I was driving to go shopping. I wanted to buy something to look nice for Brad. Our relationship was now at 6 months. He came over everyday. His nursing had caused my breasts to expand and my milk supply had increased. He couldn't get enough of it. I enjoyed feeding him but lately had begun to wonder about something. He loved to play with my breasts. We did a lot of kissing too. Was he going to ask for more? Surely a normal 18 yr old thought about sex. I decided that if he didn't bring it up soon I was going to have to. It was risky but I wanted to be honest with him. I had no idea how he would react to my telling him I was genetically a male. I had been on hormones for so long I felt and thought like a female. I just didn't have a vagina. My testicles had shrunk away to nothing and only the small tip of my glans showed. I had started calling it my clit a long time ago and that's exactly what it was. When I masturbated I would use a small vibrator in my ass and rub my clit. I had never actually had anal sex with a male. Brad would be my first if we got that far.
I parked my car and got out. I was in a hurry when I left my house and just put a t-shirt on with no bra and some shorts. As I walked to the store I smiled. The increased size of my breasts caused them to jiggle and swing. Very noticeable in the thin t-shirt. I liked the looks I got from men. I started looking through some clothes racks and picked out a few things to try on. The next aisle over I saw a couple of women. One had a small baby that I guess was no more that a couple of months old. I was about to head to the dressing room when the baby started to cry. I heard the mother say the she didn't bring a bottle in and that the baby must be hungry. I walked over to them and started up a conversation. I said that it was definitely an "I'm hungry" cry. We chatted a moment and they were starting to leave to go get a bottle. One of the women stopped and looked at me. She pointed and said that it looked like I had an accident. I asked what she meant and she pointed at my chest. I looked down and saw two large wet spots. I was speechless. My tits were leaking and I don't mean just a little bit. Somehow me hearing that baby cry had caused my milk to let down and come out on it's own.
I couldn't believe this was happening. The wet spots kept getting bigger as the thin cotton material absorbed my leaking milk. I was so embarrassed. People would see this and know exactly what was happening. It was my fault for going out braless but I had no idea my breasts would do this. I put down the clothes I was going to try on. Shopping was over for the day. I put my arm across my ample chest and started to leave the store. I got a couple of strange looks and a couple of smiles too. I made it to my car and quickly got in. I pulled up my t-shirt and looked down. Drops of milk were still forming at the tips of my large nipples. My breasts looked huge and swollen and you could see prominent blue veins crisscrossing just under my skin. I didn't have anything else to put on so I just pulled my wet t-shirt back down and started to drive home. I would have to be prepared better next time. I probably needed to buy a breast pump to drain them if I was going out. Bras were going to be necessary and I would need to get some nursing pads just in case. So this is what breastfeeding mom's go through. I smiled to myself when I thought about telling Brad what happened.
He called and said he would be over for dinner. It was Friday. I cooked him one of his favorite meals. My nipples had finally stopped dripping and I had put on a dry t-shirt. After dinner we were talking. I told him what had happened today. We both had a good laugh about it. I pulled up my t-shirt revealing my breasts to him. I said look at these things. They were huge and swollen and obviously very full. I joked and said that it was all his fault. He smiled and said they looked very sexy. He said he loved how you could see the veins beneath my pale skin. I said that a women asked me today if I had a baby I was nursing. Yes I told her, a big baby. We laughed again and I asked him if he was ready for dessert. We got up from the table and moved to the sofa. I just took my t-shirt off and was naked from the waist up. This was so routine for us now. We were completely comfortable with each other. As he started to suckle I felt the pressure start to ease in my swollen breast and it felt great. My milk easily flowed into his mouth and he drank it down. I let him go as long as he wanted. It was getting late. I looked at him and his eyes were closed. He was gently nursing and it looked so natural. I looked at his body. He was slim but in good shape. He never mentioned girls or a girlfriend. I guessed he kept to himself and probably was too nervous to approach girls his age. I looked farther down just below his waist and saw the bulge of an obvious erection. A rather large one I thought. So my tits were turning him on as well as comforting him. I guess the sex subject would have to be brought up sooner. I asked him what time he had to get home since it was getting late. He said he told his Mom he was staying at a buddy's house all night. My heart started pounding. In a shaky voice I asked if that meant he wanted to stay here with me tonight. He said yes if that was OK. Without really thinking I said that's fine.
