Written by TV Tara

5 Mar 2006

It has been some time since I have had any experiences en femme but I got an opportunity a couple of weeks back with a weekend alone. It had been some time so I spent a horney week thinking about what to do on the weekend. As my mind ran through my mental inventory of clothes and outfits, I couldn't really settle on any particular one. That is when I decided to go on a shopping trip with a slight twist! On Saturday morning I bathed, shaved and lightly perfumed myself before setting off to the centre of town wearing nothing but a loose pair of trousers, a pair of shoes and my jacket with a pair of breast forms in the pocket. It was pretty chilly but the unusual feelings added to my tension as I rode the tube into town.

First stop was M&S where I bought a pair of lovely black lace topped stockings. These went with me to a department store where I looked for some lingerie. After no short time deliberating, I settled on a deep red satiny set of basque and panties that I bought in the usual pretence of it being for my girlfriend. Instead of walking out, I went down a floor to menswear and grabbing a pair of trousers roughly in my size, headed straight for the changing room. Instead of trying on my garment, I slipped off my clothes quickly and fit the basque, positioned the breastforms in the cups, shakily rolled the stockings up my legs and shivered as I felt the satiny texture of the panties sliding up my stockinged thighs. I thrill at the daring and can't help rubbing my hands over my body as I look at the sexy TV in the full-length mirror in the changing room. I'm very conscious of the time as I curtail my exploration and hurriedly pull on my trousers and jacket over the lingerie. I didn't think much about the now empty bag and have to breath deep and hopefully appear not too flushed. I give the trousers back saying that they don't fit too well and make a beeline for the exit, pausing only once to look at a random display for authenticity.

Once outside on the street, I can really revel in my situation and I can't help but put a sway in my walk as I feel the satiny material encasing my body and the smooth friction of nylon on my legs. I dispose of the unneeded bag and make sure that the loose jacket covers up the fact that I now have breasts. Just passing by people turns me on and I stay in my jittery state as I make my way round a number of ladies fashion shops, seeing if anything catches my eye. I'm reft with indecision but in the end, settle for buying a nice black dress with a shortish skirt and a ribbon belt. It looks about right and although I feel a bit exposed standing in the queue to buy it, I make off with my purchase to a mens’ shop a few doors down where I select a jumper to try on. Stripping off my clothes, I quickly adjust my stockings and let the dress fall down over my arms and head. It turns out to be a little closer fitting than I expected but still passable. I smooth down the skirt over my suspenders and rub my semi-erect cock through the material before pulling up my trousers back over the skirt and replacing my jacket. Another excuse, a turn around the floor and it is time to move on to the next shop.

Clothes in place, I head for Soho for the final purchases: a dirty DVD and a new sex toy to enjoy in my outfit at home. Standing in the sex shop, feeling the sexy clothes under my outerware really gets me horney as I examine the titles. I take my time and move over to the sex toys looking for something different. Imagining easing each one into my lubed ass starts making my pulse race and fuelled by my excitement, I decide to go for a large butt plug, far larger than anything else I own. I picked up a tube of lube and grabbed a DVD and paid for it with a sheepish smile on my flushed face.

After I'd left the shop, I felt that I wasn’t ready to end my exciting outing yet and wanted to keep my level of arousal up and so, on a whim, I headed for the peepshow sign across the road. I paid the fee to get in and found myself in a suitably seedy place which offered not only the booths to watch a live strip but also video booths. Opting for the latter, I started the film and quickly removed my outer clothes, unpackaged the sex toy and rubbing my cock through the material of the dress as I watched the video. The action on the screen soon moved into anal penetration so I reciprocated and lubed the tip of the plug up and started stretching the entrance of my hole after pulling my panties aside a little. It really did stretch me as I slid down on it and was clearly much too much for me so I had to settle for bobbing gently on it after placing it on the bench under my skirt. I ran my hands over my breasts and gently touched my now straining cock as I watched the film, getting more and more excited. It was only then that I noticed a gap in the wall in one of the darker corners with what was obviously someone’s eye pressed up against it!

