Still Looking For My First

I'm still looking for my first time.

It hasn't happened yet, but I'll tell you what, how, and why I want it to happen.

I have had a good sex life since the beginning in 1967. Since then, I have fathered two sons, been on two honeymoons, had my share of adventures between my two wives, have enjoyed and still enjoy a long term relationship with what one might call a 'fuck buddy'. My current wife is sexy and always willing. My 'fuck buddy' and I have a long term relationship that has spanned both marriages and the time between. You will find her picture in the dictionary beside the "Low Maintenance' entry. We talked about marriage between my wives but she declined my invitation with the provision that we could continue as before. I accepted.

Since childhood, I have had a vivid imagination and have experienced many things vicariously that would never happen for real. This has led to a strong capacity to visualize ideas, something that is invaluable in my chosen profession of architecture.

I enjoy exposure to history and the day to day lives of people in different historical period and class paradigms are just some of the things that occupy my imagination. I truly try to walk a day in someone else's shoes. One of my favorite mental games is to look at an older person and see them as young or look at a young person and see them as older.

I have from time to time looked at women, envious of their colorful and comfortable clothing, and wondered what it would be like to be one. I have no interest in becoming a transgender, but I would like to experience part of being one of the fair sex for at least a brief period. I, like I suppose many men, have experimented with the silky things that women wear. It does feel good. I love the cool silky feel on my bare skin and I have experienced that feel as the man enjoying the ritual disrobing of a woman before taking her. Pulling up a long satin gown, bunching it around her waist and pressing myself home is occasionally better than having her completely naked.

Which brings me to the issue at hand: I have been the 'Fucker' for about 40 years and I would like to experience being the 'Fuckee' at least once. This thought has been vicariously explored over the years without doing anything about it except for occasionally raiding my wives lingerie drawers for a hot date with myself.

My fantasy goes something like this: I know that my lover is on his way. I know that today I will experience for the first time a hard cock. For the first time, I will touch a cock that is not my own. For the first time, I will have a cock inside my body. For the first time I will experience the feeling of a hard cock pulsing inside me as it empties its self in me. For the first time, I will feel a cock grow inside my mouth. For the first time, I will taste another's cum. I want things to go well so I prepare as best as I can for the unknown. I start out by giving myself an enema then I take a shower and carefully wash my body. I want to be clean and fresh. I take my dildo and use it to stretch and relax my virgin man-pussy. I dress for my lover, layers and layers of silky things, perfume between my legs and behind my ears, and lipstick. Bright red lipstick.

My lover comes into the room and without saying a word, tells me that he is in charge and that he will take me as his own. He maneuvers me against the wall and kisses me deeply, insistently, and urgently. I ask him what he is going to do and he tells me that he is going to fuck me and I tell him that I want him to. I tell him to go slowly and gently because I am a virgin. He says that he will take all the time I need to give myself comfortably and totally. We continue kissing while he caresses me through all those silky layers. After what seems to be forever he takes off my robe and tells me it is time. I have been holding his growing cock first through his pants then through his boxer shorts and then for the first time I touch a penis that is not my own. I know it is time and I am ready. I am nervous, I want this on an intellectual and emotional level, I am determined to know his cock inside me. I am excited but I am also afraid. It is like stepping out of an airplane for the first parachute jump: you know what is going to happen, you have trust in your parachute and your instructor and you know that it will be alright, still there is a momentary hesitation, a moment of uncertainty, a moment when you need assurance and encouragement, and a firm push. He knows this and proceeds deliberately, slowly, gently, unstoppably. Then I know that it will be alright.

Like a skilled dancer, he takes the lead and guides me to the bed, kissing, whispering encouragement, caressing, assuring. I follow his lead willingly and blindly. If he were to let go of me, I would stumble and fall. The promise of his filling me, of being filled as I have never been filled before makes my knees weak. He pushes me gently back on the bed and he steps back to take off his clothes. For the first time, I see the instrument that will change my fantasy to reality, I touch it again and pull him close so that I greet it with a kiss and hold it. Taking him in my mouth will wait for later, for now, I want him deep inside so I can wrap my arms, legs, and man-cunt while he fucks my mouth with his tongue and my pussy with this beautiful cock. He steps back and slowly pushes my gown up exposing my silky legs. He hooks his fingers through my panties and pulls them down my silky legs exposing my virgin pussy.

I help him lift my ass off the bed and place a pillow under my hips to make his taking of my virginity easier. He takes a condom and rolls it on his hard cock, takes some KY and makes sure I am well lubricated and puts more on his tool. He kneels between the knees that have opened to accept him. He kisses me. I look into his eyes as he guides his cock to my wet hole. He gently applies pressure. I push back.

The time is now, the place is here, there is no turning back, and I will know the feel of a man inside me. I will accept him gladly and hold him until he empties himself deep in me. I will feel him tense, push as hard as he can, and pulse. I will hook my legs around him and pull him inside me as deep as possible. I will tell him to fuck me and fill me to overflowing!

When he is spent, he will relax and let his weight rest on me. I will run my fingers through his hair and tell him that he has fulfilled a lifelong dream. I will also tell him that after he has rested, I want to hold his cock again. I want to take it into my mouth and feel it grow. Until today, I have never touched a penis that was not my own, but today, I have known the feel of one inside the closest thing that I have to a pussy. I have closed my eyes and for that brief period, I have become a woman and know what it is to be made love to. I want to also know the feeling of power over him by making him hard with my mouth.

That is a minimum!

If possible, I want to spend a night with him. I want to shower with him, I want to wash him, I want to shave him, I want to go to sleep with his arms around me, and I want to waken with his hard cock throbbing with promise, between my legs as we spoon.

I want him to be able to articulate his fantasy and I want to be for him what he has been for me. I want to make his fantasy live.

Three years ago, I decided that I needed to do something besides think about it, if I was ever going to experience it.

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.