A woman's first time squirting

I connect with a woman who'd responded to a post that I'd placed on Craigslist (when Craigslist was a thing). In my post, I explain that I'd done a few tantra workshops and wanted to connect with people in need of some pampering to allow me to practice my craft.

I was very clear that there was no money and no expectations of reciprocation.

After a few messages back and forth, she'd asked if we could have a chat on the phone to effectively interview me. I must've passed the interview process and she proceeded to explain that she was available that week and was happy to work around my schedule. So a date and time were set in place.

She'd trusted me with her address and I'd arrived a few minutes earlier than our planned massage date. She'd greeted me at the door, wearing a lovely white blouse and a black mini skirt. I could tell that she had indeed a gorgeous bust. She obviously had dressed up to impress. And impressed, I was.

Her blouse was light in material, see through and with no bra on. I could definitely make out her beautiful nipples and their shape. I was very distracted. I'd followed her into the lounge and she'd offered me a glass of water. I could tell she was a little on the nervous side. a lovely slender woman in her early 40s, with long soft brunette hair. And did I mention, cheeky nipples looking at me! Just me!

We'd talked for a little more and she said "OK I'm ready to rip the band aid off this bad bitch" and she led me to her room. At that stage, I was fairly new to doing home calls and hadn't sorted out a massage table. So we had to use her bed. When I massage on the bed, I'd learnt a nice technique to give me better access to more of her body than laying the towel how a normal /novice person would.

I'd laid the towel down in a certain position to maximise this access. I asked her to strip down to whatever she's comfortable with and that I have a modesty towel to cover her anyway.

She strips down to nothing but a G string. As she's laying face down on the bed, she states "Disclaimer here. Please don't feel bad if you can't make me orgasm. I've had a messy divorce and I haven't even made myself cum in the last two years!" with a loud and nervous laugh. I responded with "thank you for explaining and that the pressure is taken off me with that in mind".

I start the palms of my hands almost crabwalking down the sides of her spine from the tope of the neck down. I do this 3 times and as I come up on the 3rd pass, I purposely use my finger tips to lightly touch her sides all the way back to her shoulders.

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

Each time I'm exaggerating each circle to get closer and closer to her sides and nearer her breasts. I'm slowly testing the waters at this point to see how receptive she is to me touching her inappropriately. I check in on her and ask how the pressure is. "I'm in heaven" she responds. I'm thinking, Heaven? I haven't done much yet. Wait till I get sensual girlfriend 😈.

With that, I see my chance to glide my finger tips under her when I pass up next and I brush them over her nipples. She didn't react, so I do it a second time. This time, they felt a bit firmer. They were erect. Nice.

I then move down to her lower spine and focus on warming that area up with a few gliding strokes. I then move the modesty towel down so that her beautiful plump butt is all exposed and ready for some touching. I increase the pressure on her butt cheek and I focus on pressing on a couple of pressure points located there. I'm really focusing on making the massage about her.

As I'm pushing firmly on her butt cheeks with my left hand, I then use my right hand to glide underneath her around her groin. Now she knows she's totally naked and she knows I am totally going to touch her. This is quite a sensual move as it's not too over powering and it's not too deliberate. Like I'm flirting in the balance of providing a genuine massage/ sensual inappropriate touching. I'm literally millimetres from her pussy at times. Just enough to add to the tease.

I then pull my hand out from under her and focus back on her butt cheek and letting my fingers slip into her butt cheek to begin teasing her arsehole a little with my slippery fingers. As I'm doing this I hear a little moan happen and her butt slightly lift. She's encouraging me to do more of this. That's my cue. She's enjoying me doing little circles with my oily fingers tips on her cute little arsehole. She pushes her butt higher and a bit faster. I'm thinking, perhaps she wants me to put my finger in there.

I thought, why not push the envelope some more. So I slowly insert my index finger into her tight arsehole. She's moaning a bit louder now. Yes...she's loving this. I slowly pull it out and slowly put it back in. She's moaning and I can see she grabbing a fistful of towel below her.

I pull my finger out and then move over to her right side. I more or less repeat massaging the right side like how I'd started her left side. And then again l, I get to her butt cheek and decide to give her a bit more a fingering in her arsehole seeing that she loved it so much. Her arsehole is nice and tight and clenching around my finger.

It's such a beautiful feeling. And so intimate. It doesn't go unnoticed as to how special this position is to me. I decide to put another finger in. So now she's taking two of my fingers inside her arsehole and arse is fully in the air. What an amazing view and transformation of seeing this woman come out of her shell.

I'm quite distracted by this view, that I decide to forego the massaging of the legs and focus on trying to get her to climax. I then tap into my special massage moves and massage her pussy lips. This is such a beautiful and sensual feeling. For both her and I. Massaging lips are not done enough, and I don't think people are aware what can be unlocked when doing so. She's moaning in excitement and is squirming.

I decide to put my fingers inside her soaking pussy.

She responds with another loud breath out and a moan of enjoyment. I then use my finger inside to tickle her G spot. She's going crazy right now. She's hardly keeping still and is breathing rapidly. She's writhing that much, as if she's a fish out of water violently twisting her body left, then right, then left again.

I slowly get my fingers back and ask her to roll over. I put one of her pillows under her head and use the modesty towel to cover her eyes. In the excitement of her reacting to my touch, I hadn't noticed that I'd had a wardrobe malfunction. My towel had totally fallen off somewhere along the line. How convenient 😅.

All I see from under the modesty towel are her cute little button nose and beautiful soft lips (mouth lips that is).

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

I move down to her pubic region. She's totally bald and it is a beautiful smooth mound that I'm now touching, cupping and caressing. I slowly insert my finger in her. She moans loudly again. I then play with her clit with my spare hand while tickling her G spot with the one that's inside her. She's sort of thrusting her hips upward. I then engage my other signature move that can sometimes result in whole body orgasms or squirting.

I feel I have her in the pocket and I have nothing to lose. So I'm doing my special technique and she gasps "I don't know what you're doing to me, but keep going". So I do. My arm is getting tired and I'm thinking, hang in there, let's make her happy. Don't give up now, she's getting close!

She's breathing louder and louder and more violently. She suddenly sits up and all I can relate it to is that scene from Poltergeist where the young girl is in bed and suddenly sits up as she's possessed. IYKYK.. It was like that! Her modesty towel/eye mask falls off and she's clawing at me. Like sort of scratching/ grabbing a fistful of my chest. I look down and I see red marks that resembles something Wolverine would be proud of. She screams " I'm Cumming! I'm Cumming!".

I could here a different wetness down in her pussy developing. For those, who have made a woman squirt will know the noise Im talking about. I keep on with my technique knowing I'm near the finish line. I keep going, suddenly she's gasping and gushing at the same time. It's that ferrocious that some of that splashy/runny liquid is spashing onto my forearms and torso.

She's violently shuddering right now and I'm now resting my fingers inside her as she slowly gets herself more composed from an epic orgasm. When she stops convulsing, I slowly remove my fingers. She shudders as I slowly draw my fingers out.

She said "What the hell was that! That has never happened before. I never knew I could". I knew I'd unlocked a new beast within her. I explained that she's just had her first squirt and how amazing that was.

She smiled in embarrassment. I said don't be embarrassed. "It's a compliment to me that you'd enjoyed yourself that much to let go like that". I told her to stay sitting up right and that I'll fetch her some water. When I came back I asked " Feeling OK?" as I put my hand on the small of her back. She shudders again. She nods and says "That was intense. I've not had that ever". Thanked me, gave me a kiss and a warm embrace.