Derek's New Girl
I first met Derek during our first year of college. We were assigned roommates in a communal sort of student residence house and hit it off the first time we met. At 20, he was a year older than me and was one of those people who just radiates natural confidence with maybe a hint of arrogance but always just enough to be endearing. It didn't hurt that just as naturally he had a body to die for. He stood around 6'3" and despite never playing sports or working out he had a strong and athletic build while being lean enough to look very toned and defined. His assertiveness and charisma more than made up for my lack of anything resembling either trait. I was always a quiet and more introverted person, not to the point of being shy and anti-social, just very laid back and happy enough with boring nights at home. Standing several inches shorter and many pounds lighter than Derek combined with his charm had me quite intimidated by the guy when we first met, despite taking a liking to him immediately. He talked me into joining him at the bars and parties constantly and while we did have fun, I always felt sort of undeserving of his friendship and would try to make this up to him by cleaning up around our place or giving him some of my booze or pot if he needed. We had a blast all year and became very good friends but it wasn't until the next year that things would change between us.
As the first year of school was ending, we had remained close and one day he called me up and told me he'd taken the initiative of finding a place to live for our second year. I hadn't even considered where I'd be living or who I'd be living with and when he called out of the blue with a place, I didn't hesitate and told him I was on board. The place turned out to be a cheap two-bedroom apartment in a building that had been the original residence building of the school. Nothing fancy but cheap and within walking distance to everything we needed. This block also had a reputation in town for being one of the more... turbulent party areas for the college, which also played into our young male brains making the choice to move in. The second year started much like the first; Derek and I were both in programs we enjoyed and so were doing well in school but were far from perfect students. Fun was priority number one. With more freedom having our own apartment and no residence staff to watch over us we were constantly having friends and girls over, drinking and consuming pretty much anything else we could get our hands on. Derek was the only one with a credit card, so we had an arrangement that he would pay our bills with it and I could pay him my half in cash. This quickly turned into me doing most of the chores around the apartment and providing him with booze and drugs. Whenever I just offered him money he would say something like "Don't worry about the cash, you can make it up to me some other way." and level me with one of his cocky smiles that forced me to do his bidding.
I don't remember what exactly started it, but even though we had lived together the year before I suddenly found myself aware of any time Derek was lacking any sort of clothing. Whether shirtless on a hot day, or chatting on his way in and out of the shower, I found myself having to fight the urge to stare at his sleek, toned body like never before. He had a tantalizing fuzzy treasure trail that lead from his belly button down into his underwear that would entice my gaze whenever I thought I could get away with it. I found my alone time at night being occupied fantasizing about exploring Derek's naked body and while it began relatively innocently the imaginary Derek in my head had the same dash of boldness and I was soon picturing myself serving him however he desired. I began feeling the same intimidation around him when I did upon first meeting him. It was as though he could read my thoughts just by looking at me, and unless I got the urges out of my system every few days I would become a sniveling mess in his presence. I typically would find videos of twinky boys like myself getting dominated by stronger, bigger men. While I thought this was keeping my dirty thoughts at bay, it became a daily ritual for me whenever I had a night or some time at home alone. I imagined devoting myself to Derek's pleasure but I knew he was straight. I had some interest in girls before he filled my dreams but he would bring some new girl home every week or two and even though he seemed to live for getting laid there was no way he'd be interested in me. Shemales and cross-dressers began replacing the twinks getting fucked in the videos I watched as it was easier to imagine myself with Derek if I looked like one of the slutty girls he'd take home from the bar.
The two of us were alone at home one day hanging out in the living room watching some TV. Derek was on his laptop doing what I assumed was homework while I was loading bongs for us and passing him a fresh bowl whenever he requested. By the time we were both quite stoned, Derek stood up like a shot, remembered he had one more lecture that day and ran into his room to get ready. Laughing it off I went back to smoking and focusing on the television while his rushing around became background noise until he next spoke to me.
"Shit, I'm going to be late. Just so I don't forget, I was looking over our internet account and thinking about how it's crazy the things I can see being the one with his name on the bill." he said as I turned my head towards him just in time to see him flash me a grin and slip out the door.
