The Virgin Valentine

Blue eyes studied me for the longest time as she gently stroked my shaft with her fingers. She used my own precum to wet her fingers, sliding them gently along my length before licking them clean. I nearly blew my load as I watched her suck on each digit, but curiosity kept my head in the game. I wanted to know what new and exciting things she had in store for me. She didn't keep me waiting long.

"I'm going to need you nice and slippery for this next part," she said as she took my hand. She remained on her knees, but beckoned me to rise to my feet, pulling gently at my arm until I complied. I made no complaint, and soon my cock was swinging just a few inches from her waiting lips. I knew what was coming, but the sensation of her lips wrapping around me was something I'd never grow tired of.

I groaned as her mouth engulfed me, starting with the shimmering tip and slowly working her way down my shaft. I watched from above as her head bobbed further and further down my manhood. She'd never be able to fit all of me, but it was certainly enough to do the job, and in just a few minutes she had found a steady rhythm.

There was a mirror on the wall across from where I stood, something my roommate had put up for decoration. I'd never cared for it, but now I was grateful for the addition. When I wasn't looking down into her blue eyes as she looked up at me, I was looking up at that mirror, enjoying the view of Gwen's backside as her head bobbed along my shaft. Her tongue had some experience by now in pleasuring me, and she knew all of my weak spots. I groaned again and again as she teased the underside of my cock, urging her to carry on. Her fingers latched to my hips for leverage, leaving only for brief moments to play with my balls, testing if I'd shaved them recently. She would be pleased to find that I had.

Despite my impressive stamina, blowjobs from Gwen usually didn't last very long. She knew what she was doing by now, and she did it quite well. She also wasn't opposed to swallowing the end result, which meant I could focus more on pleasure and less on having to pull out. Perhaps with this knowledge in mind, Gwen didn't continue for long.

She peered up in to my eyes and slowly stroked my shaft with her slender fingers, testing how slippery I'd become. It was impossible not to pout, longing for those lips to reclaim me, but Gwen was planning something more than just a blowjob.

"Don't worry babe, I'm not done with you yet," Gwen said, perhaps sensing my desire for her to finish me. "I just need to make sure you're all lubed up for me."

She slowly rose to her feet, close enough that my cock remained pressed to her belly. I could already feel her saliva beginning to dry on the surface.

"I'm not sure it's going to stay slippery for long," I reminded her. It probably sounded like a please to continue the blowjob, but I truly worried this might foil her plans.

She giggled, reaching for her purse. "Don't worry, I came prepared." Her hand wandered inside for a moment before retrieving a small bottle of lube. I raised my eyebrows a bit as she opened the top to break the seal. She giggled again. "Don't get too excited!"

"Too late," I replied, glancing down to my erection, still strong and ready for action.

Another laugh escaped her lips, but she didn't respond to my joke. Instead, she positioned the bottle over my penis, giving me little warning before the stream of cool liquid made contact with the sensitive skin. She passed it up and down my length, using her free hand to stroke me until I was shiny and slick from base to tip. It was a wonderful feeling, once the cold chill passed.

"Have you ever heard of a thigh-job before?" Gwen asked, catching me off guard.

I hadn't really, but it was easy enough to figure out from the name. "I think I get the idea. Is that what you want to try?"

She blushed a bit, but giggled. "I know it sounds silly, but I figure why not? It's kind of like having sex, and it'll be something new and different for both of us." Her smile wavered a bit, hesitation slowly creeping in. "I mean, if you think it's silly we don't have..."

"No! No, no, no, I think it's a great idea," I said, watching her doubts dissipate into another grin. "I'm just surprised you thought of it."

She blushed again. "Like I said, a friend suggested it. She tried it with her boyfriend and said it was...anyway, never mind all that. I'm getting a bit antsy here."

In yet another surprising move, Gwen held up her hand and squeezed another generous stream of lube onto her palm. Putting the bottle aside, she quickly began to apply the slippery liquid to her thighs, soaking the gap completely. I couldn't help but notice the way she glistened before her fingers ever touched her skin. I suspected much of that shine would be from her own arousal.

Finally satisfied, Gwen turned back to me. "Are you ready?" she asked, wiping her hand clean on her chest.

