A Jamaican Vacation Ch. 02

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Athletic

After the events of yesterday, I slept hard. I’m not exactly sure what time we fell asleep, but I woke up from a combination of the sun hitting our room and a hardening big black cock in my mouth.

I can’t believe I slept the whole night in lingerie with Big Daddy’s cock resting in my mouth and my right hand clutched onto it like a stuffed animal.

Instinctively, I started slowly stroking his cock. I took my mouth off of him and leaned back to admire, resting my head on his abs to get a full view as his cock towered above me.

How had I gone my whole life without this? How did I ever think I could bring pleasure to anyone with my little penis? How was I ever going to leave Jamaica and just forget about this?

I must have been staring for too long and awoken Big Daddy. I felt his hands grab my pony tail and lift my head up about 12″ so I could give him head instead of just marveling at him.

I’m glad I kept my hair long. Before I felt like a cool guy with a man bun, but now it made me feel even more girly.

As I positioned the rest of my body to give him head, I felt how sore my ass was. It ached. But the ache also felt so good. It was such a foreign feeling. I clenched my butt cheeks to feel the sensation again, the ache brought me pleasure in a weird way. I don’t know if it was the actual sensation or just that it triggered the memory of the most amazing sex I have ever had.

As I serviced his big black cock, I felt a familiar feeling as Big Daddy slid his hand behind my thing and stuffed a finger in my boi pussy. He just left it there, plugging me.

Once I realized he wasn’t going to finger me, I started to slowly grind my ass into his hand while I gave him head. It wasn’t as intense of a pleasure as his big black cock, but it still felt so good.

After giving him head for about 20 minutes, Big Daddy grabbed my head and held me on top of his big black cock, shooting rope after rope of his cum in my mouth. I couldn’t keep it all in and some of it dribbled out of my mouth.

When he finally released me, I took my mouth off of his cock and used two fingers to scoop the lost cum back into my mouth. Since he came in my ass last night, I didn’t get a chance to really taste his cum. It was delicious!

“Good morning Alexis, how does that pussy feel this morning?” Wiggling his finger inside me.

I gulped, swallowing his cum so I could talk. “So good Big Daddy. Sore, but so good.”

“I figured as much,” he responded, letting out a low laugh. “Why don’t you go get yourself cleaned up. You’ve already had breakfast, but I signed you up for a workout class this morning.” He said as he pulled his finger out of my pussy.

“Oh nice, is it another spin class?”

“No baby, you are going to be cutting back on spin a bit. You will still do it for cardio 3 times a week, but the other 4 days a week you are going to be doing double workouts focused on your ass and waistline. You already have a great ass, but with a little more work you can have an amazing bubble butt with a skinny waist.”

“Whatever you want Big Daddy” I responded.

Daddy then took his finger that was inside of my boi pussy and presented it to me. At first I was grossed out, but then realized I just worshipped his big black cock and that was inside of me last night too. I sucked his finger hard.

Back to the workout, The idea of rebuilding my body to be a sexy sissy was too much for my mind to comprehend, but I was in. I was addicted to his big black cock and wanted to do anything to please him.

“Now go get yourself cleaned up. Also, I know your legs are hairless from cycling, but shave your armpits and and pubes, everything has to go.”

“Yes Big Daddy, sorry I didn’t do that last night.”

I showered, shaved, and spent a few minutes combing and blow drying my hair. Typically I just let my hair air dry and get messy like a guy. But now I wanted to take better care of it to make it more girly.

After that, I came out into my the bedroom and started putting my workout clothes on from the night before. Although I was already mostly smooth before, I felt even sexier being smooth in my spandex and tank.

“You look great! Looks like you have a little sway in that ass as you walk after that fucking I gave your pussy last night.”

I blushed. “I do feel different today. For the first time, I feel sexy.”

I looked at him, his big black cock laid obscenely over thigh. I couldn’t help but stare.

“Why don’t you go grab that other bag from last night. We need to take care of a couple things.”

I didn’t know what he meant, but I brought him the bag and stood in front of him as he sat up in bed.

The first item was a strange looking purple plastic contraption.

“Lower your spandex sweetie.”

I hooked my thumbs in the waste band and lowered them until my little penis popped out. Shit I was already hard just from looking at him. Actually I don’t know if my little penis ever got soft after giving him head this morning.

