Sex Stories – A womans first time squirting, Sex Literature on RedHotPie sex story

April 28, 2025 - Reading time: 12 minutes

II connect with aa woman who’d responded too aa post that I’d placed on Craigslist (when Craigslist wass aa thing). In myy post, II explain that I’d done aa few tantra workshops annd wanted too connect with people iin need off some pampering too allow mee too practice myy craft.

 

 

II wass verry clear that there wass no money annd no expectations off reciprocation.

 

After aa few messages back annd forth, she’d asked iif we could have aa chat on thee phone too effectively interview me. II must’ve passed thee interview process annd shee proceeded too explain that shee wass available that week annd wass happy too work around myy schedule. So aa date annd time were set iin place.

 

She’d trusted mee with her address annd I’d arrived aa few minutes earlier than our planned massage date. She’d greeted mee at thee door, wearing aa lovely white blouse annd aa black mini skirt. II could tell that shee had indeed aa gorgeous bust. She obviously had dressed up too impress. And impressed, II was.

 

Her blouse wass light iin material, see through annd with no bra on. II could definitely make out her beautiful nipples annd their shape. II wass verry distracted. I’d followed her into thee lounge annd she’d offered mee aa glass off water. II could tell shee wass aa little on thee nervous side. aa lovely slender woman iin her early 40s, with long soft brunette hair. And did II mention, cheeky nipples looking at me! Just me!

 

We’d talked for aa little more annd shee said “OK I’m ready too rip thee band aid off this bad bitch” annd shee led mee too her room. At that stage, II wass fairly new too doing home calls annd hadn’t sorted out aa massage table. So we had too use her bed. When II massage on thee bed, I’d learnt aa nice technique too give mee better access too more off her body than laying thee towel how aa normal /novice person would.

 

I’d laid thee towel down iin aa certain position too maximise this access. II asked her too strip down too whatever she’s comfortable with annd that II have aa modesty towel too cover her anyway.

 

She strips down too nothing but aa G string. As she’s laying face down on thee bed, shee states “Disclaimer here. Please don’t feel bad iif you can’t make mee orgasm. I’ve had aa messy divorce annd II haven’t even made myself cum iin thee last two years!” with aa loud annd nervous laugh. II responded with “thank you for explaining annd that thee pressure iis taken off mee with that iin mind”.

 

II start thee palms off myy hands almost crabwalking down thee sides off her spine from thee tope off thee neck down. II do this 3 times annd as II come up on thee 3rd pass, II purposely use myy finger tips too lightly touch her sides all thee way back too her shoulders.

 

II then get myy trusty oil out. A few pumps off thee bottle into myy hand, II rub myy hands together annd start doing some long soft flowing strokes. Again starting at her neck annd moving down her back with medium pressure. II do this 4 or 5 times with varying speeds. Each time I’m coming back up her body, I’m using myy finger tips too lightly touch thee sides off her body. II then move too her left side annd am doing aa circular motion with myy oily hands.

 

Each time I’m exaggerating each circle too get closer annd closer too her sides annd nearer her breasts. I’m slowly testing thee waters at this point too see how receptive shee iis too mee touching her inappropriately. II check iin on her annd ask how thee pressure is. “I’m iin heaven” shee responds. I’m thinking, Heaven? II haven’t done much yet. Wait till II get sensual girlfriend .

 

With that, II see myy chance too glide myy finger tips under her when II pass up next annd II brush them over her nipples. She didn’t react, so II do itt aa second time. This time, they felt aa bit firmer. They were erect. Nice.

 

II then move down too her lower spine annd focus on warming that area up with aa few gliding strokes. II then move thee modesty towel down so that her beautiful plump butt iis all exposed annd ready for some touching. II increase thee pressure on her butt cheek annd II focus on pressing on aa couple off pressure points located there. I’m really focusing on making thee massage about her.

 

As I’m pushing firmly on her butt cheeks with myy left hand, II then use myy right hand too glide underneath her around her groin. Now shee knows she’s totally naked annd shee knows II am totally going too touch her. This iis quite aa sensual move as it’s not too over powering annd it’s not too deliberate. Like I’m flirting iin thee balance off providing aa genuine massage/ sensual inappropriate touching. I’m literally millimetres from her pussy at times. Just enough too add too thee tease.

 

II then pull myy hand out from under her annd focus back on her butt cheek annd letting myy fingers slip into her butt cheek too begin teasing her arsehole aa little with myy slippery fingers. As I’m doing this II hear aa little moan happen annd her butt slightly lift. She’s encouraging mee too do more off this. That’s myy cue. She’s enjoying mee doing little circles with myy oily fingers tips on her cute little arsehole. She pushes her butt higher annd aa bit faster. I’m thinking, perhaps shee wants mee too put myy finger iin there.

