Gerard, a 59-year-old German, had lived in his cozy apartment for over 35 years. He had no plans to ever move again and had good relations with his neighbors. There was one lady of his own age who, like him, had lived there for many years. They’d always exchanged greetings and had a quick chat, but that was it. She was a bit reclusive, but he was drawn to her in a way. [Photo Hailey]
She always looked put together in her suits and heels, with a great figure. Lots of men were drawn to her because of that. Her name was Haley, and there was a rumor that she was transgender. She looked a bit like the singer Amanda Lear, who was popular in the 1980s because of her low, husky voice. She’d been in a relationship with David Bowie and had a mysterious haze about her sexual identity, but there’d never been any proof that she was transgender.
One day, Gerard saw a group of people gathered around someone lying in the street. He was curious, so he went to see what was going on. It was Haley lying there, making it clear to the bystanders that there was no need to call the emergency services. She had a mild case of diabetes and had forgotten to take her medication. Gerard suggested he accompany her home, and once there, she quickly took her medication, which quickly made her feel better. “You gave me quite a scare,” he said, looking concerned. “I’m sorry you were startled, but there’s no need to be,” she said with a casual air.
She said that because her illness was mild, she sometimes forgot to take her medication because it didn’t cross her mind. She offered him a drink as a thank you and poured a few glasses of pure vodka. This drink was one of his favorites, but Gerard wondered if she should have it because of her health. “Don’t worry, I can have anything in moderation,” she said, “as long as I take my medication on time.” “It’s pretty strange, actually. We’ve lived close to each other for decades, but we don’t actually have much contact with each other,” Gerard said.
She explained that she had her reasons for this and knew that people talked about her, but otherwise kept it to herself. Gerard was curious about this mysterious woman who lived in seclusion, but he didn’t want to embarrass her further, so he kept quiet about it. Haley always kept a close eye on everyone and had almost never seen Gerard with a woman. She asked him if he had a steady girlfriend. Gerard said he was actually very shy and had trouble approaching women. Haley wasn’t satisfied with this answer because Gerard looked attractive. She asked if he was gay and if he sought his pleasures more in gay saunas or gay bars. “Oh, I’m actually straight,” he replied, a little taken aback by her question. “Sorry for asking such an indiscreet question, but I do see you regularly visiting our neighbor Arthur,” she said, knowing Arthur was gay.
Gerard said he got along well with Arthur and often did a job for this gay man, who was very awkward, but that there was nothing between them except friendship. “Can I get you another drink?” Haley asked, enjoying the company of this attractive man and hoping he’d stick around a bit longer. She poured another drink and sat down next to him. Gerard could smell her perfume, which was really nice and made him feel a bit excited. Haley soon noticed that Gerard was getting aroused by the bulge in his pants.
She wasn’t going to let this tasty morsel pass her by. She immediately took the initiative by kissing him full on the mouth. Gerard was taken aback at first, but quickly recovered and opened his mouth, allowing him to exchange a long tongue kiss with Haley. It had been a while since he’d been with a woman, and he was eager to take advantage of this horny woman who was unashamedly offering herself to him. “You’re pretty horny, aren’t you?” Gerard said, putting an arm around her and feeling her blouse.
She then stroked the bulge in Gerard’s pants and felt his hard cock. She was determined to see that bulge, and she was delighted to find that he was wearing a delicious man’s thong. His big cock was already protruding above the edge of the fabric. She pulled his pants and thong down a little further, admiring his shaved cock and taking the smooth rod in her hand. She didn’t waste any time. She bent down and licked the pre-cum from the glans, then took his prick deep into her mouth and began to suck him deliciously.
“That’s pretty impressive,” Gerard said, impressed by the lady’s technique. She knew exactly what she was doing, circling his glans with her tongue. Haley was making Gerard really horny, so he couldn’t stay behind either. He decided to return the favor by searching her box with his hand under her skirt. Gerard became even more aroused as he stroked over her shiny nylon stockings, held up by her suspenders. Like a lot of guys, he got a kick out of this exclusive underwear that unfortunately few still wore. Haley knew how to drive a man crazy. When he was almost at her nether regions, Haley pulled his hand away. “Wait a minute, I’ll take off your pants and thong first,” said Haley, who noticed that the clothing was pinching his phallus. After removing his sneakers, which he was wearing barefoot, she pulled off his pants and thong. She also took off his shirt while she was at it.
Gerard stood there naked in front of her, and Haley took one look at his muscular body and gave him a thumbs-up. “Let’s sit down and pick up where we left off,” said Haley, who was now clearly aroused by his naked body. She gave him another long tongue kiss right away, and they exchanged saliva a lot during it. Gerard had moved on and was looking under her skirt for her panties, which were undoubtedly already soaking wet with her pussy juices.
Gerard suddenly stiffened with fright when he realized that instead of a tasty clam, he felt a hard penis. “Oh my gosh, are you a transvestite?” he asked, realizing that the rumors about her transsexuality were true. “No, sweetheart, I’m a real woman with an extra,” Haley said calmly. She told me that she was born a boy but had been transformed into a woman after a course of hormone treatments because she had felt from a young age that she had been born into the wrong body.
