The curious roommates continue their exploration of dominance & submission in another hot session.
Note: There is a rating embedded within this post, please visit this post to rate it. (You must be logged in to rate this story.)
Roommate Adventure – Part 2
Series: Roommate Adventure
The holidays and accompanying winter recess passed quickly, as vacation time usually does. It was soon time to return to school; studies and classes and life in the college dormitory rooming with Andrew were once again beckoning. And unlike most vacations away from school that I had experienced in my life, I was eager to return to college; I had a strong sense of unfinished business with my roommate that absolutely needed to be investigated. Given what happened the last night we were together, Andrew surely had some of the same desires sequestered in him as I did…And I was now eager to further test the waters with my cute college roommate. After all, Andrew had already spanked me once, gagging me in the process, and he became erect while punishing my ass. And he young, hot, and appealing…I spent many hours during the winter break devising a scheme to put Andrew to the test and determine the extent of his sexual desires. I was absolutely convinced Andrew was secretly gay, as I was, and was a dominant top who would find me to be a very docile and compliant bottom. I was absolutely determined to investigate Andrew’s secret desires, and was intrigued and aroused by the possibilities…
When my mom asked me her annual pre-Christmas question if I needed replacement socks and underwear for college (mothers traditionally seize the opportunity Christmas presents them to buy their boys socks and underwear as a gift, which they must buy for their sons anyway), I told her yes but asked her to give me money instead so I could shop for my own underwear at post-holiday sale prices. She was happy to do so, telling me it was time for me to get used to purchasing my own clothing anyway. As a result, one of my Christmas gifts came in the form of $100 in an envelope labeled “Socks & Underwear.” I waited until several days after the holiday and eagerly set out to the local mall to buy my own underwear for the very first time. I enjoyed the feeling of independence that doing my own shopping afforded me (like many mothers of only sons, my mom sort of pampered me), and went on this shopping trip with Andrew specifically in mind.
Although I was accustomed to wearing boxer shorts, I figured one thing I could do to impress my cute roommate was to start wearing the same underwear he did. Andrew looked really hot in his pristine white briefs, and I figured my build and appearance (similar to Andrew’s; athletic, slender, smooth, tanned, nice rounded butt) would likewise benefit from a change away from the looser-fitting AE boxers I had worn ever since entering high school. I went to the largest department store in the mall and began looking through the underwear inventory. I quickly found what I was looking for; white Jockey brand y-front briefs in my size (waist size 30). A sale price was available; if I bought two packages of three briefs each, a third package was free. I selected two packs of the standard white classic briefs, and chose a pack of the low-rise cut (advertised to ride lower on the hips) as my free set.
Excited by my selection, I then selected two packages of white athletic tank tops (“wife beaters,” in the slang) that I was sure would look sexy on me. The purchase
of several three-pack of socks tallied close to the $100 my mom had given me.
When I went to the closest cashier to check out, I was surprised to see Pete, a casual high-school acquaintance who had gone to a different college than the one I attended, manning the cash register. We made small talk about our respective college experiences, and about Pete taking a temporary job at the department store because (unlike me, whose college resumed classes a week after New Year’s Day), Pete was not due back in school until later in January. Pete was a good-looking guy, and I suspected he remembered that I wore boxers throughout high school. I wondered how he would react as I handed him my new packages of underwear.
Pete looked at the briefs, rung them up, and remarked, “Hey Alex, making the switch to tighty-whities, huh? I always thought you were a boxer-wearing kind of guy.”
I felt myself blush and hoped Pete would not notice.
I shrugged my shoulders. “Well, uh, I just thought I would try ‘em out. You know, something different for college.” I tried to make myself sound offhand and casual.
“Cool,” Pete replied. He shot a quick glance to ascertain that no one was watching him, and quickly lifted up his shirt to reveal a white waistband embroidered with the distinctive Jockey logo. “I’m wearing Jockey briefs myself. My girlfriend thinks they are sexy on me. You will like them, once you get used to ‘em. And so will your girl.” He covered up and winked at me.
“Cool. I ‘ll let you know,” I lied. I gathered my bags and said goodbye, hoping that Pete would be right about the sex appeal of my new underwear. But not for my girlfriend…
I departed the mall and made another stop before going home; there was an adult novelty store in my town that catered to shoppers over the age of 18. I had long wanted to go there out of curiosity, but now had a concrete reason to patronize the establishment. I readied my ID and parked the car and entered the place, apprehensive but excited.
