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My first time Pt7 The next level

"Ann decides to test me to see just how far she could go"

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Author's Notes

"The final part of my early years which would pave the way to some amazing experiences"

I'd always told myself that the last gang bang would be my last now that I'd been claimed by Ann, my future wife who was also now my mistress so I was in heaven. By now things had quietened down and for a while Ann had me all to herself, our sex life was amazing, she being the dominant partner she'd really put me through my paces and if satisfied I'd be allowed to fuck her, she liked me her sissy slut and I really enjoyed being her slut and lover when allowed. Meeting Ann by chance that night was fate. We still saw Steven or Mike or both together so sex was plentiful to say the least. During one session of me restrained face down on the bed with a pillow under me to allow easier access for Ann to plough me with her smaller 8 inch strap on, she said to me ' I bet you wish you'd be gang banged again like before' with something a bit bigger , an off the cuff remark I though but secretly it had crossed my mind so played along. That suggestion, or was it?. seemed to excite her to the point she suddenly thrust that strap on all the way!, I cried out then bit into the pillow to muffle the sounds, that did hurt, something she really enjoyed doing to me, but I guess being double ended she got her climax she needed. Now calming down I could feel her firm warm breasts and her hard erect nipples pushed Into my back, whilst still impaled on her strapon.

 Once she'd had her fun, we laid together whilst she 'sold' me the idea of meeting some friends she knew for that ' extra' fun whilst she watched. Well, she was my now mistress and lover and me being that submissive cum slut she fell in love with I could only answer Yes. Goody she said, here's something I want you to wear from now on when we're entertaining and produced a black dog type collar with the word Slut on it. Try it on for size, I did as I was told, it felt strange at first, don't worry my slut, you'll get used to it then she attached a lead to it, in a giggly voice ‘whoever is holding the lead, then you're their plaything until I reclaim you, understand’? I nodded, confused as to what was happening , this was new but also exciting thinking of my new role in our relationship. A few weeks later when I'd thought she'd forgotten what was said, she announced that we were invited to her friend's house for an impromptu party with a few friends, how many i asked? Two maybe three, not like before but you won't be disappointed, trust me she said with a knowing smile. With that we went shopping, not for her I was to find out but me! Through several lingerie shops for something sexy and a few other things written on a list not in her handwriting, this sort of fazed me as for once , neither of us were in control. Whilst shopping we got some questioning looks from some shop assistants as she sized things against me but eventually she was happy with the items 'required' then went round a few clothes shops to finish off my outfits, wasn't sure why I'd need more than one outfit but pleased there was. So, now ' kitted out' with some lace and satin panties, which I'd find out later were intentionally on the tight side, red suspender belt and sheer black stockings, knee length black shiny pleated skirt, silk like black blouse and a nice, but tarty, pair of high heels now I could actually walk confidently in them, the other item was by request from a sex shop, a very sexy translucent baby doll and matching panties. Whilst there Ann purchased some lube and an applicator, the assistant giving Ann a knowing smile. Up to that point I was oblivious as to what was in store for me/us? as steven or Mike never needed an applicator to apply lube and they were large, or so I thought! A sudden flash of panic and excitement came over me but was reassured that I'd be fine. Once Ann had confirmed we'd fulfilled their requirements a date and time was set, now just a waiting game until i met Ann's friends for the first time. Finally the wait was over, i was nervous as I'd not met her friends but eager to please her also. We were to be picked up at 7pm and driven over. Their request was that I come over already dressed which threw me as I'd never stepped out the house dressed as Christine so definitely a first, if not apprehensive at the thought of being seen out dressed. We both showered but weren't allowed to 'play' as I'd need to save myself for later. Once out I slowly got dressed , suspenders and stockings, I always love the feeling of my legs in sheer stockings so I had a few strokes which started a chain reaction , NO!, Shouted Ann as my cock started to swell with the sensation, Later! With that I removed my hand and continued to dress.The next item, my lace panties  that left nothing to the imagination, I'm sure we got the wrong size as even flaccid I struggled to fit in them but that was intentional I'd discover later. Next the pleated skirt which slipped effortlessly over my stocking legs. Once on,  Ann got me to sit whilst she applied my makeup so as not to get any on my blouse. On went the ruby red lipstick and heavily applied blue eyeshadow and mascara and a bit of rouge blusher to finish. On went the bra with 36C inserts creating a nice firm bust in my blouse and shoulder length blonde wig, not forgetting my slut collar, transformation complete. Once happy with her handiwork she took a few photos for our private collection and future reference. Ann then changed into a black knee length deep V neckline button up dress that glistened in the light, not only stockings visible through the thin material, but bra-less revealing an impressive outline of her breasts and nipples causing me some discomfort as an erection ensued but trapped in my tight fitting panties. This was totally different from her usual attire but found out later that was also by their request, her friends sounded quite interesting indeed. This evening was different in so many ways to our usual meetings as Ann was also the dominant partner but tonight she just looked so feminine and sultry, this was going to be a turning point in our sex lives ,  I just didn't know it at the time. Around seven o'clock an expensive looking car turned up on our drive and pipped it's horn, I slipped my high heels on and we made our way to the car, passenger windows dark tinted so at least I'd not be seen in transit. How wrong I was! I went to the back door to get in, the door opened and a fit looking tall black gentleman, mid to late 30's got out and beckoned Ann to get into the back whilst I was told to get into the front, not sure what I was more worried about, me being Visible in the front seat or Ann now sat between another black  gentleman in the back. They all knew each other so weren't overly worried, now all in, the car drove off, the driver, also black , patted my knee and said ,"Don't worry love, we'll be round ours In about 20 minutes. To be honest I was more worried about being seen dressed as I'd never ventured out the house dressed before but this was almost exactly what Ann and myself often talked about in bed, now I was getting a little excited at what might happen to us as my cock tried it's best to burst through my tight panties.

