It is not important how we met, but we did, she much younger than I, and both of us into some role playing. In this case it was decided that I would be her daddy and she my daughter—getting together after a long absence. She was in her 20’s, and we agreed to meet at the Starbucks in the shopping center and have a cup of coffee. I arrive early, got in line to get my coffee and found a table and sat and looked at the door—we had traded pictures and a number of emails, and talked on the phone too, and I was pretty sure that we would recognize each other, and when she walked she looked around, spotted me, waved and headed my way, I stood up to meet her and we hugged and then she sat down. I asked her what type of coffee she wanted, and then went to stand in line to get it for her.
When I got back and sat down we looked at each other nervously, not knowing where or how to begin. I picked up my cup of coffee and pointed it towards her and said “here’s to getting to know each other”, and she touched her cup with mine—that seemed to break the ice and we started talking a lot of things, where we had grown up, gone to school and the usual getting to know each other stuff. I was feeling more comfortable and it looked as if she was also. At one point we started to get discuss the role playing aspect of our meeting, and I told her that if she had changed her mind I would understand, and as we went through the game if she changed her mind at any point I would respect that too—she looked at me and said “thanks, but let’s just see what happens”. As we continued to chat I suggested that we really should finish our coffee and go over to Victoria Secrets and see about getting her a sleep shirt like she used to wear—she smiled and said that would be fine—a few minutes later we walked out of the store and headed for Victoria’s and went inside. It took a few minutes to find the right type of sleep shirt, but we found them and she held several of them up to make sure the one she selected would fit. Once she had found it she asked if she could buy some new underwear too, and I said of course. She told me to sit down in one of the chairs while she shopped and not to look at her and what she was interested in so that it would be a surprise. I did as she asked but I did see her heading into the changing room with several things in her hands. She was gone for a while and then came back out and found a sales person, talked to her for a moment, and the sales woman took the price tags off of what she had selected and put whatever she had selected into a bag. At this point she gestured for me to join her and I did, handing the night shirt to the sales woman who rang up the complete sale, we walked out of the store and I said that we should go to the bar in my hotel, and she said that she would follow me over in her car. It was still early but the bar had a few people in it, we found a table out of the way, and I went to the bar to get our drinks. When I returned she was looking at the contents of the bag and quickly put it down when I arrived. At this point, sort of automatically, we started into our roll playing. I toasted her and told her how great it was to see you after all of this time and how beautiful and sexy she was and that she had truly become a woman since the last time we were together. She smiled over and me and told me that she had missed me, and that she missed all of the time we had spent together and how close we had been. We talked like this for a while, and soon I ordered us another drink. After a while she smiled up at me and asked me if I had a nice hotel room and I said that I did, and she asked if I thought they would let us take a new drink up to the room so she could see it. I told her they would and went and ordered two more and closed out the tab, as I was returning to the table she was already standing up holding her shopping bag in her hand and we walked out of the bar and towards the elevators together. As we got in the elevator there were others with us so we rode up to my floor without speaking, we got off the elevator and walked over to my room and I opened is—she walked in and saw the living room first, I was staying at an all suites place so that the bed was not the first thing she saw—she walked in and then walked back to look at the bedroom, and then into the bathroom, and she came back without her bag, I had our drinks and I sat down on the couch and she sat across from me on the chair. We each had some of our drink and then I asked her what she had been doing since she had been out on her own, was she dating and what was she doing with guys? She looked at me and said “Daddy I know you are going to be mad at me but I have been a bad girl, I have been with a number of guys and even though you warned me, I let them touch me and do some things to me and did some things to them too—I know it’s wrong daddy and if you need to spank you can. I looked at her and told her I was disappointed and then I told her to stand up and come to me—she stood in front of me looking down at me and I told her to take her shoes off, which she did, then I started to unbutton her jeans, and then told her to get out of them—and her panties too—next thing I knew I was looking at her shaved pussy—I said—daughter—you shaved down there too? And she said yes Daddy I did—ok I said, come here and I grabbed her-not too hard and put her across my knee so that her butt was facing up I started to spank her bare butt—slowly and gently at first and then faster and with more power, she took it and kept saying that she was sorry and that I had every right to spank here and she would behave in the future—which I knew was a lie—so I hit her harder, after a while I moved my other hand down between her legs and pushed them apart, one of my fingers found her clit and I started to rub it, and heard her gasp, I was spanking her hard now and my finger was circling her clit, I moved my hand as I felt her wetness and then put one and then two of my other fingers into her pussy—I was still spanking her, using my finger on her clit and moving my fingers in and out of her pussy, I heard her breathing