Mila Houston First Anal
Mila Houston First Anal

It’s not uncommon for a girl to have never done anal before, most of the chicks that show up on My Very First Time are in that category…and of course that includes this chick Mila Houston! She’s got that big round sexy delectable ass and I’m sure guys all over have been dreaming about fucking […]

Aspen Reign First Lesbian Experience
Aspen Reign First Lesbian Experience

Believe it or not this is the first time beautiful brunette Aspen Reign has gotten into a lesbian experience, and man she’s doing it right in this My Very First Time update as she gets into bed with stunning blonde spinner Naomi Woods! The two make out and Aspen explores her friend’s body, kissing her […]

Brooke Myers First Black Cock
Brooke Myers First Black Cock

There are all kinds of firsts here on My Very First Time…some women have never been fucked anally before, some have never done a shoot at all, and then there are women like Brooke Myers here who have never fucked a big black cock either in their personal life or ‘at work’ so to speak! […]

Debbie Clark First Anal
Debbie Clark First Anal

We’ve got yet another red hot pornstar ready to take her first steps into the world of anal pleasure here on My Very First Time, namely the lovely Debbie Clark! She’s always been nervous about taking a cock in her ass because she was afraid of the pain of it, but now she’s ready to […]

Sophia Grace First Anal
Sophia Grace First Anal

She might be a professional pornstar now but beautiful Sophia Grace has somehow never tried anal sex…but now’s her chance! She’s here on My Very First Time and is ready to pop that anal cherry, slipping off her sexy little panties and taking this guy’s big thick dick in her mouth and pussy and ass […]

Alice March First Anal
Alice March First Anal

Cute little spinner Alice March was always afraid to take a cock in the ass because of the discomfort of it, but here on My Very First Time it’s the place to drop the inhibitions and push that envelope am I right! Alice is ready to try anal sex but she has to get warmed […]

Brooke Logan First Anal
Brooke Logan First Anal

In a shocking development, we’ve got here a red hot pornstar who is ready to try anal sex for the first time! Haha that’s right, like lots of women beautiful blonde Brooke Logan has never taken a cock up the keister before but in this My Very First Time update she’s ready to get the […]

Destiny Love First Anal
Destiny Love First Anal

For cute pornstar Destiny Love, anal sex was always something she avoided because she doesn’t particularly like pain and was always nervous about the discomfort that comes along with getting fucked in the ass! In this My Very First Time update she decided to finally give it a whirl, getting her tight little ass fingered […]

Leigh Rose First Anal
Leigh Rose First Anal

Buckle up because we’ve got another sexy girl ready to try anal sex for the very first time! Stunning redhead Leigh Rose has always been afraid to do any insertions or anything else like that “back there” as she puts it because of the idea that it’ll hurt, so she’s avoided anal sex up until […]

Olivia Lee First Anal
Olivia Lee First Anal

She had always been a little afraid of the discomfort involved in anal sex so beautiful Olivia Lee had never gotten fucked in that tight back door of hers…until today! In the update from My Very First Time Olivia holds on for dear life with her sexy round juicy ass in the air, getting fingered […]

Gia Love First Anal
Gia Love First Anal

This girl Gia Love has been a pornstar for a few different sites now but one thing she’s never done is take a cock up her ass, and in this My Very First Time update she’s about to take care of that! She’s always been afraid of the pain of anal sex but works her […]

Alex Mae First Anal
Alex Mae First Anal

There have been quite a few girls on My Very First Time who were exploring anal pleasure for the first time but I don’t know if any of them are as cute and tight and tiny as Alex Mae in this hot update! She’s a gorgeous spinner with small boobies, a tight little pussy and […]

Alaina Kristar First Anal
Alaina Kristar First Anal

It’s a pretty common thing for women (even pornstars) to have never tried anal sex before…some people consider it ‘dirty’, but I think the pain is the thing most people are scared of. Well a site like My Very First Time is the perfect place to take your first steps into a new world of […]

