Cruise Vacation with an Older Woman Ch. 01

I was home for the summer from my state college and the summer break had been nothing but boring. This was my last summer before graduating next year and all I had done the whole time I was home was go to the gym, drive for a rideshare service, and try to get a leg up on the following semester's coursework. Most of my friends had chosen colleges in other states so I didn't really even have anyone to hang around with, but since I was staying in my old room at my folks' house, I was saving up some pretty decent money. One morning after I got home from the gym, my mom called my name when I walked in the front door.

She called "Stevey! Can you come in here a minute?"

My mom knows that I like to be called "Steven" but I didn't correct her. I walked into the kitchen and my mom was sitting at the kitchen table with one of her friends. Her friend was probably mid-to-late 50s, I'd guess about 30 years older than me. She had short brunette hair that was dyed blond on the tips that was cut into a pixie style, blue eyes, and tan white skin. She was wearing gray leggings, a pink tank top, and running shoes. I could see a generous amount of cleavage in the tank top and she was sitting on what looked like a nice ass in those leggings.

When I entered the kitchen my mom said "Stevey, do you remember my friend Naomi? We became friends during your junior year of high school."

I remembered thinking she was pretty hot, but I said "sure, it's good to see you again."

Naomi said "hello, I was just talking to your mom about a bit of pickle I'm in. A little over a year ago, my husband passed away-"

I said "oh, I'm sorry to hear that."

Naomi said "thank you. That's what my problem is about. Before my husband passed, we had planned to go on a cruise together. Then a couple months later, his stroke happened and with everything that was going on, I completely forgot about it. Now, it's too late to cancel the tickets or anything and I don't want to go by myself."

I said "oh, are you going to go with her mom?"

My mom shook her head and said "I can't. I have a large case-load right now and can't get away. I thought maybe you'd want to go. All you've done is work this summer and this would be a chance for you to have some fun before school starts again."

I looked at Naomi and she said "everything's already been paid for completely. It's a seniors cruise, but I bet you'd still be able to have fun at the beach and on the ship. It's a cruise to Jamaica. Think you'd want to do me a favor and come along? I don't want the tickets to go to waste. Please say yes."

I only had to think about it for about half a second before I said "yeah I'd love to get in some sun and fun before the semester starts. This summer's been a bit dull for me."

Naomi grinned and said "great! I'll call the travel agency and get the room switched from one bed to two beds. We leave the day after tomorrow. Thank you so much for coming on this trip with me."

After that, my mom walked Naomi to the door, then came back into the kitchen and said "thank you for going with her. I know she's been lonely since Tom died and I don't think it's a good idea for women to travel like that alone. Anything could happen."

I chuckled and said "that's a little old fashioned way of thinking, mom."

She shrugged and said "maybe so. But still. Being a seniors cruise isn't ideal for you, I'm sure, but it should still be fun. And you'll get to go to Jamaica!"

I agreed and told her that I was thrilled to go.

___

Two days and a plane ride to Houston later, Naomi and I were boarding a massive cruise ship. On the plane ride, we'd talked and had started getting to know each other better. Turns out she was 58, so she was 36 years older than me. She and her late husband had been married for 27 years when he had passed away due to a stroke. She had one daughter that was a year older than me, who now worked as a veterinarian in another state. I told her about going into my senior year at college in a few weeks and how all I'd done this summer was work. Naomi asked me about my love life and I told her that I had dated one girl this year for a few months, but it just didn't work out. In turn, I asked her about her love life. She said that she'd only been out on a couple of dates since her husband passed, but she said that there hadn't been any kind of spark with any of them.

When we got on the boat, it was apparent pretty quickly that with the exception of some of the staff, I was the youngest person on the ship. That was fine with me, I was sure there was a gym on the boat and that it would probably be pretty empty. The first thing we did was find our room. Or, cabin I guess they're called on a boat. I'm not very good with the terminology. When we walked in the room, there was a small bathroom off to the side of the door, a tv on the wall, a chair, a table with a telephone, and only one bed.

Naomi said "crap, they didn't switch our room. I'll call and get us moved."

She picked up the phone and spoke with someone on the other end. I could tell from her side of the conversation that it wasn't going how she'd like.

