Jake Goes to Town Ep. 01

Jake goes to town ep. 01 - Losing the virginity

by JulieKinkyWriter

Disclaimer. This story is inspired from real life but it is mainly fiction. Hope you'll enjoy it.

This is a slow burning story and it is mainly an introduction. More adventures will come.

Please forgive eventual grammar error. English is not my native language but i've tried to do my best.

"OK, I've told you everything you need to know. For any problems, just call me. Here's your keys and welcome."

The tall, sharply dressed real estate agent gave the flat's keys to Jake, then after a quick but polite farewell, he disappeared through the entrance door.

Jake looked at the closed door and thought "My house! My first house all my own."

He took a look around. The apartment was quite small compared to the cottage where he grew up: just an open space living room with a little kitchen, a bedroom and a small bathroom.

Jake was a young IT specialist in his twenties. He was freshly arrived from a small rural town to work for a big firm. Anyway, if he was scared of his life change, he didn't show: he immediately started to unpack his stuffs, not too many to be honest, and to arrange them into cabinets and drawers. Finally, he put his laptop on an empty table inside the bedroom.

Once settled, he took his phone to order a pizza and to tell his mother that everything was fine and he was OK. While looking at the bare apartment, he mentally took note of everything he should buy. It was quite a mystery since, until last week, looking at the house was his mother's competence and he had only vague notions of housekeeping.

Some minutes later, he finished his dinner and he could finally relax.

"What can i do until tomorrow?" he asked himself. "Going out? No, i'm too tired to explore the city and i must be careful with money until i don't receive my first salary..."

At that moment, he realized that he was drenched in sweat. It had been a hot long summer day and since he left his hometown he hadn't stopped a single moment.

"I guess i can test the shower..." He got undressed and went inside the shower. The fresh jet of water made him feel better. Instinctively, he reached out for his bathrobe but he realized that it wasn't with him.

"Well, nobody will watch me anyway..." He escaped from the shower, he dried himself with a towel and then he looked at himself in the mirror.

Jake was not a strong guy. He was quite skinny because of his building and because, unlike the other guys, he had never done any sport. He had a little body hair and some traces of beard that he shaved at least two times per week. If his body was unremarkable, his face was quite good looking, although no one could have defined it "manly". His features were quite delicate for a guy. The warm hazel eyes with long eyelashes and his brown hair that needed to be cut increased the feeling of femininity.

He ran his hand through his hair. He tried some hairstyles but he wasn't satisfied with what he saw in the mirror: he looked girlish.

"I just hope I won't find assholes coworkers", he thought bitterly, thinking about the bullies that made unpleasant his school years.

Jake took a look at the bathroom door, afraid that his mother might get inside for some reason and see him naked, but then he realized that he was alone and that he could be totally naked in every place of his small apartment.

With this new awareness, Jake went to the bedroom and started to watch some porn on his laptop.

After some time of that solitary pleasure, he fell asleep on the bare mattress.

"Hey Jake, what about a beer after work?" asked Mark, one of Jake's co-workers from the IT department.

"Sounds good to me!" said Jake, enthusiastically.

During a month of hard work at the firm, Jake was able to become friends with Mark and all the other IT guys. Despite Jake's initial fear, the folks turned out to be quite geeky as him and absolutely nice. For this and many more reasons, in the IT department there was an atmosphere of comradely that, as a former lonely kid, Jake had never experienced before and that pleased him a lot. Mark was an exception to the standard IT technician: tall, blonde, strong built and athletic. Jake could bet that he used to be the coolest boy in his school. Oddly enough, Jake and Mark immediately bonded and they often hang out together.

That evening they went to a bar that was considered one of the coolest of the city and it was also Mark's favorite place. After a couple of rounds of drinks, they were both tipsy and they started to talk freely.

"Naaaa! you don't get it" declared Mark. "Image, first impression is what counts with girls."

"You must work on it. Hit the gym, get stylish clothes" he added.

"I know, buddy, but it's just that i have my own style, my own personality. I can dress more in fashion but girls will understand that i'm faking."

"OK, do as you like, but then don't come to complain to me that you can't find a girl."

"Speaking of bitches, look there" said Mark after a brief pause. "Two beauties on our right."

"Yeah, sure! Now you snap your fingers and they come to drink with us", said Jake sarcastically.

"Watch and learn, bro."

