First Timer's Luck

I can still see her, years later. As perfect as she was to me then. The thought of that night still brings my entire body to attention. 

I was 18, a senior in high school, with many girlfriends but not a girlfriend. I was friend-zoned, constantly. “I love you like a brother," all the girls said, talking to me about their crushes, teasing, as if I was one of them. I’d never been kissed and was painfully aware of the fact that I was soon to enter college a complete virgin.

My sexual appetite, unquenched, built fantastic energy in me. At times, it was all-consuming. Tight shirts or smooth legs plagued my brain while I lay in bed, slowly, deliberately stroking, fantasizing, and desperately trying to release some of the pent-up sexual energy within me. I'd edge myself, trying to last as long as I could to enjoy the bliss of desire, sometimes simply fantasizing about being held in someone's arms, kissed, lightly touched.

I decided my chances for changing the facts were slim, and so I hunkered down studying, spending long hours in front of the computer screen working my hardest to hopefully win some scholarships. Life was pretty uneventful until one weekend my older sister came home from college with her roommate, Sasha.

Sasha was from a small town in northern Washington, so home was a bit further for her. She was happy to come to our family’s place to enjoy some respite from the dorms and daily life of the university. 

And Sasha was captivating. She had curves. Beautiful, full breasts and a stomach that was not flat, not carved, not muscular, but naturally flowing like a wave. Her body was like a story, telling she’d been cared for, and that she cared for herself. That she enjoyed life and lived. Her hips seemed to be asking to be held, guided, grabbed onto.

"Kelly talks about you all the time," she told me when we first met. "She misses her best friend." I was even a friend to my sister! Not even an annoying little brother, but a friend just like every girl seemed to think of me.

Sasha treated me a bit differently, though. I'd be watching TV, and she'd sneak in a quick shoulder rub. She'd peek in on me at the computer working away and tell me not to work too hard. She seemed to respect and appreciate me as someone who had helped shape her roommate—her best friend in college—into who she was. She had a loving, honest way about her that made her even more beautiful to me, though that seemed nearly impossible.

Sasha came home a few times during that first semester. Her visits kept me going through the monotony of my high school existence. She was, of course, beyond unobtainable—her being a college student and me being, well, me, but she made me feel like I was important to her somehow. When she’d arrive home with Kelly, her attention made me feel hopeful.

One evening, avoiding an assignment—a book to read and a report to write—I was sitting at my desk when there was a knock at my door. I turned and was greeted by a sight beyond my wildest fantasies. Sasha stood in my doorway in a white bikini—the curve of her hip up on one side, leaning, beckoning. Her skin was almost the color of the white bathing suit—porcelain, and she looked softer than anything I could touch. Her breasts were full, barely held by her bikini top. I couldn’t look away—her cleavage moved slightly up and down as she breathed; I longed to kiss her collarbone. She had rendered me speechless.

"Wanna come join us in the Jacuzzi?" Sasha asked as if I was capable of doing anything but stare. Assignment be damned, now it was sheer embarrassment at my body's reaction to her that kept me firmly planted at my desk.

"No, thanks, Sasha. I'm slammed with work here," I responded, choking out the words in a jumbled mess of teenage angst and emotion.

"All right, babe. Don't work too hard, okay?" She turned to go, and as I watched her beautiful ass walk away, I felt I would never be nearer to god.

It was after midnight, and I was still typing away, attempting to summarize the book. My desk lamp nearby was the only light, making the rest of the bedroom appear illuminated as if by candlelight. Words blurred and crossed as I fought exhaustion, trying to finish sooner rather than later and finally catch some sleep.

"Hey," came from the doorway. I turned. There was Sasha again, this time in boxers and an oversized T-shirt, obviously bra-less. I choked at her sight. Even in sleep clothes, she left me breathless.

"I thought I was the only one awake," I whispered.

