Back in July, I expressed only a mild curiosity about anal sex, but more recently made the commitment to explore it more intentionally. To this end, Viktor purchased a set of butt plugs, so that we could start training my ass to receive his cock. Among our first trials of these implements, I had an amazingly orgasmic session (see my Blissed Out Beyond Belief post). It was an auspicious beginning for sure!
With such a positive introduction, I was happy to be on this journey and we continued to schedule time explicitly for this purpose. After several anal play dates, I became more comfortable with having something inserted into my ass and began to enjoy the pleasurable sensations that such stimulation provided.
On one such occasion, we left the plug inserted in my ass and proceeded to have penetrative sex. It was extremely intense and orgasmic to have the additional stimulation while having Goddess spot and clitoral stimulation. Although the plug ultimately fell out, it was a fun experience and confirmed why Mia was so partial to double penetration 😉.
By now I felt as ready as I’d ever be, so I told Viktor that I wanted to try to have PIA sex on our next date night. He readily agreed and we planned accordingly. That evening, I took a luxurious bath and consumed an edible. Once we got to the bedroom, Viktor gave me a sensual massage, further putting me at ease and in a heightened state of relaxation
For this first foray, we had decided that Viktor would wear a condom to assist with clean up and minimal bacterial contamination and, of course, we used lots (and lots) of lube. After confirming that I was ready, Viktor slowly and carefully slid his cock into my ass a little bit at a time. I’m not sure if it has been mentioned here previously, but Viktor’s cock is very thick, so this was challenging (and also why I’ve been so apprehensive about all of this). As time progressed, Viktor eased himself almost all of the way in. As he did so, I stimulated myself with a vibrator to facilitate relaxation and pleasure and also to more directly pair the orgasmic sensation of clitoral stimulation with that of anal stimulation. Eventually it became too much and I asked him to stop. Viktor immediately withdrew and quickly cleaned up, permitting us to have penetrative sex to finish the night.
Building on that positive experience, and as noted how anal sex comes up frequently in conversations with potential/new partners, I had a frank discussion about anal sex with Cooper on our second date. I had met Cooper on OK Cupid (and also matched with him on Feeld). Before we met, I had a really great feeling about him and revealed my real name early on, which he seemed to appreciated. For our first date, we met up for drinks, followed by a delicious dinner and then a PG-13 (but no less sexy) make-out session in his apartment. Throughout the evening, we seemed to connect really well in addition to having good chemistry and he soon asked me to go out again. I happily consented.
For our second date, Cooper invited me to go ice skating. We had a blast skating together on an extremely warm January night and then had dinner nearby. After our meal, we returned to Cooper’s apartment and turned our attention to each other, anxious to resume the make-out session we had started on date number one (as well as the one we briefly had before heading out to the rink).
As we quickly progressed from kissing, Cooper led me to his bedroom and began to undress me. I was soon naked on his bed and helped to relieve him of his clothes as well. He had boasted of his oral sex skills and was eager to demonstrate them and I was just as willing a participant. After I had climaxed a few times, I asked Cooper if he would like me to return the pleasure. He readily affirmed his interest.
I then asked him a few questions about his preferences before I began and then preceded to lick his cock before taking it in my mouth. After a while it was clear that he was enjoying himself, but I wanted to know more about what really turned him on. I told him that I was open to direction as well as suggestions for additional stimulation. He advised me that if he received anal play while getting a blow job that he would come really hard.
Although uninitiated, I was very interested in learning so he gently and reassuringly guided me through my first prostate massage. I guess I didn’t do too badly since the intense climax was achieved as advertised. Later, Cooper played with my ass, which was also quite pleasurable, although less orgasmic than oral sex.
I surprised myself at how comfortable it was to share the experience with Cooper. I didn’t feel shy or worried to be so open and exploratory. And he was a good teacher. When I arrived home the next day, I immediately put my new skills to use with Viktor who was very appreciative.