Hero Undercover: 25 Breathtaking Bad Boys

by Annabel Joseph

  The game was on.

  Getting up, I walked to the end of the bed and reached for my black bag that had all of my toys.

  “What are you doing? I gave you permission,” Chloe said looking at me with big, sad eyes.

  “I’m aware, but there is a lesson that you are in desperate need of being taught.” With a soft thud, I dropped the large leather bag by her feet. Then I pulled out my flogger, and a pair of nipple clamps.

  She sat up, watching my every move.

  Having all I needed for now, I placed my back bag on the ground, then with a whoosh, stripped the sheet off the bed. No hiding at punishment time for my little lady.

  With a firm grasp on her, I moved to the side and with the provided cuff and strap I fastened her to one corner of the bed. I made quick work of doing the same to the other foot leaving her legs spread wide and the lovely curls she’d teased me with on full display. Proceeding to the top of the bed, I quickly restrained her wrists as well. When she was spread eagle, I took a step back and enjoyed the view.

  “Adam,” Chloe whined, wiggling around as she tested her restraints. I hadn’t made them so tight that she wouldn’t be able to move. I didn’t want her to injure herself.

  “Quiet,” I commanded, snapping the flogger against her stomach. It was lightweight, made of soft deerskin, and perfect for beginners. I knew it wouldn’t cause her pain, but would instead bring attention to the area. I flicked again, slightly lower. “When you came to this resort, you agreed that I would be the dominant. As such, I’m the one who decides what we do and when we do it. Trying to tease or manipulate me into doing what you want to do is known as topping from the bottom. This is unacceptable, and will result in a punishment for you. Am I clear?”

  “Yes, Sir,” she answered, her reply coming out in a breathy whisper. She looked up at me with wide eyes, her pupils beginning to dilate. My naughty girl was turned on with me firmly in control. Excellent.

  As a reward, I gave her pussy a couple of thwacks and watched with delight as her back bowed off the bed. For now, I enjoyed her uninhibited reaction. In the future, however, I’d want her to stay still; it would enhance her pleasure.

  “We’re going to do a bit of practicing,” I announced. There was no time like the present to start her training. “You’ll get my lash on various parts of your body. Your tits,” I landed a light stroke there, “your thighs,” she received another well-place swat, “and all points in between. I want you to stay still. For every move you make, you’ll earn another stroke and double the time I make you wait for an orgasm. Understand?”

  “How long must I wait?”

  “Sir.”

  “How long, Sir?”

  “That’s for me to decide, isn’t it?” I dangled the flogger threads over her, so that only the very tips touched her skin, then when she least expected it, with a flick of my wrist I brought it down fully in a firm slap. When she made no movement, except a shuddering breath, I grinned. She was meant for this. Really getting into it now, I set up a circular rhythm, painting her white skin with a rosy blush. I especially focused on her swollen breasts and glistening pussy lips.

  To my new submissive’s credit, she didn’t move her body as much as I thought she was going to. When I smacked her vagina, she flinched and moaned, but her back didn’t leave the bed.

  When her breaths were coming out in little pants and her face was red from the effort of remaining still, I dropped my lash, done with it. I had her excited and ready for me, but there was one more thing I wanted to do before I claimed her.

  Grabbing the nipple clamps, I climbed onto the bed. Straddling her hips, making sure not to put any of my weight on her, I called to her softly.

  “Chloe.”

  Her eyes, which had been scrunched tightly shut, opened revealing unadulterated desire.

  “I’m proud of you, sweetheart. You stayed still for me, and did much better than I anticipated you would.”

  A smile crossed her lips and if my ears weren’t mistaken, it sounded like she purred at my praise.

  “Thank you, Sir.”

  I leaned over and planted a kiss on her lips. When she opened her mouth to me, my tongue slipped inside, entwining with hers in a dance as old as time.

  I pulled back and kissed a trail from her lips, along her neck, and down to her breasts. Taking in one of her beaded nipples, I alternated between sucking it and flicking it with my tongue. When I knew it was ready, I fastened on one of the clamps and thrilled at her slight hiss of pain.

