So I had a big Sunday planned for my boi vinny, but it was still early, and he was still snoring as I began to wake up. I love the way he sleeps. When vinny is "down for the night," he is "DOWN FOR THE NIGHT." I don't think the boy moves, other than to breathe. (Of course, if I have a need to get satisfied, he moves: I trained him well. Like one of my friends said, I'm not a patient man, but I wanted Vinny, and this time, I was ready to commit to the time it took). Today was going to be a challenging one for him, that I knew. Internally, I was laughing. I wasn't sure if taking a man's cock for the first time, or spending money on clothes was gonna be more of a challenge for him. I HAD planned to invite friends over to "celebrate" for dinner, but thought it might be a bit too soon for my vinny boy, and I asked if they guys could come next week. That wasn't a problem. I also wanted vinny to start learning more about what it meant to be a sub - MY sub. Being a sub didn't necessarily mean taking your Dom's cock - there were a lot of relationships I knew about where that wasn't part of it at all. To be MY sub, you took my cock. In your mouth and in your ass. And you did other things too. Baby steps? Hell, those baby steps were about to get bigger.
I felt vinny stirring . I ran my finger along his ear, very very gently, and whispered. "Good morning sexy?" before I kissed it . He made a satsifed groan and backed into me just a little bit further. My cock was rigid, but he didn't seem to mind (I later realized that, when Vinny was sleeping, he wasn't much aware of anything. He was just trying to feel warmer, and maybe get some more of what was making his ear feel so good. THAT he got as I began nibbling and licking. My hand went down to his cock which was rigid too. That got him awake. He smiled.
"Good morning Dave. I mean Sir. Sorry." I squeezed his cock just a little bit. "You need to get drained vinny boy?" "I think so. But that's up to you Sir." I smiled, sighed, and rolled him onto his back before I got on top of him. "Your neck please." "Yes sir," he said, as he stretched his head to the side so that I could begin scruffing him up. I was gentle: VERY gentle. It was Sunday and tomorrow was a work day. I knew he was still freaking out over the idea of showing any markings at work, so I treated him really, REALLY gently. It was enough. "OH YES SIR. OH YES. OH... DON'T STOP. PLEASE. MMMMMM. " I could feel his pecker getting more and more engaged. I needed to do something to show who was in charge. "On your belly boy. I'm gonna introduce you to something new." He sighed. He wasn't happy, because he really thought that, in maybe 30 seconds, he'd feel the bliss of an orgasm. Once I had him on his belly though, I rubbed the slightest big of lubricant between this thighs. Then I slide my cock in, and fucked him that way. I knew it felt weird to him. He said it. "It's either that, or your ass. I'd rather your ass, but I'm trying to be kind." I could hear him suck in his breath as he grunted out "THANK YOU SIR" , and I tried to be as gentle as I could in biting his ear when I shot, right through his thighs. Then I flipped him over. "Now it's your turn vinny boy. But you NEVER cum unless you get permission from me. If I catch you.. we have tools to lock that pecker up, and you won't be able to. " I began to slide my hand up and down on his cock. "Understood?" "Understood Sir. OH GOD YOU DO THAT SO GOOD." I stopped for a minute. "When we're done, you gonna tell me what you dreamed about to give you that wood?" He blushed. "I'll tell you right now Sir. I dreamed we were on your sofa, and you were kissing me. I began to fall backwards, but you held me, and you kept kissing me. And then... OH FUCK." Even though I wasn't touching him, he exploded. I smiled "That was a REALLY hot dream vinny. I hope I give you a lot more." "Can you hold me just a little before we get up Sir? I've... I've never been held closely before, for so long. And you're so.. secure." I laughed. "secure. " I wonder what he meant. He didn't mean "secure." We cuddled for about ten minutes, then I ran my finger over his nose. "So, I think you should start getting yourself cleaned up. I'm next. While you're washing, I'm gonna get breakfast together, and I'll finish it up when I get out of your shower. " I leaned in and kissed him. "Here's your assignment. You're proud of the guy you're with, and you wanna make him proud of you. So, get yourself ready with that in mind. " I knew I had just given Vinny what was going to be a difficult assignment. GOOD. I wanted to see what he thought made him look attractive. When I came out of the shower, and met up with vinny in the kitchen, he had put on a button down with a very small check pattern: blue, red and yellow. I didn't even see that one in the clothes we brought. One issue: TOO BIG. He had paired it with light colored slacks. "NICE vinny. NICE. I'd be proud to be seen with you if you wore that." He blushed. "Thank you Sir. It's not easy for me. You just put yourself together so easily." I had on a heavy weight henley with the sleeves pushed back: gray, and faded jeans. I was looking for a slightly butch look: I had a feeling vinny needed his man to look, well, "manly" as he "defined" it. "You'll learn stud . You've got a good teacher . Now, let me get to work. Pancakes?" "MMM. Haven't had them in ages. I usually grab a muffin on the way to the office, or a bagel. " "Ha ha. Once we start you at the gym, that'll change a bit, vinny boy."
