First Time Out

I'm so excited and want to relate this 100% true story quickly while it's still fresh. Please forgive any typos.

[My background: Age 48. Closet dressing in earnest for 15 years. Began with slips stockings and nighties but have collected extensive full wardrobe and accessories over time. Boobs, wig, jewellery etc. Slim with shapely legs, dress size UK 14. Sexuality, straight but bi when dressed with wig and importantly, full make up. (Too lazy and unpracticed with make up to bother very often. May appear convincing from neck down but facially not so good.) Always entertain at my home following web introductions. Have sucked a few sister sissies and real men and lost my ass cherry 3 years ago. No bum fun since then, except for dildos. Now have GG girlfriend, not living with me. She knows I dress but sadly won't indulge me dressing for sex. She likes my shaved torso, cock and balls but won't let me shave my legs.]

Last night (Wednesday) I was home alone and got fully dressed in a cute pink 36B all-in-one body briefer with attached suspenders, fully fashioned light tan stockings, pink satin lacy full slip, just below-the-knee antique rose sparkly sheer silk chiffon shift dress, antique rose three inch heels with matching handbag, long straight chestnut wig, pearl necklace with matching earrings and baby pink satin wrist gloves. The plan was to take some photos then strip to my undies and wank myself off.

BUT, for once my make up was ok, almost passable. After taking a few pics it was late, around midnight. So I decided to do something I'd never, ever done before, leave my house en femme and go for a stroll around the neighbourhood. My outfit was refined, ladylike and sophisticated if I say so myself but I felt incredibly confident, naughty and horny so into my empty handbag I put ky jelly and a couple of condoms. As I left the house I popped my keys in there too but that was all I carried.

I felt so liberated, wonderful and sexy, feeling the cool air caress my stockinged legs and flutter the hem of my floaty dress as my heels click-clacked on the path. However, whereas my shoes were comfy and ideal for indoor wear I soon realised they were just a touch too big. They kept slipping off at the heel making it impossible to strut confidently. So reluctantly, after twenty yards I turned around and went back indoors. Luckily I also have a pair of pink three inch mules which don't match my handbag but fit slightly better. With those on I left the house for the second time and went for a stroll. I had my handbag hung over my crooked elbow with my other arm swinging girlishly.

My planned route was only about four hundred yards but I hoped to be seen by a few late night folk. I passed within five yards of a couple sitting in their car. I didn't make eye contact but was thrilled to think I had definitely been seen. Next I passed a couple of young lads on the other side of the street, probably on their way home from the pub. They didn't pay me any attention at all which was fine. Then I got to the main road and walked in the direction of the traffic, hoping to show my sexy rear view to any passing drivers. I felt so completely vulnerable, only being able to walk at a very slow pace despite my relatively comfy heels. Vulnerable, yet somehow confident too.

A couple of cars passed me then, seconds later, I heard the unmistakable sound of a car slowing down. I turned to look and a taxi pulled up alongside me. The young asian driver wound the passenger window down and asked me if I needed a lift. I didn't get too close to the window but just said, in my best girlie voice, "No thanks I'm nearly home."

He just said, "Ok." and drove off.

It was exciting to have talked to another person in my guise as a woman but no sooner had he gone than I regretted not siezing the opportunity. I walked another thirty yards or so to the left hand turn which would have taken me straight home down a quiet lane. I stopped and pondered but decided I didn't want my adventure to be over so soon. So I turned around and walked back the way I had come.

Within a minute a taxi passed me on the other side of the road, travelling at speed. It went all the way round the roundabout and stopped beside me. It was the same driver. Through the window and in broken English he said, "You man or woman is it?"

In a moment of brutal honesty I replied, "I was born a man but tonight I'm a woman."

There was a slight awkward silence and I couldn't read his expression but he didn't drive off so, determined not to miss the moment again, I just blurted out, "Uh, would you like a blow job?"

He thought for a second before saying, "How much init?"

Whoa, that really took me by surprise. Here was my chance to be a whore and actually receive cash from a cabbie instead of the other way around. I was perversely flattered that he'd pay me for sex but I didn't feel like a whore. I was dressed way too classy for that. No, I felt like a lady. A sexy lady who just wanted to please a man. Besides, he had been kind enough to offer me a lift home. So I shrugged my shoulders and said, "Nothing. I just want to."