She hung up the phone and said with a sigh "the ship is completely full, we can't move to a room with a second bed."

I said "that's okay, I'll sleep in the chair."

She argued "oh no, you can't do that. The chair will probably kill your back and neck. If you don't mind sleeping next to an old lady, we can share the bed."

I asked "are you sure?"

She said "please, I insist. That thing will have you crippled by morning if you try to sleep in it."

I said okay and then we put our bags on the bed and left the room to explore the ship.

The boat was enormous. There was a casino, a movie theater, two full sized swimming pools and hot tubs, a whole shopping area, multiple gyms with rock climbing walls and saunas, and restaurants and bars everywhere. There were buffets and places to eat everywhere we went. I couldn't believe how big the ship was. All of the other guests were very nice and easily could have been my parents' or grandparents' age. After about an hour of us walking around the ship, there was an announcement that ship would be leaving the dock. We watched the land drift away as the boat left the dock and we waved to people we didn't know that were waving at everyone on the ship.

Naomi said "lets go find something to eat. I'm pretty hungry."

We ate at one of the buffets and then decided to go to the casino. I had some money with me from working all summer and wanted to see if I could win anything. Naomi and I played some slot machines for a couple of hours until it was about 10pm. I wound up winning around $200 and she broke even on the Blackjack table. The two of us were both tired after the flight and the day we had, and we decided to go to bed. When we arrived, there was couple going into a room next to ours.

The man said "hello! Or should I say 'ahoy'? I'm Rob and this is Janet. It's our first time on a cruise, I guess we'll be neighbors until we get back stateside."

We introduced ourselves and then went into our room. I went into the bathroom and changed clothes into pajamas and brushed my teeth. When I was done, Naomi did the same. She came out of the bathroom wearing a giant t-shirt that went down to her nearly her knees. I guessed that's what she wore to bed. We got into bed and we each turned off our bedside lamps. We laid there together and after a few minutes, I was about to fall asleep. Just as I was starting to nod off, I heard some laughing from Rob and Janet's room through the wall. I didn't think anything about it, but then after another minute or two, I heard the steady squeak of bedsprings and I knew they had to be having sex next door.

Naomi said quietly "sounds like they're enjoying their first cruise."

I laughed and said "sounds like it, get it grandpa!"

She laughed and then we just laid there and tried to go to sleep. I figured that an old guy couldn't possibly last more than just a few minutes and once they were done, I'd go to sleep. But I was wrong. The bed squeaking just kept on going and going. Then we started hearing moaning and groaning accompanying the steady creaking sound. I thought I could also hear a faint slapping sound. Listening to the two people having sex was starting to turn me on. It didn't matter that they were so old, I was starting to get hard in my pajama bottoms. I desperately hoped that Naomi wouldn't notice. Luckily, with the lamps turned off, it was pitch black in the room. After ten full minutes of listening to them fuck, I was as hard as I had ever been in my life. I was just thinking about trying to make up some lame excuse to go take a shower or something so I could jerk off in the bathroom when Naomi spoke up.

She said "god, listening to this is making me horny as hell. My pussy is drenched. I can't believe how long they've been at it."

I agreed saying "seriously, me too! I'm hard as iron right now."

She flipped her bedside lamp on and said "um, do you want to uh, have sex? It's cool if you don't want to of course. I can go relieve myself in the bathroom if you think I'm too old or whatever."

I said "god yes! I'm painfully hard and I've been sneaking looks at your tits and ass all day."

She let out a sigh of relief and said "oh thank god. I would not have gone into the bathroom to masturbate if you'd said no. I'd have gone and thrown myself overboard so I could drown instead of dying of embarrassment."

I laughed and said "there is literally nothing I'd rather do right now than have sex with you."

She smiled at me and said "I haven't had sex since my husband died. Except with myself. I'm probably rusty."

I leaned over and kissed her and said "I'm sure it's just like riding a bike."

She kissed me back and reached down to rub my cock through my pants. I pulled her big shirt up and ran my left hand up her stomach until I felt her breasts. I expected them to be a little saggy since she was so much older than the girls I'd been with, but they were very firm. I squeezed them and pinched her nipples. Her nipples hardened under my stimulation and she moaned into my mouth.