He smiled. It WASN'T about the gym. He really seemed to like being called "vinny boy." "I'm gonna have to go to the gym Sir?" "Yup. Probably at first with me. Then on your own. But you're going. " He looked like he had tasted sour milk. "Let's talk about that while we eat vinny. The gym is, in one way, related to what we're doing this morning.
I put down a plate of pancakes with real maple syrup and the taste seemed to shock him. "It's strong. But it's good. It goes with the coffee Sir." "You're not used to real maple syrup, I guess." "Isn't it the same as pancake syrup, Sir?" "No, not at all." "Then I guess I'm not used to it. " "Well, that's what we use around here. Anyhow, let's chat a bit about the shopping expedition, and the gym. I want you to feel comfortable." "I'll try Sir. I'm just not good at shopping for clothes. " "Well, when you need things, what do you do?" "I have a list. Some years ago - I think I was in law school - someone gave me a list of what every lawyer should have - and I shop from that list. When the things wear out, I get new ones." "Ok. That might have been fine, but you know what? That's a 'one size fits all' list. It's not good enough anymore. You're a sexy guy vinny. We're gonna work on making you sexier at work, and out of work. Because...." I got up and walked behind him, massaging his tight shoulders. "My man needs to be as sexy as any other guy in town. " "You think I'm sexy Sir?" I kissed the top of his head. "vinny boy, I think you may be the sexiest man I've seen in a long, LONG time, and I like being seen with sexy men. So I'm gonna do what I can do to dress you, and to get you built up too. " I teased him. "Those nips of yours are gonna point out of every shirt, and your arms are gonna get so big, I'm gonna have to work to keep you in line." He smiled. "I think you already figured out how to keep me in line Sir. " "OOOH. That sounds HOT vinny. I'm just gonna keep on doing it. " I kissed him again. "Ok , so why don't we get up and going? Sunday is crazy at the stores. " I figured that I didn't want to freak him out TOO much, TOO soon, so we'd go Mall shopping. I figured he'd be more comfortable there. We'd get to "gay boutique shopping in the future. "
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"The let you try on shirts, Sir? " He asked me as the clerk went off to find an opened version of the shirt I had picked for vinny to try on. "They don't like to advertise it, but they do. It increases their expenses, it's inconvenient, but you're entitled to it. "Here you are Sir. In two sizes, as you asked." I thought that for his work persona, vinny needn't change too much, but his clothes were TOO BIG. He had a sexy, wiry body that he was hiding under all that fabric. I had the clerk bring him a white shirt in the size he wore, and one size smaller. I had him try on the smaller size first. "Tight Sir. Hugs me." But he was grinning. "Let's take a look in the mirror. See how you like it." (I knew he had caught a look at himself on the way out of the dressing room. ). He was silent as he looked. The shirt didn't bag at his middle, and it looked good with a button opened. "Open the second button vinny. Let's see how that looks." "But that's so, well, ..." I gave him a look and he whispered "yes sir." I don't think the clerk was looking. I HOPE he wasn't looking, because vinny popped a boner right there, looking at himself. You could almost hear him thinking "I've never looked so good." I came up and put one hand on a shoulder. "So , here's what we can do. If you like the way this size looks, we can stop right here. You don't have to try on the other one. We'll just go through your list, but if there's something you don't like, we'll pick something else. Those are work clothes: they're on you . Then, I'm buying the shirts I want you to wear when you're off duty. " "You don't need to do that Sir" "I want to do it. Now let's go through your list." His list was fairly standard. I knocked a couple of items off, and added others. "Where did you get the shirt you're wearing vinny? That's not something I'd expect you to buy." "Christmas present Sir. My niece gave it to me. She said I needed to show off how handsome I was." "I LIKE your niece. I gotta meet her some day." "Her name is Gina. I think you'd like her. " Again, I didn't want to push him too hard on this first day. Since he liked button downs, I stuck to those, going with solid, "casual" colors. You know what I mean: the colors where you look at a shirt and say "oh, it's dark red," but its official color is "red wine vinegar." All solids, all casual colors, and all in that size. We did a repeat, getting some new slacks for work, some jeans, some corduroys, some khakis. As we went back to the car, loaded down with the bags, he laughed. "That was more than my monthly mortgage payment." Yes, but you just got enough clothes to tide you over for at least six months. And you're gonna be SO happy with them. " As we settled into the car, before I could get my hand on the wheel, he took it. "I'm happy with you Sir." I squeezed back. "And I'm over the moon with my sexy vinny boy."
