Schooldaze — Part 4

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For the next eight weeks, I sucked Henry’s cock as our desires and schedules permitted. Sometimes I would just throw on some panties, a slip, and some makeup and gulp his tool. Other times I would get the dildo out and we’d have a ‘complete’ session. For practice, I always tried to stay ‘in voice’ regardless of how long a session lasted.A ‘complete’ session usually consisted of me getting dressed up all the way — skirt, blouse, heels, etc. Then we’d fool around on the bed for a while with me teasing and stroking his panty-clad cock and him groping my tits and occasionally reaching inside my bra cups to tweak my nipples.After a while, I’d release ‘Little Hank’ from his satin prison and start sucking like it was the last cock I’d ever see. Eventually, the dildo would come out. Sometimes I would stick it to the bedrail like the first time. Other times, Henry would use it on me, sawing it in and out of my hungry hole.A couple of times we got more inventive and stuck it to the side of the pedestal sink in the bathroom. Henry would sit on the edge of the bathtub and I’d blow him while I ‘got fucked’ just bent over at the waist. Those were some of our hottest sessions.Afterward, I would shower and then slip into a satin nightgown. Henry had continued to buy me whatever took his fancy. If it was the first time I wore one of his gifts, he would jump me as soon as I emerged from the bathroom in it. It took me by surprise the first time he grabbed me.He hoisted me clean off of my feet into his arms and then laid me on my bed, my head near the edge. He hovered over me, straddling my head, his semi-erect cock conveniently close to my mouth. I opened wide and sucked him in. As he reached full hardness I pushed away from the wall until my head hung over the edge of the bed. Then Henry proceeded to fuck my face, literally, his balls all but smothering me, covering my nostrils as he buried his bone to the hilt again and again and again.After a second session like that, I would drift off to sleep. If I slept in a nightgown, I always awoke with Henry’s early-morning hard-on at my lips.Only every so often Henry would feel me up, but he never touched my cock in my panties. Once he came close, his thumbs brushed my hardness as they returned from my stockinged legs. He paused and an electric shock went through me. I thought for a brief moment that he might stroke me off. I wanted him to so very badly. But as soon as I thrust my hips up, he withdrew.Henry had a beautiful cock and I appreciated the freedom he allowed me. I loved how good he felt in my mouth and the way his cum tasted, but I was starting to hunger for more. Under Ms. Callahan’s tutelage, I seldom had fewer than three or four cocks at a time to suck, and the lack of variety was starting to weigh on my mind.Fate, however, soon intervened.It was time for mid-term exams and we were all pretty worn out. We’d been studying our brains out and working on papers and such. Henry and I had finished our last tests and were chilling out in our room when there was a knock on the door. “Come in,” we both chimed.”Hey guys,” Brendan said. We hurried to stash the beer we were drinking. He seldom made surprise visits, but his justice was known to be swift and terrible. He sat down on the far edge of my bed. He was wearing a pair of blue nylon running shorts that showed off his well-toned and well-tanned legs and a practice jersey kind of half-shirt that revealed his six-pack abs.”Relax,” he said, “I’m not here in any official capacity. I was just looking for someone to hang with for a little while. I’m not in the mood to be the RA today.””What’s got you down, buddy?” Henry asked, “Mid-term blues? Girl trouble? What?””Both, actually. Well, a combination of the two together, I suppose. I would kill for a beer right now. You guys got any?” Henry and I shot each other a quizzical glance. We both shrugged.”C’mon, guys. Hand one over. I need to unwind.”I reached down beside my bed and passed a can to Brendan. “Want to talk about it?” I said.”Nahhhh,” he said as he popped the beer open. “Not much to talk about. Kim gets this way twice every semester. All she wants to do is study. I keep trying to tell her that sex is a good stress reliever, but she thinks I’m just doing all my thinking with my Johnson.” Henry and I picked our beers back up as Brendan continued.”The last time this happened I went hunting for some