I got home about an hour later and hastened to my bedroom with my purchases. It was mid-afternoon and my parents were still at work. I opened the packages of my new underwear and quickly stripped naked, shucking my boxers aside. I chose the low-rise briefs and slipped them on; they fit well, although certainly snugger than the boxer shorts I had favored for so long. I then slipped on one of my new tee shirts and looked myself over in the mirror.
Without question, I looked good, and I could make out the faint outline of my cock in the y-front pouch designed to hold my genitals. Andrew would like this look on me, I was certain. I smiled to myself and nodded.
I then opened the package from the adult novelty store. I felt a delicious thrill as I felt the cold metal of the handcuffs I had purchased and listened intently to the metallic clicking sound as I tried them on my wrists. Perfect, I thought.
I then handled the wooden paddle I had bought. The surface was smooth and polished. I smiled to myself as I imagined Andrew applying the paddle to my cotton-clad ass.
The final item intrigued me the most. I had seen plenty of ball gags used to gag submissives to silence on internet porn sites. Now, for the first time, I had a gagging implement in my own hands. The black leather strap was wide, and the red rubber ball was large. I decided to get a look. I quickly opened wide and buckled the gag in place and cuffed my wrists in front of me and then looked at myself in the mirror. I instinctively stood ramrod-straight and clasped my cuffed hands behind my head. I really liked what I saw and my cock immediately sprang to attention. Now, I thought, I was ready to go back to school…
As the report date for school approached, I continued to wear my new briefs, getting accustomed to their snug feel and definitely liking the way the form-fitting jockeys looked on my lithe and tanned body. I smiled to myself when I thought of soon seeing Andrew with me wearing the same style of white briefs he did. I did not care if I endured some ridicule from other guys in the dorm for wearing underwear that was not currently in style because I was anxious to see how Andrew would react the first time we got back to our room from dinner and got out of our shirts and pants and shoes and he saw me stripped down to exactly what he had on. And I kept thinking about the spanking he had administered to me… I truly believed Andrew and I would soon find that we had even more in common than wearing Jockey y-front briefs and being studious!
And I had formulated a plan. I was unsure but eager to find out how Andrew would react when he discovered the ball gag along with the handcuffs and paddle I “accidently” left in a place where he would see them in our dorm room. It would be very obvious for Andrew to figure out what to do with the cuffs and gag and paddle and who they were intended for…And if after my spanking Andrew removed the gag to free up my mouth and dropped me to my knees, I was prepared to eagerly take his young boy-cock in my mouth.
My parents suggested that I return to school with adequate time to select my courses and settle in for the new semester. I agreed, and we decided I would report two days before the course selection process was to take place. I immediately emailed Andrew to inform him of the date of my arrival and added that I looked forward to seeing him. Andrew replied that his parents were bringing him back a day after I was arriving and that he looked forward to seeing me as well. I smiled at that; I was sure Andrew did not know how eager I really was to see him and put my plan in motion. I was fully committed to submitting to him, and if Andrew did not take the bait as I hoped he would, it would simply be a matter of him having found personal items belonging to me. (Andrew was quiet, discreet, and private; even if he did not do with them what I hoped, I was not particularly worried about him discovering the handcuffs and paddle and gag.)
My parents took me back to school on the day we had planned. I bade them farewell until they would come back to pick me up for spring break and I promised to contact them once a day. I unpacked my gear and settled in. By that night, the dorm was pretty full. I made my first foray to the bathroom at bedtime clad in my new briefs. Sure enough, another student made a snide remark (“Hey, Alex, nice Crawford imitation, you guys got something going?”) I simply shrugged and said (partially truthfully, at least) that my mom bought the underwear for me. The other guy laughed and let it go, as did I.
The following morning I implemented my plan. There was a table in the middle of the dorm room that Andrew and I shared for stashing our backpacks, books, and other items. I left the package of bondage gear on the table, in full view. All Andrew had to do in order to discover the cuffs, gag, and paddle was to see the package, wonder what was in it, and open it up.
I got up early the following morning, showered, and got dressed. As I pulled on my briefs, I smiled at the thought that Andrew would be seeing me in my new underwear later on this very day. Andrew arrived on schedule and texted me from the lobby. I immediately went downstairs to greet him and help him bring up his gear. We shook hands and exchanged a quick hug and got to work. I had not seen my roommate in about a month, and he almost looked even cuter than before.
Once everything had been brought up to the room, Andrew predictably stripped down to his briefs before beginning to unpack. I shot him a glance and smiled inwardly. I had some paperwork to do for course selection and I likewise stripped to my briefs and athletic tee shirt before getting to work. Andrew saw me as I finished, looked me over, and grinned.
“Hey Alex, what’s with the briefs? No more boxers on my roommate? What gives?”
