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The Old Man and the Sissy

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By *tephanie Somtimes OP   TV/TS
6 weeks ago

South Derbyshire

I had only briefly chatted to Frank but I agreed to meet him in Morrisons car park.

I knew he was in an electric wheelchair so he was easy to find.

Initially I wasn't sure about him. I liked much older men but he looked quite frail in his wheelchair. He even still had his slippers on.

I didn't want to be rude so when he invited me for breakfast in the cafe I agreed.

Frank went up to order and took control straight away which I liked.

It wasn't easy to chat with so many people about but chat we did.

Straight away he peeked my interest with talk about role play. He may have been an old man but he had a mischievous mind and a twinkle in his eye.

He asked me if I had a maids outfit and I explained I did but that I didn't like it. It was quite traditional, black cotton with a white lace pinny. I said I thought it made me look frumpy but he said he'd love to see me in it.

I told him that in all my relationships with women I was the house husband so doing chores around the home would come quite naturally to me.

I asked him about other scenarios he would liked to explore. He mentioned boss and secretary, something I really liked the idea of. He explained how he always wanted one of his office girls to crawl under his desk and suck him off.

I must admit my eyes lit up at the prospect of that, as it was always one of my fantasies.

Any more I asked?

Straight away he came back with nurse and patent. The nurse would be giving him a bed bath and he would get a hard-on. The nurse being unable to resist climbing aboard and impaling herself on his cock.

I asked Frank where he lived and he said in a retirement home but he had his own self contained apartment so it wouldn't be an issue entertaining.

We arranged to meet again at his place the following week where I would dress as a sissy maid and do some of his housework.

I found my little sissy cock getting hard in my panties. Frank was a very naughty man and I loved all his naughty ideas and couldn't wait to act them out.

Later that day I dug out my maids outfit from the bottom of the wardrobe. I'd not worn it for years so I popped it in the washer to freshen it up. It was out on the line drying within the hour. It felt so naughty hanging girly things out to dry but none of my neighbours ever mentioned them.

When it was dry I decided to shorten the length of the hem with that wonder-web iron-on stuff. I wanted it short enough to show off the top of my lace-topped stockings. At least then it wouldn't look so frumpy.

I tried on the outfit for the first time in years and with the shorter hemline it felt more provocative.

I was excited to meet Frank again he was a sweet old man like a character from Last of the Summer Wine but with a very naughty streak.

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By *rumforfunMan
6 weeks ago

Oldbury

Look forward to second part

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By *ohnsy2022Man
6 weeks ago

Chorley

Very good start xx

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By *erry55Man
6 weeks ago

Portlaoise

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By *tsuptoyou69Man
6 weeks ago

lowestoft

oh dont stop now things are getting interesting

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By *ubbbbb6969Man
5 weeks ago

hebburn

cant wait for this one xx

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By *ita99TV/TS
5 weeks ago

bognor

More please ❤️❤️

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By *lutty Sara2020Man
5 weeks ago

Stratford on avon

Loving this so far

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By *imale999Man
5 weeks ago

dudley

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By *usan 749ukTV/TS
5 weeks ago

Bangor

Good start x

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By *orkDefenderMan
5 weeks ago

Wakefield

This could be interesting

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By *tiffunMan
5 weeks ago

wantage

Oh good sounding a promising start

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By *achealtvsubtoyTV/TS
5 weeks ago

hoddesdon

This could get very kinky,,,I hope !

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By *ustjanMan
5 weeks ago

bristol

good start

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By *lasgowlatexMan
5 weeks ago

Glasgow

Very nice

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By *hris-in-WiltsMan
5 weeks ago

Chippenham

mmmmmm - you can't beat a French maid story xxx

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By *echman.1Man
5 weeks ago

Home

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By *ers_Viking_FukMan
5 weeks ago

Gorleston

Fantastic start

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By *urieMan
5 weeks ago

Ashford

I love this and fantasise about similar

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By *harlotte39cdTV/TS
5 weeks ago

rochester

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By *tephanie Somtimes OP   TV/TS
5 weeks ago

South Derbyshire

The night before I was due to meet Frank I started getting ready. I shaved and waxed my body from tip to toe. I loved being smooth it made me feel so feminine My little titties felt so soft next to my hard nipples.

The following morning and I showered and douched and applied my favourite Lacoste body lotion.

Then I had a debate with myself regarding whether suspenders should go over or under knickers. I went with over.

I opened my draw full of butt plugs. I love being plugged when doing housework. It focusses the mind and makes everyday chores more enjoyable.

I didn't want to use lube as I get so wet so I just gave the butt plug a lick and slid it inside me. I couldn't help but cum a little but I can't help that.

I laid out my underwear and the maids outfit. I couldn't decide whether to wear my white frilly knickers or the black but went for the white as it was a nice contrast with the black maids outfit.

I slipped on my lace-topped black stockings and did up the suspenders.

The back of my hand brushed against my little willy it got hard. I was having none of that so slapped it with the back of my hand and it wilted back into my frilly knickers.

The maids outfit was quite a tight fit but I loved how it hugged my body. My push up bra did the trick with my boobs and although I didn't have a cleavage they were bubbling over the bodice.

