caught

I will start with some background that should become relevant as the story progresses.

I have been married to my second wife for 10 years, we are both in our mid fifties and K is still a very attractive woman, not the same statuesque beauty she was in her twenties but now a mature sexy woman with a few more curves. I think I have always boxed above my weight as they say, with both K and my first wife being far better looking than I should have managed. Although reasonably tall and a bit athletic when I was younger, time has not been so kind to me, receding hear, far to many extra pounds in the wrong places etc has not only affected my appearance but also sexual appeal and performance - so not only has my already modest dick (4 1/2" on a good day) suffered from the extra layer of fat but also any stamina has long gone.

K has been a legal secretary for most of her career mostly on prosecution side but recently started working for the public defence office - where she comes into far more contact with the offenders than she did previously, I am in middle management, desk bound and stressed and frustrated

A couple of months ago I had been having difficulties at work and decided to have an afternoon off to relieve some stress. so I went home to do something that did just that for me - I had started wearing woman's underwear, it started almost a year ago, first just trying on some of K's, then gradually getting my own quite nice stash of lingerie.

Well I had got out my hidden collection and tried a few different combinations, admiring myself in the mirror as I went along, I ended up in one of my favourite sets, pretty pink panties and Bra (20D filled with a pair of lovely large breast forms that truly feel amazing jigging up and down as I walk around the room) a red sheer short lace nighty, hold up stocking and bright red 4" pumps, I was feeling very nice, not only losing all my work stress but also all track of time.

My bliss was shattered by K standing in the doorway exclaiming "what the fuck are you doing?"

I spun around to see K standing with her hand on her hips and a very stern look on her face "well?" as I turned redder than my beautiful high heel shoes and stammered for an answer. After a minute of composing myself I tried to explain that I had found this to be a good stress reliever and therapeutic even for my woes at work.

K was a little sympathetic to this but was concerned that I would next want to start dressing fully as a woman etc and was not prepared to be humiliated by having everybody know she was married to a sissy crossdresser. However despite her concerns, K decided that if I liked panties that much, then I was to wear them all the time and through all my male underwear out.

She also insisted that I wear my nighties etc to bed, this put paid to any sex, as she firmly told me she had no interest in having any sort of sex with a man in panties and lacy nighty (we had been having sex once a week for some time - well when I say sex usually it involved me licking/fingering K to orgasm then pleasuring her with a nice large dildo and wanking off as she finished fucking herself with the big rubber cock, as I could hardly have the energy to climb on top and try and give her any sort of satisfaction with my little 4" dick)

Over the following weeks K became more assertive with me and insisted I wear my lingerie around the house more and more, giving her constant opportunity to ridicule me about wanting to be a girl. She also started telling me about a client at work that had been trying to chat her up, he was a bad boy biker type, in his mid thirties, up on charges of extortion etc (innocent of coarse, the cops had it all wrong!!) after a couple of weeks of casually mention about this guy hitting on her, K said that she was going to accept his invitation for a ***** on Friday night so she would be a little late home.

Friday night came along and as it got later and later with no sign of K, I decided to go to bed, in my usual bra panties and babydoll nighty. I was more or less asleep when K appeared at the bedroom door, in quite an inebriated but happy state,

"I'm sorry, but I might have told John a bit much about our domestic situation"

"what are you talking about K" I replied as I awoke in a confused state

at this point I realised John (the bad boy biker) was standing right behind K

"I told John all about your fetish and he didn't believe me and wanted to see for himself"

"but...." before I had time to finish John had stepped forward and pulled the covers off me - exposing my pretty pink panties, full bra and a pink see through nighty

John stood there with a huge smirk on his face, " fuckn' hell........" shaking his head " I've seen some sick **** but this takes it for sure........."

K interrupted "John didn't believe me, he thought I was just trying to put him off, so we made a bet, he said if I was telling the truth, he would fuck me in front of you.....so you better get sucking on his cock like a good girl"

"but I just like dressing in lingerie, it helps me relax, i'm not gay..." but by this time John had his cock out and semi hard in front of my face - "you look pretty gay to me" john sneered, as he grabbed the back of my head with one hand and direct his growing cock into my mouth with the other, he was a large, much younger, fitter and more powerful guy than me, my resistance was futile and he soon had his cock in my mouth, demanding that I get him hard so he could fuck my wife properly as she had obviously be missing out badly having me for a husband.

