Wilson's Hard Lesson

by K. Anderson

  “Yes, yes, of course,” she answered, a little impatiently. She was wet and desperate for him already, her legs starting to part and her insides squirming. If he hesitated and made her wait any longer, she’d change her mind and just want him inside the regular way, seeing as she imagined that would probably bring her more direct pleasure. She’d never been an ace at science but as far as she could remember there were no pleasure sensors inside the ass for women, unlike guys who had all the fun.

  “We’ll take it slow, okay?” He looked at her intently. “And if I’m hurting you at any point, you can tell me and I’ll stop right away.”

  “How should I let you know?” She asked with a smile, reaching for the bedside table and bringing out some lube, not wanting to waste any more time. They’d already been interrupted once; she wasn’t about to let it happen again. “Should we have, like, a safe word or something? How kinky do you want our future sex life to be, husband?”

  She thought she saw his cheeks flushing slightly at that, and she enjoyed the sight of it. “I uh…I don’t know…wife.”

  “I’m just teasing you,” she laughed and leaned in to kiss him on the nose, then handed him the lube. “I guess you’re going to need to use this.”

  “Yeah, I didn’t need it last time, you were so wet,” he chuckled.

  “I am right now,” she admitted, wiping a couple of fingers between her legs and giving a soft moan of pleasure.

  “Are you sure you don’t want me to uh…”

  “You can touch me while we do it.”

  “Have you ever done this before?” He asked intently, sitting up on his knees, already very hard and obviously quite excited at the prospect.

  “No. Have you?”

  “Once or twice.”

  “Is that secret code for ‘absolutely loads’?”

  Carl blushed and leaned down to kiss her on the cheek, being very gentle and loving with her.

  “You don’t have to be so careful, y’know,” she smiled, although it was nice to have someone who very obviously cared about her, she didn’t want their sex to be ordinary all the time. A bit of spice now and then wouldn’t do any harm. “I’m not that fragile. I won’t break.”

  “Alright uh…let’s see…okay, we need to prep you first…make sure you’re nice and relaxed before I put anything too large in there.” He glanced down at his throbbing eight-inch member then smirked back up at her.

  “Okay, how do we do that?” she asked.

  He grabbed the pillow he’d been sleeping on. “Lie on your belly and put this under you…like uh…under your belly, to raise your hips and your butt up a little.”

  She nodded and did as she was told, with Carl helping to slowly ease the pillow underneath her. She shuffled around a bit and got comfy. It was actually pretty relaxing so far.

  Once she was in position, Carl took hold of her thighs and gently parted her legs, pushing them wide apart, getting himself on his knees in between them. She kept them spread nice and wide, bending her knees slightly so she could get comfortable again.

  “Good,” he crooned softly, running his hand up and down her thigh. “Mm, I’ve got a great view from here,” he added with a chuckle.

  She smirked and turned her head a little to look back at him over her shoulder, sitting up on her elbows. “Yeah? What can you see?”

  “Mmm…glistening pussy lips…all wet and dripping for me…and your cute little butt cheeks. They’re perfect. I bet you’re going to feel so tight around me.”

  She shuddered slightly at the hot, breathless way in which he was talking. She’d never heard him talk dirty like that before but it was a real turn on.

  “I can’t wait to feel you inside me,” she murmured back softly.

  “Mm well, you’re gonna have to wait a little while longer. Just be patient. I want to try something out.”

  “What?”

  “Close your eyes and relax. Just settle down.”

  She nodded and settled onto the pillow, resting her arms down too.

  Carl placed both his hands on the cheeks of her ass and separated them, then leaned down and pressed his face into the crack, sticking out his tongue and licking at the tight band of muscles that made up her hole.

  Anna squeaked and lurched forward slightly at the warm, wet sensation. “What are you doing?”

  Carl chuckled and gave one cheek of her butt a little squeeze, the pillow preventing Anna from moving too far up the bed anyway. “Just relax,” he told her. “I think you’ll enjoy this.”

