The Training Manager Saga Ch. 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I looked up to see her grabbing her breasts and massaging them harder and harder each time I kiss her. I move lower to her outer lips. Kissing her thighs and using my tongue to swirl around the outer lining of that perfect cunt. I can smell her arousal. I dip my tongue into her pussy. Just a quick swipe and listen as Samantha gasps at the sensation.

"If you are going to do this, you better do it fast because I am going to cum soon." Samantha said breathlessly.

"Already?" I ask her. "I haven't even started! You are in for some major punishment tonight. I have a lot to work out. I will give you the option though. Do you want to stay here or should we go to my bedroom?"

She chose. "Bedroom. Now."

Samantha and I got out of the tub and didn't bother drying off. We were getting wet again anyway. We ran across the hall and jumped in the bed. She lay there legs sprawled out and beckoned me to move in on her.

"Nope, I want you standing. I want you to stand as long as you can while I finger you. Then I want you to stand there while I eat you out. If you cum before I am done, I will make you stand there longer." I tell her.

As much as she hates this game, I know it is one of her favorites. Samantha puts on a pouty face but stands eagerly and pulls me in for a kiss while I allow my hands to slide between her legs. I press my fingers into her cunt and slowly rub them in and out. Samantha starts to move her hips into my fingers trying to increase the pace that I have set. I oblige for her. After all she is my best friend and I am not totally heartless.

Once we have a steady rhythm going I move my mouth to her breasts and suck her nipple into my mouth. I flick my tongue over each nipple and lightly blow on the area that I had just kissed. Sam groaned with each flick. She takes her hands and moves them over my body. Pulling my nipples and rubbing them between her fingers. I trace my kisses down her side and stop just short of her hips.

"Are you ready?" I ask her teasingly.

"No not at all. I am totally unaffected by your fingers" she said sarcastically.

My mouth grins against her mound and continue to kiss my way to her waiting slit. She spreads her legs to allow room for my head and I slide my tongue into her dripping vagina. Her knees bend at the sensation and I stop to look up at her.

"Don't you dare sit down or I will stop." I informed her.

"I can't help it, it feels so good." She gasped.

I continued my assault on her. Licking her clit, pushing my tongue into her opening, pulling it out, then completing a figure eight between her love nub and her open pussy. Her juices are dripping down my chin. She is flowing so much I can't contain it all in my mouth. I push her to the bed and bury my head into her pussy.

"For the record, you pushed me onto my back. I did not lie on the bed willingly!" She humorously explained between gasps of pleasure.

"I know, but you taste so amazing! I needed to get more. Now shut up and let me eat." I commanded.

I spread her knees farther apart and use my fingers to open her up so I can lick her inner folds and taste more of that sweet juice. My tongue is now fucking her hole and I can't get enough of it. She is so fucking wonderful. Her hands move down to her clit and she begins to rub it hard and fast.

"Please baby, let me cum. I can't hold off much longer" she whines.

I don't respond. I can't, I am too busy sucking her juicy pussy to even hear her. I continue to tongue fuck her. My hands are pumping in and out of her hole, bringing more juice out with each thrust.

"Baby, I am going to cum. I can't hold off." She warns.

Her hips begin to buck. Her hands tangle in my hair and she pushes her pussy deeper into my face. I feel her come. She is squirting her juices into my mouth. I suck them up, savoring each spurt that follows. When she is done, I continue to lick her lips, moving back to her labia, to her inner thighs, up her stomach, to her breasts and finally to her lips. We kiss for several minutes and just hold each other as her orgasm subsides.

"Now it's your turn" she says.

"I don't know if I can handle it right now. You made me cum just with your taste. Here feel." I take her hand to show her the affect her orgasm had on me.

My cunt is so wet it was running down my thighs. Her touch felt like electricity when she reached my thighs. It made me squirm when she slid her finger through the slit.

"Paybacks a bitch isn't it?" She grinned as she slid down the sheets to spread my legs.

My heart raced as she mimicked the same motions I had just done to her. She was learning. And she was an excellent student. Sam must have read my mind because the next thing out of her mouth was,

"See? You could train him to do these magical things too and then you would have the best of both worlds." She then delved back into my snatch.

