The Long Goodbye

John was my very first gay lover. I wrote a story about our first time together you can find on my page titled 'Big John'. To briefly recap, I was a 50-year-old, recently divorced man in Florida who decided to explore my life long repressed gay side and met 63-year-old John through a 'silver foxes' gay dating web site. He had a similar back story and had never had gay sex before either. We had been lovers for 3 years when I had to move back to California to settle an estate. John was also going to move back to Pennsylvania to be closer to his kids. We had a wonderful 3 years of incredible sex, and we both learned so much starting out as gay virgins and exploring our mutual sexuality and sensuality.

During those 3 years I also went to bed with several other men, but John was always the first and very special to me. He knew I was sleeping with other guys, and I never tried to cover it up. My kink was I liked to be the woman in bed, and I got very good at it. At the end of 3 years, my cross-dressing skills became highly refined, and I had a pretty impressive wardrobe of gowns, lingerie, and wigs. I could also put on make-up like a pro, had a Lady Shick Electric Razor, quite a collection of skin moisturizers, and had a sissy side that even surprised me once I heated up!

I also stumbled across a niche market in Florida. I found a plethora of men older than I that were either widowed, divorced, or had wives that were not into having sex anymore. This was a generation of men who definitely felt more comfortable being closeted. Somehow me taking the feminine role in bed made them feel less gay. A few even brought that up. Even I was not really into gay porn, culture, clubs, etc. I felt more comfortable and safer with these higher end seniors that were just looking for some sexual relief. Anal was off the table too, as it was for most of these guys. They were scared to death of STDs. There were plenty of ways to orgasm without going up the poop chute. I even got picky towards the end of those 3 years and would be disappointed if my man didn't live in a gated community, have a pool, and a nice king-size bed for our trysts. I even had a few that bought me lingerie and perfume that they particularly liked. I for sure looked better that 98% of the old ladies I saw around me in Florida and came baggage free, pun intended! I made it an artform and put some effort into it. I had morphed into a mistress for wealthy senior men kind of by accident!

I learned a whole lot about making love to older men in Florida too. Many were lonely and just talking comfortably at first was huge. Moving slowly and starting with a soft, gentle kiss on the mouth was the best way to begin and let the passion ignite naturally. I also found it helpful to be the first one to get naked to arouse my lover, as many of them were shy at first. Once I got my hands on their cock, I noticed vigorous jacking while I was kissing them primed the pump. Lots of moaning and expression of passion on my part helped. I wanted them to know they were turning me on too. Once I could get my mouth around their cock; we were off to the races. No pussy would ever feel as good as my sucking and tongue swirling. Cradling their balls in my hand as I sucked them seemed to be enjoyed too. I don't think there is any better feeling than a man filling my mouth with his precious love goo and gratitude. Some of these guys had some impressive old hogs between their legs too, and I surely enjoyed getting them up and running again. One of my lovers jokingly told me my having sex with older men was akin to restoring classic cars! If so, it was a hobby I surely enjoyed! These are the lessons I first learned with John.

I was leaving for California, and John and I decided to spend a whole weekend together 'saying goodbye'. It was pretty obvious this would be the last time we ever saw each other, much less have sex, so we wanted to make it special. And believe me, it turned out more special than we could have ever imagined. It was a transcendent experience, way beyond just a roll in the hay. In many ways it was the first time I felt fully 100% feminine down to my very soul.

I had packed for the weekend with all John's favorite lingerie, the centerpiece being an elegant evening gown he particularly was fond of. John's wife had passed, and he said the gown reminded him of her back in the day. They had a wonderful sex life according to John. I paired that with thigh high stockings, a long blonde wig, and tasteful make-up. John had a thing for thigh high stockings. He said it reminded him of Playboy cartoons in the 60's! I did a practice run the night before at my home to make sure I was perfect. I was beautiful and looking at myself in the mirror even gave me an erection! I put it all in wardrobe bag and soaked in the tub as I shaved every inch of my body smooth. I wanted John to have the best night of his life.

We had always worked it so I would arrive at the house just in my 'man clothes', then go immediately to the bathroom and change and morph into my feminine persona. We kept it as pure as we could, with John really only being exposed to 'Hedy', my female side. We had absolutely no 'man-to-man' relationship outside of the bedroom whatsoever and wanted to keep it that way to help with the illusion. I had no desire to be a woman anywhere except in bed with a man. It was not part of my regular life.

As I was changing into 'Hedy' in the bathroom, named after John's favorite old movie star crush, Hedy Lamaar, I could hear the sweet strains of Enya's "Orinoco Flow (Sail Away)" wafting through the house. I had turned John onto the New Age and Ambient music that was popular right then. There was a local radio station that played this format 24/7 and John really got into it. We often listened to this music as we made love, and it fit perfectly. Enya was his favorite and it was a prelude to us having sex. I put the finishing touches on 'Hedy' and walked out to the bedroom to meet my sexy and wonderful man.

