Redemption with Jerry (1st and 2nd encounter)

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Redemption with Jerry (1st and 2nd encounter)My story with this guy starts like a year and a half ago. Maybe two years ago. I was posting ads on Craigslist looking for guys to suck off. At the time I was watching rough porn… facefucking type stuff. So I think my ad probably asked for somebody to “fuck my face”..Little did I know… I wasn’t ready for that at the time. A guy… let’s call him Jerry… answered my ad and said he had his own apartment and he would turn me into his sissy. And it turned me on. He seemed different from a lot of guys, and I liked that he talked about being rough with me. He said he was going to train me to be his sissy fag.So I make plans to go over there that day, sometime around 2 years ago or so. At the time I had panties but no stockings. So he told me I could bring stockings next time and just to come over in my panties (under my sweatpants). So I pull up to his house that day and stood outside my car waiting for him to come and take me to his place. He lived in a 1 story apartment complex. Lots of neighbors, lots of small apartments. I see him walk out and he waves me over. He doesn’t come out and walk with me to his place. He doesn’t introduce himself formally, etc. He comes out and waves me over like “over here, slut”. So, with my panties hidden under my clothes, I follow him to his place. I walk in, he instructs me to get undressed and go in his room. It’s a small place. I think about all the different places I’ve seen the inside of, briefly before I sucked someones dick. I am really turning into a slut. Jerry is a 60-something year old white man. And I had come to this mans house just to suck his dick and be his bitch.BUT… this encounter isn’t the one I’m really wanting to tell you about. My first hangout with Jerry was actually a disappointment. This was back when I was still a little indecisive. I would come over to guys houses and get nervous, etc. Sometimes would get scared and have to leave. So this is pretty early in my sissy years. So he has me suck his dick. And immediately he is pretty rough with me, forcing my head down. I was probably a little too resistant. If you’re a sissy and you’re going over to a guys house, unless he is really freaking you out or something, just submit to him. Don’t make it weird. I was the one who wanted to go over there, I made the ad. But I was a little shy when sucking him. And he had me lick his ass “lick my asshole, fag” and he would sit on my face and grind his ass on my mouth. I wasn’t that into it but I did what I thought was enough. I licked his ass and sucked his dick. But I knew I hadn’t done the best job. Neither of us cum. He tells me next time he’s going to make me eat both his cum and my own cum. He gets up and starts getting dressed. I grab my things and leave, walking back to my car üsküdar escort afterwards. I remember my hair being messed up and thinking I probably had spit or precum on my clothes.So that one awkward encounter was all I had with Jerry. We made other plans but they’d always fall through. That was until last Friday.Last Friday (12/27/2019), I posted an ad on Craigslist. Well guess who replied to my ad. It was Jerry!!! Lol. He emailed me “you again?” Lol. So we have an email exchange and he says he’ll give me one more chance. And to come over at 10 am (one hour from then). So I agreed.So once again he led me to his apartment from the parking lot. This time I had panties AND stockings under my clothes. I was ready for him to see my body in those girly clothes. I was excited. Because this time, I was ready. The first time we hung out, it was one of my first encounters with a guy. And so it was a little awkward. But NOW, I knew a little bit about what I was doing. It was time for me to redeem myself. For other people, redemption might mean striving to achieve a goal, like a career-related one. For me, it meant being a slut for an older man and doing a better job of deepthroating his dick. I was determined to do a good job this time. I had sucked other dicks and here I was, back sucking Jerry’s dick. But it felt so right. The first time I thought his place was a little crappy. This time I didn’t care! All I was thinking about was Jerry’s big dick getting harder in my throat. And the rough treatment? I was ready for it this time. We started out that day by me getting undressed. He smacked my ass a couple times. He laid down on the bed and had me suck him there. I playfully sucked his flaccid dick until it started to get harder. Jerry’s cock wasn’t that big at first but MAN that thing really gets big after a minute. So it goes from flaccid to BIG and HARD. And I start getting sloppier with the head. There is slobber all over the place, strands of snot and saliva hanging from my face. I’m going down as far as I can on his dick and making gurgling noises. “Fuck yeah, bitch” he said, obviously liking what I was doing. This is the best part of sucking dick. It’s like a performance where you can show a guy that when you’re alone with him, your mouth belongs to him. That you’re willing to gag and choke on his big dick. It’s so hot to impress an older man like this.Jerry wasn’t all the way satisfied though. Jerry decided that his dick needed to go further in my throat. If this was 2 years ago, I would have been resistant a little bit. I would have fought back. This time Jerry placed his hand on the back of my head, and my head went down nice and easy. Well, almost. I gagged and gargled on his dick. It felt like it was so big that I could tuzla escort feel the curve of his dick up in my throat. “LEARN” he said. I could barely breathe when he pushed