Thanks for the feedback so far guys. This newest chapter explores some of the kink that I would learn that Tom was into to. I hope you're enjoying the story and would also encourage you to support Nifty as you are able.
After the morning rendezvous, we both transitioned into our roles as conference guests and attended a few seminars, walked through a trade show, and went to the awards luncheon, which was the reason the board members and the executive director were in attendance. The non-profit we were representing received some type of significant award. For most of that day, while I was with or near Tom, others were around us, so nothing really seemed unusual, other than I had somewhat of a sore throat that was caused by Tom's assertiveness as my head was laying off of the bed that morning.
When the lunch ceremony was over, some of the board members said they were going back to their rooms. Tom told me he had another seminar he needed to attend, but I was welcome to return to the room to relax. I went back to the room. In those days, there was nothing really to do in a hotel room except watch TV and read the travel books and magazines that always seemed to be in hotel rooms. So that's exactly what I did. I had been in the room for well over an hour and just thinking about all that happened with Tom, and I was extremely horny. Of course, when a guy is in his early 20's, he's always horny, but since I had no idea when Tom would return, I didn't feel like I could just whip it out and jerk off. Another hour or so passed, and no contact from Tom, nothing worth watching on TV, and having already looked at the travel magazines, I decided to take care of things in the bathroom. Of course, with what had transpired in the last 24 hours, I didn't really need to fantasize, I just thought about how Tom, this married man who hours ago I thought was totally straight, had given me two opportunities to have great man sex. Just thinking about what had occurred caused me to shoot my second load of the day in a very short time.
After finishing the deed, I went back into the room and just laid down on the bed and watched TV. It was probably another hour or so until Tom came back to the room. Since I had no idea that I'd be waiting so long, I spent a good portion of the time thinking about what might happen when he came back to the room. I assumed it would involve cock sucking, but when he did return to the room, he shared some different plans.
First, for the somewhat expected conversation, Tom apologized for being gone so long. He mentioned that he had met up with several friends, I assumed other board members, and they had a few drinks at the bar. He also shared that our group would be going to dinner as a group and that we would leave the hotel by taxi in about 45 minutes. He went on to share that he needed to call his wife. Keep in mind there were no cell phones, so he would make the call from the room.
What came next was the unexpected, especially given my limited exposure to gay sex and just general naiveness about life, sexual exploration, and kinks. Tom said "while I'm on the phone, go change for dinner and put on that cum stained underwear you used as a cum rag". I'm sure the look on my face was priceless. I started to say something like "they're dirty" and he just repeated "I want you wearing those, so put them on". I was totally confused. Why would anyone want anyone wearing dirty underwear? It went against everything I had been taught! But he made it clear, and for whatever reason I just did as I was told. Then he added the last bit of instructions, "change out here in the room so I can watch". After sharing those directions, he picked up the phone and called his wife.
The phone call seemed relatively normal. The usual expected questions: How was work? How's the weather? Tom kept looking over to me as if to say "change into the underwear", so I did. Needing to get fully naked in front of him while he's on the phone, I felt like I had to be super quiet. Of course, by the time I pulled off my current clean underwear, I was rock hard. I looked over at Tom and he smiled and wink and sort of pulled on his cock through his slacks as I pulled on the cum rag underwear. I continued to get dressed in slacks and a shirt. However, while I was doing that, I was caught off guard by Tom's conversation with his wife. Keep in mind that I'm hearing only one side of the conversation and thinking that given what had occurred in our room, I assumed his wife didn't even know I was there. I was surprised to hear him answer questions about me being with him. She must have asked how I was doing or enjoying the conference because he said "David seems to be enjoying himself and he's getting to know some of the other board members much better". He also made it clear to me that she knew I was staying in the room, because he said something like "you know I can't talk sexy to you with him here in the room" and laughed. As I look back now, that was one of the more bizarre things that occurred over the next couple of years.
Once he got off the phone, he thanked me for putting on the used underwear and told me he found it incredibly sexy. He also said he wished we had time for me to suck him off, but that we could save that for later. After that he got up, changed clothes in the restroom and said we should probably go downstairs and wait for the others, as if everything that had just happened was normal activity. I was thinking what the hell just happened, and why am I wearing dirty underwear?
