Sweet Charity

You may have heard of the phrase sweet charity, well in my case it was certainly sweet to me. I have built up a large part of my CD wardrobe through judicious visits to charity shops wherever I may be in the country. In one of my local charity shops there's an assistant called Wendy who I would judge is in her mid fifties but looking well on it. She's always well turned out in neat blouses, always a just above the knee skirt, never bare legs and 3 to 4 inch heels of various kinds. I must admit that my fairly frequent visits to this particular shop engender a feeling of hornyness on two counts. On the one hand there's the thrill that I might secure a bargain addition to my secret wardrobe but on the over hand I find myself lusting over the wonderful Wendy. I often find myself distracted with thoughts of whether she wears stockings, what it would be like to run my fingers through her neatly coiffured hair, taste her mature pussy juices, feel her ruby lips around my shaft and tongue her puckered hole etc. Well following my most recent visit, I was to begin to experience all these things and much more besides.

I'd selected a little black dress from the rack which was in reality slightly too small but the feeling of slight restriction adds to the pleasure for me so it was no problem. I'd also picked up a pair of 5" heeled sandals off the shelf and headed to the counter to be served by Wendy's mousey colleague, the usual phrase of "can I bring it back if it doesn't fit her" playing on my lips. Unbeknown to me however, Wendy had other ideas and she intercepted me, gently guiding me by the elbow into the changing area of the shop? "Don't think I don't know what your game is" she said sternly under her breath and instructed me to go into the storeroom with the impetus that she would tell all the shop about my dirty little secret if I didn't. I protested that her colleague would be suspicious but she informed me with a wry smile that Charlotte was about to go for lunch and the shop would then be shut for an hour. Once in the storeroom, Wendy pleasantly surprised me by grabbing my crotch and then forcing her tongue deftly into my mouth. I took the opportunity and placed my hand on her pert derriere which she obligingly clenched as if on cue. Unable by now to resist, I lifted her dogtooth knee length skirt and discovered that she did wear stockings. I cheekily pinged a suspender against her clenched buttock then worked my fingers round to her by now humid lady garden. I started to pull the gusset to one side when Wendy suddenly slapped my hand before telling me there wasn't time apart from time for her to give me a taste of things to come. She immediately dropped to her knees, unzipped my flies and released my straining tumescence. Following a quick lick of her lips and a refrain of "I believe you sissy boys refer to this as a man clit", she set about my member with gusto. She took all of me into her experienced and willing mouth until my balls were nestling on her chin and then drew back until only my helmet was balanced on her pearly white teeth. She then darted her tongue rhythmically and expertly around my swollen tip before licking up and down my shaft and occasionally sucking on my balls. I was reaching the point of no return by this point and was definitely not prepared for what happened next. With another wry smile she muttered something about ass pussy before taking all of me back in her mouth. I couldn't hold out much longer and finally lost it when she gave a deep quivering suck and simultaneously stuck a manicured digit up my bum. She then stood up, kissed me full on the mouth, the musky aroma of my gentlemen's relish still on her breath and said in a matter of fact voice: "Come round to my house, number 4 Shaftsbury Mount tomorrow afternoon and I'll show you what real pleasure is; make sure you come dolled up though".

I woke the following morning with a feeling of trepidation tempered with a certain frisson of excitement. After a leisurely breakfast I set about transforming myself into Michaela. I wanted to get every detail just right as I'd never been out of the house dressed as a woman before but had no choice on this occasion, given Wendy's strict instruction to turn up at her house dolled up. I always begin by painting my nails and settled on Wild Cherry, half expecting that some popping might take place later. Once my finger and toenails were fully dry, I retrieved my Lingerie and Hosiery from their secret storage. I selected a maroon basque with matching thong along with a pair of smokey grey fully fashioned stockings. Having adjusted the suspenders on the basque, I slowly teased a stocking up my left leg, my cock twitching perceptibly as I did so. I stood up to check the seam line in the full length mirror and being satisfied, clipped the stocking in place. Having repeated the process on my right leg I decided on the black 5" sandals I'd purchased on my last trip to the local charity shop. As I fastened the ankle straps, I was struck by the thought that encased in sheer nylons; my toenails looked like boiled sweets in a gauze bag, a peculiar but strangely arousing thought. I then stepped into the little black dress recently purchase before adding the finishing touches of full makeup, auburn wig and mock pearl jewellery. Having prepared myself physically I began to prepare myself mentally before stepping outside for the first time as Siobhan,in bright afternoon sunshine to boot.

