The first time was with a condom, and it felt ok. To me, it didn’t feel much different than jacking off or a hand job. The first time without a condom was life changing. Someone above mentioned cumming longer inside a woman, and I can 100% verify that.
My first time (in college 18+) was also in a condom (out of necessity) and it felt amazing for the same reasons
@EGR1972 described above. The whole body skin-to-skin contact, the actual act of making love, etc. I had obviously jacked off many hundreds of times before finally having sex, but there is simply no comparison. My whole life, when I have been in a relationship and having sex on a regular basis, I have rarely masturbated.
Straight boys, when you are inside your girl and cumming how does it feel for you and what is it like ?
Also how did it feel the very first time you spunked inside someone either with or without a condom ?
With that first girlfriend that wasn't on birth control, virtually all of our sex was with condoms. Cumming in a condom inside a vagina felt amazing and no comparison compared to cumming by masturbation. I'll take fucking with a condom over masturbation any time, any day!
Early on, she mentioned she did have a diaphragm, but didn't like putting it in and taking it out. I asked her to bring it with her the next time she spent the weekend with me. She put it into place then we started our usual long foreplay until it was time for me to enter her. She always got very wet very quickly so I was able to get the head and first inch or or into her on the first stroke, then a few stroke later I was balls deep. It felt simply amazing, and yes different from the dozens of time we had done it with a condom. That warmth and wetness of her vagina was now in direct contact with all of my penis and every in and out stroke was pure pleasure. Experiencing those sensations for the first time made for a fairly short session due to sensory overload for me.
Because of her dislike of the diaphragm, it was one weekend of condomless fun, and we had sex many hundreds more times using condoms. On occasion she begged me to enter her without one for "just a few minutes" and it took all of my willpower to withdraw and put one on before things got to the point of no return