Harry and the Transsexuals

by Marlene Sexton

  Deidre took it slow, even removing her finger and applying more lube once. Finally, Harry felt Deidre’s knuckles press against his ass cheeks. It was in. It hurt a little, but it wasn't bad. However, as she first wiggled and then withdrew her finger it felt amazing. Deidre reversed the direction and in her finger went and when she pulled it out again the feeling was incredible.

  “Fuck! That feels amazing!” Harry said and both girls giggled.

  “I told you, Harry,” Sarina said.

  After a few strokes, Deidre removed her finger completely and Harry found he missed it very much. Deidre smiled and grabbed her big cock and slapped it against Harry's balls. Harry thought that was just about the sexiest thing he'd ever seen. There was just no denying that Deidre's cock was beautiful. It was a magnificently sexual thing and Harry found himself wanting to feel Deidre's cock doing what it was made for. Fucking!

  Deidre had Harry put his legs on her shoulders and she took her cock and pressed it up against Harry’s virgin ass. It was hard, even the tip, and it quickly penetrated a short way. Deidre slowly pushed further and Harry felt his body resist. It began to hurt and he began shaking his head as if to say no, but the Sarina bent over him and took his cock in her mouth. Suddenly, Harry wasn't focusing on the pain anymore.

  Sarina continued to suck Harry's cock as Deidre forced her cock deeper into his ass. The pain wasn't horrible, but it wasn't pleasant either. Harry wondered if this was a good idea, but then something gave, the pressure he felt was gone and he felt Deidre's big cock slide deep into his ass. It still hurt, but the pain was getting better. Harry was breathing quickly and his body tensed.

  Deidre let her cock rest deep within Harry and said, “Just relax, Harry. The pain will go away in a minute.”

  “It already is thanks to Sarina.” Sarina tilted her head and gave Harry an appreciative look. Harry liked Deidre, but Sarina was just so perfect. Sweet and lovely, womanly and sexy. He wondered what she would be like once she had transformed completely. He wished he could find out.

  Suddenly, Harry's train of thought was interrupted when Deidre pulled her cock partially out of his ass. It hurt a little, but the pleasure was intense. Deidre grabbed Harry's ankles and spread his legs wide again. Harry let out a deep moan and Sarina stopped sucking his cock and asked, “Nice, huh?”

  Harry could only nod his agreement as Deidre began steadily pumping her cock in and out of his ass. Sarina absently stroked Harry's cock as she watched Deidre fuck him. Harry was already writhing in pleasure, panting loudly. He couldn't believe how good it felt being fucked like this. He felt like an orgasm was imminent, but it never materialized. Harry was experiencing constant pleasure and it was becoming more and more intense, just like Sarina described.

  Deidre let go of Harry's legs, but he left them in the air as she bent over Harry, supporting herself with her arms. Sarina leaned back and began stroking her softness, watching the show. This not only felt different, but it was more intimate. Harry was the submissive one as this pretty woman with the big cock fucked him silly. His body rocked back and forth as Deidre pounded his ass and he found he loved having her be in control.

  After a while, Deidre lay down on top of Harry, and wrapped her arms around his neck, her hips driving her cock deeper. Harry had never felt like this before, but he loved it. His cock was so hard, trapped between Deidre and himself. He could feel it leaking profusely. Deidre kissed him as she filled his ass. Fucking Sarina was good, but getting fucked by Deidre was so wildly different.

  Deidre's cock pounded Harry's ass harder and harder and he sensed she was getting close, “I wanna watch, Deidre!” Harry pleaded.

  Confused, Deidre lifted her head and looked at him, then figured it out, “Oh, Harry, I'm not even close. I can fuck you all night if you want.” Harry blushed. An hour earlier, he wouldn't have thought he'd even want to receive anal sex, much less enjoy it, but now he didn't want it to end. Deidre held Harry tight and resumed fucking him with her big, hard cock. Harry looked over at Sarina who was obviously enjoying the scene, biting her lower lip and stroking herself.

  “Isn’t it delicious, Harry? Now do you see why I don’t miss coming?” Sarina asked. Harry wasn’t sure he did, but this did feel pretty damn good. It wasn’t as good as a big, explosive orgasm but it was close. Then Harry wondered when the last time he had a really good orgasm. This was better than the half-assed climaxes he had looking at porn. Maybe he did see Sarina’s point.

  Harry began to lose sense of how long this had gone on. Deidre had gotten back to her knees, pinching her nipples as she bucked her hips in a steady rhythm. Harry's ass burned, but in a good way. It felt as if he would explode in orgasm any second, but his cock never did. He even stroked it for a while, as did Deidre, now and then, and discovered he wasn't as close as he thought but still it wouldn't take much. His cock, though, hadn’t been this hard in a long time.

