Becoming a Boy 30
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Fuck. Now that was hot! Timmy had a great pussy. I couldn't believe how tight he was or how he just squeezed the load out of me, like he needed it right then. I pulled myself up off of him. He didn't seem to want to release me, his ass was clenching my cock tight, so I just arranged myself so I was comfortable.
"I'm sorry, sorry Sir," he said. "I didn't mean to kiss you."
I grinned at him. "No worries, you were in the midst of your orgasm." He looked at me as if I might do something to him, but I didn't care if he kissed me, at least not in this situation.
"Oh god, I've never felt anything like that before. It was like all over me, not just my dick."
"Your clit," I reminded him.
"Oh yeah," he looked sheepish. "It was like all over my body. I couldn't stop twitching or shaking. It was amazing. How did that happen?"
"It happened because your body was built for that," I told him. I knew enough about a fag that you wanted to reinforce things when they happened, so they adjusted to their place and what you could do for them. I wanted Timmy to know he was my fuck toy and that I could provide that sort of pleasure to him and that he in turn would love the hell out of it happening. "You had a full body orgasm because you let yourself relax and enjoy my cock. You don't want to fight this Timmy. Your body was made to take cock. You can see that now can't you?"
I was on my knees now, looking down at him; my dick was still inside him. His feet were placed flat on the bed, his knees up still but he was looking more relaxed now. "Yeah, I mean yes, Sir." His hands were running over his chest. He looked totally calm and blissed out, drugged even you might say. I moved my hand up to his face. I wiped the cum off his face with a finger and moved my hand to his mouth.
"Open up," I told him. He opened his mouth and I placed my fingers inside. "Now clean off your load. Its good for you," I said. He just did it on automatic. He had already started licking before I told him to do it.
"It doesn't taste as good as yours," he murmured. "Every guy's load tastes different."
"I didn't know that," I told him honestly. "I've never tasted any. That's your job."
I wiped up the rest of his load from his chest and fed that to him too. "Who's your Man, Timmy?"
"You are, Sir."
"And what does that make you, Timmy?"
"Your bitch?" he said as a question. "Your fag?"
"You're my boy," I replied. "Now squeeze your pussy tight, boy. I'm going to pull my dick out and you need to keep that seed inside as long as possible. It's good for you. Will keep you chill till the next time you get some." He squeezed and as I pulled out he let out a whimper. "Feels empty now?"
"Yes, Sir, it does." I looked at what used to be his tight little hole only half an hour ago or so. I wasn't going to say anything but couldn't help myself.
"Now that looks like a pussy," I told him. "I took your virginity, Timmy. Made that hole fit my cock perfectly. I love knowing I busted that hole open." He just looked at me. I could see his hole close up, but it was not near as tightly closed as it has been.
I lay down next to him on my back. He cuddled up next to me and stuck his head on my chest. I fell asleep soon after that. My arm curled around him and he was pulled close to me on his side.
I don't know what time I woke up. I opened my eyes and there I was, in Ian's family's house sleeping in his bed with him. I was asleep on my stomach, looking at Ian who seemed to still be sleeping.
Had all of that really happened last night? I reached around to my ass and felt my hole with my fingers. Jeezus my hole felt bruised. What used to be my little hole now felt like a big gaping slit. I was all sticky. I guess from lube, maybe from Ian's load? I had no idea. But my hole definitely had my attention. It felt all stretched and a little sore. I rolled over on my side and pulled the covers up.
Why did I feel so ecstatic? I should feel something else right? I'm a guy and I just begged Ian to fuck me last night. Now what? He called me his boy. Why did that make me feel so good? How did I go from being a man to being a fag? I had no control with Ian. He had all the control. Fuck me, I liked that too. I liked being his boy.
I heard Ian moving. I didn't know if he was awake or not. Then I knew. He had his hand on my ass, didn't even say anything and he was feeling me up already. I jumped a bit when he grabbed it.
"Turn around," he said. I did as he ordered. He looked sleepy but he pulled the covers back and his cock was hard of course. "Get to work. As long as you are here, make yourself useful." I looked at him but didn't say anything. I moved the covers back off me and moved down to where his cock was poking up in the air. It was big and thick. How did I ever fit that inside me? If my ass was like my throat, I was going to be sore for a while. I remembered the first few days of my throat getting used by Ian and how it had felt stretched and bruised.
I started licking and getting his cock wet so I could go down on it. "Yeah, that feels good, boy." He put his hand on the back of my head. He started by grabbing my hair and pulling back and pushing down. It didn't hurt, but it gave him control. "That's it, suck it. Get it all slick for me." I pushed myself down on his dick and soon it was buried in my throat again, like so many times over the last few months. I wrapped my hand around his nutsack and pulled them away from his cock. It gave me some leverage to move more easily on his dick. I was working on it and he was grunting approval.
"You've gotten real good at this Timmy. You like it don't you?"
"I pulled back and answered, "yes, Sir" I went back onto it. I did enjoy it. I loved sucking his cock now. Would I get adjusted to taking it up the ass the same way? He said I was made to take cock. He was right about sucking it; I guessed he was probably right about getting fucked by it too.
"Turn over, Timmy."
"What? I'm sore, I mean my hole feels all stretched out and bruised."
"I don't care, Timmy. Sex is about pleasing me. You know that. I enjoy it and then you do too. Besides, there is no reason to let that hole close up tight already. I need to train it to be loose and ready for me."
I rolled over obediently. I knew it wouldn't do any good to fight it. I had begged for it yesterday, now he wanted it again. I could already feel his spit slicked dick sliding towards my hole. But when it started to open me up I winced. "Shit, oh man, I am sore," I whined a little. "Go slow!"
I shouldn't have said that. Ian just rammed half of it in at once making me squeal. "Shut up, Timmy. You want everyone to know you're getting fucked?" I thought to myself it doesn't make any difference, they had all probably figured that out, either from last night or like the other fags just by watching.
"Oh fuck that hurt," I told him and he shoved the rest in. I tried to get up but Ian pushed me back down into the bed. He held his hand on my head and began to slowly fuck me again. This time with no lube, just the saliva I had put on his cock.
