The First Gay Guy I Deflowered free porn video

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This is a first time story about the first gay guy who's anal virginity I had the pleasure of taking.

I am bi and had been having gay sex for sometime. I had my first gay sexual experience when I was 18. He was a friend of my girlfriend. She was bi too but we never did a threesome with her gay friend and I. He taught me how to fuck a guy, how to get suck and suck a cock. He never fucked me. I was not fucked for the first time until a few years later. Here is the story of how that happened:

It was not until a couple of years after that and after I moved 200 miles away to the city I live in now that I took the anal virginity of another guy.

I met several gay and bi guys after I moved. One of my gay lovers introduced me to the guy I would eventually deflower.

My lover and I were both vers. We would suck and fuck each other. We would also include other guys and we would have threesomes. Some of these guys were strictly bottom, some were strictly tops and some were vers. We would both fuck the ones who were bottoms only and they would end up with two loads of cum deep in them. The tops would fuck both of us and most often would cum in both of us, then we would fuck and cum in each other. With the guys who were vers we would switch off and they would fuck one of us, we would fuck them and each other, etc. It was always hot, fun, feel good sex.

One day he called me and said he has a friend of his who has been a top but only because he has never been fucked before and wants to be. He told me the reason his friend has never been fucked before is he is super tight. My gay lover has tried to penetrate his virgin ass along with others. He was thinking part of the reason no one had been able penetrate him is when someone tried he would get so tensed up and could not relax because of the anticipation of the pain it was impossible for someone to complete the act of anal penetration.

My friend remembered the story I told him of how I was penetrated for the first time and the technique that was used on me and the same technique I was still using, (and still use to this day), when a guy with a very large cock fucks me. My breathing technique to keep me relaxed so I can take the very large cocks that have fucked me over the years. He asked me if I would like to try and use that technique on his friend and wanted to set up a threesome. I said sure I would love to deflower a guys virgin ass. We set up the day and time for the threesome.

I was going to find out just how much fun this was going to be.

Over the years, through personal experience I also realized that when a guy cums before he is fucked in the ass, virgin or not, his anal cavity is tighter and harder to penetrate into. This had come in handy when I would fuck a guy and he would cum, before I would, while fucking him, and he tightened up around my cock helping me to cum deep inside of him. Or when a guy cums before I even try to penetrate him it is very difficult to open him enough to get my cock inside, but once inside it feels incredible and makes it easy for me to cum. Because of this I told my friend if you two start before I get there do not let him cum and explained why. I got the feeling this was part of the reason no one was able to penetrate his tight ass and apparently this guy could cum pretty quickly and easily with the right stimulation. My friend assured me they would not start until I got there.

The day came when the three of us got together. I arrived at my friends house a few minutes after the other guy did. We all went to the bedroom and got undressed. I told the virgin the first thing we should do is relax him but not let him cum until after or during me fucking his ass. I also assured him there will be no pain at all. He had a puzzled look on his face and asked how is that possible.

I told him the reasons:

Plenty of the right kind of lubricant.I told him for the first time lubricants like KY jelly or other water based lubricants are not the right one to use. The water based libtard do not last long enough and what off too soon. What is needed is something like Vaseline or a petroleum jelly type lubricant sage for human use.
Proper breathing. I asked him when got have tried to penetrate him do you hold your breath or start breathing really fast. He said yes to both. I then told him when I start to penetrate you I want you to take a deep breath and let it out slowly as I penetrate my cock into you. When you run out of breath I will stop and let you take another and so on and so forth. We will do this until I am all the way inside of you. He agreed.
The third reason I told him another guy had not been able to find him is likely because of the sexual position. I asked him what positions have been tried. He told me with him standing and beginning over at the waist and the other guy standing behind him. Him on his back with legs in the air or over the other guys shoulders. Or him on all fours with the guy kneeling behind him. I told him all of those positions do not allow for a virgin to relax enough to take the other guys cock. They are great if you are experienced at being fucked by a cock but not when it is your first time. But the position I am going to fuck him will.
The next reason I told him is if he cums before a guy tries to fuck you, you are even tighter because of how your prostate works. He told me almost every time a guy tried to fuck him he had already cummed his load. I told him he is not going to cum before I fuck him, but might cum while I am fucking him and I will make sure he cums after I am done fucking him. He was good with that idea.
The final reason I told him may be because he needs to be cleaned out before being fucked for the first time. I told my my very gentle technique will feel very good to him. He was really looking forward to that.

