Jeff Explores His Fantasies Pt. 06

The birthday party was a success for Mistress Jenny. Everything she had planned worked to perfection. Although it was great, it was not quite what I wanted. When I woke up the next day, Mistress Jenny had already gone home. I wanted to have a quiet birthday with just Mia and Raven. As I laid there, thinking, Mia woke up.

"Good morning baby." she said.

She adjusted herself on top of me as we kissed.

"I have another surprise for you." she mentioned.

"What would that be?" I asked.

"You need to be patient for that!" she replied with a smile.

She got up and went to the bathroom. She took a shower and put on with sweat pants and a Pink Floyd shirt and no underwear. I took a shower after her. After the shower, I decided to stay naked considering I wasn't going anywhere. We spent the day watching movies while laying under the covers. During the last movie, I noticed that she was stroking her cock. I turned to her and kissed her as I grabbed her dick. We kissed passionately. Then she sat up to take her shirt off. I kissed her neck, grabbing her breasts in my hands. I made my way down and kissed them back and forth; also licking her nipples. I felt her body squirm the minute I did. Her dick was now poking my stomach. I knew what to do next. I placed my face next to it as I grabbed it in my hand. I started by swirling my tongue around the tip.

"Mhmmm." was all she was able to say as she closed her eyes.

I ran my tongue down her shaft and back for two or three times. After the last one, I went down her dick, slowly taking it in my mouth inch by inch. I bobbed my head up and down while maintaining her dick in place with my left hand and caressing her breasts with my right one. Her dick was hard and wet now. I made my way back up to her lips. I kissed her softly as I sat on her dick, easily finding my ass. I was riding her nice and slow; our bodies becoming one. My ass was bouncing on her dick and she started slapping my ass with every bounce.

Then, she rolled me over and was now on top. She took my legs and lifted them up. She picked up the pace. However, her strokes were still slow and steady. This went on for what felt like an eternity. I just closed my eyes and enjoyed every stroke, slightly moaning. She kissed me again, not breaking stride. I grabbed her head in my hands, pulling her towards me. I held on to her for dear life. I could tell she was getting close. Her whole dick was now in me and her strokes were hard and fast, relentlessly fucking my ass. We kept kissing as I felt her cum filling my ass. She didn't take her dick out though and she remained on top of me. We kissed each other over and over, her dick still in me.

The dim light in the room and the background noise of the movie was the perfect setting for that moment. This was the first time Mia and I made love and the passion between us was electric.

She finally broke the kiss after a while and said we had to get ready for our dinner reservation at Frederico's. I was beyond myself. Frederico's is one of the most renowned restaurants and it could take months to get a reservation. As I laid there, I had more questions about her than I had answers. How did she get a reservation so soon? Who was she? What did she do for a living? But before I could ask her anything, she got off the bed to go and get ready. I was left in bed with my thoughts. Then an idea came to me.

I got off the bed as well to join her in the shower. As I got in, I stood behind her and I kissed her shoulders and caressed her back. Then I slid my hands on her stomach, towards her lovely breasts. My dick was hard and probing her ass. I pushed my dick in her ass and I heard a small pop as she let out a soft moan. I couldn't believe it. I was her first! I was gentle and slow with my strokes; I bit her neck then I grabbed her hair and pulling her head towards me. We kissed as I kept going, still ever so slow. She continued to moan and her body tensed up. I took her dick in my hands and I started stroking it. I picked up the pace a bit, going faster in her ass now. Her dick got bigger in my hand and I could feel her cumming again. Meanwhile, I flooded her ass with my cum. We stayed like this for a minute, catching our breaths. Then we proceeded to shower together.

"I love you." she exclaimed.

"I love you too." I replied shyly.

This was the most amazing moment in my life. I was in love with her. I never thought I would ever be in a relationship; let alone with the most beautiful transgender.

As we continued to shower, we couldn't stop kissing each other. Finally, we decided it was time to get out and get ready. I finished getting dressed first and went to the living room to wait for her. I had on a red shirt and navy blue pants on with a matching blazer. I knew she would choose an outfit to match mine. However, I was not expecting her to look that stunning.

