You Can't Help Who You Love

Disclaimer: All of the characters depicted in this story are fictional and over 18 years of age.

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The conflict within

I sat in my recliner looking furtively at the laptop sitting on the tv cabinet. It was a recurrent habit. I held firm, not surrendering to my 'baser' self. And so continued the internal struggle I fought daily to not visit 'those' sites.

At 42 years of age, I was six months past the dissolution of my 14-year marriage. It wasn't a nasty, spiteful separation. Both of us just realised that we were incompatible and the relationship had no future. While I missed the company around my new apartment, I didn't miss the relationship. Once the gut-wrenching decision had been made and we had both moved out of the old house we had bought together prior to our wedding, it became clear that it was the right decision.

Jessica had found someone and had begun to date in the past month. While it felt weird to see her with someone else, I wasn't in a funk over it. I wasn't in the same space mentally as her. I wasn't ready to start a relationship. I just wanted to get used to being in my own company for a while. It was a novel experience as we had done so much as a couple.

But I really missed physical intimacy. I had not been with anyone since my separation and as an active guy with a fairly strong sex drive, the last six months of enforced chastity had been very difficult. This was one of many areas of our lives where Jessica and I were not in sync. I enjoy an active sex life and I have a vivid imagination and desire to experiment. Jess on the other hand was slightly introverted and was happy to make love in the missionary position once a month. While I had tried not to pressure her, it was a source of tension in the relationship from very early on.

Though if I were going to be totally honest, the issues with my sex life were less about the frequency and variety of sexual congress with my ex-wife, and more to do with the secret that I hid even from her. The secret pleasure that I fuelled using the computer sitting on the tv cabinet. I was attracted to cross-dressers.

For a guy who styled himself as a typical masculine, heterosexual Australian my interest in seeing other guys dress up as women and get fucked was just a little hard to reconcile.

As a teenager who learned about sex more from pornography than from my absentee parents, I acquired a very limited, unenlightened perspective on the meaning of physical attraction and intimacy. I was remarkably naive about sexuality in all its varied forms. I knew from a relatively early age that I had a strong attraction to feminine guys, but I didn't identify as gay or bi-sexual. I did however, understand from growing up in a working-class neighbourhood that this wasn't something one shared. Not unless one wanted their ass kicked.

At the time I simply dismissed my attraction as raging hormones messing with my head. I was also attracted to women so I tried to focus on my more 'normal' proclivities. I would return from time to time to those videos, but I was able to live a 'normal life'. I dated girls and eventually married one.

But as I got older, I came to understand - albeit uncomfortably - that my attraction to cross-dressers and feminine men was not a passing phase. Nor could I so easily dismiss it. There was no mistaking the intensity of the physical reaction I had when I saw an attractive man who was shaved smooth and dressed to accentuate his feminine attributes.

But the thing that truly threw me was the nature of the dreams that I would have about feminine men. You might well think that with my propensity for watching porn my sub-conscious would conjure images of raw animalistic passion. Instead my sleep was filled with fantasies of intimate touching and tender love-making. These unbidden images left behind in their wake powerful feelings of conflict and self-loathing. Deep down I knew that my friends and family would be shocked and openly disappointed if they found out so I never explored my interests. These concerns continued to colour my views and actions.

In spite of this, since my separation I had indulged my habit more frequently, and about four weeks ago I had begun visiting an online site to look at ads put up by cross-dressers who were looking for casual hook ups. Initially, it was just about titillation. I would get incredibly aroused reading the vividly described offers of 'fun'. It's not as if I planned to actually contact anyone, but the thrill of thinking that an encounter was only a few clicks away was a powerful aphrodisiac.

As I sat in my recliner, resolving once again to resist the temptation to look at these sites, I puzzled at the sheer futility of such restraint. However, it would be another hour before I fetched the laptop.

