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Teacher's Crossdressing Challenge PART 2
🕑 Added 2022-09-17 17:00:05 +0000 UTC"Well, how did it go? Why haven't you called me yet?" It was Carol on the other end of the phone.
"Just busy with classes and grading papers and stuff, and a little distracted by all the attention I've been getting. It's almost surreal." I laughed.
"Kind of fun, though, isn't it?"
"Exhilarating is what it is. The boys can't keep their eyes off me, and I love it. I've even caught some of the faculty checking me out, and Dean Wagner," I paused, "holy shit, Carol." I could feel myself blush at the realization that I almost shared a lot more than I was willing to.
"What, did something happen?"
"Let's just say I may have gotten a little too much into character," I laughed nervously. I was only making things worse.
"Erica, what happened?" I could feel myself blushing and knew she could sense my nerves through the phone.
"Um, I Gotta go. One of my students needs something." I hung up before she could press me for details.
"Details, little sister..." Carol texted me. I knew she wouldn't let it go and eventually I'd have to tell her, but I had some things to figure out first.
Leaving the few boys that were still in the common room the last innings of whatever baseball game they were watching; I went to take a bath and go to bed. Day one had been long and stressful. I was going to need all my beauty sleep to be ready for day two.
Tuesday was a nice light fit and flair dress with stockings, garters and four-inch heels, I loved the way the light fabric danced around my legs as I walked across campus, Wednesday, a cute sweater dress showed off every curve in my body. I wore it with tights and knee boots. Thursday, a simple sundress that was almost too short with sandals. Friday, I went casual with a pair of jeans that looked like I had painted them on and a linen blouse that did an excellent job of just giving away how lacey my bra was. The five-inch heels accented my legs and ass perfectly in the skin-tight jeans.
Most of the boys seemed to come to grips with my new look and tried not to ogle too much, but I had to admit, when the breeze hit just right and my dress flew up and they could see the tops of my stockings, it had to be a challenge. And the way those jeans I wore on Friday fit, well, not a chance.
As the week progressed, a few of the other teachers had upped their game, but most, like the coaches, seemed to have stuck with their original idea and were happy to settle for second place. Miss Reeder was still going with the Jimmy Dean look, which I thought she pulled off magnificently. She even asked me to be her 'date' for the year-end dance that was coming up at the end of the month. I was pulling for her to get second place, for sure.
Five-inch heels are wonderful things for short periods of time, and by the time Friday afternoon got here, all I wanted to do was get them off my feet. I mean, my legs and ass looked amazing in those skintight jeans, but really, my feet were killing me. I laughed at myself as the true realization of how hard it was for women to make themselves as attractive to men as possible.
The envelope leaning up against my door was a surprise, but I picked it up and carried it through the door, kicking off my heels as it closed behind me.
"Ms. Wilson, I hope you enjoy these," was all the note on the envelope said, no signature, no name, just the note. Inside the envelope was a flash drive. Picking up my heels, I made my way to my bedroom to change, eyeing the drive cautiously, my mind racing with thoughts of what it might contain.
I set my briefcase and the flash drive on my desk and wriggled out of my jeans, dropping my blouse and my bra on top of them rather unceremoniously. My breasts bounced and jiggled when I set them free. I was learning why the first thing women did when they got home was take off their bra. I liked the extra weight; it was just nice to not have the bra digging into my sides. Even if I didn't win the big prize, I was learning a valuable lesson and would never take the effort women went through to be attractive for granted again.
Tossing my clothes in the laundry and grabbing a t-shirt, I opted to give the whole braless thing a try, catching a flicker of a thought in the back of my mind, wondering what it would feel like if I kept them.
A glass of wine from the kitchen and I sat at my desk to wrap up some grading so I could enjoy my weekend, letting my mind wander just a bit as I glanced out the window to see a group of students on their way to the pool.
"Why not?" I said it out loud, closed my laptop, leaving the grading for later and dug out one of the bikinis Carol had insisted I buy. Some very strategic tucking, flip-flops, a towel, my copy of Mallory and I headed for the pool to see what trouble I could cause.