"That's it. Just hold still, you'll find it just as pleasurable as last night. Accept that you want it and have no regrets. I would have taken your cherry regardless, eventually. It's better that you submitted it to me willingly." At the moment I doubted it. He kept his hand on my head, putting most of his weight on that. With his other hand he held my hip and I could feel each inch of his cock slowly pulling out before he shoved back in. "Yeah, tighten up on me, I love that." I forced myself to focus on what he said last night, open my hole as he shoves in and squeeze as he tries to pull out.
"This feels good Timmy. I'm glad you decided that you wanted my dick. I knew it all along. You needed some cock in you to bring out your real self."
Maybe I was waiting for this, all this time, all the guys I had done stuff for in high school, doing whatever Mom said to do. I had always been the one to follow a leader. Maybe I had been waiting for Ian all this time, a guy who would make me do all sorts of stuff. Maybe his brother was right, I was a fag, I just didn't know it until Ian came along.
"See, your pussy makes its own lube, baby. I'm telling you, this pussy was made to take cock, you were already wet for me." He was right, I did seem to be wet already. Maybe I was meant to take cock. He had no problem moving in and out of me. It was still sore, but it didn't burn like last night when he first went in. Ian pulled on my hips and pulled me up to my knees.
"Arch your back! Get your ass up in the air," He directed. He pushed on my lower back and got me positioned how he wanted. He started pulling his cock out and smacking my ass with it, then shoving it back in. "I got to get a picture of this," he said reaching for his phone on the bedside table. I heard him turn on the phone, but nothing else. "This is sooo cool," he said.
He handed me the phone so I could see what he was talking about. What I saw surprised me. He had taken a vid that showed him fucking me. He would pull out his dick and my hole would remain open, I mean wide open, until his dick was shoved back in. Just as it would start to close, he would stick his cock back in again. I couldn't believe it was my ass, or my hole. It was like a porn vid I had seen before.
"That looks so pretty Timmy. You have a nice bubble ass and now your hole is getting used to being open and waiting for me."
As he said it I reacted differently than I had ever imagined I would, I moaned. I could feel his cock sliding back in and I could watch it too. I put the phone down and let the sensations take over. I was starring in a porn vid on someone's phone "ooohhhhhh yeahhhhh, oh god. Why does it feel so good?" It was rhetorical but I knew his answer before he said it, because I was meant to get fucked.
"Because you were meant to get fucked, Timmy. I told you that. Here, I'm just gonna hold still, you start doing the work." I looked back at him and he had his arms behind his neck. His chest was huge and his arms were flexed. "Come on, start backing up on my cock. Fuck yourself."
I slowly backed up when I realized he was letting me control the pace for a moment. I got to the base of it then moved forward, then backed up again. I started trying to move my ass more and found I didn't have to move my body as much if I moved my ass more. I don't know if I was doing anything right, but it was beginning to feel good. "I can't believe it feels like this," Despite being sore, I wanted his cock. I wanted it. I kept moving quicker and shoving his dick into my hole, my pussy.
"It's a pussy, Timmy. You love it because that is what a pussy is for, my cock. You just didn't understand it until now. Get off the bed. Get back here on the edge. As soon as I was there and in a position he liked he rammed his cock back in fast, causing me to moan.
He held my hips and started to pound me harder. I used my hands to keep myself in place on the bed. He was pounding me now and really pulling my ass back each time as he drove it home. My hands were on the bed holding myself in place. This wasn't gentle like last night. This was different.
"Little bitch," he said. "You love it. Why did you take so long to beg me for it?" He reached around and grabbed my nipples and he pinched.
"Ugh, mmmph, IÉI don't know," I said honestly. "I don't know."
"Don't ever tell me you don't like this. I will use it when I want and how I want. It belongs to me. "
"Yes," I was all I told him. The way I felt now he could fuck me anytime. I understood him. I wanted it. It felt even better than when it was in my throat. Yeah, I was a bit sore, but it felt good. I could tell my dick was hard and was bouncing around, slapping my stomach as he fucked hard. He didn't touch it though and neither did I. I knew not to touch my dick when he was having sex. He kept twisting and pulling on my nipples. When he pulled or manipulated my nipples my dick would jump.
"Gonna cum, going to fill you up again," Ian announced. "Going to give you my seed, boy."
I wanted it. My head just was exploding with thoughts. I saw the video from the phone of my open hole, I saw the look in his eyes from last night, I felt his dick splitting me open right now, I felt my nipples being pulling and tweaked. I wanted him to cum inside me. I wanted him to empty his nuts deep inside. "Yes, oh, god, please fill me up." The thought of his cock emptying and the pleasure he was giving my hole was enough for me. I could feel my own load building. "Oh fuck, Oh god," I was trying not to make noise but I wanted to howl. Ian grabbed my head and covered my mouth.
"Shut up, bitch," was all he said. He pulled me back so I was only on my knees and I was leaning back onto him. His hand was clamped on my mouth. And then he moaned as he emptied his dick deep in me. I could feel it as he stopped pounding and just held his cock in me. How come I never knew before that my ass could feel this stuff? I could feel his cock pulse and the idea of being the one to get fucked by Ian; being the one he used to get off. I clamped down on Ian and watched as my cock spewed four or five shots off onto the sheets.
He pulled my head back until he could whisper in my ear. "You are my bitch. I'm going to fuck you when I want now. You need to be ready when I am." I felt one last spurt ooze out of my cock as he said this.
"You feel it, don't youÉmy cum inside you?"
"Yes, Sir," I answered.
"It's in deep, becoming a part of you. Making you part of me, making you mine. You were a good boy and took it all and it is a lot I understand. Hold my cum in you. Show me how thankful you are that I fucked you by keeping as much of that inside you as long as you can. I know I may have hurt you at first but your pussy was so soft and wet that I couldn't control myself. I'm only just beginning to have fun now, Timmy. I'm going to make you a shivering, moaning, whore for my dick. You'll get wet at the sound of my voice and be happier than you ever imagined, with less control over your life than you ever imagined you would have. You love your pussy getting filled with my dick. If you didn't like it you wouldn't cum for me like that." He twisted one nipple as he kept my mouth covered with his other hand. I moaned into his hand. "Now we are going to go shower and then head downstairs for a good breakfast."
