I wondered afterwards: just how obvious had it been? And did everyone know? When Dekker stood in front of me and simply refused to move his six foot four, two hundred pound body out of my way, was he guessing? Or taking a chance, not really caring what I was and what I wanted, gambling that I wouldn’t go crying to the police afterwards? Whatever the reason, he was in my kitchen and in my way, wearing a smile that said “What you want doesn’t really matter. What counts is what I want.”
He moved closer and put his hand on my cheek. Closer still and now the hand was holding my chin, tilting my face upwards so that he could kiss me on the lips. I didn’t resist, except to say, ‘I’d like you to go. Please.’
He laughed and said, ‘It isn’t what you’d like that counts.’ Then he kissed me again.
My heart was beating fast. I said, ‘Please don’t do this,’ and tried to push past him but I was eight inches shorter than Dekker and eighty pounds lighter and I went nowhere. He laughed. Not a nasty laugh, but enough to let me know who was in charge. Any further resistance would have been pointless, resulting only in getting me hurt more than I was going to be in any case. I stood motionless and let it happen. Went on letting it happen when his tongue came into my mouth and his knee pushed between my legs. That was what I wondered about later. Had he known?
I was twenty-one years old, a graduate, holding down my first job and living in my first apartment. Twenty-one years old and still a virgin. A virgin with women and a virgin with men. I’d had my chances with women but they weren’t what I wanted. When I dreamed; when, in the privacy of my bed I imagined lying in someone’s arms; the someone was not female. These feelings made me ashamed. Being gay would make me less than a real man, and I fought it. What I dreamed about was wrong. I couldn’t have it and I shouldn’t want it. I’d longed for a woman I could love enough that we would take our clothes off and I’d make myself a complete person. I’d fantasized that one day it would happen and I would be normal.
But now here was Dekker and I had to face the reality: that he was someone I could happily take my clothes off for. And even that wasn’t entirely true because what I really wanted was for him to undress me.
None of which changed the fact that I was scared. Frightened of being physically hurt when he did the thing I was quite sure he wanted to do and anxious about the way my life would be afterwards. Because I didn’t think I could give in to what Dekker wanted and then go on being the person I’d been before.
Dekker removed his lips from mine. ‘There’s always two ways to do a thing. The easy way or the hard way. And the good news is: you get to choose.’
I put my hands on the muscular arms that still held me. ‘Will it hurt?’
‘This your first time?’
‘Well. Why don’t we go to your bedroom and find out? You got any K-Y Jelly?’
‘No.’ I’d never needed any.
I shook my head.
I opened a cupboard and pointed. He picked up a bottle and waved it at me. ‘Extra Virgin. That’d be about right, don’t you think?’
I didn’t say anything. He took me by the hand and led me out of the kitchen, down the hall and into the bedroom, pausing at the bathroom door long enough to take a towel off the rail. ‘This could get messy. We’d better put this under you.’
In the bedroom he kissed me again and at first I let my arms hang by my sides but then I thought, “It’s going to happen, whether you join in or not,” and I brought them up and wrapped them round him. This was how my dreams had always been: me as the girl, submissive, giving myself to a strong man. I said earlier that the women I’d had chances with weren’t what I’d wanted but neither were the men. There had been gay men at college and no doubt some of them had been butch but they weren’t the ones I spotted – my gaydar was undeveloped. I didn’t want to be in bed with someone effeminate and needy – what I wanted was someone almost embarrassingly male. Someone like Dekker. Since that day I’ve got to know a number of women who, like me, prefer their own sex and I’ve become familiar with that whole butch/femme relationship. If Dekker and I had been women I suppose he’d have been the butch and I’d have been the femme.
