Sasha, the Cheating Anal Slut: Naomi Helps Me Stretch Sasha’s Holes — Part 9
I felt the head of Naomi’s strap-on fumbling around the entrance to Sasha’s cunt, and I stopped thrusting in and out of her asshole, to give her an easier target. It was going to be incredibly tight, but Naomi was insistent.
If you’re new to the series, please start from the beginning:
Previous parts: 1, 2, 3, 4, 5, 6, 7, 8
She practically jumped onto the bed, her legs landing on either side of mine.
“I know it’s only been hours, but I’ve really missed this guy,” she said, referring more to my cock than to me.
She shifted her weight forward to make space, then, with a tight grip on my erection, positioned it at the entrance to her rosebud. The fingering Naomi had given her earlier proved to be enough of a warmup because she eased herself down on my shaft, her sphincter wrapping around my cock without much resistance. I opened my mouth to grunt, but Sasha was quicker, muffling my mouth with her own. What we were doing, without any room for argument, was wrong. We were both cheating on our spouses and were doing so with the utmost pleasure and with no thought for the sins we were committing. We were each other’s secret and each other’s source of the nastiest sexual acts we’d ever committed.
Sasha rode me fervently, working my cock up her ass every few seconds, while our lips kissed, licked, and nibbled at each other. Naomi took a few playful whacks at Sasha’s ass as it bounced on me.
“Oh, you bitch!” she said, snapping out of our passionate kiss.
“Oh, you deserve it, girl!” Naomi replied. “Holding out on me all this time? Do you know how hot you look right now?”
She swatted her ass a couple more times.
“Are you going to get it all in there, babe?” Naomi asked, pushing down slightly on Sasha’s ass, forcing her to bottom out on my cock.
At her friend’s question, Sasha paused. Closing her eyes, she seemed to be focusing her energy on something, but I wasn’t sure what. I was about to ask if she was okay, but then she set to action. In one determined motion, she sat all the way down on me, her ass coming to rest on my thighs. She took the rest of my cock straight up her rectal passage, to the astonishment and cheer of Naomi behind her.
“Holy fuck, girl! You’re a wonder!”
Sasha had a proud smile on her face as she wiggled her ass at her friend. With subtle movements, she flexed her hips so that she could stimulate me more, only moving about an inch up and down, but that was enough. If I hadn’t already cum multiple times today, I undoubtedly would have erupted by now.
I closed my eyes and tilted my head back, savoring the sensation. Sasha’s hands were on my chest, her pussy was teasing itself on my trimmed pubic hair, and her ass was squeezing my cock for all it was worth.
“It’s not too late to change your mind,” she told Naomi. “I’m sure he’d fuck your ass if you let him. Best to learn with someone who knows how to do it.”
Her friend chuckled and gave Sasha’s ass one more smack.
“I admit, you do make it look tempting, girl, but I think I’m going to save my ass for my one, special guy. Maybe I’ll give it to him as a wedding gift. Who knows?”
As Naomi spoke, I could hear her voice moving to the other side of the bed. When I opened my eyes to see what she was doing, she was picking the strap-on off the pillow.
“Besides,” Naomi said as she slid the leather harness up her legs, and pumped her fist over the plastic cock. “I’ve got more fun planned for tonight.”
She moved back down to the foot of the bed, admiring Sasha’s ass.
“You know, my original plan was for you to ride him while I rode his face. I haven’t cum yet tonight, and I was really looking forward to testing your fuck-boy’s oral skills. You’ve said they’re excellent. But it’s time for the grand finale now. I think we’ll all cum with what I have in mind.”
Naomi instructed Sasha to dismount and for us to lie in a spooning position. Once there, she ordered me to enter her ass again, which of course I was happy to do. Sasha took me easily, her anal passage having loosened quite a lot today.
As I slowly moved in and out of her, Naomi lay on the other side of Sasha, facing her and cupping her cheeks. She moved in and locked lips with her. There seemed to be as much energy and passion in their kiss as there was in ours, and for a moment I was envious. I thrust a little harder to remind Sasha that I was still there, and my gesture broke their kiss for a moment.
“Oh, babe, he’s turned on by us kissing,” said Sasha. “I just felt him swell up even more. It feels amazing in my ass.”
“Oh really? Brett, does it turn you on to see two women kissing? How about this?” Naomi continued.
She lowered her head to take Sasha’s left nipple in her mouth. Sasha gasped and immediately put a hand behind Naomi’s head to hold her close. I then felt fingers grazing against the base of my cock and knew that Naomi was stroking Sasha’s pussy and clit. Sasha was clearly responding well to the overstimulation. She wasn’t only moving in rhythm with my cock, but with her friend’s nimble gestures towards her pussy and nipple.
“Fuck,” Sasha cried out when Naomi inserted two fingers into her clasping cunt.
She opened herself up further, planting her foot on the mattress. Naomi read her response perfectly and pushed further by adding a third finger.