  He leaned in again and began to lick and tongue at her little hole.

  It felt strange at first, but a few seconds later and she started to relax as he instructed, then began to really enjoy it. Soon, she was moaning and squealing and pushing back against his face as he squeezed her ass.

  With the pillow raising her hips, it also exposed her vagina which he now took advantage of by rubbing his thumb up and down the slit, then pushing his finger forwards and running it over the clit a couple of times as his tongue continued its work, alternating between poking at it and using the tip to tease at the entrance to giving long, slow laps with the flat of his tongue, mixing it up, keeping her off balance and not expecting his next move.

  Anna went crazy beneath him. She squirmed and wriggled, gasped and moaned, arched upwards and did half push ups off the bed, her eyes rolling and her mouth open in pleasure. She had never felt anything like this before and the new sensations were driving her crazy, incredibly hot. She grabbed at one of her own breasts, twisting and tugging at the nipple a little and squeezing it, adding extra sensations, then mauling and clawing at the bed as the sounds she let out became more and more obscene.

  He began to push a finger inside her vagina, just one to start off with, then two, as his tongue continued to lap at her ass and his thumb brushing back and forth over her clit. The way he was going, she felt as though she was going to climax already, but he didn’t allow her to. He stopped, just as she felt like she was on the brink, and pulled back away from her.

  She gave a gasp of protest and sat up, twisting to look at him.

  “Lie still, this isn’t over,” he said firmly, and there was a demand and order about his voice that turned her on even more. She wondered how dominant he could get if he was given the chance, and she made a mental note to test that out further in future.

  “What’s next?” she gasped, half closing her eyes.

  She heard the cap of the lube getting flicked open and a squelching noise as some of it was squeezed onto Carl’s palm.

  Her entrance still felt all wet and warm from his tongue, and already slightly opened up, but it opened even more a second later.

  She reached back with her hands and spread her cheeks wider for him. He circled his finger around her hole teasingly then slowly began to push it inside.

  She gasped and tensed up.

  “It’s OK,” he crooned. “Just relax. This might feel a little weird at first, but you’ll get used to it. Then hopefully enjoy it.”

  She nodded into the pillow and let out the breath she’d been holding, trying to relax and breathe slowly in and out.

  He grabbed the bottle with his other hand and squeezed it all over her ass, watching as it dribbled down and filled up her crack. Then he closed the cap and tossed it onto the floor.

  “Wow, that’s a lot,” Anna giggled, feeling it all squelchy and kind of cold.

  “Don’t want to hurt you,” Carl mumbled, pushing his finger in deeper.

  She gasped as it went in up to his knuckle and he reached out with his other hand and stroked gently up and down her back to calm her.

  Once it was in, he rested and just let it stay there for a moment so she could get used to it, before pulling back and starting to move it, slowly, in and out.

  Anna let out a soft whimper, experiencing a mixture of pleasure and pain, but mostly just an odd, uncomfortable sensation. Carl was right; it took a while to get used to. He reached around with his spare hand and continued
the attention on her wet clit that he’d been giving her previously, and that was a sufficient distraction to stop her worrying too much about the finger in her butt.

  She moaned louder and closed her eyes, pushing her hips back against him a bit and lifting herself up so he could get a better angle on her. His fingers slid back and forth through her wetness as his other finger did the work in her tight ass.

  He took his time, wanting to make sure she was fully comfortable and relaxed before very carefully adding a second finger to the mix, squeezing it up along with the first.

  Anna felt the stretch more this time, her muscles widening to accommodate both of Carl’s thick, long fingers.

  “Nn…” She gave a small inarticulate grunt, wondering how his entire penis would ever fit up there.

  “You comfortable?” He asked, flicking his thumb over her clitoris again.

  “I…I think so,” she nodded.

  “You’re doing really well.” He started to spread his two fingers apart slightly and she could feel them pressing against the walls insider her. She whined and kept her legs nice and wide, starting to actually enjoy the sensation.