John had already put on a robe and was ready for some loving. His eyes twinkled as he looked me over and I gave him a model's spin around and an inviting smile. The air was electric, and I could sense even then we were in for an amazing weekend. My little pee pee was already getting hard and pressing against my lacey panties.

"You look absolutely beautiful, Hedy! Prepare to be ravished!" John said as he embraced me.

One of the things I loved about John was that he was 6'3" to my 5'10". That height difference made a huge difference in making me feel more 'girly'. I had been to bed with a few men who were closer to my height, and it just didn't feel 100% right like it did with John. Of course, it didn't hurt that John was packing 8" of beautiful, thick cock that functioned perfectly and still shot incredible loads of sweet white cum! My little dick looked like a light switch compared to John's cock. I nicknamed John's cock the 'Terminator'! John loved to suck on my little pee pee clit though. He said it fit in perfectly with my 'Hedy' persona.

John held me close, and I could feel the 'Terminator' pressing against my belly. It seemed even bigger than usual! Then he kissed me, and kissed me, and kissed me. It was very romantic kissing. The vibe was very romantic and set the tone for the entire weekend. There was a tenderness mixed with our passion because we both knew this was the last time.

John whispered in my ear, "I want to savor you all weekend, Hedy. I want to make memories to last the rest of my life. Get ready for some serious loving, my sweet."

And with that John set me down on the bed and we got down to some serious kissing like we had never kissed before. He then lowered the top of my gown and started to gently kiss and suck on my breasts. My nipples were very sensitive, and I truly loved this part of lovemaking. I softly moaned and John gently pushed me back on the bed as his hands caressed my legs. We continued to kiss and look deeply into each other's eyes. We were somehow entering new erotic territory we had not yet experienced.

I was soon naked except for my lace topped thigh-highs and was working John's huge and throbbing member with my hands before I slide it into my mouth with well-practiced precision. This was not our first time at the rodeo! I knew exactly how to keep John on the edge of orgasm from past experience. His moaning was always a sign, and I would stop and go up and kiss him on the lips until I felt the edge fade a bit and then suck his cock some more. Our love making had become an artform.

I went up to kiss John again and he flipped me over on my back as I let out a little sissy squeal. John could be very playful in bed, and I enjoyed that aspect too. I knew what was coming next!

"Now I am going to show your little pee pee clit some real loving!" John said with a laugh. I giggled with delight! I was 100% in sissy mode now!

John spread my legs and took my cock into his mouth. My giggling quickly turned to moaning as I raised my hips to his mouth as he sucked. This was when I suddenly started to feel like a real woman. I closed my eyes in ecstasy and enjoyed hearing John's slurping as he sucked on my little pee pee. I remember thinking this must be what Heaven feels like.

After five years John and I had quite a repertoire of sexual positions we had refined, but the good, old-fashioned missionary position was still a favorite because we could look into each other's eyes and kiss as we orgasmed. On this night it seemed extra appropriate. After sucking my dick, John moved up to my face and started kissing me again. We knew exactly what to do to make this work from our many love-making sessions. John laid his huge cock across my belly as I wrapped my legs tightly around him and crossed my feet. My little wee wee was nestled between his big balls. Now we both had the friction and contact we needed and could control the pace of our fucking. The dance of love had begun.

Our rhythm began slow and easy as we kissed deeply. I started to moan, which excited John and he picked up the pace, with me meeting his every thrust with my legs wrapped tightly around him. This was somehow different than all the other times that we had sex. I realized I was truly feeling a feminine energy to match John's masculinity. We had really just flirted with it before now. It felt like we were melting into each other and becoming one. This was beyond just great sex. We were truly making love. We were mating.

Our lovemaking ebbed and flowed as we kept on the edge of orgasm for as long as possible. John's moaning and thrusting told me the time had come. All I could hear was the sound of our kissing and moaning, and John's balls rhythmically slapping my thighs. I whispered a line in John's ear that I knew would bring him and me to orgasm in our perfect sexual fantasy.

"John, oh John", I said softly, "I want to have your baby."

That was the closer that pushed John over the edge as he groaned and shot his huge load of 'baby seed' all over my belly. My little pee pee exploded at exactly the same time in a truly beautiful simultaneous orgasm. My stomach was covered in both our semen as we kissed in the warm afterglow and john declared his love for me. John eventually rolled off me and I nestled against his chest as we fell into a peaceful and deep sleep.

That weekend stretched into 4 days of saying 'goodbye'. John, ever the retired engineer, kept track of the number of times we came together, which was 18! I know I must have swallowed a pint of John's cum by the last day! I said my goodbyes to John with some tears in my eyes as Hedy. Then I went to the bathroom and put 'Hedy' back into the wardrobe bag and left through the back door to never see John again.