Roger Able's Cruise Ship Escapades

"Are you sure about this Rupert? There be no need in forcing yourself."

Rather than answer her directly, I wrapped my legs around torso.

"Oh Mr Able, what would they think of you upstairs seeing you encourage me like this."

I felt rather than saw what came next. Aileen was rubbing her stick, still slick with my spit, up and down the space below my own. It was a highly charged feeling. Then she moved herself lower and forward and I felt a pressure and a resistance which would surely deny her any access. Aileen rubbed my ankles as if to encourage me to relax. I tried, exhaling in and out slowly several times. Suddenly, she slipped in; I had accommodated her. There was discomfort, even pain, but a wondrous and entirely novel feeling of fullness. Aileen was...inside me.

"Holy smokes, Rupert, you are so tight. Keep relaxing...there's a long way to go yet."

I hoped that was a compliment. Tenderly, across the span of a few minutes, she pressed more and more of herself inside me, until I was sure I was at capacity.

"I'll start slow, Rupert."

I was glad of it. The pain and discomfort were fading. Aileen drew herself out and slowly, and then gently reasserted herself. As she reached her and my limit, a stab of pleasure overwhelmed any remaining pain. I blush even now to recall the soft moan which escaped my lips.

"You feel incredible."

"As do you, Aileen," I muttered with all the breath I could muster.

Back and forth with a tender slowness she went. Then, clasping my calves she raised my legs up which seemed to allow her an even deeper reach with her strokes. Every thrust stoked a feeling of ecstasy and surrender, of an animalistic need to take more and more of my companion.

"It's like you were made to fit my cock, Mr Able." I found myself unable to reply.

Switching up her stroke she began to see-saw out of me entirely, resting for a moment at the apex of her thrust before plunging back into me. There was no pain, now. I was at her mercy but completely at peace with it. My nearest relatives could have walked in and I would have asked them to wait outside until I -- she -- was done.

At the apex of her next thrust, she stopped.

"I'm gonna fuck you for real now, Roger."

"Please...don't stop," I groaned.

Idly she teased my entrance with her rod. But then she parted my legs and leant over me, grabbing my head with one hand.

"Open your mouth...wider." I did so. I looked up at her and saw her swirling her tongue around her closed mouth.

"Here." With a delicacy that belied the action, she spat in my waiting mouth. "Swallow that and then ask me proper what you want. What do you want Roger, more than else anything right now?"

I gulped her spit down before replying. "I want you to fuck me, Aileen."

She kissed me full on the lips, driving her tongue into my mouth. I wrapped my legs around her as I felt her push into me once more, this time with greater urgency. Again and again, she pressed something that engulfed me in pleasure. I could feel I was getting close.

"Oh Aileen," I whispered in her ear.

"Me too, Roger," she grunted.

Rising up once, she started to hammer into me, letting out increasingly guttural grunts while I lay helpless on the bench, my arms dangling over the sides.

"Where do you...want my seed, darlin?' she gasped out between strokes.

It hadn't occurred to me that I would get a choice.

"In me, Aileen, please...please."

"Your wish an all that."

As my own orgasm rose and spent itself on my stomach Aileen began to shudder and did the same within me. I could feel the warmth of what she had deposited and in doing so felt closer to her than at any other point in our strange meeting. Rather than pulling out, she collapsed on top of me and kissed my face and neck, murmuring sweet nothings in what I presumed was Gaelic. We laid like that for a while, hardly speaking, without a care in the world.

Eventually, a softened Aileen parted from me and began to daub herself with a washcloth which she presently passed to me. Once I had done so, I made to rise but she stopped me with a hand to the chest.

"Aileen, I'm sorry, I don't think I have another round in me."

"It's not that, Roger. Even I need a breather. It's just...could you do something for me?"

"Name it."

"Well I'm not sure it has a name but here...this." Into my sight came a stunted object with a circular base which tapered to a soft end. "I want you to take with me you to the upper decks. I don't expect I'll be seeing you again down here. Promise you'll wear it until at least tomorrow. That way, I'll be with you for a little longer."

I nodded and smiled at her, "Sure," I said.

She disappeared from view and once again I felt pressure at my base which abated quickly. The object, the plug, for lack of a better term, had sealed Aileen's remnant inside me. After her, it felt like the lightest encumbrance.

"Thank your Roger," she said and kissed me again

Here my sinful recounting of the day's events ends. The rest was proper -- and dull. Tea, dinner and drinks with my fellow upper deck passengers. Some pleasant conversations, even a few mild flirtations. Little did they know what the occasional stiffness in my pose meant. I would keep my promise to Aileen. I wear it now, even as I write in this diary before bed. Should this be my only erotic adventure it will still be an uncommon trip and an encounter I will remember and treasure for the rest of my life. But who knows what tomorrow will bring?

March 25th

I have another shocking tale of my own debauchery to disgorge into this sinful grimoire I call my journal. This time, to my surprise, on the upper decks.

I was walking along a corridor in 1st class, in the area reserved for the absolute elite, the wealthiest nobility and titans of industry, when a door to a cabin on my left opened and an airy bundle of scented lace and diaphanous purple fabric emerged, atop which was the head of a woman, about fifty. I caught the words, 'missing one, missing one' repeated a few times before she saw me and regarded me with an appraising eye as if I were a scratched jewel of a ring in her collection. Was I worth keeping, her expression seemed to say. Then she reached out and grabbed my arm in a surprisingly strong grip.

"You'll do," she said.

"Madam, what for?"

Before an answer came she had manoeuvred me through the door behind her into a small room, clearly an antechamber for the main family room next door. Arrayed before me were six chairs, only one of which was unoccupied. Sitting on the other chairs were five young men, at least I think they were men. They were all young, in their twenties. They all looked nervous. And they were all wearing women's underclothes. Their hair was styled or else they were wearing wigs. They looked a little cold in their elegant silk nighties of various feminine colours. Their nails were painted and their faces stylishly made up. They all sat primly, despite their apparel, legs together and backs straight. What an earth had I wandered into now....?

To Be Continued