Trisha Parks First Anal
Trisha Parks First Anal

Like most of the women who show up on My Very First Time, sexy little Trisha Parks here has never taken a dick in her ass before but all that is about to change! She’s ready to try anal sex for the first time and we’re invited along for the ride, so enjoy as this […]

Jessie Law First Time
Jessie Law First Time

Usually when a girl goes on My Very First Time she’s already a pornstar in the industry but is branching out to push her envelope a bit and try out something she’s never done before, like anal sex or a gangbang or what have you. In this update though we have fresh faced hottie Jessie […]

Sierra Nevadah First Anal
Sierra Nevadah First Anal

When you’re a tight cute little spinner like Sierra Nevadah here I can understand why you’d be a little hesitant about getting into anal, I mean if it’s painful for a full-figured model it must be excruciating for a tight little horndog with a skinny petite body, right? Well thanks to My Very First Time […]

Rachel James First Gangbang
Rachel James First Gangbang

It’s hot as hell seeing these horny beautiful babes enter new territory here on My Very First Time, pushing out of their comfort zones and bringing us along for the ride! Check out sexy blonde Rachel James in this red hot scene called My Very First Gang Bang, and I’m pretty sure you can guess […]

Asha Marie First Anal
Asha Marie First Anal

There have been a few girls on My Very First Time already who decided to jump into the world of anal for the first time, but I would have to say that this chick Asha Marie enjoyed it the most! Asha had never taken an anal pounding but was down to try…she slid a toy […]

Mia Monroe Very First Anal
Mia Monroe Very First Anal

This site My Very First Time hasn’t been around long but already I get the feeling that for a lot of the girls who get on the site, the first experience they choose to have on there is gonna be anal! This is I think the fourth update already with a chick having her very […]

Jade Jantzen First Double Penetration
Jade Jantzen First Double Penetration

We’ve seen a few different themes so to speak here on My Very First Time as these hot and horny girls explore untrodden territory, some were fantasizing about gangbangs and some about just doing a porn shoot for the first time, but this girl Jade Jantzen is going above and beyond in this update called […]

Leigh Rose First Anal
Leigh Rose First Anal

This site My Very First Time is still pretty new but already they’ve had a few girls whose first time experience is trying anal! I guess it’s a pretty common thing for a girl to have not tried, it’s seen as super naughty and kind of painful and Leigh Rose here was pretty nervous about […]

Maddy Rose First Gangbang
Maddy Rose First Gangbang

You may have seen sexy blonde spinner on a few other porn sites in her short career so far but one thing she has never tried is a gang bang! She always wanted to but was a little nervous about venturing into that territory, so this new site My Very First Time is the perfect […]

Kimberly Costa First Anal
Kimberly Costa First Anal

We get to see all kinds of first time experiences here on My Very First Time and unsurprisingly, one thing that some of these women have never tried is anal! Kimberly Costa here had only ever had her mouth and pussy fucked, she’d never been introduced to the pleasures of the backdoor bang either because […]

Kendra Khaleesi First Porn Video
Kendra Khaleesi First Porn Video

Here on My Very First Time we generally see girls in the industry breaking into new territory and making a fantasy cum true, but this time we’ve got total newbie Kendra Khaleesi in an update called My Very First Porn Scene! That’s right, this chick has never done a hardcore porn shoot before but now […]

Milly Austin First Interracial Sex
Milly Austin First Interracial Sex

On this site My Very First Time we get to see beautiful women who may have had a secret desire for years but never got up the gumption to bring it to life…Milly Austin for instance always had a thing for black guys but never took one to her bed, and now in this update […]

Ashley Adams First Anal
Ashley Adams First Anal

Welcome to My Very First Time, where some of the hottest sexiest girls on the net are having first-time experiences, and it’s all caught in high resolution video for us to enjoy…this time around it’s beautiful brunette Ashley Adams, who is enjoying her very first anal here. Ashley has only experienced penetration with that sweet […]