Dickgirl Diaries 3


The escapades of the teen dickgirl continue… Read parts 1 & 2 first…

////////// Chapter 3 //////////

The rest of the summer went by in a flash. Paulina and I spent nearly every single night together, most of the time in her house as my parents weren’t quite as acceptive of our relationship as hers were. Our sex was absolutely amazing, and there was a lot of it. Though our sessions mostly consisted of me licking her pussy, her sucking on my cock or me fucking her in missionary position, it always felt just as new and exciting as it had the first times. Penetrating my teen girlfriend was pure bliss each time, and she didn’t seem to get enough of my girl-cock either. I found that Paulina often wanted me to finish off in her mouth, and on some nights she’d eagerly gulp down three or four loads of my cum until we drifted off to sleep in each other’s arms. More often than not we were both sore in the morning.

Something had begun to worry me though. Many times, on the nights when we slept in my house or when I slept alone, I would hear faint sobs coming through the wall. Not all was well with my little sister Annie, I knew.

I also thought I knew what had her upset. Annie was, you see, different just like I was. I figured that she was probably going through the same identity crisis I had just recently managed to overcome myself. Only Annie didn’t have Paulina to help her with the process, and I was worried how she would manage.

Annie was a shy, good-girl type, and where I had always surrounded myself with people, she had seemed to enjoy being alone. Not that she would have been a loner or anything; she did have friends, but she just wasn’t the popular girl that I was, and I feared that made things tougher for her.

She would have had the looks to be just as popular as I was. Annie had always been just the cutest girl ever, but in the past years Mother Nature had begun shaping her cuteness into the pure, raw beauty and sexiness of a teenage girl. At about an inch over 5 foot she was almost a head shorter than I, but had the plump butt and boobs to make up for it, and a slender waist to emphasize them. Her angelic face was framed by light blonde hair reaching halfway across her back. Her smooth skin was a shade darker than mine, and her eyes a vivid ice-blue. Her supple lips would have made any young guy give his left leg to kiss them, and an arm to have them around his dick.

I had always thought her pretty, but lately I had begun seeing her as a sexual being, too. I wasn’t sure why, but I thought it was because of Paulina, who was regularly pointing out how hot my little sister was, in fact, she had done so even before we had begun our intimate relationship. Despite the fact that Annie was my sister I found her curiously sexy, and a number of times – to my shame – I had jacked off to thoughts of her.

Annie and I had used to be very close, but we hadn’t really had a good talk in quite some time by then. It was hard talking to her when all she seemed to do was hide in her room. At first I had thought she just needed some time on her own, but lately I had become convinced that she needed my help. When I told Paulina of my worries she, too, encouraged me to go and have a chat with Annie.


Then, one night when Paulina and I were staying in my house, faint sounds woke me up in the middle of the night. Annie’s crying again, I thought. Gods, the poor girl must be miserable. I wish I knew how to help her. In my sleepy mind it seemed like a good idea, and I decided to go and finally talk to her. First, though, I put on a pair of lace panties and a white nightshirt, not wanting to confront her naked.

It was dark and our parents were sleeping downstairs, so I opened and closed my bedroom door gingerly so as not to wake them. I snuck over to the door to Annie’s room, the one next to mine in a hallway upstairs with two other doors leading to a bathroom and an unfinished TV-room. I didn’t bother to knock, I never did, and cracked the door open and peeked inside.

I immediately realized they hadn’t been sobs I had been hearing this time, but quiet moans. Annie was sitting on her bed bent down, her head slightly bobbing in her lap, her ample tits and hair swaying with the movement. Her hair covered her partly, but I could see enough. Both her small hands were furiously stroking the long shaft of his thick cock while her mouth suckled on the bright pink tip. I pulled back, shocked.

Had she seen me? No, her eyes had been closed, and she had been too focused on herself. My panties felt cramped, and I realized I was feeling unbelievably aroused. I pulled my panties down enough to free my throbbing erection, just to relieve the ache. I wanted to touch myself, but I fought back the urge. This is so wrong, I thought, trying to make myself walk away, but my legs refused to move. Soon the temptation grew irresistible, and I cracked the door again to take another peek at my masturbating little sister.