She worked her tongue in and out and back around, paying attention to every sensitive area of my body. Before long Sam had my hips bucking against her face as I came into her mouth. Neither of us could stand for a while. We were both spent, so we lay there kissing and touching -- waiting for normal bodily function to take back over. Somehow I had missed three phone calls from work. I checked my voicemail and it didn't seem too important so I ignored them, took a shower, got dressed and went to find Sam's and my favorite men, Ben & Jerry. When I got out of the shower I noticed another text message. As I opened it, I noticed it was from Matthew. My heart skipped a beat.

"Need to talk to you tonight. Can we meet up somewhere?" The text read.

"When and where?" I replied back

"Store ok with you? Around 11:00?"

"I'll be there"

"Sam, I have to go in tonight, something is wrong at the store" I tell her.

"Was that Steve?" she asked.

"No, it was Matt; he needs to talk to me about something" I reveal.

"Riigghhhhttt, he needs to ' talk' to you." She said as gestured quotations in the air.

"Oh hush, I am sure it will be boring and uneventful. Will you be here when I get back, or do you have plans tonight?" I ask.

"I think I will head home. I am too spent to do much of anything else thanks to you!" She cooed.

"Alright I guess I will sleep alone tonight" I tease back.

At 10:30pm I threw on some sweats not bothering with panties or bra and headed to the store. Matt was in my office doing the nightly paperwork and preparing for the next day.

"What's up?" I ask him as I plop down in the chair opposite of my desk.

"I am working on the nightly numbers and can't find where the mid-day deposits are." He said lamely.

"You called me in for that?" I ask him.

"Well, uh, yeah. I wanted it to be done since we close together the next few nights." He explained.

"Matt, I am sure Meghan or Steve can handle it in the morning. What is really on your mind?" I am sure I sounded irritated.

About that time, Steve and Dan popped their head in and told me they were heading out.

"Want me to set the alarms before we go or are you going to be here for a bit?" One of them said.

"Go head and leave them, I will lock up on my way out. Thank guys have a good night." I take my attention back to Matthew- He was staring at me.

"What?" I ask him.

"Nothing, you just look amazing tonight."

"Thanks, now can we finish this tomorrow or was there something else?"

"Well there is something else, but I don't know how to ask without sounding like an ass hat."

"Then just ask Matt- what do you need?" I demanded.

"Umm well, I have been thinking about the other night. A lot. And I really liked it and want to do it again. I know that you didn't mean for it to happen and I know that you think I am too young for you, but I am really attracted to you and I umm, can I ,err would you ... umm."

"Christ Matt, out with it already. You know you can talk to me about anything, and the other night kinda made things a little more open don't you think?"

"Right, well, can I touch your tits? If you say no then its ok, but I just want to know what they feel like and whatnot."

I can't help the grin that spreads across my face. All that to just touch my boobs?

"Matt, come here." I reassured him.

I took his hand and guide them to my breasts. His hands were cold against my skin.

"You're not wearing a bra? Do you always go without a bra?" He naively wondered.

"I don't always go without a bra; just when I am called in after I have already showered and put on PJs. Um, are you going to do anything else or did you just want to feel me up?"

"I don't know what to do. When I told you I had no experience with women I wasn't making it up. I really have never done this with anyone." He sheepishly explained.

"How is that possible?! You are gorgeous, everyone loves you. Have you ever had a girlfriend ever in high school?"

"Nope. No one was ever interested in me." He said.

"Okay, here give me your hands and I will tell you what feels good to me."

I put my hands back on his and laced my fingers thru his. I rubbed his palm over my hardening nipples and he instinctively tightened his grip around the orbs in his hands. A sigh passed thru my mouth.

"Did I do something wrong?" He asked instantly pulling his hands away.

"Not at all baby, it feels so good. Your hands are so soft and strong. They feel amazing against my skin." I longingly said.

"Can I see your, umm, uhh, can I see them?" He mumbled.

I smiled back at him and kissed his cheek. He slid his hands around my back and kissed me back. He had not forgotten the way to kiss, albeit a little too eager. I slowed him down and he responded with more meaningful kisses.

"If you want to see them, you have to remove my shirt." I smiled.

"You are ok with that? I mean, I can take your shirt off to see what I am doing?"

"Yes Matthew, you can."

