A Freshman's Summer Class Ch. 08

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

We Continue from where we left off with our brave hero, as his adventure continues during his summer of higher education learning! This is a continuing series I'll be releasing as my busy editor(s) help me clean up my keystrokes of mess.. Much thanks goes out to them, as the editor(s) that helped will be listed with each chapter. Thanks gang!

Edited by HotandHollow

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It was Sunday morning at Ms. Kelly's. I was asleep in my pink bed with Mark next to me, both of us completely drained and tired from Saturday's fun. Ms. Kelly and her guests were so much fun to meet, and they opened doors in my mind, bringing pleasure to my life that I never knew before. I was addicted to all this pleasure now, addicted to pleasing others. It just felt good and right.

Case in point, as I started getting myself up, I felt something hard and hot rubbing against my thigh. I knew it was my sleeping best friend's cock. I re-positioned myself and started sucking it without a second thought. I wanted to re-experience that feeling of a cock getting so stiff in my mouth, with imminent signs of cum blasting forth, that I just had to feel it again.

Mark woke up, naturally, and helped me with a hand on my head. He positioned it at the back of my mouth and started pushing into my throat. It took a few minutes of trying for my gag reflex to stop anticipating it, and eventually it popped into my throat. Wow, what a feeling of accomplishment, I thought...as I suddenly realized I couldn't breathe with a cock stuck in my throat.

I almost started laughing then, like a dumb bimbo slut, but I just pulled his cock back to my mouth. Finishing him off, I swallowed about half his cum, then moved up to share the other half with him. We made out for a few minutes, smiling at each other afterwards.

We immediately went to the bathroom and cleaned up for the day. So many signs of yesterday's escapades on our bodies and on our breath, it was pretty gross to be honest! Getting dressed and downstairs we made coffee and breakfast for Ms. Kelly and ourselves.

As our Mistress came in the room, we both smiled and moved over to welcome her. Hugging her, kissing her cheeks, and then sitting down like good obedient daughters.

Ms. Kelly started the conversation, right to the point, "So, Alli, did you tell Marcie how much of a sissy slut you are? How being filled from both ends made you shoot your cummies all over your bed? A cock sucking anal sissy slut at that, huh?" She giggled as she took a bite of her toast.

Marcie actually answered before me, "Well, she woke me up by sucking my cock, so I'm going to guess Alli loved it all! Maybe I can try out your boi pussy sometime?"

I was so embarrassed...I think. My stomach was full of butterflies, and I think that's embarrassment, right? I wasn't sure anymore. It could have been excitement for what I did, for getting more of it, for letting Marcie fuck my boi pussy too...I wasn't sure anymore that I had any lines left to cross. I was getting so much pleasure from all of this, and every new thing proved to be something I wanted all along.

Truth be told, as much I was thinking about my best friend fucking me, the soreness and pain from the previous day back there reminded me that wasn't going to happen, at least not today.

The rest of the morning we spent cleaning up the house, then changing back into our (mostly) boy clothes and heading home. I thanked Mark and Ms. Kelly profusely, and clearly they knew I would be up for anything after all that. We all shared smiles, laughs, and a few kisses before going our separate ways. Mark told me he would see me at 7 like always.

The week went by like usual, at least if usual meant I was sucking my best friend's cock every day. Every morning he picked me up as usual, but my breakfast consisted of drinking his cum. I liked it and was seriously thinking how enjoyable it was to have a cock between my lips and cum in my belly. I was clearly addicted to pleasing Mark, and he had no complaints.

On Tuesday he gave me a gift after I blew him. I deserve gifts for doing nice things, I thought! And a nice gift it was, as Mark gave me my very own vibrator dildo. It was lumpy, and about five inches long, and had a dial at the bottom that you could amp up the vibrations. I kissed him as a thank you, telling him how I would be shoving it in my boi pussy as soon as I got home. He probably should have given me that gift on the way home, as the workday seemed to drag on forever, thinking about plundering my asshole with my new toy.