I nodded my answer, eyes wandering from her grin to the tiny triangle of light between her legs. It was all the motivation she needed. Gwen turned, presenting her ass to me as she bent her waist, hands on the arm of the couch for stability. She turned back to me, eyes hungry with anticipation.

I stepped closer and let my cock hover just a few inches from that tight, slippery gap. I realized how easy it would be to slip into a different area entirely, but quickly waved the thought away. She simply wasn't ready for that just yet, and I would respect her wishes. In the meantime, I fully planned on enjoying the ride I was about to give her.

Despite her eagerness, was still pleasantly surprised by the sudden contact, gasping in delight as the tip of my cock slid gently between her thighs. I gradually filled that triangle with throbbing flesh, groaning with every inch. The lube made it easy work, and I reminded myself to push slower, teasing the moan from her lips. I kept my hand on my shaft, applying just a slight amount of pressure against her lips as I slid forward, teasing her lips with my erection. The veins in my cock were bulging along its length, adding a bit of texture as I pressed against her labia and clit.

She shut her eyes and moaned louder, not daring to catch her breath until my hips were firmly seated against her rear. I could only imagine what it would be like when I entered her for real, but I had to admit, the sensation of being between her legs alone was more than I'd bargained for. Her frame was tiny beneath me, and her thighs remained tightly wrapped around me as I squeezed through. The warmth of her body gave way to cooler air, the head of my cock now within her sight on the other side.

"How does that feel?" I asked it already knowing the answer.

She turned back to me, biting her lip once more. "Fucking wonderful!" I believed her. I'd only had sex with a few girls before Gwen, but I knew the difference between water based lubricant and the real thing. I wondered silently if I would find creamy white on my shaft when I pulled out.

"Do you like it?" Gwen suddenly asked, sensing my hesitation.

I dispelled her doubts with another grin. "Let's see if I can rock your world."

Before she could reply, I pulled myself backward, the head of my cock disappearing again into her gap and rubbing against her lips. Gwen's moan was answer enough, but the true motivation came from the sight of her arousal as it covered me. There was no way I was going to let it go to waste, and I quickly pushed back into her, filling that triangular void as if it were the tight little hole just above.

She leaned further into the couch, angling her body so her clit would maintain pressure against my rod. If this had been actual sex I would have gone much slower, easing gently into her until her body could accommodate my size. With this, however, there was nothing to worry about. I wasted no time, thrusting faster and harder as her little gasps of pleasure filled the room.

"Oh fuck!" she gasped between thrusts. "Please, don't stop!"

"Not until I feel your cum flowing down your leg," I answered, surprising even myself. Dirty talk wasn't part of our usual routine, but I was glad to find that both of us were enjoying ourselves. I no longer had to keep my hand on my shaft, standing high enough against her shorter stature that my erection remained firm against her womanhood.

The tingle returned to the tip of my cock, reminding me that Gwen's little tease had brought me closer to orgasm that I would have preferred. Once again, I found myself imagining the scene that would soon transpire. Me, thrusting harder and faster between her thighs, her nails digging in to the couch as I groaned out my orgasm. Cum would erupt from my tip just as it pushed back into her view, a pearly rope soaring beneath her breasts and coming to rest on my own furniture. The next would be trapped between her legs as I pulled back, pooling in that tiny triangular space and dripping down her thigh, mixing with her own juices.

I closed my eyes as I envisioned the mess I would leave on her body, willing myself to hold on just a bit longer. I wanted to cum, but more importantly, I wanted Gwen to cum with me. I could practically hear her moan already, loud enough to wake the neighbors.

It was in this moment, lost in my own thoughts, that the slip occurred.

I pulled back just as Gwen's arms began to go weak with ecstasy. She tried to compensate, pushing herself higher and straightening her arms. Her body angled once more, just as I began to thrust forward. Rather than the squeeze of her thighs, I felt the tip of my cock begin to penetrate her virgin hole. I froze, immediately aware of the mistake we'd made.

Gwen gasped in what I could only assume was a mixture of pain and pleasure. I was careful not to move, afraid that I might push deeper inside. At the same time, Gwen made no movement away from me, and I was afraid that pulling out might cause her more pain. And so I stood there, head and crown still sheathed in her slippery warmth.