pussy in the local clubs. I found this little Şerifali Escort hottie who was out drinking instead of studying and we hooked up for the night. Just my fucking luck. It turned out that her roommate was a friend of Kim’s, so I got busted.”Boy, I thought to myself, for someone who didn’t want to talk about it, he sure was doing an awful lot of talking about it. He finished his beer and motioned for another. I handed him another can.”Christ, it took me almost three months to get back in her good graces. That’s why I decided to pay you guys a visit instead. At least I can’t get into trouble here.”Talk soon turned to football. It was hard, but I did my best to seem interested. Since I never really hung around the jocks, football was not one of my interests. However, I picked up enough of it while I was dressing for and sucking off the senior squad that I was able to keep up and not look completely stupid.We talked about school as well, and the beer continued to flow. Henry and Brendan had at least two more apiece, and I had sucked down three myself. We were rapidly approaching the end of the 12-pack when the subject turned to girls.Brendan was all but sprawled on the bed by now with one leg hanging off to one side and I could see up his shorts. He wasn’t wearing any underwear and he had cut out the built-in ‘panty’ in his nylon shorts because my vantage point left me no doubt as to what he had between his legs. Brendan talked about some of his ‘conquests’ from his first two years. Henry talked exclusively about some of the girls he’d known back in high school. As the details grew more graphic, I stole the occasional glance up Brendan’s shorts, watching his bulge grow and grow.I, of course, was at a bit of a loss for words. Henry noticed my uncomfortable silence and subtly tried to steer the topic to another subject. Instead, Brendan stood up suddenly. He grabbed his dick through his shorts and gave it a hard squeeze.”I gotta go drain this thing,” he announced. “Mind if I use your can?” Henry and I nodded and huh-unh’d in unison. Brendan went to the bathroom, leaving the door open. We heard his steady stream of relief. When he finished, he came back and flopped on the bed once more.As he passed by me, I noticed that his cock was still quite hard, tenting out the front of his shorts quite noticeably. “Toss me another beer, Marty,” he said to me. I reached down beside me and came up with the empty 12-pack container.”All out,” I said.”Shit,” Brendan said. “I could use a couple more beers.” He lay there, almost reflectively quiet. He reached down and adjusted himself inside his shorts. “Looks like I could use a blowjob too. I thought it was just a piss hard-on but I guess I was wrong.”I had to stop myself from diving mouth-first into his lap. But a sudden thought struck me.”Henry, what’s the name of that townie you know?” I asked, using the term reserved for locals who didn’t go to the university.”Huh?” he responded.”That girl you hang with whenever the coeds don’t pan out,” I said. “The one that you said could suck a golf ball through a garden hose.” If we had been sitting at a table I would have kicked him under it. I settled for giving him a “WTF” look.A light went on in Henry’s eyes as understanding came to him. “Ohh, THAT girl,” he said. “Stacey’s her name.””What the fuck are you two talking about?” Brendan asked.”It’s perfect, isn’t it, Henry?” I said, on a roll now. “She could come up here and blow you, and since she’s a townie, there’s almost no way she’d know Kim, is there?” A knowing grin began to spread across Brendan’s face.”You guys would really hook me up?” he asked.”Well, sure I would,” Henry said. “She’s crazy about sucking cock. And she deep-throats too. I’m sure she wouldn’t mind if a few of my friends join us. After all, it’s mid-term and we could all use a little stress relief.””Fuckin’-A,” Brendan said.”Tell you what,” Henry said. “You go get some more beer and I’ll go get Stacey. I’ll meet you back here at say, four-thirty. That gives me forty-five minutes to make the trip into town with traffic. That alright?” Henry shot me a questioning look. I nodded slightly. My mind was racing to come up with a story to cover why I wasn’t going to be here when Brendan got back.”Well, in that case, I’ll go to the grocery store on the other side of campus to get the beer cheaper,” Brendan said. “You wanna ride along, Marty?””Sounds Şerifali Escort Bayan great, Brendan…,” I started to say, then, “Ahhh, Shit! Four-thirty? I