Windows of Opportunity


 When I heard a tapping noise, I turned unsteadily and looked in disbelief at the window. I wasn’t the only one admiring my appearance. I felt my cheeks burning, my pulse raced, and my glossy, ruby lips parted.

“Oh no—” I glanced at the clock on the bedside table, and realised my innocent fantasy had started an hour before. Life as I knew it was surely over.


From our upstairs flat, I had watched my girlfriend Stephanie cross the road. She strode along, the hem of her short skirt flicking up emphasising her shapely legs.

No wonder the window cleaner ogles her, I’d thought. She’d mentioned it to me only the night before, and I told her it was a compliment. I wasn’t too worried, because she said she’d known him at school, and there had been certain rumours about him back then.

It was my day off, so after Stephanie left I had a late breakfast before enjoying a leisurely shower. I walked into the bedroom afterwards and caught the lingering fragrance of her perfume. As she did on occasion, Stephanie had discarded clothing onto the bed while choosing her outfit. I decided to put her things away before I got dressed. I lifted the nearest item, a black mini-skirt and caught a glimpse of myself in the wardrobe mirror.

Stephanie had often told me I had great legs for a guy. My response had always been to laugh and remind her, that we both might be blonde and twenty-three, but that was where the similarity ended.

She has a gorgeous face even before she makes herself up, and her figure is amazing.

I glanced at my legs in the reflection again as I stood naked with the small garment in front of me. It caused me to consider something. I dismissed the idea, located a hanger, and hung the skirt in the wardrobe. I lifted the pile of black silk and lace items, and stopped when I felt how soft they were. I spread the garments back on the bed and retrieved the skirt.

I had to try it, I thought—just this once. Nobody would know. The room was warm, but I was trembling. We live on the second floor with a view of the Yorkshire countryside, so there was nothing overlooking our bedroom. I glanced at the window feeling self-conscious, before sitting at the dressing table, selecting all I needed.

Living with a girl who works in a cosmetics department, meant I had more than average knowledge of how to apply makeup. Twenty minutes later, I smiled at my artistic efforts.

I had transformed my eyes, but went a stage further and added long, curling false lashes. It was easy to make my lips more pronounced. I knew that close up I looked as a young man would if he were to wear make-up, but nobody else was going to see me. Nobody would be getting that close. Using my imagination and sitting back, I could blur the edges.

It took some effort to paint my nails in bright red varnish. I didn’t intend to paint my toenails, but time was on my side, so I went ahead for the whole look.

I decided against using any of the distinctive perfumes.

As I brushed my long hair, I parted it in the centre. A glance at my face in the mirror confirmed my embarrassment. I could feel my cheeks burning, and I swallowed hard. My breathing was more rapid than normal. I tried different things with my hair including my usual ponytail, before returning to the centre parting. I found two small red ribbons and draped my hair over the front of my shoulders in long pigtails.

When I stood up, other physical signs confirmed a subliminal response to my intentions. I looked down at my hard-on and inhaled deep when I considered the effect of thinking about cross-dressing. All I’d done so far was my hair and makeup.

I was grateful to be alone for the day, and turned up the bedroom stereo.

George Michael’s voice on the radio suggested, ‘A Different Corner’ which brought a smile to my face.

It took a minute to locate a suspender belt, into which I stepped. There was a tiny red ribbon at the front. I sat on the edge of the bed, lifted a black nylon stocking, rolled it between my fingers as I’d seen it done, pulled it over my toes, unrolled it and smoothed it along my leg. As I pulled up the other, I almost tore it in my eagerness and nervousness. I clipped both stockings to the belt. I was conscious of my cheeks burning, and my breathing was faster, and heavier.

When I slipped into the lace panties and pulled them up, they were snug but comfortable. My straining cock was severely testing the material at the front. I caressed the stretched fabric, closed my eyes briefly, and enjoyed the sensation of the soft material. Having an average young man’s physique, I wondered at the point of a bra, but then I thought, if you’re going to do this—do it properly. I lifted a black lace number and got it on at the second attempt. At least my underwear all matched.

