Harry and the Transsexuals (3 page)

Deidre's cock was already hard and covered with a slick layer of her own juices. Deidre stopped stroking the shaft with her hand and held the base as she guided her cock into Harry's awaiting mouth. It was big. Deidre was gentle, but still her cock head easily reached the back of his mouth before barely half the shaft had slipped inside. With Sarina, he wanted to be gentle and loving, but Deidre's beautiful cock made him want to be more aggressive.

He took her shaft in his hand and began sucking her cock in earnest. Deidre smiled down at him and moaned. Harry knew it felt good. It would have felt good having his cock sucked like that.

“Harry, it’s so sexy watching you suck our cocks,” Sarina said softly. That made Harry want Sarina's cock again and he switched back, stroking Deidre while he sucked Sarina. Harry couldn't decide which he liked best. Sarina's small, girlish cock or Deidre's big, thick cock. Both were sexy in their own way.

For a quarter hour or so, Harry pleasured the girls with his mouth and hands. Deidre's cock leaked freely and her shaft was hard as steel and covered in big, blue veins. Sarina, on the other hand, remained only partially erect. Her cock leaked a small amount of tangy fluid, but she never managed to get hard like Deidre. Harry's cock, however, was hard like Deidre's and several rivulets of his clear juices glistened against his shaft.

Finally, Harry stopped. He needed to fuck something, anything. In Harry’s entire life he had rarely been this aroused. He sat up, grabbed each girl by her waist, and pulled them close. They smiled as he hugged them and then he turned to Sarina, concerned she wasn't excited, wondering what he might do.

“Your cock, why isn't it hard like Deidre's?” Harry asked looking into Sarina's sexy eyes.

Deidre answered, “Sarina has been through a lot to look like she does. Sometimes that affects a girl's ability to...uh...perform, Harry.”

“I rarely get hard, Harry, and almost never come, not for real anyway. Deidre hasn't done as much as I have. I'm committed to becoming a complete woman someday. For now, I enjoy the pleasure I get from pleasing others,” Sarina explained.

“So you can't have an orgasm?” Harry asked, feeling bad for Sarina, “Can you, Deidre?”

“Harry, I have big, explosive orgasms. Remember how it used to be when you were in your twenties? Well, I come like that,” Deidre replied and added, “I like being a girl with a cock. Don't feel bad for Sarina. Someday she'll be a real woman. For now, she loves a good ass fucking.”

“Makes me feel like a woman when a guy takes me like that. Wanna, Harry?” Sarina asked as she bent down on all fours and wiggled her voluptuous ass.

“Fuck you? Uh...yeah. I'm so fucking turned on. What about Deidre?”

“I'll take care of myself for a few while you take care of Sarina,” Deidre offered and then got out of bed, found her purse and returned with a few condoms and some lube, “First things first, though.”

Harry's cock was rock hard and Deidre had no problem slipping one of the rubbers over his cock. The girl then poured a little lube on the condom and some more on Sarina's ass. Sarina squealed when the cold liquid hit her anus and then shook her womanly behind at Harry again and exclaimed, “I need that cock, Harry! Make me feel like a woman.”

Harry wanted nothing more, though he couldn’t imagine Sarina being any more womanly even if she did have a pussy. Harry had done a girl in the ass in college, so he wasn't unfamiliar with the act, but he was surprised how much easier it was to get his cock into Sarina than it was with that girl back then. It only took a few seconds and Harry’s cock was deep in Sarina's ass. Deidre lay next to them watching and stroking her massive cock. Harry suddenly got that feeling again and had to try hard not to explode right then. He took a deep breath and tried to relax. Once he settled down, Harry began fucking Sarina's ass. Even through the condom, he could tell how smooth and velvety her ass was.

“Harry, I like it hard. Fuck me like a man fucks a woman,” Sarina begged. Harry didn’t have anything else in mind. Soon Harry had a hold of Sarina's generous hips as he roughly pounded his cock into the girl. Sarina moaned, squealed, and fucked back. She obviously loved anal sex and Sarina really let go.

“Oh, Harry. That feels so fucking good. I feel like I’m coming,” Sarina gushed and Harry picked up his pace.

Deidre continued to stroke her cock and asked, “Isn’t her ass amazing? As good as any pussy.”

“Yeah, it’s awesome!” Harry replied breathlessly and Sarina turned and smiled. Then, even though he was enjoying Sarina’s ass, he had to ask, “How would you know it’s better than pussy?”

