A Freshman's Summer Class Ch. 09

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

We Continue from where we left off with our brave hero, as his adventures at home draw to a summer conclusion! Sorry this may be it for a bit, its very difficult to decide which direction to take this story at now. I mean, can't keep calling it a "Freshman's" anything now that he is a sophomore...I may continue it, I may start something new. Either way, thanks for enjoying my work, and if you don't enjoy it, thanks for reading anyways! All the best, cheers! -CapnSteelBoy

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Two more weeks and school would be getting back under way. I spent most of that time working with Mark, playing with Mark's cock, and heading over to Sandra's place of business. She wasn't always there, and when she wasn't, I would hang out in the middle booth. Mark had taken me back a few times and the two of us would sit on the floor in there and suck off a few strangers before I sucked him off. It was a fun thing to do after work a few days a week.

The other times when Sandra was there, we would repeat our previous encounter for the most part. I would spend time with Sandra alone too, with Mark in a booth busying himself. I got to explore more of Sandra's body in those times, learning every curve, every intimate little detail about her body. She showed me every part of herself, scars and all. I spent much of time learning every inch of her magnificent cock. I knew the path of the veins, the wrinkles of the flesh, the shape of the head. I was confident I could identify Sandra from touch alone.

There were nights with Ms. Kelly as well. She would play with my butt plug, sit on my face, and make me drink Marcie's cum. It was all fun, and I didn't want any of it to end. But alas it had to. So after some good times on my last night with Mark and Ms. Kelly, we were getting cleaned up when she started telling me a few things.

"First, and I'm sure you noticed, but those shakes I gave you are not just nutritional shakes. They have just a little bit of estrogen and some antiandrogens." Ms. Kelly began to confess.

"I figured as much, Ms. Kelly, when my body started developing...well...more feminine traits. Its alright! Don't get concerned, if I wanted to stop, I would have!" I said, pleadingly, to this wonderful woman who opened all these doors for me.

Ms. Kelly looked relieved, saying, "Thank goodness...I was actually really worried my dear! You are so much more than I ever thought you would be, you're perfect! Second, I'm going to remove your cage. I can't send you back to school locked away, it could be dangerous. But I think with the affects of those shakes and your clear development into a butt slut, you won't need it anymore regardless."

That took me by surprise. I barely noticed it anymore, so it wasn't really like I would miss it. I just hadn't thought about it in a long time. She had Mark release me from the cage then, and he worked it free after unlocking it and sliding the sounding tube out of my urethra. I felt relief then, for sure. My little dicklet showed absolutely no sign of getting hard, and that was fine by me. I didn't need it for pleasure anymore. I did stare a little slack jawed at how open my piss slit was. If I pinched the head, the opening seemed to be a lot bigger, like a ballpoint pen could easily be slipped into my pee hole.

"Lastly, you won't need that butt plug either. You can get new ones from the stores near you up there, but I want mine back for my next boi toy project!" Ms. Kelly had said. Mark slipping the plug out of my rear entrance while she said all that.

I really was stretched out good by that point, seeing my ass hole when I bent over and looked in the mirror, or when Mark or Sandra showed me pictures, looked huge to me. It would close, but still looked all kinds of stretched out, like I could fit anything up there. That thought turned me on some. It was looking more like a pussy than an asshole at this point.

We three just spent the night chatting mostly, enjoying each others' company, reminiscing about this summer and all the progress and things learned. I couldn't believe it was all coming to an end, sadness of that reality hitting me pretty hard. I started to cry then, snuggling up to Ms. Kelly, thanking her for everything, and telling her I would miss her.

"Aww, don't be like that dearie, we still have tonight to have some fun together! Besides, I told Marcie she could fuck you before we did all this to you, if you made it to the end of the summer caged! You had to know it was all a setup to turn you into a cock craving sissy slut, right?" Ms. Kelly said between some laughter.

I knew she was right, but I didn't care. What was I before this? Someone who came as soon as his penis touched the outer lips of a pussy. I was pathetic! My small dick would have just been a life of disappointment to any woman I could trick into the sack. Let down after let down after let down would have been my gift to the women of the world. Now look at me, I can have sex when I want, and pleasure people when I want, and cum when I want! My sex life had real meaning now, and I didn't miss the old me one bit.

So with that in mind, I started working my hands on Ms. Kelly's tits, releasing them from their silken enclosure, fondling them, licking and sucking at her nipples. Taking small breaks to kiss her deeply. Feeling Mark's hands on my body from behind as I worked on Ms. Kelly, precum starting to drip from the tip of my dicklet.

