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Debbie's Place

A crossdresser gets more than he bargained for
My girlfriend, Linda, was kicking me out of the apartment for the night because her sister, Sandra, was coming to stay. Linda didn’t want her parents to know that she and I were living in sin together. I found it all a bit far-fetched that a girl of 23 years old either couldn’t or wouldn’t tell her parents where to stick their beliefs. But, I knew well enough not to argue with Linda over such trivial matters. If I started complaining she would just go on and on talking until I was exhausted and eventually I would give up.

“You can stay at Debbie’s place." Said Linda, ”She’s away at the moment on some sort of business trip and I’m sure she won’t mind. I have the keys anyway so I can water her plants. You can do that while you’re there this evening.”

Debbie was about the same age as Linda, maybe a year younger. She was quite a hottie, tall, with lovely wavy blond hair, a cute face, ample boobs and a curvaceous body. I quite fancied her and had jerked off a few times to the thought of fucking her brains out. I especially enjoyed thinking of the time we had been at the pool together, seeing her in that teeny red bikini, and wanting to pull her into the locker room for a quick rogering. The only problem with Debbie was that she was a bitch.

“Are you sure you shouldn’t ask her first?” I asked.

“She’ll be fine with it,” Linda replied, “Now please make sure you’re out of here by 5pm because that’s when I need to go pick up Sandra from the train station.”

I looked at my watch and realized I only had a half an hour to pack an overnight bag. Linda had already hidden most of my belongings at the back of the large wardrobe. I grabbed a change of clothes, a few toiletries from the bathroom, and a book just in case I wanted to read, and then I went back into the living room to tell Linda that I was ready.

Linda went to the mantelpiece, opened a small box, took out Debbie’s keys and handed them to me.

“Don’t lose them, don’t make a mess, and don’t forget to water the plants,” Linda warned me, “I’ll call you tomorrow after I’ve taken Sandra back to the train station. It should be around 2pm.”

I felt a bit miffed about being bossed about like that, but it was par for the course. I’d learned to deal with it by pretending to ignore it, but it still bothered me. However, if I compared Linda to Debbie, Linda was an angel. I’d witnessed Debbie’s wrath on a few occasions, including one time where she’d screamed at her boyfriend and slapped his face so hard it left a mark for a couple of days. With me she was distant, as though I didn’t exist in her world. It was hard to reconcile such a sweet-looking girl with such a mean temper.


When I arrived at Debbie’s apartment, I rang the doorbell a few times just to make sure she wasn’t at home. If she was, I had already planned to tell her that I was coming for the plants, and then I would have gone to a nearby motel for the night. As it was, nobody answered the door, so I let myself in.

Debbie’s place was small but comfortable, with just one bedroom, a combined living and dining room, a kitchen and a bathroom.

I put my bag down and sat on the sofa, thinking about what I would do for the evening. I could have called a friend and gone out for a few beers and dinner, but I wasn’t really in the mood and I wasn’t hungry. I didn’t really want to watch TV or read my book either. In fact I knew what I wanted, but I felt anxious about it. I’d always felt anxious about it, and I had never explained it to Linda. She would no doubt have dumped me if she knew.

I grabbed the remote and turned on the TV. I don’t remember what was on or what I watched because my mind was elsewhere. I sat there staring absently at the screen while my thoughts played tricks on me. I told myself it was morally wrong, but another part of me told me that it’s not such a big deal, and that many men do it with their wives clothes; some wives even participate in the game. But this time it wasn’t my wife or girlfriend’s clothes. I wasn’t sure whether that made it worse or not.

The fact is I had become more or less comfortable with slipping into Linda’s lingerie while she was out. I would always take it out of the laundry hamper because then I knew she wouldn’t notice if it was crumpled or if I hadn’t folded it back the way it was before. I had also tried to wear a couple of her dresses, but they were too small.

Something about wearing female clothes gave me a sense of total happiness and horniness which inevitably led to me tugging my shaft until I came. Usually I would stand in front of the mirror, watching my cock poking out over the top of a pair of pretty little panties, imagining getting a blow job and feeling the hot steamy breath tickling my balls. Whose breath it was wasn’t always well-defined. Sometimes it was Linda, sometimes it was another girl I knew, and sometimes it was just a random girl I had seen and fancied.

I glanced at my watch and saw that it was only seven-thirty. I turned off the TV and sat there for a few minutes contemplating what to do next. As I said previously, I knew what I wanted. I would have been kidding myself to say anything else. As soon as Linda had suggested I stay at Debbie’s place, the possibility of access to Debbie’s clothes was ticking away in my head like a time-bomb. It was only a matter of time before the urge would get the better of me, and that time was right then. No amount of logic and reasoning could stop me now.


