The run up to Christmas was amazing, John spent as much time with me as possible, those remarks at work saying how shattered I looked as I made for the coffee machine on a Monday morning were well earned!.
For John I was a new thing and he really enjoyed fucking it, most nights into the very early hours.
Most evenings John would put the nipple suckers on me, he really enjoyed how they looked when he pulled them off, Ripe purple, protruding, hard and very suckable.
The sensations that he created as he touched my nipples were indescribable, all I knew was every time he did that to me my resistance would crumble leaving me wide open to his advances which he took full advantage of.
This would go on until new years eve when I eventually found out just why my nipples were so important to him.
I'm the meantime I think he fucked me in every room and every conceivable position, the carpet was a bit rough on my knees but as long as he was able to inseminate me, he didn't care!.
He did want to take me on the balcony but thankfully it was far too cold for that!
That was my first inkling that John might be an exhibitionist, thankfully the cold weather precluded any such activity!
My favourite place for sex was the shower, that feeling as his hands explored my warm wet naked body , caressing my artificially enlarged nipples always got me hard, from behind he'd caress my cock, pulling my foreskin back over my glans then back again, that feeling as he touched me, resulting in the release of the most amazing amounts of sperm under extreme pressure,
Sadly ending up into the whirlpool of doom as it was sucked down the plughole, his sperm however always ended up deep up inside me as it should be.
By a stroke of luck I was about to take two weeks off over Christmas so I was able to just about be Christine 24/7 in the flat, that really felt both strange and wonderful at the same time as finally I could be the person I'd hid so successfully from family and friends for so painfully long.
Days on my own were spent with me practicing walking in heels which still needed a lot of work and makeup which was passable now but still a long way from perfection. On my birthday a parcel arrived for Christine, it was obvious who it was intended for but I waited until John came home for lunch before I dared to open it.
When John came home and saw the parcel he couldn't contain his excitement as with a kiss to the lips just said Happy Birthday, he remembered! as he urged me to open it.
Unwrapping it started to reveal something like a satin dress as I eagerly opened up the parcel to reveal a very sexy black satin maids outfit, complete with black satin frilly sissy knickers with a bow on the front.
Another smaller parcel contained fine black stockings, I knew exactly what was on his mind.
In the early stages of our relationship John was full of surprises.
I held it against me, John's face said it all, he wanted me in it but not right now, he'd make me wait until later where I'd discover very roughly just what wearing such an item of beauty and servitude would be demanded of me from a very unexpected quarter.
That time came sooner than I anticipated as that very afternoon I had a call from work from John who asked me to put the outfit on ready for his arrival and to let him know when I was dressed, suddenly I felt giddy with excitement at the thought of wearing my birthday present for his pleasure as I searched for some ‘ accessories’ to compliment my outfit with little success, I had everything I needed that came with the outfit, my only options was makeup which still a little shoddy but was improving, Debbie had taught me well.
I had time, or so I thought as I painted my nails black to match my outfit, I had bought some nude lipstick by accident which I thought I'd try which moisturised my lips into being very kissable indeed without the overpowering redness I was more used to.
A pinky hint of eyeshadow and perhaps an over application of mascara finished that look I was after, a complete slut which would be my undoing as I'd soon find out.
I'd got a few hours before John was due so thought it would be a good idea to slip on my stockings and black sissy panties then my outfit, it felt so sensational as it slipped down my body, it's elasticated waist finding mine as it softly hugged my contours. I reached for my blonde shoulder length wig, adjusting it in the mirror before admiring myself, unconsciously my hand found its way into my panties to find a rock hard cock Just waiting to be loved, I'll admit I was tempted as I drew back the foreskin over its swollen glans, momentarily I'd lost control and really started to masturbate in front of the mirror, yes I'd excelled myself as I watched this beautiful young crossdresser sensually make love to herself, if it wasn't for the knock at the door I'd of finished myself off there and then.
John was home early!.
Quickly I recomposed myself but couldn't get rid of my obvious erection poking outwards from the outfit, it was only John, he wouldn't mind seeing just how pleased I was right now, a quick spray of my more expensive perfume that I only use at home, slipping on those 4 inch stilettoes to surprise him then made for the door, it hadn't even occurred to me that John had a key! I just flung the door open expecting him to embrace me.
What I got was Jeff holding a bottle of champagne, my face dropped, I wasn't expecting this, that smirk on his face as he wished me happy birthday, then the punch line…
‘im your birthday present’
My emotions suddenly went into panic mode, this is the man that practically destroyed my arse last time and here he was, his intentions were crystal clear as he walked in, a quick kiss on my cheek as he passed me, then I remembered, condition 3!
