Many straight men are afraid to admit to anyone (including themselves) that stimulation of their anus is extremely pleasurable. The fear is that they will be labelled as gay. Homosexuality is an orientation, of course, and has nothing at all to do with where you like to be touched.
For years, I was too shy to admit this until I met Alison. Alison and I developed a very intimate relationship and I was able to open up to her (in more ways than one) about anything. One night during foreplay, her fingers wandered from my testicles to my anus and she began massaging circles around my hole. At first I tensed up, but then just as suddenly, I relaxed. She said, 'Is this OK?' I replied yes and she smiled. She grabbed a bottle of lube and lubed up both her hands. She then took my rock hard cock in one hand and moved the fingers of the other hand back toward my ass again.
She kissed me gently and told me to relax and breathe and let go. For the first time in my life, I did just that. I surrendered completely. She then slowly inserted her middle finger deep inside my asshole and rubbed my cock. Her finger massaged the deepest and most private part of my body. A few moments later, she withdrew her finger and got more lube. This time, she inserted two fingers inside me, massaging my prostate gland and rubbing my penis. That was all I could take. I began moaning and crying out like it was an out of body experience. My breathing was ragged and I felt like I was going to explode at the waist. Her pace quickened as she talked me through it...'That's it baby, let go, just let go, come on my breasts, let it all come out, it's OK, it's OK.' I then let out a roar like a mating bull. She pressed firmly in my ass and jacked my cock as fast as she could. My come came out like a firehose spraying on her breasts and face. When it was over, she cradled me in her arms as I was nearly hyperventilating and sobbing from the experience. To calm me, she took her nipple and placed it in my mouth and told me to suck and relax as my breathing returned to normal.
A while later, I returned the favor, spending a while massaging her hole and then putting two fingers deep in her ass as I rubbed her clit firmly and gently. 'Oh my God, TJ, my ass, my clit, oooooooooohhhhhhh baby, do it, do it, oooooooohhhhhhh' she moaned over and over almost incoherently. When I realised she was nearing an orgasm, I moved two of my fingers of one hand from her clit and plunged them deep into her vagina, curling them and rubbing her G spot and ass at the same time. 'Oh FUCK TJ, Oh my God I feel like I'm going to pee, ooohhhhh!!' Just seconds later, she let go with a shriek and let loose a huge female ejaculation that sprayed from her pussy like a fountain. She broke down and cried and told me she had never felt so loved and so much like a woman in all her life. It was her first female ejaculation as well and the feeling was the best she ever had. We then fell deeply asleep.
Easily one of the most erotic experiences of my life.