I couldn't tell who was more nervous at this point. Him or me? I honestly couldn't even believe that I'd manage to get him to agree to this but I'm not complaining. Pants pools around his ankles along with his boxers, bent over the edge of the bed, his beautiful ass and meaty thighs all on display at my will. His shirt disposed of a while ago, hickeys were to be soon littered on his back and shoulder and his ass definitely will be sore for his first time.
"You sure you are okay with this?" I ask for about the millionth time this night. "Shay, this was your idea, dumbass." He huff out with annoyance. "I'm making sure that your comfortable." I say as I raise my hand hesitantly to lay on his right cheek. I felt the skin of his cheek before, mostly when I was being fucked out and in need of something to hold but this felt different, it was different. "What abou- just fucking get it over with." He says in defeat as he prepares himself mentally. "Okay, your word is." He sighs. "Red and I have to call you Mommy." I smile even though his tone is as if he's unamused. I know he's always wanted to call me Mommy, he just wont admit it, it's the Mommy issues.
I take a good amount of lube into my my fingertips, some leaks off but I rub most of it onto my fingers and bring the cold liquid cover tips to his hole. He tries to arch his back to get away but I slap his thigh with my other hand before smearing the lube onto his hole. "It's cold." He complains. "Quit being a baby." He rolls his eyes. "I'm not a ba-" I cut him off by shoving a finger into his tight entrance, his stiffens under my touch, and I slowly add another finger. His hands grip at the sheets below him and he buries his head in the blanket to avoid me hearing any noise he was producing. "You were saying baby." He huff a breath out his nose. "Fuck you." He mutters into the blanket in a strained tone. I add another finger just in case, stilling my hand to let him adjust to the feeling of being stretch and unlike him I'm patient with him. "No need. I'll be fucking you soon. Tell me when." There's just a moment of awkward, not awkward silence before he taps my leg as a signal for me to move and I smirk. "Use your words, Simon." He lifts his head up, looking back at me with a death glare and I shoot him an innocent look. I definitely will be abusing my power tonight.
"Move, please." He mutters. "What was that?" He groans in annoyance as he burries his face again. "Mommy, please move your fingers." He says loud but it's more muffle but I can still hear him and decide to give in. "Wasn't that easy, doll." I slowly drag my fingers out of his hole till the tips of my fingers remained, spitting on my fingers for more coverage, I thrust them back in roughly making him squeak out a noise through the blanket and buck his hips. "Fucking hell." He mutters. I repeat the action but more softer this time, for his sake, but began to build a pace. A strangled moan fall from his lips when I curved my fingers like he had done to me and I smirk. "Does my baby boy like that?" I tease. Precum drips from his unattended cock below him onto the sheets and he nods slowly. "Yes mommy." He manages. I quicken the pace, encouraging him to make more noise, and occasionally curving my finger to make his head spin in pleasure.
To my surprise he got comfortable with the pleasure soon than I'd expect, he was buck his hip for more friction on his cock and soon was a moaning mess.
"Fuck, Mommy more." He stutters out and I happily obliged by his request. Speeding up my movement, I use my other hand to spank him and he lets out a small yelp from the mix of pain and pleasure. I was a little overstepping with the spanking but he seemed to enjoy and let it slide. I sooth the cheek with a soft caress and small kiss. "Such a good boy. You're taking my fingers so well." In a needy rut, he pushes his hips back to match the thrust of my finger and doesn't hide as much of his noises.
A bright blush fills his face from embarrassment of how much he was actually enjoying himself. A knot in his stomach beginning to form, he squeezed my fingers as a warning of his soon arriving climax and it was all so new for him. The praises didn't help either, the seductive way I'd tell him how good he was taking me, how tight he felt and how wet I was getting, it could make him cum on instant. But he wanted to last.
"Fuck me, please. Mommy, I'm ready, please." He pathetically begged in a trans of pleasure. A small patch of drool began to form on his mouth, spilling with noise and losing himself in the sensations he felt. It was a sight for sure, something I never wanted to forget. I halt my actions, slowly removing my fingers making him whimper and whine from the lost feelings. "Don't worry baby boy. You're gonna do just fine on the real thing." I take some more lube, coating his hole once more and coating the strap on evenly with a couple of pumps.
