Even although my girlfriend was to be working away from home during the summer I was really looking forward to my long break from college. Clare had been offered a summer job in Canada - I would entertain my cross-dressing fantasies while she was away. And that was just how things went until in walked Clare's dad on me, while I was dressed only in lingerie, wanking off to some television programme.
Clare's dad, Austin, was collecting a few more clothes and belongings to take out to Clare, whom he and his wife were about to visit. The apartment Clare and I shared was owned by her parents, Austin hadn't thought I was in after knocking only for me to not to hear him.. Nothing more was said other than a "we all do stupid things" type pat on the shoulder.
A week later I got a call from Austin asking if he could drop off some of the belongings Clare hadn't wanted with her. So he came around that evening. Austin had work commitments so had to come home, although his wife was going to spend some time with Clare. Late that afternoon Austin brought in the items including a present from Clare and a large box - he said what was within the large box was to say sorry for intruding on me, he also reassured me that he would never say anything about my cross-dressing desires.
I was intrigued by the box and carefully opened it - inside were smaller parcels - as soon as I picked up the first parcel I could see why Austin was being understanding - "Apres Noir- Lingerie for Men". Austin must have spent a fortune, the parcels were full of knickers, chemises, stockings, cami-tops, slips and more - so much silky satin I could hardly wait to try something on. Austin smiled as he watched me then said he'd open some wine if I wanted to get changed.
I took the box to the bedroom and picked out a few things and quickly stripped. I first pulled on a soft pair of lace trimmed knickers, my semi-hard cock felt so good against them, I admired myself in the mirror for a few seconds, then the matching camisole top, it was so light against my skin it was as if I was still naked. Then the suspender belt, and finally the stockings. I put on my dressing gown and went to see Austin - I opened the dressing gown and he smiled "you look better than I'd imagined" he stated.
I took off the dressing gown and we sat together drink wine, talking as if this was so normal. I felt relaxed with Austin even though I barely knew him, I ran a hand over my satin clad body as we spoke - Austin laughed lightly and said "You have no idea what that is doing to me" - by the bulge in his trousers I thought I had some idea at least "Want to feel how good it feels?" I asked back. At that Austin put his glass down and took mine from me too.
At Austin's request I lay back a little on the sofa, I felt vulnerable and a little afraid, I'd often thought of this moment, but in my thoughts the man with me was faceless, now here was my girlfriend's dad beginning to caress me. He ran a hand over my silky chest, then down the side of my body, down my legs, and back to my stiff cock beneath the knickers. He took hold of my cock through the silk and squeezed me before starting to wank me. I was just so highly aroused that I knew it wasn't going to take much to get me off. I lay back further, spread my legs more, felt my own body as Austin wanked me with one hand and caressed my ass with the other. I put a hand between my legs, playing with my balls, delighting in this moment, suddenly I shuddered and came, soaking the new knickers - I came so much I thought for a second I'd pissed myself in the excitement. My cock was still firm, but empty now, as Austin bent his head towards my knickers and took the head of my cock in his mouth, through the knickers and tasted my cum.
He didn't linger long with this, instead he sat up, pulled his cock from his trousers, knelt between my legs, and looked at me as he furiously wanked himself at the sight of me sprawled out in lingerie. It didn't take him long to shoot all over me.
When order was restored Austin told me that had been one of his fantasies come true, "One of?" I questioned. "I didn't buy all that lingerie just for 3 minutes of fun!" he responded. The rest of the evening we spent talking & dressing me up in the new lingerie, and pouring over the gorgeous models and clothes in a catalogue - we chose what we each wanted and Austin phoned up and put it on his credit card there and then.
As the late evening closed in Austin said he'd have to go home - I pointed out how much wine we'd drunk and that he could spend the night here. We both realised what this meant, after what we'd shared tonight neither of us would be sleeping alone. Another bottle of wine was opened and I said I was going to get ready for my bed.
Getting ready for bed meant I could try on a new night dress, a long full length chemise was spotted and I slipped into that and changed into a fresh pair of undies that cupped my cock and balls wonderfully. I began to re-apply perfume and lipstick as the door opened. "I fancy an early night" Austin said clutching two full wine glasses. It was only then I felt a slight chill of fear - sleeping with another man, my girlfriend's dad, in my girlfriend's bed " we don't have to do anything" Austin stated almost reading my mind. By "anything" I think he meant nothing more than cuddle, I smiled back.
Austin borrowed my dressing gown and got ready for bed in the bathroom as I slipped under the covers. Shortly he was back in the bedroom, and under the covers with me. As I suspected, Austin wasn't able to keep his hands off me for long, stroking my shoulder and waist, enjoying the feel of my warm firm body beneath the nightdress. I enjoyed this too, being made to feel like a woman, and it was far more special than my fantasies had ever felt.
By now my ass was being lovingly caressed , my cock rock hard, my eyes fixed on Austin's face - his eyes fixed on my flat chemise clad chest.. I began to stroke his ass through his boxer shorts and then moved my hand over his cock. Austin responded by doing the same to me, but then cupping my cock and balls and squeezing them softly. I groaned. Austin cried "Shit, I can't take much more of this" and through the covers right off the bed.