Then he let go of my mouth and nipple and I fell forward on the bed as he pushed me off his dick. I gasped as he pulled his cock out in one stroke and I felt the emptiness inside me suddenly as it was removed. I tried to close my hole. I reached around to feel it close and to make sure it was shut. That sounds crazy but I had no idea if it would ever close again. Ian had a big dick and I didn't know if my hole would close or not after seeing that video clip. I had no clue about taking cock inside me. My hole felt all puffy and sore like it had been really worked over. I needed to ask Danny or Bailey about this stuff.
Damn! Now my dick was as hard as a rock and showing in my pants. What the hell was I going to do about that? I hadn't meant to listen in, but hell, I could hear those two guys fucking 2 rooms over. I was glad the girls and Joan and Dave were already awake and downstairs. But listening to my boy fuck his bitch was HOT! I admit I was a bit surprised. Timmy looked far too much like a stud to be a fag for Ian, but what did I know about this stuff. He wasn't my type, except for that ass, now that was a nice piece of meat. I could see what Ian found nice about that. I guess Ian had found a fag to keep him busy at school. At least he wasn't going to end up married with kids if he didn't want to do that.
I walked away from the door when I heard them finish. No need to let them know I had heard it all. My dick made walking uncomfortable and was pretty visible if anyone wanted to check. I needed to get some relief from that sometime today. I would like to fuck Billy, but he isn't ready yet and I am not making a scene trying to get him on to my cock. I had fucked Jan last night so she wasn't going to want to do that again. Plus she was already working on breakfast for everyone. I was trying to stay away from Danny's cunt. Though it sure seemed nice right about now. I could get in and get off quick with him, but he was downstairs with his girlfriend Bailey. Hmmmm, now there was an idea. I bet Bailey would love to assist me in getting some relief from this hard-on. Maybe I would go downstairs and wake the girls up. I could use the bathroom down there to get some privacy.
I headed towards the downstairs to see what I would find down there. I would prefer if Danny weren't watching but hell I needed some relief and she could watch if she wanted, but still that would be torture since she was so hung up on me still. I was determined as possible to NOT fuck Danny again. Call me crazy for turning that fine twink pussy down but it was in both of our interests to find him a husband to handle that job.
When I got to the bottom of the stairs I looked around. I didn't see anyone at first but turned the corner towards the hideabed.
"Hey, Mr. McNeil," it was Bailey.
"Hey, Bailey. Where's Danny?"
"He just went in to shower. You want me to get him?" He smiled so sweetly. He really was a cocktease the way he played and looked so innocent.
"No, I wanted to let you boys know that breakfast would be ready soon. Are you coming up?"
"Oh yeah, I'm coming soon," he said smiling and tossing the sheet back from where he was laying on the bed. He had some little panties on. It hadn't crossed my mind, but yeah, that made sense, as he had no cock why wear men's underwear?
"Really? How do you plan on doing that? I seem to recall that you don't have ready access to cumming on your own," I shot back.
Bailey got out of bed and walked towards me, his eyes focused on my crotch. "I think you might have cock Mr. McNeil. You look like you are having some issues there."
"What about Danny?" I asked him. "Is he going to be awhile?" As if on cue, we heard the water in the shower start running.
"Oh yeah, He has to do his hair, Mr. McNeil. I think he will be awhile," Bailey replied. He was standing in front of me now. He put his hand out and began rubbing my already rigid cock. "What about people upstairs? Will they come down and bother us?"
"I hope not, but you better get started now if you want to relieve me of this problem," I told him. I put my hand on his shoulder and he sank to his knees. We were out of direct sight of the stairs and I hoped we would hear someone if they started down them.
Bailey unzipped my pants and reached into my boxers to pull out my cock. "Mmmmmm, you are at least as big as Ian," he said.
"Slut. You sucked my son before you sucked me. I should have kept him away from that farm, he's changed now that he knows about fags."
Bailey laughed then started going to town on my dick. I knew he would be good. Ian had nothing but good things to say. I'd thought about fucking her but there wasn't enough time. I would enjoy trying out that pussy I'd heard too much about and would want to take my time. A blowjob would need to suffice right now. I put my hands on his head and began to push into his throat. Immediately his tongue came out between his lips and lapped at my balls when I got all the way in.
"Oh shit, that feels good, girl. Keep that up and I will empty these nuts right away."
Bailey swallowed a couple times and backed off onto my shaft. He took in some air and then began going up and down, building up a good speed. It felt real good and I could provide him a reference if he ever needed one. The kid was good. I wasn't far from blowing a load. I kept thinking about Ian fucking that kid he brought with him. I was imagining my own dick going into that fat ass.
"Okay girl, you're doing well. This is just a quick blow, get ready to swallow," I told her. She doubled her speed and I grabbed her head and held it still. "You hold it all and let me see it when I'm done shooting." She nodded quickly.
Damn, she pulled that load out with her suction. She was a keeper for whoever had married her. "MMMmmmmmm, fuck," I said as quietly as I could. "Don't swallow yet, don't do it." I finally let go of her head. I may have been holding it a bit tight. I looked back down at her. She may look like a guy, but I knew she had a pussy. A real girl.
"Open up, let me see," I instructed her. "Good job." Her mouth looked full and a little ran down her chin as she tried to keep it all in. "Swallow it before you spill any more," I told her. Bailey closed and swallowed and had a big grin on her face.
"That was fun," she told me. "Too bad you didn't fuck me," she teased.
"If you're lucky, I will get to do that before you leave," I said. "Now clean up the stuff that ran down your chin." As if on cue the shower turned off. "Gotta go now. Keep all this under your hat. Danny will be jealous if he finds out," I said.
"Of course, Mr. McNeil."
"Honey, Joan and I are going shopping in a bit. Did you want to go?" Mrs. McNeil said to her husband as we were finishing breakfast. "We want to catch some of the sales going on today."
"You're kidding right?" Mr. McNeil replied. "I think all the shopping I will be doing is on which football game to watch." He and Dave both laughed at that.
"You girls go and have fun," Dave chimed in.
"Mom, I'll go," Ian said. "Timmy and I need to pick up a few things for school."
"We do?" I asked.
"Yeah, You forget already about your pants?" he asked.
I could feel myself blush, all I could manage was an "Oh," and then I said nothing more.