"You were—but I woke up and heard you still typing. Are you still doing homework? I thought I had it bad in college!" She smiled—such a beautiful smile. "Mind if I come in?" she asked.

I smiled and yawned. "Of course not," I said. She walked in, sitting on the edge of my bed behind me.

"I'm one of those who believes firmly in the 'Cs get degrees' mentality. I never worked—or work—as hard as you do on all of this," she said.

"I just really need to get a scholarship so I can get out of here and go to college next year. There’s nothing for me in this town,” I said.

"You will,” she said. “Kelly talks about you all the time. She’s so proud of you. She wishes she’d done half of what you’re putting in. You inspire her so much. I think you inspire me, too.”

I’d never had a girl—let alone anyone—say such nice things to me. I couldn’t help but blush.

“Thanks,” I said.

Sasha leaned back onto her elbows and patted the bed. “Come here,” she said. “You deserve a break.”

A simple request, and yet the thoughts which swiftly entered my head were enough to jump-start every nerve in my body, including those down below, causing me to swell. Sit on the bed next to this unbelievably perfect woman? I felt like I was dreaming and would be woken up soon.

Somehow, I got up and sat next to her, nervous as hell. She seemed to sense this and sat up beside me, placing a hand on my shoulder.

“YOU,” she said firmly, “need to relax, buddy!” She began rubbing my neck and shoulders. I breathed deeply. Her touch sent shivers throughout my body, seeming to converge in my growing erection. “Why don’t you have a girlfriend?” she asked, as her fingertips began to make their way through my hair.

I laughed quietly. “Everyone thinks of me as too good a friend.”

“Ha,” she replied. “Girls will appreciate that when you’re older.” The desk lamp made her hair glow like a crown upon her head. “Have you…ever…?” she asked with a smile.

“No. Not even a kiss,” I confessed.

She smiled, closed her eyes, and shook her head in disbelief. Then, slowly, she leaned in, tilting her head to one side, and brushed her lips against mine, quickly solving that problem. My lips buzzed. My body burned with excitement as she pulled away slightly to look at me, smile, then close her eyes and meet my mouth again. 

She parted her lips and gave my top lip a gentle lick to open them. I wasn’t sure what to do, but responded in kind, parting my lips instinctively and kissing her back, my tongue lightly moving with hers. She felt so soft, the whole moment surreal.

Sasha pulled away and smiled. “Your girlfriends don’t know what they’re missing.” Then she scooted back toward my pillows. “Wanna come here?” she asked, and I nervously followed, like a loyal dog. 

She made herself comfortable against the pillows at the head of the bed. I lay next to her, my heart pounding in my chest, nearly into my throat. She smiled and then nearly killed me—she reached for the hem of her shirt and pulled it up and over her head, exposing her breasts. She watched me as she bit her bottom lip, enjoying the reaction she got from me. I’d seen breasts before, but only in movies, and these were so much better. They hung heavily from her body, areolas light, almost the color of her skin, giving way to beautiful pink nipples, soft and smooth.

“Another first?” she asked, referring to my look of shock and confusion as to what I was supposed to do next. “Here,” she said, and she took my hand. She gently placed it on her right breast, closest to me. The feeling was incredible—so amazingly soft. She let out a small, nervous laugh as I gave a gentle squeeze and, not even thinking, ran my thumb over her nipple. Under my touch, her nipple stiffened, the skin of her areola tightening into a rippled landscape. She breathed in deeply as I explored. It was so dreamlike, seeing her in front of me, breasts exposed, my hand roaming along her skin, seeing and feeling her body react to my inexperienced touch.

“You okay?’ she asked with a smile, again a reaction to what must have been a completely uncertain look on my face. I nodded, probably too eagerly, like an excited schoolboy, but my excitement and wonder were too intense to contain. 

She laughed under her breath, then lay back more. “Lie down, baby,” she said. Her voice was loving. I felt so nervous and yet somehow totally at ease at the time. I adjusted my body and lay down, placing my head on my pillow. “I want you to try something,” she said, and she lifted her breast with her hand, guiding it toward my mouth. 

