Disclaimer: This is a work of fiction and any resemblance of the characters within to actual humans is purely accidental, as is the plot. This story contains homoerotic incidents. If such material is illegal in the jurisdiction in which you live, do not read. Those not wishing to read such things, should hit the back button forthwith or take any other evasive maneuver appropriate to the situation. There, you have been warned. Now enjoy the story.
Ned's Nylons.
One Friday afternoon at work I had gone out for a walk during lunch, and I happened to pass an adult bookstore that I had gone into on occasion. It was not very near the office so I didn't really worry that anyone from work would see me there. I eventually found myself in the transgendered section, which was my favorite. I was thumbing through a magazine gazing longingly at pictures of cross dressers, TV's, and transsexuals when I became aware of someone standing behind me looking over my shoulder. Somewhat startled, I turned to find my boss looking at the same pictures I was. "God, you scared the hell out of me, Ned," I said. Suddenly, I realized I had been caught by my boss looking at pornograhy--and shemale pornography at that. My heart jumped into my throat.
"Relax," Ned said. "I promise I won't tell anyone your little secret."
"Thanks," I said. "You know the truth is that I have never looked at anything like that before. I was just curious. That stuff actually strikes me as a little weird--you know, guys dressing up like women." As I said this, I put the magazine back and started walking toward the door. Ned followed me outside onto the sidewalk. "Well, I guess I should get back to the office," I said.
"What's your hurry, Bill? Lunchtime is only half over. Say, how's about a drink? Can I buy you a drink?" Ned asked.
Though I still felt a little awkward because of situation I had just been in, I didn't want to turn down my boss's offer of hospitality. That wouldn't be very smart on my part. "Sure, I'd like a drink," I said.
We went into a restaurant about two blocks away and ordered something to drink. I had white wine and Ned had a draft. We talked about office stuff for a while and then made small talk about other things. After a while, Ned got this amused look on his face and seemed to be watching me closely. Finally, he said, "You know, what I said back there about keeping your secret--I meant that. But I'm only going to keep your secret if you swear to keep the secret that I'm about to tell you." Again, he watched my face closely for my reaction.
"Okay," I said, "I can live with that." My mind was racing furiously trying to guess what the secret might be.
"The truth is," he said, "I crosiers myself on occasion. Usually when my wife goes out of town to visit her mother. So I don't get to do it very often."
"Wow," I replied, "That's quite a secret, but I promise I won't tell anyone. How long have you been dressing?"
"Oh, I guess about five years now," he said. "I really enjoy it, but I'm getting tired of dressing just for myself. I'd really rather have someone to share it with. That's why I got kind of excited when I saw you looking at those transgendered pictures in the bookstore. Would you possibly let me dress for you sometime?"
I thought about this for a moment and then said, "Sure, I think that would be interesting. I could tell my wife that I have to go to your house to catch up on some work stuff--that we're really behind at work. I think she would go for that."
"Gosh, that's great," Ned said. "Maybe we could get together this weekend. My wife's going to her mother's on Saturday morning to stay for the weekend."
"Okay," I said. "I'll come over to your place Saturday about noon."
When Saturday morning arrived, I was all revved up in anticipation of my meeting with my boss. I tried to imagine in my mind's eye how Ned would look in drag. Like me, he was about 5 feet 11 inches tall and fairly slender. He was clean shaven and had a fair, clear complexion, but I couldn't picture what he would look like as a woman. I guess I would soon find out.
I nervously pushed the front door bell at Ned's house and waited, half afraid that Ned's wife might answer the door. But, no. When the door swung open, there stood a beautiful tall brunette woman, who was stunning in appearance. After I stepped into the living room, I turned to look closely at the women, who I supposed was Ned. "My God," I said in disbelief, "you are absolutely gorgeous, Ned."
"Please, call me Nell," he said, ushering me toward the couch. "Nell" was wearing black shiny nylons with red heels and a matching red micro mini skirt and a taupe blouse, tight at the waist. Nell's wig was short, in a page boy cut, and her makeup was very well done--red lipstick and subtle blue eye shadow and eye liner. "Here, sit on the couch, Bill. Make yourself comfortable. Something to drink, maybe some wine."
"That would be great," I said, still staring at Nell in disbelief. I sat down on the couch as Nell disappeared into the kitchen. She soon returned with our wine. As she sat on the couch about three feet from me, she raised her glass in a salute, and we touched glasses. "Wow," I said, "I can't believe what I'm seeing. You look so feminine. How do you do that?"
"It takes a lot of practice" Nell said. "I'm so glad you approve. I've never dressed for anyone before, and I was--quite frankly--a bit nervous about your reaction. Now I'm fairly at ease because you seem to be okay with this."
"I am, yes," I said. "Wow, you look just great, Nell. I'm really glad you were bold enough to approach me about this. This is the first time I've ever been around a ... well, you know, a special girl."
"You're so sweet," Nell said. "Now sit back and let's get to know each other a little better." We sipped our wine and made small talk for about a half hour, during which Nell revealed to me some of her makeup and dressing secrets. As we finished our third glass of wine, Nell set down her glass on the coffee table and edged closer to me. When she was right next to me, Nell put her right arm on the back of the couch with her hand on the back of my neck. After a minute or so, she pulled me to her and kissed me on the lips.
I was absolutely floored. I had never been kissed by a man like this before, but I found it so hot I couldn't believe it. My body felt as though electricity had shot through it. As we continued to kiss, hotly, I put my arms around Nell to draw her closer. Soon, our tongues were entwined in wet kisses, which made me even hotter. I could feel my cock begin to swell in my pants. "Oh, Bill, you're making me so horny," Nell said. "This is so wonderful. I don't know why I waited so long to do this. Kiss me again, honey. Let me suck on your hot tongue."