But Sasha wasn’t the only one enjoying the sensation. I could feel the knuckles of Naomi’s fingers sliding against the bottom of my cock from inside Sasha, through the thin membrane separating her holes. It was surreal!
“Oh, fuck,” I grunted. “That feels fucking amazing!”
“We’re just getting started,” Naomi said, removing her fingers.
“Girl, please, go slow,” Sasha said. “I don’t know if I can take both at once.”
“Don’t worry, sweetie. You know I wouldn’t hurt you.”
I knew exactly what was going to happen even though I couldn’t see clearly. I felt the head of Naomi’s strap-on fumbling around the entrance to Sasha’s cunt, and I held still to give her an easier target. It was going to be incredibly tight, but Naomi was insistent. The silicone head pushed forward at first, pressing somewhat painfully against the base of my cock even as it was lodged inside Sasha’s ass. But once it popped in, it simply ran parallel to my shaft.
“Jesus fucking Christ!” Sasha shouted.
“Holy fuck!” I cried out.
Naomi’s movement had caused sensations unfamiliar to both of us so she paused for a moment, allowing us both time to grow accustomed to her cock while she returned to Sasha’s lips and they started making out again. At this moment, I just felt like a human butt plug, standing with my cock lodged inside this beautiful woman’s asshole, as she was passionately making out with her best friend. Not that I minded, though, but I did feel sort of left out for a minute.
Without breaking their kiss, Naomi shifted her hips forward and started working more of her cock into Sasha’s pleasure passage, forcing an increasingly high-pitched squeak out of her, the deeper she went.
On the other end, I started grunting as the ribbed silicone cock slid smoothly against my member. This was new and unexplored territory for both Sasha and me. Perhaps even for Naomi, and that specific arousal that comes only from that perfect taboo sex washed over us simultaneously.
Naomi broke the kiss only to admire Sasha’s strained and euphoric face as she pushed the last of the silicone cock inside her cunt. Sasha sunk her head into Naomi’s shoulder, biting her as I started thrusting in and out of her rectum.
“That’s it!” Naomi responded to the bite, clearly turned on by the impact she was having on her friend.
Naomi’s eyes went wide and locked with mine and pulled Sasha’s left leg around her so that it was hooking her own leg in place. We were running out of space between us. My body was pressing tight against Sasha’s back, while Sasha and Naomi’s bodies were squished against each other, their breasts mashed together, poking each other with their erect nipples. Their lips locked again and their hands anxiously explored each other’s bodies.
In all my life, I never imagined I would have been brought to orgasm by a dildo. But in all my life, I’d never imagined that a dildo would be pressed so tight against the bottom of my cock inside a woman. The ridges of the silicone cock stimulated my cock and combined with the heat and liquidity inside Sasha, it proved to be just too powerful for me.
“Fuck, I’m coming!” I shouted.
“Me too!” Sasha and Naomi immediately replied in unison.
I reached past Sasha and grabbed Naomi’s back, pulling her closer. In this tight and sensual embrace, we all came simultaneously. My orgasm was incredibly powerful, even if there wasn’t much cum left to shoot inside Sasha’s welcoming ass.
Sasha’s contracting sphincter and rectal passage felt blissful around my cock and from the look on Naomi’s face, her climax was equally powerful, her strap-on having manipulated her clitoris in just the right way.
With each of us spent, we lay entangled for God knows how long. Our bodies felt heavy and our arms were draped over each other, with our legs slumped and interlaced. The arms we were lying on fell asleep at some point, which triggered us to move around.
Naomi was the first to pull out of Sasha, who seemed to miss the invading cock in her cunt. I followed Naomi and removed my deflating cock from Sasha’s warm rear tunnel then we all rolled on our backs, with Sasha still in the middle.
“That was fucking amazing,” Sasha said after gathering enough strength. “I’m so glad we did this.”
“Me too,” I said. “You know, Naomi, Sasha had to convince me to do this as I didn’t want to share our secret. But in this moment, it’s hard to say that this evening wasn’t worth the risk.”
Naomi chuckled.
“Are you kidding? I would never betray my girl. She’s my everything, and I only feel that more powerfully now. I know Sasha thinks I’m sometimes a slut, but I can honestly say this was the most meaningful sex of my life,” Naomi responded.
“Aww, really?” Sasha said, turning to look at her friend.
Naomi shrugged and nodded her head, locking eyes with Sasha again. I could tell they were sharing a moment and thought that it might be a good time to excuse myself.
“I think I should get going,” I said. “Long day tomorrow and all that.”
“It was nice to meet you, Brett. Thanks for tonight. Hope we can do it again sometime,” Naomi offered.
I smiled and nodded.
“See you tomorrow,” I said as I slipped my robe back on, and left for my room.
As I closed the door behind me, I heard the sounds of lips smacking and I knew they were kissing again. I wondered how much longer they would go on without me and the fear of missing out on that instantly hit me. But I needed to rest.
Settling into my own bed, I was relieved to have gone through the night with all parties happy. Now, for a good night’s sleep so I would have the energy to navigate the next challenge: Maria’s arrival.
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