When Roberts finally returned a week later, we took things slow. He looked haggard, tired, even though he’d only been gone for two weeks total. His normally tight-fitting clothes looked a little baggy on his skinny frame. He was sitting on my stoop as I pulled into the driveway after work. I gave him tea and sandwiches. He didn’t say much, except to ask, in the sweetest, little voice, for me to remove his enforcer before he showered. I made dinner too, and when we went to bed, I touched him only to hold him close and cuddle.
He woke hard as iron, unconsciously rubbing against the bedsheets. With slender, delicate fingers, I teased his head while my other fingers raked softly through his hair. “Did you miss me?” I asked. When he gave me the right answer, I brought him to climax in seconds.
For the next few days he was very quiet. His youthful excitement had been dampened, I could see. Something in me felt guilty, though I don’t know why. It seems that my involvement, as slight as it was, burned in my head every time I looked at his expressionless face. I never meant for him to get hurt, not really, but of course I couldn’t tell him about my involvement now. It would only hurt our relationship with no benefit to anyone. There was no sense in lingering on the past, so I focused on the future. I took a few days off of work so that we could spend time together. I took him to the department store and spent hours dressing him up and showering him with compliments. As we shopped, I got into the cheerful spirit as well. I saw that a few well-chosen words of encouragement could shape his tastes twice as effectively as months of admonishment. I restrained myself, only buying him a few new outfits, but I realized that I could have his whole skater boy wardrobe in the trash in just a few months. That night I helped him cook dinner and the next morning I helped him clean the house. It wasn’t work I enjoyed, or felt obligated to perform, but spending time in his world seemed to make him happy. By mid-day he was back to his usual self, asking stupid questions, making silly jokes.
I took him out for a date that night, a proper date. Not to a fancy establishment where he would blush at the pretty waitresses, but a rustic-style smokehouse. Roberts felt more comfortable here, where he could make snide jokes about the trashy patrons and tell stories from his childhood. I guess his mom loved this sort of place even though his dad hated eating with his fingers. The more he talked, the more comfortable he became, until he was heatedly recounting all of his childhood fears and aspirations. He wanted to be an astronaut, I learned, and then after that a hair dresser. Eventually he settled on research assistant, but didn’t have the grades or drive for college. I realized that, for all my desire to shape and improve him, I had spent little time inside his head. In truth, he only wanted to be useful, like most boys. I couldn’t, and shouldn’t, continue this game of whack-a-mole, where I was trying to quash each of his pesky vices. I needed to work with his natural inclinations, use his wonder and naivette to both of our betterment.
When we got home, Roberts was flush with laughter and red meat. He was singing the songs he sang in choir, dancing around the room, whipping around the curtains, first like a sash on a beauty queen, then a bullfighter’s cape. “I am Fernanda, the fastest lance in the west,” he explained, whipping the curtain back and forth.
I gave him a look that startled him for a moment before he let out a giggle. I put my forefingers to my forehead and let out a snort, scraping the carpet with my feet. Him being behind the sofa, I had to vault the furniture to charge, hitting him in the middle with my shoulder as I wrapped my arms around him. The force drove him into the wall, where he let out an involuntary “oof.” I pulled him to the ground with my weight on top of him.
Roberts laughed, “You need to be careful. I just ate.”
I snorted again and licked his face. “I don’t do careful. I’m a bull,” I explained, my hand traveling the length of his body from his sensitive armpit to his more sensitive ass. I shifted a little to get my hand under my body, feeling for his already-hard cock trapped up against me. I felt it up and down. It wasn’t a large cock, or a wide one. In fact, it wasn’t particularly superlative in any way except for hardness. “I like it when you wear skirts for me,” I said. “They make your legs look great. And there’s easy access.” His panties were new too, with tight, snappy elastic and bright, vibrant colors. His partially freed cock pulsed in my hand. “Good boy,” I whispered. He closed his eyes and smiled.
I fished the pre-lubricated condom out of my pocket and pulled it over my fingers, my nails longer than what’s probably ideal, but it was too late now. I dragged the latex down his cock, over and under the scrotum, down his perineum, to the warm hole they wanted to invade. “Hey,” he breathed, but did nothing to stop me. He gasped when I entered him, his inflating ribcage outlined by his tight, clingy green shirt. I worked my fingers in and out, probing a little deeper each time, until I settled on a certain trajectory that brushed past his swelling prostate. He felt warm in my hand. “Oh!” he gasped when I rubbed his little prostate. “Nnng,” came from deeper in his throat.
“That’s good,” I told him, “you look so hot when I’m fingering you. I like how you move your body.”
