Greg Became Jen and Dom Had His Way

After reading some of my stories Greg was eager to meet for a firsthand experience.

As Greg or Jenny, neither had experienced any sexual encounters and I had helped Greg explore various scenarios explaining the benefits of being a top or bottom, if their was no preference, although I did like the thought of meeting Greg as Jenny. I could imagine her cock stuffed in to the front of her panties just the thin material of her skirt away made me hard just thinking about it.

I had always been a bottom, mainly because Mac had never really shown any sign of being submissive and, in all fairness to him, I really like feeling of being objectified by Mac and he did have a good size cock, in every respect.

I met Greg from the station and started to flirt as soon as he got off the train and i lost myself in his eyes. Greg's eyes were a bright bottle green, surrounded by a darker halo and his smile could have enticed any guy or girl. His build was slight and his dress sense really suited him, even more so when he walked in front and I could get a good look at his cute pert butt.

'I'm going to fucking destroy that' I thought to himself, in my mind I'd already undressed him to his frilly panties and a pair of sports socks'

So, Greg came as Greg but that was ok, this was our first meet and maybe Greg was new to identifying as he/she and who knows, he could have slipped himself in to some nice tight panties as he was aware of my underwear preferences.

Making small talk he came across to be a really nice guy with an idea of how he wanted his first experience to be, the kind of perfect first-time vision although he did make it clear he was open minded and was eager to have his first encounter with someone that knew what they wanted. Having always been the bottom, I'd only ever fucked women and been fucked by men so knew I wanted a role reversal.

Greg admitted he had got so aroused by the story that documented mine and Mac's encounter in the old quarry that he sat reading the rest while he wanked himself off, trying to time it so he came at the same time as when I came, imagining it was him that was being fucked.

The arrangement to meet at the station was by design, the quarry was about a 20-minute walk from where we had met and we were only about 10 minutes away.

'I hope you don't mind, Greg, we're on our way to the quarry' I explained, 'I figured that if you were as nervous as me there would be no better time and telling your before hand would only make you more nervous'

'I was nervous on the train but they've settled since we've been walking and talking' He said.

Greg was an illustrator and although his style wasn't to my taste this encounter would give him an insight of the thoughts and feelings that I encounter when Mac fucks me.

My cock isn't as big as Mac's but then Greg's hole might not be accustomed to anal as much as mine so it would be a gentle breaking in for him.

'I was hoping we wouldn't waste any time' Greg replied, with an element of excitement in his voice.

'We never did finish our conversation about underwear preferences, did we?' He said, I've been exploring that as well'

'Oh, have you now. You've got a cute pert arse, I bet it looks fantastic in a pair of fancy frilly panties' I said, 'You've made me so fucking hard'

Greg glanced down at my groin and thought I hadn't noticed.

'He's trying to size me up' I thought, 'I really want to fuck him, as we mad eye contact'

We were still a few minutes away from the secret seclusion of the quarry and I was finding it so hard to contain myself.

'You do realise, I'm going to waste no time once we're in the quarry, I stated 'You make me so fucking horny'

Mac was Scottish and his rustic appearance suited his role in our friendship and I like the fact there was a rare animalistic nature to him. Our sex was just him fucking me with his own satisfaction in mind, there was no underlying intent for it to be anything more than what it was, I liked being rough fucked with no holds barred.

Greg on the other hand was definitely a bottom and from what i could see from his mannerisms and body language was trying to hide his femininity by being overly alpha, I saw right through it but played along.

'We're here' I said, as I guided him through the hole in the fence, having a quick look around before joining him.

'We won't be disturbed?' He asked.

'No' I promptly replied, 'I've been coming here for the past 3 or 4 years, it's only ever been me every time'

'Did you want to re-enact when Mac followed me, like in my story?' I asked.

He paused before replying.

'Sure' he said, 'I can remember how this part goes'

'And you're ok with it?' I asked, waiting for his acknowledgement.

'Yes, I'm ok with it' He replied with a dirty smile that was almost a reflection of my own.

After showing him where we left our belongings and also where our secluded oasis was his eyes lit up when he saw the fallen tree.

'It was here' he said, 'You held on to it here as Mac fucked you'

'Oh, wow' I thought, Greg was really picturing the scene. His dirty smile was glued to his face as he walked around the space, looking from all angles and I encouraged his vision by bending over holding on to the trunk.

'Yes, yes' He said, 'Oh hmmm'

I made my way back out of the alcove of dense bushes and trees. Greg seemed to be off in his own little fantasy as he drifted past me to where we had arranged to get undressed and store our gear.

'I'll follow your queue' I said. 'When I see you walk down the path I'll follow behind.' 'You're still ok with this?'

