Not a Tease Anymore

At first, I was actually waiting on purpose. I even had one of those horrifically embarrassing "True Love Waits" rings. I have no legitimate excuses for my hang-ups. We weren't religious. My mother never actively discouraged me from having sex, but I was always terribly afraid of getting pregnant as a teenager. I didn't want to end up alone or stuck in a dead end job, like her. If you can't be a good example, you'll just have to be a horrible warning... I was always aware that Mom had given up a lot for me, and I just couldn't bear the idea of disappointing her. I never knew my dad. He bailed before I was born.

Once I got to college and finally made some real friends, I eventually realized that sex doesn't have to equal pregnancy and subsequent death. Unfortunately, by the time I had really put myself out there and met my people, it was my junior year. I had inadvertently missed the boat. Everyone else had already done it and suddenly I was weird.

So... since then, I have been turned down a lot. It isn't hard for me to get a date. The whole relationship thing is always simple in the beginning. Guys are into me. I wear a short skirt or tight jeans, toss my long auburn hair around. We kiss. We touch. We get close... Then, well...

I have tried a lot of different approaches. I've tried being upfront. I told some of them about my unsexed status. In return, they've all freaked out. I've gotten all kinds of ridiculous excuses, but all of them ultimately boil down to some variation of "I don't fuck virgins". With others, I've been coy and tried to hide my situation. There's nothing medically wrong with me. I've checked. The doctors swear that I don't have vaginismus. I have no problem with tampons. I can totally make myself cum. They inserted my IUD without any issues, but whenever the guys have tried to enter me... I tense up. None of them could get in... even the one with the embarrassingly tiny penis.

These instances have been so uncomfortable and shitty that I've ultimately had to dump each of them. Sometimes, I awkwardly break up with them on the spot; other times, it has been a few days later. My timing really depends on how they react. When they're kind, I have a tendency to waffle, hoping that our next attempt will be better.

It never is.

Alternatively, in a more humiliating turn of events, the guys break things off with me. Their reasoning is always obvious, even though they inevitably cite other, more socially acceptable excuses. I can always tell when it's coming. There's a certain scent in the air, like lightning, guilt, a skunk stink of secondhand embarrassment. In those instances, my soon-to-be-ex-boyfriends shuffle their feet, rub the backs of their necks, and look down at the floor like they're embarrassed by me. Most tellingly, the pet names abruptly stop. They get very formal and start calling me "Lisette" all of a sudden. They never want to cop to being the bad guy, to actually come out and say that it's over because of my inexperience.

Most of them tell their buddies that we fucked anyway. They don't let the truth get in the way of a good story. I don't correct people. The rumors serve both of us. Even my closest friends don't know the whole truth about my sexual false starts.

I had decided though, this was going to be the damn weekend. I was a senior in college, for fuck's sake. My failure was getting pathetic. Besides, I really liked Tyler. He was tall, with thick dark blonde hair. His breath always smelled like crystallized ginger. Whenever we walked together, he had this adorable habit of slipping his long fingers gently into my back pocket, then strolling along casually at my pace.

I liked his sharp cheekbones and his big brown eyes. Tyler was naturally lanky, but still strong; his limbs were long, and he loped around easily. I had seen him play a game of pick-up basketball once, and I had wanted to mount him right there. He bobbed and weaved, passing the ball and making baskets effortlessly. Tyler was laid back, and nothing really seemed to crack his calm exterior. However, despite his affable manner, I had noticed that his eyes were sharp. My new boyfriend didn't easily miss things.

His dad was some kind of hedge fund manager, and he was Tyler's hero. The guy had coached his sons' Little League teams, and been home by six on the dot every night for dinner. Tyler's mom had been able to stay at home with him and his two brothers, doing charity work and cooking from scratch. He and his brothers texted each other all the time. They always said "I love you" to each other before they hung up the phone. He wasn't even embarrassed about it.

