Jake Goes to Town Ep. 02

"Jake, Jake", Mark shouted. "What's wrong with you today?"

Jake woke up from his daydream and realized that instead of doing a routine check on the company's server, he messed up the whole configuration.

"Oh shit!", he hissed.

"OK, i see that today your mind is somewhere else. Let's fix it up together", Mark proposed, kind and patient as usual.

After about half an hour, all the issues had been fixed, but not without a good quantity of swear words and biting jokes directed toward Jake from Mark and the whole IT section.

"Thank you guys, and... sorry." said a guilty Jake.

His colleagues accepted his sincere apologies with expressions like:

"Sleep at night, dumbass!"

"What's wrong with you? Are you in love? Is he a handsome guy?"

"You're welcome, moron."

Mark stood in the middle of the room with his arms opened to demand silence: "Gentlemen, let's have a pause at the cafeteria. Today Jake is offering."

"Yeahhh!"

At the cafeteria, after everyone had an unhealthy yet satisfying ration of donuts and coffee, all the staff went back to the office except Jake and Mark.

"Have you come to your senses now, buddy?", Mark asked.

"Yes, i guess so..."

"So, what's wrong with you today? Are you sick? In love? An alien parasite took possession of your body?"

"No, it's just...", Jake looked left and right to be sure that nobody was nearby.

"I've...I've followed your advice", Jake whispered.

Mark widened his eyes in disbelief: "Hey man, when i told you to lick a toad's back to get high i wasn't serious."

"No moron, i...i had sex... with a pro."

"Hey guys, listen up! Jake has popp..."

"Shush!", Jake put a hand on his mouth. "Please respect my privacy. By the way, how do you know that i was a virgin?"

Mark laughed hard.

"So you were a virgin? I was quite sure about that but i didn't dare to ask you. Ahahahah!"

Jake looked at him with a cherry-red face because of the embarrassment and the rage for having given himself away.

"You know what? Fuck you!"

Seeing his friend's face, Mark stopped laughing and asked quietly: "OK, OK, cool bro. There is nothing to be ashamed of. Anyway, tell me everything. How was she?"

"Ohhhh! She was amazing, better than a porn actress."

"Wow, cool! Tell me more."

"MILF type, red hair, awesome body, a real slut..."

"Very good, very good", Mark approved. "I hope she didn't suck all your energy away because this Saturday I'm going to see Claire and Nadeen again."

"Who?", asked Jake.

"Claire and Nadeen, the two girls we met at the bar last week. Claire gave me her number and she told me that Nadeen said that you were cute."

"Oh yes, now i remember."

"Yes, i'm going to see them again and you will come with me. It will be a double date."

"Well, I don't know... What if i don't find anything to talk about with Nadeen?"

"Don't worry, just relax and don't be grumpy like the last time. Also, you may let her talk and just listen pretending to be interested."

"OK, sounds easy."

"Yeah! Also, don't forget to dress properly and maybe... go to see your naughty MILF before."

"Why should i see her?"

Mark looked at him with a smirk: "Never go to get groceries if you are hungry."

"Don't tell me, your grandpa again?"

"Of course."

"OK, I'll do it!"

After work, Jake got some groceries and went back to his apartment. After a light dinner, he chilled out on the bed watching videos on his laptop, then he started to think about Paula and the amazing sex he had with her.

Automatically, he closed the fan-made video about fantasy adventurers he was watching and went to his favorite porn site, browsing for "milf". After watching some videos, he realized that porn wasn't doing as it used to do.

All his life he had been taught that sex was a dirty, shameful affair. A thing that should always be kept secret and can't be spoken about. This was more than enough to excite his curiosity. Soon, he started to find out about sex through porn on his computer. Exploring that crazy underworld became his hobby other than his guilty pleasure. He often promised to himself that as soon as possible he would leave his boring town to work in the big city and indulge in every perverted pleasure he could even desire. Those had been the ideas that had been swirling in his mind during his teenage years as long as a quick jerk didn't wash them away. However, now that he had been living in the city for some weeks, he realized that the freedom he was enjoying now had somehow reduced his pleasure. The excitement generated by the risk of being caught by someone. The delightful feeling of excitement burning inside him like a fire while he waited for the right moment when he was alone and he could indulge in some forbidden pleasure. All those sensations were gone now and he realized that, oddly, he was missing his old life at his parent's home.

Searching for stronger excitement, Jake clicked on another thumbnail. He opened a video named "Veronique first gang bang".