She broke the kiss and I asked "are your boobs-?"

Naomi interrupted me and asked "real? No they're fakies. They were an anniversary present for me about 12 years ago."

I grinned and said "for you? That seems more like a gift for your late husband."

She laughed and said "no I wanted them. I was starting to feel old and unsexy and these babies made me feel like I was 25 again. What do you think of them?"

I said "I'll have to make a closer inspection."

She giggled and pulled her big shirt up and over her head. She was wearing basic beige panties, but no bra. Her tits were perfect. Each one was round and soft to the touch. The nipples were hard and her areolae were bumpy and about the size of a nickel. They were light pink and contrasted nicely with her tan tits. As I was squeezing them, I noticed a very small, thin scar under each breast where the implants had been put in. They were barely noticeable. I'm not sure how big they were, but I'd say D at least, maybe even DD or bigger.

Naomi enjoyed my hands for about a minute before asking "well? How are they?"

I said "I'll need to do a taste test. For science."

She laughed again as I lowered my mouth to one nipple and flicked my tongue around it. I heard her sigh and she started running her fingers through my hair. I switched to the other nipple after a bit while I squeezed the first. She must've had a very expensive plastic surgeon because they were magnificent.

I lifted my head up and said "these tits were worth every penny."

Grinning wide, she said "good, I'm glad you like them."

Then she pushed me onto my back and lifted her legs up to take her panties off, I pulled my pajama pants down and kicked them off. My hard prick was standing straight up, and I saw a dark triangular patch of hair above her pussy that was neatly trimmed. She rolled over on top of me and I loved the way her boobs squished onto my chest while she kissed me again. She stopped kissing me after a second and adjusted herself to a sit on my stomach. She reached behind her back and I felt her start to stroke my cock and I sighed gently.

She cooed "oh, you have a nice dick. I'm going to ride it if that's okay with you."

I nodded vigorously and she moved again to where she could guide my cock into her soaking pussy. Very slowly and gently, she lowered herself down a little at a time until her pubic hair was pressed against mine. Her cunt was hot and tight on my shaft. I didn't expect an older woman to be that tight, but I was mistaken. She was as tight or tighter than any of the girls my own age I'd had sex with before. I'd never had sex with an older woman before that point.

She didn't move at first and said "fuck, you fill me up so good. I haven't had a real cock in so long, god I've missed this."

Naomi then slowly began to raise and lower her hips on my cock while she put her hands on my chest for balance. I reached up and started squeezing her tits again. I pinched her nipples and she smiled down at me. Once she became more accustomed to my dick inside her, she started riding me a little harder. Her ass was starting to slap against my thighs and small gasps were escaping from her on each downward thrust. I felt her pussy getting wetter and wetter as she rode me. Her smell filled the small room and it turned me on even more. I let go of her boobs and with my right thumb, I found her clit as she rode me.

When I brushed against it, her eyes got wider and she breathlessly said "yes! Right there. I'm going to cum!"

It was warm in our room and I saw sweat start to drip down her forehead and between her breasts. I felt her pace quicken until she slammed down one last time and she moaned as her orgasm started. She gasped and sighed over and over again and sweat dripped down her face, she had to blink it out of her eyes. Her neck flushed red and I felt her pussy get wetter and grip me more tightly. She pushed my hand away from her clit and ground her hips against mine as she came hard. I was sweating too and I wiped my forehead as her orgasm started to subside.

Looking down at my face, she smiled and said "that was so good. Did you cum?"

I shook my head and asked "is it okay if I cum inside? I tried to hold out just in case."

She laughed and said "oh honey, I had a hysterectomy 10 years ago. Shoot in me all you like. Ready?"

I nodded and she started riding me again, harder this time trying to make me cum. I only lasted about another minute or so before I felt my orgasm start with a groan. I started cumming as she rode me and I felt spurt after spurt of my spunk flood into her sopping pussy. Naomi continued to slap her hips against mine to coax every drop of my cum out me and into her. She slowed down to a stop once she saw me catch my breath. While I was still in her, she leaned down and kissed me. Then she lifted herself off of my cock and I saw my white spunk leak out of her pussy and run down one leg as she went into the bathroom. I heard the toilet flush after a second and she came back with a washrag. She wiped her and my cum off my dick and then laid down next to me.

