Summer Ch. 02

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The drama continues, harsh truths come to light.
3.5k words
4.47
19.7k
8

Part 2 of the 2 part series

Updated 09/22/2022
Created 01/02/2015
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I didn't sleep at all that night. Philip's ultimatum, and the implications behind it, danced hatefully in my mind every time I closed my eyes. I was petrified imagining what he might want me to do. I knew it was desire that I had seen in his eyes, and it didn't take a genius to figure out where the next day's activities were likely to lead in light of that.

I won't lie and say that I hadn't thought about this before. Not with Philip, necessarily, but the idea of being with a man whileen femmehad certainly crossed my mind in the past. I didn't think that made me gay, since I was certainly still attracted to women, but was simply the natural progression of the female role that I so loved to fulfill.

It was odd. I'd fantasized about being with a man, about nearly this exact situation. Being dominated, subjugated, feminized. I was submissive by nature, so it would be hard to overstate just how appealing this was for me. I wanted to be taken, to be pursued, to belong to someone, which I suppose is yet another part of my nature that is more feminine than most guys. But now that it was a reality, I was shaking with fear. I was thinking frantically for a way out of this with my secret and my dignity intact.

But I knew it was no good. I could try to take the pictures, but Philip probably already had digital backups on his computer if he was threatening to email them to everyone. I could tell everyone myself, taking away his leverage, but that would be almost as bad as just going along with whatever he wanted to do. No matter how I looked at it, a solution wasn't going to present itself in time to get me out of Philip's clutches tomorrow.

Of course, it was always possible that I was blowing things out of proportion. Blackmail was a fucked-up situation regardless, but if his intention was to ruin my life, he could've done that without ever approaching me. And I'd never wronged him that I knew of, so he had no reason to go to that much trouble unless he just enjoyed watching me squirm, which I didn't think was the case.

My thoughts chased themselves in circles for hours. I fluctuated between terror and anticipation, my tired rationalizations doing nothing to quell the anxiety that bubbled up in my stomach as streaks of light began to invade the darkness of the eastern horizon. The time was almost here. Within mere hours I might very well be on my knees in front of Philip, or bent over his couch or countertop, or even on my back on his bed with him looming above me like some monster out of a horror movie.

I looked over at my alarm clock, the red display glaring angrily at me from my bedside table, and almost couldn't comprehend the 6:30 AM readout. Everything seemed strange now, especially the mundane, everyday things. My entire life had turned upside down in a matter of hours, but nothing had really changed. My bedroom, my house, my family, all of these things were the same as they'd been the day before. And that felt wrong. It seemed like with the momentous change that had taken place the day before, everything else should've been different, too. How could one thing change so much and everything else still be the same? How was that possible?

I could hear my parents, getting up and moving around, getting ready to go to work. Just like any other day. Like nothing had changed, even though I knew better. They wouldn't look in on me to say goodbye, I knew, because I was usually still asleep at this time, so I decided to get out of bed and start getting my girly stuff together. I didn't need to, since I already kept everything in one big duffel bag in my closet, but I did need something to occupy my mind before I drove myself crazy with my paranoia.

I had everything together within five minutes, my bag zipped up and ready to go. I looked over at my clock again. 7:00. Shit. I still had another hour to kill.

I decided to take a bath and shave my body. I kept it pretty smooth, usually, but it had been about a week since I"d last done it so the stubble was coming in. I shaved quickly but carefully, making extra sure that I didn't miss an inch. If Philip got as up close and personal with my body as I thought he would, I didn't want him to find any hairs that might remind him he was with a guy. Not that I cared if he enjoyed the experience. I was just a perfectionist. Right?

After that, it was ten minutes until eight, so I hurriedly threw on some regular clothes and grabbed my bag. Philip hadn't told me to come over already dressed, and there was no way in hell I was leaving the house in women's clothes, so guy clothes it was. I walked next door on trembling legs, feeling like I imagined a criminal felt walking up to the gallows. With every step Philip's house loomed larger in front of me, my doom staring me right in the face. I knocked, and in my heightened state of awareness the sound was as loud as a cannon blast.

