Second Chance

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After he breaks up, she'll only take him back as a girl.
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Tomsparty
Tomsparty
644 Followers

I thought I was the luckiest guy in the world when I first met Katy. She was stunningly beautiful, intelligent and incredibly hot and sexy. We did everything together and for a long time I thought she was the one I may eventually marry. Then everything changed. I don't know why but overnight the whole serious relationship thing panicked me and I wanted out. As much as I loved her I knew I was young, wasn't ready to settle down and felt I should play the field. I therefore after much sole searching decided to make the break. It wasn't because I had met someone else. I just needed the opportunity to spread my wings and experiment.

On reflection I was perhaps over confident. Having been going out with a beautiful girl I assumed other equally beautiful girls would be falling over themselves to date me. What I hadn't considered was that in reality I was what many would consider an effeminate sissy.

I was of a slight build and had a young girlish face. I hated sport and had little muscle on my otherwise toned body. Fortunately Katy didn't mind. In fact she loved my sexuality and regularly teased me about my masculinity. She liked me to play effeminate and even made me wear her panties on several occasions. She got incredibly turned on in the knowledge that I was wearing her panties under my suit or jeans and I knew that great sex would soon follow.

Needless to say she took the break up very badly. I thought she would understand but despite my greatest efforts the news hit her hard. She was terribly upset and practically pleaded with me to change my mind. It was hard for me too but I knew I had to have some time out. It wasn't that I never wanted to see her again I just felt I should play the field before settling down or getting even more comitted. She kept ringing my mobile and sending me emails. She even sent flowers and incidentally kept bumping into me around town a bit like a stalker.

Over time her tone got progressively bitter. 'You'll never meet a girl like me,' she screamed. 'I was the best thing that happened on your life.'

Which was possibly true but I had to rid the straying demon from my head otherwise I was sure it would bite us later in our relationship.

Eventually the message sunk home and she contacted me less and the number of coincidental meets disappeared until her calls stopped altogether. Free and guilt free I enjoyed myself for the first few months meeting girls and trying to date them but over the weeks I grew fed up of being constantly rejected and those who I did date vever lasted more than one night and they quickly lost interest. Worst still I didn't even get close to getting them into bed and after a few months I was desperate for sex.

I slowly came to the conclusion that no girl came close to my Katy and I soon began to regret dumping her in the first place. I wanted her back and initially thought it would be a simple matter of asking her out and perhaps admitting my mistake. After some soul searching I eventually plucked up enough courage and rang her mobile. I wanted to hear how she was and perhaps meet up for a catch up.

All in all the call went OK but she said she had met another man and that I had missed the opportunity. She said she was sorry and hoped I would find another girl. Needless to say I was very disappointed but felt there was something about her tone that made me feel she still had some feelings for me.

For the following few weeks I could think of nothing else. She didn't answer my calls, emails, or letters. She blocked me from her facebook and refused to acknowledge my tweets. I was in danger of being a stalker. Then all of a sudden when at a particularly low ebb I saw her in town. She looked stunning as always but was seemed pretty indifferent when I said hello but she did accept my offer of a coffee. But once we had sat down all she did was remind me of my stupidity and what a wonderful time she was having with some guy called Brett. I begged her to take me back but she refused to even consider it. As we finished our drink she disappeared to the lavatory for a few minutes. On her return she had a warm smile on her face and something in her hand. 'On second thoughts,' she said with a chuckle, 'You can do something for me.'

'Anything ,' I begged.

She reached across the table and clasped my hands with hers. I immediately felt something warm and soft in her palm. 'I want you to go the men's and put these on.' she said.

Obediently I went to open my fist but she held my hand tight.

'In the lavatory I want you to take off your boxers or whatever you are wearing and swop them with my panties.' She giggled and slowly withdrew her hand. 'It will be like old times.'

I looked at her confused. One minute she didn't seem to care and next minute she was teasing me with a game we used to play. Nevertheless my cock stiffened and I desperately wanted to wear her panties. I got up from the table daring not to unclench my fist.

'Good girl,' she chuckled, 'hurry back. I can't wait to hear what you think.'