What I saw blew my mind. This time, as if what she had been doing previously hadn’t been sexy enough, she was working one slender finger between her pert buttocks and into her asshole. Her other hand was a blur on her shaft and her mouth was intently working on the head of her cock.

Her light, muffled moans were becoming more intense by the second, and I was having a hard time keeping from moaning myself just from watching her. I knew it was terribly wrong to peek on my little sister like that, but she looked just so incredibly sexy pleasuring herself and I couldn’t find the willpower to go away.

Soon Annie inserted a second finger into her ass, shivering as she penetrated herself and stopping her other actions for a moment as she worked her fingers deeper. Then her head began bobbing up and down again and her muffled moans returned ever louder. In only a moment her whining grew erratic, and as I watched her tremble all over and her balls contract, she began spurting cum in her own mouth. My mind was going crazy. I heard her swallow several large gulps as her hand kept stroking and pumping more and more cum from her pulsating cock into her waiting mouth. Her fingers worked in and out of her asshole the whole moment, until finally she collapsed on her back on the bed, her dick still twitching in the air.

”Damn that was hot,” Paulina whispered in my ear, causing me to jump in panic and slam the door shut.

”God damnit Paulina, don’t sneak up on me like that!” I hissed, my heart throbbing. I pulled her by the arm in my room and closed the door. ”Maybe she’ll think it was just a draft,” I whispered hopefully.

Paulina just smiled at me devilishly.

”What?” I snapped.

”You dirty girl, watching your little sister masturbate,” Paulina teased me, her finger toying on my lips. ”Oh, and what’s this?” she continued with a feigned look of surprise, poking my erection. ”Somebody’s got the hots for her little sister!” she proclaimed. I felt myself blush, and that only seemed to excite Paulina more. She grasped my shaft and stroked my length a couple of times, causing me to involuntarily lean against her and shiver.

”Listen, we –” I started, but my words turned to a moan when Paulina dropped on her knees and promptly plunged my cock in her mouth.

”We what,” she purred, looking up and smirking.

”Nevermind,” I sighed. If this was how she teased me I was game. Her other hand began fondling my plump balls while her hungry mouth worked on all the sensitive spots on the tip of my cock.

She paused again and looked up, grinning. ”Are you thinking about her now?” she teased.

”No,” I lied.

”Liar!” she exclaimed triumphantly, standing up and pushing me on my back on the bed. Paulina was strong for a girl as slender as she was, probably stronger than me.

I would have thought she’d be disgusted or angry at me for getting hard peeking on my sister, but she only seemed incredibly horny. Her slit was practically dripping on my cock as she wriggled herself on it, finally sitting down to engulf me inside of her heavenly warmth. She let out a gasp as her pussy stretched to accommodate my girth.

”Keep quiet,” I tried to tell her, but was having a hard time keeping my own volume down as she began riding me. Her perky tits bounced and her hair swayed beautifully as she slammed herself down on me again and again. Soon she collapsed against me and started rocking her ass up and down, grinding her clit against my pubic bone. Her firm breasts squished against mine through the thin fabric of my shirt. It was such a thrill having her take me like this, usually it was me doing the fucking.

”I… can’t… blame… you,” she panted in my ear. ”She’s… hot as… hell… uhh… almost… as hot… as you… mmmhh.”

”Yeah?” I huffed back. ”What if… it was Annie… and not me… you were riding… right now?” I don’t know what made me say those words.

”I’d make… her cum… in my pussy,” she moaned, reaching back and squeezing my balls hard. She bit her lip and smiled fiendishly. I could feel her juices leaking onto my scrotum and between my ass cheeks. Her pussy was a hot, wet glove on my dick, gliding up and down and massaging my whole length. I had never felt so horny in my life, and if she had asked if we could get Annie in on the fun I’d probably have said yes without blinking an eye.

