To Overcome His Shyness

Ambrose stirred in his bed, his body turning and tumbling in a slow, sluggish motion. His limbs were heavy, weighed down by the aching reality of his life. On Sundays like this, his boredom built up to such a level that he thought it could almost break through his skin.

He dragged himself out of bed, feeling the coldness of the air around him. It was a grey morning, and rain was lightly dripping down the window. He stepped outside his small home, the rain crashing against his face like tiny pellets. He stumbled to his mailbox, not noticing the magical details of the morning, and pulled out a newspaper.

Back inside he made himself a cup of coffee before collapsing onto the sofa. As he scanned the ads, he realized that the rain had muddled some of them up, leaving him with partially unreadable bits. Still, most of it was legible enough for Ambrose to understand the message, and he enjoyed how it was like a game to figure out what the missing parts could be:

"Eleonore, 19y, blonde, slim, [blurred]ur wildest desir[blurred]pert in roleplaying!"

"Do you need a student loan? We provide all k[blurred]s of [blurred] financially. CALL US TODAY!"

"Mr Twister [blurred]ther writers to make a cameo in their own stori[blurred] flirt with him. Wouldn't it be amazing to [blurred]ck and forth and cre[blurred]f meta-story?"

"Garden Maintenance. Exp[blurred]nce in maintenance wo[blurred] large diversity of trees, plants and flow[blurred] your beautiful lawn."

"Has anyone seen my cat? She is black wit[blurred]uld be greatly appreciated!"

One ad in particular caught his interest: "Looking for an amateur s[blurred]r to provide entertainment free of charge [blurred]ouse party to celebrate the birthday of my friend Ally [blurred]tact crazypony182@tmail.com"

Ambrose had an incredible passion for singing. He was always eager to join in with songs on the radio, and when he was by himself, he often found himself humming his favorite tunes and singing out loud, as if he was in a karaoke bar after a few drinks.

He often dreamt of singing on a stage, but his crippling shyness had always stopped him from pursuing this dream. This ad seemed to present an offer to perform for a small group of people, which he thought could be a good chance to push past his introverted nature as a first step, before eventually taking the stage in front of larger audiences.

He replied to the ad, and a few days later he received an answer from a girl called Penelope. The party was the following night at 8 in Ally's house. Ambrose replied to confirm his presence, and the next day he mustered up all the courage he had to show up at the door.

Penelope answered the door with her blonde hair pulled back in a tight bun and a hesitant but welcoming expression. Ambrose could feel his heart fluttering as he introduced himself to her. She stepped aside to let him in, and he was immediately taken aback by the vibrant atmosphere of the room.

Four girls were seated around a circular table in the corner of the room, all dressed up in their finest attire, each holding a glass of wine and chatting away animatedly. Penelope gestured for Ambrose to move closer and meet the others.

"Hey ladies," Penelope announced "it looks like our entertainment for tonight has arrived. Let's take a moment to get acquainted before we get to the exciting bit, shall we?" She sounded quite eager to hear him sing, he really hoped he wouldn't disappoint her.

One by one, he was introduced to the girls: The first was birthday-girl Ally, a brown-haired beauty with bright blue eyes and plenty of freckles. She wore her hair in a long braid and looked very gentle and likeable. The second was Samantha, a tall, statuesque woman with long red hair and a laugh that filled the room. She was confident but not at all arrogant. Next came Sarah, a sweet-looking girl with curly black hair and doe-like brown eyes, who appeared to be almost as shy as himself. Her face was weather-beaten, but her youthful spirit still shone through.

Then there was Grace, a stunning blonde with a wicked smirk and piercing green eyes. He wondered what it would be like to wake up next to her every morning. Her tanned skin looked smooth to the touch; he wanted to run his fingers across her shoulders, down her sides and along her arms... Finally, we had Penelope herself, who had a mischievous glint in her eye that Ambrose couldn't help but find alluring.

Ambrose's heart raced as he took in the sight of the women. He had never been in the company of such a group of beautiful and confident women before. He felt his cheeks flush and his palms grow sweaty, but he tried his best to appear confident and composed. Grace whispered something in Ally's ear and they both giggled.

