Fiona and Brian Chapter 7 — Payments and Rewards

I was finally able to pull my head out from between Fiona’s legs after she started to come down from her fourth orgasm. My mouth, nose, and chin were wet with her fragrant juices. My tongue had started to ache after her third orgasm but I knew I could get her there one more time.

“That was fantastic, baby,” she cooed and tried to catch her breath,” you really know how to work that tongue.”

“I’ve had a lot of practice since I met you,” I said, smiling.

I wiped my chin and nose with my hand and then licked it clean. I never wanted to waste a drop of her. She wasn’t a squirter as you see in some videos, but she got exceptionally wet when she was aroused.

“I need another shower but I don’t have time,” she said, “can you be a dear and get a washcloth and clean me up a bit? I don’t want everyone to be able to smell my cunt all day.”

“Of course,” I said, standing up, my knees aching from being on the hard floor for so long.

The movement brought back to my attention both the chastity cage that was locked around my cock and balls, and the new plug that was filling my ass. The chastity was the same custom-ordered 3D-printed model that I had been wearing for close to a month now. The plug was a SnugPlug size 5. It was a 2-inch diameter silicone plug with two weighted balls inside. At least it had a flat T-shaped base instead of the protruding ring that my last one had. I could now sit in relative comfort, but its girth and those damn balls rattling around made me squirm whenever I walked or moved around.

“Oh, look at your poor little cock trying to get out of its cage,” Fiona said with mock pity as it came into view. “Maybe I’ll let you cum soon if you continue to be such a good boy.”

I just smiled and nodded and put my hands together like I was praying or begging, and bowed slightly making her chuckle. I hadn’t been allowed to cum since the last time the cage was off. She had started controlling my orgasms soon after we started dating so I was used to giving her pleasure without expecting a release, but the time between my orgasms was getting longer and longer.

I walked to the bathroom, grabbed a washcloth from the basket beside the sink, and ran the water until it was hot before getting it wet and then wringing most of it out. I might have been tempted to wash my face while I was there, but I knew Fiona liked for me to keep her scent on me so I just checked myself in the mirror before I returned to the living room where Fiona was still slouched down on the sofa with her legs spread wide and her glistening pussy on display. God, she was gorgeous!

She had picked up her phone from the side table while I was gone and was typing. It had chimed in the middle of her second orgasm so she was probably checking her messages now.

“Carson is going to be stopping by later to drop off the straps for your chastity,” Fiona said absently as I knelt once again between her long shapely legs. 

It had been a little over a week since we visited Carson and Brandy when he had taken the measurements and discussed various options with Fiona. It had also been my first time leaving the apartment completely nude! The experience had been both thrilling and mortifying, to say the least.

“Okay, is there anything I need to do before he gets here?” I asked, knowing that “put on clothes” would not be one of those things.

I gently pressed the warm wet cloth between her legs, making her sigh. I let her get used to it before I started gently cleaning her beautiful smooth pussy.

“No…ooh, god…ahh…I’ll be at the gallery when he comes so just be a good boy and do whatever Carson tells you,” Fiona said as I made her squirm.

I ran a cloth-covered finger down between her ass cheeks, making her purr. She had made me start off licking her asshole, which she loved, but that would never make her cum. Once her juices started flowing, it trickled down and I used it as lubrication to slip a finger into her ass while I licked her pussy and clit. That’s how I got her to her first orgasm so quickly.

“Yes, ma’am,” I said, smiling, as I finished off by wiping the last of it from her thighs.

I moved back a little and she scooted her ass back onto the cushion so she was sitting upright, then stood up shakily. I was still on my knees in front of her, so her beautiful slit was right there in front of my face and I couldn’t resist giving it one more kiss.

“Stop that or I will never get to work,” she said, tousling my hair before stepping around me. She pushed her skirt down from where it was bunched up above her waist, twisted it around so the front was actually in the front, and then tried to smooth it out as best as she could. The hemline fell about halfway down her thighs. Just enough to keep anyone from knowing that she wasn’t wearing panties – as long as there wasn’t an updraft.

 

It was just a little after noon when the buzzer from the front door of the building sounded. I walked over to the intercom beside the door. It had a small screen that showed a grainy black-and-white video feed showing the front entrance of the building. I could see it was Carson, as expected.

I pressed the talk button. “Hey, Carson, come on up,” I said, then buzzed him in.

The display went dark and I waited there by the door, fidgeting. I realized I could still smell Fiona. Was it just from my face or did the room smell like her sex? I wondered if Carson would notice. Well, there was nothing I could have done about it at that point regardless.