The path untraveled

Settling back down into the seat my pulse raced with excitement as I signed in and opened my browser. With practiced familiarity I found the cross-dresser link on the personals site and clicked on it. One hundred and forty-three ads flashed up for my city, 11 of them were new. Glancing through the titles there were the usual ads from the usual suspects. Married men seeking to get off, 'bucket listers' whose curiosity would end once someone responded to their ads and the reality of the situation dawned on them, and then there were the same group of femboys whose ads were always up.

Tonight, I happened to come across a new ad by a 30 year-old simply titled, 'New and curious'.

I clicked on the ad and read the lengthy description. The author indicated that he had been cross-dressing in private for years, but was fiercely shy and had only recently decided to reach out. He described himself as trim, 5' 8" tall with nice legs and ass. He admitted to having some unsatisfying random hook-ups before he had come to realise that what he was looking for was to feel sensual, be treated like a girl on a date and be made love to gently. Most importantly, the ad stressed, he wanted to be viewed as a lady and not a guy in drag. His, or should I say her, honesty appealed to me.

There was also a photo attached. When I clicked on it there was an image of her from the waist down, standing side on and bent forward slightly. She was in a very short, yet elegant silver, sequin dress that ended just below what appeared to be a nicely curved, pert ass. It was a far classier shot than most of the ads on this site. Her legs were stunning. They were milky white, smooth and toned, without the bulky musculature that I had seen in many other cross dressers. In truth, from the waist down I would not have thought that this was a man.

I was strangely drawn to talk with this person. Apart from finding the ad appealing, I hadn't actually been able to talk to anyone about my interests and desires and this person sounded like they were at a similar point in their exploration to me.

Without stopping to think I clicked the link to contact the advertiser. But what should I write? I began to describe myself and where I was at in my journey. As I wrote I found the words came more freely and I opened up about my hidden desires, my struggles and explained that I wanted to meet someone who wasn't just seeking another score. I described my dreams and their more gentle, intimate nature. I asked if the person would feel comfortable sharing a little more about herself. Before I could second guess myself I hit send.

Immediately I felt a tremendous sense of excitement wash over me. I had balked at this step so many times and finally I had plucked up enough courage to act. The site provided an indication of when the message was received by the advertiser and the marker changed colour to indicate that this had indeed occurred. As I pondered whether this person would respond to me the marker changed colour again to indicate that the advertiser had opened the message. I had not even considered the possibility that the person might be online at the time.

My excitement and nervousness battled for domination as I sat stupefied staring at an unchanging screen, waiting and hoping that I would get a response. Yet the minutes dragged on and with mild disappointment I decided to get a beer. When I got back to my seat there was a message in my inbox. My heart nearly leaped out of my chest as I clicked on the message.

The sender thanked me for my sincerity and told me that her name was Becky. Her message explained that she had received a number of approaches from people in the short time that her ad had been posted, most of them explicit or including lewd photos. Becky told me that mine was the first message she had read that she had wanted to respond to. My experience, it turned out, wasn't far removed from her own. Becky had always been attracted to men and was submissive from an early age, but had hidden her desire to dress and be treated like a woman for fear of being ridiculed and ostracized. This was her first attempt to reach out with her true self and she confessed to being intensely insecure about the move.

As I read, I became increasingly certain that Becky was who I had been looking for. I began to write back explaining that I appreciated her sharing something so private with me and that I was relieved that she was looking for the same things as me. I confided that I thought from what I had seen of her, she looked stunning and that I was impressed that a newcomer could have appeared so feminine. I decided to share a bit more information about myself. I described what I looked like, some of my interests and the type of work I do.

This it turned out was to be the beginning of a stream of messages that we shared that night. Becky indicated that she too liked hiking and camping. She also thanked me for the compliments about her appearance and attached another photo that she hoped I would like. The photo was of her from the shoulders down in the same dress as before. Her hips curved invitingly in the shot, hugged flatteringly by the form fitting dress. Her hands were clasped in front of her revealing a small, indiscernible tattoo on her left upper arm. Becky had no cleavage to speak of, but she seemed to fill the dress nicely all the same. Dark chestnut hair cascaded down over the front of her left shoulder, which I assumed to be a wig. All in all, she looked stunning.