Inside the mens lavatory I darted into a cubicle. There I deftly took off my shoes, dropped my jeans and stepped out of my boxers. Naked from the waist down I took a minute to see what she had actually given me. It was a pair of pretty white lace panties adorned with a tiny rose on the waistband. I hadn't seen them before and for a brief moment wondered if Brett had. I held them to my nose and was immediately reminded of her sweet feminine perfume. I smiled as I slipped them up my legs and was rewarded by a massive erection.

As I walked back to our table, my boxers stuffed in a pocket, I revealed in their soft feminine tightness on my cock and butt.

'Well,' she said with a broad gin as I sat down, 'I bet they feel real nice?'

I nodded.

'Now let's do a swop. You keep my panties and I take your boxers.' she laughs as I amicably hand my boxers over so no one could see.

'Are you going to put them under your pillow?' I laugh but her reply hurt.

'No way I don't think my Brett would appreciate the sentiment. Anyhow,' she said brushing away the very idea. 'I don't want you to hide my panties away like some perverts I want you to wear them as if your own and next time we meet, whenever it may be you can show me that you are wearing them.' With that she said her goodbyes and was gone. No second date, no promise of a call, nothing. Just a pair of sexy panties that she made me wear. Alone I immediately felt self conscious and wondered if the other customers knew what had gone on.

Mystified and excited I did as she asked. I wore them all that day and loved every minute. I masturbated in them that night and even wore them the following day but the day after that I was back in my trusty boxers. That's when, ironically, we bumped into each other again on a train. She sat next to me and after a brief exchange she asked in a hushed whisper if I was wearing her panties. I called her bluff said yes but she demanded to see. Disappointed she pulled from her handbag another fresh pair which she surreptitiously past to me.' I'm very disappointed,' she said, 'but you can redeem yourself by slipping into the trains lavatory and putting this pair on instead and giving me what you are wearing.'

I tried to not look too eager as I popped into the lavatory and repeated the switch just like the other day. This time her pretty panties were red with black lace trim and very tiny. I struggled to keep my cock in them but nevertheless loved the feeling of the lace and the knowledge that they once adorned her own heavenly body.

Again once I sat back down she took my boxers from me and disappeared, this time at the next stop. I spent the next coupe of hours in a dreamy bliss feeling my cock twicth between the silk and lace and like the previous night I masturbated in them when I got home and wore them for the next day.

Three days later I bumped into her just as I was leaving the office and this time she asked me almost straight away. And no I wasn't wearing her panties. Again she seemed disappointed and grabbing me by the hand she pulled me into an alley. There in between two trash cans she slipped off her shoe's and hiked up her own skirt. She made me turn my back but I still heard the rasp of nylons and her exited squeal as she slipped of her hose and stepped out of her panties. 'Hurry,' she said, '..before anyone see. Drop your jeans, take off your boxers and socks and put these on.' She dangled her skimpy panties before me. 'And this time,' she purred, 'I want your socks and you can wear my hose too.' This wasn't so easy but I was fair game and so after an embarrassing struggle I had her pretty panties on and was sliding her silken hose up my hairless legs. They felt wonderful, warm, fragrant and very feminine. Then just like the other night she pocketed my boxers and was gone.

This game continued over the following weeks. Each time she managed to catch me not wearing either her panties or hose until I had no boxers left at home and had nothing else to wear but her pretty panties.

I didn't mind. I liked wearing them. I felt really naughty wearing them under my suit for work and found the whole sensation thrilling. I felt closer to her and despite not actually dating very connected. I even wore her hose and just hoped no one would notice that I wasn't wearing socks. Then it finally happened she came into the office during her lunch break and asked to see me. I met her in reception and thought she was beginning to melt and wanted to go out for lunch. Instead all she wanted to know was if I was wearing her pretty panties. Fortunately, and for the first time, I was and she was delighted. Yet despite this mini victory she still refused to go out for lunch and told me to be patience and my courage would be rewarded in time. That night she rung my mobile and wanted me to meet her round her flat.

This in my estimation was a massive leap forward and to celebrate I wore a cleanly laundered pair of hose and what i considered her prettiest panties under my jeans.

At her flat I felt immediately at home. We chatted about old times and for the first time I felt I had a chance.