I didn’t think I would ever get used to answering the door naked, and this would be the first time I would be alone with Carson. Even though I had gotten to know him a little (including an intimate session with his cock), I was still nervous and had this desperate need for his approval. He had been one of Fiona’s mentors, but it was more than that. I felt like, in some way, he might be a role model for me. He had also been his wife’s submissive at the beginning of their relationship and maybe he still was and always would be, though they seemed to be more like equal partners when we visited them.

The knock at the door startled me from my thoughts. I steeled myself, tried to smile and not look nervous, then opened the door.

“Brian!” Carson said as he stepped in, and put his hand out.

“Carson,” I said, taking his hand, both of us delivering a firm manly handshake as if we were just two guys and one of us wasn’t naked and wearing a cage on his cock and a plug in his ass.

Carson had a handful of narrow leather straps.

“Thanks for bringing those by,” I said, closing the door behind him.

“I think they turned out pretty well,” Carson said.

“They look great!” I said, admiring them. “I love that burgundy color.”

“Yes, Fiona has excellent taste. I cleaned them as much as I could after I stained the leather but they still might bleed a little onto your skin for a while,” Carson explained. “It’s a plant-based dye so it won’t hurt you and it should wash off with a little soap and water.”

“Okay, that shouldn’t be a problem,” I said.

“If you have any problems with them, just let me know,” he said. “Shall we try them on?”

“Sure,” I said, trying not to sound as embarrassed as I felt knowing that he was going to be handling my cage again momentarily, “where do you want me?”

Carson scanned the open loft for a moment, looking for a good spot.

“How about over there by that chair,” he said, suggesting my desk chair.

We walked over and he placed the straps on the desk then sat in the chair and motioned for me to stand in front of him. He reached down the side of the chair and found the handle that would lower the seat until he was at eye-level with my crotch. After going so long without an orgasm, a gentle breeze would keep my cock filling the tiny cage. As he grasped my balls with one hand and started examining the cage more closely, my cock began to try and squeeze through all the small openings and I inhaled sharply. I hated being so close to the edge already. I would be mortified if I couldn’t hold back, plus Fiona would kill me.

“You seem to be on a hair trigger today,” he said, smiling. He knew I wasn’t allowed to cum without Fiona’s permission but he had noticed my reaction and decided to test my resolve by nonchalantly rolling my scrotum around in his hand.

I wasn’t expecting to be teased like this and held my breath, fidgeting a little, but let him continue – as if I had a choice.

“That really is a nice cage. Fiona sent me the info on where she had it made. I need to order one for the new guy.” he said as if chastity cages were just a normal topic of conversation. Maybe they were while you were actively fondling another guy.

“Oh, are you and Brandy taking on a new sub?” I asked, my voice sounding a little husky.

“That submissive couple we were telling you about the other day,” Carson said, switching to more of a gentle kneading, “They are coming over tomorrow for their first session.”

“Nice!” I squeaked, not knowing what else to say. Does Hallmark make cards that say ‘congrats on your new subs’ I wondered trying to distract myself with a little humor.

I closed my eyes and tried to think of something other than his skillful manipulation of my anatomy. I knew better than to try and pull away or ask him to stop. Fiona might have sounded cute when she told me to be a good boy, but she meant it. My behavior reflected on her and the training she had given me. I didn’t want to let her down.

“Let’s get these cords off,” Carson said, finally releasing me from the pleasant torment.

I started to reach for the knot on my left hip, but he was already there, pulling on the end that would set them free. I decided to just keep out of his way and I put my hands up behind my head.

“This was pretty inventive as a temporary solution,” he complimented.

“Thanks, I was a boy scout when I was younger. I still remember a few things,” I explained, starting to regain my composure.

“That will come in handy if you get into rope bondage later,” he said, letting the two ends drop so they just dangled down along each thigh.

Carson worked the cords loose from the base ring on one side and pulled the end through the loop and then out from under the ring, then repeated the same process on the other side.

“These straps will work pretty much the same way as your cords, but they loop around the ring and have these snaps to hold them in place,” he explained.

Carson showed me how they worked before attaching them to either side of the ring. There was a row of snaps on each end to adjust the length so it would fit snugly around my waist. He adjusted them until they fit the way he wanted.

“Remember that, you should be able to use the same ones every time, but the leather might stretch a little as you break it in. Kinda like your ass,” he said tapping on the base of my plug.

I jumped a little, surprised by the little tremor it sent through my stretched sphincter.

“Is that a new plug?” He asked. “You had a steel one in when you came to the house.”

“Yes, Sir. Fiona just got it for me a few days ago,” I replied.

“Looks like a pretty good size. How’s it feel?” he asked, now rubbing his finger across the base.

