Glasgow
Scotland
Monday, 1st June 2015
I wandered around the front lawn, swinging the hover mower left and right until I had the lawn trimmed to look more like a deep-pile carpet than a garden. When I was satisfied with the lawn, I grabbed the shears and started cutting the surrounding hedge to create a neat finish.
“I may have to invest in an electric hedge trimmer to do this properly,” I murmured.
I paused occasionally to appreciate the tranquillity of the area where I lived. Bearsden was recognised as a district where many residents were better off, if not simply wealthy. I didn’t count myself as rich, but I’d worked hard to own a house in such an area. Three years earlier, I’d snapped up the house I was in, at the end of a tree-lined street and loved that the back end of our cul-de-sac overlooked a golf course. Only two months earlier, I’d taken early retirement on my fifty-seventh birthday.
My first wife had left me after twenty years, and when I remarried at fifty, it was to Kathryn, a divorcee a few years younger than me. Her daughter, Janine, was a grown woman with her own family, and for my own reasons, I was pleased that she lived in Sydney, Australia. I made all the right noises during our video chats, but I had no interest in getting close to my new wife’s daughter or her family. When I first told Kathryn that I didn’t want to fly to Australia on a 6-week holiday, she was upset that I didn’t want to meet her offspring. I softened the blow by suggesting that, instead of me accompanying her on her annual trip, I’d be happy for her to go twice or three times each year.
I paused in my hedge trimming. “Insisting that you went to Australia alone was one of my best decisions, Kathryn.” I grinned as I continued snipping and moving along.
It was only after she’d left on her most recent trip that I allowed a lifelong fantasy to become a reality. Kathryn called two days after departure to let me know that she’d arrived safely in Sydney, and after the brief call, I’d stripped and prepared to enjoy a new pastime. Unlike Kathryn, I still had a healthy sex drive, so whenever she wasn’t around, I’d get undressed and stroke my cock while browsing porn on the internet.
Things had stepped up for me while my wife had been away on her last trip, because I’d become bored with simply watching couples, lesbians, threesomes and gang-bangs. I had taken Kathryn to the airport, and that night, I spent an hour browsing porn, but looking for something new, and I found it. I wasn’t that interested in naked gay men, but something was stirred in me when I watched crossdressers getting together. I wasn’t sure when it had started, but in my younger days I’d occasionally had an urge to slip into something feminine. As the years passed, the naughty urge had faded and disappeared. When the desire returned more recently, it was strong.
Three days after Kathryn set off to Australia this time, I’d stripped and pulled on a pair of her panties before my porn browsing session. I had the most exhilarating wank of my life, and I wore a different fabric each night during that week. As the next week got underway, I wore tights and loved the feeling of the nylon on my legs. I was delighted to find stockings among Kathryn’s hosiery and lingerie collection, but I wasn’t prepared for how sexy they felt when I paired them with high heels.
I was finally enjoying my early retirement, having completed various minor projects around the house and in the front and rear gardens. With all those things done and my wife away, I had the solitude to work on writing my first novel. I would also be slipping into something feminine for a relaxed, but exciting porn browsing session in the evening. Our house lent itself well to me walking around in lingerie because the living room window was big, so I had lots of natural light, but there was no view of the room because it was obscured by the big hedge that bordered the front garden.
I was blessed with good neighbours too, because although we might occasionally pass the time of day if we met, they didn’t pry. Tony, who lived in the house to my left, was forty and worked in the finance sector. He had a lovely wife, a nice home, and a smart car, but to round off his perfect life, he was handsome and kept himself fit. In the house directly opposite lived Jeff, who was thirty-five, and also had a pretty wife, a decent home and a modern car. Another similarity was that neither of my close neighbours had children because both couples were career-minded.
I finished trimming the hedge and stood back to check my work, but it was uneven, so I reduced the height by a few more inches to make it flat on top and level. It was lower than I’d planned, but at least the entire garden looked neater. I put the gardening tools in the shed and went indoors.
I had intended to sit in the rear garden with my laptop and write for a while, but my urge to view porn was strong, so I went upstairs and stripped. I felt my arousal beginning as I went through Kathryn’s underwear drawers, and I anticipated a long and enjoyable wanking session. I lifted out lace panties, and then hold-up stockings, and a short, sexy nightie, but couldn’t decide which to wear, and then I decided to wear stockings, a nightie, and high heels.
I lifted one of the stockings and sat on the edge of the bed, ready to roll it up my leg. When I paused and looked at the few short blond hairs on my legs, another idea occurred to me. Two minutes later, I was in the en suite, lathering my legs with shaving gel. I carefully shaved my legs from the ankles to the top of the thighs. When it was done, I placed my razor on the washbasin and ran my fingers over my smooth legs.
