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your hand and promise to be there."
For a few minutes, I contemplated how I should proceed until she reminded me she was waiting.
"Im trying to decide how to do this, Dani. I dont have any way to duplicate any of what they do. Let me think for a minute or two."
The dildo I would preferred to use was in the trunk of my car, in a bag Id started carrying for whatever opportunity might arise. Searching through my old toys, I found a medium thickness vibrator of about nine inch length. It was cock shaped but there were ridges down the sides of it and I wondered if it might irritate rather than pleasure her.
"Im going to use something I have available, Dani. If it irritates you or if it is very uncomfortable, let me know and well have to think of something else."
She nodded but I noticed she was still chewing her lip. "I guess Ill just have to have you get up on your hands and knees."
As soon as I said it, I saw the panic flush over her face. "Do we really have to do that, Samantha?" she asked.
"Its part of the orientation, Dani, but I promise to be very gentle and go slow."
She moved to the middle of the bed, with her feet over the end. I gave her some pillows and once she arranged them the way she wanted them, I spread her knees wide and gazed at her virgin anus. I couldnt deny that I was hungrily wanting to do this. After liberally applying a coating of lube to the vibrator, I drizzled some into my hands to warm it, then began working into her crease and over her beautiful pink anus. She tensed, but didnt say anything and it wasnt until I moved a finger tip into her that she displayed any second thoughts.
"Samantha," she cautioned.
"Just a little more lube to make it more comfortable Dani," I replied, as I moved my finger into her, applying lube to her anus and rectum with my finger. As I did so, I moved my finger around in her to try to open her up a bit more before introducing the second finger.
"Ow, oh shit, Samantha," she cried as the second finger slipped in. Pumping both fingers into her slowly, I added more lube and moved them around inside her rectum.
"Ok now, Dani. You need to relax completely. Youll feel a bit of pain for a few seconds but thats all. It helps if you push back, kind of like youre passing a....well, you know."
She didnt replay and I waited for a few seconds as I stroked her back and hips tenderly to help her relax. Spreading her cheeks wide, I moved the vibrator over her anus a few times to let her get the feel of it and when she once again seemed to relax, I forced the tip of it into her.
"Oh fuck," she cried as
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it slid past her sphincter and once again as it moved past the inner muscles but then she settled down as I began moving it deeper and deeper with each short stroke until it was buried in her rectum. I left it there for her body to accept, then I began slowly, adding just a bit of speed to each long stroke. I was wishing I had a strap-on but Id never bought one. Id had no reason to, but as I continued fucking her virgin ass, I decided that it was the next thing I was going to purchase.
When she began pushing into the vibrator, I began going faster and deeper until she was verbalizing her first ever oncoming anal orgasm. It hit her hard as I rammed the vibrator deep and left it there while I forced two fingers into her pussy and began driving into her. The orgasm seemed to go on forever and I finally pulled my fingers out and began rubbing her back and shoulders to help settle the spasms.
When she had calmed, I climbed onto the bed next to her to take her in my arms, kissing her tears away and telling her she was beautiful, which was the absolute truth. We held each other close, stroking over each others bodies as she drifted off to sleep. For a while, I just lay quietly, watching the rise and fall of her breasts as she slept and then I too dozed off, happy in the knowledge that Id passed my first test, regained her friendship, and at last tasted her on my tongue, heard her in orgasm and knew we were just beginning a new level of affection for one another.
By the time I began to slip off to sleep, I knew that I was entering a new level of pleasure and maybe more. There wasnt a doubt in my mind that I was ready for it.
When Jillian called me the day after orientation, I knew that training or whatever it wound up being, was about to begin, and I also knew Id made a wise decision to skip orientation. She proposed a meeting to discuss the lists and information Id been given.. After discussing several dates, we agreed on the following Tuesday at one of the smaller meeting places. I took down the location, noting that I was familiar with the area, having a close friend that lived nearby. The office complex was one of three that were destined to be demolished for construction of a new hospital and research center. Nearly all of the tenants had relocated already and the others were in the process of doing so.
"Just casual, Samantha. Jeans, or whatever. Ill be sure to have some snacks and refreshments. I think Beth is bringing some other training materials so well be busy."
Oh, I had no doubt of that, remembering the lust in the womens eyes when last wed met.
When I opened my calendar on the computer, I
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