"Well Ambrose," Penelope went on, as she moved towards the makeshift dancefloor with a large stereo set next to it. "I imagine you didn't come here to exchange small talk with us, so I suggest we move on to your little show. Perhaps you brought some music to accompany your performance?"

As Ambrose followed her, he realized he hadn't really given that much thought beforehand. Now he regretted not bringing some music, since that would certainly have helped him to keep the rhythm and tone. Well, no point fretting about it, it was too late now anyway. "No, that won't be necessary, just a microphone is all I need."

"Why do you need a microphone, baby," Grace interjected "did you plan to bend over and allow us to get creative?"

Laughter broke out all around the table, but Ambrose didn't quite get what she was implying.

"I don't understand," he said "I always use a microphone to get the best vocal performance. Do you mean you don't have one?"

The surprised look on their faces immediately told him something was off. Like someone in an orchestra had just played a very audible false note.

Penelope broke the awkward silence: "Honey, you never mentioned you were going to sing during your striptease. That sounds kind of weird to be honest."

Ambrose froze in place as he suddenly realized his stupid mistake. The illegible word in the ad hadn't been 'singer' at all, it was 'stripper'. Because of his desire to sing before an audience, he had jumped the wrong conclusion far too quickly, and now he found himself in quite an awkward situation. He decided to be honest and admit his mistake.

"Uh, I think there has been a misunderstanding," Ambrose began, feeling his face heating up in embarrassment. "I thought you wanted me to sing. I didn't realize it was for...um...other entertainment."

The girls looked at him skeptically, and Ambrose could feel his heart pounding in his chest. He had never been much of a ladies' man and the thought of taking his clothes off in front of a group of strangers was terrifying.

"Are you serious?" Grace asked, a smirk playing at the corners of her lips. "You thought we wanted you to sing? That's precious."

Ally put a hand on Ambrose's shoulder and gave him a sympathetic smile. "It's okay, honey. We all make mistakes. But if you're not comfortable with what we're asking, you can leave. No hard feelings."

Ambrose hesitated. Despite her comforting words, Ally had a sad look on her face, while Grace and Penelope looked somewhat angry at his confession. It was obvious the girls had really looked forward to this moment. He was already here, and the thought of walking out and leaving the girls disappointed made him feel guilty. He took a deep breath and tried to compose himself. Maybe there was a way he could make it work.

"I don't want to disappoint you all," he said slowly. "And while I'm not exactly what you had in mind, maybe I could still provide some entertainment. I could sing a song while I...um...strip." He cringed at the thought of what he was proposing, but he knew it was his only chance to salvage the situation.

The girls exchanged a surprised glance, but then they all broke out into laughter. Samantha clapped him on the back and said, "Now that's what I call creative problem solving!"

Ambrose felt relieved that they were taking it well. He had no idea how he was going to pull this off, but he was determined to try. Penelope put on some background music and gave him a mic.

Standing on the dancefloor, Ambrose closed his eyes and took a deep breath, then started to sing. His voice was smooth and soulful, and the girls immediately quieted down to listen. As he sang, he began to move his body to the rhythm of the music, slowly unbuttoning his shirt and exposing his bare chest. The girls watched with rapt attention; their eyes fixed on him.

As the song reached its climax, Ambrose took off his shirt and swung it around his head, revealing his toned abs and muscular arms. The girls cheered and clapped; their eyes bright with excitement.

Ambrose couldn't believe he was doing this, but at the same time, he felt a sense of liberation that he had never felt before. For the first time in his life, he was letting go of his inhibitions and embracing his sexuality.

He sang another song, this time taking off his pants and revealing his underwear. The girls gasped; their eyes wide with anticipation. Ambrose couldn't help but feel a surge of excitement as he danced around the room, his body glistening with sweat.

When the song ended, Penelope leaned in and whispered something in his ear. His heart skipped a beat when he heard her words: "Don't you think Ally deserves a private lap dance and a close-up view of your manhood?"

Ambrose glanced over at Ally and saw that she had a little half-smile on her lips. He took this as an opportunity to make things right with the girls, so he gave them all a wink, and moved closer to Ally while he started his next song.

