Maybe, It Gets Better

Even while I sucked and played on Casey's breasts, my cock remained inside of her. For a moment, I felt that just her squeezing me was going to feel so incredible that I was going to cum. I was embarrassed just by the thought, but it quickly passed.

But I decided I needed to do more for Casey. I put my hands on either side of her body, lifted myself up, arching my back. My hips thrust forward, driving my cock more deeply inside of her. Casey moaned and bit her lip. I pulled my hips back, letting my cock slip a couple of delicious inches out of Casey's hot pussy. The cool air felt alien, and I thrust my hips forward again, sinking deeply inside her warmth again.

"Yes...Ana, oh! Fuck my wet cunt!" she moaned, as I slowly began to pick up the pace, thrusting my cock in and out of her. I giggled.

"Language, young lady!" I teased.

"Fuck me, fuck me, fuck me!" Casey moaned, impervious to my scolding. I heard a soft giggle. While I continued to thrust, I looked up. I had almost forgotten that Chloe and Natalie were there. I continued to thrust into Casey's beautiful body as I looked up at the other girls.

Chloe was still sitting on the cot, her legs spread. But Natalie wasn't kneeling in front of her anymore. Instead, she had turned around, her lithe, beautiful body clear to me now. Her perky, pierced breasts sitting high on her chest, her legs looking impossibly long. Her hands were on Chloe's thighs. And as I watched, she lower and raised herself gently, slowly. I looked between her legs, which were spread slightly, and I could see Chloe's hard cock slipping in and out of her pussy.

Chloe's hands were on Natalie's hip, helping the girl to rise and fall on the hard cock. But as I watched, Natalie began to move herself up and down much faster. It was clear that Natalie didn't need Chloe's assistance. Chloe sensed it too. Her hands rose from Natalie's hips, finding Natalie's narrow hips, and then her ribs. Finally, Chloe's hands moved across Natalie's breasts, eventually slipping her palms over them. I watched as Chloe gently squeezed her friend's breasts, and Natalie moaned appreciatively in response.

Natalie thrust her hips down once, gasping as Chloe's cock pushed deeper inside of her. Natalie paused turned her head over her shoulder, looking at Chloe saw her, and their lips met. I saw their tongues licking one another's lips, tasting each other giggling. Natalie broke the kiss and began to rise and fall on Chloe's cock again. Chloe kept kissing Natalie, on her back now while still massaging Natalie's breasts.

Watching the two girls make love have been so beautiful, I hadn't even been thinking about what I was doing. I was still thrusting my cock in Casey's warm pussy. In fact, while I wasn't paying attention, I had been thrusting harder and faster inside of her, reacting to the excitement of watching Chloe and Natalie. Casey reacted out that new intensity, drew my attention back to her as she moaned loudly.

"Oh my god, oh my god!" Casey panted. I looked down at her, saw that her eyes were slammed shut, her face beautifully contorted with pleasure, "Oh Ana, don't stop, I am going to cum!" Casey begged. I kept thrusting, but instinctively, my head dropped, my mouth finding Casey. She had just opened her mouth to moan and my tongue plunged inside of her. And I kept thrusting my cock inside of her, if anything getting faster.

Natalie and Chloe heard Casey moaning. They slowly stopped moving. Chloe looked around from behind Natalie's back so that they could both watch Casey cum. I leaned back slightly, and my hand found its way between Casey's legs. While my cock thrust in and out of Casey's body, I felt my thumb land on Casey's clitoris. She felt it as well, as her eyes shot open and her body began to tremble.

"Don't stop! Don't stop!" Casey begged. I kept thrusting my cock into her and, at the same circling my wet thumb around Casey's clit.

"Cum for teacher, you little slut," Chloe said, giggling a little. Natalie whistled. Casey's head rolled back and she saw her friends watching her. She smiled at them, and it was like knowing they were watching pushed her over the edge. I heard a loud croaking noise in the back of Casey's throat. And then I felt her thighs close around me, her legs wrapping me. She pulled me in, hard, so that my cock pushed deeper than ever. Casey's entire body was shaking wildly, and her croak had turned into a loud moan. Her eyes were slammed shut and her mouth was frozen open. I felt all of her muscles tighten. And then, slowly, loosen.

I had made a student cum. I'd fucked her with my cock. But I didn't have time to think about it. Even as I was slowly pulling my cock out of Casey's dripping pussy, the other girls were ready for me.