Eventually, Gwen's breathing returned to normal, and I thought it safe to pull out. Slowly, I eased backward, listening carefully as I did. She gasped once more as I exited her body, but to my relief this one sounded more pleasure than pain. Perhaps I was being a bit paranoid?

"I'm so sorry, Gwen." I could already feel my erection beginning to fade. "It was an accident. I just kind of slipped."

She straightened her back slowly, but when she turned to face me she was smiling. "Not exactly how I imagined it would happen, your first time entering me. But don't worry so much, it's perfectly fine!"

I sighed in relief, glad to see she wasn't upset. "Are you mad at me?"

Another laugh. "Of course, not silly! It was an accident, and I'm fine! Seriously, don't worry about it."

With that, she pulled herself in to me for another long, passionate kiss. Her breasts pushed firmly against my own chest, and the sweat on both our bodies caused her nipples to slide against the smooth skin. My erection was quickly returning, but I wasn't sure if that was such a good thing. As though reading my mind, Gwen broke the silence.

"Now come on, I'm not putting my clothes back on until both of us have had an orgasm!"

Whatever dread remained inside of me disappeared with her words, and I reached down to grab her hips, determined to make up for the little mishap. To my surprise, Gwen pushed my hand away gently.

"Actually, perhaps we should try a different position?" she suggested. "Might make it easier to avoid another slip. Besides, my arms are getting tired!"

Gwen laid on the couch as she spoke, lifting her heels high above her, legs stretched out to nearly straight. Her thighs still glistened wet, and any reservations I had about making a mess on the couch were quickly overcome by my own horniness. I climbed up and put her ankles around my head, holding her thighs together as I searched for her thigh gap with the tip of my cock, careful not to repeat my earlier mishap.

The angle was quite different, but as I slowly slid back into position between her thighs, I was pleased to find that this would feel much better. Her clit would rub gently along the underside of my cock with each thrust, a much more sensitive area than the top. The smoothness of her mound was a welcome treat, and I realized now why Gwen had decided to shave for the occasion.

"Don't keep me waiting," she teased below me, playing with her tits. "I'm so close to orgasm I can practically feel it. Come on Ryan, don't you want to make me cum?" She bit a finger between those pouty lips, teasing me like a pro.

"Yes ma'am." With one leg off the couch and the other knee firmly planted on the cushion, I began to thrust again, careful not to slip out of her gap. It was much easier in this position, and her legs were angled to give me a glorious view of the action below. I picked up the pace, pushing faster with every second, and her moans grew louder in kind.

Within minutes Gwen's eyes were shut tight, and her hands flew to the arm of the couch above her. I watched her tits push higher as her back arched below, the first indications that she was on the cusp of orgasm. She was close, and this only fueled my desire to please her. I thrust harder between her legs, glad to feel the added juices from her body to make the task easier. The gentle sound of my balls smacking against her lips grew louder as I pounded, a reminder that I would probably cum soon as well.

It then dawned on me that in this position there were only a few places my cum could go. New images filled my head, but before I could push them away, Gwen's squeal announced her climax. She had finally cum, and suddenly the images in my head were becoming reality before me.

My eyes were closed as we came simultaneously, her moans and gasps giving way to a new sound altogether as the tingle in my cock became true release. Beneath me, Gwen began to tremble with pleasure as he waves of bliss overwhelmed her. I felt this despite the throbbing in my manhood as my balls began to empty on to Gwen's body. I didn't need to open my eyes to know I'd made a mess. I continued thrusting as I came, a soft groan the only other sign that I was cumming. I felt the powerful ropes leave my body every time I pushed through to the other side, until my orgasm came to a quiet end with my tip between her thighs.

When I finally opened my eyes, the first thing I saw was the small pool of pearly semen gathering around Gwen's pussy, flowing around her lips as I finished ejaculating between her thighs. My eyes then traveled north along her body, from her tummy to her heaving chest, all of which I'd claimed with my own seed. I finally met her eyes, surprised to find that even her lips and chin were marked with pearly white.

