2026 Jun - hey wow, I'm still alive!

SISSY CUCKOLD HISTROY 1067.
My weeks’ vacation in Naples Italy was lovely although the city is filthy and run down but in that aura I found sissy cuckold success.
Late afternoon on the 164 bus coming back from the huge Market they have there on the route a lush of a woman got on the bus, old in her sixties messy blond hair piled up on her head a short tight denim skirt very high scuffed black high heels and a tight low-cut top showing off her impressive but wrinkled old tits with heavy makeup.
She was swigging out of a bottle of lager beer and stank of cigarettes, alcohol and was quite drunk, I knew as soon as she clocked me on the bus she would sit on the seat opposite me and in that assumption I was not wrong.
The other thing about her was the cheap perfume very slutty and the unmistakable aroma of sex on her, somehow we managed to converse in queer English and Italian and she was slurring her admiration of transvestites, we ended up in a bar in her local area a real dive of a place where we had a few drinks.
Ended up being taken back to her home which was surprisingly very neat clean and tidy, that was about the only clean and tidy thing about her as she was delighted that I went down on her in the state she was in sticky and stinking she had been out all night and was a dire mess.
Of course, it transpired she was a working lady and had been for many, many years and although elderly she still had some good looks and as it was she that picked me up there was no charge in fact the only thing I did that evening was take her out for a meal.
Lovely Lady was Maria.

It would be a shame if one of my pics accidentally slipped into someone else's sissy gallery...

SISSY CUCKOLD HISTORY 1066.
For a feminized sissy cuckold one of the most humbling things it can witness and have to cope with is its wife indulging in anal sex after that subject being utterly taboo during their marriage so much so that even had sissy looked as her bottom the wrong wat it could provoke actual physical violence from the wife.
Think then how emotionally painful it is then that once the wife becomes a Cuckoldress the first thing sissy see’s when she returns home from a date with a lover is her anus fucked to obliteration and she is crowing over how fucking sexy it was to be fucked in the ass and the shattering anal orgasms she was having being plundered by cocks up her back passage that make yours look what it is miniscule.
Not only that your new cuckoldress will delight in making you lick and suck clean anal creampie which as we all know smells and tastes totally different to the pussy variety.
Then there is the actual witnessing of seeing your wife’s butt hole greedily devouring massive cocks in her ass either on their own or part of multiple penetration sex even double anal penetration and the gusto she throws herself into these sordid displays in front of you grabbing all the pleasure she wants from the acts.
As a feminized sissy cuckold, you will suffer emotional damage because she forever spurned your efforts to even lick her bottom let alone put your silly little penis anywhere near her back passage and you will also with that hurt feel so sexually tormented and aroused over the illicit act.
But worse is yet to befall you sissy cuckold as your wife will gleefully look forward to the day when all the huge cocks she is having pounding her anus causes her bottom to prolapse often as it’s so loose and she then gets you her loving faithful feminized sissy cuckold to lick and suck on her protruding anal meat all spunk and shits slimy till it’s clean and retracts back inside her.
Once she had obtained this state of bodily function like many cuckoldress wives they will deem it essential that sissy cuckolds on bottom prolapses like hers thus starts dildo training and eventually gross homosexual acts to bring that about.

SISSY CUCKOLD HISTORY 1065.
Shortly after my first wife and cuckoldress Anne left me I was picked up one night at one of those divorcee nights that used to go on mid-week by a German woman called Janet who was at the place with a girlfriend of hers.
Janet was a lot older than me but still pretty with long blond hair and nice figure and attracted me due to the sexy black dress she had on along with heels and black hosiery.
The night ended up with Mary her girlfriend dropping us off at Janets once the club had closed, of course I was trying to do the man stuff that night, but when it came to the crunch with Janet in her bedroom I failed miserably.
It did not pass Janet’s attention that my body was smooth shaven, and it was not long before she was making some cheeky comments about how small my penis was and her laughter seeing my clit get very hard under her verbal jibes.
Of course, it ended up with her getting her rocks off with me licking her pussy to orgasm a couple of times and me disgracing myself by ejaculating onto her bed sheets as I licked her.
Over coffee afterwards it all came out about my cross-dressing and that I knew I was pathetically endowed and what my ex-wife had been to me with her having boyfriends.
Janet maybe because she was liberated and German was not fazed by my revelations and suggested that the next time we got together I should wear some of my lingerie and stockings.
So, two nights later with invite for a meal I arrived at Janets flat that was in a tower block fully in Carla mode make up and everything.
What an evening we had as Janet had dressed up as well and there was lots of oral for her as well as use of her sex toys on her holes while for me she had purchased a large cucumber while she had been shopping for the ingredients for our meal.
While I was there her girlfriend Mary phoned up and I listened in shivering humiliation at their conversation as Janet had told Mary everything about me and what she had me doing that evening with her.
Janet’s thing was that she liked to piss so I was subjected to drinking gladly all her urine whenever she needed to loo that night.
Of course, we arranged to meet again but I got a call from her late one night before our agreed date and she told me to dress and to come round to Her’s quick which I did en femme again as I was home alone all dressed up anyway.
Janet let me into her flat that stank of sex and so did she and she explained that one of the men she often saw had just left and she was swimming in sperm and wanted me to lick her clean.
Of course as you would expect I did not turn down that sort of offer and dived in eating her dirty spermy pussy and ass till all traces of spunk had been removed and Janet had spasmed through a series of very hard climaxes.

SISSY CUCKOLD HISTORY 1064.
For many women the change from having a husband to finding out they want to be a feminized sissy cuckold with all the bells and whistles as the saying goes is quite something to take on board and you can understand why this may lead to divorce.
Strange as this might sound but its not only in the best interest of the wife the split happens but also the want to be sissy cuckold husbands as now the truth is out each can move on and find what they really need in life.
Another odd aspect of this is that more than a few separated couples who are trying to rebuild their lives end up back together at the insistence of the wife.
You see the woman will of course spill the beans to her girlfriends and it will arouse a lot of hilarity but also some serious comments about wow girl your husband was willing for you to have your cake and eat it.
After a short time, the ex-wife will fuck her first post marriage lovers and rediscover how great sex is not the pathetic fumbling’s and labia nudging her husband could only attain with her.
It’s with all these strange pressures, comments, suggestions and not a little exploration by her on the subject of the sissy cuckold that the ex-wife starts to look at the whole thing in a different manner.
She sure misses the fiscal security her husband afforded her and the fact that without knowing why she recalls that she wore the trousers in their marriage anyway with her husband doting and adoring and doing anything she said.
Quickly then she will start to wonder wat it would have been like to openly have lovers while she and her husband were together and if he would have been able to cope with her infidelity like he stated when he confessed to wanting to be a sissy cuckold as the fantast would be nothing like the reality.
What also catches her imagination is how these cuckoldress wives she has read about utterly swamp the marriage and the feminized husband is locked in chastity and used as a maid, slave and general dogs body
That the Cuckoldress wife can use and abuse to her hearts content.
If the separated pair are still on good terms the now mostly crossdressing husband in his new accommodation will notice an up tick in visits from his ex and see’s that she is getting comfortable around his new female persona and how in command she appears to be and not only that she will let it be known that she has a whole new sex life which of course as painful as it is for the dumped husband he is finding as a feminized sissy cuckold that it’s so exciting.
By this time it will most likely be the wife that says she wants to give their marriage another go with strict new rules that as a Cuckoldress wife she can say and do anything she wants and this total turn round of the wife captivates the desperately in love feminize sissy cuckold husband and soon they are together again as a married couple living the correct lifestyle for them.