As he sang, he moved closer and closer to Ally until he was right in front of her. She looked up at him with a mix of curiosity and excitement. He could feel her warm breath on his chest as he leaned in, and he felt a shiver run down his spine.

He started to grind his hips against her, moving to the rhythm of the music. She giggled and blushed, but she didn't pull away. Instead, she wrapped her arms around his waist and pulled him even closer.

The other girls cheered him on, shouting encouragements and catcalls. Ambrose felt like he was on top of the world, the center of attention of a group of beautiful women. He moved his hips faster and faster, and Ally let out a little moan. Now it was time for the grand finale!

He grabbed the waistband of his underwear and flung it to the side, revealing his fully erect cock. The girls looked at him with amazement and a hint of lust in their eyes. Ambrose felt a rush of adrenaline as he danced around the room and sang, his cock bobbing up and down as he went. He danced back towards Ally, who was looking at him with great anticipation, while the other girls kept cheering him on.

"Come on, Ally, touch it!" Grace shouted, and soon the others joined in, chanting "Touch it! Touch it".

Ally reached for it and stared at it, she had never seen a penis so close before, and she couldn't help but be impressed. When she touched it, it felt warm and throbbing, like a tiny animal trying to escape its cage.

She wrapped her hand around it and gave a little squeeze, and Ambrose let out a sharp gasp. Then she went ahead and gave it a little kiss. Ambrose looked at her with a surprised expression on his face and then he gave her a little smile. Ally smiled back and moved in to give it another kiss. She kissed it over and over again, while the other girls yelled encouragements in the background.

Penelope had moved behind him and her hands were molding his naked ass, giving him a little massage. In this moment, Ambrose felt like he was the center of the universe, and all the girls in the room were there for him.

Ally started to move her hand up and down his shaft, while Penelope was still standing behind him moving her hands all over his body. Grace also got up and removed her shirt and bra, presenting her wonderful breasts to Ambrose, who didn't need much encouragement to start licking them.

He looked around and saw Sarah glued to her chair, watching the whole scene with amusement. And then he caught Samantha, who had slid her hand under the table, it was pretty obvious what she was up to.

Ambrose was the center of attention of a group of beautiful women. He was the man of the hour, and for the first time in his life, he felt like a real man. This was the moment he had been waiting for - a moment to let go of his inhibitions and be himself.

Penelope suddenly had an idea and whispered in his ear: "I know Ally's biggest fantasy is to sit on a man's face, if you understand what I mean. I can't force you, but you could give her the perfect gift to make it a birthday she'll never forget."

Ambrose gave it a bit of thought, then nodded, and she pointed at the couch where he could lie down. Then she fetched Ally while also whispering in her ear. Ally's eyes lighted up as she realized what Penelope had planned. Slowly she began to undress, then took place above Ambrose, before she let her vulva sink right above Ambrose's mouth.

His eyes widened as he looked at the beautiful sight in front of him - her delicious wetness just inches away from his face. He licked it gently at first, tasting her sweetness for the first time. She moaned and pressed herself against him, pushing his face into her pussy even more. He moved his tongue around her clit, feeling its hardness against his lips.

He pushed his tongue deeper, exploring every inch of her tight little hole until she gasped in pleasure and writhed against him. His fingers joined in the exploration too as he reached up to rub and caress her nipples while his tongue continued its journey around her wetness.

Because he was so focused on Ally, the sudden hands on his body came as a huge surprise. They went over his chest, belly and legs, before taking his penis in a tight grip. As they slowly started stroking his shaft, he felt a second pair of hands on his chest. He could still see Samantha and Sarah at the table, so it was clear Grace and Penelope were having a bit of fun of their own. He wondered whether his dedication to please their friend Ally had something to do with it.

Either way, the combined attention was just too much for Ambrose, and soon enough, his body responded with an explosive orgasm. As the waves of pleasure washed over him, he felt Ally collapse on top of him in a similar state of bliss.

When they both recovered from their climaxes, the girls thanked Ambrose and asked him to stay for dinner. There was something special in the air now, something that wasn't there before. It seemed like Ambrose had earned their respect and admiration - and maybe even something more!

...to be continued...