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By (user no longer on site) OP
over a year ago
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Hello all. I have recently discovered this site and thought you might like to hear what happened to me, a while ago now.
I am a 58 year old cross-dresser living in the UK. Although I remain in the closet I have discovered there's a wealth of wonderful bargains to be found in the local charity shops. Therefore I have become a shopping diva, boldly buying up any ladieswear and accessories I fancy. The elderly ladies who tend to staff these shops are always very friendly and appear more than happy to make any sale. So apart from the great value for money, it's usually a fun, relaxed experience. I'm not so brave that I ever try anything on in the changing rooms but everything is so cheap, it doesn't matter if I occasionally get something which is a poor fit. If I do ever make mistakes I tend to donate them back for some other lucky girl to find.
One time I was out of town and popped into one of these shops. With no fear of running into anyone who knows me I allowed myself a long, leisurely browse through the ladieswear rails. I had discovered heaven. I couldn't believe the array of assorted silky, sheer, satiny dresses, skirts and tops. All the feminine delights which caused me to become a cross-dresser in the first place and all in my size! I even found a couple of pretty, lacy full slips and a pink silky nightie in the lingerie section. (I ADORE slips and nighties.) Following my initial browsing I almost paniced for fear that another shopper may spy MY goodies. So I greedily grabbed at least fifteen delicious items and eventually struggled to the counter. It was so funny. As I laid them on the counter, gravity and slinkiness combined in an effort to slide all my new treasures onto the floor. The lady and I had to struggle to keep control of all the lovely things as she rang up the sales. On this occasion the assistant was a younger lady, about my age and I wondered how she might react. I needn't have worried, she was very professional. More than that, as she held up and carefully folded each item before placing them in a bag for me, she was smiling and commenting on how pretty everything was. I was positively glowing that she approved of my purchases. I'm not even the least bit camp but I did enthusiastically agree, never saying they were for me but of course she knew the truth. (Perhaps I should have asked for her phone number but I wasn't bold enough for that.) I didn't care about the long queue forming behind me or what the other shoppers may have thought. As much as I enjoy wearing the clothes, the moment of purchase, when they become MINE, is always such an indescribable thrill. It's not even sexual, just pure joy. I'm sure this must be how real women feel when buying pretty clothes.
Anyway I am digressing. It was about a year ago when I was in a local shop and I noticed a lingerie item which I've always wanted but never been able to find, even online. It was a baby pink, light control, shiny lycra, all-in-one corselette with four shiny, detachable, ribbon covered, metal clip suspenders. This was not some sturdy foundation your granny might wear. Everything about it was absolutely darling, cute and girlie. It had half-lace, half-satin, soft stretch cups with a dainty bow in the centre of the bustline, shiny narrow shoulder straps with front metal adjusters, a smooth tummy panel and exquisite stretch lace on the front of the hi-cut leg openings. The adjustable crotch fastened with two rows of three metal hook and eye closures. Being an older style garment, probably 1980s vintage, it had a full back too. I like my bottom to be constantly caressed by silky nylon so modern thong styles just don't do it for me. Better yet, despite the fact there was no original tag, I could tell from it's pristine condition it was unworn old stock. The only question remaining was the size. It appeared rather small but as I looked inside I was thrilled to discover the label which said 36A. I also noted it was a Marks and Spencer creation! (No wonder it was such a beautiful design and made from such high quality fabric.) I am very slim so normally take a 36B in bras, using my silicone breast forms to fill them out. However due to the stretch of the corselette I knew it would fit and hug me all over, including my chest, without the need for false boobs. I adore the feeling of bra cups against my skin, even if it leaves me looking like a flat-chested little girl! I checked the item once more for any flaws or missing suspender ribbons but it was absolutely perfect. I was so excited I took it straight to the sales lady without browsing any further. I paid the ludicrously low price of three pounds fifty and scampered home to try it on. I live a short distance from the town centre so was home within a few minutes.