"You know," Chloe said, her hands moving up and down Natalie's body, "I have always sort of wondered what it would feel like to be with another transwoman," she raised her eyebrows. Any nerves were now gone for Chloe, she was back to her commanding self. And suddenly, I found that alluring rather than annoying. Natalie slipped off of Chloe's cock, stood in the room.

"She is so tight, Ana. And I got her asshole very wet," Natalie said, lifting herself up off Chloe's hard cock. I felt my own penis twitch at the idea.

"I've never fucked anyone in the ass before," I said, honestly, "My husband wouldn't let me."

"We are both virgins then, no one has every put anything..." and Chloe looked at Natalie, "Anything bigger than a finger into my ass. We can have some firsts together." As she suggested it, Chloe started to rise up off of the cot, until she was standing.

"God, this is going to be so hot," a voice below me said. I looked down at Casey. She had twisted her body around to look at Chloe, even though she was still panting. I returned my gaze to Chloe. She hadn't been waiting for me in the meantime. She had laid down on her back on the floor. She had immediately spread her legs and pulled them up, so that her knees were almost in her armpits. Her asshole was glistening with Natalie's spit, facing towards me, her small balls just above it. Her hard cock was pressed into her stomach, still wet from Natalie's pussy. She reached over on the floor and grabbed a bag, her back. She dug through it quickly and pulled out a large bottle of lube.

"I thought this was only going to be for masturbating," she said, laughing. She squeezed some of the lube into her hand and quickly moved it down, massaging it against her asshole. It was sexy just watching her massage the gentle folds of her anus. Natalie picked up the bottle of lube and squeezed it into her hand.

"Stand up, Ana," Natalie said, and I did as I was told. I walked around Casey's body (and she sat up, her breathing now under control). Natalie walked over towards me. I kept watching Chloe, spread-eagle, spreading lube on and in her cute little ass, her small, perky breasts spread out on her chest. I wasn't even looking at Natalie as she wrapped her hand around my cock. I just a little, the lube had made her hand cold.

"Sorry," Natalie said, and giggled. But she gently began to spread the lube on my cock. Her hands were soft, gentle. But they moved quickly. Somehow, I managed to turn my eyes away from Chloe, turning to look at Natalie. We didn't speak, just looked in one another's eyes. And then my eyes closed and I leaned into her. I felt her lips against mine, her tongue licking my lips, as she continued to stroke my cock and coating it in lube. I felt her pull away and groaned a little, I could feel her lips smiling. She moved her head, so that those delicious lips were against my ear.

"Fuck her little ass until she cums," she whispered, and I felt a nasty warmth flow through me. I turned again and looked at Chloe. She had moved her fingers away from her ass, and she was now just staring at me. At my cock. She saw me looking, and hooked her finger at me.

Almost in a trance, I moved towards Chloe and dropped down onto my knees in front of her. My cock was dripping wet with lube and harder than it had been in...a decade. As I got closer to Chloe's body, I could see her smooth, beautiful skin, feminine curves, and cute, hard cock. Her body smelled sweet, inviting.

"Don't worry about hurting me," Chloe said, almost reading my thoughts, "I will take it. I need it," she said. I nodded, and reached down, grasping my cock. Natalie dropped down next to me, leaning over Chloe's leg, biting her lip, watching.

I positioned the tip of my cock against Chloe's crinkled anus. I looked up at Chloe, her eyes sparkling She was smiling. She thrust her hips down, bouncing her asshole off of my cock. Chloe wanted it bad. I pushed my hips forward. I felt the tip of my cock press into the Chloe's anus. I felt pressure and a small amount of friction, her virgin body resisting me. Chloe whimpered a little.

"Shh..its okay," Natalie said, soothingly. She reached her hand down over Chloe's thigh, her fingers finding their way to the tip of my penis and Chloe's anus. She gently massaged Chloe's asshole with the tips of her fingers, and I could actually feel Chloe's whole body relax. I felt Natalie's fingers find the tip of my penis. I released my cock, letting Natalie gently guide me.

There was still some slight pressure, but not nearly as much. Natalie's delicate fingers felt wonderful on my cock, and I felt Chloe's body open for me. Felt her asshole open to me and the tip of my hard cock slipped inside of my student.

"Oh God!" Chloe moaned, her body writhing. I could see Natalie smiling. She leaned down and placed a gentle kiss, right where my cock was entering Chloe's body, touching us both. Then she leaned back, just watching. I kept steady, even pressure with my hips. I looked down, watching as Chloe's asshole stretched further and further, and my cock slipping deeper and deeper inside of her. She was unbelievably tight, tighter than Casey's sweet pussy. The insides of her body pillowy and constricting, but well-lubed and friction-free.