He drained my breasts and we got up off the couch. I went and put on a nightgown. It was very short and almost see thru. I was wearing a lace thong under it. I really didn't have to tuck anything since there wasn't much left to hide. There was no way to tell what was there. The nightgown used to fit me but now my breasts were straining against the thin fabric. Brad was the first one to see me wearing it. When I came out of the bedroom he looked at me and smiled. I twirled around for him and then pointed at my tits and said that this used to fit. He smiled and said it looks perfect to him. I had a couple of glasses of wine to calm my nerves. I offered him some but he said no thanks. Finally I decided we needed to go to bed. I had no idea where tonight would end up but I took him by the hand and led him to my bedroom.
I got in bed first and turned the light off. There was a night-lite in the bathroom that I left on so there was a dime light in the room. He stood by the bed and got undressed. He left his boxers on and got into bed next to me. We lay there next to each other. I wasn't sure what was going to happen so I waited. I was about to ask him if he was OK when he rolled on his side to face me. I felt his arm go around my waist and he pulled me closer to him. His face came towards mine and we started to kiss. It was a passionate deep kiss that seemed to go on forever. His hand went under my nightgown and up to my breasts. He squeezed and kneaded them. I moaned into his mouth as we continued to kiss. We continued to embrace, holding each other tightly. I could feel his cock swell and become erect, pressing into my thigh. I figured out he really didn't know what to do next. I knew what I wanted so I rolled him on his back and got on top of him. I reached down and pulled my nightgown off over my head. All I had on was my lace thong. I leaned forward letting my tits hang over his face. He grabbed them and proceeded to lick suck and bite my nipples. He was a little rough with them and I liked that.
He had a raging hard-on and I decided I wanted to see it. I pulled a nipple out of his teeth and slowly started to work my way down lower. I kissed his chest and then his belly. I grabbed his boxers and started to pull them down. His cock sprang free and I got a good look at it. It was a good size. Much larger than I expected. He was intact too. Definitely not something I expected. My hand wrapped around it. It felt warm and alive and throbbed. I stroked it a little. His foreskin would roll back and expose his cock head. It was very large and swollen. If I let go the foreskin would roll back over it. I pulled his boxers all the way off so he was naked. I moved my face down lower and kissed his big cock. He moaned. I moved lower and taking his balls in my hand kissed them too. They were large too. I inhaled his scent. Even though he was only 18 he smelled like a man. It was intoxicating. I took his cock in my hand. I really needed to use two hands. I bent down and kissed the tip of it. His salty pre-cum was flowing. I sucked the head of his cock into my mouth. My tongue played with his foreskin. I started going up and down on his cock taking him deeper. He was breathing hard now. I stopped and asked him if this was his first blowjob. He nodded yes. I told him to just relax and enjoy it and when he felt like cumming to just let go. He said OK. I was able to get most of his cock down my throat. He was lasting much longer then I thought he would. I started to feel his balls tighten up so I knew he was getting close. I stroked his cock with my hands, pulling the foreskin back. I took his fully exposed head back into my mouth. Since it was usually cover I knew it would be super sensitive. I moved up and down quickly on it. I heard him cry out that he was going to cum. I pulled back leaving just the head in my mouth. I sucked hard on it while stroking his shaft. His cum rose up and exploded in my mouth. It was very forceful and he shot a huge load. I swallowed as best I could. Finally spent his cock started to soften and I released it. I rolled off of him and we both laid there breathing hard.