The other guy and I had him take a shower first. We had already taken one before any of us got there. He went and took a shower.

While he was in the shower our mutual friend and I got in bed and started making out. We kissed and stroked each other's cocks. We suck which others tits. I then had him get behind me and penetrate my ass. It has been a while since he fucked me and I was aching for it. He has a very large cut cock, at least 9” and thick. Once he was in my ass he made passionate love to me. Responded to his touch and wonderful cock deep in my ass by moving on top of him and riding him. I was controlling when he was going to cum in me. I would edge him then back off. I wanted him to cum inside of me just as the other guy walked back into the room and I would jerk my cock and cum all over the chest of the guy I was riding.

I continued to ride him. We heard the water for the shower turn off. I started riding him harder and faster because I knew they either guy with be coming back in the bedroom. I knew my liver was getting close to cumming and I really wanted to be filled with his load. I was also ready to blast my load all over his chest.

They either guy came back into the bedroom and right then I started cumming and my love filled my tight ass with his juicy load. The other guy got hard right away and said he could not wait to be fucked.

I got off of the guy who just fucked me and he got up. We surrounded our virgin lover on each side and started to make out with him. We then moved him to the bed and had him lay on his front. We told him we are going to make him feel really good and relaxed so he will be able to take my cock and anyone else's with time and experience.

To clean him out we used a warm enema that was there fluid used in the Summers Eve women's douche. Our mutual friend warmed it in a pan on the stove before we got there. The mutual friend and I, the guy who fucked me, put the douching fluid into an enema bag with a very small nozzle. We then told him how we we are going to clean him out. He responded by putting his ass in the air. We lubricated the nozzle, told him to take a deep breath and let it out as we put the nozzle inside him. He used the breathing method we recommended and we put nozzle in him and started to squeeze there warm solution into him. We had a towel to catch it when it flowed back out of him. We removed the nozzle and the fluid followed. We only needed to do one treatment. He started moaning in pleasure during the treatment.

After we were done cleaning him out I lay on his legs and started to eat his ass out. I kissed and tongued his crack and beautiful rose bud looking hole. I massaged his tight opening with my tongue and got him to loosen up even more. I got my tongue deep side of him. He tasted clean and sweet from the cleaning we did. He was really turned on by this time.

I asked if he was ready to really experience pleasure. He answered by moaning and putting his hot ass in the air. The other guy who already fucked me handed me the container of Vaseline. I took some and put it on the outside of his cute pink hole. I then started working my finger around his hole and put in him and started to fuck his ass with my finger. He moaned even more. I then added a second finger to the first. He moaned louder. I told him to take a deep breath and and let it out as I add a third finger. He took a breath and as I penetrated him with my hand he let it out slowly. I got my finger in him up to the last knuckle and then fucked my hand in and out of him. He then stated, very plainly, he wants my cock in him.

I positioned behind him to line the head of my hard cock with his tight hole. I told him he will feel a lot of pressure but as long as he controls his breathing the way I told him there will be no pain. With that i started penetrating his very tight hole. I got the head of my cock about half way in and just before he had to take another breath i pushed in just enough to get the head off my cock all the way in and to right where the shaft and glans meet. I did not move after that because I knew he had to take another breath and I wanted him to get used to my thickness. But was was incredibly tight and it felt amazing. It was all I could do to not just start to ram my cock in and out of him until I emptied my balls deep in his tight virgin ass. He continued his breathing and I started to gently penetrate further into his ass. The more I penetrated my 6” to 7” cock the better it felt as his anal cavity gave way and opened for my cock. I could literally feel my cock pushing his rectum/colon open as I entered him deeper and deeper. I did not have to stop until I got all the way in to the base.

My other lover, the one who fucked me earlier was sitting there jerking his cock as I deflowered the anal virgin.

