A Freshman's Summer Class Ch. 05

**All characters are of legal age for adult content.**

Thanks for reading and rating, its much appreciated, and humbling to see so many folks enjoy this story. I'm pushing out about 2 chapters a week, and will continue with that pace. Thanks again for reading!

Chapter 5

I awoke the next morning in the pink bed of Ms. Kelly's daughter, images of the night before immediately filling my mind. The familiar tightness of my cage was there, and I ran to the bathroom to relieve myself. I sat down to pee, as the cage necessitated it. I was running my hands over my smoothly shaved body, allowing images of sex and lust to enter my mind. How the hell was I going to look at my best friend after last night? I'm not gay...come on Alan, that doesn't even matter, does it? It felt so good. So right. How am I supposed to function as a human when I'm this horny?

I put on my girly clothes from the night before. A lacy thong, the tight pink cutoff shirt that showed off my stomach area, and small short black gym shorts. The shorts hugged everything tight, and left absolutely nothing to the imagination of the onlooker. I couldn't help but feel a bit sexy in this outfit, as I knew I was cute in it.

Walking down the stairs to the kitchen, you could overhear Mark talking with someone...that being Ms. Kelly! When did she get back? They both noticed me and gave their greetings, Mark smiling at me a little longer than Ms. Kelly. I was speechless, because frankly, I couldn't get sex out of my mind. I just sat there like a doll, eating the food they put in front of me.

"Mark tells me you begged to be released last night, even after pleasuring him? Didn't you want to learn how to pleasure people better? Didn't you want to be a good boi for Ms. Kelly?" she insisted. Hearing those words I immediately went to maximum level of arousal. I was leaking through my panties and the tight shorts in no time. A wet spot betrayed my condition to anyone who saw it! As I panicked and stood up to run out of the house, they both saw my humiliation stain.

"Well my dear, that does look like a problem! You look so cute and pretty, but you're such a horny boi that you leak just seeing Mark...and me? Why don't you go to your room and lie down. Ms. Kelly will come help you in a few minutes. I'll teach you how to take care of such an issue, my dear, sweat, good boi!" she soothingly told me.

I returned to her daughter's room...she called it my room oddly...and laid down on the bed. I couldn't think straight, just thoughts of sex, ass, cocks, chastity cages, dildos, running through my mind. Ms. Kelly came in a few minutes later. She was wearing a silk robe that barely hung past her ass cheeks. It was slightly open, and abundantly clear she was naked beneath.

She sat next to me and whispered encouraging things to me. "Good boi, cute boi. You're so sexy, you make Ms. Kelly all excited to see you dressed up so cute. Don't you want Ms. Kelly to make you feel good and teach you more?" she inquired seductively.

I was learning to pleasure others, wasn't I? I weakly responded with, "Yes Ms. Kelly. I want to feel good. I want to learn more."

I started to breath in a scent that was not familiar to me. I was drawn out of my mental stupor just enough to notice Ms. Kelly was playing with herself. The odor was the smell of sex, her sex, filling my nostrils.

If I wasn't already at peak arousal, the scent of her hitting my brain receptors surely sent me there. My penis was straining against the chastity like never before...puffing, softening, puffing, softening...red and angry. It was almost like it was breathing!

Ms. Kelly's fingers found there way into my mouth, and I tasted her for the first time. It was sweet, and heady. Not bad, not great. But it kept my arousal level maxed the way she just did what she wanted to me...and I let her.

She spoke then, "Good boi, taste my nectar. Do you want to make Ms. Kelly happy? Do you want to learn how to pleasure a woman?"

All I could do was nod while sucking and licking her fingers. She pulled my face to hers and kissed my forehead before pushing down on my shoulders slightly. I knew what to do from all the years of porn watching.

As my face moved down her body, I laid gentle kisses along her. Worshiping kisses on her neck, on her torso, between her breasts, past her belly button...as something then tickled my chin. I kept moving down her body and my eyes were level with a large hairy patch then, as my kisses then were landing on her pussy.

I marveled at the way she kept the hair neatly bound to just above her vagina. It was long and wild looking, until you noticed that she didn't let it overgrow to her stomach or thighs. Smooth there, but large and proud just above her pussy. I was fascinated by this and turned on completely. The tightness in my groin was almost excruciating.

