Being Jack!

[MsBloom]

1. The Boy in the Mirror

It was an early Saturday morning in mid-July, two days after her sweet sixteen when Jackie stood in front of the full body mirror in her room and looked at her naked body, ran her hands over it, cupping her small but firm breasts, giving the bright pink nipples a pinch and a twist, causing herself to moan. She was tall and slender without any particularly feminine forms. Her hips were narrow and gave her a straight contour rather than an hourglass like shape. Her arms and her legs were toned and muscular. Had it not been for the breasts and the absence of a cock and testicles between her legs she could easily have passed for a young man. She smiled at herself and grabbed her cunt, gave it a squeeze and let out yet another moan.
The house was quiet and everyone else was asleep, her mum and dad, her older sister, even the dog and the two cats were still down for the night. It was for this reason she was up as early as she was. The previous afternoon she had been first to the post office to pick up the package she had ordered and then stopped at a barbershop and cut her copper tonedd hair really short. Of course this also added to the possible illusion of a male body and if she turned off the lights the illusion would be there.

She felt excited as she reached for the package and first removed the discreet brown wrapping paper to uncover the box inside. Inside the box was an object she had desired for quite a while but not had the courage to buy until a few days ago when she had put the order through to feeldoe.com and bought a Realdoe Stout (NSFW). Her hands actually trembled as she took it out of the box. It seemed massive, much larger than any of the cocks she had seen in real life. It was the first sextoy she had ever bought, or even been remotely interested in. It had cost her nearly a hundred and fifty dollars but whe knew now that she held it in her hand that it would be worth every cent.

She used the lube she had purchased at the same time on the saddle before opening up her labia and slowly inserting the it into herself. She moaned as it opened her up and then when she felt her vaginal muscles grip it and close around it she took a deep breath and looked at herself in the mirror again. It looked amazing, it was huge but so beautiful. Now to complete the illusion she had a few more steps to take, the first of which was to wrap gauze around her chest to flatten her breasts. She had bought two rolls of it for this purpose and when she did put on a flannel shirt on top of it the illusion was almost complete. The last stage included the fake moustache she had bought at the shop that sold theatre props.

Once that was in place she slipped on a pair of baggy jeans leaving the cock to stick out through the fly. She smiled at herself, or rather she smiled at Jack, or rather still, Jack smiled at himself. She pulled up her desk chair and sat down in front of the mirror. As she softly caressed the cock she began to feel its effect inside her. She wrapped her hand around the shaft and began moving it up and down the way men jerked off. Inside her the saddle moved with each tug and soon she was lost in pleasure. The image in the mirror, of Jack, stroking his big cock, was enough to cause Jackie's cunt to explode within a matter of seconds, squirting inside the jeans, and then again a minute later, and again, and again , each orgasm more intense than the one before until she quite literally couldn't take another.

She let go of the cock and just sat there grinning happily at Jack in the mirror and he was grinning back at her. It had been exactly as right as she had imagined it in the days since she placed the order. The jeans were soaked in her juices and it looked like she had pee'd herself, something she had tried a few times before and quite enjoyed, especially wearing jeans with nothing between the jeans and her cunt. It always felt so good to rub herself through the soaked fabric.
”Well. It looks like Jackie will have to clean up after Jack's made a mess. Such a naughty naughty boy he is.”

 

[MsBloom]

2. A Day to Himself #1

That first morning when Jack became a significant part of Jackie he kept stroking that cock in front of the mirror until the sun shone in through the bedroom window and he heard stirrings from the room behind that mirror. It was Sophia, Jackie's sister, getting out of bed. He could hear her moving about in her room for a little while, probably laying out the clothes she would wear that Saturday and then he heard her door open and close, footsteps moving past Jackie's room towards the bathroom where Sophia would soon be stepping into the shower.

Even though he knew that it was time to become Jackie again he closed his eyes and conjured up an image he had never quite been able to shake. It was that of Sophia face down in her bed and away from the door with her ass lifted off the bed and two fingers noisily moving in and out of her cunt, deep and fast. His mind then wandered to all those times he had seen Sophia buck naked, like in the shower, or when she was changing clothes in front of Jackie, her slender body without an ounce of extra fat on it, her shapely ass and legs, from the front her thighs and her clean-shaven crotch formed an almost perfect heart shape. Her breasts were a perfect hand full with large bright pink nipples.

