My First Taste

I couldn't sleep. My stomach ached, and not just because Diane had squeezed and stretched my ball sack to the point of pain, but also because I struggled with my emotions around the act. I kept seeing the calm, casual expression on Diane's face as she administered the message. And I wanted more.

We were almost halfway through my parent's vacation overseas. My mom had asked Diane to check in on me throughout the week to make sure I wasn't up to mischief. I'm sure it never crossed my mom's mind that her 38-year-old friend would initiate her 18-year-old son into a sexual awakening. Especially one involving me eating my cum, creampies, and now obedience and pain. Such things would never even enter the minds of our conservative household.

Thinking back now, I never questioned what my mom would have in common with a sexually dominant woman like Diane. Then again, why would she? Diane was discrete. She never dressed provocatively. Most of the time, she wore jeans and a tee. Although she often went braless, her small breasts made that seem tame. She had auburn hair that she left in loose natural curls much of the time, gathered up in a clip. Light freckles across the bridge of her nose gave a patina of innocence belied by her piercing blue eyes.

The latest turn of the wheel from Diane had me questioning everything. Last night she had said, "I could own you completely, Matt."

The tone in her voice was confident and unquestionable. She would do what she said. It was as much a promise as a warning.

"I could take away all pleasure and take only my own. I could fuck anyone I like and bring you only the mess."

Eating my cum had been the first act. Eating another man's come from her pussy had been the next. She called me her cum slut. And she promised more.

I should have run for cover with threats like those, and yet my thoughts became full of such scenes. "Lock you up forever. So you never, ever come again." How? In my room? In her house? In a cell? My sexual awakening was so new, the concept of a cock cage was entirely foreign. But I felt the draw of being at her beck and call, waiting for her to release me from my longing.

(From the present day, wearing a cage around my cock and balls, waiting for my mistress to show me any kind of kindness, I can only laugh at my naivety. Oh, to feel it again, that tightening in my stomach the first time the lock clicked.)

Lying in bed, I kicked the sheets off my sweating body. I reached down and circled my fingers around my balls. I pulled them down and squeezed, trying to recreate the strength and firmness, the eerie familiarity Diane had with the limits of my endurance. I could not equal her technique. I couldn't push myself as far as she did, but I found the act comforting and soon fell asleep with the dull ache.

The restaurant where I worked was dead. I kept hoping to be released early. But Teresa and Carla got to the manager first. As the newest hire, he would hold me for the end. And Molly was still around because the manager had a thing for her. Plus, she had regulars that tipped well and bought drinks. I kept catching Molly's eye, which only increased my anxiety following the whipped cream prank.

Being slow gave me time to think about my embarrassment. The entire staff knew by now that I'd lost my virginity to Teresa and had eaten her pussy after I'd come inside her. The teasing stopped after I kinda owned it, but now I got pitying looks, which was worse. Honestly, I saw nothing perverted about what I had done. Diane loved it. And Teresa thoroughly enjoyed it while I was doing it. Only after did she have second thoughts.

On her way out earlier, Teresa stopped me and apologized. "I didn't think it'd get around like that," she said.

I'd had time to think about my response since Teresa had texted last night. "I thought you were a kinder person." Her face fell, but she squeezed my shoulder and nodded. The aroma of her skin and that dance of loose, dark curls around her face made me want to say more, to hold on to her a little, maybe start over with her; but I thought about what Diane would say and realized that it was better to let Teresa sit in this feeling longer, even though I really wanted to fuck her again.

As the shift went on, Molly had me sidelined. She was going to cover every table, and the manager would let her. She even had me bussing for her. Plus, she seemed to like one regular. He had the look of a lawyer. He often sat at the end of the bar after lunch and worked on a laptop. I think he liked to keep his scotch habit out of the office. He had graying hair but an athletic build that he likely paid a personal trainer to maintain. I laughed to myself, thinking about him being yelled at and scolded to "Go for more, bruh!"

I didn't see him leave, but after he was gone, Molly disappeared, too. I finally picked up a table -- a couple of old gals who ordered salads. They were going to talk for hours, leaving me with nothing to do but top off their waters for a five-dollar tip between them.

Between waters, I hung out in the break room, scrolling my phone. Molly came in and smiled at me.

"Dead table."

"Yeah."

"Wanna see something?" she said.