She kept pushing then, and I moved myself between her thighs then. Taking in her scent. I did what I thought was next, and dove on in, face first. Her hand snaked through her forest and spread open her pussy for me. I didn't really know how to do it right, so I did what Mark had told me last year before I went to college, "If you find yourself between a woman's thighs, man, I've heard that you just spell the alphabet with your tongue!"

So there I was, spelling out words with my tongue, pushing as much of my mouthing inside of Ms. Kelly as I could. She was very moist, and her nectar kept flowing onto my face and into my mouth. I swallowed as much as she fed me. I could hear her moans, I could taste her satisfaction, her pleasure.

A small feeling of inadequacy entered my mind as I realized a few things. First, that I couldn't fuck this goddess in front of me, as my little dick was trapped away in its plastic prison. Second, I couldn't be exactly sure if my spelling bee was the source of her pleasure, or her hand was. You see, her hand never left her pussy, and in particular it was teasing her hooded nub that I knew to be her clit. So was my mouth the source, or her own hand? That doubt and second guessing made me feel less a man for sure.

Just as my jaw was getting tired, she pushed my head away from her sex. She moved me to lay on my back then, as Ms. Kelly then positioned herself above me, straddling my face.

"Be a good boi, and keep Ms. Kelly happy, sweetie," she moaned at me from above.

"Yes Ms. Kelly," was all I could muster, as I looked up to stare straight at her ass and pussy above me.

She brought herself down to my mouth again, burying my tongue inside her slit, and pushing my nose into her ass crack. This was all so new to me, and so damn sexy. Ms. Kelly was a goddess, there was no doubt in my mind that I should follow her to wherever she took me.

She leaned forward then, pushing and pulling to get my shorts and panties off. I started losing control of my excitement as she started fidgeting with my chastity cage. YES! I thought to myself, she's going to release me!

Just as my thoughts turned to freedom and release, she started riding my face. Sliding herself from clit to crack along my mouth and nose. I just stuck my tongue out and licked whatever part of this goddess rode along my face. I was tasting pussy. I was tasting asshole. I was loving it all.

I felt the cage release from my shaft at that moment, and could feel my dick spring to life. It was lightly touched and stroked by what felt like just a finger or two. Gently. And thank goodness for that! After being trapped in that cage for what felt like eternity, the feeling of freedom and my level of excitement, it felt like I could blow my load from just a stiff breeze hitting me.

"Good boi! Time for some more fun. You've earned your release for your pretty little penis, and Ms. Kelly is going to give it to you. That sweet reward you've so needed. Rewards are given to good bois and gurls, right Alli?" Ms. Kelly seductively asked of me, staring into my eyes after climbing off my face, boring into my soul with her question.

"Yes Mistress!" I yelped in reply, calling her what the boys in my videos called their madames. Completely ignoring her calling me Alli. I didn't care, I just wanted to cum so badly!

Ms. Kelly moved on top of my penis then, smooshing it between us, as she put her pussy on top of my cock shaft. She rocked back and forth and the feeling was overwhelming! I thought I would be able to last longer after training myself, but I was clearly going to blow my load at any moment.

Just as Ms. Kelly positioned my cock to enter her hot moist outlet, I started cumming. It felt like it lasted a full minute, as my body spasmed and I groaned uncontrollably. I was slowing down as I felt Ms. Kelly move up my body, and she immediately put her pussy to my mouth again.

"Clean me up now, my little early shooter!" she giggled at me, humiliating me back into my useless cock mind, as again when presented with fucking a pussy, I blew my load on contact.

I licked all around her snatch, cleaning my cum from her lips, from her hair, from her thighs...god, I sprayed a lot. Licking it all up and swallowing was all I was good for beneath this goddess...beneath the owner of my pleasure. She released me and all my penis was good for was shooting its load. I failed again at pleasuring a woman with my penis...but I was pretty confident I gave Ms. Kelly some pleasure with my mouth.

As I finished cleaning up Ms. Kelly's pussy, she cleared up how I was doing in my training. "Clearly you're little pee pee isn't going to be doing any pleasuring, my cute little Alli. Right? But you're mouth does show promise. You did good, little gurl, that's why I let you have release. I was hoping you could fuck me real good and long...but alas, my little Alli isn't meant for that kind of pleasure, are you, sweetie?" she inquired, devilishly.