“It…it…keeps me very full,” I stuttered, trying to focus despite the sensation, “And it has a couple of weighted balls inside that rattle around when I move.”

“Oh, very nice!” Carson exclaimed.

I could feel the precum leaking from my compressed penis. He was going to make me cum if he continued to tease me like this. I wanted him to, but I would be in so much trouble. Finally, in a brief moment of clarity, I decided to try and shift his focus back to the straps.

“I assume I need to take them off when I shower,” I said, then added, “I took the cords off, even though I probably didn’t have to.”

My plan worked, he stopped fiddling with my plug and picked up one of the straps from the desk.

“You might want to,” he explained, “I used some beeswax to polish them so they should be somewhat water-repellant but if they get soaked, you should press as much water out as you can with a towel and then let them dry flat. If they dry on your body, they might curl or twist.

“And they will absorb sweat and oils from your skin over time,” Carson continued, “You will need to clean them occasionally with some good leather cleaner and then polish them with some wax again. If I had thought of it, I would have brought some, but I’ll just send Fiona a message with the brand I recommend.”

“Sounds good,” I said

“I think that’s it. They should hold that cage in place with no problem, especially since it’s so light,” he said with a little tug on the cage, making me flinch. “I usually prefer a steel cage for my subs but they are so much heavier. You could probably run a marathon in that thing and forget it was even there.”

“Well, I don’t know about forgetting it’s there, but I do like the way it feels compared to any of the others we tried,” I said.

“There are a few other straps here that you guys can use as needed. One is more of a jock-strap configuration that will go across each cheek and connect to the ring behind your balls. And there are two back straps. This slender one,” he picked it up to show me, “that will just slip between your cheeks like a thong, and this one that has the panel for holding a dildo.”

I knew Fiona was looking forward to trying the one with a dildo. I wasn’t so enthusiastic.

“Thanks. So, what do we owe you?” I said

Carson pulled the handle on the side of the chair again and let it rise back up to its full height.

“I don’t want any money, but I will take another one of those blowjobs,” he said looking up at me with a half grin.

I almost did a double-take! I didn’t expect that response. It never even crossed my mind, though, In hindsight, it probably should have. His was the only cock I had ever sucked ‘willingly’, so to speak. For all my other cock sucking experiences, I had been blindfolded and bound to a chair while my friends essentially fucked my mouth. After a while, I became more complacent (some might say eager) about sucking their cocks and I did my best to improve my technique as much as I could, but I was still mostly a passive participant. This arrangement continued, in large part, because I still wasn’t allowed to know which of my three friends was using me as a cumdump. 

When we last visited Carson, Fiona had been bragging about my skills, and Brandy had suggested a little demonstration. With Fiona’s approval, I crawled across the floor to get between Carson’s legs and actively suck his cock. So, the precedent had been set. But that was still with Fiona’s approval and with both her and Brandy’s supervision. It still felt like something that I wasn’t choosing to do. This time it would be all on me – well, mostly. Fiona had told me to do whatever Carson wanted…

Carson noticed my hesitation and got a thoughtful look on his face before speaking.

“Brian, have you ever filled out one of those online profiles where it asks for your sexual preference?”, Carson asked

“Yes, of course,” I said, a little confused as to where this question had come from. “Fiona and I have accounts on a few different sites. Why?”

“Brandy and I do too,” Carson said. “And what do you think I put on my profile?”

“Umm, well,” I stammered. I wasn’t sure what to say. Would he be offended if I got it wrong?

“Don’t worry, you probably won’t guess anyway,” he chuckled, “most sites don’t even have a good option for me to choose from. But what do you pick?”

“Oh, well, I think they all say ‘straight’ right now because I haven’t updated them in a while,” I said, trying to remember. “I suppose I should change them to ‘bisexual’ now.”

“You could. And I’m not telling you who or what you should be, that’s for you to decide,” he said, “but let me ask you – are you attracted to guys, Brian?”

I was a little shocked for him to ask that question. I had wondered about that myself recently. There was a time when I would have flatly answered ‘no’. But it wasn’t so simple now. I sucked cock regularly and had even taken multiple cocks up the ass as well as Fiona’s strap-on. I didn’t choose to do this in the beginning but I also didn’t say no, and lately, I had even asked for it a few times. But while I loved Fiona and women in general and enjoyed looking at their bodies, I only craved the feel and taste of cock and semen in a needy sexual way. So would that make me bi?

“Well, sort of, I guess,” I said hesitantly, “but not the same way as women. It’s like…”

“Don’t try to decide right now,” he said, cutting me off. “You don’t need to tell me at all unless you just want to talk about it with me. It just seems like this is something you might be struggling with so I wanted to give you some advice as someone who has been there before.