Their house was situated just outside a village down some narrow lanes so no chance I'd be seen? I happened to catch a glimpse in the rear view mirror to see that Ann was now the centre of attention, top buttons of her dress undone and her breasts exposed to the attention of the two men with her head back and eyes closed as they played and sucked at her breasts. I can't describe how I felt seeing this as this was the first time I'd see her with another man in my presence and obviously enjoying it ,the ultimate tease but this was a taster of our new lifestyle to come as a cuckold , one I'd have to get used to.

We finally arrived at what looked like an old converted barn. Ann by now had managed to recompose herself and button up her dress, stepping out the car helped by one of the men. I got out and got used to my high heels again when Ann said , Christine, have we forgotten something? Holding the lead in her hand. She came to me and attached it to my collar and calmly asked ' who wants her' one of the men from the back reached over and grabbed it , looking into my eyes saying ' your mine for now' All this was new so not sure what was expected of me, so a steep learning curve. We walked into the building into a lavish large room, I had a feeling I'd seen this room before then recognised it from one of Ann's photos of her naked on the carpet. Ann made an excuse for both of us to use the bathroom, just to finish off her eyeliner she said. Once there she gave me the applicator bought from the sex shop, now filled with a thickish lube, use this, you may need some. Now I was unnerved, she knew something that I was about to discover. I inserted it and pushed the plunger to feel the cooler lube make its way in, lining my passage. Once done she applied some eye liner and we rejoined the group. We all sat down, me now sat between the two men that had played with Ann in the car and the driver sat with Ann on a smaller sofa facing us. My temporary master ordered me to the kitchen to get us all drinks, slapping my bottom we both  got up as he walked me to the kitchen.