I smiled awkwardly. “Well, my mom bought new underwear for me for Christmas.” (Again, at least partially true.)
Andrew was still smiling. “Cool. I guess the other guys are going to make comments about the two of us.”
“Yeah. Got a little bit of that last night, in fact.”
Andrew made a dismissive gesture. “Screw ‘em. It’s only underwear. Who cares?” I noticed him steal a quick look at my bulge in the y-front pouch. “And, by the way, you look really good in ‘em.”
My heart quickened and I felt a preemptory twitch in my cock. “Thanks,” I replied shyly, and quickly sat down at my desk. I was really pleased by Andrew’s reaction, and was feeling better by the second about Andrew taking the bait and dominating me.
We went about our business throughout the afternoon, getting work done and setting up the room. We talked about what we had done over the winter break, “in addition to you breaking in your new underwear,” Andrew joked. (I really enjoyed that offhand remark.) At one point my heart quickened when Andrew saw the package of bondage gear on the table top and moved it slightly to make room for his backpack. He did not open it, but had at least noticed it.
I left the room twice during the afternoon; once to go to the vending station and get a Coke and once to go to the bathroom. When I returned the second time, I saw that the package was not in the exact same position it had been when I had left. I was now reasonably certain that Andrew had become curious about its contents and opened it.
If he had, my roommate showed no reaction and continued to interact casually with me as the afternoon progressed. My plan was going as I hoped it would. The worst-case scenario would be that Andrew knew I had bought some bondage gear over the winter break. And the best-case scenario would involve him using those implements on me, and soon. I could only hope…
Dinner time approached. As we dressed, we rehashed some of the highlights of the January NFL playoffs and other casual news. That conversation continued during the hike to the cafeteria. As was our custom, we split up and sat at separate tables, to engage in idle conversation with other students. I was nearly finished when I received a text message.
“Alex – Done early. Going back to the room. This afternoon I found some interesting items on the table. I am quite sure my naughty roommate left them there intentionally, and for a reason. You and I have some unfinished business to attend to from last semester. I’m sure you remember; you weren’t that drunk. Guess I didn’t spank you hard enough. Get back here now.
I quickly looked around the cafeteria. Sure enough, Andrew had left.
I finished up and began the walk back to the dormitory. My heart was racing and I walked fast. Andrew’s text could only mean one thing; that my sexual desires, having been whetted by the drunken spanking Andrew had administered to me a month ago, were about to be realized in full…
My hands were trembling as I fumbled with my room keys to unlock the door. I stepped in, apprehensive and unsure of what to expect but extremely aroused.
The room was dimly lit. I blinked my eyes to adjust and spied my roommate. Andrew was already stripped to his briefs and socks and was standing next to his desk. My eyes went wide as I saw the handcuffs and ball gag in his hands and the cruel smile on his face.
I could only stand perfectly still as Andrew approached me. He was grinning every step of the way. In seconds he was standing face to face with me.
My roommate placed the implements of my impending captivity on my desk beside me. His left hand went to my chest and firmly pushed me against the door. His right hand was quickly and tightly clamped over my mouth.
“Yes, roommate, we have unfinished business. You want to finish what we started last month, don’t you, Alex?” His voice was a commanding whisper and the left hand came up to grasp a handful of my black wavy hair and pin my head in place.
His smile and purring whisper was driving me crazy with desire. “You got yourself young-boy undies and got me toys. You really want it bad, don’t you, boy?”
My eyes remained wide and he was gazing intently at them. I slurred a trembling reply behind the hand covering my mouth: “Yes, Sir. I need it.”
Andrew nodded and freed my mouth from his hand. His voice was curt and commanding. “Sir or Master from now on. Understood, boy?”
“Yes, Master,” I whispered.
My roommate was in full domination mode. “And remain absolutely silent. What happens in the confines of this room is our secret and ours alone. And no one else hears or suspects a thing.”
“Yes, Master,” I whispered again.
“Very well.” Andrew snapped his fingers. “Strip down to the briefs and socks, and be quick about it. Then feet together, stomach in, head down, and hands behind the head. Do it.”
In seconds I was in complete compliance, standing ramrod straight stripped to low-rise briefs and socks in the pose described.
Andrew looked me over and expressed his approval. “Very good. This is the inspection pose. You will assume it each and every time I snap my fingers. And now, I will inspect my boy.”
With that, Andrew looked me over, up and down, front and back. I could only stand perfectly still and silent as my cock began to stiffen. And then Andrew slowly slid his thumbs under the waistband of my briefs.
My cock pulsed and twitched and I gasped. “Wait,” I blurted softly.
