The Wallflower and The Star Athlete (closed for Poprockz)

[Poprockz]

His inability to get his finger inside her initially was due in part to her nervousness. She trusted him, of course she did, but it was an entirely new experience for her and she wasn't sure what to expect. As such, she couldn't help but clench a little. Only when she urged herself to relax and take a deep breath did her entrance give way to his insistence.

"It feels... odd," she admitted, "but not unpleasant. You can keep going- I'm okay." Olivia gave him a reassuring smile.

 

[Mr_Positive]

He smiled at her reassuring words, slowly and very gently working his finger deeper into her ass. He took his time, stopping almost every millimetre, before continuing his journey into her most intimate hole.

Slowly, but surely, his finger was finally fully in her ass. He held it for a minute, allowing her to adjust to this brand new sensation. He wondered how she could handle his cock fully sheathed in her pussy and now his finger buried in her ass.

 

[Poprockz]

"Your finger feels really big," she chuckled, "Are you all the way in?"

Never had she ever imagined that she would ever have two of her holes filled at the same time, and yet here she was. There wasn't any real movement, so she couldn't say for sure whether she liked it yet. It wasn't painful like she thought it might be though. Maybe that happened more when someone tried to roughly force their way in without regard to the person whose ass they were plundering. Thankfully Adrian was a gentleman even with a finger in her ass.

 

[Mr_Positive]

“Yes my love. I am fully inside you, twice”, he said with a chuckle.

He slowly pulled his finger back, almost to the point that it slipped past her tight muscle, before slowly inserting it again. He could feel her ass loosening all so slightly. Its grip on his finger was just below the point of painful. But he was in no position to complain. The girl that had his heart was allowing him to penetrate two of her holes at the same time.

He then started matching his finger movements with his cock, again going very slowly.

 

[Poprockz]

The moment transformed the sensation into something different, and at first she was tentatively uncomfortable. However, when his cock started moving as well, once again things changed. His strokes had been pleasurable before this exploration began, so when he started to thrust gently within her in rhythm with his finger, his finger started to also feel more pleasant. In order to help this along, one of her arms snaked underneath herself and between her legs so she could rub her clit at the same time.

A soft little moan came from her. It was as though the wall between her ass and her pussy were being massaged on both sides, and she found that she quite enjoyed the sensation.

 

[Mr_Positive]

Her moan was deeply encouraging to him, emboldening him to increase the speed of his strokes. Despite how slowly he was going, the familiar feeling of his pending orgasm was building. The erotic and almost taboo nature of what they were doing was affecting him much more than anything they have done until now.

“I’m close, Liv”.

 

[Poprockz]

She wasn't yet close to her own orgasm at the moment, but he hadn't gotten the chance to cum yet at all. So when she heard that he was close, she found herself pleased that he was finally getting a taste of the same sweet nectar she was. Just because she wasn't going to cum at this point didn't mean it didn't feel good though.

"Cum inside me then- cum with your finger in my ass, baby," she purred, hoping it didn't sound too cringey or slutty. Dirty-talk wasn't her forte yet, and she still felt a bit tentative about it.

 

[Mr_Positive]

Hearing Olivia’s dirty talk was so surprising, but so arousing. He didn’t last long after that.

“OH FUCK”, he almost shouted as his exploded, filling up the condom. He almost held still as the intensity of his orgasm took hold.

Once he calmed down, he removed both his cock and finger from her. He went to the bathroom to dispose of the condom. While he was there, he grabbed the complimentary bottle of lube and went back to Olivia. Something told him their night was not done yet.

“How was that, my love?”

 

[Poprockz]

She was lying on her stomach on the bed, her ass no longer in the air as she rested. "That was a new experience. I think I liked it." There was a little laugh before she added, "I mean I did like it. I thought it was going to hurt, but it didn't hurt at all. Have you ever done that before?"

 

[Mr_Positive]

Adrian smiled at her as she spoke.