I looked up. "C'mere," she said with a smirk. Then she went into the supply closet.

Confused, I stood up after a moment and followed her in.

The inside of the closet had that strange combination of scents -- pine cleaners, dust, and fresh linens wrapped in plastic. Dimly lit by one old bulb, it was a quiet place used occasionally by us when the break room got too busy. I'd caught Carla reading in here before.

Molly leaned back against the shelves. She had an air of conspiracy to her and I wondered if she was going to share some gossip or bust my balls.

She said, "Teresa really fucked you over, didn't she?"

I sighed. Crap, I thought. Molly was bored. Was she going to bring this up to entertain herself?

She said, "It's OK. I think it was shitty. But she's stupid."

"OK." I felt the awkwardness of this longest conversation ever with Molly being about my sexual kinks. However, she was so pretty, I hardly believed she'd talk to me at all.

"Actually," Molly said, "I want to see something of yours." She shook off the clear confusion on my face and added, "Besides... everything else... Teresa said you're packing." After that failed to clarify things for me, she said. "Your dick, bonehead."

My mouth literally dropped open, eliciting a smile from Molly. She enjoyed throwing people off balance. I said, "It's not really."

"Look, I'm curious. It's dead. Let's see whatTeresathinks is big."

"Uh, I'm not really... ready?" I said.

Molly, stepped close to me. I froze in uncertainty, which she took as acquiescence, unbuttoning my slacks, lowering my zipper. Then she stepped back. "Don't disappoint me, Matty," she said with an exaggerated pout.

My heart racing and my mouth dry, I felt the furthest thing from excitement, but the amusement in her eyes as she leaned back against the shelves while her eyes fixated on my open fly, sparked me. There was something about being under the casual gaze of a confident woman that made me want to obey.

I pulled the fly apart and dropped my pants to the ground. Standing now in just my white briefs, I felt the stirring of excitement. Still, the panic rising in me was suppressing any further movement.

"No sense stopping now," Molly said.

I tugged down the waistband of my briefs and dropped them, too. Now I stood only in my uniform shirt and the absurd short apron we had to wear. My poor dick and balls were pulled up tight.

"I... I'm a... grower," I apologized.

"You must be," she said with a snort. "I think I know what will help... motivate you." She gathered her skirt in her fingers and slowly raised it up her thighs, pulling that and the apron up like a rising curtain, until I gasped as she revealed her bare pussy. She wore no underwear. She had a small patch of hair above her vee. I couldn't see her lips in the smoothly shaved split, but it was shining with wetness. Holding her skirt with one hand, she lowered the other to her pussy and spread herself open. Leaning back further, she lifted her hips slightly so I could clearly see her open pussy dripping with cum.

"Fuck," I muttered.

"Thought you'd like that," she said. "And apparently, so doeshe." She sighed softly as she watched my cock quickly filling with blood. In seconds, I was fully hard and in seconds more, almost painfully so.

Molly ground her clit with her finger while she gazed at my cock. She said, "I guess Teresa'snota liar. Do you think my pussy's pretty?"

I nodded.

"You like a creamy pussy, then?"

I swallowed hard.

"Yeah, you want it, don't you?"

I shook my head. The idea scared me.

"No?" she said. "Do you only eatyourcum, then?"

I couldn't speak. My head pounded. I kept thinking about eating Diane's pussy after another man had fucked her, and after I'd pumped more of my seed into her. My mouth watered. But this was a random man's. I pictured the strong lawyer rutting into her in the back seat of his Cadillac, Molly's moans echoing in the car. What did she sound like when she came? Would we get caught if I dropped to my knees and sucked on her right there? I was curious to explore her pussy, which had smaller lips than Teresa or Diane. Who knew there were so many types? I wanted to try them all. But the overwhelming drive was that a dominant, pretty womanwantedme to perform for her.

She said, "Show me, Matty. Jerk off for me. Let me see it spit."

I drooled into my hand and stroked my cock. It wouldn't take much.

Molly said, "That's it. That's a good boy. Make yourself cum watching me." She rubbed herself furiously. "Jeff's not as big as you. And he didn't make me come. I need to come so bad. You gonna make me come, Matty? You gonna squirt for me and..."

I groaned as I came, barely getting my hand under it to catch all the flow.

"Fuck, that's a geyser," she yelped as her fingers squelched in and out of her snatch. "Do it. Do it, please."