“Oh my god, that feels so sexy.”
I gazed at my beaming face in the mirror for a moment, feeling hints of guilt and embarrassment, but the desire to continue was strong. I undid the scrunchie from my hair and let my short ponytail loose so that my blond hair fell to my shoulders. My reflection smiled and nodded back at me, and a moment later, I spread shaving gel under my armpits, on my chest and over my trimmed pubes.
“That’s much more like the crossdressers in the videos,” I whispered, “but I still haven’t gone the whole way yet.”
I placed one foot on the edge of the bath and reached into my crack, where I felt a few tiny hairs. I wet the area and applied gel, and with a few careful strokes, there were no longer any little hairs under my balls or around my pink hole. I stepped into the shower and enjoyed coating my smooth body and legs in fragrant shower gel.
“Now, it will be worthwhile to wear more than one item.”
I sat at Kathryn’s dresser to use her hair dryer, but as I blew and brushed my hair dry, I paused again to look at my face. My gaze drifted down to the tidy arrangement of makeup, and I felt my cock respond to my latest naughty thoughts. I finished drying my hair and arranged the makeup items as I thought they ought to be used. I’d stick to the basics and use a minimum amount.
Fortunately, I had a box of tissues and wet wipes handy, because it took me four attempts to make myself look even remotely feminine. I felt I was doing okay with the eye makeup and the lipstick, which helped give the right effect. My quest wouldn’t be fulfilled unless I dealt with every detail, so I chose a bottle of bright red nail polish, and with time and care, I had my nails painted and glossy in a few minutes.
“Sam, I think you’re enjoying this,” I whispered as I looked down at my throbbing cock. It wasn’t big, but I was pleased that I’d been circumcised because the glistening pink head made it look a bit bigger. I sat still for a few minutes, knowing I ought to wait for the nail polish to dry.
With makeup, hair, and nails all done, I spent longer choosing what to wear and opted for a matching black lace bra and panties, and black hold-up stockings. When I worked out how to fit the bra, it fell flat, so I used pairs of flesh-coloured tights to pad the cups. I remembered watching a video of a crossdresser showing how to tuck away her balls and tuck her cock back, so that was something else that took several attempts before I succeeded.
“Patience, Sam,” I whispered more than once as I adjusted the bra, smoothed the panties and stockings, and sat down to squeeze my feet into black, sling-back high-heeled sandals. When I stood and glanced at myself in the full-length mirror, I gasped. It was the first time I’d seen myself wearing makeup and more than one item from Kathryn’s wardrobe.
Five minutes later, I was squeezed into a short red dress and looking for jewellery that would be easy to wear. I found a pendant on a fine chain, a bangle, two rings, and clip-on earrings. When I stood in front of the full-length mirror again, I was aroused, of course, but beyond the psychological desire to transform myself, I could feel the physical effect. My small cock was straining in its tucked-back position in the panties, and that made me feel even sexier.
“I may never do this again, so I have to take some pictures.”
After switching on my laptop, I selected the camera and timer functions. It took me about five minutes to find a good distance from the machine and the ideal place to set the laptop.
“There isn’t enough room in my study or the bedroom, so it looks like a trip downstairs.”
Wearing high heels felt sexy, but even while I was posing, I knew they’d be difficult to walk in. I closed my laptop and, taking careful steps, made my way downstairs to the living room. I placed my laptop on the living room windowsill and then posed at different distances. I repeatedly took a few steps back into the living room away from the computer before adopting my next pose. I glanced up, out of the window, realising I could see over the freshly trimmed hedge. My heart thudded.
“Thank God, Jeff and Elaine are both at work on a Monday, so nobody will be walking past.”
I lifted the hem of the dress and attempted what I thought were a few sexier poses, and I got carried away. I continued to go to the laptop, pressing the key, and quickly getting into a new pose. For some reason, once again, I looked out of the window at my freshly trimmed front hedge.
Jeff was standing on the other side, staring straight at me, his lips parted and his eyes wide. He slowly shook his head from side to side before mouthing something and turning to walk down my driveway. He pointed towards the door, and a smile replaced his surprised look.
“Oh shit,” I whispered. “What have I done?”
Strangely, it wasn’t Jeff catching me crossdressed that worried me; it was thinking about how I’d convince him not to tell anyone else. I had no choice but to carefully go to the front door.
I opened the door but stayed well back. “Jeff, I—”
“You dirty old dog.” He remained outside, looking good in his white T-shirt and sports shorts. “Now I understand why you know so much about crossdressers.”
