He called and asked if he could come over after school. His name was Brad and he was 18 and a senior in high school. He worked in the local grocery store and would take my groceries out to my car. He was a nice boy and we would have conversations. He said I reminded him of his Grandma. I laughed and said I hope that's a good thing. He said yes and that he and his Grandma were very close and she basically raised him. She had moved and he really missed her. He said she is built just like I am. He smiled when he said that and I knew he meant my bust.

I have been transitioning for years. Hormones have given me significant tits. I wear a 38 D bra and probably should be in a DD. I always dress nice when I am out as a woman which is almost 100%. I am very passable and suspected he had no idea I was a genetic male. I was going to tell him this but decided not to. We got to know each other better and after a couple of months I felt good enough about him to give him my address and phone number. I told him if he ever wanted a home cooked meal or just to talk he could call me. After about a week I figured he had blown me off and then out of the blue he called.

My heart was pounding and I told him sure he could come over. I expected him about 4pm. What was I going to wear? What was I going to do? I had a couple of hours. I showered and spent extra time with my makeup and hair. I wanted to look nice for him but not slutty. I decided on a nice bra and panty set. I would just wear my house robe over that. Something his Grandma might do. I put some light perfume on. I stood in front of the mirror trying to decide how to work the robe to show off my cleavage but not be too forward.

I made some fresh baked cookies. That smell is always comforting. I was pacing around trying to think of anything else to prepare when the door bell rang. It was him. I adjusted my robe and opened the door with a smile. He was standing there and looked me up and down and smiled back. As he entered my house he said I looked great. I blushed and thanked him. We sat at the kitchen table. I offered him some cookies and he took one. I sensed he was nervous so I started the conversation. I asked him to tell me more about his Grandma and their relationship.

He said when he was 4 or 5 his Mother worked nights. His Grandma was living with them and basically took care of him. He started to have a lot of nightmares and had trouble sleeping. His Grandma would hear him crying and she would come into his room and lay down in bed with him. This helped a little but he was still very restless and didn't sleep well. One particular night he was having a nightmare and she heard him. She got in bed with him and he laid his head on her ample chest. He was still upset from the dream when she opened her nightgown and pulled out one of her breasts. She brought the big nipple to his mouth and told him to suck on it and that would make him feel better. He took the large brown nipple into his mouth and started to suckle on it. Soon he was fast asleep.

This soon became a routine for them. Whenever he felt anxious or was having difficulty sleeping she would nurse him like a baby. This went on for years until in his early teens when she moved away. I listened to his story and could tell how much he loved her and their special connection. He asked me if I thought that was weird and I said absolutely not and that I would have done the same thing. He sat there in silence for a minute or two. He said he had a confession to make. I told him to just relax and he could tell me anything. He said that after we first met he thought about me all the time. He looked forward to when I came to the store because it meant he got to see them. I said them? He blushed and pointed at my breasts. I looked down and saw that my robe had fallen open some and my large breasts were on display. I smiled at him and didn't close the robe.

He said lately he has been dreaming a lot about us and that I am in his bed and he is suckling my breast just like he did with his Grandma. I knew what he wanted to say next but he seemed too scared to say it. I decided to just put it out there and see if I was right. I told him I could tell he and his Grandma had a very special connection and bond. I also said I could tell that he really missed it. He nodded. I asked him if he had the chance would he want to suck on her nipples again? He said more than anything. I took the plunge and asked him what about my nipples? Would I be a good substitute for Grandma? His jaw dropped open and without saying anything he just nodded.

I stood up and took his hand and led him over to my sofa. We sat down and I asked him how he wanted to do this. He laid on his back putting his head in my lap just below my breasts. He asked me if this was OK. I smiled at him and opened my robe more. I reached into my bra and pulled out my big breast fully exposing it. My large nipple was rock hard from the excitement. He stared at in for a moment and then reached up with his hand and brought my nipple into his warm mouth. I watched as he started to suckle on it. I put my arm under his head to cradle it and bring him closer. I closed my eyes and leaned my head back lost in the experience. This was the first time since I developed breasts that anyone had done this. I now knew I could not live without it.

I let him stay latched to my nipple as long as he wanted. After some time though it was starting to get a little sore because it had never been sucked like that. I asked him if he would switch over to the other one. I decided to take my bra off to be more comfortable. He got back in position and latched on to a fresh breast. I felt so comfortably with him doing this. As I held him to my breast I could tell he had fallen asleep. His mouth and tongue were still moving in a suckling motion though. I looked at the clock and it was after 6. He had been nursing for almost 2 hours. I stroked his hair and patted his face to wake him up. He opened his eyes and looked up at me with my nipple still in his mouth. I told him what time it was and asked if he needed to go home. He blinked and reluctantly released my nipple from his mouth. He sat up and for a moment I could tell he was figuring out where he was. I closed my robe and waited for him to get his bearings.

