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The Firsts Continue

Category: Anal Sex
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She was lethargic from the intensity of that last orgasm. She had no idea that having his entire hand inside her would make her body explode like that. It was amazing. He had left the room a moment ago and she heard him in the bathroom, probably washing all of her cum off his hand. Her pussy clenched again with the vibrant memory. Hell, she didn’t even mind the ball gag any longer. It would be so easy to fall asleep right now…

He stepped silently into the bedroom and looked at the blindfolded, gagged woman tied to his bed. Was she asleep? She looked relaxed enough to be, and her breathing was heavy. But that could also be due to the gag.

“Wake up, sleepyhead,” he whispered, and kneeled next to her head.

She hummed around the gag.

He gently raised her head off the pillow and released the gag. She opened and closed her mouth a few times, wiggling her jaw side to side.


“Yeah, it’s fine,” she mumbled.

Yep, she was definitely asleep. He massaged her jaws lightly, running his hands around her face, down her neck, into her hairline. Eventually her breasts called to him and he went to visit them as well.

Her nipples were soft, velvety, but they quickly hardened when he palmed her breasts. Pushing them together, he ran his tongue up the valley of smooth then sucked the right one into his mouth. She liked it when he bit, so he nibbled not so delicately.

That woke her up. She gasped and arched toward him.

“Wanna try something else?” he asked. “Let me rephrase, are you awake enough to try something else?”

“I am now. And besides, it’s your fault that I’m sleepy right now. That orgasm kicked my ass,” she grumbled.

“Speaking of your ass…” Moving to the foot of the bed he untied her legs from the footboard. One hand and a slight push on her thigh convinced her turn onto her side. He ran his hands up and down her legs, petting on the way up, scratching on the way down. She groaned her approval.

“Do you want to take off the blindfold?”

“Yes, please”

So polite. He untied the scarf and tossed it toward the dark closet.

“What about my hands?” Polite, but impatient. She liked to play with him just as much as he liked to play with her, and he knew it was killing her to take all of the pleasure and not be able to return it.

“Nope, they stay tied.”

“You suck,” she stated.

He slapped her ass for the comment, and she laughed and squirmed like always.

Reaching over her, he grabbed the bottle of lube from the dresser. He ran the plastic bottle up her stomach, between her breasts, around her nipples then back down to skim her hip bones.

“Guess what this is.”

“A bottle,” she answered.

“Yes, it’s a bottle. But a bottle of what?”

“I don’t know.”

He scissored her legs apart and slid the cool plastic over her clit, making her gasp and try to move away from it. But he was right behind her and she had nowhere else to move.

“It’s a bottle of lubricant,” he explained. The bottle dropped to the bed and he slid his hand under her upper thigh. Her cunt was still hot and wet as he dragged his finger from her clit down and around to her ass.

She figured it out pretty quickly. “Are you going to ass fuck me?”


“Am I going to like it?” That was the main question.

“Yep.” And he was quite sure of the answer.

It was certainly a night of firsts for them: the gag, fisting, and now this. He’d have to make sure she put this in her little diary so they could revisit the evening every once in awhile.

He knew she was nervous, but he also knew he could make it good for her. Reaching over again, he pulled a C-shaped vibrator off the dresser. He had jacked off earlier, so he wouldn’t rush her through anything. His dick was hard, but nothing he couldn’t ignore for a bit.

Taking a handful of her thigh, he lifted her leg and dropped his head onto the other leg. He buried his face in her pussy. God, she tasted good…salty and creamy and sweet. Rubbing his tongue over her clit made her cry out and her thighs clenched around his head. He didn’t want to get her off yet, just get her going again. His tongue moved down to the hole of her cunt and stabbed inside, pulling out more hot cum that his fist has produced just minutes ago. The juice of her body smeared over his nose and face.

He pulled away and opened the bottle, slicking his fingers with lubricant. With the other hand, he grabbed the little vibe and turned it on low. It would make her feel good, but wouldn’t be enough to make her come.

“Open your legs again.”

She did, and he inserted the vibe. Half went inside her to rub against her G-spot, and half stayed outside to apply pressure on her clit.

She moaned, “Oh, Jesus.” Her hips began to writhe with the vibrator.

One large hand pressed over her belly while his wet finger found her asshole. It was small and tight, but he gently pushed his finger in. It spasmed around him, and he swore he could feel it in his dick. It wasn’t so ignorable now. He kept his finger circling slowly inside her.

“Okay so far?” he asked.

“Yeah,” she whispered. “Weird, but okay.” By the sound of her voice, she was more focused on that vibe than her ass. Good.

When her sphincter muscles relaxed, he pushed his middle finger up. Fuck, this was going to feel so good once he had her open enough to get in. His cock jerked against his stomach in anticipation.

Ignoring, ignoring, ignoring he kept thinking to himself. Three fingers and she hadn’t pulled away yet. Her breathing had changed though, and he thought she might be uncomfortable. His free hand swept up her belly to massage her breasts again. He petted each one, being slow and soft until she relaxed against him again. Then he pinched down, hard, on her stiff nipple and she almost screamed.

“You like that?” he asked, knowing the answer.

“Yes, more.” Her voice pleaded with him.

He pinched the other nipple just as hard, then moved his hand back down to the little vibe caught in her pussy. She was ready now.

Turning up the vibe just a fraction caused her to whimper. He pulled his fingers out of her ass and lubed his dick. The urge to pump his hand up and down was strong, but the lure of her tight asshole was stronger.

He spread her cheeks open and nudged the tight hole. His pre-cum and the lube moistened her up nicely. Gripping his own cock, he pushed forward slowly. Her sphincter opened just a little and he slid in, then it tightened down on his sensitive head.

Christ, he wanted to come already.

She seemed okay still, no complaints, so he moved a bit more. Her hips jerked back against him, just a little, but enough that he knew she was enjoying herself. Stopping was hard, but he did to go tickle her nipples again.

Every time he solidly pinched a nipple, her cunt and ass would bear down simultaneously and the vibration of the toy would shoot straight to his balls. He hadn’t realized he’d get any benefit from the vibe. Bonus.

Her ass finally opened up around the head of his cock and he could enter her deeper. But she was still so fucking tight, it was like a fist gripping him. And the farther in he got, the more that little vibe did for him. Through the small space that separated her pussy from her ass, that vibrator sent tingles into his belly, his balls, his knees and certainly his dick.

She was snug, but he was able to thrust in and out, in and out. And when she pushed back against him in a silent plea for more, he wanted to sing hallelujah.

“Roll over on your belly,” he whispered hotly and moved his hand back to the vibe in her crotch. As she rolled, he turned the vibe on high and moved on top of her back.

With a squeal of excitement, her ass thrust up against him, pushing him deeper than he had been yet. The vibrator buzzed both their orgasms closer and he wasn’t sure he would outlast her. He plunged in and out, her sphincter clasping him tight.

He could actually feel it as her body readied itself for climax. Everything got tense and it felt so fucking good around his cock that he couldn’t wait. He shoved her down on the bed so the vibe was sandwiched between her clit and the mattress. The additional pressure pushed her over and she screamed as she came. The vibration of the toy and the spasms of her ass milked his cock and he shot his load with a shout. She kept clamping around him and he kept spurting, over and over. Her body fairly sucked the cum out of him.

She was shaking beneath him when the room finally stopped spinning. “Turn it off,” she pleaded. He quickly worked his hand under her tummy and dialed down the vibe. She was so sensitive after coming that she couldn’t handle the continuous massaging. It would literally make her cry eventually.

They lay there together, him on top of her, his now soft dick still buried in her hot ass, for a long time.

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