First Time Porn Stories
Page 449

First time with a man (or two)

Hi there, ive been a member of xhamster for a while so i thought it was about time i added my own story, so here goes. This is a true story about my first sexual encounter with a man, which turned out to be with two men in fact.

I had been curious about gay sex since i was in my teens but i never had the guts to do anything about it til i was in my mid twenties. i didnt lose my normal virginity until i was 20 and then at 25 i lose my arse cherry. I was single at the time and a friend of mine, whom i was very open with, had told me in conversation that another friend of her's was gay and t... Continue»
Posted by diggerdoug 3 years ago  |  Categories: Anal, First Time, Gay Male  |  
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First One, Then The Other

When this happened, it was the summer after my graduation from high school.

I'm an only c***d and live with my mom and dad. My dad is a Vice President at a local bank and my mom teaches elementary school. She has a s****r, my Aunt Tina, who also lives near us and also teaches in the same elementary school as my mom.

It was the school I first went to and it was weird having them both there, they're identical twins and really do look quite alike. But, now I would be going away to college though I was able to see my aunt a lot since that summer.

It was then, that her husband of ten years... Continue»
Posted by zopri 3 years ago  |  Categories: First Time, Taboo  |  
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first time public

My First Time In Crowded Place As Cross Dresser

about 2 months ago, i got up the courage to go to a crowded public place dressed for the first time
i put a post on craigslist saying where i was going and what i was wearing
then i drove to shopping center parking lot and dressed up in the car, make up, red lip stick, red finger and toe nail polish, blond wig, ear rings, necklace, rings, watch bracelets, thigh high stocking and gatrer belt, black 5" heels, black mid thigh dress
i drove to a closer parking spot and took a breath, put on sunglasses, grabbed my purse and stepped out into publ... Continue»
Posted by cdamanda 4 years ago  |  Categories: First Time, Shemales, Voyeur  |  
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When did Mom Start Wanting Me

Back shortly after I was born dad was in a bad accident that killed him while on the job at work, which left my mom, s****r, and me, to live without a husband and dad.

Some years later mom met a guy and they got married and even thou he never really tryed to just step in and take dad's place in my life, which was a good thing at the time, he did treat me like a friend and not like a k** and he did the same with my s****r too.

The one thing I didn't really like the most about the guy was, he never let me go with him deer hunting and fishing. He said he didn't have time to teach me how to ... Continue»
Posted by HankWilliams1956 1 year ago  |  Categories: First Time, Taboo, Voyeur  |  
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First time with my Aunt

I would like to let everyone know this is my first story and if it is well received i would love to share many more of my stories with you. All criticism is welcomed and actually expected.

Where do I begin, i assume the best place would be to describe my aunt to everyone. She is about 5'4 and very curvaceous. I am talking about a huge ass and very nice D-cup breasts that aren't perky but actually sag in a nice way. At the time she was 25 and i was about 16 so the age difference was definitely noticeable, however i was very mature for my age which sounds cliche but it is true.

My aunt m... Continue»
Posted by Instig8 4 years ago  |  Categories: First Time  |  
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My First Time Part I

A little back ground information to start things off. I was 25 and in college at the time and had been curious about being with a guy for quite sometime. At that point I had only been with females (a decent number) but was going through a dry spell. It had been close to a year since I had last had sex, but had fooled around a little bit in between. During that time I was getting to be quite horny all the time and would be frequently masturbating, mostly to straight porn, but when I could bored of that I would masturbate to gay porn (mostly mmf threesomes).

My curiosity had been getting the... Continue»
Posted by imcanadian1919 4 years ago  |  Categories: First Time, Gay Male  |  
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Jack's adventure #1

Hi all, I’m Jack, a 19 year old guy and I want to share my story of how a girl turned me bi and probably gay.

So it all started at the end of our summer break. The last week had started and the new school-year was almost upon us once more. I had tonnes of essays and book reports due the first week. But, being me, I haven’t started yet on any of that.
Now while I had to sit down inside, and work nonstop for this whole week to have a chance of finishing it all, but nature, humanity and generally the whole universe were against that.

