Chapter 2

The next day after my first experience in The Room, Fiona wanted me to talk about how I felt about what I had done, or what she had made me do, or what had been done to me. I was still sorting it all out in my head. Ever since she introduced me to her kinky side, we had talked about our fantasies as well as our limits. She had never crossed a line before and she didn’t that night either. She knew that I was a little bi curious and most everything else we had done before. It was just the combination of things and the way she had “forced” me into my first bi experience. If I had to be honest it was almost exactly how I had always wanted it to happen. I was just caught off guard, but somehow that made it even more exciting. I was also still extremely concupiscent and the cream that she had used to keep me from being able to cum still hadn’t worn off completely.

“I’m not sure how I feel,” I said after a thoughtful pause.

I was sitting naked on the sofa with her sitting beside me, fully clothed, with her hand on my knee. My cock was still semi-hard from last night and my inability to orgasm.

“You aren’t upset with me, are you?” she asked, genuinely concerned.

“No, no, not at all!” I assured her, “It was just a huge surprise, I wasn’t expecting quite, um, so much.”

“Well, he wasn’t that big, but he did cum a lot,” she chuckled at the word play.

I blushed, remembering how the cock felt as it grew and got harder in my mouth making my own cock begin to rise again as I laughed at her little joke.

“Yes, he did,” I admitted as I looked down not wanting her to see my face, “but you know what I mean.”

“Yes, I understand. I just remember how you described your fantasy of being forced to suck another man’s cock and I wanted to make it happen for you, baby.” she said, placing her hand under my chin and lifting it up so she could look into my eyes again.

“You definitely got it right,” I said and smiled.

“And I know you are still desperate to cum. I might have used a little more of that cream than I needed, but it was the first time I’ve tried it on you and I wanted to make sure you didn’t cum,” she explained, “I wanted you to stay on the edge to make you more willing, you know?”

“It definitely did the trick,” I said as I tapped on the now hard shaft between my legs.

“Don’t worry, it will wear off soon and I will make him feel all better,” she said, reaching over and stroking my cock, making me produce a little moan.

“And how do you feel about being a cock sucker, now?” she asked, holding my gaze as she continued to tease me.

“That’s the part that I’m not so sure about,” I said, my voice breaking a little.

“I’ll bet, before long, you will be looking forward to your friends coming over for your training sessions”, she said.

“Does this mean we are going to do this again?” I asked, a little afraid of the answer, “and a lot?”

I was so close to the edge that I was already producing precum. Instead of answering me right away, she milked a large drop onto her fingers and brought them up to my lips. I sucked her fingers into my mouth and licked them clean.

“I think we both know the answer to that,” she said as she brought her hand back down and resumed pumping my cock.

We talked for a while longer and I felt better afterwards. It really had been an amazing way to pop that particular cherry.

Over the next few months she continued to repeat the experience at least once a week, sometimes more. She always made sure I was bound and unable to resist just like the first time, but slowly I started to become a more willing participant. She also continued to keep me blindfolded so I wouldn’t know who was the recipient of my oral services. She would only tell me that I knew him well and saw him frequently so that I would continue to wonder which of my friends knew about my secret perversion.

I knew there were at least three different guys. I kept trying to discern some clues about their identities but, between the earbuds and blindfold, all I had to go on were the details of their cocks and balls. One was thicker than the others and one was so long I couldn’t take the full length without gagging. They were all shaved smooth. The thick one and the regular-sized one were both circumcised. The long one was not. The regular guy had the biggest balls. The thick one’s balls were always tight against his body while the other two had theirs hanging a little lower. I was also starting to notice differences in the taste of their cum, but I didn’t know how any of these details was going to help me identify them. It’s not like I could just randomly ask my friends if I could see their cocks.

Fiona had always liked to tease me and deny me orgasms while making me give her as many as she could stand, but I was noticing a new trend. She kept me denied much more often. I realized that she was making me hold off until my “training sessions”, as she liked to call them. She hadn’t used the special cream on me since that first time. Instead, she would use a slim vibrating wand with a slanted head to massage my prostate while she stroked my cock. She would bring me to the edge multiple times while I sucked and swirled my tongue and tried my best to make the mystery cock cum as quickly as possible, but it never worked. He would withdraw his shaft when he started to get too close and I would be forced to suckle his balls until he calmed down and then he would feed me his cock again. Meanwhile Fiona would stop and start her ministrations as well to keep me right on the edge. The two of them would coordinate their efforts so my own orgasm was synchronized with his climax into my mouth.

