First Time Porn Stories
Page 5

One Crazy Trip

Being a virgin in your late twenties isn’t a cool thing I should say. I think the issue goes back to my middle school years. It was a tough period for my f****y, we lost few of our beloved ones during a span of two years and back then my f****y was literally falling apart. As you guessed it already my head was a mess, plus I was self-conscious of the fact that I was very skinny so to say that I was very insecure was understatement. Obviously I wasn’t very popular among pupils, I’m not even talking about my relationships with girls because there wasn’t even such a thing for me!

After I grad... Continue»
Posted by eros77ua 6 days ago  |  Categories: First Time, Hardcore  |  
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Daughter in Love with her Daddy that Summer.

'You need to get to know who your father is', was all mother said to me. He and mother had parted ways shortly after I was born, so I never got to know him, let alone see him, except for photographs.

I had learnt through the f****y g****vine he was homosexual and that had been the reason for their breakup, but mother never talked about him, anger I suppose being duped into marriage and a baby to follow, I could not blame her for seeking love elsewhere, albeit as a used woman, her stock had fallen, and her new beau was a man as old as her own father, lucky him, as she was still a vibrant and... Continue»
Posted by Fridagirl 6 days ago  |  Categories: First Time, Gay Male, Taboo  |  
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Truth or dare gangbang

My wife had a longtime friend of hers’ that was roughly 10-15 years older than her, but they were always close. They were always there for each other, even though they were separated by state lines and then some. She’d come stay with us when my wife needed her and vice versa. One day my wife, Jessica’s phone rang with her friends’ ringtone and I half listened to the conversation. Her friends’ daughter was getting married and she needed help with the rehearsal the weekend before the wedding. I knew she wasn’t going to say no. She told me I was going to have to hold down the fort and that she wa... Continue»
Posted by WereIT 6 days ago  |  Categories: First Time, Group Sex, Voyeur  |  
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"Poker Night" - The Leatheress, episode

"The Leatheress"
Episode 1 - "Poker Night"

I hadn't gone to Bruce's house that night with any expectation that I'd be finishing the night by blowing him on is black leather sofa, but that is the way it turned out. Don't get me wrong; I'd had an interest in him ever since the first time I saw him reporting on my local evening news, but it's not like I truly ever had envisioned a scenario where such an interest would grow to become anything more. It is just funny how things work out, sometimes.

I guess we should probably start with some backstory. Myself, I always had an interest in dre... Continue»
Posted by SexyLeatheress 6 days ago  |  Categories: Fetish, First Time, Gay Male  |  
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77 Her mother’s gardener.

77 Her mother’s gardener.
I was just finishing my breakfast, sat mopping my plate of the last of the egg-yolk when my wife Margaret suggested that while we were out we ‘popped in’ to visit her mum.
Not one of my favourite occupations visiting and I spluttered a bit but knew if she wanted to ‘pop in’ then pop in pop in is what we would be doing, my life would be less happy if we didn’t, all husbands know that ‘a suggestion by the wife’ is actually a plan set in concrete in most regular marriage`s. They tell me that some wives are subservient ‘yes dear’ ladies, well mine [and millions of oth... Continue»
Posted by alibodge 6 days ago  |  Categories: First Time, Mature  |  
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Go For It!

As I was going thru puberty my older b*****r told me to always go for it! If a girl gives you an opportunity to have sex I should go for it. I had many girlfriends but never had sex. I came close a time or two but for some reason never closed the deal. I had the biggest crush on one of my teachers all thru high school.
Her name was Mrs. Sue Foster. She was not really hot per say, but there was something about her that made me want to fuck her. I could tell that she had a fairly smoking body, nice sized tits, nice ass. She was about five foot eight inches tall, dirty blonde hair about mi... Continue»
Posted by zimabean 6 days ago  |  Categories: First Time, Hardcore, Mature  |  
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My first time at 18 years old

At this time I am 18 years old and its summertime. Having just graduated from high school it was to be an exciting summer with new plans on the horizon. Throughout my teenage years I was always very much a straight guy and still am to this day. The only difference is that I had a secret longing to be touched by an older man , a fantasy of sorts that I had decided I would soon experience. Back then the main social media was Myspace , it was all the rave and one horny night on the computer I stumbled upon the page of an older man in his late fifties who happened to live in the same town as me. ... Continue»
Posted by MichiganJock 7 days ago  |  Categories: First Time, Gay Male  |  
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Fucking my slut Chloe!