"So if we can ride along, that would be great," Ian said.
"Sure dear. Anyone else interested?" Mrs. McNeil asked.
Of course the twins were interested but everyone else declined. Great I was going shopping with the women and Ian. I know I needed new pants but I didn't imagine going shopping with everyone when I did it. Maybe we could all go our own way once we got wherever we were going.
We all got into the minivan. Ian climbed in first and went to the far back so I followed in and sat in the seat next to him. The girls were in the middle and his aunt up front in the passenger side with his Mom driving. I wondered why he had wanted the far back. There was less leg room back here, but whatever I thought. Once we got going though I knew pretty quickly why we were back here. I could feel Ian's hand on my back and he was sliding it lower towards my ass. I couldn't believe he was going to be so touchy here in the car with his relatives around.
I squirmed but Ian kept his hand on my back and then began to slip his fingers into my pants and then my underwear. I was looking around the car checking what everyone was doing. There was music playing on the radio, the girls were engaged in some conversation with his Aunt. I couldn't here much of what they were saying between the music and road noise, but still, what if they looked around and saw his arm? I couldn't believe he was doing this. I looked over at him but he was not looking in my direction. He was purposefully looking forward as if he wasn't slipping his hand in my pants.
Unless I made a scene here in the car, I wasn't going to get his attention. I reached around behind and grabbed his arm and tried to pull it away from my ass. He just used his bigger muscles to keep his arm there and I had no leverage to move his hand away. But, he did look over at me. He had a frown on his face. He moved his other hand up and silently shook his finger side to side at me, as if I were a kid, giving me the "No" sign a mom would give her child. I silently looked at him to ask why he was doing this, but he just grinned, and moved his finger toward my asshole.
As it was, my butthole throbbed a bit. I still was having trouble realizing what I had done last night, hell done this morning too. I had allowed Ian to fuck meÉno I had begged him to fuck me. I was a faggot. I was one of his conquests. I already knew that he treated me as his boy. The last couple of months I had become his go to for cocksucking, I had begged him to go further and he barely paused before shoving his cock in me.
I thought back to the incredible feelings from last night. I had really never had anything close to the orgasm I had last night. Everything shook inside me. My head, my legs, my dick, everything seemed to be twitching as I shot a load. As usual when it involved Ian, I didn't even touch myself. I just exploded in so many different areas it felt like at the time. As I was thinking this over, Ian tapped at my hole with his finger. He was running his middle finger around my hole. He pushed at it gently and I remembered his first explorations last night. I relaxed some. I could still feel the slight soreness that his finger was emphasizing now. I don't know why but I could feel every little thing he was touching there.
Maybe I was meant to be a faggot. It felt good to let him run his finger there. Other than the fact I was in the car with all of his women relatives. What If they turned around and looked? I could sense everything it seemed. I wasn't aware till now that I had so many nerve endings right there in my butt. I felt my hole differently now. He just kept tapping at it and I could almost feel it open up a bit. I didn't want it to, but it seemed to have a mind of its own and soon his finger was pushing in to my ass. I looked over at him again and shook my head no. I wanted to scream no. What if all that cum inside me came out when he did this? What happened to it up there? Did it really become part of me like he said? Did I absorb that part of him? I had no clue. I was truly clueless about all of this.
Thankfully after a few seconds of this, Ian pulled his finger out of my hole and his hand out of my pants. He held his finger under my nose, the put it to my lips. I could smell my butt and I could smell sex. It smelled like a mix of Ian's maleness and my butt. Not what I imagined but not different once the aromas were presented to me like this. He mouthed the word "open" at me as I looked at him. Seriously? He wanted me to open my mouth? I hesitated and his look grew dark. I did not want to anger him, so I did it. I opened my mouth and he stuck his finger inside my mouth. I closed my mouth and ran my tongue around his finger. As I cleaned it, he removed it with a huge grin on his face. The taste was not really anything awful as I had imagined it just echoed the smells. I already knew what his cum tasted like and there was a bit of that there. It was like a mix of me and of him. Fuck that made me shiver a bit. I hoped my butt would go back to the way it had been, I kept wondering if all that cum would leak out of me.
Daddy, Grandpa, and Uncle Dave were watching football as usual. Billy was cleaning up the kitchen from the big breakfast and starting laundry. Bailey and I had just sat down on the back sofa away from the men and the TV. I looked at them. All of them made me horny. I really wanted Daddy, but at this point frankly Uncle Dave or Grandpa would be fine too. I just wanted a man to give me a good fuck. It had been at least a week since someone had fucked me. I hadn't cum then so I was really wanting to cum.
"How do you do it, Bailey?" I asked out of the blue.
"How do I do what?" he wondered in reply.
"How do you manage to not drive yourself crazy if you can't cum? I mean, your balls are inside somewhere and you still make the stuff that makes you want to cum, you know, to get a release. Does that make sense?" He smiled, and then laughed.
"Are you horny?" he teased.
"Fuck, yes," I replied. "I'm usually always horny. I can't get hard and I can't cum just rubbing my dick. If I try rubbing it, it wants to get hard, and that hurts, so I don't even bother with that any more, but I get so horny!" I know it sounded whiny but I couldn't help it.
"You have to focus on what feels good, Danny. I know you have cum from getting fucked, you've told me that," he said. "Why aren't you trying to get more dick?"
"I don't know," I started thinking about it. There were guys at the farm all the time, but I hesitated to always ask them or beg them in some cases. I waited for Ian these days to fuck me when he was around. But if he is getting some from Timmy, I didn't want to get in the middle of that either. I just don't go up and ask, I guess. For a while Daddy didn't let me do stuff like that."
"I don't want to sound mean, Danny, but hear goes: your Dad isn't going to fuck you, I heard him say as much in the car over here. You need to make use of the men around you. You have to ask, Danny. Some won't know you want it, and others won't offer it unless you ask for it."
"But where? I'm not going to ask Ian with his new boyfriend, and the only other guys are Uncle Dave and Grandpa. It isn't like they are going to fuck me," I said. Bailey grinned big but didn't say anything.
"What? What?? Are you kidding me?" I said. "Did one of them fuck you? When"
"Last night when you were already asleep. I went to get something to eat late and bumped into your grandpa. He's really a very sexy man, Danny. With a nice cock, too."