She had on a dark red dress that reached slightly above her knees along with matching shoes. The dress was tight on her body and I could see her curves through it. She had her hair up in a ponytail and light makeup on. We hadn't left yet and I wanted to tear that dress off and make love to her again.

"We better leave if we want to be on time." she said.

I couldn't take my eyes off her. I was caught in a trance. Seeing I wasn't budging, she grabbed my hand and guided me to the car as she smiled. We made our way to the restaurant. Upon arriving, we were quickly shown to our table. It seemed as if we were being taken care of with extra care by the staff. I brushed it off and continued to enjoy dinner and Mia's company. After a while, the waiter came over and asked us how we were doing. I asked for the check but the waiter just smiled and said everything was on the house. I looked over at Mia, perplexed.

"The owner would like to meet you both." the waiter exclaimed, snapping me off my stupor.

We both stood up and followed the waiter towards the kitchen. Frederico came rushing out of his office to greet us.

"Hello Mia." he said with excitement in his voice.

"Hi Dad!" she replied as she hugged him.

"Dad?!" I asked.

"So this is the man you've been telling me about?" he asked as he looked over at me.

"Yes." she replied.

"Hello, sir. It is an honor to meet you." I said.

"Polite. You did good this time." he said as he motioned us to follow him into his office.

We chatted for a few more minutes about the upcoming cruise but it was a busy night and he had to get back to work.

"Take good care of my daughter! And have fun on your cruise!" he said before he disappeared in the kitchen.

Mia and I left. We were quiet on the way home. I was surprised to meet her dad without being told. I was not ready for that. I handled it better than I expected however.

"Are you okay?" she asked as we reached home.

"Yes baby. I am fine. I just didn't know your dad was Frederico. That's all."

"I had a bad experience in the past and I didn't want to make the same mistake again. I didn't want you to be with me because of money."

I took her hand in mine and kissed it softly.

"I'm not like that. I love you for who you are. Not for your money."

I got out of the car and went to her side to open her door. She got out and right there I kissed her. The moonlight shined on her face and she was irresistible. We couldn't wait as we tore our clothes off on our way to the front door, into the house and straight to my room. We laid down and we cuddled and kissed until we fell asleep.

The next day, we woke up early to get ready for our cruise. I was starting to pack my bag when she stopped me.

"No. You won't need all that. I want us to be naked the whole time in our room. The only times clothes are allowed is when we go out to get food."

"I am fine with that."

It was now 7:53 in the morning. We had to be there by 10. So I decided to make us breakfast while she put the bags in the car. We only took a couple of outfits and our toiletries. When she came back in, her breakfast was ready. As I was making my breakfast, Raven popped out of her room to see what was going on.

"I smell coffee." she said as she walked in the kitchen.

"Ha. Look who's finally up." Mia said.

"Good morning." she added before kissing her.

"Stop it. I'm getting jealous." I added with a slight smirk.

"You don't have to be jealous. I love you too." Raven replied.

She came over to me and kissed me too as I handed her a plate. Her lips were so soft. I wished she could've gone on the cruise with us.

One day!!! I thought to myself. The ladies chatted as Raven ate her breakfast and I hardly said anything as I ate mine. After we were done, I did the dishes and told Mia we had to leave. We said bye to Raven and left.

"Enjoy your trip." Raven said as she and Mia winked at each other.

They were not even trying to hide it either. I don't know what they were planning but they were up to something devious. Everything went according to plan when we got to port and we were on our way. As we walked to our rooms, I couldn't help but stare at Mia's body. Her yellow sundress was enticing. When we got to our door, I wasn't gonna wait. I took her arm and pushed her against the door. I went straight to my knees, lifted her dress and started sucking her dick.

"Naughty. I didn't know you had in you." she said.

She leaned her head back and let me go to work. With my eyes closed, I was enjoying her dick. Just as I was about to take it all in, she tapped my shoulder. When I opened my eyes, I realized she was looking down the hall. When I looked, there, standing at the end of the hall, was a couple that was staring at us. The woman was a redhead. Her short hair didn't go past her neck. She was about my height and she had a pair of shorts on and a white t-shirt with the word "cruise" written on it. The man was a tall black man, very muscular and with short black hair. He also had shorts on and the same t-shirt.

"You two started early." said the lady.

Mia and I starting blushing and we didn't know what to do.

