an: this was written by LashtonsFlowerCrown
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I open up Kik, smirking when I see a message from my sugar baby.
Baby Boi: Good morning Daddy, I hope you had a good sleep. I couldn't sleep, I kept thinking of yesterday ;)
Call Me Daddy: Good morning Baby Boy. Of course I slept well, I was thinking of you the whole time. I'm sorry you couldn't sleep, but of course I'm glad you were thinking of me.
Baby Boi: I'm glad you sent me that present in the mail last week Daddy. I haven't had a chance to use it yet, but my parents left for a week this morning so I'll have plenty of time to use it and send you all the pictures you want. Even videos if Daddy requests it.
Call Me Daddy: Well you can start with a picture of you in a thong, you know how much I love those pictures of you.
Baby Boi: *camera picture sent*
Call Me Daddy: Very nice Baby. But it would be even better if those were stuffed in your mouth, my hard cock thrusting into your ass as you cried out in pleasure.
Baby Boi: Daddy those are very naughty thoughts.
Call Me Daddy: Am I making you hard Baby Boy? Am I teasing you? Making you want stimulation? Don't lie to me, you know I always find out.
Baby Boi: Yes Daddy. I just want you in me, pounding into me. I've never let myself with another man this whole time you've been my Daddy. I just want to feel you inside me, fucking me mercilessly.
Call Me Daddy: Get the toy I got you. And lube, you'll need it. Send a picture of them on your bed when you have them ready.
Baby Boi: *camera picture sent* What do I do now Daddy?
Call Me Daddy: Play with your nipples. Roll them through your fingers, tug on them
Baby Boi: Okay Daddy.
Call Me Daddy: Call me. I want to hear your voice.
I got a call less than thirty seconds later from him, and I picked up. The app we used had a voice filter so that we wouldn't know each other's true identity.
"Hello Baby Boy." I chuckled, pulling my grey sweatpants down just far enough so I could pull my cock out since I wasn't wearing boxers. All I got in response was panting and a high pitched moan. A smirk formed on my face and I stroked myself, getting myself hard to the sounds of him pleasuring himself. "Are you hard Baby?" I got a hum in response. "Okay stop playing with your nipples. Message me a picture." His moaning stopped and I heard him fumbling with his phone.
I opened Kik and looked at the picture, smirking at his fully erect nipple with a bar piercing going right through it. "Such a good boy, doing what Daddy tells you to do. Roll over onto your stomach and get some lube on your fingers." I heard fabric rustling and liquid spurting out of a bottle. "Don't take your thong off, just move it to the side. Push a finger in and slowly pump it Baby Boy. I don't want you stimulating yourself too much." I heard a quiet moan as he pushed his finger in, causing my dick to twitch in excitement.
"D-Daddy it feels so good. Don't wanna stop." My baby spoke between moans and pants, obviously working himself over without letting himself release.
"Put in another finger baby, stretch yourself. Don't be shy, I want to hear you." I slowly stroked myself, back arching as I flicked my wrist. He started moaning louder and more often as he worked himself before I told him to put in a third finger. "I want you to fuck yourself on your fingers. It's okay if you cum, but that doesn't mean this is over Baby Boy. Understand?" I instructed, smirking when I got his approval. Less than thirty seconds later I heard him cry out in pleasure, indicating his orgasm.
"Was it good Baby? Fucking yourself on your fingers like Daddy's little whore?" I hadn't worked myself up to my release yet, but I was getting close.
"Y-yes Daddy. Felt so good." His voice was quiet, his body tired from the orgasm.
"Good. I want you to put my present in you. As far as you can fit, don't push yourself too far. Then I want a picture of my baby." I heard fabric moving again and lube being poured, presumably onto the dildo. He moaned loudly as he started pushing it in.
"S-so big." He whimpers. I could only imagine how good he looked, body wrecked, cum stained all over his lace thong, a dildo the exact measurements of my cock sticking out of his ass. "o-OH!" He cried out. "I-it's in Daddy." I got a notification on Kik telling me he had sent a picture. I opened it, smirking at the sight. His ass was perked up, the dildo sticking out of it. But what intrigued me the most, were the posters in the background. My best friend Tyler had the exact same ones. In the same spots...And his parents left this morning for a week long business trip.
It didn't take long for me to put two and two together. I was a Sugar Daddy, and my Sugar Baby was my best friend, who I coincidentally had a crush on for most of my life.
"D-Daddy what now?" Tyler said breathlessly.
"There's a suction on the bottom. Suction it to the ground and I want you to ride it." I got up and tucked my cock back into my sweatpants, pulling on a shirt quickly and getting shoes on. The pop of the suction sounded and then a cry of pleasure as he sank down onto the toy. I grabbed my keys and stuffed them into my pocket as I left my home, walking down the street to his house. Tyler's moans filled my phone speaker as I walked quietly, encouraging him to keep going.