He was breathing hard now, almost to the point of hyperventilation. His hips rose and fell with my fingers, his legs pulsing with the effort. And then, the most beautiful thing happened. A bead of clear liquid formed at the tip of his penis. Then some white joined it and the first bead dropped like a diver off the end of his pink head. Something deep in me melted watching that. It was just so incredibly hot. I couldn’t help but sink a hand down the front of my jeans as I kept up the pressure with my other hand. Sure enough, his cock kept going, sputtering out (not with much force) his lovely little boy cum. Roberts was now moaning audibly, driving his hips up and down such that I was barely moving my hand. “Good boy,” I exclaimed, “Very good.”
That night, when he fucked me, he lasted longer than ever before. His cock felt great for the first while, although, I was so wet that he was hardly making any friction. I rode him for a while, but after his cock slipped out for the third time, I just about lost my patience. Nor could he get me off when I leaned over the side of the bed and he stood on tip-toes. I could feel him trying to drive his cock deep into me, but his hips just bounced off my ass before he got very deep. Then the bitch had the temerity to slap my ass. I looked at him sternly. “You like that, baby,” he asked. His face fell a little and he broke my gaze to return to staring at my ass.
“That’s enough,” I told him. His little boner faded quickly as we sat on the edge of the bed. “You’re going back in chastity,” I announced, “but I just got the best idea.” I had him pay for it, although he had to take out debt from me. Only $50 or so, but it was still significant to the relationship. Now he had a contractual obligation to me. I picked out the dildo, an eight-incher with nice girth, plus a vibrating head. I got a second one too, but I paid for it. The second one was smaller, smaller than any of the toys I already owned. I even had Roberts explain to the woman at the register that he was buying a new cock to fuck his girlfriend because his wasn’t good enough. She seemed to understand.
“Get pretty for me,” I instructed as I made myself a drink. He made the right choice, the choice I hoped he’d make, and came back in his manliest pink skirt and sheer white crop top, all over black fishnets- both stockings and sleeves. I could just imagine what his skater boy friends would think seeing him all dressed up like that. He had put on make-up too, some nice blush and lipstick. “You look gorgeous,” I told him, which seemed to make him happy. Next came the harness, which I helped him into, over the fishnets but under the skirt. His own small package tucked neatly into a pocket of the harness. Then I put the cock on. It was black and ribbed, probably twice the size of his own pitiful erection. “And now look,” I exclaimed, “you’re looking just like a man. Anyone who didn’t know you would think it’s your own.” The hanging cock tented his pink skirt in the most delicious way. “You want to get me ready, baby?” I asked, sitting in the living room and taking a sip of my drink. Roberts sat in front of me, big obedient eyes staring up into mine. “You can start with my feet.” I watched his skinny ass as he rubbed and the suckled on my feet, first the left and then the right. I was ready for his mouth, which he offered generously, sucking and licking my steaming sex greedily, lapping up my folds and suckling my button. As I’ve said, what he lacked in ability he made up for in enthusiasm. I had him sit in the chair as I straddled him, working the new toy inside, cold against my aching cunt, but only for a moment. Soon the dildo was glistening with Roberts’ spit and my own juices, sliding in and out of me with greater ease. This was what fucking is supposed to feel like. I lowered myself down slowly, with great determination, until my cunt was filled completely. “Yes,” I moaned, lips on Roberts’ ear, fingers holding tight to his hair. “Yes, that’s how I want it. Finally a proper fuck out of you.” He was thrusting with all the force of a timid doormouse, but I’ll be damned if it didn’t fill me up just the way it should. “Fuck, fuck,” I grinded up and down his abdomen, jamming my clit against his body as I rode the surrogate cock, listening to the hushed panting he made as I pushed the air from his lungs. “Harder, harder!” I insisted, for all the good it did me, but in the end, I brought myself to a pretty decent orgasm, the best I’d had with Roberts’ assistance.
When I was ready, I dismounted and pulled the cock from its holster. “Now it’s your turn,” I explained. Of course, naive dear he was, looked to his crotch. I shook my head, trying hard to suppress the smile. “You’re going to cum the way that I did,” I told him. “I’ll help.”
Roberts was suddenly serious, the playfulness gone from his tone. “I really d-d-uh-don’t please I de-duh-don’t want to d-d-do that. I’m not r-re-uh-really feeling-”
“Oh please, baby,” I insisted. “Please. It’s just so hot. I love watching you like that.”
His voice was low and desperate. “I don’t want to.”
“No fun,” I sighed. I took the harness off of him and inserted my own dildo anyway. When I pulled up the harness, the small dildo’s other end sank into my pussy, significantly smaller than the previous delight, but enough to get purchase inside of me. I walked around the room, admiring my new cock. I even gave it a stroke or two, which manipulated the other end in a most… interesting way. “Are you sure you don’t want this,” I asked, looking down at myself. “I mean, I look like a sex goddess. Look at me.” He looked, but his face did not change. “Okay, that’s fine,” I said. “That’s fine.”
“Are you still going to let me out?” he asked, meek as a schoolboy.