Mark started to send some looks to the girls who, after a while, started to giggle and to look back at him. After some minutes, the four were drinking together and flirting. To be exact, only Mark was flirting. Don't find anything interesting to say, Jake was sipping his drink watching the two girls looking fascinated at his co-worker taken by the brilliant chat.

"So, do you work with him?" asked one of the girls.

"Wh...what? Yes" he answered, but before he could add something she started to talk with Mark again.

His glass was almost empty and he wasn't able to enter the conversation. Not that Mike was doing much to involve him.

"We must go now" said the other girl.

"Let's be in touch, i might need you to fix my lappy" she said to Mark with a wink. Then she gave him her phone.

"Yeah, sure, no problem", he smiled at her.

Jake went back home feeling ravenous with himself and utterly depressed. The day after, at work, he immediately faced Mark.

"Here's the playboy of the department" he said sharply. "So tell, how it ended up?"

Mark stared at him with patience, then said: "It ended up that we are going to meet again. Her friend said literally that your friend, you, was cute but he clearly need to fuck and this made her feel uncomfortable."

Jake calmed down a bit. "Oh... does this mean that she likes me?"

"No genius. This means that you have to empty your fucking balls before getting close to a girl."

"What can i do if i can't get close to a girl? It's nonsense."

Mark smiled at him sweetly and whispered to him. "Dude, this is why whores have been invented."

Jake was shocked. "Bu...But, how can i find one? And what about diseases? And they are expensive, and..."

Mark gave it a rest. "OK listen, you can find them online. There are some sites that host their announcements. About diseases, if you go to a pro who works in an apartment it's likely that she will clean herself after a meeting and if we talk about money, dating girls, buy them flowers and presents, offer them drinks and dinners, it is fucking expensive and after this effort she may decide that she doesn't want to have sex with you because... reasons."

"Well, it makes sense..." he admitted.

"Just another piece of advice" added Mark. "Don't forget that whores are also women. If you show up clean and well dressed, they will treat you better. Also, don't forget to be polite and do not ask any kinky stuffs at least at the first meeting.

"Any other advice, captain cuntbreacker?"

"Yes, never ask for discounts, they will think that you are a cheap person. And never give tips! If they think that you are generous, they will ask you more and more. Just pay what they ask without negotiate."

"OK, got it. But, how do you know those things? I thought that you had no need to pay to have sex."

"I don't. The advice comes from my grandpa."

The two friends started to laugh so loudly that the whole section turned to see what was going on.

At his home after work, Jake was sitting in front of his laptop. His house started to look like it was actually inhabited and on the bed there were now warm red sheets and some candles on the bed tables.

"OK, let's find a pro" he said, cracking his knuckles.

He googled for escorts in his city and he found several interesting ads. One in particular caught his attention: "I'm Paula, a mature, sexy lady and i'm waiting for you to live together moments of extreme pleasure. I'm an expert in every erotic technique and i'm ready to realize every erotic dream of yours. Inexperinced boys are mostly welcome."

With the ad there was also some pictures of Paula. She was a buxom sexy redhead in her forties.

Jake took a deep breath and decided to dial her number. He felt his hearth pound while he was waiting for an answer. After some interminable seconds, somebody answered.

"Hello" said a voice surprisingly neutral.

"He... He... Hello... Is this ms. Paula?" he asked.

"Yes it's me honey" she answered sweetly.

"Is that... that I... I've seen your ad..."

"...and would you like to meet me. Am i right?"

"Errrr... yes. Where can i find you?"

She gave him her address.

"And what about the... honorary?" he asked, don't knowing the exact term to use.

"We'll talk about it once you'll be here."

"Oh, OK."

"So are you coming or not?"

"Yes, yes. In an hour. It's OK?"

"Yes, it is. Call me when you arrive and i'll open the door for you."

Jake couldn't believe himself. He made a reservation to have sex with an actual prostitute. He followed his friend grandpa's advice: he took a shower, shaved his sparse beard, brushed his teeth and wore his best shirt and trousers.

He checked his pockets: phone, yes. Wallet with cash, yes. Keys, yes. Then he opened the door and went out feeling like he was in a trance. Paula's apartment was in the same zone where he lived just some blocks away.

Once he got in front of the palace, he did as she said: he called the number again, saying that he had arrived.

"OK, come up. 4th floor."