Tyler had shown me a picture of their beautiful contemporary brick house. His family had a pool, fourteen acres, and an overweight bulldog named Spud. His upbringing was a far cry from all the lonely nights that I had spent in our little decrepit tract house, waiting for my mother to come home from work with cold take-out.

Honestly, even though Tyler clearly came from money, the thing that I liked best about him was that he didn't judge other people by what they had. He was genuinely kind. His friend group was diverse. They came from varied economic backgrounds. When he took me out, I noticed that Tyler always tipped at least 20%. He was unfailingly polite to servers, janitors, and the unhoused. He treated everyone with the same measured respect that I observed him give our professors, friends, and his boss.

I'd met him through a friend of a friend at a party, and we'd been seeing each other for almost a month. However, due to circumstances beyond our control, this was going to be the first time that we'd had any real privacy. One weekend, I had to visit my mom. The next week, he had the flu. After Tyler recovered, our roommates had been perpetually holed up in our respective rooms, studying obsessively for midterms and writing papers. The stacks had been equally full of people cramming for their tests, so the library hadn't been an option. Also, we'd had our own assignments to worry about, and neither of us had cars, so there had been limited options.

I mean, it wasn't like we hadn't done anything. Tyler and I had made out all over campus. (He was a great kisser. He used the perfect amount of tongue. Do you know how rare that is?) I'd given him a few handjobs, and he'd fingered me under my skirt and through my jeans, but we hadn't had a chance to strip down together and really take our time. Anyway, I knew that it was going to come up (pun intended) over break.

Unfortunately, that first night, I kind of lost my nerve. We lay on the hard bed, making out, pretending that we weren't listening to our friends fuck. They were all loud, which made me even more nervous about my performance.

I tried to relax as Tyler slipped his tongue into my mouth. He gently slid his fingers under the lace on my camisole, over my breast, expertly feeling me up. As we dry humped, the front of his boxers practically fused to my panties with his precum and my juice.

Each time Tyler moved his hips against mine, the flimsy headboard knocked loudly against the wall. When he whimpered into my neck, begging me to grab his cock, I decided that it was time to blow him. My oral skills were top notch. I'd had a lot of practice. As a rule, things generally didn't go sideways for me until I tried to go further.

When I kissed down his neck, then his chest, Tyler grinned. It seemed that he had figured out where I was going. I licked down his body, tweaking and twisting his nipples until goosebumps bloomed on his fair skin.

Teasing has never been my problem. I knew all the tricks; every time I was going to hook up with Tyler, I wore the same perfume. After a few dates, any time he smelled it, he got that feral look in his eyes. I loved watching him want me. I had amorphous plans to wear the scent when I met his parents. I wanted to watch Tyler lose his mind across the antique table that I pictured in their formal dining room. I loved seeing him desperate, horny, and unable to touch me.

I smelled the musky, inherently male scent of his skin, sucking and nipping my way toward his package. I licked my lips in anticipation, easing his boxers down. It was the first time that I was going to see his penis. Some dicks gave me the immediate ick, but I was happy to see that I really liked looking at Tyler when he was exposed. His cock was about seven inches, with an oversized, circumcised mushroom head. He had a prominent vein running up the left side, and I could see his heart beating with every pulse of his erection.

I rubbed his cock head on my cheek seductively, running my nails lightly up and down his thighs until chill bumps bloomed on the thin skin. Then, I sucked his head purposefully into my mouth. As I deepened the stimulation, Tyler groaned, low and very deep in the back of his throat. I had noticed that my new boyfriend didn't tend to make a lot of gratuitous noise when we fooled around, even when he came, but I really liked the little rumbles and hums that seemed to signal his arousal.

As I blew Tyler, he tensed up until I could see the cords bulging in his neck. His pale cheeks blushed a light red. I gradually worked his cock into my throat, and Tyler wrapped his big hands around the metal spirals of the headboard, mindlessly fucking his hips up. With each leisurely pass, Tyler pulled on the rails. I could see his biceps bulge; his forearms were strung tight. He always looked so fucking hot. I still couldn't believe that he was with me.

