slowly and listen to the instructions that I give you."

Hesitantly, and somewhat self-consciously I started stroking my cock in front of her. She watched me for a bit, then watched me watching her for a moment.

"We need to change something up here. Keep up that pace." She said as she got off the bed and went to one of her drawers. She came back from behind me and put one of those blindfold masks over my eyes. "Keep stroking!" She reminded me.

As she moved around to get back to her spot on the bed she said, "I need you focusing on my instructions, on you cock and how it is feeling, not on me or my body right now."

I stroked slowly and in silence for a while. I could feel her eyes watching me, though I really had no idea, until at one point she started asking questions.

"When you are stroking, how does it feel when you start feeling your orgasm is building?" she asked.

I thought about that for a moment. I had not really paid too much attention to how it started to be honest, I was usually far too busy just enjoying the experience. I told her that, but added "Thinking back, something I feel it build in the base of my cock and explode out and up from there. Other times I feel it start towards the top, just under my head, at the front of my cock."

"When you say 'front of your cock' you mean the side facing me right now?"

I replied "Yes." I could imagine her nodding after I said that.

"Stroke a bit faster!" She instructed, and I picked up the pace of stroking.

After a bit she asked, "How much time between when you start to feel your orgasm build, and it actually happens?"

"It varies," I replied, "because it depends on how fast I am stroking. It has been quite a while since I have had sex, but I do remember being able to hold it back a bit if I tried, just to keep going longer, but it helped to slow down or stop."

""Perfect!" She said, and for some reason I could almost hear a grin in her voice. "Has a girl ever let you cum in her mouth?"

"Yes." I replied, and I told her about my high school girlfriend, who dated me more to be the same as her other friend I think, and how abysmal her blowjob skills had been, but she let me cum in her mouth once, so she could tell her friends about it. I did not have pleasant memories of that relationship, although she had been nice and really cute, just not dating me for the right reasons.

Other blowjobs I had had, had been foreplay, or had been finished by simply stroking. One girlfriend from university seemed to really enjoy doing it that way.

"Don't slow down. As a matter of fact, go a little bit faster. " Amanda said, and I realized I had gotten distracted, so I sped up.

"At this rate how long before you feel like you are going to cum?" Was her next question. I consider the speed I was stroking.

"A while, I am not really close right now." I said.

"I want you to speed up to where you think you could orgasm in, say a couple of minutes." She said but followed it up with "But you don't have permission to cum yet! You need to tell me when you are close, like maybe 20 strokes away. Just say 'close' or 'there' to indicate when you get there. If you get too close, stop stroking and use those skills you talked about to hold it back."

I did as I was asked. I stroked faster and got the point where I could feel the orgasm building from the base of my cock, I moaned a little bit, and kept going until I felt it build enough and I said "There!"

"Stop! Take your hand off your cock." She commanded.

I reluctantly stopped and removed my hand. I could feel my cock standing up, twitching. I waited to see what Amanda's next instruction was. Then I felt her thumb and forefinger on the head of my cock. I had a full body twitch at the surprise of her touch, and my cock twitch at the sensation.

"Hmmmm, you are leaking." She said. Her fingers left my cock head, then I heard her say, "Mmm, does not taste bad at all." Just listening to her say that was making my cock twitch more, and my balls ache so badly.

She started talking to me again, "We will call that being close to the edge. Our next step is to get you closer still. Now that you have context, what we are going to do is get you used to, and skilled at, getting closer and closer to the edge, maybe even to the edge and holding back that orgasm, but it will likely take some time to get there. for today I will settle for getting you to the point where you are three to five strokes away. So get back to stroking."

For who knows how long she had me stroking and working closer and closer to the edge. She enjoyed scooping up the pre-cum and telling me she was enjoying it. She really enjoyed it when I started making frustrations sounds every time she had me stop. I really don't know how close to the edge I got because she never let me prove it. The ache in my balls through this just kept growing and growing.

Finally she told me to stop, which was a relief, but not the relief I wanted. I heard her get up off the bed, and walk off, then heard her come back. At that point she took the blindfold off, and I noticed that she was once again hiding her beautiful body under her bathrobe. I had no idea how much time had passed at this point.

