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brandonnsdiego
05-25-2009, 02:09 AM
This is a true story. It happened to me years ago when I was a young man. I hope you enjoy.

I had been seeing a nice and sexy girl for some time. We were not serious but got together form time to time. She had lived near me and I was upset when she moved away. One night I was feeling very bored and horny. It was just my luck that she called me that evening. I was very surprised because I had not heard from her in months. She had recently moved back into town, but in an area very far from me. I really wanted to see her though but was not looking forward to the drive. She gave me the address and directions to her place. She also said that she was in the mood for something different that night.

Every time I had been with her I had been the top. She told me on the phone that wanted some of my ass that night. I had never been topped before and was not sure if I wanted to do so that night. I just really wanted to see her. She also gave me some instructions on what to do to prep myself before coming to her place. I like to please my partner so I did as she instructed. I got ready and drove the 45 mins to her place. Even though it was very late, I was wide awake with excitement of seeing her again.

I arrived at her place at about 2AM. It had to be late because she went out with some friends earlier that evening. She looked as beautiful as I remembered. I gave her the gifts I had brought to her, some wine and flowers. We sat down and talked a bit to catch up on what we had been doing since last seeing each other. It was a nice time. We opened the bottle of wine I had brought and continued our talk. I was really enjoying her company. Well after getting a little more loosened up by the wine she suddenly kissed me. It was so nice. I had missed her sweet lips, but that night she was even more aggressive than usual. I was enjoying it very much. After making out for some time she told me to get more comfortable and to remove my clothes. As soon as I had taken them all off she went down on me. It felt so good. I had almost forgotten how talented she was with her tongue. I got so hard and had to have her stop before cumming. I wanted this to last for some time.

She then took off her panties and pulled out her beautiful dick. It was not hard yet and she said it was her turn now. I wanted to make her feel good so I went to work on her huge monster. It tasted so good and I loved the feeling of it getting hard in my mouth while hearing her moan in pleasure. Then she got even more aggressive and started to shove it down my throat. I had never really taken it down that far and was having some trouble doing so because of her size. She told me how she wanted me to suck her and I listened. She grabbed the back of my head and forced her cock down my throat and held it there. I could not believe I was taking the whole thing. She then began to fuck my throat very forcefully. After doing this for some time she said she was ready for some of my ass. I was in new territory so I did not know what to expect. I was in for some surprise. She asked me if I had done the things to prep myself before coming and I said yes. She was very pleased and said it was time to get fucked. I was scared and nervous but in a good way.

She told me to get on all fours on her couch and before I knew it she was licking my ass. I had never had that done before and it felt so good. While she was doing it she was also slapping my ass. She then asked if I was ready for her dick. I told her I did not think so but was willing to try. She lubed herself up as well as my hole. She got behind me on her couch and spread my ass as she started to put the head of her cock in me. It was hurting and I asked her to stop. She told me it was going to be OK and for me to relax. I tried to do so and when i did she pushed the whole monster inside of me. I screamed out in pain and asked her to stop, but she would not. Then she became very domme. She told me it felt too good to stop and that I was not going to be a tease. She liked how she was the first to take my ass and that I need to relax. I asked her to stop again but it was no use. She told me I was hers and that I would not have come all that way and done as she instructed if I did not want it. She fucked me slowly at first and I was still feeling the pain and burning of her big cock in my ass. Suddenly she pulled out and told me to go to her bedroom. She said I had had enough warming up and now it was time to get fucked like a good bitch should be.

I got up and went to the bedroom. She had me lie on my stomach and got on top of me. I felt her lags spread mine open and she plunged her cock in my ass with one push. It hurt once again but not as bad as it did a lil earlier. She began to really fuck me hard. I was yelling out for her to stop but she just kept fucking me and telling me not to fight it. She said I was gonna get fucked until she was done. I was there to please her and that I was her bitch for the night. She said she liked it when I screamed and that it made her harder. She told me how good my pussy felt and even though it hurt I was turned on by how much I was pleasing her. As I continued to get pounded by her cock it began to hurt less and started to feel good to me as well. I was shocked I was enjoying being fucked by her.

She then turned me over and had me on my back. She grabbed my legs and started to fuck me hard again as she held my legs spread wide and was looking me in the eyes telling me how good it was. My dick began to get so hard and she told me to play with it while she fucked me. I could not believe it but I started to feel like I was about to come, she told me not too until she did. She then began to fuck me even harder and said she was about to cum. She asked if I was ready for her cum and I said yes. I thought she was about to pull out and shoot it on my stomach, but she had other plans. She began to yell she was cumming and shot her load in my ass. As she did that I began to cum so hard it shot all over.

She asked if I liked being her bitch. I was afraid to answer her. She told me that even though I did not answer she knew I did. We then fell asleep for a few hours. I was awoken by her big cock being pushed in my mouth once again. She said that she had to have some more before I went home. I was a lil sore but she said that I would get used to it. After another round of being fucked she decided that she wanted to cum in my mouth. When it was time for her to explode she pulled out and moved her cock to my mouth and made me eat her cum. She said that I was broken in the right way and that I would never be the same again. She was right. On my long drive home that day I could not stop thinking about what had happened the night before.

brandonnsdiego
05-26-2009, 08:52 AM
You are so lucky. I remember the first time for me and was feeling her in me for days. Cant wait for your next story.

Thanks for reading my story. I was feeling her for days as well.

Anubis1079
05-27-2009, 10:59 PM
After living in SD last year, I'm curious as to the identity of the girl.

brandonnsdiego
05-28-2009, 02:49 AM
After living in SD last year, I'm curious as to the identity of the girl.

I won't kiss and tell, but it was many years ago and she moved away. I think she lives in LA now.

Westroadmichael
05-05-2010, 07:35 AM
I would love to meet her myself!!

Rancour
05-16-2010, 08:37 AM
Thank you.

catgrrl
03-27-2011, 11:25 PM
Great story...Thank you

canihavu
05-23-2011, 03:42 AM
Wow...

AnnaV
05-30-2011, 07:53 PM
I'd love to know if you went back for more

dickgurl69
08-17-2011, 06:34 AM
I hope my first time with a TS is similiar to that!

urBIGGESTfan
08-21-2011, 06:03 PM
great story i want to be fucked so bad right now!

Ilovetranny
04-27-2012, 03:59 PM
It's awesome. This story makes me hot.

cbrowneye
02-21-2014, 05:20 AM
Good story although I don't understand certain aspects of it.

admirer123
06-25-2014, 11:08 PM
Would love that now

knighthawk
06-27-2014, 04:49 AM
Very Cool Story :D

must93
06-27-2014, 05:29 AM
My first time and only time was with a top. Never planned it to be that way. We were kissing on the bed naked and I was on the bottom. Next thing I knew she was going in and before I could stop her she had half of herself in, It was wild and I can't get it out of my mind. She came in me and said I was so tight so she only got about half in. She said I must have liked it because I was hard the whole time. I wish I had a TS GF. It was the best sex I ever had. I think more and more men are seeing the wonders of being with a special woman.