XP07
Keywords: XP07,
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[Note: Jenny's story (Punch Line (BDSM section)) should have been called XP07 really. It is intermediate between XP06 and this story.]
"We are still at Mr and Mr Prentice's "literary luncheon". Jenny's story has left everyone feeling slightly maudlin. Mr Prentice, wanting to lighten the mood, looked sternly at his transvestite maid, Betty. 'Come on, Betty. Tell us how you became my slave.'"
Like Colin, I answered an ad in the lonely hearts. I had always regarded myself as a masculine man but, in private, I sometimes fantasized about being the passive partner in sex. I would pretend my wife was a man as she went on top. I would open my legs as her vagina gripped my penis, her legs straight, between mine. I would put my arms up around her neck and pull her into a kiss as I imagined her pumping into me, instead of the opposite that was really the case. Of course, we had normal sex too, and I never told her of my fantasy. When she left me – I had been seeing another woman – I discovered that she had left some of her clothes behind. The other girl had chucked me too and in a bored, frustrated moment, I decided to see what it would feel like to wear a dress and high heels. The dress was too tight to zip up but, luckily, my wife had had big feet, the same size as my rather small ones. The image of myself in the mirror in a pretty satin dress and high heels had me wanking myself silly in no time. After a couple more tries, I decided to order an outfit that would fit and sent off for stockings, bra, knickers, a dress, make-up; the lot.
I don't want to give the impression that I did it a lot, but occasionally the mood would take me and I would dress up and potter about the house at weekends. It always ended in a massive, self-induced orgasm. I fantasized about daring to go out like that but I never did, and knew I never would. Then I saw the ad.
*Transvestite*, 40s, 5'5", slim, convincing, WLTM understanding M for f/ship & romance.
Something grabbed my attention. I think it was the 'convincing' – something that I definitely wasn't, even with the wig I had now bought, even with a corset to pull my belly in. No, I wasn't slim or convincing. What would it be like to meet a real trannie? I would have to fuck her/him of course. But maybe – just maybe – he would return the favour, dress me up and fuck me; let take the passive rôle. I wrote to the box number and enclosed a photograph.
A week later, I had almost forgotten the ad. Then the phone rang.
'Hallo.'
'Can I speak to Barry?' said a voice of ambiguous sexuality.
'Speaking.'
'My name's Sally. You answered my ad in the paper.'
The memory flooded back. 'Yes,' I said and paused, waiting for the voice to take the lead. There was silence.
'Thanks for ringing' I said, 'I glad you did'.
'Could you tell me about yourself, Barry?'
'Well, yes, of course. I'm about your age, a tad taller than you. Not bad looking, Own teeth, tiny bit of hair loss, and–'
'Are you gay?'
'No. I mean, er . . . I suppose I must be bisexual.'
'Suppose?'
'Well yes. I usually go with women. What about you?'
'You have to meet me to find out, Darling.' The voice definitely sounded feminine now, as if the talker had slid into the rôle gradually.
'OK. Do you know a good place.'
We arranged to meet in a wine bar that Sally suggested.
'Oh, one more thing,' I said. 'How will I, er, recognize you? Will you be–'
'Yes, I'll be wearing a dress – a red one; shortish blond hair, matching red leather bag. Don't worry, I've got your photo.'
She rang off.
I wondered if I could go through with it. If she wasn't 'convincing' it might be terribly embarrassing. But curiosity and arousal got the better of me. On Saturday, I washed and shaved and put a suit on. Better to start off smart, I thought.
I got to the wine bar early and took a bottle of designer lager to a corner table. The place was busy but not crowded. I had a clear view of the door. I was on my second bottle when she walked in and looked around. Blond, tight red dress, matching bag. It had to be her. She was gorgeous; impossible to believe she was really a guy.
She sashayed to my table. I stood. 'I'm Barry,' I said, still not one hundred per cent sure.
'You look like the photo, Barry,' she said, taking my offered hand and sitting down.
'You look lovely,' I said, still incredulous.
'Thank you, kind Sir. Shall we have a drink or move on?'
'Oh, sorry; how rude of me. What would you like?' I stood up again.
'A glass of the Chablis please, or Sancerre if they haven't got any.'
I returned to the table with a bottle of slightly overpriced Chablis and two glasses.
'What do you do?' she asked.
'I'm an accountant. Boring, eh? What about you?'
'I'm a photographer; fashion mostly.'
'Sounds more interesting than my job at least. Do you get to meet lots of famous people?'
'Sometimes. But any job has its routine side. It's not as romantic as most people think. Hard graft sometimes.'
'Do you – I mean do you always, do you always–'
'Dress like this? No, Barry, I revert to type during the day. The vamp only comes out at night. I'm not transsexual you know.' She smiled.