I crept into the bathroom like a burglar, for no good reason other than I was nervous, and looked around. There were loads of bottles, sprays and tubes on a shelf above the sink, along with a lot of other typically female paraphernalia such as a hairdryer and curlers. I noticed a couple of lipsticks next to the sink before turning my head toward the wicker laundry hamper sitting in the corner, brimming with Debbie’s washing.

My heart raced as I lifted out the contents, remembering the order in which to put them back. There was a pair of stockings on the top, then a bed sheet, and then a few panties and bras. Next I found a blouse and a lighter sweater, followed by a few more panties. I took a mental note of which panties I was going to try on, my cock starting to swell already. Toward the bottom of the basket I lifted out a pretty yellow sleeveless summer dress which I knew immediately would fit me, just by holding it up in front of me.

I took off my clothes in a hurry and slipped into a pair of silky light- blue panties with a white lace border. My cock was pounding so hard I had already left some pre-cum on the material. I then put on the matching light-blue bra and filled the pouches with a couple of balled up panties. Finally I slipped the summer dress over my head and struggled to pull up the zip at the back. The dress fitted nicely but I wasn’t used to fastening zips behind me. Finally I managed, realizing why women sometimes ask their partners for help.

I looked at myself in the mirror, and the familiar buzzing of happiness started. I saw the girl I wanted to be looking back at me. I felt pretty and contented, as though I was always supposed to be that way. I felt like the only thing separating me from a real girl was that I also happened to have a massive boner.

I reached out nervously and took one of the lipsticks, then the other. One was light orange and the other was dark red or maybe purple. I applied the dark one to my lips, helping to complete the picture. I stood there posing for a few minutes, swirling around as the hem of the dress lifted gently with the flow of air I was creating. I blew a few mock kisses and winked at my admirers. I liked to tease, and of course I was teasing myself at the same time, seeing the girl in the mirror air-kissing and winking back at me.

I was really getting into it, especially as it was the first time I had worn a dress that actually fitted, and despite the fact my cock was demanding attention I didn’t want the overall feeling to stop. I decided I would spend some time dressed as a girl, just relaxing and watching some TV.


“What the fuck!” Debbie yelled, making me sit bolt upright before I realized the situation.

Debbie was home and I had been asleep on her sofa wearing her dress, her underwear, and her lipstick. The bathroom was still littered with her washing. I was so busted that I couldn’t even speak, although I tried.

“Goddamnit!” Debbie continued in a very loud voice, putting her hands over her head and covering her eyes. She was walking round in circles, hunched over as though she had just heard the worst news possible. “Fuck, fuck, fuck, fuck, fuck.”

I sat frozen on the couch, contemplating making a dash for the bathroom, but my legs were like jelly and I wouldn’t have even been able to stand up, let alone run.

“Shit, shit, shit, shit, shit,” Debbie said in a quieter but still very audible tone, “What the fuck are you doing?”

She stared at me incredulously, her mouth slightly open. I had no idea what to answer, especially as what I was doing was quite obvious, given the fact she’d caught me doing it and was currently watching me still doing it. I thought an apology might be a good way to start defusing the situation, but I couldn’t get the words out.

“I knew there was something wrong with you,” Debbie asserted, “Does Linda know you’re a fag?”

Before I could even think about answering, Debbie kept on talking.

“I feel like putting you out on the street like that so you can go crawling home to Linda and explain yourself. What do you think she’d say if she knew you were dressing up in women’s clothes? I’ll bet you never told her about your sissy faggot ways. She says she likes you because you’re easy, and now we know why. It’s because you’re not a real man. You’re just a pathetic little loser who puts up with a woman pushing you around just so you can wear her clothes behind her back. Isn’t that what sissy fags do? I’ve read about your type. I bet you like other men sticking it up your ass too, don’t you?”

She walked away toward the bathroom. I sat there wondering what I could possibly do to get out of the mess I was in, and especially how I could keep Linda from learning about what happened. I thought about a profuse apology, perhaps some begging, and even money came to mind. I wondered how much it would take to pay her off, but before I could finish that thought, the tirade started again.

“Come in here!” Debbie yelled from the bathroom.

I managed to stand and wobbled my way to the bathroom. All I wanted by now was to get out of her clothes and back into mine. I felt deflated and humiliated.

“Pick them up and put them back in the basket.” She ordered, pointing at her stuff strewn all over the floor.

