Reflections

After he’d had a shower James went into Jessica’s room with a towel wrapped around his waist. He found her in her bathroom, drying herself off having just finished her own shower.

“What should I wear today?” He asked.

“The light grey three-piece suit, with a white shirt and no tie,” she replied while rubbing the towel through her hair again.

“Okay,” he said and trotted off happily to his room.

He only used his room to shower and store his clothes and things, he spent his nights in Jessica’s bed, although it was nice to have a space that he thought of as his. But he wouldn’t truly feel at home here until he had the photo of his mother.

James fixed his hair, splashed a little aftershave on and donned his suit, the first time he’d ever worn one. He liked the way he looked when he examined himself in the mirror, the waistcoat pinched his waist and made his chest look bigger. He put his finger through the loop at the top of the jacket and slung it over his shoulder and felt rather sophisticated as he walked down the hall to Jessica’s bedroom.

He found her sitting naked at her dressing table applying the finishing touches to her make-up. Jessica did a double-take when she saw him.

“My god, you look fantastic!” she said, getting up.

“Thanks,” he replied coyly and blushing.

“Honestly, James, you look so handsome. I’m not sure I’ll be able to keep my hands off you.”

James looked her up and down, he was still getting used to the casual nudity she displayed around him and felt his cock rising in his shorts.

Jessica grinned, “Sorry, we don’t have time right now, save it for later. Speaking of later, I thought we’d start our final lesson tonight.”

“Our final lesson?”

“Well, you never stop learning about matters of love, but as far as introducing you to sex goes, there’s one last thing we need to cover,” she said, then got up went over to the drawer by her bed. She opened the drawer and pulled something out, holding it in her closed hand so he couldn’t see it.

When she got to within an arm's length of James she opened her hand, in her palm was a shiny chrome butt plug with a bright gem on the end.

“Your final lesson is anal.”

James’ eyes lit up.

“Back in the day, when I was in that poly at Cambridge, I used to love anal. One of the guys in particular had a thing for butt plugs, over time I grew to love them. But not having a regular boyfriend I’ve kind of got out of the habit of using one. Anyway, I thought today would be a good day to start.”

She went back to the drawer and pulled out a bottle of lube. She squeezed a little onto the end of the plug, then a little on her finger and put the lube down on the side. She turned her back to James, spread her legs then rubbed the lube on her finger over her anus.

“Wait, you’re putting it in now?” he said, his face a picture of surprise.

“Uh-huh, I’m going to wear it for our meeting with Dani.”

“I…you’re…I mean…okay, wow. That’s so fucking hot.”

“If you think that’s hot, wait until you see what I’m wearing.”

He was about to ask what that was when she placed the plug between her butt cheeks. He stood and watched as she bent forward a little and gently eased the plug in, pulled it out a little then pushed it back in again, at which point it slipped inside as if being sucked in by some unseen ****, leaving the little red gem decorating her peachy bum.

“There now, it’s in.”

“Oh my god, Jess, I’ve never seen anything so hot in my life.”

She took a tissue from the side, wiped the excess lube from her butt and finger then walked over to him and kissed him, “Thank you,” she said.

James sat in the chair in the corner of her room and watched as she got dressed. First, she placed a lacey beige suspender belt around her waist, fastening it up so it sat snuggly on her hips. Then she sat on the edge of the bed and slowly pulled sheer, light tan stockings up her legs and one by one attached them to the belt. Over the top of this, she wore a pair of beige knickers, with sheer lace at the front that showed glimpses of her pubic hair. When she showed James the back of her knickers they were full and completely covered her bum, but were see-through, allowing the red gem to sparkle through the fabric. The last of the underwear was a white bra. He thought it was nice and had some lace trim but it didn’t seem to fit the rest of the ensemble.

Jessica noticed the confused frown on his face and smiled at him, “You’ll see why I’ve worn a bra that doesn’t match in a moment,” she said as she placed it around her waist, fasting the clasps at the front then twisting it around the right way and pulling up into place.

James was fascinated by the process and how erotic she made it. It was like a performance, a kind of reverse strip tease.

Jessica walked out of her room into the small connecting dressing room where the majority of her clothes were kept, she looked over her shoulder and said, “Are you coming to watch or staying there?”

“I’m coming,” he said, briskly walking across the bedroom to catch her up.

She selected a cream-coloured long-sleeved silk blouse from a cupboard and put it on. As she fastened the buttons James nodded.

“Ah, I see, you needed a white bra for the top you’re wearing.”

“Exactly. You can see a little of the lace of the bra through the fabric. If it were any other colour it would look odd.”

Next, she selected a tight, knee-length beige skirt with a sort of tweed pattern and stepped into it, pulling up the zip at the back and fastening the button. Then she pulled a pair of tall beige heels from the shelf and sat on a stool to fasten the thin strap around her ankles. Last of all was a jacket which matched the skirt.

Jessica checked herself in the mirror, pulling her skirt down a little, pushing a strand of hair behind her ear and adjusting the blouse in the waist of the skirt.

“There now, all done and ready to go. How do I look?”

“Like a million dollars. You look stunning.”

“Thank you,” she said. “Here, come and stand with me for a second.”

James stood next to her and she placed her arm through his as they admired the sight of themselves together in her full-length mirror.

“I think we make a good couple, don’t you?”

“Two weeks ago I’d have never thought this possible, but yes, yes, we do.”

“Did you like watching me dress?”

“It was fascinating, I’ve never seen a woman get dressed like that before, not even in porn films, they tend to just take clothes off, not put them on.”

She looked down at the bulge in his trousers, “Hmmm, I think you found it a little more than fascinating. Does that need taking care of before we leave?”

“No, it’ll be fine, it’ll go down soon. Besides, we don’t have time and you’re all dressed and stuff.”

“True, we are short on time. But we can’t have you walking about with a huge hard-on now, can we?”

“Well, when you put it like that,” smiled James.

She opened a cupboard, inside was a laundry basket, she reached in and pulled out a hand towel, then sat on the stool with the towel on her lap.

She beckoned James over to her with a waggle of her finger. When he was within range she unzipped his fly and pulled out his cock.

She licked her lips and said, “God I love your cock,” then sank her head down on the length.

She took as much of it as she could in her mouth, then clamped her lips down and pulled it out again.

She smiled and looked up at James, “Let’s leave that lipstick mark there, later on I’ll see if I can fit more of you in my mouth. But for now, let’s get you finished off.”

Jessica expertly wanked the base of his cock while her mouth bobbed up and down on the tip at a speed James didn’t think possible. Having this beautiful woman servicing him like this was the stuff of his fantasies, it was almost too much to compute. He stared down at her dark red hair and bright red lips and those painted nails and imagined the lingerie she was wearing and pictured the plug in her butt. All of this combined with her fantastic technique meant he didn’t last long, perhaps five minutes.

“I’m gunna blow,” He said.

Jessica used her free hand to hold the towel under her chin as she finished him off in her mouth. His load was not too big, given that he’d already come once this morning. Even so, it was still a lot to handle, she only just managed to keep it all in, letting it slide down her throat.

“There now, all done,” She said, carefully placing his cock back in his trousers and zipping him up.

“I’ll just put a bit more lippy on and we can go.”

As she walked off into her room James caught sight of himself in the mirror, hardly recognising the man staring back at him.

He grinned and said, “This is the new you James, best get used to it.”

“What was that?” shouted Jessica from her bedroom.

“Nothing,” smiled James.