Sally’s confusion continues.


Following the last encounter Sally was in turmoil.


Sue suggested that maybe it would be worthwhile contacting a site through google that would allow me to ask questions of others in this predicament and maybe find people who had been in similar situations. I looked up cross dressing in google and had hundreds of hits. I contacted some sites that specialised in T/V, cross dressing and T/S questions. I was particularly hoping for people to contact me who had long time partners and were caught cross dressed unexpectedly. I had loads of responses but one in particular was of particular interest, just not in the way I expected. A man e mailed saying although he had never had the experience I described he had always wanted to get into conversation with a straight man who dresses as a woman. He believed that ones sexuality could adjust according to the mind set of the person at the actual moment of encounter and that sexual preference could alter depending on the company, the surrounding atmosphere and their own state of mind.

This unusual mail prompted me to contact him and ask him to expand on why he believed such a theory. His logic was simple: different times, different places and different people created different responses. He suggested that one way to discover if his theory was too far fetched was for me to get dressed in my sexiest outfit when Sue was out and e mail him. This would allow him to put some ideas and thoughts to me. I agreed to give it a go, just for a trial obviously.

Two days later, on Monday morning, I put on my loveliest white lace bra. I love this bra because although it doesn’t do anything to give me big boobs it does shape what is naturally mine. I get a recognisable cleavage and my nipples show through the material and when I get excited they become quite prominent. I topped this with a silky peach button through blouse. The outline of the bra could just be made out through the material. I slid my tight fitting white satin knickers over my manhood and the squeeze of the material effectively gave me a flat silhouette. A lovely velvety flared skirt of pure black was next. It reached to just above my knees and the effect was super. My favourite bit was when I spun around. The rub of the velvet against my knickers was sumptuous and as the skirt flared up there was a most sexy glimpse of my panties. I put on my strappy black shoes which were difficult to walk in but they made me stand up very straight and caused by bum to give a most appealing wiggle when I walked. I sat at the P.C. and tentatively sent the e mail.

‘Hi’ came his reply. ‘Describe to me what you are wearing’. I did, in glorious detail.

‘How does it make you feel?’
‘Very sexy’

‘But what exactly is it that makes you feel so good?’ he asked. ‘Why does this feeling get so strong?’

‘Probably because it is not normally accepted practice.’

‘So is it the excitement of the difference that gets you going, entering a world of make believe with a stranger pretending to be something you aren’t normally?’

I thought for a few seconds and realised that he had pretty well hit the nail on the head.

‘Yes. I suppose it is.’

‘So while you are sitting there reading my mail you are comfortable in the knowledge that I know you are not a ‘normal’ woman but a man feeling very sexy as a woman?’

‘Absolutely. Mind you it is anonymous and I feel great.’

‘It may be anonymous but to me you are Sally and you sound very sexy as well as very turned on. Is that fair?’

‘Yes’ I knew he was right so far.

‘Is it also fair to say that your knowing I am really aroused by the thought of you increases your own feeling of sexiness?’

‘Oh yes.’

‘How would you feel if right now I was lucky enough to be in a position to run my hand under your skirt. You described beautifully how soft it all felt and I would love to stroke your thighs and feel the softness of your silky panties.’

I couldn’t help myself.

‘Mmmmm it sounds heavenly?’

‘I would love to feel your nipples through the soft lace of your bra, even better I would like to undo the buttons on your blouse and suckle your breasts through your bra, feel your nipples getting harder and when I pull away the dampness left by my mouth would cool your nipples and they would stand out even further. How does that sound?’

‘Gorgeous.’

‘My hand moves over your crotch and I can feel your hardness wriggle at my touch. I would take your fingers and you would undo my trousers exploring my firm cock.’

I knew then that he had managed to wrap me up in this fantasy and our imaginations started to run.
We exchanged rapid mails, each one explaining what we do and how we would feel. It was very exciting and felt dangerous and fun. I came in delirious joy and he informed me that he did at the same time. Obviously we can’t tell if it was actually mutual but the idea was lovely.

A day later he mailed me again.

‘What did you think about yesterday?’

‘It was magical and I haven’t slept much replaying it all in my mind.’

‘How about we meet and we can discuss it further?’

‘I’m not sure if that would be appropriate.’

‘Why. Are you scared.’

Well quite honestly I am but the gauntlet was cast.

‘It isn’t that, it’s just that I don’t know what Sue would say.’

‘So don’t tell her.’

It all sounded so easy. After a bit of pressure I relented and he said he would fly in the following weekend. Sue was away for the weekend otherwise I would never have agreed. The condition was that I meet him whilst I was cross dressed. I am still not confident about being seen in public on my own in daylight so we agreed that he would land at Heathrow and he would come to the short stay car park at terminal 4 and wait by the 3rd floor exit. I would then collect him in my car. The plane landed and an hour or so later I saw someone arrive at the nominated door. He was wearing the coat just as he had described and was clearly looking for someone. I assumed it was me for whom he was waiting.

