Bob's Memoir: 4,000 Years as a Free Demon Vol. 1 - Cover

Bob's Memoir: 4,000 Years as a Free Demon Vol. 1

Copyright© 2022 by aroslav

Chapter 18: In 1492, Columbus Sailed...

Fantasy Sex Story: Chapter 18: In 1492, Columbus Sailed... - "Hi! I'm Bob and I'll be your demon tonight." But Bob is not your ordinary textbook demon. He was not imbued with any traits of evil. He's just your everyday, slightly horny, happy-go-lucky (mostly lucky) demon with 4,000 years of history as his teacher. This is the way Bob remembers it happening and he was there! (Tell that to your history prof!) It's a romp through the annals of time from a unique perspective. A little bit spooky. A little bit sexy. A lot funny. Vol 1: Before Caesar (Mostly)

Caution: This Fantasy Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Consensual   Romantic   BiSexual   Heterosexual   Fiction   Historical   Alternate History   Paranormal   Demons   Harem   First  

“AFTER YOU LEFT...” Esmeralda started her tale.

“Was imprisoned,” I corrected.

“After you were cruelly and brutally forced into a dank dark cell and kept there without food or water or human company,” she started again, rolling her eyes, “Grandmother discovered you had never been on a sales trip in all the years you were taking casks away. There was no one outside our valley who had ever heard of our wine. The money had all come from you as you stockpiled the wine in your bag. She almost opened the bag just to demand the money.”

“That would have been unwise,” I grumbled.

“So she figured. Anyway, she had enough money to keep the vineyard producing and was able to buy another wagon and horse to replace the one you stole.”

“I didn’t steal it! She trapped it inside with me.”

“Uh huh. She hired helpers for the vineyard and then she and her son loaded the wagon and took it to surrounding villages. After sampling the vintage, the road houses and taverns all wanted to buy as much as they could. Our Chianti became the most popular primitivo table wine in all of Tuscany. She reckoned that if you had actually taken the wine to sell, we’d have earned twice the paltry sum you paid for it.”

“That was not a paltry sum!” I bellowed, and then lowered my voice. “She certainly never complained about money when she was spending it.”

“I’m sure. Great Grandmother Esmira always exaggerated when she spoke of you. To hear her talk in her older years, you were so well hung she had to take a day’s journey by horse just to get to the end of your cock.”

“It’s not that big,” I said.

“I saw. Big enough, though.”

“When did she tell you all of this?”

“Some of the stories were passed down from my mother or her mother. Anyway, Esmira’s children got married and had children. The more she thought about it, the more Esmira decided you couldn’t have actually been the father because her children showed no sign of any demonic traits.”

“I wonder which of my traits she considered demonic,” I sighed.

“Most of them. Really, the kids didn’t even look anything like you according to her. One was so dark-skinned she was sure the father was African or south Mediterranean. I have just a bit of her color.”

“Well, she was right. I cannot father children,” I confessed.

“I need have no worry about having sex with my grandfather then.” I looked at her sharply, but she just continued. “Everyone worked on the farm, but Esmira was always the head of the family and the boss, right up until she died. She continued to acquire land and began raising goats to make cheese that went well with the wine. By the time she died a couple of years ago, the palazzo was among the wealthiest and most illustrious in all of Tuscany.”

“She died a couple of years ago and you just got around to opening the bag?” I raged. Quietly.

“She shoved it into my hands just before she died and told me to keep it next to me always. There was an inheritance dispute among the descendants. As a result, I was shipped off to a convent at San Michele a Monteripaldi. That reduced the number of heirs. It’s funny how no one has ever touched or even mentioned the satchel.”

“The look-away spell,” I said. “I’m glad it is still working. I need to refresh it so it doesn’t fade.”

“Well, I can see it. It’s right ... Wait! Where did it go?”

“You could see it while it was in your possession. Now it is in my possession.”

“That’s not fair. I wanted to go inside.”

“Someday. Just not yet. I need you out here. Now continue the story.”

“I’m still too young to take the holy vows. I was just considered one of the orphans they cared for. Though I understand I came with a rather sizable gift to the convent. Then Father Calvino arrived. He’d recently been promoted to Cardinal and was all full of himself in his red robes and pointed hat. He got the appointment so he could carry ‘certain papers’ to Spain on behalf of the Pope. But that was all he had. He had to find a seaport and book his own passage. The ports around Rome are still too dangerous as Turkish pirates harry the Spaniards. So, he came north. He stopped at the monastery, looking for a secretary. They sent him to the convent. The convent gave him me because I could read and write.”