His girth made my eyes water. With every up and down, thick spit lubricated his erection. I made sure to look him in the eye as I hummed and he shuddered. It was obvious that Tyler liked it when I dominated him. He was trying to let me control the pace, but with every practiced deep throat and his subsequent clench, the cheap metal smacked hard against the blue-painted drywall.

Tyler's breathing was labored. I could see his smooth chest sharply rising and falling. He had started moving his hips gently in a practiced, unconscious rhythm. After a few minutes of careful trial and error, he found that I could take his thrusts without gagging. When I didn't object, Tyler started fucking my face harder. I looked up at him through my eyelashes submissively while I dominated his dick like a champ. He seemed to appreciate the contradiction.

After a few minutes of that steady stimulation, I could feel his balls pulling up, toward his body, so I backed off. I edged him, running my tongue up and down the sides of his erection, then sucking gently on the tip, using my hand and my mouth in tandem for a second, until Tyler started trying to fuck my mouth again. Every time he did that, I intentionally changed my technique. When he grunted with frustration, I pulled away and shook my head teasingly.

I leaned up, still stroking, and murmured in his ear. "It's going to feel so fucking good when I finally let you cum..."

When Tyler moaned, I pulled back, then shook my finger at him. I bit my lip suggestively. I was still putting on a show for him. My palm moved up and down on his lubed erection, just enough to keep him right on the edge. He tried to thrust again, and I loosened my grip. I was not going to give Tyler enough pressure to get him off, not just yet.

I bit his earlobe and panted into his ear. My voice was throaty when I purred, "You cum when I say you can cum. Does that feel good, baby?"

He breathed deep; "I want to fuck you."

I shook my head again. Tyler bit his full lower lip, nodding. His voice was quiet, but still forceful, sure.

He reiterated, "I want to fuck you, baby. I want to make you feel good."

I was tempted. The room smelled like sex. I could still hear our friends, and I was incredibly turned on too. Tyler's flexing cock looked ready to explode. Jacking him off, all my saliva was almost gone, but he was making plenty of his own lube. The head of his cock was swollen, almost purple. I knew that my boyfriend couldn't last much longer.

I inched down his body and took him back in my mouth, descending smoothly, my lips gripping him all the way down to the root. Tyler seemed surprised by the sudden stimulation of my sneak attack. When I swallowed and my throat massaged his shaft, he grunted, burying himself as far as he could in my throat, using my mouth again. After a few long, slow strokes, Tyler whimpered, then he fired off shot after creamy shot down my throat. I drank down every drop of his cum. Not all guys taste good, but Tyler's jizz tasted like caramelized, bitter salt. I'd never tasted anything quite like it, and I couldn't get enough.

When I pulled away, I was surprised to see that Tyler was still hard. I gestured at his swollen phallus and raised one eyebrow.

"Does that thing ever go soft?"

He shook his head sheepishly.

"Not around you..."

I had to make a game time decision.

"Can you cum again?"

Tyler grinned at me and sighed in my ear. "Hell yeah. Fuck yeah. It will probably take me a little while too."

I felt myself blush.

"Look, I want to. I really do, but... I've never done that before."

Tyler looked incredulous. He drew back and I mentally winced. This reaction was very familiar to me.

He rasped, "What?!"

I covered my eyes.

"Yeah, yeah. I know. I have a certain reputation, but it just... hasn't worked. They can't ever get in, then they get frustrated... They call me a tease, and suddenly I'm a fucking freak."

I buried my face in his chest, feeling utterly pathetic.

Tyler gently lifted my chin between his thumb and index finger. He raised my face slowly.

"Really?"

I nodded, shamefaced. When I tried to hide my expression from him again, Tyler wouldn't let me. He looked deep into my eyes and smiled. His big brown eyes danced. I was confused by his sudden mirth.