I thought it was a pretty good deal but never-the-less he upped the stakes, asking, "You do anything else?"

Ooh, the smooth talker! That was music too my ears so I replied, "I've got condoms and lube."

He simply said, "Get in."

Out of habit I climbed into the back seat. I could have got in the front but was glad to be in the back. It made me feel more ladylike and special, especially as I sat there being chauffeured with my knees demurely together and my handbag clasped on my lap. He radioed back to base and made up a story about taking a fare to a local village which would take him thirty minutes or so. (I don't know how he covered for that later but maybe he did end up paying for me after all?) As he drove he asked me a few questions like, how old I was and if I did this often. I told him I was 42 (tee-hee) and that this was the first time I'd ever been outside dressed. He seemed nice and friendly, even a little shy and told me he was 25 but didn't have a girlfriend. I told him, he did tonight. He asked again how far I would go and I told him I'd do whatever he wanted. I couldn't believe what a slut I was being but it had been too long since I'd been with a man. And I can't stress this enough, despite his few words in less than perfect English, he struck me as trustworthy, a real nice guy. I felt safe.

He drove for only a mile into an industrial complex, which was deserted at that time of night. When we stopped he turned and asked, "You come in front or I come back?"

Rather than being nervous and submissive as has been the case with my past (indoor) encounters, I felt oddly powerful and confident. Perhaps like a real woman? So I answered, "Come and sit in the back with me. There's more room here."

He climbed in and sat beside me, looking a little unsure as what to do next. I asked if he wanted to kiss but he declined. (Pity that, I love kissing.) So I put my hand on his thigh and asked, "Can I kiss your cock then?"

That did it. I didn't get the chance to undress him as he frantically struggled with his belt, button and the zip of his trousers. With them dragged down to his knees he quickly pulled his underpants down to reveal a hard little cock, sticking straight up in the air. Wow, that was soooo flattering. He had a hard on for ME and I'd barely touched him! He immediately apologised for being so small. (Less than four inches.) However, for sucking, that's my ideal size. I put him at ease by cooing, "Oh no, no. It's lovely. It's beautiful."

He smiled and said, "Yeah?"

I leant forward into his lap, saying, "Yeah, oh yeah."

I proceeded to express my genuine delight by kissing his spongy head and sliding my lips down his shaft until I had taken it all into my mouth. He hissed and sighed his pleasure as I suckled on him while tickling his balls with my pink satin fingers. Bearing in mind he had been working all night and the fact he was asian, with possibly a spicy diet, I was surprised at how neutral he tasted. He was obviously a nice clean young man and I could have happily spent hours sucking his lovely little boner. I had plenty of room in my mouth to swirl my tongue all around and over his tender mushroom. God, I was loving it. So was he. His breathing was hot and heavy, his moans becoming ever more urgent. After, and I kid you not, less than a minute, he lifted my head up, saying "Fuck your pussy now. You got condom?"

Well now it was my turn to scramble into action before he shot his cream too soon. I grabbed my handbag and took out a condom, quickly opening the wrapper and rolling it down his hard on. I pulled my dress and slip up and struggled with the snap crotch of my all-in-one. However my pink satin gloves just didn't provide enough grip so I practically ripped them off, throwing them on the seat before freeing my boy pussy from it's tight confines. I took the ky from by bag and smeared a dollop on my finger before pushing it straight into my ass.

He asked, "What that?"

I told him it was lube, just to make things easier. But it suddenly struck me, had he fully understood me earlier? Did he think I was a TS with a real pussy? Being sat next to him and with my dress covering my recently squashed, boy parts he probably hadn't seen my soft clitty. I didn't dwell on it though. I just made my move.

I kicked off my heels and in the dim light I saw my pink painted, stockinged toes swing over his thighs, closely followed by my calf, knee and thigh, until I was sat squarely straddling his lap. I love it when a woman guides me into her wet waiting hole, so I did the same for him. Holding his hard prick, I manouvered it between my cheeks until it was tickling my tight pussy. Then I sat right down, feeling him slide, deliciously inside me. He gasped anew and grabbed my hips outside my dress, sliding his hands all over my lovely layers.