  I licked my way to her other breast and gave it the same treatment. When I was finished, I sat back and savored the sight of the clamped rosy tips and the fast rise and fall of her breasts.

  “Hmm, it appears that someone likes nipple play.” To further prove my point, I tugged lightly on the connecting chain, causing her to moan.

  Bending to her lips again, I repositioned myself as I kissed her deeply. Hovering over her, I aligned my cock with her slick channel. I was trembling with anticipation as much as my Chloe was when I finally plunged myself inside. Knowing it had been a while for her, I stopped once I was fully embedded and let her adjust. Raising my head until I could see her eyes, I asked, “You okay?”

  “Oh… yes…” came her husky response.

  With a grin on my face, I started to move. Toying with her, and making her wait was as much torment for me. Soon, I pumped in and out of her, relishing every slick, tight inch of her. Struggling for control, wanting to make sure it was good—great—for her, I dropped my head into the curve of her neck, pressing open mouth kisses there, and up to the sensitive spot behind her ear.

  “Adam,” she moaned.

  “You may come,” I whispered, before gently biting the lobe.

  She came beautifully, screaming as she found her release. Her entire body spasmed as she rode wave after wave of pleasure.

  The entire time, I continued to pump in and out until with one final thrust, I buried myself deep and found my own orgasm. Chloe’s inner walls clamped down hard on my cock, milking from me every last drop of seed.

  When we finished, both of us panting, I fell to her side, replaying every minute of the best sex I’d ever had. I’d never had a submissive be so responsive to my play. What we shared wasn’t enough. I blinked, realizing when it came to Chloe I might never get enough.

  It took me a moment to recover. Once I did, I moved back between her open legs and started to lap up the abundance of juices.

  “What are you doing?” she asked, her voice coming out breathy.

  “I’m getting you ready for one more orgasm.”

  Getting back to my work, I dove my tongue in and out of her opening, mimicking the motions my shaft had just made inside of her.

  After I had enough of that, I traveled up to her clit. Gently drawing it between my lips, I began to suck. In moments, Chloe’s entire body started to shake. She was getting close.

  Not ready to send her over the edge just yet, I released her swollen bundle of nerves and kissed my way up to her breasts.

  “These need to come off,” I murmured, touching one berry red compressed nipple. There’s going to be a bit of pain when I release them. After, I’ll make it better, and you’re free to come whenever you like.”

  “O-okay.”

  As I released the first clamp, she cried out as the blood rushed back. I started to suck, knowing it would help. I also let my fingers travel down to her swollen bundle of nerves and rubbed small circles on it.

  Chloe tensed up her legs continuing to shake underneath me and she let out another scream of pleasure, even louder than the first. When she seemed to be winding down, I freed her other nipple and it spurred her pleasure on even further.

  Hovering above her, I couldn’t help but notice how absolutely stunning she looked as she came.

  Lowering my head, I gently placed my lips on her, silencing the remainder of her moans. When I pulled back she was mewling like a newborn kitten.

  “You’re all right, sweetheart
. I know that was very intense,” I said. “Hang on a minute and I’ll hold you,” I quickly moved around the bed freeing her from her bindings.

  Gathering her up in my arms, I held her close, while massaging away any aches in her wrists from the cuffs. When I was satisfied her circulation was good, I moved down to her ankles, released and massaged those too.

  Once finished, I dropped down at her side and cradled her to my chest again. Her eyes weren’t open. In fact, they had been closed since her last orgasm.

  “You okay, sweetie?” I asked, feeling a bit concerned.

  Her lashes fluttered open and her lips curved up, a goofy grin lighting up her face.

  “That was awesome.”

  I couldn’t help but laugh at her as any fear I had disappeared. It appeared she enjoyed herself as much as I did. So much in fact, that she appeared stoned.

  “You stay right here, honey, and I’ll draw us a bath. Afterwards, we can go downstairs and grab some breakfast. Does that sound good?”

