Entry 5.5: Awkward First-Timers
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"Did you for real?" I giggled, opening my door to the sight of a clean, well-groomed looking young man with some wild flower tied together. Trek came at night after dinner time to take on my offer to 'repay' him unofficially.

He definitely got his hair done, his clothes was clean, not new or expensive but definitely better than what was everyone's wearing on a daily basis. The quote unquote bouquet of flower he got me was 4-5 flowers of different color standing side by side together in a small clay pot with water inside. 

"Er... Did I not do it right?" Trek asked.

"This is something you should do to your love interests, a nice and well-mannered girl, even a fellow adventurer you might meet along your journey, but not a prostitute. Come in."

I was not wearing the new clothes he gave me, I was saving it for tomorrow when I go to bathe in the river. So I was itching to get it out, though it's best to not surprise him. I sat on the bed and gesture Trek to sit down with me.

"You can put the flower on the table, though I would advise you to bring it back for someone more deserving."

I said, resting my chin on my own hand while looking at the young, tall man.

"But Tanya, why are you talking down on yourself so much? I think you're a good person, too." He replied, sitting down right beside me.

"How so?" I asked

"... Um, it's... Complicated. I shouldn't- not..."

Trek started to fidgeting with his fingers and looking around the room looking for distraction, so I knew he got something to hide, so I wrapped my arm around his shoulder, brother to brother, man to man per se... It was funnier to me, who knows that I was a dude, but to Trek, he just looked at me dumbfounded.

"Speak, that's a command."

"Uhhhh- The people- Oh god, Talvic is going to kill me." Trek cleared his throat before continuing, 

"There are gossips going around that you're actually an enchantress who were sent here to help the town, since you came... Hewi seems really happy and even donated some Qo to our funds, Desmond also said he haven't experienced the feelings you gave him before? He didn't specify but he's gone travelling now- Uhh, the adventure team from yesterday, especially the blue guy said he's happy and will return to visit Deshla really soon after his next quest. Overall, everyone's mood really got up and the people made some profits, even Botol said she's happy to have you here when I came."

I widened my eyes, surprised. Having sex with men brightened their mood? Well, yes, that's obvious but. That much? I would understand from David's point of view because he's a man whore that likes to do his thing and be satisfied alone, but Desmond and Hewi... I don't believe I've done much for them, rather, I inconvenienced them, I'm still have not paid Hewi's debt for the notebook and quill, while Desmond carried me all the way back to town safely after I passed out.

"You're one gossiper huh, are you going to describe our night to everyone in town tomorrow, too?" I chuckled.

"No no! Of course not! No... Can I? No no, I won't."

"Just kidding, I don't really care, I'll take that as advertisement."

I looked at him and tapped his shoulder, we both got a little laugh out of it, but I can definitely hear it, the beating heart of an anticipated man for his first time. I supposed it's his first time per what Botol said earlier this evening, but I can't know for sure since I never asked Trek. I should have asked him something more, I would like to get to know the folks of Deshla more, but I got carried away by my thoughts and did what I did.

"You can look." I said, standing up to lock the door, before taking off my clothes in two motions that I deliberately made slower. Taking off the top with just a pull from the hips to over the head, and taking off the pants by just pushing it down and took both my legs out. And as expected, Trek was staring; it was more flattering for me than I'd like to admit. I can get used to this, he's still frozen in time and eyes still staring at me as I made my way back to sit next to him.

Trek haven't been saying anything, the young man just looked at me with pure amazement and emptiness, visibly inhaling and exhaling, I smiled and raised my hand to rub his hair.

"I feel bad, to be honest with you, Trek" I said, before turn to whispering, "I shouldn't take a young man's virginity, it is too, can be something sacred."

"You think so?" He answered, his eyes definitely looking downwards, but he tried not to admit by looking up to make eye contact from time to time.

"What do you think?" I asked

"Everyone agreed that it's an achievement to get as many girls as early as possible, so I don't really believe it's sacred or anything." 