my head all the way down. “Just leave it in there”… he released his hand and I laid there on his bed, between his legs. I was playing with my little clit in my panties, and his dick was still all the way down my throat. He watched football as I just laid there with his big dick all the way in my mouth. I mean my mouth was wrapped around the base of his dick. The whole thing was in there. I couldn’t breathe but I could still use my tongue so I licked the underside of his dick while my mouth was still filled up with Jerry’s dick. “Now you’re getting good” Jerry told me. He stood up. “Put your head there”… he had me lay my head on the edge of the bed. I knew what was coming. Jerry hovered above me with his dick head going in and out of my mouth. I laid my hands on the bed, hoping he would hold them down and use my mouth like a pussy. Instead he lays all the way on top of me and just puts his dick all the way in my throat. I gagged, but not much I could do except take his dick. He had his weight on me, which wasn’t comfortable. But I realized between our first encounter and this one that it’s not about my comfort. When I’m hanging out with older men, I need to be making them happy. So this 60 year old man lays on top of my 25 year old body, all of his weight on me and his dick pumping in and out of my throat. And he was all the way in there too. I gagged and gurgled to his delight. “Oh YEAH baby”.. he loved the noises coming out of my throat. He took his dick out and put his balls in my mouth. “Lick and suck em like you love em. Do you love my balls?” Jerry really liked how i was licking and sucking his balls. He had me go from sucking to licking balls, repeat. And he must have been really turned on. Because then he sits up a little bit and just sits his asshole right above my mouth. “EAT MY ASS” he screamed at me! “Eat it like it’s your girls pussy” Jerry’s tone had noticeably changed. He was serious now. And part of me was afraid but I was also excited. And it’s weird because his enthusiasm really made me want to work harder. I licked his asshole so good. I licked it up and down, side to side. Tongue all the way into his manly asshole. During this, sometimes he’ll palm my dick and balls in his hand all at once. He wraps his hand around my whole package, the small cock and balls fitting easily under his hand. This is very hot to me. It is very emasculating to have someone hold your entire package in their closed hand. So I’m licking this 60 year old mans asshole while he’s SCREAMING at me to go faster, go harder, etc. and during this I realize in my head that pendik escort holy shit, I LOVE THIS. I am having such a good time being a fag for this older man. “You gonna be my regular sissy fag?” Mmhmmm I agree, with my tongue still deep in his asshole. He had me lick his ass for a few more minutes and then he laid back down on the bed. He wanted me to lay over one of his legs. So he could feel my ass and my little sissy dick with one of his hands, while I laid across him and sucked him. I immediately start deepthroating “slow down, fag, suck it slowly” he tells me. So I suckle the head. And give his big dick long strokes of my tongue up and down. It’s wet enough that I stop and jerk it for a little bit. He likes that, too. Then he has me suck again. “All the way” he tells me. I don’t do it, gagging and going back up for air. “ALL THE WAY” he yells. He forces my head back down on his dick. I choke and spit comes out of the side of my mouth as I gag with his whole big dick in my mouth. “Practice” he says. And then he smacks me. The first one wasn’t that hard but I kinda liked it. At first I was startled. We had talked about this before, but I wasn’t sure if he was going to really slap me. And the way we were emailing, he knew that he could pretty much do what he wanted. So Jerry gets comfortable. He smacks me a few more times with his dick all the way in my throat. “PRACTICE!!!” He yells. At one point he smacks me about 10 times in a row while I am going up and down on his dick. I am trying to fit as much dick in my mouth as I can but he is like a boss that is never happy. I take the abuse, knowing that I deserve it. “SUCK!!!!” He yells at me, smacking me again. It felt like I had an adrenaline rush at this point. My heart is pounding. I am going as fast as I can and as deep as I can, gurgling and gagging on this mans dick. I am jerking it, it’s all wet with spit. I go back to sucking it. But he is still smacking me. I hate to admit it, but this is so hot to me. For him to use me like this. For him to know that he can do whatever he wants with no repercussions. And it was hard to find someone like him! Most guys like sensual BJ’s and not all the rough stuff. Jerry was a guy who obviously enjoyed it. And once he started smacking me, I almost called it quits once or twice, because of how hard he was hitting me. But this time I knew I was going to take it. The first time we hungout, I was shy. This time I was into it! I was showing him that I can do it! I can lick, suck, jerk, and get that cum out! And my daddy can smack me and yell at me and it’ll just make me work harder!He didn’t cum that day, but we played for about an hour and a half. We would alternate between the rough play and just laying there with me sucking him slowly. And then at the end of it, he sent me on my way. I hope we hangout again, but I know we will. “You did a good job sissy” he told me as I was leaving. This time I KNEW my hair was messed up. I was gagging and spitting everywhere too, so I’m sure I looked like a mess. But it was fine because that day I got to show my daddy what I could do! And I had fun doing it

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