He reached for the hem of my hoodie and began to pull it over the top of my head. As he did, the material grazed across my sensitive areolas and they began to tighten into knots. When my shirt was off, I was left standing there while he looked in awe of my tits. He reached his hand back out, he lightly brushed over my nipples and squeezed the full part of my breast. I could feel his nervous tension through his hands. He was shaking. I moved toward him, pressing my body into his and could feel his hard cock through his khakis. He was much bigger than I imagined. I let his hands explore my body. I can't describe why I was so turned on by this. My gynecologist does the same thing every year and it had never been this exciting. I go back to showing Matthew where to touch me and then let him explore on his own.

I kissed his neck and grazed my teeth over his neck. He inhaled sharply every time that I did this. His hands became rougher with my breasts. I ground my hips into him and began kissing him harder. I ran my hands around his waist and down to his ass. It was firm. I pushed him harder into my body and I could feel his erection grinding into me. I reach to touch him and he quickly pulled away.

"I'm sorry. I got carried away. You were making me feel so good." I say breathing heavily.

"No, it's not you. I just wasn't expecting that and... umm, I want to do more but I don't want to turn you off. I know what I see on the internet, and I want to do those same things to you." He fumbled his words.

"Let's take it one step at a time. You can touch anything above the waist. You can kiss anything above the waist. Once you are okay with that we can move on. And Matthew, the minute you say stop we will okay?"

"I'm not a kid, you know. I do know what feels good on me and what I want to do to you. I just am new to it all."

"Then tell me everything you want to do to me. Show me what you want to do to me."

"I can't. I mean, I can, but I don't want you to think I am weird or something."

"Matt, you are a lot of things, but let me determine what is weird. Okay?"

I decided that second base is plenty for him tonight. Even though I wanted him to do more, he was pretty worked up. Maybe I would invite him over soon.

*****

A few weeks passed, and Matthew and I continued our little flirting. It was starting to get difficult to hide our relationship, if that is what you call it. Not that anyone off the street would notice, but a few of my employees were starting to talk. I decided that I should call Matt back into my office for another meeting. This time I had him keep the door open because of the nature of the discussion.

"Matt, I feel like our flirting is getting in the way of our jobs. Other employees are beginning to notice us and I don't want them getting any ideas. I will be changing the schedule to have us separated more to avoid any further fraternization between us. I cannot have our store family feeling like I am treating you any different on the work front then they are treated. Because you and I are the best at setting the store for each season, with the holidays just around the corner we will alternate the overnight resets" I explained.

The look on Matt's face told me he was not reading between the lines. I smiled at him and tapped my phone. I had sent him a text message telling him we would still see each other plenty. He opened his phone, read my message and then the realization reached his eyes.

He got up from my desk, walked out of my office and announced, a little too loudly, that he didn't want to do overnights alone and how unreasonable I was being. I had to roll my eyes. This kid definitely did not take drama class, or if he did, he was not very good at it. I packed up my bag and headed for home around 7:00 that night. Before I even hit my car, my phone was buzzing in my hand. I looked at the screen to see a text from Matt-

"Can we talk tonight while I am here being punished? : ) ".

I rolled my eyes and replied back "I guess."

At 11:00 pm on the dot my phone buzzed. The store was closed and everyone was leaving. Matt was already bored or horny.

"Send me a pic of your tits" I waited at few minutes and obliged. Another text.

"Send me a pic of your naked tits" Again I obliged.

Then another.

"Come here and let me see them in person"

"How about I stay here in my nice warm bed and get your sets done?" I responded back.

"Can I come over after I finish them?"

That should have been my clue that he was already done with the sixteen feet I had assigned to him, but I missed it. Or maybe I wanted him over tonight.

"I guess" I quickly tap back

An hour later there is a knock on my front door. Matthew is standing there his hands shoved in his pockets.

"What are you doing here?" I ask him

"You said I could come over when I was done. Remember?" He looked worried.

"So, I did. Come on in. Want a soda or some water?" I asked.

"Nah, I am good for now. Besides, I want something else." He grinned.

So, we were going to play this game tonight? Silly boy, I perfected this game a long time ago."And what is it that you want?" I ask while pulling him closer to me, "Do you want me?"

"Uh-huh" He confirmed.

