She must have sensed that I had grown compliant, for she lifted her head, let go of my hair and jumped off the bed to retrieve a cardboard box under the bed. Out of it she lifted a small, black velvet bag with some lumps in it, then a bottle of what I could only guess was lube. She put the box back on the ground and then held up the black bag dramatically, prying open the top with her other hand. Out of the top emerged a flash of color, then the rest of the velvet fell away to reveal a full 8-inch purple dildo with a thick 2 1/2 inch swirly bump protruding at a right angle from the top. A small cord traced out the back to a remote, so I decided it must be a vibrator as well.
“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 Meg, 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.
Meg 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 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?”
“Hmmm. Maybe a little…” she whispered. “But now you’ll know how we feel, the first time a girl takes it in the ass.” Oh God. What could I say? Like I said, I had taken her in the ass a half dozen times- and though I always tried to be gentle, I had also driven forward with lust. I craved her ass, the feel of it, to be inside her… did that mean she wanted to be inside me?