Helpless to resist those images Jack rubbed out one last orgasm, fast and hard, while first hearing Sophia taking her morning pee, flush and then the shower turn on and then off again some time later. He was so lost in his pleasure that he had no idea if it had been five minutes or half an hour since Sophia entered the bathroom but as he tried to gain control of his breath again he heard the bathroom door open and close again, footsteps passing outside Jackie's door again.

He wasn't caught in flagranti delicto but Jackie had just managed to remove the last remnants of his moustache and temporarily hidden the RealDoe in her bedside drawer when there was a knock at the door and Sophia's voice asking if she was up. Wrapping herself in her black silk kimono with a hand-stitched floral pattern Jackie opened the door and faked a yawn. Sophia was quite the vision even if she wasn't wearing anything special, Short jeansshorts with a plain black camisole top. Her red hair, still damp from the shower, curling down to the top of those beautiful round breasts.
”Sure sis. I'll be down for breakfast as soon as I've showered.”
Sophia nodded content with the answer and headed downstairs. Jackie lingered a few moments to watch her sister's ass sway from side to side. She then closed the door behind her and went into the bathroom. She sat down to pee. After all the orgasms she had had that morning the bladder was full. As she sat there she noticed the black and red stiped panties Sophia had most probably worn for the night. She picked them up and brought them to her face. Yes, they smelled fresh and the scent of her sister sent shivers through her body. For some reason she wouldn't be able to explain she used them to wipe herself and then brought them with her into the shower and used them to rub out yet another orgasm before washing herself.

Two days later Jack was getting ready again.

Jackie's parents had gone to the summer house for the one week when their vacations synced and Sophia was going to spend the day with her boyfriend at his parents house and the night at a nearby motel. It was their six months anniversary so there was a higher probability to win the jackpot on the lottery than for Sophia to return home before the next morning. He had the whole day and night to himself.

Jackie's breasts were being flattened with a roll of gauze, the moustache came on and last but of course far from least the RealDoe went in. Jack then logged on to the chat of the online community for erotic stories he had created an account for late the previous evening after having gone to bed. He wore nothing but a pair of boxers and a simple t-shirt.

Hi … I'm Jack. Nice to meet all you lovely girls, he typed and got a few smiley faces and hellos back but initially not much more.
While keeping an eye on the chat to see if any interesting topic showed up he browsed through some image galleries, amazed at just how willing so many girls were to show off their bodies in various states of undress, not that he complained.

For the most part it was the mature women that did catch his eyes, women old enough to be Jackie's mum, maybe because it somehow seemed naughtier for these mothers and wives to show themselves off to anyone who wished to look, leaving themselves open to all and any kinds of fantasies. The one that most caught his eyes was a woman who went by the name of RedSally. She was in her late forties but had a truly remarkable curvy body with large but still firm breasts that as far as he could judge were all her own. She was even showing her face in some of the nude selfies, of which the one where she stood in front of a mirror with her free hand between her legs and a look of pleasure on her face was the one Jack liked best. He was just about to send her a private message to compliment her on her body when a sharp ding alerted him to someone having sent him a request for private chat. He accepted the request which was from a woman calling herself EbonyMilf.