  “M-more,” she murmured.

  She heard him chuckle softly and he started to move his fingers a little quicker, back and forth, over and over, in and out, the lube helping.

  “Are you ready for me, baby?” He asked quietly.

  “Definitely.”

  He slowly withdrew his fingers and stroked down her butt cheeks and thighs.

  With her ass properly lubed and ready now, Carl used his hand to coat his rock hard cock with the same slick stuff. Then he took hold of her thighs and carefully rolled her over onto her back.

  “Just lie on your back for me, sweetheart,” he said.

  She obeyed and rolled over, automatically spreading her legs again.

  “I want to look into your eyes while I do this.” He took hold of her ankles and raised them up, lifting her legs up off the bed a little to get the right angle.

  Then he scooted forward a bit, guiding his cock between her legs until he felt the head against the greased puckered hole it would be penetrating, biting his lip and moaning quietly in anticipation. After moving the tip up and down to let her know he was ready to begin, he centered it and began to push firmly but gently forward, feeling the muscles give way and accept him inside, the head wedging between the soft edges of Anna's ass. He went very slowly, not wanting to rush her or hurt her, knowing the size of his length was considerably more than the two fingers he had been warming her up with a few seconds earlier. He watched Anna’s expression with keenness.

  First of all, her eyes widened in shock and surprise. Then she let out a wincing gasp of pain. It definitely hurt, but it wasn’t quite as bad as she was expecting, and she didn’t want him to stop. She just squeezed his arm a little and stayed as still as possible, trying not to let her body tense up too much.

  Carl eased himself into her bit by bit, allowing her to feel every bump and ridge until his entire eight inches was where the both of them wanted it – burrowed deep into her ass, filling her up entirely.

  Anna moaned softly and fluttered her eyes closed. “Mm, feels good…you’re so big.”

  “And you’re so tight and perfect,” Carl murmured back, leaning down to kiss her gently on the lips.

  Once fully seated inside her he waited, letting her ass open up and get used to his size, while she squirmed and wriggled blissfully under him.

  "Are you ready for this?" he asked.

  "Ready and willing,” she whispered, forcing her eyes open to look at him, wanting to enjoy every second of this and savor it.

  Slowly, he drew his cock back until just the head was inside the opening.

  Carl paused there for a few seconds, before plunging his cock all the way back in until he could feel his pubic hair brushing against the soft insides of her cheeks. She moaned from the exquisite pleasure, and his sounds echoed hers as he repeated the process again, setting themselves into a slow and steady rhythm that gradually began to get faster over the course of the next five to ten minutes.

  Anna’s body writhed on the bed beneath him, thoroughly enjoying the sensation of his cock crammed into her, with Carl also receiving his pleasure as her tight ass squeezed and released his hard length.

  Gradually, he began to increase the pace, driving himself hard and fast into her as she pushed back against him silently asking for more. He slammed her forwards with the force of his thrusts, then reached down and slapped her ass with one hand.

  “Ah!” She cried out in pleasure. “Again!”

  “You like that?” He paused a little, slowing down and looking at her.

  “Yeah. Harder.”

  He smirked and raised his hand again, bringing it crashing down on her soft skin with a delicious noise that rang out around the room.

  “Again!” she begged, lifting her legs in the air.

  He grabbed her by the ankles and put them over his shoulders, creating a whole new angle for them both to explore, starting to drive back and forth into her again.

  He really started giving it to her then, and they both knew they wouldn’t be able to last for very much longer at that pace. Over and over, he pulled his cock back, paused, and drove it into her ass again. Every time she felt his hard, thick cock surging into her and the exquisite feeling of it splitting her ass apart, Anna pushed back to meet him, until her soft cheeks were pressed against his thighs and his cock was completely embedded in her. The blissful moans she uttered were her loudest and most heartfelt yet. Carl's happy sounds were just as loud and just as sincere, but as pleasurable as it was for both of them, however, Carl was also experienced enough to understand that Anna would be unable to climax unless he gave her some extra stimulation.