"I...I...I'm sorry, Ms. Kelly. I thought my training was going well. I'm so...so sorry. Please give me another chance to please you with my pee pee!" I replied, stammering, even referring to my dick as a pee pee...what the fuck was I thinking?

Mark walked in then as Ms. Kelly continued to berate my penis' performance. Mark had a warm wash cloth and was cleaning up my genitals. It felt nice, but my dick was just not responding due to the assault I was mentally taking for failing to pleasure with it. I felt Mark repositioning the chastity cage over my pee pee then, and locking it back into place. This was my new normal, I thought to myself.

"Marcie, did you bring the other tool I asked for?" Ms. Kelly demanded of Mark.

That was weird, did she just call him "Marcie"? Like a girl? Is that like "Alli" to me, my girl name? I was conflicted and in mid thought when I felt Mark pushing my legs up toward my shoulders.

"What are you...?" I started to stammer, when Ms. Kelly put a finger to my mouth and shushed me.

Ms. Kelly continued to me then, "This is your next step in training, my sweet Alli! You're so cute and pretty, but you're not good at sex, are you sweetie? No doubting that now. I tried training you, and all you could do is shoot your dirty cum cums on my pussy. You didn't even make it inside me! Its pathetic!" Giggles filled my ears then as well.

My heart sank at those words, because she was right. That's twice now I couldn't handle a vagina with my dick...my...pee pee. Ms. Kelly wasn't lying to me, she was just stating facts that I knew to be true.

"So sweet Alli, now we have to train you in other ways. Its exciting, really. You'll be able to give pleasure in new ways soon, and we won't have to worry, or care about, you're little pee pee. You won't need it!" She laughed after telling me that last part. My heart sank at those words...

Ms. Kelly continued then after her laughing died down, "Mark told me how much you like getting pleasure from your boi pussy, so I'm going to help train you more down there."

"But...but Ms. Kelly, it was the cage that made me..." I started defending myself with.

"Oh shush now, or I'll gag you! Why do you continue to lie to me? Mark told me all about your slutty backside in the tub lastnight. We both know, so stop pretending now that you shot your dirty cum cums!" She berated me.

And it worked. I clammed up then, just sulking in my humiliation. It was bad enough that it was all true about how I acted with my best friend in the tub, but it was more humiliating that more than the two of us knew about it now. This woman had me defeated mentally at this point.

She sighed a bit, then smiled at my acceptance then. Ms. Kelly then continued, "This is a butt plug, a small one, yes, but its a start. I want you to keep this inside you at all times, except when you're having a movement or cleaning up back there. Don't forget to keep the plug clean too!"

With that she took the device she was waving in front of me, a shiny chrome thing that looked like a playing card's spade, but three dimensional. It had a point and grew larger before suddenly tapering down to a thin portion, with a jeweled end cap on it. I saw her lube it up and then she positioned it to my asshole and started pushing.

Its an odd feeling to have something put in your butt, when you're used to things just leaving it...but just like my finger the night before, it slowly made its way inside. I could feel the swollen portion as it started stretching me out, somewhat painfully. It was more a burning sensation than anything, with a small ping prick of pain as it moved inside me and seated itself into position.

Ms. Kelly squealed with delight at how cute I was, and Mark just stared at my jeweled asshole with...well, with a look that seemed of hunger. The feeling of fullness kept me occupied some, and oddly enough I could feel my cage getting tight again. This was definitely turning me on to be used and stared at like this. I was so humiliated at my failures, all of them forefront in my mind at this point, but somehow I was still getting turned on. My mind was a mess!

She handed me an ipad then and a pair of headphones. "Here you go Alli, just lie here and relax. Watch these videos and sleep if you need to. Get used to the feeling in your rear, enjoy it," Ms. Kelly instructed me.

They both left the room in each others arms, as I was left alone on my pink bed, with an instructional video now playing about performing enemas. I had never heard of this before...so I watched intently to learn new things. I thought I would find this stuff gross, to be honest. The truth is, I found it fascinating. I did have this new feeling of wanting to be cute and pretty, and keeping myself clean back there seemed like a natural thing to want.

