Schooldaze — Part 4

It was the first day of college orientation, and I wandered around the dorms more than just a little confused looking for my room when I heard a familiar voice shout, “Hey, Martin!”It was Henry. It was because of Henry that I’d gotten into this school — a school well-known for its technology programs but better known for its football program. Well, Henry and Ms. Callahan; they had both written extremely persuasive letters of recommendation to the school’s admissions office.”Our room’s up here, buddy,” he said.”Our room?” I said as I looked at him quizzically.”Yeah, our room,” he answered. “I mean, how lucky could we get? It turns out that our Resident Advisor was also one of Ms. Callahan’s boys when he went to high school.”I pondered the possible implications.”The room’s awesome,” he continued. “We have the only other room on our floor with its own bathroom. It used to be the Assistant RA’s room, back when they had them here. C’mon. Let me help you with your stuff.”We lugged my stuff upstairs. Henry had already put his things away, and volunteered to help me with mine. I politely declined. I had brought a few things with me that I wasn’t sure I wanted Henry to see. At least not right away. He said he’d catch me later and hustled out the door.We essentially had three small ‘rooms,’ if you could call them that. Just inside the door were two small study cubicles, each with its own chair. Past that was our communal closet. Around the corner and you were in the ‘bedroom.’ Two twin beds were shoved against opposite walls, making a narrow walkway between them that led to the private bathroom that Henry had mentioned. Each bed had a chest of drawers at its foot. It didn’t look like there was much room to improve the way the space was laid out.I unpacked my belongings, mostly clothes, and put them away. I was careful to hide my bras, panties, and other lingerie under my more mundane boy-clothes. I had also brought a few blouses and skirts, but those were kept hidden on hangers underneath bulky sweaters.I emptied my school supplies into the desk and then stashed my dictionary and thesaurus in the top drawer. My high heels went into the box that had previously held my school supplies, and went on the back of the shelf above my half of the closet. My breast forms, wig, makeup and vibrator went into the same box. I guessed I was as ready as I’d ever be.When Henry didn’t return, I went to the auditorium for the Dean’s welcome and then went along on the freshman tour afterwards. The tour dumped each of us off at our respective dorms, where the RA’s for each floor were waiting to give us their orientation. We all went upstairs to the common room on our floor and listened to Brendan, our RA, for about 30 minutes. Then he made us go around the room and introduce ourselves by room number and tell everyone what our major was. It was then that I noticed that Henry still wasn’t there.After all the introductions were made, Brendan asked for questions. As the other freshmen fired questions about parties and girls and drinking at Brendan, I studied him closely as he gave the ‘old school’ answers.He wasn’t too tall, but he wasn’t exactly short either. He had an athletic build and an end-of-summer tan. He was wearing a red sleeveless tee and gray athletic shorts. His feet were covered by the white sneakers he wore, though he didn’t have on any socks. His sun-bleached blonde hair was close-cropped, almost like a military haircut. The blue of his eyes was piercing, especially contrasted against his tanned face. A pair of Oakley’s with a neon-green leash was perched on the top of his head. I had trouble imagining him wearing red panties for Ms. Callahan as she fucked him with ‘the Terminator.’As I thought about the Terminator, my mind drifted aimlessly, reliving each and every thorough fucking I’d received with it. It made my ass twitch just a little with wanton remorse. I was sure going to miss that beautiful black dildo.”Okay then,” Brendan said, jolting me from my reverie. “If there are no more questions, then have a good night. Remember, if you need anything; don’t bother me after 9 p.m., that’s when I study.” He laughed. The rest of the room laughed too, and then we all went our separate ways.I went back to my room, thinking that I’d catch a quick nap or do a little light reading before dinner time. I didn’t really know anybody here except for Henry, and I had no desire to follow him around like a lost puppy for the next few days before classes started.When I rounded the corner in our room, I found Henry on his bed facing the wall. Since he appeared to be sleeping, I went into the bathroom and closed the door before switching on the lights. I gasped when I looked around.The medicine cabinet door was standing open. One side was rather sloppily stuffed full of Henry’s and my shaving stuff. But the other side had all of Stacey’s makeup and other beauty needs neatly