The door opened, revealing Philip's grinning face. He was clad in just boxers and a wifebeater, and even as frightened and angry as I was with him I noticed just how hard and masculine his body was. My heart sped up and my palms began to sweat, and I told myself that it was because I was just that scared. That I stepped meekly forward at his gesture because I had no choice, because he'd destroy me if I didn't.

"I didn't think you'd come," he admitted as he closed the door behind me. "But I'm glad you did."

"Like I had a choice," I snapped, my frustration at the situation seeping out into my voice. "Seeing how you're blackmailing me and all."

To my surprise, a look of hurt flickered across his face. "I know it doesn't seem like it now, but I really am doing this for you. I'll admit that I don't know everything, but I do think you'll be glad that this happened later. I won't make you do anything painful or public, and nothing disgusting either. Anything we do here stays between us. Okay?"

It shocked me that what he said actually made me feel better. He had just laid to rest a lot of my fears. I wouldn't get hurt, and my secret would still be safe when I left here today. Assuming he was telling the truth. But I decided to trust him. I was here, so it was time to make the best of it.

"Go get dressed," he prodded me gently, pulling one of the photos from an envelope on the coffee table. "Wear this first. This one was my favorite."

The outfit in the picture was my favorite, too, and most of the others were variations on the same basic theme. A short, pleated black skirt with a tight, candy pink top, with matching pink bra and panties underneath, and knee high black boots to round it off. The panties were just regular bikini panties instead of the usual thong. I had thongs, but I generally didn't wear them under a skirt unless the skirt was a more form-fitting one. I couldn't explain it, but I just liked regular panties better under a skirt.

Philip pointed me to his upstairs bathroom, the master bath. "Ellen left a lot of her shit here when she left. Makeup, clothes, stuff like that. Go ahead and use some of the makeup, make yourself nice and pretty for me." He shot me a flirty smile.

I blushed and quickly looked away, scurrying up to the bathroom before I embarrassed myself further. As I closed the door behind me, it dawned on me that I was slipping into my role already, without even thinking about it. I was obeying anything Philip told me without question, and I had all but giggled and batted my eyelashes when he'd flirted with me a moment before. It was disturbing in a way, that I was feminine on a level that I hadn't even imagined. How could I know so little about my own mind? Was I just afraid to look too closely?

I shook myself, not wanting to get lost in thought now. Philip was waiting for me, and I still had to get ready. I glanced around at the cosmetics spread across the counter, and it looked like Philip's ex had left nearly her entire makeup case behind. Everything I needed was there.

I got dressed quickly. I had years of experience in the clothing part, so that was almost second nature by now. The makeup, however, was a different story. I didn't have much experience with cosmetics, since they were such a pain to put on and take off. I was also afraid that makeup would leave behind traces that I wouldn't notice but my mom would. So it was saved for special occasions when I was sure to be alone for a long time.

I did the best I could, which wasn't bad, all things considered. I liked dark eyes and pink lips, and I hoped Philip did, too. I put a little glitter on my eyelids, some shimmer on my lips, and brushed my long hair out until it was straight and glistening. I was ready.

I sauntered downstairs, the small heels on the boots forcing my hips into a sultry sway. The soft, downy fabric of my skirt brushed my bare legs as it moved with my body. Philip was standing at the bottom of the stairs, his appreciative stare caressing me all over. As I came closer he stepped forward to meet me. When I reached the second to last stair his strong hands gripped my hips and lifted me to the floor beside him. I marveled at his strength, and blushed profusely at the girly squeal that had escaped my lips when my feet left the ground.

"Damn, girl," Philip said, his hands sliding from my hips to my ass, gripping firmly through my flimsy skirt and pulling me tightly against him. A frisson of warmth rushed through me, both at being called a girl and at the feel of his hard length pressing against my belly.

I moaned as his hands wandered further down until he was squeezing my bare thighs, then back up underneath my skirt. My pink bikini panties were now the only thing between his hands and my bare ass. He ground his erection harder against me, and I shuddered at the feel of his hot breath spilling over my ear. I was so turned on by now that I pressed myself closer, wrapping my arms tightly around his neck while his tongue explored my ear and throat.