The TV had now shifted to the out of focus background noise as I sat there simultaneously wondering what he was talking about and yet somehow knowing deep down what he meant. Seeing his laptop sitting open on the couch, I grabbed it to put it away in his room and noticed that the window open on the screen was displaying the internet history on our network which of course he was paying for and so had access to. The feeling of shock fully set in as I started scrolling past listings of gay and transexual videos and websites. I set the computer on his bed and fell to a seat beside it, trying to process what I'd just seen. There was no way I could see of denying that amount of videos, I was watching some sort of incriminating porn nearly every day at this point so there was no blaming accidentally clicking a wrong video. Panicking, I merely deleted the built up history log and decided that was the best I could do. If he'd already seen it I was fucked regardless and if he miraculously hadn't seen it somehow, which seemed impossible given his comment before he left, then I could defend a deleted internet history easier than a ton of gay videos. Having no clue how he would take all of this, I just left his room and left for the night hoping to avoid seeing Derek. I met some classmates and ended up getting very, very drunk. I stayed out until early into the morning before I figured I might as well stumble back to my room and sleep, having dreaded my return and facing Derek all night. Thankfully, I arrived to a quiet, dark apartment and quickly made my way to my bed.
I woke late in the morning, having missed my first class of the day and feeling like death with a pounding headache and a stinging feeling of something wrong in the back of my mind. Resigning myself to a day of recovery asleep in bed, I decided a quick shower would at least make me feel a little better. I dragged myself out of bed and into the hallway, passing Derek's room on my way and noticing the door was closed. I hoped he was still asleep and I could go unnoticed into the bathroom.
"Morning buddy!" his voice shattered the dull silence of my hungover reality and I snapped my head to the kitchen where he was leaning on the counter eating an orange. "You were out pretty late last night, I didn't even hear you get back. You manage to get some tail? You look rough, man, shit."
He popped an orange slice into his mouth and smiled at me as he chewed, his eyes giving off a new sense of knowing as they bored into me. He had verbally jabbed me in the ribs, not coming out and directly saying what we both now knew but doing the next best thing. I had no good answer for him.
"Ugh yeah well I don't feel any better than I look. Went out with a few guys from class and got a little out of hand I guess." I tried to play it off with an unenthusiastic smirk and started moving again towards the bathroom, eager to be out of his presence.
"Hey thanks for putting my computer away yesterday, by the way" he managed to say when I got halfway to the bathroom.
"Oh, no problem, man. You were in a rush I guess, figured I'd put it away for you." I said as I was closing the bathroom door and locking it. I thought I heard him chuckle as the door was closing but couldn't say for sure.
Leaning against the shower wall as the water rained down over me, I came to a little and the events of the day before came to the forefront of my mind again along with what he had just said to me. He never outright said he knew, but he was able to wreck me with a mere gaze implying he most definitely did know. On the bright side, he hadn't beat the shit out of me or kicked me out, but I was still scared of how he would react if I openly admitted anything and so I couldn't even bring myself to ask him to keep my secret. I decided if I never brought it up, the whole thing would fade from our memories. Making a beeline to my room out of the shower, I spent the day tossing and turning in bed trying to get some sleep and make sense of my life at the moment.
The next few weeks had me swearing off anything pornographic that wasn't a man and a woman. I hoped that by trying to forget what had happened I could put this behind me and return to normal. At first it went well, but after a few episodes of giving in to drunken urges and getting off to a few videos of skinny guys getting railed I got scared and felt that creeping paranoia coming on again that I was about get caught and outed to everybody. I needed a way to get my perverted rocks off without anybody knowing. Luckily, while I'd never had the balls to go inside, there was a sex shop in the mall nearby that I decided would save me. I skipped my next class and hurried over to the mall to see what I could find.
I was happily surprised when I walked in to a nearly empty store. Appearing not to notice me, a woman who looked to be in her 30's was behind the cash and the only other occupants were a couple of older guys wandering around the video section. I had planned on merely picking up some videos I could play incognito but wasn't into browsing gay and shemale porn with the older guys so close by. I decided to kill some time looking at toys and stopped in my tracks when I saw a shelf of super realistic dildos with balls, suction cups, vibrators, and even some that would "cum" lube for extra realism. Just looking at them got my own dick semi hard and I knew I needed more than a couple of DVDs. Why settle for watching somebody get fucked and imagining myself there when I could do the next best thing with one of these lifelike rubber cocks. As much as I'd been trying to fight it, this would be much more fun to fantasize about Derek pounding me as well. Before I lost heart, I grabbed a large 8" dildo off the rack and picked up a set of very girly hot pink bra and panties with black thigh high stockings. My heart rate was through the roof while I was buying it all but I didn't care. I could just picture myself dressed up and bouncing on the dildo while moaning for Derek and any reservations left my head.
I picked up some other essentials on my way home and dumped my pile of new playthings on my bed. My dick was hard as stone at this point so I just pulled the dildo out of the box and nearly came just holding it. It felt so good and big in my hands, the texture was very close to holding the real thing and I quickly stuck it to the wall and dropped to my knees. Despite some intense urges, I had never touched another man's penis before and so was surprised at how big the dildo felt when I stuck it in my mouth. It did the trick, however, making me feel very submissive even sucking on this bodiless rubber cock stuck to my wall. Slapping my own face with it and gagging myself as I tried to take it deeper and deeper, I came like I hadn't touched myself in weeks and sat back thinking about how much fun I would be having with my new rubber Derek.
