He found her online, on a website where she-male escorts advertised their services. It was the best and safest way to get what he wanted. She was the only Caucasian on the site among mostly Hispanics and a few blacks. He flipped through the gallery of her photos and read her stats. She was good-looking in a way that clued him to how she probably had looked as a man. Age 27. Her height was listed as five-nine, weight 135, and her photos confirmed she had a good body with large implanted breasts. The description promised “nine inches, fully functional,” which gave him pause, and he wondered it were true. The only way to find out was to make a date.
She was available that afternoon. She instructed him to drive to the general area of her location and call again. On the second call she identified the hotel and room number. It was a high-rise adjacent to a shopping mall. She opened the door wearing a red silk or nylon robe and red boudoir slippers. He saw that she did look like her photographs and probably was five-nine, nearly as tall as he was. He hoped the nine inches would turn out to be factual. He imagined he could handle it if it were.
He handed her the envelope with the “300 roses” and she tucked it in a pocket of the robe without counting it. They broke the ice by exchanging first names and after some small talk she invited him to get comfortable, which he understood to take off his clothes. As he undressed she spread a bath towel on the bed, removed the robe, and kicked off the slippers. She wore only a red thong and tattoos. He looked her over and was pleased. Shoulder length brown hair, perfect makeup, clear, smooth skin from top to toe. The implants with small pink nipples. He couldn’t discern any signs of masculinity. Maybe the broad shoulders and narrow hips. And the bulge in the thong.
“You have a beautiful body,” he said, “and a great ass.”
“Thank you,” she said. “It’s my second-best feature.” She winked and grinned as she said it, implying the nine inches nestled in the thong was best. He couldn’t wait to see it.
She seemed relaxed, no hurry to get down to business. She asked a few questions, sizing him up. Was he married, in a relationship? No he was not married, and he was not in a relationship, and he liked women but lately had become interested in exploring other things. He told her there had been several women over the years, and recently, finding himself curious, a few men. He had embarked on a quest to freely investigate the full range of human sexual experience.
She moved closer to him and pressed closed lips to his mouth and took his cock in her hand. The implants felt rigid against his chest. He was about half-erect and his cock responded to her touch. She sat on the side of the bed and took a condom from the bedside table, tore the wrapper, and removed it. She placed it on her tongue and bent forward and expertly applied it to his cock with her tongue and lips. She started working his cock with her mouth. Her mouth felt very hot on his cock and it swelled as she sucked it and moved her lips up and down the shaft.
“That’s really good,” he said after a minute. “Why don’t you lay back and let me have a turn.”
She looked up at him with deep brown eyes. “You want to suck me, baby?”
“I like a girl to enjoy herself too,” he said, and grinned down at her. He didn’t come for a blowjob.
She rolled back on the bed and pushed herself up to lay back on the pillows. He knelt on the bed next to her and eyed the bulge in the thong. He tugged at the waistband and she lifted her hips off the bed to help him get it off, releasing the biggest cock he had ever seen outside of porn videos. The sight of it made his heart beat faster and he bent forward to go down on it.
“Wait for a condom, baby,” she said, turning to get one from the bedside table. She removed it from the wrapper and gave it to him. “Here. You put it on.”
He couldn’t resist touching it first, and as he fondled it, the smooth hulk responded quickly and became fully erect and rigid. If it wasn’t nine inches he judged it as damn close. With quivering hands he put the rubber on it. He straddled her legs and took the cock in his mouth and tasted the dry latex as he massaged the head with his tongue, working up saliva to get it wet. He began to suck it, gently at first, then more aggressively, causing her to moan. He opened his mouth as wide as he was able and tried to take in as much of the long shaft as he could. He moved his head up and down on the shaft, maintaining a tight grip with suction, letting it hit the back of his throat. Spit dripped on his hand. Not the first time he sucked cock. Nothing that big.
She arched her back and said, “Mmmm. Oh, yeah, suck it baby.”
Several minutes and he was at the peak of desire. He took her cock out of his mouth and said, without looking up, keeping his gaze on the cock, stroking it, wanting it so badly, imagining how it would feel, ripping into him, “Are you ready to fuck me now?”
“You made me ready,” she said. She rolled over and sat on the edge of the bed. She took a tube of lube from the drawer next to the bed. “Lay back,” she told him, touching his shoulder, and he stretched out on his back.
He had expected she would fuck him from behind, doggie position or bending him over the bed. He looked puzzled, but before he could ask, she said, “I want to fuck you missionary so I can see your face.” Applying lube to her dick. “And I want to watch you come. Okay?” Not really asking permission, she was asserting control, dominating him. What he wanted.
“Spread your legs.”
He opened his legs, more excited by submitting to it, willing to take what he considered the female role. He studied this person he did not know, blending genders with the salient parts of both, man and woman, tits and dick—Was he safe with her?
Using her left hand, she lifted one leg, prompting him to bend his knees, and went for his ass with the right. The lube on her hand was cold. One finger slipped into him, then two, and she began moving gently in and out, opening him up. He closed his eyes and moaned.
“You’re pretty tight. Relax, I don’t want to hurt you.”