"You're not a freak. I love fucking virgins. Hell, making someone feel THAT good for the first time... Like, being the first guy there... It just really gets me off."

While Tyler spoke, he was gently rolling his palm over my nipple. I gave myself over to the stimulation, getting wetter with every pass.

He asked, "Have you ever had an orgasm?"

I blushed and nodded. Tyler's face was serious.

"By yourself? I know you haven't cum with me yet."

I was shocked that he had noticed. His predecessors had never seemed to care. With my panties on, and us always being adjacent to the public, I'd felt too exposed. Tyler hadn't been able to get quite the right angle. I had really thought that I had done a passable impression, but apparently he hadn't been fooled.

My cheeks flamed in the low light. Tyler was right, I had never cum with another person. When other guys clumsily fingered me, it either hurt, or didn't really do much. They always got frustrated and acted like it was my fault, as though I were somehow broken. I had found that it was just easier to put on a little show, to fake it and let them feel good about themselves. I couldn't stand it when they pouted; it dried me right up and made me start to hate them.

When I finally nodded, Tyler continued. "Has anyone ever gone down on you before?"

I shook my head slowly. Tyler mirrored my gesture playfully, but his face was derisive.

"Seriously, none of those guys ate you out? Of course they couldn't get in. Also, selfish of them to make your orgasm all about their egos." He paused, clearly thinking about what I had said. "Shit. Just for the record, you give the best fucking head I've ever had. Clearly, you've had a lot of practice. Only chumps don't reciprocate. What is wrong with these guys?"

Tyler kissed my neck, sighing in my ear, still playing with the same nipple gently. He whispered, "Let me make it good for you, honey."

With that, he moved his other hand down. Tyler slid my panties aside, easily finding my clit. He did this light pinching thing that felt amazing. It wasn't a motion that I had ever tried myself, but I immediately liked the pressure. He talked dirty, very softly in my ear, mumbling, still breathing hard.

Then, Tyler ran his fingertips down my sides, feather light. His mouth followed. He sucked on my other nipple, running his tongue in slow circles around my aureoles, then my belly button, finally delving in with just the tip until I shivered.

Tyler lifted his head and grinned at me. Damn, he was cocky. Then, he put his head between my legs. I exhaled hard, trying to relax. I was suddenly worried that I smelled, or maybe tasted bad. I didn't want him to think that I was too wet, or that I wasn't reacting to his touch the right way...

I reminded myself internally. "Tyler said he likes this. He wouldn't be doing it if he didn't want to. Breathe, dumbass."

It seemed that Tyler was thinking something similar as I visibly tensed up. He stopped his ministrations and lifted his head. His chin was slick when he whispered, "Relax, babe. You taste amazing. I love your pretty pussy. There's nowhere else I would rather be, promise."

I took a deep breath as Tyler tapped with his tongue and rubbed with his nose, hitting something good, my hips suddenly arching up against my will to meet him. He put his tongue inside me, licking, rotating, lapping. Then, he was back at the top of my cunt, sucking insistently at my clit. His fingers were a practiced piston, stretching me gently, perfectly, balanced right at my hymen.

I concentrated on my breathing, looking at the clean mop of dirty-blonde curls moving gently between my legs. In and out, slow and even, matching the timbre of his tongue. Suddenly, everything went soft around the edges. My eyesight blurred, and then I was having an orgasm with another person for the first time.

I could feel myself shuddering. My legs went rigid around his head, trying to keep the pressure on my clit exactly the same. Tyler kept licking me, practically making out with my pussy. Surprised by the rolling waves of intense pleasure, I bit my tongue so hard that it bled. I think that I might have squeaked aloud. Everything that he was doing just felt so fucking good, I never wanted him to stop, but eventually I was too sensitive. When I finished my involuntary jerking, Tyler leaned back and removed his fingers.

My boyfriend looked triumphant. He was obviously proud of himself. He licked his lips, then his fingers, like he couldn't get enough of my essence. Tyler watched me intently as my breathing gradually slowed.

