I love getting a massage. Over the past twenty five years, Iāve had more than I can count. Some good; some mediocre and a few that were just plain bad. And then there a a few that were memorable and became cherished memories. This is one of the cherished memories:
His name was Greg and he advertised in the gay newspaper in Orlando under the "therapeutic massage" section in the classified ads. This was back in the early 90ās, before there were so many online options. Platforms like RentMasseur, Masseurfinder, etc., did not exist then.
I called and he answered. I inquired about his massage services, and he detailed the length of sessions available, costs, his training, and his availability. I was in town for a meeting and explained that I would be busy most of the day but available in the evening. He offered both in-call and out-call services, and I opted to have him come to me at my hotel. We settled on 8:00 p.m. for the appointment. A few minutes before eight, there was a soft knock on the door.
When he first arrived, I had no idea where this night would take me. A massage was what I expected. It became much more than that.
I had taken a quick shower beforehand and was wearing a robe when I heard the knock. Opening the door, I was greeted by a man around 5'11", with beautiful blue eyes and short brown hair. He wore a tight white polo shirt and shorts, which accentuated his well-defined physique, especially noticeable with the tightness of the shirt showing off his pecs and the shorts containing a very visible package. A day's stubble lined his face. I would later find out that he was 33 years old. He entered with a massage table, we shook hands and proceeded to set up the table, covering it with fresh linens. When he asked if I wanted a drape, I told him it wasnāt necessary. "Good," he said, "a drape just gets in the way of a good massage."
He excused himself to wash up and instructed me to get on the table, face down. After a few minutes, he returned from the bathroom
To my surprise, he asked if I minded if he took off his shirt. "No," I replied, "make yourself as comfortable as you want.ā He removed his shirt, and even though I was on my stomach, I turned slightly to catch a glimpse. A perfectly sculpted chest covered with a light coating of hair led to a happy trail that disappeared into his shorts. He turned off one of the bedside lamps walked back to the table and placed his hands on my back. "Letās start with some deep breaths," he said, coaching me with the breaths, and breathing along with me.
As we continued, the atmosphere in the room grew increasingly intimate. Greg's hands moved with precision, exploring every inch of my back with deep, soothing strokes. The firm pressure of his fingers working out the tension in my muscles. I could feel myself relaxing further into the table.
Greg's touch soon evolved beyond a traditional massage when he shifted his focus to my ass, his hands massaging the firm cheeks. After spending time on my glutes, His fingers worked their way downward toward my hole. Before going further he stopped and asked me if I wanted him to massage my ass and perineum. He also said he could do a prostate massage if I would like.
I appreciated his asking and not just assuming it was ok. I told him that I would definitely enjoy it. He then began to massage my ass, moving his fingers in circular motions around my asshole. The sensation was wonderful. He then moved on to perineum and reached under me to feel my cock, which was fully hard, He began to apply a generous amount of lube to his fingers and my hole. Once the area was thoroughly lubricated, he started to insert a finger, slowly and deliberately. The sensation was intense, and I couldn't stop the moaning. Encouraged by my response, he added a second finger, scissoring them to prepare me further. Each movement brought immense pleasure
Greg continued to massage my prostate. His touch made me feel intensely aroused and relaxed at the same time. He paused momentarily, looking into my eyes with a mischievous grin. "You like that, don't you?" he whispered, and I nodded, unable to form coherent words.
Greg then gently removed his fingers from my ass. He gave me a moment to adjust, ensuring I was comfortable before continuing.
Greg then suggested we move to the bed. "Let's make ourselves more comfortable,ā The prospect of what was to come filled me with a mixture of nervousness and excitement.
As we moved to the bed, Greg removed his shorts. He slowly undid the waistband and let the fabric slide down his legs. As the shorts fell to the floor, his impressive erection sprang free. His cock was about seven inches long, similar in length to mine, but noticeably thicker. The girth was imposing, the shaft well-defined with prominent veins running along its length. His large firm balls and were lightly dusted with hair.
I couldn't help but admire his body, the muscles defined by the dim light of the room, and his impressive cock was the centerpiece of his athletic frame.
"Do you want to taste me?" he asked, his voice low and seductive. With no hesitation I leaned forward, taking him into my mouth. The sensation was intense, and I reveled in the sounds of pleasure he made as I explored him with my tongue. His hands moved to my head, guiding me as he began to thrust gently into my mouth. I could feel his cock growing. I was determined to bring him as much pleasure as he was givingAme.