There you are sitting across from me at the table, trying to be so prim and proper as we sip our drinks and talk about our lives. You must be getting bored with the discussion because I see you fidgeting with the bottom of your short little mini skirt which barely covers anything!

I am telling you about that annoying bitch at work and you couldn't care less 'cus all you want is sex, sex, sex. You have been doing nothing but complain for the past hour about how you aren't getting any. On and on as if you thought you might die if you didn't "get some" soon.

As your knees start spreading, ... Continue»
Posted by image-fapper 7 days ago  |  Categories: First Time, Hardcore  |  
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My Daughter and My Wife Go Black

Our white daughter is 19, attends a nearby college. To save money still lives with us. She has her own bedroom and sometimes has male friends over when we are out. It took a while, but we got used to it.

This one Friday night my wife and I were supposed to go out for dinner as usual, but there was a long line at our favorite restaurant. We decided to just grab a couple hamburgers at a drive-through and head home -- a couple hours earlier than usual.

As we sat in the kitchen eating our hamburgers, we heard the bed squeaking in our daughter's upstairs bedroom. My wife and I looked at each ... Continue»
Posted by GotBBC 7 days ago  |  Categories: First Time, Hardcore, Interracial Sex  |  
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First Night Out as a Sissy Pt 2 (By Crystal_ed)

So picking up where I had left off from my last published story…. I had just ventured out for the first time as sissy, determined to find a man. I went to a local sports bar dressed in in my tightest jeans and favorite panties and teased a group of guys. Was able to get one of them into my car for my first blow job ever and after swallowing his enormous load, his friends busted us before I could know the pleasure of him inside of me. After being busted (but feeling sweetly naughty) I was going to call it a night before I realized the bar tender still had my card because I hadn’t closed my tab.... Continue»
Posted by Crystal_ed 7 days ago  |  Categories: First Time, Gay Male, Shemales  |  
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Meeting my Neighbor

I live in a small but growing city, but most everyone (including me) is on the DL so there's never a lot of action. I saw a post on Craigslist last night from someone in town. Since I couldn't get away I figured it was a missed opportunity, but I emailed him anyway hoping that maybe we could work something out another time. I was pleasantly surprised when he emailed me back this morning, and he was still looking and could host. He was only a couple blocks away, too.

I made my normal excuses ("going to get some exercise") and walked over to his house. He met me on the porch and we chatt... Continue»
Posted by boernesucker 7 days ago  |  Categories: Anal, First Time, Gay Male  |  
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My first abuse and humiliation

I can't see, my nipples are on fire and my throbbing cock is being teasingly stroked, all's well.

I don't get to cum without my partner and due to an extremely busy week with no physical contact I'm extremely pent up, my balls are full and my mind has been utter filth for the last 4 days. In our time apart I am permitted, no, encouraged to touch myself, edge, tease, but never cum. That is her semen, her orgasm and her property between my legs, but she always likes to have her fun before I get my release.
I answered the door in just a dressing gown, she kisses me and smiles, quirking an eye... Continue»
Posted by damage_case 7 days ago  |  Categories: BDSM, Fetish, First Time  |  
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Wife's Sexting Gangbang

My wife had a longtime friend of hers’ that was roughly 10-15 years older than her, but they were always close. They were always there for each other, even though they were separated by state lines and then some. She’d come stay with us when my wife needed her and vice versa. One day my wife, Jessica’s phone rang with her friends’ ringtone and I half listened to the conversation. Her friends’ daughter was getting married and she needed help with the rehearsal the weekend before the wedding. I knew she wasn’t going to say no. She told me I was going to have to hold down the fort and that she wa... Continue»
Posted by WereIT 7 days ago  |  Categories: First Time, Group Sex, Voyeur  |  
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Cuckold Teen 2

