Sissy Sessions Ch. 04

Note: Sissy Sessions is a series of short stories you can read individually. Sometimes, I'll use characters from previous chapters. However, I plan to keep as many entries as possible as standalone stories. I hope you enjoy. Thanks for reading, and don't forget to star and comment! 

Our eyes locked, mine gazing upward from below. I batted my eyelashes in a seductive manner. I adore putting on a show for him. The look of lust in his eyes demonstrated how much he adored my performance. He didn't dare look away from me.

I close my eyes to help amplify my other senses. I revel in the taste and take in the scents. The sounds emanating from the action in his groin area almost bring me to a climax, but I resist. It's so rare for us to have open schedules. We live busy lives. 

With my eyes still closed, I begin to raise my head. My lips leave a shimmery ring on his pubic mound. On my way up, I loosen the grip my lips have on his shaft. I built up a solid amount of saliva and need to allow it to seep out and coat his shaft. A slight twist of my head to create a rotating motion makes sure I don't miss a spot, as a low hum escapes me. 

He's sitting in his favourite chair. He looks like a king reclining on his throne, pulling away at his vape pen. For a brief moment, there's a faint scent of the vapour in the air as he exhales towards the ceiling. It doesn't last long. The pungent scent of sloppy oral sex overwhelms my nostrils. It's a mix of saliva, the slimy substance from deep in my throat, his sweat, and the musk from his balls. 

I've missed this. What started out as curiosity and exploration is now a passion of mine. It didn't take long for me to realize how much I enjoyed kneeling for this man. I feel at home between the safe confines of his legs. It's a welcome release from the pressures of modern male social norms. I set aside all the stress and worries of everyday life in favour of servitude. I love fulfilling this role for him. I love serving this man. 

I slightly adjust my positioning, both for comfort and his pleasure. Without removing my mouth from his cock, I shift back. I remain on my knees. I raise my ass in the air to give him a better view of the thong between my cheeks. I often wonder if he can also see my heels from this position, but I never get the chance to ask. With my hips further away from him, I have some room in front of me to place my palms on the floor to steady myself. 

It's tough to make eye contact in this new position. Instead, I pick up the pace with the rotating motions as I bob my head up and down the length of his shaft. I can hear him moaning. He's enjoying me as I make sure to get everything as slippery as possible. He loves it when I get extra sloppy. It took some time to get used to it. The smell was the biggest factor. I was originally unsettled by the smell of my saliva, but I've come to love it. 

When my playground is sufficiently slippery, I readjust to bring my body closer to his groin again. I'm nestled between his spread legs. This will likely be the last time my hands are dry during this session. So, I take the time to feel up his body. Starting at his ankles, I slowly rub my way up his hairy legs.

As my hands make their way over his knees and onto his quads, I look up into his eyes. This whole time I've been pleasuring the tip of his swollen cock with my tongue, alternating between swirling my tongue around the tip and massaging his frenulum. The friction of my lips and tongue along the crown of his tip drives him wild. 

With some words of affirmation from him, I take my time with this motion. My hands caress his powerful thighs as I lather the tip with my tongue. I seal my lips just below his crown. He can't see my tongue motions, but I don't think he minds. 

As my hands approach the base of his cock, I lower my left hand under his shaft and reach beneath his balls. My index finger is against his body. I'm dangerously close to his taint. His scrotum sits neatly in my palm as I close my hand around it and use my thumb to lightly massage his balls. I love when his sack expands; it hangs so low. Simultaneously, I wrap my right hand around the base of his cock. My pinky, ring finger, and middle finger rest on the mound of flesh above his cock, while my thumb and index finger create a firm ring around the shaft. 

I angle his meaty cock further up. His cock has a natural downward sway. I like the positioning, but there's certain aspects of a blowjob I prefer to do at a different angle. 

I take my lips off his cock and blow him a kiss. I can see my lipstick all over his shaft and tip. I always overdo my lip makeup for our sessions. It took a lot of trial and error to find the right products for sucking his dick. Today's colour is a deep, darker shade of red; almost burgundy.