She hung up the phone and, after a couple of seconds, the front door opened with a buzz.

Jake entered the elevator and pulled the button with the number four. The elevator went up and so did his excitement. He was overcome by a mix of curiosity, desire and fear. One part of him was wondering if Paula was real as he saw her in the pictures or if she was fat and ugly or if there was a surgeon with two gorillas ready to bind him on an operating table and take his organs away.

The elevator doors opened on a desert corridor with some doors. One of them was half open. Looking carefully, Jake could see some hair as red as antique copper sticking out behind it. Once he moved towards the door, the person behind opened it wider to let him in, but she was still hiding behind. Once the door was closed behind him, Jake could turn and back and he could finally see Paula. She was even more beautiful than she was in the pictures. Her hair was a bit curly and it fell free on her shoulders. Her green eyes looked at him with pleasure, as she was happy to see him. The full lips of her mouth were open in a warm smile. Jake looked again and he saw that she was wearing no clothes but a black transparent corset made of lace and nylon with suspenders and stockings.

Jake was ecstatic and it was Paula who broke the silence.

"Nice to meet you Jake. I'm Paula. I'm happy that you've found me."

"Thanks...You..."

Paula tilted her head. "Me?"

"You...You are gorgeous!"

Paula kissed him on the lips.

"You are gorgeous too" then she asked "are you OK?"

"Yes, it's just that...I've never kissed a woman before."

Paula was amazed and said loudly: "So, you are a virgin! You are a virgin, right?"

Jake blushed. "er...Yes."

Paula hugged and kissed him again long, playing with his tongue and grabbing his cock, which was now rock hard. The shyness and the excitement made Jake rigid. He tried to caress her wonderful hair and he found his hand shaking.

"Why are you shaking?" Asked her delighted.

Jake took that question as a stung on his pride: "It...It's just..."

"Don't worry, i'll give you a wonderful first time. You'll never forget my mouth and my pussy baby."

Those lewd worlds made Jake even hornier and somehow helped him to relax a bit.

Paula took his hands and drove them to her butt.

"You can touch me as you want just don't squeeze me like a stress ball."

Jake chuckled at that remark and, finally at ease, he started to explore her heavenly body while Paula was kissing him as there was no tomorrow. The feeling of her silky hair, her smooth skin, the softness of the lace of her corset, her lovely humps... All sensations so new but so long dreamed.

Then Paula broke the contact. "Shall we go to the bedroom or do you want to fuck me here at the entrance?"

Without waiting for an answer, he took Jake's hand and pulled him to the bedroom. Jake followed her obediently looking at her bubble butt.

"Undress now. I want you naked, but don't forget my present."

"The present? Oh yeah. How much is it?"

Paula seemed to think about it, then she said: "OK, since you are a cute virgin, 60 will be enough. Usually i ask more."

He pulled out the bills which disappeared into her hands, then he started to undress frantically and in less than a minute he was naked. Paula made him lie in the middle of the big bed and she knelt on top of him, caressing his body.

"Mmmmmm what a beautiful boy... Do you like my lingerie baby?" She added when she saw Jake's hands touching her nylon-sheathed legs.

"Yes Ms. Paula, it's supersexy!"

Paula answered with a grin. "Would you like to see more?"

She cupped her hand on her breast and pulled out her boobs from the corset, exposing them to his greedy sight.

"Touch me little perv. Touch my tits."

She grabbed his hands and guided them on her bare chest.

"Do you feel my nipples? They are so hard, aren't they? It's because i go crazy for boys like you."

She grabbed his cock and she started to stroke it gently.

"I'll make you cum as you have never done before."

"Yes, please."

Paula went close to his balls. Jake could feel her breath on his ball sack.

"What nice nuts" she said. Then she took them into her mouth, looking straight at a bewitched Jake. The play of her tongue on his balls made him moan.

After the balls, she took care of his dick by licking the shaft and then wrapping her tongue around the red hat.

"Ahhhh yes! Take it all!" said Jake.

Paula gave him a knowing look and, with consummate skill, took the dick into her mouth in a deep throat.

"Ahhhh it's better than porn!"

"You like to jerk on porn, don't you little perv? Today you'll have the real thing."

Paula kissed Jake again.

"Can you feel the taste of your cock on my mouth perv? You like it, don't you? Say that you like it."