I got up and went to the bathroom to clean up a little. When I got back he went to do the same. He got back into my bed and we spooned. My back to his chest. He reached around and grabbed one of my breasts. I felt his cock press into my ass cheeks. We fell a sleep like that. I woke up at sunrise. We had moved around while sleeping. He had one of my nipples in his mouth. He also had a raging morning erection. I was able to pull my nipple out of his mouth without waking him. I put on my robe and went to the kitchen and made coffee. I knew we would have a talk about what happened last night. I also knew there was a good chance that he would want to do more. He came into the kitchen yawning and rubbing his eyes. He had put his boxers back on. I gave him a cup of coffee and sat next to him. He smiled at me but didn't say anything. Finally I broke the ice and said so about last night, how did you like your first blowjob? He smiled and said it was fantastic. Better than he ever imagined. I asked him if he ever had come close to letting a girl do that. He said a couple of times but he chickened out because he was afraid of what they would think of his uncut cock. Every other guy he knew had been circumcised as a baby. Girls might think he was a freak. I told him that any girl that thought that was an idiot. I told him I loved his foreskin. Really he said smiling now. I told him it was perfect.
I asked him about his Grandma. I wanted to know if they had ever done anything like that. He said that when he when through puberty they had talked about it. She told him she loved him and when he was ready she would have sex with him. He said he was about to tell her he wanted to when his Mother found out about him sleeping with his Grandma and nursing at her breasts. They got into a big fight and that's when his Grandma moved out. I really felt sorry for him. I said so you never got the chance to have sex with her? He just shook his head. I didn't say anything. I waited for him to say it. He took a sip of his coffee and looked at me. He said he loved my breasts and getting to nurse on them. Last night was the greatest night of his life and it just made him want more. I said more blow jobs? He shook his head no and said more sex. He shyly asked if I would be willing to have sex with him He said he wanted that more than anything. So there it was out in the open. What do I say now?
My heart was pounding. I said I am your Grandmas age. Why would you want to have sex with me? He said that didn't matter. He thought I was hotter than women half my age. He felt very comfortable with me and he trusted me because it would be his first time. I had to tell him. I asked him if he knew about the different ways to have sex? He looked a little confused but said yes. I asked if he knew about anal sex. He said yes. One of his friends was with a girl who let him have anal sex with her. He said it was way better than regular sex. I looked at him and said that I was willing to have sex with him but that anal was the only way we could do it. He looked a little confused and said OK, but why? I stood up from the table and let my robe drop. I slipped out of my panties and said that this is why. It was the first time he had seen me totally nude. He looked between my legs. He said that I had a big clit. He still had not figured it out. I sat back down on the chair and spread my legs open. I pointed and asked him what was missing. He looked again but still didn't get it. Finally I pointed. I said a vagina was missing. I didn't have one because I was born as a male.
I got up and put my robe back on and stood next to the sink and started to cry. In a moment I felt him standing behind me. He wrapped his arms around me and hugged me tight. He whispered in my ear that things would be OK. He said it didn't matter, he still wanted me just the same. He was accepting me the way I was. I turned around and kissed him. He kissed me back with no hesitation. We sat back down and told him my story. I had always thought of myself as a female. My body never looked like a male's and after some hormone help I developed and started my transition. I said I had every intention to have sexual reassignment surgery but for now anal was the only option. I smiled and told him he would be my first. We would be two virgins trying to figure it out. He said he had to go but he would be back tonight. I knew what that meant. We were actually going to have sex. I kissed him goodbye and had to sit down because my legs were shaking.
