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Ann introduces me to cuckolding

"Early in our relationship, Ann tries me out with her friends"

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Author's Notes

"Apologies, this story is out of sync but if you've read the others you'll know it's the second to last in this series"

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 also was 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!, that did hurt, 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 stil impaled on her strap on.

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 attached a lead to it. Then she said that whoever is holding the lead I'd be Thier plaything until she reclaimed me. Ok I thought, this is new but also exciting, thinking of 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 thongs, which I'd find out later were a little 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 untill 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 came 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 wasn't allowed to 'play' as I'd need to save myself for later. Once out I slowly got dressed , suspenders then stockings, I always love the feeling of my legs in sheer stockings so 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 mesh thong that left nothing to the imagination,I'm sure we got the wrong size as even flaccid I struggled to fit in it but that was intentional I discovered 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 handywork 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 the tight fitting g string. 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 for the better, 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 African 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 Visable in the front seat or Ann now sat between another African gentleman in the back. They all knew each other so wasn't overly worried, now all in, the car drove off, the driver, also an African gentleman 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. 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,the ultimate tease but this was a taster of our new life style to come as a cuckold couple, one we'd enjoy A LOT!

We finally arrived to what looked like a old converted barn they were renting whilst staying over on a business trip.

Ann by now had managed to recompose and button up her dress and stepped 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 forgot 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 before then recognised it from one of Ann's photos.

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 Ann had 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 as I got up then showed me to the kitchen. Once in the kitchen I got 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 telling me how I'd be loved tonight like never before.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 Thier humiliation of me 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 of mike's fully erect. On your knees slut, I'd what I was told,he moved in front of me and told me to pull his boxers down, slowly I tugged at them untill over his hips,only his cock now 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 unvailed 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, I think he got about five, maybe six inches in my mouth and throat and that was it, he tried to shove more in but I just choked. I guessed I could see another five or six inch in front of my face. This site had Ann openly playing with herself at the spectical unfolding in front of her, the man next to her rubbing her leg with encouragement.

Right slut, hands and knees here pointing to the carpet. 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 pleasurable 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 stil a fat cock. 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 the end of his swollen cock found me and he pushed ever so gently forward untill 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 thier 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 love making began as he slowly started to rythmaticlly 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, what a slut I am I thought as thrust by thrust bought his friend to his climax  shooting copious amounts of salty spunk into my mouth. He withdrew and let his friend has his fun 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, 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 to mine. He lowered his head to my neck and kissed my neck as his swollen cock finished it's mission to inject all his love  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 friends heart was beating frantically against me as his last drops of his seed made its way into my now willing body, I was enjoying the fact 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 lead back to the sofa where the three of us sat down, from behind one of the doors I could hear Ann , her cries of ecstasy were unmistakable, as was the bed they were on, creaking with evey thrust of another massive cock trying to seed her. 

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 wearing her unbuttoned dress 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 jucies, 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 jucies and a bit of pre cum. His cock was solid so 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 penatrated with his  condom encased monster cock. With  the mixture of her jucies and the lubricated condom, he effortlessly slid straight in causing Ann to buck and twist 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 and encouragement when the tip of his cock hit home. 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 taughtness 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, one we'd enthusiastically embrace.

Once he withdrew from her I was ordered to remove the remains of the condom and clean him up before turning to Ann to clean her up for her final fucking,  my tounge worked around her sloppy fanny, 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 thier 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 12+ inches into her, 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 penatrated. I watched as he lubed his smaller cock and placed it at her enterance, slowly he pushed into her untill his balls were touching her bum cheeks. Never 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. A few pushes and amazingly he was in! 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. 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 fanny quickly followed by the other

They collapsed ontop of each other as I was 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 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 totally stretched, 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. 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 disheveled, 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 missing a few buttons, covered in dried on spunk. 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 thought cuckolding was good for us, Ann agreed with a sneaky smile on her face. 

Published 
Written by Christine63

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