I was curled up on the sofa but I reached out and whacked Bailey on the arm. "You slut! I can't believe you seduced my Grandpa!" I told him. Geez, I had no idea my grandpa would fuck guys. "But, he's my Grandpa," I said. "I can't just ask him to fuck me."
"Why not," Bailey asked. "Don't ask him, just put the moves on him."
"Nooooo, no I couldn't do that. I'm notÉI'm just not good at that. My own Grandpa?" Bailey laughed again.
I tried imagining putting the moves on grandpa. I couldn't get very far in my head.
"Look," Bailey began saying. "You need to get fucked. You are like me, Danny. We both need to be fucked to cum, and cumming is a good thing. It releases all that build-up tension and stuff that we have inside." He looked at me as if he wanted to make sure I understood all of it. "Cumming is healthy, it's why Johnson will milk you if you haven' t cum at all lately, so you release the build up. But you know it isn't anything as good as getting off with fucking."
He was right. I didn't mind the milking routine, but it didn't feel good or exciting like fucking.
"You need to really think back to the times you enjoyed cumming like this. How it felt and how your throat or your hole felt. You can get stimulated that way. It's part of learning Danny. I love to feel a cock inside me, in any of my holes. I just no longer needed to cum through jacking off or touching myself. It didn't bother me in the least once Tom said he wanted to give me a pussy."
"You can't be serious," I said. "I mean I am not doubting you, I just can't imagine it," I told him.
"Tom just put the idea out there one day," he continued. "He had taught me to focus on my holes already. I know people don't think about a throat or an ass as a sex organ, but to me they are. It is like every time I deep-throat him or take his cock in my ass it is incredible. It took awhile yeah, but I learned and I love it. I stopped playing with my dick. It helped that he locked it up to start with, but after a short time, it didn't need that even, I just left it alone. By the time he suggested it, I was ready to accept it as a possibility. When I thought about it for a couple days, I told him I wanted it too."
"And you can just do the same with any man?" I wondered. "It doesn't have to be your husband, Tom?"
"No, it is any man that I am pleasing, because I am getting the same pleasure. I love to feel a cock in my mouth and in my throat if it is big enough to get that far." I laughed at him. "And If I get really lucky and take one in my ass or my pussy then I especially love that and my nipples get firm and I just enjoy the feelings I can feel throughout my body."
"I don't know," I told him. "I just have felt that stuff when Daddy or Ian have been using me. I mean, don't get me wrong. Sometimes when the guys at the farm fuck, I start feeling good, but it isn't nearly as good as when it happens with my family. I'm a freak," I told him.
"Let's go downstairs," Bailey said. "Let me show you something."
"Just come on." Bailey got up and headed off. I got up and followed him.
"What are you doing?" I asked.
"I'm going to work your pussy with a big dildo until you cum," he answered. He dug around in his travel bag and brought out a decent sized dildo. It wasn't as thick or as stiff as one that I owned. It seemed real rubbery.
"Oh please, it isn't the same," I told him.
"No it isn't, but you need to work on your mental images. I don't mind helping you do it. It's like two girlfriends helping each other out. Get out of your clothes," he said a little too forcefully. I laughed at him.
"Sorry, it sounds funny coming from your mouth." He laughed too.
"Okay just get naked and get on your knees. Practice deep throating this thing."
"Eewwww. Where's it been?" We laughed at that. I knew where it had probably been, I also knew Bailey was fastidiously clean.
"I put it in the dishwasher," he said. "Get over it."
I tried. I held the dildo and tilted my head back. I started putting it in my mouth. I got it all wet and tried to go down on it, but all I tasted was vinyl or silicone or whatever chemical this was. "It's tastes awful," I complained.
"Doesn't matter. You need to work on your attitude. Think about how good it is going to feel when it gets in your throat. Lay on your back and hang your head off the side and close your eyes."
I did as he suggested and he took the dildo. He started feeding it into my mouth. He pushed until it got to the back of my throat. He pushed a little but stopped when I gagged.
"Relax, get it real slick. Once it gets in your throat it's gonna get all slimy anyway."
He pushed it back and forth in my mouth and tried to push again into my throat and it went in this time.
"Okay, put your hand up on your throat. Feel it going in?" he asked. "Just lay your hand up there as I go in and out."
I did as he said. I could feel my throat bulge and then the dildo move down inside me. It felt pretty weird on my hand as I felt my neck.
"Feel that? See how good that is," he told me. "You feel the stretch? Just like a man's cock," he continued.
"mmmmmhhmmmmm" I gargled a reply. I don't know why I bothered.
"Your nips sure are bigger than the last time I saw them," he said. "You must still be working on pumping them. Well start playing with them. They should make you feel hornier."
I started playing with my nipples. That did feel good. I liked how big they had gotten and how they stuck away from my chest. I wasn't muscular at all, but my nipples made it look like at least something was there. They stuck out in most everything I wore. I brushed against them lightly and felt electric tingles in my body. Every few strokes, Bailey would pull the dildo out of my throat long enough for me to catch my breath. With my eyes closed it seemed more realistic. I began to think about Daddy's cockÉwait no, I told myself. Think of Ian's cock, Daddy doesn't want your throat. I thought of Ian's cock, going in and out of my throat. I knew it wasn't him because he was quicker and rougher than Bailey could ever be, but the feelings inside were the close.
I focused on my nipples. I pulled on them a bit, again, gentler than Ian would be, but I twisted and pulled then just lightly rubbed them, it felt very good.
"Get some slime from the dildo," Bailey said. You should finger your cunt."
"What the hell are you boys doing?" Fuck! It was Uncle Dave! When did he come down here? I jumped up and the dildo slid out of my throat. Bailey jumped and dropped it. We were caught! I was naked and kneeling on the bed, Bailey was standing next to it.
"Uhhhh," I made no response after that attempt.
"Did you really think that was going to help him?" Uncle Dave said looking at Bailey. "And you," he said pointing at me, "did you really think a toy is going to feel as good as a real cock?"
Bailey and I looked at each other.