He picked me up and laid me face up on the bed. I watched as he undressed without haste. When I saw the size of his cock I felt a moment’s nervousness – that thing was going into me and how could I possibly take something so big – but the nerves were overshadowed by something much more important; my dreams were going to be consummated at last. He had a huge barrel chest and a mat of hair that extended all the way down over a flat stomach to what promised to be the organ of my deflowering. I felt a shiver of lust. Then he was on the bed with me, unbuttoning my shirt, unhooking my belt, unzipping my shorts. I lifted myself so that he could get them down, closed my eyes and waited for him to stop. He did. I knew without looking that he was staring at what he had found. They weren’t the lacy, sexy ones I wore when I was getting into the mood to pleasure myself – these were girly pink gingham with a little bow at the waist and a rosebud on one leg. They weren’t, though, remotely masculine.
I opened my eyes. I’d been afraid he might be disgusted but the smile on his face was friendly. ‘Do you always wear these?’
I shook my head. ‘No. Only when I’m not going out and I don’t expect to be disturbed.’
‘I’m sorry to have spoiled your expectations.’ He lifted up the pillow beside my head and pulled out the shorty nightdress. ‘You’ve got all the gear, then. Is this how you see yourself? As a woman?’
‘Look,’ I said. ‘You’ve found me out. Okay? Now why don’t you just get on with raping me? That’s what you’re here for, isn’t it?’
He put his hand to my cheek. ‘Hey. We were getting along. Weren’t we? I offered you hard or easy and I thought you’d taken easy. It doesn’t have to be rape. You can be my submissive girl and I’ll be your masterful man. Is that a tear?’ His finger touched the corner of my eye. ‘Why are you crying?’
There are times when telling the truth is a blessed relief. As I spoke, the single tear became a flood, rolling down my cheeks and falling from my chin onto my chest. That chest that I had longed so often could look like a woman’s. ‘A submissive girl,’ I sobbed. ‘That’s what I’ve always wanted to be. Nature is so cruel.’
He kissed me, gently and with apparent affection. He took hold of the waistband of my panties. ‘Well just lift your bottom, honey, and you can submit to me.’
There wasn’t any point in pretending that I was being forced because the hardness of my cock told a different story. He folded the towel and tucked it under me. He spilled a little oil into the palm of one hand and then, kissing me all the time, he began to stroke me towards my climax. I wrapped my arms around him and let it happen. The tears had stopped. I was going to get what I wanted – what I had wanted for so long.
It didn’t take long. I came on his hand, on my stomach, on my thighs. He lay beside me and nuzzled my face. ‘Thank you,’ I said.
‘Now I know why you live alone,’ he said.
‘Someone like me needs privacy,’ I said. ‘Imagine a flatmate wanting to borrow something and going through my panty drawer. Or inspecting my laundry.’
‘Are you ready for what comes next?’
I kissed him on the hairy chest. ‘You’ll have to tell me what to do.’
‘Turn onto your front, honey.’ I did that and he said, ‘Hey, are you still James when you dress like this? Or do you have another name?’
‘Penny. Penelope if I’m feeling formal.’
‘Okay, Penny. Now you asked if this would hurt and the answer is that it will. I can’t change that but I can make it as painless as possible. I’m going to massage oil into your extra virgin boy-pussy – quite a lot of oil, which is why I needed the towel – and then I’m going to rub some on my cock. It will still hurt, but less, and I won’t leave you with any lasting damage.’
I felt quite brave about what I said next. ‘When I’ve dreamt about doing this, I always imagined I’d suck the man’s cock before he put it in me.’
‘You ever do that? Suck cock?’
‘No. Never. But I’ve watched it on videos.’
He lay back on the bed. ‘Okay, Penny. Go for it.’
All the times I’d imagined it, I’d never known quite the feeling of joy that came as I took him in my mouth. It wasn’t just what I’d seen on the screen that I was copying; I’d thought about it so often I knew exactly what I wanted to do. I stroked his balls gently as I licked and sucked him. Then I took him out of my mouth, held him between thumb and forefinger and licked his balls all over – on top, underneath, at the sides and in the soft place between the sac and his ass. Then I took him into my mouth again. He’d been hard when I started but he was a ramrod now. At last he took my head gently in his hands and lifted it. ‘Any more of that and you’ll be holding onto your cherry a bit longer. On your front again, sweetie.’
