It was a beautiful evening when I saw signs of human intervention admists nature over the horizon, I looked back to Hewi, reassuring to oneself that the man was still behind me, there I have the most random thought to ever exist or crafted inside a mind; would he be looking at me down low? I believe I would not be free of sin being in his shoes, but a man's value is different from another, especially a knight, so I wouldn't assume even yes or no. Rather I elected to asked him a few questions.

"Now that you reached the town, you are done for the day, may I assume?"

"Yes," Hewi answered "Do you have any plan for yourself, Tanya No Lastname?"

As the question went in both of my ears, I turned around to look at the town and down on myself. A jobless, pennyless and unnamed woman in medieval time with magic, such a perfect combination to be killed and forgotten somewhere down the road, buried if lucky enough.

"Prostitution, I hope. How much would that make?" I answered and asked.

"Do you think a knight would know that?" He replied, annoyed.

Without a reasonable answer for my lack of world knowledge. I stared at him quietly.

"..." He also stared at me whilst we walked

"Around 20 Qo"  Hewi looked towards the town, "Allegedly"

"Allegedly" I repeated.

The town was far from what I've imagined a medieval living space would look like. Rather from a sad, cramped and unhygienic slum. I see a vast place, walls made of a type of brighter brick or stone, diverse shapes of roof from spruce or dark oak, green bushes from here to there trimmed and cleaned, with a near stone path leading wanderers like myself through town.

"Mister Cocksworth! I didn't know you had a girlfriend!"

A young man, rather somewhere below 20 but close enough yelled with his arm up waving. I haven't noticed this, but Hewi was walking in front, rather than behind me now and we're heading somewhere towards the center of the town.

"Just doing my job, Treg." He replied.

Everyone here got a terrible name, now that I'm writing this and trying to sound out their name, it could be Trek.

We made our way to a three story, noticable bigger building than the rest. It's defintely more refined, too and I noticed the sign calling it an inn. I would believe it is like a motel or such? I'm afraid I am not familiar with this term. But it is an overnight resting place for people who had nowhere to go and travellers, such as Tanya here, or me.

---

I have to get out of character a bit here and I do apologize. But Hewi just woke up complaining that my oil lamp is irretating so I would like to try and keep the rest of this entry as short as possible, then get myself some rest.

Brothels are legal, but not allowed in certain areas such as Deshla here, but the inn is a legal loophole. The owner here; rather I'd say a nice lady named Botol, allow prostitutes to stay for half price. But whenever a guest picked their room, the corresponding 'worker' who occupying that room got to leave or convinced the guest to let them stay, and we can all make of that information as we wanted. By which she would take a third of what they made from the guest.

Staying is 4 Qo per night, so half of that is 2 Qo for me and two other prostitute.

I also learn that Hewi did not need to pay for anything; a room is reserved for him because the owner expected him every seven days passed, and whatever else he wish to spend are recorded to be deduct from the owner of the establishment's monthly tax.

Hewi didn't think I was right in the head saying I am prostitute, so he offered to find me a job, though I declined, for I am concrete about what I would want.

"Here." He hestitated, but handed me a small leather bag, inside was a notebook, a miniture quill and some ink while we were browsing the streets to familiarize me with the place.

"I can't pay for that." I answered.

"It's been at the capital's Lost and Found for a year before I took it, you can sell these to start your life, you don't seem that crazy."

I contemplated, but then took it, that's how I started my diary journey.

"I will try to repay you when we meet again, Hewi Cocksworth." I said, knowing it only takes seven days for Hewi to make a loop back here, and I won't be leaving anytime so soon.

"Or you can treat those as my down payment for you." He replied with a straight face.

It took me two hundred years to process what he said. I was exaggerating, of course, more like eleven seconds, all for me to understand the implications.

Never have I ever thought that my first time would be with someone named Hewi Cocksworth, though.

"What do you mean first time?" He asked me, confused.

"Did I say that out loud?" I asked, snapping out of my thoughts.

"Yes, Tanya No Lastname."

"Then this is my actual first time, you heard correct."

He seems confused, a virgin prostitute with no identity or money is a fairy tale to most. And that is not incorrect, I might say, I am a virgin in my past life too, for fifty-ish years.