I spent the rest of the day figuring out how to prepare for it. I searched the internet and found some advice for first time anal sex. They was some warnings about a cock that might be too big. I thought about Brad's and started to worry some. He was big. Much bigger than anything I had put in my ass. I didn't want to disappoint him and not be able to take it. They said use lots of lube and just relax. It might hurt some and I would probably be sore for awhile. Some that had tried it said they hated it and some said they loved it. I hoped I was one of those. I would have to take the lead on this, at least until he was inside me. I made a plan for positions and hoped he would last so we could experiment with some. If he liked it I am sure there would be a second time and possibly many more times. The idea of using a condom crossed my mind. He was a virgin so I saw no reason to use one. That meant he would be ejaculating inside me. Taking him bare would create a special bond between us. I knew he would shoot a big load inside me and I really wanted to feel that.
I picked out something sexy to wear. A couple of hours before he arrived I gave myself an enema to clean out. That was the gross part but necessary to enjoy our first time. I took a bath with some scented soap. I put the lace bra and panty set on. It had been a while since I bought it. I tried to position my breasts in the bra. I wasn't having much luck. I needed a bra about 2 cup sizes bigger. It barely contained them. I was spilling out of the top and sides. Finally I just figured it wasn't going to stay on long anyway and it would work OK. I had some high heels that matched the red color. They were really tall but made my legs look long and sexy. I had practiced walking in them and felt confident I could. I had gotten my nails done to match as well. I looked in the mirror and thought I looked pretty damn hot. The one thing I wish I had at that moment was a vagina. I decided right then to have the surgery. There was no reason not to. I was going to do it for myself but I also knew Brad would enjoy it.
The door bell rang. It was him. I walked to the door in just my bra and panties and heels. I opened it and he came in. He looked me up and down and just kept saying Wow. I said thanks. He did say that my bra might be the wrong size. I put my hands on my hips and said it used to fit and now it doesn't thanks to him. He laughed and said it looked amazing. He then asked if I had a dress or something to put on over what I had on. I said yes but asked why. He said he wanted to take me out. That really surprised me. I asked like a date? He said yes just like that. I could tell he was serious. I said OK just give me a few minutes. I looked through some dresses and tried a couple on but the bust didn't fit me well. I settled on a black leather mini skirt and a silk blouse. I put a wide belt on that matched my red shoes. I decided that since my bra really didn't fit right I should just take it off. I knew it was a little risky with my recent spontaneous lactation episode but I would go braless anyway. The silk top was loose fitting but I am sure people would be able to tell my big tits were swinging free.
I walked back out and announced I was ready. Again he said wow and I took that as an approval. He came over and gave me a hug and a kiss. He looked down at my chest and reached out and grabbed a boob. He said no bra? I said it didn't fit so I took it off. He smiled and said let's go. His car was old and worn out so we took mine. I let him drive. We went to a small sushi place and had a light meal. I watched for looks from the other people there. I might have noticed a couple but nothing obvious. After we ate he wanted to go to a movie. I thought that was cute and I let him pick the show. It actually was a good movie. He held my hand during it. We walked back to my car and he drove us home. I was nervous walking up to my door because I knew what was about to happen. I was about to unlock the door when he grabbed me by the waist and pulled me close. He gave me a long deep kiss. I smiled and asked what that was for? He said he never had kissed a girl at her door before and he wondered what it would be like. I smiled and asked if he would like to come inside? I opened the door and we went in.
I told him to go sit on the sofa and I would be right back. I went into the bedroom and took off my blouse and my skirt. All I had on was my tiny thong and my fuck me shoes. I really like the way my ass looked. It had filled out and was nice and round. When I walked back in he was sitting on the sofa in just his boxers. I smiled and walked around making sure he got a full view of my ass. I made him a drink without asking. I wanted him to relax a little. I knew I had to lead this encounter. We sat on the sofa and had our drinks. He reached over and played with my breasts some. We kissed and I reached down and squeezed his hard cock. After finishing our drinks I told him I wanted him to suck my nipples. I laid back on the sofa and he got on top of me. He grab my tit and sucked and licked my nipple. My milk started to flow some and he drank it down. He switched breasts and sucked and nibbled on that nipple. I could feel his erection pressing into me. He was really working my tits over and I was getting worked up. I told him to sit up. When he did I took off his boxers and knelt in front of him. I reached out and stroked his big cock and played with his balls. I took his cock into my warm mouth and went up and down on it. I didn't want him to cum yet, I just wanted him to want me more.