What had I gotten myself into? I thought John was joking about the conditions just to add a bit of excitement and uncertainty, well uncertainty it suddenly wasn't, I'd become John's whore as well as friend, lodger and lover.
I think, looking back, that was the moment I'd figured out I was more than just John's friend, I was anyone's John wanted me to be, essentially I was being made his cuckold slut, a position I'd find myself in many times over the years, either myself or my future wives, an eventually id not even considered at this time.
Jeff handed me the bottle and told me to get two large glasses, this was a celebration, well for him as he made himself at home on the sofa.
Coming back into the lounge he grabbed the bottle and opened it, letting out a loud pop as the cork flew off.
Quickly he poured the champagne into the glasses to avoid making too much mess, holding his glass up he motioned me to do the same,
‘To us’ as his glass met mine
As a young man that really freaked me out, what had I got myself into? John was certainly a dark horse, not for one minute did I imagine he'd be sharing me with his friends,I really thought he was joking about my ‘ terms and conditions’ well I was living rent free, perhaps this was how I was to repay him for his kindness, a bit similar to my landlord but definitely not to this extent!
Jeff hunched up closer to me as we sipped the champagne, he seemed interested in my past, well what past I had at such a tender age as I talked about my early years. He was most interested in my first time with my friend and asked a lot of embarrassing questions about it.
Well I'm not a champagne person, the second glass made me a little giddy, me not being much of a drinker as I started to relax in his company, maybe too relaxed as his hand slipped under the top of my outfit and started to explore my chest and now erect nipples.
He pulled the top away from my chest to gaze at my over sized nipples from the constant nipple training John put me through.
Jeff softly kissed me on my neck as an exploratory hand made for my nipples.
His first touch sent sensations through my body that I cannot conceivably explain as they were already hard and appeared to grow slightly larger, their tips now protruding as he gently rubbed a finger over them, so soft, so ohhhhhhhh as he used my body against me as I savored every touch as he increased my levels of excitement, my cock which had mostly lay semi dormant in my panties now started to swell to full hsrdness in anticipation, a far cry from when I'd opened the door and let him in, then I was dreading his presence, now I was slowly warming to the fact this brute was setting me up for a painful fucking, I knew it would be but somehow just to his touch was hypnotizing and at that moment I would have done anything for that man not realizing that would become a reality very soon but for now I had to try and tame this man to be a bit more gentle with me, somehow Jeff yet again would prove he was no shrinking violet when it came to fucking young men especially dressed in the way I was, I stood no chance ever since he walked through the door there was an inevitability he'd be fucking me again, thank heavens I'd remembered to clean and lube myself with some Vaseline but that was for John later, not Jeff's monster cock which would afford me no mercy in it's efforts to breed with me.
Jeff's fascination with my nipples was getting him excited, I could tell by his breathing next to my ear as his softly kissed my neck before he did something I wasn't prepared for as he turned my head to his, gazing into my eyes was a man totally besotted with me as he moved in for a full on kiss, I'd never really been kissed by another man so I was really apprehensive as our lips touched, a quick peck before pulling back to see my response, seconds later he went back and forced his lips over mine, parting them with his tongue as he french kissed me.
Ok, I was for once shocked! I didn't know how to respond to this mature , more knowledgeable man experienced in this type of mating game, all I could do was respond which encouraged him to be even more assertive, now that was a mistake as he took that as a signal I wanted to go much further, much quickly with him, ok, he wasn't wrong! By now he'd really had me excited, or was that the champagne?
Looking at the table the bottle was empty, as was my glass, Jeff's was half full and had been all this time, I wouldn't be able to fight off his advances even if I wanted to, he had no idea how much I'd been looking forward to seeing him again and here we were, only minutes away from being coupled to each other by his long thick veiny mature cock.
Whilst he held me tightly he told me to put my hand on his crotch, no nervousness this time as I knew what to expect.
What I didn't expect was that it felt like a rod of iron in his pants, it felt funny as I slowly rubbed his rock hard cock. Even that didn't feel like I remembered it, its thickness really stood out.
I remembered how it felt last time when he fucked me with that, part of me wanted to get away from him so as not to get that repeat anal battering like last time but strangely I was being drawn to the very idea, like a moth to a flame and yes I would get burnt again but I just couldn't help myself.
Jeff released me from his grip on me and stood up, Jeff was always full of surprises as he practically lifted me off the sofa and picked me up like we were newly weds as he carried me to the bedroom, his voice of excitement as he told me he'd been dreaming of this moment since the last time he made me cry.
