The clouds had been stolen by the sun this morning, and its warm rays made it through the skylight to illuminate my cabin, waking me softly from a restful slumber. My second night aboard the 46.1 Beneteau sloop, my new retirement condo.
It had taken me a couple months to divest my possessions and close the apartment. At only 51 years old, the company I worked for decided to close the operation at this location, but hey, I was offered a generous severance, and pension with benefits. The severance amount was enough to purchase a used boat, and this model must have been a well-cared for - dock queen, as there was no discernible wear and tear, and only 20 hours on the engine.
My plan was to explore the southern seas and anchor in bays where I could immerse myself in the local culture, savor the delicious food, and enjoy a cold beer. I had the boat stocked yesterday, and tomorrow morning I'll set sail for my first leg of a shakedown journey to the Bahamas.
Today, I had some time to make sure everything was in order before setting off in the morning. I'll motor until the wind picks up, then set sail.
On my way to the marina's café, I couldn't help but notice Lola greeting me there with her usual bright smile.
"Whatcha up to today, handsome?" she asked with a smile.
"I'm taking a test cruise before I head out tomorrow for a few months."
"OMG, take me with you? I've always dreamed of just dropping everything and doing something crazy like that!" She giggled.
"Wish you were serious Lola, I love your personality, and you are easy on the eyes to boot. I think you'd look great sunning naked on the foredeck as we sail." I joked.
"I could be naked all the time for you stud." she said giving me a smoldering look.
"You sound so serious, girl. "Guys can be a bit dense sometimes, but I've always seen our teasing as friendly customer service. I bet every guy has hit on you, and I must be 15 years older than you!
"So, age is just a number, right? And I'm really impressed with what I see. You're a fit, kind, and respectful gentle man. But I've got a chance to make a life milestone happen, and I'm serious if you're not joking. I've been saving up a lot, and I can take care of myself. I'm only sharing a place with two other girls, and this job isn't a career. Just say the word, and I'll be yours!" Then squeezed my hand.
"I came in for a breakfast sandwich and left with a gorgeous first mate!" I exclaimed with a smile. "I'd be thrilled to have you on board. If it's not for you, I'll drop you off at the first port and you can take an island-hopping flight back. I think you'll need some time to pack a few things."
"The other server will bring your meal. Bet I'm back before you finish. Everything I have will fit one bag."
"OK Lola, I'll take my time, see you in a bit."
Watching her perfect ass sway in her booty shorts as she left, I was mulling over what had just transpired. She looked over her shoulder as if knowing my eyes were on her, and gave a grin as she passed through the door. Well that just happened.
I was making some notes, and sipping the last of my second cup when her fresh smiling face came back with a backpack.
"That's it? I asked looking at her lack of luggage.
"Yep. Seriously don't keep much but passport, laptop, phone, and a few clothes. I figure the need for toiletries are going to be minimal on board."
"Ok, lets' start off," I suggested, and lead the way to the boat. Lola took my arm, and glowed like it was her best day.
Once aboard, I gave a tour. "Here's where I sleep, and there's a guest room there as well."
"I was planning we'd be keeping each other company," she winked.
I took her into my arms gently and gave her a long kiss. "This OK? You have options, and we can go at whatever pace you feel is comfortable."
"I wouldn't have come knowing the closeness we'd be living in, unless I was comfortable jumping in with both feet. It's not like we just met in a bar, we've chatted for months while you were getting ready to move to your boat, and hanging at the marina. This is the next step for me."
Ok, well I'm very comfortable with you too, and see nothing but us growing closer and exploring each other's kinks," I winked. "You can use the spare room to store your gear and for some private time if you feel the need."
"I'll show you the gally and heads/shower, etc. then we can start off. It'll be fun showing you the ropes -- literally."
We got everything sorted, and it was time to start the engine and cast off. Lola was a natural learning how to raise the sails and trim them. We were underway with a steady, medium breeze and I was checking our course and track. When I looked up, my eyes popped, as there Lola stood in her birthday attire. She had a couple beers in hand and a wicked grin knowing she was going to shock me with her surprise.