I spent a few more minutes worshiping his cock. I let it pop out of my mouth and I stood up. I took his hand and led him to my bedroom. I sat him on my bed and said I would be right back. I went into the bathroom. My heart was pounding with anticipation. I took off my thong. I had a bottle of lube and put some on my finger. I slide one finger into my ass. I was very tight and my finger felt big. Was I ready to take his cock in there? I got some more lube inside me and made sure I was clean. I got a towel and the bottle of lube and walked back out into the bedroom. I told him to stand up. He was still rock hard. I sat down on the bed and squirted a little lube in my hand and stroked his cock. I looked up at him and asked if he was ready. He nodded yes.
I got up on the bed on my hands and knees. My big breasts hung down below me. I presented my ass to him. I told him he could rub it and kiss it if he wanted too. He did just that. He rubbed and squeezed my big ass and even covered it with kisses. I loved the feeling of his hands on me. I asked him if he liked my big ass. He said he loved it. I decided it was time. I told him to rub the head of his cock across my opening. His foreskin was still covering the head and he was leaking a lot of pre-cum. I moaned when I felt it touch me. I adjusted my position a little to make sure the angle was right. I told him to go ahead and try to press the head inside me. I felt one of his hands on my ass and the other one guided the tip of his cock to my entrance and he started to push it in.
I felt myself start to be stretched open. He was so much bigger than I expected. He said I was so tight. I told him I was OK and to go slow, but keep going. He was able to make more slow progress. I could actually feel the tightness start to peel his foreskin back off his swollen glans. I was biting the pillow and suddenly his head popped all the way in me. I put my hand on him and told him to just wait a moment. Let me get used to him. He said I felt so hot and tight inside. I took some deep breaths and told him to start pushing again. He let go of his cock and now had both hands on my ass. I tried to relax the best I could. Slowly the shaft was going in and he was going deeper inside me. I felt so full. As he continued to go deeper I could almost feel him way up in my gut. I held my breath until I felt his balls touch me. He was all the way in.
He held still for a moment loving the feeling of being deep inside me. I was getting me pretty worked up and I told him to slowly start stroking his cock in and out of me. Slowly he pulled his cock out until just the head was still inside me. The he pushed it in again until he was balls deep. Each time he stroked I could feel his foreskin moving back and forth over his head. I started getting used to his size and pushed back into him some. He was rubbing me in just the right spot and I felt some pressure building. I thought about changing position but I felt we both were getting close. I turned my head toward him and said harder, fuck me harder. He grabbed me by the hips and picked up the pace. He was taking full strokes in and out of my ass now. I heard him say that it felt so good. He was really banging me now. We were making a slapping sound as his hips slammed into my ass. I grabbed one of my tits. It was wet. My milk was squirting out on its own as he fucked me. He said he was close. I told him to grab my tits. He reached under me and took one in each hand. He squeezed then and pulled on my nipples. I told him to do it harder.
I was close, very close. He was so deep inside me. I heard him groan and cry out. I knew it was happening. I could feel his cock swell up even bigger and it erupted when he was the deepest inside me. He squeezed my tits as this happened and I lost it. My ass spasmed and I had my first anal orgasm. Clear fluid came out of my urethra. My body shook all over. He was straining to shoot ever last drop of his sperm deep inside me. My ass muscles were clenching his cock and milking his load out. He stayed deep inside me until he was empty of cum. Finally we both collapsed on the bed with him on top of me. We held each other close. His cock was still inside me. He started to pull it out and I winced a little. Finally the head popped out and I felt a little empty. His big load was deep inside me but I knew it would probably leak out eventually. We were both no longer virgins. That was a bond we would always have. The bed was a mess but we didn't care and fell asleep in each others arms.
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