Interlude 13-77

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.

Her left leg raises, and rests her foot on the vanity chair. Bending slightly, she reaches around and attaches the back garter on the left side. Crossing her cheek, the back ones are the most difficult to secure. However, the look of a 6 garter arrangement versus a garment with only 4 makes the small trouble well worth it.

Finished with the left side, she repeats the process with her right leg. Being right handed, the right back garter was the most difficult of the six to reach. However, she's had some practice at it, and has no trouble getting the clasp positioned properly.

Turning her back to the mirror, she looks back over her right shoulder. Very nice, she admits to herself. The lace up back really gives a vintage look, something that really ought to turn him on. She tugs on the back garters a little bit, making sure the back seams in the stockings are straight. A quick check in the mirror confirms she is at her sexiest, and everything seems to be in place.

She's decided to go without a bra this time. She's also left the 5 inch heels at home, thinking they will get in the way. She's likely to be moving her rear end around a lot, and it will be easier without worrying about poking him in the eye with the stiletto points.

She cracks open the bathroom door, and slips out into the bedroom area. He has nodded off on the bed. Understandable, since she's been in the bathroom for over an hour prepping herself. Quietly, she walks over to the edge of the bed. Reaching down, she pulls the robe back away from his groin. The little monster has gone to sleep as well. Moving around to the foot of the bed, she then slowly crawls up on it. Carefully, so as to not wake him, she moves up and over him.

Bending over his dick, her tongue darts out and touches its tip. It jerks involuntarily in response. Glancing up at his eyes, he still seems to be asleep. Good ... a little wakeup surprise would get the evening off to an excellent start.

Her tongue gently moves up and down the length of his flaccid shaft. With each of her movements, she can feel it growing. Concentrating on the underside just beneath the mushroom head, she flicks the tip of her tongue back and forth. That's the spot. Now it is rapidly growing, and quickly reaches its full length. Quickly, she turns her head slightly, and pulls the entire head into her mouth.

With a moan, he stirs. Eyes opening, he sees her with his dick halfway inside of her mouth. What a grand way to wake up! She bobs her head up and down a couple of times, and then pulls back off of him.

"Rise and shine. Time to get to work, little boy," she taunts him.

He reaches down and grabs by the right wrist. He pulls her up towards him, and then pushes her off to the center of the bed. Rolling over on top of her, he pins her arms down with his. Without a word, his lips descend onto hers. Her mouth opens to meet his, their tongues touch and intertwine. Hungrily, they press there mouths together, tongues dancing. His left leg swings over between hers, and his thigh starts moving against her crotch. Her moans escape from between their lips.

He slides down the bed a little, and moves between her legs. He hooks his arms under her knees, raises her legs, then pushes them back against her chest. Her pussy is fully exposed. He bends over, and dives right in. Normally, there would be some extended teasing in his foreplay, but they are both so worked up that waiting just wasn't going to happen. His tongue darts straight into her opening.

Her eyes open wide, and she gasps in response to the penetration. Hands reach down and grab him by the hair, and pull his face into her womanhood. He hungrily darts his tongue in and out. He feels her silky smooth inner lips, the heavy natural moisture her pussy is providing, and her clit rubbing against his nose . He moves his face side to side a bit, tickling her love button with the tip of his nasal protuberance.

She is trembling with his efforts. Not wanting to take her over the edge so soon, he backs away.

"No, you fucker. Don't stop, please," she pleads.

"Sorry, we've got a long way to go tonight. You don't get to cum so soon."

She pushes herself up off the bed, grabs him, and pushes him back against the pillows. "OK, if you're going to do that shit, I'm going to tease you some," she says.

She sits on the edge of the bed, and opens the top drawer of the nightstand. She grabs a tube of 'Anal Ease', and the little vibrating butt plug she had purchases a couple of days earlier. With an evil look, she holds them up in front of him, letting him wonder a bit.

"One of my girlfriends told me that I needed to try this. She said that having this up my ass while you are fucking me will set us both off. In honor of your birthday, I thought we'd give it a try. You don't mind, do you?"

Not quite trusting his mouth to work properly, he just nods up and down.

She swings back over him, straddling his hips but facing his feet. She runs her hands down her sides, the fabric of the waist cincher making soft swooshing sounds as she passes over it. She look back over her right shoulder at him. His gaze is locked on her back, taking in the sexy look of the lace up garment. She gently grinds her hips a little, pressing against his cock.

She bends over onto all fours, and then backs up. She stops when her butt is over his nipples. She reaches down between her legs, and passes him the lube.

"Make it wet, baby. Nice and slick, please."

He slaps her cheeks softly, and rubs them around. The sight is an awesome one for him. Her pussy and ass crack are framed by the crotchless panties. The garter straps cross her pale white cheeks. His hands grab the flesh, and pull the cheeks apart. He gazes in wonder at her openings, so clean, so slick, so inviting.

Taking the lube, he squeezes a generous portion onto the index finger of his right hand. Gently, he touches the tip of the finger to her anal opening. The lube is a little chilly, causing her to squeal a bit. The flower opening contracts a bit, and her butt cheeks clench his finger. As the liquid warms to her body temperature, she relaxes. He moves his finger across the sensitive flesh, a slow circling motion. He can feel her body relax against him as she gets used to the sensation.