Well my shock was physical and a wave of adrenalin washed my body. Despite my obvious reaction, the eye stayed there and it dawned on me that he must be enjoying what he saw or he would have pulled back earlier. Well, that encouraged me and I made a conscious effort to relax, part my legs a bit and slide a little further down the dildo. I made a great show of rubbing myself all over and crossed and uncrossed my legs to expose my stocking tops and panties. It was odd since I wasn't made up and didn't even have my shoes and wig on but he pulled back and replaced the eye with an uncircumcised cock pushed through the hole. Well I needed no invitation and kissed, licked and sucked the cock, holding it with one hand while I used the other to push the tip of the buttplug into and out of my hole. The position of the hole in the wall made the angle awkward and my friend groaned with frustration as he tried different approaches. Eventually, he pulled back and suggested that we go to a cinema to do it properly. Well, I'd never been to one and said so to which he replied that he knew a good one not far from here. I was a bit flustered and said that I prefer to put on some makeup and shoes and he laughingly said 'fine, meet me there later. Here is my business card so you can text me when you're ready.’

I heard his cubicle door close as I put the dildo back in the bag with its packaging and pulled my outer clothes back on. I rushed out (as I guess many punters in those sort of places do) and wracked my brains about where to get the things I needed. I knew of one transvestite shop I'd used a few years back and assumed it would still be there. Likewise, I could pop into Boots for some emergency makeup. In the end it took some time but I bought what I needed including a slightly longer than shoulder-length auburn wig and a wonderful pair of black pointed toe stilettos with an ankle strap. After my spree, I stopped in a bar to have a drink and text Mike (as the name on the card indicated). Time had passed and it was getting dark very quickly and people were starting to come out for the night. I got a response about 20 minutes later and it contained directions to the cinema from the peepshow club we were at. Finishing off my drink, I made my way there still nervous but very, very excited. It was funny to think that just wearing the clothes concealed in public was a thrill earlier but now I was going to a place deliberately to give a near stranger a blow job!

I got to the place and paid my entry fee to the guy behind the counter. I walked down a stained carpeted corridor reading the signs and turned into a small cinema with dirty burgundy seats and a smattering of people about it not too attentively watching a BJ scene on the screen. I looked around nervously, trying to catch the eye of whoever Mike might be and noticed a toilet sign to the side. I walked down the back of the rows and down the aisle to the door and entered into a bit of a grubby loo and locked myself into one of the battered cubicles. Judging from the sounds coming from some of the other cubicles, I wasn't indulging in the worst things that happened here so I sat down and started applying my makeup with the use of a compact mirror, including some false lashes I’d bought.

I was just putting the final touches to my eyes when I was startled to hear my phone go and pulled it out to see that Mike had sent me a message saying that he was there and was sitting in the 3rd row on the right hand side. Well that was it. I stripped off and put all of my outer clothes apart from my jacket in my bags, buckled on the new shoes and donned my wig. Adjusting my stockings and tightening the suspenders a little, I listened to make sure no one was moving outside and opened the cubicle door. A quick stop by the mirror to check my wig and try and smooth out some of the creases in my skirt and I sauntered nervously back into the cinema. I was incredibly nervous but it felt like I was going on a date as a girl and I beamed a smile as I tried my best to move seductively up to who I assumed to be Mike. Thankfully he smiled back and eyed me up and down before moving his coat from the seat next to him. I smoothed my skirt behind me and tried to sit down in as ladylike fashion as I could, crossing my legs as best as possible within the confines of the cinema seating. My cock was incredibly sensitive pressed between my thighs and the suspenders of my basque clearly stood out as they left the point they were clipped onto the body and attached to the lacy stocking tops under my skirt but I tried to play calm and slipped my jacket off my shoulders. I could feel the other customers looking at me but, right now, didn’t care as I was with my guy and felt somehow safer that way. Mike leaned over and whispered ‘Ooh you look great’ into my ear and put a hand on my thigh which sent electric signals all over. We leant together and kissed deeply with tongues and I reached straight for his crotch to release an already rigid cock from his trousers. I was vaguely aware of people around me as I moved down and engulfed his cock in my lipsticked lips but didn’t care a bit even when I realised that there was more than one set of hand rubbing my tits, legs, body and pantied cock. I sucked and licked and bobbed my head for all I was worth and was only interrupted when I felt someone get down beside my legs and start to lift my skirt. ‘No’ Mike said ‘She’s mine and I don’t want to finish with her yet’. I lifted my head from his lap and saw an old guy on his knees, still holding the bottom of my dress and looking a bit crestfallen.