After the formalities, she didn't waist anytime wanting to know If I was wearing her hose and panties and it was with a sense of pride that I said yes. She was again delighted and as I hoped wanted proof. So I stood up ready to drop my jeans but instead she stood in front of me and and looked me squarely in the eye and unbuttoned my jeans. She didn't even flinch as she eased them over my bottom and the cotton of the jeans rasped alluringly against the nylon hose. She bent at the knee and lowered them down inch by inch until they were around my ankle. There she lifted one foot slipped off my sneaker and pulled them off. My cock throbbed as she did this to my other leg then stared motionless at my bulging cock in her panties. She rubbed it lovingly with a hand and stood up. She stepped back and admired my legs in her hose. 'Very nice,' she said unable to resist stroking them up and down. 'I've always loved your legs.. they are so very feminine.'

I blushed as she walked around me inspecting them from every angle. 'You have an enviable pair of legs ... so long and slender. Many girl would want these. You should show them off more by wearing a dress or skirt. '

I laugh nervously but secretly loved the idea, especially if it was hers.

She tugged my t-shirt down as if a skirt so that the hem fell just below my crutch. She pinched butt playfully. 'Careful you don't show too much thigh or you'll get a bad name.' she giggles.

But any attempt on decency on my behalf was hopeless as any untoward movement caused my t-shirt to rise and brazenly as I flashed my panties.

As I stood there feeling rather awkward she stood up put on a cd of some smoochy music and fetched me a bra and pair of bright red high heels. I could hardly contain my excitement as she slipped them on my feet. 'That's better,' she said, 'Now come and sit down beside me and lets talk.'

But as soon as I sat down my t-shirt rode up my thighs and openly displayed my panties and bulging cock. I blushed but Katy ignored my blushes. 'So,' she said finally wrapping the bra around my chest, stuffing the cups with tissue and feeding my arms through the tiny straps. 'Whats next?'

Her bra was the turning point. As she fastened the clasp something snapped in me mentally. As the slender straps pulled against my shoulders and the clasp pinched my back I felt myself change literally gender. Up until now wearing her panties had been a sexy hetrosexual game but teamed with her sheer hose, sexy high heels, lace panties and with no trousers I felt decidedly girlish. I shuffled oddly on the chair and smiled to myself as my panties slid deliciously against my skin. I no longer felt like a guy trying to date a girl but a girl herself casually chatting with another girl. The whole sensation made my stomach whirl and though I was enjoying myself beyond my wildest dreams I didn't want my feminine side becoming too prominent and spoiling the task in hand.

'You do look lovely dressed like this,' she said. 'You really do have a gorgeous figure I cannot see why you haven't been able to get another steady girlfriend.' She giggles mockingly. 'I suppose theres not many girls who want a man who likes to wear her clothes.'

'That's not fair,' I say you asked me to dress up for you .' She laughs mockingly reminding me that I could have refused. ' I imagine most girls would find you a threat. Looking so good'

But dressed as I was I felt decidedly girly and all my assertive plans of persuading her to go out with me again dissolved. Instead I sat their perched on the edge of the couch with my legs crossed in my high heels tugging my hem down like a nervous teenager trying to hide my embarrassment. And Katy dressed in jeans and shirt had taken on the more assertive role. Flirting and teasing me like a submissive girl on her first date

'So darling,' she finally says flicking an imaginary hair from my brow, 'where does this lead us? Where do we now go from here?'

I look at her sheepishly and uncross and cross my legs nervously as her eyes roam up and down my legs hungrily.

'I want to carry on where we left off,' I sob, my eyes beginning to water. 'I now realise what I had.. how much you meant to me and I want to make amends.'

'Oh darling,' she coos wiping a tear from my eye, 'a lots happened since you ditched me and I'm not sure if that's possible.'

'Please,' I plead. We were so good together. Give me another chance.'

'You know I've not stood still moping around waiting for you to ask me out again. I've met another man and he's very possessive and so strong. Unlike you he's a real man and treats me like a beautiful lady.' she smirks and lays a hand on my knee and pinches my nylons between her fingers.

But ... that said..' she paused and lent forward and whispered in my ear. 'I still find you very exciting.'

I smile broadly and go to kiss her but she pulls away sharply.