Once in the kitchen I was given a large tray ,glasses and a bottle of scotch and vodka, whilst shutting the cupboard door he came behind me and hugged me round my waist whilst pushing something into me ‘ have you ever been with a black man before ‘ he asked me . Suddenly I became all flustered, not quite sure what to do, instincts kicked in as i reached round best I could to feel what it was being pushed onto me Oh my god I thought to myself, he was getting excited at the prospect of fucking me but what I was feeling was large like I've never felt before. He reasserted his dominance over me with another push before saying , come on slut, were going to fuck you right in front of your woman. With that he grabbed my leash and led me back to the other room with the drinks. A few drinks later we , well at least I was, more relaxed which the two guys sensed so started my  humiliation in front of Ann which was her plan after all?. The two men with me had now removed their trousers and shirts wearing only boxers, my eyes opened wide at what I saw, that lump was his cock! still flaccid but already huge, not far off  Mike's fully erect cock.’  On your knees’, I did  what I was told as he moved in front of me and told me to pull his boxers down, slowly I tugged at them until over his hips, only the top of his cock stopping them dropping down completely due to its now growing size. The outline of it, large, very large. I ran my hand over it, as far as I could tell it was bigger than mike's plus it was fatter. Finally I unveiled what was hiding in there, my eyes widened, I saw Ann giving it a concerning look as well as it wasn't fully erect. Ok sissy , suck it, make it ready for you. I nervously licked what precum was on the tip and spread it round the bulborous head to help me take it in. It would have been impossible to take it all in as the thickness was making my jaw ache as I sucked on that massive shaft, I think he got about five, maybe six inches in my mouth and throat until I couldn't breathe, this was a new sensation for me as I guess I looked more vulnerable, just what he was looking for, for the moment , I was his and his to do whatever he wanted to me.  That was it, he tried to shove more in but I just choked. I guessed I could see another five or six inches in front of my face. This site had Ann now openly playing with herself at the spectacle unfolding in front of her, the man next to her rubbing her leg with encouragement. Right slut, hands and knees here pointing to the very carpet Ann had been previously fucked on. :You look like a tight sissy so I'll lube myself'  hearing that was a relief given I'd already lubed myself so should make the experience more manageable for me at least.

 Once done he got on his knees behind me for the inevitable entry. His friend now disrobed at the front with a more manageable 8 inch but still a fat cock, he put a small bottle under my nose ‘ sniff it bitch, it'll make it easier for you’ no idea at the time what it was, I took a deep sniff, the room started to spin as suddenly I was very relaxed, suddenly I was theirs to humiliate me in front of my partner, what would she think about me after this? 

The man behind, who's name turned out to be Simon, tried several times to mount me but failed as his girth was large so his monstrous cock kept slipping past my sissy hole. His next attempt was more successful as my sphincter suddenly relaxed, the end of his swollen cock found it as  he pushed ever so gently forward until my body accepted his hungry cock, the first inch or so stretched me open and slowly slid in, Initially it was painful but as I got used to this oversized cock my body started to accept him and slowly the pain subsided, both our lubricants were doing their job. Ann had watched intently as her friend slowly forced that monster cock into me inch by inch, her hand pleasuring herself had now been replaced by her friends hand, the unmistakable tenting of his boxers were failing to hide he also had a large cock but was told to look away by the man fucking my face. By now I'd guess I'd got a good eight inches in me, stretching me in all directions as he now slowly moved in and out, pushing deeper on each stroke. Ann was called over to see his handy work, enjoying yourself slut she said, through gritted teeth I replied yes as he tried to get the last few inches into me. With that Ann and his friend disappeared into another room whilst his friends had their fun with me, his last push effortlessly sank in, slight pain then nothing, hey look at this he said to his friend, she's managed to take it all, his friend laughed then the frantic fucking began as he slowly and  rythmaticaly  started to slide in and out, going slightly deeper each time then pulling right back, I didn't think there'd be any danger of him slipping out, each push back into me forced me forward to engulf his friends cock deep into my mouth, I was actually enjoying this, probably more than should have as my cries were stifled by the cock now fully in my mouth.

 What a slut I am, I thought as thrust by thrust brought his friend to his climax shooting copious amounts of salty spunk into my mouth, I did my best to savour it's texture and taste as his cock spurted his creamy spunk into my mouth, I managed to hold some back in my mouth and roll it around to savour it's texture, seeing this , he withdrew, show me bitch, opening my mouth to reveal his fresh warm sperm waiting to be devoured, ‘ swallow it bitch ‘ without hesitation I consumed all of it in one go , ‘ show me’ opening my mouth revealed id done what any good submissive cum slut would do, now empty with just a dribble at the side of my mouth. 