Long story short, I was in the same room with a man whom I only met for an evening, undressing my new self for the first time with my back turned while I hear metal sounds of his armor clunking behind. I took the time to look at myself; untattered, womanly, smooth skin and little to no fat. This body is that of an average woman in this perticular period of time but not appreciated enough, I would believe from my limited knowledge. And my teeth are... surprisingly white, wondered me if this body was randomly generated like a dice; or rather my consciousness continued existing from a random woman.

After all the clunking and rustling, Hewi Cocksworth was finished and I turned to look at him. We met eyes sitting on a small bed and observed one another's naked bodies top to bottom. This shall be the first great sin since Cain and I was, indeed, more nervous than expected of myself. Born as a man and lose virginity to a man is not a life someone would imagine.

"Mr. Cocksworth, would you mind leaning back just a little?" I asked

He did, putting his arms behind on the bedsheet to lean back on it, giving more space in front for me to calculate my actions. I believe as a prostitute, it would be best if I learn how to be on the offense. I crawled towards him to admire; the most average looking face in a crowd with blue hair. Looking down, the same color was to his Cocksworthhhh~!!%&***~

I spilled some ink holding back my laugher, my apologies, the entry is too long now for me to rewrite the whole thing so to anyone who might read this, I apologize and would attempt to lessen the jokes about his name being Hewi Cocksworth.

His... cock was hairy, like Hewi? hairy? Oh so I should finish this entry fast then go to sleep. Hewi is covering his face with my pillow now that I looked over.

---

Blueish pubic hair... Strange to me, because of his hair color? I had black hair my whole life and never seen much of another man's or woman's other hair parts to make a concrete observation. But this came as a pleasant surprise, I crawled towards until I was basically on top of him, a trained body I see. People in older times had nothing better to do than put on muscles, this does not interested me, but it does intriguied my curiousity, squeezing it was fun. 

I leaned in for a little smooch, which sparked an ignite of surprisation in Hewi's eyes as he held my nape, mistaking it for a deeper kiss. Which I didn't think I'd hate, so I followed through and rest my hands on his chest as an instinct. His breath was bad, but the dominancy of his tongue running through my mouth and whirling around my own was sensational, a feeling of emptiness in my brain, turned into mush from the unforeseen pleasure surprised me. My eyes went to rest, giving in, but I quickly realized that was not professional so I pulled back. 

"Wow..." I whispered

I slightly smack my lips, breathing through my mouth I stared blankly at Hewi's. I know exactly where I am, but my brain seems to not as it told me very loudly to have one more go and indulge in more pleasure. I took some heavy breathing and shook it off, down I goes to his chest, I can; but barely, make out a reverse triangle body, impressive to the eyes. I hovered my mouth over his chest, then slowly let my breath covered a nipple, smooching it with my tongue quickly brushing back and forth on the small thing. My other hand went to work down at his crotch, I finally hear it for the first time; his suppressed moan with shut eyes.

"Hmphh... Tanya."

"You forgot No Lastname." I teased.

He didn't respond, but clearly enjoying this, as he laid down completely on his back, I was now sitting on his stomach, bending my back downwards to suck and bite on his nipple, while my other hand gently rubbing his dick.

"Do I really have to say that...?" Hewi whispered, placing a hand on my thigh in an attempt to hold back pleasure.

"Nom" I bit his nipple as a response. Which made his cock noticeably hardened up.

The young knight was now breathing audibly through his mouth, neck pointed upwards in pleasure he squeeze tight onto my butt. I sat up straight, hand still rubbing yet with a slower pace, I slithered up to give him a little forehead kiss. While taking a deep breath, we met eyes.

"You're fine at this, Tanya No Lastname."

"Thank you." I smiled, "Though I can see that you are still doubting if it is actually my first time, am I correct?"

"I don't, no." He replied, "Prostitutes don't kiss, unless asked."

"Oh." I was surprised, but laugh it off. Though I believe it was more of a giggle.

I then looked downwards, I see my boobs dangling covering my view from Hewi, barely. This position prompted for a riding position... I think they called it cowgirl? Such weird terms. I put my weights onto my knees to elevate myself just a little, aligning myself with the man's dick, but I was slightly confused, I've heard... In biology classes, gossips and pornography that the vagina have three different holes and it's possible to insert it wrong. I was determined to be professional, but my worries were answered; Hewi held my arm.

