u/50_CaliBear

This roleplay is about two best friends, a Male and a bottom TransFem or Futa, and how they end up fucking rough and raw right behind everyone's backs.

It's no secret how big of a part I played throughout your adult life. I was one of the first to befriend you in college, and stuck by your side since then, through thick and thin. Celebrating the highs of your life with you, and saving you during your lows. I've seen every other friendship you had flourish or fall. Along with pretty much every relationship you had. We were pretty much inseparable.

But one thing always bugged you... It always felt a little one sided, that I helped you and improved your life, more than you did mine, without asking for anything in return. It seemed that you couldn't express the true extent of your appreciation for me.

And that's when it clicks. There is certainly something you could offer, to a perpetually single man with an unfortunate luck in ladies and a lot of pent up frustrations... Let's just hope no one finds out about it, including your current partner ;)

Any further details can be discussed in private.

This may include themes and kinks such as Casual Sex, Cheating and Sneaky Sex, Facefucking and Deepthroat, Rough Sex, Deep Creampies, Rimming, Cock and Ball Worship, Breast Play, Public/Outdoor Play, Condom Play, possibly Romance and potentially much more.

This roleplay is about two best friends, a Male and a bottom TransFem or Futa, and how they end up fucking rough and raw right behind everyone's backs.

It's no secret how big of a part I played throughout your adult life. I was one of the first to befriend you in college, and stuck by your side since then, through thick and thin. Celebrating the highs of your life with you, and saving you during your lows. I've seen every other friendship you had flourish or fall. Along with pretty much every relationship you had. We were pretty much inseparable.

But one thing always bugged you... It always felt a little one sided, that I helped you and improved your life, more than you did mine, without asking for anything in return. It seemed that you couldn't express the true extent of your appreciation for me.

And that's when it clicks. There is certainly something you could offer, to a perpetually single man with an unfortunate luck in ladies and a lot of pent up frustrations... Let's just hope no one finds out about it, including your current partner ;)

Any further details can be discussed in private, here or on Discord.

This may include themes and kinks such as Casual Sex, Cheating and Sneaky Sex, Facefucking and Deepthroat, Rough Sex, Deep Creampies, Rimming, Cock and Ball Worship, Breast Play, Public/Outdoor Play, Condom Play, possibly Romance and potentially much more.

I am 18+ and all participants and characters must be 18+

This roleplay is about two best friends, a Male and a Futa, and how they end up fucking rough and raw right behind everyone's backs.

It's no secret how big of a part I played throughout your adult life. I was one of the first to befriend you in college, and stuck by your side since then, through thick and thin. Celebrating the highs of your life with you, and saving you during your lows. I've seen every other friendship you had flourish or fall. Along with pretty much every relationship you had. We were pretty much inseparable.

But one thing always bugged you... It always felt a little one sided, that I helped you and improved your life, more than you did mine, without asking for anything in return. It seemed that you couldn't express the true extent of your appreciation for me.

And that's when it clicks. There is certainly something you could offer, to a perpetually single man with an unfortunate luck in ladies and a lot of pent up frustrations... Let's just hope no one finds out about it, including your current partner ;)

Any further details can be discussed in private.

This may include themes and kinks such as Casual Sex, Cheating and Sneaky Sex, Facefucking and Deepthroat, Rough Sex, Deep Creampies, Rimming, Cock and Ball Worship, Breast Play, Public/Outdoor Play, Condom Play, possibly Romance and potentially much more.

This roleplay is about two best friends, a Male and and a bottom TransFemale, Futa, or Hermaphrodite, and how they end up fucking rough and raw right behind everyone's backs.

It's no secret how big of a part I played throughout your adult life. I was one of the first to befriend you in college, and stuck by your side since then, through thick and thin. Celebrating the highs of your life with you, and saving you during your lows. I've seen every other friendship you had flourish or fall. Along with pretty much every relationship you had. We were pretty much inseparable.

But one thing always bugged you... It always felt a little one sided, that I helped you and improved your life, more than you did mine. It seemed that you couldn't express the true extent of your appreciation for me.

And that's when it clicks. There is certainly something you could offer, to a perpetually single man with an unfortunate luck in ladies and a lot of pent up frustrations... Let's just hope no one finds out about it, including your current partner ;)

Any further details can be discussed in private.