I didn't waste much time once I did get home. Forgoing dinner, as I'd stopped eating solid foods, I only drank these shakes that Ms. Kelly gave me. She said it would help me lose some weight, which sounded great to me.

Anyways, I got to my room after my shake and shower, and immediately began pleasuring myself. Sure, it was nice to run my hands over my body, but I was getting the most pleasure now from tugging on my nipples and shoving things in my boi pussy. I started by sucking the vibrator and pulling on my nipples before moving the dildo into my ass. I had to ball up my panties and stick them in my mouth each night, as otherwise my parents would think I was dying in here!

So here I was, with my new normal, fucking my ass until I came before falling asleep. No more videos, no more audio files for me. A swift vibrator to my pussy had cum flowing like a river out of my little dicklet in no time.

A few weeks went by like this before Ms. Kelly had us over again for a weekend. My summer was getting close to being over, and I wasn't sure what I would do once I returned to college. I would have my own studio apartment this coming year, so that was a comfort that I didn't have to share a dorm room.

But what would I do without my best friend's cock in my mouth every day? Without my Mistress and her friends to pleasure?

It was approaching the end of July. I had subsisted off of Ms. Kelly's health shakes for almost three weeks now, and they clearly were having an effect. My legs were getting skinnier and toned, my abdomen was almost muscular, with just a touch of softness over the muscles there. My arms were leaner. The only place where the fat seemed to stick around was under my nipples, as small breasts could now easily be felt by hand, and my ass itself seemed bigger. I chalked that last one up to my legs and abdomen thinning out, giving an appearance of a derriere.

I noticed over that time that my dicklet no longer tried to get hard in its cage anymore. Even when Mark or Ms. Kelly would remove it for cleaning, my little pee pee would just sit there and not even try to get bigger. It was pathetic at this point, maybe sticking out an inch from my body, two balls beneath it that looked large at this point in comparison to the one-inch wonder above them.

It didn't seem to bother me, as I was getting all the pleasure I wanted simply by fucking my boi pussy or sucking on Mark's cock. It's not like I used my dicklet for anything other than going to the bathroom. It never worked well enough to please a woman, so my body was just adjusting to that new reality, right? That seems like a completely normal thing, once you realize your dick, err, pee pee, isn't good enough for sex, then it should just stay small and cute!

The skin on my face and body cleared up a lot too over those weeks. I didn't have pimples or anything, just seeming to be softer and more feminine now. I would spend hours just smoothing my hands over my body, exploring these new feelings and sensations.

My parents did tell me at one point they were worried about my weight loss, but I told them it was no big deal, I was so fat from my freshman year, I needed to lose some weight. I reassured them that when I got back to school, I would lift weights to put some muscle on, that all this weight loss was from the shakes and working outside all day. That seemed to calm them down, mostly. I think they may have wanted to comment on how I acted far freer now, with my long hair, swishing hips, and effeminate movements, but they didn't want to broach the subject. I had a feeling they didn't want to be the parents that ruined their son's life by hating his sexuality.

I knew they knew at this point. I wasn't hiding anything in my room anymore. Panties, bras, hosiery, and even my toys. My mom had to have seen them by now and must have told my father. But they were so trained not to be upset about those things by society, that they didn't want to be the parents who shut out their kid, etc., that they just accepted things, it would seem.

The next day it was raining, so I didn't think I'd have work. I texted Mark to see if he wanted to hang out, and he mentioned we can go work indoors for a client instead. After picking me up, I moved to suck Mark's cock, but he stopped me. "Hold off for now, bud. Let's see about this client first," he said.

After about fifteen minutes, we arrived at a small building along the major shopping strip in our suburb. It was mostly stores and car dealerships, and we pulled into the adult store lot. Excellent, I could find some new toys before we went to the client.

