Teddy Reaches A Goal
A hole, perfectly gaped open, so circular a billiard ball could fall right in.
Teddy’s phone buzzed. #48 had finally replied to the photo they sent, proving mission accomplished.
“29 days later and it finally fits. Good. I’m impressed, slut. I’m running an errand. When I get back you better be hooded ass up on my couch. Your name is with the front desk. Let yourself in”
They took a moment to bask in the brief glory they felt, knowing the power one picture can hold. They scrolled back up to admire the photo of their backside one more time before getting ready.
In the pic, they kneeled, ass to feet, with their slender frame and shoulder-length bleached hair visible. Their ass was pale, outlined by a sun-kissed tan (admittedly artificial), sinking inward toward a pink gash. A hole, perfectly gaped open, so circular a billiard ball could fall right in. They loved how smooth they are. Not a body hair could be spotted, even if someone held a magnifying glass up to them. “Laser hair removal DEFINITELY pays off,” Teddy thought. They couldn’t help but marvel at their own achievement.
Teddy’s phone vibrated one more time, sending a pleasant chill down their spine to the nape of their back. “#48 shared his location with you.”
About a month earlier, in mid-January, Teddy had met #48, as all good sluts do, in their DMs. #48 followed his brief introduction with photos of himself. A necessary courtesy considering, from his alt account, no face photos were visible. He had a salt and pepper, rugged appearance and kind eyes; the type you’d love to look deeply into as you’re gagging on a foot-long dildo. Teddy replied with a few photos of themself. A face pic, body pic, locked cock, and tight hole.
“Good slut,” #48 said. “What’s a dad have to do to get the keys to that pretty little locked clitty?”
“say the word and they're yours,” Teddy replied, half serious, but vibrating with the idea of handing over control.
“When was the last time someone held your keys?”
“tbh never”
“We’ll have to change that, slut.”
The two of them continued to chat, discussing limits and confirming that they both live in New York and that they’re looking for a Dom/sub relationship. They swapped numbers and moved the conversation over to WhatsApp. Teddy offered to text, but #48 preferred to keep his boys and his toys in separate spaces.
Teddy had spent the last year retweeting videos and photos of guys in all sorts of kinky scenarios from an alt account no one knew about, but in reality, they didn’t have much kink experience. They owned a nub-sized cock cage that they would wear every once in a while when they were alone and a few plugs, but nothing too big. The idea of diving into something more in-depth was novel, but exhilarating.
“i fantasize about a long-term lockup where the only way i can unlock is by reaching a goal,” Teddy added.
“What kind of goal did you have in mind, slut?” #48 replied.
Teddy paused and ran through their rolodex of fantasies in their brain. One desire came up over and over in each scenario they thought of: taking a fist. Fisting had been on the 25 year old’s mind since they happened upon a video on Tumblr nearly a decade prior. They could remember the moans of pleasure, the eyes locked with passion, and couldn’t shake the thought of it ever since.
“i’ve always wanted to take a fist, sir, but never had someone help me train for it,” Teddy typed, nearly shaking from the titillation.
“You’ve come to the right place,” #48 responded. “How’s this sound: you lock your little nub up, meet me at a coffee shop by my place, and put your keys on my keyring. In exchange, I’ll give you a bag with a plug to work into that pretty pink hole of yours. Once you get it in, we can talk about unlocking. Although by then, you’ll probably be so reprogrammed from your lockup that you’ll beg to keep it on.”
“what if i can’t get it in?”
“I have faith in you slut. Now, lock up and meet me at Jumping Bean in Long Island City at 3pm.”
With only two hours to kill until #48’s proposed meeting time, Teddy had quick decisions to make. Do they hand their keys over, without making emergency duplicates, to essentially a stranger? How can they trust that he’ll ever give them back?
Teddy hastily replied, knowing time was ticking. “before we meet, can we establish some ground rules? it’d make it easier to hand you my keys.”
“Of course, slut,” #48 replied, “what did you have in mind?”
Teddy pulled up the notes app on their phone. About five notes down there was one titled “groceries.” Below a list of mundane needs laid what they were in search of. A list of keyholder parameters they had written on a late subway ride home. They copied and pasted into Whatsapp.
“1. as a keyholder, you are entitled to daily check-ins on-demand. check-ins will include a photo of my locked nub, a description of how i’m feeling, and details on any hole stretching i’ve done.
2. as a sub, i will not alter my physical appearance or endure anything too painful/that will harm me.
3. while locked, i will train my hole on a schedule provided by my dom.
4. while locked, i will not be allowed to cum via cock/cage stimulation. no vibrators or touching of the cage is permitted, unless it’s for cleaning. this is non-negotiable.
5. i may play with other guys while locked, but must get Sir’s permission first. Sir may ask for photos/videos of me playing with others and i must oblige.
6. in case of an emergency, you will unlock me if needed. i reserve the ability to call this off and unlock immediately. Sir must oblige.”
“Seems fair enough,” #48 replied. “As long as the keys are on my ring and I know you’re being a good slut.”
“Thank you, sir.”
An hour later, Teddy drew a heart on the keys to his cock cage in red sharpie and dropped them in a ziplock bag with a note saying, “take good care of them.” They made their way down the three flights of stairs from their walkup apartment on the Upper East Side and began to walk to the subway. Their cage rubbed against their jeans with every step, reminding them of the challenge they were about to take on.
They were nervous about handing their keys to an almost stranger, but was ready to take the risk. After all, they could just break the cage off if the situation came down to that…right?