John pushed his cock in and out of my mouth, getting harder all the time, stroking his shaft every time he pull back out, lubricating himself in preparation for my wife. John paused, his attention drawn away toward K, she had removed her skirt and blouse, and in a very cruel trick, she was wearing matching bra and panties to me ( K, however, looked stunning in them unlike me who looked somewhat ridiculous) John laughed, noting the comparison himself and suggesting K was bit kinky herself, but said it mad him very horny.

John was no longer interested in me and stepped toward K sitting on the edge of the bed and immediately directed his big cock into her mouth, K was really enjoying her work

"you need to take lessons of your wife" John laughed "she knows how to suck cock, you are going to need a lot more practice you stupid little faggot" as he again approached me and pushed his cock into my mouth "now suck me properly, work my cock in your mouth you little pussy" I took his cock as far into my throat as I could, gaging continuously, doing my best. I must of been getting it right as he began telling me I was a good little cock sucking bitch. He then returned to K, who had been enjoying the show and encouraging John, but now wanted his attention, Johns cock was now rock hard and K was admiring it and stroking him with both hands on his impressive shaft.

"do you think I will enjoy this" K asked me in a very mocking tone "looks like my favourite size....BIG, i'm sure this cock wouldn't fit inside a pair of girls panties... god, look you can't even tell there is a dick in your little panties....you really do suit panties"

K continued her *********** "I think I might get my first good fuck in ten years tonight..." then with a naughty grin and a wink ".....and I think you might too", John burst into laughter "yeah maybe your right, I might fuck your girlfriend as well, that will be a cute threesome with you two in matching lingerie" K joined in the laughter then instructed John to fuck her hard so that they could show me how a real woman enjoys a big hard cock

to be continued

Nice start!
Cuck who loves a creampie.

Very nice indeed!

thanks for positive comments

What followed was the most amazing display of raw sex I have ever seen, I could describe every little detail of his big cock stretching her pussy etc, but I know most of us have read that sort of description many time before, suffice to say John fucked K in front of me and moments are etched into my mind that I will never forget. The way K's hips rose and gyrated as she took his full length, this natural reaction and enthusiasm was something I had never seen in over ten years of trying to please my wife - not even when I was younger and fitter and able to pump away with my little dick did I ever get anywhere near a reaction like that.

The vision of a virile 30 something stud, fucking my 55yo mature wife to ecstasy and orgasm after orgasm seemed so natural. It occurred to me, I could never deny her this pleasure again. Unlike my over weight, out of condition and under endowed self, K, with the right partner, could enjoy the same sort of intensely great sex she did in her thirties (she had shared some stories of her wild times catching up after marrying far to young the first time and getting divorced in her early thirties) and she had clearly missed it.

Another outstanding memory was K's verbal appreciation of Johns physic, equipment and stamina, K had mostly been demure with such language and behaviour during our weekly sex. I was also hearing what she really thought about my lack of ability to satisfy her over the years, ******** honest and impossible to deny in light of what I was witnessing in front of me but still very deflating to my already somewhat confused ego.

John was something of a machine, big, fit and very physical - he fucked K to a number of intense orgasms, in various position (another point of envy - exotic position play is not something one can easily achieve with a 4" dick) John finished his performance in classic missionary position, filling K's pussy with spasm after spasm of cum, again K expressing her pleasure at this. Another curse of the aging male, well this aging male anyway, ejaculation is now less than spectacular to the point of sometimes being a none event

After savouring the feeling of cuming deep inside my wife's pussy John rolled off and rested for a minute or so while K lay exhausted beside him, however still able to caress his still reasonable hard cock, it appeared she still had plans for him.

the next thing I know John had jumped up and grabbed me by the back of my head and dragged me forward, this time however, it was my wifes pussy he was directing me to, rather than his big cock. He pushed my face down between K's spread legs an ordered me to lick her and eat his cum. I did not mind this duty, as licking pussy was something I am quite good at (with a small dick you need to be good at this to at least give woman a good orgasm that way) and had wonder what it would be like to service a woman after she had been well fucked.

I took to my job with quite a bit of enthusiasm, and could hear K moaning with approval, I noticed a change in noise and glanced up to see K sucking and stroking Johns cock, working hard to get him fully hard again. I returned to concentrating on K's pussy thinking she would soon be enjoying another vigorous session.

