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Introduction:

Columbus petitioned the court of Ferdinand and Isabella for years, always being told his estimates of the size of the globe were far too small, that he was a fool for thinking he could cross to the Orient by sailing into the endless great Atlantic Ocean. Then suddenly he had hi ships and the rest is history. What changed? Here's one fun idea...
“Your majesty? You called for me?” I asked as I entered the very small bedchamber, more suitable for a servant than the queen of Spain.

“Ah yes. Please come in Christopher,” she said and patted the bed beside her. “I assume you are still intent on leading an expedition for this supposed western route to the orient?”

“Yes!” I said excitedly and sat where she had indicated. For ten long years I’d been petitioning the courts of Portugal and now Spain, trying to obtain ships for such a treacherous journey. Excitedly I repeated, “Yes your majesty!”

“Good, then you shall listen to my proposal and on agreement I shall grant your request,” Isabella stated and I eagerly awaited her next words. Her husband King Ferdinand had been the only reason I stayed in Iberia rather than continue on through Europe to find a benefactor for my trip. He truly believed in my ideas, yet his fool experts said I was underestimating the circumference of the globe. So excited was I that it was clear I had a hard time sitting still as I patiently awaited her next words.

She seemed to delight in my anxiousness so preened a bit before explaining, “I have acquired the contracts for several ships for my personal... indulgence.” She let that sink in for a moment then continued, “As such I shall give them to you for each… indulgence you give to me.”

Having stressed it twice I couldn’t help but ask, “Indulgence, your highness?” unsure what I could possibly give her. I was the begging pauper of the two of us.

“Yes,” she stated and then removed her shawl to show me her bare shoulders and the tops of her breasts lifted up by her ornate and custom fit corset. “My husband has been away on his preparations for war to expel the last of the Moors from Southern Iberia and rid the continent of their blasphemy.” As interesting as that was I wasn’t following why she was unlacing her clothing, “Yet as noble and just as his plans may be, that leaves him away from my bed for far too long.”

“So you wish for me to…” I gulped finally grasping her intentions. We were both fully adults and had families. My wife had many years ago died, but I had a new lover and a son with her, though she refused to marry me. “No your highness, I couldn’t betray the king’s trust like that. Should anything happen…”

“You will be long gone on your voyage,” she interrupted and continued to slowly remove her complex clothing. “Besides it is too late for you to refuse now. Should you fail to even attempt to please me I shall have no other choice then to summon the palace guards and have you beheaded instantly for attempted rape.”

“But… I… I… I…” I gasped and then she grabbed me by frock and pulled me into a passionate kiss. It wasn’t a kiss for lovers, or even a married kiss. It was simply passion and lust as her tongue forced it’s way inside my mouth. I knew what she said was true, now with her lipstick coating my face I was either her willing adulterer or food for worms in the grave. And if this was the only way to finally get the ships I so desired, then by all the hells I was going to do it. I kissed her back and pushed her back onto the bed as I stood.

“Ah!” she laughed up at me. “I see that you have acquiesced?”

“So it would seem,” I said loosening formal coat jacket before taking it off and throwing it over a chair. “So the deal is one ship for each indulgence?” I asked coyly. She just nodded and I simply lifted her long enveloping dress enough for me to duck under it and burrowed between her thighs. She quaked and laughed, but delighted in my directness. In the dark I found her womanhood uncovered by any further small clothes so went right to work.

My face pressed into her soft Venus flower and sampled her natural womanly aroma finding it sweet and tempting indeed. Then with long, languid strokes I extended my tongue and licked up and between her moistening folds. With instance and excitement she pressed down on my head through her skirts to press me deeper, so I took her buttocks, one in each hand so that my thumbs could extend to her groin and pull her petals apart. Now able to feast on her tenderest bit directly I speared my tongue inside.

Never in my wildest dreams had I considered becoming a consort to a queen, but she had clearly been planning this for some time. She began loudly moaning out her pleasure loudly to our empty room, making me worry about those guards she had claimed would execute me on the spot if I should refuse, yet none came. They clearly knew the difference between get cries of ecstasy and those of anger. As I moved my tongue all around her canal I wondered how many other lovers she might have had that her husband didn’t know about. Surely it couldn’t be many as rumors would have gotten out far before now, but maybe her staff and guards were just that good and loyal?