Since I know you're not here for restaurant details, I'll skip over the next few hours quickly by just saying we went to a very nice Latin restaurant. I remember one of the female board members who was an attorney volunteered to pick up the bill, which I'm sure was huge. One of the things I don't recall is did I have anything alcoholic to drink. This happened in 1984 or 1985, and I just read that the drinking age in Florida didn't become 21 until 1986, so it would have been legal for me to do so.
By about 8:30ish, our meal was complete, and we were back in a cab. Tom and I rode back with another board member, so nothing unusual occurred, except for my mind going back to "why am I wearing dirty underwear?" After about a 12-15 minute cab ride, we were back at hotel for whatever was about to come.
Once we got back to the room, I was about to learn about underwear fetish play, which I quickly realized was one of Tom's kinks. We had not been in the room 30 seconds before Tom brought up that he had been horny all night and couldn't wait to see me in my "cum-stained underwear". He immediately started issuing commands, and like a new puppy at an obedience class, I just complied. "Strip down to your underwear". My shirt, t-shirt, and pants come off. I sat on the edge of the bed and started to remove my socks, but I'm given my next order. "Leave those on". He told me that I looked very hot and that I should lay back on the bed, which I did. He begins to walk around the bed providing me with compliments on how sexy I look. The he tells me to "spread my legs wide." The instructions just keep coming. "Lift one knee up"", the other one, "Spread your legs some while in the air". I basically felt like I was doing some type of perverted modeling, which at this point was doing nothing for me. But I could tell Tom was getting off on it.
At the point, Tom begins removing his clothes. He took off his shoes and started taken off his pants. As he did this, more instructions. "Role over to your left side". "Right Side". "On your back again". "Lift your ass off of the bed". You could tell he was truly getting off on it. I also noticed that he was getting a wet spot in the front of his grey boxer briefs. That's one of the advantages/disadvantages of wearing grey. They easily show the wet spot. I continued to move around on the bed like I was in some crazy type of aerobics class when Tom made a move that I wasn't expecting. Without any discussion or warning, Tom quickly steps out of his grey boxer briefs and just shoves them in my face. Initially, I was revolted by what he had just done and sort of yanked my head away. He just moved his hand to cover my face with his underwear once again. My head yanks away again. The thoughts going through my head at that moment were sort of like being on the playground as a kid with some other kid trying to fart on you or something. You both know it's unacceptable behavior so you try to get away because you know every kid on the playground will laugh at you if you get farted on. The ironic thing, especially as I think about it now, despite my disgust and resistance, I never asked for Tom to stop or move his underwear off my face. One thing I can say for Tom is that he knew how to read me so well. For the brief moments where I kept moving my face away from him as I laid on the bed, he knew exactly what to do and say. "David, just calm down. What I'm sharing with you tonight is something that you'll come to enjoy as a gay man". There was a pause and he said something along the lines of "remember how you enjoyed smelling my cock and balls last night, you're going to enjoy this as well". In my mind, I wanted to laugh because I was thinking that he was a freak and there's no way in hell I'll enjoy sniffing another guy's underwear. One thing did make me question myself. Looking over at him, there was a fairly thick strand of pre-cum hanging from Tom's piss slit that had to be at least 3" long. He was clearly getting off on this scene.
As I shared before, Tom had a calming and caring way with me. So even though I thought this was beyond weird, I just decided to go with the flow since he was clearly enjoying himself. While I never said anything, he just read my body enough to know it was okay to proceed. With his cock fully hard and leaking, he began his lesson. "Take of deep breath David". "Can you smell my hot masculine scent?" I responded yes, even though I wasn't smelling anything but the cloth. "Do you like it, David". I think I replied it's okay.
Tom then asked me to turn over on my stomach. I had no reason not to trust him, so I did. He started the same line of commands as when I was laying on my back. "Spread your leg." "Lift your ass up." He was reminding me how hot I was and would occasionally hold his underwear up to my face. "Don't they smell good David?" This went on for a good ten minutes. Finally, he told me to get up on my knees and move towards the foot of the bed. As I was doing that, Tom took off his shirt and undershirt. He was standing at the foot of the bed completely naked and holding his underwear in his hands.