I was surprised by a large hand firmly pressing in the middle of my back and my panties torn down, my babydoll night pushed up over may waist, leaving my bare arse in the air - very startled, I looked up at K, to see her with a very wicked smirk "you have been pretending to be a girl for long enough, now you are going to find out what it's like to be taken like a girl"

I felt Johns cock starting to press between my butt cheeks. I began to protest, but john just added more weight to the middle of my back, ******* my face hard into K's wet pussy and raising my arse even more, I was pinned and my struggling was not helping, in fact just adding to John and K's mirth.

K through John some lube, which he generously poured over his cock and my bum crack. I then felt a searing pain as john ****** his cock into my virgin arse, even with John's weight on my back, my reflex reaction allowed my head to rise enough to look at K, I must have looked rather pathetic, there was almost a tone of sympathy in K's voice "oh Honey, does that hurt a little, it always hurts a bit the first time, all girls know that, but you wanted to wear pretty girlie underwear, then you will just have to get used to being fucked like a girl, won't you"

I was struggling to both comprehend what was happening and accommodate john inside me, but as I got used to the invasion and began to relax, the pain did transition to a strange sort of pleaser, john clearly sensed that I was beginning to accept his cock inside me and began to push in and out, moving both hand onto my hips, there I was on all fours, head between my wife's legs, nighty pushed up and my false tits bouncing under me as john began to get his rhythm, I can only imaging what that looked like but i do know that I definitely felt like i was being fucked like a girl, especially with the constant comments to that effect being made by both K and John.

John thrusting was affecting me, massaging my prostate, i had never had a feeling like it before, something like a orgasm but deeper inside me, not a tingling in my groin and the building to a few spasms of ejaculation, this was inside, all my body quivering. i raised my head, showing obvious enjoyment, my bliss interrupted by K voice between her laughter "honey it looks like you are enjoying that much more that the last time you came - i recall you hardly managed a dribble and a little shiver"........."you really suit being a girl don't you" .... a positive "hmmmmm" was all i could muster for a reply

the experience was too much for me and i collapsed, exhausted and unable to move let alone hold myself up, i had not been able keep up with John any longer and he was less than impressed, apparently looking forward to cumming inside me and consummating my "girliness" as he put it. John retired to the Bathroom to clean up and told K to help me into the spare room so that they could spend the rest of the night having more fun

i woke in the morning to the unmistakeable sounds of K and John having sex, the moans, grunts and rhythmic creaking and banging, i looked at the clock on the side table it was 9:30 in the morning, i starting running through the event of the night, good god and they where still fucking, incredible. then i notice a note on the side table addressed to me, i gingerly opened it and began to read

"Honey when i caught you in woman's underwear i was disgusted, i couldn't believe it, you looked ridiculous and the amount you stashed away was very concerning, but it did explain some things, especially your lack of performance in bed.

I decided to test you, unbelievably you willingly wore girly underwear when i asked you to, never trying to protest and apparently enjoying it, even wearing pretty pink panties, bra and nighties to bed complete with those big false boobs stuck on, knowing you would never have sex with me like that.

It became obvious to me you had changed and this girly stuff is more than just stress relief, am i wrong?

So finally i decided to see how far you would go being a girl, and you sucked cock, eat cum and let john fuck you, and enjoyed it, am i wrong?

It appears that you want to do more than wear lingerie sometimes for stress relief, but rather be a girl all the time, am i wrong?

Now on the dresser are two sets of cloths
One, men's Y fronts, singlet, business shirt and tie, trousers, plain sox and black shoes
The other, lacy pink bra and panties, suspenders and stockings, pretty red dress and your red 4" pump

It will be time for breakfast when you read this

If you come out of the room wearing the men's cloths, i will get up and make us all something to eat and John will then go for good and nothing more will be said about this and we will return to as it was before.

If you choose to wear the girls dress etc, you will be expected to make breakfast for john and i - you will wear woman's cloths ALL the time from then on and never join me bed again, you will do all the house work and john will be my permanent lover and also fuck you when ever he wants - but more likely it will be some of his jailbird friends who got a taste for sissy arse when they where inside, but going on last nights performance you will enjoy that, am i wrong?

I'm betting we will be going shopping for lots more dresses tomorrow, after all you will need a whole new wardrobe for work won't you, am i wrong?"


