A Night WIth an Escort!!!

Disclaimer: This story contains explicit description of sexual acts with characters of the LGBTQ spectrum, and might not be palatable for all audiences. If you can keep an open mind towards that, read on. I have never written on this topic (LGBTQ) before but I tried to handle it with the sensitivity and the respect it deserves. If I offend any sentiments, it'd be unintended and I would like to apologize in advance.

Rishabh had promised himself that he’ll be open to new experiences. He had always had a very high sex drive and an open mind to go with it. His approach to sex could be described as hedonistic and carnal. Fortunately, his partners in the past had shared his knack for wild and exploratory sex. But as anyone who’s ever been addicted to anything, Rishabh needed more and more of it to feel gratified. And after a while, his partners just couldn’t keep up with his escalating need for new and different experiences. 

Lisa, his last girlfriend, had walked out on him when he’d suggested something especially depraved he wanted to try. And that was thirteen months ago. Finding women who’d be okay with Rishabh’s real self was proving to be a challenge. And he was always bad at pretending to be something he was not. So he started experimenting, trying things he’d never done before. He signed up on Grindr and set up a date with a guy, after having awkwardly waded through tens of guys who’d ask “T or B?” or “What are your likes?”

After a fairly pleasant evening, Rishabh ended up at the guy’s apartment. But he couldn’t initiate anything. He felt like he’d bitten more than he could chew. But the guy was really suave and after a long evening of pleasant conversation, they actually managed to get a little intimate. Rishabh approached it like he approached everything else, with an air of exploration. It was another human body after all, albeit different from the ones he was used to, but similar too. They kissed and while it was a little weird, it wasn’t all that bad. The other stuff did get mildly awkward, but Rishabh realized that he was very curious about the human anatomy. And there’s a lot of power in giving pleasure to someone. So he started enjoying himself once he realized that what he was doing was actually driving the guy crazy.

That opened a whole new can of worms. While Rishabh wasn’t inherently attracted to other men, he realized he could enjoy having sex with them, even if the moments after sex could be extremely awkward. But the realization came with its own set of confusing moments. Rishabh had never believed in labels and now that he was dabbling with something new, he felt like he needed to define what he was. Was he bisexual? Or bi-curious? Being with women was definitely easier for him, and it wasn’t awkward either. Being with men felt like a lot of work. So was he bi at all? Or maybe he was just a straight guy with an abnormally high sex drive?

Between all this, one day, Rishabh came across an advertisement for an escort, while browsing one of those classifieds site for some strange. The pictures showed a buxom transsexual woman, with a set of intense eyes that he was immediately drawn to. Her appearance had a strange mixture of feminine and masculine features that intrigued Rishabh. And this was something he had never explored. He was tempted to give her a call, but hesitated, not because she was a transsexual, but because he had never paid for sex in his life. After deliberating for a day or two, Rishabh finally mustered up enough courage to ring her up. 

She called herself Mishti. She sounded like a deep voiced woman, her enunciation more feminine than most women. He told her the name of the site where he’d come across her profile and she asked him what he had in his mind. He replied with a shy ‘I don’t know’. She laughed a little and said she’ll hang up and drop him a text, which might help him choose. Moments later, Rishabh received a text from her, which listed out details about her, like her vital stats, what services she provided, the charges per hour and per night and her location, etc. Her next message read: “Give me an hour heads up before each appointment.”

Mishti’s apartment was in a crowded part of Delhi and reaching there by cab was a challenge, thanks to the narrow roads. And besides, she had shared a ball park location, to protect her privacy and had asked him to call when he was in the vicinity. He was dropped a few blocks away from her lane and he felt like all eyes were on him when he was walking towards her area. When he finally reached the lane, she gave him a house number and asked him to come up to the second floor. It was an old building with a narrow stair case. Climbing up the stairs, he couldn’t help feeling a little nervous and claustrophobic. She had kept the door unlocked. Mishti was only wearing a towel, draped over her ample breasts. She was short, stocky and dark and her voice was a little hoarse than it sounded over the call. 

She invited him in and asked him to take his shoes off in the living room and join her in the bedroom. He quietly obliged. He awkwardly sauntered into her room, which was heavily furnished, and I mean like ‘rich-people furnished’ – a large bed set, a TV table, and side-tables with lamps and drawers. In fact, with all the furniture, the room was a little congested for space. She asked him to settle down on the bed. He did. He hadn’t realized it, but his heart was pounding hard in his chest. He was very nervous. In contrast, Mishti was pretty composed. She sat next to him, leaning on the headboard, her towel-covered breasts making a big arch, under her chin. 

“So, tell me about yourself, Rishabh,” she asked, with an overtly seductive voice.

“I, erm, I am kinda new to this,” he muttered, nervously. She placed a hand on his shoulder and asked him to relax. It helped a little. He told her about himself, rather honestly. She listened carefully. And when he was done, she asked him what he was looking for. But instead of answering her question, he asked her about herself, “I want to know about you.” She looked at him with mild amusement and then let out a sigh. “You have been pretty honest, so I am gonna give you the less rosy version of my story,” she said.