The students were deep into a game of water volleyball and rather than inject myself into their fun; I found a spot to get a little sun and just read. I wasn't naïve enough to think I had gone unnoticed and found I was enjoying how the boys were trying not to get caught checking me out. For all intents and purposes, I was an attractive woman. That made me smile.
The warning bell sounded for dinner and the game broke up, the boys heading back to their dorms to change and me to Barrington for the same reason.
"You know, Miss Wilson, you really look like a woman. All the guys think so. I think you're going to win." It was young Mr. Weiss. "Maybe one day I'll have a girlfriend as pretty as you." He blushed and ran off to catch his buddies. I was betting he would.
I was still smiling when I got to the dining hall, many of the students seemed to have gone home for the weekend and our scout troop was off camping, so there weren't many people here, "I could actually relax a little, who would know and who would care. A whole weekend break from makeup, bras, and all that other stuff. The off-campus faculty get a break. Why shouldn't I?"
The idea was gaining steam and then Mr. Weiss saw me and waved and the smile I had been wearing since he had caught me leaving the pool and told me how pretty I was, how much I really looked like a woman returned. It occurred to me I hadn't minded fixing my makeup for dinner and that it was a conscious effort to pick out an outfit I thought looked not just nice but showed off my slim fit body and nice butt.
Yeah, the heels hurt sometimes, and the bra could get old, but I enjoyed having boobs. I was enjoying this, all of it, especially the way the men and boys at the school were treating me, even the ogling and slightly rude comments; I even enjoyed sucking off Dean Wagner off in his office.
I finished my dinner and went for a long walk around the campus, enjoying the cool evening air and the rustle of the breeze through boughs of the hundred-year-old oaks trees that lined the walkways. Every student I passed called me Miss Wilson, and it just felt right.
All I could think of as I made my way up the step of Barrington Hall was, that, if I continued this path for the entire challenge, I might never go back, and I just might be ok with that, too.
"Red Sox are playing," it was Mr. Simpson in the common room.
"I've got some grading to finish up, if they're still playing when I get done, I'll join you for a while.
"I'll save you a seat," he motioned to the empty room and laughed.
I hated grading grammar tests almost as much as my students hated taking them, so I forced my way through them and entered the grades. Leaning back in my chair as I started to close my laptop, and I saw it, the flash drive, sitting there where I had dropped it.
"I hope this thing isn't some kind of virus." I flicked it open and inserted it on the side of my computer, as curious as I was trepidatious about its contents. Pictures, dozens, and dozens of them, all of me taken during the week; at least he was talented with a camera. Some of these were very good, a few even caught some almost risqué moments when I sat just the wrong way, or the wind caught my skirt and showed a little too much leg.
There were pictures of small feminine moments, times when I pulled my hair back with my finger, pursed my lips, or smiled invitingly. There were shots of me looking over my shoulder, my hair flying behind me, pictures of a touch of lace showing through the opening of my blouse caressing the breast underneath, and more suggestive moments like me bending over, stretching the denim of my jeans almost to its breaking point.
I had a stalker.
My mind drifted through the week, trying to place the photos, trying to figure out who had taken them and wondering why they had left them for me without leaving a name. What did they want? What should I do about this kind of attention?
Scanning through the pictures once more, I decided it wasn't so bad. I had never felt this desirous as a man and the care I was taking to look feminine was evidence that there was more to the way I was dealing with this challenge than just the money.
Amidst all the pictures, there was one Word file. Curiosity had won over trepidation, and I clicked the icon and read. It was a short story about a young man at a private school with a crush on one of his teachers; a teacher who was openly transgender. Enthralled, I read on as they built a special relationship, finally culminating in explicit, detailed, erotic, sensual, carnal knowledge. I read all the things the student wanted to do to the teacher and all the things he wanted the teacher to do to him; I read about their tender kisses and the boundaries that they shattered together, all in the realization that, when he graduated, they would never see each other again.
When I had finished, I read it again, and went to change out of my cum-soaked panties. My mind swam in the images the writer had portrayed. What would it feel like to have a man inside me? Dean Wagner had been in my mouth, but in my bottom? Why wasn't I revolted by the idea? Why was my heart racing and why was I licking my lips as the images ran through my imagination?
