It all started when... By MG comments welcome to crashmatt@gmail.com
It all started when... well, perhaps that's not a great way to start. It's difficult to say exactly when it started, or perhaps even what "it" is. For the purposes of this story "it" relates to an episode at Halloween, yes I know, another Halloween story. But, you see, in the UK Halloween isn't the event that it is in the USA, and crossdressing for Halloween is certainly not a popular choice. So you could say it all started when my work friend, Kerry, suggested that a few of us go to a fancy dress Halloween party. Or, you could say it started many years before that when I first tried on my sister's underwear and had a hard on you could cut glass with. Either way, this starts out as a true story, you can decide for yourself at what point it becomes fantasy.
"We should go in fancy dress!" said Kerry.
"I'll be a zombie" said Amy.
"I could go as a witch" I blurted out, before I could stop myself.
"Yeah! That would be great" Kerry enthused.
"Wicked, you totally should!" said Amy.
I had been dressing in women's clothes for years. I was in my early thirties, and I had a fair collection of women's underwear. But no outer clothes. I'd been to a crossdressing fetish club before, which was pretty awesome, being able to just wander about in lingerie all night... mostly with a hard on! But this would be different, I would going out in women's clothes surrounded by normal people. I had a look online and found a Hell Bunny Kitty Dress, that I thought would be perfect. So I showed the picture to Kerry and Amy, still rather testing the waters... they thought it was just fun dressing up and I didn?t want them to know I was a crossdresser. They both thought it was perfect. So I ordered it.
It arrived, and I went to try it on. I put on a corset, to give me some shape, and attached some stockings to the suspender straps. By this time I was hard as a rock, but I ignored my cock pulling some dark red knickers up my legs and over my throbbing cock. I slipped the dress over my head, and after some gymnastics, I managed to get the back of the dress zipped up.
I looked in the mirror. From the chest down, I looked pretty good. But I wasn't confident enough to go out like this, without some reassurance. So I took a couple of photos. The next day I showed them to Amy and Kerry, "You look great" and "Wow, that's fantastic!" were the responses. So I started looking for the rest of the outfit. I found some costume stuff, Witch's hat, broom, long ginger wig etc. I even found some stockings with a skull pattern on them. I told Kerry that I'd got everything, but that I wasn't too confident about going out dress up... she suggested that she come round and I have a dress rehearsal.
A few days later we went back to my place from work and Kerry stayed downstairs, whilst I got dressed upstairs. When I came down, Kerry was thrilled, and came over to get a closer look, "are you wearing a corset?" she asked.
"Yes" I replied, rather nervously.
"This is more than just fancy dress, isn't it?"
"Yes"
She gave me a big hug, and asked me all about it. I told her everything, how long I'd been doing it, that it was a sexual thing, that I was bisexual and had been with men while dressed up. She was so accepting and supportive. I felt completely ready to go out.
A few days before the party, I booked in for a waxing. I didn?t want to be showing off a hairy chest in my dress, but also I wanted to be smooth all over. I was a bit nervous about the waxing but it went fine, and wasn?t all that painful, sort of soothing after a while. When he started working around my cock, I got hard, but he just carried on, told me not to worry, as it was easier to wax the shaft when it was erect. After all the hair was gone he began to moisturise my skin, all over, leaving my crotch till last. Unsurprisingly, I got hard again! After he'd been running his hands, well covered by moisturiser, all over my hard cock for several minutes he spoke.
"I should probably stop doing this," he said, looking me in the eye. "It's probably a bit unprofessional" he paused "unless you don?t mind?" he added. I wasn't too sure what to say! I didn't mind him doing it, it was very nice, but it was a bit unexpected, so I just mumbled "that's ok, thanks", meaning, "that's ok, thanks, you can stop now". But he took it as "that's ok, thanks for doing it, carry on."