After a while, Greg pulled back, his breathing ragged. "You're incredible," he murmured, his eyes dark with desire. Greg told me he didn't want to cum yetāhe had other things in mind. āLetās take our time; thereās so much more we can do tonight," he said. Such as, I asked. His answer was in the form of a question when he asked me if I wanted him to fuck me.
Absolutely. As a bottom there was no way I would turn down the offer to have this beautiful man fuck me.
Greg then rolled a condom down his cock and applied lube to his cock and my ass, preparing me to be fucked. He took his time, applying a generous amount of lube both to his condom-covered shaft and to my ass. As he finished lubing up, Greg moved closer. He instructed me to lie on my back, and I complied. He then lifted my legs, placing them gently over his shoulders. This position allowed me to spread my legs wide open, exposing my ass to him while maintaining eye contact.
"You ready?" he asked, his voice low and intense. There was a mix of concern and desire his question and I was touched that he was concerned that I was comfortable with what was about to happen. I nodded.
With a gentle but firm grip, Greg positioned himself at my entrance. He paused for a moment, looking into my eyes to ensure I was still okay with proceeding. Seeing my nod, he slowly began to push forward. The sensation was intense as he breached the opening, his size stretching me in a way that was both exhilarating and a little daunting.
I took a deep breath, trying to relax and allow his intrusion. Greg moved slowly, giving me time to adjust. His hand found mine, squeezing gently as he continued to enter me. As he pushed further inside, the initial discomfort gave way to a growing sense of pleasure. The fullness was incredible, and I could feel every inch of him as he filled me.
Once he was fully inside, Greg paused again, allowing me to acclimate to the sensation. He then began to move, his thrusts slow and measured at first. Each push sent waves of pleasure through my body, and I couldn't help but moan softly. Greg's movements grew more confident, his pace increasing as he sensed my enjoyment. From this angle, Greg could watch my face closely. After he was fully inside me and I could feel his balls up against my asshole, he leaned down to kiss me. Our tongues danced together in sync with the rhythm of his movements. His eyes remained locked on mine.
Every thrust brought me closer to the edge. Greg's rhythm was perfect, hitting just the right spot each time. The friction and pressure were overwhelming, and I could feel myself nearing my climax. Greg took my hands and placed them on my cock and said āI want to see you cum; jerk off for meā
As I approached my peak, Greg's thrusts became more urgent. He leaned down and whispered in my ear, "You're so tight; I want you to cumā Those words pushed me over the edge, and I climaxed with a loud moan. Cum shot out in thick streams, splattering across my chest and stomach. The sensation was overwhelming.
Greg continued to thrust. I knew he was getting close to cumming. He leaned in and kissed me passionately. As he reached the point of no return, he groaned deeply, his thrusts becoming erratic. He told me he was going to cum. With a few hard thrusts, he released inside the condom, his body trembling with the force of his orgasm.
After the intense climax, Greg slowly withdrew from me, his movements deliberate and careful. His breathing was still heavy, and he lay beside me for a moment, gathering his strength. He then carefully removed the filled condom.
After resting for a while, we decided to take a shower together. We stood facing each other under the spray. Greg knelt down and took my cock into his mouth. The sensation was overwhelmingāsending waves of pleasure through my body. I moaned as he used his tongue to trace the contours of my shaft. When I told him I was going to cum, he smiled and took my cock further into his mouth.
After I came, I returned the favor, kneeling down and taking his cock into my mouth. After a few minutes of sucking his cock and pulling on his large balls, Greg told me he was a going to cum. I moved up the shaft and sucked on the tip as I felt his cum shoot into my mouth. I swallowed his cum, savoring every drop.
After the shower, we dried off and dressed, still feeling the afterglow of the intense encounter. We sat on the bed and talked for a while, getting to know each other better. Greg reached out and held my hand as we talked. The conversation was easy and natural. As the night drew to a close, I offered Greg payment for the massage, but he refused.
"This wasnāt a massage," he said with a smile. "This is something unexpected that happened because we both wanted it. This was a magical evening, and I'm honored to have shared it with you."
His words touched me deeply. I was sad that this would be a one time experience and that this may be the last time I would see him. I was only in Orlando for two more nights. Greg asked me what I was doing the next evening and I told him that I had a work dinner. I told him that I could get out of it if he was interested in meeting me for drinks and dinner. He agreed and we settled on a time and place to meet not far from the hotel.
The next night we Greg picked me up at the hotel and we went to a nearby restaurant for an early dinner. As the dinner drew to a close, he reached under the table and placed his hand in my crotch. I smiled and no words were necessary. The bill was paid and we made our way back to the hotel for another memorable experience.