I recognized the writing and understood exactly what the envelope was. I knew if I went to watch the last inning or two of the baseball game, they could infer it as an acceptance of what the story implied. Mr. Simpson wrote the story. He wanted to be with me. One of my students wanted to have sex with me, sex with me as a woman.
Alan was a senior and almost nineteen, most definitely not a virgin, and as captain of the lacrosse and rowing teams, hard and cut like a rare diamond. But he was also my student. Could I do such a thing? Did I even want to do such a thing? Did I want to live out the fantasy he described in his story? Did I want to be with someone that could make me cum just with his words?
"What's the score?" I sat on the couch next to him, but not too close.
"Were playing the Angels. It's not even close," he smiled at me and turned back to the game. We sat in silence until the game ended.
"Did you like the pictures?" he turned toward me, his arm across the back of the sofa, his long arm just long enough to touch my shoulder. I felt a spark of energy run through me when his finger touched my shoulder; I could feel it in my crotch.
"Yes, they were very nice. You have a good eye; however, a few were a little, um, inappropriate." I smiled and turned toward him, pulling my shoulder from his touch but raising my knee onto the couch inches from his. "You wrote the story very well. I don't think you should submit that one for a grade, though." It was a tossup who blushed worse.
"I'm glad you liked it," his hand fell from the back of the couch as he leaned a little forward, landing on my bare knee. My god, this nineteen-year-old boy knew more about seducing a woman than I did, and I was five, yeah, a whole five years older than him. I could feel my breathing getting faster, my heart beginning to race. The pictures he had painted with his words screamed through my mind; I could feel myself trying to get hard.
Scanning the room to make sure we were truly alone, I couldn't help myself, everything was coming to a head, all the attention, all the praise, the blow job for Dean Wagner, the compliments, the feelings, the textures, the click, click, click of my heels, I was breaking, and I knew it.
"Alan," I put my hand on his, gazing into his piercing blue eyes, noticing how much he reminded me of Henry Cavill, his broad shoulders and strong arms, wondering what it would feel like to be wrapped in them, "do you really want to do all those things you wrote about in your story, because right now, I'm so confused, so excited, so in the moment" I squeezed his hand in mine, "I can't think of anything I want more?"
I knew it was wrong. I knew I was putting my job, my career on the lines. The blow job I could at least justify. Fucking a student was unforgivable; I cried. He slid across the small couch and wrapped me in those wonderful arms, helping me to my feet and down the hall to my room.
When the door closed, he pushed me against the wall and buried his lips in mine. I had been with women, more women than a lot of men my age, but I had never had someone kiss me like this. It was raw, primal; it was hungry, almost violent in its passion. I wrapped my arms around his neck and drove my tongue into his mouth, chasing, sucking his tongue with mine as he inhaled my very soul.
Without breaking our embrace, kissing, and touching each other, leaving a trail of clothes from the door to my bedroom, our passion climbing ever higher and higher, we finally separated as we fell onto the bed.
I watched in awe, trying to catch my breath, trying to find some fraction of common sense that would let me stop what was about to happen, mesmerized as he pulled his t-shirt over his head, exposing his perfect chest, firm pecs, tight abs, my god he was gorgeous.
Slowly, he ran his eyes over my body, imagining what lay beneath the skimpy lingerie I had on. Bending at the waist, he pulled his boxers down his muscled legs, exposing the most magnificent erection I had ever seen.
"What is wrong with me?" a small voice screamed in the back of my head. "I'm a man. This isn't right. This isn't what I want." The voice became a whisper and disappeared as Alan climbed on top of me like a hungry cat, lowering his face to my stomach, leaving a trail of kisses and licks all the way up between my breasts.
"You are so beautiful, truly amazing, you know that don't you?" his fingers caressed my side, drawing a circle around my breast and giving my boobs a gentle squeeze. "Wait, these are real?" He sucked my nipple into his mouth and sucked hard.
Oh my god, I love my boobs.
Pulling his lips to mine I kissed him passionately, my hands roaming across his back, tracing the outlines of the muscles, moving slowly down and across his wonderous glutes, I squeezed matching his moan with one of my own as he ground his cock into my stomach.