He whispered in my ear. "Did that feel as good as it looked?"

I didn't answer. I wanted him to fuck me then, there, anytime, always. I pressed my lips to his as though Tyler were my only access point for clean oxygen. I could feel his hard cock balanced between my legs, he was still rigid, practically throbbing, slick with his cum. His lips were pliable and full against mine. When Tyler massaged my tongue with the tip of his, I could taste myself. I was shocked to find that it wasn't bad. I tasted clean and tangy, like some kind of exotic fruit with a mild, sweet aftertaste. Tyler rubbed his shaft against my clit, teasing me so good.

When the kiss broke, I quietly pleaded with him, practically begging for his dick. "Fuck me, please. God, you feel so fucking good."

Tyler bit my earlobe and whispered, "You still want to? Are you sure?"

I nodded, still slightly shook.

Tyler looked into my eyes again. His gaze was deadly serious.

He said, "Honey, I need you to tell me that this is what you want. Consent is sexy. Tell me exactly what you want me to do."

I could tell that he desperately wanted to be inside me, that Tyler was very deliberately holding himself back. His jaw was sharp, his eyes hard and full of lust.

I said, "I want it. I want you inside me. Fuck me, please. Make me feel good again."

"Do I need to wear a condom?"

I shook my head side to side. I knew that Tyler was clean. He'd been thoughtful enough to give me an unprompted STI report from the Student Health Center right before we left on the trip.

"I don't want to get you pregnant..."

I shook my head. "I have an IUD, and I'm on the pill. Can you please try to pull out though, just to be extra safe?"

Tyler nodded seriously, then he placed his big dick at the entrance of my vagina. When I felt his slick head, I waited for that familiar, unwelcome tension to fill my body, but I was surprised when there was nothing. I was spent, entirely too relaxed to muster my usual anxiety. The primitive parts of my brain really just wanted to cum that hard again.

Tyler kissed me hard as he notched himself inside. I felt a sudden, sharp pinch. He was probably only about three inches in, but it felt as though he were splitting me open.

He groaned, "Oh, God. You're so fucking tight. Your pussy feels so good."

Tyler pulled back slowly and I whimpered, thinking that it was over, that I had somehow managed to fuck it up again.

He said softly, "Everything is fine, baby. I'm just going to get a little lube. Hold on."

Tyler strode to his bag and grabbed a little red bottle. When he got back to the bed, he poured a few drops into his palm, then stroked himself with both hands, applying the glassy liquid all over his dick. He closed his eyes for a second and sighed, massaging his slick head.

Before he tried to get inside me again, Tyler gave me another deep kiss, lots of tongue. He breathed into my mouth. Then, as he gently pushed forward, I could feel myself opening for him. My walls dragged on his cock. He tried two small, almost experimental thrusts, and then Tyler balanced his chest right above mine, carefully supporting his weight on his hands.

He breathed, "Are you ready? This is going to hurt a little bit."

I nodded hard into his neck, and then Tyler drove home. He effectively broke through my barrier and buried himself deep inside me with a low groan. The initial pinch easily gave way to a dull ache, but he still felt good inside me, the sudden sting intensifying the pleasure of his pubic bone pressed tightly against my clit as the twitch of his cock massaged me from the inside out.

Tyler held perfectly still, even though I could tell that it was hard for him.

"You let me know when you're ready, baby. I'll be really gentle; just breathe and take a minute to adjust."

I knew how to do Kegels. I lay there for a minute, then carefully squeezed his erection with my cunt. At the new pressure, Tyler exhaled in a gust. I could feel his legs straining. He was obviously still trying to overcome that innate male instinct to repeatedly plunge his cock into me.

"Oh, God. You're so fucking tight."

I squeezed again, just to torture him, then I panted for him to move.

"Go slow, please. I feel so full. Fuck, you feel good."

Tyler started moving gently, and then we were both breathing hard. Every time the crown of his dick rubbed against the remaining raw edge inside me, I shivered.