almost forgot. I’m supposed to meet that girl from my Psych class — you know, that Latina with the huge tits — at the library in twenty minutes. She needs help finishing her paper. I’m already so fucking late.””No shit?” Brendan said. “Well, that’s too bad Marty. I guess I’ll have to drink your share of the beer. Maybe you’ll get lucky with your study date.””Well, you take my turn with Stacey then,” I said. “Maybe Liz will feel like showing me some gratitude.” I went to my desk and started rummaging through books and papers like I was looking for something.”Well, let’s get going then,” Henry said, grabbing his car keys off of his dresser.”Fuckin’-A,” Brendan said again. “My dick ain’t getting any softer.” Henry and Brendan headed past me and out the door while I made a good show of stuffing some papers and other crap in my backpack.”Good luck, guys,” I said.I gave them a good head start and then followed them down the stairwell. I heard Henry’s car starting up, and I saw Brendan pulling out just behind him. I made a display of dashing out the door, just in case Brendan was looking in his rear-view mirror.As soon as he disappeared around the building I did a sharp U-turn and sprinted back up the stairs. I had less than forty-five minutes to get Stacey ready for her college debut.As soon as I reached our room, I threw my backpack into the closet and retrieved the box that held my heels. Fortunately, I had already been half-planning a ‘complete’ session with Henry to celebrate the end of mid-term exams, so my outfit was already pressed and on a hanger. I quickly stripped out of my boy clothes and stuffed them into the box, placing it back up on the shelf in the closet.I grabbed my clothes and heels and headed for the bathroom, stopping to get my lingerie from my dresser drawer. I assumed Henry would be coming back sooner than forty-five minutes and I wanted to be ready when he got back, if possible. I figured he’d want to talk about what was going to happen and I wasn’t sure I wanted it too planned out beforehand.I started with the lingerie. I had picked up some new stuff as a surprise for Henry. I slipped into the padded underwire demi-bra and then fitted my breast forms in place. I checked their look in the mirror. The bra was a zebra print and the satin and scalloped lace trim was hot-pink. Next came the matching garter belt. I was glad I had shaved (all over) before we started drinking the beer earlier.I rolled my black seamed stockings up my legs and clipped them to the garter belt. I checked my seams as best I could to be sure they were straight. The matching thong panties were next. I loved the way thong panties felt snugged up between my ass-cheeks. The lace on the front of them formed a sexy ‘V’ pattern. I tucked my maleness back between my legs as I had done hundreds of times before. I checked my profile in the mirror and liked what I saw.I decided to slip into my skirt before I did my makeup. It was a black leather mini-skirt. Although I wasn’t short, I’d bought my size in petite — it was 2 inches shorter than the ‘misses’ length. All in all, I’d say it was about sixteen inches long with a zipper in the back and a small walking vent, more for decoration than function I was sure.I had applied my foundation, eyeliner, eye-shadow, and blush before Henry came back. I hadn’t bothered to close the bathroom door and he came in, watching me intently. He had never seen me in mid-transformation before, I realized.”So you really want to do this?” he asked. “I can still tell Brendan that Stacey wasn’t home.””But Stacey is home,” I said. “It will be alright, Henry. It will.” I was already speaking in my femme voice. An extra eight weeks of practice and I had all but perfected it. “Why, are you worried?””Well, no… yes… I don’t know,” he stammered. I was slipping into my black patent leather Dorsey heels. They had 5″ spike heels and ankle straps. They gleamed brightly in the light.”I’m not sure I understand, Henry,” I said. I put one foot up on the toilet and fastened one of the ankle straps. Henry had seated himself on the edge of the bathtub.”Well, it’s just… I… What if he finds out who you actually are?” he finally blurted out.”So you’re worried because you think you Escort Şerifali have as much to lose as I do if I’m discovered, right?” I fastened the other ankle strap.”Well, I suppose so, yes.” I turned and leveled my gaze at him.”Henry, aren’t you the one who told me that I’m a great