“We need to take edirne escort care of that,” he said pointing at my little penis, “go get me some a cold soda from the fridge.”

I walked over the fridge and brought him a can of Coke. He took it and placed it against my little penis until it went soft and shrunk back to my normal size.

“Good thing I got extra small! I almost feel bad for the women you tried to pleasure with this. They probably have no idea how good sex can be.” He said matter of factly.

Next thing I knew, he was sliding the plastic device over my penis, and locked it in place. He then took the key and laced it through his necklace, so it hung from his neck.

My penis was locked in captivity.

“This will keep you from getting in trouble walking around with a boner here. Even though it’s so small and hidden from the public eye, I don’t want you being tempted into playing with it.”

I didn’t know what to say, I just nodded and looked at the floor. I was mortified and kind of nervous. How would I get this off? What if he disappeared on me?

“Please can we not do this? I won’t touch myself, I promise!”

“Sorry sweetie this is just a precaution for right now. This whole world is new to you right now, this will help you adjust. Here, this will help, lay down on your tummy across my lap.”

I did as he asked, afraid to say no now that he has be under control. As I laid down, I felt cold lube hit my asshole and something start to enter me.

I was more sore than I realized, but the further this object went in, the more relief it provided.

It was small compared to Big Daddy, but still felt big. I never saw what went in, but eventually he pulled my spandex up over my ass and spanked me to stand up.

“Alright, let’s get you to your training session!” He said as we headed to the door, no discussion of what just transpired the last 5 minutes.

As we walked, I felt my ass sway thanks to what I assumed was a large butt plug, as well as the deep fucking I received last night. I wonder what people thought, me a small white guy who in girls clothes walking down the hall hand in hand with this gorgeous black man.

Big Daddy dropped me off at the gym, and re-introduced me to Veronica, the lady from last night who dropped off the bags. She did have an amazing ass.

“So I assume last night went great you two lovers!” Veronica said, giving me a wink.

“Hey V!” Said Big Daddy. “It sure did! So Alexis here is already working with a pretty sexy feminine figure. She’s an avid spinner, but I want you to focus on getting her that Kardashian bubble butt and thinning out her waist a little bit more.”

V scanned me up and down. “Yea absolutely. This will be a pretty easy task. She does have a great body. 2 sessions a day and we will get her into amazing bikini shape by the end of the week.”

I shuddered. Bikini shape? I couldn’t wear a bikini in public. But also, how sexy would that be! All the people watching me flaunt the sexiest beach body at the resort. I felt my penis twitch, but couldn’t get hard. Maybe it was good after all! I wasn’t going to have to hide my erections anymore.

Big Daddy noticed the wheels spinning in my head and my hands going to my crotch as I worked through this all. He knew I would have had a boner.

And then, ‘BUZZ’. Shockwaves went through my body as the plug in my ass started an intense vibration. My knees went weak, Big Daddy caught me.

“So that plug I put in you this morning. It’s just a little something to remember me by. I have the remote, and will let you know throughout the day when I’m thinking of you by turning it on when I’m working behind the bar!”

Oh my god. I just nodded. I couldn’t function with that much pleasure rushing through me. Thankfully, he turned it off.

“Wow shes wired for pleasure!” V laughed, “look at that wet spot on the front of her spandex.”

“No joke!” Big Daddy responded, “I made her squirt in the first 20 strokes from this monster!” As he lewdly grabbed his cock.

I didn’t even think of that. Like I said, I have almost been quick in bed, but I’ve never cum as fast as I did at the hands of Big Daddy last night. Also, 10 seconds of vibrations from this plug and I was already leaking. This was too much!

Big Daddy leaned in and gave me a deep kiss.

“Have a good workout,” he said “I’ll be in touch with you later!”

Over the next 2 hours V kicked my ass! She knew what she was doing. She explained to me exactly which workouts would shape certain parts of my ass, and how to keep my waistline minimal. It was also just kind of fun doing these exercises with the plug in my ass. No body crunching buzzes from Big Daddy, but just a gentle reminder of why I was doing this.

After the workout, she sent me on my way back to my room with a smoothie for lunch. I was feeling pretty good about myself!

When I got to my room, it was cleaned up from last night and there was a note on the table with a couple of boxes.

