My Diapered Boyfriend Ch. 04

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I hopped into Lily’s car when she arrived at my house. Nervous, I straightened out my skirt for the tenth time before sitting, feeling the diaper I was wearing beneath.

“Did you bring a spare?” She asked, smiling.

Still too nervous to speak without fumbling my words, I opened my handbag and showed her the extra diaper and wipes I brought along.

“Always better to have the option to change than not,” she told me as she started the car and headed towards the city.

Ever since Lily suggested we hang out, we had brainstormed places we could go, and the topic of where we had gone as kids came up. At one time or another, we had visited the city with our families, so we settled on that.

Later, after thinking about it, I worked out it meant that Bobby had worn his diapers around thousands of strangers in the city. It got me curious — and excited. I had a million questions and worked up the courage to tell Lily how I felt. Her advice was to capitalize on my excitement and to simply act on it.

It led me to wearing my diaper into the city with my boyfriend’s sister to satisfy my curiosity as well as understand Bobby a little better.

We parked in a garage downtown, but as soon as we stepped onto the street the doubts creeped into my head.

I clung to the straps of my handbag, staring at the sidewalk.

“It won’t do you much good staring at the pavement,” Lily said, giggling.

I took a deep breath and started following her lead, acting casual and wishing it could be for real.

The enveloping softness of my diaper rubbing between my legs at each step left me hyper-aware of it the entire time. I averted my eyes from all the strangers I came across on the street because I felt so nervous.

I kept telling myself there was no way they could know I was wearing a diaper but thinking about it nonstop made everyone around me seem psychic. Their disgruntled faces said to me, ‘I know what you have on under there.’

Seeing my escalating sheepish behavior, Lily grabbed my hand, pulling me closer to her.

“So,” she asked, “do you think it has changed much since you were little?”.

I knew she was trying to put me at ease. Even so, it worked a little.

“Well, I recognize some of the buildings, but they look different, newer,” I said.

“Yeah, a lot of old ones got bought and changed up,” she told me. “The department store we’re going to use to be a warehouse before they renovated it.”

“Cool,” I responded, not knowing what else to say.

“What did you do here as a kid?” She asked to keep the conversation going.

“Um, I remember going to the Natural History Museum. We went there a lot.”

“That must have been fun.”

“Yeah,” I said, getting into it, suppressing the thoughts of my diaper for a second. “We spent the whole day here, even staying for dinner. And afterward, we drove into the nearby mountains to see the city all lit up at night.”

She chattered on, putting me at ease until we reached her favorite department store where we tried on a range of outfits. I kept an eye out for skirts and pants that would hide my diapers. Lily pointed out it meant I was already thinking about wearing them around people which got me to blush.

In the changing room, I hesitated to take off my clothes, recognizing only a thin door with cracks at the bottom and top separated me from exposing my diaper to everyone. After I worked up the courage to undress, I heard its crinkling at every move I made. The ambient music pulsing through the store did nothing to hide it.

Since it took me longer than I expected, Lily asked if I was alright, motivating me to swallow my anxiety to bursa escort bayan finish changing.

When we left, Lily took me to a surprise extra boutique store that sold a wide variety of bras and panties. Inside, she whispered to me to just find a cute bra since my diaper already maxed out the cuteness below.

I giggled, growing accustomed to her swings at opening to me, yet still looking away from embarrassment because I had already spotted a bra that looked like a good compliment to my diaper.

I pretended to browse elsewhere until I could check it out on my own. Seeing my chance, I picked up the pink bra with white ruffles lining the tops of the cups. It made me think of a diaper a princess would wear.

“I’d like to see you in that one,” Lily said from an aisle across.

Startled, I jumped or backed into the table behind me, but I regained my composure, smiling at her and nodding. I was becoming accustomed to her assertive side.

We entered the changing room together. She took off my skirt while I removed the white blouse I had bought at the previous store. I liked it so much I just had to wear it when we left. She stood behind, clasping my new bra into place.

“There,” she said. “You look like a diapered princess in a fairytale.”

Just snickering at first, we laughed out loud when we realized how similar our thoughts had been. Like my blouse, I wore my princess bra underneath it after we had paid. We then headed to our next destination.