I sat looking at the two piles of clothing, the first thing that struck me was how boring the male pile was and how much more appealing the girls cloths were, those red heel were just so sexy! God was i really thinking this way, how could i go to work on Monday in a dress? (i even pondered how i would approach the situation with my female head of department, she might understand and be quite accepting) why was i even thinking about that?

I lowered my head and was instantly confronted by the view of myself in the badydoll nighty, bra and lovely boobs and my tiny flaccid penis, so small it was hardly visible. looking down i realised that i had become so accustomed to the girly underwear and glued on tits, that it had all become so natural, had I forgotten any other way? did i want to go back? could i go back and never do it again? and what about the sex? being fucked by a virile man was fantastic actually, far more pleasurable than my feeble attempts at intercourse in recent years anyway.

I had seen K in absolute ecstasy with John, would it really be fare to go back to how it was? a lazy tickling of her clit and a rubber dildo to get her off once a week, paled into insignificance compared to what she just tasted, could she really give that up? maybe we could compromise? the wearing dresses to work was worrying me, maybe K could keep John and i would be a girl all the time but at work? could K accept that, i could do everything else she wanted, cook, clean, she could have her lover and i would even accept his friends having their way with me?

How do i approach this, if i go out in the dress i have accepted the conditions in the letter and it is a fate comple, with no position to negotiate from. If i wear the male cloths (which she is clearly not expecting me to) there also may be no debate on the outcome.

to be continued

cannot wait for the next update! i am totally envious. i know that you are going to cum to love your new position(s). perhaps you might also find a gurl friend or two!!
i do hope that you will share a few pics sweetie! (of the three of you)

I'm glad you are enjoying my adventure, there is a bit to cum for sure!


As I sat pondering what I should do, I re-read K's note over and over again. I realised I had completely misinterpreted her reaction. I had mistaken her "testing" of me, for some acceptance and support for my new found fetish, so as I embraced the opportunities to dress up and play with it, and my willingness to delve even further into this depravity, sucking Johns cock, eating his cum and ultimately enjoying being taken like a naughty little slut, to me was a bit of experimentation, but to K this was undisputable evidence that I had totally committed to being a girl, was she right?

my thoughts were broken by something, the shower was running, the sounds of sex had stopped - I glanced over at the bedside clock, it was after 10:00. I felt pressure building to make a decision, they would be up soon, wanting brunch, I must make a decision. my mind was whirling, more time passed. The shower stopped, I began to panic, I stood and removed my nighty and bra, my glued on breast forms hung unsupported, I was distracted looking at myself in the mirror and feeling the weight, and thinking how great my tits looked and felt.

the shower started again, the time had come, I had to give K my decision. I gingerly entered the master bedroom, K was sitting in her robe at the dresser doing her make up, she looked at my reflection in the mirror. "whats this" she responded sharply, I began to explain all the things I had been thinking about, particularly my concerns about work, I pointed out that I really needed the job, we had nice house, cars etc but still a bit of debt. I pointed out that suddenly appearing at work dressed as a girl might cause some employment issues which could be bad for us financially.

K interrupted "yes, that is a reasonable point, however it is obvious you do not want to be a man again, or else you would not have come in here nude, so do you have a proposal for me?"

At this point John appeared from the bathroom, sneered "what the fuck, put some cloths on you pathetic creep"

"we are just negotiating that now John" K replied " well Honey, continue"

"I can agree to all the conditions, except going to work dressed like a girl, as I said, I think that could cause us financial trouble" I continued

"so, except for being at work, you will dress as a girl and do all the other things in my note" K questioned

"yes, everything but work" I replied feeling quite happy with the compromise

K looked to John and he shrugged "well she better hurry the fuck up and get that pretty dress on then, i'm hungry"

I began to leave, K called me back "you definitely understand, a girl all the time except your work?" I nodded, K continued "a complete girl, we never expect to see you without full makeup, perfectly groomed and dressed" I was a bit taken a back with this, I had not gone that far before, and what was the point I would be at home all the time I thought, but again nodded my compliance "you will need a wig and a manicure, you will need to lose weight and have a corset to give you a real woman's figure, we will do that later, now go and get dressed and come back, we will start your makeup lessons" K said with a definite air of authority