arranged Åžerifali Escort on the shelves. Hanging from the shower curtain rod on a hanger was a sexy baby doll nightie.It was sort of a pale aqua color and was made of shimmering satin. The front had three bands of inverted V’s made of delicate ivory lace. It looked like a piece of vintage lingerie from the 50’s. I reached out to touch it, and the spaghetti straps slid easily from the hanger. I caught it, the cool satin enveloping my hands and arms. The hanger swung gently back and forth, waving a pair of matching thong panties as it did so. So much for it being vintage!Just holding the soft material in my hands caused my dick to stir in my pants. Gingerly, I hung the garment back up. I looked over and on top of the toilet tank was a box that I recognized, and on top of that was an envelope leaning against the wall. A name was written on the outside of the envelope in Henry’s handwriting. It was addressed to Stacey.I put the toilet seat and lid down and sat down. My hands trembled as I picked up the envelope. Only the bottom of the flap was sealed, and I opened it, pulled out the handwritten note inside, and began to read.Stacey, this is just my way of letting you know that I consider this room asmuch yours as mine and Martin’s. I know that we did a lot of thingstogether that last semester of high school that guys don’t normally like totalk about. I know it was a great pleasure for me and the rest of the guys,and I like to think that you enjoyed it too. I want you to know that thereare no expectations here, just this open, honest offer. If you desire to dressup in our room, I want you to feel comfortable doing it. Just because you’redressed does not mean that I expect any sort of sexual gratification from you.Of course, if you ever get the urge, I’d also like you to know that I’m ready foryou any time!HenryP.S. I think that baby doll nightie would look better on you than thosesad, worn-out gray cotton shorts you always sleep in!I was stunned. When I’d packed all of my things to come here, I hadn’t even considered who I would be rooming with. And now I had an open offer to enjoy the freedom of being Stacey as often as I liked. I wasn’t in a position to look in the mirror from where I sat, but I know my mouth must have been standing wide open. The rest of my body, however, wasn’t quite so immobilized. I could feel the tightness of my nipples, hard under my cotton tee shirt, and I had to readjust my crotch to make room for my now hard cock.I stood up and looked in the mirror. Then I glanced at my watch. There were at least a few hours before the dining hall opened. I decided that there was one sure way to thank Henry for this special present. I slowly opened the door and looked into the room. Henry hadn’t moved. I quietly opened one of my dresser drawers, grabbed a few things from the bottom of the drawer, and then returned to the bathroom. I silently locked the door.I stood at the mirror and applied my makeup, as I had done hundreds of times before. Next, I stripped out of my plain boy-clothes, taking special care to not smudge my makeup job as my shirt came off. I slipped the baby doll off of its hanger and half-folded it on top of the toilet seat. I pulled the satin panties from the hanger next. I slipped them up my legs and then tucked myself back between my legs as best I could.I took the stay-up stockings I had brought from my dresser and proceeded to pull them on. They were white with Cuban heels and had a seam running up the back. I clipped my bandeau-style white bra around my chest and then opened the box on the toilet tank. From it, I took out my breast forms and fitted them into the bra. Now that I had the right shape, I slipped into the baby doll.I slowly pulled the cool satin up my legs and onto my chest. I slipped my arms into the spaghetti straps one at a time, and then adjusted them until the fit was perfect. I looked at myself in the mirror, stepping back as far as I could to see as much of me as possible. I twisted around, making sure my seams were straight.One more dip into the box on the toilet tank produced my auburn shoulder-length wig. I didn’t have the time to style it properly, so I just shook it out as best I could and gave it a quick finger-styling. I placed it on my head and then appraised myself in the mirror one last time. I blew myself a kiss and then took a deep breath to calm the butterflies in my stomach. I opened the bathroom door and stepped out into the room.Henry was still lying with his face toward the wall. A sudden thought struck me. Had I remembered to lock the door? I tiptoed past Henry to check the door. A good thing I did, too! It was most certainly unlocked. I turned the deadbolt and then headed back to give Henry a pleasant wake-up surprise.His voice stopped me dead in my tracks. “I was right,” he said. “You do look Åžerifali Escort Bayan better in that than you do in your ratty old shorts.” He was sitting up in his