Hello there Jack, I see you live in the next town from me, the message read and when he checked her profile that was indeed the case and on top of that she was super hot. First of all her skin was like dark chocolate, like 85% pure chocolate and had a swimmer's body, lean and muscular but still very feminine with small but very nice breasts, not unlike Sophia's in shaper and size.
Hi, he typed and added a smiling face.
Nice to meet you. He added and then returned to browsing her image galley.
There weren't many full nudes but lots of pictures of her in lingerie and some topless, and they were not selfies either so that meant someone ese had taken the pictures.
So what are you up to today, she asked and it was obvious she was not looking for just a casual chat about world events or the weather. Why else would she have mentioned the easily commutable distance between them in her opening message?
Not much. Just looking at som pics and rubbing my cock, Jack replied and added a winking face followed by one with the tongue out.
Found anything you like then, she asked and Jack smiled as he figured she was fishing for compliments on her own pictures, and he decided to indulge her.
Yea. You.
Mmmm … Which one is your favourite then?
I really like the one in the bright red bra and panties where you've got one hand casually resting over your crotch and the other brushing against your beautiful lips.
He added a row of smiley's with hearts for eyes at the end of that message and was now actually rubbing his cock, rocking it back and forth and letting out a soft moan.
Mhmm … That's a really hot one, she replied after a little while.
I'm actually wearing that right now, she added and even if Jack suspected that was not really true he didn't care enough to question it. Instead he asked her if she was rubbing herself too. She said that she was and then to his surprise asked him if he wanted to watch her. He didn't have to show himself she assured him but she got a kick out of showing herself off to hot young studs.
Sure, he typed back and couldn't believe his luck when the next thing that happened was a request for video popping up on the screen.

He accepted and there she was, wearing the outfit from the picture. She was sitting in an office chair with a window behind her. The blinds were drawn so there was no clue to what part of the next city she was in but it was probably to avoid the neighbours seeing what she was up to on a Monday morning that the blinds were drawn. She was touching her lips and occasionally flicked her tongue at the fingers and occasionally she sucked on the fingers.
”You like my lips Jack,” she said and her voice was warm and sexy, seductive might be the more accurate word
Very much, Jack wrote back, They're so sexy. I bet you're a great kisser.
”Mmhmm,” she said and slipped her other hand, that up until then had been resting almost as if laying i wait on her lap, up along her belly to her breasts.
”Imagine my lips wrapped around your delicious cock,” she said and Jack moaned out loud enough that it was a good thing no one else was in the house except the two cats, or else anyone would have heard it.
”Fuck yea,” he said to himself in a voice that in the heat of the moment forgot that it wasn't Jackie speaking out loud and then he typed the exact same phrase into the chat window.

EbonyMilf disappeared partially from the screen and returned moments later with a large cock-shaped dildo of approximately the same colour as the RealDoe Jack was now tugging on quite vigorously, working his way towards his first orgasm of the day. She ran her tongue along the shaft seductively and then gave the head a gently, loving kiss, as if she was teasing a real cock.
How big is it, Jack asked.
”Ten inches,” she replied in that soft seductive voice, winked at him and slipped it between her lips.
Sweet holy mother of fuck, Jack thought to himself, that is so hot.
Wish that was mine, he typed and then let out a long groan as that orgasm hit him.

He closed his eyes momentarily to savour the orgasm to its fullest and when he opened them again a few seconds later he couldn't believe his eyes. She had that dildo more than half way into her mouth and was still pushing it deeper. Was she actually goiing to take all of it in her mouth. His left hand quickly grabbed the RealDoe again and started stroking. Right from the first tug it was obvious he wouldn't last long before being overwhelmed by a second orgasm. When she did pull the dildo out slowly it was covered in a thick layer of saliva and she smiled into the camera.
”Have a girl ever done that to you Jack,” she said and as if she could also see him he shook his head but fuck how he wanted it to happen. Those thick luscious lips wrapped around his RealDoe cock, pushing down until he felt her nose against his pubic bone.
I'm cumming again, he typed and then he did.
”Good boy,” EbonyMilf said and winked at him again.

The next thing he saw was her pulling her red lace panties aside and slowly pushing that dildo into her wet cunt and start to fuck herself with it. Pounding her cunt hard and deep with both hands on the dildo as if she was stabbing herself over and over. From that moment on she didn't speak. It was all just guttural noises, moans and little cries of pleasure until she let out a long groan and her belly started to contract, her thighs started to tremor. Her head was thrown back and about a minute later when she pulled the dildo out a small amount of clear liquid gushed out of her. Barely out of his second orgasm a third one hit and this one hit hard. In fact it hit so hard that the same kind of clear liquid gushed out of the part that was Jackie, not Jack, but in his mind it didn't matter. He had squirted and that was what mattered. Seconds later she said she had to go and the video cut out. Jack was left alone on Jackie's bed messy and confused. He barely had any concept of what had just happened to him. All he knew was that whatever it was it had blown his mind and he could easily see himself getting addicted to it.