Austin moved down the bed, pushed me flat on my back, pushed my nightdress up around my waist and pulled my knickers down just enough for my cock to pop out. It was all done in a second or two, but it felt like slow motion as Austin closed his mouth around my cock and began sucking and licking my cock. For a second I thought of Clare blowing me - but then she never did - so I pretended I was Clare being licked out by her dad - I almost exploded at that thought. Austin was slurping away on my throbbing cock, he grunted and snorted as he took as much as he could in his mouth, and then he began to finger my anus. I bit on a finger and writhed in joy, thrusting my cock further into Austin's mouth, he shoved a finger into my ass and used his other hand to wank me off as he sucked. Soon enough my cock was twitching and I was ready to cum, I called out to Austin who took his lips from my shaft and sat back and watched as I shot my load into the air.
We both panted as Austin crawled up the bed again, I felt his hard cock brush against me, I figured if he did me, I had to do him. So as Austin collapsed beside me I slid down to his crotch and pulled his boxer shorts down. I was glad to see Austin had a decent cock, similar to the one I saw in fantasies, only he was hairier down there. Cock-sucking wasn't high in my fantasies so I went in slowly and began to tongue his head, the feel was good, he was wet already and the taste didn't put me off. I then closed my mouth around his shaft and began to enjoy exploring Austin's cock with my tongue, lips and teeth.
As I bobbed up and down on Austin he began to stroke my shoulders and back, then I heard him soft say "Clare, baby!". Fuck, here was I giving Clare's dad a blow job and he's pretending I'm Clare. This drove me wild, I again pretended to be Clare, and coo-ed "Oh dad" as I sucked, Austin called out "Clare" louder this time and began swearing, I was driving him nuts. I could feel my cock getting really tense again, so soon after cuming before, I then really began to wank Austin hard until he came too.
We lay together, cuddling, sipping our wine - "one of" Austin's other fantasies had come out. Austin told me he didn't want to fuck his daughter, he knew it would never happen, besides his real fantasy was for boys in dresses and lingerie - and that way he said he could create a daughter who would do all the things a man wanted. So that was that, when I dressed up I was to be Clare, to be whatever Austin wanted - his daughter, or the girl next door, a bride or a dirty little whore. Summer loving!
Austin slipped out early in the morning, but true to his parting words he phoned me later. He couldn't come back that day, but would call round the next again day. I had one full day to pleasure myself, really explore all this lingerie and Clare's wardrobe. Included in the box of lingerie I was delighted to see a small make-up set and really surprised to see a wig - the same colour of hair as my girlfriend had- her father, that dirty devil! The next again day, a Friday, the catalogue order arrived - sheer heaven - let the games commence. I went out to stock up on wine and food for I knew Austin would be having a busy weekend.
In the late afternoon I got ready for Austin's visit. One of Austin's choice's from the catalogue was a black skirt suit with a short, pleated skirt - I figured this was the office-girl fantasy so after his week at work he might appreciated it. On Austin's arrival I opened some wine and we relaxed on the sofa. Like the dutiful wife/daughter I asked how his day at work had been. Of course he didn't bore me with details, so I asked him if there was any girls at work he wanted to have. He told me of a few, but told me a few years ago was the best time - he had overheard these younger guys talking about a summer intern, what they'd like to do with her and so on - the summer intern had been Clare.
I instantly grew hard and moved to try to prevent my cock from ruining the lie of my skirt, but Austin didn't care. He got up and moved to the chair opposite where I sat, he told me to touch myself. I happily obliged, he played the voyeur, watching me as I stroked my stocking clad legs, parted my legs slightly to allow him to look up my skirt, at my black panties. I rubbed the area between my balls and my anus through the silk, with my other hand I began to feel my chest through the satin blouse I had on, I closed my eyes, raised my legs a little and pulled at my cock in my panties.
I wanked myself slowly, loving the feel as my cock slipped back and forth in the soft material. I opened my eyes as Austin moved between my legs, he didn't touch me, not until I came , thrusting my cock hard against the front of my panties, soaking them. Austin loved this, as he had done before and as he would do many times over the summer, he bent his head in and sucked my cock through the cum covered silks. With Austin between my legs, sucking on my panties and softening cock , my mind filled with dirty thoughts of him licking Clare out, and doubtless I was not alone in these thoughts. When he had is fill of me Austin sat back and sipped his wine, and caressed my legs.
We needed to eat - Austin called for home delivery of Chinese and asked me to get changed into some evening wear, he hinted I tried the wig on. I did as he asked as he made a phone call to his holidaying wife. Keeping on the stockings and suspenders I dressed again in black underwear, this time the soft satin of french knickers and camisole top. A figure hugging red dress was included in the catalogue order, my choice, coming down to just below the knee, it felt as good as it looked in the picture. With make up and perfume added, I took the light brown coloured, long haired wig from it's cover. I pulled it on and looked hopefully at the mirror - I looked nothing like Clare, but I thought I looked good.
