We both texted about the happiness and sexual stimulation of that night. We were so well matched even though there was a 14 year age difference. I had managed to learn her body and how to stimulate her to a maximum level of pleasure and challenge. Although we hadn’t really met her Craigslist posting initial vision, we had found more than either of us had intended. Neither had planned for love. Was that how it worked? Was love more likely an accidental discovery or development?
Spring slowly arrived and the budding trees gave me hope that another night with Luna would come. The life forces of the planet encouraged me to avoid frustration and gain happiness from all of the new life bursting forth. The bright blossoms and flowers were always cheery and I smiled as the plants in my yard burst forth with strong energy. I didn’t pressure Luna for a date because I didn’t want to add to her existing pressures. I lived day to day ready to be with her, but determining by sundown that I would have another night alone in bed.
Every day included periods of unhappiness about my situation. I was in love with a woman who didn’t have enough time in her life to be able to share even a few hours. I did my best to banish thoughts of low self esteem but they came every day regardless of my efforts. Some days I sensed anger growing from my frustrations. Was I getting angry at Luna or just at the situation? I felt as though my life were on hold. I was in my middle 60’s with my life’s end visible. Luna was in her early 50s with lots of life left. She could afford more patience than I could.
The days moved slowly forward with no change in sight except my attitude. One of Luna’s children was being bullied in school and the troubles increased significantly. Her anxieties were properly focused on this challenging situation and the well being of the child was uppermost. It felt as though the universe was conspiring against us, leaving us with no opportunities to be together.
I began to think about the couples in the military where one was posted out of the country for six months or more. How did they manage? Perhaps their youth made the time go faster. For me a month without Luna was an eternity. As April arrived my hopes for being with her were regularly dashed. Each day I gave up hope earlier and worked to find activities that would use up time. I didn’t want to spend each day focused on her, but I did anyway.
The best way to avoid thinking of Luna was to be out of the house. She had provided me with so many images of us in all of the rooms in my house that there was no respite being indoors. I went to the ocean even though it was still far from warm enough to be comfortable. The chilly wind bit at my cheeks and I kept my hands in gloves or stuffed in the pockets of the jacket. I didn’t do this as punishment but simply to have an escape from the torment of being alone in my own house.
Cooking for just myself provided no pleasure because I wanted to be cooking for two. I wanted Luna at my table enjoying my food, knowing that we would be naked soon thereafter. I wanted to see her smile and sense those feminine smells. My hands wanted to reach out and touch that soft flesh that provided so much pleasure.
I thought about taking a trip somewhere but then decided that I couldn’t risk missing a last minute opportunity to be with Luna if she got free time. I was mired in a plot of my own making. Staying home was painful but traveling was too risky.
I had no interest in wanting a different woman, but as Easter arrived, I thought about sex with men. She hadn’t asked me to reduce my time with men but to be always safe in anything that I did with them. If she were going to be unavailable, she would have to live with my choice to be with men. I needed a sexual outlet and hoped that spending naked time with men would reduce the frustrations I was having with Luna.
I reconnected with a couple of men who I had been with multiple times. They were glad to hear from me and I set up a playdate with each of them a few days apart. John was my first entertainment. He was a submissive man who enjoyed taking my cock in both of his openings. He was very skilled at sucking and I enjoyed fucking his smooth ass. He was around my age and had shaved off all of the hair on his head. He had just an average size dick so my focus was going to be on him pleasuring me.
He arrived smiling and departed with a larger smile an hour later. We went to the massage room because my bedroom still had my feelings for Luna fully attached there. John didn’t even bother to take off any clothes before he dropped to his knees and pressed his face against my jeans. I pulled his head in closer and he massage my legs to increase the bulge in my pants. When I was halfway engorged, he undid my jeans and pulled them down around my ankles.
John’s warm mouth quickly slurped the head of my cock inside and he sucked with pleasure for both of us. Soon I was hard and massaging the back of his throat. I was glad that there was nothing about him to remind me that Luna was not the one taking my cock. He was totally masculine but loved to suck and bend over. “Your cock tastes so good. Are you going to fuck me with your big dick?” I had anticipated that we would get to that state, but I wanted to tease him.
“You have to lick my balls first,” came the reply. John bent over so that his tongue could be underneath me. He hungrily did as I directed. He used one hand to stroke me while his mouth stimulated my testicles. I hadn’t orgasmed in a few days and was concerned that he might get me off this way. “Assume the position,” I told him.