He prepared me with fingers coated in oil. First one, then two and when the third joined them I began to feel that if I could take this I could take him. It was still a shock when the fingers went, he pushed my knees apart, knelt between them and began his penetration. I thought it was going to end in failure but he was not to be denied. The first inch or so was the hardest because after that I couldn’t have kept him out if I’d wanted to. Eventually and after what felt like enormous pressure on his part and impossible acceptance on mine his hips were tight against me. He lay still, kissing the back of my neck, while I became accustomed to this intolerable intrusion – and then he began to move. Although I felt I would be ripped apart, I did not ask him to stop because (a) I didn’t for one moment believe he would and (b) I didn’t want him to. It hurt. I had known it would, he had said it would and it did. It hurt. But it was what I had wanted for so long. I heard him gasping, felt the rapid in and out as he took me, and then – with a final gasp that was almost a shriek – he was pumping his seed into me.
He lay prone, pressing me face down into the mattress. Then, his cock now soft but still in me, he whispered, ‘How do you feel?’
There were so many answers to that and I gave him all of them. ‘Sore. Hurt. Fulfilled. Satisfied. Female. Happy.’
He lifted himself from me. ‘Stay just like that.’ He left the room and when he came back he had a warm, damp face cloth in his hand. Tenderly he wiped clean the place where he had – let us use the word – fucked me so imperiously. Then he dried me. And then he wrapped me in his arms and I put mine around him and we lay side-by-side, nuzzling each other. I felt myself drifting off to sleep.
When I woke, I was alone. I got up, pulled on the pink gingham panties and, wearing those and nothing else, went into the sitting room. Decker was on the balcony with a glass, a bottle of bourbon, an ashtray and a pack of cigarettes, one of which he was smoking. There was another, empty, glass on the table. He hadn’t found any of those things in my apartment.
‘I went across the corridor to my place. You don’t seem like a smoker to me so I came out here. I didn’t want to leave the smell.’ He held up the bottle. ‘You want a drink?’
‘Not of that.’ I went to the fridge, opened a bottle of white wine, poured myself a glass and brought glass and bottle out onto the balcony. Then I went back, emptied a pack of pistachios into a bowl and set it down between us. I sat down and remained that way for about three seconds before I got up again and brought a cushion from the sitting room. ‘You a bit sore down there?’ asked Dekker.
‘I sure am.’
‘Was it worth it?’
‘It sure was. We can’t be seen from here, can we?’
‘I don’t think so. If anyone does see you they’ll probably think you’re wearing shorts. But if you feel uneasy…? We can probably be heard from other balconies, though. You might want to be a bit careful about what you say. Or whisper.’
‘Okay,’ I whispered, and laughed.
‘So,’ he whispered back. ‘Is it secret? Or are you going to tell me your story?’
‘Oh. There’s nothing much to tell. It’s just the way it is. Since I was a small boy I’ve felt I was in the wrong body. It’s no big deal. Worse things happen to other people, I know that. I’m not thinking of gender realignment surgery – apart from anything else, I wouldn’t do that to my mother. I don’t want her to feel she’s been a failure. I live alone and when I don’t have to go to work I pretend I’m the girl I should have been.’
‘You mention your mother. What about your father?’
‘He left when I was six and no-one’s heard from him or seen him since. My mother raised me and my three sisters on her own. It wasn’t easy but she did it.’
‘One boy in a house with four women.’
‘Yes, I know, and if you want to read something into that I’m sure you will. Yes, I did envy them, and yes, I did try on their underwear but no, I didn’t want to be them. What I wanted was to be me but to be loved by someone who might love them – a man, a real man, a bear. Which I got when you came to my apartment this morning. Now it’s your turn because you haven’t explained how you came to be there.’
‘That’s easy. I came to fuck you.’
I stared at him. I didn’t know whether to laugh or protest. ‘Explain?’