So he began running his other hand over my balls, and perineum, and I found myself parting my legs to give him access. His grip tightened a little and his rhythm increase a little, as his finger tip found my asshole, I moaned aloud, his finger just pushed in a tiny bit as his hand quickened, I groaned, pushed my head back and released an enormous spurt of cum. It splattered all over my chest and face.
After giving me time to come down, he took some tissue and wiped me clean, then left the room to allow me to dress. I got dressed in the clothes I'd brought with me, which included a matching bra, knicker and suspender belt, with lace top stockings. Just looking at myself in my lingerie, all smooth and bare, was enough to give me another hard on - which I covered up with jeans and a baggy hoody.
So after that unexpected encounter I went home and began to get everything ready for the party. I laid everything out on the spare bed, ready for Saturday night. There was the black dress, ginger wig, witches hat and mini broomstick, a pair of black ankle boots and the lingerie. Oh, the lingerie... A black corset, with lace trim, and suspender straps. A pair of matching satin and lace panties, and a pair of stockings with a skull and crossbones motif. I was hard just looking at the lingerie, leaking precum into my panties!
I held back from playing with myself, and got dressed up. I was very nervous about going out dressed, but as we were going to a fancy dress party, I thought it would be ok. Whilst I was still very turned on, and had rather damp knickers, my hard on had gone down due to the nerves. So shortly after I was ready, the girls arrived, with Amy's boyfriend, Ben, driving us there and Kerry's boyfriend, Chris, with us too. Amy and Kerry did my make-up, lips, eyes, blush, nails... all looking fabulous! Then it was time for the party... we arrived at the pub, and it was clear very quickly after we walked in that we were the only ones in fancy dress! Turned out that there was a kids fancy dress party earlier in the day!
Still we were there, there was a band, and there was alcohol... So there was drinking, laughter and fun! We were there for a few hours and got a bit drunk!
The fun really started when we got back to Amy and Ben's house...
We took a taxi back, and had more booze, chatting about all sorts of things. Ben fell asleep on the sofa, Kerry was half asleep cuddling Chris, and Amy and I were chatting about our scars. We were talking about our appendectomies, Amy pulled down her skirt waistband and showed her scar, without thinking, I lifted the skirt of my dress up to show mine. Amy got a good look at my suspenders, stockings and knickers!
"Check you out!" she exclaimed, "look at all these sexy undies!"
I just blushed a bit, and responded "I'm not the only one, look at yours" pointing with one hand towards the top of her lacy knickers visible about her lowered skirt.
She reached out and twanged one of my suspender straps, "Mmmm" I groaned.
"I want to see all of this!" she said, reaching behind me to unzip my dress.
I was soon stood there in my corset, stockings, heels and knickers. Something of a fantasy come true! She snapped one of the straps over my ass, again making me moan!
"Your turn" I mumbled, as she moved round in front of me again. She raised her eyebrow, "come on", I said "you can show me your underwear now."
She gave me a wicked little smile, and quick as a flash her shirt came off and her skirt was round her ankles. A very nice simple black lace bra and knicker set, with lace top hold up stockings. "You've been enjoying yourself tonight, haven't you?" she asked, "your knickers are soaked!"
She reached out and cupped my cock and balls, the dampness was obvious, and my cock very quickly grew to full hardness. "You like dressing up, don't you?"
I nodded.
"You've done this before, haven't you?" she asked. I hesitated, she squeezed my shaft harder, "Haven't you?"
I nodded.
"Are you a sissy?" she asked
I nodded.
"Damn, that turns me on. I'm so wet now. Here, feel." She took my hand, and pushed it between her legs. Her knickers were absolutely soaked.
"Do you like cock?"
"Yes. I like both. I mean, if I'm dressed up I like cock. But I've always fantasised about being with a girl when I'm dressed up too."
"Fuck. I'm so hot right now." Amy looked over at the sofa, and saw Ben was still sleeping. "Your tongue is going to do some work! Kneel down."
