Teen Stud and the School Therapist

"Well...I ended up cancelling on him Monday night, just saying vaguely that I needed to cancel. I made up an excuse and...well I took Jessica out instead, last minute. I spent all night worried about how he'd react."

"Well, yesterday he strolled up to me while I stood with Jessica and asked where I had been the previous night. Jessica's a bit intense okay? So she answered that I had been with her, and whether he had a problem with that? He gave her a grin but then just ignored her. I saw her turn a bright red as he continued to address only me. He just said that he hoped to see me that night, and that he could really use my help."

"When he walked away, Jessica started yelling at me for not standing up for her. We had planned on a date last night too and she reminded me about it before she walked away, fuming. Well...I ditched her."

"To tutor Ryan?" I asked.

He nodded his head slightly. "I don't even know why I did it really. I just know that Ryan had been so nice to me and she had been so terrible. I had had such a nice time with him during our last session..."

"Well, I went over, right? While I was there he kept complimenting me, this time on my body and even stranger things, like my lips, my hair. I didn't know what to do with all his compliments. I tried to brush them off, to dismiss them. But, honestly? I think I was enjoying the attention a bit. He just kept flirting with me, or at least I thought it was flirting, as I tried to tutor him. And...god help me...I...I started flirting back! I mean he's just so hot...so...big..."

Chris's eyes glazed over as he evidently pictured Ryan.

"Ch...Chris?" I had to clear my throat, which had become dry.

"Right, sorry. Well, somehow...we made it through the tutoring session. As I stood up to leave though, he grabbed my arm and gently, though insistently, turned me around. He pulled me into another hug and this time I pressed into him immediately. He cupped my ass and I...I just couldn't help it, I moaned."

Chris suppressed a slight moan now as well before continuing. He barreled on, as if he needed to get it all out in one breath. "I began running my hands over his body as he continued squeezing and cupping my ass. Then he took a step back and told me to take off his sweater. And...god help me...I did."

Chris gulped, "Have you seen his body? It's like he's carved out of stone. I continued to rub my hands all over him, uninvited, I didn't even know what I was doing, I just knew I needed to touch him...to feel him. Do you know what I mean?"

"Yeah..." I answered, without pausing to think. "I mean...I think I can understand that, Chris."

Chris didn't respond though, he just stared at the wall behind me, his eyes glazed.

"Chris. Stay with me."

Chris snapped his head to me and flushed crimson red. "Right...sorry about that. I really didn't meant to tell you all that...TMI right? Anyways, just then my phone started buzzing and it kind of snapped me out of it. I answered it, stepping away from him and...well it turns out it was Jessica. She was fuming, screaming. I told Ryan I'd better go and practically fled."

"Well...yeah she broke up with me. I don't even care so much though to be honest...I'm just thinking about Ryan now. Like...does he want to be my boyfriend? I don't know..."

"Mr. Caldwell? I don't know what to do about all this. It's wrong, it's all wrong but...I don't..."

"Chris," I interjected, "do you want to be in a relationship with Ryan?"

"I...I don't know. I don't...think so? You know? I mean if I try to think purely rationally, then no. I'm straight, plus it's so against my and my family's beliefs. But...at the same time...when I picture him..."

"Okay. But Chris, we have to listen to our minds. Not to our...body...if you know what I mean."

"I understand..." Chris's voice got quieter and quieter as he looked down towards his lap. "How should I handle this?"

"Next time you see him, I want you to make clear you want this to stop. That you don't enjoy his flirting and that you find it predatory and offensive." I couldn't help it, I felt I could kill two birds with one stone this way. I would help Chris, and, at the same time, show Ryan he didn't control all.

He nodded, more enthusiastically now. "Right. Right. Okay, thanks."

"Of course, anytime. And Chris, please come see me again next week and we can discuss this again."

"Okay." He answered, looking determined now.

As he walked out, he glanced back at me. "He...he calls me Monique, you know." He grinned slightly, embarrassed.

"Okay..."

As Chris walked out I couldn't help but look. His ass wasn't as nice as Janelle's...or mine. I immediately vanquished the thought.

———

That night, I ate and watched some tv, putting my troubles out of my head for some time. I tried to resist drinking, as I was still feeling like crap from the previous night's binge. After watching a couple shows, I went to clean up and go to bed. After my shower, as I went through my underwear drawer, my eyes fell on the drawer next to it.