"Keep going. Don't mind us." the man added.

So I went back to sucking her cock. The couple walked over to stand in between us; the woman to our left, the man to our right. The woman kissed Mia as she pushed my head down her dick. The man pulled down Mia's dress to expose her breasts and started caressing them.

"Maybe we should take this inside." Mia suggested as she broke the kiss.

"I'm Chloe and this is my husband John." said Chloe.

"I'm Mia and this is my boyfriend Jeff." Mia added.

With introductions in order, Mia opened the door and we walked in. As soon as we walked in, John took Mia's dress off completely and she laid down on the bed as I left our bags by the door. I quickly took my shirt and my shorts off and I picked up where I left off. Meanwhile, Chloe and John got undressed themselves. I felt soft hands caressing my back but I could also feel a hard dick probing my ass gently. Then I heard a whisper in my ear.

"That's right dear. I'm also a transgender." Chloe said.

With that, she inserted her dick in my ass and went all out. She was merciless as her cock went in and out of my ass. She was surprisingly strong for her size as she had her hands on my hips to keep me steady. It was hard to moan because I had Mia's dick in my mouth. I looked up at Mia to see if she was enjoying it. She was sucking John's cock which was nice and thick as he played with her breasts. This was too exciting for Mia and she came in my mouth. This sight was too much for me as well and I came too.

"Baby, looks like we are gonna enjoy this cruise more than we thought." said John.

"Yes. This is gonna be so fun." replied Chloe.

As she said that, she took her cock out and turned me over and told me to get ready. Without even giving me a chance, she shot her load all over my face and mouth. Simultaneously, Mia took all of John's cum. Then she pulled me up towards her and we kissed as we shared John's and Chloe's cum with each other. Meanwhile, John decided he wanted to take a turn at my ass. I honestly didn't think I could handle it.

"Get your ass up." he ordered

I quickly did as he requested. I wouldn't want to piss him off, seeing how strong he was. I grabbed the sheets and placed them in my mouth to muffle my screams. Across from me on the other side of the bed, Mia was fucking Chloe like I've never seen before. She was going just as hard as Chloe was. Chloe took my face in her hand and kissed me. John was a bull. I couldn't take it anymore and tried to get away.

"Where are you going you little bitch? Stay right here." he barked at me.

He grabbed me by my hips and tightened his grip. I could feel my ass expanding. That's how huge he was. My body just went numb and I had no control anymore. He kept going stroke after stroke. After what felt like an eternity, he finally took his cock out. I didn't notice it at first but my ass was filled with his cum. I tried to get up but that was impossible. My legs were shaking as soon as I stood and I had no choice but to lay back down on the bed. Mia didn't cum in Chloe; she was saving it for me. Chloe got off the bed and I started sucking Mia again. This time, it didn't take long and she came almost immediately. Unable to speak, we just laid on the bed as Chloe and John got dressed and left. We fell asleep right away. When we woke up, it was already dinner time and if we didn't hurry, we were gonna miss it. Having missed lunch, we couldn't afford to do that. We needed food. We showered, got dressed quickly and walked out of our room. In the hallway, we met up with Chloe and John.

"We two still look exhausted." said Chloe with a laugh.

"We are." I replied.

"Care to join us for dinner?" John asked.

We agreed and we all headed to the dining room. Dinner seemed short. We made small talk and before we knew it, the night was upon us. I invited Mia to dance and John asked Chloe. As the song finished, we switched partners and I was now dancing with Chloe. It was a slow song and I could feel the heat of her body on mine, her head on my shoulder. Surprisingly enough, I could sense a passion between us. When the song ended, she lifted her head and we kissed for a brief moment. That moment was broken when I felt John's hand on my shoulder.

"Shall we take this to the room?" he asked.

We all nodded and we went to their room, grabbing a bottle of the finest bourbon at the bar. When we got to the room, the ladies didn't wait around and stripped out of their clothes. John had put some soft music on. The ladies started dancing as he poured me a drink then poured himself one. We sat on the bed, watching them. They were moving as if they were one under the fluorescent lights. I looked over at John and I could tell he was getting excited. He was talking about the upcoming NFL draft. I wasn't paying much attention anymore. I got off the bed and kneeled in front of him. I pulled his pants down along with his underwear. His dick was hard as a rock. I took it in my mouth but barely made it halfway. That's how long and thick he was. At this point, he had stopped talking and his hand was on my head as I bobbed up and down on his cock while using my tongue. The first song ended and Mia and Chloe came over to us and sat on the bed next to John.