A hot blonde woman with huge boobs was sitting on a couch. She was dressed, so to speak, with a lace bra and thong. A garter belt, also made of transparent lace, was holding his nylon stockings. She was sitting alone, smiling at the camera. She looked happy and excited. An off-screen male voice asked: "Would you start by introducing yourself?"

"I'm Veronique and I'm 35 years old."

"How long have you been in the porn industry?"

"I started 3 years ago, but before, i used to make amateur videos with my husband."

"Does your hubby know about what you are about to do?"

She chuckled: "No, I want to surprise him with the video."

"He will love it."

"Yeah, for sure!" Veronique caressed her voluptuous breast: "he loves to see me fucking other men."

"So we must thank him if you are with us now."

"Yeah! Thank you for having turned me into a slut, honey. I love you", she blew a kiss to the camera.

"She looks so happy", Jake thought, while a part of him asked what the sex could be from the point of view of a woman.

"Let's introduce the guys", said the male voice.

Some guys got inside the camera range. They were all studs with big muscles. Veronique stood up, welcoming the men who were about to fuck her. She looked at them with desire. The gang got closer and started to touch her, their big cocks already hard inside the boxers. Jake could observe the scene from different angles: the guys caressed her butt and groped her boobs, making them come out from the skimpy bra she was wearing. Veronique grabbed the shaft of two guys. The feeling of those meat sticks made her squeal delighted.

"It seems that women have the most of the pleasure and they can have it many times", Jake thought. "That's unfair."

In the video, Veronique was now kneeling and sucking the two cocks she groped before while the other guys were around waiting for their turn.

Jake asked himself if he could ask Paula about how it feels but he soon realized that it could be a very stupid question to ask. Then he remembered a certain paper bag he left in his wardrobe yesterday evening and a crazy idea came to his mind. An idea that made him feel excited and scared, as he used to be the first time he discovered porn.

Jake paused the video and jumped down from the bed, then he recovered the bag and let its sinful contents fall on the bed. Jake spread that soft black mass of lace and nylon and he recognized the garments that Paula was wearing when he took his virginity: a transparent corset with suspenders, a thong and a pair of nylon stockings.

With his mouth watering already, Jake took a few moments to admire his lewd souvenirs. He caressed the nylon, trying to recall to his mind the feeling of Paula's legs, then he tried to smell it and he felt her perfume mixed with the wild musk of her pussy. He was mesmerized by those scents. Searching for a more extreme stimulus, he sniffed the thong's crotch. The smell was very strong; he would have judged it disgusting in normal conditions, but now he was horny and automatically he took the dirty thong and put it on his face, inhaling deeply.

Jake was at the peak of his excitement but he didn't want to make himself cum, not yet at least. Instead, he caressed the soft corset and when his hand reached the empty cups he had a crazy idea.

"What if... if I try it on?", he thought.

With his hands made shaky by the excitement, he took the corset and tried to wear it like a t-shirt. It was a little tight for him and, afraid to break the soft fabric, he desisted. Then he tried to put his feet inside and pull it up. This time it worked. Jake could feel the nylon and the soft lace creeping over his skin. As a guy that obviously had never worn anything like that in his life, that new feeling gave him a shiver.

Jake pulled up the garment in place and put his arms inside the little shoulder straps. Except for the cups that looked sadly empty, all the rest was as tight as a second skin.

"Why has it to feel so good?", he said to himself.

Jake moved a little and he felt the hard cold suspender's hooks against his thighs.

"Oh, this is annoying... Unless..." he looked at the nylon stockings and the thong left on the bed.

There was no way that his hard dick could fit into that small thong, but Jake wanted the full experience and he wore it. Again, the feeling of soiled lingerie against his balls made him feel even more excited. After that, he grabbed the stockings. Wearing them was tricky, but finally he made it.

"Oh my, i ended up wearing it."

Dressed like Paula, Jake got on the bed next to the laptop and he pressed play. He looked at Veronique's oral performance. Now she was sucking another guys while she was jerking the previous two.

Jake's hands were caressing his sexy outfit while his mind was full of obscene ideas: "Mmmmm, being a porn actress... Taking cocks..."

Jake's hand caressed his hard rock shaft. Soon, he had a powerful ejaculation that hit his face and left white splashes of cum on the black corset.

As if a switch had been flipped, all the excitement and the desire disappeared. Quickly, he got naked and went to take a shower.

"OK, it was an experiment", he declared to himself. "I must return those things to Paula."