After I got all the way in I asked him how it felt. He told me it is the most incredible thing he has ever felt and asked me what was next. I told him I am going to do to him what he likes to do to other guys, I am going to fuck you. I pulled back just before the head came out and pushed back into him. I kept this up a few times and each time he liked it more and more and he got more and more comfortable with it. I started increasing how hard and fast I was thrusting in and out of him. He started moaning like the whore that he is and yelling he wanted more. I started to feel his ass massaging my cock. I knew it was the stimulation cause by his prostate as I fucked him harder and harder. Some call it the male “G” spot. I could feel myself getting closer and closer to cumming in him. He was moaning really loud at this point. I told him I am about to cum. He pushed back hard against my cock and it sent me over the edge. I pushed as hard and deep as I could into him and emptied my load. He started yelling oh yes he could feel the thumping of my cock and a huge warm sensation as I came and came.

When I was done I let my cock soften so it would be easy to pull out of his hot, cum filled ass. When I did a large amount of cum came with my cock. I figured he would be very tender after being fucked. He rolled over on his back and sat up. When he did I saw the huge wet spot on the bed. He shot a large load of cum of his own. I asked when he did that . He said right when I was cumming in him. Our other lover, the guy who fucked me first, came to the bed, his massive cock very hard. The guy I just deflowered told him he wants his cock in him next.

He got on his back and put his ass and legs up. Our friend got between his knees and without hesitation shoved his 9” cock deep in his ass. The newly deflowered guy started moaning and wriggling his ass around as his tight ass was being fucked deep and hard. I moved around to where his head was and fed him my cock into his mouth and throat. He gladly started deep throating my cock. Our friend who was fucking him indicated he was going to cum. I was close to cumming again too. Before we both started cumming I bent down and took the newly deflowered guys cock in my mouth and throat. The friend fucking him started cumming first, this sent me and our mutual lover over the edge and we started cumming in each others throats.

When we were done our friend who fucked me first was spent and was not going to be able to get hard again any time soon and so was I. But the newly deflowered guy was still able to get hard again. He fucked our mutual friend first. He got on all fours and took the deflowered guys 7”uncut cock deep inside of him. Because he still very horny it did not take long for him to cum. After he did he pulled out and saw me on my stomach with my ass in the air expecting his cock. He did not take long to get hard again. He mounted me and shoved his cock in my ass. Because he had already cum three times he was able to take his time with me, which is what I wanted. He started slow and then increased his thrusting. I responded by pushing up and back against his cock. I also started to squeeze his cock with my ass and letting it go. When I would squeeze his cock I would push back and pull away. I could tell he was getting really close to cumming. He grabbed my hips, very hard, and started pumping and thrusting even harder. All of a sudden he slammed into me and I could feel his cum pumping in to me. I have not felt a harder thumping cock pumping cum into my ass before or since then.

His cock softened and he pulled out. I felt his huge load of cum run down my balls and both legs.

All three of us lay there and relaxed, naked, with cuming leaking out of our asses and the scent of sex in the air.

We still have hot, gay sex with each other to this day. Sometimes as a threesome together, sometimes with one or the other and we have had threesomes and more with other guys.

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“What’s wrong? What’s wrong?”Anthea looked up at her mum as she sat down at the dining table. “Nothing is wrong,” Anthea responded watching as her mum hurriedly dried her hands with a tea towel.“Is the baby okay? Are you okay? Is Jack okay?” she asked as her husband came into the room and pulled up a seat at the table.“We’re all fine Mum,” she responded exasperated with her mum’s anxiety. “I have something to tell you.”“Sit down Helen,” her dad snapped. “Give the lass a chance to speak.”Anthea...

2 years ago
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Gayathri Love And Virginity

“Ah! Ah! Ah! Yes! Yes! Yes! Aaaahh!!” Gayathri screamed as Sammy came inside her. She felt her inside filled with his warm semen. She looked sideways as Sammy collapsed on top of her. He was still inside her and was licking her neck. She could see her bra, panty and clothes scattered everywhere. That morning when she woke her up she was a shy, conservative virgin, but now, she lay there naked, little blood trickling down her thighs, moaning with pain and pleasure as she had sex for the first...

