Trapped Between Two Alphas (Katerina)
Chapter 55

"WHAT is that?" I asked, suspiciously.

"That is for you, my love, and you're going to learn to like it. I'm going to teach you."

"Oh Kat, I don't know..."

"But I do. So relax. Lean back, and enjoy it. I promise you, we won't do anything you don't like. I'm going to break you in sloooowly."

Something about the way she said that last part got my adrenaline going, and probably helped overwhelm whatever hesitation I was feeling. "OK," I laughed nervously. "You're the boss."

"That's right," she said, without missing a beat. "Now, put your legs up."

I did as I was told, bending my knees so that my feet were flat on the bed. She reached down and grabbed a pillow and a towel lying at the foot of the bed. "Lift up." I did, and she slid the pillow under my ass and covered it with the towel. I sat back down, my ass now elevated a couple inches off the bed.

"Now. Are you relaxed?"

I laughed. "No. I have no idea what you're going to do to me."

She looked at me in the eyes. I couldn't see the green of her eyes in the candlelight, but I knew they were there. "Well, do you trust me?"

"Yes."

"OK. Then relax. You're going to like this..."

"Yeah?"

"Yeah."

She stayed kneeling beside me on the bed and leaned over to take my cock back in her mouth. While making wet, slurping sounds, she reached for my balls with her right hand and began tugging them lightly. It felt really good, but also soothing. Soon her hand strayed southward and she placed a single fingertip on my ass and began rubbing in circles. I could feel myself clenching, but since she wasn't pushing there wasn't any resistance- just light friction on the surface. Once I started to focus on the sensations, it felt pretty good.

"Do you like that?" she asked innocently.

"Um, yes, actually. That feels good."

"Good," she smiled. "Now I'm going to give you a little lube."

My heart was racing. She was lubing me; wasn't that dirty? Would she think I was less manly? But I didn't think less of her for taking my cock in her ass, and anyway she didn't seem anything but excited. I relaxed and tried to focus on the anticipation, turning it into something pleasurable. After a second, I felt her finger return, now slippery, and it probed gently at my entrance. The sensations were new, but with the lube there was barely any friction.

She returned for more lube, spreading a large drop on her fingertip and then circling and massaging it gently inside. As she worked more and more into my ass, my resistance melted and soon she had her moistened finger in past the first knuckle. She began making slow, sensuous circles inside, pulling gently against the muscle. I felt myself resisting, then releasing, relaxing with her massage. She tugged a little farther and I let her stretch my tight spincter. It was weird, but it felt sexual and vulnerable too. What was happening to me?

"Still feel good?" she inquired.

I nodded. As if my rock hard cock didn't tell her.

"Good. Now, I'm going to pop your cherry."

"You are?" Stupid question.

"I am. Focus on relaxing. Relax your body. Focus on the feeling." I tried, but part of me was still resisting.

She withdrew her wet finger and applied another drop of lube. By now I was enjoying the sensation of being "wet"- almost like her pussy, I thought. Is this how girls feel? Wow, I thought, if I was going to say anything... if I was going to stop... this would be the time. But I didn't.

She dobbed the lube at my entrance and pushed her moistened finger back in to the first knuckle. She met the back spincter but, instead of stopping, she pushed slowly but insistently. After only a second, she pushed past the resistance and was in to the other side. I expected that she would pause, but instead she kept going and pushed her wet finger all the way in.

Woah! Before the sensations were coming from the sensitive nerves around the outside. This was different. There was a violation and a pressure from inside, but a good kind. My ass was trying to close but it couldn't. It was strange, vulnerable, but I liked it.

"There. I told you you would like it." I hadn't said anything, but she must have seen it on my face. "Now, I'm going to loosen you up. Keep relaxing." She took her finger and began moving it back in and out of my ass, just an inch out and an inch back in. As she drew out I could feel a little bit of a vacuum, and when she drove back there was a satisfying feeling of having the vacuum filled again. She started taking longer strokes and at the end, she would twist a little, screwing into me. I was still tight, but I was definitely lubed and there was no doubt she was fucking my wet ass with her finger. There was no resisting it. Maybe it was that realization that did it, but psychologically something shifted. I started to focus on the feeling and really relax. I gave myself over to being fucked by her. My mind relaxed and my spincter released too, which to my surprise only increased the pleasure. Whereas before I was clenching tight against her, now she was able to withdraw entirely and easily dip back inside my wet and open orifice. When she withdrew and added a second finger, I clenched for a second but she pushed right past it, taking surprisingly little resistance. It went in with a bit of a wet sound, and now she began pumping faster with her whole arm.