"I've never..." I whispered in his ear as our lips parted, gently rolling him onto his back.
"It's ok, whatever you feel comfortable with," he smiled up at me. "Whatever you want to do is fine with me. I just had to be with you. I just had to taste your lips at least once."
Lifting my hips, I pulled my panties down, letting my own erection loose, noting that I was almost as large as Alan and getting a seditious grin in response, we both knew that what we were about to do was an affront to everything Wellington taught and neither of us cared.
I had just straddled him when he threw me on my back and climbed on top of me, pinning my arms above my head and kissing me hard. "Me first." He gave the most deliciously evil laugh. I trembled a little in anticipation.
Leaving a trail of kisses from my neck to my navel, with an extended detour to my breasts, Alan had me writhing in anticipation. When his hand found my erection, I immediately started leaking, the clear liquid serving as a lubricant for his slow metered motions, up and down with a slight twist. His hand felt wonderful on my shaft. I closed my eyes and moaned loudly as his kisses moved to the inside of my thigh and his free hand urged me to open my legs.
Down my leg to the back of my knee, Alan abandoned my aching cock. His kisses and licks sending surges of pleasure coursing through my body. When he began massaging my feet and sucking on my toes, I thought I was going to explode, but he wouldn't let me, holding me on the cusp. All I could do was float and writhe in the slow waves of wonderful feelings that were engulfing my soul.
"Are you ready?" he whispered in my ear. I had no words. I just nodded.
"What are you ready for?" he was toying with me.
"Whatever you want, anything, just please..." I could barely make the words.
He left me for just a moment, another ploy. The absence of his touch was worse than being trapped on the edge. I reached for my cock to try and finish what we had started, only to be greeted with a gentle slap, knocking my hand away.
Alan was back between my legs, taking my cock in his mouth, sucking it slowly, teasing it with his tongue, bringing me back to the precipice as he pushed my knees gently up toward my shoulders. Subconsciously, I must have known what he was doing, but I didn't care. This beautiful young man had played me perfectly; At this moment, I would do whatever he wanted.
When his cool, slick fingers started massaging my hole, all I could do was moan and press into them. I was lost. When they pressed inside, I knew they were preparing the way for the release I so badly needed. "Yes, Alan, yes, please." I begged.
First there was the pressure and then the sting of being violated, followed by the fullness and then something, something different from anything I had ever experienced. I never knew my ass was so sensitive, so eager to be played with, so hungry to be used like Alan was using it. He moved into me slowly at first, his eyes locked onto mine, reassuring me while his hands moved over my body, fondling my breasts, and then moving out my arms to pin my hands to the bed above my head as he plunged deep inside me.
I exploded, my hot juice coating his and my stomachs. My body froze, spasms and tremors of sexual energy coursing through me. It was an orgasm unlike any I had ever had. There was no quick release. This went on and on, surge after surge of intense pleasure coming from somewhere deep inside me and as Alan thrust his cock into my bowels, the tremors kept coming one after another after another.
Men aren't supposed to have multiple orgasms, but I wasn't being fucked like a man. I never got soft. I came twice, three times, Alan's cock driving me from one peak to the next, our lips locked in passionate kisses until I felt him pulse inside me. At that moment, I was his. He had claimed me like no one ever would again, his seed deep inside me, my virginity would always, and forever, be his.
"Alan, that was amazing. I didn't know I could feel like that." I wrapped my arms around him as he collapsed on top of me, my feet curled behind him, holding him inside me. My god, what had I done?
Gently kissing away the tears that filled my eyes, Alan lifted his body from mine, both of us covered in cum. "My pleasure, but I think we could both use a shower." He smiled and kissed my lips.
My mind was numb in the realization that I had just had sex. One of my students had fucked me raw. I let him lead me gently to the bathroom. Like a small child, I stood and watched as he started the shower. Like a toy doll, I stood there as he removed my bra, like a puppy on a leash, I stepped into the hot spray with him, closing my eyes and relishing the feel of his hands on me again as he gently washed the residue of our sex from my body.
"Are you going to be, ok?" he wrapped me in his arms and kissed my shoulder from behind.