With his left hand, he squeezes a bit more of the lubricant out of the bottle. The drops gently hit the top of her ass crack, and slowly slide down towards the finger that is teasing her hole. The drops mingle with the moisture he is working with, and the excess rolls down towards her pussy.

She is softly moaning now, and her hips are ever so slightly rolling. His index finger pushes inwards a bit while circling, placing pressure on the opening. The pressure finally overcomes the tension in the opening, and the finger slides inside up to his first knuckle. She gasps, motion freezing, butt cheeks clenching, and then relaxes again.

Slowly, his finger starts sliding in and out. Not far at first, just up to that first knuckle. Her moans are getting deeper. Her arms wrap around his thighs, as she leans over and rests her chest against his body. Ass up in the air, breasts smashed against his dick, she starts moving against his finger. Her rhythm forces it deeper inside of her ass. The lubricant is slick, the movement is easy. Her opening is tight, he can feel the muscles of the opening clamping down on his digit as it moves in and out.

He stiffens his index finger so that it becomes a mini-penis for her to ride. He stiffens the middle two fingers, and positions them just behind her womanhood's opening. His pinky likewise straightens out. Slowly but forcefully, he extends his hand. Index finger slides up all the way into her ass. The middle fingers slide into her pussy, which is so wet that it needs no additional lubrication. The pinky slides down across her clit.

Her gasp is a cross between moan and cry of delight. Her motions increase without conscious thought, driving her rear end back onto his hand. The sensations of both hole being penetrated at the same time as having her love button stimulated is intense. She has never had this combination of stimulation before, and it has her body acting on its own.

He can feel her start to tense. It is too early to let her have an orgasmic release, so he pulls his hand back away. Soft whimpers escape, signaling her displeasure. Her hips continue to move, trying in vain to push her over the edge. Finally, she stops, and resigns herself to a bit of sweet frustration.

"You bastard," she blurts, face buried between his legs. "Slide that little fucker inside of me before I punch you in the nuts!"

Presuming she is talking about the butt plug and not his dick, he chuckles a little. He dribbles some more lube, letting it run down her crack. Taking the plug in hand, he drips a bit of lube around it, and then spreads it evenly around the surface. While not big, it would be uncomfortable if it was pushed in dry. The plug itself is flesh colored, and shaped like a short penis. The mushroom head and shaft are about an inch and a half in diameter. About two inches long, the plug sharply tapers at the back, and then flares back out to form a base/grip. Other than its size, it is a pretty good looking cock!

He places the head onto the flower of her entrance, and slowly, gently starts circling it around. It must feel good to her, her hips start grinding a little. After 30 seconds or so, he pushes the head into the opening just a bit. A gasp and a low moan escape her lips in response. Knowing that even though the plug was small in comparison to a real cock, it was still big for something going into that opening, he is gentle. It is clear to him that she is enjoying having her ass toyed, and he does not want to ruin it by hurting her.

"I'm going to hold this little guy. You push back onto it at your own pleasure. You control this, OK?" he asks.

No verbal response comes back, just another contented moan. She wastes no time in moving back against him. One thrust against him pushes it about halfway in. She then wiggles her ass, and bit by bit the rest of its length slides in. The lube helps, but it still feels a lot larger than it really is. Finally, with a last small push, it slides all the way in. Her sphincter muscles collapse the opening around the narrow taper, trapping the length of the plug inside of her.

"Fuck, that feels good. Push it a little, please. Make sure it is all the way in," she asks.

Resting his index finger on the base, he pushes it in, and gives it some rotation. It is indeed all the way in, but it certainly seems to heighten her sensation by pushing some more against her opening.

She pushes herself up off his legs, and repositions herself. Facing away from him, resting on her knees in a reverse cowgirl, she places her pussy over his dick. Reaching down, her had grasps his cock and hold it upright. Rising slightly, she places the head against her lips. Slowly, she slides down its length, impaling herself on him. With his full length inside of her, she leans back slightly and breathes deeply. Savoring the sensation of being filled front and back, she soaks in the pleasure. Fucking, especially fucking him, was always pleasurable. However, being completely filled this way was a new level of sensation, one she was happy to be experiencing.

Rolling her hips, she grinds against his groin. His dick moves inside of her. Her right hand finds its way downward, the index finger finding her clit. She doesn't feel the least bit guilty about stimulating her love button. She is close, very close to the edge. Her hips move faster. Her left hand grabs her left breast and squeezes it. She's on top, and he is not going to deny her release this time!

He knows that her movements are a prelude to an orgasm. He wants it to be a memorable one. He grasps her nylon clad ankles, and holds them in place. This gives her more leverage in her movement. He watches her as she flies towards orgasm. Her ass cheeks as they move back and forth across his lower belly. Her head is thrown back, hair swaying in rhythm to her body's movements. The lace up garter cincher, black fabric and lace stand in contrast against her pale skin. The stockings on her legs are so sexy. He wished he could see her breasts as they jiggled in time to her rocking motion. It was like starring in his own porn movie, except the feelings coming from his dick were very real.