During my two weeks in Athens in December, I stayed in Kallithea where there weren’t any tourists but there were numerous preparations for the Christmas holidays including caroling in the nearby park. In the evening there were holiday lights with people ambling along on the commercial streets or gathered in the outdoor coffee shops. The weather was mild and people wore light jackets and smiles graced the faces of young and old alike.
I was most fortunate to have had encounters with two very sexy Greek men during that period and when it was just a few days before I would be departing, I knew that neither of those men would have the ability to visit with me again. Had it not been for that situation I might not have accepted another invitation from a Greek man in his fifties who wanted to meet me for a sexual experience.
Peter’s profile didn’t provide much information beyond age and body type which was hairy and a bit overweight. He was very urgent in his requests to meet me and service my cock. I was ready for such an event and accepted his suggestion to come that evening. It was an occasion of the small head winning out over the brain.
I provided him with the name and location of the plaza near my Airbnb condo where we could meet. We arranged for 7 PM and I arrived there early so that I could have some time to observe the local residents enjoying themselves in the park underneath the holiday lights. Small children were playing tag while parents sat on nearby benches having adult conversations. Peter arrived on time and walked briskly to where I was sitting on my bench. I had provided him with my face picture so that he could spot me easily which he did.
Peter had a portly build but also wore a very jovial smile with an attractive demeanor. We made our Greek greetings and I offered to show him my space. He readily accepted and we walked to the nearby building. I learned that he was a doctor who was just returning from a business trip and was not expected to be home until later that evening. Between the two of us we filled up the small elevator that took us to the top floor of the building where I was the only one there, providing great privacy.
I unlocked the frosted glass entry door and welcomed him to my space. He was not at all interested in looking at my apartment other than the bedroom and bathroom. Peter had commented in one of his emails that he liked to wear panties while playing with a man and I had informed him that it didn’t do anything for my arousal but if it pleased him then it would be fine with me. I had noted that Peter was carrying a small bag when he approached me in the plaza and I suspected that it had his desired items for sex.
Peter promptly removed shoes and clothes within a few minutes of entering my space. This was a speedier process of getting naked than was usual for me but seemed to be quite comfortable for him. From the bag, he took a new pair of black panty hose which were put on with skill, demonstrating that he had done this many times before. Peter didn’t have panties, but slipped into a pair of black stiletto high heels. He didn’t have small feet and I wondered how difficult it had been to buy them and keep them hidden from his wife. Did they belong to his wife? I should have asked but didn’t.
He was an incongruous site sitting on the edge of the bed in black pantyhose and black stilettos with a bulky hairy chest attached. He had a very manly five o’clock shadow and nothing was feminine about his manners or body. There were times I had been with men who became semi passable from behind when dressed in sexy women’s clothes. I only found that arousing when they were small framed with cute asses so that I could pretend I was with a woman. Peter was none of that.
Nevertheless, I had made a bargain and I would hold up my end of the deal. I didn’t remove my denim shorts but took off my sandals. I walked over to Peter and placed my crotch in his swarthy face followed by slowly lowering the zipper on my shorts. I wasn’t wearing any underwear and I pulled my soft penis out to expose it for him. I expected that he would initiate some oral action but when that didn’t happen, I decided to become more aggressive and be the alpha man that he needed.
I pulled his head into my cock and I rubbed the shaft on the waiting, grizzled face. The friction stimulated me and I became hard enough that I could rub my cock enticingly on his lips. “You want some cock to suck?” I asked aggressively. “Open your slutty mouth and take it then.” He did as commanded and I slid my half hard dick into the warm mouth. Peter began to apply some pressure which helped get my cock harder. I slowly thrust back and forth into his compliant mouth. I pulled his head hard against my body and kept it there while I thrust deeper into his throat. He gagged and I pulled back to let him have some air.
My cock was now hard enough that I didn’t have to hold his head so I reached down and roughly twisted his hairy nipples. I continued thrusting into his wet mouth while I pulled hard on the nipples. I filled his mouth with my firm dick and he tasted my precum. I pulled back so that he could lick his lips to savor the salty taste.
“I want to see your big ass,” I commanded as I dropped my shorts on the floor. He obediently got on all fours on the edge of the bed and I smacked both sides of the wide ass hard but not enough to leave an impression. I avoided looking at the site because I knew that it wasn’t going to be appealing to me. I rubbed my hard shaft on the black pantyhose which had a good effect on my cock. I roughly pulled the pantyhose down exposing his opening. “Don’t cum in me,” Peter cautioned. That hadn’t been my intention and I said, “Don’t worry. Just bend over.” I rubbed my dick on the opening while I continued to smack his now bare ass cheeks. I was fairly certain that I would lose my erection if I put on a condom and tried to fuck him.
“Turn over with your face up on the end of the bed,” I demanded. Peter obediently complied and I could see that his cock wasn’t very hard. I stood over his head and slid my cock into his mouth. “Stroke your fucking cock,” I directed and he began to get his dick aroused while mine was sliding in and out of his mouth. He was getting really excited and I was getting ready to be done. “Let me see you shoot your cum,” I commanded. I took my cock out of his mouth and nestled my balls there instead. “Lick my fucking balls and make them wet you bitch. You are MY bitch now!” I continued stroking my dick and felt confident that I would be able to orgasm in this position.
“Do you want my cum in your mouth or on your face?” Peter requested the load on his face, so I said, “Keep stroking your cock and shoot your cum now.” My own load which had three cum filled shots, landed on his grizzled face and lips. It’s a good thing he had his eyes closed. My orgasm led him to stroke harder and seconds later he put his shot on his hairy round belly. I stood up and Peter exhaled deeply as he relaxed into the mattress.
I had some tissues nearby for him to wipe his face and belly which he did. Peter didn’t lay on the bed for more than thirty seconds before asking to use the shower. I directed him to the contiguous location and provided him with a towel. I lay down on the bed and rested. I had zero interest in being in the shower with him. He returned from the bathroom, freshened and ready to return to his manly clothes. I had intentionally lay on the bed to encourage some resting time and an opportunity for my questions, but he had a different plan so I had to make my queries while we got dressed.
I learned that he had started cross dressing and playing with men about ten years ago. Peter mostly had opportunity when he traveled and was reluctant to connect with anyone local, so he always looked for travelers who could host. He was completely closeted and no one had a clue because he was so hairy and masculine in appearance and behavior.
I escorted him to the plaza where we had met and he displayed a much happier smile at departure than he had at arrival. As Peter blended into the holiday crowd, I took a seat on a nearby bench to return to the pleasure of watching the small Greek children at play under the multicolored glow of the Christmas lights. There was a part of me that was happy he had quickly departed.
Peter reconnected with me the very next day to see if I were available again that evening. He had really enjoyed his time with me and wanted to play again. I knew that I had filled my quota of crossdressing for the month and declared that I wasn’t available. I was leaving for Thailand the day after and needed to prepare for my travel. Unless Peter reads this story and recognizes himself, he will never know how much I used my acting skills that evening.