I held his arms in place. "I don't know. What we did, it's so wrong in so many ways, I never should have..." I couldn't finish the sentence.
"What was so wrong about it?" he kissed my cheek.
"I'm a man, you're a man, and I'm your teacher." I let out a long sigh.
"Ok, the student teacher thing, I get that," he turned me to face him, wrapping his arms loosely around my waist. "But you a man? I don't think so. For the past week, you have been the most feminine woman anybody on this campus has ever seen. You brought three suitcases of clothes and makeup back with you, you love being a woman. Tell me I'm wrong."
I couldn't.
"I'm sorry, Miss Wilson, you are not a man, not to me or anybody else at this school, anyway. And even if you were a man, so what? We're both old enough to make those decisions, right?" Dammit, he kissed me, and I melted into his arms, knowing what he said was true. The only part of me that anyone could construe as being a man was rock hard between us.
Taking my arms from around his neck, I reached down and took us both in my hands, fondling our members as I wrestled with my new reality. This was so wrong and so right. I just wanted what, what did I want? My mind lost in the too fresh memory of what we had done, it was spinning with the realization that I had wanted, had needed, to be taken like a woman. What I wanted was for him to take me again.
I turned and leaned against the wall of the shower, pushing my ass out, inviting him to use me.
"Are you sure about this, Miss Wilson?" his hands found my hips.
"Shut up and fuck me, Mr. Simpson." I closed my eyes and let out a loud moan as he pushed inside me again, losing myself in the carnal act, erupting under the warm spray as he filled me with his seed a second time.
I was surely going straight to hell, but oh my, what a trip it would be!
Waking up alone in my bed was a mix of relief and angst. Alan had stayed well past the shower, and we had done things to each other that only existed in my deepest, darkest fantasies. We had used and enjoyed each other over and over. Well, mostly he used me, and I loved every minute. If he had stayed, there would have been a genuine chance someone would have seen him leaving my apartment.
My angst centered on what our relationship was going to look like going forward. I knew all he had to do was ask and I would do it all over again.
I did my makeup, put my hair up in a ponytail, put on a cute romper Carol had picked out for me, and headed for breakfast. They set weekend meals up on a buffet system, letting students and what little faculty was on campus come and go as they pleased. I took Mallory with me to dissuade anyone from bothering me. I didn't really want to read as much as think about what I had gotten myself into.
Just a week ago, I was going out, full of determination and trepidation, dressed as a woman, to go shopping with Carol. Today, I was going out, my stomach and my ass full of a student's bodily fluids, dressed as a woman, trying to figure out what the hell had happened.
The rest of the weekend was relaxing. I spent some time at the pool and watched a baseball game with the guys in the common room. Mr. Simpson and I crossed paths a few times. Neither of us said anything about what had happened Friday night.
By Monday morning, I was believing all I had to worry about was my 'review' with Dean Wagner.
My homeroom class was filtering out when I noticed Mr. Simpson slipping into my room. He smiled and waved at me, purposely letting the rest of the students filter out of the room before he closed the door behind them.
"Can I help you Mr. Simpson? Don't you have somewhere you need to be?" I had a suspicion what was going on and couldn't believe he would try to pull something like this.
"I do and I need your help with that," he smiled, "I have a huge calculus test and I'm so distracted thinking about what we did, what would happen if anybody found out," the way he said it carried a very strong implied threat. "I just don't know what to do about this." He unzipped his pants and pulled his erection out of his pants.
"Really Alan? Here? Now?"
He just nodded. "Here. Now."
Fuck, this was ridiculous. I had gotten myself into this and didn't see a way out. I locked the door and dropped to my knees in front of him, taking him in my mouth and twirling my tongue around the head of his cock while my hand jerked him furiously. It didn't take but a few minutes before I felt him tensing, driving him down my throat. I squeezed his balls and let him empty them down my throat. Part of the problem was, I enjoyed it. I didn't want to think about all the other issues with what had just happened.
Kissing the tip of his softening member, I put it back in his pants and got to my feet. "Mr. Simpson, first, threats aren't really necessary. I believe we both enjoyed Friday evening and, second, this is neither the time nor place for this. If you're horny, let's please be more discreet, ok?"
