Higher Education (Part II, Ch3 & 4)

Higher Education
Chapter Three : The First Talk

I don’t remember the last time I spent so long taking a shower. Usually I’m in and out quickly, but then normally I am showering alone. Jake and I spent so much time in the shower that the skin on our feet was beginning to shrivel up by the time we were done.

We didn’t really do anything of a sexual nature while in the shower, but there was a lot of touching and caressing as we lathered each other up thoroughly. It felt really nice, and actually kind of natural to bath Jake, and have him bathing me. It really felt good when he shampooed my hair, while I was kneeling in the shower stall with my back to him as he lathered up my hair and gave me the best scalp massage I ever had. Not that I have had that many scalp massages.

We finished showering almost an hour later. We dried off and went back into the main part of our dorm room. Neither of us felt the need to get dressed, and we sat down on the sofa and clicked on the TV. We didn’t really watch anything; it was more for having back ground noise during any of those occasional moments of awkward silence.

“So can I ask you a personal question?” I asked Jake breaking our initial moment of silence.

“Ahh,” He looked over to me. “I think after what we just did the past couple of hours there really couldn’t be any personal questions that I wouldn’t answer.”

“Yeah I suppose so,” I laughed. “Well I was just wondering about your body hair.”

“Or lack there of?” Jake asked, interrupting me.

“Yeah, that,” I said. “So do you like shave or use some hair removal cream or something?” I reached over and tickled the few short pubes he had just above his cock. “I mean do you do something to keep yourself like this?”

“Nope,” Jake said, blushing a little bit. “That’s all natural. “I have never had much hair. My older brother never had that much hair either. I think it’s in my DNA to be almost hairless.” He lifted his left leg and rubbed it down to his ankle and back up. “I’ve never even felt a hair growing on my legs.”

“Really?” I asked inquisitively as I ran my hand up and down his leg. “I noticed earlier how smooth and silky your skin was; I just figured you used something to remove the hair.”

“Nope all natural,” he laughed then looked over to me. “Does it bother you that I don’t have much hair?”

“No quite the contrary,” I laughed. “When I first saw you naked earlier, I was like awed at how sexy you looked without any hair except for this little patch of shorties.” I again reached over and tickled his small amount of pubes. “I’m glad you are this smooth and silky.” I said as I rubbed his stomach and let my hand wander down his leg and back up to his hairless balls before running my finger through his pubes again, making my two fingers like a pair of scissors, I ran them through his pubes, they weren’t even long enough to stick through my fingers. “I think you’re damn sexy just the way you are.” I blushed and turned away and whispered. “Oh my god.”

“What?” Jake asked in a sensitive tone, leaning his head down to look up at me as I looked down and away.

“I just never,” I shook my head and looked at the TV. “I never thought that about another guy, let alone said it.”

“What, that I’m sexy?” Jake smiled at me with his big toothy smile.

“Yeah,” I half whispered. “I feel foolish having said that.”

“Well don’t feel foolish,” Jake whispered as he reached out and placed his hand on the side of my face and turned me to look at him. “I’m glad you find me sexy. I think you’re damn sexy too, just in case you were wondering.”

“Oh really?” I laughed. “I never had a guy say that to me either.”

“Well I bet you’ve had girls tell you that you were sexy.” He said as he traced a finger around my chest, circling my nipples and then down into my pubes.

“Yeah that I have,” I laughed and watched as his fingers were running through my pubes. “So am I to hairy?”

“Well,” He kind of laughed as he ran his hands back up across by belly and to my hairless chest. “Not here you’re not,” he said and then let his fingers run down to my legs and caressed my legs with his hand. “Nor down here. But,” He continued as his hand reached by balls and he circled through the pubes around my cock. “You do have a bit of extra floss here.” He laughed.

“Yeah it is a little bushy,” I said looking down, watching his fingers run through my pubes. “Hey I have an idea.”

“What?” Jake asked looking up from my crotch.

“How about as the first part of your punishment you give me a nice trim job down there.”

“You’d trust me to do that?” He looked me in the eyes.

“Well, I trusted you enough to let you cum in my mouth and have me taste cum for the first time. And I trusted you enough to suck my cock until I came in your mouth, so yeah, I trust you.

We both laughed long and hard.

“Cool, I’d love to trim you up nice and neat, especially on your balls and down here,” he said poking a finger between my legs and into my butt crack. “And maybe shorten these up a little bit.” He added gently tugging at my pubes. “I floss enough; I don’t need it when I suck.”

“Okay,” I said. “Do you want to do it now?”