‘I like being a man, and I don’t feel like being anything else. I’m not like you, because I accepted a long time ago that I’m gay and I don’t think you are – you’re a straight who happens to be in the wrong shaped body. That was a mistake I made when I watched you. I got the wrong idea.’
‘You watched me?’
‘I’ve been watching you for weeks. What I thought I saw was someone effeminate. What I see now is a girl, which is not the same thing; a girl who has the bits that interest me in a man.’
‘That must have been a disappointment.’
‘Nothing of the sort. That fuck today was the best I’ve ever had. I love it that you’re in panties. I love it that you sleep in a nightdress. If you hadn’t given yourself to me willingly I’d have taken you by force. You wouldn’t have been the first. But what we had was much better than rape.’ He lit another cigarette. ‘Are you doing anything tonight? Or would you like to spend it with me?’
‘I’d love to spend it with you but I don’t think I can face another fucking quite so soon.’
‘No problem. You’re the best cock sucker I’ve ever known. That thing you did with your tongue on my balls was unbelievable. But we need to eat something. Do you know the Mayfair?’
That gave me pause because although I did know the Mayfair, I’d never even thought of going there. Entering that place would be like advertising your gayness which wasn’t something I’d ever thought of doing. Really, I’d assumed I’d spend my whole life wishing for something I couldn’t have. Dekker coming to my door with rape on his mind had changed that. ‘I’m not sure I have the courage for the Mayfair.’
‘I’ll look after you. No-one’s going to hit on you when you’re with me. And they do a really good London Broil.’
It was decision time. I hadn’t quite got over Dekker’s admission that, if he hadn’t got lucky, he’d been prepared to use force to get his way but nor could I overlook the fact that he had brought me contentment of a sort I’d thought I’d never know. Maybe I’d have to review my ideas about the things I’d thought impossible. I made up my mind. ‘Okay. The Mayfair it is. But you won’t ask me to wear a skirt?’
He laughed. ‘Not this time, at any rate.’
I got dressed – like a man, except that under my loose cotton matelot pants I wore an equally loose fitting pair of French Knickers – if you’re not into lingerie, those are the kind with legs loose enough for a man to put his hand into.
Dekker was known at the Mayfair and we were welcomed and shown to a booth. Dekker ordered bourbon on the rocks for him and a bottle of California Shiraz for me. He also ordered a bottle of water. From the menu he chose the London Broil he’d mentioned which he wanted well done; I went for a spicy Mexican chicken dish.
It was fascinating to watch the men at the bar (they were all men, though in some cases you had to look hard to be sure – the only woman in the place was a waitress). It was obviously a pickup joint and some of the more feminine looking young men behaved in an outrageously flirtatious way that – secretly – I admired. Where did they get the courage to be themselves? While we waited for our food, a group of four came in and sat at the table near us. The two older men were clearly powerful businessmen (or mobsters – the power was obvious but not so clear was where it came from) while their dates were much younger. One of the young men turned to one of the seniors and asked, ‘How do you want us? Boy, girl, boy, girl?’ and the older man smiled and said, ‘Sit down and stop playacting. You can go through your routines later.’
Dekker put his hand on mine and pressed gently. I should have been shocked at this open demonstration of man to man affection – I could not imagine ever consenting to it in a more “normal” venue – but somehow here it seemed right. I turned my hand over and squeezed his. I was aware that anyone watching would have seen me staring into his eyes and smiling and it amazed me that I simply didn’t care. ‘You feeling okay?’ asked Dekker.
‘I feel great. I’m so happy you came into my life today.’ And I was. It was like all the dissembling, all the pretense, all the denial that had been part of me since I was quite a young boy had been taken away. If Dekker had asked me to get under the table, kneel between his legs and suck his cock I might very well have done it. Fortunately, he didn’t ask. What he did do was to put his hand on my thigh, slide it up until it was between my legs and stroke me to hardness. I said, ‘You’ll make me come inside my pants,’ and he said, ‘So open them,’ and to my amazement I did exactly that. He put his hand up one leg of the French Knickers and, at the very moment the waitress was putting our meal before us, I gave a little jump and a loud gasp as he stroked me to orgasm. The waitress gave me an understanding smile. ‘If you guys can’t wait,’ she said, ‘I’ll keep these warm while you use one of the private rooms.’
