Rebecca's Secret Ch. 03

byWannabe Chick©

Around 10:30 AM, we both woke up and began our day.

Rebecca climbed out of bed and walked into the bathroom. She approached the toilet and stood there with her back to me. Through the gap between her bare thighs, I could see a stream of yellow piss falling into the bowl. I leaned on my elbow and watched her as she shook out the last few drops, then flushed. Next Rebecca turned to the sink. She put toothpaste on her brush and began cleaning her teeth vigorously. When she turned back to face me, I could see her penis wagging back and forth as she brushed her teeth. Rebecca smiled at me.

"Good morning," she said around the tooth brush.

"Is it morning?" I asked. "I could have sworn I was still dreaming."

"No cheesy lines allowed," she said.

"Sorry," I said. "I guess love makes you say stupid things."

Rebecca turned back to face the mirror. I slipped out from under the covers and joined her in the bathroom. I stood behind her and wrapped my arms around her waist. I leaned down to kiss her neck. As I did, I slid my right hand down into her soft patch of pubic fuzz and played with the black hairs. Rebecca spit, then turned her face towards mine. We kissed and I could taste her minty toothpaste in my mouth.

Rebecca pulled her lips off mine and smiled at me. She began rinsing out her mouth as I turned to the toilet to relieve myself. A minute later, we were both done, and she followed me back into the bedroom. I sat down on the edge of the bed and pulled her on to my lap. We kissed again, taking as much time as we needed to lose ourselves completely.

"I invited Kate to come back tonight," I told her once our tongues finally parted.

"That's cool," she said.

"I hope you're not jealous, though," I said. "It was fun with her last night but . . ."

"But you're in love with me?" she said, smiling. I blinked in surprise.

"You heard that?" I asked. Rebecca nodded.

"Hearing you say that was better than all the cheesy lines in the world," she told me. "Thank you."

"You're welcome," I replied.

"There's one more thing, though," she said, biting her lip in a gesture of nervousness. "It's something I was going to suggest before Kate walked in. I didn't want to mention it in front of her because I was afraid it would put too much pressure on you."

"What is it?" I asked her.

"I was wondering if you'd like to try anal sex," she said after a short pause.

"What?" I asked. I was confused. "We did that last night. Plenty of it."

"No, dumby," she said. "I mean with you on bottom."

It got through my thick skull at last. Rebecca wanted to have sex with me on bottom, meaning she wanted to put her dick into my ass. It hadn't even occured to me until now. Granted, my understanding of male and female had been changed literally overnight, but I still believed that the man was the one who did the penetrating. Rebecca had opened herself to me and allowed our bodies to become one, but wasn't that what the woman is supposed to do, even if she has a cock?

Plus there was the issue of the physical sensation itself. Rebecca liked it, but I might not. Would it hurt? And what would it do to change my life? Could I go into a sports bar and watch the Yankees and drink a few beers with my male friends, knowing that twenty minutes earlier I'd been sweating and grunting on my hands and knees with my girlfriend's six inch penis all the way up my butt?

I was being a complete idiot. Obviously this was important to Rebecca and, if I truly loved her, I should at least try it once for her sake. It wouldn't make me gay or any less of a man.

"I'm sorry for asking," Rebecca said, blushing. "I should have known you wouldn't want to try it."

"Hang on a second," I said, holding her back as she tried to climb off my lap. "I didn't say 'no.' I was just thinking it over."

"You don't have to if you don't want," she said. "I just wanted to please you the way you pleased me. I thought it could be another way for us to express our love for each other."

"You're absoutely right," I told her. "You were willing to let me into your body because you love me. I'm willing to do the same because I. Love. You."

Rebecca wrapped her arms around my neck and kissed me. I lay back on the bed, pulling her on top of me. She straddled my waist with the tip of her cock brushing my stomach and kissed me fiercely. When the kiss was over, she crawled off me, and knelt beside me on the mattress. She instructed me to roll over on to my stomach. I obeyed. She moved closer so that she was kneeling directly beside my ass. She placed her hand on my left butt cheek.

"Ready?" she asked.

"Let's do it."


Rebecca wedged the four fingers of her left hand between my ass cheeks and spread them apart. She repositioned her hand and then splayed her fingers even farther, exposing my hole. She popped her right ring finger into her mouth and sucked at it to get it wet, then put it against my anus. She rubbed it in a circle, then sucked on her finger again, and continued rubbing. She leaned her head closer to my crack and spit, dropping a large dollop of saliva on my asshole. She rubbed again, working in the natural lubrication, so her cock would slide more easily in and out of me.

