She made me lick her ass as well and was riding on my face. Within a few minutes she came so much and I felt some bubbles bursted out of her pussy and some sticky liquid inside my mouth. It was the best night I ever had with her and she agreed to do a STRAP-ON sex with me that weekend. So, we went to an adult store and bought some harness and medium sized dildos, had some wine and started watching porn. We both were a little high and started getting horny and decided to start pegging. So, without any delay, she ripped my clothes and under pants and pulled me to the edge of the bed and bent me over. I was very excited and scared as well. I already shaved pubic hair and cleaned my ass using an ENMA bulb and hot water to avoid unnecessary mess. She put some lube on her fingers and on my ass and started inserting them while she pleases herself. After little preparation I helped wearing the harness and dildo attached to it. She asked me to give blowjob on that dildo. I was a little hesitant at first but don’t want to disappoint her. So I gave a nice job to that dildo and she bent me over again on the edge of the bed. she applied some lube on the dildo and some on my ass hole and started inserting it.
She thought it will go very smoothly as how a dick goes inside a pussy. With out any warning she gave strong stroke. I was in lot of pain. She said sorry and helped me relax the muscles around my ass. We waited for 15 min to calm down my pain and I was very sad that it went wrong the first time. I was scared to take that pain again but do not want to miss the chance of getting pegged. If this doesn’t work out tonight it kinds of break our deal as she already warned me about the pain. After some time I asked her again to try out this time but gently. Even tough she did it slowly it was giving me so much pain which I couldn’t take it. I think that dildo was not for beginners (website suggested it wrong). We tried some other small dildo but nothing worked and we stopped doing that and she left saying we are not doing this again. We only met few times after that for our regular sex and later she moved to a different city. So, the thought of getting pegged was still my dream. I did not stopped using butt plug and watching FEMDOM porn and pleasuring myself.
I got so frustrated as this was running back of my brain everyday. So, one day I decided to try this out one more time to see if this will ever happen, if not will stop thinking about it. My fuck buddy did not accept my request but suggested to hire someone for this. One of my friends gave me a stripper contact long back and I thought will give it a try and what harm it could cause. So, I called her and told her that I got your contact from some one and directly asked her if she can provide some sort of service. She said yes and quote very high price. She gave her Instagram id to check her profile and can decide on it. She was very hot and a professional dancer and looking at her couldn’t control my thoughts and called her again. I told her that Im not looking for regular sex but instead asked her to fuck me in my ass. With out any thought she said ok and this shocked me a little. I was very happy that she accepted and asked her one more time if she is really ok.