"Obviously you don't have dick enough to fuck him," he said to Bailey. "If you did he wouldn't be thinking a plastic imitation was going to help. So just go on upstairs and do laundry or dishes with the other one." He must mean Billy, I thought. "Keep the men amused so they don't come down here."
"Uhhh, ok, yes Sir," Bailey said after a few seconds. He didn't run, but left quickly.
"You," Uncle Dave continued, "you need to practice on a real cock."
"Uncle Dave?" I managed to croak out.
He didn't pause in any of this. He stepped forward and began unzipping his pants. He pulled out a good-sized dick, one that was plenty thick. "Get back down on the bed, you're face hanging off the side," he told me.
"But, Uncle Dave, what if someone hears you?" I asked.
"I'm guessing your little sissy friend will keep that from happening," he answered. "Now do what I said so you can get some real practice.
I did as he said. I lay back down on the bed looking up at Uncle Dave. I wondered about the twins and if they knew their Dad was into getting his dick sucked by guys. What did Aunt Joan know?
"Open up!" he directed. I did and he stepped forward; his cock jutting out of his pants that were still around his waist. He hadn't even pulled them down. He aimed his cock toward my mouth and pushed in, he didn't stop at all until he was buried all the way in me. Fuck he was thick.
"Nice!" he exclaimed. "You do have a good throat. Been a long time since I had anyone swallow me like that." He pulled back and went in again. "Get your hand up there on your throat. Feel it like your girlfriend told you."
Crap, he had heard a lot of what we were talking about. Then I realized I was totally naked and my dicklet was showing. As if on cue, he started talking about it.
"So now I see why you cant just jack off. Whatever dick you have is pretty stretched already and locked down to your hole. Who the hell did that and why don't you just undo it?" He pulled his dick out long enough for me to answer.
"My last boyfriend did it. He didn't want me to touch it. I don't have the little key thing to unlock the rings."
He stuffed his cock back in and I stopped talking. "Go on, start fingering your cunt, as your girlfriend told you to do. You're just getting me wet so I can fuck that hole." I put my other hand down to my butt and I slipped a couple fingers inside. I moaned reflexively around Uncle Dave's dick.
"Lift your legs up," he ordered. I did so and he grabbed them with his hands and held them. He used them to gain leverage on my body and start thrusting harder. I had one hand at my pussy and one on my throat. Uncle Dave was trying to step out of his shoes as he kept fucking my throat. I was being pulled this way and that as he twisted around getting those shoes off.
Once he did that. He let go of my legs, pulled his dick out and began yanking his pants and boxers off. He grabbed my legs again and spun me around. Now my pussy was facing him and I could look at him from the right direction. He still had his shirt on but now he was naked from the waist down.
"I don't believe in condoms," he told me. "So I hope you're on birth control, I don't need more kids." He aimed his dick at my cunt and laughed as he began to push. "Jesus your ass looks like a cunt," he told me. "That's a wide slit. You're a faggot alright."
"MMMmmmmm," I moaned as he entered me. "Ohhh Uncle Dave, you're thick."
"The fag or two I have fucked over the years seem to like that," he grinned down at me. Did all the men in my family fuck fags, I wondered? "You've got some nice nipples there, Danny. Too bad those aren't real tits. I might like to play with those."
I reached up and felt my nipples. I started to play with them, for Uncle Dave and then I realized for me too. It felt good. I wondered if he really thought that? Would a Man like me better with real tits? Uncle Dave was watching me rub them and twist on them as he started fucking me harder.
"Geez, your ass is like a pussy, Danny. You've had a lot of dick in here, haven't you?"
"Yes," I said and nodded. "I love getting fucked."
"Always figured you as a queer, Danny. Just no one told me. Why are you holding out on me?"
"I guess I haven't had time to tell you or the rest of the family," I explained lamely as he began pounding me.
"Your hair is girly, your attitude and movements are girly, your nips are girly, hard to not notice the change."
I had nothing to say. The changes that Daddy had put me through HAD made me look different and they felt right for me. I liked being more sissy looking. I liked being a sissy fag.
Uncle Dave had worked up a good pace already I didn't think this was going to be a long fuck. I began to think hard about my pussy. I started squeezing and releasing, as I had been trained. I began to notice how his cock rubbed a spot inside me and where it felt the best. I arched my back a little and put a hand under my back. It increased the angle of the fuck and I felt that cock even more. I continued to use my other hand to rub my nips. "Oooohhhhhh, you feel so good. Fuck me Uncle Dave."
"You feel good too, you little fag. Someone taught you how you use your cunt muscles well."
I kept thinking about feeling my body and what Uncle Dave was doing to it. I ran my hands over my chest and kept tweaking my nips. They could be so sensitive. Uncle Dave pulled my legs up more and pulled them apart. I was balanced more on my shoulders now and he had ahold of my hips and he pounded harder.
"You're leaking boy, I can see your dick leaking," Uncle Dave told me.
"Oh yeah, ohhh goddddd, it feels so good," I moaned. His hands were stong on my hips. He held tight and I could tell he was grasping hard to keep ahold of me as he pounded. My nipples were humming from me playing with them. They were very sensitive today. I was squeezing and releasing Dave's dick and I felt a subtle change, he was getting harder, swelling before he shot a load.
"Fuck, take it, Danny. Gonna empty my nuts inside you." I arched my back as much as I could and he pounded the spot in me that felt so good. I felt a warmth spread through me as Dave slammed hard and grunted. I felt the warmth take over and I knew I had leaked a load out. It wasn't as earth shaking as I had hoped but still, I had cum from someone besides Daddy or Ian.
"Uunnnggghhhhh, fuck, tight cunt when you want it to be. Fuck feels so good." Uncle Dave was grunting and jerking and kept buried deep. When he finished he let go of my legs and I fell onto the bed and his cock slid out. I clamped down hard and could my ass close up, but I think some of his load slid out anyways.
"Clean up my cock," he told me."I can't go shower right now and I don't want to smell like your cunt all day in case Joan gets back before I shower," he said.
I spun around and swallowed his cock and slurped up everything on it, leaving it shiny.
"Remember, you keep this to yourself. And tell your girlfriend too," he added. "I don't need to explain what I do to anyone, Chuck or Don or especially the girls," his eyes burned into my brain with his stare.
"Yes Sir. Thank you Uncle Dave," I told him.