“I like girl’s too, Harry. I love fucking pussy, but not as much as Sarina’s ass.” Diedre said grinning. Harry could hardly think of the blonde transsexual pounding a pretty girl with her big cock. It was too exciting.

Watching Deidre pleasuring her own cock was incredible too. It was so long and hard and she seemed to love stroking herself. Deidre’s cock glistened with pre-come and occasionally she all but stopped stroking, her body shaking slightly as if she was about to come. Harry knew exactly how she felt. His cock was leaking inside the condom and despite the rubber sheath Sarina's ass felt amazing. He wanted to come so badly, but wasn't about to let this end and somehow found the willpower to keep going.

Sarina’s sweet cries of pleasure and watching her voluptuous body ripple every time Harry’s hips met her fabulous ass were sexy as hell. From this angle, he could have imagined Sarina was a real woman, but he found he liked thinking of her small cock leaking as he fucked her. It didn’t matter; Sarina was the most feminine creature Harry had ever seen. Cock or not, she was all woman.

Sarina seemed to be having one long orgasm now and she screamed, “Oh, God! You’re cock feels so good, Harry! Fuck!”

Harry loved watching her like that and said, “Sarina, you’re such beautiful woman. The most feminine I’ve ever fucked.” She looked back and smiled gratefully. Harry knew she would like hearing that, but he meant every word.

Sarina's body was flush and beaded with sweat. The scene was surreal like some porn movie. This couldn’t be happening to him, Harry thought. He hadn’t fucked like this in twenty years. The room was filled with moans and grunts, each of the three deep in pleasure. The sights, sounds and sensations proved too much for Harry and he finally had to stop.

He pulled his cock from Sarina's ass, grabbed the base, and squeezed. Deidre shot him a look that told Harry she was feeling the same way as she forced herself to stop stroking. Sarina collapsed, her ass gaping for a moment, seeming to want to be filled again. Harry finally let go of his throbbing shaft and white semen oozed out. He didn't come, but he was very close and the small ejaculation relieved much of the pressure he felt.

Sarina turned over, her ample chest heaving as she caught her breath, “Damn, that was awesome. Harry, I felt so close to climax. You're wonderful.” Sarina sat up gathered some of his ejaculate on her finger and sucked it off. Then she kissed him, sharing the creamy ejaculate with him. Harry wasn't repulsed in the slightest. In fact, it tasted good. Sarina broke the kiss and licked her lips as Deidre cuddled up behind Harry and hugged him close, her cock pressing into his back.

“Sarina how did that feel? Was it good? Are you satisfied? I can't imagine not coming,” Harry asked curious and concerned.

“It felt wonderful. I like to imagine that's what a woman feels when she gets fucked. Just wave after wave of pleasure washing over her. No, sudden intense orgasm. Just beautiful, constant pleasure,” Sarina explained and then added sensing Harry's concern, “I hardly miss ejaculating. It felt amazing, I promise You were wonderful, Harry.”

“I'm glad. I wish I could make you come for real though. I just can't imagine how you can't miss that.”

“Wanna find out?” Deidre asked as she softly humped her cock against him.

“What do you...,” Harry began to ask, but then figured it out and exclaimed, “Get fucked in the ass? Uh...I'm not sure.”

“Harry, it feels so good. You should let Deidre fuck you,” Sarina urged.

“Yeah, Harry. I'll be gentle. Please?” Deidre pleaded seeming to genuinely to want to fuck him.

“Uh...yeah, what the fuck? I've gone this far. Does it hurt?”

“We'll start slow, Harry,” Deidre assured him, “Lay down on your back.”

Harry did as instructed, slightly nervous but highly aroused. Deidre snuggled in between his legs, lifted them into the air and spread them wide as Sarina stuffed a pillow under his ass. They had done this before apparently. Deidre pulled a condom on her long cock, worked some lube onto it, and then applied a little to Harry's ass.

“Deidre knows what she doing Harry. She was my first. She’ll make you love it,” Sarina assured harry.

Instead of her cock, Deidre used her finger to first smooth the cold gel around his anus and then worked her finger into his ass gently. It felt strange, but good. There was no pain until she tried to work the finger deeper. Harry already felt like Deidre's finger was completely inside, but as she slipped it in further he realized it had barely penetrated him at all.

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.