"Leave some for the rest of us." Chloe mentioned.

She kneeled down next to me and started sucking him too. His dick was really wet now. Mia pushed us off and she sat on his dick. Chloe laughed.

"Someone is eager."

"Y...e...s! He's...so...big." Mia managed to say.

"I know." Chloe said with a big smile on her face.

"I agree." I added.

"I want your ass too." she told me.

With that, she sat on the bed and I started sucking her long enough for her to get hard. Once she got hard, I did the same as Mia and sat on her dick. We were both grinding and going up and down on their dicks. They just laid back as we did all the work. After ten minutes, they still hadn't cum and we were getting a bit tired. They felt it too. We switched position and partners. John easily picked me up and wrapped my legs around his waist. What followed was unbelievable. He slid his whole dick inside of me. I never thought I was able to scream as loud as I did. It felt like he was trying to break me in half with every stroke, each one as hard as the last.

Mia was on her back with her legs being held up by Chloe as she was getting fucked just as hard. She was moaning constantly with every stroke. Chloe spread her legs and kissed her passionately as Chloe slowed down her pace. She was stroking Mia's dick and all of a sudden Mia's cum covered her stomach. John saw that and he pushed me onto the bed. Then Chloe sat on Mia's face and was fucking her throat.

"Lick all her cum now, bitch." he ordered.

I didn't need a second invitation. I got on all fours and licked her cum as I made my way to her dick to suck it. John saw that as an opportunity to keep fucking me. He placed himself behind me and it was easier to get in this time. He kept the same pace as he shoved my head down Mia's cock while she sucked Chloe's.

"I want all your cum in my mouth." I said as I caressed Chloe's back.

"Of course you do." she said.

She came over to me and started fucking my face too. She held the back of my head and I could feel her cock deep in my throat. I felt both of their cocks tense up at once. Suddenly, I felt the warmth in my ass and it was so much that some of the cum had started leaking out. Chloe's load went down my throat and I swallowed it all. John was still cumming. Chloe sucked him off to get the rest. With a mouthful of cum, she kissed me to share his cum with me. In turn, Mia joined us and was kissing us both as we shared the cum between the three of us. Chloe walked over to kiss John too. She pulled him down to the bed and continued their kissing. She caressed my leg and I caressed hers. We all bundled together and cuddled until we fell asleep.

The next morning, Chloe woke us up while John was in the shower.

"Rise and shine lovebirds." she said as she kissed me then Mia.

"Good morning." Mia replied, rubbing her eyes and smiling.

I stretched myself out and replied to her.

"We're going swimming today once we reach the shore. Would you like to come too?" Chloe asked.

I looked over at Mia with a suspicious look and she answered instead of me.

"Well we would but....we don't have any more clothes than what we need when we go back home."

"Oh that's okay. You can buy some when we get there." said John as he walked into the room.

"That's a great idea." added Chloe, jumping up and down with excitement.

As we were finishing getting ready, we heard the announcement over the speakers that we had reached the Bahamas and we had three hours to explore the city. The four of us hurried to leave the boat. Chloe had a white bikini top on, no shirt and a pair of shorts. John had orange swim trunks and a red shirt on. We had breakfast in a small restaurant then did a bit of window shopping before heading to the beach. On the way there, Mia bought herself a blue bikini with flowers on it and I bought a matching pair of swim trunks. We paid for them and changed quickly before heading out. Once we left the store, we got to the beach and ran to the water followed by Chloe and John right behind us.

Chloe swam to me; John to Mia. We held on to each other as the waves hit us. We were joking and laughing uncontrollably. I pulled Chloe closer to me and kissed her as she was laughing. I knew I took her breath away then. I pulled away from the kiss and looked her in the eyes. I winked as I dove under. I kissed her underwear first before pulling them off with my mouth. She was enjoying it because she was rock hard already. I swam back up to get some air. She immediately kissed me as I stroke her cock.