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MissLesley's Stories | xHamster

Older Women and being sissy- some musing part 1

As a lifetime lingerie slut I often reflect on what made me this way.Cerrtainly the proliference of older feamles in my life from a young age has shaped my interests. Certainly in the case of underwear to peak my interest it must have the style and fabric form the 50's and 60's. Big Knickers are so erotic.The fact that an older woman in them allows for so much manouvering room to play with a cunt has to be a big bonus. Whilst these days my preference is for the shaved clitoris of a sissy, there is still an attraction to admiring the cunt of a woman, I remember when in the last year of school a… Read more

Posted by MissLesley 7 months ago 17

Huge Clit Experience

I had been having telephone sex with a trans girl for some time when we decided we should meet for some fun. She was in her early 30's and was a manager at a chain electrical store in the Scottish borders at a small town just in England. I arrived early evening and got changed into my blonde bob cut wig , navy lacy bra with breastforms , full cut matching panties & suspender belt with ff seamed black stocings and patent heels. Fully made up I was ready for a night of girly fun. She wore a black bra and tiny panties. The amazing thing was that she had a huge thick clitoris -probably 7 inche… Read more

Posted by MissLesley 11 months ago 19

G/F in a corselette and condom wank

I was about 19 when I met a girl a little younger who was exceedingly pretty. Not only was she pretty but lived with older parents . Her mother clearly had idea about her daughters choice of underwear. One evening we were in my car in a rural location making out when I started to fumble inside her dress. I was amazed to find that she was wearing a hook crotched corselette . Well I nearly came on the spot. I was allowed to undo it and finger her cunt after she stuck a finger in herself to declare that it was okay as she hadn't come 'on' the rag. I so much wanted to stick my little clit against… Read more

Posted by MissLesley 11 months ago 4

Feeling very Girly -Aneros Penetration Pleasure

Well tonight for the first time in forever I felt the real need to be penetrated in my sissy cunt. My cunt is very tight so I was very surprised that a pea sized blob of lube was all it needed to take my aneros straight inside me. I was lucky that one of my girly friends one to watch messaged me needing to wank off. She was super excited when I told her I was fucking myself anmd it took a very short bconversation before she spunked off in the jonny i had gort her to wear (she always has a jonny ready for when she is going to milk her clit for me. I'm hoping someone else wioll need my help toni… Read more

Posted by MissLesley 1 year ago 6

Some of my Fetishes Before I feminised

I was with an older woman in my early 20's. In those days I was a total sex addict and needed to cum at least 2 or 3 times a day. Contraception was important and it was part of our sexual activity to practice different methods as she couldn't take the pill. Condoms of varying types were available then from rubber to natural skins. We had often had mishaps with rubbers breaking so she had an IUD (coil fitted). As that wasn't reliable we would use a jonny or sometimes if she pleaded for bareback (I didnt enjoy bareback much) we would use something called Delfen which was an aerosal foam injected… Read more

Posted by MissLesley 1 year ago 3

How I Achieved My Small Clitoris

I always had issues with my genitals. An incident with a cricketball probably didn't help!A a youing man I had constant testicular pain which was certainly relieved by wearing tight pantes /pantiegirdle. I was diagnosed with epididimitis and had surgery to remove some clacified tubing in my testicles (how I wished they needed removal). Well I asked thesurgeon if I could becircumcised at the same time. Well it wasn't a very neat job and far too much scarring and foreskin remained. Fast foward a few years and following further testicular surgery I was still unhappy with my clitoris.I did some re… Read more

Posted by MissLesley 1 year ago 13

The 'Cunt Free' Club

In my new found role as mentor to my many Bi and trans friends I have learnt that many of them are happily 'Cunt Free'.By this I mean that although living with a woman they have not had sexual intercourse per vagina with these women for many years. It is pleaseing to know that so many Special ladies here are of this pursuasion and it gives me great pleasure in being to enable them to rid themselves of their 'nasty boy juice' without resorting to penetrative sex with a woman's cunt. I welcome oontact anyone who feels the need for cyber relief by msg only on this site. Genetically born women/ po… Read more