I hastily scuttled off to my room, my stuck on boobs bouncing as I briskly walk down the hall, I couldn't believe how excited I was, I was quite happy with the out come, I really enjoyed dressing in girls cloths and would now be indulging my fetish for the majority of my time from now on. the extra detail K had added, had not really fully registered to me at this point, but makeup etc was a new dimension that on the surface was quite appealing. So I quickly strapped my tits into the nice bra K had put out, suspenders and stockings, panties ( I was pleased with myself for remembering to put my panties on last, always makes it easier to go to the bathroom later, I congratulated myself for so naturally thinking like a real girl as I dressed, I could easily have forgotten such detail in my rush I mussed)

The dress, although it was a very pretty dress, K was correct, it did hang like a sack over my male shape and was less than flattering really. I was suddenly motivated to loose all those extra pounds (funny I should have done it years ago and would probably helped me have better sex with K, but now to become a better girl I wanted to start immediately and couldn't wait to see the results, how selfish of me, K definitely deserved a better man) I needed a much more feminine shape to wear dresses, I finished putting on my heels and returned to K in her bedroom.

K was waiting for me, sat me down at the mirror "I going to do your makeup this morning, you watch and learn, we don't have time for you to try and do it yourself" K pick up a net and put on my head, I must have looked a bit confused "its a wig cap, I have an old one here we will use for now, we'll do your makeup then put the wig on, that's how you do it, ok" I nodded and K started applying foundation, K was actually very quick and in no time I was getting the finish touches, lipstick and the wig.

I was reasonably impressed, I think you would still pretty easily tell I was in drag, I thought my face looked quite feminine, as I stood up I was now even more disappointed with my shape, I thanked K as we discussed some of the finer points of makeup. K again in her authority tone instructed me to go and make lunch.

Yes it was no longer mid morning, and as I entered the kitchen, John snarled at me "typical fucken' woman, takes forever to get ready, i'm fucken' starving, get cooking". there was a menu and recipe on the bench that K had just hand written, basic stuff, eggs benedict, bruschetta bread etc. I went to the pantry to get the items from the recipe, only half of the thing required were there, oh well i'll just ask someone to go and get them while I prepared the rest.

The agreement with K was now about to really bite - "No that is your job now, cook, clean, grocery shopping all your new girlie duties, you better scoot down to the store now" K calmly reminded me. I was frozen to the spot, obviously stunned at the realisation. "yes Honey, remember you are dressed like a girl for everything except going to work.....quickly off you go......John is hungry, he is getting grumpy.....hurry up"

I began to totter off in my 4" heels, not sure how I was going to cope "honey, you will need a purse....I will give you an old one of mine for now" K suggested , John called out " for fucks sake, that will take forever, why don't we all go to the Mall, I can get myself lunch at the tavern, while you two bitches are off doing your girl shite,
and i'll have a few beers while I wait for you to come and get me after you're done" K seemed happy with that suggestion and grabbed her bag and a purse for me, we were off to the Mall before I knew what was happening.

I sat in Johns redneck hot rod pickup truck, feeling very out of place and anxious about getting to the mall, being a girl in the privacy of our home was one thing, even the activates of last night seemed to pale in comparison to my impending exposure. the fact I was about to go out in public for the first time very shortly, had my heart racing. I was struggling to stay calm, realising I was about to be fitted for a shaping corset then visit various woman's clothing and accessory stores, my god was I going to be trying on dresses in store?

Not only was I a nervous wreck, I was excited, the beginning of getting a more feminine figure, trying dresses on in a woman's fashion store, this was going to be a very special day. My apprehension was slowly being replaced by anticipation!!

to be continued

Before long we were parking, no too far from the Tavern but a little farther to the shops us girls were intending to visit, John gave K a long kiss and headed of for lunch and said he would see us later in the bar. at that point it struck me that after our shopping I would be going into the Tavern to meet John dressed as a girl, amazingly, instead of being instantly terrified, I was actually thinking to myself - oh, I hope the corset works, I really want to look my best when we go to the bar, oh my god, you are such a girl now - just a short few months ago I would not have cared how I looked going into a bar!

K and I made our way through the Mall, a few people did not pay us any attention at all, many noticed but did little more than raise and eyebrow or smirked, a few more made it more obvious, pointing me out or a comment but nothing to bad really.

