Paradiso Ch. 15

"I have to fuck that ass." Leah announced.

My heart jumped and Jessie grinned. Leah looked down at me, waiting for permission. I nodded.

"Go ahead."

Leah repositioned herself between my legs and pulled my ankles upward, resting them on her shoulders. Marina had loosened me up but Leah's penis was truly massive. This would be as big a challenge as the first time with Jessie. I only hoped that she would take things as slowly as Jessie had, giving me time to adjust.

Marina handed Leah a bottle of lube and she began applying a liberal amount to her long, thick, curving member. She then reached down and began lubing up my asshole with two fingers, then three, the lube mingling with the load of cum Marina already left inside me. When she judged that I was ready she replaced her fingers with the tip of her enormous member.

Jessie pulled her own impressive dick from my mouth and a moment later Leah began pushing inside of me. It was smart of Jessie to get her cock out of my mouth because as my asshole desperately stretched to try and accommodate the huge, blunt head, I bit down hard. Leah moved slowly, but it wouldn't have mattered if she had taken a week. Stretching wide enough to take her girth was bound to cause discomfort. I resolved to simply ride it out because I knew the pleasure that was to follow would be worth it.

After maybe three minutes of pushing and prodding before finally giving one last hard push and the widest part of the head slipped past my sphincters. I stifled a cry and Leah began stroking my legs, just holding there for a time to let me loosen up a bit more.

I heard panting and looked over to the other side of the bed to see Sierra fucking Riley in the ass doggy style.

"Fuck, Riley." Sierra moaned. "Your ass feels so fucking good."

"And your cock feels really good fucking me." Riley answered. At that moment I knew what each one meant. Being fucked like that felt amazing and Riley's ass was a little slice of heaven.

The stretchy soreness in my ass didn't completely subside but it became more bearable and Leah began to slide more of her giant girl-cock inside. The movement was slow, thankfully; almost imperceptible. Each inch was a challenge. Even though her cock wasn't that much bigger than Jessie's, it was as if that little extra bit of width crossed the line of my endurance.

When Leah was about half way inside the discomfort became pain; sharp and raw. I sucked in my breath and held up a hand in a gesture of pleading.

"Are you alright?" Leah asked with a look of genuine concern.

"I don't know if I can take all of it."

"Yes, you can."

For the moment Leah ceased the assault on my tender rectum and just lay on top of me. I could feel her plump tits pressing into my chest.

"Just relax." She said before pressing her lips to mine. For the next couple of minutes our tongues danced together and she caressed the muscles in my arms and chest. I started to relax when she drew back her tongue and started kissing my cheeks and then my neck. When she reached my ears I knew she had my number. Her mouth worked every curve and soon I felt the pain in my asshole subside and my cock beginning to stiffen at the same time.

Leah's inward thrusting resumed, slow and steady. Another inch disappeared inside of me and then another. It was uncomfortable, but the sharp pain never returned and soon her hips were pressed tight against mine, my asshole stuffed to the brim with hard t-girl cock. She left it there, buried deep in my bowels, to let me grow more accustomed to her remarkable thickness.

To my right Sierra and Riley had switched positions and the adorable little pixie was riding Sierra's thick, black rod reverse cowgirl style and squealing with delight as she was doing it. To my left Marina was actually deep-throating Jessie's cock. My eyes widened at that sight. It was like she had no gag reflex, the way she was taking that giant slab of meat. I was duly impressed.

The discomfort in my ass had faded enough that Leah was finally able to establish a slow pumping motion. A few inches out, then a pause, then a few inches back in. Every couple of minutes she would stop part of the way out of me to add another squirt of lube to her enormous shaft. Each time she did the in and out motion was a little smoother and easier.

Soon she made her thrusts longer and quicker and the pleasure I was getting from the prostate massage was beginning to outmatch the fading discomfort of my asshole being stretched wide. Before I knew it I was getting a real fucking; long, smooth strokes with her entire length.

"Hold your legs up." Leah instructed.

I did as she said and grabbed my legs behind the knees, freeing up her own hands. She took hold of my erection with one hand and my balls with the other and began stroking me in time with her fucking of my stretched anus. It seemed impossible, but I was taking her obscenely large penis inside me and was actually beginning to enjoy it.

"Don't stretch him out too much," Sierra joked "or the rest of us won't have any fun." I felt a little slutty being talked about as if I was a sex toy to be passed around, but not in a bad way. It felt kind of good to be a bit of a slut for these hot dickgirls. Leah's big round tits bounced and giggled as she pummeled my asshole. The pressure on my prostate was causing my cock to leak pre-cum like a faucet, which was lubricating her hand as she stroked my hard-on.

Suddenly, Riley was there. She and Sierra shifted positions back into doggy style and Riley's face hung over mine. She smiled down at me and then lowered her face to mine. As we made out softly she started pinching my nipples. It was all too much stimulation and I felt my groin and ass muscles tighten and spasm. I moaned into Riley's mouth and felt the first squirts of cum flow out of me to run over Leah's hand.

The rhythmic tightening of my anus added a little extra sensation for Leah's cock because about a minute later she buried her dick in me to the hilt and her face and neck turned a bright red. She didn't cry out but her eyebrows knitted together and her mouth hung open as she shot a load of her shemale cum in my asshole.