Now  his friend was about to finish me off as now, his thrusts into me were getting more powerful as his balls were slapping against me on each stroke, thankfully he was getting close to cumming, a few more minutes of his steady deep thrusts then the inevitable, his hands now around my swinging breasts inserts , he gripped tight and said ' time to breed you, you sissy slut' and with that he pushed hard into me and pulled the lead back forcing my head upwards to arch my back, I must have screamed the house down as his final thrusts felt like he was splitting me in two ! he made a loud roar as his glands swelled, the familiar twitching, then a warmer than normal sensation as he came powerfully into me, several powerful spurts followed by a few smaller spurts as his spunk made its way from his body deep into mine. He lowered his head to my neck and kissed my neck as his swollen cock finished it's mission to impregnate me as the last remnants of his seed found its way  Into me. His friend now hard again, wanking himself ready for his next conquest , building up his seed, though not for me as I'd soon find out. His friend's heart was beating frantically against me as his last drops of his seed made its way into my now used  body, I was amazed that  I made him cum so hard into me, what a transformation from my first fumbles with my friend a few years ago! Once his climax finally subsided and he was soft enough to pull out, we went for a shower to clean up, much fun was had in the shower as I cleaned his massive cock, unaware it was now for Ann. I was told to put the baby doll outfit on and the black satin panties plus a pair of hold ups he'd got me to wear. Collar and lead back on, I was led back to the sofa where the three of us sat down, from behind one of the doors I could hear Ann , her cries were unmistakable, as was the bed they were on, creaking with every thrust of another massive cock trying to breed her, thank god she was on the pill! 

‘I think we should see what going on’ his friend with the smaller cock said, and with that we all entered the room to see Ann flat on her back on a grand four poster bed, legs raised,  her unbuttoned dress splayed out under her to reveal her firm breasts and slender body, her face and chest bright red showing she had by now climaxed several times being fucked relentlessly , each thrust pushing her deeper into the mattress. On seeing us enter the room he stopped and slowly withdrew his large cock, about ten inches at a guess, glistening with Ann's juices, she looked frustrated that he'd withdrawn before cumming but he wanted me to suck what cock I could fit in my mouth, I slowly moved over and started to suck the end, the familiar taste of Ann's juices and a bit of pre cum. His cock was solid so I was wondering how Ann managed to take it all. He reached over to produce a condom, bit late I thought, here put this on me, I want you to see something. With that I opened the packet and with some difficulty after stretching it to fit over the end of his cock rolled as much of it down as physically possible. Once satisfied I was told to kneel at the side of the bed so I could witness at close quarters Ann being penetrated with his condom encased monster cock. With the mixture of her juices and the lubricated condom, he effortlessly slid straight in causing Ann to buck and twist and cry out as he filled her again. Once fully home he started fucking her, his buttocks rising and falling at a fast pace like a well oiled machine. Ann was loving this judging by her moans, her fingers clawing into his back as she held him tightly,  the tip of his cock pushing deeper into her that I ever could, a sobering thought. 

I noticed as this went on the condom looked very tight on his cock , each thrust putting more strain on it, suddenly he increased his thrusting into her as his climax was about to happen, I could see his full length push into her, the rubber straining to contain his cock as he pushed in, the tautness of the condom suddenly went slack as it finally failed to contain his monster proportioned cock and enter her again ,his final climatic thrusts into Ann inseminating her, I must admit I did find that very erotic and exciting to watch even if it was to humiliate me into showing me nothing was going to stop Ann getting impregnated by him . I guess this was our first steps into the cuckolding scene together as a couple , one we'd enthusiastically embrace. Once he withdrew from her I was ordered to remove the remains of the condom and clean him, his taunts of, “ I've got your bitch pregnant, she's having my baby’ I don't know if he meant it or just saying that to humiliate me, my partner bred in front of me and I couldn't do anything. Did he know she was taking contraception I wonder? 

