our break getting more intimately acquainted. During the first semester in college Bobby and I had discussed sex, but had yet to do anything other than mutual masturbation on a couple occasions.
One night before we took off for our break between semesters, we sat across the table from each other drinking wine and talking about sex well into the night. After a bottle of wine I’d become a little amorous in my inebriated state, so I reached across the table and took one of Bobby’s hands into mine. As my fingers explored his hand I stroked and admired his fingers, telling him what great looking hands he had. I remember telling Bobby that I would enjoy having him explore my anal cavity with his delightful looking middle digit. He replied that he would enjoy doing me with it. He asked me if I had ever been diddled or cornholed before. To which I replied, no. He told me he wanted to change that very soon. I asked him why we didn’t try it that night. To which he responded only when the time is right.
Bobby had asked me during our conversations about my sexual experiences thus far in my life. I told him that my sex life had been limited, but now that I was free of parental control I wanted to expand my wings and fly. I went on telling him how I played with my asshole a few times when I was younger and what an exhilarating feel it produced. I told him how I would wet my middle finger with saliva or baby oil, playing around rubbing the entrance to my asshole of a night while I lay in bed jacking off. Also, when I took a bath or shower I would soap up my ass and play with my asshole. However, the few times I’d actually inserted my finger in my rectal cavity I withdrew it finding fecal matter attached as well as nasty stink of shit to my finger. So, by the time I was in high school I knew my asshole was super sensitive to touch, but also came with an offensive odor.
As we sat across from each other I told Bobby that I’d heard and read that some guys found anything penetrating their assholes to be repugnant and taboo. Others found anal sex play to be a very enjoyable and sensual experience. I informed Bobby that I thought I would enjoy anal sex, and moan out in ecstasy if he were to diddle my asshole with one of his beautiful fingers. I also told him I thought that I was one of those who would find cornholing to be very sensuous. Bobby interrupted telling me that is why he wanted to wait until we were away from the dorm before doing anything.
My roomy told me that he wanted us to be alone and free, so we might sing out gleefully as we sexual stimulated each other. I told Bobby that for me to be finger fucked while receiving a blowjob would probably be the ultimate in sexual pleasure, bringing on wanton wails of desire from me. I told him that during recess in junior high school I’d heard stories from the older boys about them finger fucking their girl friends. Of course, they always wanted to pass the odoriferous digit under our novice noses for everyone to sniff the scent of the freshly finger fucked girlfriend. I also heard stories about guy’s cornholing each other. Although curious I had never indulged.