Cleavage Cruising

Chapter 1

Long story short, I managed to be awarded a free cruise to the Bahamas. The award is certainly cool, but there was a big buzzkill attached to the cruise: I would be going on it by myself without anyone else that I knew. I wasn't sure what I was going to be doing on a cruise by myself, but I supposed it would be cool. After all, I was a single 35-year-old. I was sure I could find something to do.

As I stood in line to check on to the boat, I happened to notice a woman who was a couple of people in front of me. I reckoned by the look of her facial features, she was possibly ten or so years older than me. And going by her facial features alone, she was nothing special. I wouldn't say she was all that pretty. As for her body, she was kind of on the short side. I'd say she was a good foot or so shorter than me, which put her at 5'2" probably. She also wasn't very skinny. And that was putting things nicely. The woman was certainly on the plump side, and that may have been putting things generously as well. But what the woman lacked in classical beauty she more than made up for in chest size. I'm not kidding! Her breasts were enormous. And they managed to look plump, even though they hung down to probably her belly button.

All I could do was stare at them, and frequently gasp at the sight. Her tits were magnificently humongous. Full disclosure: I had always been a fan of ladies with huge boobs. I mean it. The bigger the better. Maybe some dudes who are into big tits have a threshold pertaining to how big they like their boobs. If I had such a threshold, I had yet to find a girl that crossed. So, I was in awe of this woman. After gawking at her for a long time in the line, I started to take tabs on who she was talking to and hanging out with in the line. I guess I hadn't noticed that she wasn't saying a word to anyone else while she was standing there, because I guess I was too busy staring at her magnificent rack. I mean good God! If I had to guess at her bra size, I would have guessed H-cup or larger. But back to my reconnaissance work. I needed to figure out if she was here with a husband or boyfriend. Either of those possibilities and she would be off limits. And if I were lucky enough to catch her here single, I wondered if she was cruising with her children maybe. That possibility wouldn't be great for me either. Kids can be a cock block. Anyway, since I was sure she wasn't here on a cruise alone - who would be doing that here besides me - I was hoping she was here to party on a cruise with some friends of hers. If that were the case, then that was my best bet of getting close to her.

Chapter 2

On the first night of the cruise, I sat down at a blackjack table at the casino. Then, to my surprise, the lady I was drooling over sits down next to me.

"Is this seat taken?" she asked. "This is a crowded place, isn't it?"

"Big time," I responded, "and no this seat is not taken. You're more than welcome to it."

She then admitted, "I'm not the strongest blackjack player. Any advice you might have for me would be greatly appreciated."

"No problem," I said. Then I got to thinking. Why would this lady sit down to play blackjack without knowing how to play? Could it be that she was kind of into me as well? I certainly hoped so! I decided I would do my best to find out.

"So how much cash would you like to play with?" I asked, "Or better yet, how much money are you comfortable losing? Not that I think you'll lose. But it's better to do the math beforehand."

"Oh wow. I would have never thought about it like that," she looked at me for a good moment, "I bet you happen to be a lot more intelligent than me."

I thought that was a funny comment. "Just hold off on that probably," I replied, "and first let's see how well we do here at this blackjack table.

"Then you and I are a team tonight?" she asked.

"Sure," I responded, "let's hope you picked the right teammate."

With that she said, "I'm here on a semi-work cruise, and I don't know another person on this ship. I'm pretty happy to have a teammate of any kind actually."

"That's crazy. I'm traveling alone on this cruise as well. I was awarded a single cruise ticket for being a good money maker in my department. I thought it was the strangest gift ever! But since I'm getting paid to be here on the boat, I wasn't turning the opportunity down, I promise," I informed her.

With that the two of us played blackjack for several hours while constantly chatting. I found out her name was Teresa, she lived in South Dakota, she was 48 years old, AND she was single. Luckily, the cards were being kind to me, as I won both of us several hundred dollars on the night. She was drinking a little heavier than me. I wouldn't say she was shit faced drunk, but she was sitting at the table trying to get her buzz on. And as she became more and more buzzed, the more she wanted to touch me. After a while longer, every hand that I helped her win was rewarded with a deep hug directly into her massive chest. After a little longer, she looked at her watch and turned to me.