cocksucker?””Yes. Hell yes!””Has my femme voice improved since we came here?””Yes.””So once I get my lips wrapped around his cock, do you think he’s going to bother to check to see if I’m all-girl?””Probably not.””And once I’ve swallowed a big load of his sperm, do you think if he found out that I’m not a girl that he’d go telling everybody that he got blown by a guy?””Definitely not!””And would he tell everyone that you had fixed him up with a guy? How would he explain it to Kim?” I gestured and Henry handed me the hanger with my top on it. It was a fuchsia slit-sleeve tee top made out of a polyester/spandex blend. It had a sexy draped neckline that would really accent my cleavage.”I’m starting to see your point,” he said. I slipped it on over my head, being careful not to smudge my makeup. I surveyed myself in the mirror.”Good,” I said to both Henry and my reflection. I reached for my lipliner pencil and tube of lipstick.”But…,” Henry began.”But what, Henry?” I carefully outlined the shape of my lips with the practiced hand of someone who has done it a million times.”What if he… I mean… Say he isn’t, you know…” I filled in my lips with a dark pinkish-red Revlon shade called “Cherries in the Snow.””What, Henry? Come on. Tell me.” He sighed. I blotted my lips on a piece of toilet paper.”What if a blowjob isn’t enough?””Huh?” I said.”What if he wants to fuck you, too?””Why would he want to fuck me?” I asked. I arranged my ‘trademark’ shoulder-length auburn wig on my head.”Because…,” Henry said, his voice dropping off mid-thought.”Because why?” I said. His voice dropped to an almost inaudible whisper.”Because I’ve thought about it, too,” he said. I turned and looked at Henry. He looked like he had just swallowed his Adam’s apple.”What did you say?” I asked him. He flushed.”You heard me,” he said.”Say it again, Henry,” I said, “I want to be sure.” He sighed.”I said I’ve thought about it, too,” he said.”Thought about what, Henry?””C’mon, we both know what about,” he said evasively.”I need to hear it, Henry. I need to hear it from you directly and in the most unambiguous terms possible. Tell me.” Henry was silent. I waited.”I’ve thought about what it would be like to fuck you in the ass,” he finally blurted. I waited some more. He continued, rambling now.”Well, I mean, I’d like to fuck Stacey’s ass. I mean, uh… I don’t look at guys’ asses and think I want to fuck them. It’s just like I’ve fucked other girls in the ass before and enjoyed doing it, and then I thought well; one ass is as good as another. And I do think of Stacey… er… you… er… when you’re dressed up I only see you as a sexy girl and since I know you like having a dildo in your ass, I figured you might like to try the real thing a few times just to see if you liked it, you know….” I placed a finger on his lips to quiet him.”It’s okay, Henry,” I said. “I understand; really, I do.” Shit! I realized that I had almost forgotten to do my nails! I grabbed my Max Factor quick-dry polish and sat down on the tub next to Henry. As I applied Pink Flame (how appropriate!) to my nails, I continued to explore this new development with Henry.”So how long have you been thinking about this?” I asked.”Well…,” he started but trailed off.”Okay, let’s start with an easier question first. How many girls have you fucked in the ass?””Three,” he said matter-of-factly. Then, “Well, two I suppose. The third girl agreed to try it but then said it hurt too much. I barely got the head of my dick inside her before she was crying and screaming at me to pull it out.””And you liked it, I assume.””Hell yeah.””Why?””Well, I don’t know. It’s a lot tighter than most pussies, of course. But I guess the biggest turn-on is the taboo — the idea that you’re sticking it to some girl where it isn’t supposed to go, you know?””How many times did you fuck these two girls in the ass?””Oh, the first girl did it only once. She said it was okay, but that she didn’t enjoy it as much as I did. Now the other girl was a real ass-slut. After we fucked, she’d blow me hard again and then take me back up her ass. She really got off on it.”“Okay, and when did you start thinking about fucking me?” I blew gently on the nails of my left hand and switched to painting the right ones.”It’s hard to say. I guess it’s been growing in my mind for some time now. I remember how hot that first night here with you was. You looked so sexy slamming yourself onto that dildo.”

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