Jeff carefully placed me on the bed, i started to remove my stilettos but was told to stop as he undid his shirt to reveal his six pack. For a man in his late 60’s he was impressively fit.
Off came his shoes then the most memorable part as he unbuckled his belt, his trousers slipped down effortlessly to the ground to reveal he was actually wearing stockings and suspenders and skimpy panties that really couldn't hold back his manhood as it poked towards me, trapped behind just a flimsy piece of material.
‘Surprise’ he said with one of the biggest grins I've ever seen.
This man was going for broke with me. Now I knew I'd done the right thing by preparing myself as I knew for a fact I was going to struggle again but I think that's what Jeff liked about me, fresh meat!
Removing his panties, his cock sprang up ready for action as Jeff approached the bed, my eyes could only look at one thing as his huge penis, erect and slightly wet pointing in my general direction like an old expectant friend.
He got on the bed next to me and moved in, more attentive kissing ensued as his hand found its way underneath the hem of my outfit and onto the top of my knickers, my own shaft now solid and aching for some action itself but first Jeff would have his fun.
First, his fingers found my nipples again and started their dance as they circled the very tips creating a feeling I've yet to be able to describe which sent tingles through my body and into my now throbbing aching cock. Jeff knew exactly what he was doing to me, it was looking like he'd had a lot of practice over the years as he now pinched my nipples hard and pulled at them creating some pain but also a pair of beautiful mini breasts.
He held them outwards whilst his finger and thumb rolled my nipples around which was far from pleasurable for me but for Jeff, he was loving the sight of my nipples outstretched and my obvious discomfort of him doing so which then led to some very heavy petting as he kissed my neck again only this time giving me a love bite, working down my body he did the same until he got to my hard erect nipple.
For a good five minutes he kissed, licked , sucked then suckled at them like a baby until a wondering hand finally found my cock.
A very inquisitive finger stroked it's whole length, stopping at my foreskin, probably seeing Just how wet from my excitement it was, my moans of frustration clearly audible as Jeff continued to tease me then suddenly stopping.
I needn't have worried as he went to the end of the bed then grabbing at the heels of my stilettos, pulling me down the bed, the straps digging painfully Into my feet as my legs went over the end of the bed, quickly by him sliding my knickers over my satin stocking legs.
Now a treat for me as his head disappeared between my legs, now forced wide open and draped over the bed, a sudden warm feeling as his mouth engulfed my cock, his tongue masterfully flicking over my glans with a bit of head bobbing to mimic fucking, this was just beyond my capabilities to hold back and I think Jeff knew it as I did what I shouldn't and started to fuck his mouth, that sensation as my cock slipped through those tightly clamped lips down my shaft. I don't know why he did it but he suddenly stopped, my frustration was now off the scale as I actually shouted at him ‘ please, please don't stop, finish me off’ My god, what a fucking slut I'd become so easily!
Well that was embarrassing, he'd brought me so far only to deny me at the crucial moment, thankfully I was wrong as he was just adjusting his composure for the finale, those warm lips yet again wrapped themselves around my rock solid Shaft and teased it, his tongue dancing on every erogenous zone it could find, this was a very dangerous thing to do to someone almost 45 years his junior.
He'd prepared my body for what would be my most intense orgasm to date as he teased away, he really thought he was in control but how wrong he was as that now familiar tingling around my glans suddenly grew to an unstoppable conclusion.
I only had seconds to respond to my orgasm of such magnitude I almost ripped the bed sheets as my cock just exploded catching Jeff completely off guard, the first and most painful powerful jet of sperm must have made it half way down his throat as he choked making his eyes water, a second equally powerful jet of spunk shot out more or less hitting the same spot but Jeff was an experienced cock sucker and recovered quickly to save the last couple of volleys of my young rich creamy sperm into his mouth.
I had a good idea what he was about to do as he made his way up the bed and planted what was the wettest spunkiest kiss ever as my mouth filled with my own sperm, his order was clear and simple, ‘ swallow it you fucking slut ‘ well not what I was expecting but I did it for him and showed my empty mouth to him like the dutiful sissy slut he'd made me become.
‘good girl, now daddy's going to fuck you, on your hands and knees bitch’ thank heavens this was on the bed and not the carpet which would have left burn marks the way he fucked.
I had a feeling this was coming even though I'd made myself ready for such an event with John I wasn't expecting this from Jeff, the next 30 minutes I’d be taught a valuable lesson in life, as Jeff moved in to complete what he actually came to see me for, I could feel the heat of his body behind me as he adjusted himself to get the right angle for penetration this time he said he was going to do me right.