The only thing that gave her away as a former boy was her penis, which she was perfectly happy to get rid of. “Can you still get a hard-on and produce sperm?” he asked, amazed. “Of course. With the right hormone treatments, that shouldn’t be an issue. Plus, I can always turn to Viagra if needed, but I don’t anticipate needing it just yet.” Gerard was taken aback. He had just been making out with a guy? “I’ll put your mind at ease,” Haley said and stood up. She took off her robe and, at first glance, looked like a beautiful woman. But there was a bulge in her panties that showed there was no pussy there. After this, she took off her nice bra, and a great pair of buns popped out, making her look like a beautiful woman.
As she looked at Gerard, she slowly removed her panties, revealing a rather impressive piece of anatomy. Gerard was taken aback, though he hadn’t anticipated this. Haley had caught him off guard. “I’m proud of my body and I’m still sexy,” she said, turning around and pulling her buttocks apart to show off her beautiful backside. Gerard had already had sex with a woman in this position and knew how nice and tight it felt.
“This is why I’ve been living a reclusive life, but as of today, I’m ready to share my identity with the world,” said Haley, who seemed relieved to reveal her true identity. “Just so you know, I may have a penis, but I’m a woman first and foremost,” she said.
She sat down next to Gerard again and tried to give him a tongue kiss. Gerard paused for a moment, but gave in because Haley was a great kisser. Before long, they were enjoying each other again, and Gerard was so excited that he dared to lick her, which felt amazingly soft. He took her hard nipples into his mouth one by one and licked them.
Meanwhile, Haley was massaging his genitals, and Gerard tensed up for a moment as he felt her stroking his penis with her finger. “I want you to fuck me,” Haley said, her voice excited. She knelt in front of Gerard, who pulled her buttocks apart and looked at her inviting arse, which seemed to be asking to be touched. Gerard asked, “Shouldn’t there be some lube on it?” Haley firmly rejected this idea.
“No way! I’m used to it by now because of the rubber dildos I regularly lower myself over,” she said with a seductive smile. He carefully penetrated Haley’s anus, who encouraged him by saying that she wanted to be taken as deep and as hard as possible. Gerard didn’t let her say that again and with a strong thrust, he pushed his cock into Haley’s intestines, who let out a loud cry of pleasure as Gerard penetrated her. Gerard liked the warm sewer and started to fuck her with long strokes. “This is great. Take it out, then you can go right back in,” she moaned, lying on her back with a pillow under her ass.
Gerard got what she was after and pushed his cock back into Haley’s stretched hole while he had a view of her fairly large cock that she was jerking off in front of his eyes. The sight of a woman with a penis masturbating so aroused him that he began thrusting into her more vigorously, his testicles striking her buttocks. She was really turned on and it wouldn’t take long for her to cum, but I decided to wait.
She pressed her thumb and forefinger firmly against the head of her clit for a moment to delay her orgasm. “Can I fuck you now?” Haley asked. Gerard wasn’t sure, though. Was he gay? “Don’t you think it would be interesting to find out what it feels like for a girl to be taken in her pussy? Now’s your chance,” Haley said with a little persuasion. “After all, I’m not a man, but a woman, as you should remember,” she said.
Gerard thought quickly, realizing this was a unique opportunity. “I want you to be really careful, and if it’s not what I’m looking for, we can stop right away,” Gerard said, feeling a little anxious but also curious about this anal deflowering. Haley was pleased she’d been able to persuade Gerard because she herself wanted to stimulate a man’s anus again. The last time was at least 15 years ago. Gerard got ready on his knees and waited nervously for things to happen. Haley quickly grabbed another tube of lube, as she didn’t want to penetrate Gerard’s unpracticed anus without it.
She applied a blob of lube to his anus with her finger and also squirted a little into his prostate, which she gently penetrated with her finger to prepare him internally as well. That finger was fine because he’d had a finger in his hole before from girlfriends who’d given him a prostate massage, but a hard penis was something else. Haley sat down behind him, and he felt her pressing her vulva against his anus. “Just relax, and it’ll be easier,” Haley said, repeating a phrase Gerard had told his exes countless times.
He felt Haley slide her cock into his ass gently. It felt a bit uncomfortable at first, but it quickly gave way to an incredible sensation that Gerard had never experienced before. “Are you okay?” Haley asked kindly, and Gerard replied that it felt good.
Gerard’s poop hole was filled with Haley’s sausage, and he felt a rush of excitement in his cock, likely caused by prostate stimulation. Gerard felt his pre-cum dripping from his glans, which Haley caught and licked from her hand. She was really getting into it. Once he was used to the sensation, Haley began thrusting into Gerard’s anus with long, slow strokes. Haley was close to ejaculating and started thrusting faster and faster, panting and moaning as she spurted her poop into Gerard’s hole.
He could tell from his own experience that this was a source of great pleasure for her. Gerard was surprised that he hadn’t noticed Haley’s squirting cock more. He’d always assumed that a girl would feel the warm jets of semen. “What a delicious ass you have. Should I milk you?” Haley asked, having enjoyed Gerard’s tight pooch.
After Haley put a couple of towels on the couch to catch the cum that was slowly running out of his anus, she asked him to sit down on it. She started to give Gerard a blowjob, rolling his balls in her hand. Before long, Gerard came, moaning and spurting his seed into Haley’s mouth, which she eagerly swallowed. Haley snuggled up against Gerard, and they lay there for a long time, resting after the intense sex.
Gerard was now used to Haley, and they continued kissing until their lips were chapped. They continued having sex several times a week, and their relationship grew stronger. They sold their house and bought a bungalow in Portugal, where they lived happily for many years.