I wanted to get some stimulation myself so I looked up at Mike and asked if he could finger my still-moist ass if he promised to leave my cock alone. It would make me hornier and suck him all the better. Well, he considered for a second then said ‘OK, you’d better get on your knees’ which I did, raising my butt in the air. The old chap folded my skirt onto my butt a little and pulled the thong of my tight satin panties to one side, causing waves of pleasure in my cock, compounded by the tongue I felt touch my ass! I obviously twitched as Mike sternly said ‘Fingers only!’ and I felt first one then two digits penetrate me as I resumed sucking on Mike’s member. Well this was blissful and I was right on the edge for a long time before I hard a voice saying ‘You can’t do that in here! Get out!’. I rather reluctantly disengaged myself and clambered to my feet. Both Mike and the older guy were standing up and I grabbed my bags and jacket as we filed our way passed an angry looking guy in a black puffer jacket. I was getting all sorts of looks but the one thing in my mind was frustration as I was dressed and horney and wanted nothing more than to swallow Mike’s cum, a thing I’d failed to achieve in 2 attempts today.

As I teetered up the aisle, Mike locked arms with me and leant over to whisper in my ear ‘Let’s fuck’. I wobbled a little more at that and was about to turn to him incredulously when he added ‘We’ll get a taxi to my hotel room’. I’d never been out dressed in public before, let alone the centre of London but I really didn’t have any choice given that I was being thrown out then and there. That more than anything sent me clipping along the pavement with my arm linked with Mike’s, the evening revellers opening looking me up and down. Mercifully, Mike was quick to flag down a black cab and I climbed into the back after him. Once inside, I calmed down a bit but couldn’t make myself meet the driver’s eyes as Mike give him instructions to take him to a hotel in Holborn. My erection had subsided and my legs were clamped firmly together but for some reason, my attention was caught by a smudge on the toe of my shoe which I bent forward to clean off. ‘While you are down there, you can carry on where you left off’ Mike said with a touch of humour in his voice. I looked up somewhat incredulously and saw him already unbuckling his trousers. I was still very conscious of our situation so I made some, no doubt terrible, show of being tired and resting my head in his lap. I didn’t want to bob too obviously so gently eased my lips round his pole and used them to provide resistance as I allowed it deeper and deeper into my mouth and down my throat. This tight, wet throating and the public exposure clearly worked for Mike and after only a few turns, I felt his cock stiffen and erupt in the back of my throat. Because of the position, I found it very difficult to swallow so I clamped my lips tight around him and slowly withdrew my head, trying to retain as much spunk as possible. The long build-up clearly had its effect on Mike too as his cum nearly entirely filled up my cheeks. I lifted my head, pushed my hair aside and carefully opened my mouth a little to show Mike his products before swilling a little bit for show and swallowing it in 3 gulps. Pleased with myself and with the inside of my mouth still sticky and tasting of cum, I reached up my skirt to start playing with my now-erect cock only to be interrupted by Mike holding my hand and saying ‘Not now. Give me a while and I’ll be ready to fuck you. You’ll enjoy it more if you haven’t come yet.’ I don’t know what it was but he certainly dominated me and I tidied myself up a bit and sat with my ankles crossed and an aching cock and gaping ass under my clothes as we completed the journey. The trip inside the foyer was a little embarrassing but I clung on to Mike’s arm and we made our way up to the top floor in the lift. Mike opened the door onto quite a smart suite and I almost died in my heels as I walked in to be confronted by a middle-aged woman drinking wine in front of the TV!

Upon further inspection, I noticed she wasn’t dressed as you would expect someone passing a lazy Saturday afternoon; short leather skirt, black stockings and a satin bustier under a bolero jacket with mid calf stiletto boots. ‘Look, I brought someone back – Jade meet…’ Mike said, ‘Tara’ I stammered. Jade gave me a very appraising look and smiled rather noncommittally. ‘Your tastes never fail to surprise me Mike’ she said. ‘Jade has been performing services for me for some time’. Mike said. ‘At least whenever I am in London for work. Tara has a great oral style Jade. I think she should show you while I get myself a drink.’

‘OK’ Jade said as she slid forward in her chair and peeled off a small pair of sheer black panties. She opened her legs and beckoned me forwards. This really wasn’t what I was expecting and I was a little hesitant. ‘Go on Tara’ Mike said from the background. ‘Lick her out and I’ll fuck you when I get my strength back.’ I’d never been with a woman while en femme and was a little uncertain of the dynamic here but I got on me knees and gently licked her slit. After a couple of minutes, Jade started getting wet and opening up for me and said ‘she isn’t bad is she Mike. Bury your tongue up me you slut’ after which she grabbed the back of my head and rammed it into her quim. I tried to push my tongue in as far as it would go although she did taste a bit bitter. ‘Now my ass’ she said as she pulled my head away and stood up, facing away from me. Again, I hesitated as it was doing nothing for me. ‘Go on’ said Mike who had now sat in a chair with his drink. ‘Put on a show to get me horney again.’ So as he sat there sitting his drink and rubbing his cock, I tentatively liked Jade’s tight hole. ‘Part her cheeks and stick your tongue right in’ Mike said. I was still a bit hesitant and Mike said ‘I think she needs something in return. Get one of your vibrators out for her tranny ass.’ So Jade stood up and went to a large leather bag next to one of the chairs. After a short bit of rummaging, she pulled out a big pink cock shaped vibrator and a small silver one. ‘This should do’ she said ‘spit on that’ as she pushed the big pink one into my mouth. ‘Make sure you make it wet as it’s going right up your ass.’