Luckily, his front door was unlocked so I slipped in, trying to make minimal noise. I slipped my shoes off and walked upstairs to his room. His door was ajar, his back to the door, meaning I could watch without getting caught. He was bare minus the thong, of which the string was pulled to the side. My breath hitched in my throat as I watched him rise and sink along the toy I had sent to him.
"D-daddy are you still there?" His voice cracked as his body shook with pleasure.
"Yes Baby." I cancelled our call and stepped into his room, taking my shirt off and discarding it on the floor. Tyler shrieked and craned his neck, eyes widening when he saw me.
"J-josh?"
"It's Daddy to you." I stepped closer to him and pulled him off the toy, leaving him kneeling on the floor. I spread his cheeks and smirked at his puckered hole, stretched from the dildo. Tyler turned around, still on his knees. "I see you like the toy very much. But how about the real thing?" I tugged my sweatpants down ever so slightly, my v-line showing and leading to a hidden point underneath. Tyler gulped but nodded, his hands pulling my pants down to my ankles, helping me step out of them. My length was hard and leaking slightly with pre-cum. Tyler gently grabbed the base and pumped a few times, causing a moan to escape past my lips. His lips wrapped gently around my tip, sucking slightly and giving kitten lips, doll eyes looking up to meet mine with such an innocent look. My fingers wove through his hair and tugged him more, which made him start bobbing his head around my length. He always boasted about not having a gag reflex, so I decided to put it to the test and I pulled his head away.
"Breathe." I instructed him. He took a breath and I pushed him down, seeing how far I could go. His nose brushed against my pelvis and I smirked, using my other hand to feel his throat and feel my cock inside him. "Such a good baby boy." I let his head go but he didn't move, his tongue working around my length. He swallowed and caused his muscles to contract, making me moan even more. Tyler took that and started bobbing his head even more, little hums of approval vibrating around my shaft. His hand wrapped around my balls, playing with them gently as he worked me to the edge. Eventually I came, with a loud moan, down his throat. Like the good boy he is, Tyler swallowed and licked my length clean as he pulled away. His eyes were rimmed red with tears. I helped him to his feet and gave him a short kiss on the lips.
"Was it good Baby?" I held his hips gently, fingers rubbing his sides. He nodded and shuddered under my touch. "You were such a good boy, taking Daddy's cock like that. You looked so good riding the dildo, how would you like to be fucked by the real thing?" Tyler nodded eagerly, so I reached down and pulled the toy off the floor, a smirk upon my lips. I nudged him over to the bed and had him get on his knees. I pushed his torso forward so that his hips and ass were in the air. He whimpered in pleasure as I slapped him a couple of times. I pulled a condom out of his nightstand and rolled it on myself, pumping a few times to get hard again.
"It's gonna be a stretch okay." I pushed in gently, slowly sinking all the way down. Tyler let out a muffled whimper and I gently rubbed his back letting him know it was okay. Slowly, I pulled out and pushed back in a few times before pulling out completely. He whimpered at the loss of contact but I pushed in the dildo about an inch or two before pushing myself back in. Tyler moaned quietly and fisted the sheets, biting down on his lip hard enough to draw blood.
"This okay?" I asked him quietly, not wanting to hurt him. He nodded and gently pushed back against me, letting me know it's okay to keep going. I pushed myself in and as I slowly pulled out, I pushed in the dildo. I kept a steady rhythm going of alternating before I left the dildo pushed in and pushed myself in all the way.
"F-fuck Daddy." He whimpered. His length was leaking all over his panties and he was shaking but he knew better than to cum without me telling him he could first. I pulled the dildo out and roughly grabbing his hips, causing him to yelp. My hips snapped up to his bum, causing a wave of pleasure to run through my body. "R-right there. P-please." Tyler begged.
"Right where?" I smirked, slowly rocking my body to hit his prostate ever so gently over and over.
"P-please Daddy!" His voice shook, his body trembling with pleasure. I smirked and started pounding into Tyler mercilessly, the sound of our skin colliding every time edged me more. I finally came into the condom, telling Tyler it was okay to let himself release. I thrusted one more time and he came undone, his body going limp. I slowly pulled out and patted his bum, gently rolling him onto his back. I disposed of the condom and used a piece of clothing from the floor to gently wipe him down, discarding of his thong. Tyler curled into my body and I held him close,smiling at him. Who would've thought that my Sugar Baby would end up being my best friend? I surely didn't, but I wouldn't change it for the world.