Andrew slapped my face hard, cutting off my protest. “I told you to be quiet. Put your hands to your side and open wide.”
I obeyed. In seconds Andrew expertly applied the ball gag and buckled it tightly into place.
“That should shut you up and discipline your naughty mouth. Hands behind the back and turn around.” I obeyed, and the cold metal cuffs were cinched tightly on my wrists.
“Now, I will complete my inspection of my cuffed and gagged boy. Face me.” He looked at me with that cruel smile and again inserted his thumbs under the waistband of the briefs. My eyes lowered in shame. “Look at me, boy.” I looked up, eyes wide and pleading. Andrew was really grinning now.
“You look really cute in these low-rise jockeys, but they are coming down. Right now. Just deal with it.” He locked eyes with me and slowly – excruciatingly slowly – lowered the briefs. I felt my pulsing, rigid cock spring free.
Andrew chuckled and reached down. My body convulsed and my cock jumped and twitched as he took firm hold of it.
“Well,” Andrew purred, “What have we here? A very erect and naughty boy-cock saluting me that clearly requires my attention. I shall see to that in time. But first, I am going to paddle your sorry ass.” Andrew slapped my cock hard, raised the briefs (which did the best they could to hold a very erect cock in place), took me by the ear, and led me to his desk. As he quick-marched me, I caught a glimpse of his straining, rock-hard cock tenting his briefs
Andrew grabbed a pillow from the bed to raise the target, placed it on his desk, and none too gently shoved me face down into spanking position.
“Last time you surely remember I spanked your sorry ass by hand over your boxers. This time, let’s try a harder implement and a bared ass to make a more lasting impression.” Andrew stood beside my rear end and continued to build the anticipation for my impending spanking by gently massaging the now-quivering cotton-clad skin of my buttocks in a slow circular motion with the smooth, cool wooden surface of the paddle. “Once I begin paddling my naughty roommate, I want to hear him count the strokes through the gag plugging his insolent mouth. Work real hard at that, Alex, and there will be fewer blows for you to endure.”
He withdrew the paddle, and I held my breath. He reached down and grasped my erect shaft over my briefs, causing me to gasp inaudibly as my cock twitched and throbbed in his hand. I closed my eyes and steadied myself…
The first blow really stung and sounded like a gunshot; I winced in pain and counter out “One” as best I could through my gag. Each successive blow increased the sting and I hoped my punishment would stop at twenty. He in fact stopped, and I made the mistake of beginning to stand.
I was forced right back down. “Not quite yet, roomie. I told you a bared ass would make a more lasting impression.” I moaned behind my gag as the briefs once more slowly came down to expose my quivering ass. The paddle again caressed my now-bared and burning cheeks, and then he resumed. I was close to both crying and ejaculating when he stopped after I had counted thirty.
“Up and at attention, Alex.” Andrew had to help me stand. I watched in silence as he reached down and took firm hold of my semi-rigid cock. I felt my shaft immediately come to attention and pulse and throb in his hand.
“Now that your mouth and ass have been disciplined, let’s attend to this naughty boy-cock of yours and punish and tame it and put it in its proper place.” Andrew released my fully erect cock and reached down for my briefs. “No need for these now, roomie. I need my boy naked for a session of prick tease.” The briefs were dropped to my ankles. “Step out of ‘em, boy.”
I obeyed and stood nude and helpless and erect before my dominant roommate. My eyes went wide as Andrew produced latex gloves and a tube of lubricant from his desk. (I realized that Andrew had done some shopping of his own over the winter recess as a consequence of our spanking adventure in December.) Andrew had a cruel smile on his face as a gloved and lubed hand took gentle hold of my twitching shaft. It jerked spasmodically in his hand and I began to squirm.
He winked at me. He set an alarm on his watch. “Thirty minutes of edging for your naughty boy-cock, and then I milk you down.”
The next thirty minutes were agonizing. Andrew expertly stroked and manipulated and fingered my slippery shaft, causing it to jerk and throb and twitch. When my muffled pleas and pulsing cock and writhing body signaled that I was ready to burst and climax, he would remove his hand and slap my prick and pinch my nipples and then resume tormenting my cock. I alternated between desperately hoping the thirty minutes would elapse and wishing that the time would never pass.
The timer finally went off on his watch and Andrew stroked me hard past the point of no return. I was dripping sweat and my entire body convulsed and shuddered as I erupted and broke and splattered into his gloved hand.
Completely spent, I went limp and slumped to my knees in exhaustion before him, positioning me exactly as he wanted. Andrew unbuckled the gag and removed it from my mouth. “Clean up your mess, boy,” he ordered, as he forced me to lick my still-warm ejaculate from his gloved hand and swallow it.