He apologized for falling asleep. I smiled at him and asked him if he enjoyed doing that with me? He said it was so great. Just like with his Grandma but even better. He told me he loved my big breasts. He said my nipples were way bigger than his Grandma's and that he loved them. I played with his hair and told him he could have them anytime he wanted. His eyes got wide and he said really? I said yes and told him I really enjoyed it too. I walked him to the door and before he opened it he asked if he could see my tits one more time. I opened my robe and presented them. My nipples were bright red and swollen from his suckling. He reached out and took one breast in each hand feeling their weight and gently squeezing them. While still looking at them he said that these were perfect. He leaned forward and gently kissed each nipple. I moaned a little when he did that. He gave me a quick kiss on the lips and said thank you and left.

I sat down at the table. I opened my robe and looked at my breasts. I cupped them and felt my swollen nipples. They were sore but a good feeling. When would he call? Will he want to have a repeat encounter? Would he get scared and this would only be the one time? I would have to be cautious. Don't push things. Let him take it at his pace. He thinks I am a woman like his Grandma. I will have to tell him the truth, but not yet.

The next day I kept checking my phone to see if he called. He hadn't. I went to bed that night think the worse. I got up the next morning and while making coffee my phone rang. It was him. He apologized for not calling the day before but he had to work late. He was off today and wanted to come over again after school. I told him yes trying to hide my excitement. I wanted to look nice for him again. Make him feel comfortable. I went shopping and bought a new bra. I went to a pharmacy and told the clerk that my daughter just had a baby and was breastfeeding. I said her nipples were getting sore and dried out. Was there an ointment or cream that would help? I bought the one she recommended and would use it after our session.

I could hardly contain my excitement when the door bell rang. It was him. I opened the door and he looked me over. I was wearing a thin silk robe that barely covered my ass. I actually have long shapely legs and I was showing them off. He smiled and just said Wow. I pulled him in and gave him a kiss. Not too hot but not Grandmotherly either. I wasn't sure how far he wanted that to go. I just asked him if he and his Grandma would kiss a lot. He said yes as he got older they would do that. I looked at him and said for him to show me how. He said it was on the sexy side and asked if I was OK with that. I just smiled and said of course. He came close to me. He was a little taller and he put his hand on the back of my neck. He pulled me to him and our lips met. I felt him open his mouth and I did the same. Our warm tongues met and twilled around. I was becoming lost in the embrace and the kiss. He slowly released me broke the kiss. He smiled and said that's how. I said he was a great kisser and that he could do that to me whenever he wanted.

I led him to the sofa again. I loosened my robe and he got into position. Instead of pulling a breast out of my bra I reached down and undid a clasp and the front panel opened exposing my breast and nipple. I had bought a maternity bra. I asked him if he liked it. He said his Grandma ended up buying some of those. He said he liked them but also like it with no bra. Soon my nipple was in his mouth and once again we shared an intimate moment. This became our routine. The weeks went by and usually 4 or 5 times a week he would come over and nurse. Sometimes it was everyday, even twice a day. My nipples were getting used to it. The cream helped. Nursing was having an effect on my breasts. My bras didn't fit well anymore. I was defiantly bigger. I went bra shopping and found I was a full cup size bigger. I looked at them in the mirror. They were bigger and when I felt them the were heavy and swollen. My nipples were a little darker too. I was OK with the changes as long as he was and he kept wanting them.

It had been about 3 months. He was obsessed with my tits. Our sessions were lasting longer. Not only was he suckling he was also playing with them. He would fondle and squeeze them. He told me he could tell they had gotten bigger. I said that was his fault and we laughed about it. One day when he was over he was gently suckling my nipple. My breasts felt really tight and swollen that day. He started to suckle a litter harder and I felt something strange deep inside my breast. It was like a warmth was moving down toward my nipple. He kept nursing and it felt like he swallowed. He let go of it and I thought he was going to switch sides. He looked at me and opened his mouth. I looked inside it and was amazed. I asked him if that was milk? He closed his mouth and swallowed it and said yes. It was my milk. I told him to try the other one and he did. Sure enough he was able to get milk from it as well. He asked me if I wanted him to stop and I said absolutely not I told him if he liked the taste he could go as long as he wanted. The more he sucked the more came out. I couldn't believe it. I was lactating. All his suckling had caused me to produce milk. This was going to be a new adventure now.

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