When i was about 18 years old, I was feeling super horny and i just wanted to fuck. I had no boyfriend and i didn’t really want to lose my virginity to someone from school. I was also attracted to older guys of the age 30 and lower. I went searching for a guy on Craigslist when they had the personal ads. I started talking to this guy who was 26 years old at the time. He seemed really into the fact of fucking a virgin with a tight pussy. We exchanged pictures and his dick was huge! He had it up against a red bull can. We made plans to meet up and fuck in his car. I chickened out and never went through. I just sat in his car for like 2 minutes and started panicking. He was very sweet and understanding. He said he didn’t want to pressure me. Fast forward to when I am 19 years old. I came back home from college on break. My mom was out of town and i was feeling horny. I decided to contact him again. At the time i really wanted to fuck. As the time came closer for us to meet, my stomach would just ache. I tried backing out of it. He was telling me nothing bad would happen to me. I had expressed to him how I felt he can be some guy trying to kill me. We were strangers and didn’t know each other at all. He said all he wanted was to fuck and we can go our separate ways. Anyways, he picked me up in his car and we tried tucking in the backseat. His dock was so big that the tip barely fit. It was getting uncomfortable and I stopped because it also hurt. He was nice about it despite he was not able to get off. I just left him with a huge erection. Now fast forward to today. I am planning to invite him to my apartment when my mom is at work. I want to ride him on the couch. Should I?
Source: reddit.com/r/gonewildstories/comments/bn70bs/should_i_f
Wow i wish I can see it
Question is do you really want to?
Are you actually sure this time?
You guys should hangout first so you two can be more comfortable with each other.
I second the the pre fuck hang out, being comfortable is probably the most important thing. You will enjoy it more if you are comfortable and kinda like the guy.
I assume you are not a virgin anymore, right?
So, what are you afraid of? Physical pain or else?
Is there some aspect of this where you’d like your first time to be CONSENSUAL non-consent with off course a safe word? In my opinion the best safe word is red as in red light, yellow light, green light. Red or red light are pretty universally understood as want to stop and in this situation would not revolve around you saying no. It seems like you’ve progressed with this man from a 2 minute chat in a car stopped by anxiety to the tip of his dick barely inside you stopped by pain and possibly anxiety again. If he’s big and you haven’t broken your hymen through sports or physical activity then it’s going to be fairly painful.
Would he be willing to get a hotel room to spend the afternoon, evening, night and morning in with you? Rushing fucking each other in your apartment with Mom out may not set the best stage to calm your anxiety and fuck several times so you can begin to enjoy it.
I think you’ve found a pretty awesome guy to experience sex the first time with.
Do it
Foreplay is a vital
Use lube
Good luck
Get a boy friend and take things slow. Some one closer to your age. There is no need to rush sex with a stranger 29 years older then you. Also advice from a sex stories forum is not the best place for this kinda of thing.
Your first priority should be trusting the person your with and being comfortable. If you can’t say these things then don’t get involved.
Just think if you have sex with him. He may not just disappear especially since you have now called him 3 times. Keep that in mines.