#Try Not To Get Caught Challenge🤭

#Try Not To Get Caught Challenge🤭

#Try not to get caught challenge🤭

More Posts from Jessica-roberts88 and Others

3 years ago

Friday night

I’ve just got home from work. Looking forward to a weekend to get femmed up and relax. (I don’t get the chance to do this much during the week as I’m not really “out”). I walk in the door and do a shot of whiskey and grab a bottle of beer out of the fridge.

I start a shower and hop in. Scrubbing myself down getting nice and lathered and shave everything, including my face, which I don’t actually do during the week as I have to present more masc for my job.

Standing there. Hairless and silky smooth. I sip my beer while rubbing my smooth fresh thighs together, I’m so happy I get to enjoy a few more days of this before going back to my other life…

I scroll through tumblr and Grindr and interracial porn scenes on the internet getting myself all worked up. Cleaning my ass for a good workout later this evening occasionally using one of my smaller dildos just for a little foreplay. I don’t want to start so early before I have the time to really dress up and get myself outrageously horny and in the mindset.

I run out of hot water so I get out and dressed, slip on a thong and leggings. I start to put on a bra and my friend calls interrupting my moment of femininity.

Fortunately it’s Valerie, she’s been my best friend for years and also happens to be a lesbian… well… mostly. We have hooked up on occasion since I’m not like “other guys” in bed. Another perk is she knows I like bottoming, although she really isn’t in on the loop of how far I take it as far as dressing and shaving. And how I just LOVE the idea of being a girl.

I tell her to come over so I take off all but the thong and put on my masc clothes.

She gets here and we sit at my bar, talking about life , her girlfriend problems, my opinions on the matter, 90’s alternative music(both of our favorite genres), and of course drinking. I’m mostly drinking whiskey and beer and I keep making her moscow mules.

A few hours later were both pretty buzzed and in classic Valerie fashion our talks end up turning fairly sexual. I really wasent trying to fuck her since I wanted to cum like a girl all weekend and not lose that pent up urge to just get absolutely fucked.

I need to figure out a work around for this.

I run to my room real quick and grab my lovense lush and bring it down. I hand it to her and say let’s try this out. She’s hesitant but puts it in, not sure what to expect. I put it on slow just to get her warmed up and she’s really really enjoying it. I start to increase the power and she starts gripping the bar counter and the stool trying to compose herself. She absolutely loves it.

I also realize that this was probably a terrible idea since shes just getting more worked up and I’m going to have to finish what I started.

“I’m heading to your room… are you coming?” She asks rhetorically

I head up and start to eat her out after a quick make out session.

“You’re always the best at this… oh my god”

“Mmhmm, I love it…” I mumble with my face between her thighs and tongue on her clit

She tells me to get up, she wants to ride me.

At this moment I actually mildly panic since in the heat of all this I actually forgot I was still wearing my girly panties. Also at the same time it hits me she knows a lot about what I’m into. I’m all in. Fully committed now! Let’s go, if anyone is going to know it’s going to be her!

“Hold on one second” I say In a hurry as I reach under my bed for my “toy box”.

“Why don’t we try something a little different… fuck me with one of these… you pick”

“Ok… Uhmmm wow…. This went somewhere totally unexpected…” she shockingly said to me looking at the box and back at me and back to the box.

I looked down at the box as well and my heart jumped into my throat. I left EVERYTHING in that box. Not just my dildos and the harness…My breast forms. Sexy lingerie…everything!

She bites her lip and looks up at me Grabs one of my doc Johnson 8” realistic dildos. “This one” she says excitedly and hands it to me. “You know I’ve kind of always wanted to do this ever since you told me about it” she continued. “And I’ve always wanted you to as well, Val.. I kinda figured You’d be good at it” I replied grinning ear to ear.

She puts on the harness and I’m so aroused right now seeing her kneeling on the bed, her girl cock hanging between her thick thighs.

“Hold on a second.” I tell her as I grab the vibrator she used earlier. “ Here. Use this, I don’t want to be selfish!”

She eagerly puts the lush back in and I put it on a pattern that gradually builds up as time goes on.

