Str8 Turn Out Ch. 07: Living The Dream

Str8 Turn Out 7: Living The Dream

Sissy dreams really can come true -- even nightmares!

Thanks to all for all the comments! I truly appreciate them and please keep them coming.

This is a tale of male-on-male sex with some non-consensual elements including forced feminization as a young man comes to terms with his evolving sexuality, so if that offends, please look elsewhere.

Everyone mentioned is over 18 in this twisted tale. This is a work of fiction with some unsafe practices. Please be careful in real life encounters.

SHIT!

Bad enough that I'd just had a couple of sissy nightmares, but now I also had to deal with my panties being soggy with cum. My alarm was going to go off in about an hour and I was so stressed from the wet dreams there was no way I would get back to sleep, so I decided to hit the shower and start the day early.

I finished in the bathroom and put on a fresh pair of red panties. Slipping them up my smooth legs reminded me of the nightmare I just had of helplessly plunging down a silken chute. I pulled the panties over my butt cheeks and the sensation calmed me down. But that started a whole new avenue of self-doubt.

Was I becoming a cross dresser? I couldn't resist running my hands down over my crotch and up over my pantied ass. I admit I loved how the material felt on me. Would I enjoy them as much if they were men's underwear in the same material? Maybe I should slip into my nylon running shorts instead. I opened the draw I kept them in and rummaged around looking for a fresh pair. Just as I pulled out the red ones, I had an awful but unescapable realization.

I had a lingerie drawer!

An entire drawer of my dresser was filled with featherlight, wispy, silky lingerie that I had been openly wearing in public without even giving it a second thought. Oh, sure. Guys didn't call it lingerie. We called it compression gear, warmup gear, tech gear, under armor or whatever, but it was all just lingerie for men. We smiled at the claims that it supported our muscles during a workout, or wicked moisture, or kept our muscles warm and ready to go, but the truth is that it feels amazing on our bodies, soft and silky like our girlfriend's pantyhose feel on her legs. We wear it to display our bodies for potential sexual partners, but we like the sensation so much that we cover ourselves in layers of the stuff!

How many times had I slipped on a pair of silky spandex sport briefs, then a pair of shiny compression tights that I then covered with a pair of filmy nylon shorts. Upstairs, I'd wear a tight silky top that wicked moisture and a satiny smooth warm up jacket. Only now did I realize that this was all just socially acceptable lingerie for guys and I had been wrapping myself up in layers of it for years! I tossed the shorts back in the drawer and closed it. Little wonder that I had succumbed to panty wearing so easily. I'd been in training for it for since...since I was an eighteen-year-old senior on the soccer team!

That disturbing dream where I was naked on the soccer field in just panties and my eighteen-year-old teammates were all a bunch of sissies called the Pantyboys, suddenly made sense. I hadn't joined the soccer team just because I loved the game...it was because I loved the UNIFORM! I decided to go out for the team right after I saw it. The silky sport shirt style top and the butt cupping nylon shorts just looked so good on me and felt even better to wear.

I had been unconsciously indulging in a nylon fetish for the last ten years without even realizing it. I pulled out my old yearbook again and sat studying the pictures as I sat on my sore ass having my morning coffee wearing just a pair of red panties. I looked at my headshot of a goofy looking eighteen-year-old in my dad's tie without a care in the world. I was so innocent back then. I was just an amiable straight jock who had never even considered doing anything with another guy. At least that's what I had told myself since then, but that isn't the whole story.

Back in my senior year I had a regular jerk-off buddy. Tony was a friend from way back who lived just around the corner. One of us would text the other when we were horny asking if we wanted to hang out and play video games. Video games was our code for two eighteen-year-old knuckle heads getting together to share a hot jerk off session. Tony was a little guy with fine longish hair that was fun to hang with even when we weren't getting our rocks off.

After some initial awkward sessions, we fell into a groove. Instead of video games we would watch a porno sitting side by side jerking off. I almost always came first, so then I would turn to Tony on my left and start to jerk him with my right hand instead of my left. I would put my left arm around his shoulders and hold him close. Tony would pant in my ear with his head on my shoulder as we nuzzled like lovers until I coaxed him to climax. When he came, I would hug him tight and he would bury his moaning face in my neck. We came as close to kissing as young men could without actually kissing.