We walked into the specialty underwear store, an professional woman of a similar age to us, approached immediately and asked how she could help. K advised her we required a shaping corset, and we were lead to a fitting room, the assistant motioned toward me "for........" "yes" replied K "....well if you could take your dress off, I'll get you measured up" I stood in front of her in just my underwear and shoes, K and the assistant had been making small talk as I undressed and continued as the assistant began to inspect me.

"how long...."motioning at my underwear but looking at K "I first caught him a couple of months ago, but suspected for quite some time before that, but she is most definitely a girl now"...."we actually get a lot of middle aged men buying underwear, some pretend it is for the wife, but we can tell most are for themselves" she continued to measure and finally looking at my pantie clad groin commented to K "these panties fit nicely, has she been on hormones?" "No" replied K "hmmmmm wasn't to much of a man to start with then" the assistant said with a chuckle "only 4 inches" K replied with distain "ha you won't be missing anything then... you must have a lover, my husband is quite small also, i've had a lover for years" the assistant confided "well, I haven't till now but....last night....well lets just say he made woman of both of us"

I was blushing by this point, the assistant looked at me "oh goodness sweetie, that's wonderful for both of you, it's so good to be fucked properly by a real man isn't it" I shyly nodded to what was surely a rhetorical question "right, i'm sure we will have the correct corset to short your figure out, back in a minute" While she was away K seemed to be delighted that the assistant now knew that I not only like wearing girls clothes but had also been fucked like a girl "are you enjoying being out honey? everybody you meet, knowing you like being fucked like a girl" K had real pleasure in her voice "I had not thought about hormones, we will have to see doctor Peterson about that, he won't be to surprised I wouldn't think, I have discussed my concerns over your lack of manliness with him before" this line of conversation was cut short as the assistant returned

I was soon trussed up in a very elegant and firm corset, quite uncomfortable to be honest but non the less what a difference, I admired the transformation in the mirror, I certainly had a much more womanly profile. I had a radiant smile, as I ask if I could put my dress back on, "of coarse dear, lets have a look at you now then............yes that is much better, a belt will really show off your new figure" as the assistant stood behind me and pulled the dress in around my waist. She was so right, what a difference, I was still over weight but wow I had a females figure, I was in heaven. k agreed and we thanked the assistant paid the bill and made our way to the next store, I felt much more confident walking through the Mall this time, much more passable as a girl I thought.

we entered a fashion store and started to look through the racks, again we were joined by a sale assistant, much younger though this time, she enquired how she could help. K replied "my girlfriend needs a new wardrobe......lets start with some skirts I think", " right this way please ladies.....there should be something here for you". K picked out a couple of sexy pencil skirts and blouses "these should look great on that new figure of yours honey........can we try these on please" the young assistant paused, taking a long look at me, finally looking a little uneasy "we only have female changing rooms here......is that alright" K reassured her that is fine "she is very much a girl now, specially after last night" winking at me, I blushed uncontrollably again.

We visited a number more stores and purchased ensembles and accessories from all of them, and I must say it was a completely enjoyable experience. Trying on dresses, walking out of the changing room and doing twirls and posses for K and the assistant was a wonderful experience, even getting positive comments form other customers, what a buzz.

As I had my red heel on, we decided a red above the knee pencil skirt and jacket with off white almost sheer blouse would be nice to wear to the bar. We stopped at a beauty saloon, on the way, to have my makeup touched up for a more evening look as it was already late afternoon by now and it was looking like we would be at the bar well into the night, they made a very nice job and when I stood back and looked at myself in the full length mirror, I looked fantastic, even if I do say so myself, quite a transformation and I felt fantastic also, I couldn't wait to get out and show off, I was confident I was a more than passable girl in both appearance and attitude now.

By the time we got to the bar it had been quite a few hours and John had been joined by a group of his friends, the affects of the number of beers he had consumed was obvious, he was even more boisterous, arrogant and louder than ever. "wow, here's my girls, 'bout fuckin time....lucky i'm at a bar" he laughed, and gave K a passionate kiss, he looked at me "well...you look quite fuckable now don't you.........Hey guys" he shouted to his friends "most of you know K, my girlfriend and this is her husband, they are both really good fucks but K is mine only remember guys" a deep voice came from across the bar "introduce the sissy fuckin properly, what's her name?" I shot a look of fear at K, what was my girl name going to be, K quickly replied motioning toward me "this is Roxanne" a chorus of "Hi Roxanne" filled the bar.

