AGE GAP | ANAL PLAY | NEW EXPERIENCES
A Pleasant Surprise At The Rear Entrance
Blake experiments with new sensations.
“So, why haven’t you ever tried it?” His words appeared on the screen after the dots stopped pulsing. Blake bit her lip, fingers hovering over her keyboard as she formed the reply.
“Honestly, it kinda scares me.” She hit the send button, letting the words cross the distance to Walter’s device.
“Afraid it’s going to hurt?” His reply came a lot faster than hers.
“Yes, that’s definitely one of the fears. But I also worry about whether it will be messy,” she typed back. “And then there’s the usual concern — what if I’m terrible at it, you know?”
“Those are legit fears.” It felt good to have Walter confirm and not downplay it or tell her that she was silly. “But there are ways to ensure that it will go well, things you can do ahead of time to prepare.”
“Like what?”
“Will you try it if I give you some instructions?”
Blake leaned back against the pillow on her bed where she had been sitting. She liked Walter and their conversations have gotten rather intimate. They’d talked frankly about their prior experiences, of which he had way more. But this would be taking another step, doing something physical based on his directions. Would she follow through?
“I guess it depends on what you want me to do,” she finally told him.
“Next time that you’re playing with yourself,” just reading those words made her cheeks flush, “gather up all that moisture from your pussy and slide a finger back towards your asshole. Just rub a finger over it, absorb the sensation, enjoy how that feels.”
Her pulse picked up and her thighs pressed together a little tighter. That didn’t sound so bad. She could imagine herself doing that.
“That’s all?”
“Just to start. The next step would be getting a bit of Vaseline or proper lube, coating that finger, and slowly trying to push it past the tight rim of your asshole. But you can save that for another time. Baby steps.”
That didn’t seem too objectionable, though Blake wasn’t sure how much she would enjoy doing that. But when she tried it that night, she was pleasantly surprised. She set a goal for herself to just enjoy her solo session, as much as she ever did. Getting into the zone was key — she watched some rough BDSM porn that always made her wet and teased her nipples the entire time so that they were ultra-sensitive.
When she made her way down to her center, she slid her fingers through the moisture lazily, moving back and forth and building up the tension. By the time she pushed two of her digits inside her pussy, her hips were bucking towards her hand, wanting all the stimulation inside her. She didn’t forget about Walter’s instructions though and it excited her to follow through on a task given to her by the older man across cyberspace.
She pulled a finger out of her pussy and drew it back to her rear hole. Yeah, circling it with moderate pressure definitely felt good and she imagined how she would report this back to Walter. She pressed a bit more firmly and felt the hole widen slightly underneath her fingertip. This didn’t hurt, she thought, but the sensations that it added definitely made her whimper with pleasure.
She would go even further, she decided, reaching for the tube of lube in her nightstand. She squeezed a dollop on her finger and brought it back to her rear entrance. Massaging as she added pressure felt so good! She breached the tight rim with no problem, pushing her finger deeper. It was fantastic! Using her other hand on her clit, she tipped over the edge quickly, coming with her finger in her ass.
“I told you, with the right prep and taking it slow, it will feel good,” Walter typed when she described to him her solo session. She could almost hear the smugness in his voice at being right.
“What should I do next?” she asked him.
“I’d recommend getting some training butt plugs. They’ll come in different sizes and should be smooth silicone. It will give you a chance to start out small and work your way up. Carefully, using lube, taking time, playing around.”
This seemed like a step into a new fetish zone, but Blake didn’t mind. She was twenty-eight and couldn’t really describe herself as having any fetishes just yet. She liked watching BDSM videos, but all the real sex that she’d had before had been rather vanilla. Trying something new, especially under Walter’s guidance, was a fun little project.
Walter checked in with her about her progress but didn’t pressure her for more. His demeanor was supportive and encouraging and she felt comfortable discussing all this stuff with him. She even looked forward to it.
“I have one in right now.” She bit her lip after sending the message and watched impatiently for a response.
“That’s cool,” he answered. “What size?”
“The medium one.”
“I know we haven’t gone there before, and feel free to say no, but how would you feel about sending me a picture?”
Blake’s knee bounced as she reread the request. She was rather proud of herself for doing this and for enjoying it as well. Discovering this new pleasure had been a rather big deal for her and she was grateful to him for easing her into it the way that he did.
She set up her phone camera on a timer. It was a careful maneuver of bending over, pulling aside her panties in the back only, and lining up the shot just right. She didn’t want to reveal too much. After a few tries, she had a picture she was happy with and while her fingers trembled, she hit send.
“Wow, that looks fantastic,” Walter replied. She was quite proud of herself, both for having the confidence to share a picture and for exploring a new area of her sexuality.
She felt an easy connection with Walter, appreciating his advice and getting more and more comfortable sharing with him. Pictures were sent in both directions regularly now, both of her experiments and of how much he enjoyed them. And then came the phone calls, conversations that lasted into the night. Some were entirely innocent and others delved into deep, dirty places she hadn’t imagined going with Walter a few weeks ago.
“I would just feel so much better if you were the one who did it for the first time,” Blake finally confessed to Walter.
“If I did what?” A brief silence extended between them. “Tell me.”
“If you were the one to fuck my ass for the first time,” she blurted out. “I’d be a whole lot more comfortable knowing that it’s you and you know what you’re doing.”
“I think you’ve built me up a bit much there, Blake,” he chuckled.
“You’ve introduced me to this whole experience and you have been so patient and so… not pushy. It’s almost like you’ve held my hand through this whole thing and I want to feel the real thing now.”
“Tell me what you want to feel.”