  Deidre's blonde hair was matted against her neck and face and droplets of perspiration glistened about her tanned, supple form making her look even sexier. She had been fucking him for maybe twenty minutes, thirty? Honestly, Harry wasn’t sure, but he was enjoying it immensely. Harry wanted to share this with Sarina and bade her to lie on top of him. Sarina seemed to know what he wanted immediately.

  The girl straddled Harry’s face and then lowered her torso and began sucking Harry's engorged cock. The hard cock in his ass combined with Sarina’s soft warm mouth was incredible. Way beyond any pleasure he had ever experienced with natural woman. It was all so foreign, but it felt fantastic.

  Harry began sucking Sarina's nearly hard cock and licked her pink balls. Harry's mind went into overdrive. Was he really doing this? A cock in his ass and another in his mouth, both attached to a beautiful girl. It was all so strange, but incredibly exciting. He never wanted this night to end, but suddenly he wanted to come badly, but not before he made Sarina come

  Harry didn't know if he could make her do something that Sarina had told him she rarely managed, but he was going to try. Harry wrapped his hand around Sarina's thighs and massaged her balls as she fucked his mouth. Deidre had settled into a slow, steady beat obviously tired but unwilling to stop. Sarina slowly and softly sucked Harry's cock, seemingly understanding he was on the edge.

  Harry worked hard to please Sarina, using every trick he could think of to pleasure her. She obviously enjoyed the attention as she bucked her hips with increasing speed and intensity. Sarina was moaning, though Harry’s cock muffled the sounds. Still, many minutes went by and Harry needed to come in the worst way. Suddenly, he had an idea, slipped a finger into Sarina’s ass, and began slowly fucking her. Sarina squealed and sunk her hardening little cock deeper into Harry's mouth.

  Harry sensed this might be enough to push her over the edge, but made sure when he grabbed Sarina's balls and squeezed, roughly massaging them in his palm. He felt Sarina’s cock swell and it was almost as hard as his or Deidre’s. Sarina tensed and her mouth left Harry’s cock as she screamed, “Oh my God! Yes! Yessss!”

  Sarina's cock twitched and filled Harry's mouth with warm semen. She fucked Harry's face insistently as several busts of hot cum filled Harry's mouth. Harry was surprised at first, but managed to take every drop of her. Harry savored the creamy, warm gift as Sarina quickly got up after she had finished coming and began kissing Harry, sharing her cum with him.

  “Oh, Harry! That was amazing. Thank you! You’re just perfect!” Sarina whispered between kisses. She looked at Deidre, who now looked as if fucking Harry had become more work than pleasure and Sarina asked, “You ready, baby?”

  “Yeah!” was Deidre's only response. Harry's cock ached and his ass felt raw, but the intense pleasure still washed over him with every stroke of Deidre's cock. Sarina looked at Harry as she snuggled against him and whispered, “You're turn.”

  Sarina began slowly stroking Harry's cock. It was slippery with his pre-cum and Sarina's saliva and her hand glided effortlessly up and down the shaft. Deidre slowly withdrew her cock t
o both Harry's relief and dismay. He already missed the sensation of that sexy dick in his ass, but Sarina’s hand felt even better. Deidre began furiously stroking her cock. Harry had never seen anything more erotic that a woman jacking her own cock like that.

  It took several long moments, but finally Deidre shouted, “I'm gonna come!” Harry watched as her balls tightened and then a ribbon of white liquid exploded from Deidre's cock. It landed, warm and creamy, on his cock and balls and up Sarina's arm. Deidre was grunting as her cock surged. Harry felt himself getting closer as Sarina's hand quickened its pace. Deidre's cock exploded several more times as she panted loudly, covering Harry's cock with her thick, white cream.

  Then Harry came. As Deidre's cock expelled its last drops of semen, Harry's cock exploded. He screamed as the first ribbon of cum launched high into the air. Deidre bent and offered her small tits and face and Sarina made sure Harry hit the target. Suddenly, Harry felt like a teenager as glob after glob of hot cum splashed on Deidre's tits and face. The relief was overwhelming. His cock finally oozed the last of his load and Deidre bent lower to lick it from his cock and Sarina's hand.

  Sarina gently continued to stroke Harry's cock as Deidre let her legs flop from beneath her and she lay with her head on Harry's thigh. Harry tensed as the electric pleasure still surged through him. He no longer ejaculated, but he wasn't quite done. Harry grunted one last time and his muscles went limp and Sarina relented. Sarina played in the puddles of Harry and Deidre's semen with her fingers, while Deidre closed her eyes, spent.