2 years ago
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Older Fat Gay Guy Got Horny

I was on Squirt, chatting with a guy about sucking and fucking each other. I am 76 yrs old, very overweight, at 270 lbs., and of course, not getting any relief from most all guys. I used to say I was BI, but have decided that I must be gay, because I enjoy watching gay porn so much. Mostly, guys fucking. Several years ago, I let a guy fuck me, and enjoyed it a lot. Although I had several occasions to suck cock and get mine sucked off, most just did me and left. Over the last couple of years,...

Hardcore
4 years ago
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Uther

Uther By Ellie Dauber (c) 2006 Introduction According to the legends of King Arthur, Merlin changed Uther Pendragon into a double for Duke Gorlois, so he could spend the night with Ygraine, the Duke's wife. Ygraine and Gorlois had three daughters: Elaine, Morgause, and Morgan le Faye. During their time together, Ygraine became pregnant with the child who was to become King Arthur. Uther's men killed Gorlois that same night. This is my TG (of course) version of what...

4 years ago
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Gayatri fulfills Rahul8217s long hair fetish 8211 Part 3

We had very much fun hanging out in the evening. Gayatri had put on her favorite light blue salwar kameez, looking gorgeous. Her hair is done in a thick, silky braid reaching her waist. Kavita was well dressed, with her hair done in a monstrous braid-bun. Most people don’t even get one girl. Here I was, roaming with two beautiful ladies I was going to fuck in the night. We went to a restaurant for dinner where I could see many people staring at that monstrous bun of Kavita. I didn’t like men...

2 years ago
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Gayatri fulfills Rahul8217s long hair fetish 8211 Part 1

Hello Readers. My name is Rahul. And I live in Mumbai, Maharashtra, from a typical Marathi middle-class family. I am 28 years, and life was going great until 2020 happened. I have a beautiful wife, the love of my life Gayatri. Gayatri and I were childhood friends from school when I had a huge crush on her. It was love at first sight when I saw her. We dated for a few years after completing our Bachelor’s degree and married a few years later. We reside in a good society with 3 buildings and a...

3 years ago
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Hot Gay Sex With The Stranger Guy

Hi, I’m darshan from Bangalore working in an MNC. I’m 5 ft 11 inches tall well built and have a 5-inch sized penis.I’m married and my sex with my wife is good. The sex story I’m narrating is a real incident which happened around 1 week ago due to my internal desires. I had a desire of getting fucked by a man, being cum slut to him which resulted in this incident. I wanted to be totally submissive to that man. If anyone is interested in having gay sex with me can contact me at I’m bisexual also...

Gay Male
2 years ago
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Carruthers Bride

The the wind howled around the quayside as I stepped onto terra firma for the first time in weeks, the wind threw sharp shards of ice to sting our faces as we looked up at the sails as they were finally furled and stowed as our captain grinned at our discomfiture, "Au revoir!" he joked as if he knew we should soon be recalled. Those such as were left, and we were few enough, I shuddered. My best uniform packed securely in my Valise, awaited me, and just a few more duties before I...

4 years ago
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Gayatri fulfills Rahul8217s long hair fetish 8211 Part 2

Now that my fetish was not hidden from Gayatri anymore, my load of burden was gone. She and I became even closer and used to have sex almost daily. She had become a very close friend to Kavita. At night, Gayatri showed me Kavita’s long hair pictures while she caressed my dick. I don’t know how she used to manage to get such pics of her, but I was enjoying it very much. Gayatri even used to give me a hairjob most days. She took care of her hair very much after knowing I had a hair fetish. I...

3 years ago
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Two Guys Find Gay Love

You could say this is part two of my first story but can be read as a story of its own. Like I said, a lot of straight guys from my section of Brooklyn don't have any problems with having a queer suck their cock. I found out, that I don't have a problem with it either.  Unlike the straight guys in the neighborhood having my cock sucked by a queer was more than just another sexual option.  It was having sex with another guy that was more important to me.  I found out I was queer that...