"I'm just going to tease it a bit with my fingers," she told me reassuringly. "I'll let you know before I stick anything in."

"Teasing" was the perfect word to describe what she did. She rubbed her thumb against my asshole, occasionally pressing it against the rubberly orafice, and moving her thumb in a circle. As she continued the motions, I could feel myself getting looser. Each time she massaged my rectum, I could feel the flesh giving way to her touch, as if my body itself were becoming more at ease with her fingers probing me. She would step every thirty seconds or so to suck on her fingers again. Lubrication is the key to good anal sex, she explained. Trial and error with her dildos had taught her that lubrication and patience were the main components of a sufficiently loose butthole.

"Now I'm going to put my pinky finger in," she said. "You'll barely feel it."

She sucked her little finger until it was covered with spit, then positioned it against my asshole. She was right. I could barely feel anything except a strange friction as her wet finger glided into my body. Once her finger was buried up to the knuckle, she wiggled it in a circle to stretch out my sphincter. The sphincter is the part of the colon that keeps the nasty stuff inside until you're on the toilet but it's also the reason anal sex hurts so much if done improperly. Rebecca knew that loosening up my sphincter was the most important step before relal penetration.

"Now I'm going to use my middle finger," she said. "This will feel a little weird but only for a minute or two. Just relax and keep breathing."

I gave myself over to her care. I lowered my face into a pillow as she slid her pinky out of my butt and soon replaced it with her middle finger. I felt the friction once again, but also pressure as my sphincter tightened around her finger. I followed her instructions. I kept my breathing normal and tried to let all the muscles below my waist relax. Once her finger was as deep as it could go, she wiggled it around, this time harder than before. It hurt at first but, as the muscles become less tense, the pain subsided. She began to slowly pull her finger out, about half way, then push it back in again. It didn't hurt at all. Actually, it felt pretty good.

"Mmmmm . . ." I murmured.

"Feeling OK?" she asked.

"Very OK," I told her. "I can see why you like this so much."

"I'm going to use two fingers now," she said. "My middle finger and my pointer finger. Just keep still."

She pulled her middle finger out of my butt and popped it into her mouth, along with her index finger. She sucked them both for a moment, then went back to work. The two fingers glided gently into my anus. I felt pain again but ignored it, knowing it would vanish in a few moments. Once the fingers were inside, Rebecca spread them as far apart as she could, and turned her wrist in a half circle. My sphincter continued to stretch until the pain was gone and only the pleasant sensation of her fingers rubbing against my prostate remained. Then she began slowly pulling the fingers out and pushing them back in until she met no more resistance from my sphincter.

It was such a bizarre sensation to have something inserted into my ass. I was only used to things going out, not going in. But, although it was bizarre, it was pleasurable as well. I took a deep breath and sighed. Everything below my waist felt warm and relaxed. Rebecca's fingers working inside my colon was the only stimulus my brain was receiving, which suited me fine.

"You know what's funny?" I asked.


"If someone in high school had told me that some day I'd be lying naked on a bed with you while you shoved your fingers in my butt, I would have laughed my head off," I said. Rebecca laughed.

"It's too bad," she said. "I think we would have enjoyed high school a lot more."

"Yeah, that's true," I remarked.

"Well, sweetie," she said a moment later. "I think you're ready. How do you feel?"

"Like I'm about to melt," I answered.

"Perfect," she said, slapping me on the ass. "Now let's pop that cherry."


First, Rebecca needed her cock lubed up. She could have just as easily spat on her hand and rubbed herself wet, but where's the fun in that? Instead, she walked over towards my head, on her knees, and presented her nearly-hard cock for me to suck. I opened my mouth eagerly as she lay her slab of meat right on my tongue. I wrapped my lips around it and sucked it all the way into my mouth. The taste immediately triggered my salivatory glands and I used my tongue to rub my spit all over her six inches. When she at last removed it from my mouth, it was dripping with frothy saliva.

She crawled back over to my ass and straddled the backs of my thighs. I could feel drops of spit falling on to my ass crack as her cock was poised to enter me. She asked me if I was ready. I told her to hurry up. With a laugh, Rebecca leaned forward, and pushed the head of her dick against my crack. It slid easily between the two cheeks. She grabbed her shaft and guided her beautiful shemale penis towards the entrance to my butt. I could feel warm precum leaking out of her pee hole and lubing up my ass.

