My First Taste

My First Taste -- Ch.03

I had a problem. Diane said that she wouldn't take my virginity. If I wanted to sleep with her, I'd need to lose it with someone closer to my age. I was 18, and Diane was twenty years older, one of my mom's friends, and most recently something of a tutor for me. It started when my mom asked Diane to check in on me while my parents were away on holiday, and when she made her first drop-in, her surprise inspection found me in my underwear watching an R-rated movie. Caught literally with my pants down and unable to hide my excitement, it mortified me. However, she found me 'quite sufficient' to use her words and then taught me how to finish what I started, along with one of her favorite tricks -- cleaning up after myself. As a sheltered kid, anything sexual was novel and exciting, and I was eating it up so-to-speak.

With few close friends, being painfully shy around girls, and having no game to speak of, Diane was a miracle to me. She clearly enjoyed playing with me, and I found comfort in following her instructions. When she told me she wouldn't take my virginity, it devastated me. I moped around the whole next day, replaying the events of the past two nights. She had shown me how to masturbate properly, which included getting rid of the evidence -- swallowing the prodigious cum. And she taught me how to eat a woman properly. Hearing her moans and screams when I finally got it right fueled all my dreams -- day and night. I didn't want anyone else but Diane.

But it was her boundary, and if I learned anything so far, it was that I was happiest when I obeyed her.

She came over in the evening after work. She wore jeans and a t-shirt like normal. I don't know what she did for work, whether she changed after or if this was her normal attire. She didn't dress to entice me. Her body was enough. She came over and I was overcome.

Tonight, "Strip," was her only word to me.

I quickly shed my clothes. She pointed to the floor.

"We could go upstairs," I said, pointing to the ceiling. She shook her head.

In hindsight, neither my single bed nor my parent's marital bed were acceptable options for her. The hardwood floor was cool on my back, but my shiver was more at the anticipation as she unbuttoned her jeans and pulled them off along with her underwear. I pursed my lips, seeing her pussy exposed. She had a short patch of light-brown hair. Her labia were parting and pink. She had given me a full anatomy lesson and tutorial on how to tease and build her orgasm. Lying on the floor, I hoped she might just sit down on my mouth. She ran her fingers through her folds. I saw the shine already. I felt my pulse quicken. Her excitement meant she had been thinking of what she wanted to do tonight. It was making her wet. The memory of her taste -- bright and earthy -- made my mouth flood. I swallowed.

Leaving on her tight tee, she sat down across my hips. I winced as I felt my bones bite into the floor. She grinned -- a slight turn of one side of her mouth. If I hadn't been fully hard already, that sly little smile would have brought me there all on its own. She scooted in, bringing her pussy closer to my cock, then she moved a little more until I could feel the heat of her labia pressing against the base of my cock.

"So close, and yet..." she said as she lightly dragged her fingernails along the length of my erection. I shook my head. Already, I panted. I reached to caress her nipples standing up beneath her tee. She shook her head, and I dropped my hands back to my sides.

"All I need to do is slide up," she said, lifting and dragging her pussy along the bottom of my shaft. "And over." Tilting her pelvis, she lighting kissed the crown of my cock with her pussy.

"Please," I said, betraying myself with the high, wavering pitch of my voice.

"And down," she said. She eased back and dragged her pussy all the way back down the length of my shaft to the base. I felt the air cooling as she painted my cock with her wetness.

She rewarded my long moan with that sly grin.

"So, tell me who are the candidates." She followed her question by opening her mouth and letting a long string of saliva drip down onto my cock. She stroked me to spread the liquid around. I had been using all my strength not to come. I cried out, and she grabbed the base of my cock, holding it tight until I nodded in relief.

I tried to think of who might want to sleep with me. I wasn't in school anymore and I hadn't started college yet. Once, I think a girl from church might have had a crush on me, but I never had the courage to act. She had a boyfriend now and likely was saving herself for marriage, anyway. The only place I knew any girls was at the restaurant I worked as a server (a role that seemed made for me, now that I thought about it.)

Molly was a tall blond girl -- all smiles, and flirty with the customers. Teresa was petite and curvy, with light-brown skin and unruly hair that fought with whatever band or tie she attempted to tame it with. Carla had no filter. She had brown hair and a round face with a wide mouth. She had a lip piercing that I fixated on. She talked all the time with the cooks and seemed approachable.

"Any of them flirt with you?" Diane said. Her fingers lightly tapping my cock again.