Once in my bedroom I stripped completely. As always, when getting dressed en femme, I squirted myself with a little body spray. Rimmel Magical as I recall. Then I stepped into my yummy new item and luxuriated in the feeling as I slid it up my smooth legs. I was so glad I had freshly shaved my entire body the previous night. I tucked my male parts as far back as I could and quickly drew the pantie section of the corselette up to restrain and smooth away any unwelcome bulges. I stretched and smoothed the rest of the heavenly pink garment up my body until I could slip my arms through the shoulder straps. I didn't even need to adjust them. It was the perfect fit I had hoped for. I felt so hugged and snuggly with the thin lycra stretching tightly but lightly around my torso. I looked in the mirror. Oh, even I had to admit, I looked cute and adorable!
Of course there was still the small matter of the shiny, dainty suspenders tickling my thighs to attend to. I opened a new pair of jet black 10 denier stockings and took my time, teasing the soft nylon up my legs. I fastened the suspender clips, taking special care to arrange the shimmering ribbons neatly inside and outside each clip. I stepped into a pair of three inch stiletto heels and took another look in the mirror. Wow, my legs looked so feminine, just like my body! Of course I felt sexy and gorgeous as I paraded in the mirror for a while. Every step brought delicious shivers of delight as my new lingerie and stockings stretched slightly, caressing my skin, especially the tight confines of my intimate places. I always tuck and feel so special with my sex organs cossetted in exactly the same place as a real girl. However the nice thing with me is that when I'm wearing what I consider to be my best lingerie, my male parts are strangely respectful of their joyous, beautiful, feminine surroundings. Ok, on this occasion they were tightly tucked away but even in looser-fitting 'best' panties my private parts tend to remain soft and 'polite'. I'm very lucky that way because it I don't like to make a mess or even leak pre-cum into my favourite pretties. Naturally I do have lesser quality silkies, for when I need to find sticky release but I love for my crotch to appear as feminine as possible. I particularly like the feeling when my balls pop back inside their body cavities and my maleness is totally hidden. I don't know if that makes me a sissy. I kind of suspect so. Anyway, this particular day my body and pelvic area looked totally authentic. With the full length mirror angled to cut off my male face, I could almost believe there was a sexy young woman in the room with me.
I could have spent the rest of the morning playing dress-up, enjoying the sensual thrill of my silky slips, skirts, blouses and dresses gliding over my stunning new foundation garment. However I only ever dress fully after dark, when anything seems possible. Also it was getting near lunchtime and I was feeling very pleased with myself. I wanted to celebrate my newly found, beautiful bargain. So I decided to treat myself to a pub lunch back in town, while remaining dressed in my gorgeous undies.
I slipped out of my high heels and donned a pair of thin black nylon ankle socks. They are menswear but made in Italy and so much finer than my normal socks. I knew they wouldn't snag or damage my stockings. Similarly I found a pair of loose-fitting, dark green, lightweight cotton trousers. I thought there was a slight possibility my rear suspender clips might be visible when walking but that just added a little excitement to the adventure. For my top I chose a cream t-shirt. Obviously there was a danger the shoulder straps of my corselette may show through so, with it being a mild day, I also wore a lightweight, sleeveless jacket, unzipped. After checking myself in the mirror I was satisfied that the lacy cups of my corselette were flat and invisible through the t-shirt.
I left my house and began the walk into town. Although I was now wearing trainers on my feet, I was instantly aware that my corselette and especially my tightly tucked privates were causing me to walk with a more feminine gait than usual. Far from being worried, I positively enjoyed the thrill of knowing I may have been giving a slight clue about my little secret. Again it was lovely, feeling the gentle stretching and teasing of my beautiful undergarments, especially with the light fabric of my trousers drifting over my stockings. It was even more exciting when I put my hands in my trouser pockets and felt the satiny smoothness of my suspenders through the thin cotton. The short walk was uneventful but thrilling all the same. There were very few people around to notice my semi-mincing footsteps. I was very careful crossing the roads though. I certainly didn't want to pay a visit to the hospital emergency room dressed as I was and of course I would have hated to ladder a new pair of stockings!
Once in town I was feeling confident and a little bit naughty so I allowed my jacket to flap open now and again. The high street was very busy but I was sure no one would be paying me close enough attention to notice anything out of the ordinary. I was just having a little fun with myself.
