There are some problems for me that complicate the process of getting it done. The first and biggest is that I don’t know how to go about arranging it. Experiencing this with someone that I know or work with does not seem like a good idea.
The biggest thing for me is to be careful that it doesn’t get known that I have experimented. I would not want to explain to my wife, family, or colleagues. Close behind that is that I do not find men sexually stimulating except those times when I am deep in a fantasy of being made love to as a woman. I’m not homophobic but the gay lifestyle is not attractive. I am not interested in exposing myself to HIV or any of the other long and scary lists of STD’s.
Having said all that, I think that it is possible, or I believe that it is possible for me to find a way to fulfill my fantasy. I knew that I did not know enough to do this thing so as is my wont; I made a study of the whole process by reading up on the subject in Literotica. I learned about the process of accepting the invader into my man-pussy. I knew that I did not want pain, and I knew that I could not get one finger in my ass without working at it. I did not want the experience to be painful so I started stretching my sphincter a bit at a time until I could take what I think is a fairly representative dildo with out pain. I experimented with different lubrication and found that KY is the most effective and with the least complications in clean up. I even found and bought some female condoms and tried them so I could be protected while affording my lover the pleasure of ‘bareback’. They were uncomfortable for me and were very difficult if not impossible to use.
I started out by browsing some of the adult dating websites and settled on joining AFF. I categorized myself as being bi-curious, and got dozens of responses. Most of the responders seemed to want the fantasy to play out on the computer screen. I wanted (and still want) a real encounter. It seemed that extensive and repeated descriptions of the desired scenario were the object. I didn’t mind playing that game, but the brief and inarticulate responses to my missives were totally unsatisfactory for me. I don’t mind giving but I want something in return in the form of nutrition for my fantasies.
There was another category of responses that was equally unsatisfactory, those who would take care of my itch in a way that involved pain and domination. I am not interested in either inflicting or receiving pain. I am not interested in either dominating or being dominated.
Then there are those who would take care of me on the way home from work, they could devote all of 40 minutes to the encounter. If I am going to experience being a woman, I want what a woman wants: Time.
One guy seemed be a good candidate, but insisted on not using a condom. I want to get fucked, I’m not stupid.
It looked like I was going to get what I wanted with one man. I traveled to another state and had prepared for the encounter by extensively discussing what we were going to do and how we were going to do it. I had gone to a lingerie store and bought stockings with a garter belt, some black lace panties (his choice of color), a black silky nightgown, and a matching robe. I had also bought some perfume and red lipstick. I had condoms, lots of KY jelly, and fleets enemas. We met at a bar and talked a bit and decided that he was going to let me have 15 minutes to go to the room and get changed and ready. He failed to show up. He later told me that his wife called to tell him that she needed some baking powder and he needed to get it for her.
I met another man in the hotel room and we talked and kissed but nothing else happened. Neither of us was prepared to take the lead.
That happened about a year ago and I gave up on the whole thing recently I decided to give it one more try. My man-cunt is re-stretched and I am ready to give it another go. Is there anyone out there with some good advice?
I’m still looking for my first time.