A Freshman's Summer Class Ch. 04

Story Info
A college freshman's summer in learning new things!
3.1k words
4.62
27.9k
25

Part 4 of the 9 part series

Updated 06/10/2023
Created 04/24/2020
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

Edited by HotandHollow

**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 helpful editor(s) help me clean up my mess.. Much thanks goes out to them, as the editor(s) that helped will be listed with each chapter. Thanks gang!

Chapter 4

Another morning, another day. Waking up, I did feel a little regret. I shouldn't have these thoughts about Mark. I decided to stop looking at his body and try to avoid these thoughts. All the same, I still pulled a fresh thong into place, then some shorts and a tank top. I ran out the truck, on time, with my Pop Tart and coffee.

"Hey man, you look like you got a good rest. Ready to work?" Mark asked as I climbed in the passenger seat.

"Sure, bud," I replied. "Slept like a baby."

Mark shook his head a little and said, "Look man, don't feel weird about yesterday. We both like to wear panties, it's not a big deal. If you decide you really like it, don't be afraid to ask any questions, or for more. My sister has left so much stuff at home, she'll never miss any of it. You could try those stockings next, or even a bra if you want! No one would know but me. Hell, I'll wear the same stuff too if it makes you feel better about it. But you should probably shave before going that far. Or wax. I can help you if you want. Some spots are hard to reach. You can help me too, in return!" He was excited now.

My plan to ignore Mark's body lasted a whole three minutes, as thoughts of us shaving each other flooded my mind. You've got the willpower of a priest, Alan. "Look man, I like hanging out with you — we're best friends after all. But this is all so new to me, these feelings...uhm...I mean, like wearing these panties has been fun, but this cage...the chastity cage...it's really tight now, and I can't stop thinking weird thoughts. I think I may need your help getting Ms. Kelly to let me out," I pleaded to Mark, whining a bit.

"Sounds like it's working then, man," Mark replied. "Look, keep going for a few more days and I'll take you back over to see Ms. Kelly. Besides, she's still out of town, so nothing we can do about it for now." He had a point. It's not like she was home anyways.

To work we went. I tried to focus on my work as best as I could. It was hard, and Mark definitely saw me grinding my backside against a few things. I can only imagine how silly I must have looked, but I was so turned on all the time now I didn't care during my search for pleasure.

He made a phone call after lunch and I could tell he was talking to Ms. Kelly. They spoke for about five minutes and Mark came over to me to discuss what they talked about.

He said, "Ms. Kelly said she was so happy you were still going, watching the videos, and using the audio files. She said while she is away, we can use her place to hang out and drink if we need a break from our parents. She said there's food in the fridge — behind the beer. Haha!"

So after work, that's where we went. No young man could turn down free food and beer, it's in our DNA! After we ate and had a few beers, we moved to the living room couch where Mark served me a fresh glass of beer. We watched some TV for a bit while bullshitting a little.

As my beer got close to empty, Mark asked, "So, want to go ahead and shave some of that nasty hair off your body? Be smooth and sexy like me, bro? Ms. Kelly loves how smooth my body is...can't keep her hands off me!"

Intrigued by it all, and how I felt so loose after those beers, I said, "Why not?" If it works for Mark, it will work for me, I thought. Mark jumped up, excited. I giggled at his level of excitement. I guess I was excited too.

We both ran up to Ms. Kelly's room. Her room was so nice, and smelled so good. My mind immediately went back to my first trip there, where Ms. Kelly had sucked my dick and made out with me, feeding me some of my own cum. I even thought closely about her making out with Mark too, knowing he was tasting my cum as well. My cage started to get real tight.

"Stop spacing out, and take off your clothes already," Mark chastised me. Feeling completely normal with being nude around Mark at this point, I peeled out of my clothing, and stood there with only my plastic prison around my dick covering any part of me. Mark undressed too, wearing just a pair of panties.

His cock was hard again, like the day before. As I looked back up to his face, I saw him smiling again. "Go ahead into the bathroom and get the water going, I'll help you out since this is your first time. And help with the hard-to-reach spots," he said. Mark stayed behind in the bedroom, laying out a bag's contents onto the bed.

Walking around naked with just my best friend around wasn't weird to me. I felt a little pride for some reason in my ability to see it as normal and fun. I got the water running in the bathtub to a nice hot temperature, dropped some of the fruity smelling soaps into the running water so it bubbled slightly. I got in and started washing myself with a scrub rag and body soap.

My back was to the door but I heard Mark enter the bathroom. He knelt on the floor outside the tub behind me and handed me some shaving cream and a pink ladies razor that must be Ms. Kelly's. He said, "Go ahead and get started lathering up your chest and arms." He got some music going.

I thought he would play some rock and roll or whatever, but it ended up being calming music, like the audio files Ms. Kelly had given me to help me sleep while in chastity. It was relaxing, and kept me feeling pretty good.