Jake went back to the bedroom, he turned off the computer and got inside the sheets. "What is wrong with me?" he asked to himself. Then he started to think about his life and how it had been lonely. He recalled how the other kids avoided him. How he was considered the weird one. "Maybe they were right. Maybe I'm a weirdo...", he thought.

He recalled old memories and pondered over those things for a while, then he felt in a dreamless sleep.

The next morning, he woke up earlier than usual and full of energy. He brewed himself some coffee and saw the lingerie he played with abandoned on the floor.

"I must bring them back to Paula, but I'd better to wash them before."

After a quick search on the web about how to properly do it, Jake tossed all the stuff in a bowl with cold water and some soap, then he rinsed and hung them in the bathroom to let them dry.

Later at work, Jake met Mark: "Hey buddy, i have news", Mark said, "Claire called me yesterday. She said that they would like to meet us tonight. Is it OK for you?"

"Yeah! Sure. I just have to make some arrangements."

Mark grinned: "go to call your MILF."

Minutes later, trying to speak casually, Jake made his call to Paula.

"Hello! Paula? It's Jake. Yes, yes, it's me. I was wondering, could we meet this afternoon once I've finished work? Yes? Wonderful! See you later then. Bye!"

The working day dragged on slower than usual. At 5pm, Jake walked fast toward the exit and then to the bus that led him home. He went to the bathroom for a quick shower and to take the things he wanted to return to Paula but, unfortunately, they were still damp. Jake decided to let them stay and he quickly walked to Paula's home. Again, he followed the procedure to access and he arrived on the right floor in front of a door ajar. Behind it Paula was waiting for him with a warm smile and a long satin rope. She closed the door behind Jake and kissed him passionately.

"I'm happy to see you again", she whispered, "I'm sorry for the last time. I wished you could have stayed longer with me, but I had to throw you out."

"It's OK Paula, I know it was because you had to work", then he remembered her gift, "about your stuffs, I've washed them but they were still damp. I'll take you back next time."

Paula smiled: "so you had to wash them? Have you used them to masturbate?"

"Yes", he admitted.

"Good boy, play with mommy's naughty stuffs as long as you want."

"Do you want me to keep them?"

"Let's say that I don't need them right now."

"Thanks Paula, but I promise that I'll bring them back to you next time."

Paula looked at him in an inquiring manner: "what's wrong? Don't you like it?"

"No, I love them. It's just..."

"It's just?"

"I don't know how to explain... Yesterday I was watching a porn, a girl having a gang bang and..."

"Come on. Spit it out. I'm not going to judge you or anything", Paula reassured him.

"I don't know... She was so beautiful, so exciting, so happy to be there, used by one man after another, exposed to the whole world and I... I wondered how it could be to be her and I wore your stuffs. Please don't think I'm a weirdo, I'm feeling confused, I'm..."

Paula's kiss stopped that stream of words.

She hugged him tenderly: "it's all OK. You are not a weirdo. You are just exploring, trying new things. There's nothing wrong in that."

"Really?"

"Really! And you know what? There are many men who enjoy wearing female clothes. I've met several of them."

"You mean that your customers do that with you?"

"Yes, some of my customers do it, but my husband also."

Jake looked at her with wide-open eyes: "are you married?"

"Well, I should say my ex-husband. We are not together anymore, but we are still good friends.

"Oh! I see."

After an awkward silence, Paula took the initiative.

"I'm quite disappointed actually. I thought i could enjoy that young powerful cock of yours."

"Oh yes babe!"

The two moved to the bedroom and, to his surprise, Jake noted that the bed and the pillows were lined with a shiny, red bed set that seemed to be made of plastic.

Paula took her cash from a mesmerized Jake and said: "You know? I was sorry for the last time, so I promised to myself that if you decided to come again I would do something very special for you."

Paula opened her robe and let it fall on the floor. Underneath, she was wearing a pair of black ribber stockings and a one-piece swimsuit that looked made of the same material.

"Get naked now and lie down on the bed", she ordered.

In less than a minute, Jake got rid of all the clothes he was wearing and climbed on the bed. The smooth bed set embraced him with its scent of rubber.

"Face down, babe", Paula commanded again.

With some concern, Jake turned himself. His face among the pillows, his ass naked and exposed. He felt Paula climb on the bed then move over him. Her mature yet sexy body wrapped in shiny latex was creeping slowly and sensually on her young lover.

"I want you to relax". She slid down her swimsuit shoulder straps revealing her generous breasts, then she took a bottle of lotion from the night table and poured a large amount on her boobs and on his back.