bed with his blanket still up around his waist. “I want you to know that I meant every word of that note. No pressure.” He grinned. “But I am glad you decided to let Stacey share our room,” he added.I stepped up to the foot of his bed. “Mind if I sit down?” I asked. I was using Stacey’s voice. I knew it wasn’t a perfect femme voice, but I knew the more I practiced it, the better it would get.He patted the bed beside him. “Please do.”I sat down close to the foot of his bed. “The stockings are a nice touch,” he said. “Very sexy. I’ve always liked girls in stockings.””Thank you,” I said. “For everything, I mean. This lingerie is lovely and it really was very considerate of you to even think about Stacey.””No problem. And I really do mean what I said. No expectations here.””Henry,” I said, “you need to know one thing. I think you already suspect it on some level because of all the ‘research’ you did into my dressing before that fateful night in the locker room. Dressing up for me has always been a purely sexual thing. As you well know, I usually dressed up and masturbated, sometimes using a vibrator on myself, and sometimes not.” I placed my hand on his shin. He shifted around a little bit, but his eyes remained fixed on mine.”Until that night when you first met Stacey, I had never even considered what it would be like to actually be with a guy. I don’t know about you, but I was nervous as hell. Even though I must have sucked you off a hundred times that last semester, I still remember what it felt like the first time I touched your hard prick.” I ran my hand up his leg to just above his knee. “I still remember my first taste of your pre-cum, the way your hot shaft felt on my tongue and the way your throbbing cockhead felt when I first closed my mouth on it.” My hands traveled further up his inner thigh.”I guess what I’m trying to say, Henry, is that before that night, before you and the rest of the guys, before Ms. Callahan and the Terminator; before all of that, I guess there was some kind of void in my soul that hadn’t been filled. And all of my dressing and whacking off and vibrators was just my way of searching to fill that unknown space. I guess what I’m trying to say, Henry, is thank you.” My hand was near his crotch now and I had to slide a little closer up the bed to stay in range. I locked my eyes onto his.”I’ve all but had this forced upon me from that first night, Henry, although I’ll grant you that I didn’t take much persuading. From now on I want it to be different. I want to do this because I WANT to do it. I want to do this because YOU want me to do it.” I took a deep cleansing breath and then opened up my soul. “I want to suck your cock, Henry.” I moved my hand up and grabbed his hard dick through the blanket and began to stroke it gently. “I want to suck your cock because I’ve missed having it in my mouth. I want to suck your cock because YOU want to feel my lips wrapped around it once again.”Henry groaned. “God, yes,” he said. “Suck my cock, Stacey. Fuck my prick with your pretty little mouth. I want to feel your lips and tongue on me again. Go ahead, Stacey, suck me.”I pulled back the covers and gasped in surprise. Henry was wearing a pair of flame-red satin panties. His beautiful cock was tenting out the front of them. There was some writing silk-screened across the front. I allowed myself a giggle as I read it, “I’m Your Obsession.” The i’s were even dotted with little pink hearts.”They were sort of a going-away present from Callahan,” he said. “I guess I just got so used to wearing them for her — wearing them when I was with you — that it seemed, somehow, natural.””I like them,” I said. “Knowing that you wore them just for me makes me want you even more.”I caressed his hardness through the satin, running my hands up and down his length and tracing the outline of his bulge with my fingertips. He moaned softly at my touch. I slowly leaned forward, hooking my index fingers into the waistband of his panties.I pulled down and his cock sprang free from the stained satin that had recently contained it. It wasn’t free for long, however. Before it had a chance to rebound my mouth was on it. I immediately slurped as much of it into my mouth as my position would allow.Henry groaned as most of his cock disappeared between my painted lips. It had been almost three months since I had sucked any cock. After school let out there was never any real reason for those of us under Ms. Callahan’s thumb to get together. Except that one time.”Mmmmmmmmmmm,” Henry said. “I’d almost forgotten what a great cocksucker you are, Stacey.” I slipped him out of my mouth for a moment.”Well, I know I’m a little out of practice. It seems like it was ages ago that Escort Åžerifali I last had you in my mouth.” I shifted to a better position and went down on him once more. As my head bobbed up and down in his lap, he recalled our last meeting aloud.”I remember the last time we