Suddenly she stopped, and her eyes went wide and her mouth spread to a big grin, as if she’d just come up with the greatest idea ever. ”Let’s ask her to join us,” she whispered, exhilarated.

”What?!” I gasped, feigning shock. ”She’s my sister!” My cock throbbed impatiently, and I pushed up inside Paulina a couple of times.

”Oh come on, we both know you’re hot for her,” she teased. “And besides, she could use some cheering up, I think.”

”And what if she doesn’t want to?” I asked, blushing because her claim was true.

”Oh, she will,” Paulina assured knowingly. ”I’ve seen the way she looks at us.”

The thought of seeing my hot little sister fuck my beautiful girlfriend was so thrillingly sexy I felt my balls contract just from the idea. My cock felt so hard it hurt. I guess it should’ve felt like a horrible idea, but frankly I was so horny I would’ve been open to almost anything Paulina could have suggested.

”Fine,” I said, again thrusting up inside her sweet pussy a few times, trying to relieve the ache in my dick.

She just stared at me for a while. ”I can’t believe you actually said yes,” she said, genuinely surprised, then smiled happily. ”Let’s go!”

She stood up, my cock slipping out of her slit with a small pop, and scooted to the door.

”Well? Come on,” she rushed me. I got up and followed her to the dark hallway.

Cracking Annie’s door open we found that she had turned her nightlight off and was now sleeping. We snuck in her room and closed the door. The walls of her room were the lightest shade of pink and covered in Taylor Swift posters, while her bed was a waist-high twin bed. Annie was sprawled naked on it, laying on her side without covers, her plump butt towards the door.

”What now?” I hissed in Paulina’s ear.

”We wake her up,” she said.

I was starting to have second thoughts about Paulina’s idea, but then Annie rolled on her back in her sleep and I was distracted. Sister or not she looked just so damn cute. She had the prettiest boobs ever, two soft fist-sized balls that fit perfectly on her small frame. Her fat, limp cock lay against her thigh. I thought it weird that I found even her dick attractive, but I supposed it was because it was attached to a girl, not a guy.

“Annie,” Paulina whispered. “Wake up!”

Annie whined lightly in her sleep.

“Annie!” Paulina whispered louder, this time gently shaking her by the shoulder.

“Wha…? Uhh?” Annie murmured drowsily, opening her eyes.

When she saw us her eyes went wide with shock, and she jumped to the back end of her bed, making a vain attempt to cover herself with her bedsheets. She looked like some cute, alarmed little animal, and I had to let out a giggle.

“Wh– what are you guys doing here?” she asked in a meek voice.

“Don’t be alarmed,” Paulina purred in a soft, seductive tone. Annie squirmed awkwardly. “We’ve got a proposal for you,” Paulina continued, standing up to her full length.

Only then Annie seemed to notice that Paulina was naked. Her jaw dropped and she just stared at Paulina’s boobs.

Paulina opened her mouth to speak, but stopped as she caught Annie staring. She grinned wickedly. “You like them?” she cooed.

Annie bobbed her head in approval.

“What about this?” Paulina asked, turning around and bending over, granting Annie and I a clear view of her ass and pink slit. Annie gasped. My girlfriend really played the part of the seductress quite convincingly.

I just watched the show she was putting on, feeling anxious and horny at the same time. I noticed a bulge had appeared in the bedsheet Annie was using to cover herself. Paulina turned back around, smiling coyly.

“I see someone likes me, at least,” she purred, tracing a finger along the bedsheet to the tent in Annie’s lap. Paulina leaned closer, and closer, smiling that wicked smile, and though Annie looked frightened she remained still, her eyes alternating between my girlfriend’s lips and tits.

And then they were kissing, or more like Paulina was kissing Annie, trapping her against the wall. Paulina’s hand fondled Annie’s bulge, causing her to whine in my girlfriend’s hungry mouth. I felt my own cock throbbing as I watched the incredibly erotic display.