Conscious that I hadn't shared any photos yet with her, I grabbed my phone and set it on the tv cabinet, propped against the monitor and took a few experimental shots. I adjusted the angle of the camera to avoid getting my face. I liked this girl, but I wasn't about to provide something that could be used to blackmail me. Noting that the shirt I was wearing was a bit baggy, I made the snap decision to remove it and take a shot of my bare upper torso. Now, I don't have a chiselled physique, but I am not overweight either. Once I had taken a number of photos, I selected one and included it as an attachment to my message.

Almost the same instant that it was sent the marker indicated that the message had been opened. Becky, it would seem, was as excited by our exchange as I was. She wrote back quickly to tell me that she loved the photo and confided that she found me attractive.

The photo seemed to make her a little playful. She asked what I would like to do if we were to meet. With all of the messaging I no longer felt any hesitation in responding, "would you like to find out?"

Becky did not respond immediately. I was starting to worry that I had pushed things too quickly for her when her response appeared. She wrote, "if it isn't too late you can come to my place."

I replied quickly to let her know that I would like that and she sent me the address and told me that she lived alone.

"See you soon," was my short response. I closed the laptop and sat in quiet disbelief. I was about to find out if this was what I really wanted. I had no doubts about Becky. She seemed genuine.

I hopped up and jumped in the shower to clean up. I quickly shaved and brushed my teeth. Feeling somewhat fresher, I got dressed in smart casual shorts and a button up short sleeve shirt.

I went to my bedside table and picked up a couple of condoms that I had ambitiously bought and not used after my separation. I also picked up some lube that I kept for 'self-stimulation'. The latter, to my frustration, had seen considerably more use than the former.

As I hopped in the car the nerves began to hit. I was really doing this. I drove the short distance and stopped outside the small cottage-style house at the allotted street number. Pausing briefly, I prepared myself that Becky might not have mastered hair and make-up yet and may look more masculine than her photos would lead one to believe. l certainly didn't want to offend her with a sudden look of surprise or disappointment as the door opened.

The cottage was surrounded by a dense cottage garden and was set back from the road. The effect meant that the front door was completely screened from the casual observer walking by. As I reached the front porch, the door opened and I was presented with a vision in black. Becky stood smiling coyly in a black chiffon, shimmer dress that ended at her upper thigh. Her chestnut hair brushed over one ear and her dark red lips accentuating the smooth pale skin of her face. If you looked hard you could see the slightly square jaw and Adam's apple in her neck, but it would not have been readily apparent if you didn't know what you were looking for.

All my preparation went out the door. I stood there gobsmacked.

"I take it you like" she said in a soft voice accented by just a hint of masculine baritone.

Regaining my wits, I smiled wryly and mumbled, "very much."

Becky turned side on at the door gesturing for me to come inside. My eyes never left hers as I approached the threshold. She was smiling deeply at me, her pretty features radiant in the porch light. She was just so incredibly captivating. I stopped directly in front of her as I entered, placing my hand lightly on her waist and leaned in to softly kiss her. There was no hesitation as her eyes closed and our lips brushed furtively across each other. My other hand found her cheek and I held her face as my lips again found hers and continued their tentative exploration. Becky's tongue just barely grazed my lips as we parted.

I paused for a second intoxicated by her presence and her perfume, which carried just a hint of jasmine. As I walked through the doorway, the hand on her hip slid across her stomach, the chiffon moving freely across the smooth skin beneath.

I heard the door close behind me and Becky walked over taking my hand and asked if I would like a drink.

"Sure", I replied.

"What can I get you?" She asked, her eyes catching mine as I took her in.

"Whatever you're having will be fine, thanks."

She pulled out a chilled bottle of white wine and poured two glasses, handing me one.

We sipped the wine, standing less than a ruler's length apart, staring into each other's eyes. Becky lent back against the island kitchen top. She lowered her glass and asked, "so why me? Why now?".