"Yes, Miss Wilson and thank you for the, um, help," he grinned, turned, and left for his calculus class.
The rest of my morning was a nothing out of the ordinary, sophomore and freshman comp, senior classical lit, and then lunch, followed by my conference period, which meant I would be on my knees again, this time in Dean Wagner's office.
"Miss Wilson, I do believe you are beginning to enjoy our performance reviews, perhaps twice a week. Why don't you stop by on Wednesday as well and we'll see how it goes?"
I licked the last drops of cum from his cock and got to my feet. "If you feel it would help the situation, then I don't see why not." I sighed a heavy sigh and turned to leave.
My afternoon was totally unproductive. All I could think about was the extracurricular activities that seemed to be taking over my life, and how much I was starting to enjoy them. Mr. Simpson was in my last class, senior comp, and was, thankfully, a perfect gentleman. When the bell rang, I went straight to my room and took a long hot bath, skipping dinner and sequestering myself in my room.
Tuesday morning, I dressed as conservatively as my wardrobe would allow, which wasn't very, and did my best to not run into Mr. Simpson or Dean Wagner. I made it through the entire day and was starting to feel a little better, until I realized Mr. Simpson had stayed after the rest of the students had left.
"More math problems, Mr. Simpson?" I took a deep breath and looked at him.
"You might say that" he walked to the door and locked it.
"I thought we had an understanding." I leaned back against my desk.
"We do. This is much more discreet than last time, don't you think?"
"Alan, really, this is too risky," I made the mistake of licking my lips as he started to unzip his pants.
I took my time this time, relishing the feeling of him in my mouth, enjoying the feeling of him taking control and fucking my face, driving his cock down my throat, and holding it there while he spewed his seed into my stomach.
Fixing my makeup, I let Alan leave well before me to ease any suspicions. Of course, there would be none. It was common for faculty to have students in their rooms after the day for tutoring or counseling. Most of my concern was that it would be difficult to call what Mr. Simpson and I were doing either of those.
I passed coach Tanner in the hallway and got a very interesting look, or was it just that the gaudy makeup he and the rest of the coaches wore that made it look like that?
Wednesday, I sort of got a reprieve when Mr. Simpson gave me the day off. Of course, there was Dean Wagner to take care of, but I looked forward to that.
Thursday, the wheels came off. Alan stopped by my room on his way to breakfast for a quickie, but it was in my apartment, and I knew no one would see us. I think he got an extra jolt out of it because I was still in my underwear when he showed up.
It was lunch where things went sideways. I had just finished eating when my phone buzzed.
'Saturday 7:00. Don't be late' and an address. A video of Mr. Simpson face fucking me in my office followed the text.
I scanned the room furiously, looking for a clue who had sent me the message. Nothing.
"So, round two tomorrow night, just like last week?" it was Mr. Simpson.
"Sure, why the hell not?" I got up and left him standing there. My life ruined. Why not go out with a bang?
To say I was worthless the rest of the day and all-day Friday would be courteous; I was a basket case. I was looking forward to Alan fucking my brains out again just to take my mind off the fact that someone had video of him doing just that; it was ironic to the extreme.
When he finally knocked on my door, opened it and yanked him inside. "Erica, I just came to apologize. We don't..." I didn't let him finish his sentence. I pushed him against the wall and covered his lips with my own, driving my tongue deep into his mouth and running my hand straight to his crotch.
It would have been a fair assessment to say I raped him that night. The sex was raw and primal. I sucked him hard, and he fucked me like there was no tomorrow. I spewed my seed all over the both of us as we went at each other again and again. We fucked in my living room and in my bed, then in the shower, only to go back to my bed and do it again. When we were both so exhausted, we couldn't go on. I broke down in his arms and cried.
"Erica," he had never called me that before, "what's the matter?"
I showed him the text.
"Oh, any idea who?" he asked in a whisper, holding me while I continued to sob.
"I saw coach Tanner in the hall after you left that day. He looked at me funny, but with him, you can never tell, so not really. I'll just have to show up and see. I don't really have any choice; I could go to jail for what you and I have done."
