The First Time

Chad and I had been together for a few months now; he was always good about listening to me when I told him to stop if we were going too far, and he would always just smile and kiss me on the forehead whenever I told him I just wasn't ready yet. I don't know why I wasn't ready - I think it was because all my friends had told me their stories about their experiences where it had been painful and they hadn't been able to have an orgasm - I had an extremely low tolerance for pain and didn't even want to imagine what that was going to feel like.

Chad and I had, of course, done other things, but we had only done under-the-bra groping and hand-jobs, we hadn't progressed to the oral sex stage yet. Whenever he would begin to slide his hands down my jeans, I would carefully remove his hand and kiss him, letting him know that was too far. It had gotten to a point where he actually didn't even try anymore, and was seemingly content with our heavy-petting.

A few more months passed when my mum announced to me over dinner that she and Brad (her boyfriend) were going to take an anniversary trip to the city the upcoming weekend. They were going to leave me alone, however, with daily phone check-ins. The moment their words left their lips, I realized that I was perhaps ready, and my mind sprang into action as I began to formulate my plan. First, I would buy something extra special from the lingerie store. Second, I would find some way to make Tawni not come over for the night (but not before I got some of her tips from her many experiences.)

Third, I would invite Chad over under the innocent pretence of our usual Friday movie nights. I genuinely wanted to be with him, and had reached a point where I knew I was ready. And when the night came I put on some comfortable clothes and met him at the door as usual; his smooth brown hair and dimpled smile reminded me why I was so crazy about him, and why I wanted to do this, and I opened the door wider to let him in.

We popped in the movie and got comfortable, my head resting on his chest and his arms around my shoulders. After a while, I excused myself to the bathroom, returning back in a black teddy and lacy thong. I cleared my throat, leaning against the doorway, a come-hither look on my face.

His jaw dropped and he lost the ability to form words as he looked back at me. I had to admit, I looked great; while I wasn't slender, I was taut with curves and C-cup breasts. I walked over to where he was sitting on the couch, pulling him up and leading him up the stairs to my room. He stopped, halfway up and pulled me towards him, wrapping his arms around my waist and kissing me fiercely. I smiled, pulling away, "be patient," I whispered in his ears, leading him up the rest of the stairs and into my room. As soon as we were in, I closed the door and turned around, wrapping my arms around his neck and kissing him passionately. He moved his hands down to my ass and squeezed as I opened my mouth and let his tongue slide in.

I pushed him down onto the bed, climbing on top and straddling my legs on either side of him, leaning down to kiss his neck. He moved his hands under the lacy fabric and rubbed the small of my back. Then, he stopped, pulling away, "babe you know I love this, but I can't do this if it's not gonna end in something - I'm sorry." I nodded, smirking as I kissed his neck to his ear, whispering, "Who said it's not going to end in anything?" I giggled, feeling a shiver go down his body, and kissed some more. He smiled incredulously, "are you sure?" Instead of answering, I sat up and slowly untied the pink string in the front of my teddy, shrugging it off my shoulders and letting it slide to the floor, my perky breasts exposed. He couldn't move, he was shocked as he stared up at me. I smirked, grabbing his hands and placing it on my chest before leaning down so that my boobs were right above his mouth. He buried his face in them, sucking and biting as I let out soft moans, feeling my pussy getting wetter and wetter. I sat up and pulled him with me, pulling his shirt up over his head and running my hands over his smooth and chiselled body. I pressed my boobs against him as I kissed his shoulders and neck, grinding my pussy against his crotch. I could feel him growing hard, and his breath became more laboured. I pushed him back down, kissing down his chest and abs until I was right above his jeans. I unbuttoned them, sliding them down his legs and onto the floor, and then began to tease him by rubbing his dick gently through the thin fabric of his briefs. I slowly pulled his briefs down, inserting all 8 inches of him into my mouth, feeling him getting harder and harder as he let out a groan. I moved my hands up and down as I circled the tip of his dick with my tongue, one hand playing with his balls. He groaned again, flipping me over so that I was on my back. He pulled off what little underwear I had left and slowly buried his face into my crotch. I gasped, running my hands through his hair as I began to grow closer and closer to an orgasm. As his tongue flicked and sucked on my clit, I could feel my toes start to curl, and I arched my back as I climaxed.

Panting and ready for more, I pushed him up and back onto the bed, straddling him I lowered myself down onto his dick slowly, preparing myself for the pain, and let him enter completely inside of me. Gasping from the pain, he sat up, pulling out to see if I was alright, and I kissed him, reassuring him, and climbed back on. After riding him for a few minutes, I felt him shoot his load inside of me and he pulled out, his strong arms holding me against his chest. He kissed me, and I kissed him back ferociously, "sleep over tonight," I said through our kiss, rolling off of him and laying my head on his chest. He nodded, and exhausted, we both fell asleep.