As I started to cum, Tasha opened her mouth and pearl white sticky cum streamed from my rock hard cock into her mouth, there was a heavy load and it started to trickle out the corners of her mouth. "Hold my cum in your open mouth" as I again grabbed my phone and opened the camera, a few photos then video, ensuring that Stuart was in no doubt how hard she had been face fucked, her mascara had ran down her cheeks and this little cum bucket had a mouthful of my cum in her mouth "swallow my cum you little slut and tell your pathetic boyfriend hoe it tastes" I commanded, Tasha gulped my cum and eve... Continue»
Posted by lovelong 7 days ago  |  Categories: First Time, Group Sex, Taboo  |  
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Early Morning Encounter With Transwoman

Was walking back from town early in the morning, was stranded in the outskirts of the city which is distant from my own home in one of the suburbs. I had left the warmth of the house of my friend in the city, and ventured out into the early morning, 1:00 or 2:00 o clock, it was cold, but not as cold as it could have been, the clouds in the sky made sure of that, and for that i was happy, despite the occasional light to medium downpour.

I had been texting a Lady friend, a woman, asking her to let me in and stay and in exchange i would eat her pussy, she agreed and was horny however she was ... Continue»
Posted by trueblue934 7 days ago  |  Categories: First Time, Masturbation, Shemales  |  
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The Sissy Trainer Part 2 – Taking A Virgin

Ken raising my dress higher to have a better view of “loosening me up” and told me to rest my heels over the other end of the couch. As he fingered my butthole, his hard cock continued to slap against the side of my body as he wiggled and shook his finger. The more I thought about Ken finally ramming his cock in my tight butthole the harder I clinched. “Lisa, I need you to relax some, take a deep breath” “Ken” I asked “Is it going to hurt much?” “You are super tight, but I brought lots of lube…I think you’ll be fine.” “Thank you” I whispered. Ken pulled out his finger. “You know this is not go... Continue»
Posted by MatureBrownMan 7 days ago  |  Categories: Anal, First Time, Gay Male  |  
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a story about me and not my s****r

My life is a bad start, already at the age of 6 I i was in c***d homes because of a difficult f****y situation. Until I was 13 I have lived in five different boarding schools and in foster care. While during the time I lived in the foster home, my guardian to arrange was that I could live at home, only then my mother died.

Janet, 20 years older than me (not my s****r, because we can’t talk about i****t), Janet, decided to take care of me and take me into her f****y. She was married and had a son by four at the time. Her husband was an international truck driver and was often days, sometimes... Continue»
Posted by Vertel 10 days ago  |  Categories: First Time, Masturbation, Taboo  |  
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waking up after the night out!

i was away with my mates on a night out and it was a going to be a mental one as it was a my friends stag-do. we had gone to Soho London and we were stopping over. we were hitting the town and we were going to pull what we could as when the cats away!!
my wife said just be safe and don't catch out with a smile on here face knowing what i am like.

so we were out and the drinks were flowing all the lads were still together but as the night went on it was just 2 of us sat in this bar pissed waiting to go back to the hotel cos as we were the old ones and we were knackered. a couple of lads ca... Continue»
Posted by naughtydarksecret 10 days ago  |  Categories: Anal, First Time, Interracial Sex  |  
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My sexual Awakening.

This story, like the other ones I write, is either true or based on something in my life that happened. Sometimes it’s impossible to remember exact names and dates of things; just like some of the details. I’ll let the reader decide how much of some of them are true. I’ve been a male slut for most of my life, I have taken a lot of big black cocks (because I love doing that) and did start to be sexually active at a pretty young age. Yes, I did get very good at cross-dressing and loved that part of my life. I did begin to have orgasms – while being fucked – at a younger age and, as in the one st... Continue»
Posted by swat412 10 days ago  |  Categories: Anal, First Time, Gay Male  |  
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A surprise at the party - Part 2

In part one of this story I've told the tale of how I met Tanya. A party at my friend's house, in which we were introduced with no pretext. A few drinks and a slow dance later, We were running up to find a bedroom, like a high school couple in a college party. An hour more went by and we were standing together in the shower after an unusual, yet very pleasurable sexual encounter. She was tall, beautiful, and had soft East-European facial features I just couldn't resist.

As we were standing in that small shower cabin, and I was washing off the soap off of me, she leaned in to kiss my back, w... Continue»
Posted by GalFa 10 days ago  |  Categories: Anal, First Time, Shemales  |  
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