I astonished myself by saying, ‘It’s all right – I think I’m done for now.’ The waitress laughed and Dekker patted me on the thigh.
There was a floorshow and, after we’d finished our meal, we stayed on for a while to watch while I drank my wine and Dekker ordered more bourbon. He said, ‘I think we’d better take a cab back. I don’t want to spend the night in a cell on a Drunk In Charge instead of in your bed. Or my bed,’ he added. ‘How would you feel about that?’
‘If we go to your place, you’ll be able to smoke. So let’s.’
‘You’re a honey. Do you ever see your mother? Or your sisters?’
‘They’re in Dayton, Ohio. Where I grew up. I came to Southern Cal to be as far away as possible. Not because I don’t love them but because…’
‘I understand. I wouldn’t want my family to know how I turned out, either. Although I’ve completely lost touch, so they could be living in the same building and I could run into them.’
That saddened me a little – the thought of losing all contact with the people who brought you up – but Dekker’s life was his business and not mine.
All through the evening, men who obviously knew Dekker well stopped by our booth to speak to him. I was aware that some of them – most of them if I’m being honest – were giving me the once over. I was also aware that I met with their approval.
The floorshow was amazing, at least to me – I would have expected that sort of action between half naked men to be illegal and I certainly would not have imagined that I would ever be present while such a thing was going on but there was no denying the effect it had on me and, even though Dekker had so recently brought me to a climax, I could feel the fever of lust growing once more. Perhaps the wine had something to do with it – I don’t believe I had ever drunk a whole bottle on my own before, even without the glass of white I had had at home. This was turning into a day in which I amazed myself and I did it once more when I said, ‘How would you like to take me to bed?’ He didn’t say a word – just called for the bill. I said, ‘Let’s split that,’ but he said, ‘Next time. Tonight’s my treat.’
Dekker’s apartment was very like mine which – as it was in the same building – I suppose I should have expected. Looking at it, I could see something I had not seen before, which is that mine was furnished and decorated in a feminine manner – it was an apartment in which a single young woman could feel completely at home – and that was not something you would say of Dekker’s. I suppose being raised in a family with four women and no men was responsible for my taste, while Dekker’s was suitable for a bear.
I went briefly to my own apartment to pick up my nightdress and a clean pair of panties for the morning. When I came back, Dekker was smoking a cigarette. I said, ‘I won’t be long,’ and went into the bathroom. When I came out in my nightie, Dekker put down his cigarette and took my hands in his. ‘My God, you look beautiful,’ he said. ‘You’re right, you should have been born a girl. Except that, if you had been, I wouldn’t want you.’
‘And do you?’
‘I can’t remember ever wanting anyone this much. Why don’t you get into bed and wait for me?’
He didn’t take long, and when he came to bed he was naked. I pressed him onto his back, knelt between his open thighs and did once more with my tongue what had given him such pleasure earlier. This time, instead of lifting my head away, he held it in place while – once again, let us use the word – he fucked my mouth until he came. I had never tasted a man’s sperm before and I knew in that moment that I would want to taste it again and again. He held me tight. ‘Tomorrow is Sunday. I don’t have to work. Do you?’
I shook my head. ‘I’m strictly Monday to Friday.’
‘Can we spend the day together?’
‘And the night, I hope.’
He smiled. ‘And the night. And maybe on Monday morning your soreness will be gone.’
‘I hope so. But even if it isn’t, I don’t think I’ll tell you so.’
We fell asleep wrapped in each other’s arms.
I woke at six. Dekker’s arms were still around me and one of his great paws was on my stomach under my nightie. I took hold of it and moved it down, holding it in place as he stirred into wakefulness. His warm lips bussed the back of my neck while his hand closed around my cock. Slowly it began to move. I rolled onto my back and put my arms around his shoulders as he rose over me, bringing me yet again to orgasm. I said, ‘What would you like from me?’
