Tony had been coming to me for afternoon massage on a monthly basis for more than five years. He was in his middle 50’s and extremely handsome. He reminded me of Alec Baldwin including the mischievous smile that told you he would be fun in bed. He had pale smooth skin that covered his typical dad body. I knew that Tony was married long before he told me. His dark hair and bright blue eyes made me wonder if his attractive qualities had landed him in bed with women who were not his wife. I easily envisioned women in his office masturbating in their own beds while wishing that Tony were in bed with them. Likely, they were imaging the manly sized cock that he actually had in his pants.
His work in sales allowed him to have an hour of personal time now and then and it may well be that I wasn’t the only one who had pleasure time with him but I never asked about any additional extra curricula activity. The first forty minutes of our sessions were always strictly massage which he needed to help ease the work tensions in his shoulders and lower back. He didn’t touch me and I provided the therapeutic massage that he valued.
In the early era of our meetings, we became sexual with each other within ten minutes after he turned face up. We restricted ourselves to oral activities which included his very sensitive nipples. Teasing and kissing his nipples led Tony to the hardest erection. When I would be focused on taking his thick seven inches of cock into my wet mouth, he would play with both of his nipples himself. Did his wife pleasure that area for him as well? I was certain that she didn’t know he liked to suck cock.
Tony was versatile in his play with me, but often he loved to be on his knees while I fed my thick cock to his eagerly open mouth. Invariably, I was the one to initiate the sexual activity. Part of that was connected to the subservient mental role he liked to play. Part of it was the attractiveness of his cock which I wanted rubbing against the back of my throat. His shaft had a slight curvature which allowed it to slide comfortably all the way down my throat without creating any gagging sensation. It was a perfect cock for me to suck and I always smiled when this handsome man knocked on my door.
Over time Tony became interested in extra massage of his ass. He had a wide masculine man ass with nothing feminine about him. Like most married men he didn’t trim his sexual parts and there was a light covering of dark hair around his anus. I knew that he was becoming interested in activity there by the way that he spread his legs while I sucked his cock on the massage table. I applied oil to my middle finger and rubbed his frenulum before sliding further down to touch his opening. The moaning corroborated his interest and he found the stimulation too much to keep from shooting an orgasm into my waiting mouth.
Eventually, we got to digital penetration of his ass and the massage of his prostate seemed to be a new sensation for him. I finger fucked him gently while I sucked his cock and that always took him over the top. I wondered at what point he would want me to penetrate him with something bigger. Around this same time, Tony began to take an interest in my firm smooth ass. As I sucked him, he squeezed one cheek and grabbed firmly when he orgasmed. He seemed to want an equal experience with me and to use a finger to enter me as well. When his finger wandered there, I knew I had to add some oil so that his finger wouldn’t cause damage or pain. This might have been his first experience with anal fingering. I wondered if he had put a finger up a woman’s ass, but I never asked him.
“I want you to fuck me,” came the inevitable words from my handsome client. He didn’t have the type of ass that I naturally found attractive, but I knew that I could easily maintain enough erection to penetrate him. I also knew that the best way for a novice to be penetrated was by a cock smaller than mine. I would have to work hard to get him to relax in a bent over position. This positioning of him spread eagle over the end of the massage table would give me the most control for squeezing my hard on into his manly body.
While he was still on the table, I used my middle finger to gently penetrate him. I rotated my finger around the inside of the opening to stretch his anus enough to push in two fingers. The wincing on his face told me that he was having some pain but it was going to be inevitable given his virgin ass. His sphincter was very tight and always closed up around my one finger when I rubbed his prostate. I made sure to use a lot of lubricant that would stand up to a condom covered cock.
When I thought that his ass was as relaxed as I could get him, I walked my cock up to his mouth for him to get me very aroused for his penetration. He knew his task and accepted the role of servant to my process. I sensed his mind questioning if he had made the right decision to get fucked. I wondered that myself.
With my cock veiny hard, I directed him to the end of the table and pressed him down into the position I knew I needed for sliding inside. I put on a condom and heard his concerned voice say, “Use lots of lube.” I swathed my cock and his ass and I was surprised to discover that his sphincter had already returned to its unrelaxed state. I penetrated him with my finger and stretched his opening as much as I could. I removed the finger and slid my cock up and down his ass crack to get him mentally ready for the discomfort that he was about to feel.
I squeezed the head of my cock to be as firm as possible and pressed against the opening I had prepped. The large amount of lube made it slippery and it took me a few tries before I was able to get the head of my cock inside. I heard him gasp and his ass clamped down hard on my cock. “It hurts!” he winced. “I know, I know, just breathe,” I responded as one of my hands massaged his back to help him relax. He tried to relax but quickly said, “Take it out. It hurts too much.” I withdrew and allowed him to relax his breathing. “That’s enough of that for today,” I said as I directed him back onto the massage table.