Gwen had given me blowjobs before, but each had ended with her swallowing my load. I'd never asked her how she felt about finishing anywhere else, let along on her face. I felt a bit awkward at the moment, but her trademark grin flashed up at me as she traced a finger along her jaw, pushing my cum between her lips for a taste.

Her eyes eventually went lower to study the aftermath on her slender body. "Oh my, you definitely made a mess on me, Ryan, Marking your territory?" she asked, still grinning.

I laughed. "Sorry babe. I probably should have asked."

"Don't be sorry," she answered. "I'm definitely okay with this." Her hand traveled up to her breast now, where she found more of my semen to play with. My erection, which had slowly begun to fade, was quickly finding new life, though I doubted I'd be able to make use of it.

She giggled again, then slowly pulled herself to her elbows. "Do you think I could get a towel or something to clean off with?"

I studied my handiwork one last time, impressed by how thoroughly I'd left my mark. Her body was like a canvas and this was my masterpiece. I'd almost be sad to see her clean, but her body was a work of art regardless.

There were clean towels in the dryer, but rather than let Gwen wipe herself off, I suggested we jump in the shower together. I'd had enough experience with personal lubricant to know that wiping it with a towel wouldn't be enough. Her thighs were still slick, and not just from the bottle of lube.

It wouldn't be the first time we'd bathed with one another, including a particularly risky moment in the communal shower back at her dorm. She quickly agreed, and after a brief cleanup with a paper towel, we were off to the bathroom, our clothing still on the floor.

My shower, like so many other features in this cookie-cutter apartment, was not built for more than one person. For once this worked in my favor, forcing us to squeeze past one another fairly often as we traded turns beneath the water. Lucky for her, I'd narrowly missed her lovely hair, saving her the trouble of washing it. She kept her hair in a bun while we rinsed, a sight that I found quite adorable.

We took turns washing one another. If she preferred a different scent of soap to the one I had to offer, she didn't complain, as I gently lathered her body from shoulder to toe. I reached around to wash her back, and butt, pulling her body against mine a bit longer than necessary. We were slippery and I enjoyed myself, watching the suds drip down her curves before vanishing under the flow of warm water.

I didn't need to tell her this with words. While my hands were busy with her curves, her delicate fingers had found something to play with down below. It was impossible not to grow harder to her touch, and Gwen seemed extra determined to ensure that I was clean. When the suds began to die, she added more soap to her palm, stroking my many inches again and again as we began to make out against the cool tile of the wall. Her hair would get wet, but Gwen didn't complain as I parted her lips with mine and introduced my tongue to hers.

We stayed in the shower far longer than I'd anticipated. My hands eventually wandered lower on her body, slowly working their way down to her womanhood. She parted her legs for me, allowing a quick tease with my hand before sliding a finger in to her pussy. She moaned and writhed beneath me, pinned to the wall now as she continued to stroke. She was trying to make me cum again, but I knew I would be the winner of this particular race. I was still in recovery, but she would soon be begging for orgasm once more.

Just as I predicted, her body began to quake in my arms just seconds later. My finger continued to work her g-spot as my palm massaged her clit. She held on to my cock but was no longer stroking, her mind unable to focus on anything but the bliss I was causing. It didn't matter, not to me.

"Oh Ryan! You're so fucking good at that!" she moaned into my ear as I held her against the wall. I didn't relent, continuing to tease her from both inside and out, until finally the release came. She gasped in my ear and pulled my body tighter against her own, her nipples hard against my chest. The orgasm washed over her like water, warming her body in ways that the shower head could not.

My finger continued to wiggle, driving her orgasm as far as she'd allow, only giving in as her thighs clenched tight around my hand. Her body reacted on instinct, unable to withstand the amount of pleasure I was delivering. It was a proud moment, and one that I finished with another long, passionate kiss.

When our lips finally unlocked, Gwen's blue eyes were shinning back into mine, her smile unlike any I'd ever seen before. Her breathing began to slow, and her trembling legs were slowly regaining their strength. There were no words exchanged. Everything important had already been said, now washing down the drain as the water rinsed her thigh.

"Well," I finally said, "I think you're clean now."

She giggled. "Then why do I feel like such a dirty little girl?" She said it with a smile, hinting that this wasn't necessarily a bad thing.