All I had to do then was pluck up the guts to actually go and identify myself. I waited a short time, like all girls it felt good to make him wait. I finally plucked up the courage and drove across the car park.

‘Hello Sally sweet thing.’ He said with a boyish twinkle in his deep blue eyes. ‘I hope you aren’t disappointed by what you see.’

I was taken off guard by his easy welcome and gave a really weak giggle. ‘I hadn’t thought about it.’

‘Now that must be a lie.’ He said. ‘You have arranged to meet someone who is a sort of long distance lover and never thought about their appearance.’

Once again he had caught me off guard with his directness and the accuracy of his words.

‘Ok. You are right. You are a bit shorter than I expected but not too bad.’ This was said with a wink and a smile.

He took my comments with a wide smile and showed a fine set of bright white teeth while he climbed in next to me throwing his bag in the back. He took my hand, kissed it sweetly and told me it was lovely to meet me at last. I thanked him and we made our way off for the 1 hr drive home. I managed to make small talk about music and England and other bland stuff you discuss on a first date.

I pulled up in the drive and we went into my house. The place I have shared with Sue for 10 years and where I have not even kissed anyone else without her knowledge. I had prepared a simple meal of salmon and salad and accompanied it with a crisp, cold Chablis. As we were sitting across the dining table he produced a little package.

’For you’ He said. ’I hope you like it.’

I opened it and found a lovely simple gold ring with a single blue stone glinting beautifully.

‘It is a stone called Tanzanite.’ He told me. ‘I hoped the colour would match your eyes and it is a pretty good match.’

‘No-one has ever given me anything like this before.’

‘I should hope not. Do you like it?’

‘It’s beautiful.’ I said as I slipped it on my second finger. It fitted perfectly.

‘I am pleased, it took me ages to decide whether it would be appropriate.’

‘Oh yes it is perfect.’

He leant across the table and kissed me gently on the lips.

‘I told you that the right atmosphere, the right person and the right mind set would allow you to do anything.’

‘I think you are probably right again.’ I purred loving the softness of his breath. We kissed again and I loved the feel of his tongue dancing exquisitely with mine.

He took me by the hand and led me to the fireplace. ‘You are really quite gorgeous and I want to do to

you what we mailed about. Is that OK.’
‘Oh you sweet thing, please, please me.’

He laid me to the floor and rained my face and neck with the softest sweetest kisses I could ever imagine.

‘I will treat you like the lady you deserve to be.’

I had never been so excited, my heart was jumping the way it did on my first kiss as a teenager and when I lost my own virginity whilst I took Sue’s. My whole body ached with emotion. I cried small tears of joy as he moved his lips over my breast and kissed and sucked on my nipples.

I couldn’t resist a moan ‘Oh yes sweet thing’. I held his head there as delighted my body with his tongue.

He moved his head further down and, just as he had described, the dampness left on my bra caused my nipples to swell even more. I wanted so much to find a way to please him but he continued his slow, methodical edging towards my crutch. His hand lifted my skirt as he rubbed the silken panties. He learned that I was wearing the same pair I had when we e mailed. He moved his fingers over the smooth material. I couldn’t bear much more so I asked him to kneel up with me. We faced and as we kissed deep and long I removed his shirt and undid his trousers. He stood as I stripped him completely. His erection was at face level and I gave it a loving lick and tried to take him into my open mouth.

‘Oh no my darling Sally. Tonight I intend to treat you as a lady.’

We continued to caress, stroke and kiss. He moved his hand around to my bottom and felt my little hole. He had some jelly on his fingers and slowly and lovingly moved his digit into my puckered anus. The feeling was fantastic. He eased me onto my back and removed my very wet knickers. ‘I will be gentle lover.’ He whispered and I felt his knob nudge the entrance to my passage. He raised my legs and mouthed ‘relax sweet Sally’ I tried to let my body relax but the unusual feeling was leaving me tense. The gradually increasing pressure was slowly parting my entrance and the feeling of being full was immense.

As he entered me the small amount of pain was replaced by sheer pleasure. I looked into his eyes as he filled me and very slowly I took all of his glorious erectness into my body. ‘Fuck me’. I said with a croaky voice. ‘Please fuck me.’

‘Oh sweet Sally I promise you that is what I am doing.’ I felt him move in and out and he seemed to expand and fill me even more. He began to move himself with a bit more urgency and as my legs wrapped around his body he lowered his lips to my breasts. The urgency in his breathing increased and I knew that he was now in the throes of total ecstasy. I felt his prick start to vibrate and in the few seconds before he exploded I just managed to say ‘Fuck me my own sweet thing.’ And he flooded me with his love juice. He removed himself quite quickly from within and he held me in his arms while he stopped shaking from his exertions.

‘My God, that was fantastic’ He said, but what about you, how would you like me to help you orgasm.

‘My dear sweet thing.’ I said shakily. ‘I came at exactly the same time as you. I didn’t need to have anything touch my man clit. The pleasures of your orgasm sent so many ripples through me that I came automatically. It was fantastic.’

‘Oh my sweet lover you really are special.