I met his gaze as I recalled a recent conversation we’d had in the local pub.
Jeff smiled. “I’ll be back in a few minutes for coffee … oh, and please don’t change.”
***
“I may have to invest in an electric hedge trimmer to do this properly,” I murmured.
I paused occasionally to appreciate the tranquillity of the area I lived in. Bearsden was recognised as a district in which many of the residents were better off, if not simply wealthy. I didn’t count myself as rich, but I’d worked hard to own a house in such an area. When I took early retirement five years earlier, at the age of fifty-five, I snapped up the house at the end of the tree-lined street and loved that the cul-de-sac overlooked a golf course.
My wife had left me, and when I remarried at the age of fifty, it was to Kathryn, a divorcee, a few years younger than me. Her daughter Janine was a grown woman with her own family, and for my own reasons, I was pleased that she lived in Sydney, Australia. I made all the right noises during our video chats, but I had no interest in getting close to my new wife’s daughter or her family. When I first told Kathryn that I didn’t want to fly to Australia on a six-week holiday, she was upset that I didn’t want to meet her offspring. I softened the blow by suggesting that, instead of me accompanying her on her annual trip, I’d be happy for her to go twice or three times each year.
I paused in my hedge trimming. “Insisting that you went to Australia alone was one of my best decisions, Kathryn.” I grinned as I continued snipping and moving along.
It was only after she’d left on her most recent trip that I allowed a lifelong fantasy to become a reality. Kathryn called two days after going to let me know that she’d arrived safely in Sydney, and after the brief call, I’d stripped and visited her wardrobe. Unlike Kathryn, I still had a healthy sex drive, so whenever she wasn’t around, I’d get undressed and stroke my cock while browsing porn on the internet.
Things had stepped up for me this time, because I’d become bored with simply watching couples, lesbians, threesomes and gang-bangs. I had taken Kathryn to the airport, and that night, I spent an hour browsing porn, but looking for something new, and I found it. I wasn’t that interested in gay men, but something was stirred in me when I watched crossdressers getting together. I wasn’t sure when it had started, but in my younger days I’d occasionally had an urge to slip into something feminine. As the years passed, the naughty urge had faded and disappeared. When the desire had returned recently, it was strong.
Three days after Kathryn’s recent trip to Australia, I’d stripped and pulled on a pair of her panties before my porn browsing session. I had the most exhilarating wank of my life, and I wore a different fabric each night during that week. As the next week got underway, I wore tights and loved the feeling of the nylon on my legs. I was delighted to find stockings among Kathryn’s hosiery and lingerie collection, but I wasn’t prepared for how sexy they felt when I paired them with high heels.
I was finally enjoying my early retirement, having the solitude to work on writing my first novel every day, and slipping into something feminine for a relaxed, but exciting porn browsing session in the evening. Our house lent itself well to me walking around in lingerie because the living room window was big, but there was no view of the room because it was obscured by the big hedge that bordered the front garden.
I was blessed with good neighbours too, because although we might occasionally pass the time of day if we met, they didn’t pry. Tony, who lived in the house to my left, was forty and worked in the finance sector. He had a lovely wife, a nice home, and a smart car, but to round off his perfect life, he was handsome and kept himself fit. In the house directly opposite lived Jeff, who was thirty-five, and also had a pretty wife, a decent home and a modern car. Another similarity was that neither of my close neighbours had children because both couples were career-minded.
I finished trimming the hedge and stood back to check my work, but it was uneven, so I reduced the height by a few more inches to make it flat on top and level. It was lower than I’d planned, but at least the entire garden looked neater. I put the gardening tools in the shed and went indoors.
I had intended to sit in the rear garden with my laptop and write for a while, but my urge to view porn was strong, so I went upstairs and stripped. I felt my arousal beginning as I went through Kathryn’s underwear drawers, and I anticipated a long and enjoyable wanking session. I lifted out lace panties, and then hold-up stockings, and a short, sexy nightie, but couldn’t decide which to wear, and then I decided to wear all stockings, a nightie, and high heels.
I lifted one of the stockings and sat on the edge of the bed, ready to roll it up my leg. When I paused and looked at the few short blond hairs on my legs, another idea occurred to me. Two minutes later, I was in the en suite, lathering my legs with shaving gel. I carefully shaved my legs from the ankles to the top of the thighs. When it was done, I placed my razor on the washbasin and ran my fingers over my smooth legs.
“Oh my god, that feels so sexy.”