Ever since Derek had first hinted that he knew what I'd been looking at online, we had been kind of distant. Most of it was probably my own fault, but I didn't mind. I was obsessed now with using any spare minute of alone time at home playing with my dildo, wearing my sexy new lingerie, and keeping myself groomed. I had quickly taken to shaving myself completely beneath the neck, bathing with fruity smelling solutions, and fucking myself silly with the dildo. But I started craving more. Now it wasn't enough to be fucked by this rubber cock and imagining Derek was taking me from behind, I needed something new. In a trance of lust, I knew what to do. Every Tuesday evening Derek had a night class and because of the odd hour, they got a half hour break at around 9PM. Like clockwork, Derek would make the five minute walk home, roll a joint, and take a shit before going back to class after about 20-25 minutes. I used to tease him for it before I was scared that he would shoot back with accusations of me loving cock, but he would always laugh it off and tell me he enjoyed it. We had a shared storage room in the apartment that was just beside the bathroom that Derek had kind of just taken over it and used it for his own long term storage and I'd never argued with him. Among other things, he left a set of workout equipment in there that he never touched with an adjustable bench and full set of weights to go with it.
Once Derek left for his night class the next Tuesday, I nearly broke my neck running into the storage closet with my armload of supplies. I had been turning this over in my head for days and was about to explode now that I was able to put it in action. I had a couple drinks to soothe my nerves as I got all dressed up and waited. With about ten minutes to go before Derek would walk in the front door, I raised the back of the bench to a 45 degree angle and lay on it chest down before tying my feet firmly to the underside of the workout bench. Sticking the dildo to the leather beneath me, I played one of the videos I'd bought of a pretty little sissy boy getting ravaged by his frat brothers on low volume that I could hear but the sound was contained in the small closet. I tied my hands similarly to my feet and plunged my lubed up asshole down onto the dildo and began to ride it instinctively as I watched the video in front of me and waited. The bench squeaked noisily beneath me as I rocked up and down, so as soon as I heard Derek's key in the lock I froze, my heart beginning to beat like crazy. I turned on the vibrator to an intense but sporadic pulsing mode and bit my lip, knowing that there was no going back as I heard the door opening and my roommate entering the apartment.
Now that I had no choice in the matter, I felt panicked. I started regretting what I had just gotten myself into. Derek might have forgotten the internet history, but if he walked in on me now there could be no doubt I was a slut for cock. I was set up so that if anybody opened the closet door, they would immediately see me from behind, fastened to a workout bench, dressed up like a sissy and taking a fat, vibrating rubber cock up the ass in a dark closet lit up by a video of a similar little sissy getting used like I was. I fidgeted a bit which caused the workout bench to clang hollowly against the floor and I froze. My heart was absolutely pounding in my chest, sounding so loud in the small confined room that I was sure Derek could hear it from outside. Soon enough however I heard him leaving his room, and could sense him walking in my direction. I heard the bathroom door next to me open and he turned on the lights and vent fan to suck away the pot smoke. With the cover of the fan noise, I rearranged myself on the bench as much as I could, not able to tell if it was my position or the vibrator in my ass that was rendering my lower body numb. As I moved I felt a huge burst of pleasure as the vibrations hit the right spot and it was all I could do not to moan like a bitch and give myself away. Biting on to my arm, I lay on the bench with my heart racing from a mix of pleasure and fear.
Maybe it was just a feeling of time moving slower because of my delicate situation, but if not Derek took almost twice as long as he regularly did on break that night. After I heard him leave the bathroom, it was difficult to track where his steps were coming from in the apartment. My panties and the bench below me were completely drenched in the pre-cum that had poured from my cock trapped in the skimpy underwear, I had tears running down my face from the unexpected exertion of keeping myself in that position for so long without making a sound, and I could still feel my heart skip whenever I thought it sounded like Derek was walking my way and I was fucking loving it. Feeling so helpless was a huge turn on and as soon as I heard him leave the front door I began riding my ass up and down on the vibrator and within seconds was soaking the workout bench with a massive load as my dick emptied spurt after spurt of satisfied cum. I breathlessly collapsed on the bench and fell asleep in a sticky mess. I woke before Derek got back and managed to clean up without incident. Feeling totally satisfied, and honestly kind of proud of myself, I knew I had found my new source of pleasure.
