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on my lips, licked at my slit, dove for my clit, sucking it into her mouth, then lapped at it so fast I almost screamed. I had been so aroused that she quickly brought me to not one but two hard orgasms without letting go of the sheets. I knew she was going to fly through her orientation but then, as I climbed off of her face, I remembered the anal penetration. How could I prepare her for that without frightening her away?
"Dani, youre doing fine." I advised her, slowly trailing my fingers over her and wanting to take her completely but knowing I had to restrain myself. Hopefully, there would be more opportunities in the future.
"Is that all?" she asked.
"No, honey, not all," I replied. "Im just trying to find a way to prepare you for the rest without violating any rules."
"Samantha, I know youre trying to make this easy for me but I need to know. I cant stand going through all of this only to change my mind at the last minute. I wont do it again if I do and we both know it."
"I know," I agreed.
"Is it painful?" she asked, and I could hear the stress in her voice as it quivered. She was nibbling on her lips as well.
"Dani, there is some pain at times, but is replaced by pleasure. Do you remember when you lost your virginity? Its something like that but a little more painful at the beginning. Then it becomes pleasurable."
"When I lost my virginity, it hurt like hell because he didnt know what he was doing and I had a thick hymen. I kept waiting for it to be what everyone told me it would be but it never became something I wanted. It burned and he was in such a hurry, he came right away and as soon as it was over, he left. I never talked to him again."
I smiled, remembering my first man. It hadnt been much better than her experience though. "Its not that bad, Danni, but Id be lying if I didnt tell you that it does hurt some."
She laid there for a few seconds, allowing my fingers to work their magic on her nipples as she pondered her next statement.
"I think Id rather have you do it to me the first time. Can you, without getting in trouble?"
I thought for a second, then made a decision. "I cant duplicate what you will experience, Dani. For one thing, I dont have the equipment that they have, and for another thing, I think Id be violating my confidences if I did. What I can do is to let you experience a small sample of it so you can experience the feeling without the pain. Is that all right?"
"Id like that, Samantha. Would you just take it slow though? Im such a big chicken."
I laughed and bent to kiss her. "No youre not, Dani. You just needed someone to hold
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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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