I'd taken longer than I'd thought to get ready, as I was surprised when the food arrived before I'd returned to Austin. Teetering in my black high heeled shoes I eventually showed myself off , almost falling as I turned. Austin appreciated the look I'd achieved. The food was all laid out, wine glasses filled, we began to eat. I tried to be feminine without being camp as we ate, talked and joked.
We had both finished our first dish of the meal when Austin turned his body to me and touched me. He studied me, watching his hand as he moved it over my lap, across my flat stomach and chest, and back down the side of my body. I admired myself and became aware that Austin was staring at my face. He softly spoke "Do you like spending time with your dad?", I smiled and said "Yes" as he touched my face and then he kissed me on the lips. I responded by opening my mouth a little as we kissed again, then "Woah!" I thought! I pushed Austin off and said "I'm sorry" and kicking off my shoes I rushed to the bedroom.
I wasn't gay, what was I doing, I fancied women, I liked dressing up as women, I didn't have any desires to be with a man, only my faceless fantasy man -or did I, maybe I did want this, I led Austin on certainly, I could have said no, but I wanted to please him. So many thoughts rushed across my mind. Austin opened the door "I brought your shoes back, Cinderella" he said in a tone that was understanding. He sat on the bed where I lay. He had his back to me and said he was sorry, he was confused. He kept his back to me and talked, told me of his confusion, his feelings, his desires - they all seemed to match mine.
"Dad," I said, in my Clare character, "hold me!". Austin slowly turned and lay behind me, wrapping his arms around me. He held me for a while, but I knew he couldn't keep his hands still for long and soon he was feeling my body all over again. I was enjoying this again, feeling him, without seeing him. Austin paid particular attention to my small ass, fondling it, squeezing it. Then I felt him lift my dress slowly, and drop it around my waist. His warm hands massaged my satin clad ass before he glided the knickers down to expose my ass. I rolled over so I was flat on my stomach and chest, Austin hung over me, feeling my back, my ass and my legs. Austin sat back and said "It's OK, I just want to get undressed" - this didn't bother me at all, I heard him strip and return to the bed beside me. My cock was rock hard, I was loving this, it felt like my fantasies now I couldn't see Austin's face, and it felt even more like it when my anus began to get a fingering.
I turned slightly to see the tube of moisturiser on the bed just as Austin picked it up, I wanted this so much now I had come this far. I moved to crouch on all-fours, exposing the crack of my ass to Austin as if to say "I want this too". Then the cold smear hit my ass, Austin fingered my anus lovingly as he applied the lotion, more and more was applied, I heard him sigh happily as he wanked some lotion onto his cock and then say "I love you so much Clare".
I braced myself, not fully knowing what to expect, Austin stretched my ass and pushed the tip of his cock against me, he fumbled for a second then his cock, steadied by a hand, began to push at my hole. I cringed, half wanting this, half wanting to be a million miles from there, the tip of his cock forced itself in, Austin grunted, I whimpered in panic, my eyes bulged with the fear of the unknown, Austin pushed a little further inside, I let out a low moan of complaint, the head of the cock was now right inside me, and suddenly Austin pushed in hard to my tight hole - I screamed and swore, this hurt so much, I wanted him out of me, Austin repeated "Sorry, sorry" but didn't move, he tried to re-assure me it would ease, I lay panting, almost crying as my ass throbbed away, I knew the trickle of liquid I felt was blood. I felt Austin move again, withdrawing his cock, but he then pushed back inside me again, more gently than before, but still enough to make me wince and swear again. Austin repeated this until eventually the burning pain at my hole was dulled as I relaxed a little more.
And then the real buggering began, Austin quickly pulled out, pushed in, and out again, then in-out-in-out - his hands rested on my waist, I buried my face in the bed, panted, moaned, groaned, my cock throbbed, my legs were like jelly, Austin went deep then almost right out, plunging my depth time and time again, the sensation was wonderful. He stroked my ass with one hand, he panted, huffed and puffed, swore. With his cock deep inside me he grabbed my shoulders and began to pump slowly and deliberately, "Oh Clare" he called out as his balls slapped into me time and time again, I eventually called out "Daddy" and Austin filled my ass with a shuddering climax - the warm sensation filling me ass was the last thing I knew as I passed out with Austin hanging over me.
Buggered- sodomised- fucked, I woke to find Austin fully dressed, soaking a patch on the bed where my blood had dripped, he had cradled my throbbing ass in a damp towel, I felt as if I had been hit by a bus. Austin brought my wine to me and said he'd leave me for a while, but that I should try to have a shower. I lay there, clothes all pulled and sweat stained, I closed my eyes and wanked off. I got undressed and went for a shower before dressing again, this time in my proper clothes.
I felt OK, I went back to the lounge where Austin was picking over some of the cold food. It was as if nothing had happened, I was glad, this is how I wanted it- "Clare" was Austin's lover not me, and my lover was the faceless man, not Austin.
I became Clare again that night and for most of the nights during the summer - after all Austin had spent enough money and bought enough lingerie to ensure at least 3 months of fun!
And maybe, just maybe, I'll dress up for you one day too.