"I know what that feels like." Jessie declared. "Doesn't that ass just cry out to be fucked?"

"It sure does." Leah answered, catching her breath.

"His cock is pretty good too." said Riley, pulling her tongue out of my mouth.

"Well in that case," said Sierra as she continued to hammer away in Riley's ass "I think maybe I should get some of that too. What do you say, Gary? Once you've got your wind back how about giving my ass a nice pounding?"

All I could do was smile breathlessly as Leah eased her deflating horse-cock out of my bruised and battered asshole.

For the next hour it went on like that. The five of us sucked and fucked one another until we could take no more. Occasionally one or more of us would head to the shower to rinse off the sweat or head to the kitchen for a glass of wine. Aside from that it was fuck, rest, repeat.

Sierra was indeed the next one I fucked. Her smooth, dark ass was incredibly warm and tight. After that Jessie took another turn in my ass, talking dirty the whole time about how she had turned me out and made me crave cock. She took full credit for setting me on the path that led through my first gay experience with Liam the night before and when she flooded my rectum with her hot seed she called me her little bitch boy.

After that I fucked Riley again in several different positions until I pulled out and squirted my cum over her stomach and pretty little titties. Sierra then licked the cum off and shared it with Leah in a long, sexy kiss. The whole time I was banging Riley's sweet little ass the other four were going at it with each other. Marina laid on her back with Leah on all fours between her legs, sucking her off. Sierra fucked Leah in the ass while Jessie fucked Sierra.

For the grand finale I started in a sixty nine position with Riley, sucking her cute little girlcock while she did the same for me. Then Marina appeared in front of me and I began sucking her larger cock. I couldn't quite take all of it the way I could with Riley, but Marina didn't seem to mind and whispered encouragement as I tried to coax another load out of her.

After a minute I felt someone moving behind me. I couldn't turn my head to see who it was because my mouth was full of girl-dick. Feminine hands caressed my ass and I knew that soon another penis would be penetrating my well worked asshole. I did my best to relax my sore anal muscles and a few moments later a column of hot meat was making its way inside me.

The cock pushing up into me was not splitting me in half, so it couldn't have been Leah or Jessie. That only left Sierra and her smooth, dark, uncut member. After the stretching I had gotten already it was not much of a challenge to take her full length and before long she was fucking me with long, smooth strokes. I was being spit roasted!

After a while I heard Jessie tell the others to turn me over. Two minutes later I was lying on my back and the three horny t-girls were working me over; Riley sucking my straining cock, Sierra fucking away in my ass and Marina straddled my head and was humping her cock in and out of my mouth. I was very much enjoying the feel of the stiff flesh plunging in and out of my willing holes.

My vision was mostly obstructed, but out of the corners of my eyes I could see the feet and legs of Jessie and Leah standing to either side of me. I didn't know what they were doing but I was too focused on the cocks and mouth that were driving me ever closer to my next orgasm. Pre-cum was flowing freely from Marina's caramel colored tool and into my waiting mouth. Each thrust from Sierra teased my enflamed prostate gland and Riley's mouth was pure pleasure wrapped around my manhood. All around us was the smell of sex and sweat and semen.

Marina was the first to cum, flooding my mouth with mildly sweet t-girl spunk. I swallowed eagerly before it could fill my mouth and make me gag and when she was finished she rolled off of me and made a sound like someone who had just had their first drink of water after walking through the desert.

"That hit the spot." She chuckled before giving me a quick peck on the lips.

When I looked up I saw Jessie and Leah jerking each other off with one hand and fondling each other's tits with the other. The hot sight of it was that last little push I needed and I moaned aloud as my groin tightened and my asshole clamped down on Sierra's delicious cock. Riley shuddered as I treated her to a taste of my own hot cum.

A few moments later Leah started bucking her hips wildly, just as she had in her little show earlier. Ropy little jets of semen burst from the oversized head of her massive cock and landed in streaks across my chest and neck, with one big drop landing on my cheek. Less than a minute later Jessie added her own load to the sticky mess splattered on me. When she had finished Riley crawled up next to me and began licking off the sperm with a look of total bliss on her face as she swallowed each drop.

When Riley was done cleaning me up she started making out with me and her tongue tasted of salty jizz. While two of us ate each other's mouths Sierra cried out and exploded in my asshole, adding another load to the several already filling me.

For the next little while we all lay there together, caressing each other's bodies and kissing. I reveled in the erotic beauty of these amazing transsexual goddesses. Fifteen minutes later we went for a group shower and lingered under the hot spray as the sweat and semen floated away and we were left feeling relaxed and clean. As we dried one another off Jessie spoke.

"So, Gary, I hope this isn't the last that we'll see of you this week. My cock has taken quite a liking to that hot, tight asshole of yours."

I smiled back at her. All self-consciousness about being ass fucked was gone.

"Keep this up and it won't be tight for long." I joked. That brought a laugh from everyone. "Well, ladies, this has been a lot of fun but I think I'd like to get back to my place and see what Sara is up to."

One by one each of the five sexy t-girls said goodbye with a hug and a kiss and I walked out into the fresh, midday air.