"Let me." He said.

He carefully changes our positioning, I was with my back against the bedsheet, looking upwards to a man with sharp eyes looking down at my naked body. On one hand he anchored himself down right beside my head, the other he reach downwards to align himself...

I expected to smell a strong scent, sweats coming from Hewi. But he barely made a drop, while I was already sweating bullets, I couldn't keep my mind from racing with thoughts, combining with the heat from each other's body tangled with each other made every moment better, made my heart racing faster than ever as seconds passed.

"Will it hurt?" I huffed.

"I heard so..." He whispered "Any regrets?"

"No... Go ahead."

I brace for it, a traditional pose as Hewi placed the tip of on where I felt as my clitoris; he pushed his hips forward ever so slightly and I feel the strangest sensation ever, the flesh inside my body opened up as he made his way inside, almost like it was forced to, my womb was being told to make more room for a man's meat. It was tearing me apart inside out, I do not see or understand what was happening and anxiety took over as I tried to hold onto him, but I was unable to with my limited reach from this position.

I waited, anticipated for him to finish insert, it just kept coming and pushing in deeper and the pain amplifies. It did not feel this big when I was groping it. I buried my nails deep onto the sheet and bit on my own teeth, but it finally ended, he inserted balls deep and no more, it definitely isn't that long; but I can feel it up my throat.

I took short, quick breaths, feeling at ease when I feel Hewi slowly pulling out, I suppose a slight satisfaction of sexual intercourse as our private parts intertwined making friction.

"Wait..." I whimpered, realizing what to come next.

Hewi Cocksworth pushed, no, he thrusted his hips in faster than anticipated, I yelped, audibly, but embarrassment was the least of my worries as the pain decuple (times ten). My eyes widened, my irises gone upwards, mouth opened wide gasping for air.

"Hah... You're tightening up, I see you're enjoying this huh?" He asked.

Fuck no Hewi, I was in pain far greater than an nut kick, and more shocked than finding out Nemo was suppose to breed with his dad.

"Lord... Hah..."

It was unbearable, I took another big breath as my mind went numb, more and more as time passed. I could not; for the life of me, understand why would this sinful act be desirable for any living creature. 

The young knight continued, he pulled out with a smooth, consistent motion yet the insertion that follows was hellish and unpredictable. I could not move my eyes to look at him for the life of me, but I can feel his hands moving; from my ass, to my thighs, then he lifted it up, me laying down flat was an undesirable position for him so now my hips are raised up for easier entry.

It only took him one hand to keep me in that pose and prevent me from crawling away, the other he placed on my tits.

"Oh... Fuck... Tanya..." Hewi muttered.

Biting my own lips, I tightened my muscles in an attempt to relief the horrendous torturement happening from the inside. Hewi seems to be enjoying this, now I understood all the jokes I've once heard about men getting off but women can not.

But then I learned, to relax, to go with the flow of the situation and with the fabrics of the reality in front, I tried to relax, to not tense up. It was like catching a ball from height; I anticipated when the next thrust will be and move with it to reduce the energy, and let the friction happening between our genitals lead us to enlightenment. 

The pain was still apparent, yet I started to see light amongst the darkness, I can see the pleasure amidst the pain it brings, I'm starting to get use to it... Just five percents of pleasure among one hundred, combined with Hewi's tattered yet delicate and soft hands on my body gives me unexplainable tingles. I moaned for the first time.

"Mm...A-"

spurt

I was barely even getting in the mood when I the dude nut inside me, my disappointment was immeasurable and my day is ruined. Being defiled might be the worse feeling ever, maybe the foreplay was enjoyable.

I do not have the courage to tell him that it was an unpleasurable experience, and I do not have the rights to since I'm a paid prostitute.

We laid next to each other and drifted to sleep, but I decided to stay up and write these entries. From 0 to this, I will try my best to update on my life.

Dear to anyone who might be reading this.

I am Tanya No Lastname, and I'm from another world. As of writing this entry, I am in a town called Deshla, in the same room as a knight named Hewi Cocksworth.