John removed his sweat clothes and leaned against the door frame which was one of the positions we had used before. I put on a condom and provided lots of lubricant to his ass before sliding my hard dick against his ass crack. I grabbed him by the shoulders and pushed him lower to better expose his opening and to give him a greater sense of being taken by a dominant man. His hole was fully exposed in this position and I pushed the head of my cock directly in. I held it there while he adjusted to being penetrated. My thick cock always gave him a little pain on entry.
“Please give it to me,” he requested, but I slapped his right cheek with the flat of my hand for speaking out of turn. I smacked the left side and said, “I’ll give it to you when I’m ready.” With that I pushed a couple more inches of the shaft inside and I heard John take in air but not exhale. He knew not to say anything but just take what I was going to give him. He released his breath and I sensed that he was relaxed enough to take all of me but I only thrust in and out with a few inches, making him want all of me even more.
Without any indication, I suddenly pushed my whole hard cock inside and pressed my wet balls against his smooth ass. “Oh God, that’s a lot of cock,” came his response. I was aware that he hadn’t been fucked by anyone with more than six inches so my extra inch of shaft touched him in places that didn’t normally get stimulation. John took some deep breaths and used his sphincter muscles to close tightly around my hard dick.
The stimulation had a good effect on me and I was ready to fuck with abandon. I pulled back all of the way and slowly slid all of my cock back inside him. I kept up this slow, deep penetration for a few minutes before I needed to increase the speed. I fucked him hard for another couple of minutes before I sensed that my orgasm might be close. I slowed back to the original thrusting style and John responded by tightening his ass again.
“Stroke your dick,” I commanded because I knew that I couldn’t hold out much longer. John liked to orgasm while his ass was full of cock, so now was the time for him to take his dick in hand. That always caused his ass to tighten further which increased my arousal. I returned to the hard, fast fucking and quickly sensed my cock getting thicker. That stimulation led John to orgasm which came with a loud yell. I grimaced as my own orgasm spurt into his naked body. Both of us were gasping for air as our bodies tried to normalize.
With one final squeeze, John pushed my softening cock from his ass. The condom was extremely full and I had to quickly remove it so that it wouldn’t make a mess. John righted his aging body with difficulty but he was fully satisfied. “I’ve missed you bud,” came his grateful words. I smacked him playfully on his bare ass to return the compliment. We had never been ones for small talk between us; our relationship was strictly sexual. John cleaned himself in the bathroom and returned with his sweat clothes back on his body. “See you again soon, I hope,” were his exiting words as my front door closed behind him.
John was a delightful distraction from my object of obsession but the relief was short lived. Luna’s absence made me desire her more and there didn’t seem to be any way out of this situation that didn’t include suffering and loss. All I could do was proceed with the second playdate and enjoy the distraction as best as I could.
Ray was a young bearish man with an average size dick. He wasn’t as furry as many bear men can be, but he had the larger body that went with the type. He was tall with a very pleasant personality and always arrived clean smelling as though he had just come from a long shower. As a total top, he wanted to be sucked enough so that he could proceed to a rapid penetration. I had a sense that he was bisexual because he liked to have the lighting reduced.
Over time I came to understand that he also enjoyed sex with a man who was wearing women’s clothing. I had learned early on in my bisexual exploration that wearing feminine items didn’t do anything for my arousal. Nor did they enhance my sense of being sexy. For some reason, it was different with Ray and I sometimes chose to put on black, lacy, women’s underwear that had belonged to a girlfriend. When I put on a loosely fitting black silk shirt and tied it up under my pectorals the way that women do, I felt I was more appealing to him.
For this meeting, I decided that the black outfit was called for. I told him that I would leave the front door unlocked and I would be waiting for him upstairs. We had made this kind of arrangement in the past and we were both comfortable with the scenario. He was due to arrive at 7 PM when the light of the day was long gone. There were lights on downstairs for Ray to find his way in, but upstairs I only had one dim light on in the massage room. I planned to be waiting for Ray at the top of the stairs.