This was a night of many firsts and it was certainly my first time riding a man. I had dreamed and fantasised about it for so long but finally it was happening. I'm not one to boast but I seemed to have a natural talent for it too as I rotated and rolled my hips, making him moan and pant. I have to admit, I wished he had been a touch larger because I could barely feel him inside me at times. He wasn't big enough to hit my sweet spot but that was ok. My pleasure was the mental satisfaction of knowing I was being a good girl and giving pleasure. It was so lovely, having my long hair flowing around my face as I rode him and I was glad I remained soft down there. At one point I must have been too enthusiastic because he slipped out and I didn't even notice. (Oops.) However, once he pointed it out, that gave me the chance to put him inside me again, allowing me the joy of being penetrated once more. I really squashed down this time and gripped the underside of his hairy, muscular thighs with my hand so I didn't lose him again. I also tickled his balls with the fingernails of my other hand, which really made him moan and buck into me.

God I felt so whole, complete, dirty and slutty, being fucked by a man in a car, in a public place. I wished it would never end but after probably no more than five minutes of my urgent gyrating he cried out as he came. I continued to ride him but he told me to stop. Reluctantly I climbed off him and let his spent cock pop out of me. As he sat there, recovering from what appeared to be an earth-shattering orgasm, I glowed with pride. Then reality set in and he asked if I had any tissues. Of course he didn't want any cum on the seat of his taxi but I hadn't thought that far ahead. As I said, the only remaining item in my handbag was my front door keys. So, I said, "Don't worry about it." And...

I had been hoping for a mouthful of his gooey stuff at the start of our encounter. Getting fucked was a huge bonus but I also wanted my tasty treat. So I peeled the condom off his softening cock, balling it into my hand and immediately replaced it with my lips, sucking the slick remnants of cum from his cock. He cried out again as I licked him clean. That's one thing a real girl can never know, just how tender a post-orgasmic prick can be. So I understood when he begged me to stop. Even so I sucked all the way up his cock before letting it noisily slurp from my lips. He tasted lovely :)

He sat there for a moment longer, composing himself, before pulling up his underpants and trousers. Then, and I was really touched by this, he handed me one of my shoes. I knew he was a gentleman. (grin) There was another awkward silence. I don't think he knew what to say. So I took the initiatve, kissed him on the cheek and said, "Thank you, that was lovely."

He didn't say much apart from, "Mm, yeah, I take you home now."

During the short drive home I didn't bother to re-snap my crotch but I did put my ky back in my handbag. He swore me to secrecy about our little illicit affair and I said, "Of course, I don't even know your name and I'm not asking either."

He didn't ask for my name either but he did ask for my phone number. Now this is really strange. I let him have my mouth. I let him have my boy pussy but for some reason, nice as he was, I didn't let this stranger have my number. However, he dropped me right at my front door and I made sure he knew my house number. He did ask if we could do this again and I said, "Yes, drop in Friday night." (I have another night off from my girlfriend then.)

So I'm terribly excited by the prospect that he might call on me but Friday will be a busy night for him. I have no idea what time or even if he will appear. Anyway, tomorrow night I am going to get fully dressed and made up as a slutty, mini-skirted whore. (I'll still give it away for free though, tee-hee.) I'll be ready by 9pm and just sitting here waiting for my man to appear.

Oh, I almost forgot to say. In all the excitement I stupidly left my only pair of pretty pink satin gloves on the back seat of his taxi. Or maybe I did it subconsciously, just to make sure he has an excuse to call? Oh well, never mind, I have a similar pair in white.

If he doesn't arrive by say 11pm I guess I'll be going for another stroll..... Either way, I hope to post tomorrow's adventure here as soon as possible.

It's taken me ten times as long to relate this event as it actually took to happen but please believe me, it's 100% true. I wouldn't want to waste your time otherwise dear reader.

If you are a closet, wannabe sissy like I was, you may take inspiration from my experience. However I appreciate how risky and potentially dangerous my actions were. I could have been beaten up or dead in a ditch by now. But I took a leap and it worked for me. Oh God, how it worked. I feel so fulfilled and satisfied, yet still yearning for the next time. I can only urge you to follow your desires as safely as possible. We're only here once eh?

Hugs and Love

Nancy

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