The weather was great, the beaches were finally starti... Continue»
Posted by alexnl 4 years ago  |  Categories: First Time, Gay Male, Group Sex  |  
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The Awakening of Christine

My wife, Chris, and I live in an urban center on the east coast. We're both successful lawyers who work downtown and have been married for 15 years; 14 of them in total monogamy. I am 50 years old and she is my second wife.

Chris, who is 38, stands 5'5" tall, has short brunette hair, 116 lbs., beautiful legs with breasts in total proportion to her body; a lovely figure with a defined, European face...big eyes and soft lips. (Her parents came from Sweden.) We don't have any c***dren by choice. And though she dated a little in high school and as a freshman in college, I am the only man with w... Continue»
Posted by p318i 5 years ago  |  Categories: First Time, Group Sex, Mature  |  
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Teaching Erin

I arrive at your house late in the afternoon. You're alone with a summer dress tainted in pink and red. You take me by the hand saying nothing, to your room, and sitting on the bed while I keep standing. Even though it's summer the shutters are almost completly closed, just letting in enough light to allow us looking in the eyes.

As you let your dress slide down your golden body I feel the vains in my cock to starting to throbe harder and harder.
The sight of you lying on the bed with, is giving me such an urge I feel I'll not be able to control myself but i know it's too soon. St... Continue»
Posted by mistermister1000 5 years ago  |  Categories: Anal, First Time, Voyeur  |  
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Sea Adventures

Part I

Anniversary

When we first arrived in the small village on the island in the Mediterranean, I almost started crying. It looked like a place from the third world, with stone built houses, and so peaceful as if no one actually lived there. My mother knew my wild side very well and I could swear she picked this place on purpose, just to prevent me from staying out till dawn every night.

Soon I discovered that the place had just one hotel, one tavern, two small pubs and an open air cinema. There was no way I could even think of shagging someone... I lost my virginity just a year ago... Continue»
Posted by sellena 3 years ago  |  Categories: Anal, First Time, Hardcore  |  
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First With Mom

I was in my final year at high school and had never had much luck with the ladies. I had only kissed one girl time. I do not think that I am ugly or anything, it is that I am scared of girls.
My parents were much older when they had me. I was the product of a weekend they were away and they thought they could not get pregnant. Mom just turned sixty, she is tall with nice perky boobs. She has wide hips and is kind of skinny. She has brown hair to the middle of her back, it has blonde highlights but some gray too. Mom also has the warmest brown eyes I have ever seen on a woman. I had seen ... Continue»
Posted by zimabean 4 years ago  |  Categories: First Time, Mature, Taboo  |  
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nailed the nice niece

It happened about 5 years ago and I live it in my head like it was yesterday.

I married into a big f****y of 6 girls the next s****r up to my wife had a little girl about 22 yrs ago and fell in love with her as soon as I met her. Emma was cute and as she grew up we fell in love like father and daughter as her father pissed off to live with another women, I had fucked her mother my s****r in law on a few occasions and had enjoyed awsome sex god knows why her hubby left her, sexy body, awsome bj's top rate hand jobs and mind blowing sex with orgasms that would deafen you when she cum.

Well... Continue»
Posted by rodma 3 years ago  |  Categories: First Time, Masturbation, Taboo  |  
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Our first time with a stranger

This is a true story that happened to my wife and I just over a year ago. It wasn't planned it just happened unexpectedly.

I had booked us a show and a nice hotel in the west end of London. We have done this before and it usually leads to us having a few drinks after the show, stumbling back to our hotel room and having noisy sex. That night was no different. After our drinks, we took a walk through Soho and looked at the sex toys on display in the "naughty" shops. My wife took a shine to a G spot toy so we bought it. We couldn't wait to get back to the room and try it out! In the lift in... Continue»
Posted by 69nik 1 year ago  |  Categories: First Time, Group Sex, Masturbation  |  
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A Tall Chicken Story, and Three Orgasms

I once saw a friends father, put his cock in a chicken carcass, before putting it in the oven.
We both sat there dumbfounded, as he unzipped his trousers and took it out, went really serious, and masturbated until he had an erection, and then pushed it in the end and started having sex.
Moments earlier, his wife had called out to him, not to forget to 'Stuff the bird', and he looked at us sitting there, said, 'Right Girls, Watch', and did it.
He stared at both of us, as we watched him, our captivated attention on his penis drove him to 'Stuff it', longer than he intended, and gave him a rea... Continue»
Posted by MarieL 5 years ago  |  Categories: First Time, Group Sex, Taboo  |  
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First time with hubby and a stranger

My First Time With My Hubby And A Stranger
Hubby kept telling me how sexy it would be to watch me with another man, and how hot it got him. I could see, from the erection that was being subdued by his pants, that what he was telling me was true.