I complied eagerly. She walked over and put her pussy right against my face. I opened my mouth and pressed my tongue against her knicker covered pussy. I reached my hands behind her and cupped her ass, pulling her pussy on to my mouth. I sucked her juices through her knickers before hooking my fingers into the waistband and pulling them down. Then I swiped my tongue up her pussy lips, making her groan out loud. Her hand were on my head, her fingers twining into my long ginger wig hair. I dipped my tongue in to her pussy, licking up towards her clit, eliciting another loud moan.
Her knees started to shake, so she knelt down and lay out in front of me. I moved forwards, on knees and lowered my mouth towards her pussy again. As I move my head down, I glanced across at the sofa. Ben and Kerry were still asleep, but Chris was awake and was rubbing his crotch, I flashed him a quick smile.
I set to work again, long licks up each lip, between the lips, towards the clit. Circle the clit, flick with the tip of my tongue. Her breathing was becoming more and more laboured, she was squirming round more and more. We both knew where this was heading?
As I was really getting in to licking her, I felt a hand rubbing my ass. I was a bit startled, but guessed it had to be Chris. I wiggled in what I hoped was an encouraging way, and was rewarded by more strokes and a second hand massaging my ass. I moaned in to Amy's pussy, gaining a long drawn out moan from her. I looked up and she was watching something behind me, from the movements I could feel, I realised Chris was getting in to position behind me. Felt my knickers being slid down my legs, over my stockings and down to my knees. I lifted my knees off the floor for a second or two, and they were off. My ass cheeks were parted and a tongue started to lick at my asshole. Now I really did moan long and hard. Amy pulled a little at my head, regaining my attention and reminding me that I was supposed to be looking after her.
So whilst a big wet tongue was pushing in to my asshole, I resumed work on Amy's pussy. I looped my arms under Amy's legs and pulled her pussy firmly against my mouth. I ran my hands over her firm belly and over her boobs. I lifted her bra over those delicious little pretty titties, stroking their smooth surface, gently stimulating her nipples. Whilst I was busy licking, the tongue was removed, and a finger started to press at my asshole. I started licking harder and faster. Amy was really wriggling about, breathing hard, I pinched her nipples and flicked at her clit with my tongue. Her hands clamped my head in place, and her thighs squeezed my head tightly. Her hips bucked her pussy in to my face and she let out a series of loud moans and grunts before pushing my head away from her pussy.
After a couple of minutes, she wriggled away and propped herself up against an easy chair. With a large smile on her face she said "Fuck that was good. Ben won't lick me, and you really know how to use your tongue!"
I was panting and moaning quietly, as there were now two fingers in my ass. I wasn't a virgin, but I hadn't done much of this. Only twice before.
"Shit, this is so hot" said Amy, watching Chris fingering me. My cock was rock hard and there was precum dripping on the floor. "Chris, use the oil in the kitchen" Amy suggested. Chris removed his fingers, and moved quickly to the kitchen, coming back with a bottle of olive oil. There was a pause, then I could feel the oil dripping all over my asshole. The fingers were quickly reinserted, making me moan with pleasure. A third finger joined in.
"Here, let me help" came an unexpected voice. It was Kerry, she must have woken up at some point, without us noticing.
She came over and took the oil bottle from Chris, and started to oil up his cock. She didn't seem bothered at what we were doing, which was a relief. It didn't take long before his cock was well lubed, Kerry brought his cock to my asshole, lined us up, and whispered "Fuck him."
Chris pushed slowly into my ass. I could feel my ass opening as his cock pushed in. I was stretching around his girth, opening up around him. His cock felt so amazing inside me. He slowly kept pushing, and before long I could feel his pubes against my skin. My cock was throbbing hard!
Kerry moved round next to Amy, taking the oil with her. The two girls had often flirted and played around, jokingly touching each other up. They'd called themselves "upstairs lesbians" before, both liking boobs, but apparently not being interested below the belt. Kerry took the oil, and poured it on to Amy's chest, whilst reaching behind to undo her bra. She rubbed the oil over Amy's boobs, and Amy quickly began to remove Kerry's clothes, to return the favour. Before long, they were both mostly naked and covered in oil. They were rubbing over one another, playing with each other's breasts, and there was definitely some rubbing of pussy against leg. I wondered how long the "upstairs" part was going to stay in force!