I did my make-up keeping it simple. Just foundation, lippy and mascara. I picked the blonde bob as it suited me best.

I rarely go out dressed but Frank had asked if I would arrive as a girl as he wanted his neighbours to see. I was nervous about this but it was still winter so I was able to wear my full length quilted coat with the hood up. Purely because I didn't want my neighbours to know about me.

I had pink pumps to drive in and I would put on my 5 inch heels outside Frank's apartment.

Frank had mentioned that his apartment wasn't in the main residential home but in a little bungalow outside

Soon I was ready to leave the house. I checked my look in the full length mirror, put on my coat grabbed my heels and headed for the car hoping none of my neighbours were out and about.

Frank's was only 15 minutes around the corner. I pulled up outside his bungalow slipped my heels on, threw my coat in the back of the car.

I felt very vulnerable walking those few yards to his door with my stocking tops on display and the cold air blowing up the shortened hem of the maids outfit.

I could see his net curtains twitching so I knew he was watching me.

I knocked the door but he took ages to open it making me squirm I felt so exposed. Eventually he did open it and I told him he was a naughty man for making me wait. He laughed and said he wanted to be sure his neighbours saw me.

Frank looked very smart in his beige check shirt and green tie, a lovely fairisle jumper and thick corduroy trousers and slippers. I gave him a peck on the cheek and noticed a lovely fresh masculine smell of shaving foam.

Straight away his hands were all over me, under my skirt and toying with my stocking tops.

I don't know what it is about old men but my little willy was already hard.

I could see there was washing up to be done and I told Frank off in no uncertain terms.

I set about doing the washing up, making sure to bend over as often as I could but while still retaining the butt plug in my ass.

Then it was the vacuuming. I felt like Freddie Mercury as I sang the song, "I want to break free", although I think I looked more like Roger Taylor in that video than Freddie.

I looked over at Frank and I could see he'd got his cock out.

I told him he was a very naughty man but that his cock looked delicious.

I stood next to his wheelchair and bent down keeping my legs straight and my bottom in the air. His cock was fat but totally flaccid but I still enjoyed taking it into my warm mouth.

As I was sucking it he told me that the doctor had said he could go on Viagra if he ever met a woman and that he'd booked an appointment to get some.

I told him not to worry as I was enjoying myself regardless.

He slipped his hand into the back of my panties and found my butt plug. I was getting so wet by now it just fell out and rolled along the floor.

He didn't waste any time and started fingering me.

With his other hand he pulled down the front of my bodice and started pinching my nipples.

My legs started to tremble when he found my prostate.

Oh my was he good, he certainly knew how to milk a girl like me.

For an old man his upper body was quite supple and he managed to suck on my little willy while pinching my nipple and fingering me.

My legs were trembling and I put my arms around him to steady myself.

My moans got louder and louder his fingers working magic up my ass.

I couldn’t hold out any longer and just exploded in his warm mouth.

I collapsed down across his wheelchair.

He pulled my frilly knickers down and spanked my bottom really hard telling me I had been a very naughty girl.

I told him that he was the naughty one for making me cum when he hadn't. I apologised and told him I had failed as a maid and as a sissy.

He said that I was wonderful and had given him a wonderful reward and that next time when he got the Viagra he would fuck me senseless.

Then I noticed that he had cum, so I did my duty and licked him clean, redeeming myself in the process.

I offered to help shower him but he said he had some bath in bed wipes, they just needed to be warmed in the microwave.

I went back to my sissy maid duties and duly cleaned him up helping to change his Y fronts and putting some washing in the machine.

When all was done he thanked me and he showed me to the door. He asked for a kiss and we had a lovely gentle kiss, not full tongues but very lovely which again made me hard.

He said next time could we role play the boss and the secretary. I smiled and said is that the one where I crawl under your desk and suck you off. He blushed and said yes, I said I would love to.

We kissed again and agreed to meet the same time next week.

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By *lasgowlatexMan
5 weeks ago

Glasgow

Excellent story

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By *achealtvsubtoyTV/TS
5 weeks ago

hoddesdon

Naughty, Naughty very naughty,,,lol,,,xxx

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By *ndiesguy200Man
5 weeks ago

naas

Lovely story

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By *erry55Man
5 weeks ago

Portlaoise

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By *imale999Man
5 weeks ago

dudley

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By *ndrews642Man
5 weeks ago

exeter

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By *echman.1Man
3 weeks ago

Home

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By *ranthamfun63Man
3 weeks ago

grantha

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By *oLadyTV/TS
3 weeks ago

crewe

Splendid…..my knicker elastic is suddenly much tighter.

Btw……panties are ALWAYS, ALWAYS, ALWAYS worn OVER suspenders.

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By *oannacd70TV/TS
3 weeks ago

worcester

Can't wait for the viagra episode

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By *ashtoolMan
3 weeks ago

belfast

hope to hear about the boss

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By *xhibitionist500Man
3 weeks ago

Chester le street

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By *oose1Man
3 weeks ago

doncaster

Lucky man

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By *emdad73Man
3 weeks ago

Wirral

Definitely more of this please x

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