During my last couple of years living in my house in New Jersey I became sexually involved with a bearish man in his late 30’s. He was round and furry with an average size cock and not the sort of man that I usually found attractive. He was a handsome total top and always arrived very well cleaned with a pleasant manly fragrance. Perhaps I was attracted by the effort that he put into his preparations and his desire to please me.
Over time, I decided to increase the way in which I pleased him. I knew from his online profile that he liked feminine men and crossdressers but I was neither of those. I decided that I might increase his pleasure if I put on some black lace panties that a girlfriend had left behind. I left my front door unlocked so that I could wait for Rob in my bedroom with my “pantied” ass directed to the bedroom door. When Rob noted my attire, I heard approving sounds and sensed his interest increase. When he removed his clothes, his cock was already pointing in my direction. We had a very passionate and intense session that included some powerful thrusts of his hard thick cock plunging in between my smooth ass cheeks.
For Rob’s next visit I added a dark blue silk shirt that was a very soft and shiny fabric. It was a short sleeve button down shirt. I did a couple of the top buttons and then gathered up the rest of the fabric so that I could make a knot to secure the shirt at my chest level making my bare midriff visible. In this outfit I met Rob at the top of the stairs where he could enjoy the sexy view as he climbed up to me. He always arrived in the evening and I kept the lighting subdued to improve the illusion.
I remember feeling a little bit sexier and more attractive in this outfit, but the experience didn’t lead me to be less masculine with any other partner. It was special for just Rob until I encountered Joe during one of my visits to Tucson. He wrote a note of interest after seeing my profile on a website where men connected with each other. I was surprised to get his note because Joe clearly indicated that he liked feminine men and crossdressers. My photos showed my facial hair as a very finely trimmed white moustache. It was no mistaking it on my tanned face.
Joe was a little older than me and was about twenty minutes from my hotel. He was tall with an average body and cock. I replied to his note and indicated that I was interested and available but would be checking out of my hotel by 11 AM the next morning. He declared that his wife would leave the house at 9:30 AM and he could shower and get to me by 10:15 AM. I was able to get a noon check out from the hotel, which allowed for a less rushed encounter.
The plan was in place but Joe had some more thoughts about me. He asked if I always had the moustache and I sensed that he was having buyer’s remorse. I informed him that I had had the facial hair since I was 18 and the couple of times in my life when I had shaved it off, I discovered that it changed my face completely. So, it was there to stay. Joe confided that he had only been with feminine men and crossdressers and all of them had been more than one night stands. He wanted to find out if he could be sexual with someone more masculine. I knew that the moustache was going to stay, but I offered to put on the black lacy panties that I had used with Rob. “That would be great!” That seemed to be enough to put his worries to rest and our plan was affirmed.
The next morning, I made sure that I shaved all of my playing area and trimmed my moustache very finely so that Joe would not be put off by my masculinity. I put on the panties and just a touch of cologne before I took a black sleeveless athletic shirt and created the same bare midriff effect that I had done for Rob. I didn’t have any breasts to fill out the shirt but at least I made an attempt to meet Joe’s needs.
At the appointed time, there was a soft knock on my door and I stood behind the door while I opened it so that my attire was not visible to Joe until the door was closed and I was in the subdued lighting of the room. As Joe took off his shoes, I took a position in the doorway to the bedroom with my ass facing him. Just as with Rob, I heard sounds of approval before I felt his manly hands squeezing my ass cheeks. He kissed me on the back of the neck and I arched my back to press my ass against his body.
Joe had removed most of his clothing but his underwear was still shielding his sexual parts. I reached behind and stroked him through his shorts until I felt some increase in size. Joe cupped his hands where breasts would have been on a woman and finding none there, he lifted up my shirt to reveal my nipples. He twisted both of them while his breathing felt hot on the back of my neck.
I moved to the bed which I had turned down. I took a seat and pulled Joe by his underwear closer to me. I released his shaft which had a good thickness with average length. I wanted to take my time and put just the head of his cock into my warm mouth. Joe approved of my actions and so did his dick. He held the back of my head with both of his hands while he pushed his way further into my warmth. He gently tousled my hair while I sucked his cock to a full erection. Any performance anxieties had been banished from the room.