We were both full from the pancakes, so we didn't stop for lunch, and I was beginning to get nervous. Today was the day I was introducing vinny to the art of anal sex. I was taking deep breaths. He knew something was up, but he didn't know what. I had to get myself together. So far, vinny had been so far "ahead of the curve" in taking in his new life, that I had been challenged to change things up. This was BIG stuff though. Well, let's see.
I was pretty silent on the way back to my house. So was vinny. He asked at one point "Is everything ok, Sir?" I smiled. "Oh yes, just thinking. Just thinking." "Anything I can help with?" The question was sincere. If nothing else, I had made a good friend. That wasn't something to sneeze at. "You trust me vinny yes?" "Oh I do Sir. Honestly, I had my doubts at the start, but you've been on point and honest. " He also smiled. "You know, at one point you said 'I can handle you, I'm not concerned,' and I thought 'that's a cocky bastard.' But you can. And you do. You deserve to be the alpha Sir. " "SHIT WHY WAS HE MAKING THIS THIS HARD?" I thought, and not about my cock, and my cock WAS hard. "Good. I won't do anything to hurt you. Just understand if you say no, and I say yes..." "Then the answer is yes. I know that Sir." We pulled into my driveway. Let's get this stuff inside. Maybe we'll get a fashion show later." We put everything at the side, and I smiled at vinny. "how about some day drinking?" I pulled out a bottle of a good red that I had, and two glasses. "I won't say no, Sir." I poured, and toasted. "To us." "To us Sir." I reached over and began gently massaging his earlobe. He purred a little. "OOOOO. I love how that feels Sir." I took a big swig of my wine. "Know what it's time for vinny? " He reddened. He did, but he wasn't quite ready. "I don't think so Sir." "I smiled. "Yeah, ya do. It's time for you to learn a little more about what my vinny boi needs to do. And that's to take my cock up his ass." He looked down, then looked at me. "I don't think I'm ready Sir." "Yes, but I am." vinny gulped. I smiled and squeezed his hand. "Finish up your wine. It'll help to relax you. It IS happening." He was shaking as he tried to drink. "vinny, this isn't going to be rape or violent, or anything like that." I was going to say " that comes later when we get to roleplay," but thought better of it. "Another glass?" "No Sir. I guess..." he shrugged his shoulders. "I should feel it the first time." I got up and kissed him. "Let's go. I'm going to be honored to be your first."
xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx Well, we got up to the bedroom, and he started to undress. I stopped him. "No. We're gonna do this right, my sexy sweet vinny boy." I came up to him and held both of his hands. I kissed him and whispered. "I have wanted this since day 1." "I know Sir. I'm sorry I made you wait." "You didn't make me wait vinny. " I kissed him some more and, in the kiss, I gently moved him to the bed, on his back. I lay next to him. I had an idea of how to get him primed, and I began licking his ear. "OOOOH. OH GOD SIR. That feels so good. " "know what I'm gonna do vinny boi? I'm not gonna do anything other than play with your ear, until you ask me to go ahead. " In the short time we'd been together, I had learned exactly what areas of vinny's ears were most sensitive. They were not the same on both ears, and I was working on his left one. Slowly, I ran scruff up the frame of his ear, before darting in with my tongue. I had positioned myself so that he couldn't fight what was happening: I pinned his wrists down. Every now and then, I'd make an animal noise in his ear. I knew he liked those. They got him really, REALLY hot. After about ten minutes of this, he began to tremble. His tongue was moistening his lips and he whispered. "Ok Sir. I'm ready. Please go easy. " I moved my mouth over his and kissed him. "I will vinny boi. thank you." I slid down to the foot of the bed and got his shoes, his pants, and his briefs off. He was hard. No question about it. The work on his ear had him stimulated. I reached in and slowly pulled out his butt plug. "Good boi vinny. You kept using it. It'll make things easier." I reached over, for lube and a condom. He looked and said softly "Thank you Sir. I was hoping." I just smiled as I got the condom on me, and gently rubbed lube into him. "Ok, vinny boi. Grab hold of something we've done that you liked. "THE FIRST TIME YOU KISSED ME." He began to breathe hard. He was focusing