by Various
That was the start of it. After a couple of months he’d picked up enough confidence to be a bit better in bed, quite good really, because he would always do exactly as he was told and never tried to push me where I didn’t want to go. He’ll lick for hours too, and not just my pussy, because he likes me to sit on his face so he can stick his dirty little tongue up my bum while I get myself there with a vibrator.
All my friends seemed to think I’d made a really bad choice and was pining for Macho Man, who most of them fancied as well. None of them fancied Dog Boy, and some of them didn’t even want to associate with me while he was my boyfriend, which is pretty crap. I’m stubborn anyway, and won’t let people push me out of the choices I’ve made, so I stuck to him and contented myself with all the great orgasms he gave me.
We’d been going out maybe six months before I discovered his secret. He’d invited me to dinner at his flat and left me in the house while he went out to get a bottle of wine. Being a nosy so-and-so I started to look around. I was also sure he had a huge stash of pornos and I wanted to embarrass him with them and make him grovel for me. I got more than I bargained for.
He had a stash all right, but they were not what I’d been expecting. It was in the chest of drawers next to his bed, the first one I opened. There were loads of them, and every single one devoted to cross-dressing. I knew about it, sort of, but I had no idea he was into it. It freaked me out a bit at first, though I couldn’t help but look at some of the mags and I quickly realised there was no harm in it, just that it’s a bit odd.
That wasn’t all either. I started to put the mags back, not sure how to handle it if he realised I’d found them, and as I shoved the drawer in it got caught on a jumper. I had to pull open the next drawer up to sort it out, and when I did I caught a glimpse of pink in among the clothes. I don’t suppose I’d have even noticed if I hadn’t just been staring at pictures of men dressed in everything from frilly undies to ball gowns, but, as it was, I couldn’t help but stick my hand in. I pulled out a pair of pink knickers, which had me laughing, until I realised they were my own.
It’s a bit weird realising your boyfriend is a complete and utter fucking pervert. It would have been bad enough if I’d thought he’d pinched them to toss off into but, after seeing his magazines, I knew he’d have been putting them on. I also remembered having to walk home commando one night because I couldn’t find my knickers after sex. I wanted to kill him, and I took the knickers into the kitchen and put them on the table where he couldn’t fail to see them as he came in, and sat down to wait. He came in five minutes later, but when he saw the knickers he looked so sorry for himself I really thought he was going to cry.
I suppose I must be soft underneath because, instead of having a go and storming off, I ended up telling him it was OK but that I would have liked him to ask. I got the whole story, about how his parents were divorced and his mum had always put him down, saying how worthless he was and how wonderful his sisters were so that he’d grown up thinking of men as basically a waste of space and women as the ideal in every way. He was in tears by the end, and I couldn’t help but feel sorry for him, so I ended up giving him a hug and doing the cooking while he sat there feeling sorry for himself and asking over and over again if I really minded. I kept telling him it was OK, but he didn’t seem to want to believe me. He wouldn’t stop it, so I eventually told him to strip off and get into the pink panties to serve me dinner.
I’ve never seen a man move so fast. He was stark naked in about a second and had my knickers pulled up over a rock-hard erection in about two. I’ve always liked the sight of a man’s cock inside a pair of pants, and the silky pink material made it even better: kinky as well as horny. I’d sat down again, and he brought me dinner like that, shaking with nerves so badly he nearly dropped a plate.
By the end of the meal I was really enjoying myself. He’d always been obedient, but now he was really grovelling, and looking at me as if he worshipped me. It’s hard not to get off on that, for me anyway. He’d stayed hard all the time, and I really thought he was going to come in his pants, or my pants, but he’d brought out the bitch in me like never before.
I led him into the main room by his cock, holding it through his pants, then told him to fetch me a drink. He served it to me on his knees and stayed that way, kneeling at my feet and staring at me with a sort of dumb adoration. I was already quite drunk after most of the bottle of wine, and getting more and more horny over what I was doing to him. After a bit I took my bra off, down my sleeve so he wouldn’t get a peep, and told him to put it on. He did it, shaking harder than ever.
With my bra on he looked so comic I made him put my shoes on too and walk around the flat like that, then my skirt, then everything else, so he was dressed up like I’d been at work. He really did look feminine, sort of, if not actually like a woman, and I had great fun making him go around the flat like that, just enjoying myself nicely while he was getting in a bigger and bigger state.
In the end I took pity on him, told him to lie on the floor and mounted him with his skirt turned up and his cock pulled out of my pink knickers to go in me. It felt weird, to be stark naked on top of him while he was dressed in my clothes, but it felt good too. Not that I get off on having a man in women’s clothes, but to have all that power was a real kick. He stayed in my knickers and bra all night, and I have never had a man so grateful or so constantly turned on.
That night was the real start of my relationship with Dog Boy. I’m not claiming he’s perfect, but it’s the best I’ve ever had. We can talk, for one thing, because there are no barriers between us and if I’m not into cross-dressing in that it doesn’t turn me on, then I do get off on the change of roles and having all the power in the relationship. Sex has always been about exchanging favours anyway, or a lot of it, so I’m more than happy to indulge his fetish in return for having him as my plaything.
