"Are you ready for me, sweetheart?" He asked, stroking her forehead and tucking her side bangs behind her ear. They were on his bed with him on his hands and knees, over her body. She was aroused but very nervous.
The last time she had had sex was a year ago with her previous boyfriend and she was worried a similar occurrence was about to repeat itself. She knew her opening was especially tight for some reason, but her ex wasn't very sympathetic to her pain and worry. He seemed to only care about his pleasure. Things ended soon after he realized she couldn't give him what he wanted, leaving her alone to pick up her self-esteem and convince herself it wasn't her fault that he left.
"Yeah, I'm ready." She said, forcing a convincing half-smile.
"I can't wait to be inside you, baby." He leaned down to kiss her as he lowered his hips and guided his cock to her opening with his hand. He rubbed the head around her entrance and began to slowly push in.
"Mmm, fuck, you are so tight." He whispered as he attempted to enter her pussy.
She could feel that her entrance was not loosening up and her mind was in chaos trying to block out her previous trauma. She wanted to enjoy herself but she didn't know how to get herself to relax.
He barely got the tip in when he heard a hushed squeak. He moved his gaze from her pussy to her face to verify if he had actually heard her make a noise. Her expression confirmed it - she was in pain.
"Woah, hey - princess, are you okay?" He stroked her temple and looked her in the eyes. "You're in pain, aren't you?" He asked.
"Yes...but it's always like this. I don't know what's wrong with me." She was hesitant to admit how she felt. It was such a vulnerable position to be in.
"Hmm...you mean you've had pain during sex with your other partners as well?" He laid down on his side and rubbed her belly instinctively.
"I don't really want to talk about it but... yes." She couldn't look him in the eyes, worried that he may be resentful for not being able to give him what he wants.
"That's okay, we don't have to push anything. Have you been okay playing with yourself? You know...when it's just you?" He seemed to be switching into doctor mode. His hand was warm and comforting on her belly and it made her feel better that he wasn't trying to get distance between them. But she still couldn't look him in the eyes.
Her face flushed pink. She had never discussed masturbation with any of her partners before.
"Well...I mean, I can play with myself just fine, but it hurts if I try to use a dildo. My whole body tenses up." Her voice dried up a little at the end from admitting that out loud.
"Aw, sweetheart. Don't be embarrassed with me. I just want to help." He leaned in and kissed her cheek. "Have you seen a gynaecologist about this before?"
"No...I haven't." She said, hesitation emanating from her voice.
"Why not?" He asked gently.
"I'm nervous...I don't want them to hurt me by trying to figure out what's going on." She was fidgeting with the furry blanket she was lying on top of.
He was watching her carefully, assessing her reactions to figure out what she needed. "Ok, let's not talk anymore about this for now. I can tell it's difficult for you." He changed the subject to avoid causing her anxiety to flare up even more. Buut...if you're feeling up to it, would you mind if I played with you a little?" He smiled up at her.
"I-I don't know. I don't think that will change anything." Her body was starting to tense up just thinking about him trying to enter her again.
Seemingly reading her mind, he said, "Don't worry, I promise I won't try to enter you at all." He looked lovingly into her eyes but she wasn't sure she could enjoy something like that after what just happened.
"C'mon, kitten. Your sweet little pussy is still so wet. You need to be taken care of tonight and I want to give you that in any way I can." No guy had ever framed pleasure that way to her before. She looked like she was deep in thought.
He continued, "I'll be gentle and if it doesn't feel good at any point, we'll change things up or stop, if that's what you want." He threaded his fingers with hers and squeezed her hand.
"Okay...I think that would be okay..." She said it more to convince herself than him.
He smiled. "Oh, good." He let out a sigh of relief and looked her in the eyes. "Thank you for letting me do this for you." He started leaving kisses down her neck, slowly moving lower with every kiss. His warm lips against her skin seemed to distract from the chaos in her mind.
"I'll go slow, okay?" He whispered as he reached the spot between her legs. She nodded and braced herself as she watched his lips approach her slit. Being pleasured with no ulterior motive was going to take some getting used to and she wasn't sure if her mind was going to allow her body to believe that that's all he wanted.
When he finally licked her pussy for the first time, she was surprised by how tenderly he started. It was so gentle that it almost felt like a feather had just brushed along her clit. She watched as goosebumps became visible on her arms.
"Does that feel okay?" he asked, looking up.