I hurriedly bent over and grabbed handfuls of clothing and pushed them back into the basket. Once I was done, I managed to ask her if I could get changed.

“No,” She answered solemnly, I haven’t decided what to do with you yet. Go into the living room.”


I went back to the living room and sat down on the couch. Debbie followed and sat down next to me. There was a heavy silence for several minutes, but it felt like hours. I was thinking about what she had said and the fact that she wasn’t far wrong on all counts. I had even gone as far as fantasizing about a guy doing me in the ass, although I had never actually tried.

I glanced over at Debbie. She was poker faced, not letting a single emotion show. I figured that she was probably beyond angry, and was planning what to do about the situation. I knew it wasn’t going to be good news when she finally opened her mouth, but she took me by surprise.

At first she started snorting in little bursts. Her lips quivered, and all of a sudden she burst out into the strangest laughter I have ever heard. I thought she might be having some sort of fit, but after a few seconds she calmed down a bit and started laughing more normally. I looked at her, trying to understand what was so funny.

“For fuck’s sake, smile!” She said, reaching out and poking me in the tit, or should I say poking her bunched up panties in her bra.

I watched her, not sure what to think at first. I was wondering if she was tricking me somehow. Then she poked her tongue out at me in a childish manner, making me smile.

“You think it’s funny?” I asked, quizzically.

“I think it’s fucking hilarious!” Debbie responded, “I come home and find my best friend’s boyfriend asleep on my couch dressed up like a doll. It doesn’t get much funnier than that.”

“But you were angry.” I continued.

“Of course I was angry, you idiot,” Debbie responded, “I wasn’t expecting to come home to that, although now I’ve seen it, it makes a whole lot of sense. Linda always told me you’re gentler than most men.”

“You won’t tell her, will you?” I asked.

“I won’t, but you should.” Debbie answered.

“She won’t like it. No woman would like it.” I sighed.

“Actually you’re wrong,” said Debbie, “Some women find it quite exciting to have a kinky partner.”

“I haven’t met any,” I went on, “Or at least as far as I know I haven’t.”

“You’re sitting in front of one.” Debbie whispered.

My heart thumped loudly. Debbie the bitch was into kink, and I was sitting next to her wearing her clothes. I had no idea what to say other than to ask her to reconfirm what she had just said.

“Really?” I asked.

She didn’t answer me, but instead got up and went back into the bathroom. I could hear her rummaging around for a minute or two and then she called me to join her.


“First of all you need more make up,” she said, “Your complexion is awful.”

Debbie sat me down on a stool and started to apply creams and powder to my face, followed by eye shadow, mascara and lipstick.

“What do you think?” She asked, gesturing e to look in the mirror.

I couldn’t believe what I saw. Already before I thought that I looked the part, but now I could easily have walked out into the street and nobody would have known any different. Well, for my face at least.

“I look very pretty. Thank you.” I answered in awe of what she had done.

“We’re not done yet.” Debbie responded.

She went off and came back with a black wig, cut in a bob. She hastened to put it on and brushed it into shape. While she went back out of the bathroom, I looked at myself in the mirror once again. The transformation was unbelievable. The wig had completely changed the dynamics of my head. I looked really cute; so cute that my cock was swelling up once again.

“Here, put these on,” said Debbie, handing me a small pile of clothes before leaving the bathroom.

It took me ages to get out of the summer dress because of the zip, but finally I managed. Debbie had given me a pair of beige stay-up stockings, and a cute matching set of silky cami top, cami pants and a light bathrobe. I hastened to put them on in order to join Debbie in the living room, only she wasn’t there.


“I’m in here,” Debbie called from the bedroom.

The door was slightly ajar and I could see that the room was dimly lit. As I opened the door, I saw Debbie lying sideways facing me on the bed. She was dressed in all black lingerie, with black stockings, a garter belt and panties, with a black corset top.

My cock was aching to pop out of the panties, but I had managed to lodge it sideways so that it didn’t protrude too much. I kept hoping that it wouldn’t suddenly release and spring forward.

Debbie patted the bed and beckoned me to join her. For the first time since I had been busted, the reality of the situation hit home. I was about to get into bed with Linda’s best friend.

“She won’t want you back anyway.” Debbie said softly, as if she had read my mind.

I slipped onto the bed next to Debbie. We lay there for a minute just looking at each other and then the next thing I knew we were kissing frantically. I rubbed my left hand up and down her back, and then caressed her panty-clad butt while she slipped a hand inside my bathrobe to rub my chest.