Before Jake could protest about the unexpected shower, Paula leaned on him rubbing his back with her big boobs.

Jake moaned as he enjoyed that incredible massage. Paula expertly guided her soft tits onto his shoulders, then down to his legs and then up again to the crack of his butt where she teased his tight hole with her hard nipples.

"Ahhhh! I've never felt anything like this", Jake screamed.

"You like my nipples on your little hole, don't you?"

"Yessss!"

"Do you want more?"

"Yes! Yes! Please!"

With both her hands, Paula opened her butt cheeks, then she licked his anus.

"Ahhhh Paula. What are you doing?"

"I know that this is the G-spot of you guys", she answered. "Do you know that you can have more?"

"More? How? Ahhhhh", Jake moaned as Paula penetrated him with a finger.

"In this way, babe. Do you like it?"

"Oh my! Oh my!"

"I have an idea. Let's try this."

Paula took a small vibrator from the night table. She rubbed it with some lotion and turned it on. The unknown buzzing alarmed Jake, who asked, with a shade of panic in his voice: "What's that?"

"Don't worry babe, just relax."

The little, well-oiled toy got easily inside Jake's virgin ass. The contact of that vibrating thing with his prostate gave him a wave of pleasure like he had never felt before.

"Now turn, look at me."

As ordered, Jake rolled on the now slippery bed and faced Paula, who was above him on her knees.

"Do you like it? We ladies use those toys when we don't have a handsome boy to fuck. After meeting you, I used it on me thinking about you babe."

"Ahhhh Paulaaa."

Paula added more lotion on her breast, then massaged his chest and then his erected cock.

"I like you so much, Jake. I was afraid you wouldn't come to see me again."

Paula looked delighted at the veiny texture of his dick, then she started to lick the shaft as it was the most delicious ice cream.

"Mhhhh, your young and powerful cock..."

She jerked and blew him, caressing his purple hat with her greedy tongue. The expert mouth of Paula and the vibrator still buzzing in his ass were just to much for Jake that with a scream delivered a big load of cum right into Paula's face, who giggled amused.

"Ahhh, so much fresh cum."

She licked him clean, then she took off the vibrator from his ass.

"Jake please, i need you to make me cum. Use the toy."

He was still recovering from the powerful orgasm but the sight of a dirty Paula with his cum still on her face made him move. He shifted the crotch of her swimsuit and started to kiss her pussy with passion as if it was a lewd, post-orgasmic cuddle. Paula grabbed his hair and moved his head to make him lick her clit.

"Mhhhh yeah. What a tongue that you have. Stick that toy inside me now!"

Without stopping his licking, Jake grabbed the vibrator and stuck it inside her wet cunt.

"Ahhhhh! Yes! Ahhhh! Jake, you fuck me so good! Ahhhh! More, lick me more."

He licked her with all he got, delighted by the obscene scent and the shiver that every stroke gave to her.

"Oh baby! I'm cuuuuming!"

A huge stream of liquid erupted from Paula's pussy. He knew what it was. He had seen in porn: he made Paula squirt. Excited, Jake tried to slurp her love juice while Paula was lying on her back almost passed out after that powerful orgasm.

"Oh my... You made me squirt... Kiss me now."

They kissed passionately, in their mouths the tastes of their pleasure. After some minutes of that depraved make out, the two lovers cleaned themselves up in the shower. After a while, Jake broke the silence.

"I am surprised."

"Of what?"

"I didn't know that you liked me so much."

"It is so weird?", she asked rhetorically.

"Yes, I mean no, it's that... i thought that nobody liked me."

"Oh babe! I do like you and I'm sure that I'm not alone."

"I don't know... I've never had a girlfriend in my life."

"Oh come on! You are a nice cute guy. I'm sure there were many girls who wanted to spend time with you when you were at school."

Jake recalled that time as he did yesterday evening before sleeping.

"Now that you make me think about that...", he started, "I believe that maybe there was some but I've ended up ignoring them."

"Oh no! Why did you?"

"It's complicated... Girls were a mystery for me. I didn't know how to manage them."

"Manage them? What do you mean?"

"I mean that i don't know what they wanted, what made them happy, not even what they did during their free time. And...", his eyes got a little watery, "I couldn't ask anyone. My parents just wanted me to be like the other guys. Like playing football and stuff. But I've always hated that. I was the weird guy already. I thought that if I had spent time with girls, my parents and the other people around me might think that I was gay or something like that."