PeculiarChangeling
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A Sensitive Guy - Part 1 of 2
🕑 Added 2023-05-22 20:47:27 +0000 UTCContains: Premature Ejaculation, Humiliation, Pull-ups
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Timberly Swinn, 27 F
Happy for fun, would love something deeper. Sex positive, unless you’re a fuckin’ creep.
I’m interested in technology and writing on the human psyche. I like board game nights with friends when we want to keep things low key. For a high energy date I’ll teach you how to play pickleball–I’d say, ‘Loser buys drinks afterwards’, but I don’t need free drinks.
I’m not going to quit my career for you, don’t even ask.
Looking for a sweet, sensitive guy who isn’t terrified of emotional vulnerability.
Sam scanned the dating app profile, hesitated, then looked at her picture again. She was chubby and tan and didn’t appear to be more than five foot even–only an inch shorter than himself–with a short pixie cut. She radiated confidence in her selfies; attractive, self assured, and her bio got his interest.
(Sure, why not?)
He sent her a message.
…
It took two weeks of chatting before Sam could work up the courage to ask Timberly out for coffee. She countered with dinner and drinks at a local club, and he fumbled typing his response so badly he sent ‘Y3<s’ by mistake.
She just…got him. They’d quickly moved off the dating app and onto a little chat app she’d recommended, and whenever he heard its notification jingle he felt his heart flutter. Timberly was funny, successful, and confident in her attractiveness–Sam thought he was just a little funny, and not in the ‘good at telling jokes’ way. He worked as an underpaid stage hand and lived out of his parents’ basement because there was nowhere else he could afford rent. What did she want out of him?
He kept expecting her to drop him, to move on to someone better. In fact, he found himself almost pushing for it–he didn’t try to hide the fact he was dirt poor or put on a persona of success.
Timberly didn’t mind. She insisted she was interested in who he was as a person, not the lack of a comma in his bank account.
So, anxious about being underwhelming but willing to give it a try, he’d put on a shirt that properly buttoned and tan pants, walked forty minutes to the bar she’d recommended, arrived twenty minutes early, and sat on a bench outside waiting for–
“Sam?”
He hadn’t heard Timberly’s voice before, but he recognized her from her photos in an instant–though she hadn’t been wearing a vest over a crisp white shirt that gave her a look of strength and solid poise. Sam momentarily worried his jaw would hit the floor and his tongue would roll out like a red carpet, but he managed to come up with a reply instead.
“Timberly,” he nodded his head, looking her up and down and answering all at once. “I–I feel underdressed.”
“Don’t worry, I think you look just right,” she said, nodding at the restaurant door. “I’ve got us a table–and, please, you can just call me Tim.”
She led him in, ordered drinks for them when the waiter came around, and let the conversation slip into talking.
Sam knew he was doomed, then–he was head over heels for her. She knew what she wanted, and she was getting it. They talked about work–he had fairly little to offer to that conversation–but her ambition made him want to go run a marathon or climb a mountain or something, just any activity to match her intensity. They talked about growing up–there, he had more in common, they’d both been to charter schools and he had stories to swap.
“You’re cute,” she said, after placing their dinner orders.
“I–” He spluttered. The direct complement had short circuited his thoughts, and his cheeks started to burn. (Oh god, you’re blowing this. Just…breathe.) “Thank you, you look fantastic.”
“Thank you,” she said, the corners of her eyes crinkling when she smiled. “But that’s not all I meant. Did you know your ears wiggle when you get excited?”
“They do? I didn’t…” focusing on the sensation, he realized she was right–his ears were wiggling. “I didn’t know that.”
“I read people for a living. Spotting little tells in people is my business–and it can tell you a lot about a person, too, besides just which muscles are connected to which feelings in their head.” She shrugged, her body language indicating that she found the quirk endearing. “Do you know what you want to do with your life?” she asked, pivoting the conversation so quickly it gave him whiplash.
“I guess…I’d really like to be in a band,” he said, knowing it sounded lame.
Tim sat back, reaching into her purse to take out her phone. “A band, huh?”
“Sure, it’s kind of the fantasy, isn’t it?” And it was true, it’d been Sam’s fantasy…when he was twelve. Now, he just gave that answer because he didn’t know what else to say. “Up on stage, popular…”
Eyes off him completely, Tim said, “I guess so. You don’t strike me as the ‘popular’ type.”
