Chapter 55. A First Time/ Part 2
Jackson Johnson's House - Sanctuary - The Hamptons
Jackson Johnson
Before continuing, I got out of bed and searched for my dress pants. I found my wallet, and inside it, I found the condom. I closed my eyes for a moment, thanking Jacob for his birthday joke a year ago when I turned thirty. "For when you need one at an unexpected moment," were his words. When I opened my eyes, I turned to Lilly, who was still trying to cover her body. I smiled, just as nervous as she was. I approached and climbed back over her body. Her brown eyes were still dark, a thin ring confirming her excitement.
"Ready," I whispered before pressing my lips to hers. When I pulled away, she caressed my face with both hands.
"Are you ready?" she asked. I nodded confidently. She bit her lip for a moment.
"I just need to put on the condom and..." I stopped my explanation when I saw her blush.
"You have to take off your boxers," she whispered.
"Yes, of course..." My breathing started to become unsteady just imagining what was about to happen.
With one hand and quick movements, I removed my boxers. I stayed sitting on my calves while still between Lilly's legs. She lifted her head to see more. My erection was at its peak, and she gasped when she saw my "friend" standing tall.
"It's... big," her eyes widened with surprise.
"Oh," I blushed. I handed her the condom. "Can you help me open it?" She nodded and easily tore it open with her teeth, but she didn't look away from me. She handed it to me, and I clumsily took it out and was about to put it on when she stopped me.
"Wait." I looked up at her. "I-I'll help you," she said, sitting up and reaching out to help. "This stretches like this," she began to say. I shivered when her hands touched the skin of my member. With some clumsiness, she adjusted it well, and I even thought it was pretty tight. "Perfect," she whispered, then her eyes locked onto mine. I leaned toward her and cupped her face before kissing her again. I shifted to kneel between her legs. Slowly, I guided her back to lie down with me on top of her. My hands went to her breasts, and I began to caress them. Her gasps and moans started to drive me crazy, exciting me even more. I broke the kiss to kiss her neck, then moved down to her breasts and caught her nipples, nibbling on each one. She moaned more, writhing restlessly beneath me until... I positioned myself and placed my member at her entrance. She gasped, and I could see her breathing become more erratic.
"I'm going to..." I breathed heavily, placing the tip and starting to push in slowly, like I had seen in many adult movies. I focused on her, her breathing, her face, and the sound that escaped her lips until I stopped. She was too tight, and I feared hurting her.
"Do it," she whispered, reaching out to find my hands and caress them. "Just push more..." she insisted when she saw I was still.
"I'm afraid it'll hurt you..."
"Do it..." she whispered again, pulling my hands to bring me closer to her. She raised her pelvis to seek friction. I didn't dare until her hands slid to her mons and reached my member. Her fingers barely brushed the skin, and I shivered. Slowly, I began to enter her.
"Oh my God..." I groaned through clenched teeth as it started to hurt. "I can't..." I gasped.
"Don't stop, don't stop..." she moaned, causing more pleasure in me. I felt something pinching my tip. I closed my eyes, but Lilly caught my face. "Look at me." I opened them. "Yes, push more..." I pushed painfully a little more until I felt relief and some pleasure. She bit her lip and then gasped. "Now move faster, we'll lubricate more, and it'll be easier..." I nodded with clenched teeth. I placed my hands on either side of her body to move, and then I began... the pleasure was indescribable.
"Oh my God," I murmured as I moved more. From my position, I saw her breasts moving to my rhythm. I leaned one hand on the headboard and lifted her leg with the other for better access. Her moans increased.
"Yes, like that... keep going..." I sped up more and more until the bed began to shake a lot, the headboard banging against the wall, which I didn't care about. "I'm coming..." she moaned, and I quickened my pace. I felt her interior clench around my member. I was about to lose control of my own climax. I couldn't stop. She screamed so loudly it distracted me, her nails digging into my chest, causing pain. I resumed the thrusts until I came after her. The sensation that came over me was... inexplicable. I felt my body tremble, a shiver running from head to toe. My vision blurred, and our breaths were unsteady, as if we had just finished a marathon. Carefully and with some pain, I withdrew from her, took the used condom, and disposed of it in the trash can when I got out of bed. I almost tripped due to the weakness in my legs. Then I returned to bed to lie beside her. She looked at the ceiling, then turned to me. She snuggled up next to me, and I ran my hand over her head and caressed her bare back.
"And that's how you lose your virginity."