I shyly waved to them all. then leaned across and whispered in K's ear "Roxanne?" she quietly replied back " the slutiest name I could think of, these are mostly Johns jailbird friends, i'd say you are going to be fucked by more than one of them tonight, you will undoubtedly be their slut by the time they have finish with you.... you have made all this effort to look like a sexy woman, surely you did not expect a sissy like you to get out of a bar like this without being fucked senseless tonight, john and I will be going onto a nice restaurant shortly, he has told his friends to make sure you get home safe at the end of the night"

I was speechless, I entered the bar feeling like a confident, sexy lady, I loved my new womanly figure, accentuated by the elegant pencil skirt and quite convincing makeup, I felt very much like the pretty girl I had been trying to be for the last few months. Had I made it as a girl? in a bar surround by men that wanted to fuck me, apparently I was about to find out as John and K said goodbye to everybody and left me at the bar with a group of horny ex cons.

Brad had been the first to start talking to me, he had hardly left my side, appearing quite protective of me from the other guys, it appeared he had staked his claim and they were respecting this. Brad was a large line backer type and dwarfed most everybody in the bar, I was feeling very special, I actually, wanted him to take me home, I was cuddling into him and letting him fondle my bum, he was now making it quite clear of his intension to have me for the night.

He told to me that after a few years in jail he had become very partial to white sissy arse and I was the finest bit of sissy arse he had seen in a while, the truth was I couldn't wait, I had gone out dressed like a girl , been picked up at a bar and was about to be taken home and used like a girl. I suggested to Brad we should go back to my place, as I could wait no longer.

Brad hesitated then whispered in my ear "not sure that will fly with the rest of the guys, they have agreed I get you first but most of the guys are looking forward to having a turn on that arse of yours after me." a wave of fear ran through me, and it must have shown on my face "why do look so surprised, John and K arranged this last week, they told us they would be bring her slut cross dressing husband to the bar tonight for a gang bang in the back of the bar.......K told us you were up for it and would fuck us all, that's why so many of us are here" I felt weak at the knees and held on to Brads arm tightly to support myself, trying to process this information.

"last week?'" I questioned Brad "yeah last week she promised to bring you along - K's been telling us about her sissy cross dressing husband since John first started fucking her nearly two months ago. We have been asking her to bring you along as soon as she told us about you, and we are not disappointed, we are all looking forward to fucking you" - "johns been fucking K for two months?" I questioned Brad again "yeah, he's been trying to get into her pants for ages, she's the hottest MILF at the public defenders office for sure.....then a couple of months ago she call him and arranged a date.....she had just caught you dressing up and was really pissed off, so John scored big time, we have heard all about you"

K had planned all this as some sort of revenge? I had seriously underestimated K distain for what I had done, my god had I been duped into this, was K getting me gang banged as punishment for experimenting with woman's underwear? I had to re-evaluate, yes only an hour or so ago I was ecstatic about my transformation into a girl and even wanted Brad to take me to bed and fuck me, but now I was feeling totally betray and tricked into this situation.

"Brad" I whispered " i'm not ready for this, last night was my first time......with John, and this is the first being out, completely dressed like a girl, I really like you and would love to be with you, but I can't fuck all these guys, I can't do it, i'm not ready, please....please...can you get me out of here" I pleaded tears welling in my eyes

Brad looked at me with compassion in his eyes "I might be able to get you out of it tonight, but you will have to fuck then all soon or later, they do not like being cheated OK" I nodded "anything I just can't do it tonight, i'm not ready, please......please" Brad calmed me down and said he would clear it with the guys and take me home.

How could I have misjudged K's reaction so badly? what was going to happen when we got home? god what a mess, I had so enjoyed today at the mall, I felt so good, looked good, I actually do feel attracted to Brad - I wanted to be his girl, should we go to bed tonight and worry about the rest of the situation tomorrow? will I have any choice? does Brad expect to fuck me when he gets me home regardless?

to be continued

Can't wait for the next section of the story!

Cuck who loves a creampie.

Wow great story and a nice twist in the last piece, cannot wait for more.

