Glasgow
Monday, 30th July 2018
For the second time in a few months, I was without a job and wondered if I’d ever find one that suited me. It was half past ten, and I’d already checked the usual recruitment websites online, so I went downstairs to make a coffee. I noticed my stepdad’s newspaper on the worktop and flicked through it, looking for the Classified Ads and Situations Vacant.
I came across an interesting story on the fourth page.
‘Sexecutive Sweet
Charles Dean, a businessman from London on a weekend trip to Glasgow, had a minor mishap that got out of hand in a major way. On Saturday, 28th July, he left a conference saying he wasn’t feeling himself. When he was spotted later, he wasn’t looking like himself either.
Mr Dean had returned to his room, freshened up, changed his clothes, and tripped at the revolving doors as he left the hotel an hour later. He twisted his ankle and had difficulty getting back on his feet. A hotel staff member raced to the door to find a well-dressed lady on the ground, minus one high-heeled shoe. The lady was Mr Dean.
The embarrassed executive was helped back into the building. Minus, his long brunette wig, he was quickly recognised by two of his male colleagues. The crossdressed man’s embarrassment was increased when another guest took a snapshot with a phone and posted it on social media. This resulted in a frantic telephone call to the hotel by Mr Dean’s wife.’
“That’s not a good way for a woman to find out something like that about her husband.”
I continued reading the story, but there was nothing of interest. It looked like a reporter had simply taken the opportunity to embarrass a wealthy businessman and suggest that his secret pastime highlighted our diverse society.
When I got upstairs with my coffee, my mind was no longer focused on job vacancies. I wanted to read about crossdressing, the men indulging in it, and their reasons. The first article I read briefly mentioned that both women and men crossdress. It wasn’t thought strange for a woman to wear a trouser suit, but it was considered kinky for a man to wear a skirt. I didn’t realise I was going down a rabbit hole, as the subject captured my imagination.
After reading about crossdressing, I read about the related subject of fetishes. Of course, I knew of such things but never thought about it much. All I could recall was that, once again, men were highlighted as the main ones who enjoyed it. I couldn’t imagine feeling a sexual attraction or being aroused in any way by an inanimate object, but I found another interesting article.
‘Stiletto-heeled shoes and lingerie are the most popular items that draw the attention of men. Nylon tights, stockings, and panties are thought to be attractive, not only for the sensuous fabrics but also because they can be worn under normal clothes. It has been suggested that secret crossdressing helps relieve stress. It’s also a pastime that can evolve from the lack of a regular sex life so that a man might become a fetishist or crossdresser.
It’s believed by many sexual therapists that some men are victims of Autogynephilia. This is defined as a condition where the thought or image of himself as a female sexually arouses a male.’
I shook my head slowly. “I haven’t had a steady girlfriend for months, and a few minutes watching porn is enough to stimulate me. I don’t have to wear tights or panties when I give myself a handjob.”
As I said the words aloud, I imagined myself in no more than a pair of tights. It was peculiar, but reading about these things had begun to arouse me. I followed up on the articles by visiting a porn site to see what appeared under the heading of fetishes.
Two minutes later, I looked down a list on a site I’d visited several times. The categories were in alphabetical order, so I found fetishes easily. I’d browsed porn occasionally when I needed a little extra stimulus, but I’d never taken much notice of fetishes. I was stunned by how many were considered to be ‘common’. Stiletto-heeled shoes and thigh-high boots were sexy on a woman, so they were no surprise. Neither were nylon stockings, tights, panties and other lingerie. Other popular items I now noted were leather, plastic and silk clothing and, of course, phallic dildos. It was also no surprise that apart from inanimate objects, breasts, buttocks, thighs, feet and other body parts were loved by some fetishists.
I selected tights, and the screen filled with video previews of people in tights. It was obvious that some were men, while it took a second look at others to be sure. A few wore a wig, had applied makeup and nail polish, and wore a bra or a nightie. Many were convincingly female.
My next choice was men masturbating in tights, and this produced a new selection of videos. I selected one in which the person had a feminine-looking face and hairstyle, but upright, inside the black tights was an obvious cock. I played the video expecting to hear heavy breathing but was surprised by the soft, melodic voice.
“Hi, I’m Sandy, and it’s so good of you to view my video. Giving myself a handjob is lovely, and wearing tights is exhilarating. Combining the two things is incredible. Before I slip into my tights, I ensure that my legs and pubic area are shaved smooth so I can appreciate the sensual nylon.”
As the attractive crossdresser and fetishist continued, more special than the naughty suggestions, was when the camera zoomed in on Sandy’s fingers caressing the straining nylon over his, or was it her cock.
“Why don’t you … slip into a pair of tights … and join me … so that we can wank together. Oh, and remember … shave first … so that you get the maximum pleasure … from the experience.”
I was panting and realised my cock was stretching my boxers. I returned the video to the beginning and paused it before visiting my twin sister’s bedroom. Juliette attended Glasgow University, so she was rarely at home except in the evenings. Although she didn’t attend university over the weekend, she had a part-time job that took up much of her free time.
I paused in front of her dresser and panted. “What am I doing?”