'Oh, ye, definitely'

His prompt reply was more than what I needed and we both disappeared for a few minutes.

I was wearing a pair of white and black over the knee socks combined with a heavy black Lycra 6 strap suspender belt that worked perfect with the socks, the straps fully extended so they would reach the tops of the socks. The wide elastic straps stretched tight across my arse cheeks at the back and the feel of them rubbing as I walked made my cock dribble precum almost instantly as it started to seep through the front. I pulled the front of my panties down to rearrange myself.

My cock was rock hard and throbbing so hard my helmet had turned a deep crimson as the light bounced off it.

Keeping an eye out for Greg's movement, a few minutes had passed until I saw a slim pale figure making its way down the path that led to the secluded space, our rendezvous point.

My heart stepped up its pace, the figure was slowly walking down the path as I stepped out of the treeline as I closely followed.

I could see his body was completely hairless and pale, the contrasting black Lycra French knickers where tight and had ridden up his arse and were extenuating the pert roundness of his butt. He had also donned a white camisole top that met the white and pink suspender belt, the straps where flailing with nothing to clip on to. His white socks finished just under the knee and the little pink ribbon bows were cute and suited the whole ensemble. He had even changed his shoes to some bright red Converse with pink glittery laces, an outfit I was jealous of but knew I could never pull off.

His pace slowed to a holt as he stood shifting his body weight from one leg then the other, he knew what he was doing, he was such a tease and I lapped it up.

My breathing grew heavier as he cupped his arse cheeks, parted them as the gusset of his panties disappeared as he let them go.

'Oh, you naughty girl' I thought' Greg or Jenny, they had a super sexy body and the outfit was so fitting, the black panties in contrast were perfect as the light reflected off them giving them that shiny outline.

He moved on but this time at a slower pace, almost enjoying the freedom of the secluded space, knowing that it was just him and me and we were both enjoying the feeling of our attire.

He turned left, I left it a few moments before slowly approaching the small opening in the bushes that give you a prime view of the fallen tree, from this angle you can see enough but not too much to give too much away.

His stance matched mine and his detailed vision of my story was astounding, almost like he was able to see it through my eyes.

Almost like it had been prearranged, the sun came out covering the area with a vail of dappled light with a wide beam setting the scene as it projected down on to Greg, bent over the trunk with his legs slightly parted but enough to show the bulge in the front of his panties that I could clearly see, threw the gap between his thighs, from this angle.

I took a few steps closer, the snap of a small twig made Greg aware of my presents as he slip a hand down the front of his panties and started to fondle with the contents.

I would have loved, to have stood there and just watched him perform his teasing routine but I couldn't wait any longer. To savour the sight of the wonder of Greg in his sexy little outfit would have been enough but I knew we had other plans and I was eager to feel his supple skin, hear the tremble in his breath and to feel the tightness of his arse hole as I slide my throbbing cock up inside him and feel his smooth pasty body against mine.

I made no attempt to tread lightly as I made my way over to him, my footsteps where heavy and deliberate, his stance changed as I got closer but his hand still remained down the front of his panties.

'Stay where you are' I requested, 'You are stunning, I love the way you're teasing me'

'Mmm, I heard your footsteps, the anticipation, I feel it, oh god' He panted.

It sounded like he was psychoanalyzing and comparing what he was feeling with what I had described in my story, A real art for an illustrator.

The way he was moving and pleasing himself knowing I was standing behind him, watching him, knowing that he was arousing me, his mind games made him even more sexy as I stepped closer.

I could hear his heavy breathing and his response to my gentle touch as I rested my finger tips on his hips. His body was hot to the touch and he was trembling as my hands lay flat against him and drift up under his camisole, he bent over further to push his butt out as I stepped closer to receive it. My hard cock pushed against him and seemed to naturally lay between his arse cheeks as he gently gyrated, wanking me off with his movement.

'Oh, you are naughty, very naughty' I said.

'Am I a naughty girl?' She asked.

I was glad he identified as a she, I wanted to understand the dynamic of Greg and Jenny.

'Oh, you are a naughty girl, are you a dirty girl?' I asked, receiving no reply.

I wrapped my hands around her torso and brushed past her erect nipples causing her body to jolt as she pushed her arse harder against me.

I pulled her body up from its bent position as it became parallel with mine. Her hand still down the front of her panties, pleasing herself I allowed my hands to drift over her soft skin, every so often glancing over her nipples that were sensitive to even the suggestion of touch. She tilted her head back as I pushed my cock hard against her, venting a trembling breath in her ear which made her groan in acknowledgment of my arousal.

Her hand drifted round and I felt her wandering fingers find their way down the waistband of my panties making a 'B' line for my cock, gripping it with hot firm grip.