Once I'd finished cleaning the cock that had just impregnated Ann it was time to clean her now gaping pussy  for it's final fucking, my tounge worked around her sloppy pussy , retrieving a heavy deposit of his sperm. All this time I hadn't been allowed to cum myself so the frustration was getting evident with my rock hard cock leaking precum into my panties, one of the men pointed it out to the others and laughed. I'd get to cum by someone's hand soon though. We all had a rest and a few more drinks. We both had a large vodka and Coke. It was now getting to 11pm so we're shown back to the bedroom, we hadn't planned on staying the night, however they had plans of their own. I was ordered to put my heels back on and lie on the bed, my cock now really straining at my panties to be used. the man with the biggest and fatest cock then laid next to me and asked Ann to straddle him, this would be difficult as from experience of him fucking me earlier she'd not get him all in, WRONG! I watched in amazement, she slowly sank all 11+ inches into her, his cock was a real monster as we were both sore days later! Once satisfied he told her to lay down on top of him, then the guy with the smaller cock came behind her so she could be double penetrated. I watched as he lubed his smaller cock and placed it at her anus, I didn't think she was Into that sort of thing but here she was, right next to me double penetrated!

slowly he pushed into her until his balls were touching her bum cheeks. Never have a camera when you need one I thought. Then it was my turn, the other came in from the bottom of the bed and grabbed my heels and pulled me towards his now fully erect cock, glistening in pre cum, in one movement he pulled my legs up onto his shoulders and ripped off my flimsy satin panties and placed the tip of his huge cock next to my now vulnerable hole. It's head parted what was left of my sphincter and pushed in, the next part was a little painful as he the forced his cock into me, inch by inch he pushed into me, I cried out as he mercilessly pushed ever deeper Into me, it was a relief when I finally felt his balls pushed against me, he was set, now it began.

Ann grabbed my hand as all of them fucked us. The two men now fucking Ann had a system of pushing in and out alternativly which Ann was enjoying by the sounds she was making, not her first time I thought! .

 The man fucking me was a bit more tactful given I'd not long been fucked by the biggest of the cocks I'd ever seen in the flesh! Nice long steady strokes, Ann however was being fucked at a faster pace now as the two cocks pushed into her causing the bed to creek with every thrust . I think the naughtiness of the situation got the better of them as they both started to breathe deeply as their cum made its way up and into her now well used pussy quickly followed by the other into her arse, Ann squealing with delight as they pumped their hot sperm into her.

 They collapsed ontop of each other, Ann sandwiched between them as I was still being fucked., suddenly he grabbed my cock and wanked me off quickly as he shot his final load Into me, I was so pent up I couldn't hold back as I just shot ropes of cum up my body and chest with one spurt landing on my lips which I licked In, that did the trick as Simon continued to fill me with his warm spunk. Once finished he slowly pulled out, my hole now sore and totally stretched, my now gaping hole  unable to hold his load of spunk, it leaked out onto the bed. Ann at my side also leaking copious amounts of sperm onto the bed sheets, what a mess they'd made of us. Right slut Simon said to me , shower and dress. Yet another shower and dressed back into my skirt stockings and blouse I went back and sat down waiting for Ann. I could hear sounds from the bedroom, the creaking bed, these guys were insatiable! A few minutes later Ann came out, red faced and went for a shower, half an hour later we were all having tea like nothing had happened, although my sore gaping hole was telling a different story, Ann had similar complaints!. By now it was just past midnight so we were offered a lift back home, arriving in a bit of a state, both of us looking a bit dishevelled, making sure the neighbours didn't see us like this. Once dropped off at home Simon said to us, see you soon, I didn't get the opportunity but I know Ann did. One afternoon she went and arrived back at 2 in the morning, her face, hair and dress, which was ripped and missing a few buttons, covered in still wet spunk stains . Apparently a few friends popped over unannounced ending in a bukkee shower.. I wish I could have seen that, Ann patted her bag and said we'll see. I said to Ann that I enjoyed it, not so much watching other men fuck her but I guess that's par the course if your a cuckold partner, I said to her perhaps we could do it again once I'd got used to the idea Ann agreed with a sneaky smile on her face, what was she planning?

Published 
Written by Christine63

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