After I swallowed every drop he had to give and licked his shaft clean, as she had taught me to do, she would bring her hand to my lips so I could clean up my own cum as well. She had been feeding me my own cum almost since we started dating so that really wasn’t anything new, but it was especially humiliating that one of my friends was watching me greedily suck the cum off her fingers as if I hadn’t gotten enough after his massive load. I felt like a true cum slut in those moments.

I knew she was doing all of this to make me associate my own pleasure with sucking cock, but even though I was aware, it was still working. It was humiliating to admit, but I began to crave the taste and feel of a dick in my mouth. I liked feeling it grow and get hard as I worked it with my tongue and lips. Most of all I wanted the reward at the end, the salty-sweet taste of the semen, the gooey feeling on my tongue that lingered even after I swallowed.

Once she knew I was hooked she started adding a few little extras just to make sure I was humiliated as much as possible. I had to say “Please sir, may I have your cock” before I was allowed to take his member into my mouth, and then, after he was done and I had eaten both of our emissions and licked him clean, I had to give him one more kiss on the head of his penis and say “Thank you sir, I can’t wait to do that again very soon”. My reward became a pat on the head like a pet.

In between training sessions, she started making little comments about random guys we would see and ask if I thought he might have a nice cock, or lewd references about my sucking technique and how the guys had told her that I was becoming the best cock sucker. She especially liked teasing me about how much I was starting to look forward to having them cum in my mouth, just like she had promised I would.

One day she came home with a bag from the local adult store.

“Is that for me?” I joked.

She just smiled and said “Actually, it is. Let’s try it.”

She handed me the bag and I opened it cautiously. You never knew what she might bring home. Inside was a new gag that she had found - it was essentially a double ended dildo with a fat ball in the middle with leather straps on either side of the ball.

“Since we started your training, I’ve kinda been feeling neglected,” she said as I pulled the toy out of the bag.

I looked a little surprised, since I eat her to multiple orgasms whenever she wants.

“I know, you are great at eating my pussy, but sometimes a girl needs a nice hard cock,” she said before I could reply.

I started to say that I had a perfectly good hard cock right now, but she put her finger on my lips.

“I know, baby. Just go wash it and then bring it back here so I can put it on you,” she said.

Without another word, I took it to the sink and washed and dried it, then came back to where she was sitting on the sofa.

“Good boy,” she said, taking it from me, “now, open up.”

I opened my mouth wide and she slid one end of the dildo into my mouth until the tip of the dildo was touching the back of my throat. I started to gag and she backed off a little. I cleared my throat and swallowed to get more saliva back there like I was learning to do with my long-cocked friend and when I recovered she tried again. This time I was able to take it. Only a tiny bit more and the ball was wedged between my teeth. She then brought the straps around the back of my head and buckled them into place. The tip of the dildo was now just touching the back of my throat. It tickled and made me want to swallow reflexively, but there was no way for me to push it out so I just relaxed and tried to get used to it.

“This should help reduce your gag reflex so you can take that long beautiful cock all the way to the balls soon,” she said as she grabbed a bottle of lube from the end table, pushed my head down between her legs, and leaned back.

“Mmmm mmm,” was all I could manage as a reply.

She never wore panties so she just lifted her short skirt and helped me force the other end of the dildo into her already wet cunt. After a few strokes to get it lubricated, I fucked her until my neck and mouth ached and she had more orgasms than I could count. Her cream covered my face when we were done and I could smell nothing but her sex.

This quickly became one of her favorite toys and when she’d had enough, she would roll over and curl up, satisfied with her well fucked pussy. I would get up and remove the gag, clean it up and put it away, all while sporting a throbbing unsatisfied hard on. As much as I hate to admit it, however, it did help me get over my gag reflex.

There were other similar games she liked to play. Most with the same ending for me. She made me promise not to masturbate without her permission and that became another of her favorite activities - making me strip and stand naked stroking myself while she watched. I jerked for her in the kitchen while she made dinner, beside the sofa while she talked on the phone with her friends and family, in the bathroom while she took a shower. Sometimes she would decide to drive when we were going somewhere and I would have to pull down my pants and jerk in the car. Occasionally she allowed me to cum from these masturbation sessions, but only after edging myself many times over several days. And I always had to catch and drink every drop of the cum I produced. Other times she would make me go for days without touching me or allowing me to touch myself. I’m still not sure which was worse.