By this time my cock had become dislodged and was pressing firmly against the silky material. I could feel there was a lot of pre-cum from the wetness of the material.

I kissed her neck before rolling her onto her back, straddling her across the hips. I started undoing the eyelets of her corset stopping occasionally to kiss her, rolling our tongues together and gently biting each other’s lips. She reached forward and undid the bow holding my bathrobe closed. I slipped out of it and tossed it on the floor, before continuing to undo her corset. When I got to the last eyelet, she arched her back and slid the corset off to the side, then tossed it on the floor to join my bathrobe.

Her breasts were absolutely delicious. They were natural but firm C cups with quite sizeable nipples to suck on. They smelt exquisite too, a combination of her natural scent along with a hint of sweetness from her perfume. I lapped at her nipples for a while and then went back to kissing her neck. She moaned when I nibbled her ear lobe, so I teased her like that for a while.

“Ooh, someone has a problem in their panties!” Debbie laughed, grabbing my shaft through the silky material. “And you’re not the only one.”

She took my hand and placed it on her crotch. She had soaked her panties.

“You’d better go help.” She giggled.

I moved backwards until my face was level with her thighs. The sweet musky smell of her pussy was amazing. I licked her through her panties for a short while. She moaned softly, enjoying the attention as much as I enjoyed giving it to her. Then I pulled her panties down and ran my tongue softly up and down her pussy, occasionally pushing my tongue inside and then licking her clitoris.

“Yes!” She moaned, “Keep licking there!”

I obliged and she writhed about in orgasm. This happened at least three times, which is more than I’d ever seen from Linda. I was really happy to pleasure a woman that much and I wanted to continue.

“What else do you like?” I asked.

She didn’t miss a beat. She told me to lie and my back and then she proceeded to straddle my face. I was in heaven, enjoying the taste of her pussy, looking up at her beautiful body and her perfect breasts bobbing above me while she rocked back and forth to self-pleasure on my tongue and lips.

A short while later she placed her hands against the wall in front of her, arched her back, and came violently, squirting pussy juice in my mouth and all over my face.

“Oh yeah!” I exclaimed, “I love the taste of your juices.”

Debbie turned around so that she could suck me off while I continued to pleasure her, but first she stroked me through the silky material, teasing me about wearing girls’ clothing.

“You’re a naughty little thing, aren’t you, wearing skimpy girlie panties. Does it make you feel pretty to be all dressed up and made up like a sissy? I bet you’d enjoy having to wear a dress every day.”

She pulled my shaft out from under the silk and sucked the tip at first, and then she swallowed the entire thing. I almost came at that moment, but luckily managed to hold back.

“Slowly!” I gasped, “I almost came in your mouth!”

“That’s OK,” Debbie answered with a laugh, “We’ve got all night. Just be a good girl and enjoy it.”

She continued to suck and lick my cock more gently while I teased her pussy with my tongue. We stayed like that, enjoying the attention and giving attention to each other. After a while Debbie tensed up and came once again, less violently than before, but still with a trickle of pussy juice that I licked up and swallowed wholeheartedly.

Debbie got off me, but stayed in the sixty-nine position with her hands and knees on the bed, and her bottom pointing in the air.

“Take me from behind” She begged.

I didn’t need any encouragement. Her behind was sublime. I knelt behind her and slipped the tip of my cock inside her. She was tighter than I had expected, but once we had built some momentum my shaft slid in and out of her with ease. I grabbed her ass and pumped her until she came again.

“Oh fuck!” she moaned, “This is wonderful. I need to keep you girl.”

As she said that, I was overcome by the fact that I was dressed up like a girl and fucking a girl who was enjoying it, and who seemed to want to do it again in the future. My balls tightened and then I shot several pulses of streaming hot spunk inside her while she groaned with pleasure.

We collapsed on the bed, and ended up wrapping our arms around each other and tongue kissing again. The next thing I knew, it was 3am on the bedside clock. I woke up Debbie just to get into bed and pull the covers over us. I spooned with her, wholly aware of the silky material I was wearing and how good it made me feel. But even more than that, I was happy to have found a girl who actually liked the idea of a guy who dresses up as a girl.


In the morning we had breakfast and spoke about the night before. We had both enjoyed it immensely and we were prepared to do it again sometime. Neither of us were sure how or when, but we both knew something had changed dramatically between us.

“Before, I always thought you were a bit of a bitch.” I said.

“Before, I always thought you were a bit of a square.” Debbie responded.

We laughed and kissed.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

Copyright © 2015 Lars Kaiden. All rights reserved.

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