He loves me to boss him too, to do my housework and have me swat his bottom if he doesn’t make a good job of it, or anything that makes him feel feminine. OK, so his idea of ‘feminine’ is straight out of the 50s and would make any modern feminist foam at the mouth, but what do I care? He’s the one scrubbing the floor dressed in frilly knickers and a tarty mini-skirt.
It didn’t take long for me to bring up my kink for watching men go together. He admitted he would do it, after a bit, but insisted, and still insists, that it’s not because he’s into other men, but because having me order him to do it is so humiliating. That night I made him masturbate while I told him how I’d like to watch him go down on a gay man and take a mouthful of spunk, which made Dog Boy come so hard it went in his face.
Just thinking about it kept us going for a while, but I wanted more and when he saw that it was what I wanted he made it very clear that he was willing. My first thought was to take him to a gay club and make him do it in the loos, but I wasn’t sure how the gay men would react to a woman. We started to scan the web for possibilities and came up with several, but one was far and away the most satisfying. I didn’t want him to suck off a gay man or even a bisexual man. I wanted him to suck off a 100 per cent straight, macho shithead of exactly the sort I’d been out with so many times, and I wanted the guy to think he was getting it from a girl.
Dog Boy was completely freaked out at first, but he had to admit it was possible. With his small size, slim build and years of practice pretending to be a woman he was pretty good at it, certainly good enough to pass as the real thing in a dim light.
We had great fun practising. First off we got some new outfits, because all the stuff he had for himself was frilly or pink and generally the sort of stuff no real woman would be seen dead in. It was great making him buy bras and panties in lingerie departments, and even better having him try on a skirt in a changing cubicle with me, which got him so hard I made him toss off in his knickers and wear them home all wet and sticky.
Training him to behave like a woman was even better, first taking him out at night and then in the c
ar, always a long way from either of our areas. At first he got noticed quite a lot, with odd looks from both men and women, but nobody ever challenged him. He was better than me at make-up from the start. More practice, then once we’d got his hair right and he’d learnt to speak more softly, the odd looks became rarer and finally stopped altogether.
By then I knew exactly what I was going to do. While searching the net we’d found out about dogging carparks, and how you generally get loads of men for every couple, really. That was perfect: after dark, with a guaranteed supply of horny men and a quick getaway if things went wrong. I even thought of swapping roles completely and having me as the boyfriend getting off on making his girl suck strangers’ cocks, but I couldn’t swing it and decided to be a butch dyke with a bi girlfriend instead.
I went a bit over the top, maybe, because, let’s face it, I haven’t the least idea what the well-dressed butch dyke is wearing this year, but I was banking on the men in the car park not knowing either, or not caring. I felt good anyway, in men’s work boots, ripped jeans, a black top without a bra, a leather jacket and my hair up underneath a cap.
Dog Boy wanted to call himself Letitia, but I was sure it would make them suspicious and made him go for Emma instead. I also had trouble getting him to leave the flouncy stuff and go for a short PVC skirt, stockings and heels, with a black top and a pink plastic jacket that was pretty hideous but had the big advantage of hiding the major defect: no tits. He, or she, looked a right tart, but that was the idea.
Our first outing was a failure. Nobody turned up, but before the second I’d read that the best thing to do was to advertise on the net in advance so plenty of men knew we’d be there, and the second time it worked a treat. We parked up carefully, facing the exit so that if there was any trouble we could make a quick getaway, and close to some thick bushes so Dog Boy’s face wouldn’t be too easy to see.
I flashed the lights as you’re supposed to do to signal that you’re up for fun and we waited. I was pretty nervous and he was shaking as badly as when I’d found my knickers in his room. We almost lost our nerve when a man stepped out of the shadows: a black guy, quite young and really furtive. I did the talking, and it was one of the weirdest conversations I’ve ever had as I explained that I was deliberately punishing my girlfriend by making her suck strangers off. He just loved that, the bastard, and out it came, a fat black cock, already half stiff, which he flopped out at the back window.
I could just about see Dog Boy’s made-up face looking right at that big black penis, his mouth a bit open, knowing he wanted to suck it but unable to make himself move. I did it for him, taking him by the neck and shoving his face right against the man’s cock. It felt wonderful, and if that makes me a sadistic bitch then I’m just going to have to accept it, but it wasn’t half as wonderful as seeing Dog Boy’s mouth come properly open and take in the man’s cock.
I could have come right there, just from the expression on Dog Boy’s face as he sucked on another man’s penis, loving and hating it at the same time. The man was great too, well into it and never once suspecting it wasn’t a real woman sucking him off. He even started to call Dog Boy a bitch, just before he came right down the poor bastard’s throat. Dog Boy was nearly sick, but I’ve had enough men make me swallow not to be too sympathetic, while knowing he’d just swallowed spunk got me off almost as much as seeing him suck cock.
That was it, the first time. There were other men about, but Dog Boy bottled out. I didn’t mind, because I badly needed sex but wasn’t about to do myself in the car with a load of men in the bushes. Back at my flat I made him describe how it had felt to suck another man all the way, while I lay back on the bed with my vibrator. It was just the best orgasm.