As if she would have forgotten how to use her hand the bedsheet slipped from Annie’s grasp, revealing her blossoming breasts once more, and as Paulina leaned in even closer their supple tits squished together. Paulina’s hand groped and squeezed and petted Annie’s erection through the thin fabric, making the smaller girl tremble and moan in a light voice. I felt a sudden, strange surge of jealousy, but the emotion somehow only made me hornier.

After a long, hot moment they parted, and Paulina asked, “Do you want to hear our proposal?”

Annie just nodded, looking absolutely bewildered and breathing rapidly.

“Come with us,” Paulina purred, taking Annie by the arm. “I’m going to make you feel really good.”

Annie smiled for the first time that evening, a silly, lucky smile, like a little girl who finds a pretty butterfly. She wasn’t a little girl though, but a lustful teenage beauty who just happened to have a cock instead of a cunt. All the other womanly parts and shapes she had, though, making for a stunningly sexy package. I admired her perfectly shaped buttocks as Paulina led her past me. For a moment I even wondered what’d it be like to slide my cock between those firm buns of hers, before I caught myself and followed her and Paulina to my room.

“So… how are we doing this?” I asked nervously after closing the door behind me.

”Tell you what, you guys sit like this,” Paulina instructed, making us sit on the bed reclining on our arms, facing each other with our legs spread and our butts together, so that our balls touched and our girly cocks leaned against each other. Annie’s was a little smaller, and the head was a brighter pink in color. I wanted to touch it so bad. It felt so hot against my own shaft. The position felt kind of awkward despite my lust, but Annie seemed excited as ever. Her beautiful tits were rising with her rapid breaths as her eyes traveled across Paulina’s body and mine. I took my shirt off and flung it to the floor to let Annie see my tits, too, it only seemed fair.

After admiring us for a moment with a smile on her face that said, ”I’ve got you both for myself,” Paulina knelt next to us and ducked down to kiss the tips of our dicks. Annie gasped when Paulina stuck out her tongue to swirl around our glans, and began whining ecstatically when Paulina started stroking our shafts at the same time. Our dicks rubbed together as Paulina pleasured them. In only a moment Annie’s moans began growing louder, and Paulina stopped.

”Now now, don’t cum yet,” she told Annie with a mischievous smile, then returning to work on our dicks.

Soon Paulina started sucking the pink heads in turns. When her lips first engulfed Annie’s cock my little sister shivered all over and her hips jerked up to meet Paulina’s mouth. Paulina took her time with her, slowing down her slurping and stroking when Annie seemed close to orgasm. Finally Paulina switched, placing her mouth on my cockhead in turn and causing Annie to let out a small disappointed huff. I shuddered when Paulina began sucking on the tip while stroking both of us with her hands. It didn’t take long for my climax to approach, but Paulina felt my cum building up and ceased her excerpts, leaving me and Annie panting expectantly.

”Hold on,” she said. ”And don’t move,” she continued, drooling all over our cocks until they were sopping wet and she seemed happy with the result.

Then she stood up, turned towards Annie and began squatting down between us. I was granted a glimpse of her bare slit and ass as she lowered herself in our lap, her breasts brushing against Annie’s face. I was puzzled. Was my girlfriend going to ride my little sister and leave me unattended?

When Paulina was low enough she grasped Annie’s cock and guided it to her entrance. ”Don’t move,” Paulina reminded her again, gingerly sliding just the first inch of Annie’s throbbing member inside of her. Annie whined impatiently, but remained still. Then Paulina’s fingers coiled around my saliva-coated cock, and I realized what she was doing. She pressed my dickhead against her pink asshole, and wriggled herself down until the tip popped inside.

”Oh shit,” she squealed. I watched the sight in awe and disbelief, my swollen girl-cock vanishing between Paulina’s perfectly pert buttocks. It felt intensely tight. I couldn’t believe she was taking me in her ass!

Then without warning Paulina dropped down, impaling both her holes on our cocks. I shivered as I felt myself slide into Paulina’s ass for the first time, but Annie almost cried in pleasure as her young virgin dick sank in my girlfriend’s pussy. Paulina’s breathing came in short puffs as she sat there completely full of cock. No one moved in a while. I pulled myself up against Paulina, who in turn was leaning against Annie so that we all kind of embraced.