This will includes themes and kinks such as Casual Sex, Cheating and Sneaky Sex, Facefucking and Deepthroat, Rough Sex, Deep Creampies, Rimming, Cock and Ball Worship, Breast Play, Public, Condom Play, possibly Romance and potentially much more.

This roleplay is about two best friends, a Male and Female/TransFemale/Futa/Hermaphrodite, and how they end up fucking rough and raw right behind everyone's backs.

It's no secret how big of a part I played throughout your adult life. I was one of the first to befriend you in college, and stuck by your side since then, through thick and thin. Celebrating the highs of your life with you, and saving you during your lows. I've seen every other friendship you had flourish or fall. Along with pretty much every relationship you had. We were pretty much inseparable.

But one thing always bugged you... It always felt a little one sided, that I helped you and improved your life, more than you did mine. It seemed that you couldn't express the true extent of your appreciation for me.

And that's when it clicks. There is certainly something you could offer, to a perpetually single man with an unfortunate luck in ladies and a lot of pent up frustrations... Let's just hope no one finds out about it, including your current partner ;)

Any further details can be discussed in private.

This will includes themes and kinks such as Casual Sex, Cheating and Sneaky Sex, Facefucking and Deepthroat, Rough Sex, Deep Creampies, Rimming, Cock and Ball Worship, Breast Play, Public, Condom Play, possibly Romance and potentially much more.

This roleplay is about two best friends, a Male and Female/TransFemale/Futa/Hermaphrodite, and how they end up fucking rough and raw right behind everyone's backs.

It's no secret how big of a part I played throughout your adult life. I was one of the first to befriend you in college, and stuck by your side since then, through thick and thin. Celebrating the highs of your life with you, and saving you during your lows. I've seen every other friendship you had flourish or fall. Along with pretty much every relationship you had. We were pretty much inseparable.

But one thing always bugged you... It always felt a little one sided, that I helped you and improved your life, more than you did mine. It seemed that you couldn't express the true extent of your appreciation for me.

And that's when it clicks. There is certainly something you could offer, to a perpetually single man with an unfortunate luck in ladies and a lot of pent up frustrations... Let's just hope no one finds out about it, including your current partner ;)

Any further details can be discussed in private.

This will includes themes and kinks such as Casual Sex, Cheating and Sneaky Sex, Facefucking and Deepthroat, Rough Sex, Deep Creampies, Rimming, Cock and Ball Worship, Breast Play, Public, Condom Play, possibly Romance and potentially much more.

I am 18+ and all participants and characters must be 18+

This roleplay is about two best friends, a Male and Female/TransFemale/Futa/Hermaphrodite, and how they end up fucking rough and raw right behind everyone's backs.

It's no secret how big of a part I played throughout your adult life. I was one of the first to befriend you in college, and stuck by your side since then, through thick and thin. Celebrating the highs of your life with you, and saving you during your lows. I've seen every other friendship you had flourish or fall. Along with pretty much every relationship you had. We were pretty much inseparable.

But one thing always bugged you... It always felt a little one sided, that I helped you and improved your life, more than you did mine. It seemed that you couldn't express the true extent of your appreciation for me.

And that's when it clicks. There is certainly something you could offer, to a perpetually single man with an unfortunate luck in ladies and a lot of pent up frustrations... Let's just hope no one finds out about it, including your current partner ;)

Any further details can be discussed in private.

This will includes themes and kinks such as Casual Sex, Cheating and Sneaky Sex, Facefucking and Deepthroat, Rough Sex, Deep Creampies, Rimming, Cock and Ball Worship, Breast Play, Public, Condom Play, pissibly Romance and potentially much more

Kik: 50.CaliBear

I am 18+ and all participants and characters should be 18+

This roleplay is about two best friends, a Male and Female/TransFemale/Futa/Hermaphrodite, and how they end up fucking rough and raw right behind everyone's backs.

It's no secret how big of a part I played throughout your adult life. I was one of the first to befriend you in college, and stuck by your side since then, through thick and thin. Celebrating the highs of your life with you, and saving you during your lows. I've seen every other friendship you had flourish or fall. Along with pretty much every relationship you had. We were pretty much inseparable.

But one thing always bugged you... It always felt a little one sided, that I helped you and improved your life, more than you did mine. It seemed that you couldn't express the true extent of your appreciation for me.

And that's when it clicks. There is certainly something you could offer, to a perpetually single man with an unfortunate luck in ladies and a lot of pent up frustrations... Let's just hope no one finds out about it, including your current partner ;)

Any further details can be discussed in private.