Andrew then roughly grabbed a handful of my hair and pressed my face against his groin. His cock, still hard, was pushing against the fabric of his underwear. “Start licking it, “Andrew growled. I obediently worked my tongue against the fabric that was straining against the pressure from within. “Stop. Not much time,” Andrew panted. Andrew worked fast and lowered his briefs; I realized he was close to ejaculating. A large, erect cock sprang free in front of my face. I had been completely subdued; Andrew’s ownership and domination of my cock and control of my orgasm ensured that I would be docile and compliant. And I desperately wanted Andrew’s young cock anyway…I went slack-jawed as he puckered my lips, opening my mouth. Andrew slid his shaft in, grabbed a handful of my hair, and deliberately and methodically fucked my mouth. Seconds before he came, he withdrew his cock and erupted onto my face.
“Roommate just got christened. Hope you enjoyed your first facial,” he growled. “I have marked you as my own. Get up and turn around.” I obeyed, and he removed the handcuffs. “Now, turn back around and clean it up.”
I dutifully complied, collecting his salty fluid in my hands and licking it off and swallowing it.
“Good boy.” He snapped his fingers. Weary and utterly broken, I managed to assume the expected pose.
“You have five minutes to recover, and then we are going to the bathroom and clean ourselves up. We will take ten minutes to shower and brush our teeth. Put on your underwear, get a fresh pair of briefs, and get ready. Move!” He hurried me along to my dresser by slapping my still-sore behind.
I pulled on my discarded jockeys and hastened to my dresser to grab a clean pair of briefs. We stood in the darkness, breathing heavily and sweating, just as we had when he spanked me a month earlier. The five minutes expired, and I dutifully followed Andrew to the dormitory bathroom, not daring to make a sound. Fortunately for us, the hallway and bathroom were quiet and empty. We used separate shower cubicles and stalls and quickly stripped naked, showered ourselves clean, toweled dry, and brushed our teeth. Cleaned and refreshed, we walked back to the room, ignoring a cutting remark (“Hey, look at the boy-undie twins!”) delivered by the one student we encountered.
Once inside, Andrew suggested that I sit down and relax while he went to the vending area to buy us Cokes. Our D&S session was over, and it was time to get things back to normal as much as possible. My roommate returned, and we sat down in our underwear and drank our Cokes and opened up and talked.
I was pleased and relieved when Andrew admitted to me that he was a closeted gay and had a crush on me from the first time he saw me. I told him I was the same and had felt the same way about him, and my underwear fetish led me to enjoy every opportunity I had to see him stripped to his sexy briefs and led me to purchase similar underwear. (Andrew likewise admitted to an underwear fetish, which did not surprise me in the least.) We both confessed how much we had enjoyed the first spanking episode in December, and how we had hoped the experience could be repeated. We were clearly destined to be boyfriends, but since we were discreet individuals and serious students, our sexual encounters would be limited to Friday or Saturday nights to keep our relationship private and to allow us the time we needed for study and school activities.
It was soon time for bed. Andrew suggested that we continue our practice of only appearing before each other in our underwear in the privacy of our room. I eagerly agreed and suggested that we try a future encounter stripped to jockstraps, which led us to plan for each of us to order a sexy jockstrap for the other partner who would be required to wear it the entire day both leading up to the session and for the session itself. Andrew told me he believed he was a switch and in the future would want to try being the bottom and at the very least wanted to suck my nice cock. I told him I definitely liked that idea.
We rose, hugged each other, kissed each other on the cheek, and went to bed. Before I drifted off into a deep and contented and dreamy sleep, I smiled as I realized that never in my life was I so glad…to be back in school!
Hey! Thanks for the question!
I think it’s great that you both have found something that you can both explore. As far as what to do… that’s really up to you. I know that sounds like a cop out but the truth is that you have to do what feels right for the two of you.
What does that mean… feels right for the two of you? Master/slave relationships DO involve a lot of trust. So with the trust that you share with your man, explore what it is that you and he both like.
With you the master, he will follow your lead. And what can you do? As the master, you can really do anything you want.
You may want to try looking up some master/slave sites on tumblr and checking them out. Maybe they can give you some good ideas of the things that you can try together.
I also have followers who are masters and some that are slaves. I have no doubt that they can give you more information about things that you can try. Maybe one or two of them will “like” this post and you can look at their pages and talk it through.
I wish I had more experience here to be able to help further. I think it’s great that you are both exploring this together. So come back sometime and share with us what you have learned. I think it’s great to hear how different people connect with their partners!! RAWR!
I hope that helps!