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Meghan's diary - Part 3

Jamie introduces Meghan to the world of self pleasure. Enjoy!
A month has passed since that crazy experience with Jamie. Nothing ofthose sorts has happened since then but Jamie used every opportunity to remind me of it. I swear she was flirting with me and teasing me all the time now. Therefore, I'm sure you guys want to know what happened the past month. Well, I worked on my make-up skills, grew my hair out, bought new clothes and even got some sex toys. I was extremely shy about using them however as I never had anything besides my fingers in my ass.

It was Friday and Jamie and I just finished work so we decided to go grab something to eat. We weren't in the mood for anything fancy so we just went to McDonald's. We soon got into our usual conversations about and work and this led to sex. Fitting, as we work in an adult shop. I showed Jamie the toys I bought and this sparked something in her, I could tell.

"Wow sweetie these are great you have great taste. I'd love to use them with you," Jamie said with an excited tone in her voice.

"Hmm...I don’t know about that..." I blushed and looked down. I was really nervous since I never used them before.

"What's the matter honey? Is anything wrong?"

"No it's nothing...I just...I just never used any toys before. I never had anything in my ass that’s bigger than my fingers." I stuttered.

"Well I did finger your ass last time and you seemed to love that. What about that guy you met? Didn't you want him to fuck you?" Jamie inquired.

"Of course I did have fingers in my ass but that's all. Please let's not talk about that guy, okay? ..." A tear rolled down my cheek and I had to be careful not to cry. I was still hurt and got sad every time I thought about this guy. Jamie just leaned over to hug me, which I must admit felt great. I felt her breasts on top of me so I got a bit horny. I squeezed my thighs together but that only made it worse.

"Meg, let's meet at my place later and I will show you how to use these toys, how does that sound? We go home, get out of our work uniforms and slip into something sexy and then we meet at my place at around 6 pm."

I got really excited now and of course agreed to meet her. Back at my place I took a shower, shaved everywhere, which didn't take long since I don't have a strong hair growth on my body and applied lotion all over. I ran my hands over my body and shivered I felt great I could only imagine how I'd feel when Jamie touched me. Next step was deciding on an outfit but it wasn't tough this time. I just had to wear my tight black dress I bought recently and was dying to wear.

I put on my black stockings with the bow on top, a black thong and purple bra, the same underwear I wore for my date. I then put on my five-inch ankle strap heels and applied my make-up. One last look in the mirror and I was stunning. I recently got into a habit of only looking in the mirror once I was completely done. That way I only allowed myself to see the final product. I appeared more and more feminine every time and seriously considering hormones but I don't think I'm ready for that yet.

Right on time I arrived at Jamie's place and when she opened the door for me, I was amazed. There she was wearing white thigh high boots, a pink leather miniskirt that barely covered her ass and a tight white top with no bra underneath as I could see her nipples poking through.

"Wow Jamie you look great." That was all I could get out. In all the years I knew her as a guy, I never saw her dressed this sexy even for her boyfriends. I immediately noticed my panties getting super wet as pre-cum oozed out of my clit (as I called my dick whenever I was all dressed up).

We quickly went upstairs into her room and settled down on her king-sized bed. I remembered sitting here with her a lot back in the day. Back then, we were just talking and watching TV but this time it would be a lot different. We spread out my toys across the bed I had a purple five inch vibrator, a medium-sized butt plug and a very realistic looking seven inch dildo with a suction cup. Jamie took every toy one by one and explained the affect it is supposed to have and the numerous ways you can use it. She did this in such a professional way you could tell she earns her money this way. We started out with the vibrator. Out of pure instinct and excitement, I took off my panties and yanked up my dress.

“There you go girl I love how you get going right away,” Jamie purred and stared at me seductively.

She slid over to me on all fours and reached down to suck me. I got super excited, as even though we fooled around together before I can’t recall her ever giving me a proper blowjob. Jamie stopped however and only kissed the tip. Instead of sucking me, she went lower and started licking my ass.

“You didn’t think I was going to suck your dick, did you? Oh no a pretty girl like you gets her pussy licked.”

Jamie grabbed the vibrator now and turned it on teasing my ass with it. She circled it around my hole, which I must admit felt amazing. I leaned back, bit my lip and moaned quietly. I pulled my dress up higher and reached underneath my bra to pinch my nipples.

“Mhmm that’s my girl baby keep going I can tell you love it.”