‘How would you like to use that magnificent tongue again?’
So that is what I did.
And then we settled once more into a state that was half asleep and half awake and it was eight when we began to think about the day. Dekker pressed his lips to my throat. ‘To think that I was ready to take you by force yesterday. What a waste that would have been. Why don’t you take a shower while I think about breakfast?’
I came into the kitchen after my shower wearing only the clean panties that I had picked up the previous evening. He smiled at me. ‘Eggs? Bacon? Toast? Coffee?’
After breakfast, I loaded the dishwasher while Dekker smoked a cigarette. He said, ‘Anything special you want to do today?’
‘Yes. I want to be with you.’
‘Right answer. You said last night that you wouldn’t go to the Mayfair in a skirt. Does that mean you have one?’
‘I have skirts and I have dresses. But I only ever wear them in my own apartment. I don’t want anyone else to see me like a woman.’
‘Does that include me?’
‘Of course it doesn’t include you. But it does mean I don’t want to be seen outside my apartment dressed as anything but a man. Even for the short distance from there to here.’
‘Well, maybe we’d better spend the next few hours at your place. And you can show me what you look like as Penelope.’
While Dekker sat on the balcony with his cigarettes, I went through my wardrobe. I chose a long flowing dress on which I had spent more than I really should have. When I came out of the sitting room onto the balcony, Dekker stood up. The expression on his face warmed me to the very heart. ‘My darling Penny, you look beautiful.’
‘Thank you. And you look like what you are. A red-blooded male.’
‘Do you find it hard to shop for this stuff?’
‘Not online. I don’t think I’d ever have the courage to go into a store and try something on.’
‘It’s a good job you don’t have hairy legs.’
‘I shave them.’
‘You do? Where did you learn to do that?’
‘I grew up with three sisters. All older than me.’
‘Of course. You haven’t brought a cushion to sit on.’
‘I’m not sore any more, my darling.’
‘Oh? Really? You mean it?’
‘I do. But I’m hoping some time today you might want to change that.’
‘You want to feel sore again?’
‘Not really. But I want to be fucked again and if I feel sore after it, that’s a price I’m ready to pay.’ I thought about what I had just said. ‘Do you have any idea how big a change you’ve brought about in me in twenty-four hours?’
‘It couldn’t have happened if you hadn’t wanted it.’
‘I know that. And you cannot know how grateful I am. There was a door in my life – I knew it was there and I knew it would always remain closed. Then you came and you opened it and I walked through.’
‘I’d be insane to regret anything. You completed me. You fulfilled me. You made it possible for me to be me.’ I leaned across the table and kissed him on the lips.
That’s my “First Time” story. Everyone has one – everyone, that is, who is not a virgin. We all come into this world with no sexual experience and I’m aware that for some people their sex lives are so unsatisfactory that they wish they could leave the world in the same virginal state. It hasn’t been that way for me. Whether I would ever have accepted what I really was and given in to lusts I believed to be wrong had Dekker not decided he was going to have me anyway is something I can’t say. But he did.
Thirty years have gone by since the story I’ve recounted here. My mother died ten years ago; two years later I came out to my three sisters, who laughed and told me they had always known. Dekker and I did not last long as an item because, whatever he said about loving me and finding the person he’d been looking for, the reality was that love was not what Dekker wanted. He only felt fulfilled when he used force. Eight months after we had met, that desire to rape came up against someone less submissive than me; his victim went to the police and, so far as I know, Dekker is still in jail. I expect he finds enough of what he called “boy-pussy” there to keep him happy but I imagine he sometimes hankers after one of Mayfair’s London Broils.
And me? I have a bear of my own now. We share a house and a life. Thank you, Dekker. Flawed you may be but I couldn’t have got here without you.
Note from Author
I hope you enjoyed this story. If you did, you may like to know that you can find my novels and novellas here.