I had been reading a long time on different social sites about "gurls" describing their first time out with a man. As I get older, I began wondering what this would be like. As my wife does not know about my "other self", plus living in a small, conservative town, it has been almost impossible to satisfy my curiosity. Until now. This may turn in to a rather long story, but I hope it is worth it. It was to me.
My wife has been under the weather for awhile. It was determined she was going to need surgery then a long, slow rehab. I will try to make a long story shorter by saying she had the surgery and it was successful, but she had to spend several weeks in a rehab center.
Due to the length of time involved, I began signing up on several TG dating sites. I know online dating is not the safest nor always best, but given the current circumstances, it was the only way. I had plenty of preparation time as it worked out. I met a couple of nice gentlemen online from nearby towns. One was close to my age and the other was about 25 years younger. The flirtations with each of them was exciting. Both sent me several pictures. Finally, my wife had her surgery, began her rehab and I now had the opportunity I had long been waiting for. I set up a date with the older gentleman first.
He is around my age, give or take a year or so. Very distinguished looking, he had been a widower for about three or four years. He lives in a city about an hour or so away from where I live. We made plans for a dinner date at his house for 700 pm on a Tuesday evening. This was the day after my wife entered the rehab center. I visited her very early in the day so as to have the rest of the day all to myself. I told her I had home repair projects to get started on.
On the way home, I stopped by the drug store and purchased several makeup items on sale. It is never good to let makeup sit too long and I figured what I had was probably too old since I had not used it for awhile. When I returned home, I retrieved my "stash" from the box in my closet. I washed the clothes I intended to wear while taking a nice, long, hot bubble bath. It was very relaxing. I shaved all of the hair on my body from head to toe. I shaved my face twice to make it extra smooth. When I got out, I rubbed in peach body cream. It smells nice and helps keep your body soft. I threw my clothes in the dryer and proceeded to give myself a nice manicure followed by a pedicure. Being conservative in my older age, I used a nice hot pink nail polish.
I then proceeded to attach my silicone breasts using the proper body adhesive. Following this, I put baby powder on my lower body and slid on the latex vagina panties purchased a while back but never used. This gave my lower body the real feminine look. It also adds the proper amount of inches to the rear, hips and thighs. The skin match is almost perfect to my real body tone. I then put on one of my wife's nice, satin robes while applying my facial makeup.
Once my makeup was applied, I attached my wig firmly to ensure it would not slip & slide. I applied leg makeup to make my legs look shiny and extra sexy. Once the leg makeup dried thoroughly, I tightened up my corset, slipped on my dress, shoes and jewelry. I was ready to go. In my mind I was not totally passable, but did look feminine enough to pass muster.
I texted my date to let him know I was on my way, plugged his address in my GPS and headed out for what I hoped would be an exciting evening. My nerves showed as I headed out but seemed to ease once I was on the road for several minutes. I must say it was hard driving in sexy 4 inch heels, but I adjusted.
I arrived at my date's very nice looking home, parked in the driveway and headed to the door. It did not take long for him to open the door. He was much nicer looking in person than his pictures showed. Athletic looking, a full head of beautiful gray hair and an ageless face. He smiled, complimented me on my appearance and showed me into his house. After showing me to the couch, he opened a bottle of white wine, poured then handed me a glass. He sat down on the couch next to me. We sipped the wine as we conversed about different subjects. Before too long, he noticed my empty glass and refilled it.
I do not know how long it was before I began feeling a bit light headed. It may have been the excitement, an empty stomach or just my willingness to give in, but I soon felt like I was having an out of body experience. I was very much willing and eager to give in to any of his demands. He must have sensed how I was feeling as he moved closer to me, put his arm around my shoulder, lifted my chin with his free hand and proceeded to give me a nice, soft, romantic kiss on my eagerly waiting lips. This man knew how to kiss! The deeper the kisses got, the more I was getting turned on. He moved his hand down to my leg and began caressing it very slowly. This made me feel more sensual than I ever thought I could. He began to nibble at my ear, then moved down to my neck. I was feeling more feminine than I ever thought I could. He then whispered in my ear how hot I made him feel. That stoked my fire even more. He asked my to put my hand between his legs. I did as he suggested and immediately came across his massive bulge. The more I rubbed it, the more turned on I became. I then, instinctively I guess, proceeded to unzip his fly, undo his belt and reach my nervous but eager hand under his undershorts. He began moaning as I was stroking his manhood.
It did not seem like I was stroking him too long when he whispered in my ear to get down on my knees between his legs and pull his pants and undershorts down to the floor. When I did so, his thin but long dick sprang up. I proceeded to fondle his balls, then I started to flick my tongue along the underside of his dick. It was not long before I had his dick in my mouth and began soaking it with my tongue and mouth. His moans became louder and longer as I continued to suck. It did not take long before he wrapped his large hands around my head, started pumping for all he was worth, then shot his load down my throat. Even though, he shot more than I ever thought possible, I managed to swallow it all. It was absolutely delicious. I savored the taste and volume. Long after he came, I continued to kiss and lick his lovely manhood.
As he relaxed, he asked me if I wanted another glass of wine. I declined because I was still savoring the taste of his load. It was yummy! I then decided it was time to move to the bathroom, redo my makeup and head out. As I was ready to leave, he kissed me on the cheek and forehead, thanked me for a lovely time. He told me that any time I wanted to come back and relieve his load for him, I was more than welcome to do so. I then exited the house, got in my car and proceeded to return home. I thought about the experience the entire way home and into the next day. I concluded that if this was what it was like to be a cocksucker, then I now understood why so many are proud to be that way. I could not wait until the next time I got dressed and got on my knees.