"You're so fucking sexy," he growled, pulling away enough so that he could see my face. Then, to my surprise, he kissed me full on the lips.

My lips parted automatically, and his tongue invaded my mouth before I could think to stop him. My back hit a wall and Philip was there, filling my senses with his impossibly masculine presence. His tongue claimed my mouth, forcing me to taste his essence, while his eternal stubble scratched my face almost to the point of pain. My hands roamed up and down his broad back while his thick cock pressed insistently into my stomach through our clothes. My own dick, which I always tucked back when I was dressed, was rock hard and straining against my panties.

He pulled away suddenly, but before I could protest the loss of sensation he spun me around and pressed my face into the wall. I moaned loudly, loving the way he was taking control of me. Then his body was flush against mine again, his angry pole now pushing hard against my ass. He kissed and licked the back of my neck, using one hand to hold my hair aside, while he ground harder into me. I could practically feel the veins on his cock through my wispy panties and his boxers, and the heat baking off his pulsating organ was sending an answering heat through my own body.

"Will you do something for me, baby girl?" Philip breathed in my ear, accentuating his words with another slow, hard grind against my backside. I nodded without thinking, without even registering what he was saying in my lust-addled mind. It wouldn't have mattered. I was past saying no to him.

"Will you suck my cock?"

"Mmmmmmm," I moaned loudly, and this seemed to be enough answer for Philip. He backed away from me quickly, and I felt cold at the loss of his body against mine. I turned to face him and found him already naked, with his impressive tool sticking straight out in front of him. I felt some trepidation, but I knew I wanted this. I dropped to my knees before him and pressed kiss after kiss after open-mouthed kiss up and down his shaft and balls, leaving sparkling pink lipstick stains over every inch of his member. He moaned loudly, over and over again, as he jerked his hips toward me, unconsciously seeking more contact.

Emboldened by his reaction, I wrapped my lips around his rod and began enthusiastically bobbing up and down. The rich, fleshy taste of his cock filled my mouth, and I made love to it with my lips and tongue. I found myself eagerly anticipating his climax. I ached to taste his seed, and swallow it down like a devoted girlfriend would.

His fingers wound themselves into my hair and pulled my head further down on his pistoning shaft, until his balls were slapping against my chin on every stroke. I almost gagged, but with an enormous effort I managed to suppress it. Philip was moaning louder now and I could feel his cock began to pulse in my mouth. I pulled back until only the head of his tool remained between my lips and waited for the explosion.

I didn't have to wait long. Within seconds, hot semen filled my mouth, salty and succulent. It was the taste of freedom and submission all at once and I gulped it down with gusto. Philip grunted loudly as he emptied his load into my greedy, wanting mouth, twitching as if he were being electrocuted.

Moments later it was over and his cock was softening in my mouth, dribbling out the last of his ejaculate onto my lapping tongue. When his flaccid member finally slipped from between my pink lips I felt an acute disappointment, and a burst of shame so intense that I had to fight back tears.

I couldn't believe what I had just done. Even if I'd been blackmailed, I'd still dressed like a woman and sucked another guy's cock. Even worse, I'd enjoyed it. How could I call myself a man after that? And if I wasn't a man, then what was I? I felt a burst of self-loathing, sadly all too familiar, and looked silently at the floor.

"Come here, baby girl," Philip said a few minutes later, his tone gentle. I got up without replying, and walked over to him where he sat on the couch, fully clothed again. We sat silently for a while, me stewing in my own guilt and misery, Philip just watching me.

"Do you wanna know why I did this?"

My head snapped up at the unexpected question. I had thought about it, but I didn't know Philip well enough to even guess. We were never close before, just two guys that would hang out occasionally.

"I wondered," I intoned, my voice hoarse and scratchy. "I guess I was just more worried about the blackmail itself than whatever reason was behind it."