He arrived on time and I welcomed him to the house from upstairs. He took off his shoes by the door and started climbing the stairs. This was the first time that I greeted him from this position and he was pleasantly surprised to see me there with my ass pointed towards his upcoming face. “That’s appealing,” he complimented as one of his hands squeezed my right ass cheek, while the other held onto the railing for safety. I moved forward so that he could achieve the landing. He pushed his large body against me and cupped my chest with both hands from behind. I enjoyed feeling the bulge in his pants pressing against my ass.
“How nice to feel you,” I said while pushing my ass more fully against him. He made a pleasant humming sound as his hips pushed back in response. “Come with me,” I encouraged as I went into the massage room. We usually spent our time in the bedroom, but I was still reluctant to have sex with men in the space that I had been reserving for Luna. Ray didn’t mind what room we were in as long as he was going to have my warm mouth on his cock.
He readily followed me and remained standing while I dropped to my knees. I rubbed my face against the very firm protuberance restrained by his pants. I undid his belt as well as his zipper to allow his pants to fall to the floor. He wasn’t wearing any underwear which was unusual for him, so I was a little startled to have his firm shaft in my face right away. His overhanging belly required me to turn my head to the side to take his cock into my warm mouth. I never minded that he was overweight because he was always able to be hard in an instant.
Ray ran his hands through my smooth hair while my mouth bobbed back and forth taking him as deep into my mouth as he could go. “Oh, you suck so good, baby. I missed you.” His words of appreciation drove me to suck harder and I tasted his sweet precum with pleasure. Neither of us wanted him to orgasm in my mouth and it wasn’t long before he said, “Let me see your sweet ass.”
I loved the way that his words made me feel and I wanted to have his hard dick sliding inside me. I stood up and turned around while he took off the rest of his clothes. I knelt on the edge of the futon and he came behind me with his cock pointing straight toward me. His beefy hands massaged both of my ass cheeks while his dick pressed against my black panties. He gave me a light slap on one cheek and used his other hand to pull those panties down.
I had lubed up beforehand knowing that the only anal activity Ray enjoyed was penetration with his cock. He put on a condom and slid his dick up and down my ass crack to add some of the lubricant to his shaft. In one sudden move, he pressed his cock downward and pushed all of it inside me. I gasped from the quick entry but was thrilled to have a cock inside me again. I loved the intimacy of feeling a manly man entering me. I especially loved it when it came from behind like this.
I hadn’t allowed that during the eight months I had been with Luna. I had used a toy to keep myself loose enough knowing that at some point I would truly want to feel a man inside me. The toy had done its job and I didn’t feel any pain from Ray’s rapid thrust. He held me in place for a minute while I got used to his hard cock. I enjoyed the feeling of his hands holding my hips and relaxed into his body.
He accepted my signal of readiness and pulled his cock back before returning with speed. He pulled all the way out and pressed back in multiple times before he began slapping my ass with the flat of his hand. The smacking seemed to arouse him and didn’t cause me any pain. He picked up the pace of his thrusting and it wasn’t long before I felt his dick thicken with excitement. His testicles weren’t large, but I felt them smack against my ass with this increase in activity. He didn’t make any sounds as his sperm rushed into my warm opening. His hands tightened against my hips to keep me in place with as much of his cock inside as possible. “Oh, wow,” slipped from his mouth along with his deep exhale. I felt his body relax but his hard cock was still pulsing inside.
His beefy hands massaged my back in appreciation for the pleasure that I had provided him. I knew that he wouldn’t attempt to do anything with my cock which had only gotten slightly aroused while he fucked me. My pleasure came from knowing that I could bring him to an exciting orgasm. With his sexual energy spent, Ray let his cock slip back out and he exhaled another deep release.
He went to the bathroom to clean while I took a seat on a towel I had placed on the futon. I also exhaled and enjoyed the feeling of being freshly fucked. I was glad that there hadn’t been any pain and I felt satisfied in how I had brought Ray to orgasm. He returned to the massage room and even in the dim lighting his smile added to the ambience. “I’m so glad you got in touch,” he declared while returning to his street clothes. On other occasions when we had used the bedroom, we spooned in the bed with his arm wrapped around me. I enjoyed that but was reluctant to do anything that might engender emotions and Ray seemed to sense that.
“See you soon, I hope,” were his parting words as he headed down the stairs. “Yes,” I said softly not knowing where my sexual future was headed. If Luna kept her distance, then I would see Ray and John again soon. If Luna became available, then I would have to make some decisions. My body was happy but my mind was confused and unclear.