My cock had relaxed a bit, with no stoking happening, but Amanda had noticed there was once again a build up of precum, so I watched as she reached down, squeezed the head of my cock to move it to her fingers, and then lick her fingers, while looking me directly in the eyes.

"Time to put your cage back on for now." She said, "Teresa will be dropping by after her game and you should be properly attired when she gets here. Come join me on couch when you get it on."

It was almost like she knew that after what she had done, I would not be able to get the cage on with her here staring at me.

I gave my cock some time to calm down, then finally was able to get the cage back in place. I then went out to join her and hander her the necklace with the key on it. She had poured me a glass of wine which I picked up as I sat down. She moved over to snuggle with me, she locked arms with me and leaned her head into my shoulder.

"Thank you." She said quietly. I wasn't sure what she was thanking me for, but she sounded humble and genuine. I made a note to ask her about that at some point, but I did not think that right now was the right time.

She had a tv program going, a sitcom, that I did not really pay attention to. I disengaged my arm from hers, to put it around her, and snuggled into my side even more. It was nice, but my overwhelming feelings were of how desperate I was to cum, and how achy my balls were.

At a little after 9PM there was a knock on the door.

"That would be Teresa." Amanda said. She disengaged from the cuddling, patted me on the leg and said "Go open the door for her."

I got up to go to the door as Amanda found the TV remote and turned it off. She then went towards her bedroom.

I opened the door, partly behind it, because I was naked after all, and Teresa came in.

She looked me up and down as I closed the door behind her and said "Now this is the right ambiance to walk into! Looking good!" She leaned into me and kissed me, before looking for Amanda. She was just coming back from her bedroom with a collar and cuffs for Teresa.

Teresa walked to stand in front of Amanda and started taking her clothes off. That had my attention right away. It was moderately painful but well worth watching Teresa strip, fold her clothes neatly, and put the cuffs on, while Amanda put the collar on her. Once she was all locked up, including the chain, keeping her hands dangling just below her chin, Amanda pulled out a reddish-pink plastic thing that looked like an elongated egg with a long tail. There were creases or ribs in the middle of the egg part.

Amanda said "I was not sure if you had your vibrator, so I came up with a better idea." Teresa's eyes got a little wide as she looked at it.

"Is that...?" She started to ask, and Amanda just nodded.

"Shall I put it where it belongs?" Amanda asked as she pulled out a bottle of lube from her other pocket.

Teresa just nodded at that and raised a leg to put it on the end of the couch, to provide more space. She looked a bit unsteady, so I helped stabilize her, and watched. Amanda put a fair amount of lube on the top of the device, then reached down and but that end against Teresa's pussy, she twisted in semicircles, and moved it up and down, which had Teresa moaning already. She then made small circles with it as she pushed it inwards. There was a bit of back and forth, but then it just slipped right in, leaving this reddish tail still poking out of her pussy. My cage was trying to do gymnastics at this point, which was not comfortable, but I was not complaining. Amanda then went to her phone and tapped the screen a few times. I heard a buzzing from the device, and Teresa's eyes closed and she started moaning at the sensation that it was causing.

"Oops, maybe a bit too high." She said and tapped her phone again. The tone of buzzing changed, and Teresa took a deep breath.

Amanda then said, "I know this feels a bit rushed, but we all work tomorrow. The weekend will definitely be different. So first, tomorrow -- I talked to Mike and he is good with euchre night here at my place. I was thinking I would order pizza, everyone brings their own booze like last time, and we are all on our best behaviour, unless you want Mike to find out about what we are doing?"

I said "Best behaviour, yes!" Teresa just nodded in agreement. Her distractions at the moment seemed a lot more immediate, so I understood not sparing the energy to talk.

"Good!" Amanda said, "I am thinking that we do girls against guys, and what is on the line for you two is which of you gets to have an orgasm first. If the guys win, Tom you get lucky first, but if the girls win, Teresa, you get to cum first! How does that sound?"