Although I'd paraded around the house in high heels on numerous occasions I'd never set foot outside in them. Consequently I felt pretty self conscious as I sashayed down the road but no one seemed to notice that Siobhan wasn't a real lady. Thankfully it was only a short walk to Wendy's house and I was ringing her doorbell before I had time to be any more self conscious. She opened the door within seconds as if she'd been standing guard in her hall. Regardless, I was soon stood fully to attention when I took in the vision of mature femininity stood before me. Her entire outfit was either 1 inch shorter or longer than normal. Her feet were encased in a pair of patent red 5" heeled peep toe shoes; her legs resplendent in a pair of Cuban heeled mid tan stockings under a pin stripe skirt resting an inch above the knee. Her outfit was topped off with a diaphanous cream blouse neatly accentuating the white basque she was wearing underneath. She beckoned me in with a scarlet tipped finger and bluntly announced "don't be expecting a cup of coffee or any of those other clichés; I want to get straight down to fucking". With that she led me into her bedroom and pushed me down quite f***efully on her king-size bed. "I'm going to give your man clit and ass pussy a thorough going over" she announced whilst hoisting the hem of my dress above my waist. The front of my thong was pushed to one side in seconds and once again I was balls deep in Wendy's warm inviting mouth. Just as I was about to reach boiling point, Wendy ordered me to turn over on to my front. She then pulled my thong down and over my ankles before tossing it into the corner of the room. Before I knew what was happening I felt her tongue gently rimming my puckered hole. She certainly knew what she was doing as she reached under me and began stroking my throbbing cock whilst simultaneously darting her tongue in and out of my ass pussy. I could soon take no more and arched my back before shooting my load over Wendy's duvet. As I turned back over another vision of lust entered the room dressed in an identical outfit to Wendy. I jokingly asked if they were twins but Wendy curtly told me that this was her friend Denise and that she was going to join us to spice things up a bit.

Wendy and Denise soon had me rock hard again as I watched them kiss and fondle each other. Whilst taking a breather from licking Wendy's clit, Denise noticed my stonking hard on and shuffled across the by now dishevelled and love juice stained bed. She gave me a long lustful stare and then set about performing fallatio on me. She was just as good as Wendy and I was soon away in my own little world. I was conscious enough however to obey Wendy's command to get on all fours at which point Denise positioned herself beneath me her head directly under my manhood and the rest of her body behind me. She resumed her oral duties and as she did so, I noticed Wendy removing a large strap - on from her beside drawer along with a tube of lubrication. I thought that I was going to be treated to another lesbian show but how wrong I was.

Wendy climbed onto the bed, the strap on bobbing wildly and then positioned herself behind me. I suddenly felt a drop of cold gel on my anus and then Wendy began to work her fingers in and out of my ass pussy. The fingering soon stopped however and I felt a hard object pressing against my ring. It was then I realised that Wendy intended to use the strap- on to penetrate me. Wendy began to push forward and at first my sphincter muscles would not accept her substitute cock but then as if by magic my rectal gates opened and Wendy was probing deep inside me. The initial feeling of intense pain soon gave way to one of pleasure and I relaxed and waited for what could only be a thundering orgasm with Wendy pegging away in my ass pussy and Denise deep throating me. The action suddenly ceased however and I was conscious of the musky smell of pussy directly under my nose. As the royal pounding of my ass pussy had resumed at this stage, I assumed that I was about to savour the labial delights of Denise but as I started licking, sucking and lightly chewy the clit before me it was Wendy's voice that I heard saying excitedly "oh yes, more, more". In a state of confusion I opened my eyes and saw that the strap-on was laid on the dressing table and in the wardrobe mirror I could see that it was Denise pounding away in my arse with her meaty man clit. It turned out that Denise was actually Wendy's toy boy husband who had a penchant for cross-dressing and ass fun. I was just getting accustomed to this new state of affairs and enjoying the cherry popping I was receiving when Wendy instructed Denise to withdraw and come round the front for me to suck her off. I started off gingerly, having only performed oral on a dildo before but I soon got into the swing of things. Not wishing to be left out, Wendy attached the strap-on to her mature form once more and resumed giving my ass pussy a right royal seeing to. My mind span with the complexities of the situation and the fact that I was being spit roasted by a husband and wife and damn well enjoying myself. I didn't come again that night as my balls had been drained of every last drop of spunk but Denise treated me to a liberal spurt of baby gravy and I gave it to Wendy in both holes using the strap on as back up. Both my mind and body were well and truly fucked on that memorable afternoon.

100% (14/0)
Categories: Shemales
Posted by SiobhanSeeDee
2 years ago    Views: 994
Comments (5)
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2 years ago
Gotta go to the trift shops more often greeart story
2 years ago
Nice turn of events, eh? Great story. Makes me want to head to a "charity" shop and take my chances!
2 years ago
incredible story ... nice to read some well written erotica on here
2 years ago
love it
2 years ago
Great story! Maybe I'll get lucky in a thrift shop!