"Well, we're here," Mark said. "Grab the tool bag out of the back. They have a few things we need to fix up inside."

Entering the front door, we were greeted by a fantastic site. Sandra, Ms. Kelly's friend, was beaming at us as she said hello and welcome. I hadn't seen Sandra since I sucked her cock and ate her cum while Mrs. Whitehall fucked my boi pussy. My mouth started producing a lot of spit for some reason, well, the reason being because I thought about sucking her cock.

"Hi, bois! Thanks for coming over today. So, Alan, just F.Y.I., this is my place of work. I happen to own this chain of stores here in town. Yup, I peddle smut to the masses!" she said, laughing a bit at her little quip.

We spent two hours fixing lighting issues throughout the store. Most were just bulb changes, and the others needed new ballasts or dimming switches installed. Didn't take much time.

"All done? Awww, I like having you bois here with me. Alli baby, you want a tour before you go? Maybe you'll see something you like?" Sandra inquired. I quickly agreed, as spending time with Sandra was paramount in my mind.

Sandra suggested, "Mark, why not go hang out in the booth while I give Alli the tour?" Mark nodded and went off to the back hallway. Sandra told me she would show that as part of the tour.

As we walked around the store, she showed me the volume of porn DVDs they had for sale, and explained they were all sorted by kink or fetish. She showed me a few specific offerings: one from the female domination section, one from the trans/shemale section, and a third from the feminization section. I wanted to take all of them, but let's be honest, with the internet, I didn't need DVDs. Sandra swore people still bought the hell out of them though, turning her a nice profit.

Sandra led me to her massive selection of dildos, butt plugs, pocket pussies, chastity cages, lubes, and various other sex toys. It all looked awesome, and I spent a few minutes fondling all the big dildos on display.

Sandra blurted out toward a coworker, "Hey Mike, mind the front while I show my guest the back, please!" The dude grunted in response, with a curt nod. He was in leather and looking a bit goth to me, not judging though, really.

Sandra took me delicately by my hand and led me to the back. There were four doors along one wall, and two on the other. The two doors were clearly the bathrooms by their signage.

The four doors on the other side were different though. The first door's sign read, "Employees Only." The second, third, and fourth doors all had keypad locks, and a light above each door. Currently, the second and third rooms had green lights glowing above their doors.

"If I know Mark," Sandra explained, "he is in the second door. Usually, when the light is on, you can't enter the room, but I know the master code, so I get to go in."

As we entered the dark room, I noticed a few things right off the bat. First, the room was about five feet wide and eight feet long. It had a window at the far end that looked into a space that was dark, and a flat screen TV playing porn. Second, the room was dark, with barely any light, just enough to see. There were no soft surfaces, everything was hard and industrial looking. I assumed to make it easy to clean, as I knew what a jerk off booth was.

Lastly, I noticed that there was a cock sticking through a hole in the wall, and Mark was kneeling on the floor sucking it.

Sandra closed the door quietly behind us, as we stood there, her back against the door, my back against her. We watched Mark work that cock with his mouth, him voluntarily grasping his hands together behind his back. He clearly heard us come in but did not stop his work on that dick in front of him.

As it got more intense, I was getting excited. Sandra's hands were moving up my sides and found their way to my chest where she massaged my tits and pinched my nipples through my shirt. Being turned on in this manner had my libido revving up, and I started humping at the air, pushing my backside into Sandra's crotch. I immediately felt her growing hard in her pants, and the images of her magnificent cock sprung up in my mind.

This went on for a few minutes, when Mark finished off the cock in his mouth, as it started shooting cum first in his mouth, then on his face and chest when he popped it out of his mouth. The softening dick withdrew into the wall, and Mark slid the towel dispenser back over the hole to hide it. That's pretty smart, I thought, don't make it too easy to tell what happens in this room.

When Mark stood up, I could see he was naked. He gave us both a look before sitting on the countertop at the front of the room. He spread his legs and sat back against the glass.