After a while I entered a pub I'd been to a couple of times before. I ordered a pint of beer, a light lunch and sat down at a low table on an equally low stool. There were a few other folk in there but no one sitting close to me. However I was feeling a little more self-conscious. Now I was seated, my jacket kept falling open. I nervously checked my chest and noticed that in this position the centre bow and lacy edges of my corselette's cups were creating a slight tell-tale effect through my t-shirt. So I fiddled with my jacket to keep my chest covered. Also the formerly loose-fitting trousers were now quite tight on my thighs. The tabs of my suspenders were producing a definite bump through the thin material but with no one around I didn't worry too much.
The meal was very good but the beer was even nicer. I had a taste for it. So, still celebrating my earlier shopping success, after I'd finished eating I went back to the bar for another pint. When I returned to my seat a chap was sitting at the next table, diagonally opposite to me. Now, I'm a friendly kind of chap and so was he. Before long we had struck up a casual conversation. I was even more concerned about my lacy secret now and continually adjusted my jacket. I wondered about the little bumps on my thighs too but didn't dare look down for fear of leading his gaze there. From where he was sitting he could have easily seen the outline of the suspender clips if he looked close enough. After another minute or two of chatting he introduced himself as John and offered me a hand shake. We were almost sat close enough for that but it did mean I had to lean forward a little. I felt my jacket gape open as I shook his hand. We maintained eye contact so I was sure I hadn't been rumbled. However I was quite clumsy in my haste to grab the jacket closed again. A minute later he asked me for a light. I produced my lighter and should have just given it to him but he leaned foward for me to light his ciggy. I also had to lean in and again lost control of the jacket. This time, especially due to relative angles involved, I was sure I saw his eyes drift past the tip of his ciggy and onto my chest.
I was feeling even more nervous now. Also the beer was starting to go through me. What with that and the fact my privates were tightly tucked and getting tender, I excused myself to go to the toilet. As I left the table I had to pass closer to John. Oh no, had he now smelled my delicate feminine scent too? I had barely taken two steps when he didn't ask, he TOLD me he'd get me another pint while I was gone. He knew what I was drinking. That had been the topic of one of our conversations. We had also discussed the fact neither of us had to work that afternoon. How could I refuse? I thanked him and tried to walk off in as manly a fashion as possible.
Due to the restrictive nature of my underwear there was no way I could stand to pee so I had to use the single cubicle in the gents. I dropped my trousers, sat and pulled the crotch of my corselette aside to allow my squashed privates and my bladder relief. As I sat there gazing at my black stockings and pretty pink suspenders I wondered what I was getting myself into. I finished peeing, dried myself thoroughly and tucked everything back in place. I re-adjusted my stockings before pulling my trousers back up and tried to stretch my t-shirt out so it was a looser fit. It was probably too late for that to make a difference now but it seemed the prudent thing to do.
When I returned John was sitting as before except now with the fresh beers. I noticed he was already some way down his second beer and hoped he didn't make some wise crack about how long I had been in the toilet. He didn't, he just smiled and we continued to chat about this and that. Everything seemed fine, casual and relaxed like before. I was pretending to be relaxed anyway. In fact the beer was helping with that. I stopped fiddling with my jacket now that my t-shirt was not so tight. Before long it was my turn to offer John a beer and he accepted. This time as I passed by him, and I'm not sure if this was deliberate or not, his knee moved slightly to brush against my leg. The contact was fleeting and light but it sent a delightful shiver through me as my nylon coated leg received the brief caress. As I went to the bar I was again nervously aware that my rear suspenders might be noticable. Not only that but my jacket was rather short. Was I also displaying a pantie line as I walked? While waiting to be served I looked in the mirror behind the bar. John was definitely looking my way and possibly checking-out my bum. Call it the effects of the beer or flattery but I suddenly felt very naughty. I 'accidentally' dropped some loose change and bent down to retrieve it, knowing for certain John would see my pantie line and the outline of my suspenders. I immediately regretted my boldness and couldn't bear to check the mirror again but was sure I could feel his eyes lingering upon me. Trembling, I fetched the drinks, squeezed back past him and sat back down again. That was when everything changed.
