In my teens I had a close female friend and we felt that sex between us would spoil our friendship. She had a boyfriend and I had a girl friend at the time and a group of about 10 of us went to a party at a house in the town.
During the evening she and her boyfriend were intimate and after a couple of hours they disappeared. About half an hour later her boyfriend reappears in an agitated state. He comes over to me and says that she needs to see me upstairs. He takes me up and opens the door. She is lying on the bed naked and looking ravishing.
She explained that her boyfriend had wanted sex but on seeing his dick she was concerned. She asked if, as a favour, I would hold her hand whilst they had sex and make sure he stopped if it became painful and regrettable on her part. of course, I agreed, well he stripped and never before or since had I seen such an engorged phallus.
They recommenced foreplay with me sat on a chair holding her hand. She was definitely enjoying the experience and becoming very moist. He pulled himself on to his knees and prepared himself for penetration. For 10 to 15 minutes he tried to open her fanny enough for the head to penetrate without success. He coated his dick in her juices but, it would not stretch enough. Eventually, frustrated he gave up and got up and dressed. She just lay there devastated.
He left the room and I cuddle and consoled her. After about half an hour she sat up and started crying, She explained she was a virgin and was determined to lose it that night.
We lay there for the rest of the night and at daybreak we got up, dressed and left the house.
She has always stayed close friends, never had sex and I never saw her lose her virginity.