“Your cock in my ass.” She was completely confident that that was what she wanted.
He had agreed and would drive the hour and a half the following weekend. Blake was a bundle of nerves waiting for him to arrive Friday night. She was incredibly attracted to him, despite the fact that she had never before dated a man who was that much older than her. Walter was fifty, but she saw his age as a sign of his experience and she was eager to learn from him.
“So, did you prep for me?” he asked, after they had been sitting on the sofa chatting for a while, their glasses of wine now empty.
“No,” she told him, suddenly feeling nervous again as if she screwed up. He smiled.
“I actually hoped that you hadn’t, so I could do it for you.” He leaned in to kiss her then and it was all the warmth and comfort of their conversations melting into her and spreading like a high-proof liquor.
He undressed her, slowly, kissing her lips, neck, and breasts as he did. There was no rush. It had been a decade since she had lost her virginity, but now it felt like such a similar sensation — the combination of nerves and giddiness at what they were about to do. The major difference was that unlike with her eighteen-year-old boyfriend, she believed in Walter’s collected level-headedness and knew that he was not freaking out about this. He knew what he was doing and how to handle her.
In the bedroom, he leaned over her upturned ass, giving it plenty of attention. It came as a shock to her when his warm, wet tongue slipped over the rear hole, prodding it. She mewed as he worked the buttplug into her, slowly, as if this was a pleasure in itself.
The weight of his body over hers served to make her wetter and she welcomed the stretch that came with his cock pushing into her pussy. It felt entirely different with the buttplug in place. Parts of her were stimulated that she hadn’t been aware of before. Her head rested on her hands as he took his time, rocking into her from behind. The friction of her breasts with her soft, cotton sheets was a pleasant addition as her body ramped up towards the climax.
Blake moaned and Walter’s movements seemed to slow to a crawl, as though he wanted to stretch this out. Was she too sensitive? Too close to coming too soon?
“Please, don’t stop,” she pleaded with him.
“I don’t want you to come yet,” he told her in a calm voice. “Not until my cock is in your ass.” Blake felt her pussy clench around his shaft at those words and that didn’t go unnoticed. Walter chuckled softly above her. “Oh, I know that’s what you really want. But are you ready?”
“Yeah, I’m ready,” she told him.
He pulled out and she angled her ass higher, getting up on her knees.
“No, not like that,” he told her. “Come ‘ere.”
Walter laid down on the bed, on his side, and pulled her into him like a little spoon. She remembered now that he had mentioned this before, a long time ago, before she even started experimenting, that he liked the spooning position. He said that it was easier, more relaxed this way.
He draped his arm around her, kissing her neck and shoulder. Blake wiggled her ass against him, feeling his erection between her ass cheeks. He was still entirely hard and reached a hand to play with her breast while she humped her ass against him. Things were going far slower than she had expected and she was starting to get impatient.
“Don’t rush it,” he said against her ear as if he could sense her excitability.
He reached down between her ass cheeks and played with the buttplug, twisting it this way and that way, then pulling it out part of the way and pushing it back in. It felt incredible but Blake could barely stand it. Her body was supercharged and all the stimulation kept her on the very edge, so close to exploding. She moaned and whimpered while he played, taking his sweet time with her. And when she thought she couldn’t handle it any longer, she reached a hand between her own legs, thrusting her fingers into her wet folds.
“Not yet.” He caught her wrist in a move that she hadn’t expected. “Be patient and I’ll get you there,” he told her.
He pulled her hand up over her head and asked for her other one as well. With her wrists gathered in his grip over the pillow, he resumed fidgeting with her plug. When he had pulled it all the way out, the head of his cock replaced the toy at her rear entrance. It felt warm, simultaneously hard and velvety. He lined up and pressed in carefully, just the tip.
There was a sting to the stretch, but along with it an incredible pleasure. With the head of his cock firmly notched, he lifted her leg up and hooked it over his hip before pushing further in.
“Oh God!” She couldn’t contain her cry as he pushed further and further inside her. It felt different from vaginal sex and from the plugs and fingers she’d inserted there before. She felt tighter and more full, like he was filling her much more completely this way.
Each thrust became more pleasurable, ramping up to something that Blake could not imagine. Where there was friction at the start now was an arousing, building pressure. He picked up speed, his cock sliding into her with ease and retracting almost all the way before he slammed back in. The quiet slapping sounds of flesh added to the experience. And when the orgasm hit, Blake couldn’t pinpoint where it had come from.
Her body pulsed and quivered, waves washing over her, and it all came from somewhere deep inside her that she hadn’t expected at all. Walter grunted behind her, keeping his rhythm steady while she continued to fall apart.
He pulled her to himself, as if he couldn’t get close enough or deep enough, even though his cock was buried to the hilt in her ass now. Each one of his strokes sent aftershocks through her. Yet he still reached a hand down between her legs and pinched her clit between his fingers, as if the orgasm she already had was not enough. Her body jerked with new force and Blake cried out. Everything buzzed from overstimulation and she couldn’t contain it anymore. Walter slammed deep and stayed there, breathing heavily. His hand was cupped over her mound and he held her tightly to him while he emptied into her. She could feel the throbbing of his erection inside her and stayed still, absorbing it.
“I hope that didn’t disappoint,” he whispered in her ear then kissed her neck again.
“Not at all. How could it?!”
“I’m glad.” A beat of silence then, “You had been scared of it before. Remember?”
“Ah, yeah. Something like that.” Blake’s eyes had fallen closed and she relaxed into his chest. She didn’t regret meeting this man or trusting him with her body. She could imagine doing this again.
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