First Time Giving Head Novels & Stories

Even though Lena and I were best friends and had seen each other naked a million times, I still felt my face heat up. "I'm fine, really. I don't need it," I muttered, feeling embarrassed. "Don't play tough. I can tell," Lena said, giving me that all-knowing look, like she was diagnosing a patient. I fidgeted with the tube, avoiding her eyes. "Is it really that serious?" "Absolutely. The first time can cause small tears, bleeding, or even inflammation. If you're not careful, it could lead to infections or, in rare cases, affect your reproductive health," she said, sounding like she was giving a medical lecture.

She gasped in my arms when I thrusted in, just by an inch. I raised my face with a groan when felt her walls tightening around me, gripping me immediately. “You are so tight, baby,” I quickly kissed her lips and started taking deep breaths, trying to remind myself that this was her first time, Grunting to myself, I moved one inch further and waited. A cry fell off her mouth and a drop of sweat slid down my temple. My hand reached up to wipe the tears off her face, trying my best to be gentle with her.

She gasp fidgeting with her hands as I ready myself to thrust into her. Before I will push my erect manhood I caress her clit to add some pleasure. She likes it as she opened her legs wide open for me. I hold her thighs tightly and started to push a hard thrust when she screamed. I was startled looking at her in shock. "I'm sorry babe." I uttered caressing her face while my left hand stroking my manhood before thrusting into her. I was halfway toward her when she cried again. It was too late for me to realize it was her first time. Fuck!

I think it's a condom. Once he leaned up again, I closed my eyes. He's wearing it. He leaned down in between my legs. I gasped when something hard was poking me. He grabbed my head. This is scarier than I thought. I shuffled but he held my waist in place. "It's your first time. I'll be gentle," he said. I relaxed. "One, two, three," he pushed in. I gasped. That hurts. I held his arms. He pushed in against and out.

I was afraid of gagging myself, so I only took the first two inches in before pulling my head back up. When I went down on him again, he started moaning. I didn't speed up, but I continued lifting my head up and down for the next few minutes, until he started shaking. He hadn't uttered any further protest, which made me happy. Even though his cock had been hard when I first came in, after ten minutes of blowing him, he was even harder. My pussy was throbbing, demanding my attention. It was time to give it some. Lifting my head all the way off his penis, I sat back on the heels of my feet.

"Don't act shy now. You wanted to do something for me, right? So do it. You should be happy I want to do something sexual with you after three years. Do you want me to get it somewhere else?" She shook her head, still swimming in tears. I didn't even hit her. Is she on her period or something? Soon her warm breath brushed over the head of my cock before she finally took me in. Just the tip at first. Clumsy with no fucking skill. She was licking it like it was a damn lollipop. I groaned in frustration, thrusting my hips forward to push deeper. She gagged instantly, pulling back. "Fuck," I hissed. "I know it's your first time, but what the hell was that? Don't make me go soft and regret this."

“Very well, then. Keep your eyes to the mirror. Let’s give you your first experience. Come here.” He slowly pushes the head of his cock inside me. It tears into me as though it’s my first time having sex. I shudder from the pain, though what follows after is a kind of pleasure I never thought is possible. Tears fill my eyes from the overstimulation. “Shhh…” He leans over me, brushing a strand of hair from my sweat-slicked face. He moves slowly, gently pushing his length inside of me. I whimper, my breath heavy. I moan incoherently. “Good girl. You’re taking me so well. I’ll be as gentle as I can with you, okay?”

It was in control, and it wouldn't let me stop. I pushed so that the head of my cock was just entering her flower, spreading her just a little bit. She closed her eyes, obviously scared. I leaned down and kissed her, the first kiss I had given her since we had started this. I felt her whole body relax as she deeply kissed me, her tongue going into my mouth. I tasted my own pre cum as she no doubt tasted her own wet pussy, but I was way too turned on to be grossed out.

It was as if she knew the exact way to move her head to pleasure me. “Fuck!” I groaned as she made slurp sounds, going up and down. My hands instinctively found her head, and I held her as her head went up and down, pushing me all the way to the edge. I had never orgasmed from receiving head, but this was most likely my first time. I was barely able to push her off before releasing my seeds on the floor. “I wanted it in my mouth.” She smirked, bringing out a piece of gum from her pocket. She opened it and threw one in her mouth.

“I don’t know what Alpha Harold and Luna Farrah have told him about a woman’s first time and I can’t see Alpha Quirin being comfortable enough to sit through that conversation. So you need to be prepared to make him slow down, take his time with you, so that you don’t tear too badly. If he takes his time, the pain isn’t too bad, and the pleasure makes it worth it. Don’t be surprised if you bleed even the first couple of times, that’s normal. Just try to talk to him first. Try to get him to take it slow the first couple of times. Once your body adjusts and the two of you find what the other likes, it will get better.”