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First Time Porn Stories

A First Time Out

First TimeShemales

I'd always fantasized about going out to a bar or a club, dressed as a woman, and after a few drinks managed to find the courage to do so. By the end of the bottle of wine I was dressed up and ready to go, suspenders, stockings, a corset on so tight it was hard to breathe underneath a loose, knee length skirt and close fitting top. My make up was done, a touch up of lipstick after the long black wig had been smoothed down and the last of the wine polished off. I'm always told I look gorgeous when I dress up, but I'd never been out before. Before it had just been for other people in private,… Read more

Posted by amylee-jones 3 years ago 1 1,954 91%

A Flatmate's First Time

AnalFirst TimeShemales

My name is John and it all started for me the same as most CDs; I was 13 and had stumbled upon my mother's underwear draw and for some reason I decided to try on my mum's pantyhose. The feeling was divine and I was immediately hooked. Over the next few days I experimented more and more with panties, bras, shoes, clothes and make-up. Ever since then I have had several unsuccessful attempts to quit my habits. I am now a 24 year old closet CD who lives in London with my flatmate Katy. She did not know about my dressing until that one wonderful afternoon. It was a Friday afternoon and as of the… Read more

Posted by amylee-jones 3 years ago 2,073 100%

her first time

First TimeGroup SexInterracial Sex

I was dating Dee a recently divorced 5 6 natural blond with new swimmers body. She had been married and got divorced when she found her husband had lost interest in her and was involved with someone else. She was angry and frustrated and very niece. she was 38 and had only had sex with her husband and one other man. She was ready to act out and try new things. She said her ex had never liked oral sex and had not had sex with her but 3 or 4 times in 15yrs. She was not pretty but had beautiful legs and was ready for anything. The first thing i did was take her home and stip her naked and… Read more

Posted by hotguy111111 3 years ago 3,519 100%

1st M2M Anal

First TimeGay Male

I have never been the receiver of m2m anal sex until this night. Since being in college, I have sucked, fingered and fucked men but never had it done to me. I have a gay friend (let’s call him Dave, even though it’s not his real name) I would play and hang out with regularly. Dave knew I was Bi and that I had a girlfriend. I went over his house one evening to hang out, watch TV and drink some wine. We sat together and had the wine, finishing the bottle. We started kissing pretty hot n heavy and soon he asked that we go to his bedroom. We get there and soon start making out hot n heavy again… Read more

Posted by windsurfer2 3 years ago 11 3,084 98%

1st GH suck

First TimeGay Male

When I was in college in the 90’s I use to go to an ABS by campus, first to buy some porn and then eventually to get my cock sucked whenever I got horny. I went into the store one night and purchased my coins and headed to the back for another quickie blow job. I went to a booth I knew had a GH and soon had a video playing and my cock out in my hand, hoping someone would enter the booth next door. I saw a light in the other booth through the GH in the wall and soon saw an open mouth with a tongue sticking out. I needed no urging or invitation and stuck my hard cock through like always and he… Read more

Posted by windsurfer2 3 years ago 21 2,802 100%

Linda and my mom

First TimeHardcoreTaboo

Linda and my mom I still remember the summer when I was three before twenty. Our next door neighbours had a daughter, who was several years younger than I. She was a noughty girl and I was fingering her pussy very often. She had never shown me her pussy, but she came over to my house every day. We used to play cards or do something similar to that. Then we pretended that we were cold and put a blanket over us. That gave us the possibility of putting one hand into each others trousers and feel what there was. She grabbed my cock and held the shaft tight. I had my hand in her panties… Read more

Posted by bullustampur 3 years ago 3 4,172 100%

Lesbian Paradise at Land's End

First TimeLesbian SexVoyeur

The sun was starting to set. Kea had been sitting there for a while gazing beyond the ocean line horizon. That huge rock, a couple of yards above the white-powdered sand, was like a throne from which you could see the whole beach. When she went to the travel agency some weeks ago, looking for a lonely place to reward herself with a two week holiday after finishing her grad studies, she never thought that there could be such an isolated paradise on Earth. They recommended this unknown place, a tiny fishing port far from anywhere, with a unique beach you could only reach after a half an hour… Read more