He waited about five minutes for some kind of message from EbonyMilf but none came and a bit disappointed by the thought that perhaps he wouldn't hear from her again he got up and decided to shower before getting dressed.

 

[MsBloom]

3. A Day to Himself #2 (No More a Virgin.)

In the shower Jack jerked himself off once more, slowly and sensually at first but with an increasing passion until he felt his legs starting to shake and he had to sit down on the tiled floor of the shower. Like they had over the last two nights when he'd been jerking off Jack's thoughts and fantasies now went to Sophia, Jackie's older sister, which meant she was his older sister too he supposed. He was imagining her coming home early from her boyfriend, maybe they'd had a big fight, and caught him sitting there. Maybe she had noticed what Jackie had done to her panties two days earlier and he too had done to them in the days following. Maybe he looked up from the floor of the shower cabinet and saw her stand there, fully dressed of course, in tight fitting jeans and a t-shirt that exaggerated her breasts more than it hid them but with a sly seductive yet imperious smile on her lips, hands resting on her hips, looking down on him.

She did nothing, said nothing, just stood there looking at him, naked in the shower jerking his cock, and did he ever jerk it. He tugged on that RealDoe so hard, so fast it almost hurt but the orgasm was worth it and again he squirted from parts within Jackie rather than himself. He sat there catching his breath, confused and aroused with the water running over his body before reluctantly removing the RealDoe, the only thing in that situation that was him, that was Jack, and for almost fifteen minutes reverted back to being Jackie to clean up and wash his hair.

After the shower Jackie went through the procedure that was now starting to become something of a routine, she bandaged her breasts until they were flat against her body, stepped into the same baggy jeans as that first day she had become Jack, buttoned up the same plaid flannel shirt as well and finished the look with the stubble and moustache. Instead of the RealDoe, which was quite uncomfortable to walk around with the transformation was completed with a pair of rolled up socks down the front of Jack's underwear. Happy with what he saw in the mirror Jack then went downstairs to make himself some lunch, a grilled cheese sandwich with ham and Dijon mustard. While he ate he logged on to that site again through his phone and saw that there was a message in his inbox. It was from EbonyMilf sent almost a full hour after the live feed into her bedroom had shut down.
I'm sorry for disappearing on you like that but my daughter almost walked in on me. I haven't been able to stop thinking about you and your delicious young body and your big cock. I want to meet you.

Jack read the message and tried to swallow down the piece of grilled cheese sandwich in his mouth but it was absolutely impossible, he tried washing it down with a coke but only just barely managed. She wanted to meet? He couldn't do that, could he, NO. It just wasn't possible. And yet he felt his entire body tingling with excitement and arousal. There was nothing he wanted more at that moment. He checked her profile again, browsed the pictures of her and his desire for her grew a little more with each picture. How was he going to explain in a way that she understood, that didn't disappoint her or make her angry with him for … lying? No, but distorting the truth, stretching it quite far. He did notice that she was online and he sent her a video request. He might ass well just grab the bull by the horns and run as far as he could with it.

When she accepted his video request she was dressed as before, in just that red lingerie. Perhaps she had undressed back to that when she was the request was from him, perhaps she had been searching for someone else to tease and possibly hook up with.
”Hey,” he said and smiled.
”I … umm ...”
She smiled back at him and without letting him finish his hesitant sentence told him again that she was sorry about before and that she still did want to meet him.
”I can come to you if you don't have any way of coming to me,” she added.
”Or we could meet at a motel. I think that might perhaps be best, right?”

He nodded and swallowed hard. She was so sexy and he wanted her so badly even though he didn't even know anything about her other than that she had a daughter and that she was easily old enough to be his mum. He didn't even know her name. He hesitated on what to say long enough for her to ask what was wrong.
”I … umm … I have a confession to make,” he said and smiled nervously at her.
”See the thing is ...”
He cleared his throat and shot her another nervous smile. Instead of telling her he unbuttoned his baggy jeans and completed the transformation by taking out the rolled up socks and inserting the RealDoe. He heard her gasping but it took a while before he dared to look up and meet her eyes.
”I see,” she said when he did and the smile on her face suggested that even if it had not been what she expected it was apparently not an absolute deal-breaker.
After that nothing was said between them for a long time but he could see that her left hand did drop to her crotch and he saw the arm moving in a very suggestive way. He himself ran his hand up and down the shaft of the RealDoe, slowly and what he imagined to be seductively.
”You know where Milligan's Rock Motel is?” she then asked after what was probably no more than five minutes but had felt like hours to him.
Jack nodded but also said that he had no way of getting there.
”That's alright Honey. I can come and pick you up. Shall we say in an hour?”
Jack nodded again and tried to swallow but his mouth was dry.