I moved my tongue up to the top of her slit, finding her firm little nub eagerly awaiting my slathered caresses. To accompany my shift in oral focus I slid two fingers from my right hand into her birth canal to continue to stimulate her insides. For her part the queen was boisterously enjoying my work and I could tell her first ‘indulgence’ was already nearing. I flicked my tongue like that of a candle flame, gently but quickly, and then felt her clench around my invading fingers as it arrived.

“Oh God! Yes! Yes!” she screamed to the heavens, though I did not yield just yet. I wanted to give her no cause to doubt my seriousness in this endeavor, so continued to lick her erect Devil’s teat and wiggle my fingers in her churning quim. Her first climax was ending and I’m sure if I’d been given the time her second would only be minutes away. “Enough,” however the queen dismisses me and pushes me away.

I emerged from beneath her long multilayered skirt to see her breathing hard, making her half covered breasts heave most appealingly. “Oh, Chris you make me feel like a girl again,” she said with a giggle. Then something lights her eyes. “For that I grant you the Santa Clara.”

I knew the ship, a small fifty ton caravel nicknamed La Niña, Spanish for The Girl, a pun on the name of her owner, Juan Niño of Moguer. Either way it was a poor start for such an endeavor. “But your highness it is but a small trade ship. Built to sail the Mediterranean, not the open ocean.”

She brought her foot up to my groin and pressed her stockinged foot against my bulge as she smiled, “Then perhaps you should make any further indulgences more… substantive.”

“Very well,” I said and released my belt to drop my breeches and hose, then exposing my naked member to her.

“Mmm, very nice,” she said appreciatively and then sat up to inspect it more thoroughly. Her fingers were soft and adroit as she took hold of my still somewhat soft manhood. I clearly wasn’t the young stud I once had been, but she didn’t seem to mind. In fact I was actually surprised when she took the squishy mushroom head into her mouth.

“Ah, your highness…” I gasped at the unexpected pleasure she brought me with her warm soft lips. “You don’t have to…” but she wasn’t to be dissuaded. Her hand gripped tighter at my base and slid more of my member through her tightly pursed lips and across her warm wet tongue. All I could do was sigh as I closed my eyes and enjoyed the wanton monarch’s oral ministrations.

“Don’t let this go to your head,” the queen teased as she continued to stroke my hardening cock with her hand. “I’m not your whore, but rather you are mine.” Then she pulled my hips around and forced me to sit upon the bed if I wanted to keep my penis attached to my hips. Then, with a flourish Isabella unclasped her skirts and tossed them over her head, leaving only clothed by her tight corset as she pounced upon me.

Once more she grabbed my erection as she placed all her weight on her hand pushing my chest down into her plush feather bed and thick goose down comforters. “Your desire for my ships makes you my prostitute to use how I wish.” Then with her tightly squeezing hand she pointed my dick up and then forced it up into her snatch. After that I knew what it must be like for those poor women who were used by the rougher of sailors after a long time at sea.

I’d seen them take one man after the next, sometimes only minutes spacing between one and the next, and the queen rode me hard and fast like she couldn’t get enough of me inside her. She must have been still quite excited from the licking I’d given her, and maybe treating me like a man-whore turned her on. Her hips thrashed, not really thrusting, but grinding me up inside her as she focused on making her velvety walls like a vice trying to squeeze me out.

Only her previous ensconcing of me with her mouth gave me the rigidity needed to endure her almost violent thrashing atop of me as she quickly achieved her second orgasm of our encounter. Once again the noble woman revealed her devotion to our lord as she shouted out as her pleasure. “Oh, fuck. Oh… Jesus Christ!” I felt bad that I’d really not done anything to affect her pleasure other than being a warm post for her to writhe upon, but then I remembered that my reward was conditioned upon her pleasure. Better to hold out on my release for as long as possible and net the most I could out of this once in a lifetime chance.

“Oh Chris, you make such a great whore,” Isabella moaned as she came down from her high. “I think then for your next reward you should have a whore’s ship. So I’ll give you that painted one owned by Cristobal Quintero.”