"Whenever I thought about taking the plunge and meeting someone online, I had a very specific set of criteria for what I was looking for. I guess I never really thought I would find it. Then when we were chatting tonight, I realised that you were exactly who I was looking for. It doesn't hurt that you are stunning either!" I smirked.

Putting down her glass and moving towards me Becky purred, "you are most definitely the man that I have been looking for." Reaching her hand up, she pulled my face down to hers and kissed me seductively. I fumbled as I placed my glass on the counter and took her in my arms as the kiss intensified. Our lips parted and her tongue found mine, caressing it as her lips pressed more insistently into mine. My hands slid over the curve of her back, luxuriating in the feel of the fabric on her soft skin. My fingers traced their way down until they were just above her bottom. Meeting no resistance, I gently slid them down to cup her firm ass and pull her into me.

Becky cooed as she felt my hardness press into her stomach. She draped her arms over my shoulders as she lent further into our embrace. Our tongues were relentlessly exploring as our bodies mashed together. Her small form fit perfectly against me. My hands grasping the pliant flesh of her ass.

I bent lower and kissed her jaw and her neck, trailing kissed down to her collarbone and back up to just below her left ear. Becky moaned deeply and pulled my head into her harder. Taking this as guidance, I opened my lips and kissed her neck more firmly, running my tongue up to pull her earlobe between my lips. Sighing again, she kissed the side of my face hungrily. I bent down and feasted on her exposed neck, tracing my way down to her collarbone. My hands ran up and down her body taking all of her in.

Becky looked up at me between gasping breaths. "I want you," she whispered. She extricated herself from me with some difficulty and grabbing my hand led me towards the hallway. We took another four steps and I moved up behind her pulling her back into me. With me pressed against her back I reached around her wrapping my arms around her waist and holding her in place. My mouth found the nape of her neck and my teeth lightly grazed the supple skin. My hands ran up over her chest, finding her nipples and gently squeezing them.

Becky pressed her ass back firmly against my hard cock as I continued to paw and maul her. With laboured breathing betraying the effect that I was having on her, she begged me to follow her to her bedroom.

Not releasing her from my firm grip, we walked in crab-like fashion forward, both of us laughing at the absurdity of it. Stepping inside the room at the end of the corridor I saw soft candlelight illuminating the nightstand and head of the bed. It was the only light penetrating the room and gave a romantic glow. Turning in my grasp, Becky took my face in her hands and looking deep into my eyes, she whispered, "will you make love to me?"

In answer to her question I lent in kissing her tenderly. She sighed into the kiss. My hands roamed her body as hers snaked under my shirt and traced along my bare torso and chest.

Reaching around I found the zip to her dress and slowly drew it down. The dress, momentarily held in place by our bodies, fell instantly when I stepped back. Becky wore matching sheer black lace bra and panties. There was no sign of any bulge. She was so incredibly sexy. She stood back for a moment, a glimmer of hesitation in her eyes as I continued to take her in.

"You're stunning, Becky!" I offered quietly, breaking the tension.

Smiling again, she stepped towards me and began to gently unbutton my shirt. I stood there letting her work, my hands lightly caressing her exposed skin. When she was finished, she worked the shirt over my shoulders, leaving my upper body exposed to her gaze. Leaning down she ran the tip of her tongue from my abdomen up to my nipple, taking it gently into her mouth. I groaned at the sensation, making her smile.

Her hands slipped under the waist of my shorts and pushed them down. As they passed my thighs they fell in a pile at my feet. My cock stood in proud relief against the cotton briefs. Becky stared down at my concealed erection with thinly veiled desire. Falling to her knees, her face mere inches from my throbbing manhood, she looked up into my eyes as her dark red lips enclosed gently over the brief-clad tip of my cock. It was hands down, the sexiest thing I had seen in my life!

Her lips opened and her tongue probed the sensitive underside of the head of my dick. Leaning forward she took more of the cotton-clad head of my cock between her lips applying gentle pressure. I closed my eyes and moaned loudly at the long-forgotten sensations. I could feel the wet heat of her mouth through the thin fabric.