First Step of Becoming a Real Sissy (M/m) (F/m)

Quick background before any of this. Yes, I identify as a femboy. A sissy. A trap. Whatever you want to call it. I'm bisexual and submissive to both genders with a tendency to fantasize about what I suppose are typical fantasies for someone like me. Well, most are typical. The others are, well, atypical. I'm 5'2 due to some strange twist of genetics, I weigh 120 pounds. I go to the gym as much as I can, though this has left me with a flat stomach and a bubble butt more than it has given me definable muscle. I've got rounded, a pixie cut, and a generally petite figure. To top it all off, I've got a below average manhood topping in at a "staggering" 4.5 inches. Until a few months ago, I was a virgin at 19 and this is the story of my first sexual encounter.

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It was a few weeks after New Years. I'm doing that incredibly stupid thing where you take a break from school after high school in an attempt to figure out what you want to do and where you want to do it along with just generally taking a break and so I was left with nothing to do. A friend of mine, we'll call her Sarah, invited me over to spend time with her and her husband during the evening to relax and blow off some steam. This wasn't anything unusual. She and her husband, he'll be called Vince, both knew of my secret, accepted it, and we hung out regularly so I felt rather comfortable around them. Sarah's a tattoo artist and the only person I'm familiar with that is actually smaller than me, though that's not important. Her husband, Vince, is the polar opposite of us size wise. He's 6'6 and 240 pounds of muscle from his job as a trainer. He helped me get on my workout routine when I was still a scrawny bag of bones.

Anyway, I readily accepted. Later that day, I showed up wearing a pair of loose, soft gray high waist shorts that managed to show off my thing waist without squeezing too tightly with a gray and white baseball shirt with the front tucked in under my shorts and the regular pair of black panties that I wore underneath it all. To top it off, I had on some grey knee socks and black converse sneakers. Not my most fashionable outfit, but it was comfortable and that was what mattered.

When I arrived, I learned that Sarah had to work(I later found that this was a lie. They have an open relationship and they were both turned on by the thought of dominating me). It'd didn't bug me as much as Vince's dress did. He wore nothing but a pair of boxers that, despite being loose, did nothing to hide the massive bulge of his flaccid cock that swayed softly with his steps. Even then, I thought I noticed a smirk on his lips as he saw me looking at his manhood as he walked me into the living room. He had me take a seat on the couch and told me to find a movie on Netflix while he went to make some popcorn. I ended up putting on Bruce Almighty just as I heard the ding of the microwave and that shuffling sound of the popcorn being poured into a bowl.

When he sat down, he sat down right beside me with his arm put on the couch behind me while he sat the popcorn on his lap. This left me with conflicting emotions. On one hand, I had thought I just saw the tip of his cock and if I had my god was it huge. On the other, I was no longer guilty of staring at his crotch like a dog at a bone. Instead, I was able to halfway focus on the movie with the other half of my sex addicted brain considered just how much larger his cock was than the toy I used at home to stretch myself. To cope, I absently used my left hand (I'm left handed, by the way.. Not that it matters) to scoop popcorn from the bowl to my lips. We weren't even 30 minutes into the movie when Vince pulled a move straight out of a porn flick. While I wasn't paying attention, he had moved the bowl. This left my hand free of interruption as it traveled to his crotch. At first, I hit his thigh though I slid down a bit more thinking he might have shifted the bowl which led my fingers to brush over the exposed head of his cock. I was right, it had slipped out but I couldn't tell how big it was. So, feigning innocence, I risked a feel as my fingers wrapped around the semi-erect tip of his cock. Suddenly, I was rock hard and throbbing as I realized that his semi-erect manhood was easily larger that my raging hard on. Hoping he wouldn't noticed, I pretended to be shocked as I pulled back my hand. To be honest, it wasn't too much of a stretch. I was shocked.. Just more by his size than actually touching him.

"H-holy shit. I'm so sorry." I stuttered, my cock head throbbing under the elastic confine of my panties to match the beat of my heart in my chest.