It was a bit difficult to concentrate, with a nice hard cock pushing in and out of my ass! I was focusing more on the feeling of his cock rubbing against my prostate and sliding in and out of my asshole!
"What the fuck!" was the surprising cry from the sofa! I guessed that Ben had just woken up. Chris didn't stop pistoning my ass, the girls didn't stop rubbing at one another, so Ben was just left sitting there wondering what the hell had been going on!
"Dude. Just join in!" Was Chris' advice. I looked up at Ben, mouth open and gasping as the cock in my ass continued to pound me. Ben was staring at me, I licked my lips, and before long his trousers were round his ankles and he was knelt before me with his cock pointed right at my mouth.
Out of the corner of my eye, I could see that both girls had a hand in the other girls' pussy. Clearly, downstairs was now on the cards! They were kissing passionately, and vigorously fingering each other. I didn't think it would be long before there were more orgasms...
I was distracted from thinking much more about this, as a thick hard cock was introduced to my mouth. We both moaned as his cock was engulfed by my mouth. His hands either side of my head as he set a steady rhythm gently fucking my face. Chris was uping the pace in my ass, and cock was swelling up, hard as anything.
I tried to make eye contact with Ben, but he was looking elsewhere... from the look on his face I was pretty sure he was engrossed in the view of the two girls. I went to town on his cock, I really wanted his cum. I sucked, I used my tongue, I used one hand to massage his balls, and before long the combined stimulation was too much for him. He was groaning and panting, Fucking my face faster. And faster. And faster. Then he stopped, his cock swelled up, and then it came out, shot after shot of hot cum. He filled my mouth and I had to swallow fast to keep up with the torrent of cum. I kept sucking until he was soft and pulled out of my mouth.
I was so turned on and so ready to cum. I started to clench and release my ass muscles around Chris' cock. He started to fuck me harder and faster. He was banging on my prostate. I was milking his cock. He was grunting now. Banging my ass really hard, giving me a really good hard fuck. Then his cock swelled up even more, he groaned, and began filling my ass with cum. Feeling that cum shoot up his cock and it to me was what it took to push me over the edge. I shuddered, moaned and began to cum. So much cum poured out of me. I'd been on edge and stimulated all evening, plus a really good long fuck, I was shooting gallons and gallons of cum out, as I felt Chris' cum shooting in to me, and I could still taste Ben's cum in my mouth. It was amazing.
After a minute or so Chris removed his softening cock. Soon after I could feel his cum running out of my ass and down my legs and stockings. I looked over at the girls, they had clearly satisfied themselves.
We slowly recovered our wits, Amy and Ben sat together on the sofa; Chris and Kerry started to get dressed again. I pulled on my dress, and Amy got up to zip me back up. I bent to pick up my knickers, and Amy took them from me. "Nope" Amy said with a smile "I'm keeping these as a souvenir!"
I smiled a goofy smile, as she handed me hers "You get to keep these."
She reached up under my dress and gave my cock a gentle squeeze "Maybe next time I can have some of this as well as your tongue" she whispered in my ear.
I rapidly got hard again, thinking about next time, and with Amy's hand on my cock. She span my round, lifted my dress and gave me a hard spank on the ass! That made my cock swell again, apparently, I like spanking! That's a new one to try!
Anyway, it was time for me to go home, slightly drunk and well fucked. My cock was still hard and throbbing, but the big skirt and petticoat hid that, so I was ok. I walked out the door leaving Ben and Amy to head to bed, Ben had an obvious hard on, and Amy was rubbing her boobs, so I think I know what was happening next in that house! Kerry and Chris wasted no time jumping in a cab, and were kissing passionately as they drove off.
I took a slow walk home, in my heels and stockings, cum slowly running down my legs, thinking about the night we had just experienced. And looking forward to the next time!