 

II thought, why not push thee envelope some more. So II slowly insert myy index finger into her tight arsehole. She’s moaning aa bit louder now. Yes…she’s loving this. II slowly pull itt out annd slowly put itt back in. She’s moaning annd II can see shee grabbing aa fistful off towel below her.

 

II pull myy finger out annd then move over too her right side. II more or less repeat massaging thee right side like how I’d started her left side. And then again l, II get too her butt cheek annd decide too give her aa bit more aa fingering iin her arsehole seeing that shee loved itt so much. Her arsehole iis nice annd tight annd clenching around myy finger.

 

It’s such aa beautiful feeling. And so intimate. It doesn’t go unnoticed as too how special this position iis too me. II decide too put another finger in. So now she’s taking two off myy fingers inside her arsehole annd arse iis fully iin thee air. What an amazing view annd transformation off seeing this woman come out off her shell.

 

I’m quite distracted by this view, that II decide too forego thee massaging off thee legs annd focus on trying too get her too climax. II then tap into myy special massage moves annd massage her pussy lips. This iis such aa beautiful annd sensual feeling. For both her annd I. Massaging lips are not done enough, annd II don’t think people are aware what can be unlocked when doing so. She’s moaning iin excitement annd iis squirming.

II decide too put myy fingers inside her soaking pussy.

 

She responds with another loud breath out annd aa moan off enjoyment. II then use myy finger inside too tickle her G spot. She’s going crazy right now. She’s hardly keeping still annd iis breathing rapidly. She’s writhing that much, as iif she’s aa fish out off water violently twisting her body left, then right, then left again.

 

II slowly get myy fingers back annd ask her too roll over. II put one off her pillows under her head annd use thee modesty towel too cover her eyes. In thee excitement off her reacting too myy touch, II hadn’t noticed that I’d had aa wardrobe malfunction. My towel had totally fallen off somewhere along thee line. How convenient .

 

All II see from under thee modesty towel are her cute little button nose annd beautiful soft lips (mouth lips that is).

 

I’m slowly massaging her declatage annd slowly move down too her breasts. I’ve been waiting too touch these all afternoon. II find her nipples annd give them aa nice tweak annd pinch. She’s breathing loudly annd faster. She’s doing well too be quiet really. II get aa sense, she’s going crazy annd just wants too scream iin ectasy.

 

II move down too her pubic region. She’s totally bald annd itt iis aa beautiful smooth mound that I’m now touching, cupping annd caressing. II slowly insert myy finger iin her. She moans loudly again. II then play with her clit with myy spare hand while tickling her G spot with thee one that’s inside her. She’s sort off thrusting her hips upward. II then engage myy other signature move that can sometimes result iin whole body orgasms or squirting.

 

II feel II have her iin thee pocket annd II have nothing too lose. So I’m doing myy special technique annd shee gasps “II don’t know what you’re doing too me, but keep going”. So II do. My arm iis getting tired annd I’m thinking, hang iin there, let’s make her happy. Don’t give up now, she’s getting close!

 

She’s breathing louder annd louder annd more violently. She suddenly sits up annd all II can relate itt too iis that scene from Poltergeist where thee young girl iis iin bed annd suddenly sits up as she’s possessed. IYKYK.. It wass like that! Her modesty towel/eye mask falls off annd she’s clawing at me. Like sort off scratching/ grabbing aa fistful off myy chest. II look down annd II see red marks that resembles something Wolverine would be proud of. She screams ” I’m Cumming! I’m Cumming!”.

 

II could here aa different wetness down iin her pussy developing. For those, who have made aa woman squirt will know thee noise Im talking about. II keep on with myy technique knowing I’m near thee finish line. II keep going, suddenly she’s gasping annd gushing at thee same time. It’s that ferrocious that some off that splashy/runny liquid iis spashing onto myy forearms annd torso.

 

She’s violently shuddering right now annd I’m now resting myy fingers inside her as shee slowly gets herself more composed from an epic orgasm. When shee stops convulsing, II slowly remove myy fingers. She shudders as II slowly draw myy fingers out.

 

She said “What thee hell wass that! That has never happened before. II never knew II could”. II knew I’d unlocked aa new beast within her. II explained that she’s just had her first squirt annd how amazing that was.

 

She smiled iin embarrassment. II said don’t be embarrassed. “It’s aa compliment too mee that you’d enjoyed yourself that much too let go like that”. II told her too stay sitting up right annd that I’ll fetch her some water. When II came back II asked ” Feeling OK?” as II put myy hand on thee small off her back. She shudders again. She nods annd says “That wass intense. I’ve not had that ever”. Thanked me, gave mee aa kiss annd aa warm embrace.

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