Feels like the First Time

“So have you ever done this before?” I asked.

“Well...I have…” Emma replied nervously, “Just not...with someone his age before.”

“It’s simple.” I replied nonchalantly, “Just pretend to be super slutty. That always gets him turned on and squirming. You have to remember he’s just a dirty old pervert. He’s 40 years old and you’re only 20, so use that to your advantage.”

I could tell that got to her, she looked away shyly, but a glimmer of a smirk betrayed her lips.

“Unbutton your blouse another button.” I said, “And remember, don’t be afraid to talk dirty. It really gets him going.”

“Got it!” she nodded, obviously psyching herself up.

“Are you sure you want to do this?” I asked sincerely. Wanting her to know there’d be no hard feelings if she felt too weird.

She took a deep breath, then looked up at me and grinned from ear to ear, “Definitely! It’s always something I wanted to try, ever since I heard about it!”

“Alright then,” I smiled, turning the door knob, “Here we go…”

*******

The door opened to a bright, pink nursery that I had meticulously painted and decorated with the most feminine, adult-sized baby materials I could find.

My husband was sitting on the ABC playmat, stacking blocks and pretending like he was actually enjoying it, no matter how much I doubted he did. He was wearing a white, ruffly princess dress with pink fringe. His miniature pigtails swung around when he looked up as soon as we walked in.

His eyes met mine, then widened as soon as he saw I had a guest. His face immediately flushed when he saw it was a much younger, hotter, college girl.

“Hello, Mikey!! Look who I brought to meet you!!” I cooed in my Mommy voice. Not that I needed to point him in her direction, he couldn’t stop staring. His jaw dropped so far that his 4 inch penis paci fell from his mouth, dangling on the string around his neck.

“This is Emma!” I told him, “She’s going to be your babysitter tonight!”

It took a while for his big baby brain to even register what I said. But finally he blinked a few times and took his eyes off her to look at me.

“M-my what?” he asked.

“Your babysitter.” I repeated. But when he continued to blink and gape at me I could tell he still didn’t get it. “Well you don’t think Mommy could just leave her wittle baby alone while she goes out with other men, do you??”

That one finally registered. He cringed at the thought of me with someone else, even though he long ago suggested it, I don’t think he ever actually thought I would follow through with it. He probably didn’t expect me to keep him caged for as long as I did either, but what can I say? He’s the one who gave me the power. Not my fault I got drunk off of it.

“Hewwo Mikey!!” Emma said. Stepping forward and leaning over to talk to him as if he were a toddler. She even made sure he had ample view of her cleavage as she smiled at him. Pinching his cheeks and making them even more red. “Aren’t joo just the cutest wittle thing!!” she teased.

Michael was so dumbfounded he didn’t know what to do. Just sat there with eyes darting back and forth from me to her cleavage.

Emma made a dramatic sniff of the air. “Uh oh...did somewon have a wittle accident??”

Michael’s eyes went wide with horror. He never made that face with me. Well, not anymore. He had long since gotten used to me changing his diapers. It still excited him–don’t get me wrong. But over time it didn’t have the same…effect…as it used to. The humiliation he so craved started to dwindle long ago when he became desensitized to his wife seeing him in a poopy diaper. But now I wasn’t the only one, now there was someone else seeing him in his messy situation. He was practically cowering from new, fresh bouts of shame and embarrassment as Emma reached down to grab his skirt and lift it up, exposing the Pink Princess Pampers underneath.

Emma seemed to take it all in stride, despite this being her first time seeing someone like this as well. She only hesitated for a millisecond as she placed a hand at the front of his crotch. Rubbing and pinching the area. “Hmmm...let’s see...it is a little warm...did you go pee pee in your diapy, Mikey??”

Michael was biting his bottom lip. In addition to his renewed reluctance at being teased, he was probably getting a rush of hormones from having a girl half his age putting her hand on his padded bulge.

Emma was a natural, though. Knowing it was driving him crazy, lingering around that area as much as she could, and dialing up the degradation.

