The old “mercy f*ck”. Problem is that the longer they wait, they shyer they get about finally losing it. My college BF had a 24 yo brother that was a virgin, and he was pushing me to hook him up with a friend to take care of his “problem”. Problem is not many girls willing to do it. Finally I told the bf I’d do it. Brother finally agreed, and at first it was totally weird. Unlike before, this was more like a teacher / student thing, and when I took off my robe and got in bed next to him, he was shaking like a leaf. I tried to calm him down, telling him it was okay, and gently massaging his chest. I moved my hand under the covers, touched him, and he immediately orgasmed. I told it was ok, we would just cuddle and wait. I took his hand placed it on my breast, then moved it to my vagina. I had to show him where my clitoris was, and how to finger me, and he got it pretty quick, and was erect again. I went down on him, and again he immediately orgasmed. Again I reassured him it was okay, and used the time to teach him how to do oral on a girl. 20 minutes later, he was ready for the “plunge” and I guided him in. The look on his face was priceless, and once again 3 or 4 thrusts, and he was done. We waited again, and finally he lasted about 10 minutes before his 4th orgasm. He was so sweet thanking me, and I lied and told him he got me off too, which made him feel better.