And then, like magic, I felt Chloe's soft balls pressing against my belly. And my cock was completely inside of her. Chloe's asshole clenched, and I groaned, I had never felt tightness like that before. I looked up now, now longer watching my cock slip in. I saw Chloe's penis, and hard and laying against her smooth belly. I my eyes moved up, over her perky breasts, to her pretty face. She was looking down at me, her eyes wide in amazement. I had never seen her look more beautiful.

Chloe's lips were just slightly open. I couldn't resist. I leaned forward, driving my cock deeply into Chloe. She groaned, her mouth opening wider. But I caught her moan in my mouth as my lips came down on hers. I felt her tongue press into my mouth, fervently. Our breasts pressed together, there was no daylight between our bodies, I could feel her cock hard against me. My own penis, buried deeper than ever inside of me.

Chloe broke the kiss, and I moved my mouth down to her neck, sucking and licking on her skin. I could feel Chloe's breath against the side of my face, and then to my ear. At first she just panted and moaned into it, but eventually, I could her speaking. Just barely a whisper, so that the other girls could not hear.

"I am so glad you are who you are, I can't believe it," she said and I thrust my cock harder into her, making her shiver. "Now I know that everything is going to work out. That I can be me," she said. I laughed a little, moving my lips away from her neck. I moved my lips to her ear.

"I am a middle aged, divorced woman currently putting my career in jeopardy in the...most pleasurable possible way. How do you get that?" I asked. Chloe giggled and wrapped her arms around me. I felt her cock sort of seize against my stomach.

"You're alive, you're healthy, and you're beautiful. Thank you," Chloe whispered back, kissing my lips again. I looked into her eyes as she spoke, I could see them sparkling even more than before. Almost tears. And I felt a flood of affection for her. And relief as well. Remembering how I had hung back in fear earlier, when her peril was at its greatest, I found that I had been given a second chance. I was, just by living, the person that I had needed as a kid. Chloe felt that. I kissed her again, trying not to cry myself.

"Come on, we want to see more, enough of this lovey-dovey stuff," Casey said from behind us. Chloe and I froze for a moment, and then started giggling. It was like, for a moment, Natalie and Casey hadn't existed.

"Let's show them what girls like us can do," I whispered.

"I am all warmed up, don't hold back," Chloe responded. I pushed back, coming back onto my knees between Chloe's body. I felt her soft breasts, and then cock, fall from my body and felt cool, missed their sensation. But now I was perpendicular to Chloe's body and I could look at her. I started to pull my hips back, my cock slipping a few inches out of her. Then I thrust back in, hard, burying it home. I heard the smack of my balls against Chloe's body, saw her cock jiggle with the impact.

"Fuck, like that!" Chloe moaned, her hands rising up to squeeze her own breasts.

"Yeah, like that!" Natalie said, still sitting beside Chloe. Natalie sort of moved, so that she was kneeling next to me, on the other side of Chloe's leg, watching from roughly the same angle I was. I kept thrusting my cock into Chloe's tight asshole, feeling her squeeze around me. I watched her breasts and her cock bounce with each thrust.

I reached down, wrapping my hand around Chloe's hard cock. Her skin was incredibly soft, but her cock was like warm steel beneath it. I stroked my hand up and down on her, letting my palm circle around the tip, coating it with pre-cum. Chloe moaned and shoved her hips down, driving my cock in deeper as I stroked her.

"You don't get to have all of her!" A voice to my side said. Casey had crawled up next to Chloe on her knees. She reached forward and gently took Chloe's hard cock from my hand. She stroked it a few times, looking up towards Chloe's face. "She looks so cute when she is getting fucked!" Casey added.

"Stop talking! Put that dick in your mouth!" Chloe begged. Casey laughed a little, turned her hand and slipped Chloe's cock effortlessly into her throat. I had never seen anything like it. The cock just disappeared inside of her. Once second, Casey's lips were around the tip of Chloe's penis, and the next her nose was against Chloe's hip. She choked a little, pulled the cock out, and then went back down.

"Damn, she is good at that!" Natalie said, and I turned and looked at her. At the same moment, I felt Natalie's hand press against my spine. Then, as I was still thrusting into Chloe, Natalie's hand snaked down, between my ass cheeks. After a moment, the damn, warm pads of her finger found their way to my asshole. She starting to circle her fingers around me. The very tip pop gently inside of me, I jumped a little. Natalie giggled and pulled her hand back. A moment later it, was back. I realized that she wasn't just gently massaging my asshole (though that felt nice), but lubing me up. I turned towards her and kissed her, even as I continued to thrust.