"It's almost 2 am, James. I'm ready to go to my cabin," She told me.

I must have been unable to hide my disappointment as I responded with, "this blackjack party sure died. I guess I'm heading to my room as well. Thanks for sitting down with me tonight though! I had a really good time."

After I said that, she got super close to me. Then she whispered, "I want you to come with me, silly. Don't you want to come?

Quickly, I responded with, "YES."

We got up from the blackjack table and headed to Teresa's cabin. I had a rock-hard boner for the entire walk.

Chapter 3

We got to her cabin, and she immediately put her massive tits on my chest and said, "I noticed you couldn't keep your eyes off my chest for very long tonight. Do you like them?"

"Yes!" I responded, "they are amazing."

"Do you like girls with really big tits?" she asked.

"I always have," I replied, "but yours are quite enormous. You have the biggest titties I've ever seen."

With that she chuckled and said, "I owe you one for teaching me how to play blackjack. What would you like to do with my 'titties?"

"Can I have sex with them?" I asked.

"You wanna pound your penis in between them?" she replied.

"Yes definitely," I told her, "My God, they make me so hot!"

With that, she took off her top exposing her massive bra. Even though the bra was huge, they didn't hold her tits in very well. They were spilling out of the top of her bra. I decided I would be the one that unhooked it. So, I used my hands to reach around her chest and felt the area that would unclasp the bra. After I took it off, I had a look at its size. Her bra was an incredible 44 HH.

"Oh my God , Teresa. Your titties are humongous!" I exclaimed.

"I know," she replied, "and they're all yours tonight, sweetie. Do you still wanna make love to them."

"Oh my God yes," I panted, "I'm gonna fuck your big titties hard!"

Chapter 4

I sat Teresa down on the couch. We started making out while I squeezed on her tits. My God they felt good. Her titties were super heavy. The harder I played with them, the louder her moaning was becoming.

"Is this ok?" I asked. "Let me know if I'm squeezing too hard. I'm sure I could get carried away, babe."

With that, she kind of stopped me, and said, "What makes me happy is making you happy, sweetie. What I really wanna do is whatever you tell me to do, okay. The more you take control, the hornier I get. I want you to literally tell me exactly what you want me to do."

This was incredible news! I thought for a second and said, "pull my dick out, Teresa. I want you to start playing with it."

She immediately obeyed my command and unzipped my pants. In no time, she had my dick out, and was stroking it. This went on for about 10 minutes. We were making out while I played with her giant titties and she played with my ever-growing boner.

After about 10 minutes, I decided to test the waters a little bit regarding her submissiveness. "Get on the floor and on your knees right in front of me," I commanded, "and wrap your big titties around my dick."

She did exactly as she was told, both promptly and with a big smile on her face. She squeezed her mountainous cleavage around me until you could no longer see my dick. I was completely lost in between her chest. She started to move them up and down, slowly at first. It didn't take long before her pace quickened. Her boobs were bouncing on my dick.

"Oh yes!" she exclaimed. "You've got a super big boner, James!"

"Your big fat titties are making it hard as a rock, baby! "I yelled out. "That's it. Squeeze your boobies tighter. I love your big fat titties, Teresa."

"My boobies love you too." She replied.

All this huge titty sex was starting to make me want to sperm. I stopped her and said, "you're titties are gonna make me do it soon. I can't help it. I want you to get on the floor and lay on your back."

Teresa was one hundred percent compliant. She laid on her back, and simply looked at me. She was awaiting further instruction. This was amazing! I got on top of her and positioned myself so that my dick was hovering right above her boobs.

"I want you to wrap my dick super tight in between your big titties, and just hold them in place," I instructed her, "I'm about to fuck your big boobies hard."

"I want you to ejaculate in my titties, Jamey!" she shouted. "Fuck them boobies hard okay."

With that, I started ramming my pecker in her titty flesh harder and harder.

"Squeeze them tighter, baby! I shouted. Your big titties are gonna make me sperm so good!"

"I can feel your fluid, sweetie. Your cock is pulsating. I can feel it in my titties. Please shoot the load in my boobies."

"I'm cumming, Teresa. I love your big titties. Ahhhhhh! Your big boobies make me cum! I love fucking your tits! "I ejaculated in her titties and filled her massive cleavage with cum.