Redemption With Jerry (1st And 2nd Encounter) free porn video

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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 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 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 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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SurprisesChapter 13 Jerry

I woke up the next morning alone in bed but otherwise feeling fine from the night before. I wasn’t the only one feeling fine, though. I could hear fun and games through the open doors between my bedroom and the hall and the hall and my parent’s bedroom. I pulled my robe from the closet and wandered down the hall. Once inside their bedroom, I could clearly hear my mother crying out, “Fuck my ass! Fuck my ass!” She and Daddy were screwing in the shower. I waited for them to finish and then...

4 years ago
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181AVISS holiday at Jerrys family home

181 Jerry`s holiday at home Jerry told Jaz and me to dress in see through blouses, no bras, short skirts, panties and garter belts to hold up our stockings and stiletto heels. When we finished, he placed a collar around my neck and we headed out for the day. We went across town and into his old neighbour-hood and pulled up next to a large tenement building. I could see a few black men milling around and Jerry got out, "Wait here" he told us and went over to talk to the men. They soon...

1 year ago
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Dear Uncle Jerry

Dear Uncle Jerry I moved back to Jacksonville after selling my business in Modesto for a nice profit. I liked northern Florida. It was more populated with native-born folks, rather than New Yorkers, Canadians, and other refugees from the North, who preferred the southern half of the state. I took my time looking for another business opportunity because I knew pretty much what I wanted to do. Of course, I had to fend off a lot of "old friends," who had an endless list of business ventures for...

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3 years ago
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Jerryrsquos World Terri

“So did Tiff settle alright” I asked while I thought of ways she could repay me, Terri looked at me and smiled, “Yes, you must have worn her out” she said giggling and if nothing else was getting me hard listening to her sexy husky voice certainly was, “Is she ok sleeping with you then Terri?” I asked trying to dig a little deeper, her eyes widened giving me a warm smile, “Oh yes Jerry, she loves a cuddle and the affection” she answered and I could tell by the look in her eye exactly what she...

2 years ago
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Jerryrsquos World ndash Dr Goodwin

I walked across to the doctors office which was in fact in the basement and slowly and carefully went down to the front door and rang the bell, my jaw dropped when the door opened.Maybe I was expecting a pretty receptionist but I certainly wasn’t expecting an old man well into his 70’s dressed in a button up white coat and from what I could make out, not much else.“Hello, I’m Dr Goodwin, I am a doctor you know” he said very professionally while looking me up and down, “You must be Jerry” he...

2 years ago
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Running naked in front of Jerry

Jerry and I used to meet at a local park in Sacramento late at night. Jerry loved to see me naked. Many times he would walk over to my car and demand that I strip and walk over to his car totally naked. I would comply ... removing all my clothes except my running shoes. I have a runner's body ... having run several marathons. And I keep running now.If other cars were in the park, obviously other guys, Jerry would invite them to park behind him car to watch a "naked guy" walk through the...

3 years ago
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Jerryrsquos World ndash Mrs Roberts Part 2

I made my way downstairs and luckily my cock was semi at best; I still had no idea where my shirt was so went to find Mrs Roberts who wanted to see me before I left. I entered the lounge and could hear some music coming from out in the garden, I walked up to the open patio doors and OMG there was Mrs R laying on her belly on a sun lounger, my initial thought was she was naked however on closer inspection I could see the thin white string of her thong wedged between the cheeks of her sweet...

2 years ago
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Jerryrsquos World ndash The Aftermath

I think Kay had led a sheltered life having to look after her elderly Grandpa which must have taken up a lot of her time, she was amazed at how I enjoyed sniffing her panties which told me that her Grandpa wasn’t into that and as she made his tea she encouraged me to do it more, OMG this was so horny.The old man was already flagging as Kay put his tea down, “He’ll be asleep soon Jerry” she said with a giggle, “Got time for another beer?” she asked as she watched me sniffing and licking her...

3 years ago
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Jerryrsquos World ndash Mrs Roberts

I don’t know why but I was a bit nervous as I got off the bus and walked up the street to Mrs Robert’s house. I was sweating in the heat and realised I was a little bit early but decided to go along anyway.As I approached the house which was in a leafy street in one of the better parts of town I noticed Mrs Roberts pottering around in her well kept front garden, she hadn’t noticed me standing by the front gate as she had her back to me so I stood quietly soaking up the atmosphere.From what I...

3 years ago
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Jerrys World Decision Time

Roger explained that the room wasn’t ready yet so there was no rush in making a decision and he wouldn’t be advertising it which was a great relief as I didn’t want to make a quick decision especially as things were looking better with Bev, he was so kind and considerate even inviting me over any time I wanted any physio or just to hang out, for me it was a win/win situation.“How are the hips this morning son?” he asked as I was getting dressed and I had to compliment him on his expert...

3 years ago
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Jerryrsquos World ndash Doctor Surprise Part 3

Time had to move on and eventually she reached forward and with one hand she cupped my balls while the other wrapped around the shaft gently pulling the skin back exposing the swollen head which for some reason looked bigger as it glistened with precum.She gently squeezed my balls feeling every inch like she was counting my pubic hairs with her fingers while she just held on to the shaft with the other, “Mmm Jerry, your testicles feel so nice Jerry, no lumps” she said which was reassuring and...