He didn’t reply. He was concentrating on the sensation of the fingers thrusting slowly in his ass, wanting more. He focused on relaxing, surrendering to her hand. As she pushed, he took deep breaths to force his ass muscles to slacken.
“This your first time?” Softly, almost a whisper.
“Uh-huh. I’ve played with dildos . . . ”
“Were they as big as this?” she said, rising on her knees, stroking it, showing him.
“Uh-huh. I guess. Maybe.” Too much effort to compare now.
With the dry hand she pushed his legs upward until his hips rolled up and his thighs pressed against his body. He felt the cock nuzzling between his cheeks, groaned in anticipation. With her right hand she guided it and he felt the big head claim entry. He moaned again, involuntarily, aching for penetration. Eyes pressed shut, he took a deep breath and bore down to open himself to it. Cock getting into him, splitting him in two. He felt the burn as his asshole strained to resist. His sphincter clenched, and when she felt it, she stopped pushing and held in place.
“You’re still very tight, baby. Is it hurting you?”
“It hurts a little,” he said hoarsely, “but don’t stop.”
“You still want it?”
“Yes.” Swallowing hard, “Put it in.”
She pushed again, gently, entering slowly, and he gasped with pain and the sensation of fullness. He accepted the discomfort, knowing from penetrating himself with dildos that when it went in deep it wouldn’t matter anymore and be worth it. Pain would dissolve in pleasure. She moved her hips, thrusting in and out slowly. He matched her moves as much as he could with his legs pinned to his chest. Gradually she went deeper until her cock slipped through the inner ring of his ass and moved against his prostate. The indescribable sensation it produced forced a sob out of him, and hearing himself, he felt frail and vulnerable. His asshole was totally slack, and her cock moved easily. She was steadily and leisurely fucking him and the whirl of sensations flooding him overrode any concern about what she might be thinking about him. He allowed himself to moan, not caring anymore about anything but fucking.
He opened his eyes and stared into hers. Words weren’t needed. They were locked together in the most intimate act, the communion of their bodies. Using his ass muscles, he opened to every inward thrust and squeezed down on the cock as it withdrew. Rocked his pelvis in unison with her. The tight expression on her face told him she was into it just as much as he was. She wasn’t pretending.
They panted as they worked toward a climax. Her nostrils flared and she closed her eyes and turned her head to the side. She was thrusting faster, her balls slapping his ass. She turned back to him and opened her eyes. Her mouth opened and she moaned. She slowed her movements and stared into his eyes. She alternated shallow thrusts, pulling almost out, with deep, hard, driving stabs that drove him out of his head. Impaled on her huge cock she owned him and he succumbed completely, giving himself over to it, body and soul, letting her fuck him anyway she wanted.
“Oh, baby,” she groaned. He felt her cock getting bigger and knew she was going to come. He grabbed his cock and squeezed and pulled, desperate for release. Feeling spasms in her cock pushed him over the edge to a long aching orgasm and a huge spurt of semen erupted from his cock and splashed hot on his chest. She continued thrusting deep in him, grunting, still coming, causing him to feel another, weaker orgasm, and more cum oozed from his softening cock.
She stopped finally and stayed inside him. She bent forward and kissed him on the mouth with closed lips.
“Oh, baby, that was so good.” She pulled out and helped him straighten his legs. She moved away to sit on the edge of the bed. She grabbed a handful of tissues from the box on the bed stand and wiped the come from his body. She smiled. “We came together.” Seemed surprised.
“Yeah,” he said, “we did, didn’t we?”
“I don’t usually come, but I couldn’t hold back.”
“You could try thinking about baseball,” he said, chuckling, but her blank expression told him she didn’t get it.
She handed him more tissues then got up and went into the bathroom. He wiped the lubricant from his ass, and saw traces of blood on the tissue. His anus felt soft and supple, as completely wrung out as he felt. Good chance it would be sore for a while.
She brought back a wash cloth and towel. “So you can clean up.”
Looking in the bathroom mirror he saw his face and chest were mottled pink. He wet the wash cloth and washed himself cursorily, knowing he would shower at home. He felt a little foolish the way he had carried on getting fucked. Moaning and groaning like that. He couldn’t control it. Even sobbing once, out of his head, like a woman. He wondered what she thought about it, if she regarded him as silly or effeminate. He had enjoyed the experience, had craved it even, but did getting fucked mean he was less of man? He wondered what she would say if he asked, but he knew he wouldn’t. He imagined that prior to hormone treatments and implants, there had been a gay man who probably took it in the ass himself, as she does now with many johns.
He wished that he could get on top of her, fuck her good to see how she would act with his cock in her ass.
She had the robe on when he came out. In bare feet an inch shorter. She smiled at him. He dressed himself, at a loss for something to say. Feeling the wet between his legs as he put on his clothes, he recalled everything they had shared. No need to tell her it was good. She knew. She had told him so. “Oh, baby, that was so good.”
She put her arms around him and kissed him again with closed lips. He wanted more, open mouths with tongues exploring, but he knew more germs lived in the mouth than the genitals. He hugged her, knowing it was unlikely they would ever meet again.