Jake was somehow aroused by that question. "I like it, Paula. I love your mouth that tastes of cock."

Jake grabbed Paula and made her to lie on the bed, then he started to grope her tits and suck her nipples.

"Yes, good boy. suck mommy's nipples."

Paula grabbed Jake for the hair while, with the other hand, she shifted her thong, exposing her shaved pussy.

"You licked my boobs so well. Do the same to my pussy."

She pushed his face against her exposed and wet cunt. Jake pulled out her tongue and had a taste of her salty juice. He loved the taste and started to lick frantically. It seemed that Paula got wetter at every stroke and Jake decided to sip the abundant liquid.

"Yes kid. Drink my love juice. It's good for you. Mmmmm yes, i'm ready for your cock."

Paula took a condom from the night table and put it on Jake's quivering cock.

"Give it to me. Stick your young strong cock into mom's pussy."

Jake put his hat on her moist lips, then trusted his cock inside. The gentle pressure of the humid warm walls was wonderful. Instinctively, he started to push and pull rhythmically. Again, Paula grabbed his hair and pulled his face against hers. Their lips met and she kissed him passionately.

"Mmmmm. Jake, you are such a stud. Fuck me like the whore that i am."

"Ahhhh. Paula. I'm about to cum."

"No don't. I want you to finish in my mouth."

Jake pulled out his cock and got close to Paula's face. She removed the condom and pointed his cock toward her greedy face. Immediately, a white flow of cum fell on her face and into her open mouth.

The powerful orgasm mesmerized Jake. Again Paula took the initiative and kissed Jake with her mouth still full of cum.

"The cum tastes good, am i right?"

"You made me drink my cum" said a disgusted Jake.

"Yes i did. Is it a problem for you? After all, it's yours, it's not from another man" she reassured.

Paula continued: "I hope you have enjoyed your first time."

"Yes. Totally. You are incredible. Can we do it again?"

"Thanks honey. I gave my best because i like you a lot. Do it again? Now? I'm afraid that it's not possible. Another customer is about to arrive in half a hour. By the way, i have to get ready for him. He wants to be dominated this time."

At the time that Jake got dressed again, Paula got off her lavish lingerie and, completely naked, she went to the bathroom to refresh herself, then she opened some drawers and fetched the outfit that she was going to wear: a pair of long stockings, a pair of long sleeved gloves, a corset made of shiny black rubber, a weird harness that looked like a thong to Jake but it had a like a socket on the front, a black, 8-inches long sex toy, some ropes and a whip. She placed all the lewd stuff on the bed and she started to smear some kind of lotion on her legs.

"Don't mind me, take your time", she said. We have some time before he arrives.

"It seems you two are going to have a lot of fun", Jake observed. Amazed by the items he saw.

"He would. About me, i'm not sure. He's not one of my favorite customers. He always asks weird things but he is quite old and he has no energy thus i think the thing will be over soon. He is also quite annoying sometimes."

"So why do you...Accept him?"

"Because he is filthy rich. He gives me 300 bucks every time we meet, but this time i asked him for 500. He wants to see me in latex, he wants me to whip and fuck his flabby ass, he wants me to tie him up... By the way, there are customers way worse than him actually."

"Really? Like how?" He asked.

"People who are rude, cheap, drunk or high, smelly pigs, the ones who want crazy stuff without asking me first...

"Again, Mark's grandpa...", he thought.

"I wish i could meet only young, nice guys like you are. I like you also because you are effeminate. I literally go crazy for that."

Paula's words made Jake remind him about the school years. Finally, Paula wore her rubber stockings and looked at Jake.

"I'm sorry to kick you out in this way. I wish you could stay longer. Please don't make that face," she said, looking at his frown.

"It's not that...When i was at school the other guys told me similar things..."

"Oh, i see...I'm sorry", Paula got up from the bed and hugged Jake.

"It's OK", said Jake, trying to smile.

"Let the past be in the past", Paula suggested.

"Yeah", he whispered.

"I know what you'll cheer you up...", Paula took the stockings, the corset and the thong that she had worn when she had sex with Jake. Then she took a paper bag from somewhere and put the sex-scented lingerie inside it.

"I don't do this for everyone."

"Wait...Are you saying that this is for me?"

"Not exactly, i'm lending them to you. You can use them for masturbate and when you come to see me again you'll bring them back. Please be careful."