“Sure, I’d love to,” He said and then paused. “Hey wait a minute; you said ‘first’ part of my punishment. How many parts will there be of my punishment?”

“Well, we can discuss that if you want,” I felt myself blushing, and Jake must have noticed my face heating up and turning red, for he interrupted me.

“Oh you’re blushing just thinking about it,” He laughed. “It must be something good. So come on, tell me, I have to know now.”

“Well I was thinking,” I paused again. “Well you know, I like really liked what happened tonight, and I was thinking, and you can say no if you want to, but…”

“Oh come on Toby, spit it out.” We both laughed at the play of words.

“Well I was wondering if for your punishment you would be willing to be like my sex slave or something for this semester.”

“For the entire semester?” He asked.

“Well only if you wanted to,” I whispered. “I’d like to do this some more and like not just once or twice, and I thought that for your punishment, it could be an on going punishment sort of, you know, since if we do this again, you’d be getting some enjoyment out of it so that really wouldn’t be a punishment for you now would it?”

“Oh I see where you’re going,” Jake smiled. “You want to do this again with me, and just so you know Toby, I really want to do this again with you. But when we do this it really wouldn’t be punishing me for what I did with your fragrant underwear.”

“Yeah, I mean you’d enjoy it too much, so that wouldn’t be a punishment would it?”

“No I guess it wouldn’t,” He laughed. “So you want me to be like your sex slave for the semester? You want me to be ready to do whatever you ask me to do, wherever you ask me to do it even if it isn’t totally sexual?”

“Yeah kind of, I guess.” I looked at him and smiled, praying he’d agree to do it.

“Okay,” he said, “But only if it’s for the entire time we are together at school.”

“The entire time at school?” I asked wondering if he had read the part in the flyer about roommates having first choice to remain roommates each year if they so choose. “Before I say yes to that, do you know about the roommate policy here?”

“You mean where we can dorm together every year if we so choose?”

“Yeah.”

“Yup I know about that, and that’s kind of what I meant. I know we just met, but I’d like to be your roommate as long as we both go to school here.”

“And you’d be my sex slave every year?” I asked, feeling a twitch in my groin.

“Yes, if you want me to be, and we could continue it through like emails and web cam during breaks,” he smiled and then looked down at my crotch. “I think we know his answer.” He laughed as he reached down and rubbed my once again hard cock.

“Well I don’t want to disagree with him.” I said looking down at my cock, wrapped again my Jakes hand. “It’s a deal then. Shake on it.” I said extending my hand.

“No, kiss on it.” Jake said as he leaned in and pressed his lips to mine and we embraced in a long kiss. “Now let’s go get the first part of my punishment done.” He stood up and grabbed my hand and pulled me to the bathroom. “I’m glad you’re hard again, it will make it easier to shave down there.”

We headed off to the bathroom for my first collegiate haircut, with Jake leading me by my hard cock.



Higher Education
Chapter Four : A Proper Haircut Opens a New Doorway

I stood in the center of the bathroom, legs slightly spread apart, Jake was stilling holding on to my hard cock with his left hand as he opened his cabinet above the sinks. He pulled out a small electric trimmer, a pair of scissors, a comb and a razor.

“Are you sure about this,” He asked, smiling at me and gently stroking my hard cock. “It’ll grow back anyway.” He added as if to assure me.

“I know it will grow back,” I laughed. “That just means you’ll have to do barber duty every so often.”

“Cool,” he smiled and knelt in front of me. “Let’s start with trimming back the bush here.” He said as he ran the comb through my pubes, staring at the base of my cock and combing upward. After he had combed all of my pubes up, he ran the comb through them and stopped about a half of an inch from my skin and started cutting with the scissors. I watched clumps of my pubes fall to the floor. Next he combed through the thin strip of hair that ran from my pubes up to my belly button.

“We’ll want to save your cute treasure trail,” he said as he looked up at me and smiled. “But I’ll trim it up so it is really a cute little trail.” He combed through the thin strip of hair and cut off about half the length of the hairs and then picked up the razor and ran some hot water into a bowl and dipped the razor into the water and shaved up the sides of my treasure trail on both sides until only about a quarter of an inch of short hair was left. He picked up the electric trimmer and trimmed straight across the top of my pubes and down the sides, squaring them off. Next I watched him shave all the hair from the base of my hard cock up about an inch so that there was a bald spot between my cock and the start of my pubes. He ran the electric trimmer over my balls, pulling then slightly to tighten the skin. He removed most of the hair from my balls this way and looked up and asked as he rubbed the front of my thighs.