“I know I’m not really attracted to guys, but I learned (pretty much the same way you are) that they are fun to play with,” he said smiling and reached out to cup my balls again.

“Ooh, umm, makes sense,” I stammered as he started to fondle me. I didn’t think it was possible for me to get any bigger in my cage, but I was wrong. 

Carson continued, “I know how embarrassing it is at first, to take a cock in your mouth and swallow some guy’s cum. But then you discover that it’s not so bad. You might even kinda like it, but then it’s even more humiliating that you are actually enjoying it, maybe even craving it.”

“Mmm hmmm,” was all I could manage. He knew just how to manipulate my testicles for maximum effect.

“You think about how it feels, how the cum tastes and you want to do it again but it’s humiliating to ask for it,” he continued as if he had read my mind. “And you just got fucked by a real cock for the first time recently, so you are probably thinking that at some point, you are going to be craving that feeling too. If Fiona has been pegging you regularly, you probably already do.”

I identified with everything he was saying and him knowing this about me was even more embarrassing. I felt like he was seeing right through me. He was watching my face closely as he continued to play with my balls.

“And I will bet you a blow job that you get off on all that humiliation even more than the act itself,” he said, seeing from my expression that he was right.

I was so completely mortified (and on the edge) I was almost shaking. He was right about everything, but I didn’t have words to respond. I realized it was time to stop hesitating. I knew from the moment he mentioned it that I was going to suck his cock. But somehow I felt better after talking to him.

“May I please suck your cock now, Sir,” I said in a low voice, looking down at the floor. 

“I was starting to think you would never ask,” he chuckled.

He released my scrotum and allowed me to sink to my knees in front of him. The plug in my ass sent vibrations into my prostate to remind me it was still there.

He was wearing khaki shorts and a Hawaiian shirt again. Not the same as the first time we met, this was just his style, apparently. I lifted the clasp on the woven cloth belt he was wearing and pulled the end through, unfastened the button at his waist, and then lowered the zipper. He stood up so I could pull his shorts down to his feet, revealing his bulging package encased in tight blue silky underwear. I would have almost considered them panties but they were made with a pouch in the front for a man. 

With my fingertips, I traced the outline of his cock and balls through the thin material for a moment and he began to breathe heavily. Then I reached up to the waistband on either side and peeled them down his legs on top of the shorts. His hardening member, released from its confinement, bobbed in front of my face. Just like the last time, his cock and balls were completely smooth and the rest was neatly trimmed. I remembered his scent from before as well. I couldn’t resist a little taste and I stuck out my tongue and licked the head.

Carson sighed, as he sat down in the chair before I could do any more and slid forward to give me better access. I pulled the shorts and underwear off of his feet and tossed them aside so he could spread his legs farther, making room for me between them. I crawled forward until my face was only inches away from his cock. I lifted the shaft with my fingers and guided just the head into my mouth. He wasn’t fully erect yet and I wanted to feel it grow. Still holding it with my fingers, I licked and sucked and teased as it became longer, thicker, and more rigid. 

Satisfied with the results so far, I took it fully into my mouth, savoring the flavor of his precum. I sucked and flicked my tongue across it then started to bob my head up and down slowly. I took his balls in my hand and fondled him the way he had fondled me earlier. I could hear him moaning softly over my occasional slurps. I got into a rhythm and tried to give him the best blow job he had ever had, stopping only to catch my breath and swirl my tongue around the head, or to slowly take the whole length down my throat for a few moments, and then go back to my steady pace. 

I got lost in my fervor to please him. I don’t know how long I continued but suddenly I could feel him squirm in the seat and get just a tiny bit larger. He was almost growling so I knew that he was going to cum soon. I decided to try and stretch him out a little longer and pulled his cock out of my mouth. He moaned in protest and reached for my head to put me back to work, but I ducked under his hand and started licking and sucking his tight smooth balls while I jacked his cock with my hand. He stopped trying to take control and just laid back and let me continue.

I worshiped his balls until I thought he would have come down from the edge before returning to his cock. Wrapping it tightly in my fist, I worked on just the head, sucking it and using my tongue to tickle the glans underneath and flick back and forth across the tip. This made him squirm again and make guttural noises which I took as my cue to plunge it down my throat until I could stick my tongue out and lick his balls. I kept it there as long as I could and swallowed, letting my throat muscles massage the head of his cock. When I finally pulled back, I had to cough but then returned to just teasing the head. I repeated this a few more times until I thought he had had enough and then went back to bobbing fast and deep. 