My next jerkoff buddy was my college roommate, Dylan. We had been rooming together for almost a year, when one drunken evening we had our first jerkoff session. Once the ice had been broken, we were masturbating each other at least three nights a week. My roommate was always the one to get things started, like one night after we didn't jerk off, Dylan must have found himself extra horny in the middle of the night. "Dude, you up?"

"Hmm?" Well now I was...kind of. I felt the blankets move and the mattress in my twin bed sag behind me. "Dude, What the fuck?!" I protested groggily. Dylan was crawling into bed with me!

"I'm so fucking horny. Let's play around." Dylan's larger frame ate up most of the bed and I was mashed face first against the wall. He'd already pulled down his underwear and his rigid eight-inch cock was rubbing against the nylon shorts I usually I slept in.

"C'mon...I'm sleeping..." I protested weakly. I wasn't being coy, Dylan had decided to jump into my bed just when I was in a really deep sleep mode.

Dylan didn't care. He wrapped on muscled arm around my neck while his big cock humped the crack of my ass. "Dude, it feels so good he husked in my ear." His cock glided luxuriously up and down in the nylon valley between my firm butt cheeks. His thrusts forced my own hard cock to hump the blankets bunched beneath me. Dylan was bigger than me and he had me pinned to my mattress, so there was no way I could escape, even if I wanted to. His thrusts came faster and harder, forcing my cock to hump faster and harder. "Ohh, fuck..." I moaned as I came in my underwear. Dylan humped faster and squeezed me tighter until he shot a huge load into the small of my back. He collapsed on top of me, gasping for air with his chin on my shoulder and our cheeks pressed together.

Soon he was dozing on top of me with his arms wrapped around me. I drifted off to sleep being spooned by my roommate, basking in the strength, warmth and weight of his body. That was the first time that I sexually submitted to another male. As you know by now, it would not be the last.

When I awoke the next morning, Dylan had already retreated to his bed, which left me feeling used and abandoned. We would never have another jerk off session. From that point on I was Dylan's hump toy. For the next three years, every couple of nights, he would climb into my bed and hump me until he covered me with his cum. As time went by, Dylan became more aggressive while I became more submissive. When he wanted to use me, he would just announce "Bedtime." I would stop what I was doing, change into my baggy nylon shorts and get into bed on my belly, with my ass presented and my face in the pillow. Dylan would turn off the lights and mount me like an inanimate sex doll. I kept my legs together and cocked my ass for him as he climbed on top of me nude. With his legs outside of mine and his chest on my back he would hump my crack, whispering how hot my pussy was and telling me I was a sexy girl. I would moan in a higher pitch then normal to maintain his illusion that I wasn't a dude and what we were doing wasn't really gay. I would moan about how good it felt, how big his cock was, call him daddy and tell him that I was daddy's little girl whenever he prompted me. Our talk would grow dirtier as Dylan approached orgasm.

"I'm getting close, little girl."

"Give it to me, daddy."

"You want it you little slut?"

"Yes, daddy! Make me your little slut."

"Here it comes...NUHN, NUHN, oh, fuck..."

"Oh, daddy..."

Dylan would unload hot jets of sperm on my back and shorts and then collapse on top of me. We would stay like that, plastered together by his sticky loads sharing a quiet moment of intimacy. I relished this moment as the beta male who had submitted completely to the dominant alpha male who had marked me as both his inferior and his property.

He would then wipe us off with a towel and ask if I had come. If I hadn't, he would roll us onto our side in a spooning position and I would reach down and jerk myself off. I didn't mind because while I was yanking it, Dylan would snuggle with me, nuzzling my neck, running his hand over my thighs, butt and pecs until I climaxed and shot my own load in my shorts.

Then came the moment I dreaded. Typically, Dylan would pat me on the butt with a "Thanks, dude," before heading for his bed. I died a little inside every time he did that. He wasn't being mean, just an alpha who had marked his prize and moved on.

But sometimes I was rewarded with the moment that I cherished. If Dylan didn't move right away, I would pull the blankets over us, and we would drift off to sleep. I would stay awake as long as I could, relishing being spooned and cuddled by my dominant roommate. I felt safe, protected and owned, as all too soon I drifted off with Dylan snoozing in my ear.

