Cross Dressing, Pegging and the Promise of a Three

After my last session with Ann, the gorgeous older woman (we’d call her a MILF nowadays) who’d discovered my love for cross-dressing, things were quiet for a couple of weeks. She’d only ask me to visit her when she knew her husband and son would not interrupt which so far meant when they had gone off to watch their football team playing away. It seems that they had a run of home games.

Mind you, keen as I was to play with Ann again I did also enjoy replaying our sessions whilst lying on my bed, dressed in my mother’s lingerie, and having a good satisfying wank.

I was particularly keen to see Ann again after she had introduced me to the pleasure of anal sex in our last session. If you haven’t read that have a look here:

Actually if you haven’t read any of the earlier episodes maybe you should now:

I was getting a bit desperate to enjoy Ann in person but she was always very cool when we passed on the stairs – she lived in an apartment on the floor below mine. Anyway just when I thought I couldn’t bear it any longer she came to my front door one afternoon. “Hi”, she said “I saw your mother going out and I wondered if you’d like to pop downstairs with me.”

I was surprised because this was mid-week in half-term so there was no way that there was any football and her son was, like me, off school.

“Don’t worry they’ve gone off to Aberdeen on business. We won’t get interrupted.”

Grabbing a key to let myself back into the house I accompanied her downstairs where she took me into the sitting room. She looked me up and down and said “strip”. I did as she asked, not too quickly but not too slowly. She smiled as I peeled my pants off to release my already rigid cock.

“Stay there” she ordered, before leaving the room. I did as instructed even though I really wanted to stroke myself. Ann came back with an arm-full of clothes. “Put these on”.

“These” were a collection of girl’s school clothes for one of the local schools. “These were mine” she said, “I think they will fit you”.

In fact they were a bit on the small side but I did manage to squeeze myself into her school knickers – a dreadful green colour – and her bra. There was no suspender belt or stockings so I had to pull on some heavy woollen knee socks. Next I put on a white blouse, though as these button up on the different side from boys it was a bit of a struggle, and rather tight too. Finally I squeezed into her dark-green school skirt (which would have fitted better if I hadn’t had a massive hard-on) and some brown school shoes.

Ann went out of the room and came back with a long blond wig which she proceeded to fit onto my head. She then ringed my mouth with lipstick, applied mascara to my eyes, and powdered my face.

It wasn’t the first time I’d dressed up as a school-girl and neither was it the first time I’d worn the uniform of this particular school (see here but I felt a bit uncomfortable as the clothes were rather tight on me.

“You look like a right fucking slut” said Ann, in an angry sounding voice. “Look at you, your skirt is so fucking short I can’t just see your skanky knickers I can see what you had for breakfast.” Shocked, I tugged my skirt down “and what’s that fucking bulge between your legs?” she shouted.

As I looked down she said “show me what’s causing that” so I pulled my knickers down and lifted my skirt so she could see my huge erection.

“You are a dirty little whore and I’m going to teach you a lesson. Come with me.”

Frankly I was shocked, I’d never seen Ann act like this before, she had always been tender and loving but today she seemed angry and violent.

In the bedroom Ann pulled off her sweater revealing a lacy black bra. She then loosened her full skirt and let it drop to the floor. When I saw that instead of wearing panties she was wearing a leather harness and what looked like a cock I almost shot my load.

Ann picked up a tube of what I later found out was KY Jelly - “turn round” she ordered, “bend over”. I did what I was told and she moved behind me. I felt her finger stroke my arse-hole clearly slippery with whatever was in the tube, and insinuate itself inside me. She stroked my hole surprisingly gently and I found myself enjoying the sensation very much.

After a few minutes she withdrew her finger from my rectum and said “I think you’re ready now”. I turned my head around and saw her squeeze a large amount of clear jelly onto her hand and commence to massage it onto her artificial cock. “Open your legs” she said “and face the front”. I felt her cock slide into me with less resistance than I’d imagined. It wasn’t painful but it wasn’t pleasant either. Uncomfortable. But then as she started to move the cock in and out of my arse I found myself enjoying it far more than I thought possible, but I didn’t think I was likely to cum anytime soon.

Ann had thought of that so whilst she was shagging my arse she also wrapped an arm around my waist and wanked my cock. Fuck, it was good and it didn’t take long until I gushed a load of spunk in three or four powerful jets.

I collapsed on the bed, the aftershock of the powerful orgasm leaving me twitching in pleasure. Ann sat beside me and gently stroked my arse cheeks, bending close to kiss them.

“I enjoyed that” she said “and it looks like you did too”. I indicated my pleasure with a long “mmmmmmmmm” and she laughed. “Shagged out are you?” Still enjoying the pleasure of a massive cum and a tingling arse I said nothing. “I think it’s time for some champagne” said Ann, going out and leaving me in the warn afterglow of awesome sex.

We lay side by side on the bed sipping champagne and holding hands. “You really liked that didn’t you?” “Yes.” “Have you ever done anything like that with another boy?” I laughed “God no, that’s the first time anyone has fucked my arse”. “But have you ever played with other boys. Maybe dressed up with them?”

In the afterglow of our sex I admitted that, yes, I had indeed enjoyed sexual games, including dressing up in female clothes, with other boys. I told Ann about my first love (read it here and she was very aroused, so much so that she used her rubber cock on herself as I told her all about it – and at the same time she wanked me off. And she called me a slut!

Our immediate sexual desires sated for the time being we lay side by side. “I’ve always been turned on by the thought of watching two boys have sex. Do you think your friend might like us to have a threesome?” The idea appealed to me, which became apparent as my soft cock started to stiffen again. “Well you certainly fancy that” she laughed.

I said I’d ask him next chance I got but as I was getting hard again maybe she should do something about that. She did. God that woman had such a soft sensual mouth.

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Posted by daviea9
7 months ago    Views: 637
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7 months ago
It was all the more exciting being my first time. But not the last.
7 months ago
I'd been having fantasies about arse play and your story came at the perfect time. It had all the right elements,: girls, discipline, school skirts and lube. Perfect, by me.