I wasn’t able to push at least half as it is very tight and she is in total pain. I closed her mouth with my hands and slowly pushed my dick inside. It took almost 2-3 minutes to completely get inside of her. She is full pain and I started to move my dick slowly. I closed her mouth with mine kissing and was drilling her and increased my speed. After a couple more minutes, she also started enjoying and she is in sync with my movement. After 5 min, I reached climax and shot my cum on her naval as I don’t want to take any risk of releasing my cum inside her. It was a huge pleasure for me as she is a virgin and her pussy is so tight that I came in just 5 min. She is exhausted and she fell on my chest and breathing heavily. I asked how was the first experience and she didn’t say anything but kissed my lips and sucked them. We laid there about 20 min cuddling and it was around 4:15 pm. I started to kiss her and fingering simultaneously and she opened her legs while I fingered her. My dick. He gave no indication to have any sexual advances to me whatsoever. I did ask why he was talking to a crossdresser and he replied he looked up people who had sports on their profile. We chatted about sports for a while and then he said he had to get up early and signed off and said he was going to be in town all week. I didn't think much about it.Two days later, my work day had an early ending so I was given an opportunity to dress again. I was back on webcam drinking another bottle of wine when my friend from the previous day messaged me again. We were both watching the Thursday night football game, and chatting about the plays and other sports junk. He said he was bored and asked if he could come over and watch the game. Thinking better I responded I was straight and had no interest in sex of any kind with men and meeting would not be appropriate. He responded he had no interest in anything other than drinking a beer and watching the game. He also said he would be happy to take.
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