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https://www.cuckoldplace.com/SISSY CUCKOLD HISTORY 740.
Wendy was the Third of my ******* girlfriends that got her hooks into me?
Wendy was slightly older than Pamela and Fran and nearing sixty at the time and she was a Midwife I recall that she came from Sussex I cannot remember exactly where? but had moved to Lincoln where she now lived and worked she spoke very proper Queen's English and I do not know if it was her manner at work but she spoke at a slow tempo and very clearly?
From the day I was first introduced to Wendy she treated me like a filthy little boy and talked to me in a very condescending manner that I found strangely exciting!
As a woman an educated woman it always felt that Wendy was probing you when she talked with you finding the cracks and winkling out the real you and as a Midwife she was a great one for trying to help you if you were distressed or anything I suppose that was a natural part of her demeanour being in a caring Medical career.
Of course Wendy being nearly sixty had more than a few wrinkles and long wavy grey hair she had a what I would call a slim pinched face some would say she looked very ordinary? but I had seen Wendy with make up on and dressed up and for her age she was still a very attractive mature woman
Wendy was also a chain smoker and would talk down to me as she exhaled smoke out through her nostrils rather like what a dragon does.
Dress wise if she was not in her dark navy blue dress uniform she tended to wear smart good quality knee length grey or black skirts and matching jumpers with a blouse of what ever colour underneath.
Wendy's legs obviously captivated me as she wore black for work and a mixture of colours and tones from black to light grey and a variety of tans in tights.
On her own Wendy worked out that I was a budding cross dresser, later when it all came out about me Wendy told me that she felt something was not right with me from the moment we met and through observations she made and the gossip she picked up about the fancy dress party that I went to dressed as a woman helped by my ****** Wendy started to piece together the clues!
Finally there was another outing for me dressed as a woman? My ****** worked for this jewellery company and she and another company agent were putting on a meet and greet i the grand city of Hull as they were looking for new sales reps up there and Mum had this wonderful idea that I should model the jewellery making me a woman for the evening till I was exposed as her *** and actually a male all a good laugh both she and her work colleague Eva decided and press ganged me into doing it for them (of course I made like it was not something I was overboard with but secretly I was in paradise being dressed up as a girl again and going out in public.
You have to remember that I had already gone through the incident where my tiny little penis had erected against my ******s nylon coated foot and she ousted me saying she knew I was filching her hosiery to wear making me then go put a dirty pair of her tights on to show her and then instilling into me that I was to daily delve into the laundry basket in the bathroom and put her prior days soiled tights on!
Of course Mum could not just let me run round the house in just her dirty tights so she rifled through her wardrobe and found me out three short silky nighties a pink light weight ladies robe and a pair of black fluffy slippers with a wedge heel to wear with her filthy used tights around the house
Wendy for some rea*** was on this trip to Hull and I felt so self conscious as we headed to Hull in the small bus that ****** and Eva had hired to get the Lincoln girls there dressed differently as a woman this time as ****** had done much more heavy make up daintier lingerie and very sheer tights along with one of her severe fitted skirt suits the jacket if which had a red velvet lapel with the skirt hardly covering my nylon coated knees and finally I was in a very high pair of black matt Mules that I had needed to practice walking in for three days prior to the event just to be able to walk.
Wendy seemed to be analysing me with her eyes all through the trip and when she spoke to me it was in that condescending teasing manner she had.
The meeting went down well and the women when they found out that I was actually a guy Enid s *** whooped it up in glee and I got quite a few really nice comments about how feminine I looked which did my budding sissy ego a power of good!
On the return trip home Wendy insisted that I sit on the bus next to her thus she was able to talk to me without us being disturbed and it was here that Wendy brought up the fact that she did not think that I was solely dressing up as a woman to aid ******s business idea's and that she suspected there was more to it than that?
I heard nothing more for a couple of weeks then one evening when I arrived home ****** informed me that I was going to Wendy's home for tea.