”Gods,” Paulina groaned. “You guys are… pretty big.”

Annie whined and squirmed the whole time, until finally she started humping up inside Paulina and her whines turned to light shrieks. I could only imagine how mind-blowing it must have felt for her to have Paulina’s wet pussy surround her inexperienced member. I didn’t have to imagine how good Paulina’s ass felt, though. It was just unbelievably warm and tight, and as I began thrusting up in her the pleasure grew absolutely overwhelming. When I felt Annie’s cock rub against mine through Paulina I completely lost it, my hips jerking involuntarily as I thrust myself in Paulina’s ass again and again.

“Oh – my – Gooo – ood,” Paulina cried as she felt our two thick shafts moving inside of her. “Oh fuck!

Something made me reach around and hug Annie against Paulina’s chest. To my surprise Annie put her arms around me, too, pulling me against Paulina’s back. We were all so close to each other. It felt like we were connected somehow as I sat there with my butt against my little sister’s butt, our girl-cocks gliding inside my girlfriend’s pussy and ass only inches from each other. Annie and I had always been close, but this was close on a whole new level. I was incredibly happy for Annie, who seemed to be in seventh heaven inside Paulina’s pussy, but at the same time I was a little jealous because, well, another cock got to enjoy my girlfriend’s body and give her pleasure.

Annie was spasming and moaning uncontrollably as she pistoned her engorged cock in and out of Paulina’s soft, supple tunnel. Her scrotum rubbed against mine and her cock against my cock through Paulina’s flesh. She pounded like a small jackhammer, utterly lost in the pleasure of her first intercourse with my girlfriend. She gasped and moaned each time she thrust up between Paulina’s thighs. Paulina was equally ecstatic, her hips gyrating almost instinctively and rising and lowering to meet our strokes. I fucked her ass in wild abandon, my cum building up with each thrust.

Soon Annie’s strokes slowed down and she trembled and shivered and finally she just buried herself all the way in Paulina, screaming and crying as she began squirting her cum in my girlfriend’s pussy.

“That’s it baby,” Paulina moaned, kissing her. “Cum inside me like a good girl!”

I could feel Annie’s balls contracting and her cock twitching as she ejaculated. She pounded between Paulina’s legs, thrusting her cock in and out as she sprayed her load in my girlfriend’s acceptive vagina. It must have felt blissful for Annie as she literally cried while cumming in Paulina’s tight pussy.

I felt Paulina’s ass clenching around me as she, too, began cumming, driven over the edge by the sensation of my little sister’s sperm rushing inside of her body. She moaned in Annie’s mouth while they came together, rocking their hips against each other.

Hearing and feeling their orgasms was too much for me, and the ache in my balls grew to a storm of pleasure taking over my whole body. I slammed my cock in Paulina’s asshole, pulled out and slammed up again, a torrent of cum erupting out of me as my cock slid back inside the tight, hot tunnel between her buttocks.

“Oh fff-uuuuck,” Paulina moaned as she felt my cock spasming inside of her. “Cum in me Jenny!” she panted. “Cum inside my ass!”

The sensation of ejaculating in the snug squeeze of my girlfriend’s ass was just out of this world dizzying. I held onto Annie and Paulina like my life depended on it and humped against Paulina’s butt, sliding my throbbing cock in and out of her warm asshole as I trembled in the ecstatic pleasure of releasing my girl-cum.

Once I was finally spent I just collapsed on my back, panting and shaking in the aftershocks of my climax. Paulina rolled off us on her side, plentiful amounts of cum pouring from her slit and ass as our softening dicks slipped out.

“Holy shit,” Paulina exclaimed after we had all been quiet for a while.

Annie just smiled the biggest grin I’d ever seen, still sitting in the same position. I was feeling really, really sleepy, which wasn’t that surprising considering it must have been close to dawn by then.