I gazed at my beaming face in the mirror for a moment, feeling a hint of embarrassment, but the desire to continue was strong. I undid the scrunchie from my hair and let my short ponytail loose so that my blond hair fell to my shoulders. My reflection smiled and nodded back at me, and a moment later, I was spreading shaving gel under my armpits, on my chest and over my trimmed pubes.
“That’s much more like the crossdressers in the videos,” I whispered, “but I still haven’t gone the whole way yet.”
I placed one foot on the edge of the bath and reached into my crack, where I felt a few tiny hairs. I wet the area and applied gel, and with a few careful strokes, there were no longer any little hairs under my balls or in the area around my pink hole. I stepped into the shower and enjoyed coating my smooth body and legs in fragrant shower gel.
“Now, it will be worthwhile to wear more than one item.”
I sat at Kathryn’s dresser to use her hair dryer, but as I blew and brushed my hair dry, I paused again to look at my face. My gaze drifted down to the tidy arrangement of makeup, and I felt my cock respond to my latest naughty thoughts. I finished drying my hair and arranged the makeup items as I thought they ought to be used.
Fortunately, I had a box of tissues and wet wipes handy, because it took me four attempts to make myself look anything close to feminine. I felt I was doing okay with the eye makeup and the lipstick, which helped give the right effect. My quest wouldn’t be fulfilled unless I dealt with every detail, so I chose a bottle of bright red nail polish, and with time and care, I had my nails painted and glossy in a few minutes.
“Sam, I think you’re enjoying this,” I whispered as I looked down at my throbbing cock. It wasn’t big, but I was pleased that I’d been circumcised because the glistening pink head made it look a bit bigger. I sat still for a few minutes, knowing I ought to for the nail polish to dry.
With makeup, hair, and nails all done, I spent longer choosing what to wear and opted for a matching black lace bra and panties, and black hold-up stockings. When I worked out how to fit the bra, it fell flat, so I used pairs of flesh-coloured tights to pad the cups. I remembered watching a video of a crossdresser showing how to tuck away her balls and tuck her cock back, so that was something else that took several attempts before I succeeded.
“Patience, Sam,” I whispered more than once as I adjusted the bra, smoothed the panties and stockings, and sat down to squeeze my feet into black, sling-back high-heeled sandals. When I stood and glanced at myself in the full-length mirror, I gasped. It was the first time I’d seen myself wearing makeup and more than one item from Kathryn’s wardrobe.
Five minutes later, I was squeezed into a short red dress and looking for jewellery that would be easy to wear. I found a pendant on a fine chain, a bangle, two rings, and clip-on earrings. When I stood in front of the full-length mirror again, I was aroused, of course, but beyond the psychological desire to transform myself, I could feel the physical effect. My cock was straining in its tucked-back position in the panties, and that made me feel even sexier.
“I may never do this again, so I have to take some pictures.”
After switching on my laptop, I selected the camera and timer functions. It took me about five minutes to find a good distance to stand away from the machine and the ideal place to set the laptop.
“There isn’t enough room in my study or the bedroom, so it looks like a trip downstairs.”
Wearing the high heels felt sexy, but even while I was posing, I realised they’d be difficult to walk in for more than a few steps. I closed my laptop and, with slow and careful steps, I made it down the stairs and into the living room. I placed my laptop on the broad living room window sill, and set the timer before trying a variety of poses at different distances. I repeatedly pressed the key and took a few steps back into the living room away from the computer before adopting my next pose. I glanced up from the laptop and could see over the hedge that I’d trimmed, and it caused my heart to thud in my chest.
“Thank God, Jeff and Elaine are both at work on a Monday. Nobody will be walking past.”
I lifted the hem of the dress and attempted what I thought were a few sexier poses, and I got carried away. I continued to go to the laptop, pressing the key, and quickly getting into a new pose. For some reason, once again, I looked out of the window at my freshly trimmed front hedge.
Jeff was standing on the other side of the hedge, staring straight at me, his lips parted and his eyes wide. He slowly shook his head from side to side before mouthing something and turning to walk down my driveway. He pointed towards the door, and a smile replaced his surprised look.
“Oh shit,” I whispered. “What have I done?”
Strangely, it wasn’t Jeff catching me crossdressed that worried me; it was thinking about how I’d convince him not to tell anyone else. I had no choice but to carefully go to the front door.
“Jeff, I—”
“You old dog,” Jeff stepped inside. “Now I know how you know so much about crossdressers.”
I recalled a recent conversation we had over a few drinks in the local pub.
Jeff smiled as he closed the door behind him. “Should I call you Sam, or Samantha?”
***
Katya Cumming Erotica 