3 years ago
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A few days at Jerrys V

Laying on jerry's lap and him rubbing my dick made me feel better. When the movie ended he said he had to get something. He went to the bathroom, when he came back he had a towel and lotion. I started to get excited. He sat down and pulled me across his lap with my butt centered on it. He rubbed my butt a little and said to relax. He spread my cheeks open and rubbed lotion on my butt hole. It felt good as he circled around it. He said to take a deep breath, when I did I felt his finger push in....

2 years ago
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Jerrys World First Viewing

I went up to shower before dinner and didn’t even think about shutting the bathroom door, why would I anyway as Bev was cooking plus it’s not that kind of household, privacy is not only hard to come by its also deemed unnecessary. I was happily soaping my body and as often happens was a bit over zealous in the nether regions but then my parents had always instilled in me to give that area a good clean, it’s something that has stayed with me all these years so it was no surprise that I ended up...

2 years ago
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Trish and Jerry

It was raining cats and dogs, but I didn't give a good goddamn! Herdin' a semi down the road was better than watchin' them damn soaps. Retirement-reshmirement, it sucked. Being retired ain't nuthin' but waitin' to die. Not me, not anymore, I'm workin' again. I pulled the big rig into the diner and parked for easy egress later on. I only had a couple of hours more road time, but I was hungry. The construction project would have to get along without its rebar till I filled my belly. So...

1 year ago
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Becoming A Slut Husband Jerry

I hit the post office on my way home from work and, as usual, my box was full of junk mail and bills. I leafed through them and dropped most of them in the trash can next to the table. Between the Visa statement and the Conoco bill was an enveloped addressed to me in the flowing handwriting I knew only too well. I'd been getting one a month for over a year. She had figured out that I was having my mail forwarded from the old address so she wrote and sent it there so it would be forwarded to...

4 years ago
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Jerryrsquos World ndash Gymnast Fitness Part 2

Mia was doing a great job and I wasn’t backwards at telling her, she loved the encouragement and was eager to know what was next.“Ok Mia, your doing great, now I want you to face me and bend down so I can check your shoulders and back, you can hold on to my hips for support” I said giving her then next set of instructions, “OK sir” she replied enthusiastically and spun around straight away noticing my shorts were halfway down my legs.“Oops sir, your shorts are down” she said with a giggle as...

4 years ago
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Jerryrsquos World ndash A Chance Meeting

It was a lovely evening so I decided to have a walk home to familiarise myself with the area as I didn’t know it too well. I took a shortcut through a small leafy park and found I was bursting to use the toilet and luckily tucked away in the corner I saw an old toilet block, happy days.I walked in and with only some old guy standing at the urinal I happily pulled my cock out the top of my shorts and let out a big sigh of relief as I emptied my bladder.I wasn’t paying much attention to the old...

4 years ago
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Jerrys World Beverleys Friend

I wasn’t sure if Lynn had ever seen a cock before but there was no mistaking I was aroused, “WOW Jerry” she sighed softly as she looked at my angled bulge, my shorts were a snug fit and I was only glad the button was holding out. Lynn giggled as she looked at the pulsing bulge, “Have you ever seen a penis before Lynn” I asked with a cheeky wink and she looked up at me taking another gulp of her beer.“It’s not something I am really interested in” she replied confirming her sexuality and I...

3 years ago
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Jerrys World First Agency Job

I had a feeling today was going to be a good day and after my morning routine with my dear sister which involved taking my daily pill I got an alert from Sophie that I had a booking come in from a lady called Alice who wanted me to look at some odd jobs for her. She gave me the heads up that when she booked me online she gave her age as 48 and occupation as school teacher, I just hoped she wasn’t one of my old teachers although I don’t remember an Alice, Sophie also remined me to take a...

3 years ago
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My friend Jerry returns

Jerry and I had been friends since we were nine or 10 years old, we played together, and learned about girls together over the next couple years as we started puberty. Whenever we were alone together we would talk about girls and get so horny and masturbate together. I don't remember exactly when, but at some point we both became curious and began to wonder what it was like to touch another guys cock and so it began as we explored each other. We both found it very exciting to touch and play...

4 years ago
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Jerryrsquos World ndash Andirsquos Surprise

So I am a nudist now eh! Well at least that solves the problem of what to wear for the interview process and as I hadn’t even got dressed from my shower I didn’t have too much preparation so I sent a quick reply.. “Hi Andi, yes can interview you this morning” and it was seconds before she replied, “See you soon x” which was an interesting use of the ‘x’, was it a sign of endearment for a job interview?I decided that it may not be appropriate to answer the door naked so I slipped...

1 year ago
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Jerrys World Ella and Sam

“Come on Bev, lets do some girly shopping” Sam said which excited my sister, “Ella has homework to do” she continued which Ella accepted, “Can I help you with it?” I asked trying to break the ice and make her forget about her mummy going shopping without her, Ella smiled sweetly, “Hmm, yes please Jerry” she replied and I told her to call me Jez, “Thanks Jez” she said with a giggle as she sat on the sofa and got a couple of books out her bag, “I do love your shorts Jez” she said softly with a...

4 years ago
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Randis Vacation Part 3 of Randi

Randi's Vacation Randi woke up to his alarm and quickly silenced it. A quick glance to his left confirmed the Denise was already up. She almost always got up before him preferring some extra time between getting ready for work and needing to walk out the door. He preferred to have enough time to get ready, eat and go. He walked to the bathroom which was right in the master bedroom. The condo they bought was a bit extravagant but provided plenty of room and they could afford it on...

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