I take viagra and 1 - it does give me erections. 2 - they are very hard. 3 - once I cum, I can usually get hard again shortly after.
I've been with the same woman for 20 years. I know the spark is long gone. I don't need anything when I masturbate and I would hope I wouldn't need it if I was with a beautiful T-girl for the first time. But, I would definitely take it because I'm sure I would be totally nervous.
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