Tony had lost his erection, but attention to his nipples quickly helped him leave the anal pain behind and allow his rod to expand fully. I didn’t massage his prostate or penetrate him with a finger, but squeeze his ass while I sucked him to orgasm to relinquish the hold that the pain had taken on his mind. He would ask me again to fuck him, but it would be a few sessions before he got brave enough for the second attempt.
Over time, we were able to get all of my cock inserted and he grew to enjoy it fully, but it always took an effort to get his sphincter to relax enough for me to slide in. Once we were successful, if I weren’t fully hard, I couldn’t manage to get even the head inside. We came to accept that this play was not going to happen after every massage session. What did change was that he came to explore penetrating me. He didn’t ask about it, but decided to take control during our play time and just pushed me down into the same position at the end of the table that I used for him. He knew where the condoms were and put one on before his hard cock went anywhere near my ass.
His dick was hard and thick and I had some pain when he pushed inside. It might well have been the first time that he had fucked someone in the ass, but having been the recipient of dick, he knew the pain potential and stopped after the initial entry point to make sure that I was OK. I had to take a deep breath or two before I encouraged him to proceed. He quickly became excited and thrust into me with speed and force. He held my hips to keep me in place while he took control of my ass for his pleasure. He treated my ass like a pussy and just kept on thrusting until I felt his body shake as his sperm rushed inside me. Once he was done, he didn’t linger but quickly withdrew and removed the condom before heading to the bathroom to cleanse himself.
I always encouraged him to return to the massage table after his orgasm and cleansing. Often, he was able to afford the time to relax further, but on occasion he needed to rush back to work or to a client. He always departed happy and appreciative of our time together. Over time he revealed more about himself including sports and music likes and dislikes. I never asked about his family or work life because I respected his privacy. Based upon casual comments he had made, I knew that politics was a poor topic for us.
During one of our sessions where he was in his subservient mode, he encouraged me to get on the carpeted floor on my back. He took a place between my legs to continue sucking my cock to its fully aroused state. I encouraged him to turn around so that his dick could be in my mouth at the same time. He was happy to oblige me. I pulled his thick shaft into my mouth and found that my arousal increased. In this position he could always bring me to orgasm. I made sure that he came in my mouth as well.
It was during one of these 69 sessions when Tony decided to take his cock from my mouth and put his ass over my tongue instead. I was very reserved about rimming especially with an ass that was hairy. By this time, we had been together for five years and were open to expanding our sexual exploration even though we never spoke of it. I decided that Tony’s ass was similar to a full bush pussy which I was always willing to eat. Although I began gingerly licking and tonguing him, I quickly moved to the pussy fantasy in my mind and became an eager muncher of his hairy ass. As soon as he managed to get my cock to spurt into his mouth, he moved to a kneeling position with his ass firmly in place over my face. He stroked his manly, thick dick until I felt his legs tighten against the sides of my body and his warm, white fluids flooded my tanned, smooth chest. When his breathing returned to normal, he grabbed a wash cloth from a nearby table and cleaned my chest before he headed to the bathroom to clean himself.
This new position became his favorite and penetration became less and less a part of our sexual time. I was certain that I was the only one in his life who knew how much his ass liked attention. He was such a straight appearing man that no one would have imagined him sucking on a cock, let alone taking one up his hairy ass. Our society had many such men and with the advent of the Internet they were better able find outlets where they could explore their bisexuality.
After I returned from my year outside of the United States, I spent a couple of months in New Jersey to renew time with friends. Covid-19 was becoming more serious again and I was determined to stay safe, but also to be with friends one on one which would limit our risk of sickness. Tony learned of my return and wanted to see me for a massage plus, but his concerns of sickness were even more than mine. Although we kept in communication, the two months passed without us managing a session.
I had decided to Winter in the warmer Western states and didn’t return to New Jersey until March of the next year. Tony was even more eager to have some man on man time which was difficult since I couldn’t host where I was staying. I decided that a hotel was the best situation and was willing to take on the cost to be with my handsome sexy friend. We made certain of a day when he would be able to have free time for us to reengage. Both of us eagerly anticipated our reunion after almost two years. I was gratified by his interest and looked forward to being aroused by his sexy body.
I arranged the modest hotel room and informed him of the room number. He had planned a couple of afternoon hours when he could get away from his responsibilities. I brought the massage oil, condoms and lube which we might need. Tony had requested that I wear a black jock strap for the massage. I had used it once before with him and he appreciated the look. I always wore some kind of covering for my sexual parts while doing the therapeutic part of the massage so that I didn’t have to think about where my parts might be dangling. It also sent a message to clients that I wasn’t open to anything sexual until after the therapeutic aspects were completed.