'Oh, you're not wasting any time, are you? Tell me what you want' I requested, as she started to wank me off while my hands still explored her smooth chest and responsive little pale nipples.

'I want to feel what you felt in your story' She said, 'I want to feel you inside me'

She let go of my cock as we gyrated against one another, my hands slid down here sides to her hips, my thumbs hooked the waistband of her panties as I pulled them down as I dropped to my knees. She pulled her hand out of her panties as she naturally assumed the position and bent over the trunk of the tree.

Kissing the small of her back and slipping a hand between her legs, I started rubbing my thumb around her perineum, applying a small amount of pressure while my kissing lips discovered the sexy dimples in her lower back. The gentle rotation of my thumb was making her anal sphincter relax as my kisses drifted between her arse cheeks as I landed little pecks on her puckered arse hole.

I could feel her hole throbbing through my lips as she started to push her it out as it gently relaxed.

'Is that ok?' I asked.

Her response was inaudible as she just mumbled and moaned and reached around to push my head back in between her cheeks.

My kisses soon turned in to gentle licks that quickly turned in to me lapping at her dilated hole as it winked back at me.

She never removed her hand from the back of my head; she just used it to drive my face deeper allowing me to push my pointed tongue through here ring so the tip could tickle her hole from the inside.

'Oh, hmmmm, oh god... Dom, oh' She groaned as I left the area sloppy with saliva.

I stood back up and slipped my panties down to the thickest part of my thighs, holding on to her hip with one hand and guiding my cock up to her hole with the other, she gently started to push back against me.

'Oh, your cock feels great pushing against my hole, just push it up, I want you inside me' She instructed.

I emptied the saliva from my mouth as it dropped and landed at the top of her arse crack and slowly slid down as it cascaded and dribbled around my cock. I pushed hard at the same time as Jenny pushing back against me and my engorged helmet forced its way through her entrance and kept slipping deeper until she slid down to the base of my shaft.

'Oh god, oh god, ohhh God. You're really in me; oh, I can feel you deep up me' She groaned as I slid my cock out until she got to the end of my length and then I drove it back up her.

Starting off slow the pace soon quickened until she started screaming out to be fucked harder.

'She really was a dirty girl' I thought and I was going to screw the arse off her.

She took her top off and threw it to the ground, revealing a large tattoo of a pair of broken wings and from memory symbolizing a fallen angel. The surrounding area wasn't as dry as the rest of the ground and you could see hoof marks pressed in to the mud from the wild animals that would congregate at the tree from time to time. This had churned the soil and made it a little loose, her garment had landed on top of a heavily disturbed patch.

Her arse hole stayed tight as I felt it gripping my shaft, she threw her head around like a rag doll as I fucked her.

'Hold me down on the ground and fuck me, fuck me on the dirt' She demanded as I withdrew and she laid face down on the soft soil, her arse raised, her cheeks held open by her hands that firmly gripped and pulled them apart as her cock was against her top that she had discarded earlier.

'Fucking hell' I thought' She's so fucking wild'

'Come on, fuck me' she shouted.

I dropped to my knees and hovered over her until my cock was up her arse, then with my feet hooked over the backs of her legs and my hands pinning her arms to the ground I pushed my cock up her as hard as I could, with shallow deep thrusts pushed it harder and harder as I felt it inch a little deeper each time.

'Oh yes, fuck me, fuck me' She shouted, 'stretch my man cunt'

She started to struggle so I gently released my grip on her arms.

'No keep going' She demanded, 'I like it, this is my fantasy'

She continued to struggle so I tighten my grip, still pushing my cock deep up her, the sense of urgency made me fuck her faster and harder as she writhed around in the dirt, the weight of my body pinning her as I fucked her.

'Say nasty things to me' She said, 'Tell me I'm a dirty slut and you're going to fill me with your cum'

This wasn't what I was expecting, I wasn't dismissing it, this was also one of my fantasies so I could associate with her completely, I just wasn't sure how far I could push it as we hadn't previously discussed it.

I leant back and pulled my cock out of her, quickly replacing it with two fingers that I repeatedly violated her with until I could fit a third inside of her. Still putting up a fight I held her down while forcing my fingers up her deeper still. Pushing and ramming, stretching and hooking my fingers inside, probing deep up her.

'Oh, please no, no. You have to stop, please' She shouted.

I pulled my fingers from her, holding her arms and pinner her down again. This time my cock found its own way as I drove it right up her, instantly fucking her arse, hard and fast, the squelching and slapping sounds echoed around our secluded oasis. Panting and moaning in her ear as she gave up the fight and just laid there, I was almost there and wasn't going to slow until I had creamed that pie.