An hour later and a half later he followed Brianna, as her name was, into a small but clean and modern motel room. Every nerve in his physical being was on edge and his skin felt like it was on fire. He was already aroused beyond anything he had ever felt before. She told him to sit down on the bed and then took off the lilac jacket she was wearing to reveal that red bra which she left on. She also left the knee long black pencil skirt on. She just reached under it and pulled off those red panties which she tossed at him.
”Now you,” she said and to give him the privacy to complete his transformation she turned her back at him and pulled the skirt up to her waist, giving him a front row view of her toned dark chocolate ass, and a hint of that pink slit already opening up like a bud in spring.

He slipped out of his jeans but kept the boxers on, slipped the RealDoe inside of Jackie's sex and stood up. He adjusted the boxers and took two steps towards her before dropping to his knees behind her. He placed his hands of her buttocks and leaned in close to that glistening pink slit. He took a deep breath and with a deep loud moan he ran his tongue along that slit. It was almost like a sensory overload and he actually had a small orgasm just from that first taste of a woman. She moaned too and parted her legs even more to give him better access and soon he was lapping that delicious cunt, sucking on the labia, poking his tongue at the tight hole and flicking it at her clitoris. He heard her moans, her groans and her little yelps of pleasure. He sensed her thighs starting to tremble as her breath got increasingly laboured and then almost without warning there was that gush of clear liquid all over his face. Her legs started to give way and she slowly sank deeper and deeper down.
”Oh my fucking GOD,” Brianna called out as a second gush of clear liquid poured out of her.
”I want you to FUCK me now Jack,” she said and got onto the bed looking up at him with her legs pulled up and spread wide open.

Jack wasn't one to be asked twice. He was on top of her in seconds flat and aimed the RealDoe at her soft warm and tight opening. He pushed inside and started to move his hips furiously. His mound slapping against her mound, the RealDoe moving inside both of them and it wasn't long before both of them cried out almost at the same time. His hands were on her beautiful breasts which she had released from the confines of that red lace. He sucked on the nipples and as he felt the orgasm rise up inside he kissed her on the lips, pushed his tongue inside her mouth and closed his eyes as his hips started to buck uncontrollably. He felt her abdomen and her thighs tremble against his skin and they both squirted almost simultaneously.

Afterwards they lay there and shared a beer and a cigarette. Jack was still a bit confused at what had just happened but he was also brimming with confidence. He had just lost his virginity and now knew that there were women out there who would accept him for the strange boy he was.
”Y'know what the best thing is about you Jack,” Brianna said and rolled over on her side to look at him.
”You're ready to go again already.”
She stuck the cigarette between her lips and rolled on top of him, guided the RealDoe inside her and started to ride him. She looked like an ancient African goddess with her breasts bouncing and that gaze of desire and lust she looked at him with. She rested her hands on his chest and leaned in to kiss him.
”Your cock is so wonderful Jack. I wish I never had to stop fucking it. I wish I could have it buried deep in my cunt forever.”
Her voice was low and came in laboured gusts of breath. Soon after she orgasmed again and so did he.

And so the afternoon went on. They fucked six or seven times in the six hours they sent together in that motel room. They did it in every way Jack had ever been able to imagine, from behind, up against the wall, on the bed, on the small desk, him on top, her on top. She even gave him a long and loving blow job and he licked her as often as he got the chance to do so.

Half an hour after they had both showered and got dressed Jack was outside the Café where Brianna had picked him up and with a dumb smile on his face he shoved his hands into his pockets and walked back home. He was not a virgin anymore and he could not remember a time when he had been happier in his entire life.