A Jamaican Vacation Ch. 04

Rebecca studied me up and down.

"What happened to you?" She asked.

"I...uh...I..."

Ty cut me off, "you look like you are in shock Rebecca. Let's fix you a drink and I'll explain everything to you."

"Make it a double," she said as Ty started to make her a screwdriver.

He handed her the drink, grabbed a joint, and ushered us outside.

Rebecca sat down in one chair, Ty in the other. There wasn't anywhere for me to sit, so I stayed standing, leaning against the railing.

"Come sit here and smoke your joint Alexis," Ty said as he slapped his legs.

I took the hint and reluctant sat on his lap.

"So what, you are some sort of faggot now?" Rebecca asked.

"I...um...I guess" I sheepishly responded. Finishing my joint. The weed had me so self conscious.

"I have an idea," Ty chimed in, "since you are having a hard time explaining this all to her, and don't you show her."

"Please Big Daddy, don't make me do that in front of her, this is humiliating."

"This is nothing! I fucked you in front of like 50 people last night. Sucking my black cock in front of one person is nothing."

Rebecca nearly spit out her drink.

"You did what?" Rebecca screamed.

I looked down, too ashamed to answer her. In my silence Big Daddy explained how he fucked me on the beach with Jess last night at a party.

"Alright time to show her," Ty said after telling her about last night.

"No, please," I pleaded, but Ty cut me off.

"I'm not asking," Ty said matter of factly, pushing me off of him. "We can do this the hard way or the easy way."

I didn't want to find out what the hard way was. This was clearly happening one way or another. I turned towards him, put both hands on his knees to spread them apart to make room for myself as he sat on the chair, and dropped down to my knees.

I stayed like that for a minute. I could feel Rebecca's eyes on me. I could only imagine what was going on in her mind.

"Alex, are you really about to suck this man off right now?" She asked.

"I...I...," I stuttered, not able to formulate a full sentence.

Big Daddy jumped in, "Alexis is going to have to if she ever wants my big black cock ever again."

Big Daddy was so confident. He knew he had be wrapped around his finger. Would have I preferred to not give head to a black man in front of my ex fiancé? Yes. But it was better than the alternative of never having his big black cock in me again.

I gave in.

I stared at his crotch and reached for the waist band of his shorts. I tugged, but couldn't get his shorts down around his ass, and I knew his black cock was too big to simply pull out of his shorts.

"Big Daddy?" I pathetically asked, looking up at him.

Rebecca nearly spit out her drink upon hearing me refer to him like that.

"Yea Alexis?" He asked, playing hard to get. He knew what I was going to say, he just wanted me to say it in from of my ex.

"Can you please lift up your ass so I can pull your shorts down? I can't get to your big black cock."

He took another hit of weed, and leaned down to give me a kiss, blowing it into my mouth. I didn't need the encouragement, but it still felt good as the high washed over me.

He lifted up his ass, and I started lowering his shorts.

All of my attention went to his big black cock. I have pretty much been on his big black cock in one way or another 24:7 the last couple of days, but I still got so excited every time I saw it.

The base of his shaft was just being unveiled as I slowly lowered his shorts. I saw the thick, heavily veined shaft and instinctive bit my lower lip. I was completely transfixed on his big black cock.

I pulled further, another inch, then another, and another.

"OH MY GOD, how big is that thing?" I heard Rebecca shout.

I couldn't respond, I just stared at it as I lowered his shorts further. It felt like I was pulling forever. I didn't realize it in the moment, but my mouth was salivating from excitement. So much so, that I inadvertently drooled a bit on his shaft while looking down.

"You are such a slut Alexis, you literally just drooled on my cock!" Big Daddy laughed out loud.

I didn't even care, I took my hand to wipe my mouth and went back to the task at hand.

All that was left was the massive head of his black cock. I get the elastic straining to hold his big black cock down. With one final tug, I freed the entirety of this big black cock, which sprang to attention, slapping the underside of my chin along the way.

I heard both of the them laugh as I fumbled to catch his big black cock in my hands as it bounced around in front of my face.

I finally caught it with both hands, and began to stroke it up and down with both hands.

"That is the biggest cock I have ever seen!" exclaimed Rebecca, "I didn't know they made them that big. And you take that...in your ass?"

I moaned a affirming "mmmmhmmm" while I took him into my mouth.