"I see. So the value of a man is not based on his achievements in the physical sense or the respect he earned via hard work and contributions, rather how many women laid down for him..."

"Err, You seems rather negative about this, Tanya? I think there's a correlation between those, too. If a man did many great things and achieve lots, women would rather choose him over any other guy, right?"

"Maybe," I answered, "Then how about prostitutes? Like right now, would you count me, too? Even though you conquered nothing."

"I would.. Yes, but still, if a man can afford a worker then it's still an achievement on him for having enough money to spend, right? In my case, "

I stayed quiet for a moment.

"I think you just taught me a new way of thinking, thank you, Trek. I should not ask stuffs that ruined the mood like this. Do you want to continue?"

"Yes... Of course- Can I... Uh, can I hold them?" Trek replied, looking away, though his finger pointing at my boobs.

To be honest, young man, that's what I'd be, too. No shame in being shy.

"Go ahead." I said, puffing up air in my chest.

Trek was visibly shaking, he then firmly got his hand onto to grab my breast and squeeze it, he smiled brightly and I also did. If one have to say, he was the most unprofessional yet enthusiastic man ever. He squeeze on my tits and suck on my nipples vigorously, as if a cute rabbit was nibbling on it, though I felt more ticklish and small tingles more than real pleasure. 

To the heart's content, the young man slowly laid me down to bed and focus solely on the boobs, I'm heartened by the thought of how much he's enjoying this, the moment seems to last forever, Trek got both his hands on underneath to cup them for ease of feasting... 

The moment was lovely, I put my hands on his hair like nurturing a baby, while my eyes glazed on the quiet night sky outside, the oil lamp was the only thing keeping us from indulging each other in the darkness. I get used to the bliss and started to let out slight moan, noticing that Trek also changed his approached, as if he learned how to pleasure a woman that fast, he stayed away from over stimulating the nipple; rather massaging the skin just right around it, keeping my mind in constant anticipation before surprisingly squeeze on or bite on it, heaps amount of pleasure crashes by like a wave amidst the storm. 

"Mmhm... You are... One lovely young man~" I whispered.

"Mmpf..." Mouthful of tits, Trek didn't reply properly.

I hugged his head in, rubbing my bare skin against his hair was like brushing against tall grass, he's getting better and better as every second flew by. The pleasure goes up by the seconds, my breathing became more heavy and audible, even as a prostitute... I feel like I'm the one getting all the fun, I curled myself down, resting my mouth near Trek's ears as I whispered moans and begging "more..." for him to continue. I am acting like an actual whore, drowning in pleasure given by my own client, shivers ran down my spines and I can feel it's getting very wet down there, just a little more... Just a little bit more pleasure and I would reach my climax, I believe, but I can hold on. 

It felt like it's been so long since he started fixating on my chest. Because it is, when I had sex with Hewi, the lamp never died out for as long as I am conscious, but for Trek... He's been hugging my breasts for longer than the full duration of a real sex, is it because Hewi's weak or Trek's just really good at holding back his dick? I do not wish, nor have a place to complain, but it's getting sore.

"Does it taste good?" I asked.

Trek finally got his mouth out and take a breather.

"It's... addicting! How were these kept away from me all my life?"

"PFFT" I laughed out loud, literally covered my mouth just to laugh at the absurd comment he made. "Well there's more to come, the night is still young. Do you need help taking off your clothes?"

"Oh, I'm fine."

I sat up again next to Trek as the young man undresses and put his clothing right next to mine on the chair, he's definitely on the meatier side... Medieval intensive physical labor shaped the men, I looked in awe for a moment, I could get use to seeing these things, and feeling normal getting turned on by them. I looked down and gently brushes my hand over his thigh, nearing his throbbing penis though not directly touching it yet, but I can see my little tease made an impact as the thing stood up high out of the sensation I briefly gives, it was hairy for the most part, but not that much hair that I'd care, the length was like a quarter of the penis itself.

"Um... Tanya, I wanted to try something, can I?" Trek said.