  “Mm hm,” she answered, as her eyes drifted shut. With one more kiss, I left to set up the bath I’d promised.

  After our bath, we went downstairs to the community room for breakfast. I was starved, having worked up an appetite from our romp in the hay earlier.

  Adam held my hand as we walked along, looking so handsome I kept giving him sidelong glances. He had on a pair of dark jeans that fit him like a glove. Matched with a dark blue t-shirt and his violet broach, my man looked good enough to eat. It made me wonder if he’d let me go down on him. Blow jobs were something I very much enjoyed doing. There was just something empowering about them, and I couldn’t wait to make this powerful man shake with desire until I slurped up his seed.

  Shaking my head to dispel my current thoughts, I reviewed the age play rules Adam had explained while we were in the tub. One was what to call him outside our suite.

  “Daddy, may I please have a princess plate?” I asked, pointing to the ones stacked at the front of the buffet line.

  To my surprise, I didn’t feel weird about calling him Daddy. I thought I would have, but it actually felt natural to me. Based on the huge grin that crossed his face, he felt the same way.

  “Of course, sweetie.” He handed me the plate and matching utensils. As we walked down the buffet line, he helped me get the food I wanted since my hands were still a bit shaky after the morning.

  Once we had loaded up with scrambled eggs, sausage, croissants, and fresh fruit—every breakfast dish I could imagine, and even some I couldn’t like these yummy-looking blueberry cheese blintzes—we found a booth in the corner and took our seats.

  Diving into the meal, I didn’t realize how sloppy I was being until Daddy moved beside me and wiped my face. “If you’re this messy at every meal, I’m going to have to buy some bibs.”

  My cheeks warmed at his comment. They really heated up when I looked down at my shirt and realized he was right. I was normally very neat when I ate, but I was so hungry this morning I hadn’t been paying attention at all.

  “Sorry, Daddy. I’ll be more careful,” I reassured him.

  “It’s okay, pumpkin. Baby girls have been known to be messy eaters. You have nothing to apologize for.”

  For the rest of the meal, I paid more attention to making sure the food on my plate got into my mouth and nowhere else. I also noticed that my Daddy kept shifting his eyes around the room. A few times I turned my head wondering what he was looking for, but when he returned to his breakfast, I thought maybe I had imagined it.

  As I was eating, I thought about how easy it was for me to slip into my little girl headspace. Before I came here, I thought it was going to be really hard for me to do. Calling a stranger, ‘Daddy’ and letting him take care of me. It sounded crazy. But now that I was here, it felt right.

  It felt even better to call him sir and let him master my body. For the four years that Roger and I were together, he never made me come like Adam did. In fact, he was such a selfish lover, I considered myself lucky to come at all with him. If I wasn’t careful, I could get addicted to the orgasms Adam doled out.

  When I finished before Adam, it gave me a moment to look around the room at the other couples. Everyone smiling, chatting animatedly, or laughing, and enjoying themselves. All the age groups were represented amongst the littles. Most wore little girl dresses with bows in their hair, a few had on rompers or footie pajamas like very young babies, and some others, the ones in short plaid skirts, knee socks, and pig tails were obviously the teenagers.

  I was wearing a white dress with colorful polka dots all over it.

  There was one girl who had on a very pretty blue dress with one of my favorite My Little Pony characters, Rainbow Dash, on the front. I wanted to go up and talk to her, but couldn’t because she just skipped out of the room, her caregiver following behind her.

  “Are you ready to go, honey?” Daddy asked as he stacked our used dishes on a tray.

  “Mm hm,” I responded, following him to the return bin for all the dirty stuff.

  As we left the dining room, he took my hands in his again-something I really liked—and asked, “So what do you want to do today?”

  “Can we just explore?” I remembered reading about all of the different play rooms the resort had to offer, but because Daddy and I had gone on a walk the previous night, we missed Mr. Burke’s talk about the different activities that took place in each one.