were together. It was the night of the Senior Sports Banquet, two weeks after school let out. You were wearing the school colors that night — a short black leather skirt and a silky gold blouse. The rest of us had to wear suits and ties. I remember how Callahan told Coach that she’d make sure we were all presentable for the senior photo. He had us meet her in the locker room an hour before the dinner started.””She strapped the Terminator to a toilet seat in the last stall and had you hike up your skirt and sit down on it. Then she had us get dressed in our suits. One by one, she checked us over, made sure our ties were tied correctly, made sure we had our panties on, and then sent us into your stall.” I slurped at his dick as he continued.”There were only twelve of us seniors that night, and you blew every last one of us. I remember that she told us we weren’t allowed to cum in your mouth that night; that we had to shoot our loads all over your face. I went first, and the other team’s captains were right behind me. After I blew my load I went and stood on the toilet in the next stall.” I moaned softly. All this talk of that night was turning me on immensely. I took Henry’s cock all the way down my throat.”Yes,” he hissed with a sharp gasp. He bucked his hips a little and placed his hands on the back of my bobbing head. Then he continued.”I stood up there and watched you with the other guys. You looked so hot bouncing up and down and fucking yourself with that dildo while blowing them. Just the sight of their red panties, the black dildo, and all those messy globs of white cum dripping from your chin and staining your gold blouse were enough to get me hard again.” I came up for a quick breath of air and then went back to deep-throating Henry. His hands stayed on my head, guiding my efforts.”Callahan was so busy making sure everyone was cleaned up afterwards that she didn’t have time to notice that I went back for seconds. When I stepped back in front of you, I don’t think you even realized it was me. You looked like one of those women in those low-budget porno flicks. Your makeup was all smeared and your face was covered with spunk, some of which was drying into a white crust and the rest of which was running down your face to drip off of your chin.” I pulled up from his cock, took a deep breath, and went back down one more time. His re-telling of that night was making me hotter and hotter and I wanted so badly to taste his cum.”You just leaned forward and took me between your cumdrenched lips. The whole scene was so hot, watching my cock slide in and out of your messy face that I didn’t last very long. I pulled back and blasted another load…” I interrupted his train of thought by suddenly coming up until just his cock head was in my mouth. He moaned as I licked it and suckled it.”Oh, God, Stacey. Uh-huh. Mmmmmmmmmm. Yeah, just like that. Uh-huh.” He was on the edge now, and I knew what I wanted was mere heartbeats away.I gave him just a few more seconds of intense head-sucking and then I plunged his entire length down my throat. He raised his hips and moved them in time with my bobbing head, fucking my face. Every time I was on the way up, I came almost all of the way off of his cock, shoving it back down my throat each time I went back down. Henry was going nuts.His hands were clutching the back of my head now and grinding my nose into his pubic hair. I had to fight to pull my head back up each time. He started moaning again, and I knew that this time he was coming for sure.He came up onto his knees, forcing me to slide off the bed and onto my knees beside it. He had a good grip on the back of my head, and now he was fucking my mouth fast. He shoved his cock all the way into my throat and then pumped short strokes before pulling back and going again. I did my best to keep my balance and still move with his thrusts.”Oh fuck!” he cried out. He buried his bone to the hilt and pulled my face as close to him as it could go. “I’m coming, I’m… ahhhhhh,” was all he said before he exploded in my mouth.I felt the first big spurt deep in my throat. His hands were locked in a death-grip on my head, but I pushed against him. The second spurt hit the back of my throat. I got his cock almost all of the way out of my mouth until I was able to catch the rest of his load in my mouth. Henry was still trying to hump my mouth and made little grunting and groaning noises as he spent his all of his pent-up lust between my lips.I was moaning too, savoring the flavor of Henry’s spunk once again. I swallowed every drop and kept him in my mouth as I felt him going limp. I sucked and sucked on his soft tool until there was nothing left to get from it.Henry dropped back onto the bed. His face was bright red, almost as red as his panties, and was covered in a fine sheen of perspiration.”God, that was so fucking fantastic!” he said. I was slumped on the floor next to his bed. “Thank you.”