I'm not sure what he meant by that just then but by the time he'd finished with me I would definitely know that I'd been fucked like never before, it would be a couple of years before a man came along who could better what Jeff was about to do to me.
I'll give him one thing, I don't know where he hid the bottle but highly relieved when the all too familiar coolness of lube was squirted down the crack of my arse and tantalisingly ran down towards my soon to be very sore sphincter, a finger teasingly explored my entrance as I tried to remain in position, sperm still hanging down from my recent orgasm from the slit of my now semi erect cock.
Jeff easily slipped another finger inside me, ‘ I see John's been keeping you busy then’ as he easily wiggled his fingers inside me, teasingly stretching that tiny muscle which was about to be stretched to near beyond its capabilities by John's massive cock.
Jeff moved as close as he physically could, his cock resting on my crack and lower back, that was my first inclination that Jeff was actually larger than I remembered!
It's weight on its own as it rested against my young creamy soft skin ready to fuck me was quite impressive if not worrying, the last time he fucked me I was sore for days afterwards but here I was , a willing? slut to be taken by him again, yes the champagne was doing its job of relaxing me to a point I'd do anything Jeff asked of me, then it was time as he shuffled into position, his excitement unmistakable as his glans easily slipped over my crack and directly to my unsuspecting hole, he wasn't even going to play first as his cock easily found its target and forced me open, whether it was the alcohol or the lube? Possibly both as he pushed into me with ease as my sphincter stretched and involuntary wrapped itself around Jeff's invading shaft.
The first few inches seemed to just glide in unlike last time where I struggled and screamed out, I guess Jeff was expecting that again ,but no. I was now more experienced or so I thought as the last inches of his solid cock forced me open to accommodate such a worthy cock, now I cried out with real tears running down my face as Jeff forced his way home inside me, for one terrifying moment I thought he'd gone too far as the pain inside me really was intense.
Jeff knew what to do and just rested inside me, stroking my back to comfort me and take my mind off the fact I'd got a cock far larger than I could cope with now successfully lodged deep inside me.
Jeff was mindful of the fact I'd struggle with his cock so a few slow strokes for it to bed in so to speak and let both our lubrication take effect which was quite noticeable as his cock slowly started to slip back and forth with little pain, however Jeff was only pulling a few inches out of me, when the time came he'd show me just how inexperienced I really was in taking a large cock.
Still coupled we awkwardly shuffled up the bed so he had full control over me, then it started with a long Ahhhhhhhhhh as he pulled backwards, some discomfort as it felt like he was pulling my innards out, then a slow push back in, that's when reality kicked in as it felt like a trunction being rammed into me, my reaction was predictable and expected as I cried out, quite loudly, thank heavens it was mid afternoon and most people in the complex out to work?
My response pleased Jeff as he repeated his actions, his withdrawal so slow before a quick reinsertion, this time more pain as I just couldn't comfortably accommodate such a large penis.
That didn't stop him though, my submissive cries and whimpering made him feel in total control, more than last time and he was savouring every minute as he drove into me again and again, slow but deliberate strokes which would test my resilience to the maximum.
One thing I remembered most was how it felt as his glans pushed mercilessly deep into my narrow passage; its shape very discernible now as it slid back and forth into what was for his cock, still a virgin hole.
I guess Jeff was taking his time on purpose to make me experience the full majesty of a mature solid cock as it kept my sphincter stretched to accept that monster cock sliding back and forth then he suddenly stopped, I thought he'd given up, highly unlikely! It was just to squirt some fresh lube on his shaft, the next 10 odd minutes were about to prove a mixture of both pleasure and pain in equal amounts as Jeff built up to a climatic ending.
The first few minutes were almost bearable as the full length of his cock now slid back and forth, the sounds he was making reinforced my assumption he was enjoying this.
A sudden out cry from Jeff as he now sped up, so much so he had to hold me tightly by my hips, that just made it easier for him to push just that little bit further into me, now there was pain as my body had found it's limit, Jeff trying to go beyound them as he now really started to fuck me, my once semi erect cock now fully erect again and swinging violently with every thrust into me, Jeff stopped for a moment to catch his breath and to give my nipples a good squeeze and painful twisting then it was back to finishing fucking me.
His hands now back on my hips, a few slaps on my bottom and he was off.