“But…” I’d heard it called La Pinta, but couldn’t remember it’s true name. Its captain had the ship’s bow all painted up with barely clothed women to go with its lifelike wooden figurehead. They sure liked the female form and no wonder with the captain’s notorious reputation for visiting every brothel in the known world. I wanted to complain, but at least La Pinta was slightly larger of a ship than the first I was granted use of, and I still had my strength to try and secure at least one more vessel. “Thank you your grace.”

She stood up and extracted herself from my length and I wetly bounced free, still standing erect. “Good, now you are truly ready for what I desire.” She crawled back onto the bed and placed her head on her hands as she left her ass up and suck out over the edge of the bed with her feet. “I want you to thrust deep and hard. I want your final indulgence to leave me sore enough to remember until my husband returns in a fortnight.”

Spurred on by her words I stood up and approached her generous rear end and hair covered mound split by her puffy pink neither lips. The normally concealed skin of her fair posterior was white as China porcelain contrasting harshly against her black curly hairs. I would have been tender with her by nature, but her words told me she didn’t want tenderness, but excitement. With a gentle slap I laid one hand against the bare buttocks and she giggled with a little surprise before saying softly, “Harder.”

I spanked her bottom again on the other cheek and she just moaned again. I laid two more, one on each cheek, then grabbed my rod and poked it’s tip up the seam of her womanhood once more. Strangely she pulled away. “No man but my husband is allowed to defile my womb with his essence,” she teased.

“But..” I began and then she lowered her hips and placed my erection into the small of her back.

“Yes… my butt,” she said, though I’d understood without her explanation. I’d never found that as enjoyable as all the bawdy sailors joked about. I’d also heard of more than a few ‘good Christian’ whores that somehow thought being Sodomites was somehow less of a sin than giving up their first blood chastity. That way should they ever marry they could still claim to be virgins for their husbands. I would normally refuse such an offer, but this was my last chance to garner a true oceanic ship that could lead my miniscule fleet.

“As you wish your highness,” I agreed as I repositioned my love spear into her Demon’s hole. It was tight, though I could tell this was not her first time doing this. Her rear passage stretched tightly to allow me entrance, then clamped down once I was halfway inside.

“Oh yes Chris!” she moaned as I thrust in deeper, taking the rest of her that she had held back. “You are so much bigger than my husband the king! You are truly exploring new territory tonight!” Somehow that made it feel even better. There are not many times when you can get more praise than a king, particularly not one as intelligent and accomplished as Frederick, so now I found I couldn’t hold back from thrusting as deep as I could making her scream with pleasure, and scream she did.

Through the thin interior walls of her flesh I could suddenly feel something on the underside of my penis. With a glance I could see she head several fingers inside her, and trying to work the rest of her hand in, thrusting and pushing as she worked as hard as I was to bring about one final orgasm, clearly the best one yet by her praises to God. I was right on the edge too, as her excitement was as arousing as the feelings of her body clenching tightly around my manhood.

“Mother of God!” she started clenching tighter and I knew both of our peaks were near. “That’s the ship I’m giving you!” she screamed out. “The Saint of Immaculate Conception, mother of our lord...” she gasped and shuddered, "Jesus Christ!"

I couldn't hold on either past the erotic vibrations and thrashing my lover was experiencing as I reamed her ass deep and hard. But I also couldn't help but recognize frigate, much larger than the first two ships she gifted me, whose actual name was La Galatia after where it was from, yet of all the ships was the only one with a depiction of the virgin Mary as a figurehead. With double delight I buried myself deep in her bowels and groaned out, "Santa Maria!" as my torrent of ejaculate injected into her rectum.

"Yes! Yes! Yes!" the spasming ruler shouted out as she was overtaken by the same ecstasy. I pinned her to the bed, riding out my climax atop of the woman I'd just sodomized as we both collectivity breathed heavily. When the last of my seed was expunged I rolled off of my new lover and laid down next to her, still panting and dizzy from my trials.

"So... Christopher, do you think that those three ships will be enough to successfully complete your journey?" Isabella asked with a devious smile. I was about to assure her that they would and thank her with another kiss, but we were distracted by a sound outside. "Shit! They're early," she exclaimed grabbing at her discarded gown and running for the bathroom. Likewise I hurriedly pulled my breeches back on and ran out into the living room, plopping down on the couch and turning on the TV to pretend I'd been there the whole time.