“So how far down your legs should I go?”

“How far do you want to go?” I asked.

“About down to here.” He answered drawing a line with his finger about three inches above my knee. “There isn’t much hair there anyway.” He said as he smiled up to me, as if to be begging please.

“Sure, go for it.” I replied and rubbed his head.

Jake shaved the front of my legs and then had me turn around and using the trimmer shaved the back of my legs and up into the crack of my ass. He stood up and turned the water on in the tub.

“Hop in,” He said. “I’ll do the finishing work in here. It will be easier to keep you wet.”

“Oh you’re keeping me wet,” I laughed as I pinched the tip of my cock with my thumb and forefinger and pinched out some pre cum. “Very wet.” Jake grabbed my hand and licked my pre cum from my fingers.

“Hee-hee, you’re so punny.”

I stepped into the tub and knelt down and leaned back. Jake climbed in in front of me and splashed warm water over my legs and genitals and proceeded to use the razor to give by legs, balls and around my cock a close shave. When he was done, I was as smooth as silk. He turned me around and splashed water on my ass and began to use the razor to shave the hair from my ass crack. He carefully ran the razor around my asshole and up and down the insides of my butt cheeks. He splashed some more water on my ass and caressed my ass and legs.

“Oh so smooth.” He commented.

“Just like you.” I laughed as I turned my head to look back.

“Yup,” he laughed. “Now your ass is kissable soft.”

“Well then maybe you better kiss it.” I told him.

Jake leaned in and I waited for him to kiss my butt cheek, but instead I felt his hands spread my butt cheeks and he placed his lips directly on my asshole and kissed it.

“Oh my god.” I screamed and jerked forward and half turned around. “Dude?” I asked, surprised.

“I’m sorry,” He blushed. “I didn’t mean to freak you out or whatever.”

“Did you just kiss my asshole?” I asked still surprised.

“Yeah,” he said softly as he blushed even redder. “Sorry if I went to far.”

“No, no it isn’t that,” I said as I sat down in the water and faced him. “I just wasn’t expecting that. I never had anyone kiss my asshole before.”

“How did it feel?” he asked with an inquisitive yet eager for a positive reply tone.

“Well I really don’t know,” I replied. “It took me by such surprise I didn’t really stop to think about how it felt.”

Jake sat there looking at me and then looked down and splashed water unto my crotch. He whispered softly.

“Would you like me to do it again to see how it feels?”

“Ah,” I looked down at him; he looked so embarrassed. “Do you want to?” I asked trying to sound reassuring.

“Yeah, if you want me too.” He looked up and half smiled at me.

I lifted myself up out of the water and turned around so my ass was facing him. I felt his hands caress my ass and then spread my butt cheeks. I tensed up a little in anticipation, and then I felt his lips on my asshole. He gave my asshole a slow tender kiss.

“How did that feel?” He asked.

“It felt pretty good actually.”

“How about this?” He asked. I soon felt the wetness of his tongue as it circled around my asshole and then slid across it.

“Oh fuckin yeah!” I screamed out. “That fucking feels awesome Jake.”

Jake continued to lick his tongue across my asshole as he reached between my legs and began to stroke my cock. I felt his wet tongue circle my ass and flick my asshole. But when he stuck his tongue into my asshole I freaked.

“Oh holy fucking Christ.” I yelled. “Don’t stop, god don’t stop! This feels so fucking great.” I screamed as his tongue licked and entered my asshole. “You’re tongue feels awesome in my asshole Jake, yeah tongue my ass my little slave.”

Jake buried his face in my ass and tongued my asshole with a passion like no other. I couldn’t believe how sensitive and sensual my asshole was. I’d never had anyone so much as touch my asshole before, but now that Jake was tonguing it, I didn’t want it to stop. But alas after a few minutes he sat down in the water and splashed water up in my ass.

“I take it by your reaction that you enjoyed that?” He asked.

“Oh god yes,” I said as I turned and sat down in the tub facing him. “What made you think of doing that?”

“It just felt like the thing to do,” Jake said splashing water on my crotch. “And honestly, that was the first time I ever did that.”

“Wow, I feel privileged.” I smiled and splashed his crotch with water.

“And well you should be,” He laughed.

“This seems like a night for ‘firsts’ for both of us.” I said as I reached out and gripped his shoulders and tried to turn him around.

“What are you doing?” he asked.

“Well,” I paused. “I don’t want you to be left out of that great feeling.”

“Really,” he said excitedly, his eyes grew big and a huge smile formed on his face. “You want to do it to me?”