'I can feel you growing wider inside me' She said, 'I've never felt anything like this before'

Moments later my breathing became heavier as I could feel the fit of my cock inside her becoming tighter, pounding as she pushes back in to me our thrusts synced and I could feel I was driving my cock deep as i felt the tension of her inner sphincter.

'Oh fuck, you're fucking me so hard' she said. 'Are you going to cum up me'

'Just shut up and take my cock, you dirty slut' I spat 'I'm going to cum up you alright, you filthy teasing whore'

I repositioned myself and grabbed her hair, pulled her head back, which made her scream and I could feel her hole tighten around my shaft as she closed her legs.

'Oh my fuck, I'm gunu....' my act of aggression pushed me instantly over the edge, a few thrusts later, I pulled my cock out of Jenny's arse just in time, ribbon after ribbon of spunk sprayed across her gaping arse hole, covering it with my pearlescent ejaculate as it started to pool in the creases of her arse cheeks and tops of her thighs. Her hole was still open as the cum slowly migrated inside of her.

I got up off of her and she just laid there, catching her breath, her hole gaping, empty and glistening from the liberal coating of cum. Seconds had passed giving me more than enough time to think over the two options, leave the violated vixens anus covered in my seed or clean her up thinking about how much further she would be prepared to go if I carried on.

I lent in and slipped my tongue between her thighs, lapping up my creamy deposit as I caressing my way to her throbbing arse hole, gently rimming and cleaning up the mess I'd made. Planting my thumbs firmly, I parted her cheeks so I could lick up every last drop that had seeped through her tight arse cheeks, gently probing and licking her hole and feeling the heat caused by my penetrative assault just moments earlier..

'Mmmmm, that feels nice' she said 'he he, you a dirty boy' she giggled.

'Turn over' I demanded.

'Why, what are going to do' She asked.

'Just turn over' I repeated as I grabbed her hips, 'I'm not finished yet'

She flipped over and presented me with her throbbing cock, pulsing and waving as I moved closer.

Her cock was around 5", quite thick, veiny and crowned by a bright pale pink bulbus helmet, glossy with precum and covered in lines caused by the creased cami top she had been laying on.

She laid there on her back looking vulnerable and innocent with her arms folded up and held close against her little pale boy titties but moments before had been teasing and begging to be pinned to the ground and fucked.

Her arms were red in the areas where I had pinned her to the ground and everywhere else that wasn't on her camisole top had signs of her struggle, minor grazes and soil marked her pain skin but still she beckoned me down to finish her off.

Poking my tongue out to tickle her frenulum, it instantly made her gasp and moan as her cock responded with a long hard throb. It came to rest back on my tongue and leaked it's clear salty nectar. Tracing around the rim of her helmet I teased her, as she did me, as she started to fuck the air between the end of her cock and my sloppy lips, the tip just about reached as I pulled back just out of reach.

'Dom, please don't tease, I'm so fucking horny and ready to blow' She begged.

Tight lipped I offered my mouth up to the end of her cock as she pushed it in to be greeted by a hot wet cavity and a tongue that lashed against it. I didn't need to bob my head because within a few thrusts of her sexy hips she grabbed my head and started fucking my closed mouth.

'Oh my god, she's so fucking hot' I thought. As she fore filled another one of my fantasies.

I was so turned on by her newly adopted commanding role as she enjoyed fucking my mouth.

The saliva started to build up as she thrusted her cock in and out, you could hear it squelching as she penetrated my tightly closed lips. She pulled her cock out of my face, allowing the spittle to saturate her cock and balls quickly returning to the same pace of thrusts. I reached up and slipped my fingers around the base of her cock, holding her foreskin back, the feeling of her pumped helmet in my mouth felt amazing and seemed more delicate than Mac's, although I never sucked Mac's cock for long, he was more interested in fucking me than me sucking his cock.

Jenny's moaning was sensual and passionate even if the act wasn't, her pace and moans sped up as she buried my face in her pelvis spreading my spittle across her thighs and leaving most of it dripping from my face. Her grip tightened as she grabbed more of my hair, I forced her cock to the roof of my mouth with my tongue as I felt her cock swell and she took a deep breath and held it. With slower thrusts I could feel her cock throbbing, her whole body went rigid as my gratifying moaning led to her to reach climax. With a sharp exhale her whole body relaxed and started shaking as she came hard, her throbbing cock pumping cum in to my mouth. I struggled to swallow all of it and some escaped and trickled down her shaft. As she lay in her trembling state, I took over milking every drop from her until her cock grew limp and she started laughing because it had become too sensitive for me to continue.

During that time my cock had become hard again but i could see she was so blissed out that it wouldn't right for me to force myself on her again, besides, there was always next time.