TV Beginnings - Caught by NeighbourbyNylontease©
I started crossdressing at quite an early age, 'borrowing' items of my mum's underwear and furtively dressing in them when she was at work. As I was an only child, and mum and dad had separated, I had quite a lot of time to indulge my little hobby! I used to love wearing her tights, the sexy feel of them encasing my legs and cock, and the way they made me feel so girly when I admired my reflection in the long mirror in our hallway. I would also wear her big full-cut knickers and doreen bra, and complete this with a lace slip and a pair of strappy heels or mule slippers that I could fit into then. I used to get so turned on that I would come in my tights without even touching myself, and I would stay hard all day in them. This little habit continued until I finally left home in my early-20s!
I remember one morning I was in my usual favourite position - gyrating my hips in my best girly way in front of the long mirror. I had on a matching blue bikini set, barely black sheer tights pulled high up over my waist, and a pair of black strappy high heels. I was rubbing and stroking myself into a frenzy when there was a loud knock at the front door - which was only inches away from where I now stood. I almost jumped out of my skin, and was thankful that I had pulled the curtain over the door. I stood there motionless and silent, my heart pounding in my chest. The knocking got louder and more insistent, and someone shouted 'open up!', all the time pounding on the door. I decided I had to answer it, so drew back the curtain just enough to allow me to open the door a couple of inches. I stuck my head round the door and was startled to see mum's friend Geoff. 'There's been a few burglaries in the street, and I just wanted to check everything's OK here' he explained. He was trying to look past me into the house, so just I mumbled that everything was fine, and moved to close the door as fast as I could. As I did so, the door stuck, and I realised my own foot was in the way. I quickly moved it, but I'm sure Geoff had caught a glimpse of my tights and heels.
Shaken by all of this, I got undressed and put on my regular clothes. About 20 minutes later there was another knock on the door. It was Geoff again. 'Everything alright? You seemed a bit jumpy before. Can I come in?'. Geoff was one of these older retired guys who like to look after the community - neighbourhood watch and all that. He was a widower and a bit lonely I think, and had taken mum under his wing after the divorce. I let him in and we went through to the kitchen. I made us both a cup of tea while he explained about the burglaries in the street. Then out of the blue he said 'Did I see you wearing tights and high heels before?' I went bright red and didn't know what to say. 'It's alright, I won't tell your mum, not that there's anything wrong with it anyway - lots of men like to dress in women's clothing. Do you want to know a little secret? I did too when I was a younger man like you!
I was astounded and embarrassed but felt a strange sense of relief - and something else stirring inside. 'What do you think about when you are dressed as a woman Peter? Are you Peter, or do you imagine yourself to be a woman, with your own girly name?'
'I imagine myself as a sexy woman, with a woman's body, dressing in lovely sexy women's clothes' I answered, feeling strangely turned on now.
'And what's your girly name?' asked Geoff.
'Fiona' I said. (I had chosen the name because of a girl called Fiona who lived up our street. She was very tarty, with a fantastic figure, and always wore lots of makeup, tight blouses, mini skirts and high heels, with her toenails painted bright red or pink).
'That's better, I'll call you Fiona from now on' said Geoff. 'In fact, why don't you get dressed for me now Fiona, and I'll make us another nice cup of tea. Be quick'.
Heart pounding I went up to my room and took out my stash of clothes. Mum's underwear tastes didn't run to anything too saucy, but I chose the smallest pair of bikini panties I had, and a matching pink lace bra. I put on a pair of dark tan tights, and a nice little A-line dress that buttoned up the front and came down to just above my knees. I glanced quickly in the mirror and felt my cock twitch at the womanly figure I saw reflected back at me. I took a deep breath then went back downstairs.
'You look lovely Fiona' said Geoff, clearly admiring my figure. Gaining confidence, I put my hands on my hips and assumed a glamour model pose for him, glancing coyly over my shoulder at him and letting my dress ride up my thighs a little.
'Gorgeous in fact' he continued. He put down his tea cup, strode over to me, and took me in his arms. 'And do you fancy men Fiona?'
'Older men Fiona?'
Geoff moved to kiss me, and suddenly felt incredibly feminine and receptive in his arms. Our mouths opened and Geoff began to French kiss me. I could taste tea and a hint of cigarette smoke on his breath, and loved the intimate feeling of his tongue on mine. As we kissed, he unbuttoned my dress and slipped it off my shoulders. I shrugged it down over my hips and stepped out of it, and fell back into Geoff's arms. He pulled me into him and I could feel his hard cock pressing into my stomach. 'Take out my cock' he said, pushing me to the floor.
I unzipped him, my hands trembling, and took out his meaty cock. He was semi-erect, and his shaft was very thick, with a dark red bell-end. I wanked him a few times and felt him grow solid in my hand. It felt fantastic and I was now completely uninhibited. I licked his now-glistening bell-end then began slurping it noisily, loving the salty taste of his man juices and the sound of his moans and heavy breathing.
Abruptly Geoff stood me up and lifted me on to the kitchen table. He stroked my thighs and cock through my tights a few times, then pulled my tights and knickers down to my knees. 'Lie back' he said, then he raised my legs so that my knees were under my chin and my ass was all exposed. I suddenly felt his tongue and hot breath on my little 'fanny', and he began licking me, first up and down my ass crack and balls, and then inside me. Then I felt first one then a second finger replace his tongue, and he began fingering me whilst wanking himself off.
(Now I knew what the real Fiona must feel like with her boyfriends. My little fanny felt electrified with pleasure and I could feel a girly orgasm building up inside me. I felt like a slut and it felt great.)
Geoff removed his fingers then placed his cock against my little ass. I spread my legs wide and Geoff gripped my ankles and leaned into me so that his cock started to enter me. I helped it in with one hand then wrapped my legs round Geoff's back. He thrust slowly into me, first his bell-end entering me, then the whole thick veiny shaft. He started slowly fucking me, and leaned forward and French kissed me again. I could taste my own musk on his tongue and loved it. His fucking got more urgent, and he started calling me a dirty transvestite slut over and over again. I raised my arse up so that he could thrust deeper into me, and I could feel his balls slapping against me. Then he suddenly withdrew and started cumming, wanking himself and spraying hot spunk over my cock and balls. I wanked my own cock and started cumming too, and with my other hand I massaged his and my spunk into my balls and arse crack, and then fingered myself to finish off my girly orgasm.
Geoff zipped himself up and said 'Your little secret is safe with me Fiona - as long as you are good to me! And with that, he left, though it wasn't long before I was to meet him again!