Posted by teira 3 years ago 4 1,526 100%

Sitting With the Sitter

AnalFirst TimeMasturbation

There have been a lot of things going on in my life and for once I now feel a bit relaxed. I just turned 60 and am retired but my wife still works so basically my days are all mine to do whatever I want. No more do I have the hustle and bustle of a daily routine. Some days I go swimming at 8 AM or 10 PM; go to a movie at 11 AM or 6 PM; whatever I want to do, when I want to do it. Hell some days I don’t get outta bed till almost noon. However, yesterday was a bit different. Our daughter and her f****y live about 5 minutes from us so whenever they need or want to borrow something or just ask… Read more

Posted by bigsoftee 3 years ago 9 5,717 90%

How my Ex loses her virginity Fantasy, part. 1

First TimeGroup SexHardcore

It was dusk, and the darkness was crawling through the woods rapidly with no hesitation. So swift did the darkness come, we were enveloped in its embrace within minutes. It was just the few of us, Laura, Steve, Bill, Mike, Dmitri, and I wondering through the woods at that point, lost and out of energy to think of a way out. I never knew how cold it could have gotten, with f***eful chills running down my spine. It was unbearable, and I can tell that the others were feeling the same cold sensation as I was. As we walked more towards god-knows-where, we decided that we would find a place to… Read more

Posted by HuggableCactus 3 years ago 1,565 100%

Rebecca's summer vacation (By: Jarvis80)

AnalFetishFirst Time

It's the Easter holiday, everyone is heading to Church in the morning to go to service and to get the Easter egg hunt ready for the k**s and have dinner as well. I sadly have to get dragged along since a friend recommend that I go since Easter is such an important day for Christians. I go to the church with him, I arrive in the parking lot next to his car, he's dressed very sharp but I can't stand it since its so annoying to wear suits and slacks. The women are dressed in long dresses and skirts, with ribbons and other things that are conservative and stupid in my opinion. "Can we get on w… Read more

Posted by bibiliz 3 years ago 1 3,603 100%

Aaa "Strawberry ice cream"

FetishFirst Time

This is my first of many stories to come, so don't be shy to leave comments of advice and I tneveryou in advance for reading my stories ;). I been waiting my whole life to let these stories out and now I finally get a chance.(All my stories would be true and just give me credit if you choose to repost.) Since this is my first story,I'll tell you about my first time eating her special strawberry ice cream;). I was under the age of 10 and my mom drop us off over a close friend of hers house while they go out to club and party. Shelly was the lady daughter who job it was to watch over us.Shel… Read more

Posted by stiffman305 3 years ago 1,148 100%

My first adventure

AnalFirst TimeGay Male

I joined the army after I quit school in the 12th grade. After joining the army it put a crimp in my dressing up as a girl. I did wear panties whenever I got the chance but I really wanted to dress up completely as a girl. I wanted to go out dressed and I have to admit I was attracted to several guys in my unit. My third year in the army I went to Viet Nam in December 1967. I was in the 101st Airborne. I had a best friend in my unit and we were friends since we were both assigned to the infantry unit. He didn’t know anything about my sweet secret. We had planned to go to Thailand for Rest & Re… Read more

Posted by pamalacd 3 years ago 3 3,621 100%

Step Mum ( True Story and needed to tell someone!!

First TimeMasturbationVoyeur

going to keep this short about what happened as id like to know your thoughts and comments. my step mum and me have always got along for years and often at parties and get togethers if tipsy we have flirted, nothing serious or heavy just comments to each other and once she pinched my bum and ive done the same to her all light hearted stuff. ive had a terrible couple of years and got invited to there place in spain, to cut a long story short I was over there for 2 weeks and my father ( a miserable man) and step mum was there for my first week but then went home, it rained on the Friday an… Read more