"Tyler, I want you to just fuck me until you cum. I don't know what I'm doing."

He shook his head firmly. "Don't worry. I'll get you there; just hold on for a second."

Tyler shifted his hips slightly, then he pushed my thighs further apart. He started a slow, intensely pleasurable grinding motion, rotating his hips slowly to the right. With every modified thrust, I sucked in my breath. I knew then that I was going to cum, it was just a matter of when.

Tyler was gripping the headboard again for leverage. His breath was ragged, and his face was flushed.

Every time he bottomed out, he involuntarily muttered, "Oh, fuck."

Tyler kept that up for a few minutes, turning the smarting inside me into a deep, inexorable need. As I felt the pressure building, Tyler suddenly reared up. He snaked one hand between our bodies and started that same, two-sided stimulation on my clit.

I whispered, "Oh, fuuuuuck. That feels so good. Don't stop. Please don't stop."

I was practically incoherent. The internal sear and the pleasure blended together and the orgasm washed over me like an unexpected wave, practically taking me under. With every clench, there was an answering twinge that made everything feel even more intense. As I came back up for air, I registered his low, husky voice.

Tyler was practically growling. His tone was needy, strung out. "Fuck, I don't want to pull out. You feel so fucking good. I know I already came, but it still might be a lot. It feels so good right now. I can't stop. Fuck, baby. Make me pull out. I'm going to cum. I'm right there. I'm going to cum. It feels so fucking good. Fuck. I have to cum. I have to cum."

With that, I felt his cock give a giant twitch. I shook my head hard against his neck, back and forth, my eyes suddenly open wide. I didn't want him to cum inside me. Even though it sounded fucking hot in the moment, I knew that I would worry later. Obviously, my fear was entirely irrational. I had already been irresponsible. The damage was done. Precum was an issue, and there was the obvious leftover sperm from his last ejaculation, but I rationalized at the very least, it hadn't been a full shot. No velocity.

My wheedling tone matched his. "Pull out. Please, Tyler. Pull out. I want to see you shoot your cum all over me. Cum as much as you need to, babe. Just spray it all over me. You don't want to get me pregnant."

When I mentioned him knocking me up, Tyler's cock jerked again and he shuddered, hard. Apparently, the idea really turned him on. I filed that kink away for later exploration. His eyes were closed and I could see all of the veins in his eyelids. I suddenly felt like I couldn't breathe. I was still writhing under his weight, feeling this odd sense of gravity. The risk was largely imagined, but I was shocked to find that acting out the possibility of my biggest fear was somehow super fucking hot for me too.

When Tyler opened his eyes, I could see that his pupils were blown wide with lust. Two long, slow thrusts later, when he finally pulled out, I squeaked again. It immediately registered that his absence physically hurt. It was like I had gotten used to him inside me. When his cock was no longer there, I could feel all of this new, piercing space inside me. The negative was suddenly a tangible feeling.

For a second, I thought that Tyler had successfully denied his orgasm, but just as he managed to clear my waxed mound, my boyfriend blew his load all over me. His release was hands-free, silent but obviously intense. I could see the hole in his dick contracting with every hard spasm of his cock. Tyler's back arched. He clutched the headboard so hard that his knuckles turned white. I watched his lean stomach ripple as he humped hard into the empty air, spraying me with thick strings of ejaculate all the way from my chin to my belly button.

Tyler kissed me once more. Our open mouths met sloppily. Then, he collapsed heavily next to me as his cock finally deflated. Lying there, I felt safe with him in a way that I had never experienced with anyone before, let alone a man. I couldn't stop smiling as I suddenly realized that I might be able to really love Tyler. Even if we broke up, I instinctively knew that he was a good person, that I wouldn't ever regret doing this with him.

When Tyler got his breath back, my new lover leaned up on an elbow and looked possessively at the mess he'd made all over my freckled skin. He grinned wolfishly and pointedly raised an eyebrow.

"So, do you want to go again?"