It had been several weeks since I'd been expertly fucked by Steven, my friend and I kept up our regular meetings although I desperately wanted another night with him, especially after what he did to me, and remembering how dominant he was which I really enjoyed . Then the golden opportunity presented itself. My friend had got a job in London and a leaving party was organised, he told me Steven would be there, for a moment my heart raced at the thought he'd be there but then the sudden realisation that it would mean a pub crawl type leaving do, my heart sank although it shouldn't have if I'd have known how the night would pan out, especially for me! Arrangements were made for Saturday in two weeks time, we'd all meet up at the pub and go from there. Saturday slowly arrived and I was excited at seeing Steven again, not so excited for him to see me in male mode though. We arrived to find a good portion of the party hadn't turned up, typical! I saw Steven at the bar and some people I didn't recognise.
Sorry guys, he said it looks like it's just us tonight. We had one drink when he suggested we all go back to his house. I noticed Steven wink at my friend out the corner of my eye when he said that . Ok he said and ordered a couple of taxis. We ended up in a secluded cul de sac with about 4 large detached houses. We all went in, us and four strangers who'd not taken their eyes off me since we arrived. We were shown into a spacious front room, my friend seemed more familiar with the layout as he walked in like he was at home. The room was very minimalist I thought, with a large telly, a large sofa and music centre. Steven put some music on and grabbed a box of beer from the kitchen. It looked like this was part of his plan but I was still a bit naive at this stage so dismissed it as there were quite a few people here although, again,I did notice the odd glance from some of them, looking at them I guessed they were all at least twice my age if not more! My friend and myself, obviously the youngest people there, initially made me feel nervous but as my friend was talking with them I felt more at ease with it all and joined in. Is it his leaving party after all?
So TV with football on, beers and music, not so bad after all.
Steven eventually came over to me and asked how I was and to apologise for making such a mess of me when we first met. Cool as a cucumber I replied ‘ to be honest I did enjoy it, especially the end part, Steven looked surprised at my statement which kind of caught him off guard, looking at me as if he now had a plan, he replied ‘well maybe we could do it again later’ he said with a smirk on his face and walked off to his other guests, I couldn't believe what I'd just said, had I given him the wrong impression of me, I think my nerves had got the better of me which I'd dearly pay for later. I now saw Steven chatting with the men and looking in my direction, my friend amongst them, a few smiled at what he was saying then dispersed back to the telly or kitchen for drink and nibbles.
Steven came back over and asked if I could follow him upstairs , yes I thought, it's going to happen, us together, alone.
We got into his bedroom and switched the light on, I immediately saw on the bed a pink maids outfit, satin I think, it looked like my friend had told him when he'd dressed me in similar attire, stockings and a suspender belt, pink satin panties and some high heels, I had been practising walking in a pair at home after our last meeting, not easy!! But proficient enough to do so. I noticed a bra with some silicon breast moulds in them, well this is new I thought to myself and unsure how to fit them but Steven would help me with that later.
Steven said, he and the guys were wondering if I'd come back down to the party in this?, call it a bet he said in a convincing voice.
I was flabbergasted, I wasn't expecting this. he went on, it's all in your size even the shoes. Looks like my friend really had been making notes between fucking me when I wasn't looking, sneaky!!
I wasn't sure, scared, apprehensive that more and more people would recognise me but Steven had a way of calming my nerves , he hugged and kissed me, ‘come on Christine, for me’, well I just melted in his arms, and agreed, what do you want me to do I asked, oh you'll be our maid serving drinks and party food, there was no mention of me actually also being on the menu!, that thought was only one I'd shared with my friend in bed, did Steven also now know my fantasy? “I just want to show you off and show how beautiful you are”, I blushed at his compliment.
I thought about this and with an unexpected rush of excitement and enthusiasm, perhaps too much! said I'd do it for him, good girl he replied, the bathrooms on the left so you can freshen up. I'll let the guys know and left the room.
I went down the hall and tried what I thought was the bathroom but it was locked, okaaaay I thought to myself but realised it was the door opposite, obviously I thought nothing more about that as I must have not been taking everything in given how excited I was
Showering, I prepared myself, dried off, and went back to the bedroom and started to become Christine.