On those nights, it wasn't unusual for Dylan to start humping me in the middle of the night and we would have a second round just like the first. Sometimes when his girlfriend wasn't putting out, Dylan would have me stick my butt in the air and dry fuck me between my thighs. That was as close as a guy came to boning me until that guy in the sports bar years later.

About once a month, Dylan would surprise me by telling me to roll over onto my back. The first time I wasn't sure where this was going but did as he asked. Dylan climbed on top of me, his handsome face with tousled dark locks and strong body illuminated by the light from the street bleeding through the curtains. I looked down as his legs moved between mine, spreading them until his hard cock touched my own painfully hard rod tenting my nylon shorts. My eyes raked up his abs and muscled chest until we locked eyes. He started to slowly hump me and I gasped and instinctively wrapped my legs around the back of his thighs like a cheerleader at homecoming. No words were spoken. It was a moment of domination and submission between us. His eyes bore into mine as our hips humped each other. I ran my hands along his sides, his shoulders, biceps and vee shaped back. It was the first time I had explored another man's solid, muscled body and Dylan moaned in approval of my caresses. Dylan hadn't penetrated me, but he was fucking me and I was eagerly submitting. We both knew that he could take me right then and there if he chose to, but that was a line too far at that point in our young lives. We kept humping with our eyes looking into each other's souls, moaning and gasping until he came on our torsos, coating them in dripping lines of scalding hot man cream. His orgasm triggered my own and I unloaded into my shorts, maintaining eye contact the whole time. Dylan wiped us down and made a move to get up, but I held onto him and made a simple request, "Stay." He looked at me a moment and let me wrap my arms around him and pull him down on top of me. That is how we drifted off to sleep, with Dylan on top of me between my splayed legs, my hands caressing his broad back, savoring his strength, warmth and weight on top of me.

Those were my early male lovers whom I spent the next few years referring to as "jerk off buddies".

Where did that leave me now? I suppose I could officially list Tony as my first jerk-off bud, even though I regretted that we never made out. That could have been a special memory.

Dylan was another story. Although his cock had never entered me and we had never kissed, in retrospect I would have to list him as my first male lover. More than that, he was my first Dom. He indulged and encouraged my nylon fetish and I must now admit that he also introduced me to sissy play and trained me at it for three years. How many times had I breathlessly told him, "I'm daddy's little girl," while he humped me in a missionary position with me eagerly accepting the female role.

The same thing had happened with Tyler last night, except he had dressed me in full drag as a sissy maid and then actually fucked me while in the missionary position. We were barely into a six-week lockdown and Tyler made it clear that he wanted to do it to me again and again and again. If Dylan had wanted me to be his personal sissy maid and fucktoy I would have submitted to him gladly. The difference between the two Dom's was that Dylan made me feel good about being his sub, whereas Tyler simply made me feel like shit.

I stared into my congealing cold coffee as I tried to process the chilling reality that some twisted part of me got a deep thrill out of being treated like shit. I could easily send Tyler a text telling him that I would no longer participate in his twisted games, block him on my phone and never open my door to him again.

The trouble was that Tyler knew how to trigger my submissive impulses. I was like an addict that wanted to quit, knew how destructive his addiction was, but was always chasing the next high. I had the chance this morning to abandon my panties and slip into something else, I could have easily torn all my panties to shreds and tossed them away, but here I sat at my dinette in my sexy red panties, secretly loving how naughty they made me feel.

I knew that in a few hours I would obediently be sucking Tyler's cock and swallowing his disgusting load. Tonight, I would knock on his door so he could doll me up like a sissy maid. I would clean his apartment and then bend over for a good fucking. I would hate every minute of these humiliations, but I would never be able to get enough. I felt like I was sliding down the silken chute in my dream, but while the fall terrified me, I knew I would relish every inch of my descent.

It seemed that my only hope for escape was that Tyler would get bored with me. My phone pinged. It was a text from Tyler. Fat chance that he would get bored with me anytime soon.

"sissyboy,

Don't bother coming at lunchtime but be prepped for tonight. See you at six.

BTW - I left something on your door for you.

Master Tyler"

Shit! What embarrassing thing could my tormentor have left on my door?! I ran to the door in just my panties, opened it and peeked around the door. Whew! It was nothing more than a plastic shopping bag hanging on the handle. I grabbed it and shut the door quickly.