"Oh? And what can that might be?" I answered.

He scratched his head, and it took us a while to figure out what he meant when he was just too shy to just say the words lick and suck. Trek laid down and told me to come up, I thought he would be into a cowgirl position, but he immediate told me to turn around, so I was like, a reverse cowgirl? But then he said no no no and fumbled with his own words, covering his face while trying to finalise his thoughts. Is this what it's like to be a virgin? To the wandere who might stumble across this journal/diary, help me answer this for I am not going to ask any male.

But soon, I came to the conclusion, that he was asking for 69, for those of you at home unaware of this, I'm on top giving him a blowjob and he's below eating me out. I am very good at explaining, yes.

I felt uncomfortabe sitting down on his face, rather the expection was really weird. Have you ever sit down on something that can open its mouth and eat your genital before? I have not, and the thought of experiencing it was rather scary. I tried to conjure up the courage needed for this act of bravery, but god this is embarrassing, just hanging my crotch right above someone's eyes, the more I hestitate the more I couldn't do it and lower myself down.

"It's dripping." Trek commented, turning his head away.

"Shut up." I replied.

"..." I took a deep breath, and finally have to ask of him, "Can you just unexpectedly pull me down? I can't... Bring myself to sit down."

"Sure I can do that. Ready?"

"Yeah, go ahead."

"Three, two, one."

".....Huh? Why didn't you pul-."

yoink

"Eek! Fuck-"

I asked for an unexpected pull, and my man Trek delivered. He counted down from three for me to brace but only pull after I've lowered my guard down.

To describe it, it was like sitting down on a cold stool that immediately gets warm, but only difference is there's a small hole in the middle of the stool that a tongue came out to lick your insides. I yelped out in pain, bending down to hold onto his thigh. The young man's getting down on business again, getting my pussy eat was a different thing, a sensational phenomenon that words couldn't possibly describe justice for. He would kiss the flaps of skin outside and slightly chew on it (?), I can feel my clitoris being suck on violently, before Trek changed his focus on my insides and mercilessly twist his tongue around.

Before I could even get to retaliate and suck him once, I came, juices pouring straight onto his mouth him, and I can hear slurping sound followed.

"Oh god... Should I pay you instead?" I jokingly said, trying to lessen the mood.

"I'm enjoying my time, Tanya."

I'd feel terribly terrible if I were to pass out or exhaust myself without properly caring for a client (even though I offered the night for free), so I tried to ignore the immense coming pleasure and get down to his dick... This size is what I would call lovable, I believe human should be this size, compatible for a human; like me and not whatever race that adventurer; David was, I do not wish to have a client like that any time soon in the future.

I grab onto his cock, feeling it went from soft (not flaccid) to hard right on my hand, I positioned it in place, opened my mouth wide, closed my eyes and bend down. It went in easy, I was able to take in the whole of it, but as soon as I tried to close my mouth around it; I gagged and immediately have to back out with water coming out of my eyes as a defense mechanism. Of course, I've never swallow anything in this size before in my lifetime and I'm not used to it at all.

Maybe the problem was I'm trying to go in too deep, as you might say; deepthroating it, so I clear my throat and tried again, I open my mouth wide, and close Trek's dick in just at the tip.

"Ouch! Your teeth."

Another problem arises, teeth touching, I've heard this is a problem when doing blowjob.

I panicked, he's doing so well down there, is it because the man's just so good at adapting or I'm just really bad? Or is it a problem about different sexes' anatomy.

"I'm sorry... I never... Uh-" 

I tried to defend myself, but can not, I've already had sex with three person, but the closest I've ever got to doing blowjob was getting forcefully throatfuck which can't count.

Trek didn't answer, maybe he didn't hear me, but I elected tried my best. I knew how to masturbate so I could probably applied this to other men, right? It's been too long, but it's better than nothing.