I couldn't help it. I groaned...

"Good! I think you're ready now." She withdrew her fingers with a wet pop, wiped them on the towel, and reached for the big purple toy. Shit. I had almost forgotten all about it, I had been so intent on feeling her fingers inside me. I watched as she positioned the bulb end at the edge of her pussy, and then slowly pushed it in so that the base of the toy went right up against her pubic bone. She then locked it in place with a small leather belt that looped up between her ass like a g-string. Her nipples were erect and she looked really sexy with the seven inch purple phallus extending straight up from her groin. But I felt anxious, and I could feel myself tightening back up.

"Oh God..." I let out, breathlessly. "Is this going to hurt?"

Still kneeling, she rolled a condom down over the toy and positioned herself in front of me. My legs were still spread, but now she lifted them off the bed and scooted closer so that she was sitting with her folded legs under mine. She reached back and pressed the remote control, once, twice, and the toy began a low but persistent hum as she nudged it up against my lubricated hole. My brain lit up as the vibrations against my nerves fired a cascade of sensations.

"Can you feel that?" she asked.

"Yes!" I let out. "Can you?"

"Yes," she nodded. "The bullet is in the head, but it kind of spreads throughout the toy. So there's some stimulation from the part inside me, and the part up against my clit. And of course from watching your face."

"Ohhh..." I said, somewhat nonsensically. I was focusing on the feeling spreading around my pelvis. I could feel the tip pressing against the sensitive flesh and something was taking hold of me. She hadn't penetrated me, but now I wanted her to. I trusted her, and I wanted her inside me. I wanted her to fuck me.

Holding my cock with her right hand, and positioning her toy with her left, she pushed gently and my ass stretched to accommodate. The head of her toy was pressed hard up against my backside, half an inch in, and the vibrations spread all throughout my ass. It felt amazing. My back spincter resisted, though- it was just too big.

"Tell me what you're feeling," Kat whispered.

"It feels... good," I responded, somewhat vaguely. But she wasn't satisfied.

"Baby, I want to see the look on your face as I press this cock inside you. I want you to tell me, too. Tell me how you feel. In detail."

"It feels... warm. Exciting. Sexy. Vulnerable."

"Keep going."

"I like it. My heart is racing. I'm afraid, but I also want you..."

""You want me' what?"

"I want you to keep going."

"To keep going, what?"

It all came tumbling out. "To fuck me. I want you to fuck me. Please, fuck me. I trust you, it feels so good, I want you to fuck me, even if it hurts."

Her eyes lit up, and she looked so happy. "Good," she whispered. "Because that's what I'm going to do. I'm going to fuck you with this strap-on, and you're going to like it. I'm going to make you moan, and I'm going to make you scream, and you can cry also if you want to."

And with that, she doubled the pressure and I could feel the vibrating purple head pressing up hard against the second ring of my ass. I felt myself opening, involuntarily, physically and psychologically. I realized I wasn't going to be able to resist her, and in only a couple seconds, she popped the head into the other side. I felt a quick stab of pain, and then a rush of pleasure as I got used to the new situation. "Goood..." she said, encouragingly. "Good boy. I knew you could take it. Just relax now. Breathe. Enjoy the feeling."

I did as she told me. As I breathed in and out, I could feel myself relaxing and the pleasure increasing. The vibrations almost seemed to be massaging my insides, and without really trying to I could feel my resistance lessening.

"Does that feel good?" she asked.

I nodded. "Yes."

"Now I'm going to show you something else. Something you'll like..."

This was all new, and I already liked it, but what did she have in mind? I could feel the vibrating bullet inside the head of her cock, causing a rush of new sensations inside me as the vibrations spread through my ass. It was intense, but also arousing and completely vulnerable.

With her previous lubrication, she pushed and effortlessly gave me another inch, and then another. There was no friction to the smooth intrusion, but I could feel my insides filling up and a pressure and a strange warmness. Was this right? Was this wrong? I didn't have time to decide, it was all just happening.

Then she settled into place and I noticed a different sensation, emanating from deep inside me but spreading into the inside of my cock. It felt half like I was going to come, and half like I was going to urinate- it felt good, but I was also worried I might actually pee. She had the head of her cock pressed up at an angle against the roof of my ass, and the vibrations were spreading through my nerves there and doing something...