Since then we’ve been out three times, and every single time Dog Boy has sucked at least one man, and always until they come. We always choose dark places, and never once has anyone been suspicious, even when Dog Boy’s had to refuse to lift his top. On the best night he did four men, one after another. It was so dark we could hardly see anything, just the outlines of the bushes against the sky, and the men, one after another, coming forward to flop out their cocks, right into poor Dog Boy’s mouth, to make him suck them until they spunked up, and never once suspecting he wasn’t a girl.
One man gave him bukkake, pulling his cock out at the last moment and doing it in Dog Boy’s face to leave his make-up running in the streaks of spunk. That was so good I just had to come, so we drove a little further, to be alone, where I could turn on the car light and bring myself off while I watched Dog Boy wank with the man’s spunk still trickling down his face and his mouth full of it. He was so high he looked like he was on drugs or something, and at the last moment he put his hand in the mess and smeared the other man’s spunk all over his cock, adding his own as he came all over his hand.
That made me come so hard, and I was so turned on I didn’t know what to think about – the state my boyfriend was in as he wanked in another man’s spunk, watching him suck the men, or because they all thought they’d had blow jobs from a girl when really they’d been sucked off by a man.
Yes, I know it’s wicked. I know I’m an evil bitch, but I don’t care. I love it.
So were you one of them? Did you go out to a certain car park not so very long ago and get a blow job from a bi girl with her dyke partner? If you did, it was us, and you’ve let another man suck your cock. Now I’m going to go away and come over it.
– G. H., Warwickshire, UK
Angelo’s
‘I’m so excited! Thanks so much for giving me the time off! I’m going to Europe!’ I gushed, while bouncing about with the vigour of a five year old.
‘If you keep bouncing around like that, I’m going to get excited.’ He snickered in a way that made me a little uncomfortable.
I had been working for Angelo for about a year. When I applied for the job at his family restaurant, it was only meant to be a temporary fix, but he and his family were so kind and accommodating that I had never had the heart to leave.
‘I guess I’ll finish setting these tables and then I’ll get going,’ I said, leaning across the table with a plate.
‘That’s fine. I better get something nice for letting you go on vacation with such short notice,’ he said in his thick Italian accent, his face a bit more serious than I had expected.
‘I’ll bring you a bottle of the best wine ever!’ I smiled, grateful to be leaving for my holiday.
‘There are things that are a lot better than wine . . . maybe something else?’ His tone once again was making me uneasy.
‘Ha ha,’ I joked sarcastically, knowing full well what he was implying and afraid of giving him anything else to go on.
I wasn’t sure what had gotten into him. I knew he was a bit of a womaniser and had been involved with women outside of his marriage in the past, but he had never spoken to me that way. We always had more of a father-daughter type relationship, or so I thought.
He was in his mid-50s, and certainly not much to look at, especially in the eyes of a 20 year old. Angelo dressed very much the part of the wannabe suave European male. He wore overpriced colourful sweaters, and dress slacks, and way too much cologne. He was not very tall – I’d guess only a couple of inches taller than me – his hair was thinning and almost non-existent, but he managed to grow what little he had long enough to pull it into a tiny little ponytail at the nape of his neck. And then there was the goatee; it seemed he had more hair on his face than on his head.
‘Are you gonna give me a hug?’ he asked, opening his arms for me as I got ready to walk out the door.
‘I’m only going for a week.’ I tried to avoid the looming embrace.
‘Come here.’ His eyes opened wide as he wrapped his arms around me, holding me uncomfortably tight.
‘You have a good time,’ he snarled into my ear, his hands rubbing my back and inching their way lower.
‘Thanks. I will. Bye!’ I called out, pulling away and booting it towards the d
oor, hoping that his newly found interest would pass before I got back.
My week in Europe was great and I quickly forgot about Angelo’s odd behaviour. I was back at work the night after I returned from my trip. Tired and jet-lagged and very glad to have returned on a slow night, I managed to sit for a few minutes and enjoy a cup of coffee with Rosanna, my boss’s wife. She was a heavy-set woman with a warm smile who loved to chat and bake. ‘Take a cookie, they’re fresh.’ She smiled, practically shoving the cookie down my throat. ‘So, your trip was nice?’ she asked.
‘So good! I really needed it,’ I said, collapsing back into my chair.
‘Really needed it, eh?’ I heard Angelo’s voice. He had just walked in to take over for Rosanna, who clearly didn’t catch what he meant.
‘Hi, sweetie, it’s nice to have you back.’ His tone changed to one that was more appropriate.
‘Thanks. Oh, those customers look like they’re ready to go, I’ll be back,’ I said, dashing off. When I went around the back of the bar again, Angelo was just standing there with a grin on his face.
‘Where’s Rosanna? Did she go home already?’ I asked as I pottered around the bar looking for a corkscrew.
‘No, she’s in the back getting changed.’ I heard his voice getting closer behind me.
As I went to turn around, I felt his hands press against my hips, holding me there, unable to move. Before I could say anything, I felt his body press against me and a hand run along the back of my thigh, just under my skirt.