Joe reached down with both of his hands and returned to twisting my nipples. I appreciated the stimulation and gave more vigor to taking his cock into my throat. I swung myself to the side and Joe slipped one hand under my panties to give my smooth ass cheek a good squeeze. “Let me lay down.” He removed his shorts and socks before taking a naked supine position on the bed. I kept both of my clothing items in place as I returned to giving his shaft my attention.
I put my ass near his torso where he could easily reach me with at least one hand. I was surprised when he slipped his hand into the front side of my panties and pulled my partially engorged cock out. He stroked me to a full erection quickly and moved his head into a position where he could take me into his eager mouth. I hadn’t anticipated that he would suck me so it was a most pleasant surprise. After a few minutes in this position he asked, “Can I fuck you?”
I had hoped that he would want to penetrate me and I had cleaned very well in anticipation. I had placed some lubricant by the side of the bed along with some poppers in case they might be needed. The lube was necessary but the poppers were not since Joe was an average size that didn’t require adjustment on my part. I removed my panties and applied the lube to my entry point as well as his firm shaft.
I moved myself into a doggy position on the edge of the bed and relaxed myself to limit any discomfort. Joe used a thick finger to prepare my hole for something bigger and I enjoyed the feeling of being fingered. Soon his cock head was pressing against my ass crack. He kept one hand firmly grasping my hip while the other guided his dick to the right spot. He pushed in gently and held himself in place to make sure that I was not in pain. I encouraged him to slide in and he was happy to hear those words. I appreciated the care that some married men took when performing anal penetration.
He did a few thrusts in that position and I sensed that he was not fully steady. Joe pulled his cock out entirely and directed me to be on my side with my eager ass pointing in his direction. He pushed my upper leg toward my chest fully exposing the recently used hole. Joe kept one foot on the floor and kneeled on the bed to position his cock back inside me. He took one quick thrust that got most of him inserted. He adjusted the positions of his legs so that he could get his balls snug up against my body while all of the shaft was inserted.
Joe kept one hand on my hip for balance and the other stroked my cock while his slid in and out. He kept up a good rhythm and I heard his breathing increase its intensity. I enjoyed feeling this masculine man taking my ass and cock into his control for his pleasure. His gentle but direct approach led me to feel that he was likely a good lover with women. He certainly spoke to my internal female side. Joe slowed himself and I sensed that his orgasm was coming too quickly for him. We had plenty of time and I was happy to let our sexual encounter continue.
“You feel so good,” I complimented him. “You’re getting me very excited,” came the reply. With that comment Joe returned to thrusting with vigor. I sensed that he had made a command decision that his orgasm couldn’t be held back anymore. “I’m going to cum inside you.” I felt his body tense and his cock harden before he pushed multiple spurts of cum inside my wanting body. Joe kept his hard cock firmly inserted until he exhaled softly as his body relaxed slightly. “You made me cum faster than usual,” he admitted.
I took the comment as a compliment and returned, “Well, I’m glad that you were able to be stimulated.” He remained in the same position until his cock softened so much that he couldn’t stay inside anymore. I rolled into being flat on the bed with my used ass facing him. I encouraged Joe to lay on top of me and relax but he declined so I reached for the washcloth that I had placed by the bed, to wipe his member clean. I went to the bathroom and applied warm water to the cloth so that I could more fully tidy the area that had been so well used. I used a small towel to dry him and returned to the bathroom to clean myself.
When I came from the bathroom, Joe was fully dressed and putting his shoes back on. I knew that he had a time constraint but I also sensed that he didn’t want to see much of my moustache. “Let me know when you will be back in town. I’d like to see you again if I can.” I told him that I most certainly would. Joe’s interest in departure left no opportunity to ask about his bisexuality and the complications of his married life. I also wondered about his experiences with the other men he had been with. I would have to meet with him again and ask questions beforehand. My suspicion was that he did this same quick departure with his other amours as many married men did. I opened the door and bright sunshine rushed in as Joe hurried out.