I could feel him reaching the edge again and I had one more trick up my sleeve. As I continued the rhythm, I slid my fingers down the shaft and across the balls, collecting as much of the slippery saliva as I could, then I went lower and worked my fingers between his cheeks until I found his asshole. I rubbed around the rim, feeling the pucker of his sphincter. Carson emitted a growl and spread his legs a little wider to give me access as I slowly worked my finger into his tight hole. I only got the first knuckle in before he exploded, but he bucked and my finger was shoved past the second knuckle! He howled as he flooded my mouth with ropes of hot semen. I swallowed as fast as I could, not wanting to lose a drop. I twisted my finger in his ass trying to tease as much out of him as I could.

As he stopped convulsing and started to relax, I slipped my finger out of his rectum but continued to milk his cock with my hand and mouth until he finally pushed me away.

“Goddamn, Brian, that was better than the last time!” Carson exclaimed.

“I have been practicing,” I laughed as I licked the last few drops of his cum off of my lips.

We were both breathing hard and neither of us moved for several long minutes. I watched his penis deflate as he lay there in the chair looking almost exactly like Fiona had this morning. A few more drops of semen oozed from his cock and I quickly caught them on my fingers and licked them clean.

“Fiona has trained you well,” he said and I just smiled.

“Would you like something to drink,”  I asked, finally.

“Sure,” he replied.

“Whiskey, or….” I started to ask

“Just water, please. I’m going to have to drive home soon,” he said, shifting himself back up in the chair.

I stood up and walked across the open room to the kitchen, receiving more vibrations from my not-so-little friend, and brought back a bottle of water from the fridge. I loosened the cap and handed it to him. I continued to savor the taste of his cum in my mouth, as I had been taught to do.

He took a sip before saying “Thanks.”

He complimented me on my skills a couple more times as he recovered himself and got dressed.

“Fiona said something about a special chair you guys put together. I’d love to see it,” Carson prompted.

“Sure,” I said and led him down the hall to The Room, as we called it.

“Wow, that’s pretty nice. You did some of this work yourself?” he asked, looking at where the eyebolts had been welded on as tiedown points.

“Yes, I do a little welding and metalworking,” I said. “Mostly it’s for art projects but occasionally I get to do functional stuff.”

“Well, that is fantastic!” he exclaimed. “Brandy and I could use something like that in our private dungeon.”

“We found the old chair in an antique shop. If you look around and find one, I would be happy to make any repairs and improvements it needs,” I offered.

“We might take you up on that,” he said.

He admired the chair a bit more and then took in the rest of the room for a few minutes.

“Well, I had better get back,” he said at last, “you let me know if you have any problems with the new straps.”

“I will, and thanks for the advice and stuff,” I said, holding the door for him and then closing it behind us.

“Maybe it will help, maybe it’s just an old man rambling,” Carson said as we continued towards the front door. “If you ever need to talk about anything, just reach out. I don’t think Fiona would mind.”

“I appreciate that,” I said.

When we got to the door, he said “We’ll have to do this again,” and winked, then we both laughed.

 

When Fiona got home that evening, she immediately wanted to see the new straps. I modeled the one I was wearing and showed her the others.

“Everything turned out great, I think. How does it feel?” She asked as she examined the one for a dildo. 

“It’s not much different from the cords. I think it will be just as comfortable and it definitely looks better,” I said, shifting around so she could get a good look.

“And how is your new plug feeling?” she asked, noticing it peeking out between my ass cheeks.

“It’s fine, It never lets me forget that it’s there,” I replied. It had been giving me little vibrations as I moved around to show off the straps.

“Ooh, has it been keeping your cage nice and full today?” she cooed.

“Yes, and I almost lost it today when Carson decided to play with me a little when he was putting on the straps,” I said. 

“Oh, did he, now!” she said, reaching out to grab my balls and roll them around in her fingers the same way Carson had earlier today. 

I moaned softly. Her fingers were softer and smaller than Carson’s, but she was an expert in manipulating me and after all the excitement today, it was seconds before my cock was straining against its prison.

“Was this part of his payment for making the straps?” she said, still in her sultry voice.

“Y..yes,” I said, trying very hard to think of something else so I wouldn’t cum.

“What else did he do?” she asked, letting go and lightly tickling my balls and cock (where it pressed through the cage) with the tips of her dark red fingernails. 

“Mmmmm….I sucked his cock,” I said, tilting my head back and closing my eyes.

“Oh! Really!” she exclaimed, seeming to be truly surprised. “That dirty old man!”

She stopped her teasing and just held onto my caged member like it was a handle.

“Yes, ma’am,” I said, “you said to do whatever he asked.”

“Good boy!” she said, her face beaming. “I am very proud of you. You really are a little whore now, aren’t you? Sucking cock as payment.”

