Date: Tue, 6 Jan 2015 02:40:23 +0000 (UTC) From: Beaumonte Bill Subject: Bill and Ann Part 10 I am an older married man who has dated many cross dressers and transgender women over the years. At first it was a kinky "walk and the wild side" but over time I came to really have feelings for the person, and that became more important than the intimacy we had. The movie "Soldier's Girl" was very moving and helped me realize that I really wanted to LOVE a transgender woman. I have had several truly wonderful loving relationships, and have come to believe that if I knew what I know now when I was young, I would have married a transgender woman. This series is a fantasy in which I imagine what that life might have been like. It is set in the late 1960's, when I was a teen. –Bill (oral_guy_2000@yahoo.com) Bill and Ann Part 10 On my next visit to Ann's, she received me with the wonderful kiss I had come to love so much. We joined Helen in the living room and both sat on the couch, facing her. "We were talking about my former virginity," Ann said, smiling. "That seems like something you shouldn't discuss with your Mom," I declared. Helen interjected, "It is something rarely discussed in family, but I am pleased to know of the blessed event. While many men regard taking a girl's virginity as a conquest, you have made it a noble and memorable event, and I welcome sharing whatever part of it you both may be willing to share with me. Knowing that Helen was very different, still I was caught by surprise. However, I agreed, saying, "I never anticipated having this conversation with you, but trust and care for both you and Ann, so please ask me what you will." "I would really like to know what it was like, entering Ann?" she asked. "It was like heaven on Earth," I said, "being one with Ann – it felt wonderfully tight and warm, and gazing upon Ann's beauty was so very wonderful. I don't have the words to really describe it, but that's the best I can do." "And for you, Ann," asked Helen. "I heard it could be painful, but it was anything but that – Bill was so gentle, he felt so wonderful inside me. Joined as we were, it was joy to look upon the man who has brought out the woman in me – I am so glad to give myself to him!" "I've read quite a few romance novels," said Helen, "but have never heard it described as you two have." "I'm glad we could share this with you," I said, "It is a very private matter, but one I'm glad to have shared with you, Mom." "Were you telling me the truth yesterday when you said you had lost your virginity as well," asked Ann "Yes my love, I have never lied to you," I responded. "But what about the other transgender girl you were with – did you not take her?" Ann inquired. I paused, thinking of Eydie, and then answered, "I had the opportunity, but did not – I just gave her oral pleasure." "Certainly few men would pass by such an opportunity – why did you?" asked Helen. "I wanted to, but after all she had been through, it just wasn't right," I said, "She was surprised as well" "Why was it not right?" asked Ann. "Eydie's father gave her to other men who raped her, and paid her father," I explained, "every entry she took was a rape – never out of love and caring, so I pleasured her in other ways." "So it seems that you have always been a gentleman, dear Bill," said Helen, as Ann nodded, "have you no skeletons in your closet?" "I'm not sure what you mean – I have no skeletons in my closet or bodies buried in the back yard," I said. "I just mean," continued Helen, "is there nothing about your past that is less noble than the young man we know now?" I paused, not sure what to say. Finally I summoned the courage to say, "There is, and I am ashamed of my past, and ask that you not press me for details – at least not for now." "When you are ready, you shall tell us," assured Helen, "We have talked of very private matters, and when you feel comfortable, we will listen without judgment." "Judgment," I said, "I fear that if you knew what I have done, neither you nor Ann would have anything to do with me." "I've seen nothing but goodness and caring in you," said Ann, "Even if you were an axe murderer, I would still love you!" "I'm no axe murderer – nothing like that at all," I replied, "but I have done very shameful things, which I cannot bring myself to tell." "We will drop this dear boy," said Helen, "I shall not ask of it again." I felt relieved, but knew that one day I would have to confess my past. At least I was safe for now. Ann stepped out and Helen said, "I was perhaps indiscrete when I told you that I was still a virgin." "I'm sorry you have not had the opportunity to share what Ann and I have," I replied. "There is more," Helen continued, "I have never had a climax, and really wish I could." "I'm sorry you have missed such a wonderful thing," but it's not too late," I said. Helen dropped her head and hesitated, saying, "I don't know how." I was astounded, and my heart went out to her, so I continued, "May I tell you how you can do it yourself?" "Myself? I've always thought that was such a dirty thing to do!" she declared. "Dirty? That's an archaic Victorian belief!" I said, "fostered by the kind of religous nuts that tortured Ann." I continued, "When you are taking a bath, reach down between your legs and find your clitty, at the top of your vagina. If you gently rub your finger across our clitty it should feel good. If you keep doing it you should reach climax." "I'll try that," said Helen, "but please don't mention this to Ann; I'm embarrassed about it." "I hope it works," I said, "and thank you for trusting me." Helen kissed me on the cheek just as Ann came in, and said, "What have I missed?" "Just a fine son comforting his Mom," Helen responded. I took Ann by the hands and pulled her to me, kissing her. "Shall we go upstairs?" I asked. Ann quickly agreed and led me up to her room. I lovingly unbuttoned Ann's blouse and draped it over a chair. Taking Ann into my arms, I reached behind Ann and unhooked her bra. As I removed it her ample breasts were revealed. I cupped one in my hand while kissing her, our tongue mingling in our mouths. I wanted to please Ann in every way I could. I removed Ann's skirt and panties, kissing her clitty as it was exposed, then briefly sucking it into my mouth. After sucking a few minutes I let it fall from my mouth and stood up, again holding her tightly and kissing her. We moved to the bed and I set out a jar of lube and warm wet wash cloth. I positioned Ann on the bed on her hands and knees, with her pretty ass in the air for me to attend to. I kissed her pretty rosebud and then pressed lubed fingers into her, preparing her to receive me. Once she was ready, I turned her over onto her back and put her legs up onto my shoulders. I pressed my hard cock to her rosebud and gently pressed into Ann. I whispered, "please tell me if I'm going to fast." Ann smiled and I slid in a bit more, pausing for her to adjust to the feeling. I pressed in further until all the way in. Ann was smiling with delight. I stroked slowly in and out, almost overwhelmed by how wonderful Ann felt around me. She was clearly enjoying it as much as I. I had heard that some men finish quickly and leave their partner unsatisfied. I didn't want this for Ann, so I tried to hold back. I took some lube in one hand and fondled Ann's lovely clitty while pumping in and out of her. Her arousal was apparent and soon she was screaming with her climax. I saw that her nipples had hardened and knew she had truly climaxed. I released her clitty and in a few strokes I was pumping my seed into her. I paused to admire Ann's beautiful smile, before slowly withdrawing. I took the warm wet washcloth and cleaned Ann, both back and front, and then went to the bathroom to clean up myself. Upon my return, I lay next to Ann and held her, making sure she felt wanted and cared for. I had inadvertently left the door open when I returned from the bathroom, and found Helen looking in on us. She entered and pulled the covers up over us, and said, "It is so wonderfully tender the way you cuddle afterwards. So many men just get up and leave afterward." "I wish I didn't have to get up and leave at all," I said. "If you can make arrangements to stay the night, I would be glad to see you two sleeping in each other's arms. I liked the sound of that, and resolve to find a way to make it happen. Sadly, it was time for me to get home, so I got dressed and departed, savoring a long kiss with Ann at the door. To be continued . . . Feel free to contact me with your comments or requests. –Bill (oral_guy_2000@yahoo.com)