I brought my hands up quickly before I could change my mind. I looked her in the eyes as I sucked the cum from my palm. It tasted so sweet and good. It was gooey and runny and I could barely get it all before it dripped between my fingers and down my wrist.

"Fuck, that's... that's fucking nasty," she said, but it only edged her closer. "Eat that spunk. Fuck, eat it up, you fucking..." She didn't finish her sentence as she climaxed. She wriggled and rubbed her clit for a few more moments as she calmed down. I watched her in amazement as her fingers coated with sticky cum. Panting, she stood up and held her dripping hand out in front of my mouth. "Tell me you don't want it."

I stared at the creamy mess on her fingers. I could smell the combined aroma of her cum and his. I worried for a moment what Diane would say if she knew. Would she be proud of me? Angry? Jealous? Before I could think any more, I opened my mouth and sucked Molly's fingers. I moaned softly as the tastes mingled in my mouth. I swirled my tongue around her fingers. She pulled them out slowly, letting my lips clean them. Her wicked gaze told me I wasn't done. She pressed her fingers deep inside her again and brought them out.

"What a sweet boy," she said each time she fed me until I could taste only her, which was sweet like almonds. At last, she patted me on the cheek, kissed me lightly on the lips and said, "Well, that wasn't boring." She let her skirt drop, washed her hands in the utility sink and left the room without so much looking back.

I stood there with my pants around my ankles, dumbfounded, alone in the supply closet, with my cock dribbling down onto the floor. I pulled myself back together, wiped the floor and washed up as she had done. Rinsing my mouth with water from the sink, I looked at my face in the mirror. On the mirror a sticker read, "Smiles bring tips!" and I laughed at the private joke. What the fuck was I?

I knew what Diane called me. "Cum slut."

Molly didn't much look at me for the rest of the shift. She smirked once or twice. And as we clocked out, she reassured me, "Between us." I nodded, grateful that she wouldn't betray me as Teresa did. I feared she didn't want word getting out that she'd been so intimate with a guy like me. But as she left, she actually winked at me, and I felt a rush of desire and relief.

Still, on the drive home, doubts and fears crept in. What would Diane think? I felt guilty, as if I had cheated on her. Of course, Diane wasn't my girlfriend. She'd even refused to sleep with me until I'd lost my virginity to another girl my age, so she wasn't asking for exclusivity. Yet, I felt this bond with her. I'd lost another kind of innocence with her, and it made me feel like I belonged to her.

Alone in the house, I cleaned. Domesticity comforted me, as if I were preparing a nest for Diane and I. Hoping she might come by and, wanting to please her, I needed to make her comfortable, and possibly earn her praise. Imagining her walking in at any moment, I maintained my adopted uniform -- dressed only in my white briefs -- replaying all the sexual adventures of the past few days in my mind to keep myself hard.

Which is why it shocked me to hear her voice behind me in the kitchen as I cleaned my dinner dishes.

"How's my little helper?"

Nearly dropping the plate in my hand, I spun around to see her nonchalantly sitting on a stool across the counter at my side. I don't know how long she had been watching me, but she looked me up and down and said, "You dress like that for me?"

I stammered, and she waved me off with a laugh. "Oh, I love this for you -- expectant, vulnerable... hard."

My cock stretched the front of my briefs out and I realized the tip was poking out now. I wanted to hide it; and I wanted her to see it. So, I stood still and waited.

She licked her lips and paused a long time before shaking her head. "Anyway. We need to talk, and that is distracting."

I frowned, uncertain how to solve her problem.

"Just grab an apron or something," she said

I opened a drawer and pulled out one apron and draped it over my head, tying it in the back. Fortunately, it wasn't anything frilly -- just a simple canvas apron that stopped just above my knees.

"Good," she smiled. "It was making us hungry." Then she smiled mischievously. "Still, now that I'm seeing this, please take off those briefs."

Blushing, I reached back and peeled my underwear down to my ankles. I stepped out of them and stood naked except for the apron now tented over my erect cock.

She bit her lip and gestured for me to turn around. I slowly turned, giving her a clear view of my naked ass. She could also see my shaft from the side pushing out the flap of the apron. When I returned to face her, she smiled.