“Tell me what you did, Mikey!” she prodded, crooking an eyebrow, “Did you go pee pee in your Pampers?”

Michael was obviously intimidated by this girl’s forwardness and authority. “Y-yes...yes I did!”

She slapped him lightly on the wrist and pointed in his face. “You will call me ‘Miss Emma!’ is that understood?!”

“Yes Miss Emma! I did go pee pee in my diapy…” he squeaked. His voice already getting more whiny and high-pitched. The way it did when he was dropping into subspace.

“That’s what I thought...and did you go poo poo too?” she asked, but didn’t even wait for an answer. She already had the back of his skirt pulled up and the waistband of his diaper peeled back.

“Ohhh!!! You sure did! You little stinker!!” she gasped.

I couldn’t believe how well this was going already. I figured when I put an ad out on Craigslist for an “Adult Babysitter” it was going to be a crapshoot. Which, it was, for the first 50 or so respondents. Most of them thought I meant “A babysitter that was of Adult Age” not “a babysitter that was taking care of someone of Adult Age.” Even those thought it would be for someone in their 80’s or 90’s that needed medical assistance.

But no, I needed someone that knew exactly what they were getting themselves into. Someone that would be dominant, but also hot and young enough to drive Michael crazy. And from the way he was clenching his legs together, I’d say it was working…

“Lay back on the floor, Mikey!” Emma said sweetly.

Michael glanced at me for reassurance as if to say “is this really happening?” To which I replied with a curt nod. As disheveled as he made himself appear, I knew deep down he was enjoying every second of this.

He sighed as he slowly plopped backwards on the floor. Whimpering as Emma giggled and started lifting up the ruffles of his skirt.

“Let’s see what kind of present the wittle baby has for me inside her diapy!” Emma cooed as she unsnapped the tapes. Michael’s face became more and more red with every second of anticipation until Emma finally opened up the soiled diaper.

Anyone who has changed a real baby’s poopy diaper knows the feeling of when that smell hits you. But few know what it’s like to have the stench of a grown man’s full, dirty diaper smack you square in the face. It is damn near impossible not to gag.

To Emma’s credit, she held back the most miniscule of gulps for fresh air, turned to the side just for a second, and blinked her watery eyes.

“My goodness!” she exclaimed, somehow managing to stay in character as opposed to running for the hills. “That is quite the stinky mess you made!!”

If Michael could cringe and shrivel up any further in shame, he would have folded in on himself. But by now he knew--after several corrective measures were issued--to not hide or cover or touch anything during a diaper change. He had to stay stock-still. On full display, covered in his own filth.

I can’t think of anything more dehumanizing than being forced to soil oneself. But to have it be inside of a diaper, a pink one at that, a dress, and in front of a teenage girl? Well...that’s about as emasculating as it gets.

I held up the pack of wipes,  “Would you like me to do this part?” I offered.

Emma hesitated, just for a second, glancing back between me and the mess. But finally sighed, smiled, and took the wipes.

“I got it.” she said with a wink, and began the arduous task of cleaning up Michael’s dirty bottom.

I was so very proud of her. Anyone will tell you the worst part about having a baby (of any age) is changing their dirty diapers. To me, the humiliation and joy it gives Michael is worth it, but to have Emma step up like that and take the initiative really let me know I’d found the perfect candidate.

It takes a lot of wipes to completely clean a muddy butt. Especially an unshaved one. But Mikey has been clean shaven down there for months now. Further feminizing him, but also making him easier to clean.

When it came time to do his crack, I placed a hand on her arm to stop her.

“Let me show you how he likes this part done…” I said. Taking a wipe and draping it over two of my fingers like it were a tiny ghost. “Then you just press into his hole–as deep as you can–and crook your fingers upwards.”

Michael didn’t actually ‘like’ this part too much. But he didn’t hate it either. He knew that a few fingers in his bum was a small price to pay for relief.

Emma nodded and draped the wipe over her fingers like I showed her. She looked a little unsure as she led the mini-tent down between his legs.

“You don’t have to do it,” I said again, “He can go another week or two without a milking.”

