Shy GF Turns into Slut Pt. 01

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Shy GF shared for first time turns wild once started...
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Part 1 of the 5 part series

Updated 06/08/2023
Created 04/21/2017
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shyone121
shyone121
24 Followers

Before we get started, let me describe my girlfriend Jess.

She is a tall slim and young brunette girl, with perky little breasts and, for her size, she has a great thick butt too.

Otherwise she is very shy, only having been with 1 partner before me and quite naive too, especially in the bedroom. She always seems very surprised when she watches porn in front of me and also tells me that she has no fantasies outside of vanilla sex, so I have to be the one to try and spice things up, but am always careful not to be so strange as to put her off.

The fact she hasn't had sex with another gives me great security in knowing that she doesn't know what she's missing so she won't look elsewhere for satisfaction.

Jess fell for me because I am very athletic and she likes a guy with slim build (as she tells me often). She always tells me that she loves my size and hates men with big muscles and that also makes me feel a lot better.

I also have some sexual problems in the fact that my dick is quite small and I always ejaculate way too fast which has always bothered me, but Jess always reassures me saying she thinks my dick is perfect size and I last long enough for her to enjoy herself.

Anyway, for as long as I can remember I have had some irregular fantasy relating to imagining my girlfriend having sex with other guys. Of course I have always been quiet about it because I'm certain that my girlfriends will find it really strange, but, because it never goes away, I decided with Jess to finally put a plan together to introduce it into our sex life, mostly for my sake to live out my horny fantasies.

It started very light with getting Jess into the habit of looking at porn videos with me of other couples and eventually introducing a dildo into the bedroom for some role play, all of this work being introduced at particular times when she'd had some alcohol in her system.

Jess doesn't drink often at all, but when she does she changes into a different person, turning into a confident, talkative, playful and often horny individual when we get home after a night on the town. Some of the best sex I've ever had is when we are both really drunk and just let our inhibitions go, and she is completely accepting of anything I bring into the bedroom at these points, as long as it's just role play.

After slowly bringing her out of her shell, I finally found the best hint that Jess' mind was starting to wander, which got me insanely excited at the thought of.

One weekend, we were getting ready to go for a drink with some friends and she left her phone on the sofa while she went up to take a shower, which I immediately used as an opportunity to be curious about her browsing history.

As it turned out, a few days before (the evening that I was out of town working), she had been watching some porn! And not just any old porn, she was searching for things among 'cheating', 'black cock' and 'threesome'.

This was a revelation! My cock got instantly hard at the simple thought of it. But I wondered whether I should bring it up or not. Seeing as I was beginning to feel drunk from preparing for the night out, I thought the best idea would be to mention it.

She finally finished showering and came downstairs giggling and wearing some modest clothes: jeans and a shirt.

In my slightly tipsy state, I had a plan that would be the ultimate finale to my new findings, but it was risky to mention. I didn't care, my cock was pulsing from the thought of it and I approached her with a scheme in mind.

"You look beautiful Jess," I said as I stepped over to her and grabbed her butt from round her waist.

She giggled, "Thanks, I'm glad you like it."

She had also been drinking and I could see her starting to get into her carefree mode.

I joked, "But how can anyone get quick access to your panties when you're wearing jeans? Where's that tight little skirt I bought for you?"

"It's in the bedroom ready for you tonight."

"But I want to see it now," I demanded, "go and squeeze into it."

"OK, but we haven't got much time before the taxi arrives!"

Jess ran upstairs and came back down a minute later wearing a tight small black skirt that made her ass look even bigger than in jeans, in fact you could nearly see her pants peeping out of the bottom.

"Maybe you should just go out wearing that, you'd get a lot of attention in the club."

I saw her hesitate for a minute at the thought of what that entailed, before laughing it off and saying "You know I couldn't do that."

She looked at herself in the mirror and turned to admire her round backside.

"Come here Jess. Sit on my knee, I have something to tell you."

I beckoned her over, sat her on my lap and kissed her on the lips.

I then crept my hand up her skirt so I could feel her soft lace pants, and realised she seemed to be a little wet.

I then began to tell her everything as a whisper in her ear whilst I moved my fingers around beneath her skirt, trying my best to get her in a sexual mood.

I whisper softly, "I think you're starting to get a bit wet thinking of wearing your sexy little skirt to the club. And I also think that you are excited at the thought of the attention it'll bring to you.

"Feel my cock. Do you know why I'm so hard? I know what you've been looking at. I know you want to seduce other men. Is that true? Because that's precisely why I need you to wear that skirt out."

As I was talking, she didn't say a word, she just breathed deeply as her hole got wetter and wetter.

Finally she spoke back "Yes. Yes. I want some attention. I wanted to wear the skirt in the first place but was scared that you'd think I was a slut."

"Well I do think you're a slut for wearing it. and that is exactly what I want. Let's play a game tonight. Here's your one chance to fulfil your fantasy.

"If you successfully attract the attention of a guy at the club and he flirts with you, you have permission to flirt back. Not only that, but if you can convince him, we can go to a hotel tonight, all 3 of us, and have some additional fun together. How about that?"

She thought I was testing her. "No I couldn't possibly do that, I am faithful and you know that."

"I'm really very serious," I said as I used her hand to show her just how rock hard I was inside my trousers.

Suddenly we heard a taxi pap its horn outside the door and shot up to leave. On the way out, Jess took one last look in the mirror, quickly pulled her skirt up and gave her booty a quick squeeze to reinforce the size, all whilst completely ignoring me.

Was this going to be the night?

shyone121
shyone121
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