Ms. Kelly slid her body down the couch flat, so I could get in position. I kissed my way down her body, licking along between kisses, until I reached her bushy peach. I dove in and performed all the cunnilingus skills that she had taught me, giving her multiple orgasms over the next hour.

At the same time, Mark positioned himself behind me and was sucking my boi pussy while fondling my little penis and balls. I didn't get hard no matter what he did to me down there, but it felt amazing all the same. Having someone eat me out as I was eating someone out was spectacular. This could easily become a new favorite of mine. The feeling of tickles followed by instant pangs of pleasure, allowing someone access to such a private part of me, inside me, brought an explosive feeling of fulfillment and joy.

Eventually he stopped and rose behind me, before pressing the head of his erect member to me. Pushing ever so slightly, he slid in with ease. I was worked open for so long, there was no resistance to cocks like his anymore.

We enjoyed one another for the rest of the evening, eventually all three being sated. Sleep took the two of them quickly, as I got cleaned up and dressed. I walked home that night and slept in my bed. My father would be driving me back to school the next morning.

With just two large ruck sacks and my computer bag, I was ready to leave. Having packed the car early, my father and I had breakfast and left with coffees in our hands. I drove the whole way there, as my dad and I caught up some. My parents were both such good people, and truly cared for me. I was really touched and found myself fighting tears back several times as my dad and I reminisced about my childhood some. Overall it was a great trip, and really set my heart at ease with my dad. I knew he would convey this to my mom, so I didn't have to worry about her either.

I told him about getting a job, and he said that was fine and smart, as long as I didn't work too much. I still needed to do the school stuff first, he would say. After arriving at my new apartment, he helped me upstairs. We met the realtor there who gave me the keys. We stepped inside together, and after about a ten second pause of silence and open jawed looks, we both started laughing.

Good healthy belly laughs. We talked about how lucky I was to get a studio apartment all to myself on the way up, and now seeing the place, we couldn't help but laugh. The room was small, about 15 feet by 15 feet, with an open bathroom in the corner, a kitchen in the other, and a closet separating the two. The rest of the space had a bed, a small couch, and a desk to study at.

"Well son, I guess this is what $1000 a month will get you here in the middle of no where, with only the state university as it sole source of jobs!" my Dad announced, sarcastically.

We said our goodbyes then, dad showing himself out and back to the car. I made the best of my time remaining in the day. Unpacking everything, getting a shower and cleaning up. I went down to the street and found the closest grocery, bought the soy milk I need to mix with my shakes, along with some fruits and vegetables.

I stopped at the book store to pick up my texts for that semester too. Teachers posted their syllabus online nowadays, so you knew what materials you had to buy before the first class. This helped, so I could get the books used.

With all that done, I settled into my new place. Turning on the TV, I watched some music videos, deciding it was a good time to go ahead and relieve myself. I took out the vibrator Mark had given me, got undressed, lubed it up by sucking on it, and went to town on my boi pussy. It didn't take long before a little stream of cum cums dribbled out of my dicklet. I caught it in my hand and cleaned it all up, tasting the devilishly good flavor of my opaque productions. I sent a picture to Mark and Ms. Kelly, wishing them sweet dreams!

I had a few days before classes started, and thought that I would go find Sandra's store tomorrow. I texted her before falling asleep that I planned to stop by it tomorrow and inquire about a job. She texted back that she would call them and let them know I was to be hired, no questions asked.

Waking up that Monday morning was odd. At first I panicked, as I didn't know where I was...remembering after a few seconds that I was at my new studio apartment at school. I groggily made my way to the kitchen for coffee. Sipping it, I surveyed my abode again, trying to see the positives.

First positive, the bed was a queen size. So if I did have company, there was more room for us to play! Second, the bathroom and shower being part of the overall room was really weird, but the positive side, there was no hiding here. I could see my guests go, which seemed real kinky to me! Third, off the kitchen there was a sliding glass door to a small balcony with enough room for two people to stand there and smoke a cigarette. So that was cool!

Alright, positive things, boi, positive things! Time to hit up google maps, see where Sandra's shop was, while I downed a shake for my morning sustenance. I mapped it all out, it was about 10 blocks from my place, as google said it was about half a mile. I hit up a coffee shop on the way for some better roast, and made my way down the street to Sandra's joint.

Upon arrival, I noted that the place was supposedly open 24 hours. That seemed a bit drastic, but whatever. I opened the door to the sound of an electric chime in the back room. Out walked a tall brunette with a welcoming smile. She cheerfully greeted me, and said her name was Samantha, but I could just call her Sam. We exchanged pleasantries, and I told her I was a friend of Sandra's from back in the city.