There isn't a lot of body hair on me, to be honest, so after lathering up my chest and shaving it, and then doing my arms, I thought this was going to be nice and easy. Mark helped do my back, telling me we should shave over every inch just to get it all, even if my back looked pretty smooth to begin with. He lathered up all the way down to my ass crack, and shaved just as far. It felt pretty good when he put his left arm on my shoulder, or my side, or my waist to hold me still while his right hand worked the razor over my sensitive skin.

When he finished with my back, he told me to go ahead and sit on the edge of the large soaking tub so I could start working my legs. As I sat on the edge, I got my first view that Mark was actually completely naked. His dick was sticking straight out and up, bobbing as he moved. A feeling crept into my stomach. I thought it was nervousness...but being honest with myself, it was excitement.

He had no hair anywhere on his cock or balls, and it looked so cute to me. Mark caught me staring, again, and smiled. I wanted to look at it more, but was too embarrassed under Mark's gaze, so I got to work on my legs. Mark gave me tips as I went along: which direction to go, to not go over anything that doesn't have shaving cream or soap covering it, and other tips to avoiding razor burn and cuts.

I was appreciative of the advice, I didn't want to fuck this up. I wanted to look as good as Mark does when hairless and smooth. Cute and hair free, smooth and sexy. I was panting slightly as my sexual excitement level was ratcheting up from being naked with my smooth and hairless best friend. We would look so pretty next to each other when I was done!

When I finished with everything within reach, I tried to hide my newfound excitement at the thought that now Mark was going to help me with the hard-to-reach spots. He'd already done my back, so that left behind my balls and my ass. If I hadn't been in chastity for almost a week, if I hadn't been wearing sexy panties, if I hadn't been drinking all night, and lastly, if I hadn't been playing with those two spots to give myself pleasure, I'm pretty sure I wouldn't be doing any of this, let alone being excited at the thought of someone else touching those spots.

I sat there, nervously waiting for Mark to give me direction.

"OK, you ready for the fun parts? This is going to be weird the first time, at least it was for me, but I'm here, bud. I got you. So go ahead and get on all fours, facing away from me," Mark directed me.

I complied, probably a bit too quickly, betraying my excitement. He had to know how excited I was to feel someone's touch, but I didn't care at this point. It didn't lower my excitement at all when Mark climbed into the tub behind me, the exact opposite to be honest. I was panting slightly at this point with the lewd thoughts of Mark sitting behind me, his face probably only inches from my asshole. Mark finally spoke, "You are so going to owe me after this, man. Big time."

"Anything," is all I could muster in reply. I sounded like those horny sluts in all the porn I've watched. Shit! I'd probably be better off having said nothing...

Then Mark started. I felt him pour warm water over my ass, trickling down my asshole. I could feel my pucker flinching like when I rubbed my finger over it. I was excited for more.

"Here, push your back down so your ass sticks out more, it will make this easier for me," Mark instructed, while pushing down on my lower back with his hand. "Now move your legs apart more," again he said while pushing my thighs apart slightly.

As he smoothed shaving cream over my entire behind, I felt the razor glide over my upper thighs and ass cheeks. He then moved to between my legs, behind my balls, slowly applying shaving cream to my sensitive areas. Electric bolts crashed up my spine as Mark moved my balls and caged cock out of the way of the razor. He washed it all off and ran his hands over my ass checks and taint. I was open-mouth panting at this point.

"OK, time for the hardest part. I'm going to apply the shaving cream and shave your ass crack now. You ready, bro?" Mark queried.

"Uh...yeah. Yes. I...I'm ready," was all I could muster, sounding faint and weak. I was in such a state of compliance, I'm surprised I didn't say anything more embarrassing!

I yelped in a high-pitch voice when his hand spread shaving cream in my ass crack and on my asshole. He really was working the lather up. It was driving me crazy, and my body on its own started humping back onto his hand. "Calm down, you fucken' slut," Mark said, followed by a hard slap on my ass cheek. A second high-pitch yelp escaped me.

Mark shaved my ass crack and around my asshole with some speed. I felt cheated when he was done. I wanted more. I was happy to be on all fours in water, that way no one could see how much precum I exuded thanks to the water in the tub. In my mind, it was gallons.

Another slap on my ass followed by Mark saying, "OK, all done! I think it looks great, bud. I think you look real...cute too...," he trailed off.

I started to stand my upper body up off my hands, and sank down into the tub to sit in the water. When my ass came down, I was sitting right in Mark's lap, his cock trapped between my ass and his abdomen! I stopped dead, "Sorry man, shit...I really didn't think you were right there. I'm real—"

Mark grabbed my waist and pulled me down tight against him as I tried to get back up. I was off balance and fell back down on his cock again. His mouth was right next to my ear, and he hissed at me, "Just go with it. I know you like the feeling back there. I saw you humping back at my hand like a thirsty slut. Go ahead and start grinding, just like you know you want to!"

I was frozen in place at those words. Did I want to? For the reasons stated above, you're damn right I wanted to. I was craving a foreign touch to my now overly sensitive and hairless body.