“And he took you because you have tits.”

“You noticed?” she asked excitedly. “They’re not as big as Mother’s or Grandmother’s, but I think they’ll grow.”

“I noticed,” I said. “We need to disguise them to keep you from looking so desirable.”

“Desirable,” she sighed. She was not getting the point.

“See here, Esmeralda. If you follow around a priest and look like you are ready to fuck, someone will. Or they will imagine that I already am. Either way, it would put us both in danger. Until we have fulfilled our current mission and delivered the papal bull, we need to lay low and not raise any suspicion. If I have to use magic to protect us, they will do their best to find and destroy us.”

“I understand, Bob. But can I have them out to display when it’s just the two of us?”

I groaned. She really looked delectable. And to think her great grandmother had been shocked speechless when I removed her clothes.


I’D LAST sailed just a century and a half ago, but I was amazed at how far the technology of shipbuilding had come, even in that little time. The Spanish galleon was a large and fast ship with passenger cabins below deck. I thought fleetingly that Poseidon would have had a tougher time with this ship than he had with my tiny boat. I’d like to see the Scylla attempt to crush this one!

I quickly silenced my thoughts lest they be overheard as a challenge.

By the time we reached Catalonia, I had made sufficient alterations to Esmeralda’s appearance that she would not draw attention. I also worked on a modified ‘look-away’ spell that would keep her from unwanted notice. It wouldn’t make her invisible like the effect on the bag, but she would be unremarkable and simply not draw attention. She was more androgynous in appearance but I didn’t want her to look too much like a boy. There were many in the religious orders who preferred that gender. I had not told Esmeralda what Calvino had actually intended to do to her. It would make her constipated.

We disembarked and were met by a small detachment of mounted soldiers and a few priests. The priests did obeisance and the soldiers watched impatiently as our luggage was loaded onto the top of a carriage in which we rode to Castile, where Isabella had recently consolidated her control by ousting her aunt and legitimizing her claim to the throne. I was transporting three large trunks and had no idea what was in any of them. How many possessions did a priest need? We stayed in inns along the way and no one thought it the least bit strange that my secretary nun stayed in my room.

A rumor grew that she was a bodyguard and people were better warned away. Of course, I had no part in starting that rumor. I did, however, spend time making sure she knew how to defend herself and she took to the instruction well. When we were in private, Zhi emerged from the bag to give her lessons in hand-to-hand combat.


IN CASTILE, we were conducted to a suite of rooms in the local diocese and given two days rest before the monarchs summoned us. We immediately began unpacking the trunks to see what on earth was in them.

What I found made me smile. Some twenty-five years before, a man in Germany had succeeded in making multiple copies of the Bible with a machine he called a printing press. Since that time, many books had been printed in Germany, Italy, France, and even England. I pushed the trunks through the gateway to the infinity room and the ladies unloaded the books for our library and refilled the trunks with normal clothing and household goods so they weighed about the same. Then they pushed the trunks back out to me. I had a new collection of books and looked forward to the time when I could sit and read.

My libraries had grown quite extensive, as I noted during my time in captivity. I’d collected works from some of the largest libraries in the world, not just those of Europe and the Middle East. But it was not appropriate for me to just steal all the books from wherever I saw them. I developed a replicating spell that I could pass a thing through and make a copy of it. I had first discovered the spell when I replicated Odysseus’s boat on the infinity room sea. With only a few modifications, I was able to rapidly send books through to the infinity room where they were replicated exactly and then I put the originals back on their shelves. But sometimes, I simply saved books from disasters or from ignorant people who decided too much knowledge was a dangerous thing and were devoted to destroying them. Or from luggage I inherited from a dead priest.


FERDINAND WAS besotted with his wife, Queen Isabella. In fact, I’d say totally pussy-whipped. He’d made a play to be declared ruler of Castile when her father died, but it did not take long for the nobility to set him straight. Isabella was Queen in her own right and as she was adjunct to him in Aragon, so he was adjunct to her in Castile. Together, they brought the rest of Spain and Portugal under one rule, at least in name: The Catholic Monarchy. Ferdinand might have been upset about his position in Castile, but he was overwhelmed by his wife. I did not witness anything Isabella wanted that Ferdinand didn’t jump to provide. More about that later.

The papal bull I brought to them was exactly what she wanted. It put control of the Inquisition in her hands rather than in the hands of the church. Of course, priests would investigate and try the accused, but the queen’s soldiers made the arrests, consolidating the power of law under the monarchy rather than the pope. The priests did not need an army.

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