Lily took me to a fancy hotel I believed was older than my grandparents. The ones from my family trips had looked less grand, yet I remembered getting a kick out of running around and exploring those.

Inside, I spotted a very luxurious restaurant. When Lily headed toward it, I slowed down.

“Hold on,” I said, “are we going to eat there? I don’t think it’s in my budget.”

I had spent most of the money I had earned from a new part-time job on the clothes I just bought. I had found the job to pay Bobby back for the diapers he ordered for me.

“No worries,” Lily told me. “It’s my treat. As thanks for coming out with me today. I saved it for a special occasion, and I can’t think of anything better than this.”

How could I say no after that? And till now I thought my diaper had made me self-conscious. So, I ended up enjoying a delicious, filling meal after such an overwhelming day, but it wasn’t over yet.

Near the end of what we supped on, Lily asked me, “So…what have you been able to do in it?”

It took me a moment to realize she meant my diaper, but then I was at a loss for what ‘do’ meant. A kaleidoscope of images flashed through my mind of what I had done with and to Bobby, and what I had done on my own. I could feel my face burning red.

“Let me put it another way,” she said, seeing me struggle to come up with an answer. “When you decided to wear it out with me today, it made me happy because I got to see you coming up with new possibilities.”

I hadn’t seen it that way before, but it made a lot of sense.

“You shouldn’t limit yourself,” she went on, “don’t be afraid to make mistakes. Trust me, you’ll be surprised where you end up.”

I thought about what she had just said as we finished up. I kept thinking back to those family trips. And when I did, I squeezed my diaper between my legs, feeling my urges bubble up in a new, unexpected way.

“There…there is something I want to try, but it’s embarrassing,” I offered.

As usual, Lily’s probing motivated yet also intimidated me. It made it difficult for me to let my guard down around her when she read me so well.

“That’s fine,” she said, “just do it. Don’t let me stop you.”

“You mean it?”

“Of görükle escort course.”

“And you wouldn’t mind if I did it on my own? It’s a little embarrassing”

“Do whatever you want,” she chuckled.

“Okay,” I said, getting up, “but I don’t know how long it will take.”

“I’ll be here for a while. Just call if you need anything, or you want to change plans.”

“Thanks, Lily. I really appreciate it.”

I took my handbag, left the restaurant and headed for the nearest elevator. My finger hovered over the button for the luxury suite level and pressed it.

At the top of the hotel, I wandered up and down, hearing every crinkle of my diaper in the quiet, deserted hallways.

I froze when I saw a cleaning maid exit one of the rooms. She looked at me. I waved my hand to keep from feeling too awkward. She just smiled and pushed her cart down another hall. I waited till I heard her go into another room.

Regaining my curiosity, I approached the door she had just opened, but I never heard it fully close. I checked, and it swung open from a little push.

I searched around to see if I had been noticed. Satisfied I was alone, I entered.

Closing the door behind me, I expected anything above nice, but nothing as grand as it turned out. The door opened to a living room with a shining wooden coffee table and two long couches on either side of it. Beyond that, a dining table stood by the floor-to-ceiling window looking over the city.

A pristine bathroom with a shower and jacuzzi occupied one end while a well furbished bedroom filled the other.

Following my inspection, I stood in the bedroom and opened the curtains, gazing down at the view. I loved the sights, height, and privacy.

I realized, even in front of the window, no one could see me in my diaper, which emboldened me. I removed my skirt and exposed my diaper to the city below. I spread my legs and touched the front of it. I had never felt this unrestrained before.

My nervousness and excitement from the whole day caught up to me. The strong need to go rushed in all at once, so I pushed and pushed, pressing my hand against the glass until I started wetting my diaper.

It streamed out easier than last time, and I continued posing in my soggy diaper in full view through the window, feeling a big, dumb smile grow on my face.

Giddy at how astonishing it felt to be doing all of this, I ran around the whole suite with my wet diaper sagging, and I leapt onto the king-sized bed. I stared at the ceiling, catching my breath.

So, this was how it felt to be independent: to let loose. I wished Bobby was here to experience it with me. I believed it would do wonders for him.