“No, never. I had never even really thought about it, let alone bring it up with a partner. But see you…..displayed like that, it just looked so inviting”.

He lay down beside her, his hand idly stroking her ass,

“Would you like to explore it more?”

 

[Poprockz]

His answer brought a flush to her cheeks. So he hadn't done that with anyone else? It made her feel a bit of pride to hear that. He felt comfortable enough to bring it up and pursue it when the fancy struck him, and he had found her ass attractive enough to decide to do so.

She blinked in surprise, "what do you mean? Like you want to finger me again?"

 

[Mr_Positive]

Adrian smiled, finding Olivia’s surprise all too cute. He had to remind himself she was still very inexperienced. Not that he had that much more experience.

“I loved it doing it. It was so erotic. But only if you want to. I will never push you to do something that is uncomfortable or doesn’t bring you pleasure”.

 

[Poprockz]

His enthusiasm for it made her excited, and she very much considered agreeing to it again. She had a thought though- if he hadn't ever fingered anyone that way, that meant he hadn't fucked anyone that way either. Coming into the relationship, she had been completely inexperienced while he at least had one or two previous partners to be intimate with. The fact that this was uncharted water for them both made her heart quicken. Olivia wanted to have something that would be forever imprinted in his memory- one of his firsts.

"Do you want to try... actually having sex that way?" It felt embarrassing to suggest, but she continued forward. "I want to know what it feels like, and I want to explore it with you." Her blue eyes shined hopefully, waiting for his reaction.

 

[Mr_Positive]

A slightly serious look went across Adrian's face, studying hers to see if she was being serious. The playful look in her eyes told him all he needed to know.

"You are incredible, always surprising me with how much you want to grow. Absolutely, I want to experience this with you. Let's take our time."

He encouraged her to lay on her side, drawing her knees towards her chest. This exposed her most intimate hole to him in the most comfortable position for her. He knew she would need more finger probing before he could begin to attempt to put his cock in her.

He lubed up his finger and spread some more around her tight ring. His earlier fingering taught him to be patient and how apply the right pressure to encourage her muscle to relax. He lay close to her, allowing her to feel him right there with her. He then lowered his finger and began to tease her, taking his time.

 

[Poprockz]

“We have all night,” she responded with a smile and a gentle kiss to his lips before she got into the position he directed her to take.

It felt odd at first just like the last time, but she got used to it more quickly this round. Olivia knew to try to relax and breathe, focusing on not clenching around him. What they were going to attempt to do was pretty kinky, she thought. Perhaps anal sex was lower on the list of things many might consider as “outside the norm,” but it was still something not everyone partook in.

 

[Mr_Positive]

He couldn't believe the position they were in - how did they get here? Just a few weeks ago, Olivia was a virgin and he had only been with one other person in his life. Now they were preparing for him to fuck her ass.

But as strange as it may have sounded, it felt right with her. Their strong connection from the moment they met in the soup kitchen had blossomed into a relationship built on love and trust. Only the most foolish of men would throw that away.

His free hand stroked her body as his other hand very slowly finger fucked her ass. It was so surreal, yet so erotic. Despite his very recent orgasm, he could feel the familiar sensation of his arousal rising again.

 

[Poprockz]

His finger felt even more slick when it was lubed up like that, and she eventually found him easily sliding in and out of her puckered hole. Despite how it looked on paper, it was moments like these that she truly felt close to him.

He was so gentle and understanding- it made her want to give him every last part of herself, having found the only person worthy of it. She felt so incredibly safe laying there side-by-side with him as his fingers caressed her skin.

“Mm… what did I do to get so lucky?” She spoke, turning her head to look at him over her shoulder with a smile. “Being with you feels like a dream.”

 

[Mr_Positive]

Adrian smiled as she turned to look at him. Her words mirrored his own thoughts.

"I am the lucky one. I, somehow, got chosen to see you blossom from the untrusting, very guarded person I met in that soup kitchen, to the free spirited, sexually open woman you are now".