I told him that I would try it, if he agreed to set it up, and control the whold episode. He agreed that he would take care of everything.

Well, it was about 2 weeks before he brought up the subject again. He told me that he had been chatting on sls with a single guy, and that he was to come over to the house after dinner. I was a little upset... Continue»
Posted by gsb42 4 years ago  |  Categories: First Time, Masturbation, Mature  |  
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Cum on me part 2

As the day approached more men agreed to come along and participate. Some simply wanted to watch and wank on me, whereas others wanted to wank on me and fuck me.

I planned to have toys available for those who wanted to penetrate me but not with their cock, so I packed up dildos, butt plugs and vibrators for them to use as they wished.

I confirmed the time and place with my gangbangees and I turned up on the day about an hour before to see what he had sorted out for the venue. When I arrived there was a big bed in the middle of a room, allowing access from all around. He had laid on refr... Continue»
Posted by horny48 4 years ago  |  Categories: First Time, Group Sex, Voyeur  |  
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Her 1st Big Black Cock

My girlfriend is 27 short with curves in all the right places, a great ass with large breast that are made for attention, she has a sexual appetite that would give any man a run for their money. I'm in my early 40's 6 ft slim and have a respectable 7.5" cock that she loves to ride, we have been francizing about her trying another guy in a 3 way for quite some time and had been watching the local postings on CL and AFF.
I responded to a CL posting by a black male looking for woman to hang with and friends with benefits, he was 27 well-built and had a big 9.5" cock. He was interested and after... Continue»
Posted by wheels247 4 years ago  |  Categories: First Time, Interracial Sex  |  
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The Secretary(Merry Christmas)

It was Friday December 23, and the boss just dumped a pile of paper work on my desk to get done before our year-end in 8 days. I was hoping to take a few days off over the Christmas week,
but guess not now. As I sorted through the paper work some of it was insurance stuff. I just hate insurance paperwork, and I knew that asshole of an agent would be gone. Agent’s have the easiest jobs, they take time off, take your money, and cry about how hard they work. Well the only good thing about this agent was his secretary.

She was a doll, in her upper 40's with a hour glass figure, blonde hair, so... Continue»
Posted by PornApocalypse 3 years ago  |  Categories: First Time, Mature, Taboo  |  
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The Sleeepover – Chapter 6

The Sleeepover – Chapter 6

by samslam

"How did it go?" Alex asks when we walk in with my stuff.

"He agreed!" Lauren says, looking at Kristina who is grinning ear to ear.

"There are a few more boxes in the car," I announce. "I have to save my strength so you girls better get them," I laugh. The girls take the boxes into my bedroom and then gather in the living room anxious for the fun to begin.

"I found these in one of the boxes," Alex says, holding up a box of condoms. "I figured we'd need them."

"Before we do anything," Lauren takes charge as usual. "Brandon w... Continue»
Posted by TreborCox 1 month ago  |  Categories: First Time, Taboo  |  
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bbw babysitter pt 1

i remember when i was young i always fancied my babysitter chelle. She was 24 and i was 16 when i finally had my fantasy become real. This is my story of how i got to pop my cherry with the best woman ive ever had sex with.

chelle was a full figured woman, curves in all the right places though.A sweet girl that for the last 8 years had been my sitter whenever my parents were away. since that first time she came to sit ,i had played thinking of comming over her big milky breasts. But never thought i would get my wish, until one night when i had been moaning to my mum about being too old for ... Continue»
Posted by falconmaster 5 years ago  |  Categories: First Time  |  
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