"I don't know. I can never tell."

Diane shook her head and tapped her fingernails along my cock. "My poor boy. Each of those girls already knows if she would sleep with you. You're not ugly. Maybe awkward, a little skinny, but that doesn't matter. Most girls aren't attracted to looks alone. You're clean and you smell nice, which is table stakes."

I shook my head.

"Poker, Matt. The money to ante up and play. They won't mind a shy guy either. It's better than some bro hitting on them."

"If you say so."

"OK, Matt. Do any of them poke fun at you? Make a little joke, perhaps."

I thought about it and Carla sometimes bossed me around. And I knew now that I liked that, but she didn't joke about it. And Molly didn't talk to me at all. She was too busy.

"Teresa sometime jokes," I said. "Yesterday, she made fun of the way I took too many trips from the kitchen to get orders out."

"Did she show you how to do it right?" Using her hand to stroke me from base to tip, she made sure I got the double entendre.

I sighed, trying to focus. "Yeah, she showed me her plate stacking technique. She called me hopeless."

Diane laughed. "Yeah, she's the one, Matt. That's like standing behind you to help your tennis swing."

I recalled how Teresa smiled even while shaking her head at my ineptness, and the way her fingers brushed my forearms as she moved my hands the right way. I hadn't thought of that as flirting, but she could have just told me how, or not said anything at all.

"She gave me her attention," I said.

"Right. It's an invitation -- not to fuck her, but to talk. How old is she?"

"Same age, I'm pretty sure. We talked about graduation."

"And does she have a boyfriend?" She twisted her grip around my cock on the word boyfriend.

Suddenly, I felt jealous. "I don't think so. She did, but then he went to State."

"She worked in that detail, which should give you an idea."

"So, I should...?"

"Just tell her you like talking to her, and you'd like to talk more. See if she'll meet you for lunch or dinner."

Diane signaled the matter settled by stroking me firmly from base to tip. With my cock standing up in front of her flat belly, decorated by a line of fine hairs trailing down, I had the strangest sensation that she had a cock rather than me. It was a convincing optical illusion, like she was stroking herself while straddling me. In a real sense, my cockwashers now. I didn't control it; she did. For a moment, a scene flooded my mind. Her stroking her cock, making it hard so she could enter me. I felt my asshole pucker. I shook my head, eliciting that grin from her.

"There it is," she said.

"What?"

"Your need. You're my eager boy, ready for me to own you."

I gulped. "Please."

She opened her hand, leaving me twitching. Then she dripped another string of saliva down onto my cock. Slowly, she lay down over me, trapping my cock between her belly and mine. My eyes opened wide as she wriggled on top of me. She ground into me, forward and back.

"Fuck," I moaned.

"Yes, it feels like I'm fucking you, doesn't it?"

"Mm hm."

She thrust against me, sliding against my cock.

"I...."

She nodded and kissed my shoulder. "I want you to, Matt. I want you to squirt all your load between us. Make a big mess."

"Oh, God," I cried as the flood of sensation led to the flood of cum pumping into the warm space between us. I didn't know if being inside a woman would feel better, but this was amazing. She cooed into my ear as she thrust against me, making a slick, sucking sound with our skin. When I stopped twitching at last, she kissed my cheek and pushed herself back up.

Looking down at the sticky pool on my belly and the dripping curtain of cum on hers, she shook her head. "So much," she said. She ran her hand along her belly to scoop into her hand. She brought it to her mouth and slurped it in. She swallowed it, sucking her teeth. "So, sweet Matt. I'm sorry, I just needed a taste before your greedy little mouth took it all."

She trained me well enough in just these couple days that I felt jealous. I scooped up some from my belly and held my hand over my open mouth, letting it drip in.

"Fuck, yes," Diane said. She pulled her shirt up, finally exposing her small breasts, nipples hard. Breathing heavily, she ran her fingers through the spunk on my belly and pushed them into my mouth to clean. It excited her to see my enthusiasm. I went to a place in my mind where all my senses were on the taste, texture, and scent of my cum. All I cared about was licking her fingers like a slut. When we got all we could with our hands, I raised up, pushing her onto her back so I could lick her belly clean.

When there was nothing left, I curled up next to her as we caught our breath. After a few minutes, I looked down at Diane's naked body curled next to mine. The warmth of her small breast against my ribs, the curve of her hipbone pointing down to my new favorite meal.