"Hey, look at this! I've got a beer for you captain, and I'm now officially dressed for this trip. What do you think? This is the package, good or bad," then did a slow turn.
"Wow, you're absolutely incredible! You could have anyone you want, and you'd still be the most amazing person. It's such a privilege to be in your presence."
"Only problem captain, is you aren't in regulation uniform!" Lola smiled.
I put my beer in the holder and joined the party undressing for the occasion. "Hope you aren't disappointed hon."
"Uhhhh Im not a size whore, but you are packing a decent package sailor. I hope by bedtime I've had that in every hole all over this boat!"
The boat handled beautifully. With the leads coming back to the cockpit, adjustments were easy, as well as tacking upwind to head towards the first marker offshore where we turn towards the first destination. We chatted about many things snuggled together sipping beer, soaking up the sun and sounds of the boat making way.
"Do we have to go back this evening? Why not just head to our first stop today?" Lola asked.
"I was thinking the same thing. With two of us, it's far easier to manage the boat. You are picking everything up so fast, I'm sure we can work out any bugs as we go. So, agreed? Bermuda first stop?"
"You betcha. Hey, you hungry? I can fix a snack."
"Sure, we can hove-to for a break. I'll show you how to set the boat to more or less stay in one spot so we don't have to keep watch for a while."
The nudity was getting to be kind of natural. Still a feast for the eyes. Lola was about 5'6", thick DD, firm, no sag, shaved Mons, heart shaped ass, and everything in proportion. My balls were blue trying not to pop a raging erection. Now we had no duties to focus on, it was just each other, and nature had its way of interfering.
Lola spotted the sign and slipped to her knees enveloping my rod in her shapely lips. Her bright green eyes smiled into mine as she slid down until all 7 inches were buried in her face. As she slid out, she worked the head with her tongue sending shivers through me. As she could tell I was fully aroused, she stood and whispered "fuck me Steve, I haven't had a good fuck in over a year, and I want your seed up in this. Brand me yours. This pussy is all yours, and I want you to fill it anytime, anywhere you have an urge."
And that's what I did. We fucked in the galley, then the couch, then we went to the master suite and pushed her feet up to her ears and cored her sex hard. She moaned and gasped as my cock hit places inside she hadn't felt in ages, then she pushed me back.
"I want my ass filled. I want to feel you unload your cum in it this time. Just go slow at first, but push straight in, even if I scream."
She rolled over on her front and raised her bottom for my access. I had some lotion in the bathroom, so fetched it quick and used a finger to penetrate her anus while applying lotion inside. Next, I coated my hard cock, and aligned the evil eye with her starfish. I pressed firmly, and the cinnamon ring parted easily taking me in to the interior ring where I met resistance. As per her instructions I kept pressing as hard as needed until it relented and the rest of my cock slammed home.
She moaned the whole time, and let out a muffled yelp as I broke past the last barrier.
"Fuck it hard Steve! Rip it wide! Make it hurt!"
As I slid back and forth, taking the full length of my cock, I increased my speed while she moaned encouragement begging for harder abuse. I was slamming my balls against her taint over and over as she began to wail. I felt my cock tingle with pre-orgasmic sensations and after a few more strokes Lola began to shake all over. She screamed and cursed, as I began to shoot ropes of seed into her chasm. We both collapsed from exertion, and slid beside each other in a loving embrace as she softly cried on my shoulder.
"Lola, you OK? I thought all your sounds were from excitement, have I hurt you?"
"Yes Steve, I had some physical pain, but it's just what I hoped for. Mentally, you made me feel so lusted for, and its exactly what I needed. Im moved you gave me exactly what I needed in the moment, and my tears are those feelings of joy and desire leaking out.
My asshole will feel tender a while, and I'll delight in the sensations my man gave me making me his, the way I needed. I hope I haven't upset you."
"If this is what you want and need, I will lovingly do whatever it is you ask for. I feel concerned though, I don't want to be responsible for injuring you."
"I don't think anything is bleeding, it was just pure pain in a way that makes me feel desired, and drove me to a really deep orgasm. Call it a kink, but I need that sometimes, and I wanted our first time to be memorable."