As we continued to talk I noticed John making what looked like an OK sign, except his hand was overturned and held between his legs. I'd never seen such a sign before. I suspected I knew what it meant but tried to ignore it. However a couple of minutes later he made the gesture again and with his eyes, directed me to look. This time it was more obvious. It looked like he was waggling an invisible pole in front of his crotch. He was offering me his cock!
I can't say I found John an attractive man because I don't fancy men at all. He was about my age, well-built and quite masculine. He certainly didn't strike me as gay, in fact he had been talking about his wife earlier. Although I have never considered having sex with a man, truth to tell, I have had a few meetings with other cross-dressers over the years. The urge to have my own cock sucked sometimes becomes overwhelming and I've been prepared to give in order to get. These have always been last-minute decisions. It's not the fact of being dressed in women's clothes which makes me so horny. It's when I apply lipstick my imagination runs riot and I envisage my lips wrapped around a juicy cock. So yes, I have sucked a few tranny cocks before but it's been a very seldom occurance. I particularly like hosiery so stroking a pair of legs in stockings while I suckle a clitty-cock is a large part of the fun for me. One thing I have discovered is that I actually like the sensation of a cock spurting in my mouth. I love the taste of cum and especially the after-taste. It seems to remain for hours, coating the inside of my mouth and serving to remind me what a nasty little sissy I've been. It seems quite addictive too. Long after my lovers have left I'll be savouring the taste and wishing for another helping. Tasting my own is never the same. If it wasn't for my annoying gag reflex I would suck and swallow a 'sister' much more often.
So when John made his obscene gesture, despite the taste of beer and cigarettes in my mouth, I experienced a sudden flavour flashback to the last time I tasted cum. Of course I was also more than a little tipsy by now. My underclothes were screaming SISSY at me and I was sure John had figured out my secret. He may have been all man but that meant he had what I wanted, CUM. So I blushed furiously as I nodded and mouthed a silent "Ok." to him. He smiled and moved to sit beside me. The pub was almost empty by now and the background music meant there was no chance of us being overheard. Even so, we furtively whispered the arrangements to each other. I could have brought him home with me but decided that was a little risky with a total stranger. I had already noted that the toilet cubicle was fully enclosed with a fairly heavy wooden door.
I wanted to get myself ready for him so asked him to meet me there three minutes later. Just to make sure things didn't get out of hand I also suggested a few ground rules. My heart was pounding and I could scarcely believe what I was saying as I told him a blow job was all that was on offer. He grinned and said that was fine with him but it was very much a one-way deal. No way was he going to blow or even wank me. I said that was cool, I just wanted to suck. I also told him how I'm not very experienced and mentioned my tendency to gag on big cocks, so asked him to let me control the pace, in order that we might both enjoy it. Again he was happy with that but he secured my promise that I would swallow.
I couldn't look him in the eye and I felt like such a slut when I whispered in his ear,
"Of course. That's the best bit."
I also asked him for another couple of favours, to make it more fun for me. Specifically that I would like him to verbally abuse me while I sucked him. I noticed him raise an eyebrow as I suggested, "sissy slut" would be a good place to start. He agreed but made his own demand, no kissing.
With all the preliminaries out of the way there was no more to be said so I headed off to the cubicle in the Gents. Luckily it was empty so I went inside and bolted the door. I quickly removed all my outer clothes and hung them on the hook on the back of the door. I adjusted my stockings, pulled my tiny natural boobs up into the cups of my corselette, sat down with my knees together and waited. My tucked cock remained soft but I was excited and nervous all at once. My only regrets were that I wasn't wearing a nice pair of heels and especially that I didn't have any lipstick with me. I licked my lips to at least give them a glossy sheen. Moments later I heard the outer door open and there was a light tap on the cubicle door.
John whispered,
"Sissy?"
Remaining seated I undid the bolt and let him in. With the door securely closed again I looked up into his eyes and asked,
"Hope you like my undies? I just bought them today."
He chuckled out loud,
"Bloody hell. I didn't know you were a tranny. Just thought you were gay."
He gave my smooth feminine frame the once-over.
"Mmm, nice though."