Over the summer she added another little game to our relationship - when it was my turn to cook or do some of the household chores, she started making me strip and put on nothing but an apron. She would tease me the entire time, running her fingernails over my bare flesh, rubbing against the bulge in the front of the apron and penetrating me with her finger if I had to bend over to do something.

One day while I was working in the kitchen in my “uniform”, there was a knock at the door. I gasped and started to head to the bedroom.

“No, don’t go. Keep doing what you are doing. I’ll get the door,” she said, then smiled and added, “this time.”

I was torn. The kitchen was on one side of the large open floor plan. The living room area was between the kitchen and the door, so when the door was open, there would be a clear view across the room to the kitchen, but there was a long waist-high bar so they would only be able to see the upper part of my body. As long as I was facing the door, they might not even notice I was bare chested behind the apron. At least this is what I was telling myself as I grabbed a towel and started wiping down the counter top.

Fiona opened the door. It was a UPS delivery. As she signed his device with her finger he noticed me in the background and gave me a little nod and I just raised my hand in reply. His eyebrows raised and he started to take a closer look at me, but Fiona was handing his device back and he took it and he handed her the package, then headed back up the hall. Fiona closed the door and brought the package over and put it on the bar.

“See, nothing to worry about,” she said.

“I think he noticed,” I replied, blushing.

“Noticed what? You were behind the bar,” she said dismissively, “besides, we can do what we want in our own home, right?”

This was her view about a lot of things so I knew there was no point in arguing the point.

She pushed the small box across the bar.

“Is this for me?” I asked.

“Yes, just a little ‘upgrade’ for your uniform,” she said, smiling deviously.

Her little gifts were almost always a double edged sword so with a little trepidation, I opened the box, which seemed heavier than I expected. Inside was a lump wrapped in bubble wrap which I peeled it away to reveal a shiny new butt plug! It was made of stainless steel and was shaped so it wouldn’t easily come out with a rather large (in my opinion) bulb-shaped head followed by a slender shaft and a flattened ring handle at the end. It was one of the higher end designs that he had been looking at online recently, but how did she know? He had been careful to clear his browser history.

“Oh, wow, you shouldn’t have,” I said sarcastically.

“We have been talking about this for a while, I thought it was time we gave it a try,” she said chuckling.

“Isn’t it kinda big?” I asked, picking it up and feeling its weight.

“I did some research. It needs to be big enough so it won’t slip out easily. The thin shaft will allow your sphincter to close around it keeping it in place. You should be able to feel it inside you but it won’t be constantly stretching those ring muscles so you can wear it for extended periods of time,” she said, sounding like a professor of analology or something.

“Extended periods?” I queried, those being the words that stood out the most.

“Yes, well, maybe not at first, but over time you should be able to keep it in 24/7 if I want,” she said.

“Let’s take it slow, okay?” I said, nervously looking at the large head of the toy again.

“Of course, sweetie. Have I ever pushed you too far, too fast?” she asked.

“No, I know you take your time with me and that I worry too much sometimes,” I replied.

“So, let’s try this thing on,” she said, motioning me towards the sofa.

She sat on the middle seat and scooched all the way back. This was her usual, over-the-knees spanking position.

“Hand me the lube and the plug and then lay down here,” she said, patting her lap.

I did as I was told. This was one of the most humiliating positions, I always felt like a child and incredibly exposed. She started by pushing the outside leg off of her knee to spread my legs and give her better access to my puckered little hole. Then I heard the snap of the cap on the bottle of lube and felt a trickle of cool liquid drip right on the spot. The cap snapped closed and then she started working the lubricant around the rim and then into the hole itself. When she was satisfied that she could get two fingers into me past the second knuckle, I heard the lube cap snap open and then closed again. The next sensation was the cold steel plug touching my anus.

“Are you ready, baby?” she asked.

“Yes, just go slow, okay?” I replied nervously.

“Of course, but you have to relax for me. Just relax and let it happen,” she said soothingly. This was one of her favorite phrases.

I tried to relax my sphincter as she started to press the fat metal bulb into my ass. I whimpered as my muscles stretched around the invader. She backed off for a second and spun it around to make sure everything had plenty of lube, then pressed again more firmly. I moaned a second time but she didn’t stop. There was a squishy plop as the head passed through the ring and my involuntary reaction was to squeeze it closed, which sucked the plug the rest of the way in, right up to the handle.

“Oh, god, that felt huge!” I exclaimed, feeling a slight ache in my anal muscles.

“Good, boy. That was so amazing to watch,” she beamed.