Once I began thinking about him, I couldn’t stop.

I imagined him here with me, walking through the door, admiring the suite and holding hands while we inspected all the rooms.

After settling in, we would order room service, drinking coffee at the dining table. We would go from looking at the view out the window to glancing at each other and snickering when our eyes met.

My hand rubbed my wet diaper as I consumed the fairytale scenario in my head.

Then Bobby would carry me in his strong arms like the princess I was to the bedroom, and all the while I would hear the crinkling of his diaper till, he laid me down on the large bed, pushed open the curtains and let the sunlight beam in on me.

My sensations went into overdrive thinking about Bobby.

He would stand in front of me, taking off one piece of his clothing at a time. He would do it slow, building up my anticipation before revealing his diaper.

In my fantasy, it mattered most that he smiled at bursa escort bayan me while he did so: it covered up how much he wanted to get ahold of me, and his tantalizingly slow pace masked the aching in his diaper for me.

I moaned out loud and my hand moved faster.

“Bobby,” I called out, making the illusion more real.

Bobby would then lie beside me, his diaper exposed, cuddling up as we rubbed our diapers together.

Oh God! The images overtook me. I squirmed left and right, unable to stop the mounting euphoria inside my wet diaper.

“Bobby, I gonna cum!” I yelled into the empty room.

He would then attempt to remove my new blouse but fail halfway as he saw my breasts in my princess bra. Bobby would cream his diaper at the merest sight of them.

I hit my limit at the point in the fantasy where Bobby was recovering while I undid his tapes when he was at his most vulnerable: just after cumming in his diaper. And then my climax hit so hard my mind went blank.

I kept my eyes closed, catching my breath. Awareness of the forbidden room returned, but I paid that no mind. I was still not able to get Bobby out of my head, wishing he was here even more after the powerful orgasm he gave me.

Even as I longed for him, I heard voices outside the door to the suite. It sounded like a family trying to force the key into the lock. I held my breath.

I was about to be caught, lying half-naked on a bed in a wet diaper right after masturbating to fantasies of my boyfriend! One of the parents though pointed out they had read the number wrong, so they moved on to a different suite.

I breathed a long sigh of relief. I told myself I took my adventuring as far as I could today, but I would do it next time with Bobby.

Feeling the front of my wet diaper, I decided to change, giving thanks to Lily’s advice for bringing a spare. I never could have anticipated anything like this happening when I got into her car, but I was glad that it did.

Dressed and snug in my new diaper, I waited until I was sure no one would notice me as I left the luxury suite. I strolled down the hallway, slipping my used diaper into the trashcan by the elevator, and rode down.

Wearing a fresh diaper reinvigorated me. I fidgeted with it between my legs. I could not stop thinking about Bobby as new possibilities overran my thoughts. By the time I reached Lily, my desires took charge again, so I proposed to her that Bobby should pick me up from the hotel.

“Interesting. What do you expect to happen?” She asked.

I could only look away, swaying back and forth, and pressing my hand against my diaper. These possibilities I had not yet fully decided on tickled my insides in a way that left me speechless.

“I see,” she said and did not press me for further details, but she knew what I was thinking. She kissed me goodbye and headed for home.

After calling Bobby, and asking him to pick me up, I waited for him out front.

I contemplated where I could direct my titillating desires from here. I really appreciated that he had gone along with driving to the city for me without asking questions even though that’s what a supportive boyfriend does. I felt lucky to have him, and I needed to show him how much.

It began to rain, but the hotel’s canopy kept it off me. Watching the water fall to the pavement, I new plan popped into my head that made me so happy I wanted to hug my diaper in thanks.

I stuck my upper body into the rain, keeping my skirt and diaper dry under the canopy. I wrapped my hair into a bun and clenched it tight in my hand to prevent it from getting soaked, but I made sure to drench the thin fabric of my white blouse.

Once done, I pulled back, shook out my dry hair and waited.

I hoped Bobby would arrive before my efforts went to waste.

He drove up in the same Prius. I jumped right in, stuffing my bags on the ground behind my seat. I was very excited at what I was about to do!

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