She moves over and pushes me down on the bed and pulls my pants down exposing my girly thong. “Hmm. You know what, we’re going to make this even more interesting”. She grabs my breast forms and orders me to put them on. I’m super excited and super terrified about this simultaneously but I follow her orders.

“You’d make such a good girlfriend…. I think I’ll call you Jessica for the rest of the evening”

I’m so lost in the moment I can’t even come up with a response to that. Here I am in front of my best friend in a bra with breasts, totally shaved and girly panties while she’s lubing up her girl cock…

She’s standing on the edge of the bed and reaches up and grabs my ankles dragging me to her She grabs my legs and lifts them onto her shoulders and started to work her new found cock to my asshole. Slowly at first only about half way in. She puts my legs down and I wrap them around her waist as she leans over and kisses me. “Are you going to cum for me, Jessica?” I’m speechless. I just shake my head yes as she picks up the pace and slams the whole thing into my. She’s Gripping my breasts and starts fucking me faster and and harder. I can slightly feel her vibrator through the dildo. She’s panting and thrusting to the pattern. The waves of pleasure are rushing through my body and seeing this gorgeous girl fucking me as a girl while my boobs are bouncing to her pounding are so much it sends me over the edge and I cum all over myself. Grunting. Moaning. She isn’t stopping and keeps thrusting as I continue to shoot my cum all over my stomach. She slows her pace for a moment and we catch our breath. She reaches forward and scoops up my cum and brings her fingers to my mouth. “Be a good girl Jessica….” She says as she pushes her cum soaked fingers into my lips and in my mouth. “You better swallow it all” she says to me as she pins my legs back and starts to thrust with all her force into me. It’s such a shock I just swallow my whole load right there. She leans over ontop of me still pinning my legs back and she starts panting frantically and switches from full thrusts to grinding in me. She continues with a long drawn out high pitch moan as she stops. Still inside of me Apparently that vibrator and the harness on her clit sent her over the edge too. She lets go of my legs and leans over me and says in my ear “Oh yeah, You’re definitely my new girlfriend…. Jessica…”


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10 months ago
Did We Just Find The Loch Ness Monster On Tumblr?!?

Did we just find the Loch Ness monster on tumblr?!?

London mutuals what is there to do that’s cheap and not alcohol based?

2 years ago

I freaking love this!

I love the idea of free use, but not with strangers

With friends

To have a group of male best friends who I genuinely love and see as pals

We hang out normally all the time

But if one of them gets a little horny

Or if they need to take their anger out

They come into my house unannounced and fuck me senseless

We have cute video game and pizza dates as a friend group, but they slip something into my drink, and I wake up to them acting casual as if nothing happened and a dull ache between my legs

They always let me hit the blunt as much as i want because they know when I get high I basically become a sex servant

I want to be sat on the couch with all of them and one of them announces that he’s taking me to another room to fuck me, and no one bats an eye

They’re protective over me like brothers because my pussy belongs to them

I send them pictures of every outfit I wear incase one of them wants to use me in it

I want to be one of the guys, but also their personal fleshlight


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3 years ago
Digital Bath Is Quite Possibly The Most Erotic Song Ever. Not Only Do The Vocals Present Themselves In

Digital bath is quite possibly the most erotic song ever. Not only do the vocals present themselves in a very sexual way but the way the song is composed literally builds and explodes like the best orgasm you’ve ever had

You move like I want to

To see like your eyes do

We are downstairs

Where no one can see

New life break away

Tonight

I feel like more

Tonight I

You make the water warm

You taste foreign

And I know you can see

The cord break away

'Cause tonight

I feel like more

Tonight

I feel like more

Feel like more

Tonight

You breathed

Then you stopped

I breathed

then dried you off

And tonight

I feel, feel like more

Tonight I feel like

Feel like more

Tonight I feel like more

Feel like more

1 year ago

I’m sure nobody is gonna see this because 99% of my followers are bots ….

But you need to listen to some “shadow boxer” by Fiona apple. Suuucch a fuckin song

Fiona Apple

Fiona Apple


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1 year ago

89. Have you ever been penetrated by more than one person at the same time?

I have not…. But I’ve always wanted to try.


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jessica-roberts88 - Jessica Roberts
Jessica Roberts

35years old. NB, assigned male at birth but really exploring my fem side Considering fully transitioning.

146 posts

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