  He reached down with one hand and found her wetness, slipping and sliding his fingers through it easily, her juices dribbling down her leg slightly she was that wet from him. He found her clit and gently pinched the little nib between the two folds of her inner lips and started stroking her in the same tempo as his thrusts.

  She felt like she was about to lose her mind with pleasure. Her whole body was tingling and alive. She couldn’t concentrate on forming words or even seeing properly, her eyes half closing and her vision blurring out, all her thoughts knocked right out of her head with the wave of sensations that were washing over her. There was no way she’d be able to hold on for much longer and she didn’t want to.

  Carl drove himself over and over into her tight, needy hole, fondling her clit at a faster pace as she raised her hips up to meet each thrust, moaning and gasping, letting out sounds she’d never even imagined capable of uttering, her throat almost sore and harsh with the amount of screams she was letting out, sobbing and whimpering at the excruciating pleasure she was receiving.

  Then the volcano erupted and she could hold back no longer. She let everything go and her toes curled over in pleasure as she finally climaxed.

  Carl pushed a single finger inside her just so he could feel her clenching and twitching as she came, and she gasped and cried out his name through her quickened, short breaths, her fingernails scratching at his back, clawing at him.

  “Ohhh baby,” Carl groaned in pleasure and continued flicking his thumb over her clit for a few moments longer before letting go and grabbing her thighs again, which Anna was quite relieved about. She felt extremely over sensitive down there now and was still coming down from her climax, her whole body tingling with it and her chest heaving up and down.

  It was the final stretch for Carl too, and he didn’t hold back anymore, holding her thighs as he ploughed into her again and again, speeding up even more for the last few seconds as he hurtled towards his orgasm, finally toppling over the edge and giving a cry of pleasure, his head tossing back.

  Anna watched him, savoring the expression on his face, his features twisted up in bliss and the sounds he was emitting like music to her ears.

  She could feel the first gush of whit
e hot cum as it burst from his cock, and he shot a further two loads into her, filling her with it as they both moaned in unison.

  Then he was done, and he collapsed forward on top of her, breathing heavily and resting his head in between her breasts, his cock still deeply embedded inside her and slowly going soft again.

  "That was wonderful," Anna whispered to him, her hands wrapped around his back and gently running her fingernails up and down.

  "It was,” he agreed breathlessly, clinging to her and panting, until his breathing gradually got back to normal. “This might feel a little weird,” he mumbled.

  “What might?” She lazily looked down at him.

  He sat up, then slowly began to pull out from inside her.

  She gasped and winced slightly. He was right, it did. And it was pretty sore down there too.

  “Sorry,” he whispered, leaning in to give her a kiss on the forehead as he lay down beside her.

  “No, no, it’s fine, you didn’t hurt me.” She rolled onto her side and slid an arm around his waist, snuggling up close.

  “Did you enjoy that?” he asked with a smirk.

  “Heck yes,” she chuckled and kissed his lips tenderly. “Hey uh…can I tell you something?” She asked hesitantly. The words had been at the forefront of her mind, but she was worried about saying them out loud. At this point though, she was fairly sure that Carl felt the same way.

  “Of course, baby, anything you like.” He smiled and squeezed her waist gently.

  “Well uh…I…I love you,” she murmured quietly.

  His eyes lit up and the most beautiful smile graced his handsome features. She enjoyed seeing him smile. It made everything just…better. “You do?”

  She nodded and gave him a small smile back.

  “Well that’s just great, baby. Because I love you too.”

  “Really?”

  “Of course I do. And I’m pretty sure the trial period is most definitely over,” he added with a chuckle.

  “Uh yeah, I guess so.”

  “So uh…marriage then.”

  “Yep.”

  “Want to make it the real deal?”

  She nodded again and smiled broadly. “Please.”