Finally my dick head entered her wet and very tight pussy. She was extremely tight and I gave a pretty quick push through to get in. I had to push h...rder than expected and finally I felt her pussy give way and I slid in. Her expression was priceless and I just then realized what had happened. She was a fucking virgin! I never considered it. She was almost in tears from the initial shock of pain, but with a few slow strokes she said it was hurting but wanted to continue. I pulled back and. The winner was her first boyfrind from highschool, Darcy. i guess the deal was whoever won could either tell the loser what clothes to remove or do it themselves. Darcy told my girlfriend to stand up and turn around. i noticed as she stood up her pussy was wet. Darcy stood up, wearing his pants and i assumed under wear. Approached my girlfriend and put his hands on her shoulders. There was at one time a little history with these 2 when she was 15. they dated for about 6 months at the time. More

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