In one swift motion, Jamie pushed the vibrator deep in my ass and turned the vibration to the maximum. I screamed as if I got shot and came instantly. Rope after rope of sticky cum shot out of my clit and onto my stomach. I was shocked at the sight of this. Never before did I cum without touching myself and this was one of my most intense orgasms ever. This moment made me feel like I truly was a real girl that squirted from playing with her pussy.

Jamie got on top of me to lick off the puddle of cum I left all over me. She kissed me passionately sharing my load with me. The second time I ever tasted cum and I absolutely loved it. Sweet but salty at the same time I felt so naughty having all of this in my mouth, even though it was only my own.

“I’m so proud of you baby! You mastered your first step with expertise. The way you just came was amazing just like a real girl! Now are you ready for the next step?” Jamie asked me and kept kissing me passionately.

I was surprised what she meant with the next step but it wouldn’t take long for me to find out. She reached for the drawer and pulled out a bottle of lube. Lovingly Jamie rubbed it all over my now not so tight ass. She pressed in one and then two fingers to lube my ass from inside. The lube was cold but the sensation of Jamie’s fingers in my ass sent a warm and tingling sensation through my body.

After what felt like forever, she seemed satisfied and reached over to grab the butt plug. This allowed me a perfect look at her ass. I can’t even describe it it’s just perfectly heart shaped and so tight. Jamie pushed the butt plug in gently but determined until it was in all the way. I was breathing really hard and it wasn’t easy to get it in all the way but once it was inside I felt like it was going to rip my ass apart. I never felt something this intense it was a strange mixture of pleasure and pain but I knew I didn’t want it to stop.

I was lying on my back for a while, took my dress off and just played with myself. I caressed my body, stroked my clit, pinched my nipples and sat down to feel the plug press against my prostate. I felt like a complete girl at this moment no doubt or any manly thoughts at all. I just enjoyed filling my hole with everything I have and being used as Jamie’s little play toy.

Speaking of Jamie when I looked back at her, she was naked except for her stockings and heels. Inside her dripping pussy, my own dildo was buried deep. She must have gotten horny from all the action and had to satisfy herself. The movement of her hips mesmerized me when she switched between riding the dildo and fucking it doggy-style. Without even noticing, I was stroking my clit, which was hard as a diamond. It seemed like I had an internal conflict one moment I felt like a complete girl but now my manly side was aching to take over. All I could think about was fucking Jamie. That thought came from deep inside and I didn’t have such thoughts for a long time.

Back when I lived as a boy I always had a crush on Jamie, in fact, I was jealous of her boyfriend’s getting to fuck her. Ever since I began living as Meghan and working with her in the store, these thoughts were all gone, she was simply my best friend who I loved like a sister.

I was acting on autopilot now I got up and went over to Jamie putting my cock in her mouth while she backed into the dildo. I was fucking her mouth like a maniac all eight inches of my big hard throbbing cock disappearing completely in her mouth. Muffled moans escaped her mouth, her eyes tearing and spit running out of her mouth. I kept my cock there until she was choking then pulled out again. It was shining bright from her saliva now as it was dangling there in front of her face until she caught her breath again.

“Damn Meg what has gotten into you?” Jamie exhaustedly said.

“Do you want me to stop?” I asked, hoping the answer would be no.

“Don’t you dare to stop I love being dominated like this. Reach under my pillow there will be a key that opens the chest in my night drawer. Open it and use on me what’s inside.”

Quickly I did as told and what I found had me intrigued. I found a ball gag that she apparently wanted me to use on her. I was fully aware she wouldn’t be able to suck me like this so the next logical step would be fucking her tight ass and pussy. Jamie slid down off the dildo and laid down for me, her ass arched up high, her legs spread and her upper body buried into a pillow. I reached around applying the ball gag making sure it was tight but not uncomfortable. I slowly slid my eight inches inside of her dripping pussy and slammed in hard. Until now I never realized how blessed I was. I only had sex with a woman once or twice but I had the perfect sized cock for this job. Jamie was screaming even through the gag and I slapped her ass a couple of times.

“Quiet you little slut. You are my bitch now deal with it!” I yelled at her trying to act dominant.

I don’t know what had gotten into me I was still Meghan but acted like a stud fucking his girl. I was seriously the best of both worlds right now. I was pounding her pussy for what felt like hours occasionally switching between her pussy and ass until both were wide open. After about thirty minutes of hard fucking, I came deep inside her making both of us scream out loud.

Exhausted we fell down on the bed and lay down next to each other staying in each other’s arms. I removed Jamie’s gag and we both took a shower after which we went to sleep out of pure exhaustion.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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