Posted by MissLesley 2 years ago 40

The Thrill of Lingerie Shopping

When youngerr I used to regularly fully dress. One of my most erotic excercises was to go lingerie shopping out of town. A few miles away there was a large shopping Mall and it had a Marks and Spencers Store with a huge lingerie department. At that stage of my life I would get totally aroused in such a place - my little clity would get hard and very wet. To prevent this from showing I always wore a tight pantygirdle with a sanitary twel in it against my clitty to prevent any visible signs of arousal or ejaculation. In those wonderful days in the early 90's M&S sold gorgeous sets of underwe… Read more

Posted by MissLesley 2 years ago 26

My One Female Prostitute Experience.

Well I was in my 30's and totally frustrated. The older woman I was seeing would never touch my cocklet. I did some internet trawling on a site called punternet and found what interested me. Lots of research and I had an appointment with a lady on a smart new housing development. She was probably in her late 50's and very pretty. Her house was a big detasched house with all the trappings of a nice lifestyle. She allegedly was a travel agent specialising in Italian Holidays, but certainly she had something far more special on offer. I arrived at the house and the door was answered by a pretty a… Read more

Posted by MissLesley 2 years ago 10

A foolish attempt to modify my genitals

When young I was always attracted to my feminine side. Most of the people I encountered were female -Adult Aunties, pretend Aunties and of course my Mother encouraged me to play with neighbourhood girls from a very young age. I remember one day in the bath rolling back my tight little foreskin and feeling the glans 'pop' out. I was a little scared as I thought I'd damaged myself. I was intrigued by the fact that there wsas a piece of sking preventing the whole head of my penis from being free. It felt tight and uncomfortable. I decided that something was wrong ond so I got a razor blade and sl… Read more

Posted by MissLesley 2 years ago 3

My First Ever Fuck -Durex Gossamer style

Well I was about 18 and in a pub with 2 friends in a country location. They indicated that they wanted tob have some fun and told us to meet them in a secluded track not very far from the pub. We drove to the location and a short while later the girls turned up. They were no beautiful but indicated that they needed to be fucked . It was somehow decided that I would get to fuck the older one who had a c***d. . Firstly my friend M fucked her withn a jonny as she wasn't on the pill (why she already had a c***d). once he had finished it was my turn to get in the bacxk of the car with her. By now s… Read more

Posted by MissLesley 2 years ago 5

A Woodland Panty Wank Adventure

This is a true recollection of a very sexy non contact encounter. I lived in a rural area and one evening while driving along a country road I found a bra , panties and stockings just thrown on the roadside. Well I couldn't resist and went to a location I knew in some woodland. There was a track there with an embankment with a hole in the bank hidden from view.. I hid the lingerie in the hole intending to return for some dress up wank fun another day. The next time I returned to the location I could see someone had been in there an with the lingerie was a used rubber jonny full of spunk. I sus… Read more

Posted by MissLesley 2 years ago 14

First Condom Purchase and Wank Experience

Well growing up used to cycle everywhere with my mates. Went into the toilets at a local filling station / shop and encountered my first ever condom machine. Well I absolutely desired to buy a pack. Sweaty palms and a few coins later and I had a little cardboard box in my pocket. I can still remember they were 'London Brand'. I couldn't wait to try one out. I went home and locked myself in my bedroom. Trembling I tore open one of the foil packets and squeezed out the thick greasy rubber delight. My little (at that time uncircumcised) cock was stiff. I pulled back my foreskin and started to unr… Read more