After jerking off every day for who knows how long, it only took me a few days in a chastity cage to be looking for any sort of outside touch. My mind was so fogged with the search for pleasure that I didn't even care or think about sexuality, right or wrong. I was laser focused on pleasure, and pleasure alone.

So there I was, pulling forward, pushing backward, over and over, while sitting naked in a bathtub, on top of my best friend's lap. Not to mention, just like in that video where I ate my own cum for the first time, I was now the one with the smooth legs and ass that was hot-dogging a hard cock.

It felt amazing to feel something rubbing across my asshole, filling the space between my ass cheeks. It was hard, yet soft and smooth in the bathwater. I swear his cock was two-hundred degrees it felt so warm! There was a fire back there, of passion and need. I didn't care what this was, I just needed it then and there.

Mark was whispering things in my ear the whole time. He would say, "Yeah, ride it!" or "Get on it, push it real nice and smooth!" and "God you're ass feels amazing, you slut!" Along with other degrading things, making me feel like a piece of meat, a lesser being, but I didn't care at all. It added to the intensity of my arousal. Surely, I was filling the tub with precum at this point.

Finally, after who knows how long, Mark grabbed my hips with both hands and pushed me down hard. He was grunting in my ear about taking his load or some such, as I sensed him spraying me with his seed, the water we were sitting in making it impossible to feel it.

"Mark, you have to help me...please! Get this cage off me, I'm gonna lose my mind!" I pleaded. I prayed for his help.

Mark was still huffing a bit after his climax, but responded with, "No can do, bud. I promised Ms. Kelly you would remain chaste. Damn, you got a cute butt. You should always wear thongs."

WTF, was all I could think. Is this happening? Did THAT just happen? What the fuck am I going to do now? What does this even mean? My head was swimming with questions, concerns, and dire levels of arousal.

"OK, clean up. I'm going to bed. Make sure you watch your video, and listen to the audio files like Ms. Kelly told you to do. Goodnight," Mark said, and then he was gone, back into the bedroom to sleep.

I grabbed my phone and pulled up that night's video while still in the tub, thinking the

water may help. The video had the women and their boys in a new phase of relationship. Some of the guys were tied to these wooden apparatuses, with their butts pointed high. Their partners were behind them, stroking rubber cocks that the ladies had belted on.

I knew what was coming next — those women began pushing those rubber cocks of varying design into the assholes of their partners. Some of the young men were screaming open-mouthed, others were enjoying it. The ones who enjoyed it looked so happy. My hand was already in my freshly shaved ass crack, and before I knew it, I was working a finger into my asshole.

I didn't know what I was doing, and it was hard to reach properly. I was in search of the feeling of Mark's cock sliding along my asshole, and what it would be like if it slipped inside me. I curled my finger into my rectum. It was tight, real tight, making it awkward to work my way in and out with just one finger. It didn't provide what I thought it would...It just felt...well, like I was doing what I thought I was supposed to.

Removing the finger, I rubbed along my ass crack, paying attention to causing friction across my asshole. It felt real good, but not as exquisite as Mark's cock gliding across my sensitive flesh.

I did this for the whole video, about forty-minutes' worth. By the end I was tired and just couldn't go on with it. I was still heavily aroused, but my dick wasn't straining in the cage anymore, like it had just run out of gas, threw in the towel. I cleaned up and got dry.

On one side of the bed were the items Mark had laid out for me earlier: a lacy thong, a tight cutoff shirt, and small gym shorts. Clearly girls clothes. I put them on and left Mark to sleep peacefully in Ms. Kelly's bed, as I made my way to one of her daughter's rooms to sleep.

I was too embarrassed and aroused to sleep next to Mark. I didn't know what I would do if he told me to do something. Putting my earbuds in and hitting play, the audio eventually put me to sleep.

It was a bit tough after all that happened, after all that excitement, and after knowing that I'd crossed a line sexually that I used to think was a solid wall. I shaved my entire body smooth with my friend's help. I wore girlier and girlier clothing. I rubbed another man's cock with my ass...

I loved every second of it all.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
liz33ndliz33ndover 3 years ago

getting this story really heated up now, what a subtle seduction and erotic sissy training.

AnonymousAnonymousover 3 years ago
dam so hot

I would really love to be allen

Cora93Cora93almost 4 years ago
Please, longer chapters

This is an excellent wee story but I feel like I'm just getting into it before it's cruelly snatched away!

Share this Story

Similar Stories

The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
Full Scholarship Naive college kid tries to make ends meet, gets in deep.in Transgender & Crossdressers
Feminizing First Step Ch. 01 A mother begins to feminize her son. First, a new swimsuit.in Transgender & Crossdressers
"Sissified": 12 Days of Sissy-mas Straight man is turned into a submissive sissy by...in Transgender & Crossdressers
Secrets and Surrender High school can be lonely, but shared secrets can help.in Transgender & Crossdressers
More Stories