Wiping my hand off with my shirt that was on the floor, I take the thin material and rip it to my desired use. I yank his wrist behind his back, tying them together and leaving a bit of material for me to pull him back at any given time. "Mommy." He begged and I smirk. "Hush baby. You'll get what you want to soon." I cooed making him blush and hid his face once more. I take the cock into my hand, rubbing the tip against his puckering hole making him whine and push back for more friction. I yank at the material, his shoulders pull back a little at the force and he bows his head a little. "Such a needy thing. You get fingered one time and already so greedy for more." He lets out a moan at such lewd words being spoken to him as he his head only set on the pleasure he wishes to feel again. "You gonna be a good boy?" I ask as I continue to rub the tip against his hole, softly adding pressure to let it slip in before pulling back out again. "Yes, I'll be a good boy, Mommy. Just fuck me please." Who knew such a man could posses such a submissive bone within him. I loved every second of it.
Finally, I push slowly inside of his hole, with a bit of resistance, making him moan and try to relax more for me to go deeper. "That's it baby." I cooed. I moan as well as I watch the cock plunge inch by inch inside of beautiful soldier. Once all settled deep inside of him, I let him adjust once more and he takes more time this time around to adjust to the size. "Shit." He mutters as he pulses around the cock and I couldn't help but to laugh a bit. "You okay, Simon?" I ask. "Just a little bit more time, please. It still burns a bit." He speaks so shyly which was very new for me and I am a little too stunned to speak. "Take your time. It's at your pace." He nods. I yanks him up a little bit, leaning down to meet him half way, I lay kisses on his neck and back to distract him from any discomfort. "You're doing great." I remind him and I could see him smiling under his mask. "You can move now." He mutter to me before looking away. I let him fall back down, his chest pressed to the bed, I wrap the fabric around my hand tightly with one hand and put the other one on his hip. I pull out slowly, easing every inch out of him till the tip remained, pushing it back in with the same easing motion which elects beautiful muse from Simon below me. "God fuck." He moans. "Does it feel good baby boy?" He nods his head and flushes embarrass again. I take my time building up the pace, starting to thrusting in and out with a little more oomf, and Simon was bound to be a mess again soon.
When I quicken my pace, I lean down marking his shoulder with dark bruises and cresent shapes into his hip making him hiss with pleasure. "You look so beautiful marked up by mommy." My hips snapping back and forward, the sounds Simon's strangled moans, my soft pants and skin on skin fills the room soon. "Fuck you're so good. Keep going." He moan making me move faster and deeper.
I yank him up, his back pressing to my chest, he towered me, of course, but that didn't stop me from fucking him at the pace that I was. His head falls back in pleasure, I take my hand from his waist and wrap it around his red cock that was soaked with his precum. "Mmm fuck mommy. Mommy." He spoke my title like a prayer when I began stroking his cock. Swiping my thumb over the tip sent a shock of pleasure coursing through his body that he pulses in my palm. "Do I make you feel this good baby." He nods his head quickly and moans out in pleasure. "I'm going to cum." I smirk against his skin, laying gentle kisses on his back as I worked his ass and cock. I keep at my pace knowing that will make him cum sooner than going faster or harder but I do stroke his cock a little faster making him fuck my hand before pushing his ass back to meet my thrust. "Cum for me." It was like a switch immediately and he does as he was told. Twitching roughly in my palm, strings of cum shoot from his cock, and I make to milk out every drop. He falls to his forearms, I release the fabric to let him fall, shaking from his earth tearing orgasm, he pulses so tightly around the cock as I softly pull out after letting him ride his high. "Such a good boy." I kiss his cheek before he lets his body sink into the bed.
I remove the strap, cleaning it off, coming with a damp warm rag, I lift his hips to clean Simon off as he fights to keep his eyes open. "Thank you." He mutter and I smile. "No, thank you baby." I climb into bed, he wraps his arm around my waist, laying his head in my lap and I massage his shoulder and upper back till he falls asleep. Which didn't take long since he was definitely worn out after this session. I smile and lean down, missing his head. "Good job Simon." I mutter to the sleepy boy.