I stood up, looked at myself in the mirror, and became aware of my heavy breathing again. I bit my lower lip and closed my eyes as I made a token effort at reconsidering. It was pointless—I was too far gone. My fingertips brushed over the sensuous materials I was wearing, and I opened my eyes. I knew I would continue. There was no blouse on the bed, so I checked Stephanie’s wardrobe, and chose a yellow satin with long sleeves. I left the top buttons undone, so the bra was noticeable. I grinned when I considered my efforts to look sexy, except an unnatural bulge was present down below.

I held out the waist of the panties and tucked my stiff cock down between my thighs and forced it to point back. It took a few seconds of effort to hold myself in place with one hand and pull up the underwear with the other. Wow, what a difference. I could feel my arousal straining, but there was no bulge.

I lifted the black mini-skirt and stepped into it. As it slipped up my legs, I once again became aware of the stockings. I watched my reflection as I pulled the skirt up onto my waist, and it looked good; or so I thought.

While I admired my efforts in the full-length mirror I was pleased, but there was something wrong. Then it struck me—no shoes. Finding high heels was easy, but I knew my shoes were two or three sizes bigger than Stephanie’s. It struck me that I might not manage the whole outfit, but I’d try. After twice crushing my toes, I found a pair of toeless red stilettos. I secured them by using the final hole in the ankle straps. I wondered whether my toes or the shoes would give up first.

It took a few seconds to balance before I looked in the mirror again. I was wearing my usual tiny gold studs, so I replaced them with big gold hoop earrings. As I teetered to the middle of the room, I heard a noise at the front door. My heart skipped a beat, and I gasped. I held my breath as my freshly glossed lips parted.

With one hand against the wall for support, I made my way slowly to the hallway and looked nervously at the door. A magazine in a clear plastic pack squeezed through the letterbox. The package thudded onto the mat. A white envelope followed and then a postcard. I exhaled and turned back to the bedroom.

The mail could wait. This was a decision which would later haunt me.

As I entered the bedroom, I knew I’d have to gain confidence walking in stilettos. I watched my alter ego approach in the full-length mirror.

What was that thing I’d heard about a woman’s walk—step one foot in front of the other, and not straight forward like a man. I recalled hearing or reading that the thighs should kiss, or brush fractionally. I tried it and walked back and forward.

My face burned again—I considered what my mates in the garage would say if they could see me. I stopped in the middle of the room, turned around and looked back at my reflection over my shoulder. Stephanie was right, I did have a good pair of legs; at least in stilettos and stockings.


That was how I arrived in the most embarrassing position of my entire life. When I heard the tapping noise, I looked at the bedroom window. My lips parted, my mind raced, and my face burned more. Our window cleaner leant on the top of his ladder, nodding slowly and smiling.

Hanging on the top rung of the ladder was his chamois leather, and in his right hand was a top of the range mobile phone; just like mine. The camera lens was aiming directly at me. He pointed to the side window. I steadied myself against the wall, then approached and opened the window. It was too late to hide, but I still stood to the side.

I’d never seen him before, because it was Wednesday, and his usual day was Thursday. On top of this, Stephanie always paid him. He was the one who apparently ogled her.

He was handsome, looked about my age, and had blonde streaks in his long brown hair. He had it tied in a ponytail, and it hung low down his back. His upper body was bare, which showed off his tan, and toned physique. It couldn’t have taken him long to get dressed I thought; a gold chain, denim shorts, and trainers; no socks. He obviously enjoyed stripping down for his job in the summer months.

“I’ll be at the door in two minutes,” he whispered. “Don’t change—just let me in.”

I made to speak, to explain that I wasn’t Stephanie, but he inclined his head, and raised an eyebrow. He’d said, ‘don’t change’. Of course—he knew Stepanie. I stared out across the fields for a few seconds. As he descended his ladder, I walked unsteadily to the front door.

“Why did you do it?” I asked myself aloud. My mind flooded with regret and questions. How many photos had he taken? Would he tell Stephanie, or anybody else? Why had I been so stupid, to carry on my fantasy into reality? What would he say if I let him in? Importantly, what would he want to do? What should I do now? What could I do?

For a minute, I stood waiting at the door, and vague memories of something Stephanie said came to mind. She told me she had gone to school with this guy. There had been rumours about him back then. I stood trembling as I tried to remember the rumours.