She said "that was wonderful, I needed that so bad, thank you. God your mother would murder me if she knew what we just did."

I said "as far as I'm concerned, what happens on this ship, stays on this ship."

She kissed my cheek and said "sounds like Rob and Jan are done too."

I nodded and she turned the bedside lamp off again. We fell asleep a few minutes later.

___

The next morning, we woke up when the sun was coming up. I could see the ocean all the way to the horizon through our small window. I looked over and looked at Naomi's naked body in the morning sunlight. She really had a nice figure for being almost 60. Her hips, ass, and stomach had a little extra weight, but overall she kept herself in good shape. I knew she and mom went walking most mornings. Her nipples were soft and I wanted to touch her, but I didn't know if last night was a one-and-done kind of situation and I didn't want to make any assumptions.

She opened her eyes and said "mmm, good morning."

I smiled and said "good morning. About last night, was that just a one-time thing or...?"

She said "I really didn't mean for that to happen. I don't want you think I had some ulterior motive, cougar-fantasy in mind when I invited you on this trip. So if you want last night to be it, that'll be it, regardless of how horny I get. But if you maybe want to mess around again, I'd be open to it."

I said "I'm definitely open to it. I just didn't want to assume anything and make an ass of myself. Do you want to right now?"

She laughed and said "not right now, I want to get some breakfast, but later yes yes yes!"

I grinned and nodded. We got out of bed and I got dressed in my swim trunks, a light button-up shirt and flip-flops. She went into the bathroom to shower. I stepped outside to get some sea air. Our room opened up right onto a deck that had a great view of the ocean. When I went out, I noticed Rob leaning on the rail smoking a cigarette. I waved to him and he nodded to me. He held out his pack of cigarettes to offer me one, but I shook my head.

He said "probably a good thing. I've heard these things are bad for you."

I chuckled and said "yeah, I've heard that too."

He said "sorry if me and the mizzus kept you up last night. I didn't know the walls were so thin. I didn't know our bed would be so easily heard. But then I heard your bed creaking too and knew they were pretty thin."

A little embarrassed, I said "uh yeah, sorry."

Rob said with a sly look "nothing to be sorry about! When I first saw you two, I thought you were mother and son, but then I heard you all last night and I knew I'd misjudged."

I laughed and said "she's a friend of my mom. I was just tagging along because she had a ticket that was going to go to waste. Then we heard you two last night and you uh, kinda inspired us."

He laughed and said "that is one fine woman son. Good for you."

I said "she really is, thank you."

He put out his cigarette in the ashtray on the rail and then fished something out of his pocket. He held out his hand and there was a small blue pill on his palm.

He said "I need one of these nowadays, but here take this before you go to bed tonight."

I said "oh no, I don't really need those. I have no problem getting it up."

Rob shook his head and said "it ain't about getting it up, son, it's about keeping it up so you can go again and again and again!"

I shrugged and put the pill into my shirt pocket. Rob clapped me on the shoulder with a grin and then went back into his room. That explained how they had gone for so long last night. Naomi came out of our room wearing a black, one-piece bathing suit that was like a second skin on her, sandals, and a beach towel tied around her waist. I held out my arm and she hooked her arm in mine and we went off to find some breakfast. As we walked, I kept sneaking glances at her cleavage in her bathing suit. Her boobs drove me wild.

I said "you look great in that swimsuit."

Naomi looked pleased and said "thank you! I try to stay in shape so it's nice to hear that I can get a young guy's attention."

I replied "you look better than any of the girls on my campus."

She laughed and said "I'm sure you're exaggerating, but thank you again."

We got to the breakfast buffet and got our plates. A few of the other passengers were looking at us but I didn't care.

Naomi said though "they're all staring at us. They probably think I'm robbing the cradle of my boy toy."

I shook my head and said "Rob told me while you were in the shower that he assumed I was your son. These people probably think something along the same lines. He also apologized for keeping us awake."