Since I wasn't much for conversation in my current state, Big Daddy started talking with her.

"She loves my big black cock, she told me last night she thinks she might be addicted to it. Have you ever had a big black cock?"

"No," Rebecca replied, "Alex...or I guess Alexis, was the smallest I'd ever been with, but he was so good with his tongue that kind of made peace with it."

Big Daddy took another hit of weed, "you are damn right about that, she does an incredible tongue twirl around the head of my cock that drives me crazy. I mean her little penis is incredibly small, there's no way that ever gave you an orgasm, right?"

"No way, not even close. Basically the fun stopped for me when he stopped eating me out and would try to fuck me. I'd just lay there and act like I was into it so that he would cum as quickly as possible."

Daddy roared, "you are damn right about that! This sweet sissy cums so fast! I've never seen anything like it, even for a sissy!"

I couldn't believe the conversation happening around me.

Daddy kept talking, "I knew he was a sissy right when I met him, but Alexis is really next level. It's a deep urge for her. She gets so turned on just from pleasuring me. I guarantee you her little penis is as hard as it's ever been right now."

"Not a chance! Nobody actually likes giving head, it's just a means to an end," Rebecca said.

"Well, let's see," Big Daddy said as he tapped me on my head. "Sorry to take you away from your friend down there, but stand up and lift up your sundress. Show your ex what my black cock does to you."

I pulled my mouth off of his big black cock and wiped my mouth clean. There was no point in fighting it. I knew my little penis was hard as a rock. Not just that, but I could feel that the satin material of my thong was wet, I was leaking.

I couldn't look at Rebecca. I stood up, facing Big Daddy, and lifted up the front of my sun dress. As I expected, my little penis was straining against the pink satin thong, and there was a very noticeable wet spot.

Big Daddy grabbed me by the waist and spun me 90 degrees so I was facing her.

"See?" He said, "she lives for this."

Rebecca looked at my face, then my crotch, then back up to my face. All laughing, joking, and humiliating was gone from her.

"So this really is just who you are, isn't it?" She asked me. There was just a sense of familiar calm in her voice.

"Yes," I said, "this really is just who I am. I had no idea before. I guess deep down I always knew I wasn't a man. I couldn't pleasure you. I just didn't know it until I came down here and learned what a real man is."

We just stared at each other until Big Daddy broke the silence, "Do you think she needs a side by side comparison?"

He stood up, and lifted my dress over my head. I was not just standing in front of me ex in a pink bra and panty set, wedge heels, and my jewelry. For the first time, she could see my budding breasts from the smoothies and weed too.

He then pulled my panties down slightly so my hard little penis stood at attention. I turned so I was facing him again. He then grabbed my little white penis and held it next to his big black cock. The contrast was undeniable.

Rebecca surveyed the scene, "I mean I knew you were small sweetie, but I had no clue. I'm just happy you found your place. What is it that you like so much?"

Big Daddy let go of my little white penis, and stuffed my back into my thong, sitting back down on his chair. I sat down on his lap so that my back was against his chest and his cock stood up between my legs. I reached down and stroked his big black cock, staring at the difference between my hard little penis and his beauty.

After collecting my thoughts, I started to talk, "to be honest, I don't really know where to start. If I had to pinpoint one specific feature above all else, it's the enormous head. The size, the shape and the ridges, it really hits places I never knew existed. And then there is just the impressive length and width of the entire shaft. He's so big that he can take me in positions that weren't even possible for us. And his stamina, oh my god his stamina. He can fuck me into orgasm after orgasm. Then there is just his confidence and honestly my confidence too. He can fuck me so well. I was always a fumbling idiot with you. I think it's because it didn't come naturally to me. I finally feel like I am good at sex."

I turned my head to talk to Big Daddy, "at least I hope you think I'm good at sex."

He didn't say anything, just brushed my hair back and gave me a kiss on the neck. That was all the affirmation I needed!

I turned my attention back to Rebecca, "honestly, I just love everything everything about my new role. At this very moment, while I stroke his big black cock, my little white penis is harder than it ever was for a woman, and I feel a deep aching inside my ass and desire to be filled by him."

I tried not to let her know, but Big Daddy had slid the back of my thong to the side and had slipped a finger into my ass.

"How can you even take that monster?" Rebecca asked.

"Well, I just..."