I needed a plan. Perhaps I could pretend I was rehearsing for a fancy-dress party, and if he called my bluff, I could try reasoning with him. I didn’t have much time.

With difficulty, I squatted down to pick up the mail, and put it on the hall table. I turned over the postcard. It started, ‘Dear Customer …’ and went on to explain that Wednesday would be the new day for the cleaning of certain apartment windows. It was a bit late for me to find out. The card was signed, Gary. It had to be the same Gary that Stephanie had known. There was a light knocking on the door.

I stayed behind the door, and dressed as I was, it felt ironic that I was the one looking through the peephole. I stayed behind the door, and took a deep breath as I opened it for Gary to enter.

The handsome window cleaner stepped inside, and I quickly closed the door. My head was  bowed as I looked up at him from under my long dark eyelashes. I couldn’t look him in the eyes and I stood with my hands clasped in front of me. I didn’t consider my accidental pose, but I was aware he was appraising me and smiling. It was only then that it registered.

He smiled but didn’t laugh. “My name is Gary—what’s yours?”

“Chris,” I murmured. “This isn’t—”

“Chris?’ he interrupted. “That’s handy—it’s unisex.”

“This really isn’t what—”

He put a forefinger to my lips, and I got a faint whiff of the chamois. It was a clean, hygienic smell. I closed my eyes briefly and swallowed. Something came to mind as I stood there. I had to try it, and I hoped it would work. I forced my lips to curl into a brief smile.

“Leave your training shoes here,” I whispered. “Let’s go into the bedroom.”

“Okay, we must think of the carpets, eh?”

I led the way, concentrating, and applying the theory of the kissing thighs. I found I was walking more easily in the heels, and it felt kind of sexy. When I arrived in the bedroom, I turned to see Gary undoing the button on his denim shorts.

“I wish I had hair like yours,” I stepped closer to him. “Let it free, to fall over your shoulders.” His brow furrowed briefly, but he did as I suggested and undid the ponytail. I trembled as I reached out with both hands, and arranged his soft hair evenly, my mind racing. I was aware of his fresh breath, and his eyes looking from my face, down over my outfit. I was also aware of his faint smile and his toned, muscular body. I could smell him.

“That’s much better,” I turned away and stepped toward the dressing table. “You choose any outfit you like.” I swallowed and looked over my shoulder. “I’ll get the makeup ready.”

“I didn’t intend—”

“With that tanned body of yours and those legs.” I turned to look back at him. “You’d look amazing in white stockings.”

He glanced down at his own legs, and then looked at mine.

“Go on.” I pointed. “The underwear is in those drawers.” I glanced in the mirror, and saw him looking from me to the wardrobe, and chest of drawers. His hands were resting on the waistband of his shorts; thumbs tucked inside, pushing them down. No sign of underwear, or pubic hair. I don’t know why, but those things registered.

“Do you think—”

“What shoe size are you Gary?” I asked without turning.


“You are so lucky,” I said enthusiastically. “You’re only one size bigger than Stephanie.” I stole another glance at him as he opened the wardrobe, but his tan prevented me seeing if his face was beaming. Desperate to know if my plan was working, I glanced down at the open front of his shorts. My eyes opened wide, but I looked away before he caught me.

I applied more red lipstick to give me something to concentrate on. I had to think and couldn’t be caught looking at him. I didn’t have to look around, but I was aware of him dropping his shorts and stepping out of them. Gary was naked except for his gold chain. In my peripheral vision, I realised he was going through the items in the wardrobe.

I dared sigh with relief.

“Chris, what do you think of this?”

I turned to see him holding up a red mini-dress with white lace frills on the sleeves and hem.

“It’s very sexy,” I said and would look great with white stockings.

“I think so too.” He stared at me. “You’re trembling Chris. Come over here.”

As I straightened up, I had to gain my balance to walk towards him. He was standing there naked, holding white stockings in his right hand and the red mini-dress in his left. Between the garments, standing proudly from between his muscular thighs was his proud and throbbing cock. His body made me look slim and puny.

