Part 28
The good news was, Julia stopped taunting Chris about his ‘interest’ in guys. However, the reason she let up was because her focus shifted towards the nearby strap-on she had just mentioned. She told Chris to stay bent over as she got ready, and also made a point to never stray too far from him. Every few seconds, she would pause to give his ass a squeeze, reach around for a stroke or two in order to keep him hard, and eventually slipped her lubed up fingers between his cheeks.
Once she had the simple leather harness properly tightened around her waist, Julia stepped forward until her pelvis was flush with his backside, so he could feel the hard silicone between them. “Does it feel too big, Chrissy?” she asked, “If you can’t handle a cock this size . . . ”
It was the same implied threat as before. He could bail on the new and very daunting sexual experience, at the cost of not getting to do anything more with Julia after everything he had already put himself through for her. Perpetually blushing at this point, Chris nervously swallowed and replied in his girl voice, “I- I can.” Of course, that wasn’t enough. As usual, Julia made him say the whole thing. When pressed, he murmured, “I can handle a big cock in my ass.”
“That’s my girl,” Julia said, “Now, pretend I’m a boy and that this is his big cock.” She added one last round of lube with her fingertips, then shifted back enough so she could position the silicone shaft properly. Getting right to it, she pushed forward, sliding the tip between Chris’s cheeks and into his virgin hole. Considering his inexperience, she didn’t get too far before needing to gently thrust in order to work it farther. “Chrissy, relax,” she demanded, “Let me in. You said you could handle a big cock.”
Chris wasn’t trying to resist or anything. There was just already more girth than what he had just gotten used to feeling with Julia’s slender fingers, and he didn’t know how to ‘open’ for something like this. With each light thrust, Chris could feel the fake cock pushing against his hole and then pulling back slightly, going a little bit deeper each time as she coaxed his hole into opening for her. While he didn’t appreciate all the male visuals Julia had recently planted, he couldn’t deny that there was a bit of physical pleasure as she gradually made progress.
His body betrayed him a few seconds later, when a small moan escaped his lips from the sensations back there.
“I know. It feels good, doesn’t it?” Julia muttered, calling him out right away before getting on his case about the slightly masculine sound, “You need to moan like a girl, Chrissy. Show me what it sounds like when your pussy is wet.”
This was all so backwards. Chris wasn’t even the type of guy who made much noise in the bedroom, and now he was being pushed to do so as if he was the sissy everyone kept saying he was. He was also still hard, despite the way Julia was talking to him. It wasn’t that he liked his manhood being referenced like that; he was just turned on from a physical standpoint.
To elicit another sound of pleasure, rather than waiting for Chris to fake it, Julia gave a much harder thrust, pushing the toy cock deep inside of him and more forcefully stretching him out in the process.
By some miracle, he managed to keep his tone feminine as he let out an awkward moan that ended with a mortifying squeal that formed in the back of his throat as he felt himself being torn open back there. Forgetting Julia’s other instructions as things shifted from pleasure to pain, Chris instinctively tightened his muscles and his anus resisted the silicone shaft.
“Ah, ah. It’s going to hurt if you do that, Chrissy,” Julia said, “Breathe. Open up that tight little hole for me, girl. Show me how badly you want a hard cock in your sissy ass.”
He took a shaky breath, doing his best to will his muscles to relax. It was more about her warning about how it would feel if he didn’t, rather than the echo of their demeaning conversation from before.
As Julia continued to thrust, she quietly but firmly coached him through the rough anal experience. “Breathe in. Breathe out. Relax, Chrissy. Keep breathing. You’re a girl, sissy. Moan like one for me.”
Chris concentrated on her instructive words, unable to keep himself from moaning as Julia began rocking her hips harder and faster. He did as he was told, moaning like a girl in a somewhat porn-like manner as he was stimulated in a brand new way. His boobs bounced and shifted in response to her movements, and he was still rock hard despite how degrading all of this was.
Once Julia was fully inside, she kept fucking him with the strap-on while reaching around to grab his manhood. Not that she called it that.
The second her hand made contact, he throbbed in need. In response, Julia giggled. “Oh, Chrissy. You’re so SMALL. You’re not a grower or a show-er, are you? We should really do something about your little vagina. What do you think?”
Chris was in no state to think. He could barely process Julia’s humiliating insults, as he was currently distracted by the fact that one wrong move of her hand was going to make him prematurely blow his load. All he could manage was a nod, not that it mattered; Julia was the one in charge here; he was just along for the ride.
“That’s a good sissy. You ready?” Without any warning besides the smug question, Julia went right for it. One thrust after the other, she fucked Chris’s ass as hard and as fast as she could. At the same time, she gave his balls a quick squeeze to encourage a higher voice, then proceeded to jerk him off.
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