"Damn it." I thought. I know I'm not the most masculine guy in the world but I had no idea I 'looked' or otherwise gave the impression of being gay. No disrespect to any gay readers intended here but I felt doubly humiliated by his words and the fact I had got myself into this situation on a false premise, all of my own making. However his brief attempt at flattery did give me a warm little glow.
John took charge of matters now. He reached down, fondled my tiny titties through the satiny, lacy cups and said,
"Well, sissy slut, let's get on with it."
I hurriedly unfastened his belt, top button and unzipped his fly, letting his trousers fall to the ground. His erection was already growing as I ran my hand up from his balls to the top of his cock and hooked my fingers into the waistband of his boxer shorts. I pulled them out and down, freeing his manhood in one swift motion.
He had me sit forward and spread my legs so he could get closer. He urged me to rub my stockinged thighs up and down his naked legs. That was so nice for me too. Rather than allowing my male parts to escape, the motion caused a tightening in my crotch panel and I felt even more restricted and 'feminine' down there.
I leaned forward and planted a soft kiss on the very top of his cock. Then I wrapped my fingers around the head as I pulled his foreskin back. I slowly licked and kissed down his shaft until my tongue was probing his hairy balls. This was a new experience for me. My previous lovers had all been shaved down there. I didn't like the strong man smell as it invaded my nostrils but I inhaled deeply to get used to it and took each of his balls in turn into my mouth. He moaned his approval as I licked and sucked.
He was rock hard by now and I was surprised but thrilled to discover he was not well endowed at all. No more than four inches fully erect. My lips returned to his purple, swollen cock head and I devoured him all, in one long slow suck.
He gasped,
"Oh you fucking sissy bitch. That's so good. My wife never does this."
I slowly slid my lips up and down his throbbing pole while licking the tender underside of his thick blue vein. I looked up into his eyes, so he could see his shaft sliding in and out of my mouth and to show him how much I liked sucking his cock. His hands gently rested on my head as I quickened the pace. With one hand I softly cupped and squeezed his swinging balls. I ran my other hand all over my corselette then up and down my stockinged thighs as I continued to rub them up against John's powerful legs. After a few minutes I released him from my mouth and he groaned in frustration. However despite my earlier reticence I wanted him in control now. I took his cock in my hand and flicked my tongue around and under his glowing glans. Then I grabbed both his hands, placed them on the back of my head, looked up at him again and said,
"Please fuck my mouth."
He didn't need telling twice. I formed an "O" with my lips, in my best mimic of a blow-up doll and he pulled me forward, roughly plunging his cock into my mouth. He then began a rhythmic reaming of my warm, wet hole. His speed increased and his balls started slapping into my chin as I let him use me. All the time he called me names.
"Fucking slut, sissy whore, cock-sucking pansy bitch."
His words were like music to my ears. I was really getting into it and was far from passive as I continued to suck and noisily slurp with every stroke. His fucking of my mouth was becoming wilder and more abandoned. I sensed he would cum soon so I grabbed his bum and sucked him hard, breaking his rhythm while I held him deep within my mouth. With my nose firmly squashed into his tummy I sent a deep hum of satisfaction from my throat, providing vibration directly to the heart of his hot man-meat. John gasped as I sucked back up his shaft to again lick and swirl my tongue around his twitching cock head. I felt him tense a little as he forcefully pulled my hair and impaled me again. With his cock firmly in my mouth he set up an urgent rocking motion. Seconds later I felt his cock head grow and pulse in my mouth, once, twice, then the first jet of his cum spurted directly into my throat.
"Ohhhh yes, ohhhh, yes, yes, that's it, that's a good girl."
(This was one of my earlier requests, that he call me a good girl when he came.)
He continued slowly and masterfully fucking me as wave after wave of that fabulous, familiar flavour flooded into my mouth. I gulped and swallowed, almost gagging on his sticky flow but there was just too much of it. I had to pull back, allowing his spewing cock to spring free with a loud, wet "plop" as it exited my lips. He groaned as he shot another load of cum up into my hair. Then another warm jet splashed over my cheek and I too moaned in pleasure. I didn't want to waste any more of the creamy treat I'd worked so hard to earn so I quickly grabbed his shaft and noisily sucked it back into my mouth. Again, I hungrily gulped and swallowed all he had to offer. John's legs were trembling against mine as he continued to cum.