His finger was moving so freely, he gently coaxed another into her ass, stretching it open further. He continued to search her face for any doubt or pain. But none could be seen, only pleasure and trust.

"Never, in my wildest dreams, did I imagine I would be telling someone I love them, and then proceed to finger their ass", said with a chuckle.

 

[Poprockz]

'Free spirited' and 'sexually open' weren't things she had ever been described as. She could understand where she would come off as sexually open at this point, but wasn't sure where he got that she was free spirited. Olivia wasn't sure that she had really changed all that much other than learning how to love and trust another person.

The second finger wasn't particularly difficult to take, but she could feel it stretching her out more. For some reason, with all the lubrication, she somewhat enjoyed the feeling of being stretched. She could only imagine how much his dick would stretch her once he put it in.

"Believe me, if you had told me that this would be happening a couple months ago, I would have looked at you like you were crazy," she replied with a chuckle of her own. "You bring out something in me I didn't know was there."

 

[Mr_Positive]

Watching his two fingers easily move in her ass gave some assurances that she was loosening to begin attempting putting his cock in her. Her pussy was always a tight fit, but this would require patience, willingness on her parts and copious amounts of lube.

He withdrew his fingers and applied lube to both his cock and to her, ensuring the whole area around her tight ring and well lubricated. He wanted this to be as pleasurable as possible for her, with as little pain as possible.

He kissed her shoulder and neck a few times as he moved himself closer, resting the head of his cock at her well lubricated ass. He lodged between her cheeks, and then very, very slowly, began to apply pressure. She was so tight, he wondered if this would be a step too far for them, despite their willingness to make it happen.

 

[Poprockz]

Olivia breathed deeply as his head pressed against her opening, willing her body to relax and allow him entrance. His patience and dedication in preparing her ass paid off, and his head was allowed to breach her. She swallowed hard, her thighs trembling slightly as she tried to reconcile the entirely new sensation. Damn he felt large! It was just the head, and yet she could already feel the difference between his cock and his fingers.

Regardless of the fact that she already felt stretched more than his fingers could attempt, she found herself letting out a soft moan of longing. She was very turned on by the knowledge that her anal virginity was being claimed by the man she loved.

 

[Mr_Positive]

Adrian heard her moan as his head popped in, a smile playing across his lips as he knew she enjoyed the sensation. It was also not lost on him that she had just, very willingly, given him her second virginity. But this was a shared one, he had also given her his. This thought gave the moment a really special feeling.

He held still for a moment, allowing her to accept the new feeling. Very slowly, very very gently, but with enough pressure, he pressed forward. His eyes dipped, and the sight was just intoxicating. He watched as her impossibly small and tight hole seemed to just stretch around him.

"Oh my god, Olivia. This is just, wild".

 

[Poprockz]

"What?" she asked breathlessly, "does it feel weird to you?"

She had no idea what it was like to have a dick, but she imagined that the sensation of fucking a pussy was different than that of fucking an ass. Perhaps the textures were different or some such thing. All she knew was that she could feel him deeper and deeper within herself and every centimeter was a new sort of journey.

 

[Mr_Positive]

“No”, he said quickly. “It feels amazing. Very different, but a very good different. I can’t believe we are doing this”.

He reached a point where he felt her ass was not going to accept any more. He wasn’t fully in, but he was close. Not wanting to tarnish their experience by forcing anything, he held still. Again his eyes dipped to where they were joined. It was a mesmerising sight. It stirred his newly discovered dominant side. This was a very submissive position and act for Olivia. He knew the trust she was placing in him.

 

[Poprockz]

Olivia was now panting softly as she felt him rest with his full length inside her- at least that was what she assumed based on the feeling of it. It felt so very large that it seemed impossible that it wasn’t all of him. Her ass was struggling to get used to being filled, but Olivia herself relished the feeling.

“I can’t believe it all fit!” She remarked between breaths.