Posted by ddavid987 3 years ago 13 8,017 93%

Shocking f****y Tales and Dirty Sex

First TimeMatureTaboo

'Everybody get in', dad called out, and we made our way to the car. As bodies piled in, I stood behind my uncle, my head spinning, making me feel faint and dizzy. I felt his hand go around my thin waist to support me, then I was sitting in the back seat. I had d***k my first wine today, my sixteenth birthday, but it was the pill uncle had given me that made my head light and spin. The street lights had a mesmerizing effect on me as they sped past, and I lent forward and put my face onto my hands, resting on my knees. The car interior was dark and I could hear the radio and mum and dad c… Read more

Posted by MarieL 3 years ago 17 14,909 96%

Sibling Deal 02

FetishFirst TimeTaboo

sis and I are both over 18. She's my older s****r and is home from college for the summer. If you haven't read Chapter 1, you should. Now, I had to decide; we could continue with our deal and I'd wear her bra, and she'd go topless for me, or we could stop now and finish my boring summer. We don't get to real sex in this chapter, but it's not bad for a k** who's never done anything before. ------------------------------------------------ sis had taken me by surprise and shocked me. No one had ever touched me like this. But she didn't stop with touching. She handled me; played… Read more

Posted by drew1207 3 years ago 4 5,257 100%

Sibling Deal 01

FetishFirst TimeTaboo

Yep, everyone is over 18. I'm a senior in high school and the girl is a couple years older. She's several bra sizes larger than me too. You knew there had to be a girl involved. ----------------------------------------------- I just wanted to explain my side of things so no one would think I was a pervert or something. It's not like I'm into cross dressing or have gender issues. In a way, I guess I do have gender issues; I'm a guy and girls make me so fuckin' horny. That's really what got me into this mess. Leave it to sis to take advantage of me. Oh yeah, that's the other thing. It… Read more

Posted by drew1207 3 years ago 3,330 100%

The First time I sucked a dick.

First TimeGay MaleMasturbation

I was 25, Had been looking online for awhile, Before this I had only recieved head twice. One amazing time in high school from a lovely girl who later became a psycho... Well not really, but at the time I thought so. Then a second time when I was on a drive home from visiting f****y and drove past a roadside adult video store, I had been reading the Squirt pages about the place for awhile and knew they had booths and there were usually guys looking to give head in there, I was horny so I figured I'd give it a try, I had realized my bisexuality in college, but never came out, So I went into… Read more

Posted by biboy2442 3 years ago 2 3,959 100%

Sweet Teen part 2

First TimeHardcore

All my stories are based on my own experiences This is a continue story about Lou and the next time we met. Lou had just moved from high school and had started 6th form collage, after we had kinda had sex in the park, I wanted more than anything to get her alone so we could try again. A few weeks past and during this time we started seeing more of each other but never had the chance to try again, until today. Lou finished school early and my parents was out for the evening so I invited her round for a take away and we both knew what we really wanted. Lou was still in her unifor… Read more

Posted by dirtydisco99 3 years ago 3 1,121 100%

Russian Shemales 2: Electric Boogaloo

First TimeShemales

The next Friday, Serge and I take bus into the city again. He was very anxious to be there and to get pretty again. I am just anxious. Friday night is much like the previous Friday night. We move furniture, and build set, and then smoke cigarettes and drink vodka. Saturday is again the same: We are showered, and painted into pretty ladies. We take turns posing for camera in bras and panties and slips and stockings and high heels. We are both getting better at walking in heels. (If you search "Russian Shemales" in photo gallery of XHamster, you may see some of our photographs.) But… Read more

Posted by TransContinental 3 years ago 5 910 92%

ME GETTING PREGNANT BY ANOTHER BOY

AnalFirst Time

Hi, my name is Yogita, I originally hail from Mumbai. I have settled in Delhi after my marriage. I got married early at my age of 20. My husband is in automobile business along with his f****y members. Ours is a joint f****y. My marriage was a happier one as everybody would respect and care me well. But this didn’t continue for long. After few years I lost peace of mind. The reason was that I was unable to conceive. We carried many tests and done many medications, but nothing resolved. Even at the age of 25 years I was unable to have a c***d. The f****y was blami… Read more

Posted by yogita69 3 years ago 3 3,503 60%