The first night sleeping in the chastity device was SUCH intense frustration. I actually cried. I hadn't cum for a week, and I thought, Oh God, how am I going to last TWO MORE in this thing? Of course, bedtime was preceded by a session with Tyler and Shelly on the phone, first listening to her amazed fascination with the chastity tube and how "oh my gahhhhhhd" it was "SOOOOO hot" that my dick was locked up and there was no way I could cum without the device off me, and how it was "sweet" that Tyler had the key.
That was followed by me acting as Shelly's stand-in as Tyler got his balls and dick gobbled, his ass licked, his asshole tongued, and then got to fuck "Shelly" from behind. Afterwards, "she" scooped his cum out of "her pussy" and licked it all up. When they were done, Shelly said, "So she gave you handcuffs, too? Are you gonna use 'em to cuff Davey's wrists to the bedposts tonight and make him sleep that way?"
"Do you think I should?" he asked.
"Oh my gahhhhd. That would be so hot."
"Yeah, I'll do that. I'll use ropes to tie his ankles to the other posts, too."
"So is he hard now?"
"Yeah, his dick head is just sorta peeking out the bottom. He's got precum leaking from it."
"Wowwwww. But he can't cum?"
"Nope."
"Oh my gahhhd. So hot. So if he's lying in bed, and all horny like that, will he be able to sleep?"
"Eventually. Probably. I don't know."
"But he might just lie there all night and be horny and not be able to do anything about it?"
"Maybe."
"Then in the morning he'd have to go to class, but he'd still be all horny. Oh my gahhhd, that'd be hot. Would he start whimpering, you think?"
"Maybe."
"Maybe you should put a piece of duct tape on his mouth, in case he does."
"Good idea. Yeah, I'll do that."
"Oh my gahhhhhd. Oh wait! I just had an idea. Can you put your phone like... somewhere on that thing that's on his dick? Like, can you attach it somehow? And put it on vibrate? 'Cause if you can, I think I'm gonna stay up late tonight, and keep calling the phone. It would vibrate on his dick. You think you can do that!?"
"I can probably just duct-tape it. Yeah, that would work."
"Oh my gahhhd. I might just stay up all night. I don't have to work 'til the dinner shift tomorrow. Oh my god I can just keep calling. You think that'll drive him crazy? With the phone buzzing on there?"
"Hahaha, I'm sure it will."
"Wowww, oh my gahhhd. So hot."
Hot for her, maybe. Sheer torture for me. Almost the entire night, I felt periodic buzzing on the tube encasing my dick. Even if I managed to nod off, I'd awaken every time she called. No doubt she was watching TV or enjoying herself there in Kennesburg, 8 hours away, gleefully reveling in the torment of a poor boy she'd never even met, knowing he was lying in the dark, spread-eagle on his back, cuffed and tied, sleepless and intensely horny, but helpless against her capricious torture. She would call about a dozen times in a row, then maybe wait a minute, and call another eight or nine times. Then I'd get a break for 10 or 20 minutes, and she would start again. I prayed Tyler's phone battery would run down before morning. It didn't, but I think she did fall asleep around 3 or 4 AM, and I got a little uniterrupted sleep.
Three weeks without cumming just about drove me insane. I felt like I was in a trance almost all the time. Every moment, whether I was awake or asleep, I was thoroughly and completely powerless. Every single move I made was under Tyler's control. I did my schoolwork (and helped him with his) like an automaton, and the rest of the time I was cleaning the room, or licking Tyler's feet or butt, or licking his piss off the toilet bowl rim, or wiping his ass after he took a dump, submitting to his bondage and his socks in my face, and acting as Shelly's stand-in almost every night... getting my lotioned-up "pussy" fucked, sucking Tyler's dick, licking his asshole, and swallowing or licking up all of his cum.
One night Tyler told Shelly he'd really like to try anal sex with her; did she think he'd be able to take his cock in her back door? She said, "Ooooh... I don't know. I've never done that. I'm a little nervous about it." So Tyler said they could start slow: First he'd lube up a finger and put it in her ass. Of course, HER ass was not available, so he put lotion on his finger and put it in MY ass.
"Does that feel good, baby?"
"Mmmm," she cooed. "Yes. Oh, I love that. So you have your finger in Davey's ass, right?"
"Yep."
"Mmmm. So hot."
"Here, baby, taste it. I want you to taste your ass. I'm putting that finger to your mouth."
"Oh my gahhhhd. So nasty. OK, I'll taste it. ... Davey's tasting your finger, right?"
"Of course."
"Oh my gahhd. Wowww. Try putting two fingers in my ass, baby."
So of course Tyler worked up to two fingers, and then three, in MY ass, regularly pulling them out to have me suck them. I didn't like it. His fingers tasted... like ass, obviously. Not that I wasn't used to that taste by then. Better my own ass than his, I suppose.
It really hurt when he tried to put four fingers in, but he thought he might have stretched me out enough to try his dick. Even though he used plenty of lotion, he could barely fit the head in before I begged him to stop. It hurt too much. So he and Shelly agreed that we should stretch out "her" ass some more, over the next few days. That meant I was going to have either my fingers or his stuck up my ass at about every opportunity, all through the day. As for that night, they made me try and hold my asshole open with the index fingers of my two hands, and Tyler jacked off into my asshole, with his dickhead right up against it, so as much of his cum as possible would go in. Then Shelly said she wanted Tyler to put his finger in "her" ass and scoop his cum out so "she" could eat it.
By the time my three weeks without cumming finally ended, Tyler and Shelly were able to have anal sex... meaning, of course, that I could listen to Shelly on the phone, saying "Oh my gahhhhd" and "sooo hot" while Tyler fucked my ass. Incredible amounts of pre-cum drooled from my dick, leaving wet spots all over my bedsheet. When Tyler and Shelly allowed me to cum that night, they decided it would be good for me to have to sleep with my cum all over my face to remind me, as I went to sleep that night, to continue to be "a good friend" to Tyler, and "be cooperative" as a roommate. So, after unlocking my chastity device, Tyler trussed me up so that my legs were over my head, and my dick pointed at my own face. He then jerked me off, aiming my dick so cum would splatter on every part of my face. Then he got a hot washrag and wiped my crotch, then let me air-dry as he untied the ropes, re-doing them after I was lying down. He asked if I needed to piss, and I did, so he got a jar and had me pee into it. Then he put the chastity tube back on me and locked it. He and Shelly said good night, and Tyler got in bed. But after about a half-hour, he decided he was horny again, so he decided to add another load of cum to my face. He slipped off his bunkbed, got into my bed, straddled my chest, and jerked himself onto my face. After taking a piss, he clumbed up into his bunk without a word, and went to sleep.
When fall semester ended, I asked Tyler to remove the chastity tube from me before I went home for the 3-week winter break. He said, "Just because you'll be in Bellewood and I'll be in Keenesburg doesn't mean we stop being friends. You'll still have rules to follow. I'll still need to know where you are at all times, you'll still need to ask my permission to do things, and I still need to know you can't jack off without me letting you."
"But how can you let me if the key is with you, a 12-hour drive away?"
"Hahaha. Simple. Make the 12-hour drive and come to Kennesburg."
"But I don't have a car. And I don't think my parents will let me borrow the car to go that far. They want me home for the whole break anyway."