“I’m willing to try,” I replied. “But I can’t guarantee I’ll like it, so don’t expect it to last too long.”

Jake quickly turned around and raised his small hairless ass into the air. I reached out and placed a hand on each side of his butt and looked down at his smooth wet ass.

“You have a tiny ass,” I laughed. “So cute and tiny.”

“Is it kissable cute?” He laughed.

I leaned in and kissed his butt cheek. I stuck my tongue out and licked his ass. I spread his tiny smooth cheeks apart and slowly licked the crack of his ass down to his hole. I paused and then closed my eyes and kissed his asshole. He squealed out in delight. I stuck out my tongue and let it slid across his asshole. He squirmed and squealed again. I circled my tongue around his asshole and then pushed my tongue against his hole. He was squirming so hard I needed to forcibly hold him in place. I licked and stuck my tongue in his asshole for about two minutes; until my tongue became tired and Jake was barely able to breath from his excitement.

“Oh god,” Jake moaned when I stopped. “It’s good you stopped or I might have passed out from the pure pleasure of feeling that.”

“Was that the first time anyone did that to your asshole?” I asked.

“Yes, yes it was,” He replied. “But now I wish I would have been having that done a long time ago.” We both laughed.

“So did you like doing it?” Jake asked.

“Yeah sort of,” I said. “I mean I didn’t mind doing it, and it wasn’t gross or anything, as long as you didn’t fart.” We both laughed again.

All of a sudden Jake got this real serious look on his face and stared right into my eyes. I was kind of freaking out inside by the way he was looking at me.

“Toby?”

“Yes Jake.”

“I know we just met today,” He began as he stared right into my eyes and placed his hands on my shoulders. “But I really like you, and I was wondering, did you really mean what we agreed to earlier, about being roommates every year?”

“Yeah Jake,” I said looking him in the eyes. “I really meant it. And I know what you mean by just meeting but feeling something. I mean I’m not gay, and my girlfriend will be coming to visit at times while I’m here at college, but there is something, I don’t know how to say it, there’s just something about you that enthralls me.”

“I was hoping you’d say that.” Jake stood up and held out his hand. “Come with me.” He said as he stepped out of the tub. I stepped out too and we dried off and he grabbed a couple of towels and led me into the living area of our dorm room.

“I want to offer you something I never offered anyone else before,” Jake said nervously, but with a wide smile. He walked over to his dresser and came back with something in his closed hand. “I really want you to be the one for this, but if you don’t want to I’ll understand.”

“Just what is it you want to give me?” I asked looking down at his hand. He leaned in close and whispered in my ear.

“I want you to be the first guy to fuck me.”

I was speechless. I stood there frozen for a minute just looking at him. I thought maybe I heard him wrong, but then knew I hadn’t.

“Are you sure?” I asked. “I’ve never done that before, not even with my girlfriend. I’m not sure if I could even do that.”

“Will you try,” He whispered and blinked his eyes at me. “I would really like to give you my ass cherry.”

When he said that I laughed. He laughed.

“Ass cherry,” I laughed again. “That sounds funny.”

“Yeah I know,” He smiled. “And I know it seems quick, but I just feel like you’re the one I should offer it too. That is if you want to.”

“To fuck you in that cute little ass?” I asked. I stood there thinking about it for a few seconds. “I would be honored. But how do we do this?”

“Well,” he began as he opened his hand to reveal a condom and a small tube of lube. “You just put this on and lube your cock and I’ll lube my hole and we just take it from there.”

“So you want me to pop your ass cherry then?” I smiled. “How do you know you’ll like it?”

“Well I have used a dildo and other objects on myself before and that always feels good so I was thinking a real cock that was really fucking my asshole would feel better.”

“So do you like bend over and I just shove it in there?” I asked as I took the condom from his hand.

“Well that’s one way I guess,” Jake laughed. “But I’d like to see you as you do it; give it more meaning I guess.”

“So how do we position ourselves?” I asked feeling a little stupid.

“Well I thought I would lie over the arm of the sofa and you’d hold my legs up and try it that way and see how it goes.”

“Okay,” I said inquisitively as I opened the condom package. “I do like that cute ass of yours, and it tasted pretty good too.”

“So now you can feel what it’s like to fuck this cute little ass.” Jake said as he turned and showed his ass to me.

I slid the condom down over my hard cock and took the lube from Jake and squirted some on the top of my cock and rubbed it all around my cock.

“Do you want to lube me up or should I?” Jake asked.

