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Lube, alcohol and lube respectively.
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On both occasions I experienced it, these were involved.
The first I received, I can safely say it did not hurt. It was like taking a very satisfying shit repeatedly. I was sore as fuck the next day.
Second time I gave, twas to an ex-girlfriend after much weeks of begging and threats of abstinence. She said it felt weird and asked me during, 'Hurry up!', which put me off a bit.
I prefer vaginal sex, I quite like the moaning that is given.
Speaking of condoms, never use Performa. It put me off even having intercourse the rest of the night.