This will includes themes and kinks such as Casual Sex, Cheating and Sneaky Sex, Facefucking and Deepthroat, Rough Sex, Deep Creampies, Rimming, Cock and Ball Worship, Breast Play, Public, Condom Play, pissibly Romance and potentially much more

Kik: 50.CaliBear

I am 18+ and all participants and characters should be 18+

This is a roleplay between a young man and an OLDER WOMAN OR MILF

Serious requests only. Open to suggestions when it comes to ideas, but here's the premise:

Ever wanted to introduce a young man into the world of adult pleasures and fun? Take his first kiss, and his virginity away, and make him your intimate fuckbuddy behind closed doors, or open doors if you're into public play. The dynamic may remain just that, or bloom into a fully fledged relationship affair behind your partner's back, whether it be a boyfriend, girlfriend, husband or wife ;)

I may have a few ideas for your character's role relative to mine: Mom's friend. Friend's Mom. Sister's friend. Friend's sister. Neighbour. University Student. Teacher/Professor. Boss/Manager/CEO. Older friend. Celebrity (Actress, Singer, Streamer, Influencer)

Or alternatively, bring your own! Along with a ref!

This can include themes such as Light Femdom, Cock Shock, Cock and Ball Worship, Rimming, Rough Sex, Riding, Breeding, Anal, Size Difference, Legal AgeGap, Public Play, Cheating, Condom Play/Removal, and potentially more!

Hope to build something wonderful together soon.

Kik: 50.CaliBear

I am 18+ and all participants and characters must be 18+

This is a roleplay between a young man and an OLDER WOMAN OR MILF

Serious requests only. Open to suggestions when it comes to ideas, but here's the premise:

Ever wanted to introduce a young man into the world of adult pleasures and fun? Take his first kiss, and his virginity away, and make him your intimate fuckbuddy behind closed doors, or open doors if you're into public play. The dynamic may remain just that, or bloom into a fully fledged relationship affair behind your partner's back, whether it be a boyfriend, girlfriend, husband or wife ;)

I may have a few ideas for your character's role relative to mine: Mom's friend. Friend's Mom. Sister's friend. Friend's sister. Neighbour. University Student. Teacher/Professor. Boss/Manager/CEO. Older friend. Celebrity (Actress, Singer, Streamer, Influencer)

Or alternatively, bring your own! Along with a ref!

This can include themes such as Light Femdom, Cock Shock, Cock and Ball Worship, Rimming, Rough Sex, Riding, Breeding, Anal, Size Difference, Legal AgeGap, Public Play, Cheating, Condom Play/Removal, and potentially more!

Hope to build something wonderful together soon.

Kik: 50.CaliBear

I am 18+ and all participants and characters must be 18+

This is a roleplay between a young man and an OLDER WOMAN OR MILF

Preferably long-term, and literate. Serious requests only. Open to suggestions when it comes to ideas, but here's the premise:

Ever wanted to introduce a young man into the world of adult pleasures and fun? Take his first kiss, and his virginity away, and make him your intimate fuckbuddy behind closed doors, or open doors if you're into public play. The dynamic may remain just that, or bloom into a fully fledged relationship affair behind your partner's back, whether it be a boyfriend, girlfriend, husband or wife ;)

I may have a few ideas for your character's role relative to mine: Mom's friend. Friend's Mom. Sister's friend. Friend's sister. Neighbour. University Student. Teacher/Professor. Boss/Manager/CEO. Online friend. Celebrity (Actress, Singer, Streamer, Influencer)

Or alternatively, bring your own! Along with a ref!

This can include themes such as Light Femdom, Cock Shock, Cock and Ball Worship, Rimming, Rough Sex, Riding, Breeding, Anal, Size Difference, Legal AgeGap, Public Play, Cheating, Condom Play/Removal, and potentially more!

Hope to build something wonderful together soon.

Kik: 50.CaliBear

I am 18+ and all participants and characters should be 18+

This is a roleplay between a young man and an OLDER WOMAN OR MILF

Preferably long-term, and literate. Serious requests only. Open to suggestions when it comes to ideas, but here's the premise:

Ever wanted to introduce a young man into the world of adult pleasures and fun? Take his first kiss, and his virginity away, and make him your intimate fuckbuddy behind closed doors, or open doors if you're into public play. The dynamic may remain just that, or bloom into a fully fledged relationship affair behind your partner's back, whether it be a boyfriend, girlfriend, husband or wife ;)

I may have a few ideas for your character's role relative to mine: Mom's friend. Friend's Mom. Sister's friend. Friend's sister. Neighbour. University Student. Teacher/Professor. Boss/Manager/CEO. Online friend. Celebrity (Actress, Singer, Streamer, Influencer)

Or alternatively, bring your own! Along with a ref!