"Mm, no you're not." he said in a voice that was almost a moan.

He was right, I wasn't sorry. I had never wanted to do something again more in my life. I suppose he sensed that as his arm fell around my shoulders, his muscle rippling softly as he pulled my body into his own to leave my lips just a few feet away from his crotch as my ear rested on his chest.

I started to speak up, to stop him from loyalty to Sarah before he shushed me just as I began to speak.

"Not another word unless spoken to," he told me, his voice soft but stern. "Go ahead and touch, I know you want to."

My argument was gone from my lips and my hands betrayed me as the left opened the hole in the front of his boxers while the right fished his hardening cock out into the open air and before my hungry gaze. Slowly, softly I wrapped my left hand around the throbbing base of his cock. From there, I slowly stroked him to full mast with my thumb stroking over his bulbous head, smearing the pre that leaked out around the ridge that formed when I pulled back his skin to expose it. The result forced a moan from my lips as I sat there, holding a cock that was at least twice as long as my own and almost as thick as my wrist. I shifted my seating, allowing me to kneel on the couch as I held my eager lips almost a foot away from his pulsating tip. I smiled and bit my lip as I felt his left hand move to the back of my head, leaving me ready for what I assumed would be a guided blowjob. I was not, however, ready for the smack to my ass that made me rock forward with my mouth shooting open in a gasp of a alarm. In that moment, Vince pushed down. Before I realized it, my lips had parted for the tip of his cock to leave his tip buried in my mouth.

My first reaction was to pull back, though Vince easily held my head in place to force me to grow used to the feeling of his throbbing manhood in my mouth. As shocking as it still is to me, it didn't take long. Before long, I was happily licking at the slit of his cock head while my lips squeezed and massaged the ridges of his cock as he gathered both of my wrists to the small of my back where he pinned them. This left him in control of my head as I knelt over his lap with his delicious cock nestled in my mouth.

"That's better, isn't it? I always knew that somewhere deep inside that virgin demeanor of yours, there was a little sissy slut waiting to be unleashed. " he groaned as he pushed down on my head, forcing me to part my jaws to take more of his throbbing manhood. I felt inch after inch of this massive beast of a cock forcing its way into my mouth until I felt the pressure of a tip poking against the back of my throat. At first, I gagged as I wasn't expecting it. It was, after all the first time an actual cock had sought entry to my throat. All others before it had been a fake toy I brought for my own fantasy. Vince pulled back a bit, letting me recover and I rewarded him with firm, long licks along the side of his cock that massaged the vein that pulsed against my tongue. This brought a groan and another push of his hand. This time, I was ready as I felt my lips slide down his cock until I felt the shocking feeling of skin against the tip of my nose. I had just taken this massive slab of meat all of the way to the base.

Once again, Vince groaned and pushed down on my head even as his skin blocked my airway. He held me there, enjoying the feeling of my throat quivering around his cock as I slathered it with saliva. Before long, he pulled me off of his cock completely to let me catch my breath as he throbbed, coated in spit and pre-cum in the open air as I looked on at my work.

"What did I tell you? A slutty little sissy," he told me as his right hand released my wrists to move up to my head, which was at this point free of his left hand. His fingers slipped into what little hair I had and he used it to pull my head back. This left my back arch with my cock throbbing painfully in my panties as I looked at him with smeared lipstick and a look of bliss. With a smirk, he pushed my head away and forced me to the floor where he bent me over the table with my hands on either side of my body, bracing myself against the cool wood surface. The fabric of my socks kept my knees from feeling uncomfortable against the floor while my feet were left with rubber covered heels pressed together.

"Now that you've tasted one, it is time for you to find out what a real man feel likes when he is buried inside your tight little ass," he told me with a chuckle as he roughly pulled down my shorts along with my panties, leaving both pieces of fabric at my knees.