After that video, and learning the ins-and-outs, the how-tos and how-don'ts, I felt like that was something I could handle doing every morning. The video said that changing a diet to softer foods, less food in general, would make the process super easy after a while of a more restricted diet. I would just have to get up a little earlier each day.

The next videos I watched were like my normal porn at this point. Mature women in what I now knew to be wearing latex outfits of various coverage, where working on their boi toys. Their young men and pretty feminine boys, teasing them, driving them crazy, and then making them earn release.

I fell asleep while the videos continued playing.

The next morning I was awoken by Mark, well, by Marcie. Marcie was wearing white lace lingerie...the full getup. Bra, panties, tights, and a garter belt. There was not much masculine about his appearance...her appearance...except for a slight bulge in the front of the panties.

"Come on Alli, I'm going to help you with your new morning routine so you can do this every day from now on. You're going to love it, I promise!" Mark said in a bit of a high pitch voice.

He took me to the bathroom then, helping me out of my clothes. Again, this was nothing new and I started really enjoying being undressed by someone else. The smoothness of my hairless body had increased my sensitivity, making me crave the touches from others. Marcie knew this, and really could work me like putty in the hands of an artist.

That was about it for anything sexy that morning. Remembering the enema video, and now Marcie producing two products for me to use, pretty much made this anything but sexy or cute.

The first item was a large blue rubber bulb, with about a 4" tube on the end with little holes in it. Marcie explained this to be an enema bulb and applicator. I just needed to fill with water solution, lube the tube tip, and push it inside myself. Squeezing the bulb made the water flow out, and wash me all up on the inside.

The second item was something metal, stainless, and longer with a hose attached. This one Marcie explained, was attached to the shower head in a shower. This one was for big cleanings, as the amount of water was easily more...but being in the tub made it super easy to use and clean up after.

He told me there was one already hooked up to the shower here, and I should use it whenever I stay over Ms. Kelly's house. The two he was showing me I should take home to use. Great, something else I need to find a place to hide from my parents.

For the next 30 minutes or so, Marcie and I worked water inside of me, and I expelled it. He let me do it myself and just offered directions, tips, and advice. I'm going to leave the the rest of the description out, as a boi like me shouldn't talk about something so un-cute!

After getting cleaned up, Marcie proffered a set of lacy lingerie for me to wear. It was pink, apparently my new color. Just like him now, I was dressed up with sheer stockings held up by a sexy lace garter, bra and panties completing it. It was very exciting, again my sensitive skin loving the tight contact.

We marched downstairs then to the living room to find Ms. Kelly watching the news. She was dressed in full business wear, and clearly was going to work soon. Sitting down on the couch beside her, she smiled adoringly at both of us.

"Oh how sweet my gurls look! You both look so cute, I love it! Marcie, Alli, aren't you happy to make me happy? Doesn't this make you feel good?" Ms. Kelly inquired of us.

Nodding our heads, and whimpering out little, "Yes Mam's", almost simultaneously. Smiling then at each other, as we sounded like twins.

Ms. Kelly continued then, "Alli, this is how you will be when you stay at my house from now on, ok? I want you to dress as pretty as you can, with anything you find in this house. If there's something else you wish to try on, just ask and I'll buy it for you, my sweet gurl."

"You can wear your gross boy clothes out of here if you want, or while you're working, but make sure to wear your panties and bra at all times! And remember what I told you about your new toy!" She reminded me then.

Ms. Kelly closed with, "I have to go now to work. You two have fun today all you want. Allie, its a good chance to ask Marcie all about pleasuring me, and how you can be good at pleasuring me and other women too if you put in the effort."

She left then, Marcie and me just lounging on the couch next to one another. I didn't know what to think at that point. Marcie could sense this it would seem, as he started telling me a few things then.

"I know it probably feels weird to be dressed in only lingerie, I know how I felt at first. You get used to it, and as you probably already noticed, it feels really good to be dressed like this, tight fitting against sensitive skin," Marcie explained to me.

We sat and talked for about an hour about his time under Ms. Kelly's tutelage. How he was just like me, but wished he had someone else to walk him through these early steps. I was enraptured with his tale. It was such a turn on to me, images of those women dressed in form fitting latex using their boy toy's rear entrance racing through my mind as Marcie told his tale.