Sorry it is so long. It was hard for me to shorten it.
Before I separated, I was seeing a Psychologist, Doc is what I called her. She called me a pleaser and in hindsight, I was really a mess after a 24 year marriage. One of my issues was sexual dysfunction where I thought nearly anything I did was wrong, not appropriate, not normal, etc. The Doc corrected me of these notions. She told me that maybe a naked day would be a way to release my 'energy'. At first it was a weekend day to be naked as much as possible in appropriate venues. Home at first.
I had a day off on my next appointment with the Doc at one pm and declared it a naked day. I went commando in shorts, t-shirt and athletic shoes to the appointment, something I would not ever have done or considered. At the appointment Martha asked if I had a naked day yet and I told her this weekend and today. Her eyebrows raised in an interesting way. She inquired where, what and how I spent my naked days. I gave her the details like I would to a five year old asking about sex. I could see how the Doc thought my answer inadequate but instead of pursuing it, asked how I felt about it. Typical Therapy line I thought. I told her bluntly that I jacked off at least three times before the appointment thinking about how cool it would be to be naked with a Doc! She quickly told me that this was not an appropriate venue, but it was ok to fantasize if it stayed a fantasy. We spent the 50 minute hour talking about what is appropriate. I was so amazed at how distorted my thinking was about this whole subject. She was actually telling me I was very puritanical and to spread my wings. I asked if it was ok to jack off instead.
Toward the end she asked me what I was planning for the rest of the day. I told her I would like to do it outside. She wanted clarification on whether it was to be naked or masturbate. I said both. She offered some suggestions that gave me some great ideas. In later sessions Martha helped me understand that couples should be able to discuss sexuality and help understand the boundaries of a health relationship. I tried her suggestions with what became my first real girlfriend after my separation and later divorce.
I picked Kathy up for our second date at 7pm on a Saturday to go to a nice, but casual dress restaurant. I went commando in shorts, nice shirt and new trainers. Not sure if you see a pattern yet. Kathy was dressed similarly only I could see the outline of her underwear. She was an RN and I soon found very open to the discussion of sexuality. We declared that a healthy relationship should be able to discuss anything and everything honestly. It had the risk of finding out we were not compatible and the benefit was connecting at a deeper more meaningful level. For me at the moment that meant connecting with nudity, masturbation and sex. Another pattern was forming. I used to think I was the only person that would think of such. I now think all men do. Not sure about women.
It is said that you write to learn what you know. Similarly, talking with someone can reveal your boundaries and at times, stepping outside your comfort zone will help you understand your capabilities. You may not know yourself until you try new things. What we do needs to recognize our needs and respect others boundaries. What I became to understand is that my ex-wife would draw a line in the sand as a boundary not to cross when I was already leaning onto my next step. Failure was assured.
My discussion with Kathy went so well that she invited me over for a night cap. She was clear though, no sex. I was fine with that and I respected her for saying it up front. In my mind it left nudity and masturbation as possibilities. We continued our in depth discussion about sex, nudity and masturbation at her house with a bottle of wine. This lead to my forced disclosure of a sleeping naked and a naked day to burn off energy. I explained how Martha helped me understand appropriateness. In my mind I thought this was a bad, long winded one liner and would end our date. I added that I wanted to try being naked with others even when they are not. Her eyebrows lifted. I asked her about work to change the subject and learn about her. Actually I thought she was going to ask me to leave. She stuck to the theme and included some of the things she had done as an RN. It seems that the code of Nursing, or at least in her circle of professionals, that it was ok to help a patient when they were in need and unable to take care of themselves. I found this intriguing as she talked about examples without disclosing confidentially. It added to strength to my erection and help me understand how Doc was really leading me in the right direction here.
We finished off the last of the bottle of wine went to bid her goodnight. It was almost midnight when I stood and wobbled. I could not believe I was unsteady on one bottle. She told me it was our second bottle. I had been dry for three years by choice and I was not used to this much drinking. I drank a fair amount when I got married and wanted to be sober when I got divorced. I had a good buzz and Kathy took my keys. I saw it was a good decision and apologized. She offered the couch and commented that a cheap date was a good attribute in a man. She would not live with a drinker. I added that it was also a good way to make me limp. She laughed as she went and got a sheet and a pillow to use on the couch. She told me to make myself comfortable and I stripped to my shorts. I was so horny with all this talk that I had a wished I had a hard on to play with, instead I was dead to the world in minutes.
In the morning I had a huge headache and Kathy had me drink a lot of water and then coffee. I helped her make breakfast of eggs, corn beef hash and toast. She offered to let me use her shower and told her I had over extended my stay and thanked her. She gave me a hug and a peck on the cheek that seem to say she was glad I was leaving. When I was at the door she asked me what I was going to do. I told her I was thinking about going sailing. Somehow the fact I had a 30 ft sailboat escaped our disclosures. Her face lit up. I loved sailing and loved the big Lake Michigan with just wind, waves and my boat. Her face dropped. I asked if she would like to join me. Her face lit up again and she confided that she loved the water but never had been sailing, just power boating.
We met again at the dock she had brought a picnic basket full of goodies. My mouth watered as she listed the contents. When we had cleared the break water I set sail and we relaxed under the canopy. My dad and brother already had many potential skin cancer spots removed so I stayed out of the sun with a highest SPF one could buy. I blamed it on my Swedish heritage. It was only 10 am and the wind took me toward Northport. I told Kathy we could sail there by mid day, anchor and eat lunch and sail back by evening. She jumped at the adventure. Her face dropped and worried about sailing to somewhere not currently visible. I told her I started as a young kid learning how to navigate and became very good at it. Neither one of us had to be at work before noon the next day anyway.
