And what a life it will be

Erik was left somewhat speechless. He could only imagine what she was going to do with that photo. Butterflies began to flutter in his stomach and a smile crept upon his lips. But through all this happiness, he couldn't ignore the distinct smell of sweat poking through the sweet scent of Olivia's shampoo. He looked down to his side and saw his laundry basked, filled with dirty and torn boy clothes. He felt strange thinking of them as "boy clothes" and not just clothes. They looked nothing like the clothes he was currently wearing. Hardly any color, all torn and still very sweaty. He winced at the idea of changing in to them, but it wasn't just because they were sweaty. He had begun getting used to wearing more girly clothes, even in such short time. He chalked it up to him just wanting to look good for Clara, and he already wore exactly what she wanted.

He shook his head as his thoughts started to actually bother him as they were racing left to right in his head, clashing and crashing. It was all messing with his masculinity. He still had that voice in his head that told him how wrong this all was. Although he did notice how that voice suddenly disappeared when in the presence of his boss, Clara. Everything she did to him felt right in the moment. But now that he was away from her, he became claustrophobic in his clothes... his body. He sighed and got out of his bathroom, making his way to the small kitchen. He opened the fridge and was hit with a distinct smell of something rotten. He sighed once more and sifted through what he had and fished out the bowl of cereal that he ate this morning. He took off the plastic and started eating. The sogginess didn't really bother him too much, although he would have preferred it a bit more crunchy. "My bed has felt so empty", her words came to mind once more. Did she plan for me to sleep in her bed? But I'm just her assi- his thoughtful speculation was interrupted by the events of the day. The blowjob, getting molested, the shower, getting a girly outfit. Perhaps this wasn't going to be a normal job? If so, what did she have planned?

Through his thoughts, the images of being handled crossed his mind. He felt a stirring in his baby pink cotton panties. He bit his bottom lip and caressed the front of his booty shorts, making him moan. He quickly placed his bowl in the sink and made his way to his bed. He practically jumped into it with vigorous enthusiasm. He hooked his thumbs into the hem of both his panties and shorts, pulling them down to his knees. His hand slowly made its way to his tiny penis, though instead of going straight for it, he decided to slowly slide his hand over his body. Starting on his chest then slowly caressing his way across his lean stomach and over his pelvis. Finally getting a grip on his penis and slowly jerking it, he remembered having his nipples played with. Without doubt he brought his other hand up to his pecs, squeezing one of them as if they were a breast. Almost as instinct he began using his fingers to rub circles around his left nipple over his pink shirt. It felt surprisingly good, even though he wasn't as good as Clara. As the jerking and squeezing proceeded, he felt a strange sensation in his anus. Somehow he had associated this pleasure along with having something inside his ass. "Amazing!" he thought, after just experiencing anal penetration twice, he had already started to relate pleasure with anal stimulation.

After the thought crossed his mind, he became curious. The hand which was pleasuring his nipple started to slide its way across his body down between his legs, then further down. As his fingers arrived at the entrance of his asshole, he felt a slight anticipation. He made circles around the sphincter with two fingers. Then suddenly he felt something strange. His asshole twitched? He bit his lower lip as he brought his slender hand towards his face and into his mouth. As he sucked on his fingers as if they were a cock, a muffled moan escaped his mouth. After sufficiently lubricating his two fingers with saliva, his hand traveled down his body once more. His fingers now pushing against his puckered anus, the jerking of his penis began to speed up. After some trail and error, his fingers slowly started to enter his asshole which caused him to moan quite audibly. As he passed half-way up his fingers into his anus, he withdrew slowly only to drive them back in. There he was, laying in his bed dressed as girl and fingering his asshole while jerking his tiny penis. With time, the pace at which he was fingering himself quickened. Strangely he started paying less and less attention to his penis as the sensation in his ass began to overpower it. As his anus loosened up a bit, he felt bold enough to slip in a third finger which only increased the pleasure he was feeling. This wasn't the first time he'd have something in his ass but the sensation was new enough to almost shock him with how good it felt.

When he started to approach orgasm, the pace of his finger-fucking was nothing but ruthless at this point. Through out his masturbation session he had been panting and moaning as if he was a girl. He almost surprised himself when he got too deep into his ass and sent out an overly feminine gasp which was then followed up with an equally feminine moan. Jolts of pleasure were suddenly shooting through his entire body as he experienced the most intense orgasm he had even felt. Tiny jets of semen shot across his girly clothed torso, some of it even landed on his face which he instinctively licked up. Now laying speechless and spread across his bed, he looked wide-eyed up into the ceiling. Thoughts of desire and regret now mixed within his mind, the memory of fingering his own ass still fresh in his memory. Did I actually lick up my own sperm as soon as it hit my face? Why did I almost stop jerking my penis as I got closer and closer to orgasm, when the fingering of my ass only became more rapid?

He slowly pulled up his panties and booty shorts, letting his penis settle comfortably into them. As he looked down he realized that he forgot to take off his shirt. It had a streak of cum marked on it. He blushed, what would Clara think? Despite the state he was in and how early it was, he yawned and stretched. His eyes slowly shut and he slipped into unconsciousness.