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."