getting harder and then she came and I stopped spanking her but left my fingers where they were—her clit was sensitive and she squirmed around until I stopped using my finger on it and then just lay there across my lap. After a few minutes I started to stroke her butt and her legs and took my fingers out of her pussy, we stayed that way for a few minutes and then I told that she should go into the bathroom and get into her sleep shirt and get in bed and I would be in a few minutes to tuck her into bed. I heard her going into the bathroom and then I heard water running and after a while the door opened and she must have gone into the bedroom. I took a few more sips of my drink and waited for a few minutes and then went into the bedroom. She was laying on the bed about mid-way so that I could easily sit on the side of the bed. She had the covers up to her chin and was looking at me when I walked in. I leaned over and kissed her forehead and then I put my hand underneath the blankets and found her stomach and I started running my hand over it—do you remember when I used to come into your room and do this I asked? Yes she said, and I really liked it. I slowly moved my hand up to one of her breasts and felt her nipple underneath the sleep shirt and ran my palm over her nipple and around her breast—do you remember when I used to do this too I asked? Oh yes daddy I do! I then leaned over and kissed her on her forehead and then moved my hands down below her sleep shirt and moved them slowly up over her legs, gently, and up to her stomach, the sleep shirt was riding up as I moved both of my hands up and started to run them slowly over her stomach and then moved them higher and circled her breasts and teased her nipples with my fingers—I pushed the night shirt up that I exposed her body and it was bunched up around her neck, and my fingers were moving over her nipples, slowly I lowered my mouth to the nearest one and took it into my mouth, letting my tongue swirl over the nipple and feeling it get harder still, she put her hands on my head and said, Daddy, it has been so long since you have do this, I like it a lot Daddy, I always have liked it when you touched me all over. With that I moved my mouth to her other nipple and played with it for a few minutes, biting it just a little, and using my hand on her other nipple while my other hand was trailing down her stomach and stroking her just above her womanhood. I stood up and walked over to the chair and took off my shoes, pants and shirt, leaving my underwear on, and got into bed next to her—we hugged and then kissed, and I started to stroke her body. After a few minutes I lifted her up and took her sleep shirt off over her head and laid it next to her. She shivered and I asked her if she was cold, and she said no daddy, just excited but what you are doing to me. I smiled at her and lowered my mouth to her stomach and used my tongue to trace down to her woman hood, which as I had found out previously was shaved. I changed slowly moved her legs apart and moved between them, looking up at her to make sure she was ok and she smiled at me. I lowered my head and ran my tongue over her pussy lips, and then parted them and my tongue went searching for her clit—which I found, and it was already swollen and waiting for me. I circled it with my tongue, lay flat on the bed with my feet sticking off of it, and moved my tongue over and around her clit, down lower and into her pussy and back up to her clit, I could feel her moving under me, staying with my rhythm, and moving with me. I moved one of my hands towards her breasts and took one of her nipples between two of my fingers and moved them around it, feeling its hardness against my fingers. I then removed my hand and moved it lower, so that is we under my head, and slowly opened her pussy and moved one of my fingers inside. She was wet, very wet, and it did not take me long to move my second finger inside of her—and my tongue as still swirling around her clit, and every once in a while I would take it into my mouth like it was a small cock, and suck on it, and then move my tongue around it some more—she started to gasp and hang on to me and I heard her and felt her come. I stopped but did not move my tongue or fingers, just let her explosion sub-side, and then I slowly started using my tongue on her again, very gently, but then a little harder, and she exploded a second time, this one seeming to be harder than the first. I moved up so that we were lying together and I hugged her and told her what a great little woman she was. She smiled and me and we kissed and she tasted her own juices in my mouth. After a while she said, Daddy to you want me to do to you what you taught me to do? And I said yes I would-she moved over and removed my shorts and put her hand on my cock. I said do you remember how I first taught you to do this? Remember I had you put one of your fingers in my mouth and then I had you do with your mouth what I was doing to your finger? Yes she said, let’s do it what way again—she gave me her finger and I slowly started to move my tongue around the tip as she did the same thing to my cock, I move her finger into my mouth, slowly and moved my tongue around it, and she followed my every moved, I moved her finger back and forth, in and out, took it out, licked the tip and then the side of her finger and put it back it, and with each move she followed, and finally I started to move it in and out of my mouth and she followed quickly. I let go of her finger and she kept up the pace, and then put her hand on my balls and kept up moving my cock in and out of her until I came. She swallowed it, and then licked my sensitive cock head and then my shaft and then came and lay down next to me. Did you like that Daddy? Yes I said, and I want to get up and have some more to drink and then we can come back here—daddy and his darling daughter still have things to do—I know daddy and your daughter has a question about something all the boys want to do but you never taught me about—so can we talk about that too? Of course I said, you know that we can talk about anything.