  “Sure.” We headed down the hall, stopping at the first door. Inside we saw a huge swimming pool. This was exciting because I loved to swim! But, I didn’t want to go now because I had just eaten. My mother warned me to wait at least an hour after eating to go swimming or I’d get a cramp.

  We continued to the next door and peeked in. It was a huge gymnastics room filled with trampolines, inflatable bouncy houses, a foam pit, a balance beam, a rope—basically anything gymnastics-wise you could imagine. Even better, the girl with the blue dress from earlier was inside with her Daddy. They were both bouncing on one of the trampolines.

  “Oh, Daddy, can we please play in here?” I begged. I wanted to try and get to know this girl better. She seemed cool.

  “Of course.”

  I dashed over to the girl and her caregiver. When they noticed me, they stopped bouncing.

  “Hi! I’m Chloe, and this is my Daddy, Adam,” I said, pointing behind me.

  “My name is Belle and this is my Daddy, Paul.”

  “Do you want to play together?” I asked.

  “Okay!” she said excitedly, looking at her Daddy who nodded, as he got down and walked over to my Daddy and shook his hand. I took his place and started bouncing.

  “I really like your dress. Rainbow Dash is my favorite pony.”

  “Mine too,” Belle beamed. “I love your shirt with the cheetah on it. They’re my favorite real-life animals.”

  “Mine too!”

  “Do you want to be friends?” Belle asked.

  “Yeah!”

  “Cool!”

  We beamed at each other as we kept jumping. This week was going to be awesome! I had an amazing Daddy and now a new friend.

  Chapter 4

  The next morning, I awoke in the same position as the day before, and Chloe had once again wrapped herself around me. She was so beautiful when she slept.

  Yesterday had been a major success. Sex with Chloe had been incredible, and being allowed to act the part of her Daddy was surprisingly fulfilling. Before this trip, I never thought age play was my thing, but seeing how happy it made my baby girl to forget all her adult worries and return to a carefree state of mind made it all worth it to me.

  After Chloe and her new friend Belle were finished playing, we all decided to go on a picnic. As the girls ran around and played, I got to talking to Paul. He was a nice guy, definitely less strict than I was, but he was still great. He was big into sports, so as the girls played, we chatted about different athletic teams.

  When I noticed my little girl starting to run out of steam a b
it, I decided to call it a day. With promises of meeting up tomorrow, we headed back to our suite where Chloe took a nap. When she awoke, I claimed her again, this time doggy style. Since she had been behaving so well, I also gave her a fun spanking with my hand. She seemed to enjoy it so much, I gave her five swats with my belt.

  Her pussy was weeping by the time I put my implement down. I took her again, until she screamed out my name in pleasure.

  Once we caught our breath, I drew her a bath to ease her sore bottom It turned into a fun affair. Watching her play with toys in the water was pretty cute.

  Once washed, dried off, and dressed, we went downstairs to where the rest of the couples were eating dinner. Sitting with our new friends, we shared an enjoyable dinner. When we finished, the girls begged us to let them play outside. Since the sun was still out, I didn’t see why they couldn’t. So, for the next half hour, they got to run around the manicured yard having a blast.

  Afterwards, Chloe and I came back up to our bedroom where we watched an action film before we both fell asleep.

  As I thought back on how awesome the day had been, it made me realize the woman I held in my arms was truly someone special.

  The only downside to yesterday was I had failed to spot Edmund Burke. His little, Priscilla, was floating around, but without her Daddy. It made me suspicious why a Daddy would let his little roam alone, but I didn’t want to draw any attention to myself by asking questions.

  Chloe whimpered and snuggled up closer to me. A peek at the clock told me it was 6:30 in the morning, a bit early to rouse her for sex.

  As carefully as I could, I got off the bed, making sure not to wake her. She whined for a moment in her sleep, but grabbed my pillow and snuggled up close to it.

  Deciding this was the perfect opportunity, I snagged my phone, walked into the bathroom, and hit the speed dial for my boss. I wanted to give him an update on the investigation.

  The call rang for a moment before he picked up.