“I was a pretty successful advertising executive until seven years ago. I had been bit of a nerd all my life and had never had girlfriends. Then I started getting depressed and anxious. When I saw a psychiatrist about it, after a few sessions, he informed me that I had gender dysphoria, which means I was a woman in a man’s body. Now the doc gave me two options: go for a sex change process which is long, tedious and expensive, or moonlight as a crossdresser/ live as a gay man. While the latter option was easier, I have never been the kind of person to half-ass anything in my life. So I decided to transition. Got on hormones.

“That’s when the real issues started. While my family was reluctantly supportive, the people at work started behaving badly once the feminine attributes started kicking in. I thought I was resilient enough to power through but after a while, the environment got too hostile and I had to quit. My boss wanted me to stay, but everyone else was being too weird and I didn’t need the negativity, especially because I was already an emotional mess due to the hormones. So, with the little money I received after quitting, I got breast implants. I did look for other jobs but by that time, with the changed appearance, it had become hard to get employment. Also, getting new documents was a pain, and I tried to, but the government officials gave me a horrible time. So, I gave up after a while and decided to escort for a living and save up enough money for a bottom surgery. That has been the journey so far.”

Rishabh had been staring at Mishti with incredulous eyes, wondering how brave a person has to be to go through such hardships. He was genuinely taken aback by her indomitable spirit. “Do you have any questions?” she asked. As a matter of fact, he did. “What’s bottom surgery?” he asked, nervously. She gasped a little and said, “Oh honey, did you think I have a vagina? You do know I am a pre-op transgender woman, right? So I need to get the doctors to build me a vagina.” At this point, Rishabh told her that he knew she was pre-op and told her that the term “bottom surgery” wasn’t familiar to him. She explained it to him. 

Then they talked about Rishabh’s job, they also talked about advertising, movies and a lot of other stuff. “I like this,” Rishabh said, sounding excited, “I have never been with an escort, and I thought it would be weird to have sex with a stranger, but I like that we could talk and relate.” Mishti smiled at him and told him that Indian generally confused escorting with prostitution. “You pay me for my company,” she continued, “and while it does include sex, that’s not all of it.” Rishabh had become quite comfortable with Mishti now. So he asked her, “Would you mind if I kiss you?”

Mishti rolled her eye a little and pulled Rishabh close and placed a kiss on his lips. She was being cautious, lest he didn’t like it. But he kissed her back, passionately. She untied the knot which was holding the towel on her body and it just fell open, exposing her big round breasts. Rishabh was fascinated. He had never been with anyone who had breast implants. As if she read his mind, Mishti took his hands and placed it on them and asked him to feel free to explore. He could feel the hard implants under her skin. It was heavy and he was scared of pressing too hard. She asked him to suckle at her nipples, which were smaller than an average women’s nipples. 

Rishabh let his hands wander over her body, feeling it, feeling how it was different from the bodies of the women and men he had been with. That’s when he noticed that he wasn’t feeling the awkwardness he used to feel with men. Kissing Mishti wasn’t weird, it felt natural. And he must have been doing it with all his heart because she seemed visibly turned on. Rishabh asked her if that was all a part of the girlfriend experience or if she was actually excited. She just took his hand down to her genital area and let him feel her erect member. “What do you think now?” she asked him. He replied by kissing her harder and longer. 

After making out for a while and giving each other head, Mishti asked Rishabh to “fuck” her. She told him to lean over to the side table and get the condoms and lube. In a certain urgent fashion, she applied the lube on herself and on Rishabh’s condom covered erection and guided him in, as she lay with her face down. They had sex. It was fast, sweaty and exhilarating and she moaned and groaned. That was a bit of a show, because as she later informed him, she was the quiet-in-bed kind of person. 

When they were done, she got up, went to the washroom and cleaned up. She asked him to go clean himself up and he did. When he came back, she was back in her towel and asked him to “come give me a hug”. He climbed back on the bed and hugged her, all the while looking out for that post coital weirdness he usually got when with guys. There was no sign of it. Rishabh discovered a new side to his sexuality. He kissed her some more and talked to her about what he was feeling. At this point, she joked to him if he wanted to make her his girlfriend. He laughed nervously and she told him it was a joke. In a serious note, she continued, “I can never be in a committed relationship now, at least not till I stop escorting. But since that pays the bills…” She just left the sentence midway and gave a melancholy smile. “I do have clients who have become great friends. They call me to hang out with them from time to time, which I do, as friends. But once they are up here in this apartment, they know they have to pay for my time,” she continued.

Rishabh was trying to place himself in her shoes and he couldn’t. He couldn’t imagine living like she had, facing the problems that she had faced. He was slowly filling up with respect for her, and since he barely had a filter, he told her that. She thanked him heartily, kissed his cheek and told him he was a nice guy. After a few more minutes, Rishabh left her place, with a new perspective on life and its hardships. He met her a few more times, mainly because talking to her was really fun and he always looked forward to it. He even asked her out once but she told him that she couldn’t go out with him because it wouldn’t be fair. For one, she couldn’t stop escorting. She explained to him that even if he offered to take care of her financially, she’d not let him because that’s not an honourable thing to do. 

Some months later, Rishabh left the city and moved to another metropolis. Mishti became a distant memory. He never met another transsexual woman, but he never forgot Mishti and her incredible integrity and courage towards life. Strange how these chance encounters change your perspective towards life and how life-changing experiences are found at the strangest of places. Some find clarity in temples and mosques while some find it in the bed of an escort.