Michael whimpered at that. Emma laughed. “I’ve got it, Mrs. Draper. An ex-boyfriend of mine was quite fond of buttstuff…”

And with that, she gently pressed a finger into his rectum.

Michael let out a gasp and then an uncomfortable whine as Emma wriggled her middle and index fingers into him.

Emma giggled at Mikey’s discomfort. Even consoling him like a mother “Shhhh, it’s okay wittle baby! Just relax while Miss Emma takes care of you!!”

I smiled and stroked Michael’s hair with one hand, holding his chest down with the other to keep him still and calm while Emma worked her fingers in and out of him. His groans soon turned to moans as his sphincter started to relax and let the invasion take place.

“So you said to crook my finger upward?” Emma asked, concentrating.

“Yes, you want to basically press behind where his little penis is. That’s where you’ll find his prostate, or his ‘P-spot’ as I like to call it. You may feel it start to swell and pulse. That’s when you know it’s working.” I explained.

Emma nodded and bit her bottom lip in concentration. Working her fingers around inside of him.

Michael wriggled a bit, letting me know she was hovering around his little ‘button’. He always tells me it doesn’t feel that great at first. More like he just needs to pee. Probably because the bladder is located so closely to the prostate that we’re pressing.

“Ohp! He’s leaking!” Emma exclaimed, looking down at his tiny cage and laughing at the dribble coming out.

“Yes, that will happen as you press it” I told her, “But you’ll know when the big one comes…won’t she Mikey??”

I patted his reddened cheeks as he cringed. Closing his eyes and sucking his paci while Emma went to work on him.

She was getting into a rhythm now. Working her wrist back and forth as her fingers pressed upward and ran along the little walnut inside.

Mikey’s breathing started matching the tempo of Emma’s fingers. Becoming heavier and more intense.

“He’s getting close,” I warned her, “Remember what I told you.”

She nodded, and increased her pace. Practically lifting his hips off the ground with how hard she was pressing.

Mikey had no complaints, though. Little, pathetic moans escaped from around his paci. His eyes were rolling in the back of his head. It was a bit cathartic watching someone else give my husband an orgasm, but I’d be lying if I said I didn’t enjoy it too.

His moans crescendoed into a loud, almost pleading whine. He was about to cum from getting his ass fingered.

“Now!” I shouted. And Emma stopped. Pulling out her fingers swiftly.

Mikey whimpered, but continued to spasm. His hips bucked and his butthole fluttered as if begging for Emma to re-enter him.

Suddenly a jet of white, sticky goo sputtered through his cage. Emma’s jaw dropped into the most genuine smile.

“Oh my god!! I didn’t actually think it was possible!!” she exclaimed in awe as Michael continued to spasm and dribble jizz all over his balls.

“I told you it was!” I laughed, “ I have to milk him like this every other week to keep him docile. You pulled out at the perfect time though! It basically ‘ruins’ his orgasm. All that pressure building goes away, but his icky goo still comes out! It’s a win-win for everyone! Well...other than him I guess…but then again, he’s the one that told me about it in the first place! Haha”

Michael was still collapsed across the floor. Breathing heavily. He covered his face and tried to turn his head away in an attempt to escape our laughter.

Emma examined his caged area. Still mesmerized by what just happened.

“Should we...take his cage off? To clean him?” she asked, genuinely.

It had been a long time since Michael’s cage was removed, and even then it was only done when he was in full bondage, so that he didn’t get any ideas. He tended to get pretty handsy down there if left unsupervised.

“I suppose we can take it off…” I mused, turning Michael’s head to look at me and switching to my stern tone, “But you better be on your BEST behavior, and don’t try any funny business, you hear me?!”

Micahael’s eyes went wide in a mixture of awe and anticipation at the thought of having his cock be cage-free. He gulped, then nodded.

I pulled the chain from around my neck until it elevated out from between my cleavage. The tiny jingling of the key had Mikey drooling like Pavlov’s dog.

As I made to bring the key over and unlock him, Emma opened her hand out. “Can I do it?” she asked.