After kissing some more, I looked down at Nell's legs, beautifully encased in her shiny black nylons. "God, your legs look so delicious in those nylons, Nell. Can I touch them."
"Please do, sweetie," she said. I put my hand on the inside of her right thigh and ran my fingers over the slick fabric. It felt super sexy. As I did this, Nell threw her head back on the couch and let out a pleasurable sigh. I pulled her to me and kissed her again on her hot mouth, all the while running my hand over her leg. After a few minutes more, Nell reached down and took my hand in hers and guided my hand under her miniskirt to her nylon panties. I caressed her panties with my fingers and I felt a hot bulge there. I felt the fabric more carefully with my fingers and squeezed what was obviously a huge cock throbbing beneath the nylon. God, it felt big. Nell put her head back again and moaned audibly as I caressed her clittie. We kissed again.
"You're so hot--and big," I said, continuing to rub her rigid penis.
"I hope you like it," Nell sighed. Still kissing her, I pulled the top of her panties down to free the large head of her cock. In seconds, I had the whole thing out and in my hand. I stroked her up and down slowly as she squirmed and moaned. "You're making me so hot, Bill. I don't know how much of this I can take. Your hand on my cock is so delicious," she said.
"But Nell," I said in her ear, "you haven't seen anything yet. I have other plans for your sweet clittie. With that, I slid off the couch onto my knees and moved between her nyloned thighs. When I looked between her legs I saw a big seven inch cock with a pick head. I ran both my hands over her nylons as I leaned forward and took the big mushroom head of her cock into my mouth. I was in heaven. I had dreamed of this for years. Her head in my mouth felt wonderful, as I ran my tongue around her cock. I licked her cock quickly to get as much saliva on it as I could. Then slowly I slid my mouth down her shaft about three inches and then back up again. Nell squirmed her butt on the couch.
"God, that feels so wonderful, Bill," she moaned. "You're sucking my cock so good. Please suck me, honey. I want it so bad. Oh, baby, suck me." I continued to move my hot mouth up and down her shaft. She put her hands on both sides of my head as if to guide me up and down her hot pole. By this time, her cock was all juicy from my spit and going up and down her shaft was easy. I gradually took took about five inches in my mouth, and then I thrust forward and took the thing down my throat, gagging slightly. It felt so wonderful having the head of her big cock in my throat. So very pleasurable. I pulled up and sucked just beneath the head and then back down on it so it went into my throat again. God, she tasted so delicious. "You are going to kill me with your mouth," Nell moaned. "Oh, God, suck it baby. I'm getting close."
Here I was with my boss's hot cock in mouth and I was loving every minute of it. I knew now I was a born cock sucker. Nell began to lift my head up and down on her throbbing penis in motion with my sucking, and she began to writhe around on the couch. "Oh, God, Bill, suck me hard, baby. I want to give it all to you. I want you to take me all the way, honey. Oh, God, I think I'm going to cum." She was moving my head up and down fast now, fucking my mouth with her big juicy cock. "Oh, shit, here it comes," she screamed. " Suck it all, baby. Suck out all my hot cum. Drink it all. Oh, God, oh, shit. I'm cumming, baby."
Suddenly Nell's body went rigid and her legs began to shake. She held my head still for a moment, and I could feel her head swell in mouth. Her cock grew bigger and began to throb in my mouth. Suddenly, the first blast of her hot cum hit the roof of my mouth and dropped down on my tongue. It was slick, salty, and delicious. Nell was still screaming loudly. "Suck me, Billy, suck me. Suck all my hot cum. Oh, it feels so good." Before I could swallow, another big splooch of thick cum shot into my mouth. Then another big gob and another. Nell seemed to come forever. As she did, I ran my tongue around her shaft and the head and swabbed her hot pole with the cum in my mouth. God, I loved the taste of her slippery cum in my mouth. She shot again, and now I had to swallow to clear my mouth out to get more of her hot juice. I could feel the thick slippery juice slide down my throat, and instantly I wanted more of that delicious taste. She squirted again, hitting the back of my throat, and I swallowed again. Her hands were still moving my mouth up and down her shaft. At times her head popped out of my lips, but she pulled me back down again quickly. She screamed again and shot another big load into my hot sucking mouth. Her cum was now dripping out of my lips, down her shaft. I was in heaven as I sucked her hot cum down my throat. As she squirted again, I felt my own cock begin to twitch, and suddenly I was shooting off in my pants. This made me suck Nell even harder and she squirted yet another big gob of hot, salty cum into my mouth. Nell screamed again and shot another thick load into my mouth.
Gradually Nell began to heave less and less as her orgasm passed. I continued to suck her shaft and milk it with my hand, trying to get all the hot jism I could into my mouth. I took the head of her cock out of my mouth and licked it clean with my tongue. Nell reached under my arms and pulled me up to her on the couch, kissing me deeply with her tongue. "Did you save any cum for me?" she asked.
"No," I said, "like a little pig, I drank it all."
"You're a bad boy," Nell said in mock seriousness. "However, I have the feeling that your next work evaluation is going to be very good, indeed."
"So," I said, "I guess I have shown you that I really am a team player, huh?"
"Honey," she said, "you can play on my team any day. But enough about that, now let's do something nice for you."
"We'll have to wait a while for that," I replied. "Sucking you off made me so hot, I shot off in my pants."
Needless to say, Nell took care of me later in fine style. Also needless to say, my boss and I spent many weekends together trying to get caught up on that never ending supply of work at the office.