His spasms finally slowed in my mouth and with one final spurt he groaned,
"Mmmm, mmmm, you sissy-boy slut."
I continued to suck but he pulled me off his now tender, softening cock. He then wiped it around my face, urging me to lick up the last of his sticky residue which I did gladly.
He grinned down at me, saying,
"That was fantastic, you fucking dirty, cock-sucking sissy girl."
I smiled back at him as I felt the pearly drops dribble from my chin, onto my corselette and stocking tops. So much for me liking to keep my best lingerie nice and clean. This set had been well and truly christened. I scooped up the remaining cum from my face and made a show of feeding myself the last of his cream. I licked my cum-soaked lips in as slutty a manner as possible and not forgetting my manners I said,
"Thank you for cumming in my mouth sir."
John quickly pulled his clothes up from the floor and winked as he said,
"Meet me here next week sissy, same time."
"Yes." I replied meekly.
With that he unbolted the door and left. I quickly closed the door again and just sat there for a moment, reeling from the experience but loving the taste in my mouth.
God knows what sort of mess I must have looked. I didn't want to get wet patches on my outer clothes so I rubbed the last globs of his sticky cum over and into my corselette and stockings. That felt like such a slutty thing to do. Of course I felt even sluttier knowing that I'd just successfully given a great blow-job and to a man's man at that!
I dried my face with toilet paper, put my male clothes back on and left the cubicle. Luckily the toilet was still empty because as I checked myself in the mirror I saw the large patch of John's cum clinging to my hair. I combed it through with my fingers, washed my hands and went home.
Once there I went straight to my bedroom and stripped off my male clothes again. The taste of cum in my mouth had me feeling really horny. I laid down on my bed and unsnapped the crotch of my corselette with the suspenders and stockings maintaining the overall shape of my delicious undies. My cock was so happy to be freed from the tight garment, it rapidly became fully engorged.
With my beautiful lingerie already being despoiled by John's cum I decided to allow myself the luxury of stroking myself to orgasm. While wanking myself off I re-lived every glorious moment from just minutes earlier. I used my thumb and fingers to fuck my mouth as I leisurely stroked my cock and rasped my jet black stockings together. Eventually I worked myself up into a frenzy and shot my hot, sticky cum all over the front of my beautiful pink lingerie. I scooped some into my mouth, to mix with John's, then wildly spread more of my jetting goo over my silky smooth satin tummy and lacy tits. When I was finally spent I wiped my hands on my stocking tops and drifted off to enjoy a boozy, satisfied nap.
I awoke an hour or two later. Seeing the dried-on cummy mess and tasting that gorgeous taste in my mouth again, my cock immediately sprang to attention. This time I grabbed a pair of white, lace-trimmed silky nylon panties from my drawer and quickly wanked myself into them. When I'd drenched them with another helping of cum I stuffed them into my mouth and savoured the flavour all over again.
Oh, I was such a cum-sucking sissy-boy that day.
Epilogue:
This all happened about a year ago. I never did go back to meet John the following week. When I was fully sober I felt rather ashamed of myself and as much as I enjoyed it at the time, I couldn't work up the courage to repeat the performance.
However a couple of months later I did suck-off another hairy man. He was a friend of a friend. Again, I was very d*unk and as before, he didn't even know I was a tranny. He just thought I might be up for it. On that occasion I brought him home with me and asked if he minded if I wore pink stockings and a pink chiffon nightie for the event. He said he wasn't bothered either way but I wanted to be sissified so I dressed, with lipstick and pink fluffy mules this time. I successfully sucked his cock and emptied his balls into my mouth but it wasn't quite so much fun as with John.
Since then I've been lucky enough to be in a relationship with a real girl. She was ok with me dressing but never seemed totally comfortable with it. One thing I discovered is that I really enjoyed sucking her fingers and toes. I suppose I just love sucking. At times I found myself thinking it was a shame she didn't have a penis.
Anyway, that liason is finished now and I'm getting the strong urge to suck again.
So I suspect I'll be sucking more cock very soon.
I'll post the details of my next adventure here, as and when it happens.
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