A friend [F] accepts my [M] lingerie wearing kink and surprises my ass!

A very curious thing happened to me the other day and I feel I need to share it with you…

I have been ‘mildly’ crossdressing for over a year now. I say ‘mildly’ because I am not into full feminization, I just love the feel and look of lace panties when they are hugging a good looking cock, not to mention the taboo. I have taken to wearing stockings too which feel amazing, it’s like having your whole lower half caressed persistently. I have thought of wearing a bra but, although I can almost imagine how amazing it would feel, I don’t think men look as good in them as women, by a long way. Panties though, well that is a different matter. Anyway, I digress, on to the story.

Emmy’s Iron Maiden Glory Hole [Msub, Fdom, anal, exh, huml, swing, voy]

This is a continuation on from the ‘A Surprise Ass-Fucking in Panties’ and ‘Emmy’s games’ stories.

Previous stories:

A Surprise Ass-Fucking in Panties sexystories/comments/26myqy/a_surprise_assfucking_in_panties_msub_fdom_anal/

A Surprise Ass-Fucking in Panties part 2 sexystories/comments/26qic1/a_surprise_assfucking_in_panties_part_2_msub_fdom/

A Surprise Ass-Fucking in Panties part 3 sexystories/comments/26tgta/a_surprise_assfucking_in_panties_part_3_msub_fdom/

Emmy’s Games Part 1 sexystories/comments/276k8w/emmys_games_part_1_msub_fdom_anal_mast/

Emmy’s Games Part 2 sexystories/comments/27c2q7/emmys_games_part_2_msub_fdom_anal_exh_huml_swing/

Emmy’s games (Part 2) [Msub, Fdom, anal, exh, huml, swing, voy]

This is a continuation on from the 'A Surprise Ass-Fucking in Panties' and the second part to 'Emmy's games'.

Previous series here: A Surprise Ass-Fucking in Panties

A Surprise Ass-Fucking in Panties part 2

A Surprise Ass-Fucking in Panties part 3

Emmy's games Part 1


“Well? Did Suzie help you fill the condom some more?” says the text from Emmy.

I had just pulled my trousers back on after being jerked off by Suzie into a condom, which I had filled for the second time today whilst wearing panties Emmy had instructed me to wear. The stockings Suzie helped me put on feel amazing underneath my jeans. I can feel their tight grip on my thighs and the fabric rub against the inside of my trousers when I move which is a constant reminder of their sexyness.

“Yes, fucking hell, Suzie is hot! And this condom is already filling up!” I text back to Emmy.

Emmy’s games (Part 1) [Msub, Fdom, anal, mast]

This is a continuation on from the 'A Surprise Ass-Fucking in Panties' series but the start of a new series in its own right.

Previous series here: A Surprise Ass-Fucking in Panties A Surprise Ass-Fucking in Panties part 2 A Surprise Ass-Fucking in Panties part 3


“Put my panties on,” says the text message from Emmy.

It is 9:30am and I have just woken up. I look across to the bedside table and see Emmy’s panties sitting there all dried out from last night's shenanigans. I lean over and pick them up, and can’t resist the urge to hold them to my face momentarily and savour their aroma. I do as the text message asked and put on Emmy's cotton panties. They are not what I usually wear, not quite as slutty, but the fact they are hers has me rock hard the instant my cock touches them.

“They are on,” I text back to Emmy.

Immediately I get a text message back. “Good, my little panty slut. Now before you get dressed, go and put a condom on your cock.”

A Surprise Ass-Fucking in Panties Part 3 [Msub, Fdom, anal]

A continuation from Part 1 A Surprise Ass-Fucking in Panties & Part 2 A Surprise Ass-Fucking in Panties Part 2

Emmy and I make it home to my front door unseen, much to my relief, our crotches are still soaking wet from Emmy pissing on me not more than 5 minutes before. We stumble in the house punch drunk with passion and I make my way straight to the drinks cabinet to pour us both a stiff drink. I notice Emmy wandering into the kitchen and when I walk through to hand her the drink I’m surprised to see she is looking in my fridge.

“Hungry?” I ask.

“Oh Humphry, I saw you had a trifle and I hoped you would still have some squirty cream left.” she said with a wink. “Oh yay, here it is!” She says holding the can high with a big grin on her face.

A Surprise Ass-Fucking in Panties Part 2 [Msub, Fdom]

A continuation from Part 1 A Surprise Ass-Fucking in Panties

So, I am walking down the street holding the hand of a beautiful woman who, just five minutes previously, had her hand down the back of my jeans caressing my lace panty-covered arse and finger fucking my asshole. The once hot cum in the front of my panties is now cooling against the front of my crotch as I try my best to walk, still weak at the knees, down the street.

I am still unable to believe the brazen way in which Emmy just had me like that in the darkened corner of a public bar, yet here we are walking back to my house so that she can “take a closer look at the mess I made in my beautiful panties”. I breathe a heavy sigh, almost in relief, as we get further away from the pub and it is just Emmy and me walking alone. We shoot each other a look and and a smile.

“Alright, Humph?” Emmy asks.

“Yes, Emmy, although I have a rather cold crotch!” I jest, highlighting the cooling breeze on the front of my damp jeans.

A Surprise Ass-Fucking in Panties [Msub, Fdom, anal,]

A very curious thing happened to me the other day and I feel I need to share it with you…

I have been 'mildly’ crossdressing for over a year now. I say 'mildly' because I am not into full feminization, I just love the feel and look of lace panties when they are hugging a good looking cock, not to mention the taboo. I have taken to wearing stockings too which feel amazing, it's like having your whole lower half caressed persistently. I have thought of wearing a bra but, although I can almost imagine how amazing it would feel, I don't think men look as good in them as women, by a long way. Panties though, well that is a different matter. Anyway, I digress, on to the story.