Sandra purred in my ear, "Let's have some fun now, sweetie. Time to get to know each other better!"

I didn't need convincing. She guided me forward as we slowly moved toward Mark. Clothing was stripped off as we went, taking what seemed like hours to walk the six or so feet separating us. By the time I reached Mark, I was nude. I simply bent over at the waist and started sucking Mark's cock then and there. Sandra held my hips back and up, so I knew to bend at the waist, exposing my boi pussy to her. She really didn't have to help; I knew what I wanted to happen! With a slow and tender movement, Sandra removed my plug and set it aside.

Sandra surprised me then, as I felt her hot breath, and then her devilish tongue start working over my boi pussy. I had given a few rim jobs and enjoyed them a lot, but never having received one, this was new to me. Fuck was it intense to give someone that kind of access to yourself. It felt amazing and intimate in ways I hadn't felt during all this summer.

All too soon I felt Sandra's sweet mouth leave my anus. It didn't take long for her swollen member to replace her tongue. She'd clearly lubed it up at some point as it slipped right into my pussy. It was nothing like Betty, though. Sandra took it all slow and caring. She was ensuring that I enjoyed it, and enjoy it I did! As I worked Mark's shaft with my mouth and throat, Sandra worked my hole with her shaft. She would go all the way in, and slowly move until she almost popped out. After a few minutes, it was driving me wild.

"Fuck...me..." I said meekly as I tore away from Mark's dick for just a moment.

"What was that, love? I didn't hear you?" Sandra asked.

"Harder! Please, I'm begging you, fuck me harder!" I quickly and loudly said back to her.

Immediately pushing myself back onto my best friend's cock, Sandra clearly got the message, as she picked up her pace, and started really giving it to me. I was moaning and slobbering all over Mark's cock as pleasure started rippling through my body. The three of us synchronized our pleasure, moans escaping both of their mouths at each end of me.

Mark's load filled my mouth, three squirts of thick goodness that I immediately swallowed before releasing his dick. Moans of ecstasy escaped my unoccupied mouth as Sandra was quickly reaching her limit. Just as my orgasm peaked, and droplets of opaque but mostly clear liquid spilled from my caged dicklet, I felt Sandra hilt herself in me, and a flood of warmth fill my belly.

"Oh my fucking gaaaawwwwdddd!" was all I could say. What an orgasm I was going through, my whole being filled with warmth and joy. God, I fucking loved this shit!

Sandra told Mark to clean up the room, as I slowly got dressed. Sandra and I were all kisses and hugs while Mark did the dirty work around the room. I couldn't believe the feelings I had for this woman!

"Alli, thanks for letting me be your first...even though it looked and felt like you didn't even care about that part," Sandra said with a giggle. "I know it was the first real cock to enter your boi pussy though, and that means so much to me. I really like you, Alli...I mean it. You're just so fucken' cute!"

Leaning in, I kissed her deeply, so she wouldn't say more. It was enough to feel that needed, that wanted. I felt so good.

We left the room after a while, the worker up front just giving us a nod and grunt as we came back out from the back. Sandra asked me about going back to school. We talked about how I was nervous that I wouldn't be near anyone from this summer, how it would be lonely. Sandra told me some news that made everything seem like it would be alright.

"You know, well you probably don't, but I have a store up there at your school. I travel to it at least once a month, and I have a few friends in town your age, regulars to the store. I'll see you when I'm in town, and I'll introduce you to them as well. You won't be lonely at school for long!" She finished with a wink. She also mentioned I could work there too and make some extra cash. Sounded like a great idea!

My summer rapidly coming to a close, I was dreading returning to school far less than before. It truly was a blessing to have met the beautiful and enticing Sandra. I had to admit that there were definitely some feelings for her in my heart. I liked messing around with Ms. Kelly, Mark, and her other friends, but I didn't have these sorts of feelings for any of them.