On our trip home Brad and I talk about how we respectively got to this situation - myself, first tried on my mum and sister's underwear when I was about twelve and had quite a fetish through my teenage years but wained to only seldom once in my twenties, with career, marriage, kids and houses to pay for etc but now a renewed and even more enthusiastic return to enjoying girls underwear and culminated in me completely dressed as a woman siting beside a man that had every intention of taking me to bed.

Brad had had a rough upbringing and been in plenty of trouble with the law, although he did quite well at school, both academically and with sport, he never managed to separate himself from the bad crowd he grew up with, consequently and probably predictably he ended up in jail several times. Brad had subsequently got to enjoy fucking sissy little white arse and had found it very difficult to stop desiring it out of jail.

By the time we got home, we knew a lot more about each other and in fact felt quite close, I don't think either of us had confided this detail with someone else before. We entered the house and it became instantly obvious the John and K were home, the sound of orgasmic sex echoed down the hall. Brad nudged me "K's getting it good ain't she", there was no doubt about that at all!

I had enjoyed the chat with Brad on the way home, I had put my own situation to the back of my mind, K's calculated plan, Brad intentions, had I been tricked into going this far, did I want use the new found knowledge about K fucking John months ago to renegotiate, maybe back this off a bit, did I want to be a girl all the time? all these things started swirling through my mind, but now was hardly the time to confront K.

I was interrupted "Roxanne....come on where's your room" Brad asked quietly but with a ******** tone, this was it, did I try and talk my way out of going to bed with Brad or..........Brad had guessed which room was mine and dragged me to the bed, and begun passionately kissing me........I submitted and almost immediately returned his kiss in kind. I felt his cock stirring against my stomach, instinctively I dropped to my knees and released his cock from his pants, Brad fitted every stereotype and cliché and I was presented with a large black cock, I caressed, lick and sucked enthusiastically, any thoughts of not spending the night with Brad had vanished.

Brad stripped his clothes off and removed my jacket, blouse and skirt, there I was, a girl about to be taken, I was excited and willingly got into bed with Brad. I did everything I could to satisfy Brads lust and had him pumping his cum in side me many times. Again, receiving this sort of attention from a big horny male seemed much, much better than the sex I had been trying to give K over the last few years. I had a lot to think about as we fell asleep exhausted and abruptly woken in the morning by K's stern voice "you left my new friends very disappoint at the bar last night.......Brad you will have to leave now, after all you have had quite enough haven't you" K chuckled "now I have told the rest of the guys they can come over and have you now".

Brad, got out of bed and walked to the middle of the room, "K....now stuck up white bitch tells me what to do......you may be Johns woman, but I don't take orders from any woman, Roxanne is mine now, so you better get the fuck out of here before I get angry" Brad looked very menacing standing in front of K, nude with his massive arms crossed over his huge masculine frame, fire hose of a cock hanging between tree stump proportioned thighs. "K, Brad is right, you can't talk to one of my boys like that, you are just one of our bitches" John spoke from the doorway "sorry man, K will need to learn.........maybe she needs a lesson now...........K you better get suck Brad's cock.......you can fuck my girl man, better teach her place"

K spun her head around going, from her demanding stance to a very submissive "but John, it was Roxanne, I was....." john interrupted "get on your funkin knees........Brads waiting for his apology......you, your sissy husband, don't you understand you are both our bitches and we say who gets fucked around her not you.......hurry up, you are going to get some big black cock in your arse now, that will satisfy Brad, won't it mate"

Brad now had is hands on his hips, standing expectantly in front of K "yeah your bitch needs an attitude adjustment alright John........I've never had a sissy white husband and his hot white wife arses before...... have you had her arse John?" Brad queried with some glee in his voice "no man, she is in for a experience with you" answered John "thanks man, this is going to be a fun training session........are the rest of the boys coming over.... they can gang 'em both then, that teach the funkin' crazy arseholes not to fuck around with us" said Brad as he ****** K's mouth on to his swelling cock.

"yeah the dumb middle class bitch invited the whole gang over to her posh house, what do you think the neighbours will think when the boys turn up, the only thing louder than their open exhausts will be the screams and moans of her and faggot husband being fucked for the rest of the day" John laughed

K may have had a devious plan to exact revenge on me, but it was becoming apparent that she had chosen the wrong people to assist her, they were far more ruthless than her, she was just a beginner at this, they on the other hand were going to show us depths of depravity she had never dreamed of.

Please continue........
Cuck who loves a creampie.

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