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 mustache. Instead of the feeldoe, 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 as 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 saw 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 or 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 dealbreaker.

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 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. He 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.

Afterward, 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 spent 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.