My jaw dropped. “Ssssh—it’s okay, baby. It’s okay,” she said. “Open,” she instructed. I swallowed hard and did as she asked, opening my mouth. She gently slid her breast between my lips, laying her nipple upon my tongue. “There,” she sighed. “Now just suck…you’ll know what to do, I promise.”

The feeling was overwhelming—the sensation of her hardened nipple between my lips so precious. But she was right—somehow I knew exactly what I needed to do. I placed my hand back on her breast and gently, slowly, began to suck.

Sasha sighed deeply. She took my other hand, lacing her fingers with mine, and placed them on her stomach. With her other hand, she stroked my hair, smoothing it back. “Yes, like that. Perfect,” she said.

I felt immediately embarrassed as I brushed against her leg and my erection was made obvious. But she simply smiled and gave a gentle, reassuring laugh. She knew it was there; she knew I couldn't hide. “You like that, huh?” she said, as she slowly reached for me, but I began to back away in horror, releasing myself from her breast, stuttering, “I…I…uh…”

I was soaked. I knew about—even enjoyed—precum, which often appeared as I slowly stroked on those lazy afternoons of fantasizing. But this was much, much more. I was covered in it inside my pants, and not knowing that it was my body’s natural reaction toward the stimulus I was experiencing and not something wrong or to be, at all, ashamed of, I, at the time, was sure she would find this reaction of my body repulsive and just as embarrassing for her as it was for me.

I was wrong. As she reached down and felt me and felt that wetness I was covered in, she smiled even bigger, bit her bottom lip, and responded with an “mmmm.” She reached down and wrapped her fingers around my hardened shaft. She was very careful. She knew, instinctively, that my brain and body were on complete overload—too much and it would be over. She was careful not to push me over the edge.

She took my hand from her belly and began moving it down, down, down, bringing me further, closer, to a radiant, unbelievable warmth coming from between her legs. She pulled aside her boxers and laid my hand against her pussy. A tuft of warm, soft hair greeted my wrist, and as she pressed my finger, her lips parted, and I felt her wetness.

Sasha sat up. “Wait, I want to give you something,” she said, and she reached down, sliding down her boxers. “Do you wanna know what I feel like?” She reached over and exposed my cock, throbbing and ready to explode any moment. Sasha reached between her legs and gently grasped my hardness, guiding it toward her. The head suddenly felt that warm wetness we’d brought on together. My heart leaped into my throat. Sasha looked down into my eyes and, slowly, so slowly, guided me in. I’m sure both of us would have loved to savor each inch as I disappeared into her body, but she knew this was not going to last long.

Somehow, I made it all the way inside her. She was smooth, silky, gripping me from every side. It was the most perfect feeling I had ever experienced. She gave a short, quick thrust to show me what the full action of fucking her would be like, but my brain and body were too overcome by it all. I began to pulsate, ready to explode. I tried to pull out, but she pressed back into me.

“It’s okay, I’m on birth control. You can come inside me.” 

Permission granted, I released pulse after pulse of cum inside of her. She gasped, her breath quickening suddenly, too. I think it turned her on to know the power she had over me. After, she lay on top of me, her cheek against my chest as I slid out from inside her, covered in her and in me

We stayed like that for only a minute or so, before she sat up again, brushing her hand along my cheek, and simply asked, “Are you okay?” I was breathless, speechless, but somehow conveyed that I was—or at least I thought so. Honestly, I wasn’t sure I’d ever be okay ever again, or more than okay for the rest of my life, thanks to her.

Sasha leaned down and kissed me again, saying, “Thank you,” as she gave me another loving smile. She lifted herself from me, draping her shirt over her breasts like the curtain at the end of a show. She reached for her boxers and put them on. “Get some rest,” she said as she made her way toward the door.