Gay Male
1 year ago
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1 drunk straight guy 4 drunk gay friends

I just want to share with people a experience I had which left me totally blasted, especially since I'm straight! I went to watch the recent Tyson v Lewis fight with a gay friend of mine at his flat. Three of his gay friends were also there and as the fight didn't start until the early hours we set about drinking plenty of beer beforehand. We started to disuss the fight and they all said it could go the distance, but I thought it would be over quickly like a lot of the big fights are and as the...

Bisexual
2 years ago
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Gayatri fulfills Rahul8217s long hair fetish 8211 Part 4

I got up from my nap after a few minutes. I went to the kitchen to see what my lovely ladies were cooking for lunch. I went to the kitchen door and peeked inside. Kavita and Gayatri were standing near the kitchen platform. While Gayatri was cutting vegetables, Kavita was cooking something in the pan. Not as a surprise, they were both naked with just an apron covering them from the front. Their oily hair was still in the braid which I had made. I could still see oil dripping from Gayatri’s braid...

1 year ago
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Motherless Vintage

Do you know of the porn site Motherless.com? You should. I’ve reviewed it a few times on my site, The Porn Dude, although it was for different genres every time. This time around, I’m going back to this place and looking at a specific and niche little category many of you are just begging me to cover. We’re looking at vintage porn today. While it doesn’t have the same resolution and quality as the porn you can find today, it’s definitely a genre of porn that has a lot of personality to it and...

Vintage Porn Sites
3 years ago
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Althea

I should have known better. I should have remembered that old saying, "If it looks too good to be true, it is." I was in love. She was damned near all I thought about with the exception of my studies and it didn't make sense to me. I prided myself on my intellect and my ability to think logically, but there wasn't anything logical about the way I felt about Althea. She was beautiful, smart and very popular and I was not. I wasn't a bed looking guy, but I was nothing exceptional. I was...

4 years ago
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Part 2 Mandy is deflowered

The time finally came! Mandy was 18 and she was kind of chubby, what you may call a nerd girl as she never dated but spent her time studying to get in to a larger college. Mandy had full firm breats and her ass was firm and round. She was a very pretty girl and when she was naked her body fit her frame and she was very attractive. I bought a few tickets to aconcert for all her parents had done for me and the night they were to go would be the night I planned to deflower their cute...

1 year ago
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Motherless Images

Motherless. A one-word website title that says everything it needs to say. This is a site where the rules are, more or less, completely thrown out the window, morality means absolutely nothing, and there is nobody to save you from it. Hedonism is God here.The site likely is also called this due to the fact that the girls who end up on motherless.com likely have no positive female influence in their lives to keep them from it. Motherless is the place parents spend their whole lives fearing that...

Porn Pictures Sites
1 year ago
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Motherless Amateur

I always considered Motherless the “4chan” of porn. Not only because Motherless was somewhat popularized there, but because Motherless also encourages users to share their own content in a very open way. This means minimal bullshit like moderation and censorship, and a strong “anything goes” attitude that leads to free and extreme content. It encourages people to create and upload their own homegrown content, like videos of their girlfriend pissing or spycam videos of their cousin....

Amateur Porn Sites
3 years ago
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First experience with super hot gay sex

Nobody knows I have sex with men. Except those men themselves, of course. I am a tough successful businessman, happily married for 22 years to a beautiful wife and father of a beautiful three of a kind offspring. I am secretly an effeminate bottom who wants to blow men and get fucked by them. In my youth I never really engaged in homosexuality, I fell madly in love with all kinds of girls and I liked them a lot. However, I have never been in love with a man; I've never even come across a man I...

1 year ago
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Motherless BBW

What is it about Motherless that makes me fucking cum every time? Maybe it is how raw and amateur the porn on the site comes across as, or the content is just that fucking hot. Perhaps it is the fact that there is an astronomical amount of pornography just waiting for a dumb fuck like you to beat off to! I really don’t know, and frankly, I’m not going to pretend that I do.But what I do know is that if you love BBWs, the Motherless.com homepage will not be of much use! Preferably, head on over...

