Thirteen
His birthday was approaching, and she wanted to do something special for him, something they hadn't done before. Had to be sexual, of course. After thinking about it for a few days, she decided to give him her butt. He had mentioned anal sex a couple of times in passing, but had never actually come out and asked for it. He had admitted that he had never had a woman who was interested enough to allow him to experience it. So, he was a virgin, at least in that respect.
She was not a virgin when it came to her ass. She had given it up a couple of times long ago, spur of the moment insertions with men that really hadn't mattered that much. At the time, she really hadn't known what to expect. The discomfort she experienced, along with the unexpected unpleasantness that resulted, had turned her off of if. In the intervening years, she had not let herself be used in that fashion again. It wasn't that she had anything moral against it, it just didn't do much positive for her.
Determined to have an anal encounter with him turn out to be something they would both enjoy, she set out to do a little internet research. Searching for 'virgin gay men having sex', she found a plethora of texts and postings with advice on how to have your first anal encounter be enjoyable. Leave it to gay men to publicly describe how to stick something up your ass and have it be pleasant!
Armed with some insight, she made herself a mental shopping list, and started preparing for the birthday encounter.
She had already given him an invitation for a hotel encounter. That had pretty much become the norm for them. A downtown hotel, swanky, expensive, and worth it for this. She reserved a top floor suite, one that had two sides consisting of just glass walls, for an unobstructed view of the city lights. One of the very expensive King sized beds, comfortable enough to give you an orgasm by merely laying on it (almost!). Large bath with a whirlpool tub – that was for her enjoyment!, and a glass shower. She had told him to meet her there, but had intended to let him get there first and stew a bit.
Two weeks later ...
He opens the door to the suite, and walks in. She is not there, but he's not surprised. She has never been the most punctual person on Earth! He sees a note propped up on the bed – she has obviously already been there.
"Pour yourself a glass. Relax a little. Then get in the shower and scrub yourself clean – every bit, every inch. You are going to enjoy yourself this evening."
Looking over at a table across the room, he spies her normal bottle of blackberry wine, and the makings of a Tanqueray and tonic. Choosing the latter, he mixes a tall one and wanders into the bathroom. Her overnight case is already there. Resisting the temptation to get a glimpse, he does not open it.
He is tempted to hop into the tub, but chooses the shower instead, knowing he's got to get the work day off of him before she arrives. After a long, hot, soothing shower, he dries, dresses in the house robe (which is unusually comfortable) and returns to the main room. Hopping up on the bed, he leans back against the way too soft pillows, and dozes a bit.
42 minutes later, the door opens, and she walks in. It does wake him up. She walks over to the bed, smiles at him, and begins undressing. Even though she has on her work clothes, her position dictates professional clothing. Off comes the shoes, then the skirt. She makes a show of unbuttoning her blouse. She turns away from him, and drops the top off her shoulders onto the floor. Reaching around, she unhooks the bra clasp, and it too falls to the floor. She bends over and slides her panties down her legs, and then steps out of them. Though her underwear is everyday whites, they are stylish. The site of her in and out of them has caused a boner alert to be issued from his groin.
She turns back around and faces him. He starts to push himself up and towards her, but she stops him with a finger.
"Not yet. I'll be back in a little while. For now, you just sit there and think about this," she states, while sliding her right middle finger down from her belly button towards her V. "Try not to stroke that little monster too much. You're going to need all the staying power you've got."
Leaving him, she retreats to the bathroom and closes the door behind her. Normally, she wouldn't close him out, but she didn't want to give her surprise away by him seeing some of her preparations.
Her first task is a couple of doses of anal douche. The biggest reason she hadn't revisited anal sex in many years was the unpleasant reality of what goes on 'back there'. Her internet searching had identified an easy solution to that. It felt kind of weird filling herself up like that, but it wasn't bad. After disposing of the results, she stepped into the shower, which had been running hot. It was nice and relaxing. She let her mind go blank, and stood under the hot spray, letting the bullshit of the work day rinse away. After a thorough scrub down, she pulls out a new razor and smoothes her skin to baby butt consistency. Careful attention to the deep cut V above her pussy, sharpening the edges and scraping away any wayward hair.
After a good all over rinse, she steps out, and runs a hot bath. There is no way she isn't going to skip using a jet equipped tub! She drops in some scented oil that she had brought along, then steps in. Moving around, she uses the jets to massage her legs and lower back. The, sitting at the right angle, she lies back and relaxes. Her legs relax open, and the jet she had strategically put herself in front of starts gently pounding her pussy. She tries to resist sliding her hands down, but is unable. Her fingers spread her labia apart, letting the warm water caress her womanhood. Closing her eyes, she enjoys the sensations for several minutes before deciding its time to let him off the hook.
After drying off, she opens the overnight bag. After a few moments of touching up her makeup and arranging her hair, she pulls out her choice of bed wear. Since this is his birthday celebration, she had gone to an upscale lingerie boutique and bought something a little special. Slightly wild, definitely slutty, all black of course. She starts by sliding the thigh highs up onto her legs. The top of the wide, lacey bands rest a perfect 3 inches below her pussy. Next, she slides up a crotchless pair of panties. The front is black satin, with a lace V inset. She had chosen them specifically because the V matched her chosen hair style down there. The back is not her normal thong type, because that would interfere with the target she intended to offer him. The cutout in the material formed an inverse V just at the top of her butt cleavage. Narrow lace trim accents all the fabric edges.
Next item is the waist cincher/garter belt. She had chosen a long style one, with a lace up back. Although the material did provide enough stretch so she could pull it up, the laces gave the look and feel of an old time lace up girdle. The smooth material slides up her legs, gliding against her thighs. The fabrics make a wonderful swooshing sound as they rub together. A gentle tug gets it up and over her hips. A couple of wiggles settle it into place. The upper edge rests about 3 inches below her breasts. The bottom is just below her belly button. The six garters each has a little red rose embroidered onto them where they attach to the garment. The clasps are chrome metal, not cheap plastic ones. She stars with her left leg, and snaps the garter onto the top of the stocking. After it is secured, the length is adjusted so that is lies just right. Next, the middle one on the left side, located on her left hip is attached and tightened.