This can include themes such as Light Femdom, Cock Shock, Cock and Ball Worship, Rimming, Rough Sex, Riding, Breeding, Anal, Size Difference, Legal AgeGap, Public Play, Cheating, Condom Play/Removal, and potentially more!

Hope to build something wonderful together soon.

Kik: 50.CaliBear

I am 18+ and all participants and characters must be 18+

This is a roleplay between a young man and an OLDER WOMAN OR MILF

Preferably long-term, and literate. Serious requests only. Open to suggestions when it comes to ideas, but here's the premise:

Ever wanted to introduce a young man into the world of adult pleasures and fun? Take his first kiss, and his virginity away, and make him your intimate fuckbuddy behind closed doors, or open doors if you're into public play. The dynamic may remain just that, or bloom into a fully fledged relationship affair behind your partner's back, whether it be a boyfriend, girlfriend, husband or wife ;)

I may have a few ideas for your character's role relative to mine: Mom's friend. Friend's Mom. Sister's friend. Friend's sister. Neighbour. University Student. Teacher/Professor. Boss/Manager/CEO. Online friend. Celebrity (Actress, Singer, Streamer, Influencer)

Or alternatively, bring your own! Along with a ref!

This can include themes such as Light Femdom, Cock Shock, Cock and Ball Worship, Rimming, Rough Sex, Riding, Breeding, Anal, Size Difference, Legal AgeGap, Public Play, Cheating, Condom Play/Removal, and potentially more!

Hope to build something wonderful together soon.

I am 18+ and all participants and characters must be 18+

This is a roleplay between a youthful man and an OLDER WOMAN OR MILF

Preferably long-term, and literate. Serious requests only. Open to suggestions when it comes to ideas, but here's the premise:

Ever wanted to introduce a youthful man into the world of adult pleasures and fun? Take his first kiss, and his virginity away, and make him your intimate fuckbuddy behind closed doors, or open doors if you're into public play. The dynamic may remain just that, or bloom into a fully fledged relationship affair behind your partner's back, whether it be a boyfriend, girrlfriend, husband or wife ;)

I may have a few ideas for your character's role relative to mine: Mom's friend. Friend's Mom. Sister's friend. Friend's sister. Neighbour. University Student. Teacher/Professor. Boss/Manager/CEO. Online friend. Celebrity (Actress, Singer, Streamer, Influencer)

Or alternatively, bring your own! Along with a ref!

This can include themes such as Light Femdom, Cock Shock, Cock and Ball Worship, Rimming, Rough Sex, Riding, Breeding, Anal, Size Difference, Legal AgeGap, Public Play, Cheating, Condom Play/Removal, and potentially more!

Hope to build something wonderful together soon.

This is a roleplay between a young man and an OLDER WOMAN OR MILF

Preferably long-term, and literate. Serious requests only. Open to suggestions when it comes to ideas, but here's the premise:

Ever wanted to introduce a young man into the world of adult pleasures and fun? Take his first kiss, and his virginity away, and make him your intimate fuckbuddy behind closed doors, or open doors if you're into public play. The dynamic may remain just that, or bloom into a fully fledged relationship affair behind your partner's back, whether it be a boyfriend, girlfriend, husband or wife ;)

I may have a few ideas for your character's role relative to mine: Mom's friend. Friend's Mom. Sister's friend. Friend's sister. Neighbour. University Student. Teacher/Professor. Boss/Manager/CEO. Online friend. Celebrity (Actress, Singer, Streamer, Influencer)

Or alternatively, bring your own! Along with a ref!

This can include themes such as Light Femdom, Cock Shock, Cock and Ball Worship, Rimming, Rough Sex, Riding, Breeding, Anal, Size Difference, Legal AgeGap, Public Play, Cheating, Condom Play/Removal, and potentially more!

Hope to build something wonderful together soon.