Pink panties, suspenders and stockings on first, luckily Steven popped his head round to see how I was going, I asked about the bra, here let me and put the bra and silicone breast forms on and adjusted it to fit snugly, It felt like he'd done this before as he fitted it with ease. Apart from the weird sensation of the weight on my chest, it actually felt ok, Steven behind now groping the soft breast forms with a very obvious hard on pressing into my back, he stopped , that's for later he whispered into my ear, kissing me gently on my ear lobe, he left the room for me to finish dressing.
On went the maids outfit and WOW, I'd filled out the outfit with the breast forms, I looked amazing and with a little make up ( I'd been practising ) blonde shoulder length wig I looked quite convincing.
On went the strappy 4 inch heels and the transformation was complete .
I made my way to the stairs very carefully, I lived in a flat so no stairs! Holding onto the rail I slowly made my way down, once at the bottom, Steven was waiting for me , he hooked his arm around mine, to help me balance in my heels or perhaps just to show me off in front of the others and escorted me into the room and introduced me, ‘here's Christine, she's your host for tonight’ , a few wolf whistles confirmed I'd done a good job with Stevens help.
‘Ok Christine, get to work looking after our guests’ in a more authoritative voice.
Off I went into the kitchen a bottle of scotch was open ready with some glasses, I had a large glass for Dutch courage then went out to the guests serving any who wanted it. As I mingled,I got the occasional hand under the hem of my outfit and brushed over my bottom through my panties, some a little more daring with a grope round the front, I'll admit I was now a little nervous to start off with all the attention I was suddenly getting but it excited at the same time which was beginning to show, however I was now enjoying the attention, the realisation that I might be more than just a hostess suddenly hit me.
A sudden rush of excitement went through me causing me to have an erection that was now easily noticeable,
As I walked back to the kitchen a stray hand brushed against my now hard cock,rubbing my hardness, I made it to the kitchen to see my friend in a state of undress with one of the guests, he looked at me and said enjoy yourself, by now my body was screaming for attention, I made my way to the front room in anticipation of what might happen but was stopped in the hallway by a pair of arms that wrapped around me and a heavy breathing against my ear, how about we go upstairs for some fun, it was Steven! I went a bit wobbly with excitement at the prospect of being fucked again by Stevens enormous cock, what a slut I was becoming I thought to myself. Ok I said and was escorted upstairs still wobbling in my heels.
Once there he was very passionate with me, from behind he played with my breasts and cock , I could feel his excitement pushing impatiently into me. In a flash I was pushed onto the bed on my back my panties quickly removed and grabbing my legs by my stilettos pulled both me up to him to expose my hole, some lube was applied, then he started to tease me as the tip of his cock slid around my hole,sliding teasingly over it, he did this several times, he knew what he was doing then without warning he just slid slowly over and pushed it straight in, now I was impaled with a good four inches in me as he slowly forced the rest of him into me, I thought I'd easily receive him but my friends cock was no match for his monster proportioned cick.
This time there was some initial pain as he tried to push deeper into me.
Thank god, my wait was over but not how I'd imagined it! as he entered me more roughly this time, I put that down to a sense of urgency on his part to inseminate me again plus the fact he'd turned me into his fuck doll for his own pleasure and maybe a few others tonight?, at last we were as one again, I'd dreamt about this moment for some time and loving it as his 8 inches drove home, slight pain as he started to thrust into me, I closed my eyes as the ecstasy of it all took over my body, he pumped away plunging as deep into me as he had before, he was expertly making me lose control of my body as my now rock hard cock was flapping around in time with his thrusts now getting wet in anticipation of some attention of its own. Lost in the moment he continued to fuck me whilst the bed now had extra movement, I opened my eyes briefly to see two now naked men had joined us, the rest watching with hard cocks in their hands.
I closed my eyes again, I wasn't expecting this, well not tonight anyway but it was something I'd fantasised about for a while, I was about to become the cum slut I'd often told my friend between the sheets as he made love to me.
Steven just kept thrusting hard into me in front of the others like I was some sort of trophy, faster and faster until he was about to release his seed into me, judging by his breathing and extra deep and painful thrusts into me, meanwhile a hand was slowly playing with my cock as another kissed and played with my silicone breasts. A sudden shout from Steven, a violent deep thrust into me which pushed me back up the bed as he shot his first volley of sperm into me, then the familiar feeling of his warm seed filling me he seemed to be spurting more than last time and with some force as I felt each jet of his sperm force its way into me.
I was lost in the moment as he grunted loudly on each thrust as he continued to flood me with his creamy spunk. At this point I'd do anything for him, little did I know that I'd be doing just that as his friends waited their turn.