"Still distracting, but I couldn't help myself." She walked around the counter and sat herself up on my side of it, facing me at eye level. She wore a white tee and shorts. Two shadows on the shirt showed the position of her taught nipples. The fabric wrapped neatly under the curve of her small breasts. Her long legs dangled from her seat on the counter. She let them bounce against the cabinet as she watched feet thinking about what she wanted to say. Finally, she sighed and looked up.

"I made a mistake," she said.

My heart fell. A thousand thoughts ran through my mind and they all were, "No!" Reading the panic in my eyes, she said. "No, not this." She gestured back and forth between us. "I amlovingthis." She stretched her hands out and I stepped closer. She put her hands on my shoulder.

"I have a duty and, in my excitement, I dropped the ball. It's my job to take care of you."

I shook my head. "I'm good, Diane--"

She cut me off. "I know you love what we do. It's not that. I know ittoowell. I took it for granted. You're young. You're eager. You want to please me... so much." She seemed to taste the words coming out of her mouth. She closed her eyes on what she was imagining. "But. But I need to make sure you're ready. Yesterday, I surprised you in a way I should not have, bringing you another man's sloppy seconds. It is my responsibility as your... superior. To make sure you consent to everything we try... beforehand."

I shook my head. "I wanted it, Diane."

"Clearly."

"I want... more of it."

She looked down at the rise in my apron. "Clearly." She shook her head and looked back at me. "I have this fun new toy and I'm eager to play, but I also know you will do everything I ask and that's exactly why I need to be sure you know what I'm asking you to do. You need to feel you can ask me to stop, or wait, or whatever you need. Because..." She sighed heavily, "I will fucking eat you alive if I'm not careful. And I don't think you'll stop me."

"No," I said. "I won't."

She put one hand on my chest. "Then, at the very least, when we're having fun, tell you'll ask me to stop. Say, 'red' or 'yellow' and I'll stop or wait. It's very OK."

"Of course," I said, certain those words would never come out of my mouth.

"Mean it," she said. "When we go too far, or if you need a break, use the words."

"OK," I said, smiling.

"No, Matt. Mean it."

I put my hand on her chest. "OK, Diane. I will."

She stared hard at me for a second and nodded. "OK, then."

Then she lowered her hand and slid it under my apron. She stroked my cock and rubbed her thumb over the crown, which was slick with pre-cum. I leaned toward her as she caressed down to my balls and slowly, gently cradled them. Then she closed her hand. My eyes snapped to hers. Firmly, millimeter by millimeter, she closed her fingers around my balls. I felt discomfort, then ache, then pain. I swallowed hard as she continued the pressure. Our eyes locked in this new game of chicken. My face flushed and stomach ached as she squeezed harder. My eyes watered. I regretted my confidence.

"Yellow," I groaned.

Her hand froze. I panted and caught my breath. I nodded. She squeezed hard.

"Red," I yelped.

She released her grip, brought her hand up to my face.

"Good job," she said, pressing her sticky thumb into my mouth for reward. I sucked the trace of pre-cum from there. Then she returned to my cock to draw another, wetter thumbful to my mouth. She rubbed it against my lips. As my stomach knotted with the dull ache rising from my groin. I leaned my head against her shoulder and she stroked the back of my head.

"There, there," she said. "Now stroke yourself for me."

I reached down and did as she said, using my dripping pre-cum for lubrication.

"That's it, Matt." She pulled my apron up and brought her legs together in front of me. "Come on my legs, Matt. Spurt all over them."

Grunting, I furiously stroked, needing to please her, wanting to release all the pent-up cum out of my balls and onto her smooth, silky legs. She ran her fingers through my hair, tugging tightly at my locks. "Come, boy," she murmured.

"Fuck," I groaned as I gasped at the first pulses. The tightness of my scrotum awoke the ache in my balls as pain and pleasure merged to pump out of my cock and spatter her long legs. I stared into her eyes as I squeezed out the last of my cum, rubbing the crown of my cock up and down her shin.

She bit her lip. Held my head. "Beg for it."

"Please, Diane. Let me."

"What, Matt. What do you want?"

"My cum. May I lick it up for you?"

"For me?"

"For me, Diane. I want to eat it, please. I want it, please."

"Are you my cum slut?"

"Yes, ma'am. Please."

"Any cum? Any one?"

"Yes, ma'am."

She paused, now literally holding my head, straining against her grip. I imagined the long trails of cum running down her shins, wrapping around her ankles, dripping under the soles of her feet.