I am 18+ and all pariticpants and characters should be 18+

This is a roleplay between a young man and an OLDER WOMAN OR MILF

Preferably long-term, and literate. Serious requests only. Open to suggestions when it comes to ideas, but here's the premise:

Ever wanted to introduce a young man into the world of adult pleasures and fun? Take his first kiss, and his virginity away, and make him your intimate fuckbuddy behind closed doors, or open doors if you're into public play. The dynamic may remain just that, or bloom into a fully fledged relationship affair behind your partner's back, whether it be a boyfriend, girlfriend, husband or wife ;)

I may have a few ideas for your character's role relative to mine: Mom's friend. Friend's Mom. Sister's friend. Friend's sister. Neighbour. University Student. Teacher/Professor. Boss/Manager/CEO. Online friend. Celebrity (Actress, Singer, Streamer, Influencer)

Or alternatively, bring your own!

This can include themes such as Light Femdom, Cock Shock, Cock and Ball Worship, Rimming, Rough Sex, Riding, Breeding, Anal, Size Difference, Legal AgeGap, Public Play, Cheating, Condom Play/Removal, and potentially more!

Hope to build something wonderful together soon.

Kik: 50.CaliBear

I am 18+ and all pariticpants and characters should be 18+

This is a roleplay between a young man and an OLDER WOMAN OR MILF

Preferably long-term, and literate. Serious requests only. Open to suggestions when it comes to ideas, but here's the premise:

Ever wanted to introduce a young man into the world of adult pleasures and fun? Take his first kiss, and his virginity away, and make him your intimate fuckbuddy behind closed doors, or open doors if you're into public play. The dynamic may remain just that, or bloom into a fully fledged relationship affair behind your partner's back, whether it be a boyfriend, girlfriend, husband or wife ;)

I may have a few ideas for your character's role relative to mine: Mom's friend. Friend's Mom. Sister's friend. Friend's sister. Neighbour. University Student. Teacher/Professor. Boss/Manager/CEO. Online friend. Celebrity (Actress, Singer, Streamer, Influencer)

Or alternatively, bring your own!

This can include themes such as Light Femdom, Cock Shock, Cock and Ball Worship, Rimming, Rough Sex, Riding, Breeding, Anal, Size Difference, Legal AgeGap, Public Play, Cheating, Condom Play/Removal, and potentially more!

Hope to build something wonderful together soon.

Kik: 50.CaliBear

I am 18+ and all participants and characters are 18+

This is a roleplay between a young man and an OLDER WOMAN OR MILF

Preferably long-term, and literate. Serious requests only. Open to suggestions when it comes to ideas, but here's the premise:

Ever wanted to introduce a young man into the world of adult pleasures and fun? Take his first kiss, and his virginity away, and make him your intimate fuckbuddy behind closed doors, or open doors if you're into public play. The dynamic may remain just that, or bloom into a fully fledged relationship affair behind your partner's back, whether it be a boyfriend, girlfriend, husband or wife ;)

I may have a few ideas for your character's role relative to mine: Mom's friend. Friend's Mom. Sister's friend. Friend's sister. Neighbour. University Student. Teacher/Professor. Boss/Manager/CEO. Online friend. Celebrity (Actress, Singer, Streamer, Influencer)

Or alternatively, bring your own!

This can include themes such as Light Femdom, Cock Shock, Cock and Ball Worship, Rimming, Rough Sex, Riding, Breeding, Anal, Size Difference, Legal Age Gap, Public Play, Cheating, Condom Play/Removal, and potentially more!

Hope to build something wonderful together soon.

I am 18+ and all participants and characters must be 18+

This is a roleplay between a youthful man and an OLDER FRIEND OR MILF

Preferably long-term, and literate. Serious requests only. Open to suggestions when it comes to ideas, but here's the premise:

Ever wanted to introduce a youthful man into the world of adult pleasures and fun? Take his first kiss, and his virginity away, and make him your intimate fuckbuddy behind closed doors, or open doors if you're into public play.

I may have a few ideas for your character's role relative to mine: Mom's friend. Friend's Mom. Sister's friend. Friend's sister. Neighbour. Teacher/Professor. Boss/Manager/CEO. Online friend. Celebrity (Actress, Singer, Streamer, Influencer)

Or alternatively, bring your own!

This can include themes such as Light Femdom, Cock Shock, Cock and Ball Worship, Rimming, Rough Sex, Riding, Breeding, Anal, Size Difference, Legal Age Gap, Public Play, Cheating, Condom Play/Removal, and potentially more!

Hope to build something wonderful together soon.

I am 18+ and all participants and characters must be 18+