Chapter 8 #2
Meg had been wearing the medium sized plug all day to help keep her virgin hole from completely closing up tight again, but she knew she was still going to really feel it when Leo put his cock in there.
After all, he was even bigger than the plug she'd been stuffed with last night and she'd struggled to accommodate that.
As usual, Russ trailed along after them, like puppy hoping someone would throw him a bone.
Under her cute sweater and pants Meg was wearing absolutely nothing, and the effect was more than worth it when she took off first her top and then her bottoms. Both of them men made appreciative noises, especially when she deliberately bent at the waist to pull down her pants, her ass towards them, so they could see the base of the plug between her creamy cheeks, stretching her virgin ass so Leo could fuck it.
She was pretty sure she heard Russ whimper as the reality came home that this was really happening.
"Fucking beautiful, sweetheart," Leo said. "Get up on the bed on your hands and knees. Russ, you get up there and get your wife's last cherry ready for me to pop."
The crude, authoritative way he made his demands had Meg's pussy quivering in anticipation as she crawled onto the bed.
Rather than getting on her hands and knees, she lowered herself to her elbows so her nipples could hang down and brush the sheets, and her ass was pushed high in the air like the offering it was.
She felt the movement of the bed as Russ joined her, and she moaned a little in anticipation as he pulled the plug from her bottom. After all the stretching of the week, the medium size plug moved fairly easily, but her hole still started to close immediately after its departure.
"What do I do now?" Russ asked hesitantly.
"Kiss her ass," Leo said. "Use your tongue and lick that pretty little cherry for me, get it nice and wet, and then you're going to use your fingers and some lube to make sure she's really ready."
Meg could almost feel Russ’ hesitation, and she thought he was finally going to protest..
. but then, to her surprise, she felt the wet, warm touch of his tongue lave over her crinkled rosebud and she moaned at the gentle, pleasurable sensation.
It was something she would have never been willing to try on her own or if Russ had suggested it, but when Leo ordered it she wasn't going to say no.
.. and if she'd tried to resist, she would have been missing out.
The tiny hole was a little mecca of nerve endings, and Russ' licking strokes felt incredibly good.
"That's right," Leo said, his voice low but close enough she knew he was watching closely. "Shove your tongue right in there."
She shuddered, her holes clenching, pussy dripping as Russ obeyed, his tongue stiffening and spearing her asshole like a tiny cock.
It didn't get very far inside of her, but it felt amazing, and Meg squirmed against the surprising oral assault.
Her pussy was quivering, aching to be filled, envious of the attention her ass was receiving, and yet she had no desire to beg for Russ' tongue to be moved.
It felt too good right where it was, stimulating her last virgin hole and readying it to be fucked by another man.
"That's a good boy. Now take some of this and use it to lube her hole for me," Leo ordered.
Meg sighed as Russ' mouth pulled away from her ass, but she was too impatient to have Leo's cock inside of her to protest. Fingers pressed at her virgin hole and pushed in, spreading a slick, cool gel around her insides to make it passage for Leo's hard cock a little easier.
Her husband's fingers pushed in and out, working the lubrication into her tight hole, and making her moan.
She could hear Russ' panting breaths of excitement as he readied her asshole for deflowerment, and Leo's deeper, more steady but still excited small groans.
Turning her head to the side, she could see Leo watching Russ prepare her ass for him, his hand wrapped around his dick, stroking the thick length in anticipation.
"Alright, boy, move to the side."
It only took a few moments for Russ and Leo to switch places, so Leo was the one kneeling behind her upturned ass and Russ was beside them, in a position to watch.
"Now take my cock and point it at your wife's ass."
Time seemed to freeze, Meg's breath catching her throat as she wondered if she'd really just heard Leo say what she thought she'd heard him say.
"Wh-what?" Russ stammered in shock.
Which meant Leo's perverse order was real. A thrill went through her at the wickedness of having her husband holding the cock which was going to take her anal virginity.
But would Russ really do it?
"You heard me, boy. You're going to help me take your wife's ass cherry. Now get your hand around my cock and put it where it needs to go."
The strict command in Leo's voice didn't leave any room for argument, and Meg found herself holding her breath as she waited to see what Russ would do.