He withdrew and kissed me softly behind my ear lobe , He then told the assembled group ‘ she's all yours’ , a sudden realisation that this was it, what I'd fantasised for so many years and confided only with my friend was about to become a reality as the group of now naked men closed in around me, now my body was covered in straying hands . The hand that was holding my cock let go, he got up to the end of the bed, I had a quick peek to see who it was, all I did see was a massive cock pointed straight at me, the other men had backed off slightly, some slowly wanking themselves ready for their turn. ‘ok you slut, let's see how you cope with a real cock’, that actually frightened me as he grabbed both my legs, parted them and pulled me back down to the bottom of the bed like a rag doll, I hadn't imagined anything like this would happen tonight , my legs now pulled upwards and lifted up and over his shoulders as if I weighed nothing , it did feel a little uncomfortable at first but soon got used to it again.
With a pillow now placed under my back to help him penetrate me as deeply as possible
I got to see his long thick cock, slightly bigger than Stevens but thick, really thick, it was now I realised this is what I wanted, or what they thought I needed? Whatever it was there was now no going back. ‘Don't worry Christine, I'll lube it first’ to laughs from the small group he said as he rubbed some lube down the length of his cock Once done he started the ritual of sliding that massive cock around and over my now leaking hole, slowly teasing me, another body had replaced him on the bed and started playing with my cock. I wasn't sure if I could stop myself from cumming but these guys knew how to ' edge' me to the point of no return then stop short, Meanwhile the cock about to enter me was still teasing me. He sensed I was ready for him and placed the swollen purple head of his monster cock against me. He pushed, my sphincter refused , he pushed again, this time my body accepted the tip of his cock, I cried out , the width of his cock was stretching me in ways I'd never contemplated! , the most I'd ever been. More lube was applied to his cock then he pushed again, I opened my eyes to see everyone was watching as his cock slowly forced it's way into me, every push I cried out as he pushed resulting in a couple more inches forcing it's way inti me , it was painful, I'll admit it but the pain slowly subsided, another few inches into my stretched hole , the same, pain then ok, he was making sure I could take his large cock, a voice coaxed him on, go on, fuck that slut, That did the trick as he forced the last inches in, I cried out which seemed to captivate the attention of those gathered around us , I cried out again, this was a totally new experience for me ,he seemed to like that as I gripped the bed sheets tightly, again watched by these men , all at least twice my age as he finally slid his cock into my now sore and stretched sphincter.
. He waited, like a gentleman I guess, for me to get used to his meaty cock and when he was satisfied, started slowly moving backwards a little and forwards, taking deeper and deeper strokes as he did, boy, he knew what he was doing as he slowly started to fuck me in front of everyone, his cock surprisingly now started to effortlessly slide into me.
Then his demeanour changed from the caring lover into a more masterful one. His thrusts started getting harder as his excitement built up, accompanied with some pain as he pounded me backwards into the mattress. In one manoeuvre he pulled out, turned me over and pulled me up effortlessly onto my hands and knees, and ploughed straight back into me. That really made me cry out loud, I was really thankful for all the lube we both had applied, otherwise that would have been more painful than it sounded.
‘Right you sissy , now your going to be fucked like never before’
, now that did worry me as I wasn't at that time used to be spoken to like that, he continued to reposition himself to penetrate me once more
Thankfully he'd already stretched me to accommodate him but it still hurt for a moment then pleasure again. He started fucking me very hard, as if showing off to the other men waiting their turn, my little cock swung with each thrust of his cock, his balls slapping on my bottom on every stroke, I closed my eyes and prayed he'd finish in me quickly, the pounding went on for what seemed forever then the first signs of his climax started, he grabbed my hips tightly and pulled me as far back towards his thrusting hips as he could to penetrate as deep as he could, the now familiar swelling of his glands and the twitching of his cock signalled the first hot inseminating sperm shooting into me, a few more hard thrusts produced more sperm, a warm feeling in me told me he was another heavy cummer, 3 large jets I think with several smaller ones to fill my sissy body, he waited until he became soft enough to withdraw from me without causing me pain, the perfect gentleman again!
Once out another cock replaced it, a medium sized cock I guess as it went straight in to the cheers of the assembled group, now helped by the copious amount of spunk and lube still inside me.
His cock i remember well, it felt different as had a kink in it which made his urgent thrusts more pleasurable as it rubbed against the walls of my passage, a strange sensation as it rubbed past my prostate, a pleasure I'd not experienced before but over the years would increase the sexual intensity of me being taken in such a manner.