I hesitated, still mesmerized by how well she was taking all of this, but finally grinned and handed her the key.

She used it to unclasp the lock that held the device together. Gently pulling the front face of the cage off. Ropes of sticky goo came with it.

As soon as Mikey’s slimy dick got a breath of fresh air, it straightened up and hardened. Pointing straight up.

“Oh my God!!” Emma giggled. “It’s so tiny!! It can’t be more than, what? 3 inches?! Goodness! No wonder you keep him caged and Pampered!”

Mikey’s cock used to actually be around 4-4.5 inches, but after months of prolonged chastity, it had shrunken and shriveled. I didn’t bother correcting her.

“Yes, it’s quite the itty bitty thing, isn’t it??” I laughed. “Poor wittle guy never had a chance of pleasing me!”

That wasn’t exactly the truth. Michael was always fine in bed. But that was it, just…fine. Over time we both sort of came to the conclusion that there were other things we could do to satisfy our needs.

Emma grabbed the wipes again and pulled out two. She used the first to clean the area around his balls where the cum had run down. Careful to avoid the little vienna sausage that was pointing at her.

Finally the time came to clean that little sausage.

“Are you sure you don’t want me to do this part?” I offered again.

“I got it!” Emma said nonchalantly, as if touching another man’s penis was no big deal.

She gently gave two quick swipes with the wipes on the head of Mikey’s penis.

And that’s when it happened.

His dick started twitching. His breathing quickened. Emma and I sat back as we watched it unfold. Emma removing the wipes from the spasming penis.

Michael tensed and clenched and squinted as if he was trying to hold something in.

All of a sudden his dick started spurting!

Squirt after squirt of semen pumped out of Mikey’s little member. As if he hadn’t just cum two minutes prior.

Emma and I were both in shock. We sat there, slack-jawed, as we eyed each other back and forth.

Then the cackling started.

“Oh my fucking GOD!!”

“Did you see that?!”

“I barely even touched him!!!”

Emma had to cover her face and mouth to stifle her laughter. Mikey looked like he was about to cry in pure shame. Emma was wiping away tears from giggling so hard. Mikey was wiping away tears from being so embarrassed.

Honestly, I was embarrassed for him. After months of keeping him in diapers, I thought all of the most humiliating things had already happened, but this? This was a whole new level of...pathetic.

Emma finally got it together and managed to say, “Awww!! It’s okay wittle Mikey! You couldn’t help it, could you? You’re just a wittle baby that can’t control himself!!”

She used the wipe to clean up his sticky mess. Apparently not perturbed by what just happened, and not worried it would happen again (though even I couldn’t be certain…)

“Should we lock him back up to make sure this doesn’t happen again?” Emma asked me. Mikey whimpered, but we all knew it was the best course of action. I handed her back the tubing and the key so that she could slip his slimy member back inside. Clasping and locking it shut.

“Now let’s get you a new diapy on--” Emma started to say.

“Not yet.” I stopped her.

Both of them looked up at me, befuddled.

“Any time Mikey cums without permission” I explained, “he has to be punished.”

Emma and Mikey both had opposite reactions. Emma’s smile grew from ear to ear, while Mikey’s eyes produced tear after tear.

“Come on, let me show you where I keep the ‘corrective’ instruments!” I said, like a proud collector excited to show off her trinkets.

Emma followed me over to the wall next to the closet. Hanging from several nails (that Michael was forced to hang) was a variety of spanking implements. Paddles, whips, straps, floggers, crops, belts, canes, everything you could think of.

“Take your pick!” I told her, and Emma’s eyes lit up like she was in a candy shop.

She combed over the hairbrushes and ninetails. Tested the weights of the paddles. Jingled the belts and jiggled the whips. Finally she landed on the small red pingpong paddle.

“I used to play pingpong with my brothers. Never got to spank them with it though…” she explained as she took it off the shelf. Spinning it in her hand and testing the weight. “I think i’ll use this!”