She put her sleep shirt back on and I put on the bathrobe that was in the room and we went out into the living room. She went into the bathroom and came out a few minutes later and then it was my turn. I got back and poured us each another drink and we sat together on the couch, close to each other enjoying the afterglow of our earlier activities. We sipped our drinks in silence for a few minutes and then she said: Daddy, how come every time I get intimate with a boy and we have fun together, at some point he wants to start playing with my ass? One guy wanted to put his cock in my ass—I would not let him but why do men all seem to want to do that? Doesn’t it hurt the woman? It is safe? Well, baby girl, I said, since you brought up the subject let me tell you a few things about that. First of all most men believe that anal sex is the most intimate of all things which I woman can permit. It is something that she only gives up to someone who is special to her—usually. As for the rest of your questions let me see if I can answer them: First it can hurt the woman but not if done properly and by a man who understands how to make it exciting for the woman, next it is safe as long as the two of you are careful and clean. In my experience I have found three types of woman when it comes to anal, or perhaps four. The first are those who say don’t ever touch be there, the second types are those who say a little kissing and perhaps finger play is ok at the right time (when I am super excited) but nothing more, then there is the type that accepts it or likes it and are willing participants (these are usually the woman who have had a first good experience), and finally there is that small group of woman who really enjoy it, some of which can actually reach an orgasm that way. Well, daddy, I don’t know what group I fall into, it sounds both exciting and scary to me, but since you are my daddy and I trust you, perhaps you can teach me to enjoy it. Perhaps I can, my dear, or perhaps we will find out that you don’t care for it but then you will know, and in the process I won’t hurt you, and I will stop whenever you want me to. Thank you daddy, she said as she moved to knees on the floor, moved between my legs and opened my bathrobe and started to suck on my cock, I felt myself getting harder, and she looked up at me and smiled. Then she stopped what she was doing, brushed my robe further apart, pulled up her night shirt and straddled me. She lowered herself onto my cock, reached around with her hand to position me correctly, and then moved down so that I was completely inside her pussy. I looked at her, smiling, and reached over and pulled up her night shirt more and started stroking her breasts and nipples, she looked across at me and then started moving up and down on my cock—it felt great—She was good, and I could feel her pussy putting pressure on my cock as she tightened her muscles. It did not take long for me to cum—and she stopped moving and sat there as my cock started to recede, and then she got off, and kneeling on the floor once again, she started to lick our juices off of my cock and my balls where it had run down.
After a while she got up and let me to the bathroom and we both got into the shower—I was thinking about how I was going to show her about anal when I had just cum, but figured that we would just have to see. We got in the shower and started washing each other—and then she moved so that she could clean her pussy and her pussy lips while I cupped her breasts in my hands. We got out of the shower, dried each other off, and headed for the bedroom again, I went back to the living room to refill our drinks and then returned to find her buried under the sheet and blanket—waiting for me. Take off your robe daddy—and warm me up, I am chilly, she said, I did exactly that, took off my robe and got under the covers with her—and reached over and found out that she was not wearing her sleep shirt, and I hugged and kissed her and started to stroke her with my hands, along her back and down her arms, up around her neck, and I kissed her again and then I moved my mouth down to her neck and kissed and licked it and then took the lower part of her ear in my mouth and licked and kissed it also. She squirmed a little—and I could feel her enjoying my touch which I loved—and soon we were kissing again and my hand moved down and stroked her ass cheeks, moving to her crack, and my fingers gently sliding along it, no in it, and back again—I felt her twitch as I ran my hands over her ass cheeks and my finger now just into her crack—not enough to actually touch her ass hole but enough so that she knew where I was heading. She whispered in my ear—Daddy, you have more to teach me and I want to learn, please Daddy, teach me and help me find out if I like it. I did not answer her, instead I turned her on her stomach and moved her legs apart and got between them—like I was going to give her a massage—which I guess I did for the next few minutes—I moved my hands over her back, followed by my tongue, got to the small of her back and moved my hands around her ass cheeks, and started to kiss and lick her back and then right where her ass crack started. I moved my hands over her cheeks, and slowly, very slowly moved my tongue downwards, not quite penetrating her crack but certainly moving my tongue along it—she wiggled and sighed and I moved my tongue back up. I raised my head and looked down at her and then used my hands to slowly pull her ass cheeks apart—and just help them there, spread like that for a few minutes and then I let them go, I looked around and told her to hand me the pillow that was next to her and she did, I told her to get up on her knees and I put the pillow under her and told her to lie down on it, she did and her ass was raised up. She did not know what was coming