Cross Dressing
24 Jun 2025


Well I can honestly say that I didn't get much sleep last night, Simon, so lovingly and masterfully made love to  me with a gentleness I'd not often experienced with other men, or women, I'd always been that cum dump  men loved to fill.

Ive said it before but it was like he was having sex with someone else, that happy look in his eyes as his sperm made it's way into my willing body on everyone of his powerful ejaculations, My body now limp from exhaustion, my bottom sore, his arm lovingly wrapped around me in the spoons position as we slept  naked in bed, I was grateful there wasn't a hard cock poking into me, I'd been totally fucked and today was the first full day, my mind wondered as to what this horny little devil had in mind for me, yes, I was going back to the boutique for another photo session and whatever comes afterwards, last night was just a taster, later I'd see another side to Simon I wasn't prepared for, thank heavens my wife wasn't here to witness me being used in such a way. Simon started to wake up, his hips gently pressing into me, that hardness I feared started to press against my still sore gaping hole ‘ morning sleepy head' , he moved closer to kiss my earlobe as a hand now teased my nipple.

Simon knew exactly how to manipulate my body into submission as both my nipples and cock started to swell to full hardness, his hand made it's way down to be greeted by my now hardening expectant cock, now lightly lubed with some pre cum as his finger smeared it around my growing cock, me, lying there  thinking what a slut I am with a smile, for some reason Simon had a gift of being able to bring me to  full hardness without my tablets.

‘ oh you naughty girl, I think I'm going to fuck your bottom again’ , AGAIN, the soreness from my now battered sphincter reminded me, maybe not, but Simon had hit that magic button and I needed fulfilling, this I know Simon likes, to be in control.

Still in the spoons position he moved his hips again towards me, only this time I felt his cock at my entrance, this is gonna hurt I thought to myself as he applied pressure, I did my utmost to relax as best as possible, a bit more pressure applied and he just simply slipped into me, thank heavens some of his sperm from last night's sessions  was still inside me and acted as a lubricant as the bulbous head of his cock just popped past my still sore gaping  hole. Ever so gently he pushed only a couple of inches into me and just slowly fucked my poor little sore hole. Simon really had stamina for an older man but was savouring every gentle push into me, the head of his cock barely past my sphincter.

I wondered how long he'd last before filling me with cum  again after such a busy night? Well the answer was. , not long, I think the extra stimulation his glans were experiencing was exactly what he was hoping for as without warning he gripped my waist tightly but didn't  thrust into me to force his cum deep into me but just kept his cock just inside me. With a deep gasp and a whimper he came into me for a fourth time! 

There was no way I was getting more of his spunk as his glans pulsed against my now really sore sphincter, it actually felt quite nice as his cock throbbed away inside me, he was  so gentle, not like the dominant man who'd fucked me so roughly in the showers only a few weeks before.

Simon stayed inside me until he went limp and just pulled out, no spunk following his cock, had I really drained him at last? A cool wetness around my man cunt said different,  Simon asked me to lay on my back which I did without question, getting up he went  to the bottom of the bed then did something to me I totally wasn't expecting as he climbed onto the bed and between my legs, my still rock hard cock obviously his target as he closed  in on it. ‘ close your eyes and just play with yourself’ I thought he meant  my cock but soon understood as I felt the unmistakable wetness around my glans as he gently sucked on it.

 That loss of one of my senses really heightened my pleasure as his warm wet mouth sunk ever deeper down my shaft, his hands on my upper inner thighs to keep them prised apart as he just lovingly sucked my cock, it had been quite a while since I'd had a man pleasure me in this way and it showed as I started to loose control embarrassingly quickly as my hips started to rise and fall, counteracting his motions in the hope he'd deep throat me, I couldn't hold off any longer as that tingling in my cock grew until an uncontrollable outburst of my pent up sperm shot out, catching Simon by surprise as the first volley must have hit the back of his throat,  he coughed in an effort to clear my sticky mess as my pulsating cock spewed out more cum,  by now I was an emotional wreck, again!, tears flooded down my face as I cried out for my lover to keep going , that was a slight embarrassment as momentarily I'd lost it, lost in an orgasm like no other, the fact a man was doing this to me and brought me to orgasm made it even more enjoyable.

The second and third equally powerful spurts were expertly captured in his mouth as my last drops of sperm added to the pool of cum he'd made me produce.

Simon moved up the bed, his smile made me feel special as he went in for that spunky kiss, forcing my own sperm into my mouth as his tongue swirled around inside my mouth spreading it all around. His final act was to get me to raise myself to a position where he had a good view, reaching for his mobile he pointed it at my mouth now full of my own  mature cum, some hanging off my chin as he snapped away ‘ open ‘ he ordered me, opening my mouth I realised I'd released quite a load! 

Once satisfied his last command ‘ swallow it bitch’ 

There was quite a lot to swallow which took two attempts but that oh so satisfying feeling as my own spunk slowly made it's way down my throat.

A few more photos and we were done, I really hoped that was the case as I was  now totally drained.

‘ get a shower slut, you've got a busy day ‘ 

To say I had a lovely shower would be an understatement as I cleaned myself only to re enter the bedroom seeing Simon texting on his phone and it  profusely pinging away, he looked at me with that devilish smile he didn't tell me who he was in contact with he just said it was business it would be much later that afternoon when I'd realise I'd be that business he mentioned and another night of wild submissive sex , Simon was certainly making the most of me in the short time we had together and I was loving every minute of it, in the meantime it was back to the boutique for a couple of photoshoots then back to our hotel for a surprise I hadn't even contemplated, this was only the start to the grand finale I couldn't even envisage until it was too late.

Tags: crossdressing, anal sex, bareback , creampie


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