Peeking over her shoulder, she saw her husband staring at a spot behind her—she assumed at Leo's cock.
Almost as though he was in a trance, he slowly lifted his hand and Meg's eyes widened in shock. He was actually going to do it!
Leo let out a low groan of appreciation and then Meg felt the slick head of his cock pressing against her anus—held there by her husband!
"Your husband is going to help put my cock in your ass, Meg, sweetheart. Does that turn you on?"
"Yes," she admitted, breathing out the word as she pressed back against the thick, blunt head prodding at her entrance.
Chuckling, Leo patted her bottom with his large hand, as if telling her to be patient.
"Go ahead, Russ, help me pop your wife's cherry."
Meg moaned as Leo's cock moved forward, very slowly spreading her crinkled hole open, stretching her wide enough that the wrinkles in her skin began to smooth out as her asshole strained to accommodate him.
She whimpered as the head of his cock popped into her ass; it was so much thicker around than the plugs and there was no narrow part for her sphincter to relax around.
She couldn't do anything but brace herself, her asshole spasming and trying to close around the huge invader.
"Oh!" She let out a small cry as Leo's cock slid deeper before pulling away again, her focus now entirely on what was happening inside of her and not on what her husband was doing or seeing.
The sensations were intense, even though he couldn't be moving more than an inch or two of cock back and forth in the narrow confines of her ass.
Being plugged hadn't prepared her at all for how the movement would feel.
The interior of her channel felt the heat of friction despite the lube, her clenching walls seemed almost raw compared to when he was in her pussy, making her gasp with discomfort and pleasure simultaneously.
She'd thought the largest plug had been erotically difficult, but this was so much more.
With every surge of his cock sliding deeper into her virgin ass, she gripped the sheets a little harder, moaning and quivering at the tight fit.
She felt so stretched, so full, so deliciously uncomfortable.
Giving up her ass cherry, taking the stinging burn of being so strenuously stretched, for Leo.
.. it felt good. So wrong but oh so right, and Russ' hand feeding Leo's cock into her tight hole was the cherry on top of her perversion sundae.
When Russ' hand bumped against her ass, she moaned at the wicked sensation, knowing she was feeling her husband's hand around her lover's cock.
"You can let go now, boy," Leo said, sounding amused.
Russ pulled his hand away as though it had been burned, and Meg whimpered a little as she realized just how much more of Leo's long shaft she still had to take into her ass. Large hands fitted to her hips, pulling her back, and she cried out.
"Good girl... that hurts, doesn't it?" Leo asked, crooning in a way that made it clear he liked hearing her little cries of pain and discomfort, that he wanted it to hurt.
"Y-yes..." Meg's breath was coming in pants as Leo kept rocking his hips, forcing his cock a little deeper each time.
It did hurt... it hurt so good and part of her wanted to beg him to take his cock out and fuck her the right way and another part of her was wallowing in the erotic pain of being ass-fucked by his huge cock.
"And you're going to take it for me, aren't you?"
"Yes... oh... oh fuck..." She pressed her head against the mattress, closing her eyes as Leo thrust a little harder, feeling the tears trickle from her eyes as her bowels cramped... but she didn't ask him to stop.
She didn't really want him to.
"You wouldn't have done this for your husband, would you have?"
"No..."
A wild cry fell from her lips as Leo pushed in hard and finally bottomed out, his entire length splitting open her backside.
She felt like she could barely breathe, her ass was so full of cock and there was no room in her body for anything else, not even air.
More tears slid down her cheeks, but she wasn't sure if it was because it hurt or if the sensations were just so intense they felt like pain.
"That's it, sweetheart... you've taken my whole cock now." Strong fingers massaged her lower back, keeping a firm hold of her hips. "I'll give you a minute to get used to it before I start to move. Russ, come over here. You're going to rub your wife's clit while I fuck her ass, help her to relax."
She let out another little moan of arousal at Leo's deviously perverse mind.
Russ came along beside them on the bed, one hand slipping under her body, seeking out her clit, while his other stroked himself.
His own breathing was heavy, his face flushed with arousal.
She shuddered as his fingers found her wet pussy and began to rub her sensitive folds and clit, sparking her pleasure and making her holes clench and relax.