'Hold on,' she adds, 'It's too early, I do still hold something for you but I'm not sure if I want you back in the same way as before.'

'Please' I say again perhaps with a little more desperation, 'we can be so good together. We make a great team.'

She ran her hands up and down my thigh and gave my breast a squeeze.

'Hmm,' she murmured. 'Let me take you out for a meal,' she says, 'somewhere special. We should discuss it and who knows.'

She smiled almost like she used to and excused herself from the room. She was gone for a few minutes and while she was away I stood up and tottered round the room in her heels. I enjoyed the sensation of my nylon clad legs rasping together and my bra restricting my chest and my t-shirt caressing my butt. I felt so devilishly girly I wanted to have sex there and then so in an attempt to calm down I looked at the photo frames on the on the window sill. It was kind of depressing, they used to contain pictures of Katy and I but now were full of a man I didn't recognise. He was tall muscular, square shouldered with stubble and sporting a short black crew cut. He was quite a handsome hunk and could well understand why Katy found him attractive. This wasn't doing my ego any good at all and as i glanced down at my feminised form, seeing her bra around my chest my nylon covered legs and my feet perched in her towering heels i begin to wonder what she saw in me.

As I gazed at one particular photo something odd happened for the first time in my life. I imagined what it must be like as a girl and to go with a man. Almost immediately I felt my already stiff cock burst outward even more and felt my panties wetten with precum.

As I stood there listening to the cd playing in the background I was blissfully unaware that I was gently dancing to the music in a very feminine manner. And as I swayed to and through revelling in the high heels I realised I secretly yearned to feel a strong man wrap his arms around me and dare I say cum deep inside me.

At this point I was unaware of Katy entering the room and not only did she catch me dancing she caught me putting a photo of her with her new man back on the shelf. Katy was carry a dress still on its hanger.

'Do you recognise this?' she asks brandishing the dress before me proudly.

I shook my head and tried to rid my mind of the girlish thoughts that were invading my mind. I didn't. Not instantly. It was an a-line dress with three quarter sleeves in bright red with a matching spaghetti strap belt.

'No.. ,' she chuckled, 'take another look .. that does surprise me. This was one of our favourite dresses. We bought it together in London. We went to a club and stayed overnight in a hotel.' She giggled, 'you said I looked like the most sexiest girl you've ever known when I wore this dress. You must remember the hotel at least. It overlooked Regents park and the bed was huge with silken sheets.'

I remembered and smiled lustfully.

'Well,' she said scornfully you will also remember that I was wearing this very same dress when you unceremoniously dumped me a month later.'

I shifted awkwardly from foot to foot and feared another fight. I did remember. There was an awkward pause and I awaited for her to either throw it back at me or dramatically tear it in two. 'Well my darling if you want to date me again it is you who has to wear this gorgeous dress not me.'

I laugh and look at her bemused unsure if she was serious or not. She said nothing more but simply stared at me her eyes seemingly penetrating my panties, bra and hose.

'Well whats it to be.. don't you want to date me again?'

I said nothing unsure what to do.

She walked around me rubbing her hand along my back pausing to finger my bra strap under my t-shirt. 'It's not much to ask from someone who regularly wears his girlfriends.. ' She paused and corrected herself.. 'who regularly wear girls lingerie.'

I grimaced as she stood in front of me and slipped a hand into my panties. 'I know you enjoy wearing these and want to wear more.' Her fingers caressed my cock and it begins to stiffen. 'You would look so pretty in this red dress. Your shaven smooth legs would look amazing and your padded tits would fill this dress so well. You must know it's so this season. You'll look like a model. I can see you now.. You would look like the sexiest girl ever.' She smiled and held the dress up against my shoulders. I didn't back away but to this day wondered if i should. 'Wear this lovely red dress and I WILL take you out and we can relive old times.'

I looked at her in amazement. 'Are you saying we can resume our relationship.. Start going out again.. Like before?'

She smiled seductively . 'Let's not run before we can walk,' she said, 'but depending on the effort you put in to dressing up for me and how the evening goes. Who knows.' She fingered the dress and pressed the bodice against my chest. 'What I do know is if you refuse to wear this when you leave my flat I will never want to see you again.'

Tomsparty
Tomsparty
644 Followers