"You're welcome faggot."
The he got his clothes back on and went back upstairs after running his hand through his hair.
We got to the mall and I didn't freak Tim out any more in the car after he had cleaned my fingers off. I was just checking to see that my load was still inside him. It was, so I was pleased about that. He was reacting pretty well overall I thought to the fact I had plucked that cherry from him at last. Just the thought made me smile. I am sure that inside his head though his brain was running a mile a minute.
We headed first to the Macys store, one of those giant department stores. Nothing fancy, but I wanted to go check out pants for Tim definitely. I knew he was going to try to find something that fit his growing ass. I was going to make sure it showed it off as much as possible. I was proud of the work he had put into it and I was proud that he had followed my directions on the workouts. I wanted people to see it. After yesterday I was definitely feeling that his ass was mine so I could do what I wanted with it.
The twins headed off to the make-up section of the store. I survived being sprayed by any perfume sales people and we found the men's clothing. Mom and Aunt Joan were nearby looking at other stuff. I wandered over to where the pants were at and Tim followed. He wasn't saying much, so I wasn't sure what he was thinking.
"What is the size of the pants you are wearing?" I asked him "That is at least a starting place. Then we can figure out where to go from there."
"Uhmm, I think they are like 32 waist and 32 length," he said.
I started looking through the jeans. The store was divided up by different brand names, so we wandered a bit looking for other sizes. I grabbed a few pair that were "relaxed" fit to see if the same waist in a different style would work. I also grabbed a couple of 34 waist of "skinny fit" to see if those would work.
"Go try a few of these on," I told him. If you can't fit in them, don't bother showing me, but if you think they fit, then come back out of the dressing area and show me what they look like."
"You want me to come out and show you? That's like shopping with my Mom," he said.
"Well how else will I be able to tell whether they fit or not? Do you want me to go into the dressing room with you?"
"Uh, no," he said quickly. "That would look funny."
"Well then come out here and show me. I want to see if they fit you and we can find different sizes from that. And you need to come out and show me at least the ones that fit the best," I added, "Or I will come in there and watch as you try them all on."
He looked a bit sheepish. I didn't really care what he thought; I just wanted some pants on him that fit. He would get used to this. He wouldn't be picking out his clothes for a while until he adjusted to wearing what I wanted him to wear. I didn't have problems with his current clothes really, but I did want to start making him think about whether I liked what he had on. I smiled as he trudged off to the dressing room.
I wandered over after I had picked up some khaki pants too. I held on to those and waited while he was changing. Eventually he emerged from the changing room and looked around until he saw me. He wandered over to where I was.
"Turn around," I told him. "Let me see that back too." They weren't bad I guess but didn't fit right still in my mind. "What size are those?"
"They are a 34 waist relaxed fit," he said.
"Well they still look tight on you. Lift your shirt up some so I can see the waist." He did so reluctantly but I just looked him in the eye until he did it. The waist was really saggy, but the butt part of the pants could barely fit. It was about then that Mom wandered over. Tim saw her before I did, because he suddenly was staring over my shoulder. I turned around to see her coming too.
"What are you guys doing?" she asked.
"Trying to find Timmy some pants that fit," I told her.
"Oh, let me see. Turn around Timmy," she said. Surprisingly he followed her direction immediately. "Oh, honey those don't fit at all. Look at all that space around the waist." She walked right up to him and grabbed the waistband. "See, this is just going to get in the way if you need a belt."
"I know," I told her feigning knowledge of pants I didn't have. "His pants don't fit right after all the training he has been doing for the swim team," I explained.
"Well, these aren't the right size. What are they?" She looked at the size mark on the back of the pants. Mom grabbed the khaki pants I was holing and gave them to Tim. "Here, Timmy, try these on and come back out here.
While Tim was changing again Aunt Joan wandered over. "What are you doing?" she asked.
"We're trying to find pants for Timmy," Mom explained. "He doesn't fit the usual size," was how she phrased it. I could feel my grin getting bigger.
Tim came out in one of the pair of khaki's I had grabbed. They were about the right length but they definitely did not fit around the ass at all. There was some room at the waist but not as much as the jeans had left.
"Those aren't right at all," Aunt Joan commented. "What size are you trying on?"
"He's got 34 waist on now, but that is too big. Look at all the extra fabric," Mom pointed out. "But you can see that his hips are too big for these too."
"What other sizes do you have in the changing room? Joan asked.
"I don't remember," Timmy admitted. "We were just trying different ones. None of them fit right," he added.
Well, give those to Jan. I'm going to find the sales assistant and we can measure you before we spend hours hunting around." Aunt Joan wandered off looking for a sales person.
"She's right. No sense in trying on a bunch of different sizes randomly," Mom told him. "I'll stand outside the door, you handover the pairs you've already tried. Stay in there though so we can get a good measurement."
Tim looked at me for some support, but I was grinning too much to say anything. He rolled his eyes but turned around and went into the dressing room. Mom followed him. Once Aunt Joan returned with a sales person, we all trooped into the dressing room area.
"Here he is," Joan announced. "We need to get his measurements so we can find the right size pants," she pointed at the dressing area door. It was one of those doors where you could see Tim's feet, and his head but not the rest of him, only minimal privacy. Tim was now officially uncomfortable. I could tell from the look on his face. The three of us plus the sales guy were in the dressing area. "Come on out Timmy, we want to get your measurements," she said, not caring if he looked horrified.
"If you could come out in your underwear, that would make measuring easiest Sir," The salesman said.
Tim looked around waiting for me to say something I guess. He clearly didn't want to come out in his underwear and t-shirt. I just kept smiling. Tim eventually sighed and opened the little door and came out to the main area of the dressing room.
The salesman was pretty professional about it, I mean, there were a lot of people standing around so I didn't think he would try anything.
"The inseam is 33 inches," he said, measuring from Tim's crotch to the floor. "The waist is," he paused as he wrapped the tape measure around Tim's waist, "31 inches. But it is easy to see that a standard pant won't fit him," he announced. "His hips won't fit into the standard jeans. We can certainly find some slacks and business wear items that can be altered for him."
"Uhm, I don't really need slacks right now," Tim started to explain but the salesman proceeded to wrap the tape measure around Tim's "hip" area; around his ass to get a proper measurement.