The four of us continued for a few minutes. Chloe lay on her back, her body tense as she squeezed her breasts and moaned uncontrollably. Casey knelt in front of her, moving her head up and down in rapid, fluid motions. Chloe's cock disappeared into Casey's throat, pulled almost all the way out, then disappeared again. I thrust my cock into Chloe's ass as I watched, moving faster as I felt her asshole relax for me. Her insides squeezed me, pulled me in deeper and deeper. And the whole time, Natalie watched her finger circling gently on my asshole.

In the end, it was just too much excitement and attention for Chloe. She held on for as long as she could, but I don't think it was that long. I heard her cumming, knew it was happening. Her eyes slammed shut and she moaned so loudly I thought that the old lady at the front desk would hear it. I saw all her muscles seize, saw her hips thrust up hard into Casey's face. And then, I felt her anus clench on me so tightly I thought for a moment that I was going to cum too. I saw Casey sort of pull back slightly, like she was surprised.

"Oh god!" Chloe moaned as her body trembled for a long moment. Then she let out a low sigh and collapsed, panting. Chloe's asshole relaxed around my cock. I stopped thrusting, to give her a moment to enjoy savor her orgasm. At that same moment, Casey pulled back entirely, letting Chloe's still-hard cock slip from her mouth. There was cum dripping from Casey's chin. Casey rose quickly, put her hands on my cheeks, and pulled me towards her. In a moment, our lips were pressed together. Our mouths open and a large blob of Chloe's hot, salty sperm poured into my mouth. I shivered at the flavor. She tasted so savory, so lovely. I knew I should share with Casey, but I quickly swallowed all of it down, feeling Chloe's warm cum land heavily in my stomach.

I sighed and rocked back on my hips slightly. I don't know what I was intending, but I felt my hard cock slip out of Chloe's asshole heard her sigh as it moved out of her. I turned to look, watching her cute little asshole gape for a moment, before closing back up, looking as pink and perfect as ever.

But after a moment, my view was obscured. I saw Natalie's head drop down between my cock and Chloe's ass. It took me a second to realize what she was doing. In fact, I felt it first. Natalie's lips had wrapped around the tip of my cock! Still hot from the inside of Chloe's asshole, Natalie's tongue was licking and sucking my penis! Her head dropped lower and lower, until my entire cock, tasting of Chloe, was inside of Natalie's mouth.

"Oh my god, that is so nasty!" Casey said from next to me, wiping her chin with the back of her hand and then licking the cum off it. Her eyes were on Natalie the whole time. Eventually, Natalie pulled back, letting my cock drop from her mouth.

"See, you all know nothing about being a pervert," She said, and then turned and kissed Chloe's cock sweetly.

"Don't stop sucking!" I begged. Natalie smiled, turned back to me and kissed my cock again.

" Get on your hands and knees," Natalie ordered. I was unbearably aroused, and not in any position to deny Natalie anything. Without another word, I moved slightly the the side and dropped down to my hands and knees. Natalie followed me over. As soon as I was in position, she dropped down onto her back. She was perpendicular to my body and she sort of slid herself underneath of me. I felt her hand on my cock, and I arched my back down, thrusting my cock towards her face. Natalie deftly guided it down, towards her mouth.

Casey moved quickly as well. She waited for Natalie to get in place, and she knelt down between Natalie's legs. Casey spread them gently, and then dropped her head down between them. I felt Natalie's body tense for a moment, as Casey's tongue began to lap at her wet pussy. Natalie was so aroused that I could actually smell her sweet juices as Casey began to lap at them.

Soon, the only person not involved was Chloe. She was sitting on the floor now, panting a little and propping herself up on her elbows. She was looking at me, as my eyes rolled back in my head. Natalie's mouth felt incredible. Her tongue moved up and down my shaft. And any time I felt like she was getting close to pushing me over the edge, she dropped down and licked my balls. Chloe could barely see that from where she was sitting. She leaned forward, and looked beautiful.

"I am all lubed up," I heard in my voice, and hadn't even realized I had said anything. But I didn't regret it. Chloe smiled and quickly got up off the floor. Her cock bounced lewdly as she rose to her feet. It was still hard glistening with Casey's saliva. She walked up towards me. She bent over at the waist, grabbing my chin in her palm. She pulled my head up.