“Did you like that sweetie?” Paulina purred in Annie’s ear.

“Uh-huh,” Annie huffed happily.

I drifted off to sleep listening to them kissing.


I woke up to a warm and soft sensation around the tip of my cock. Letting out a deep sigh at the sweet feeling I opened my eyes and saw a cute blonde-haired figure kneeling next to me, her head bobbing in my lap. At first I thought it was Paulina, but then I remembered the events of last night, and I realized: the sexy slender vixen slobbering on my dick was my sweet little sister!

She really knew what she was doing with her mouth, which I guess wasn’t a wonder as she had apparently been practicing on herself. She let her lips slide down my length as a soft, wet ring, then applied a gentle suction as she drew all the way up to the tip of the glans. She did it torturously slowly, and I had to fight back the urge to hump her face.

This is wrong, I thought dimly, I should tell her to stop. Yet I made no effort to. God, it feels amazing. Her lips are so soft…

Soon she picked up the pace, sucking up and down the upper parts of my shaft in rapid strokes. Her skilled tongue whirled around my tender glans, finding and caressing all the sweet spots. Her beautiful blonde hair swayed and tickled my crotch as she kept up her determined oral assault on my throbbing member.

Out of the corner of my eye I noticed movement, and I glanced over to see Paulina watching the show with her hand a blur between her legs. When she noticed I was looking she smiled slyly, then, before I knew what was happening, she spun around and positioned herself between my legs.

“Wait,” I tried to say, but my words came out as a sleepy mumble.

The next thing I knew was something hot and moist tickling my delicate butthole. I jumped at the surprising sensation, inadvertently forcing my cock deeper into Annie’s mouth, but she didn’t even gag and continued blowing me.

“Relax,” Paulina cooed.

Soon the sensation returned as my girlfriend tentatively lapped her supple tongue at my untouched ass, circling the tiny hole and licking over it. I shivered. The feeling was thrillingly incredible, and I spread my legs to give her better access. At the same time Annie coiled her fingers around my shaft and began stroking my foreskin while her silky lips and tongue massaged the exposed head. Her other hand cupped my balls, squeezing and fondling them gently. I thought I’d lose my mind from the pleasure.

Just when I thought I couldn’t take it anymore I felt Paulina’s slim tongue slowly wriggle inside my ass, and I lost all self-control. I sobbed uncontrollably, my body squirming and quivering, my hips rising to meet Annie’s mouth. My balls contracted in the gentle squeeze of her hand as my cum rushed up my shaft, and I let out a sharp gasp as I finally came.

Paulina tongued my sensitive asshole and Annie stroked and sucked on my spasming dick as I began unleashing a huge flood of pent-up cum in her warm mouth. She hummed approvingly and eagerly swallowed my seed as I released it, milking out more and more bursts with her hands and lips. The feeling of ejaculating in my little sister’s loving mouth while Paulina licked my ass was absolutely stunning. Tears brimmed in my eyes from the medley of heavenly sensations.

Annie nursed on my cock as my orgasm subsided, imbibing every last drop of my sperm until I was spent. I caught myself smiling like an idiot for no reason in particular.

Suddenly the door slammed open. My mother stood in the doorway, her eyes wide as saucers.

Jenny,” she gasped. ”Annie!

”Mmmmh,” Annie mumbled, spilling cum from her mouth.

Mom took a step back, then collapsed face first on the floor.

Needless to say we never slept together in my house again.


It wasn’t the end of our sexual escapades, however, no matter how hard my parents tried to make it that, and somehow, Annie just kind of merged into the relationship of Paulina and me. As strange as it sounds it felt completely natural, and it opened up a whole world of new possibilities when it came to sex.

It changed Annie a lot. Her frowns and sulks turned to smiles and laughs, and she was just the happiest thing, seemingly without worries and careless as a bird of the skies.

One night, when we were laying on Paulina’s bed basking in the aftermath of glorious sex, Annie simply said, ”Thank you,” and though I didn’t ask what she meant, I thought I knew.