Sarah's stuff.

I hadn't opened that drawer since she was last here but now, slowly, I did. As I remembered, it was filled with some of her backup clothes...including her underwear.

I picked up pair of light blue panties I had always found sexy. I felt the smooth material in my hand and pictured them on Sarah. For some reason, I pictured her in just these panties, pressed up against Ryan, his strong hands on her butt, squeezing the panties. Then, suddenly, I pictured the same scene, only Sarah was replaced with Janelle, her beautiful ass in the same panties being squeezed by Ryan. Then, god help me, I imagined Chris...as Monique...in the same position. My imagination played these images in my head over and over - Sarah, then Janelle, then Monique over and over and over. Janelle had the nicest ass and I found myself picturing just Janelle, over and over - making out with Ryan, her feeling his muscles, his hands groping her ass.

I rubbed the material in my hand. So soft. Before I could second-guess myself I dropped my towel. I bent over, put both my legs through the small piece of fabric, and pulled them slowly up my legs. As they slid up my thighs, I wondered at the stretchy material, which applied a light pressure as I pulled them higher and higher, and finally over my ass. They felt wonderful.

They supported my ass in the most comfortable manner - like nothing my boy underwear had ever done. I felt the hem line cup the bottom of my ass cheeks, pulling them up and out. My smooth legs (I had never really grown any body hair for some reason) felt wonderfully free and unconstricted.

Slowly, I walked to the mirror. Even with the tight panties you could barely make out my little dick. I ignored it. Wow, my legs looked damn good. Long and toned. I think I even had thigh-gap! All the high school girls wanted that right? They talked about it and their other insecurities all the time in their therapy sessions.

I turned around. My ass looked great. I was surprised. I arched my back a bit and stared in wonder. How had I never realized this before. If I didn't know any better I would have thought I was staring at a girls ass, and a sexy one! The cheeks pressed out, full, round and supple, the thin blue material wedging in between them slightly. The bottom of my ass cheeks were accented by a slight depression. The light played across the depression, accenting my round ass. I wiggled my butt a bit and was rewarded with a visible jiggle. Nice.

Somehow, I thought, these looked even better on me then they had on Sarah. How would I stack against Janelle though?

After staring for a while longer, stretching and bending experimentally, I went to pull them off. About to do so, I stopped.

What the hell, I already had them on. May as well be comfortable while I slept.

I crawled into bed and closed my eyes, thinking about sexy Janelle pressed up against Ryan's broad chest, wearing the panties I was wearing.

———

The next day I woke up feeling wonderful. As I stretch luxuriously, I realized I couldn't remember the last time I woke up so happy. Certainly not since all had begun to go south with Sarah.

I couldn't put my finger on what it was that made me feel this good, but I was incredibly comfortable, my legs freely moving from side to side, no wedgie or boxer shorts twisted out of place.

As I got dressed for work, I looked at my boxer shorts in my hand, about to pull them on. I looked down and giggled. It was so silly but hey, why shouldn't I feel comfortable? Especially if it was at least part of the reason I felt so good this morning. I thought of Ryan - hey, he wouldn't know so it was fine. I left them on, finished getting ready, and left for the school.

The day went by quickly and smoothly. For the first time in a long time my head felt clear and I was able to give my student patients 100% of my focus. I barely even thought about Sarah all day! (Well...I actually thought about her constantly but at least it didn't cripple me over the course of the day).

In the early afternoon I heard a knock on my door. I glanced up but before I could reply the door opened and Ryan stepped in.

"R-Ryan?" I stuttered, taken aback. People did not simply walk into my office unannounced. "Do you have an appointment?"

"No, but whatshername...the admin...told me you were in here and didn't have any appointment for an hour."

What was with this kid? "Okay but Ryan, that doesn't change the fact that you need an appointment."

"Well..." He smiled again, a twinkle in his eye. "How about now?" He shrugged, and my eyes focused on his massive shoulders moving up and down.

I sighed. "Fine. But I won't see you next time unless you have an appointment."

"Great. Thanks." He sat down on the chaise.

I collected my thoughts and took a deep breath.

"So Ryan, what would you like to talk about today?"