I usher him to the overstuffed couch in my living room and he takes a seat in the middle. I walk past him and make sure that my T-shirt plays peek-a-boo with my ass cheeks. He doesn't miss it and he grabs my wrist to pull me onto his lap. Before I even land his hands are up my shirt, groping and rubbing my tits. He slides my shirt over my head and stops to admire my red boy-shorts. He then pulls me to his mouth for a kiss. It had been a few weeks since our last encounter. Sure, we had touched and kissed, but contact like this -- it seemed like an eternity.

"Here, let me change positions" I tell him as I turn to straddle him giving him a full frontal and very close up view of my breasts.

I wrap my hands around his neck and offer my neck to him. He eagerly nibbles my neck while pressing my tits to his chest. I arch my body up higher so his kisses can go lower. He notices this and looks up at me, almost asking for permission. I pull his head to my breast with one hand and lift my tit with the other, inviting him to take me into his mouth. The warmth of his mouth mixed with his cold hands made my skin tingle. His rapid heartbeat and his pulsing cock made my pussy wet. I was an experienced woman and was greatly affected by this boy's touch. I could not imagine what kind of sensory overload this was for him. I began to lift my hips and lower them back down - pressing my body against his and gliding back down again. Matt's hands were everywhere all at once. I had to take his hands and show him where to put them. I slid off his lap and in between his knees. I looked up at him and said,

" You've seen me, it's my turn to see you."

I reached for his belt and undid it slowly. I never broke eye contact with him. I wanted to watch his reaction and wanted to make sure that I was not pushing him too far. With his jeans still buttoned, I lowered my face to his groin and let out of breath of hot air. Matt just about jumped off my couch.

"Too much? Want me to slow down, or stop?" I ask, already knowing the answer.

"No. No please don't stop . It just felt too good." He said.

"Then come back down here and let me treat you." I smiled.

He eased back down and I continued my assault with his pants still buttoned. His cock grew and pulsed with each breath. I couldn't wait anymore. I HAD to have him in my mouth.

"May I?" I ask him as I start to unbutton his jeans.

His boyish grin took over his face

"Really?!! Fuck yes!! My friends all said this was the best thing ever and I always just laughed and played along, I have never had a blowjo..." That was all he could get out. I had his pants down and his prick in my mouth before he could finish his sentence.

There was precum dripping from the tip. I made sure to lap it all up. Every muscle in his body was tight. I slid my tongue down his thick shaft and wrapped my lips around him on the way up. I had barely started sucking his cock before I could taste more than precum and I heard Matt start to stutter.

"Umm Boss Lady...Uhh Oh Fuck.. You ...Need to Uhhh. Oh nooo. Uhhhhhh" He attempted.

It was too late for him to stop and I knew it. Cum spurted from his cock in giant squirts. He tasted so sweet and salty. A hint of musk and sweat tickled my nose. I knew, at this point. he would become very sensitive and slowly eased my assault on his meat. When he had emptied himself in my mouth, I moved my kisses from his spent member, moved up his chest and into his neck.

"Holy Fuck that was amazing. I never realized how good that would feel. I'm sorry I didn't warn you sooner. I couldn't talk," he panted.

"It's ok Matt. I love the way you taste." I said wiping my lips, "And it was my intent to make you cum in my mouth. Now, do you think you can handle more or should we continue another night?"

"I'd like to return the favor if you don't mind. Can we move to your bedroom though?" He asked.

"Yeah, come on I'll show you to my room." I take his hand to help him up, and he slid his jeans back over that perfect ass.

I was so wet that my panties have a spot on them. We enter my room and I lead him to my bed. He begins to kiss me and run his hands over my body. He is getting really good at kissing me in all the right places and with the right amount of pressure. His hands are becoming a work of art as he works my body into a fury of desire and lust. I work my hands into his jeans again and slide them down his thighs. He steps out of them easily and his penis begins to swell with the new sensations. I noted his quick recovery as a positive sign, consideringhis age.

As we kissed he pressed his hardening prick into my stomach and ran his hands down my sides to my panties and stopped. I took his hands, laced his fingers thru mine and slid my panties down my thighs. His hands instantly went to my ass. He grabbed my ass and pulled me even tighter against his body. Here we were naked, together and adrenaline pumping. I slid my hand down to his cock and felt him stiffen even more. How is that even possible? This boy is ready for round two. He throbbed under my hands.