"This is what you have to work with? No wonder you're a sissy," he told me with a flick to my balls, exciting a moan from my lips before he slipped his cock between my thighs and pressed it up against my cock and balls, effectively comparing his cock to mine. I was right in saying it was twice as large as mine, as I realized as he ground his cock against my own.

"Go ahead and ask for what you want." he growled over me.

"P-please.. Give me your cock." I begged as I wiggled my tight little ass back against his hip in desire and need. My desire was soon fulfilled as I felt the saliva slicked head of his cock pressing against the squeezing rosebud of my ass. Slowly, I parted around his tip as he guided himself into the warm confines of my rear. I moaned out as I felt my ass stretched with all of the pressure that entails. Slowly he worked the first inch and a half of his cock into my tight rear, leaving me breathless as his powerful fingers sunk into the skin of my hips. Inch after inch of his cock was slowly pushed into my tight ass in a process that took longer than I care to describe. By the time he was finished filling the tight confines of my ass, I was left with a cock throbbing with a need to release as it leaked pre-cum against the hard wood of the table underneath me. Not that either of us paid it any attention, of course. No, instead we sat there with his massive cock stretching my ass as his massive balls rested against my smaller pair.

Before long, he pulled back to the tip to begin a firm and steady pace of thrusting as he began to use my ass like the cum dump he wanted it to be. Every thrust of his hips made his hefty balls slap against my own as he pushed in and out of me again and again. The sound of our skin slapping together was the only noise in the room aside from the soft humming sound of Bruce Almighty still playing in the background. Again and again he plunged his massive cock deep into my ass, leaving me moaning like a bitch in heat.

"Here's your reward, you silly little slut." he groaned before long, only moments before I felt his cock throb and expand with the release of his massive, thick load of cum deep into my ass. He groaned as spurt after spurt of his sperm shot into the warm cavern of my ass and when he was done, he pulled out with a loud moan before giving my ass a nice, firm slap.

"Good girl." he said to me with what I can only guess was a smirk. "Now don't cum until someone tells you that you can." he said as he stood slowly, leaving to the bathroom or his bedroom while I stayed bent over the table with cum still leaking out of my ass. I was too tired to move so I merely rolled off the table and onto the floor, where I laid alone throughout the rest of the move. My cock was still hard when I heard the front door open. I didn't bother covering up even as Sarah came to the living room, wearing a pair of skin tight jeans and a Iron Maiden tank top that fit her loosely.

"I'll be damned," she said, with a smirk on her face as she stood over me with a foot on either side of my hips. "He was right. You are a little sissy."

She licked her lips as she looked me over, with my slowly fading hard-on. She glanced at the table and my stomach before giving me a evil looking grin.

"Poor boy, he didn't let you cum. I'll tell you what we are going to do. I'll let you cum if you tell me when you're about to release. Deal?" she asked, though I don't know if she expected me to nod as vigorously as I did. Without missing a beat, she lifted her left foot and pressed her bare sole against the underside of my cock, trapping it back against my body. She watched my face with a twinkle in her eye as she used her toes and the ball of her small, soft foot to stroke my cock. It wasn't long before I was left groaning, nearing my orgasm.

"F-fuck. I'm cumming." I warned her, leading to her pulling her foot away from my cock just as I released the first spurt of my seed across my stomach. She had ruined my orgasm, though at the time I didn't care as I finally had the release I had been craving. I managed to open my eyes after the second spurt just in time to see her foot pull back just a bit before flashing forward to deliver a firm but not hard kick to my still cumming balls. I'm a bit of a masochist and the feeling of the kick at the same time of my orgasm was the icing on the cake as I laid there in pure bliss as Sarah wiped her foot free of my cum against the fabric of my shirt before leaving me lying in the floor.

I ended up pulling my shorts and panties up, climbing into the couch, and passing out with my cum still on my stomach and Vince's seed still in my ass.

That, my friends, is how I lost my virginity and became a true sissy.

Source: reddit.com/r/gonewildstories/comments/32u4a9/first_step_of_becoming_a_real_sissy_mm_fm