A little more detail than my normal tale.
I had a very sheltered life; my parents had never explained the birds and bees so my limited knowledge was from school mates. As to be expected this information was not very reliable or accurate. So when Eva became my first real girlfriend I had zero experience. We had been seeing each other for the past seven months. It took three months before we got intimate but we had been making up for lost time ever since. We were lying in her bed relaxing after a vigorous event. I love oral sex, both giving and receiving and we had spent an extra longtime practicing our skills on each other. I'm not sure but I think Eva had three very satisfying orgasms and I know I had two of them.
It was after we shared a shower and I was dressing when she asked me if I'd ever had a prostate massage. I confessed that I didn't know if I did or not. She informed me that if I didn't know then I had never had one and if I would like to try one next Friday. She could fix us dinner and later we could see what I thought about them. I might mention that Eva was five years older than me and she didn't hide the fact that I wasn't her first or second or third person she had experience with. She would sometimes say things like, 'Jake and I would or sometimes Mike liked to'. Because of my zero experience she could guide and teach me so many things.
That Friday we had a pleasant meal. Meat loaf, mashed potatoes and mixed vegies. As I helped clean up Eva asked me if I still wanted to try a prostate massage. I thought a massage can't be all bad. When I played football in high school we were offered back and leg massages they felt good, so yah I was up for a massage anytime. Oh what a surprise I had coming.
Eva was a professional massage therapist so she had a regular table and all the supplies. When she told me to strip and lay on my stomach I was quick to follow her directions. I expected her to undress also and when I asked she merely said this was all about me. Later if I was able we could see about her needs. Like a normal massage she started to rub warm oil on my back. She started on my shoulders and slowly worked her way down.
It was when she finally reached my butt that things began that was maybe not what I expected. She was spending a lot more time rubbing and squeezing my cheeks. She would use both hands and spread me open. I was worried that she could see that private place. When she held one cheek to the side and a slippery finger slid down the crack I knew was exposed. I was feeling ashamed and excited. Eva was touching me back there.
My penis was kind of hard when I first lay down and I had lifted it to point up. I didn't want her to see it if I got hard and get offended. It was a good thing I did because I was getting harder. I had to wiggle a little to give it room. She slapped one cheek then the other, not hard but enough to sting. She asked me if that felt good. I just grunted. Then she hit them again harder and asked if that was better. The third time she smacked me even harder and when I cried out so told me I should have answered the first time.
I felt her long hair touching my backside and she kissed one cheek and then the other. When she asked if I was ok I told her I was. She bit me, not mean like, more a love bit. I was realizing I was likening this massage. Enjoyable and Interesting, I never would have thought that getting spanked and kissed would be like it was. She could give me a prostate massage any time.