"Oh! Yeah, Sandra did call and let me know you were coming. Its great to meet another of Sandra's friends, she's just the best, am I right?" She said, but it wasn't really a question. "Come on, I'll show you around, then we can talk about what shifts you can work, and stuff. We'll get you in the schedule."

Well, I guess I had a job...never thought it would be that easy. Either way, Sam showed me around the store, it was similar in layout to the one back home. Had all the similar merchandise and even had the booths with the keypad locks and lights too. Sam smiled a knowing smile at me when she showed me the booths. "I guess you already know how those work, huh Alli?" She quipped.

That's cool, I guess I was working as Alli here. That's fine by me, I liked the thought of that part of me being an employee at a smut shop anyways!

"Just remember though, if you're working alone, don't fool around in the booths, ok? Job first, alright sweetie?" Sam stated, again it wasn't really a question.

She was an interesting view, about 5'-8", and very thin, slight. Barely anything there for titties, and just a small bump for a behind. But clearly she had a lot of energy, and was very nice and sweet. I felt we could be friends, her positive attitude was infectious and had me feeling giddy.

Monday mornings at the smut shack were clearly not the prime shopping time, as nobody came in the store the entire time I was there. This was great, as Sam and I just bullshitted the entire time, with 3 hours going by quickly, without either of us noticing. We talked about a lot of stuff, guys, girls, clothes, makeup, the best bars for people like us. Yeah, I said that...people like us. As it turns out, Sam and I are very similar. She is a full fledged, self proclaimed, sissy slut. I am a somewhat closeted sissy slut at this point, but semantics.

We got along great, and really were enjoying one another's company. Sam was in grad school, being 3 years older than me. Had been like this since high school for her. We talked about sex, and chastity cages, hormones, eating habits, cleaning habits, etc.

I couldn't believe it, my first full day back at college, and I already made a friend. A really good friend, who I could talk about things with, explore things with, and all around just enjoy time together with. I texted Sandra a huge thanks when I got home, because thanks to her, I had met a wonderful new friend.

My schedule for the next few weeks at work would be some morning shifts with Sam on Tuesdays and Thursdays, and then full shifts with Sam Saturdays and Sundays. She would show me the ropes, make sure I understood everything the store had to offer, etc, before letting me go solo.

After leaving, I couldn't help but feel excited about what the future held for me. I was euphoric in the knowledge that I had a new close friend at school. I was happy knowing that I would meet more people through Sam, and maybe even have some fun with Sandra too when she visited. Being horny now, my pace started picking up on the way home. My asshole was plugged as usual, and the swing in my step, the swish of my hips, was really working as I quickened my pace.

As soon as the door shut to my apartment, my clothes were off and I was lying on my bed playing with my nipples. Pinching, pulling, caressing the soft flesh around them. I was moaning like a bitch in heat, as I moved a hand away from my chest, to grab my vibrator. Working it all over my pee pee and balls, and quickly down to my quivering plugged asshole.

I saw some porn lately of a few sissy gurls who bent over backwards and played with their pussies to make their cummies shoot directly into their mouths. I knew I had to try it then, so I flipped myself around and moved to the edge of the bed. Leaving my ass on the bed, I sort of slid my upper body over the edge of the bed to the floor and bent myself over so I would be in position. It wasn't the most comfortable position to be in, but I was feeling incredibly horny to be staring at my own dicklet, with my knees being pulled by gravity lower, towards the side of my head.

I used one hand to work the plug in my boi pussy, and the other to push the vibrator around my groin. I felt really submissive in this position, very weak, and that anyone who saw me, would either be disgusted by my weakness, or hopefully, so turned on they would fuck me senseless. The thought of the neighbor or landlord roughly fucking me and insulting me entered my mind, and it drove me over the edge. It started slowly, but my little dicklet did start getting hard then, getting to about 3 or 4" long before it started dribbling a stream of mostly clear cum directly onto my face and neck. I got some of it to land in my mouth, as I moaned in pleasure, eating my cum cums like a good sissy slut, scooping up the rest and smearing it on my nose and into my mouth.

I really was addicted to cum at this point, the smell of it, the taste of it, the satisfaction that submitting to cum brought me. I couldn't imagine life without cum at this point, just laughing at myself from last year, only chasing down chicks. My previous self was completely wrong in approach. Sex was so much easier now, as a sissy slut I thought. I couldn't believe how much more enjoyable everything sexual was now that I was free with it all. The previous me, the strictly hetero me, was just so sad in comparison, being just a complete failure in the sack and more of a porno watching jerk off machine. I was so lucky to have a friend like Marcie and Ms. Kelly!

My school year was looking good so far, with a new friend and a job already! I couldn't wait to see what was in store for me next!