Weekend With D… part III
My phone alarm went off and we got up and got ready for the concert. Before I put on my cloths he picked up the anal dildo and lube from the dresser where he’d put it before we bagged things up so we could lay on the bed. He tells me in a stern voice “Bend over”. I paused then started to ask him if he wanted my panties down and he quickly walked over to me and as he bent me over he told me “I didn’t ask you to speak did I?” I moved my head in a “No” direction and he quickly slapped my butt and I knew what I needed to do instantly, I said “No Sir, you didn’t ask me to speak, I’m sorry Sir.” I smiled, and held back a laugh. I just love it when he talks like that. With that he put his fingers into the waste of my panties and pulled them down so hard I thought they’d rip. He spread my legs with his feet at the same time he was spreading my cheeks. I closed my eyes tight because he was doing things to fast that I thought he’d ram it into me, I was really afraid of him doing that. (It’s not that I don’t trust him it’s that I don’t trust most. It goes back to when I was married and my husband, someone who I trusted completely tried to enter me fast and with out any lube. It was so painful and I screamed out so loud because of the pain, and then cried because he didn’t stop when I told him to. Even though the anal thing is what I desire, because of that, I have trust issues. I thought I’d let those issues fall away with J but I guess it’s a trust that has to be developed.) He must have seen how tense I was and he started to rub my butt cheeks and then when he went to spread my cheeks again he did it slower, touching me and then I hear the lube squeeze out and I felt the coldness on my anus. Then I heard him put some lube on the dildo too. He then spread my cheeks with his left hand as he positioned the dildo plug at my opening. He presses it slowly in and out a little bit, and when it was in about an inch and a half he asked me how that felt? I said “It feels good Sir”, still I was breathing deep and trying to relax at the same time while my ass was feeling invaded and incredibly stretched. He told me that he was going to push it in some more that it should be okay and that he’d do it slowly. He pushed it into me little by little with out pulling it out and then the last few inches he pushed it in fast and I gasped but it didn’t hurt he was right it was beyond that point already. It went in all the way until my anus close in around the smaller portion of the plug. I hung my head down and was still taking deep breaths. He got behind me and started to rub the head of his cock on my clit and it felt good it was taking my mind off the big uncomfortable dildo in my ass. He then started to push his head into me and I and spoke out and told him that I didn’t think I could handle both in me, I forgot about the speaking so I ended it quickly with a “Sir”.
With that he went back to rubbing my clit but, with his fingers this time then he slipped one in and he said in a surprised voice “You’re still swollen” and I nodded a yes.
He then slapped me on my but and told me to get up. I did and then he motioned me to turn around and face him and he kissed me, then told me looking me directly into my eyes. “Okay Babe now tonight when we’re at the concert I want you to stand up and clap or shout or what ever, every time the drummer lifts his hands in the air from drumming.” I opened my mouth in surprise of what he just told me and blushed. He said “Yes, you’ll be fucking your own butt every time you sit down” and he giggled. We finished getting ready and headed down to the show. All was fine till they started to play. Now you know more than one did the drumming and I didn’t realize how expressive they were with lifting there hands in the air so many times. It wasn’t so much that I had to fuck my butt each time in standing up and blocking the peoples view behind me that I told D that it’s not fair to them so he leaned in and whispered with a grin into my ear “Then bounce a bit in the chair and clap your hands with excitement., it will be the same thing” hahaha, well I did and I wished I had, had a drink or two before so I wouldn’t have to ACT so excited. They are good but not as good as my excitement had to show in order to bounce excitedly. When the concert was over I was relieved and was really wanting to get that out of my butt. Now I’ll always associate that group with my new experience D. It was fun but I couldn’t wait to get back to the room so I could remover it.