"Can I practice some more?" I said.

Diane laughed. "We have to get you ready for game day, I guess. Teresa won't believe her luck."

I scooted down between her legs. Just being there made me hard again.

"Turn around this way," Diane said, and I switched position so that my cock hovered over her mouth while I licked her pussy. I hoped she might suck me while in this position, but she pressed on my hips to keep them high. I felt exposed with my face down and my ass high. She lightly rubbed the head of my cock, which was dripping again.

Diane said, "One day we'll see how many times you can come in one night."

I could only moan. I lost myself in her pussy. I just loved the taste. It thrilled me to feel the swelling in her clit. Diving my tongue deep inside her vagina.

She began saying things. I'm not sure she meant for me or just for her. It was like she was dreaming out loud. "I'll collect all your cum in a cup and make you beg to drink it for me at the end of the night. Would you do that? Would you beg me?"

I grunted in agreement. She could have said anything and my answer would be yes. She stroked my ass with one hand and said, "Once you're no longer a virgin, you can eat your cum out of my pussy, Matt. Would you do that? Would you fuck me full of cum and let me sit on your face until all your jizz was gone?"

Her words were driving me crazy. Maybe it was just her breathless tone. "Maybe I'll fuck someone else, Matt. Maybe I'll come over after I've fucked another man."

I felt a sting of jealousy, but also the conflict of desire. I didn't want her with anyone else, but I wanted to be with her anyway that I could. If she came back to me, wasn't that a win? Her words and moans were pushing me to the edge. I blurted out, "Yes, please."

"Of course, I will, Matt. I'll bring you a fresh cream pie? Do you know what that is?"

I didn't, but it didn't take a genius to understand. I slurped her pussy in response, imagining it full of cream.

"Yes. Yes, Matt. Pretend you're sucking it all out. Show me how much you want it."

It wasn't hard to imagine; she flooded my mouth with all her delicious liquid.

She thrashed for a bit, then said, "The clit. Work it now. Oh, God."

As my aching tongue flicked her clit up and down the way she liked, and I heard her cries increase, I felt my balls tighten, and right as we both peaked. I felt her finger slide into my asshole. She pressed down inside and I swear sparks when through my eyes. I felt the pulsing of my orgasm against the pressure of her finger. I felt my cum spout all over, not knowing where. But I held my tongue's pace through the spasms of her orgasm. It was her loudest, longest yet. I gripped her finger with my ass and when she pulled her finger out, I groaned at the loss. She patted my ass and said, "I just knew you'd love that."

I sat up on my knees, looking down at her face. Cum spattered her chin, neck, and tits. She crooked her finger at me and I bent down to kiss her. We let our tongues play in the salty mix. Then I lovingly cleaned up her face. To make is easier, I turned around before working on her neck, sucking in each cooling glob, chasing the clear runners that tried to escape my tongue. Then I cleaned her chest. As I cleared each patch of skin, I ran her words through my head -- all the whispered promises. How many times could I come in one night? Would she really do that? Would she fuck someone else? Bring it here to me? The thoughts spurred my efforts. I could not deny I loved eating my cum. Would I like it if it weren't mine?

"Someone's enthusiastic," she said as I sucked on her nipples.

I moaned in agreement. She was kind enough not to ask me what I was thinking. But I think she knew.

*

Diane was right, Teresa was open to seeing me. She played down her interest, but I could see a flicker in her eyes when she agreed to a date. We met for dinner and I learned about her family and her plans for college. She was going to put in a year or two at the community college and keep working to keep from going into too much debt. I told her I was doing a gap year, but I honestly didn't know my next steps.

In a way, talking with Teresa felt like cheating, even though I knew Diane wanted this. It added to my excitement, the feeling of being bad. Plus, I couldn't think with the scent of her perfume, and the flicker of light in her eyes as she crinkled them to laugh at one of my lame jokes. At one point, I made a comment and brushed my hand over hers. She didn't flinch, so I let it stay. As we walked to the car, I asked her if she'd want to grab a beer at my place and maybe watch a movie or something. She took a minute to decide, finally looking up at me and giving me a kiss.

"Sure," she said.

The beer would be something I could explain later to my parents. It was worth the risk. Maybe I could convince Diane to buy replacements for me. When we were in the kitchen, Teresa spotted the pool outside and so we took our beers out there, talking under the stars. The kiss had broken the ice, so we sat on a chaise and soon made out.