It's not long before my lips are back on his cock. I start with an audible kiss directly on the slit. I could feel the slick pre-cum. I certainly tasted it. I take my time placing kisses down the length of his cock. Each kiss is delicate and soft. I exaggerate the motions and noises. I know exactly how to get his juices flowing. 

He's starting to become antsy. I can tell by the way he's shifting his hands. I know he's fighting the urge to grab my head and force me back onto his cock. I take this as a challenge. I want him to force his cock back in my mouth. I finished kissing every inch of skin on his cock.

I need another way to tease him. His balls are still in my left hand. I lean down to put one of his testicles in my mouth. His balls are too big for me to take simultaneously. I love feeling his smooth sack against my tongue. It makes lathering both his testicles much more fun. I switch back and forth a few times.

I think his balls have gotten enough attention.

It's time to step up my game. I need to light his fuse and bring out some aggression. I stick out my tongue and make it wide. Starting from the base, I drag my tongue all the way up the underside of his shaft. This does it. The next thing I know, he has a hand on the back of my head. As soon as my tongue flicks past his frenulum, I feel him pulling me forward. His cock enters my mouth in a hurry.

He continues to apply pressure on the back of my head. He's punishing me for being such a tease, reminding me of who's in charge. His cock quickly fills my mouth and starts pushing towards my throat. Now there's pressure on the front of my throat.

"Take it," he says sternly.

It's a rough intrusion. I didn't have enough time to prep my descent. A retching noise escapes me. He doesn't care. He applies a bit more pressure and slips in. 

"10, 9, 8," he starts to count down.

"3, 2, 1."

He finally releases the back of my head. I'm allowed to retreat. 

There's a strand of spit running from my lips to his cock. I'm trying to catch my breath. I don't want to waste any time getting back to his cock. I love when he takes charge and sets the tone. I can feel my own pre-cum leaking from my flaccid member.

I'm prepared this time. My throat is prepped. I'm ready. 

His cock is back in my mouth, willingly this time. My descent is deliberate. I lower myself to my own pace. There's a slight wiggle to my technique. I made a circular motion with my lips on my way down. He loves circular motions. I never understood it, but I always oblige. It's practically second nature for me to make the motions with my wrists and mouth at this point. There's no retching noise this time. His entry into my throat is smooth. I wiggle my ass in delight. I love putting on a show for him. It shows him how much I enjoy this. It also helps get him off.

His cock is in my throat for five seconds. It's shorter than his desired ten seconds, but more comfortable for me. Up and down I went. I throated him repeatedly. On each upstroke, I expertly massage the underside of his shaft with my tongue. I'm hoping to coax out his delicious cum. Every time I reach the bottom, my nose touches his pubic area. 

He's close. I can feel it. A few more strokes in my throat is all it takes. I feel the first spurt of cum when his tip sits between my lips. I can feel the cum shot hit the back of my throat. It coincides with his loud moans of pleasure. I don't miss a beat. I lower myself on his cock again. I love sucking out every last drop of cum. His warmth fills my mouth. It tastes a bit salty today. The slimy, soupy pudding texture is my favourite part. I love how it coats the insides of my cheek.

I swallowed a bit, but make sure to leave most of his cum in my mouth. The show's not over yet.

I take my mouth off his cock and remove my left hand from his balls. Both my hands are on his shaft now. I don't want all my hard work to go to waste. Massaging the mixture of my saliva and what's left of his cum into his skin feels exquisite. It almost feels like spreading lube around his cock.

I'm waiting for him to open his eyes after his climax. He sees me stroking him with a smile across my face. When we're making eye contact, I resume the show. My smile widens. My mouth opens, and I slowly stick my tongue out. I don't want to spill any of the precious cum I haven't swallowed yet. My tongue cradles the cum as I show off. I make an audible 'ahh' noise and bat my eyes at him. He's loving every second of this.

'Swallow it all,' he commands.

I oblige lovingly. Of course, I make a show of it. I close my mouth and tilt my head back. What comes next is one of his favourite sights. I swallow the remainder of his load with an exaggerated gulping sound and motion. He loves seeing my Adam's apple move when I swallow. I must be quite a sight kneeling in my "Daddy's Girl" crop top. 

There's nothing I love more than seeing the look of endearment on his face after a job well done.