It quickly became the highlight of my week. I avoided jerking off most other days, couldn't remember the last time I felt like sleeping with a girl, and every Tuesday after the slow burn of sitting tied up on the vibrator for the duration of Derek's break at home I would ride myself to a body-shaking orgasm while calling out his name. I seemed to have finally found something sexy and risky enough to stave off my feelings for Derek and actually found myself more comfortable around him, though still keeping up my unspoken devotion to keeping him happy around the house.
I had become so used to my sneaky sessions in the storage closet that I just stashed everything I needed hidden in a box behind some of Derek's stuff. I had still only seen him enter the room at all one or two times since I began using it for my own activities so I felt safe in the fact that he would remain clueless. One particular Tuesday night I was dancing around the apartment dressed up and playing maid to get in the subservient mood, doing some quick cleaning and already thinking about the impending fullness my asshole was going to feel. I nearly tripped over a small package sitting in the doorway and picked up. It had Derek's name on it and had just been delivered that day, he must have seen it on his way to class and just set it in the front entrance. I went to place it on his bed and continued on with my routine until I couldn't handle it and set myself up on the workout bench. I had begun going in earlier and earlier so that by the time Derek got home I was a whimpering mess on the bench, barely in control as I listened to my stud roommate going about his business oblivious to me hidden away so close. I had become used to his routine and absentmindedly listened to his footsteps tracing his path from his the front door, to his bedroom, and then towards the bathroom.... until he walked past the bathroom and my chest nearly exploded when I heard the door to the storage closet start rattling in the frame behind me.
Not wanting to believe what was about to happen, I stopped moving, stopped breathing, stopped anything that might give me away. It was of no use as I heard the door creak as Derek grabbed the doorknob, turned and pushed the door inward. A chilling draft of air crawled up my exposed ass and back as the light came on.
"Uh, Andy, what the fuck is going here!?" I heard his voice from behind me and didn't have to look at him to see the look on his face.
I turned my neck involuntarily and immediately regretted it when I saw the 'what have we here?' look on Derek's face as he was standing in the doorway holding the small package I had earlier placed on his bed. His lips didn't betray even a smirk but I could tell he was amused with what lay before him.
"My folks have been sending me old shit from back home, I was just coming in here to put this one on the shelf." he said as he held up the package before tossing it to the side as he stared at me. "I mean, I knew you were in the closet, but I didn't know you were in THIS closet doing... what are you doing, buddy?"
His trademark 'trust me' smile was now on full display as I was still reeling with what had just happened to me. I was tied down and only able to turn my head to see him with the vibrator humming away in my ass and filling the silence as Derek stared down at me from the doorway. As much of a thrill as it was to imagine him seeing me like this, now that it had happened I found myself unable to even think.
"Um, Der, I can explain thi-" I stammered, my voice wavering with each uncertain word.
"Don't bother, I thought you were going to try to explain all that gay shit you were watching online a few weeks back but you never brought it up. You didn't think I just forgot did you?"
I wasn't able to maintain eye contact with him past this point so I turned my head back and dropped in on the bench, not sure what to say for myself. He saved me the trouble.
"Andy, Andy, Andy. So naive aren't you? Look, I don't hate you cause you're a fag now. We're friends! But it's something you could have told me and the other people in your life. Don't you think they deserve to know?"
"No! Please Derek, don't tell anybody about this. I didn't know what to say before, I didn't know what you would do." I panicked at the thought of everybody I knew finding out what had gone on in this room. My dick, which had been rock hard, was now shriveled and soft but still leaking pre-cum into my panties as I lay there in shame.
"Shh, it's okay. I told you we're friends, I won't do anything you don't want me to. But I have to get back to class, it's going to be tough not to say something while I know you're locked up here like this"
"I can have everything clean and back to normal by the time you get back, you'll never know anything happened! Just please don't tell anybody!" I pleaded to him.
He stepped up beside me, placing a hand on the back of my head and turning my face to the side, so I was nearly staring him in the crotch. He reached down and grabbed the rope securing my wrists and retied the knots so I was now unable to work my out of them.
"I wouldn't count on that, man. You'll be waiting for me right here when I get back. I won't be more than a couple hours." he winked at me and with that turned out the lights and closed the door.
I heard him walking away but suddenly his footsteps froze, and came back in my direction until he stopped outside the closet door.
"I just thought when I called you 'man' just now, you really don't look like a man anymore and I think I like you better this way. So you better get used to being Brandy while you're in this apartment. It's not too far from your old name, so you should be fine." he knocked on the door a few times quickly and left.
As I heard him locking up the apartment I was left tied to the bench and it may have just been the vibrator doing it's job but as I lay there contemplating my new reality I could feel my dick twitching as it came back to life while I thought about what Derek had in store for me when he got home.
Thank you for reading! Part 2 is on the way but in the meantime I'd love to hear any feedback or criticism so please feel free to email me and I'll be back soon with the continuation xx ;)