Sadly he didn't last long and shot his load into the sea of sperm now swimming within me. He was replaced by another who tried desperately to fuck me but now full of sperm was making it difficult but he fucked fast and hard, screaming slut at me as he came, one last person decided to have a go, I was full of sperm which now was leaking out as he helped himself to my now gaping, sore behind. He pumped away for some time, slurping sounds as sperm was now bringing forced out of me, sensing he wasn't able to cum, he pulled out and came round and pushed his cock into my mouth, suck it you sissy bitch he ordered, I instinctively played with the head of his cock, a larger cock replaced him, now the pair of them fucked me, he didn't last a minute with my tongue expertly licking his glands, in one thrust he yelled out, pushed his cock as far in as he could resulting in, thankfully as he'd already inseminated me not an hour earlier, only a couple of jets of cum shooting straight down my throat causing me to cough as it slid down, I pulled back to savour the last few spurts, I really love to milk a cock dry with my mouth, Steven had taught me well! he looked more than satisfied with that, whoever was pounding into didn't last long which I was thankful for , a loud shriek announce his climax but a very disappointing amount of sperm was shot into me.
I really was starting to enjoy myself!, the beginnings of a duddy cum slut was born!
Once he'd finished I was Instructed to lie on my back, my cock pointed to the ceiling desperately wanting release, one of the group said I think she's ready to cum, the assembled group crowded around the bed for a better view, I think this is what they were all actually waiting for and an experience literally mind blowing as the guy who had been expertly edging me on and off throughout the session moved in, kissed my pre cum soaked cock and licked it off, smiling at me he grabbed a bottle of baby oil and applied some to my solid aching cock, it's veins showing prominently down it's shaft. Slowly and expertly he moved his finger and thumb up and down my shaft watched eagerly by the group. Not sure why they were taking such an interest in this but I was going to find out why very soon.
He continued to slowly move his finger and thumb the whole length of my shaft, paying particular attention to my swollen glands now covered in pre cum adding to the slippy baby oil, it felt fantastic. I think I lasted perhaps 2 minutes as I strained my hips upwards to get him to finish me off, he told some of the men to hold me down as something spectacular was about to happen to me, then it happened
A feeling I had not felt before started to well up in my groin , my balls my cock , then suddenly my cock painfully erupted, the force of it made me scream out loudly as I shot my first stream of cum clean over my head to the cheers of the group, my god I thought , what has he done to me. The second was just as forceful but hit me in the face as did the third. My body was trembling uncontrollably, I'd never felt like this ever, no wonder I was being held down!
I cannot describe it but the trembling lasted well over 10 minutes after I'd finished cumming. More Cheers from the mesmerised audience at this spectacular display of forced cumming, I was actually in tears as he bent over and kissed me then casually walked away to applause from the group.
In the corner of the room I noticed Steven and my friend sporting nice hard ons , apparently for me as we're the other cocks. I was told to take my maids outfit off, ‘don't want it ruined’ Steven said to the small horny group. Now naked, my poor cock now limp and still oozing sperm , they all approached me, cocks in hand and started to masturbate over me, another first fir me as one by one they unloaded what spunk they had left over my face and cock, they treated me like the cheap whore I'd become for them, Steven was the biggest cummer, several huge shots of sperm shot over me making a real mess of me, AGAIN ! My friend added his contribution to finishing the cum shower, an instamatic camera was produced and several photos of me covered in all their still warm cum were taken. Once finished I was allowed to have a shower to wash all their man juice off me, i didn't say anything at the time but I did eat some of their deposits off me in the shower, the texture in my mouth was divine for want of a better word I put a dressing gown on that was left for me. I came down, the party was over and Stevens' friends were gone, just the three of us.
I was too tired and sore to do anything but Steven and my friend had a good night by the sounds I kept hearing.
This was one of many gang bangs Steven arranged for me, I think he enjoyed sharing me with his friends . I had many threesomes though with Steven and his friend who gave him a good seeing to that night! His name was Mike, another 40 something who adored sissy maids. The next 18 months were the best ever!
I did see his friend again who had expertly wanked me off that night, yes he really has a talent!
There'd be more times like this as Steven pushed my boundaries and made me more daring.
The ultimate gang bang where Steven shared me with his friends was on the horizon and one I'll remember fondly for a long time.
To be continued?
