A Sissy's Awakening Ch. 01

The story of a young boy who learns he doesn't need to wear the pants in the relationship.

Also this is my first time trying to write a story, English is also not my first language so sorry if its not the best.

*****

Introduction: Skip this if you don't want a backstory.

Danny was a soon to be an nineteen year old virgin, Danny hated the idea that all his friends had got laid years before he had so much as kissed a girl. However, from a girls' stand point Danny wasn't much of a prize, he had a sleek feminine frame and facial features most girls would kill for. He had long stretching legs and slender arms that tapered into small almost dainty hands with the most beautiful shapely nails. His eyes were a light blue that shimmered in the sun like a fresh morning sun on peaceful lake. All In all, most girls didn't think much of him, he wasn't extremely smart; he didn't have abundances of cash or rich parents and his body wasn't the usual handsome hunk that the girls he fancied seemed to always fall for.

Danny also had some pretty fucked up fantasies, the result of years of jerking off to porn had driven him to constantly find more and more extreme stuff to get him excited. One of those fantasies was she males, or more precisely the thought of what it would be like to have the body of a woman and a huge cock hidden away in her panties. Of course, this lead him to discover crossdressing and later sissies, over years of learning about them and obsessing about them he slowly came around to the idea that he may be one himself. However, he always depressed the feeling and insisted on that fact he was a stone cold alpha male.

His life was mediocre, most nights were spent at home, on his computer or jerking off, with the occasional night out if his friends were having a 'lads' night'. His sex life was non-existent and this was the thing that bothered him the most. His friends all had girl friends or someone to hook up with yet he was always left with his hand and his computer. It was soon approaching his 19th birthday and he was almost desperate to get laid before he got there, to accomplish this he decided he would do something he never anticipated having to do; posting an ad on Craigslist.

Chapter I: Desperation.

He'd done it! He posted the ad, all be it with some tweaks to make him seem like less of a loser than he was. Danny decided to go to sleep and check in the morning if he had any replies, and with that he got into his bed, fired up his laptop and found his favourite porn video and got to work.

The next morning he awoke to a rather predictable but empty inbox, defeated he closed his laptop and got ready for college. Half an hour later whist driving to college his email notification sounded from his phone in his pocket, excited at the prospect of losing his virginity he fumbled for his phone and frantically checked his email. "holy shit" was all he could think as he spotted the subject of the email "interested in your CL ad". Although simple it filled him with hope.

That day was rather unproductive with Danny spending a lot of his time firing emails back and forth with the mystery girl. He later learnt that her name was Racheal, she was 19 and lived a few miles from his home. Over the course of the day they discussed random things but not so much that either one of them could decipher the identity of the other. It was plainly obvious that Racheal was a lot more confident than Danny was with her asking when and where they were going to meet.

Danny said that he was free on the coming Friday seeing as he didn't have college then and both his parents and his older sister would be at work. Racheal agreed with a simple "sounds great, I'll see you Friday" with a winky face on the end.

This sent shivers down Danny's spine, he had arranged for a girl, who he had never met to come to his house and have sex with him; with Danny the 'strong and experienced top' as he had so humbly described himself.

3 days had gone by It was Danny's nineteenth birthday, more importantly it was Friday. After his family had given him his presents they had all left for work leaving Danny alone. As soon as the door closed he ran to his room and checked his phone, 7:40, he had just over 2 hours until his special guest would arrive.

He checked the house making sure that his room was spotless and somewhat presentable. Once that was done he went and had a long shower making sure to get extra clean and fresh. He then got dressed in something comfortable but smart, wishing to make good first impression. It was 9:30 and the nerves were beginning to build, as the minuets crawled by he started wondering about so many things. What would she look like? What were they going to do? Would he manage to not embarrass himself?

Finally, at precisely 10:02 the doorbell rang, with butterflies in his stomach he approached the door, he could just about make out a silhouette though the opaque glass. It was a thin figure, but he couldn't make out much. He grasped the handle, took a deep breath and opened the door. There she was, one of the most beautiful women he had ever seen, she was stood on his door step, with her hands together in front of her mildly looking up at him with a huge pearly smile staring right at him. "Hi Danny!" she beamed. Danny quickly greeted her and asked her inside and with a meek nod she proceeded inside and walked past Danny. He quickly closed the door and upon swivelling around was met with the most amazing sight ever, Rachael was walking away from him, her perfect ass jiggling as she strutted confidently inside. She placed her small tan leather backpack by the door and Danny wondered what things she might have inside.

