I worked in the city for a small financial services company right out of college. It was an hour and a half from my hometown, so I found an apartment and settled in. I had been with the company for three years and had a small staff of accountants and clerks working with me. One woman, Mary, was 15 years older than me and was quite welcoming. She would invite me for dinner at her home with her husband, Jim, and their kids. I was often stopping over for a drink or small chat after work as well.
Jim and I had a good relationship as well and once, after a few stiff drinks, he asked if I liked watching porn. Obviously, the answer was yes, so he suggested he get a few tapes at the local video store and come over to my apartment to watch them. I didn't think much of it, certainly he couldn't sit down and watch porn in his home so this would be a good escape for him. We had a few 'viewing' sessions over the next few months. These sessions did include plenty of alcohol.
I was planning on moving home after graduating evening classes for my MBA, so Jim suggested we have one last night before his fun was over. That night, Jim said he brought something a little different than the usual hetero films he had in the past. It started out hetero enough, but soon, the man's girlfriend was seducing him into playing with her male friend. I was shocked and surprised the first time I watched a man go down on his knees and take another man in his mouth. To this day, I wish I could remember the title so I could watch that scene again.
I wanted to pull my pants down and jerk off the minute I saw that scene. I kept stealing glances at Jim to see if he noticed how much I liked it and if he thought I was gay. But eventually, the movie and the night ended, and I bid Jim goodnight and went to take care of my business.
Although I had kept in touch with Mary and Jim, I had not seen them for about 4 years. I was 28 and had a girlfriend, when Jim called, and he said he'd be in town to see a customer and did I want to go to dinner. We met at a restaurant near his hotel and caught up with the times. When we finished, he invited me back to the room to watch some porn he had brought along on his trip. Again, I wasn't picking up on anything and I was happy for the opportunity to watch.
This was the late 80's so media and video equipment options were limited. Jim had brought his camcorder (on a tripod) and hooked it up to the TV. He was playing the video tape through the camera. I was half expecting more bi content but was surprised to see it was mostly women in panties giving blowjobs. As the movie played, he kept talking about what it would be like to be a woman and wear panties and be submissive to men.
After about 30 minutes of watching, maybe because it was his hotel room, Jim asked I minded that he got under his covers and jerk off. Not wanting to be a prude, I said I didn't mind, which I didn't, and actually wished I could do if I wasn't so shy. After he did his deed with himself, he fell sound asleep. I slipped out of the room and headed home.
It was only two weeks later when Jim called again and said he had another trip planned out in my direction. Like before, we made plans to meet, only this time I would be coming from the gym, so I said I'd be a little late. He suggested I bring a change of clothes and shower at his hotel before dinner.
When I got to his room, he was already set up with his camcorder playing a tape of more young women in panties on their knees. I sat on the sofa in the room and watched and again, he talked about what it must be like to be a woman. Maybe it was the drinks or something he put in them, but I was really putting myself in the movie.
Imagining the feel of panties on my small 4-inch cock. Being so vulnerable to those men with big dicks. I downed my drink and headed to the shower. I really hadn't paid that much attention to how much I drank, but I was feeling the effects. Coupled with the images in my head of panty clad women with their seductive poses licking and sucking, I was feeling quite horny. I was almost tempted to jerk off in the shower, but I didn't want to get caught. The bathroom door wasn't locked, and I had already heard Jim come in and leave the bathroom while I showered behind the curtain. After I nice hot shower, I pulled back the curtain to reached for a towel and dry off.
I was shocked! Jim must have come into the bathroom and taken every towel and my clothing out of the bathroom. The only thing on the counter was a pair of white lacey panties. I knocked on the bathroom door from inside and yelled out, "Very funny big guy, but I think I'll need my clothes back. And a towel would be nice too."
Jim answered, "I can give you a towel, then we can talk about clothing."
I opened the door enough for Jim to pass me my towel. Only it wasn't a towel, it was a dry washcloth. Enough to dry slightly, but not enough to cover much of my exposed body.
"Come on man, I can't dry with this!" I said.
"It's big enough, I've seen your hardon through your pants and you're lucky if you have 3 inches. You don't have that much to dry."
I hurriedly dried as best I could with the small washcloth and then made another request for my clothes.
"How about you give me the washcloth and I'll give you your clothes," was Jim's reply.
So, with no other option, I passed the small damp rag back out to Jim and waited for my clothing. Instead of clothing, Jim gave me another drink.
Jim said, "You know, I think you'd look really good in those panties. And I saw how hard you got watching those pretty girls. I think you would enjoy watching in panties for the rest of the night, feeling that silky panel pressing against your tiny clitty. Besides, I put your clothing and the towels in my car, so I don't have anything to send in except that drink. Why don't you have a few sips and think about it. Besides, I really think you would look hot in them, and it would really make me happy. It's just us, so who's going to know or care? I jerked off last time you were here, so you know I'm not."
As I sipped my drink, my cock retreated like a scared turtle.
Jim continued, "You really have no choice. You know you want to do it. You know I would love to see you looking like a sexy sissy. And you really know that I have your best interest at heart. We are not going to do anything you don't want to do, just sit here in your panties and watch a little porn. You'll be amazed at how hot you get sitting here like a sissy girl."
Ugh, this wasn't going to be easy. I had thought about dressing in panties in the past. I even tried on a pair of my girlfriend's when she wasn't around. Imagined what it would be like to have a pussy and being vulnerable to a strong man with just my tiny panties to protect my sex. They were hot panties; I imagined a woman's pussy pressing against the crotch. I picked them up and smelled them. No scent, so they were new. I felt the silk panel, rubbed it against my shriveled cock.
"Come on babe, do it to. Show me how pretty and sexy you are. Let me see your tight ass in them. How your tiny clit makes them bulge. I'll give you $100 if you do," Jim teased.
"Maybe for $1000," I said as a joke.