on that. "your tongue moving around my mouth... OH GOD SIR. I never felt anything like that.." That's when I slipped my cockhead in. He didn't notice, until I was about 3 inches in. "You're there, aren't you Sir?" "I am. Are you ok?" "I can feel it. It doesn't hurt but, well, I feel full. " "Breathe vinny. Breath nice and easy. " I wondered what was the best thing to do. If I leaned up to kiss him, I risked going in faster than he was ready for, so I just held his balls in my hand and fondled them. "Such a nice set, you sexy boi. SUCH A NICE SET." He moaned in appreciation, and I got in further. If I told him I was in further than the butt plug, it might freak him out. It might make him feel good about himself, but I didn't know. I didn't say anything. "You ok vinny?" "Yes sir. " He grinned. "I thought you were bigger than that." HE WAS GETTING INTO IT! OK, time to try... " I shoved all the way in. He didn't scream in pain, just, well, amazement. "OH MY GOD SIR. YOU'RE... THICK." "This was the easy part vinny. Now, try this." I began to slide back and forth. "Tell me if something really hurts, or if something feels REALLY good." "THERE. RIGHT THERE. OH THAT'S NICE!" I had found a spot, so I just moved gently back and forth. "OH SHIT SIR YOU'RE GONNA DRIVE ME NUTS..." "Well, serves you right for how crazy you drive me whenever I see you, handsome." Now, I DID lean over and kiss him and I went in further. "GOD THIS DOESN'T FEEL LIKE I THOUGHT IT WOULD." I pushed back and forth. "You're just doing so great vinny. SO FUCKING GREAT. " I stopped and tried something. "you my boi, vinny?" "Yes sir." "You like having me in you?" "Yes sir." "Worth the wait?" "HELL YEAH SIR."
He was mine. I began to pump hard. I didn't want to exhaust him on the first try, but I wasn't ending this without an orgasm. And then it happened. I hadn't said anything to him, and how he knew, I've never found out. He tightened the muscles and I shot, not when I wanted to, but more than I expected. He was smiling as I pumped. He KNEW he had done good.
"Look away vinny. This isn't the prettiest part of this," I said as I withdrew. He had already looked to the side as I dumped the spent condom. Then, I smiled. "Such a good boi. You need a blow job?" "Everyone does Sir" he joked. And he got one. I don't do them often, but he deserved it. I extended it for about twelve minutes, bringing him to the edge, and lowering him and then starting again. When he couldn't hold it anymore, he yelled "I'M GONNA SHOOT SIR," probably so I could pull away, but I've swallowed for men I liked far less than vinny. I took down every drop. He looked at me. "But... but Sir... you're the Top. " "Yeah, so?" "But..." "I do what I want, and I wanted your cum. " I smiled and licked my lips. "No more discussion." I lay down next to him and pulled him close to me. "How are you doing, sweet stuff?" "I don't know Sir. I feel... I feel proud, confused, happy, loved, cheap, valued.. I'm flooding." "You want a nap, vinny?" "If you promise to hold me, Sir." "I can do that. Close your eyes. Rest." He did. He slept for about an hour and a half. I must have nodded off, because I woke up with his lips pressed against mine. "That may have been the best Sunday afternoon since first Communion Sir." He smiled that broad toothy grin that got me every time. "GRRRRRRRRRRRR." I rolled on top of him. I kissed him and smiled. "I am SO proud of you vinny boi, and I'm SO glad I made the move to pick you up that night." "Is it ok if I spend the night Sir? " He laughed. "I think I have clothes for work here." "You don't have to leave if you don't want to. " In fact, we drove back to his house to get a few things. I had promised to make dinner that night, and I made spaghetti and meatballs, garlic bread, salad. We had some ice cream in the freezer. "Next week, I was gonna invite the football team over. I think they wanna get to know you better. Is that good with you?" "I wanna meet all your friends Sir. I want them to be my friends too." We watched some crappy Sunday television before bed, and I introduced vinny to a new part of his life as a sub. "At my feet vinny. You can sit with your head against my crotch if you like, but on the floor. So I can keep you locked up in my legs. He actually seemed to enjoy it. And his sleep that night was solid, and unbroken. Next day, when we were both at work, I sent him a bouquet of pink roses. He didn't understand. I promised I'd tell him at dinner. I did. Right before I reinforced the lessons of Sunday.