I wondered what the man would look like. Slightly scrawny, emaciated? As a woman she looked good, slender, elegant. Yes, convincing.
'What's your – your other name?'
'For you I'm just Sally, Darling.'
'Have you eaten?'
'No, but I'm not hungry. Got to watch my figure. You have something if you want. I'll just have some nibbles.
I went back to the bar and ordered an open sandwich and a selection of nibbles. Before long we were chatting easily, the ice broken now. I had soon forgotten that Sally wasn't a girl. When the wine was all gone, she placed her hand on mine and leaned across the table.
'Shall we do it again?'
'Yes, I'd like that.' Suddenly I wanted to kiss her.
'When?'
I plucked up whatever it is that you pluck up in these circumstances and said 'Look, can I see you home. We can talk on the way.'
She fluttered her long eyelashes and smiled. 'How chivalrous. Thank you. We can walk from here. It's quite close.'
She took my arm as we walked. Her flat was in a serviced block. We stopped outside the main entrance. I pulled her toward me and offered a kiss. I could feel her breasts press against me; false I presumed.
She pecked my cheek. 'Come in for a coffee.'
My prick twitched in my trousers. Did she mean what most people meant by 'coffee'?
'OK.'
We took the lift up to her flat. As soon as she had closed the door, I kissed her. She responded, opening her mouth and pressing against me. Her hand was on my groin, squeezing my erection. She moaned as I writhed at her touch.
'Will you hurt me with such a big weapon?' she whispered suggestively.
'I'll try not to,' I said.
'I want to see him. Come to the bedroom.'
She pulled me after her. I was scared. I had never fucked a man. What would she think of my fumbling attempts?
The sight that greeted me in the bedroom flushed away these thoughts completely. The walls were hung with whips and canes. The iron bedstead was adorned with handcuffs and thick ropes. Sally's hands all over me, pulling my jacket off, loosening my tie, unzipping my trousers. She sank to her knees and I moaned as her fingers found my hard prick and pulled it free from my pants.
'God he's big,' she said, before taking the glans between her bright red lips.
I gasped as she pulled my foreskin over the ridge of the helmet. Her hand was rubbing and squeezing the shaft as she sucked and licked. It was too fantastic to describe. She knew exactly where to lick, how fast to rub, when to stop and tease and when to resume. She was more skilful than any woman. I was helpless when my body was gripped by those rhythmic contractions. I exploded into her mouth. It felt like the jets of sperm would never stop. I tried in vain to pull out of her mouth as she milked me dry, almost to the point of pain.
Eventually, she released me and stood. Her kiss flooded my mouth with my own sperm. I wanted to expel it but her kiss insisted and her arms held me tight in a surprisingly strong, yes masculine, grip.
'Swallow it all like a good boy,' she said in a deeper voice than I had grown accustomed to from her during the evening. 'Otherwise Mummy will have to punish you.'
'But–'
'Shut up and lie on the bed.'
Weakened from my massive orgasm, I didn't resist as she pushed me down on the bed face down. By the time I realized what she was doing it was too late. She had handcuffed my wrists to the bedhead. She was pulling of my shoes and tugging my clothes from around my ankles. It was "her" who was going to fuck "me"! It was what I wanted: to be tied up and raped, helpless.
'You've been a very naughty boy, Barry. Did I say you could come in my mouth? Well did I?'
'I thought you wanted me to. I'm sorry.'
'You're going to be.'
She was tying my ankles with rope. Now she was standing next to the bed holding a braided leather whip.
'OK,' I said, 'joke's over. Just fuck me.'
The pain seared though me as the whip struck both buttocks. I heard it whistling through the air again and screamed as it struck again – and again, and again. I lost count.
I was crying profusely and begging for mercy by the time she stopped whipping me. My arse felt as if it were on fire.
'You won't come without permission, will you, Barry?'
'No,' I sobbed, 'I'm sorry'.
'Good. I'd hate to have to punish you again.'
She was lying. She got off on this stuff. Why else all the paraphernalia?
'Are you going to fuck me now?'
'Would you like that?'
'I don't . . . I'm not sure.'
'Yes you are. You're a tart. Shall I fuck you with a strap-on dildo?'
'With your prick if you like.' What was I saying? My own prick was rock solid again and all I wanted was a man's cock in me.
'Don't be silly, Barry. Girl's don't have pricks.'
'But you're–'
The slap on my agonised backside cut off the words.
'Goodnight, Barry.'
She left the room, leaving me sobbing and confused. What game was she playing with me? Why wouldn't she just get on with it and fuck me? Eventually, I fell asleep, to be woken by the morning light filtering through the blinds.
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Keywords: XP07,