Rebecca placed her hands on either side of my ribs, almost like a sit up position, and lowered her crotch towards my waiting ass. At first, I felt pressure as her pink head pushed against my rubbery anus. Eventually, my body yielded, and she slid smoothly inside me. My sphincter offered almost no resistance. She still moved slowly, however, to make sure I was loose enough to be fucked. Finally, she was all the way inside. Rebecca lay on my back. I could feel her hard nipples digging into my skin. For a moment, she did not move, except to plant sweet kisses on my back and shoulders. I knew she was letting my butt get used to the feeling of a girl's cock inside it. I was grateful for her concern, but now that I had Rebecca's organ deep in my bowels, I wanted her to to fuck me. No, make love to me, the way I had made love to her.

"Stop teasing me, baby," I whispered. "Make a man out of me."

"Does this make you a man?" she asked.

"It makes me more," I replied. "After all, how many guys have the balls to let their girlfriends butt fuck them?"

"Right," she said. "And how many girls have balls at all?"

"One I know of," I said, "and that's all I need."

"Well, since you're so sweet, I guess I'll give you what you want," she said.

She lifted her pelvis and I could feel her cock sliding out of me. As it reached my sphincter, I felt a brief moment of panic, but Rebecca had cautioned me about this. Sometimes when the head touches the sphincter on its way out, it feels like something unpleasant is going to come out with it, but it's just a sensory illusion. I didn't have to worry about any kind of mess. It was just the nerves in my sphincter reacting to the friction of the underside of her cock head.

Perhaps sensing my discomfort, Rebecca pushed back in. I felt her cock rubbing against my prostate gland and her smooth scrotum pressing against my ass crack. Her thighs pressed against my butt cheeks. She withdraw again, then pushed back in. Her pace increased. Soon her balls were slapping loudly against my ass with each thrust. She sucked in breath through her teeth more and more rapidly. I thought it would hurt more if she fucked me harder but each thrust just loosened me up that much more and I could enjoy the pleasure of having my girl's warm organ deep inside my bowels more. It occured to me that Rebecca had been denied last night. She'd been waiting for hours to get a chance to fuck her loving boyfriend and now she was in a frenzy.

"How does it feel?" I asked her through grunts of delight.

"Fabulous," she said harshly. "Your ass is so hot and tight."

"Just be gentle," I said.

"No way in Hell," she replied with a laugh. "I've fantasized about this since ninth grade. I'm going to milk it for everything it's worth."

"I think you're the one getting milked," I told her.

She laughed, then threw her hair back and continued plowing my ass. Both of our bodies were slick we sweat and we rubbed together each time she went in deep enough for our bodies to touch. Still, I felt she could go deeper. I pushed myself to my hands and knees. Rebecca wrapped her arms tightly around my waist and planted the balls of her feet on the mattress. I took a moment to imagine how we must look - a girl barely over five feet fucking a guy over six feet doggystyle.

Rebecca's breath became ever quicker and she was fucking me like a demon. I knew her orgasm couldn't be too far off. Although I could have done this all day, I knew Rebecca must be dying for release.

"Do it," I told her. "I want your cum inside me."

"I love you so much, baby," she whispered with a ragged breath.

"I love you too," I said.

Rebecca let out a cry and I fould feel something white hot spurting into my colon. She thrust again and I felt a second surge. She thrust a third time, deeper and harder than before, and emptied the last of her nut into me. I slowly lowered myself back on to the mattress. Rebecca held on. She lay on top of me for a good three minutes, trying to catch her breath, as her penis returned to its normal limp size and slipped out of me. I felt empty without it in me, like I was more complete with Rebecca inside me.

Eventually, Rebecca rolled off me and on to the mattress. I snuggled in closer to her. She put her arms around my head and held my face against her chest. She was weeping softly. I knew it wasn't from sadness, but the emotions inside her had burst with that orgasm, and it would take a minute for her to get things back under control. I held her until then.

"Let's do it again," I said.

Rebecca laughed and kissed me.

"Our friends will think we're dead if we don't come down soon," she pointed out.

"You're right," I said. "Besides, there's always tonight."

"Tonight will be even better than last night," she promised. "And every night after."

We didn't leave the bedroom immediately. We lay in the bedroom without speaking, simply holding one another, feeling the strength and purity of our love. Rebecca was my girlfriend, emphasis on the word "girl." I loved her as much as any man can love any woman, whether they have a penis or not. As I squeezed her close and smelled her hair and felt the lingering warmth of her seed inside me, I knew my love for her would last forever.


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