“Hope you enjoyed cansoc.org your workout. I checked in with my friend at the front desk, he said your bag showed up. I took the liberty of throwing it out and have replaced them with a new wardrobe that is already unpacked in your room. Your mini fridge is also packed with smoothies. To help with your workout regimen, do not eat any food, just drink one of these every two hours. Also here are a few necessities I thought you might enjoy! Have a relaxing afternoon, I’ll pick you up at 7. Wear something that you think I’ll like.”

What the fuck? I thought to myself. This was all fun, but it was getting very real. He threw out all of my clothes. What was I going to wear home when this week was over and I had to get back to normal life?

I walked over to the closet, it was filled with short dresses, mini skirts, and sexy tops. I hurried over to the drawers and there were more panties and bras that I could imagine, there even looked to be garters and stockings.

I went back to the table to open the three boxes, two big and one small. The first box was a pair of black stilettos with straps. The second was a casual pair of wedges to wear to the pool. The third was a choker with a circular charm on it that said “Big Daddy”.

Lastly, I noticed that there was a clutch with a small metal box inside it and some lipstick. I opened it up and there were 20 joints in it. In the box there was a note that said “smoke one of these every other hour in between your smoothies.”

Big Daddy wanted me high and horny!

This was all too much. I decided to sit outside and smoke one of the joints and figure out what I should do next. How could I get out of this predicament?

I smoked the joint, it was nice. He had it cut with some tobacco so I could sit and enjoy the entire joint without being insanely high. But make no mistake, I was high!

As it always does, the weed has me feeling everything in overdrive. I realized I was sitting with my legs crossed like a girl. Why was I sitting like that? I felt the my tight spandex shorts cupping my ass.I felt the heavy plastic of my chastity device containing my little penis. And of course, I felt the giant plug in my ass. I wiggled my ass into the chair. Damn it felt good. I wish Daddy would turn the vibrations on. I was nice and high and horny. With the cage, this was going to be only relief. I decided to take my mind off of my horniness by taking a shower.

As I walked into my bathroom, I noticed that my bathroom had completely turned over too. The soap wasn’t unisex anymore, it was feminine. My shampoo and conditioner was nicer. There was a curling iron, nail polish, make up, and hair spray. What was I supposed to do with this?

Oh well, I hopped in the shower and got cleaned up from my workout. I didn’t know if I was allowed to take my plug out, so I just left it in.

After my shower I walked over to my dresser to find some lingerie to wear. I sifted through my new underwear, they were all so feminine and sexy. I landed on a bra and panty set that was light purple with grey lace flowers on it. I slid the panties on and then clasped the padded bra.

Damn I felt sexy.

“BUZZ!”

My knees almost buckled and I let out a moan. I caught myself by putting my hands on my dresser. I looked up and saw myself in the mirror. My mouth hung open. But I looked sexy.

I smiled and embraced it, Daddy was thinking about me. I reaching down to play with my penis, the vibrations had me all worked up.

As my hands slid to my panties, I remembered that I’m caged. I couldn’t get any pleasure from my penis. So this is why he knew I still needed the cage. I didn’t have any self control.

Instead, I decided to take advantage of the vibrations. I laid down in bed and started massaging my breasts, trying to bring myself to orgasm. It felt so damn good, but this plug wasn’t his big black cock, it wasn’t enough to send me over the edge.

Frustrated, the buzzing stopped. I laid there for a minute catching my breadth, thinking through what I wanted to do the rest of the afternoon as I waited for Big Daddy and his beautiful big black cock.

I heard a beep from the keycard entry of my room and panicked.

“Sorry I’m busy, I don’t need any fresh towels!” I yelled from the bed.

“Hah! I’m not room service. Your man sent me up here!” said a woman with a Jamaican accent as she walked into my room. “Aren’t you a doll! Ty was right about you.”

“Who are you?”

“I’m a friend of Ty’s. He sent me up here to help you out with a few things.” She said as she patted a plastic box she was carrying. “First, did you have your smoothie? He wanted me to check to make sure you are on schedule, it’s very important.”

“I smoked my joint, but I need to have my smoothie.” I said as I walked over to my fridge.

I grabbed a smoothie and drank it.

“Alright, let’s get started! First, we are going to pierce your ears. Ty likes his white bois nice and dolled up.”

Before I knew it, she had numbed my ear lobes and pierced both of them.

“So right now I just have two little studs in, but for when you want to dress up here are two hoops. I know Ty likes these. Next, let’s have a female 101 in the bathroom!”