After the concert we went to a bar and sat and had a drink, I thought and told him that I could have used it before the concert but this is good too. He told me that he didn’t want me to drink before, so that I could feel everything, physically and mentally, but that after a drink we’d go back to the room and and.. and he left it just as that, he didn’t tell me anymore, as I just looked at him waiting for him to finish and tell me what was going to happen. He took a sip of his drink and told me you’re too curious. I laughed and nodded in a knowing yes. He winked at me and told me, I like that in you, it makes me feel like I’m even in more control than I really am. We headed back to the room and all the way there I was fearful of what was going to happen. I knew that we couldn’t have regular sex without it being painful, and all that was left was anal sex and that would be what would happen after he removed the dildo plug. I was right and so we tired, he was as gentle as he could be and patient. It was erotic up until the point where I couldn’t take anymore, just getting his head in me was such a struggle. We ended up stopping. We talked about things and he thought for sure it would be just a matter of time and having more sex and more anal training, and that once he got the job where he’d come here more, that would change. I nodded and agreed but deep down I knew that we could spend everyday on it and things wouldn’t change as it hadn’t with the ex BF. I wanted to be optimistic and I wanted to really give it a go. I was more than disappointed and he was sweet because he saw in me and told me that it was okay, but really I felt like I failed him. He said he was fine with it and then told me why did I think that he’d be mad at me or disappointed for something I couldn’t help. He hugged me and held me all night long. He feels so good lying next to him with his arms around me. In the morning he ordered breakfast delivered to the room and while we ate we talked about our past relationships, he asked about my ex husband, J and R. It’s amazing how much in site you can have about things when they are over and time has passed. I asked about his past as well, his ex wife and past subs and girl friends. We ended up on the bed again and he was cautious but I wanted to fill him in me one more time since this was our last day together. So even though he said I was to be sub this weekend he made love to me. He is so open and willing to connect with me, he doesn’t separate the kinky from the romantic sex, I really like his flexibility and his willingness to connect with me. He can be both at any given time, Dom and romantic. He tells me that I’m beautiful, though he doesn’t have to. Like most woman I’ve been told that before but his sincerity and the way he looks at me, shows in his eyes that he means it, what a wonderful feeling to be desired. We are each others types and we think we make a cute couple.
Before we left, we put our bags in the car and then came back in to walk around and gambled a little. I won a little and he broke even. When we drove out he mentioned that one day we’ll come back and try a different hotel and he point to the Bellagio and then winked. I told him that where we went didn’t matter it was the time I spent with him that mattered. It had been a long time.. since that last BF, that had I spent that much time with a man. It was nice, being there and making a memory but it wasn’t necessary, I would have enjoyed his company just staying at my house. As we drove out of town I started to think about what happened with D the night before, I thought about how I normally in the past I have loved anal sex, I know that his cock is really big much like that past BF of mine. D’s is about 8 inches long and 7 1/2 inches around and that’s close to the same for the ex BF. With the ex BF we tried so many times even one day he spent about 6 hours in trying to stretch both holes and in the end nothing really changed he was only able to put the head of his cock in my ass and nothing more, and sex with him well it’s was always just once every 3 or 4 days due to recovery time. D broke the silent and my train of thought and asked me what I was thinking about, I told him and I vowed to myself to make an appointment for the doctor and see if there is anything I could do, to that I could at least take him better and have less recovery time with regular sex. He laughed and said “Oh yeah like he’s going to tell you how to make it losser when everyone else is asking him to tighten it up.” I laughed and then told him that I was serious! That it bothers me that we can’t do it all the time. He smiled and caressed my chin with his hand and said I’m not worried about it.
I know in this life and even more in this lifestyle that it’s hard to connect with someone. We connected right off when we first met on his first trip to that town south of here, I with him and him me. When we met it was just a validation since we got along so well the first time we talked on line, and then on the phone and all those weekends we met when we didn’t have sex. Our friendship grew, he was like me, he wanted a long term relationship. On the drive back we talked about the things that we wanted and what we thought about in terms of “Us”. He mentioned to me about getting me a trainer, since I’m so badly in need of one and since when he’s here he wanted to spend good quality time. Though I trust him I wasn’t sure about this. I’m not sure I could be trained by just anyone he picks. He asked for recommendations, he asked if I new anyone that could and would train me that I trusted, I thought about how I wish there was someone I trusted enough but I couldn’t as if I had found someone this far I probably would have been with them and we would not have contacted each other. I did make a suggestion but it was out of just coming up with someone, I suggested R. Though with R, I new he could do it, it is that he’s so very unreliable since he works so much and is always out of town for work as well. I know I should want to do this for him but really deep down I just want him to do the training, though I didn’t tell him. We agreed that both of us would look for someone to train me and put them all in to pot and then pick the best two and then see where that goes. He told me to contact R about what we talked about. Though I had been talking with R on line off and on, I wasn’t sure about this, wasn’t sure about R in general. Though it wouldn’t be part of the training, R doesn’t fit me either.
Well all in all it was a really fun weekend, and enjoyed and loved spending time with D, but to answer sub teach’s questions. No I’m not in love with him, I like him a lot and love the things he does and our relationship but for me (Now) love is something develops over time, through experiences and time spent with each other, getting to know the person and learn what they are about. Love has to do with loving someone, all their good and all there bad as well as the ability spend time together, and communicate, but I am in like and in lust, have been since we first met. There are qualities that I love about him, he’s a “Got his act together, no drama” kind of guy, that’s attractive and draws me to him. My pictures will be put up again soon, where I housed them before closed down; I just haven’t had the time to upload them to a new place.



Well even though you’re not in love it’s good to read that you’re in like, happy and having fun! Amazing, that’s the first time i’ve heard of a woman being so tight it hurts, thought it stretched enough to let a baby out!
i wish the best for you,
sub teach