Oh my god! I hadn’t thought of that. I gasped and turned a deep crimson as everything I had done over the past year or so seemed to flash before my eyes and I realized what a slut I had become. Suddenly, I couldn’t stand for her to see me and I tried to turn away from her, but her hand on my chastity didn’t let go. 

“What’s the matter?” Fiona asked, concerned.

“W—what you just said,” I stammered, my voice starting to break as an emotional tsunami suddenly overwhelmed me, “you’re right. I didn’t think about it like that until just now.”

I paused, not wanting her to see the threat of tears in my eyes. Her face grew concerned as she watched me struggle.

“I liked it – all of it, and I wanted to do it! And all the other things I’ve been doing with my friends and you and….”

I was able to slip out of her grasp, finally, and I turned and ran to the bedroom. I just needed not to be seen at that moment. Fiona must have understood, she didn’t follow or call me back. I just sat on the bed and contemplated what I had become for a while. 

I didn’t cry, per se, but I did tear up a little. Mostly I felt numb? No, that wasn’t the right word. Resigned maybe? But that had negative connotations. I wasn’t forced to do any of this. I could have opted out at any time and Fiona would have backed off. The truth was that I was enjoying this, but should I enjoy becoming a whore? Was that really what I had become? Fiona had intended those words as a joke so why was I taking it so seriously? There was nothing wrong or bad in what I had done today or any of the stuff I had been doing. Fiona helped me to open my mind (and various parts of my body) to all these new things. I just had to let go of my old biases and taboos and just relax and let it happen.

I was having these pivotal moments a lot lately, or so it seemed to me at the time. When Fiona first started leading me down this path, it was all just for fun, but as we took it farther and farther, it became more than just a game. It was still fun – more fun than I had ever had in my life before. I was doing some amazing things that I never would have tried if it weren’t for Fiona pushing my boundaries. And she never pushed too far or too fast. What was that saying?  Boil the frog?  You put a frog in a pan of cool water and slowly turn up the heat and he never realizes he is being cooked. I guess I was the frog, but I didn’t mind. I rarely pushed back because I enjoyed the things she wanted me to do. I liked making her happy, but it was more than that. She liked making me happy too. That’s why this worked so well for us. And I didn’t want to stop, it was just a bit of a shock, and I was probably overly emotional because I was so fucking horny! 

I continued my inner monologue for twenty or thirty minutes before I finally came out of the bedroom. I had talked myself down and decided that there was nothing wrong with what I was as long as Fiona and I were both happy. I wasn’t even sure why I had freaked out like that.

“Feeling better?” Fiona asked, as she sipped from a glass of dark red wine she had procured from the rack in the kitchen area. 

When I didn’t speak right away she continued.

“Come, have some,” she said, patting the sofa next to her.

She filled a second glass about half full as I sat down beside her, and then handed it to me. I took a small sip, acclimating my tongue to its dry spicy flavor. She seemed content to wait for me to talk.

“I’m sorry. I feel a little silly,” I said, finally, after another drink of the wine.

“You have nothing to be sorry about and you are not silly,” she said, placing her hand on my bare thigh. “You have been doing a lot of new things lately. You know you can always tell me if we need to slow down or even back off a little.”

“No, no, it’s all good,” I said, “I mean, yes, it has been a lot, but I don’t want to stop or slow down or anything.”

“Okay, but you have to talk to me. I need to know that you are alright,” she said, looking into my eyes as if trying to see my thoughts. “You have to tell me if there is something you need.”

“I’m alright, I…I guess, there is one thing, maybe,” I said, hesitantly. 

“Just tell me, baby, whatever it is,” she said.

“Can I please…uhh…may I…cum sometime soon,” I finally blurted out the last few words and looked down.

“Oh, Brian,” she said, chuckling sweetly, “of course!  It has been a while, hasn’t it?”

“Yes, a while,” I said, “but I don’t like to ask. I know you like to keep me on the edge, and usually, I like that too. It’s just…well…with everything….”

“I understand, baby,” she said as she lifted my chin and kissed me.

We made out on the couch for a while as our hands explored each other’s bodies. Mine was, of course, completely exposed to her touch. She was still wearing the blouse and skirt that she had worn to the gallery this morning. It wasn’t long before my hand was up under her skirt working my fingers into the moist folds of her bare pussy.

“Let’s go to the bedroom,” she suggested, “so we can get more comfortable.”

She stood up and took my hand. Her blouse hung open and she hadn’t been wearing a bra, so her firm breasts hung like an invitation with one of the nipples peeking out at me. I stood up as well, and she led me to the bedroom. My cock was aching in its cage as I watched her ass wiggle in that skirt that barely covered her cheeks. The plug rattled in my ass with every step.

