Bisexual Conundrum Ch. 03 – Gay Male


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Bisexual Conundrum Ch. 03

By Fantasizeandrealize

Life with Albert was a fairy tale come true for me. I worked hard at his factory and by the time the half year was up, I knew all the work and could expertly operate all the machinery and assemble all the products. When I became the Quality Control and Process Planning manager all the assembly line workers respected me because they knew I could perform any task as good as they could. I worked on streamlining work processes and eliminating practices that caused defects. I also found ways to cut costs. I loved the work and excelled at it. Albert always told me how proud he was of my work.

Since I was living with Albert and had no bills or car payments my personal bank account was growing so fast. It even grew in the first half year when I had the low salary.

Outside of work life was even better. Albert fucked me hard almost every day. I loved blowing him and getting pounded hard. We went on expensive vacations abroad and enjoyed expensive hobbies like skiing, golf, hunting and dirt biking. I loved being with Albert and we grew closer as time went on.

We also had sex with other men. Sometimes, Albert would meet up with old friends and one of his exes. I was always involved and got fucked twice on those occasions or got spit roasted which I loved. Albert would also sometimes meet younger men my age and have us play with each other before he fucked us. I loved this too and always looked forward to new sexual adventures and partners.

The first trouble arose about two years after I started my new life with Albert. He caught me jerking off to Lesbian porn. I always loved Lesbians and still desired hot women. We had a serious talk and Albert told me that now I was the woman. He asked that I stop watching any porn with females in it. I reluctantly agreed and we had a great session of sex.

The next day Albert gave me three bags full of panties, garters, stockings, sexy lacy lingerie, negligées and baby dolls.

“Since you like women so much, why don’t you start dressing the part when we are home together.” He instructed, more than asked.

Under his watchful eyes, burning with shame, I tried on a pair of lacey French cut panties and was amazed at how good they felt on my ass and balls. I kissed Albert passionately and told him I would be honored to wear this stuff for him.

“There is also a bottle of Nair in one of those bags.” He instructed, “Be sure to remove all of your body hair from neck down.”

Once again, we had a great session of sex that night. I was totally horned up from the silky lacey garments. Alberts hands felt even better caressing my body, while it was encased in lace. I really felt feminine and loved the feeling. I teased Albert for a long time, like a high-school girl, until he begged to fuck me. When I finally let him have me, he went at my ass like a man possessed and fucked the shit out of me. He came deep inside and I came without having my cock touched.

Albert wiped my cum off my stomach with the gusset of those panties and made me put them back on. I happily did so and pranced around the house in them all night. His big load slowly drained out, combining with my load, further wetting the material. I felt so slutty in them, that I wore them to bed that night. By the next morning the cum had completely dried and the material was hard and crusty where the cum had been absorbed.

I loved it so much that I wore those soiled panties to work that day. That evening when Albert saw what I had done he had me take them off and he stuffed them in my mouth as he fucked me hard. I could taste the faint taste of our loads the whole time he fucked me. So hot!

The lingerie added a new level of excitement to our love making. The problem was that I was also thinking about women more. Not a month later Albert once again caught me watching porn with women in it. He told me that I needed to be punished.

Albert called up an old friend that joined us occasionally for threesomes. He came over later that evening and watched, as I was hand and ankle-cuffed over a table and spanked with a ruler. This hurt physically, but the shame of having another man watch my punishment hurt even more. The thing was that it turned me on so much!

After the spanking they spit roasted me while I was still cuffed over that table. I got Alberts big load in my ass and his friends load in my stomach. I came too just from the ass pounding that Albert gave me, without anyone even touching my cock.

After they came, Albert told his friend right in front of me, that my punishment was not over. He said that he had a cock cage on order. I would be wearing it and would never be able to jerk off to women ever again. I was humiliated that his friend knew what was going to happen to me. However, I was intrigued about wearing the cage. I had seen them in porn that I watched with Albert and I was curious.

A week later a package came in the mail and it was the cock cage. Albert put it on me and I was surprised at how comfortable it was. I loved it! Albert fucked me hard while wearing it and my cock strained behind that stainless steel device but it could not get hard. I was amazed that I still came from the hard pounding. The cum just spurted out of my semi hard straining cock. Albert scooped up my cum with his fingers and fed it to me.

As I licked his fingers clean, he told me that since I could cum from just anal stimulation, there was no reason to ever remove the cage. However, he didn’t want my cock to atrophy so he would take it off once a week to let me jerk off. I wore that cage for the next seventeen years. It only came off once a week. Albert would let me edge myself, as long as I liked. Once I came the cage went back on till the next week.

I learned to love that cage. Since I could not jack off anymore, I was always more horny for Albert and worked harder to please him sexually. This became more important as the years went by and Albert’s performance started to falter. I would spend hours on the floor, between his manspread legs, blowing him, to get him ready to pound my needy ass.

As the years went by our relationship only got better. I had helped to grow the business. It was now the largest window manufacturer in the Northeast. Albert had me work in all the departments and I knew everything about the plant. Albert was paying me an obscene salary that once again I was mostly banking. Albert often told me that I was a star and that I was probably adding even more value to the business than he was.

At home after work. I dressed in my lacey garments and loved pleasing Albert and feeling so feminine and being taken care of. I got to jerk off once a week and was usually able to have a couple of sissygasms during the week, just from the anal prostate stimulation. I still stole glances at women while out shopping, ogled some of our hot female employees and yearned to experience pussy again. I guess I was bisexual. This I kept well hidden from Albert.

We still had regular threesomes with Alberts old friends but as the years went by it was getting harder to find young men to join us. Albert solved this by finding a few young hustlers. He loved watching them play with me and loved getting a different piece of ass every few weeks. I preferred his older friends but always pleased Albert by playing with the young men too.

Albert passed away at the age of sixty-six from a massive heart attack. It was sudden and came without warning. He was pronounced dead when the paramedics arrived at his office. All of Albert’s assets, the factory, his nice house and bank accounts were in a trust with me named as the sole successor. I was only forty years old. With years of hard work and experience to back it up, I could run the plant by myself. I hired a couple new executives, to take over some of Albert duties and settled into my new role as businessman.

I stopped wearing the cock cage but continued wearing the lingerie at home after work. I also only wore panties under my work clothes. I had no male underwear. I much preferred the frilly panties. They were so much more comfortable. I was devastated by Albert’s death and missed him dearly. I would meet up with his old friends and service them. I still had sexual needs but I could never see myself living with any of these men. The year after his death I was very lonely outside of work. I didn’t have any family.

I needed to find a solution to my loneliness.

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