"Like this!" Big Daddy shouted.

In one motion, Big Daddy grabbed my hips, lifted my up about 16 inches to clear the length of his big black cock, and slammed me back down.

I yelled and moaned as he filled me up. I turned my head to look at Rebecca, she had her hand covering her mouth and a look of utter shock in her eyes.

My feet werent even touching the ground, I grabbed the arm rests of the chair to help steady myself.

He lifted me up and slammed me back down again, all the way to the base this time. I leaned my head back and grabbed my bra encased tits.

"Oh my god!!" I squealed as the familiar feeling of a deep sissygasm hit me like a ton of bricks. I shuddered over and over as I shot several ropes of cum out of my little white penis.

Eventually, I caught my breath. I just moaned in pleasure as I leaned back into Big Daddys chest, rotating my hips in a circular motion to rotate on his big black cock.

Back to my point earlier about gaining confidence in myself as a partner in sex, I was feeling myself. Two days ago I was just a tight hole for Big Daddy as he broke me in. Now, I'm an active participant, working harder to bring him (and myself) more pleasure.

Even after my orgasm subsided, I continued to grind my ass into Big Daddy, proud of my ability to take his entire black cock.

"You must really love dick," Rebecca said, "you never came that much with me."

I looked over at her, "it's not just any dick, it's his amazing black cock that has changed my world. I was at a party last night where I had to sit on a small white dildo, it did nothing for me."

"Well I guess I need to try a big black cock, Ty think you could fuck me after you a turn with your little sissy?"

He laughed and reached around to grab my little white penis, which was softening after my huge orgasm, "believe it or not, but I'm not really into traditional women. What gets me off is turning these white bois into black cock loving sissies. I mean look at Alexis, he lives for pleasing me. I have complete control over him, women expect to much. All he expects from me is a healthy dosage is big black cock. However, I have more than a few friends who would love to take a fine white lady like you out for a spin."

"I'll let you know, but I may take you up on that offer," she responded.

I was caught up in pleasuring Big Daddy, but I saw Rebecca's hand slip under her dress, she was rubbing herself while watching me get fucked by a big black cock. She was turned on by the scene in front of her. I'm not sure why I was proud, but in some crazy way, I was happy that I was finally turning her on.

Big Daddy kept fucking me as Rebecca rubbed herself to an orgasm. About 10 minutes later, Big Daddy slammed me one last time all the way down to the base of his cock and held me there as he sent rope after rope of hot cum deep inside my ass.

"Thanks Daddy," I instinctively moaned.

I can't believe I said that. "Thanks Daddy," What was wrong with me? I clearly had it bad. Thanking a man for fucking me with his big black cock in front of my ex fiancé. I was pathetic.

"So while we're here, Rebecca would you mind going to the dresser and getting the plastic chastity device from the top drawer?"

"Big Daddy, you don't need to lock me up, you know I'm good," I begged.

"What does it look like?" Rebecca asked.

"It's small and purple, you can't miss it." He responded, both of them ignoring my pleads.

Rebecca walked into the bedroom and came back with it a few minutes later.

"Sorry for the delay," she said, "I was just admiring your collection of lingerie, you've been busy. Is this what you wanted?" Holding the device out to Big Daddy.

"That's the one! Why don't you go ahead and put it on his little white penis," he told her.

Rebecca laughed and squatted down so that she was eye level with my little white penis. She shook her head and grabbed the base with her thumb and forefinger, sliding it on with her other hand. It felt snug, but I didn't even fill it out completely.

"Do you want me to lock it?" She asked.

"Yes, thats the whole point," Big Daddy responded.

She clasped it shut and I shivered.

"Now, I want you to take this," he said, handing her the key that was around his neck.

"What do you want me to do with this?" She asked.

"Well, tomorrow night we are getting married and I think it would be fitting if you would walk Alexis down the aisle and give her away. As part of the ceremony, I want you to turn the key over to me."

Oh my god, my head was spinning. Not only was it bad enough knowing that I was going to be locked up for 36 hours at minimum, but my key holder until then was going to be my ex fiancé, and she was going to play the role of a father in the ceremony.

"I would be honored to give Alexis away," she said, giving me a wink before placing the necklace with my freedom around her neck.