She pushed me down onto the bed on my back with my legs over the edge. She let the blouse slip off of her shoulders and down her arms, giving me the full view of her tits. Her nipples were erect and I longed to get my lips on them, but she turned around to the dresser so her back was to me, and opened one of the drawers. When she turned around, she was holding the key to my cage, on the silk cord that she used to wear around her neck sometimes.

“I think you’ve earned a small reprieve,” she said, waving the key in front of me.

“Thank you!” I said, surprised and excited, as she moved down between my legs.

I felt her inserting the key and removing the small locking device. I thought I was going to explode as I felt the cage slipping off of my swollen shaft, but I managed to clamp it down. She left the base ring and straps in place for now.

“You are not allowed to cum until I tell you, understood,” she commanded.

“Yes, ma’am. I will do my best, but I am so close…” I said.

“Think about baseball or whatever guys do,” she laughed.

I started to reply but couldn’t do anything except gasp as she engulfed my cock with her warm wet mouth! It took everything I had not to cum then and there. I tried to think about baseball, work, politics, anything that might take my mind off of this desperate need as she started to lick and suck with expertise.

None of it helped for more than a second. There was nothing that could have drawn my attention away from what she was doing to me. In a way, the sensation was almost too much and I think that might have been the only thing that kept me from filling her mouth with this long pent-up load.

“Mmmm,” she hummed as she pulled my hard-on out from between her lips with a wet kiss, “you are being a very good boy. Keep it up and I might have a surprise for you.”

Once again my reply was cut short as she sucked the head back into her mouth and bobbed up and down and used her tongue to tease the glans before finally taking the full length. I struggled to maintain control as I hit the back of her throat and continued another inch or so down. Fiona was a pro and had almost no gag reflex. She rocked back and forth slightly, fucking me with her throat. Finally, she pulled me out again, leaving a long string of saliva hanging between her chin and my cock for a moment before it broke and dripped down on her tits.

I knew I wouldn’t be able to hold out if she did that again. Luckily she seemed to have another plan.

“Don’t move,” she said, standing up and walking into the bathroom as she wiped her mouth on the back of her hand.

When she returned she had a small packet. It took me a minute to realize it was a condom. 

“This should help you hold back a bit,” she said as she tore open the package and rolled the condom down over my rigid shaft. 

It was translucent and one of those that are ‘ribbed for her pleasure’. I could feel it squeezing my shaft and every touch sent shockwaves through my body. Once it was on, she slid her hand up and down my shaft a few times. I still had to work to keep my orgasm locked down, but it did reduce the sensitivity a little, and I was glad she thought of it. I wanted her to be proud of me.

“Get up on the bed,” she commanded and as I pushed myself up so I was fully on the mattress, I watched her finally wiggle out of her skirt. 

Fiona naked was a vision to behold. She was fit and toned but not muscular. She kept her body hair completely removed using the same stuff that she made me use. Her skin was creamy white and so smooth and soft as she climbed onto the bed and straddled my stomach. 

I could feel the moisture between her legs as I reached up to take one of her fleshy mounds in each hand. As I kneaded them and stroked my thumbs across her nipples, she lifted slightly, scooted back, and used her hand behind her to push my cock up so it lay pressed between my lower abdomen and her labia. 

She slowly slid forward and back, stroking my shaft with her outer lips. I moaned as she teased me and pinched her nipples between my thumb and finger, making her moan as well. Just when I thought I couldn’t take anymore, she rose and let the tip of my penis slip into her silky wet vagina.

I shuddered as she lowered herself, slowly taking my full length into her. Her hot cunt gripped my cock. If it hadn’t been for the condom dulling the sensation that would have pushed me over the edge. 

She started to ride me and it wasn’t long before she started to buck and scream with her first orgasm of the evening! I twisted her nipples, adding to her crescendo until she grabbed my wrists and forced them over my head. This meant she was leaning forward with her breasts hanging over my face so I started licking and sucking them instead. 

She growled but didn’t make me stop. Instead, she pushed herself down until her clit was rubbing against my pubic mound and then she started to grind against me. I wasn’t sure if my cock had ever been this deep inside anyone before. I think the chastity ring might have been restricting the blood flow and keeping my erection extra hard. I could just feel the tip of my cock touching her cervix. I didn’t have a ‘monster cock’ but I had always wanted to say I had ‘bottomed out’ in a woman. I felt like this qualified.

Lost in my thoughts I managed to keep my orgasm at bay until Fiona’s second orgasm took me by surprise. She fell forward and nearly smothered me with her tits as she groaned lustfully. I wrapped my arms around her and held her tight until she finally relaxed and rolled off to one side and we both just laid there panting for a few moments, with my cock pointing straight up at the ceiling.