"Hey Mike," Chet said as he looked at me, “Nice duds.”

“Thanks,” I smirked off his backhanded compliment. I knew he wasn’t entirely comfortable with me dating his only daughter, so I could only imagine what he would do if he ever found out what I’d been doing to his wife on and off for the last few years of college. Danielle alone was everything a young sexy hungry guy like me could ask for, but was so shy about sex, even after that threesome we’d had one Super Bowl Sunday right here on this couch. Her mother Cheryl however was utterly wild!

“Where’s Cheryl?” he seemed to ask suspiciously as if reading my mind. I worried that I had some incriminating evidence of out tryst showing, but just tried to stay cool.

“She’s still getting changed,” I said trying to make it sound like I was bored to death waiting for her. He just laughed and that set me at ease a little.

“Women huh?” he joked and that was finally when Danielle came in after him.

“Daddy!” she scolded him as she entered wearing her own copy of a princess’s garb that looked amazing on her. “You should dress up and come with us too. It's fun!”

"Naw, I'm fine with just enjoying a day off with a beer and my Monday Night Football," Chet answered.

“You look amazing!” I interjected honestly. Even though she was now my steady girlfriend and was introduced to sex in the presence and astrictive participation of her mother, we never told her that anything else had happened before or after we started dating. In fact there had been quite a few encounters when we’d come home for holiday visits. I don’t know why I couldn’t help myself around the older woman, but unlike Danielle who only let me make love to her in the dead of night one or two nights a week if she didn’t have an early class, Cheryl was always adventurous and seemingly always ready for a quickie.

Like tonight when Cheryl sent Chet and Danielle out to the boutique to size the dress she bought for her while we stayed at their home. Her excuse had been to give her daughter some quality father-daughter time. It wasn’t three minutes after their car pulled out of the driveway that she had her dress on and handed me a pamphlet with facts and details about Columbus and Isabella and simply announced, "You have ten minutes to get dressed and study up. Then you better be ready for your final exam… Christopher."

Her tone and inflection as she swayed her hips back into her bedroom left me no doubt about what she was planning, yet alone with her in her own house and dressed up in these costumes she was irresistible. She'd found out that I loved history back last summer so I ten minutes later I entered her bedroom an explorer and she a queen. And honestly even I had to admit it had been fucking sexy as hell!

“See!” she said smiling from ear to beautiful ear as she came over to hug me and give me the chastest of kisses to my cheek since we were in front of her father.

“I’m ready,” called out Cheryl as she emerged from her bedroom. “What do you think Chet?” she asked her husband thrusting forward her pushed up bosom just as she’d done for me.

“I think you better cover up or you’ll catch a cold,” he said putting a damper on everyone. “Weather says frost tonight.”

“We’ll be back before it’s too late,” she sighed. “Of dear you’re outfit is lovely!” she then switched topics to appreciate her daughter’s costume. “You and Mike make such a cute couple! Let me take a picture.” Then she got her camera out and took a few pics of us smiling. Before he could escape she turned to her husband, “Chet, take one of all of us.” Then she handed him the camera and got in close to my back.

Of course no one could see past their flair of skirts and posing close, but she grabbed right onto my ass cheek and squeezed it hard as her secret way of saying she really liked tonight. “Smile,” Chet said blandly and snapped a few pics of me sandwiched between his wife and daughter. Soon we’d be out to a themed Columbus Day party a friend of Cheryl was hosting, but I had the feeling it had all been her idea in the first place just to set up something like this. Well it had worked and like a fly I was clearly caught in her web. I just hope Chet never finds out because I have no doubt that no matter how bad a back and knees he has, he will fucking kill me if he does.






Author's notes:


I'm a lone amateur author so I apologize for any typos you may find (which I'm sure you will.) Though I think the stories come out fairly well all things considered.

PLEASE, if you liked this story, rate and review it.

This story was a surprise quickie sequel to one of my free series: Moms Need Love Too
3 comments

Anonymous readerReport

2016-01-14 04:47:48
Nice twist with the role playing , great job!

Anonymous readerReport

2015-11-16 15:47:20
Well played!

Anonymous readerReport

2015-11-08 18:55:38
Write more. Really liked the story and role play element. Great story!

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