‘ right you fucking slut, you like it rough do you?, I'm going to make you beg me to stop’
With that he started to fuck me , gently at first then it happened as his orgasm built up, there was no mistaking as as his breathing got more irratic, his thrusts now slamming into me so hard his testicles slapped loudly against my bottom, my poor cock felt like it'd fly off at any moment as it swung and struck my stomach with each violent thrust into me.
Yes, this was it as Jeff now started to lose it as the sounds he started to make sounded more like a wolf on heat, my sphincter now warm from the friction of his cock pumping away into me like a piston on a steam engine which was now making me feel uncomfortable.
The last 90 seconds were just a blur as the slapping sound was off the scale in frequency Jeff was certainly showing just how fit he really was for an older man, me on the other hand the receptacle of his frustrations was now making me question myself
as this man now totally dominated me, for this moment I was his and his alone John would never have believed it if he saw it. The pain now grew as he pounded away into me, Thankfully Jeff was just about there, building up to his climax whilst myself praying he'd get there quickly as well.
Suddenly his thrusts Increased, his spunk filled balls slapping away on me as he built up to that final thrust and insemination.
Jeff enjoyed my sounds of discomfort as he fucked me , then the final dominant thrusts, each one punctuated with a single word, ‘you - fucking - little - slut ‘ as the last word came out he came as I was now crying at feeling so used, his cries of joy and satisfaction echoed around the flat as that now familiar feeling of sperm being forced into my tiny passage, this time though it felt different as what was normally just a warm sensation felt like he'd shot molten lava deep into me, gripping and pulling at the sheets I cried out with real tears as I realised I'd been bred by a very sexually frustrated old man.
I don't remember just how many jets of that hot sperm he managed to put into me but it felt like he'd been saving it up just for me.
With all that exertion Jeff just collapsed on top of me, his weight pinning me to the bed as his cock pulsed out the last of his sperm into me, his cock now dangerously close to slipping out as it started to go limp.
Jeff kissed my neck and got up, pulling the remaining length of his cock out of me leaving me feeling like my innards were on fire, yes, Jeff really had fucked me hard, intentionally to teach me a lesson? I don't know but he'd fucked me and drained my energy as well, or was that the after effects of the champagne?
I was absolutely shattered and I guess I dozed off, waking up perhaps an hour later.
It was now dark outside, Jeff now gone, I was alone.
still no sign of John so I tried to clean up the mess Jeff had made of me. Looking in the mirror I looked a complete mess, my makeup totally ruined evidence of sperm on the front of my new maids outfit. John wouldn't be happy with that but worse still, sperm on the bed where Jeff had inseminated me and leaked out.
I was just about to go to the shower and clean myself up when I noticed on the bedroom floor some polaroids, the crafty bugger had used our camera . There were eight there. As I looked through them They were of me on the bed, quite a few of my face showing my makeup, my stockings which were heavily laddered with evidence of sperm close to the tops, mine or his? I don't know but now totally ruined.
On the back of one of the photos showing my ruined makeup it just said happy birthday slut.
One thing I do remember is that those cameras come with a pack of 10 instant pictures, all used but only eight photographs on the floor so I guess Jeff kept two for himself as a keepsake.
Still weak on my legs from Jeff's over enthusiastic fucking I made for the shower and cleaned myself up and cleared all the evidence of Jeff ever being there like a cheap slut I'd apparently become.
Outfit in the washing machine I found out some lingerie John liked me in and slipped on a full length dress in the hope John wouldn't want to fuck me when he got home, my sphincter was still sore, worse still it was gaping open from being used so roughly by Jeff's girthy cock so a big give away that Jeff had used me as a sissy slut for his own deviant use.
The moment John came home, like a husband returning to his wife he embraced me, and asked how I was, myself here in front of him, a sense of shame at what Jeff did to me, my body littered with love bites, there was no way I was going to get away with this, then John just asked me if I liked my birthday present!
That smirk on his face said it all, he knew all along, he just said that I deserved to be fucked by someone who could give me what he struggled to do and he wasn't wrong.
That sense of shame turned to relief as he hugged me, then he asked me a question I never expected, ‘ would I do it again with some friends of his’
This was the wake up call that I was more than just John's lover and according to Debbie not the first!
I'll never forget my birthday but that new years eve party would eclipse today's experience into obscurity.
John went to the bedroom only to discover the photos Jeff had taken.
We both sat on the sofa whilst he looked at them, some he really liked as he asked me how I felt about what he'd just asked me, by new Year's Day I'd know the answer to that which would be the catalyst of things to come for the next 40 odd years.
Oh, we didn't have sex for several days as Jeff really gave me a good seeing to but Christmas night he more than made up for it.