Sam winced. “Ouch.”
Her gaze returned to him, and softened a little. “Oh–I’m sorry, that’s not what I meant. I was thinking, though…is popularity chasing really your thing? That’s what you think will bring you fulfillment?”
He shrugged. “I don’t…I don’t know, really. It sounds cool? But when I think about all the work that’d go into that…I don’t know. It sounds exhausting. I’d really just like to be comfortable, I think–to have friends and people I care about, to have enough free time where I can have fun, to work a job that feels like it helps people.”
She set down her phone on the table and smiled. “That’s more like the Sam I know. You’ll do just fine.”
“Hmm?”
“I just mean, I’m enjoying this,” she said. The waiter finally stopped by, but she just asked for more water and waved him away. “I like you, Sam.”
“Thanks.” Trying to find a way to fill the space and respond, he asked, “What about you? I know you like your job, but is there anything else you’re looking for in life?”
She grinned. “Oh–I crave attention.”
…
The night went great. Better than great–they talked for hours. His crush deepend, and at the end, she drove him home. He had to awkwardly admit they were driving back to his parent’s place, but she didn’t mind; he got into her BMW and rode with her.
What he wanted was to go back to her place, to hit it off in a big way, but that could wait. The night had gone well, and Tim seemed happy–he didn’t mind patience, in theory.
Unfortunately, he had a tough time convincing his body of that–during the back half of the drive home, Tim had to shift the way he sat three times to hide the unfortunate erection that’d cropped up. It just wouldn’t go away, even as he kept trying to shift the conversation towards serious topics–for reasons he couldn’t quite put into words, Timberly simply made him horny.
Parking on the curb, Tim walked around to get his door, let him out, and took his hand.
“I had a really nice time tonight,” he said.
“Me too,” she replied. “I’d like to take you out again.”
He nodded enthusiastically. “Please! And–”
She leaned in to kiss him, and–
(Oh god, oh god–)
Sam’s cheeks caught fire and he found himself unable to stifle a moan that carried into Timberly’s lips.Without warning, he found himself spurting into his boxers right there on the street, mingling embarrassment and bliss.
Tim pulled back. “Was the kiss that goo–Sam?”
He couldn’t help but breathe rapidly, trying to keep his face placid, unable to totally resist the sensitive shocks of bliss currently dribbling out of him. “Um…um–”
Sam looked down, stupidly, shocked to see it’d soaked through. He’d stained his pants with the unexpected orgasm, right there at the end of the date, and Tim’s gaze followed his.
“Fuck–” he started, blush rising, before turning and sprinting into his home.
He simply could not face Tim for another second.
…
Chirp!
Chirp!
Chirp!
Chirp chirp!
Sam didn’t answer his phone until the fifth chirp. He couldn’t bear to read the rejection message Tim had inevitably sent. Things had been going well, she’d liked him, and then he’d just blown it.
(Ugh, no pun intended.)
Finally, though, he had to face the music. Checking his messages…
‘Hey, Sam, I had a really nice time tonight. Don’t be embarrassed about the accident at the end–it’s not your fault.’
‘I’d still like to go out with you again, I really didn’t mind.’
‘How does lunch on Tuesday sound?’
‘I knew someone in college with a similar problem. I didn’t think less of you, I was just surprised is all.’
‘Are you okay, Sam?’
Eyes widening, he responded to the most important part first.
‘Tuesday–lunch. Yes please!’
…
Things went great again, until they didn’t.
Sam hadn’t experienced another bout of early ecstasy since their date, so he wrote it up as coincidence. Over excitement after a long dry spell and a wonderful night. Just to make sure, he even rubbed one out the night before.
It didn’t help.
They had great food, great conversation, and this time he didn’t even have the dignity of going out to the car–she reached across the table to hold his hand, gave it a squeeze, said how lovely he was looking that afternoon, and–
(Oh god.)
He was just glad they’d sat in a booth instead of a high top, it gave him a modicum of privacy as his cock twitched and he came in front of Timberly for the second time.
“Oh, Sam–are you–” she started.
He felt he had to nod, wanting to melt into nonexistence.
She let him breathe, twenty seconds passing, before she said, “Hey, don’t worry about it. You can’t help it, so what’s the problem?”