Over the next hour, she showed me how to do mascara, apply blush, style my hair, and paint my nails. I was getting a full on makeover and beauty lesson.

I looked so hot, she knew what she was doing!

“Oh shoot, I need to smoke a joint to maintain my schedule. Want to join me?” I asked.

“I have my own weed, but I’ll hang out for a bit she said.

We walked out onto my balcony and sat down to smoke our joints. As the high washed over me, I started to get horny and sensitive to everything again. I was loving how my hair has been slightly curled and hung down on my shoulders. I felt so feminine sitting there in my lingerie smoking my joint. I couldn’t help but notice my purple nails with fake tips holding my joint.

“So tell me about Ty’s cock,” she asked, “I’ve only heard stories.”

“Oh my god,” I gasped, “it’s unlike anything I have ever seen. Not that I’ve ever been with a man before, but I’ve watched my fair share of porn. He is probably a foot long, and thick, oh my god, so thick. I mean he made me cum in like 20 seconds last night, and I wasn’t even allowed to touch my penis.”

“I’ve never seen a white penis before, can I see yours? I’ve been trying to catch a glimpse in your panties but I haven’t been able to make anything out.”

Embarrassed I stood up and pulled my panties down.

She giggled and put her hand over mouth. Kicking her feet trying not to laugh too loud.

“I’m sorry…it’s just…you are so small!!” She laughed.

“Thanks a lot, I know that now,” I replied looking at the floor. I pulled my panties back up to cover my tiny caged penis.

“Well you know what?” She said. “Who cares! You aren’t ever going to need that little thing ever again, right? You are Ty’s girl now and he’ll be able to give you all the big black cock you could ever need.”

I sat back down and crossed my legs, taking another hit of weed. Was she right? Would I ever have sex with a woman again? Now that I know where I stand in that department, could I even get over my newfound insecurities to get hard for a woman? I took another hit of weed, finishing the joint.

“My boobs are sore!” I said out loud, rubbing both of them with my hands.

It felt so good. I’d never known that area to bring pleasure, but it did now. I stopped myself after a minute because I almost felt like I was masturbating.

“Alright sweetie, well I need to get going. Have fun tonight! Ty said that he will come pick you up at 7.” On that note, she left. Leaving me in alone to my own devices.

I looked at the clock, it was 4pm, time for another smoothie. I walked over to the fridge and slurped another one down. These were tasty, and I wasn’t even hungry for other food.

“BUZZZZZ,” Daddy was thinking about me again, I felt my the vibration deep in my body.

Damn it felt so good. The vibrations kept going. Between the weed, the lingerie, and the plug this would have been like my 5th boner of the day if it wasn’t for the stupid cage. I needed to get myself off.

Lucky for me, the vibration was still going! I was determined to get myself over the brink. I ran over to the bed and straddled a pillow like I was riding Big Daddy. I used the leverage from the pillow to grind my ass in a circular motion, forcing the plug to hit different spots inside my boi pussy.

I kept riding, I was getting close. I remembered my new found erogenous zone of my breasts. I grabbed them hard and kneaded them in a circular motion as well.

I moaned in pleasure and frustration. I needed to go harder. I started to grind my ass harder, but couldn’t get myself over the edge. After about 20 minutes of this, the vibrations stopped.

I got off the pillow and stood up, walking over to the mirror. My panties were soaked. The light purple was now dark purple. I had been leaking through my cage almost the entire time, but I never had an orgasm.

I needed relief so bad. I needed Big Daddy’s big black cock so bad. He was my only source of orgasm with this damn cage.

I looked at the clock, it was almost 5. I needed to smoke my joint and get ready for Big Daddy. I needed to make sure I was perfectly dolled up so I could seduce him as soon as he got here.

I turned on some music and lit up my 3rd joint of the day. Despite my pent up sexual frustrations from the entire day, I did feel good.

Alright time to get ready. I rinsed off my body quickly in the shower, but was careful not to get my hair or face wet. I wanted to keep my makeup intact.

After drying off, I walked over to my dresser to pick out the perfect lingerie for the night. After carefully looking through my options I landed on a classic black lingerie set that included ice stockings and a garter.

I started with the black satin thong, it felt so good sliding the material up over my shaved legs. I also loved how the thong felt resting in between my ass cheeks, but also how it creates a slight pressure to the base of the butt plug.

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