Cross Dressing for Ann Again

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Cross Dressing for Ann Again
About a week after my first amazing session with Ann, the neighbour from downstairs who blackmailed me into modelling her lingerie, I was again accosted by her on the stairs.

“Hi,” she said, coming out of her front door as I was passing. “I’m glad I bumped into you” (I knew she was lying in wait behind the door watching out through the spyhole) “are you doing anything on Wednesday night?”

I said I wasn’t and she said that as John and Ian (her husband and son) were going to Aberdeen to watch the football I should come and visit with her. “They won’t be back until midnight so you can show me how you look in some more of my things.” As I turned to go upstairs she added “have a close shave too as I want to make you up a bit.”

If you have read my earlier account of dressing up for Ann you will be able to imagine my feeling of eager anticipation as I rang Ann’s front door bell just after 7 on Wednesday night.

She answered the door looking very sexy in a lovely white lacy blouse, an awesome black leather skirt, red nylons and red stiletto heels. She looked stunning and, getting right to the matter in hand as it were, and dispensing with the pleasantries of offering anything to drink, she led me straight towards the bedroom. The sight of her rear end swaying from side to side in that leather skirt and the sound of her nylons rubbing together made me start to get erect.

Turning round in the middle of the dimly-lit bedroom Ann look straight at me as said “strip”. Unlike the first time I had undressed for Ann I wasn’t in any way shy and I enjoyed watching her face react as I slowly peeled off my shirt and, having kicked off my shoes, removed my trousers and socks before slipping my hands inside my pants and peeling them off.

As I stood naked in front of Ann, my cock semi-erect, she moved towards me and cupped my balls and cock in her right hand. She squeezed me gently and as my cock reacted she grasped it with her other hand and began to stroke me. It was the first time she had actually touched me and my body reacted as if an electric shock had hit me and so my cock spat a small spurt of spunk. Ann laughed and said “careful, I don’t want you coming too soon”.

She turned back toward the bed where she had laid out the clothes she wanted me to wear that night. Picking up a very sexy half-wired bra, mid-blue satin with cream lace edging, she ordered me to turn round and proceeded to help me into the bra, padding it out with some silken scarves. She next brought a matching deep garter belt, probably eight or nine inches deep, and placed it round my body. Every time her soft hands or arms touched me I could feel myself wanting to spurt but I managed, with some difficulty, to control the urge to just let it all cum.

After that she told me to turn around and, kneeling in front of me, proceeded to pull black lace-top seamed stockings up my legs and affix them to the suspenders. The sight of her face just inches from my by now painfully rigid cock was almost too much to bear and pre-cum kept leaking from the end. Every time another load trickled out Ann laughed softly saying “all in good time; all in good time”.

After ordering me to turn around so she could straighten the seams of my stockings and tighten the adjustable suspenders Ann again knelt down in front of me and instructed me to step into the matching panties which she proceeded to pull up my legs and tight against my aching balls and throbbing cock. Almost immediately the blue satin of the panties darkened where my cock leaked some more juice.

Standing up Anne moved to the dressing table and ordered me to sit on the stool where she proceeded to apply a light make up to my face, giving my cheeks a subtle cleavage, giving my lips a generous shape, and making my eyes remarkably sexy looking. She then carefully pulled a white silk short-sleeved top over my head before fitting the blonde wig; it had clearly had a perm or something since I last wore it, onto my head.

“OK, you can stand up” she said “and put this on”. She handed me a navy blue linen skirt which when I stepped into it and fastened it up came down almost to my knees. “Now the high heels” she said, indicating the stilettos I had worn the week earlier, “and show me how you look on the catwalk”.

I did as instructed, walking up and down the bedroom floor then she told me to walk in front of her to the kitchen so she could ogle my arse wiggling. In the kitchen she had a bottle of Champagne on ice and opening it with some skill (I knew that a soft “pop” was better than a loud one) she poured us each a glass. “To my sexy lady-boy” she said, raising her glass in a toast “and to a night of fun”. At which point she kissed me hard on the mouth while pulling me close to her and squeezing my arse cheek firmly.

Glasses in hand, and the Champagne bucket in mine, we returned to the bedroom. Ann instructed me to look at myself in the full length mirror and describe what I saw. I said I saw a very sexy lady whose lipstick had been messed up by a randy lover. She laughed and moved behind me. “OK”, she said here’s a tissue and the lipstick “repair it”. I wiped my mouth carefully then reapplied the lipstick as she instructed me. It wasn’t as easy as it looked but after a few tries I got it to her satisfaction.

Still standing close behind me Ann cupped my silken boobs then ran her hands down my body and across my hips, smoothing my skirt, and finally lifting the hem up exposing my sensual underwear. The sight of the lace top stockings, held up by the blue suspenders, and my bulging cock straining against the sexy panties was beautiful.

As I watched in the mirror Ann use one hand to pull the front of my panties outwards to allow the other to slide inside them and pull out my cock. Its head was purple and shiny, and oozing more pre-cum than I ever thought possible. Taking me in her left hand she grabbed my cock between her middle and ring fingers so that there were two fingers below and two above my throbbing member, effectively encircling me just below the glans. Feeling me start to shudder she simply increased the pressure of her fingers which whilst both painful and pleasurable immediately stopped me cumming.

Using her thumb to massage the top of my knob and sliding her fingers up and down the area just under my glans Ann slowly started to wank me. “I’m told that this hold is just like the feeling of fucking a tight pussy when the woman tightens and relaxes her muscles to pleasure the cock inside her. Would you like to see if that’s true? Would you like to fuck my pussy?”

“Yes, Oh Yes” I cried “I want to fuck your pussy; I want to fuck you so hard”.

“Do you want to feel your hard cock deep inside me, deep in my warm moist tight pussy”?

“Yes, Oh God yes”

I shot my load. The spunk splashed against the mirror four feel in front of me as Ann continued to wank me, milking me of every last drop of juice.

Laughing softly Ann said “you are such a very good lady-boy maybe next time I will let you put your girly cock inside me, or maybe I’ll just suck it” and as she said this she dipped her middle finger in my spunk then licked it off “tastes nice” she said, “you try” and so saying she dipped her finger back in my spunk and had me lick it off.

We lay on the bed together, not saying much but she let me stroke her breasts through her blouse as we finished off the Champagne. “It’s a cup game against Hearts on Saturday. Will you be up for another session?” I laughed and said “after that work-out it will take me till Saturday to get up again” and she said “well don’t play with yourself between now and then and we should be OK”.

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