I peeked inside. Nail polish. Fuck.

There was a note inside.

"sissyboy

Be a good girl and paint your finger and toenails with this for tonight. It's the same red as your cocksucking lips. LOL!

MT"

My hand reached down and rubbed my stiffening cock through my panties as I read the note. I quickly replied to Master Tyler's text the way only a slutty sissy maid should, but then I ended up groveling.

"Dearest Master,

I'm so sad that I won't be able to suck your massive cock and swallow your manly sperm for my lunch today.

But thank you so much for your wonderful and thoughtful gift! I can't wait to paint my fingernails and little tootsies, cocksucker red, so they'll match my cocksucking lips. I will be on time and ready to take every inch of your powerful cock in my boy pussy.

I so want to be the perfect sissy maid for you and look forward to your harsh training and discipline to break me down to the mincing, simpering sissy slave I deserve to be.

Hugs and kisses,

sissyboy

PS: Another part of me is terrified of where this is going. I had never even thought about being a pantyboy or a sissy maid until you forced me into it. I'm afraid that if I spend the next five weeks while we are on lockdown as a sissy cockslut that I will pass the point of no return. Please let me go so I can try to return to some semblance of my former life. Please."

My finger hovered over the send button. I knew that the postscript would condemn me to being Tyler's sissy maid for the duration of the lockdown. I knew I should delete it, but my twisted side could not resist the kink of being held against my will in this sissy prison with the push of a button.

I hit send.

Of course, I immediately regretted it. I was going to have to log into work soon, so with tears in my eyes, I spent the time starting to paint my fingernails cocksucker red. My phone pinged.

With a trembling red fingernail, I opened the text from my Master.

"sissyboy

I'm glad to see that you understand where this is going. I also want you to be the perfect sissy maid for me and I'm looking forward to inflicting harsh training and discipline on you to break you down to the mincing, simpering sissy slave you deserve to be. We both know that there is no escape for you. I will NEVER, EVER let you go, no matter how much you beg me!

See you at six, bitch!

Master Tyler"

I read his reply three times. My cock was so hard that a spreading dark stain of pre-cum stained my panties. This was exactly what I secretly craved. Being used, humiliated and emasculated with no way to escape no matter how hard I begged, turned me on more than any girl I had ever seen. My hands were shaking as I quickly painted my toenails before I logged into work. A shudder went through me when I realized that my toenails matched the red panties I was wearing. OMG! I was wearing cocksucker red panties! Oh, how I wished Tyler had put the lipstick in the bag too.

I spent the rest of the day working at my laptop in nothing but my cocksucker red panties, finger and toenail polish. If the guys at work could see me now...

At six on the dot, I pressed a red fingernail to Tyler's doorbell. He let me in, "Let's see 'em, sissyboy." I held my hands out for inspection with palms down like a girl. "Sweet. Bedroom."

I headed down the hall to his bedroom and was not surprised that he had my sexy sissy maid outfit all laid out. I noticed that he had added a couple of items, black nylon panties with white lace trim at the waist and leg openings, plus a pink dog collar with rhinestones. I stripped out of my clothes and Tyler sprayed me with some girly smelling perfume. "You might as well smell like a girl too, sweetcheeks." Then he helped me get into the tight maid outfit complete with stockings and high heels. I could see my red toenails through the sheer stockings in my open toed heels. I swallowed hard as Tyler picked up the pink dog collar with rhinestone studs and buckled it tightly around my neck. "Thank you for my new collar, Sir. It's very pretty."

"It suits you perfectly," he smiled evilly. "Here's the best part." Tyler held up a pink heart shaped lock about two inches wide that said SISSY in a feminine script across the face. My hands clenched at my sides as he grabbed the collar under my chin and I heard a sharp CLICK. I let out a gasp at the sound, "Thank you, sir."

"Do your lips," he held out the cocksucker red lipstick. I took it and turned to the sissy maid in the mirror. It was still me looking back, but I looked defeated and ridiculous dolled up like a sissy maid. Somehow the locked pink collar around my neck with the heart shaped lock tagging me as a SISSY made me feel trapped. I smeared the lipstick across my bottom lip and then pressed them together. It almost looked like the sissy in the mirror was blowing me a kiss.