"I won't let that happen; I promise. I'll tell them I forced you, I blackmailed you or something."
"No, this is on me. All I had to do was say no. And that would be so obvious. I'll go tomorrow and find out what whoever it is wants." I nestled in his arms and let him hold me. That's how we woke up the next morning and I wouldn't have wanted it any other way. Alan was a good man, and I was lucky to know him. Besides, the sex had truly been amazing.
We showered together and made love under the hot spray for what we believed to be the last time. It was slow and powerful, tender, and delicious; all the things it should be between lovers. He snuck out, and I followed him a few minutes later, making our separate ways to breakfast.
I spent the entire day organizing my class notes and preparing for whomever was going to replace me when this all came out. There was no way it wouldn't. At five, I showered and got ready, only to have my preparations interrupted by another text. It was a picture of me the day I had come back to campus wearing my shorts and a tank top with those four-inch heels I loved so much. Well, that made things easy.
I put my hair up in a high ponytail, grabbed my purse, and headed for my car.
Mr. Simpson stopped me outside the common room. "I did some checking. That address is coach Smithers. They all get together and play poker twice a month. I think they're all going to be there." The look on his face almost broke me. He really cared.
"I just hope they're not all in drag, I don't think I could handle that," we both laughed, "and thanks Alan, for everything." I gave him a peck on the cheek and went to face my fate.
As high school coaches went, they were well, high school coaches, but Wellington had the highest standards and the school expected them to set a good example, so the customary fat guy with tobacco stains on his shirt was nowhere to be found. Instead, there were fifteen very fit men from their early twenties, like me, to their late fifties, like Coach Tanner. Not a bad-looking bunch, especially now that the makeup was gone.
"Hey, you made it, great, so buy in is fifty bucks, Texas Hold'em friendly game. You're on table two over there with Smithers and Jackson. Winner, take all," coach Tanner smiled at me.
"Um, ok," I was dumbfounded, "I didn't bring any cash." I was sure he could read the confusion on my face.
"We got that covered for you." His smile turned into a devilish grin. "So, here's the deal. We've been talking about it and kind of feel you cost us, as a group, at least five thousand dollars. We were planning on winning the challenge, even convinced the seniors what it should be, thinking no one would go as far out as we planned, until your sweet ass showed up last week looking like a gaddamned supermodel. So that's about $300 each which, last time I checked, was the cost of a high-end blow job in Vergas. From what I saw, you are definitely high end."
I cut him off. "So, I play 'your game' tonight and what happens to that video? It just disappears forever?"
"Pretty much. I thought you'd figure it out, so what do you say? Play a little poker, suck a little cock, and all your problems go away."
I took a deep breath and shook my head. "Fuck, what the hell? Not like I really have a choice, is it? Deal the damned cards."
They were a fun group. The banter amongst them as the chips moved around the tables was funny and spirited. I quickly picked up on their personalities and, as a result, started winning a few hands. Every so often, one of them would ask me if I wanted to take a break and we would go off to a corner and I would get on my knees.
Smithers was first and I was surprised, the man was hung like a friggen horse, ten inches and thick as my wrist, I played with it, running my lips up and down the shaft, taking as much of the monster as I could I my mouth while I used both hands to stroke it up and down. Getting one of his balls into my mouth was an accomplishment. I worked on his shaft for ten minutes before he started to tense.
Taking the huge head in my mouth, flicking his glans with my tongue, I stroked as fast as I could with one hand while I gently squeeze his balls with the other. He exploded and I did my best but ended with thick white sticky mess running out my nose anyway. It was as wonderful as it was gross.
Licking the cum from my upper lip, I smiled up at him and went to wash my face.
A young first-year coach was next and under different circumstances, I might have dated him, but he was rough and rude, calling me a bitch and a cum-slut, and tasted like cigarettes. When he came, I almost spit it out, but thought better of it, swallowed, and went to get a shot of tequila from the small bar they had set up.