I walked towards him unsteadily until we were within arm’s reach and I stopped to look into his eyes properly for the first time. My false lashes felt heavy, and I blinked several times. I watched the dress and stockings being thrown onto the bed and then I turned back to see Gary step forward.

“You have to stop trembling, Chris. Come here.” He held out his arms.

I tried to take a step and stumbled. Gary’s arms encircled me, and I instinctively put my hands on his shoulders to balance myself.

He looked into my eyes as he pulled me closer. His cock was hard and when I felt it rub against the mini-skirt I realised he would notice there was no bulge. I trembled again.

A strong hand came up and gently lifted my chin until my face was turned up to face his. He brought his lips down on mine in a gentle kiss. I tried to resist and looked at his eyes, but he had closed them. As that point registered, I felt his tongue probing my mouth, my eyes closed, and my lips parted.

While the kiss continued, I hoped he’d get his kicks from that and then leave. Maybe I put too much effort into the kiss, or I was just stupid to believe it could end there. Whatever I thought, I was wrong. He stopped the kiss and then smiled.

“Sit on the bed Chris.” His voice was soft.

I opened my mouth to protest, but he placed his right forefinger against my lips and gripped my left arm with a strong hand to pull me to the bed. I sat on the edge of the bed and looked up at him as he stepped towards me. Would he make me give him a hand-job?

“Your fantasy was getting dressed up wasn’t it?”

“Yes.” My voice was a murmur as I looked down, straight at the tumescent shaft which was inches from my flushed face. “I didn’t want—”

“What you want isn’t important now, Chris. What’s important is what I want. It’s my turn and I’d like to fulfil my fantasy.” He reached out and tilted my chin upwards again with his right hand. “I want you to suck my cock like a good girl.”

My mind was all over the place. “I’m not a … I’ve never … done this … or—”

“Don’t worry, Chris. If you’re good, you can stop when it goes soft.”

The implication of his statement didn’t register because I was in a panic. I sat there looking at the size of the thing. My mouth was dry, so I ran my tongue along my lips.

“That was sexy.” Gary’s voice was soft and his tone calm. “Now kiss the tip and lick it first, before you take it into your nice hot girlie mouth.”

I looked up at him, my lips slightly parted. I couldn’t think what to say.

“Chris, your fantasy was to get all dressed up to look like a girl, and you look good. My fantasy is to get it together with a guy dressed like a girl—now suck me dry.”

There was an aroma from his cock. It was something I had only ever sensed before from myself, but at this proximity it was stronger.

I leant forward and kissed his throbbing cock, just as he told me. I hoped he would come quickly because of the excitement. It was my only hope of this thing ending. He held my head still with one hand, and with his other hand, held his cock and rubbed the glistening head across my lips. When I gasped he pushed his shaft into my mouth.

It was bad enough that I was being face-fucked by this guy, but once again to steady myself I put my hands up—to land on his muscular thighs.

Gary lifted my hands to take them around to grip his buttocks. My fantasy was becoming a nightmare. When he spoke again, the nightmare took on new dimensions.

“This is nice Chris … but this isn’t my whole fantasy.” He moaned softly as his hips moved slowly back and forward.

I closed my eyes and sucked, imagining what I would want if I was him.

Gary held my head in both hands as he fucked my mouth steadily. The taste of his juice was getting stronger. I hoped I could pull away before he spurted into my mouth. If I couldn’t, I was sure I would puke.

Oh, shit, he’d said I could stop when it goes soft ….

“Chris, my lovely girl … I’d like to fulfil … my main fantasy … next week.”

I wasn’t in a position to reply, so I continued to suck, and started using my tongue.

“I’ll be back at the same time … next week, Chris … and I want you here … wearing that red dress … with those white stockings that we both like.” He paused and stopped thrusting, but his cock was still in my mouth.

I didn’t want him to get violent so I continued sucking, gently, still using my tongue. 

“You’ll be pretty in that other outfit … oh, and another thing.”

I stopped sucking and looked up at him—his big shaft halfway inside my mouth.

“I would suggest … you buy a large tube … of lubricantand be a good girl.” He held my face and it took a few more thrusts before I got a significant taste of what was to come.


This is a tale from the collection Coming Around: and other erotic stories