“I’d love to.” I said as I knelt down and he bent over and spread his legs. I squirted some lube on his asshole and rubbed it in a circle on his hole. I slowly slid a finger into his asshole, sliding it in and out. I then slid a second finger inside him and began to finger fuck his asshole. “How’s that feel?”

“Awesome,” Jake said and then turned around, making my fingers slide out of his hole. He lay down on his back and lifted his legs and held unto his calves and pulled his legs apart. “Squirt a little more lube on me and then try it with your cock.”

I squeezed out a little more lube directly on his asshole and wiped my hand on the towel on the back of the sofa. I gripped his ankles and held his legs up and out. I stepped forward and placed the tip of my hard cock tight against his asshole.

“Do I do it slowly or just shove it all in at once?” I asked, having never penetrated anyone’s asshole before.

“Start out slowly,” Jake said as he sighed when he felt the tip of my cock press against his asshole. “I’ll let you know as we go.”

I let go of Jakes left leg and gripped the base of my hard cock with my right hand. Jake reached up and held his leg, pulling it down to his chest and out to the side. I held unto his right leg in my left hand and looked down at him as he looked up at me and smiled. He took a deep breath and exhale. I pushed my hard cock slowly into his asshole until just the head of my cock was inside him.

“Stop, stop for a second.” Jake sighed.

“Does it hurt?” I asked.

“A little, but it feels good too.” Jake replied. “Okay, do a little more.”

I slowly pushed my cock a little farther into his asshole. Jake’s breathing became shallow and quick. He began to moan softly. I pulled back a little until just the head of my cock was inside him, and then pushed back in a little. Jake’s eyes rolled back into his head and he was panting.

“All of it Toby, give me all of your cock.” He yelled out. “Oh god, fuck me Toby, fuck my ass.”

In one swift motion I shoved my hard cock fully into Jakes asshole and held it for a few seconds before I started fucking him. His ass was so tight and the grip his anus muscles had on my cock was tremendous.

“Oh fuck Jake,” I yelled out. “Your ass is so fucking tight and hot.” I was thrusting my hard cock in and out of Jakes asshole. He would open his eyes and smile at me for a few seconds before his eyes would roll back into his head and he would moan and gasp for breath.

“Fuck me Toby,” Jake screamed out. “Fuck me hard. Oh god your cock feels great inside me.”

I thrust myself deep into Jakes asshole. I wrapped my arms around his legs and held him tight against me. With my right hand I reached down and began to stroke his throbbing cock. As soon as I touched his cock he began to cum. I stroked his cock and fucked his ass. I thrust myself fully into him and felt myself cumming. Jake must have sensed my impending orgasm for he tightened his anus muscles and they gripped my cock and pulsated, literally his asshole was milking my hard cock to climax. I emptied my load deep within him. I was sweating and my sweat was dripping down unto Jakes chest. His hair was matted with his own sweat and he was panting and moaning ‘Oh God’ over and over again. Our eyes finally met again a few seconds after we had both cum. I stood there, my cock still in his asshole, gripping his legs and holding his ass tight against me. I looked down at his cum covered chest and belly. I slide my cock out about halfway and slowly pushed it back in, Jake leaned his head back and moaned loudly. I did that a couple of more times before pulling my now softening cock from his asshole. When I did, his whole body shuddered. I gently let his legs go and leaned down and kissed him fully on the lips and then proceeded to lick his cum from his chest and belly before sucking his cock into my mouth and sucking the last of his cum from his cock. I looked up at him, he reached up and pulled my head to his and licked my lips and I lay on top of him, our nakedness touching as we kissed long and hard.

Jake pushed me up, and I stood at the end of the sofa, he slid around and sat on the sofa and reached out and pulled the cum filled condom from my still semi hard cock. When he did, he sucked my cock into his mouth and licked it clean before turning the condom inside out and sucking my cum from within it. I lifted him up and embraced him and softly but firmly held his ass in my hands.

“That,” I whispered into Jakes ear. “Was by far, the best orgasm I have ever experienced. Thank you Jake, thank you for allowing me this honor.” I looked down over his shoulder as I caressed his ass. “God I love your ass.” I leaned my head back and then leaned in and kissed him. “And the rest of you too.”

“Thanks Toby,” Jake whispered. “And I love your cock,” He said as he rubbed my softening cock. “And of course the rest of you.” He added as he rubbed his hands all over my body.

“Well I guess its shower time again.” I laughed.

“Yeah, we worked up quite a sweat didn’t we?” Jake laughed as we walked to the bathroom, with my right hand rubbing his tight, tiny, hairless ass that I had just fucked.