More fun
Want to support CHYOA?
Disable your Ad Blocker! Thanks :)

Chapter 41 by remysloane remysloane

What's next?

We use the strap-on to peg Shauna

I admired Shauna's body confidence. She was on her hands and knees in a well-lit room with two girls staring at her butthole, and she loved it. My preconceived notions for trans women, at least in this situation, were clearly wrong. Shauna was a down to earth, mentally stable, sexy person that knew exactly what "she" wanted and what role she wanted to play.

I knelt next to her and spread her cheeks more, not that they needed it. Tess licked her hairless butt and milked her small erection. Shauna's skin was perfect, and the tiny hole was slightly open and slick with Tess' spit. "Do you have sex with men, too?" I asked Shauna.

"Yes, but I still love being with women. I am super hot for you two."

"Do you... receive?" I asked, not sure the right way to ask if she let dudes fuck her in the ass.

"Yes, of course, baby. I started experimenting when I was DeShawn."

Tess took her tongue off Shauna's anus and looked at me. I grinned and said, "I brought the strap-on. Let's fuck her." Shauna went to her back and looked at me, then Tess, and a few seconds went by. "Do you guys do that?"

"It hasn't come up," Tess said.

"I'm up for that. I'd love it, actually," Shauna said.

"Stand by." I went to the living room to my small bag I'd brought in. I pulled out the harness with the large dildo still attached that I used on Tess. I came back in and grinned at the ladies. "Who does the honors? Tess, it's your birthday."

"You're good with it, since you use it with me. I want you to fuck her and I'll love watching. Keep the garter and stockings on, it will look sexy as fuck with it."

I shuddered in horny anticipation as the base of the dildo pressed against my crotch. I cinched the straps in a skilled movement, and I relished the feeling of power that came over me as the weight of the dong tugged at me. I fucking loved having a penis, and wondered briefly how Shauna could ever give it up!

Shauna and I exchanged a look. "Looks good on you," was all she said.

I grinned and twirled my finger. She got the hint and resumed her doggie style position on the bed.

I upgraded my strap-on game after Tess became a regular customer:

Now this was awesome! I felt like such a badass as I mounted Shauna and prepared to fuck her. This lowly virgin was taking charge of the threesome! I had lube also, and I squirted some on the shaft and worked it in. Wondering what Tess had been enjoying earlier and feeling like I should pay respects first before violating this pristine backside, I leaned down and twirled my tongue around her rosebud, enjoying the funky scent of her clean nether regions. I then gently probed a lubed finger in. She moaned, and her experienced muscles yielded easily to my pressure. I coated her inside with a few pumps of the digit, then pulled out and steered the tip of the black dildo to her hole. My pussy tingled with anticipation. I was fucking a trans girl in the ass! This was an incredible moment for me. "You honor me with your trust," I said.

I was right on target, and the area softened to my gentle pressure. Then rather easily, the head suddenly popped in completely! The rubbery rim of her anus clenched tightly on the shaft. She gasped in surprise, but I don't think I hurt her.

"Is that okay?" I asked.

In response, Shauna moved her haunches backwards, impaling herself. I watched amazed as inch after inch sank into her hungry ass until the entire phallus had disappeared inside her.

"Damn, I guess so! Good job, girl," I said and moved my hands to her hips. I pulled back tentatively, then drove in more confident, then again, then again, and now I was fucking Shauna's ass and loving it!

"Yes, baby, that's a big dick. Mmm, it feels so good," Shana cooed.

It was time to tap this:

"You guys look so sexy right now," Tess said. I grinned at her, and she came in for a kiss. It was surprisingly easy to make out with her to my side while fucking Shauna. I wanted to make sure the birthday girl was included on the action, as everything I did tonight was for her.

Then our lips smacked as they parted, and I turned my attention back to Shauna. "Is that okay?" I asked as I began to assert myself and fuck her harder. Her body was showing no signs of difficulty taking my dildo.

"Mmm, fuck me harder, baby," she said.

"Your tits looks great," Tess said. My over-sized, sagging hangers were as always in start contrast with my athletic body. My fucking motion was causing them to jiggle, the nipples pointing downward and bouncing around beneath the heavy breast flesh. She grabbed the one closest, then leaned down to suck the nipple.

Shauna's moans were girly, high-pitched, and reminded me of porn. Each pump of my dildo into her ass was greeted with an enthusiastic moan or squeal. That resemblance to porn triggered the kinky side of me, and I pulled the dildo out like a boss with a popping sound, leaving the trans girl open and lewdly gaping for a few seconds before her anus reflexively closed back. Then I drove back in and repeated the process a few times. It was so hot to see her respond with such enthusiasm to my strap-on skills. She was an expert at receiving anal, displaying advanced muscle control and movement in doggie pose.

I loved that her butthole looked so tiny and perfect before I was there, then devolved into this wide open, yawning chasm as a result of my administrations. It was so hot to be the "man" to a man that wanted to be a woman for me. I was the inexperienced virgin, but also the alpha male, fucking her so hard. I even loved her trans body, the male and female features mixing so well into a sexual being that I loved fucking. Her ass in my face now, athletic with narrow hips yet somehow feminine. She had the effortless full buttocks from her male attributes, bit somehow had the flaring hips of a woman. It was a glorious ass! Everything was mixed up, and I just went with it and loved it. I thrilled in the kinky moment, even as a virgin doing a sexual act few would ever be lucky enough to enjoy. Shauna was so beautiful and sexy even as my mind could not reconcile the mixed genders.

I slid the dildo out of her ass. "I want to see you, can you turn," I asked.

In a moment, Shauna was on her back, legs wide and bent back at the knees. This was different, because now her penis, the final proof of her masculinity, was visible. But it was losing the fight with her girly side. It was shriveled up and limp with a correspondingly smaller scrotum on the tall lady.

Perhaps I glanced at it too long, or maybe she read my mind. "I'm very turned on by you, Ramya. I just get soft when I'm getting fucked. I love it, trust me."

I grinned and wiped a drop of precome that oozed out of the slit at the top of her weakened unit at that moment. I wiped it on my tongue, then aligned the dildo and drove back into her ass.

Tonight was all about the birthday girl Tess, but for now, I gave Shauna my complete adoration. I maintained good eye contact throughout gentler strokes now, then I leaned down, settling my hanging boobs on her torso, then coming close to kiss. It deepened to tongue kissing, and I fucked her very slow now as we made out. I even forgot a few times and just left the dildo buried in her ass, then I'd move it again, in and out slowly.

While this erotic moment could have gone on a long time and we were in no rush, there was no clearly defined way to end it. I would not ejaculate for the typical male cumshot obviously, and Shauna could not come while getting fucked since the act suppressed her erection. I experimented a few times while fucking her, stroking her cock with my thumb and first finger, but I couldn't get her hard. The sheer amount of foreplay and the constant agitation of her prostate from the dildo was ensuring more drops of precome though, somewhat with a white tint to it now. "What can we do for you?" I asked Shauna as I broke off the kiss. "I want you to come."

Shauna put her hand down to signal a stop, and I came up to my knees and pulled the dildo out of her bum. Shauna suddenly shook with pent up sexual energy and pleasure and laughed, but this was not a climax. Shauna needed an old school release with ejaculation. Tess answered for her. "She usually comes in my pussy. But Shauna, Rammie is really good at sucking dick. Since she's too prudish to put out, maybe we can get you off that way."

I nodded at Shauna. "I'll suck you off and take your load if you want. It's my pleasure."

After dominating Shauna like this, she is about to turn the tables

Want to support CHYOA?
Disable your Ad Blocker! Thanks :)