Posted by MissLesley 2 years ago 17

The Special Panty experience

When I was young it was my habit to when alone to loook for Mothers undies to play dressing up.Now usually this was a corset or later a pantygirdle (when tights came in). Panties were nylon -pastel colours and fabric that felet like crep paper. Oh and of course a clingy nylon slip. In the bottom right hand drawer of the dressing table however was a real treasure. There was an unworn pair of knickers that I knew had strangely been a Christmas gift from our elderly widowed neighbour. These panties were special. They were navy full cut panties in a satin nylon with a lacey front panel. These were… Read more

Posted by MissLesley 2 years ago 11

Pauline -an early experience with an older woman

When I was in my late teens I still identified as male (although I loved to x dress). I was about 17 when I met Pauline. She was a bubbly blonde around 5 years older than me and worked in an office in the same block as I did. She was slightly on the chubby side and had huge breasts. She always wore very short skirts and was quite a loud outgoing person. As time progressed we became friends and she worked partime in the evenings as a barmaid at a pub my friends and I frequented. Well after a while it became apparent that she was a nymphomaniac. She loved being fucked beyond all expectations. Th… Read more

Posted by MissLesley 2 years ago 11

Condom Orgasm Experiment for an impotent Sissy

Now I have become so feminised , vasectomised and impotent I decided that I should try and masturbate my limp little clitty to see if I would orgasm.I should say that now I have very little sensation in my clitoris and that erection is something that no longer occurs. I haven't tried milking myself for at least 6 months so this was going to be a big test.Well I as usual was wearing a nice big pair of tight Suprima 1259 Navy incontinence panties with a Vivactive Maxi incontinence sanitary towel . I sat in front of my screen and pulled my panties down exposing my sad tiny smoth and limp extremel… Read more

Posted by MissLesley 2 years ago 10

Besetment Movie Mother wanking off son

Recently saw a movie called Besetment. The interesting part was when the elderly mother of a middle aged man needing his semen to impregnate a captive woman got out a condom and wanked hoim off until he ejaculated in it, held it up full of cum and then put it in a big syringe to inject in the captives vagina. The scene with the masturbation of the man by the elderly woman I found extremely sensual.....but then when I was young and able to masturbate being wanked off by older women was my preferred method of release.… Read more

Posted by MissLesley 3 years ago 12

Panty and Sanitary towel Masturbation for a femme

Well after about a gap of 6 months i thought i would try a panty wank to see if it did anything for me. I was wearing a pair of Kanga Kylie waterprrof knickers with a big inco pad.I creamed my limp little clitoris with my favourite Sanctuary Spa Body Butter and started to rub the end of my clitty where my frenum used to be between my forefinger and thumb and my peehole against the cotton of the sanitary pad. I have very little sensation now in my clitoris but the friction of rubbing against the pad began to cause my clitoris to swell a little. I was imagining being forced to rub myself in fron… Read more

Posted by MissLesley 3 years ago 5

Early Memories - a snapshot of a Transgender Girl

Going into mothers bedroom. the heady smell of her perfume and the makeup powder. looking in the dressing table drawers. The big nylon panties- pale yellow and blue. The seemed tan fully fashioned stockings and their delicious slippery feel against my body. The nylon full slips -beige ,pink and blue. Oh and the girdles -Playtex? diamond panelled front with those lovely metal and rubber suspenders. The restrictive feel -heaven. Then the thrill of sanitary towels. The stiff carboard box containing the 'Lilia' looped sanitary towels. The excitement of opening the box, the thrill of taking one fin… Read more

Posted by MissLesley 4 years ago 12

S.A.G.E. Test Results

This makes me very happy. S.A.G.E. Test Results Your Raw Score is: 495, which indicates that overall you are Androgynous Your appearance is Androgynous Your brain processes are mostly that of a Androgynous person. You appear to socialize in a feminine manner. You believe you have major conflicts about your gender identity. You indicated your were born Male. ANALYSIS: Male to Female Transsexual, who is a serious candidate for Gender Reassignment Surgery NOTES: Your Answers indicate your psychological state has likely prevailed since you were quite young.… Read more

Posted by MissLesley 4 years ago 11