She started tapping on the handle of the plug, which made me flinch and then squirm. It was just touching my prostate which was sending crazy vibes across my whole body as she tapped.

“Let’s get you up and see how it feels,” she said, finally.

It was harder to stand up than I expected. Every movement seemed to make me squeeze the plug or make it move inside of me.

“Now, go finish cleaning up the kitchen and see how it feels,” she said, smacking my bare ass.

“Yes, ma’am,” I joked.

So I cleaned the kitchen and spent the next several hours with my ass filled with this lump of steel. It felt heavy in my hole and constantly reminded me of its presence when I moved or bent over, and especially when I sat down. The handle fit perfectly between my ass cheeks but sitting pushed the plug deeper into me.

“You know, that plug is so sexy, I can’t wait until you can wear it all the time,” she told me later that evening after she had watched me bend over to put something in the bottom drawer of the cabinet we used as a TV stand.

“Are you really going to make me wear it all the time?” I asked.

“Well of course you have to take it out to use the bathroom and you will want to keep yourself clean back there,” she said.

So, after a couple months of wearing it for longer and longer periods, I reached her goal of keeping my ass plugged all the time. I grew used to its constant presence but never enough to forget it was there. It was especially present in my mind when I was hanging out with friends because some of them knew I was wearing it now. They had watched her remove it so she could tickle my prostate while I sucked their cock and then put it back in place afterwards. It was so embarrassing because it could be any one (or three) of them! I wasn’t even sure if they knew about each other. Sometimes I thought I might have seen a knowing smile when I squirmed a little and I was tempted to ask if he was one of my “cum buddies” (another phrase Fiona had started using), but I never dared to ask. I couldn’t imagine how I would explain myself if I guessed wrong.

One evening when I was cleaning in the living room, Fiona called me over to the chair by the window. I always avoided that spot when I was doing chores in my apron because the neighbors across the street could surely see inside our apartment, since we could clearly see inside theirs. They were an older couple and they seemed nice and friendly when we bumped into them in the hall. Everyone in the building kept their windows open as much as possible when the weather allowed, which was most of the year in this region.

She untied the apron and gestured for me to take it off. I glanced nervously out the window and couldn’t see anyone in the other apartment. I removed the apron and dropped it on the floor. My cock was standing especially tall that evening, probably because it had been awhile since she had let me cum. She raked the underside of my shaft with her fingernails gently.

“You know,” she said, “I think I like you better like this. I want you to stay nude at home all the time. Will you do that for me?”

This really wasn’t a huge change. I ran around in just an apron a lot, slept fully naked, walked from the bathroom to the bedroom naked, and lots of other things, but somehow, this felt like a a real inflection point.

“What does ‘all the time’ mean,” I asked. I knew she could be a bit of a rules lawyer.

“Just how it sounds. Anytime you are home, you would be nude. Some people call it being a home nudist,” she explained, “I will let you wear the apron when you are cooking. We don’t want to get anything burned,” she said, patting my penis, making it bob.

“What about when we have company?” I asked, afraid of the answer.

“I think we can play it by ear. I don’t think most of our friends would mind,” she said confidently, as if she had already taken a poll.

“I might mind!” I exclaimed.

“Oh, come on, baby, you trust me, right? What is my number one responsibility?” she prompted.

“I know, safe and sane,” I said, repeating her mantra.

“That’s right. Have I ever pushed you too far too fast?” she asked. This was another of her sayings about our evolving lifestyle.

“No, but, our friends? The guys are going to be brutal,” I said, imagining my friends laughing and calling me pussy whipped, or worse – seeing my smooth hairless body with everything exposed. My plug, oh god, what would they say about my plug?

I was flushed and red faced, but as I looked down and saw my rock hard cock sticking straight out, I knew I was going to go along with this. Fiona had known I would before she asked.

“Don’t worry, I’ve already planted the seed with your cum buddies. They have agreed to help tone down the others,” she said.

So she had been planning this for a while. The groundwork was laid. I should have known, she always seemed a step ahead. And maybe this would be my chance to finally discover who the three guys were! Thinking of my cum buddies gave me a craving for cum. It had been a while since we had any of them over. The idea of taking a cock into my mouth, or even my ass if I had to be honest, sounded good right now. Then I remembered Fiona was waiting for me to say something...

“Okay,” I finally said with much hesitation, “but we take it slow, right?”

I wasn’t sure how to slowly come out as a nudist, but it seemed like the only point of control I had.