I’d asked myself the question aloud, but I saw why I was there in my reflection. The bulge in my jogging pants was obvious, and although I already felt awkward, I had to follow through on my kinky experiment. I discovered that Juliette kept bras and basques in one drawer, panties and thongs in another, and tights, stockings, and nighties in the bottom one. I rifled through them until I found a pair of sheer, barely black tights.
I returned to my room, stripped, and sat on the bed to pull on the tights but stopped. I kept my pubes trimmed, and though I was blonde, I could still feel the hairs on my legs. I glanced at the laptop screen, exhaled slowly, and left the tights on my bed while I visited the bathroom.
A few minutes later, I returned to my room minus my pubes and with my legs freshly shaved. I caressed my legs from the ankles over my knees to the top of my thighs, appreciating the smoothness. I rolled the tights up in both hands and slowly pulled them over my feet before drawing them up my legs until they were snug from my toes to my waist. I returned to Juliette’s room to look at myself in her full-length mirror.
“Oh, wow,” I gasped, staring at my cock, fully erect, encased in the black nylon. The dark, central seam of the tights showed between my balls and up along the centre of my shaft to the waistband. I squatted to ease and smooth the material over my feet and legs to make the tights as snug as possible. When I stood to look at myself again, I felt my face warming with embarrassment.
Juliette and I were the same height. We both had long, blonde hair, and she was thick around the waist. Apart from having breasts, slightly wider hips, and, of course, a pussy, our physiques were only slightly different. I undid my ponytail, stepped forward, grabbed a hairbrush to centre-part my hair, and brushed it over my shoulders. Although I kept my hair in a ponytail, it had a natural wave. When I replaced the brush, the selection of makeup caught my eye, and a moment later, I was applying pink lipstick.
When I eventually returned to my room, my hard-on was throbbing. I sat at my desk, pressed my legs together in a feminine fashion, and replayed the video.
As Sandy made his or her suggestions, I obeyed, and my arousal ached more and more for release. I spent a little time looking down at my nylon-covered thighs, enjoying the sight before gently caressing them. I bent one knee, caressed that leg from the ankle to the thigh, and then repeated the action with my other leg. By the time I caressed my cock in the material, there was already a stain of pre-cum showing. I tried to rub myself slowly as I listened to Sandy in the video, but it was all too much. I gripped my cock wrapped in nylon while worrying my glossy lip and tasting the lipstick. As I wanked myself off, I panted so loud it was difficult to make out what Sandy was saying.
“Yes … yes … oh, yes.” I shot my load inside the tights, and the cum oozed out through the delicate but strong material over my fingers. “Fuck … that was … powerful … and amazing.”
During the next few minutes, I closed the video, left the porn site, and then slowly peeled off the damp tights. I went to the bathroom and washed them by hand before hanging them in the airing cupboard for a couple of hours to dry.
Guilt and embarrassment washed over me as I pulled on my socks, boxers, jogging pants and T-shirt. I’d started keeping a journal when I left school, and finding my first job had proven difficult. Since starting my journal, I’d written about the most interesting aspect of each day so this counted.
I opened my laptop and typed.
‘I’ve seen countless porn videos about fetishists and crossdressing, which have caused me to have some kinky fantasies. It’s never occurred to me that I would ever try anything kinky in reality.
Today, that changed.
I read a newspaper article about a businessman who had been discovered fully crossdressed. The story and the idea that it was a real incident captured my imagination. A short while after reading about the man, I was in Juliette’s room wondering what to borrow.
I chose a pair of sheer black tights and pulled them on after shaving my pubes and legs. I may not be a fetishist or crossdresser, but wanking in tights was amazing.’
I knew that when Brian, my stepdad, got home, he would ask how I’d been doing with my job search. I went to an online recruitment site and listed a few vacancies using a pen and notepad. If he asked, I would say that I’d sent email applications, but he would be no wiser if I had.
I was nineteen when Brian married my mum, and in the year I’d known the man, he continued to have two problems with me. He couldn’t understand why I didn’t attend uni as Juliette had done, and when it was only him and me around, he’d suggest I got my long blonde hair trimmed.
One day, he’d said, “I know you and Juliette are twins, but if you want to look more like her, all you’d need to do is wear a dress and a pair of high heels.”
As usual, I resisted, pointing out he wasn’t my real dad. Whenever Brian was having a dig at me about my long hair, I was always tempted to ask why I sometimes caught him looking at me. I wondered if he secretly wanted to grow his hair long and was jealous of me.
I’d resisted going to university because I wasn’t inspired to follow a particular career path. For that same reason, since leaving school, I’d worked in an office, a car dealership, a supermarket, a bar, and as a delivery driver. The delivery job was only temporary but was the one I enjoyed most. When I read my earlier journal entries, it stood out that I’d had fun driving around.
I found a vacancy for a delivery driver in Brian’s newspaper, so I applied for it. The downside was that the position didn’t have to be filled until Monday, 10th September. Even if I attended an interview and was offered the job, I’d have to occupy myself with something else until then.
When I removed the tights from the airing cupboard late in the afternoon, I absently wondered if it would pay me to have a video channel and do something unusual to attract visitors.
“Maybe I could crossdress, practice applying makeup and start a video channel like Sandy’s.”
I slowly shook my head, smiling and thinking the idea was absurd.
***
Katya Cumming Erotica 