Mikey whimpered as we returned to him on the floor. “Why don’t you come sit across my knee, Mikey!” Emma ordered, “Isn’t that how wittle babies like you get punished?”

Michael sniffled as he crawled over and climbed across Emma’s petite legs.

“So how many does he usually get?” she asked.

Usually, punishment for cumming without permission is about 20 spanks and extended chastity, but I wasn’t going to tell her that. “Why don’t you decide?”

She thought for a second, then finally said “Hmmm...I’m thinking...Fifty?”

“50?!” Michael blurted incredulously, dropping his paci.

Fifty seemed like a lot, but I didn’t want to step on her progress. She seemed genuinely excited about it. “50 it is!”

Emma smiled, taking up the paddle. She rubbed the ribbed edge along his bare ass for a bit, then brought it up and down hard.

“Aghh!” Mikey squealed.

Emma smacked him again.

“Mikey...you need to be thanking Miss Emma for every swat you receive! She doesn’t have to be doing this…” I lectured him.

Michael screwed up his face in shame, then begrudgingly intoned “Th-th-thank you Miss Emma…”

“That’s better...now maybe we should start over?” I offered, ignoring Michael’s protests.

Emma nodded, grinning wickedly as she smacked his ass again.

“Arghh! One! Thank you Miss Emma!!” Michael whined.

She brought it down hard on his other cheek, for such a small girl she sure did have a lot of force.

“TWO! Thank you Miss Emma!”

Then she started really letting him have it. Back and forth harder and harder on alternating cheeks. Michael’s legs were jiggling and his squeals were ringing.

At the count of 20, he looked at me pleadingly. As if willing me to say “that’s enough”, but I just shook my head. I smiled as I watched this young 20 year old girl put a grown man in his place.

His tears started flowing around 35 or 36. His cheeks were redder than the rubber on the paddle. But Emma showed no remorse. She had little to no attachment to Michael, despite changing his poopy diapers and cleaning the cum off of his pre-ejaculating penis.

By the time she hit 50, Mikey was a sobbing mess on the floor.

She gently turned him over and put him in a fresh diaper.

“There there…” she said, almost sympathetically, when it was all done.

“Do you mind if I coddle him a bit?” she asked me.

I really couldn’t say enough about this girl, she was just the right amount of stern and affectionate. It was like she was born to do this very job, and for $200 an hour at Michael’s expense, she was well worth it.

Emma helped him into her lap and held him like a baby. Rocking him back and forth and ‘shhhing’ him. “Don’t worry, it’s all over...for now!” she said, and started unbuttoning her blouse.

She pulled out one of her perky little tits. “Is this okay?” she looked at me for permission.

“It’s definitely okay with me, I’m sure Mikey’s little pee pee will be having a field day in his cage though! Hahaha!”

We both laughed as Emma took her breast and put her nipple to Michael’s mouth.

Mikey’s legs clenched, like there was something pinching him between his thighs. I watched him nurse from his new babysitter for several minutes until the doorbell rang.

“Oh! That must be Marcus!” I exclaimed, unable to keep the excitement from my voice.

Michael’s eyebrows shot up confusedly, and he tried to turn to look at me. “Who’s Marcus?!” he asked.

“My date.” I replied firmly.

“I thought his name was Damien?”

“No silly! I’m going out with Damien next week!”

I watched his little eyes spin as he tried to keep track of all the men I’d be seeing. We had been talking about it for months, but now that it was finally happening, I think his brain was struggling to accept the reality of it. He also probably thought he would be staying home alone while I was gone…

“Are you going to be alright with him?” I asked Emma..

“I think we’ll be just fine,” she smiled, putting his head back down on her breast. “Won’t we Mikey?!”

“Well you have my number, and if he gives you any trouble be sure to use that paddle again! Thank you so much, Emma!” I said as I went to leave the room.

“Any time, Mrs. Draper!” she called back.

I could still hear Michael’s suckling and whimpering softly after I closed the door and descended the stairs. I could only imagine what must be going through his head as I went out with a new man for the first time.

It was a night of firsts for me, Mikey, and Emma. The first of many.

The End.