Straight away I was nervous and fearful a all the things that were happening to me from ****** allowing me to dress up at home in her dirty discarded hosiery and now filthy panties as well to my often visiting to Pamela and Fran both of which delighted in dressing me up and sexually using me for their pleasure introducing me to some of the most deviant sexual practices and I was on edge as I walked down to Wendy's house which was about a mile from ours wondering what the hell was going to transpire as it seemed odd going to Wendy's on my own not in the company of my ****** as had occurred previously.
Wendy had made us a nice tasty simple tea of Salmon and cucumber sandwiches with fruit cake for afters a very nice little tea we had together and it was only after that Wendy started talking and telling me she had worked out that I was a transvestite and both my ******, Pamela and Fran were taking advantage of me?
Wendy informed me that she had talked with my ****** and knew all about the *********** night I had erected against my ******s nylon coated foot and the crushing words of penile *********** she made over my tiny size and her exposing me for stealing her dirty hosiery how then I was compelled to wear ******s dirty cast off tights and now panties daily.
Wendy also informed me that she had also had long talks with Pamela and Fran and knew about me sneakily watching Pam have sex with a man at her fancy dress party and then me kissing and sucking Pamela's stocking clad toes when I stayed behind to help her tidy up and eventually how it led to me begging to lick and kiss her pussy even though I had seen Pamela having sex with a guy and she was fucked pussy sperm filthy and how Pamela had taunted me over my tiny penis news that Fran had gleefully spread after kissing me dressed as a woman in the kitchen with her in the French prostitute outfit she was in thus copping a feel of my turgid tiny penis herself then sticking the high heel into me with her verbal *********** of my little manhood!
All I could do sitting there was to listen to Wendy not daring to argue or contradict her as everything she was coming out with was basically the truth!
I cannot put into word how much I was squirming in shame and embarrassment when Wendy informed me what Fran had told her about me and how I was already addicted to licking and kissing Fran's substantial bottom no matter what state it was in letting me know plainly that she knew I was submissively ingesting both urine and **** and both Fran and Pamela were witnesses to the fact that I was getting highly sexually aroused doing these perverted sexual acts.
I remember before we got to the point of Wendy suggesting in a commanding sort if way that she wanted to see the nylon tights and panties I was in under my trousers that I was mentally broken and I sat having a few tears of fearful shame in front of Wendy who then trying to brighten the occasion pushed me gently onto lowering my trousers
So now Pamela was added to the seemingly ever growing list of women that knew and ****** their knowledge of me being a kinky budding Feminized sissy cuckold!
When at last I shamefully pushed down my trousers and exposed my legs in a dirty pair of my ******* American tan tights and over the top a pair of her soiled pink silky panties Wendy could hardly contain the giggle that escaped her lips and she could not help herself but to reach out and fondle my stiff little pantie and hosiery covered little hard on saying that she had heard from both my ******, Fran and Pamela about how tiny I was but she needed to see it for herself!
Thus seconds later with my tights and panties tucked under my tiny hairless testis my erection was in Wendy's hand and lazily she let a cigarette while inspecting it informing me that I was shockingly small and under developed in the penis department and she could now clearly see why as a young pathetic male I was drawn to dressing in women's clothes and slowly but surely terrible fetishes and perversions were developing and come to the surface in me and that as I had a natural submissive nature I did not have the backbone refuse any order from a Female many of which would for a laugh because of the way I was ***** me into practicing very deviant sexual practices to just basically humiliate me and see how much they could get away with?
It was at this point with my stiff little penis in Wendy's palm that I lost control and started to sissygasm my weak water sissy milk shooting out some splattering onto Wendy's chin and lower lip the rest soiling her grey jumper in the area of her breasts.
This was the start of Wendy using me for her own ends and she was the one that got ****** sending me to her home often for tea already dressed and made up as a woman and my service to Wendy filled her want at having her nylon clad toes and feet worshipped by my mouth with lots of kissing licking and sucking till she would use her hand and masturbate herself in front of me as I sucked her toes like they were little cocks till she violently orgasmed.
