Lillian Takes Me to the Edge

Lillian started having me prepare for her arrival a week early, by easing me back into wearing a buttplug. As the days went on, she switched me to progressively bigger ones. Finally, the day she was flying to see me, she told me during our morning call to put in the biggest one. "I want you to be ready for pegging tonight." I managed to get it in, which wasn't easy, and let her know.

Then I started my work for the day. I work from home and I focus pretty well, so thoughts about Lillian's arrival mostly went out of my mind until around lunchtime, when she texted me. "Send a photo of your chastity devices," she instructed.

"Yes, Miss." I dug them out. It had been so long since I'd had them out that they were practically dusty. "Which one would you like, Miss?"

She sent back the photo with one circled. "Do you have spikes for that one?"

I gulped. Even though we had never played with any of the chastity devices, she remembered the spikes. I hoped she also remembered how scared I was of them. "Yes Miss."

"Put it on, with the spikes, and then send me a photo."

It took me a few minutes because I was so excited, and hard-ons don't fit into chastity cages, but I managed it and then I sent a photo.

"You're all drippy. Can't have you making a mess. Put a condom over the end." I did.

* * * * *

The chastity cage and, especially, the spikes made it harder (ha!) to focus on work during the afternoon. My mind often wandered to sex and masturbation, which made me hard, which hurt, which made me think of sex more, which hurt more, until I could finally think of something else for long enough to lose my erection.

All afternoon, Lillian kept sending me selfies showing lots of cleavage. "I love you, but ow," I texted back once, which just got me another photo. She knew exactly what she was doing.

When Lillian arrived at her local airport later, after I finished work for the day, she gave me more instructions: "I know you have a strap-on harness that fits you. Put it on now. Wear one of your kilts over it. Oh, and bring the chastity keys when you pick me up from the airport. Both of the keys." She added a list of other things for me to have ready at home.

I did as she said, then I waited impatiently for her flight to depart and arrive. I fretted and fantasized (sometimes painfully) the whole time. I found myself reading the same paragraph over and over in the book I was trying to read. After a while, I set an alarm on my phone to alert me when it was time to go to the airport and lay back on the couch.

* * * * *

The alarm woke me. I drove to the airport, parked, and watched for Lillian to come down the escalator to baggage claim. Finally, there she was. I rushed over and we hugged and then kissed for a long moment.

"Lillian--" I said, but she cut me off.

"Stop right there. You're in chastity and you're about to give me your keys. That's not a 'Lillian' kind of situation. As long as you're locked up, you will call me Goddess, or Miss if someone vanilla is there," she said. She held out her hand expectantly. I handed her my keys. My dick tried to swell. It hurt.

We got her bags (well, I got her bags), and I drove home.

Lillian wasted no time leading me into the bedroom when we got to my apartment. Once we were there, she told me to strip. I took off my kilt and my shirt and tossed them on the laundry pile. That left me wearing my collar and my biggest buttplug, with the chastity cage poking through the front of the strap-on harness. It was the first time that Lillian had seen me wear the cage or harness. She shook the chastity cage and tugged at the lock to check that it was secure, squeezed my balls hard enough to make me groan, and rubbed the condom over the end of the device between her fingers to check how much precum had accumulated in it.

Then Lillian looked over the harness. She traced its straps with her fingers. "We're going to need a dildo for this, boy." She picked one out of my collection and slipped it snugly into the harness's metal ring. I looked down at two dicks, my own natural one painfully bulging through the slots in the chastity cage and, above it, a silicone dick pointing obscenely straight out.

As I looked over myself, Lillian stripped her clothes off, removing everything but her own collar. She turned back to me. "You're going to make me cum over and over, boy, just like you do on our video calls, and then you're going to fuck me with pointy here," she said, smacking playfully at my dildo, which bounced up and down a few times.

Lillian pushed my head down and I knelt. She sat on the edge of the bed, opened her legs, and took me by my collar. I started to spread her lips with my fingers but she took my wrists in her hands and firmly put them behind me. Then she spread her lips with her own fingers. I brought my lips to hers and touched my tongue to her clit. I teased it a few times and drew it into my mouth, sucking and licking. She sighed, shifted forward, and then pressed my head more firmly into her crotch with a hand on the back of my head. I kept at her clit that way for a few minutes. I brought her to the edge, and then she was over. I heard the chattering sound that meant she was cumming. I took a quick breath and redoubled my efforts. Her orgasm went on and on, and then it faded.

"That was good, boy, but I need more. Time for the wand." She got out her wand and the remote control and lay back on the bed. I crouched over her and helped her to a dozen orgasms before I lost count. I knew just what to do because we had played over the Internet so many times previously. After a while, both of us were exhausted. She gestured to the pillow next to her, and I collapsed there. We cuddled and kissed for a while, and then spooned, with my chastity cage and dildo poking between her legs. I was horny, but I was also tired and happy that I'd given my Goddess so much pleasure, even without my own.