Danny moved her over to the kitchen and offered her a drink, coffee would be great she replied. Danny opted for something a little more potent to boost his seemingly lacking confidence. They began chatting while enjoying their drinks and Danny carefully examined her trying not to make it look too obvious. She had a thin but not tiny frame with long legs hidden beneath a pair of leggings, her toned and tanned midriff was exposed below the daringly short tank top which could barely contain her rather large and pert breasts. Moving up her face was that of a goddess, it was perfectly shaped like it had been carved by angels. Her soft plump lips looked so tender and inviting and her eyes where a rich chocolate colour, bordered with long curling eyelashes that made her eyes look so large and sultry. Finally, there was her long brunet hair that flowed down her body like a river. What Danny didn't realise was that at the same time she was checking him out. She wasn't disheartened by what she saw but she could tell he had lied a bit on his ad to get some extra attention.

After about 20 minuets Rachael leaned in and placed her hand on his chest, pushing her hips into him. She immediately felt some movement down below as Danny got more excited. Slowly she moved her other hand down towards his crotch and with every inch Danny got more and more tense. Her hand came to rest on Danny's shaft and Danny could barely contain himself. She was looking up to him, her face so perfect as she stared into his eyes looking for approval. Danny slowly moved his arms around her and placed his hands on her ass, he could feel the heat radiating off it as he began to squeeze and play with it. As both of them started to come alive with pleasure they leaned in for a kiss, Danny didn't know what to expect, he'd never done this before and he didn't exactly know what to do. Their lips collided, Danny was engulfed in a wave of pleasure as his lips met hers.

They backed away, staring longingly at one another and leaned in once more, this time a little more adventurous. Rachael broke off the passionate kiss and asked where the bedroom was. Danny's head was racing as he followed her to his room, all the while staring at her behind. He opened the door and she headed in, she quickly spun around and grabbed Danny with both hands and placed him on the end of his bed. "Wait here" she said as she trotted out of the room.

Danny was so confused, had he done something wrong? Where was she going? He lay back on his bed, a tent in his trousers as he stared at the ceiling. 10 minutes later with a quiet ahem Rachael appeared in the doorway. Danny sat up and almost fell right back down in shock. There she stood, clothed in what can only be described as a heavenly array of flesh, lace and beauty. She had the most revealing and skimpy little black thong he had ever seen, it barely contained the small and aromatic mound beneath it. Paired with a short black lacey bustier that clung to her perfect breasts revealing the small dark epicentres of each luscious mound, with a small pink bow in the valley between them. Moving down her legs were a pair of silky black stockings that truly revealed the perfection of her skin below, again topped with small pink bows. And on her feet were a pair of hot pink stiletto heels, with probably 4 or 5 inch heels, giving her a commanding height advantage of Danny.

She slowly sauntered over, making sure to show off her body as much a possible. She slowly bent over in front of him, exposing her perfect ass to him, barely feet from his face. It's safe to say Danny was fighting to hold on at this point. Then she turns around, gets on her knees and slides between his legs. She places her hands on his jeans and quickly rips them down his legs, exposing the protruding object that lurked beneath his boxers.

She began to rub it through his pants, getting him more and more excited. Suddenly she stood up, Danny opened his eyes confused and disappointed at what she was doing, but he soon realised. She ushered him up the bed and soon followed, crawling up the bed until she was straddling him. She grabbed onto the hem of his boxers and pulled them down, Danny's 5 inch cock sprang to attention, she stared at it for a second, examining its size and shape, but she then moved in. Pressing her soft red lips to his shaft sending Danny crazy, he struggled not to cum right away.

She slowly teased him, moving up and down him, licking and sucking as she went. She moved to the top and wrapped her slutty lips around his tip. She began to suck gently while stroking the head with her tongue, then she began to move her head up and down, up and down, slowly picking up the tempo, occasionally looking up to see the state of euphoria that Danny was experiencing.

After about three minutes of this Danny could simply take no more, he started to moan and grunt at the pleasure Rachael was giving him. "Rachael I'm going to cum!" he gasped. Some what surprised Rachael kept sucking until boom, Danny could hold it no longer and he shot his load right into her waiting mouth.

Danny fell backwards and tried to regain his breath from the earth-shattering orgasm that rust rippled through his body. Disappointed Rachael pulled back while still stroking Danny's cock. Danny looked up at her, she opened her mouth to reveal the half mouthful of cum she was holding and then proceeded to swallow it all, she gave him a slutty wink and Danny just about fainted.

After the arousal had faded she realised she wasn't going to get the fucking from this looser she so desperately wanted and she started to leave to get changed. Danny shot up "Wait, you can't go yet" he exclaimed. Rachael snapped "It's not like you could fuck me looser" she fired back at him. It pierced Danny like a bullet, he felt so ashamed, so pathetic in that moment he just gave up, he didn't fight back like a real man would he just accepted it, that this was his fate, some looser that couldn't please a real woman. And with that he put his head in his hands and began to sob.