"How's the water?" she said after a break.

I had lost myself in the softness of her lips and the texture of her skin, so it took a moment to realize what she meant.

"You want to swim?"

"Yeah."

"I don't think we have any swimsuits here. Mom packed hers, I think."

Teresa shook her head and pulled me up. "I'll just swim in my underwear." She bit her lip and looked up at me. I nodded as my heart pounded loud enough for me to fear she heard it. She unbuttoned her dress and let it slip off her shoulders. She wore a simple set of white bra and panties decorated in blue polka dots. Her breasts spilled out of the cups. I'd been trying to be polite all evening, but now I gave them my full attention. I reached up, but she stopped me.

"Your turn, Matty."

I pulled my polo up over my head and unbuttoned my jeans. I looked up at her for reassurance. I was getting hard already. There would be no way to hide it. She smiled at me and gave me a little nod before looking down.

I unzipped my fly and carefully separating my jeans from my underwear to avoid taking them both down together. As it was, when my jeans dropped to my ankles and I stepped awkwardly out of them, my cock had stretched out my briefs.

I looked into her eyes, but they were focused on my underwear. She nodded and looked at me. "Wanna get in?"

"Oh, yes." I said, which made her laugh because she knew what I was thinking. I returned the laugh, and we went to the steps to ease in. The water was cool at first, which made her nipples tighten up under the cloth. I saw the pointed shape of her nipples and her dark brown areolae. Once we were in up to our necks and adjusted, I pulled her in for a kiss. I let my hands roam again, enjoying the feeling of supporting her in the water, turning around. She put her arms around my shoulders and kept herself close. I squeezed her ass where her underwear exposed her cheeks.

Soon we were making out heavily and breathing hard. We touched each other everywhere but in that last place. At last, she said the most magical words, "I want to."

"Me too," I said. "Let me get us some towels."

I got out of the pool, the light air chilling my damp skin. My underwear was pulled down by the weight of water, exposing much of my ass. In front, the fabric hung on my cock. I turned back to see Teresa ogling my ass. She smiled as I caught her and let out a little breath when she saw my cock struggling against the weight of my underwear. She stood up and her bra was transparent now. Her breasts were much larger than Diane's and her nipples were darker and wider. I grabbed our towels from the box by the pool. I held out the thickest one for Teresa. She walked up the steps, bringing her soaked panties into view. The cloth plastered to the outline of her pussy. She had no pubic hair and her lips were thick and puffy, longer than Diane's. I could even see the outline of the hood of her clit and the swelling pearl underneath before wrapping the towel around her and pulling her close. It made me want to explore every fold.

I didn't bother with my towel. I slowly worked her towel around her body, drying each part. As I dabbed her chest, she reached behind and unhooked her bra, letting it drop with a splat on the ground. I worked my way down, taking time to suck and lick her nipples. She enjoyed that, putting her hands around my neck.

As her skin dried in the warm air, I worked my kisses down over her belly and across her hips. I licked under hip bones, making her shiver as I tugged the underwear down over them. I avoided her pussy as I dried each leg, only taking a moment in passing to breathe along the crease of her thigh. I inhaled the aroma of her excitement, nudging out the fading chlorine of the pool. Kissing along my path down her legs, even to her toes, which I had the impulse to suck, but restrained myself.

My knees dug into the pool deck, but I didn't care. I let the towel drop as I stared at her pussy. Without any hair, I saw more detail. In the air, goosebumps raised echoing the polka dots of her underwear. As her lips opened, I saw a thin hint of pink. That's where I planted my first kiss. She leaned into it and I grabbed her ass to pull her in close.

She tasted so sweet. Her pussy was slick and sticky. I teased her lips, enjoying sucking on them and feeling the twitch in her hips and hearing the catch in her throat when my tongue found a sensitive area.

She moaned and gasped for a bit before grabbing my arm and pulling me up. "My turn," she said. Following my lead, she used the towel to dab any remaining drops of water on my skin. I was mostly dry except for my legs, where the heavy cotton dripped water. She kissed her way down my torso. When she got to my underwear, she gently ran her fingers over the outline of my cock. Looking up at me, she pulled them down. Unfettered, it stood straight up over her face. She kissed the shaft, looking into my eyes. She kissed up to the tip and, closing her eyes, she enclosed the head of my cock with her lips. I twitched and breathed, hoping not to come before I could actually lose my virginity with her.