"See, a standard pant size made for a 31 inch waist will be about 39 inches in the hip," he said. "However, this man's hip measurement is over 44 inches. He just won't fit well in standard jeans or khakis."
"Can you alter jeans?" I asked him.
"No, they don't provide the amount of fabric needed really to alter them. They are really constructed on an imaginary standard," he replied staring over his reading glasses. "If he is going to buy jeans he should just go with the bigger sizes say a 36 waist and then use a belt if he wishes."
"That just seems silly," Aunt Joan said. "Ian, go get a pair of dress slacks for him to try on. I want to see what it looks like when he has some pants on that fit."
"Oh, good idea, Joan," Mom added.
"No, it isn't necessary Mrs. McNeil," Tim tried insisting.
"Oh no Timmy, this is great," I told him. "You've been trying to find the right pants for a while now." I smiled and walked out to find a dress slack.
"Oh, and get some extra large jeans too," Mom hollered at me.
I picked up a standard black poly blend dress pants in a 36 waist and a pair of jeans the same size. I brought them back and Tim had moved back into the small dressing room. "Here ya go," I said, laying them over the top of the door.
"Put on the slacks first," Mom told him. He did as she directed and came out holding them up.
"Let me get some pins and chalk," the salesman said returning to us after a moment.
He began to pin and mark the fabric on Tim. By the time he had finished he had gotten the waist to where it sat naturally on Tim and the ass of these extra large pants fit perfectly. It was pretty amazing, I was impressed, turned on even looking at his curves.
"Wow," Mom and Aunt Joan both said. "They look nice."
"I think we should get those," I told the salesman."
"No really," Tim began but I cut him off with a wave of my hand. "You'll need those sometime. No reason to put it off as long as this man went to the trouble of doing all the work."
"Ian's right, Timmy. You will need them at some point, and they really frame your, uhm ,your body nicely," Mom added. I saw Tim blush a bit.
Aunt Joan continued the thought. "Yes, those look stunning now. Go try the jeans on."
Tim stepped back into the dressing room and came back out. The jeans did not look good.
"See, we just don't have the industrial sewing machines to handle the denim and make the stitching the same way as they are designed at the factory." The salesman ran hs hand near the seam and pointed to Tim's ass. "The only suggestion I can make is that many men in this situation will shop for jeans in the," he cleared his throat, "women's department."
"Oh Joan, why hadn't we thought of that? His hips are shaped more for jeans we might wear," Mom stated.
"You're right,' Joan added. "Why don't you pay for those Timmy and then come over to the women's section so we can look for jeans."
"Uhm, no, that's okay, I will just get these," Tim started. "I don't need to go to that trouble."
"Nonsense. We're here, you won't be embarrassed," Mom told him. Now even the salesman was smiling with me. Tim was not comfortable. I couldn't wait to get shopping in the women's section for him.
Mom and Aunt Joan headed off to the Women's Department while Tim paid for his pants. I considered doing it myself but he pulled out his wallet so I let him continue. They said they would call him when they were ready. I let Tim know mom could pick them up and mail the package to him at school.
"Do I have to go try on women's jeans?" he asked as we left the cash register in the Men's Department.
"Of course, Timmy. Would you deprive my Mom and Aunt of seeing you in a good fitting pair of jeans?"
He just sighed.
"Plus," I added, "I really want to see if we can find some jeans that will show off all that hard work you've put in to building up your ass."
He glanced up at me to see if I was serious. "You really like it?"
"Oh hell yeah," I admitted. "You have a great ass, Timmy." He blushed and looked around to see if anyone was listening in. "I think you would want to show it off."
"This is really embarrassing, IanÉSir," he added quickly. "I don't want to change in the women's dressing room."
"Doesn't seem to be a way out of that does there, Timmy?" He didn't reply.
Once we got to where Mom and Joan were, they had already selected 4 or 5 pair of jeans for him to try on. We repeated the scene in the women's dressing room only I had to wait outside while Tim tried on the jeans. When one was acceptable he came out with Mom and Joan following him.
"Look at this, Ian," Mom called out. I grinned at her attitude. She had no idea how embarrassed Tim was. "I think we found a pair."
Tim came over to where I was near a mirror. "Look in the mirror," Joan told him. "See what you think."
Tim stood and turned around a couple times to look at his ass. He ran his hand over his ass and pulled at the waist line of the pants. "They seem a little tight," he stated. "And a little low."
"These sit on your hips," Mom told him. "That's where they are supposed to be. Stop pulling them up and they look just fine." She adjusted them to her satisfaction. They looked damn good. His ass was tight in them but he was definitely showing off that butt in those.
"Can you bend over?" I asked. He bent over as if he wanted to pick something up and nothing popped.
"Women's jeans sometimes have some stretch," Joan said. "I think it has some spandex in the material."
"I think those are the ones you should get Timmy," Mom told him.
"Definitely," Joan echoed.
He looked over to me for something. I just smiled and nodded at him. I was going to let him figure it out. He looked back at the mirror. "Do you think these are better than the last pair," he finally managed to say. "I don't want to get new pants and then out grow them quickly."
I almost burst out laughing. He was concerned his ass might get bigger. I had to turn around so I didn't laugh in front of all of them. The seam line ran right down the crack of his ass. Each bubble cheek was separated and displayed nicely. As he looked in the mirror, I checked out the front of the jeans. It looked a bit tight, but he wasn't displaying too much there. It didn't look like women's jeans had the same cut as men's. Not much space in the crotch. I think that was why Mom was adjusting them on to his hips. His underwear stuck up above the waistline, but Mom didn't mention that. It occurred to me I might change his underwear to something that didn't show so much after he adjusted to the jeans. What would low cut bikini underwear look like on him, I wondered? Like a speedo was what popped in my head as an answer.
"No, I think these have give in them," Mom told him. They will be fine. Why don't you try a size bigger of this brand in black to see what it looks like, then you can decide? And get both colors. Compared to what you had on, these are so much better looking on you Timmy."
"Jan is right," my Aunt added. "You can never have too many pants that fit well."
"Well our work here is done Joan, let's go find the girls. We'll meet you in an hour where we came in, boys'" Mom told us. "We can have lunch then."