Ryan stretched out, putting his hands behind his head. Today he wore a long-sleeve shirt but it was thin and hugged tight to his chiseled body. He wore a matching pair of shorts, similarly thin and tight. His huge legs emerged from the shorts a couple inches above the knee, displaying his defined quads. I thought that one of his legs may have been as thick as both of mine combined. The chaise seemed to groan under the massive body it was supporting.

He replied."Oh, I don't know. I guess I'm just wondering how long until I win our little experiment."

"One doesn't 'win' an experiment, Ryan."

"True. Okay how long until my hypothesis proves true." He grinned at me.

I couldn't help but glance at his lap. The thinness of his shorts showed it off more than even before. The impossibly long snake rested across his leg, the head clearly outlined on the outside of his quad all the way on the other side of his huge leg. Jesus.

Somehow, I kept my voice steady, even while I stared at his cock. "It's not happening Ryan."

"Hmm...you seem pretty convinced."

I finally tear my eyes away from his amazing cock. (Amazing? what the fuck). "Ryan. I'm not gay. I have no interest in men. I am an employee of the school that you attend as a student. Furthermore, I have a duty to maintain a professional relationship with you. If what you are saying were to happen, I would be fired, lose my license and I could even go to jail. I would be ruined."

"I understand." He fixed me with an intense stare and I was transfixed by his deep blue eyes. "It's going to happen anyways. Do you know why, Princess?"

I couldn't look away from his handsome face. I glanced from one eye to another then...for some reason..towards his lips. "W...why?"

"Because I want it to. I want to feel that nice round ass stretching around my cock Princess."

I stared. My eyes ran down his huge body, almost of their own accord. I took in his round hard shoulders, his thick arms, his mountain of a chest and his flat stomach. With his arms up and me looking at him from the side, I could see the thickness of his chest taper steadily to his thin but muscular torso, the shirt outlining each huge muscle. They continued over his powerful legs before finally, inevitably, coming to rest on his cock. My eyes ran up and down his impossibly long cock more than once.

Finally, my mouth dry, my voice hoarse, I said: "I...I think you need to leave." It had barely been 5 minutes since Ryan had walked in.

"Already?" He asked.

"Yes." I struggled to get out. "You may not speak to me that way, Ryan." I gulped and finally brought my eyes back to his face. "And you are to call me Mr. Caldwell."

"Okay. I will call you Mr. Caldwell if..."

"If what?"

"If you prove to me right now that you're not wearing panties."

My face flushed instantly bright red and I broke eye contact. "I'm...I'm not doing that. Leave."

He smirked triumphantly. "Okay. I'll be back tomorrow. I'll even make an appointment this time...Princess."

He stood and I stood with him. He continued to tower over me though. He stared down at me confidently, dwarfing me, as I gazed up at him nervously. He broke eye contact, looking down my body, and grinned. Then he turned and left. His wide frame, rippled with muscles, and muscular ass, were clearly visible through his thin tight clothing. I stared at the teen's butt as he left.

Finally, I looked down and saw a slight but noticeable bump pressing out in my pants. I had a raging (and tiny) boner. Only now did I feel it pressing against the soft material of my panties. This is what Ryan had smirked at.

Shit.

————

As I drove home that night, I realized that my plan wouldn't work. He was both more aggressive and more patient than I had expected. He wouldn't simply stop and give up if a week passed without him shoving his massive teenage cock inside of me. He was probably with Sarah right now, fucking her brains out as she worshiped his muscular body.

I sighed at the thought, I think because I was jealous of Ryan...

No...If I ever wanted to get through to Ryan, and then get Sarah back, I needed to do something drastic. What though?

———

When I got home, I stripped down to just my panties and looked in the mirror. I really couldn't believe I hadn't realized it before. I had a banging body - just...a feminine one. My hips were wide for a male, and they sloped in to a thin and toned waist. I walked to my closet and pulled out an old halloween costume. It had a short wig that I fastened on. I went back to the mirror. Shit...If I didn't know better I would have definitely thought I was looking at a girl in the mirror, albeit a flat-chested one.