Then she ask if I had done a naked sailing day. I said I had not, not yet anyway. I had no good answer to her question why not. After a pregnant pause, she said it would be fine with her if I wanted do it this time. I pondered the comment looking in her green eyes and looking away shying off the idea. I didn't want to be too eager did I? She used my words against me from the previous night and said I would never know my boundaries until I pushed them past my comfort zone. I said that being naked alone on the boat is different than with someone. She said I made her point. I said oh. She was sly. I was down to my shorts with no underwear as usual. She offered up that she was an RN and used to seeing naked bodies. I told her I would if she would. She countered that it was my boundaries we were exploring not hers. My thought was that Doc's coaching might have boomeranged. Again, she was showing her slyness. While I wanted to be naked, I realized at the moment it was Kathy I would like to see naked.
I changed the subject and we talked a few minutes really to give me time to adjust to what I knew I wanted to do. I came back around and asked her if she was sure. She nodded. Before I could finish my next sentence about what if I get an erection she reminded me that she was a RN and seen it all. I thought it was as good line as any I had tried and failed in a smoky bar. Maybe it was the delivery?
I changed the subject as if it would hide what was decided and to build my courage. Finally, dropped my shorts and looked Kathy in the eye. Those green eyes were a blaze with passion now and a sharp contrast to the cold blue water. She smiled as she looked back and told me it wasn't that bad now was it. I agreed. She scan my body and commented that I was a good looking guy. Surprisingly I was able to let my erection subside and was relaxed most of the sail. Every so often Kathy would move, say something or look at me just right and I could have sworn I heard it go boing as it snapped to attention. I thought of Wiley Coyote chasing the road runner, doomed to the sly nature. I wished I was bold enough to just jack off. But, somehow I knew it would be better to wait.
We were maybe a 1/2 hour way from our destination when Kathy commented on how hot it was. I offered to drop the sails so we could swim but suggested to wait until we anchored. As soon as we did anchor, I was telling her to jump in. Earlier she removed her clothes to reveal a nice body in a bikini. She didn't hesitate and was jumping off the bow. I was anchored far enough off the mainland so I could stay naked and jumped in after her. She loved jumping off the boat and we did that a few times. This time I dove and she followed in the same manner only to have her bottoms slide down to her knees. I would not have know it if she had not laughed and told me. I told her that skinny dipping was legal in Lake Michigan and a thrill to boot. She replied that it did feel very good and that it was not legal, but she would risk it. She flung her bottoms on to the boat after some encouragement. I wrinkled my eyebrows in the familiar way and gave her a smile. While kicking she removed her top and flung that onto the boat also. Her pink, perky nipples were visible as she bobbed. My worm moved again despite cold water. We laughed and splashed around. She dove under the boat to get away revealing a nice bottom. It appeared she was smooth shaven which I confirmed later.
We played until tired and I suggested food. As she went up the ladder, not only did I get confirmation, her lips were swollen, pink and looked edible. Her puckery pink anus was visible as she proceeded. I was throbbing now. We ate and drank more wine and beer. Oh, did I neglect to tell you alcohol may have or may not have been involved? I am sure that improve our decision making. We ate, naked and I throbbed now and then and I am sure it was only her highly trained RN educated eye that caught my penis moving. We enjoy each other and laughed out loud, naked. She was in midst of telling me how she recently had a boy about 17ish with both hands bandaged and sporting a hard on only a horny teenager could have when I quickly stood to show her mine and asked which was better. She brutally destroyed my ego by saying his because as she touched his penis during his sponge bath, he shot off so fast and hard that it even surprised an experienced RN. She was unable to cover it quick enough after he shot all over her including getting cum on her cheek, upper neck and clothing. We laughed.
Now I was so hard I could not stand it much longer. She nicely asked me to come closer. She used one hand and stroked my cock nicely, firmly and with the other massaged, manipulated my balls. I was holding out as long as I could and she told me not to. She said that I held out all day and was due a good shot. She wanted to drain me and without much more encouragement, I shot a satisfying load. She aimed it on her chest and then rubbed it in. Before we set sail for the return, we swam one more time. Again I followed her up the ladder and got an excellent view. Completely ignorant of how it felt, I wanted to slide my finger in the exposed orifices. On the next sailing date, as she went up the ladder and I asked her to stop. First I fingered one hole then the other. She thought it was interesting I had not had that experience and held still making it easy to try.
The summer was filled full of long discussions, laughter and adventure. Much of it on Lake Michigan. I learned how to enjoy the female body and what parts are more delicious than others. It was something I was not able to do when married. Being outside, the wave action of the boat added a new dimension that still makes masturbate material a decade later. Get the right combination and all but the grunt is done for you. Once Kathy held her hand still while my cock slid through her fingers with the boat rocking supplying all the energy to cum on her face. The other times are not suitable for this site.
They say a real sailor can sail nearly any weather and more importantly knows when not to sail. That summer I sailed her body like it might be the last day my boat would float obedient only to her boundaries. Some of which were only temporary lines in the sand. It wasn't until my next girl friend I learned when not to sail. What a sailor's delight!
Kathy was the angel that helped me understand us as humans. Doc was my Angel that opened the world to a new day, Naked.