I could have sucked Beacham's cock all night. He was the strength and conditioning coach and looked like it, chiseled good looks that reminded me of Wesley Snipes in his prime. His cock was a thing of beauty. Not as big as Smithers, but still impressive. It fit in my mouth easily and felt so good when I took it all the way down my throat. He could have easily started face fucking me and I would have loved it, but he let me worship his manhood like a woman should, teasing it with kisses and licks, sucking on his large dark balls and loving everything about it. When he started to cum, I knew I had to taste it, so I pulled him out of my throat until just his head was in my mouth, taking the last few spurts on my tongue, it was better than I had imagined, rich and full. Like I said, I could have sucked his cock all night.
Someone at the other table went all in and three others called, when the cards were flipped, the three who had called were done and I spent the next twenty minutes on my knees letting them take their turns filling my throat with their hot juice before they headed home.
Tackman, the head rowing coach, was next, and I let him face fuck me, eight inches of beautiful thick meat driving in and out of my throat. God, it was wonderful. When he came, it felt like it was in quarts. I almost soiled my panties. "That was amazing." He smiled down at me as I kissed the tip of his cock.
"Anytime," I smiled up at him. I don't think he realized I was telling the truth.
Walker, the head athletic trainer, came so fast, I sucked him off twice just so he wouldn't get embarrassed in front of his friends. I think they all knew he had a small dick, but I did my best to make him feel like he was right there with Smithers and Beacham. The look on his face made my night.
We combined tables when we got down to the last six, and I discovered, to everyone's surprise, that I was among the chip-leaders. I didn't have delusions of winning, but I was doing better than anyone imagined.
One by one, the last few coaches lost to Tanner, each taking their turn with my mouth until it was just him and me. No one, especially me, expected me to be in the position. Tanner had twice as many chips as me and I knew my chances were next to zero, so I went all in before the flop with a pair of threes and beat his two pairs with three of a kind. That flipped the table, and I was now in the lead.
When all the cards were dealt, there were Jacks, a spade and a heart, and nines, a diamond and a heart, with the ten of hearts showing, the possibilities were endless, anything from the two pair showing up to a straight flush, and from the way he was playing, I figured Tanner had at least a jack, maybe two, so I fidgeted around and looked like I did not know what to do trying to lull him into going for it.
"All in." He took the bait. I smiled and called, flipping over my queen and king of hearts. Yeah, I was going to suck his cock just like I had sucked the fourteen before him, but I had beaten them all at their game and was going home with eight hundred dollars and that felt good.
Tanner had a nice cock, not overly large but bigger than average, and he had prepared for tonight. He smelled and tasted good, a little fruity. I took my time, making sure he got everything he expected from me. I teased and kissed his balls, sucking on them while I stroked his shaft. I took him all the way down my throat and held him there while I played with his ass; a little surprised that he let me.
I twirled my tongue around his soft head and bobbed up and down, listening for his moans and playing his responses, driving him to the edge again and again, until he was begging me to let him finish. It was easier than I thought it should be to press my fingers into his ass and massage his prostate. The moan I got in response told me he loved I had done it.
There was no stopping him this time, and I relented, letting him fill my mouth with his warm spunk. Milking every drop from his balls and rolling back on my heels, opening my mouth to show him my prize, I winked up at him and swallowed.
Tanner let me watch him delete the video as he walked me to my car, congratulating me on my win and thanking me for being such a good sport about the whole thing, like it had been some party game. I let him know in no uncertain terms that more than one coach had let me know they were uncomfortable with the whole thing, only going along because I seemed so willing. I let him know that two of them would testify to the blackmail; it would never happen again for any reason, or he was going down with me.
Of course, I was lying, but he didn't know that. I didn't wait around for any kind of response or apology. It would have been meaningless, anyway. I got in my car and left him standing there. How I was going to face any of them on Monday was something I was going to have to figure out.
Mr. Simpson was still up when I got back to Barrington, watching some infomercial in the common room; it was obvious he was waiting for me, so I joined him on the couch.
We sat in silence for a while as some guy espoused the virtue of some product neither of us would ever need. "So, all good?" He finally asked.
"As good as it can be, I guess. Tanner deleted the video, and I won eight hundred bucks." I smiled and leaned my head on his shoulder. "Thanks for waiting up for me, by the way."
"Anything else?" he wrapped his arm around me.