I closed my eyes and began to run my hands over my body. At first I imagined I was running my hands over Sarah's smooth sexy body. But I knew what her body felt like and mine was different...I was curvier (except in the bust). My mind switched my fantasy to Janelle. I was feeling her luscious ass and I moaned as I squeezed myself, now leaning up against a wall. But that I felt my own caresses ruined the idea that I was touching someone else. Instead, I imagined I was Janelle. All the sudden the hands feeling my body grew firmer, stronger. They squeezed and petted forcefully and I moaned out loud. I was in the parking lot, leaning against Ryan's hard body, his hands on my round ass. He owned that ass. It was his. One of his fingers snaked between those round supple cheeks and I moaned again, pressing my face into his chest, which was hard as a brick wall. I went to feel him - to run my hands along his incredible body, and one of his hands left my ass. Why...why was he stopping? I whimpered and opened my eyes as my hand tried to grope him...and stopped dead against the wall in front of me.

I blinked and slowly stood up straight, holding my hands away from my body.

I...I needed to get control of this situation. The plan formulating in my head was dangerous and risky. It was way outside the bounds of traditional therapy and I could easily lose my job. But was I a superstar or not? I wouldn't be restricted by "traditional" therapies. I could benefit my patient greatly if only I would step out of my own comfort zone. Yes...what I was planning could get me fired. But it also could bring Ryan under control...and Sarah into my arms.

———

The next morning I stood in front of the mirror. I again wore a pair of Sarah's panties - light grey with cotton in the middle and lace along the edges. I bent over and gave a wiggle, pleased with how incredible my ass looked in them. I pulled on a tight light-brown skirt Sarah had similarly left behind, which ended just above my knees. I finished the outfit with a faded ocean-blue draped blouse which wrapped snugly around my chest. The fact that it was adjustable made it the only thing I could possibly wear of Sarah's, given her massive chest.

I appraised myself. I looked damn good. My face still looked somewhat male with no makeup but my feminine features and strong cheekbones did me well there too.

I tucked the wig and my Princess outfit in my bag, got dressed, and went to work.

———

When I got to my office, the admin told me Ryan would be coming by at 11 a.m. during his free period. I swallowed and thanked her.

I spent the rest of the morning reviewing my files, bringing my observations of all my patients up to date. I found it especially hard to focus when I updated Chris's file. I shifted in my panties. The material felt so smooth and comfortable against my skin.

Finally, it was 10:45. I locked my door to get ready. I changed and put on the wig. I spent 10 minutes fixing myself up in the mirror, straightening my hair and maneuvering Sarah's clothing until it looked perfect. I gave my ass a few experimental squeezes and grinned at the mirror. Sexy.

I would have thought that I would feel nervous and doubtful. But instead I felt giddy, excited. Maybe because this was what was going to bring Ryan down.

I sat at my desk, waiting for Ryan, and thought over my plan. Instead of a hard and constant "no," which would only make him more determined, I needed to bring him right up to the edge of victory - the the point where he lowered his defenses, then snatch victory out from under him.

He thought I would fuck him? I would convince him that he was wearing me down...that I was slowly submitting to his will. I would bring him right to the point of entering me, then show him that he didn't control me. I'd break him. And then he and Sarah would be mine.

Of course...my plan might require a few unconventional actions on my part...I licked my lips. But it was the cost of doing business when it came to the challenges I faced with Ryan. Ryan...this huge-bodied and huge-cocked teenage stud who was fucking everyone in sight. He thought he had license to control people? I would do the controlling, even if it meant appearing to submit to his beautiful body and face, his confidence and swagger, his godly cock...to...to a point. I would hold back anything too inappropriate, of course, keeping it restricted to innuendos and "almosts."

I looked at the clock. 11:17. He was very late. I sighed.

I stood up, intending to buzz the admin to ask for an update, when the door opened and in walked Ryan. My eyes immediately ran over his body.

He wore a white muscle shirt over well-tailored blue jeans today. The shirt was tight around his massive chest and hung loose below it. His arms and shoulders were on full display, rippling with muscles on muscles. The jeans were perfectly fit to his massive legs and displayed power with each stride.

I looked up at his handsome face and he had on a wide grin, looking at me. "Why hello, Princess!"

I blushed and looked down.

"Oh, don't be like that...you look fantastic."

I couldn't help but grin at the compliment. I had, after all, worked hard on the outfit. I steeled myself though.