One hand grabbing his balls, just slightly running my fingers through them, my dominant hand firmly around the circumferences of his dick and started moving up and down. I also got in with my mouth and just barely kiss it on the side, moving my head up and down to rub the surface of my lips as a little moisturizer for. After I did that, I can feel my crotch getting less work done to it, it's a good sign, that means he's not solely focusing on pleasuring me anymore and can feel the effort I'm giving him.

Our moans synced in a weird way, maybe one moaned and the other matched it by instinct, but there was a rhythm to it, I speed up the motion of me jerking him off as he started to raised his hips up of from the bedsheets from pleasure, I also played around with my tongue, coming from the tip of his cock and into his foreskin to 'clean' around it, fully expected to find those smegma that stuck around the rim, but surprisingly, none. People here clean their genitals? Maybe, they even got a knight that whole purpose was to clean water after all, this world is clean, and very enjoyable.

"Tanya... Tanya... I'm going to- cum, ah~"

"Go ahead... Hah... I think I'm going to- Mhm~"

He switched to his hand and started slamming his fingers into my vagina, I also am stroking his dick as fast as my hand could possibly. Soon, I feel his hand gripped firmly on my ass and his dick surging, my instincts let me know exactly what this meant, I cup my mouth over his dick and contain all the cum inside my mouth. It was the strangest substance ever, it was hot, not food-hot drink-hot but rather warm-hot if that makes sense, slushy, and savory on the tongue, in short just disgusting. But I still swallowed it just out of curiosity, definitely not recommended.

Trek's hand stopped, I got my pussy out of his face and sat next to him; a panting, sweating young man, pleasured out of his mind, eyes barely open and slightly jerking, with his penis now flaccid and rather cute, like a grape or strawberry.

I reached down to cup his cheek, seeing that of my fluids are everywhere from the sheets to his face and mouth. With questions on my mind, I bend down and kiss Trek in order to get a 'sample', it definitely tasted better than semen.

"Now I understand why... hah- gulp They liked you, Tanya. By the way, there's a hair on your, uh, lip"

"You mean Hewi and Desmond?" I asked, picking up a piece of curly hair off of my lip and blew it away.

"Uhh, And the adventurer guy, yes."

"And why is that?"

"You're... approachable? I don't know how to say it."

"Friendly?"

"Not exactly, but yes, you get the idea."

For Hewi, maybe I was just his type, since he asked for me, for Desmond, maybe it was the situation and position we were in, I mean, how many people can say they hold up a girl in their arms and bang her until unconscious in the middle of the lake out of nowhere with the morning cold air running through your skin? For David, he's a sicko who'd enjoy it when the girl fascinates him, as far as I'm concerned. And for Trek? Maybe it's his first time, and the first time are always the best memory for everything, so I'm just lucky to be his first, but in the future when a better woman, a more experienced woman came along, his comment about me would age like milk on a hot summer day.

I laid down again, I have two pillows, but Trek stretched his arm out to pillow for me, I smiled at the kind young man and laid my head down on his arm, he then turn around and hug me without much words between us. I then whispered.

"You are going to be a great man, maybe a great adventurer that I'd hear about from across the globe, be sure to not give up on your dreams."

"I will, please wait for me, Tanya. When that day comes, I will not forget about you and everything you did, but say, er, [across the globe?] That's a strange term, is it from your place? Like in a circle?"

Ah, they haven't discovered that the earth's round yet, or maybe this world is a different shape, such a weird detail that we talked about and I'm writing down.

"I invented it, it just meant across the world, don't think too much."

"Oh, okay..." Trek said, sniffing my hair, which I don't think I've cleaned since that time I dipped my hair underwater at Desmond's.

Soon, I felt something poking down at my thigh.

"Can we go again?" He asked.

I forgot from the past 3 experiences that, when someone paid for me, they paid for the whole night, this applies for when even I offered it for free. So it was rather shocking to have to be ready to work right again, but I chuckled.

"Sure."

I will close this entry here, the next part was nothing of notable, we did the missionary pose and hugged each other to sleep. One funny thing I could tell you was this interaction.

"That's the wrong hole."

"Oops."

Good night.

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