next—and I started to stroke her crack again, this time letting my fingers move deeper and lightly touching her ass-hole with one of them. I then moved my tongue to the tip of her crack and started moving it down, and into her crack as I moved, I came to her ass-hole and let my tongue swirl around it, and then I gently spread her ass cheeks and moved my tongue into her ass-hole—she squirmed some more and sighed louder and I could tell she was enjoying what I was doing. I moved my tongue, and pulled her ass checks further apart and moved my tongue deeper inside of her. Meanwhile I moved one of my hands so that I could put one, then two fingers into her pussy, and my other hand stroked her back. After a few minutes, when I felt that she was ready I removed my tongue and moved one of my fingers right to her ass-hole and started rotating it around. I moved it slowly into her—and the next thing I knew she was pushing back to help me get it into her deeper. If I needed any more indication that she was into this and enjoying it, that was my signal and I continued to move my finger forward until it was all of the way in, meanwhile keeping the fingers from my other hand in her pussy, and moving my thumb up to her clit. She wiggled around, pushed back on my fingers, and started breathing heavily. After a while I moved a second finger into position, withdrew my first finger and then started to put both of them inside of her—once again she pushed back as I was pushing forward and soon both of my fingers were deep inside of her. I moved my thumb over her clit, and the fingers in her pussy and in her ass moved also, and I moved them so that I could feel them through the thin layer of her that separated her pussy and her ass. She was moving around more and I thought perhaps it was time to move forward. I removed my fingers slowly, told her to sit up, and I stood on the floor at the edge of the bed, I had her take my cock in her mouth until it was hard and then I opened the night stand drawer and took out a bottle of KY. I told her to open it, to put some on my cock and then to reach around and put some in her ass. She did as she was told and I told her to lie back down the same way she had been, and that I wanted her to reach back and pull her ass-cheeks apart. She did so and I used my hand to guide the tip of my cock to her ass-hole and then slowly, very slowly, inside of her, just until the head of my cock was inside. She seemed fine with it, but I knew that there was a spot where she would experience some pain as I moved forward. So did two things, first I told her to start using her fingers on her clit and second I told her that she was going to push back on my cock and take it as fast or as slow as she wanted to and if at any time she wanted to stop or to have me remove it, to tell me. She was game, I will say that for her, she pushed back on me and my cock started to enter her. At one point she made a noise as if she was in pain and stopped. I told her to wait a minute, to relax and take deep breaths and keep playing with her clit, and that if she felt she wanted to continue she should start pushing back on me again. After a moment or two I felt her begin to push back on me again and I pushed forward and it did not take long for me to be all the way inside of her. I stopped for a moment and let her catch her breath, asked her was ok and she said yes she was, and so I said, keep playing with your clit, I am going to fuck your ass, and you are going to tell me to fuck your ass, and tell me to push my cock into your ass deeper. OK she said. I started moving in and out of her slowly, and felt her reaction, and felt her playing with her clit but she did not say anything for a few minutes, but when I started moving faster I heard her telling me to fuck her, fuck her hard in the ass, and Daddy, don’t stop fuck my ass, Daddy, fuck my ass. I moved faster and faster and it did not take long for me to feel myself getting ready to come. I told her, Daddy is going to cum in your ass, right now! And I did. I stopped but she continued to play with her clit and a minute or two later I heard her cum, and felt her cum. I stayed there with my cock in her ass for a few more minutes and then removed it and collapsed next to her on the bed, we looked at each other and kissed and I stroked her back and butt. We lay there for a while and talked about her first anal experience, she said that she was very excited and that it only hurt for a moment and that when I came inside of her she could feel my warm cum flowing into her and it felt good. We hugged and then went into the shower to get cleaned up. Later, sitting in the living room again, in my robe and her sleep shirt I told her that next time we would use a dildoe in her pussy at the same time, something that is called double penetration I said, some woman love doing it with two guys and I have seen one woman with a cock in her pussy, one in her ass, and one in her mouth. My darling daughter looked at me and said, I don’t know if I want to do that Daddy, I mean with 3 guys and I said, if you did I would have to really punish you. We finished out drinks and it was time to go, we agreed to meet the next time I came to town, and as we were sitting on the couch saying goodbye, she asked me if I had ever been with two woman and me, and I said, yes, I have several times—she said, I have always wanted to be with a woman and I have a friend who I think is interested, and I told her about my daddy and she is interested in you too, would it be alright it I brought her along next time? Yes, I would like that I said, as long as it is ok with you—Daddy, she said, I just want to make sure that I really please you because you make me so happy. See you next time my darling daughter I said, it won’t be long!
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