“I am very pleased you haven’t cum, baby,” she said finally, as she reached down and stroked my shaft slowly. “I think you have earned a special reward.”

All I could do was moan.

She sat up and turned so she was on her knees beside me, she stroked me a few more times and then started rolling the condom back up and off then tossed it towards the trash can beside the dresser.

“Grab the lube,” she said as she turned and got down on her hands and knees, then lowered her head until her cheek was against the mattress, putting the perfect curve into her back. 

Is there anything more incredible than a woman face-down ass-up ready to get fucked? I could have cum just from that view, but I snapped myself out of it and picked up the bottle of lube from the nightstand. I wasn’t sure why we needed the lube, I could clearly see her cunt was glazed with her own lubricant, but then she reached back with her fingers and spread her cheeks wider and I got the hint – I was going to get the holy grail! Fiona’s ass was the finest thing that the gods ever placed on the earth, as far as I was concerned. She only rarely let me fuck her there and it was always the best sex we had ever had – every time.

My cock ached as I watched her hole pulsate in time with her breathing and I didn’t waste any more time. I tipped the bottle up and squeezed a small stream right onto her anus.

“Oooh, that’s cold,” she said and flinched.

“Sorry, baby,” I said, starting to rub it around the wrinkled perimeter.

I put the next dab on my fingers and then rubbed my hands together to warm it up a little before I started probing just inside. Her hole was always so tight. I had to work to get my finger in up to the first knuckle. Then I worked it in and out until she started to relax a little and let me go deeper. I got more lube and slowly worked the entire length of my finger inside. I massaged her inner passage for a moment then fucked it with my finger while she moaned. When she felt ready, I pulled out, added more lube, and then did the same process with two fingers.

“Ok, I think I’m ready,” she said, as I was about to add a third finger, “I want to feel your cock.”

She moved her hand underneath her to rub her clit as I moved in behind her on my knees until my cock was lying between her cheeks. I was so sensitive I could feel the blood throbbing in its veins. I squirted more lube in my hand and thoroughly coated my shaft and especially the head before lining it up with her hole. She flinched at the touch but didn’t move away. I held it in position as I pushed forward, forcing myself into her slowly.

She moaned loudly as I felt it push past the first sphincter ring. I paused, partly to keep from cumming and partly to give her time to get used to the penetration. She made a little mew but pushed back against me so I knew it was ok to continue. I pushed a little further until I slipped past the second ring making her mew again. Her ass was so tight and hot. I have no idea how I managed to keep going but I did. I rocked back and forth a little, taking my time, before finally pushing the rest of the way until my pelvis pressed against her ass cheeks. She let out a long sigh as I paused again.

“Fuck my ass,” she demanded.

I started, slowly at first, pulling back until I felt that inner ring, and then pushing back in. Letting her (and me) feel every inch. Then I began to increase the pace until I was driving my hard rod into her.

“Yes, yes, give it to me,” she cried out several times, and, “fuck me like an animal,” a least once.

I continued to pound her ass until I finally felt that urge creeping into my balls and cock. That familiar tingling of all the nerves signaling the ultimate release. There was no way I was going to be able to hold it back this time.

“I’m going to cum, baby,” I moaned.

“Cum for me, baby, fill my fucking ass,” she hissed.

That was all I needed. I let it go and finally got my long-denied climax. To say it was worth the wait would have been an understatement. I exploded inside her and it felt like the cum was shooting out of me like a fire hose. She hit her third orgasm just then and we bucked and jerked together until I couldn’t stand the sensation anymore and when I pulled out, I was still convulsing with cum draining out of me and dripping on her ass.

I started to climb off the bed but she stopped me.

“Uh-uh, you know what you are supposed to do,” she said.

My brain was foggy but I knew what she was expecting.  First I scooped all the leaking cum off of my cock with my hand and then licked my hand clean. Then I licked the drops of cum off of her ass cheeks. Finally, I turned over onto my back and positioned my head between her legs. Once she could see I was in place, she sat up and brought her ass hole down to my mouth and I licked and sucked all of my cum out of her. As I suspected, there was a lot of it. It seemed like it was never going to stop trickling out of her hole.

“Good boy,” she said when I started to slow down signaling that I had got all I could. “Now give me one more good orgasm.”

She moved back and positioned her pussy over my mouth and leaned forward so I could more easily get to her clit. I sucked and licked while she rode my face and pinched her nipples. She was already wet when I started but It didn’t take long before there was an extra gush that covered my face as she writhed in her fourth and final orgasm.

She fell over beside me, spent. We just lay there, holding hands and enjoying the glow.