Shortly after moving to this position was when things started getting nice for me. Tom was still fascinated with his manscent and his underwear, but he started playing with me. He was rubbing my cock and balls through my underwear. He moved his hands to my back, my inner thighs, my butt. It all felt very good, and he continued to compliment me on my appearance, my cock sucking skills from last night and earlier in the morning. I was incredibly hard now and thoroughly enjoying his touch. Tom then started asking questions about me. Just as if it were yesterday, I can remember his first question. He had moved his hand to my butt and his middle finger was sort of massaging my hole. "David, have you ever been fucked". Immediately, I said No. That was somewhat of a lie. The guy at school I considered my boyfriend had tried to fuck me at least 10 times. Even though he had fucked other guys, he apparently didn't know how to prep or relax me. We would start the penetration process and it would quickly turn painful for me and I'd pull off of him in pain. Sometimes we'd immediately try again, but still to that point, he had never truly fully penetrated me, so even though I was lying more to protect my masculinity, I'd never really taken a dick deep. Once I said no to Tom, he continued to lightly rub my hole through my underwear and he kindly but confidently said "Someday, I'm going to fuck you". Our conversation went on for a while longer. We discussed what I enjoyed sexually and talked about the boyfriend/fuck bud that I had on campus. His questions came from a place of caring and they were really getting me even more excited, so I was feeling pure pleasure at this point. The hot conversation and his strong hands feeling my body was getting me more worked up. Of course, Tom needed what he needed so he'd rub his underwear on my face and do some dirty talk to keep the excitement level high for us both.
This had gone on for at least 30 minutes at this point. Probably closer to 45 when Tom finally asked me to take off my underwear. He also asked me to turn around towards him. When I did, I handed him my underwear and he basically directed my head to his still leaking cock. He brought my now moist cum stained underwear to his face and basically started making love to them. He was sniffing, licking, sucking and huffing on them as he fucked my mouth with his rock-hard cock. Just seeing and hearing how he reacted to my underwear confirmed to me that while Tom looked like this clean-cut conservative businessman, he certainly had a freaky side as well! Based on the way he was acting and the noises he was making, I assumed that's how the night would end since he was so worked up, but he had other ideas. He took a few steps away from bed which took his cock out of my reach. He sort of tossed my underwear that he was just getting off on back to me. "Put them back on David". Even though I had been enjoying playing with my cock as I sucked on Tom, I put them back on without hesitation. Tom asked me to get back up on my knees and move towards the end of the bed. Once back in that position, Tom started playing with my underwear covered cock, balls, and ass a little more aggressively. He also became more verbal and reminded me that one day he would fuck my ass and that he enjoyed me sniffing his underwear and sucking his cock. He proceeded to shove his boxer briefs into my mouth telling me to suck the precum out of them. All the while, he was stroking my cock and telling me to shoot my load in my underwear. I was so focused on myself at that moment, I hadn't realized that since he put the underwear in my mouth, he was also stroking himself with his other hand. Just based on the grunts, groans, and moans, it was clear we were both about to cum. A few more strokes from Tom's hand and I was filling the front of my underwear with a hot steamy load of cum. As I was shooting, I removed his underwear from my mouth as there was still somewhat a feeling of weirdness associated with what had happened. As I continued coming down from my ejaculation high, Tom basically yells "lower your ass" and pushed down on me. I had no idea what was about to happen until I felt him shooting his load all over the back side of my underwear. After he finished shooting, I felt him rubbing the load throughout the fabric that covered my butt. I reached between my legs and did the same with the cum that I had filled the front pouch with.
After all of that, my underwear was basically soaked in cum and I was ready to take them off. I was sincerely hoping he wouldn't want me to wear them to bed, but given his craziness towards this fetish, I had no idea what would happen. As I was thinking I should ask him if I could take them off, and hoping he would say yes, he answered the question for me. He was very specific with his instructions, "David, take your underwear off and hang them in the closet using a pants hanger with the clips. They need to dry overnight. You'll be wearing them on the plane ride home tomorrow".
To be continued.....
Would definitely appreciate any comments. Please e-mail me at David_McFerrin@yahoo.com