He smiled gently at her not being so cruel as to have her wait any longer then needed. Washing his hands away for the moment he kissed her forehead from her rather now open request as he would gently lie her down upon the grass, letting her present herself for him He figured this position would be best since it would shelter her from anyone watching if one came across them but also it kept eye contact with her, protect her with his body and provide some of the best depth to his thrusts.<br/><br/>He took a moment to look at her from head to toe with his eyes quietly showing an unbearable sense of need at this point. He would take aim with his erection with his left hand whilst the right rubs softly at her folds<strong>"Jessy, I am going to warn you now, this might hurt since you're new to this."</strong>He said. It was not to scare her but to let her prepare for it rather then surprising her with it. He kissed her lips as the tip of his thick cock pressed to her folds parting them. Only the tip was inside of her and he rubbed slowly against her as he leans over her now covering her form with his own body like a patio roof. One arm braced to the ground whilst the other holds himself steady.<br/><br/>He began to push into her his manhood finally entering her warm passage, now nice and sensitive from his ministrations and well lubricated. Should she have had an active athletic life or such, she may have already broken the hymen, and there would be no pain or blood. But if she hadn't he would feel his tip touch her maidenhead and then with a firm thrust he breaches her last line of defense. He did it quick so as not to drag it out. He held perfectly still when he completely entered her at first. Kissing her brow he would speak up<strong>"Let it settle inside and keep your eyes on my own. Let me know when I can move"</strong><br/><br/>When she gave a word or nod to start moving he would thrusting very slowly inside of her, not rushing this. He wanted to take his time with her so that she would not find this unbearable. He would keep his eyes upon her. As he kept going he listened and looked for any indication that she was starting to feel the pain stop. When it started feeling good he would pick up the pace thrusting inside of her. Her breasts swayed hypnotically against his chest and he could not help but smile. Shuddering from the sensations of warm flooding him his blood boiled and his warmth passed into her own. Every now and then he rolls his hips in between thrusts to try and tag different areas.