It Happened on a Dare Pt. 02

Jay awoke the next morning, John was no longer in bed with him and he found both his friends had gone so he dressed and left for his apartment but not before taking the outfit he wore last night.

Over the next few weeks Jay found himself dressing in that sexy outfit each night and as each day passed he found himself feeling more and more effeminate. He had called his two friends several times with them seemingly avoiding him which left him feeling both lonely and a bit confused since it was them who dared him to dress this way so why should they avoid him.

Another two weeks passed, in that time Jay had found a store in on-line reviews that catered to guys who liked to dress as woman and went to visited it spending over $2,000 for his new wardrobe. He would spend the next 3 weeks dressing as a woman at night and all day on the weekend before he finally worked up the nerve to go out in public dressed in a nice pair of pink Capri length yoga pants, a pair of pink tucking panties allowing him to hide his little cock, a sexy pink strapless bra holding his new b-cup silicone breasts he purchased on-line, a tight pink crop top, pink ankle socks and pink tennis sneakers. After looking at himself in the mirror he was amazed at just how pretty and sexy he both looked and felt, again he felt that deep feeling inside himself again almost the same tingling feeling of desire but his cock again was still soft and didn't know why he felt so horny but not in his cock.

He decided since he hadn't shopped in over a week he would go to the grocery store. As he walked the aisles he became ever more turned on feeling a more intense tingle deep in his loins but again not in his cock. As he walked past one very handsome older man he noticed the man's head turning following his movement down until Jay disappeared around the corner to the next aisle, Jay felt an enormous sensation fill his body only this time his cock did get semi-erect but even more so that sensation seemed to travel to his tight ass feeling his ass tighten and release several times as his blood seemed to rush from his face almost making him feel a little faint.

Jay paid for his groceries and quickly left the store still feeling both queasy & excited, as he arrived at his apartment he put his perishables away and lay on the couch. He began trying to get himself aroused rubbing his cock through those pink yoga pants but he was unable to get an erection.

Finally he decided to look for some on-demand porn, he found a trans movie with a girl whose build and looks almost match his appearance and pressed to purchase it. The movie started with the girl moving into a new apartment in need of some assistance, a young well built man offers her a hand then within a few moments they embrace. As the man's hand slides down between her legs he is in for a surprise, but what he finds doesn't derail his carnal desires rubbing her until she is very erect.

The woman slide her hand between his legs grabbing his huge cock through his jeans squeezing with her thumb and forefinger jerking him off. The two undress quickly as her panties come off her huge cock falls out, as his pants drop an even bigger cock flops out (almost 9 1/2" hard as steel uncut meat). She drops to her knees kissing & licking it before taking more than half of his shaft inside.

Jay had always been grossed out the few times he watched gay porn but something was different about these two people both with cocks doing this. He could suddenly feel that same feeling running through his body that strong tingling sensation was now very intense as he finally felt his small cock growing rock hard. Reaching into his yoga pants he began playing with himself as his eyes remained rivetted to the action on the screen. His free hand slid to his breasts squeezing and fondling them, even though they were fake he actually felt a sensation fill him almost as if they were real.

The woman on the screen was now kneeling on her bed her ass spread open wide for the stud behind her, the man hovered above before slowly pushing his massive cock-head into her expanding her hole almost seeming ready to tear her open as it popped inside her. The woman moans loudly before pushing her ass back forcing his shaft deeper inside.

As they continued to fuck Jay felt the tingling sensation almost become electric and a desire began to fill his mind, he wanted to feel what she was feeling wanting something filling his ass. Jay jumped up and grabbed the only thing he could imagine as a cock, a cucumber he had purchased at the store quickly spreading olive oil all over it, the only lubricant he could think of.

Taking his yoga pants and panties off he felt his cock fall out, he was amazed at how hard he was thinking he had never been that hard at any time he fucked girls. Kneeling he reached around spreading his ass before pressing the cucumber against his puckered hole, as it touched his sphincter began involuntarily opening and closing and his cock began twitching violently as precum started leaking rapidly out his slit. With one push the cucumber slid deep inside him, a wave of sharp pain filled him but between the action being played out on the screen and the wave of horniness filling his body he started fucking himself rapidly as he also began playing with his own hard cock.

Minutes later his eye still glued to the screen he saw the man begin shooting his cum inside her ass, each time he pushed deep cum would flood out running down her cheeks & down her thighs. Jay imagined it was him that man was fucking and within seconds shot his own load all over the cushions of his couch as he pressed the cucumber deeper and harder each time tightening his ass around it.

Without thinking he began screaming, "Fuck me fuck me harder deeper," as he realized it he put his face into a pillow screaming, "Fuck me, Fuck me," over and over before collapsing lying in his own pool of cum exhausted.

As he lay there he was astonished that this was the best sexual feeling he ever had and at that moment decided he wanted to experience what he saw for real someday. It was then he knew he needed to live more of his life as a girl and decided in his new persona his name would be Janelle...