* * * * *

I must have fallen asleep for a few minutes. When I reawakened, Lillian was standing next to the bed, stepping into her own strap-on harness. She buckled it. "I know that boys like you can cum in your cages if you try 'hard' enough. I expected you to do that," she said, "Since you didn't, I'm going to have to 'try hard' myself." She grabbed a second dildo, bigger than the one I was still wearing, and attached it to the front of her harness. "You can cum from this instead!"

Lillian looked around for something and didn't spot it. "We need lube too, but I see you didn't get any out," she said, and shushed me trying to tell her where it was. "No matter," she continued, "you can lubricate it yourself." She had me kneel beside the bed. I obediently started sucking as she put the dildo into my mouth and started thrusting. When I gagged, I tried to take it into my hands to take some control. She batted my hands away. "Boy, you've got a big dick and you aren't always careful with it. You're going to suck my dick my way, not your way." She emphasized this by inserting the dildo all the way, and I gagged hard for a moment, but after that she backed off a little and after a minute she was satisfied with the lubrication.

She had me lay back on the bed—"I want to look you in the eye"—and removed my buttplug. As it came out I compared it to the size of the dildo she'd picked out. I was glad that I'd used the big buttplug today, because it was going to allow me to enjoy the pegging. And I did. She started in slowly and shallowly, and then deeper and faster, and after a few minutes she was driving the dildo in almost to the hilt (or to the balls, I guess). It felt great, and it made me hard as can be. My erection also drove the spikes into my dick, and I knew I would feel that later, but I hardly noticed it in the horny heat of the moment.

After a time, Lillian slowed and withdrew. "Did you cum?" she demanded. She peered at the contents of the condom, still stretched over the tip of my cage. In the huge rush of feelings, I honestly wasn't sure, so I looked too. We saw that I had not. "Hmm. Despite all my efforts, you still haven't cum. I am going to have to remove that chastity cage, but I don't think you're going to like what comes next." She fished the key out of a pocket of her pants on the floor and used it to remove the lock dangling from my chastity cage. She gently pulled the tube off my dick, and then removed the rest of the pieces. My glans and shaft were imprinted with the shapes of the slots in the tube. Three angry red spots near the base showed where the spikes had dug in. All of it was sore. I stared down at myself.

As soon as my dick was released, it sprang into an erection. "You're still hard!" Lillian exclaimed. She cleaned my dick with a wet wipe. After that, she had me kneel next to the bed with my legs extended backward. I leaned forward and lay my head down. Behind me, she was fumbling with my balls. She pulled them through what I recognized as my humbler. I winced and yelped a couple of times as my scrotum got pinched when she tightened the screws. Soon, however, my balls were trapped firmly and with only slight discomfort. Then she added the ball crusher piece to the humbler. As she slowly tightened that, the discomfort transitioned from mild, to medium, and then beyond. I moaned, and maybe that was what she was waiting for, because she stopped.

"Oh!" she said, brightly. "I forgot! You wanted to adjust my collar! What do you need for that?" Despite her tone of voice, I needed to take her seriously. I told her what I needed. She got me the tools and supplies, and with my balls increasingly sore, I removed the lock from her chainmail collar and closed it instead with chainmail links, as we'd planned before her trip. I set the tools aside and looked at Lillian, hurting.

She had me assume my earlier position against the bed. Soon, I felt a condom being rolled onto my dick, then Lillian started stroking it, sliding the condom up and down. Soon I was fully hard and I felt an orgasm starting to build. Then the stroking stopped abruptly and my balls erupted in pain as Lillian flicked them with a fingernail. I felt the ball clamp being tightened further, which renewed the pain that had subsided into the background. And then Lillian repeated this, once, twice, more times, over and over again, bringing me right up to the edge and then stopping. I thought my balls were about to really be crushed.

Then, whether intentionally or accidentally, her stroking brought me right up to the edge. My dick twitched and Lillian pulled her hand away immediately. For several seconds, nothing happened. My dick twitched again once, and again, and cum spurted into the condom as my whole body spasmed just once in a ruined orgasm. In its wake, my sore dick and burning balls and exhaustion came to the fore.

I felt Lillian loosening and removing the ball crusher. Like removing nipple clamps, at first it hurt worse, and then trailed off slowly. And then the main part of the humbler loosened and dropped off. As an afterthought, Lillian unbuckled the strap-on harness from my waist and eased it off. Now I was wearing just my collar, which never comes off anyway.

"Good boy," Lillian told me. "We're almost done." While I wondered what possibly could be left, she had me lay down on the bed. Then, she brought something to my lips with one hand. "Swallow, boy!" she said gleefully, as she held up the other end of the condom and massaged its contents into my mouth with thumb and index finger. For her, I swallowed the entire load that she had collected in the condom.

And then we really were done. We cuddled up on the bed again. Both of us fell asleep almost immediately. What would the rest of her visit bring?