BBW Porn Sites
1 year ago
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Motherless Voyeur

Have you ever heard about a website called Motherless? Home to all kinds of kinky porn niches, with a side of the mainstream crap? If you are into some questionable fap content, you might want to check this website out. Plus, Motherless is a free porn website, so you can browse as much as you fucking want. Now, I am not really here to talk about the website in general… I am here to tell you about their amazing category, called voyeur porn.The world of voyeur fucking is a rather interesting one....

Voyeur Porn Sites
1 year ago
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first time gay with room service guy

He could not stop staring at my bulge in my running tights. Gay Room Service After a bit of drinking, I went back to my hotel room. After a while, I decided to order room service – a sandwich and some fries. After about 30 mins there was a knock on the door and a slim, nice looking man in his 30s asked if he could come in with the tray. I was wearing tight running leggings and had quite a bulge at this point. He put the tray down and was definitely staring between my legs. As I signed the...

Gay
2 years ago
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Aether Guardians

The Five Kingdoms of Arstoria had been embroiled in the Great Ancient War for centuries. The war came to an end when Kalace, the Wizard King conquered the five lands and brought them under his rule. Kalace, the Wizard King of Arstoria, conquered all of his opponents who were unable to deal with his overpowering magic. When Kalace had united the five kingdoms, he brought peace to the warring kingdoms and was revered and celebrated by his later generation. Kalace, however, had a dark weakness in...

Fantasy
3 years ago
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Gaynors guest

Your wife comes in from work wearing her nurses uniform, slips off her coat and bends to drop her bag in the hallway. As she bends I cup the lovely round globe of her buttock, enjoying the feel of her cotton uniform, the smooth tights underneath and the leg of her panties. Hmmm she softly moans, this must be the surprise Peter had planned for this evening.I continue to stroke her round arse, getting a good feel and rubbing between her cheeks through her clothes. Her legs part slightly as she...

1 year ago
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Motherless Creampie

Woah, did Motherless.com get a facelift? I know I suggested it in my review, so I guess they listened to me! Well, I’m not going to brag too much about it, and instead, I’m going to focus on what I’ve set out to bring you today. We’re looking at an amateur website, and I just know that many of you are begging for amateur creampie content, so that’s what we’re looking at. I know how much you think Motherless can look sickening and pretty gruesome at times, but the creampie content can be quite...

Creampie Porn Sites
1 year ago
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Motherless Cuckold

No matter what type of porn you may be in the market for, Motherless has an ample supply of it, and cucking is no different. Actually, this might help to explain how you ended up being such a pussy little cuck.The journey that brought you to my website reading cuck porn reviews started in your childhood. A fair portion of my readership is actually motherless. Why, you ask? Your guys' moms chose a life of cucking and riding cock instead of raising you fucks properly.Don't worry, gents. I'm in...

Cuckold Porn Sites
1 year ago
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Motherless Horror

I browsed the horror stash at Motherless all morning, and now I don’t know if I should jack off or go hide in the closet until the danger has passed. Then again, hiding out might give me the perfect opportunity to rub one out in the peace and safety of the dark. Who knows who—or what—might be peeping in the windows with nefarious intent if I sit at my desk and shake my dick at the screen. Just like when I masturbate at the local Starbucks, I’ve got to be sure to balance the potential pleasure...

Extreme Porn Websites
1 year ago
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Motherless Incest

Incest porn has been a staple of pornography since the very first incel caveman realized that he couldn’t find fresh pussy out and about. He resorted to sniffing a whiff of his mother’s loincloth when she wasn’t looking, and beating his old cave meat into a leather sock.Now personally I’m not into the whole mommy-son dynamic – I’m a classy guy. But it’s no secret people like to get freaky when the lights go out, and if you’ve got a stiffy in your hand and you’re on Motherless, you gotta go...

Incest Porn Sites
4 years ago
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Gayathri The Sex Bomb

Hello ISS readers, I’m Rudra 19 years old from Kerala. You can contact me at ”” Girls or aunties near Kerala or Bangalore who wants some fun can contact me at “” This story is about how I had sex with my neighbour Gayathri. She is my neighbour is 23 years old with beautiful face and assets of 30,26,32. She was a sex bomb, she lives with her parents near my house. She was not a typical mallu girl she used to wear modern dress tight t-shirts and all. I use to masturbate thinking about her almost...

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