“Right…” he said, looking down. His jeans were stained yet again, the faint smell of cum wafting out of the booth.
But when Tim smiled at him…he didn’t mind so much.
…
Their third date was the real breaking point.
A movie at the mall, then dinner. That was the plan. But then Zoe Kravitz came on screen, and–
(Fuck–)
Tim gave his hand a gentle squeeze, whispering under the sound of the action on screen. “Shh–it’s okay, Sammy.”
That only made his blush deepen.
After the film, standing in a nook by the theater exit, he tried to explain. “I swear–this was never a problem, this never happens–”
“I don’t care,” Tim promised. “I’m not judging you, Sam, it’s just little accidents that happen. Some boys are like that. But…if it’s going to keep happening, you might need to do something about that.”
Looking down, she gestured to the dark stain on the front of his jeans. It looked for all the world like he’d peed his pants.
“I don’t know,” he said. “I guess…I could just wear a condom all the time?”
She thought about it, then shook her head and took his hand–just that touch made him shudder for a moment, though thankfully he didn’t humiliate himself in front of her again. “I have another idea.”
He didn’t know what she was talking about until they were deep in the mall’s retail outlet, coming up on the juvenile potty training aisle, and–
He dug in his heels. “Woah! I’m not going to wear–” he dropped his voice into a low stage whisper, “diapers!”
“I’m not thinking about diapers,” she said, doing nothing to match his volume shift. “Pull-ups. They make them up to your waist size, and they’ll do the trick, right?”
“I, but–” he started, feeling exceptionally small–and not just in a physical sense, remembering his slim waist.
“Sam,” Tim said, looking him in the eye. “Nobody except you or I will know, and it’s better than having to change your pants every time we hold hands. I’ll buy them, and a new pair of pants so we can finish our date. Just wear the pull-ups, ok, sweetie?”
She wouldn’t stand for self-consciousness. He knew that, and he didn’t want to argue about the details of his diaper needs in the store when he knew he’d lose. Trying to match Timberly’s own assuredness, he nodded. “Sure.”
She picked up the nearest pack, one decorated with Disney princesses, and nodded. “Ok. Let’s go find some pants, get checked out, and then we’ll find a bathroom for you to change.”
…
Sam hated that the pullups worked, but, well…they worked. He found himself dealing with his ‘Boy accidents’ more and more around Tim, but at least they were contained now, and all it cost was a pink waistband and the shared knowledge that he had puffy absorbent princess prints for underwear.
They continued to date, weeks stretching into months, until the relationship had proper labels attached. “Boyfriend and girlfriend”. Quaint, but when Tim had declared that the terms were appropriate…he’d needed a fresh pull-up.
He got to meet Tim’s friends–meeting up for game night, he was reasonably sure none of them noticed when he tensed up after Timberly laughed at one of his jokes. He had to change his pull-ups in the bathroom–twice–but had a great night otherwise.
They even had sex–sort of. He lasted until she had her shirt off, but she was more than content to let Sam use his mouth and fingers to make her happy, kneeling at the foot of her bed and spending half an hour giving her the pleasure he could get in two seconds.
And she never judged him. Not once. If anything, Timberly liked that she could make him pulse with pleasure just by giving him a smooch on the cheek or a squeeze of the hand. She smiled when he got flustered, said he reminded her of a kid on the playground, blushing over incredibly mild PDA.
And it was mild, too. She could just stroke his hair and leave him moaning, and a deep-throated kiss was better than any marathon session he could imagine. If she really wanted, Tim could snuggle up to him on her couch during a movie, wrap her hands around his waist, and leave him quivering and drooling from pleasure. The third time she got him a pack of fresh pull-ups, she referred to them as his ‘happy pants’, and he wasn’t sure he could argue.
The weird thing, though–it was just Timberly. He didn’t deal with it at work, he didn’t deal with it at home, only when he was out with her. Something about that touch, or her words, or just something made him utterly unable to control himself.
He started to like it, and he was pretty sure he loved Tim, too.
Four months into their relationship, she dropped two bombshells on his head.
“Do you want to move in with me?” she asked, followed by, “And–your accidents are getting worse. I really think we need to get you a chastity cage.”
Comments
A cute change of pace!