"You remind me of someone I knew in high school," he told me. "He was just the nicest guy, always so sweet and polite to everyone. A lot like you." I smiled faintly at the look of fond remembrance on his face.

"We were never really friends. We knew each other, since it was a small school, but I had my own group and he had his. I would wave back if he waved at me, but mostly I ignored him. Then one day, someone spotted a girl's thong peeking out the top of his pants. Word spread around fast, and soon everyone was giving him shit for it. You know how high school kids are, stupid and hateful, so he had all kinds of childish shit done to him. Stupid pranks, shoves in the hallway, snide remarks, pretty much the hate crime variety pack."

My heart lurched at the morose, guilt-ridden expression that crossed his face then. I don't think I've ever seen such a lost, forlorn look on a human face before.

"I was a big part of that. I was the typical, cocky jock asshole back then. I'm not proud of it, but that's what I was." He inhaled deeply, and I realized with a start that he was on the verge of tears as well.

"One day, he didn't show up for school, and he'd had perfect attendance before. He walked into that place every day, knowing that me and all the other idiots were just waiting to make his life miserable. God, he was braver than all of us.

He was gone for a week straight before it occurred to any of us that he wasn't there. There was this girl that went around with him, I don't know if she was his girlfriend or what, but they were close. Anyway, she comes to school in hysterics, just bawling her eyes out."

Philip's jaw tightened and his fist clenched. His eyes swam, the chocolate brown irises wavering through their veil of tears.

"They found him in his bathtub. He...he..,"

I stopped him then with a hand on his forearm. I could guess the rest, and it would only hurt Philip to say it. I wanted to comfort him, but I didn't know what to say. I was only nineteen, and a sheltered kid, to boot. I couldn't even begin to comprehend his feelings just then.

"But I see a lot of him in you," he said, with a look I couldn't quite identify. "I can't bring Bobby back, but I can help guys like him avoid the same fate. I probably could've gone about it a little better, but I really was trying to help you. You're just too shy for your own good, and I didn't think you would ever do what you needed to do on your own."

"I can kind of understand that, I guess," I said doubtfully. "But blackmail, Phil? That's going too far."

"I know," he answered, abashed. "But if it makes you feel any better, I never would've sent those pictures. I just knew you'd do what I said if I threatened to do it. I'm not the smartest guy, and I do the wrong thing a lot of the time, I get that. I just think, maybe if Bobby had had someone like that, someone he could just be himself with, he might still be...I don't know. Maybe I'm just being stupid."

I was at a loss for words again. I understood the need for redemption, for absolution, but I didn't know how I could give him those things or if I even wanted to. I was upset that he'd manipulated me, even if it had turned out to be a bluff. I was also a little miffed that he'd thought so little of me, that I wouldn't even be able to muster up the courage to take my life into my own hands.

But I wasn't entirely without sympathy for him. I couldn't imagine what it must've felt like, to feel responsible for the death of another human being. It was telling that he'd been able to take that experience and use it to become a better person.

All in all, I felt more confused than ever when I left Philip's house that night. We'd spent the rest of the day lounging around, hanging out like normal, except that I was still dressed in my femme clothes. It had felt far too weird to do anything sexual after the weighty revelations we'd had earlier, and I wasn't sure yet if I wanted to go any further at all. I had a lot of thinking to do before we got together like this again.

But it had been an educational day. I wasn't through the woods yet, but I was definitely further along the path of enlightenment than I had been the day before. Soon I would step out into the light, and I couldn't wait to see what waited for me there.

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3 Comments
AnonymousAnonymousover 2 years ago

Beautifully written. It's as though you'd read mind and put on paper what has been playing over and over in my head. Philip is the man I've spend my entire life wishing, waiting for, the one man capable of freeing me from the prison I've spent a lifetime constructing.

Sadly, I squandered the youthful feminine beauty I had been blessed with on mirrors.

pantyhosefunpantyhosefunover 2 years ago

wish the story was longer.:)

JD2100JD2100almost 8 years ago
loved it and hope you do continue

Please continue this story I would love to see what happens next.

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Summer Previous Part
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