‘Now get to work rimming her’ Mike said as he took the dildo from Jade and reached between my legs to start stroking my satin-clad cock and balls. I heard a faint buzz as he started the vibrator and pushed it gently against my hole. By this time, I’d resumed licking her tight hole and dipping my tongue into it as Mike started penetrating me with the end of the vibrator. Jade had started rubbing the smaller silver vibrator around her clit and was clearly enjoying the combined experience. ‘Move back a bit’ Mike said as he got me to sit back on the vibrator braced against the floor. It was stretching me while still being only a couple of inches inside in this position. I reached up and parted Jade’s cheeks as I buried my tongue in her ass. She was moaning and I was beginning to enjoy the vibrations going through my ass over the constant pressure of the vibrator when I was startled by a flash. I hurriedly looked round and there was Mike with a digital camera taking photos of us! ‘Show me your tongue in her ass!’ Mike urged and I obeyed as he snapped another. ‘Lift your skirt so I can see the vibrator in your ass’ he commanded and I did ‘stand on your heels and squat down on it’ he said ‘hold your dress up so I have a good view.’ It was difficult to hold the pose wobbling on my new heels and the extra pressure meant the vibrator sank another inch into my ass. ‘That’s it!’ Mike said. ‘Lick her ass as you fuck yourself on that dildo’ and he moved around snapping repeatedly from different angles. I never thought that I’d be performing with some escort wile dressed as a woman when I set out this morning but Mike had this compelling personality and I couldn’t help but go along with it.

Jade had started stripping down to her lingerie and Mike made me stand up and take off my nice new dress as well. ‘Very nice.’ He said when he saw my deep red set. ‘Come here and Jade can film me fucking you.’ I stepped out of my panties to free my now rigid cock and tried to look as sexy as I could with my stockinged legs either side of the arms of an armchair sinking up and down on Mike’s newly hard cock while facing Jade with the camera. ‘Oh that is nice’ Mike said between pants. ‘Have you got that big double-ender you used with that other girl Jade?’ Mike asked. ‘No’ she replied ‘I didn’t think we’d need it.’ ‘Shame’ he replied ‘it would have been great to watch you fuck each other with it. Still, I’m sure we can make do!’ We fucked in various combinations for what seemed like an age with a notable bit where Mike had Jade and I on all fours next to each other and alternated fucking each of us up the ass. Finally, we finished off trying to fulfil one of Mike’s fantasies of DPing Jade and capturing it on film. It didn’t work out too well but I was so horny that I filled my condom in her cunt while Mike did the same in her ass. ‘Stay there!’ Mike said as he peeled off his condom and rushed to adjust the camera. ‘Now get up on your elbows, open your mouth and smile at the camera’ as both he and Jade (who had removed the condom from my now shrinking cock) stood either side of me and poured the contents of both condoms (his and my cum) into my mouth to the flashing of the camera. I swallowed it and tried to give a sultry look to the camera a I liked the drips from around my lips.

After that, Mike got himself cleaned up and give me £50 for a taxi home before he went to have a shower. Once Mike had gone, Jade gave me a flyer and said that I should call her if I wanted to help out on some of her other clients with similar tastes and she’d give me a share of the fees. I was all a bit light-headed and unpacked my outer clothes for the journey home. It was only halfway through my journey back when I realised that I hadn’t taken off my makeup or wig! Out of embarrassment, I got the taxi to stop a block early and hurried paid and got out to give me a chance to sort myself out before the neighbours saw me. After he’d pulled away, no one was coming so had a change of mind and slipped into a driveway to put my dress and shoes back on and clipped my way down the pavement for the last block. My ass was still gaping so I knew the new butplug would get more use that night. Little did I suspect setting out that my thrilling shopping trip would turn into something so unexpected but it really was quite an experience. Although being tired, I found recalling the day more stimulating than the film I bought and nearly eased the whole plug into my ass as I sat back on the floors with my legs either side of me rubbing my tits and cock.