"Alright well I have things to do this morning," Big Daddy said, sliding me off of his softening cock, "why don't you two have some fun today, maybe Jess would want to hang out too Alexis. You do need to find a maid of honor too."

I blushed. Thinking about having to ask Jess to be my maid of honor. Maybe she would throw me an impromptu bachelorette party.

"Good idea, I'll send her a text," I said as I stood up. I felt Big Daddys cum start to drip out of me and put my hand under to catch it.

"Why don't you go get your plug sweetie," he said, giving me a kiss on the cheek before pulling up his shorts and leaving.

I scurried over to the dresser and found my plug. I was so wet from the fucking earlier that I didn't need any lube as I slid it in. Once in, I relaxed.

"All better now Alexis?" Rebecca laughed, watching this whole scene take place.

"Yes I just, ummm..." I was flustered.

"Just say it Alexis. You just got fucked by the biggest cock I have ever seen, and you loved every second of it. No more secrets."

"Ok then, well, I just prefer to have something in my ass. It feels empty without anything in there," I responded.

"Well then, good thing you have that plug handy!" She laughed, giving me a playful slap on the ass.

That took the edge off. Without Big Daddy there as a distraction, I wasn't sure how it was going to be. But she was being super fun and awesome about everything.

"I could really go for a massage, how about you?" Rebecca asked me.

"Sure, a massage sounds amazing," I responded, "but first, I need to drink one of these smoothies."

"I'm hungry too, can I have one?" She asked.

"You might not want to, I don't really know what's in them. He has me on a strict diet regimen and I know these are loaded with hormones to promote boob growth."

"I thought I saw you sprouting something under that bra!"

"You noticed? That's amazing. I can feel the difference, but I didn't know what was visible to the outside."

"Well let's see," she said, walking over to me and unclasping my bra.

The breeze felt cool on my nipples, which immediately hardened.

"Oh yea, you are growing for sure. Some of my girl friends don't have boobs much bigger than this. I mean they are small, but not all women have huge boobs."

I smiled. I was excited to be able to start showing them off, no matter how small they were.

"Well don't let me distract you," Rebecca said, "get dressed so we can head down to the spa!"

I rummaged through my drawers and landed on a purple thong and bra set, and put on a pair of jean shorts and tank top.

The shorts barely covered my ass, they were so short. And the rode low too, sitting low on my hips. The tank top didn't quite reach the top of my shorts, exposing just a flirty amount of stomach.

Once dressed, we walked down to the spa to enjoy our morning, like two longtime girl friends.

Later that afternoon, we found our way to the pool bar, where Jess met us. She must have known I was going to ask her to be my maid of honor, because she showed up with the skimpiest white bikini I had ever seen for me to wear. It even said bridesmaid across the back, and had a spade on the front.

"What's the spade for?" I asked.

Jess giggled, taking another sip from her drink, "it means you live big black cock!"

"Oh my god Jess, you're ridiculous!" I laughed out loud.

"Well you do don't you?" She responded.

"I'm not even going to justify that question with a response, you know the answer."

I gave her a hug to thank for the bikini before I went to go change. Rebecca laughed when our cages made an audible clank when our bodies touches.

I came strutting back to them, I looked hot! They both greeted me with whistles and cat calls.

"I just can't believe how feminine you both look," Rebecca commented, "there isn't an ounce of noticeable masculinity. I mean I don't even see your little penises in your bikinis, and your bikinis are super tiny!"

Jess laughed and gave me a cheers, "there was a time that I would have been hurt by that comment, but that was back when I still thought I was a man. Now that I know I'm a sissy, you just gave me the ultimate compliment."

She was so true. I was now proud of how small my penis was. I still love my penis, don't get me wrong, but I love how small it is. I love that it fits neatly in panties, I love that it is thin and feminine, I honestly love that it is pretty. Also, I love seeing my thin, white, hairless penis in contrast to Big Daddys thick, strong, veiny, heavy black cock. It was a constant reminder of my place in the world and our relationship. That contrast is incredibly erotic to me.

My little white penis twitched in my cage as I thought about it all.

"Excuse me, Alexis?" someone from the hotel asked, walking up to us.

"Yes?"

"It turns out, your room was already booked for the remainder of the week by another couple. But not to worry, we have been informed that you are getting married to Ty tomorrow, so we took the liberty of upgrading you to our poolside villa for the rest of the week. Your belongings have already been moved down there."