He’d been fantasizing about it for so long but now that it was actually about to happen he felt afraid, he didn’t know if he could handle it.
“Don’t worry Connor baby, I’ll be gentle”, she told him in a reassuring tone as she ran her fingers down his spine and sides.
The sensation of her fingertips against his bare, oversensitive skin made him shiver and grunt in response.
He was naked and on all fours on Maddie’s bed as she stood behind him. She could feel he was anxious and that he needed to be touched, so she leaned over him and kissed down his back with slow deliberation all the way to the top of his ass. That made him stick his ass out at her as if begging her to start, he wanted her to take him. She licked her index finger and just ran it around the edge of his virgin rose bud making him suck in a deep breath. He knew he could trust her not to take it too fast or be too rough with him but still he wasn’t even sure he could handle her taking it slow and easy.
When he confided in her and told her what his secret desire was he was sure she would find it disgusting and turn him away, but to his great surprise she was not only unfazed by it but had actually done it before and was completely turned on by it. And that is how they ended up here, in his bedroom, with her now rubbing a good amount of lube between his ass cheeks and him biting his lips.
She was massaging his anus more firmly now, warming him up, getting him excited as she simultaneously rubbed his cock. He was rock hard and panting as he felt her push her finger against his opening with some purpose to it. He felt pain flash through him as she pushed it in to her first knuckle and he cried out. He wanted to resist her, to push the intruder out of himself and make this stop.
“Don’t fight me baby,” she told him, “just try and relax your muscles and I promise it will feel better soon.”
He nodded his head in response and tried to focus on letting go, he knew that it will be ok because she was with him. His cock wasn’t as hard now as before, the pain had made his erection subside a little so she stroked him for a few minutes before pushing her finger deeper inside up to the second knuckle. There was the pain again but this time he bit his lip and tried to focus on the hand wrapped around his cock and not the finger that was insistently pushing into his anus.
She kept her finger in him and wiggled it a little and he felt his stomach tingle with the unknown sensation. He was starting to enjoy it and get more excited about finally fulfilling his fantasy. She pushed her finger all the way in and the pain was mingled with pleasure for him, he moaned lustfully and even pushed his ass to meet her.
“You are doing so well Connor,” she leaned over him and playfully bit his earlobe. “Do you like it? Do you want more?”
“Yesssss…” he moaned in response and wiggled his ass a little.
Her finger started moving inside of him, in and out, at first slowly and then picking up pace but she wasn’t stroking his cock anymore- she didn’t want this to end too soon, she wanted his orgasm to be the prize at the end of the road for him. She kept finger fucking him for a bit, letting him feel the rhythm until he started moving on his own and pushing back onto her, at which point she thought it was time for a second finger. As he felt the two fingers going in he panicked a little, fearing that he couldn’t stand it, but his rear muscle was softened by the activities so far and took them in without much resistance or pain. actually the pain was so minuscule it barely existed while the pleasure of being full was overwhelming, it made him tingle all over and the desire to cum was very strong despite his cock not being stimulated.
“You are so sexy Connor,” she told him in her sensual voice. “Your tight ass is making me very wet and horny.”
“Oh fuck, is it really?” he moaned in ecstasy- it was by far the sexiest thing anyone had ever told him.
“Yes it is, would you like a taste?” and with that she dipped the fingers of her free hand inside her wet snatch and brought them to his mouth, coated in her juices.
“God yesssss…” he moaned as she shoved her wet fingers into his mouth and he sucked on them.
“I think you are ready for something bigger in that hungry little ass of yours, sexy boy,” she told him as she felt he was pushing himself unto her fingers harder and faster.
She withdrew her fingers and stepped to her bedside table where she pulled a toy out of the top drawer. The toy was a blue but plug about 4.5 inches in length and 1.5 inches in width, cone shaped with a wider base. Maddie turned and showed him the toy she had just pulled from the drawer.
“Do you think you can handle this?” she asked him seductively and then put the toy in her mouth, lustily sucking on it.
He gasped as he looked at her, her hand sneaking down to rub her clit as she sucked on the rubber plug and looked straight into his eyes.
“Soon this will be inside you Connor. Are you excited?” she asked with a wicked grin.
He had no time to answer her question as she pulled the plug out of her hole, all wet and shiny with her liquid and pressed it against his slightly parted lips, making him take it into his mouth. It tasted so good after having been inside her that sucking on it was a pleasure.
“I see you are enjoying yourself,” she teased him. “You better make it nice and wet so it’s ready for your ass.”
Her words made him shiver with need and desire for what she was promising him. He increased his efforts on the toy, slobbering over it to show her his desire. After a few more seconds, she pulled the toy out of his mouth and moved to stand behind him. His cock was rigid with arousal and she cupped and squeezed his balls lightly just to make him moan.
He felt the toy against his asshole as she teased him with the tip; it was so smooth and wet with his saliva. He instinctively spread his legs wider, preparing himself for the object that was about to invade his most private and sensitive place. He felt her put more lube and probe the tip of the plug more firmly against his opening and made an effort to relax so that it could enter him more easily.
“That’s right Connor baby, relax and let it in,” she told him. “You know you want to; you know it will blow your mind.”
“I’m trying,” he whimpered in response as the pressure against his puckered hole increased.
There was pain again as the plug was slowly but surely being pushed inside him; he thought of crying out for her to stop when the plug was about half way in but he didn’t, he bit his lip and held on to her bed sheets so hard that his knuckles were white.
Again she wrapped her hand around his cock, which wasn’t rock hard anymore, the pain having its effect on him. She stroked his cock slowly but with purpose as she kept pressure on the toy going into his tight ass hole. She knew from experience that the first time was going to be difficult and painful but she also knew the pleasure that the anal penetration could bring, especially to a man. The toy was almost in him, he only had to take in the wider part and then he could start to really enjoy himself.
“Connor baby, it’s going to be a bit more painful now, but I’ll do it quickly, so just hold on and it’ll get soooo good after that,” she told him matter-of-factly.
“Ok,” he nodded his head and braced himself.
“Here goes,” she said as she gave one forceful push and the plug went all the way in with a little popping noise.
Connor screamed with pain as the toy fully invaded him; to him it felt like an electric shock ran through his body. His muscles tried to push the toy out but it was not going anywhere. She kept stroking him with one hand and caressing his lower back and ass cheeks with the other, waiting for him to get used to the intruder in his rear opening.
Slowly but surely the pain started to subside and he could feel the pleasure take its place. Every part of his body was suddenly a lot more sensitive and the feel of her stroking him was electric. Despite being in pain moments earlier, now he felt like he needed to cum, and cum hard. He could not describe what exactly was happening but it was incredible and oh so good- just like Maddie told him it would be. He began moving his hips to meet her hand, wanting it faster and harder, and each time he thrust, his muscles would contract around the toy and make him feel even better.
“That’s right Connor,” she encouraged him. “Doesn’t that feel like heaven?”
It didn’t feel like heaven though, it felt like a fire ball was inside him, it felt as though he was peeing cum, as though he was about to pass out and still keep cumming. He was screaming and cumming and unable to stop or understand what the fuck was happening.
When his orgasm had finally subsided, he collapsed on the bed, breathing hard and trying to regain some semblance of self-control and logic. He felt spent and exhausted. He looked at Maddie who sat down on the bed in front of him and smiled at her.
“So did you enjoy it as much as you thought?” she asked with a grin.
“Way more than I ever thought,” he answered honestly.
“Well now it’s my turn to enjoy,” she told him with a wink.