Tony arrived at my door wearing a surgical mask, but quickly took it off once he was inside the room. His attractive smile demonstrated his happiness at being with me once again. He used the bathroom and returned to the bedroom naked as the day he was born. He climbed on the bed where I directed his position and he exhaled deeply before my hands touched his very pale body to initiate the massage.
I connected with his energy through the palms of my hands as they pressed lightly at the base of his spine. There was a lot of tension in the lumbar region and in his shoulders where he usually left his stress for me to adjust. I felt his body sink deeper into the comfort of the bed as my hands deftly located and relaxed his problematic areas. He was very relaxed by the time my hands got to his ass and he reflexively widened his legs to give me more access to an area that had likely been neglected for almost two years.
There was a new element to this massage on a bed which we had never done until this session. Perhaps it was the distance in space and time which had kept us apart influencing both of us to be more sensual. When I was massaging his legs, I caressed them to my smooth body and rubbed his bare feet against my face. His moaning response led me to go further and I found myself nibbling on his toes. He pushed his fully erect cock out from under his body where I could see his hard shaft on the bed between his legs. I sucked on each of his toes sensually while one hand gently rubbed his cock. I connected these two energy areas into a complete sexual arousal for him.
I placed his legs back on the bed and climbed on top of him rubbing my body all over his naked torso. Periodically, I reached underneath and massaged his dick while our bodies melded. I straddled his body to massage his arms and let my partially aroused cock rest against his ass cheeks suggestively. The proximity of my dick to his opening made my shaft increase in thickness which in turn aroused his ass to swivel back and forth.
I moved to a standing position at the side of the bed to massage his neck and shoulders. My hard cock was still encased in the black jock strap and Tony reached around to squeeze my naked ass cheeks pulling me closer to him. He rubbed his thick dark hair against my shaft and moaned his desire to have me released. I slipped my cock free from its constraint and rubbed my hard dick against his soft hair. My penile nerve endings were aroused and I was erect to the maximum.
Tony lifted up his head and licked my naked balls while my member pressed against his forehead. He used his tongue to wet the underside of my shaft and took the head into his mouth when he reached the top. His warmth was very stimulating and it wasn’t long before I pushed the whole of my cock deep into his mouth. He gagged a little from the fullness and the long absence of cock in his mouth. I gently tousled his hair while he bobbed up and down on my shaft with increasing pressure.
As much as I wanted to feel my dick penetrate him, I knew that he would be too tight for me to gain entry and I didn’t want our first return meeting to include any discomfort. I directed Tony to turn face up on the bed so that I could play with his sensitive nipples. He understood my intention and readily complied with my request. I hoped that his wife had at least been keeping that sensitive area used during these challenging Covid-19 times. I gently twisted both of his nipples while my hard dick rested on his face. His own shaft was pointing appealingly at the ceiling.
I climbed onto the bed to take one nipple into my mouth while one hand massaged his dick. He pulled my head firmly into his chest and moaned his approval of my actions. “I’ve missed your warm mouth on my nipples.” His words led me to continue stimulating his mind and body through attention to his chest. His shaft got firmer and I was concerned that he might even orgasm in this situation. I wanted to feel his perfect cock deep in my throat and became conflicted between my desires and his. I let go of his dick and focused on just his two nipples giving his cock a chance to calm down.
Ultimately, my own desire could no longer be resisted and I slid my head along his torso to where his shaft rested on his abdomen. In one slow lunge I took his cock into my mouth all the way to the back of my throat. He filled up all of the usable space and I felt my eyes expand along with my mouth. I pressed my lips against his dick while withdrawing back to the tip of his cock. He tasted so good to me and I plunged my head back to the base again wanting that feeling of his dick in my throat. His smooth cock head massaged deep into me and made me want more. I came back up for air, but was soon going up and down on his shaft until I knew that he was going to put his load into me.
Neither of us could resist at that point and I felt him hold my body tightly while his sweet sperm leapt into my mouth. He held his breath until he finished filling me with all that he had. His exhale forced its way out of his body and he gulped in fresh air hungrily. I swallowed all that he had provided and licked my lips with pleasure as I felt his body relaxing into the bed. I didn’t feel the need to orgasm but was content in knowing that I had given him some of the pleasures he had been missing.
I used a washcloth to wipe his torso and shaft before using the same cloth to wipe my face. We had become sexual sooner than usual and I had some massage components to complete. I oiled my hands and gently relaxed his torso and legs, giving extra attention to his feet. I stretched his neck and eased his mind using Reiki techniques. His facial muscles relaxed and smoothed the age wrinkles that were starting to deepen on his face. I even noted a few white hairs creeping into the dark hair on his head. He smiled in response to my touch and I saw his happiness increase the brightness of his expression. He went home a happy husband, perhaps even bringing flowers to his wife to share his happy day.