  Harry turned and kissed Sarina. She nuzzled close and Harry wrapped his arm around the girl and squeezed. He felt relaxed and better than he had in years, maybe ever. These girls, Sarina especially, made him feel like a man. Ironic, he thought, considering they were technically men themselves. It didn't matter. These girls made him feel like no one else ever had. Harry mused over the thought, the absurdity of the situation and the deep satisfaction he felt and then slipped into a sound sleep.

  ~~~

  Harry awoke in the early morning, his room dark except for the soft, blue glow of the coming dawn. Deidre and Sarina were gone. Harry guessed he hadn’t expected them to stay, but he missed them. He hadn't felt that young or excited in years. Maybe last night would be a catalyst for a change in his life, Harry thought. He sighed and got out of bed.

  His ass was a little sore, but it served as a reminder of previous night's events. It occurred to him he hadn't needed even one of those little blue pills to get aroused. That hadn't happened in many years. Just thinking about it made him aroused again. Harry considered the idea that maybe his mind was the problem, not the plumbing. Maybe he just needed the right motivation.

  Harry showered, dressed and left his room to meet with clients. He felt a mix of satisfaction and loss all day. He really did miss those girls, especially Sarina. He finished his meetings, changed his clothes back at his hotel room, and went to the lounge. He tried to convince himself he wasn't hoping to see the girls, but he was. They never showed.

  A couple of days later he left for home. It was bittersweet. He would always cherish the night with Sarina and Deidre, but he knew he would probably never see them again. That made him a little sad, but he refused to let it depress him. He wanted a change in his life. He liked the way he felt with the girls and wanted more. Harry was sick of being lonely and depressed.

  Harry arrived home, a small condo that was in desperate need of a woman's touch. He grabbed a beer, cracked it open and fell into his chair. Harry began to take a drink, but his cell phone buzzed. Fuck! Harry set down his beer and trudged to the table where the phone vibrated insistently.

  “Yeah, yeah!” Harry complained as he picked up the phone. Private number. He considered not answering, but it could be a client. He pushed the green button and said, “Hello?”

  “Hi, Harry,” said a familiar, feminine voice.

  “Sarina?”

  “Yeah, sorry I left like that. Habit I guess. How are you?”

  “Fine, I guess. How'd you get my number?” Harry asked.

  “I took a business card from your briefcase. Hope you don't mind.”

  “Uh...no. I don't mind. I'm glad you called. I had a great night. Really, I did.”

  “Me too, Harry,” Sarina said and then hesitated before adding, “I miss you.”

  “Really? I miss you too. I was so disappointed when I woke up and you weren't there.”

  “Just me?” Sarina asked.

  “No, Deidre too,” Harry admitted, but added, “But more you.”

  The phone went quiet. Harry wondered if he had said too much. He wondered if admitting he also liked Deidre was the wrong thing to say. “Sarina?” Harry prodded.

  “Harry, when are you coming back? Soon? I want to see you again.”

  “I only live a few hours away,” Harry explained.

  “Really?” Sarina asked excitedly.

  “Yeah. I want to see you too,” Harry admitted.

  “Deidre, too?”

  Harry hesitated. He did, but he wanted to see Sarina more. Much more. He decided to be honest, “Yeah, if that's OK.”

  “It is. It wouldn’t be the same without her.. Maybe next weekend?” Sarina suggested.

  “Definitely! Friday? At the lounge around seven?”

  “Well, be there. I should let you go. See you Friday, OK.”

  “Um...OK. Friday! Bye, Sarina.”

  “Bye, Harry,” Sarina said and the phone went dead. Harry felt like Sarina wanted to say more. Harry sat down again, took a drink of beer and smiled. He felt good. He wondered if Sarina felt like he did. He wanted to say more, but was hesitant too. He wasn't quite ready to admit to himself how much he cared for her, but he wanted to see her desperately. He hoped she felt the same. Suddenly, Harry felt like he had a new lease on life. Next Friday couldn’t come soon enough.

  ~~~

  About the Author:

  Marlene Sexton is just a regular girl with a wildly sexual imagination. She has been writing erotica for her own enjoyment. Now she wants to share her naughty stories with others. She enjoys writing about hot and steamy sex between characters that her readers can connect with in realistic, but exciting, situations. Marlene loves writing about married couples, lesbians, transsexuals and all manner of dominant woman fantasies. Of course, all of Marlene’s characters are consenting adults.

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  If you enjoy transsexual erotica, try High School Reunion or The Virgin Wife by Marlene. Find them at your favorite retailer!

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