The Following story depicts the purely fictional account of sex between two grown men, one however is dressed as a woman. You know the rest but I'll tell you anyway. This story should not be read or shared in way shape or form with anyone below the legal age of consent which in most states is 18 years old.
Cure For Lonliness
By CiaTV c112233tv@excite.com
It was about 6:30 and the Bulls had just started another of what was sure to be a depressing attempt at playing basketball. I was at my older brothers condo, just kicking back with him downing a couple of beers, and generally doing guy stuff. Denny and I had never really been that close before, but after this his third divorce, he seemed really serious about getting to know me better. At least that's what he had said but I think it really boiled down to the fact that he had always had someone to come home to for the last 13 years and now being alone in his 3 bedroom condo in the evenings wasn't quite cutting it.
Denny and Gina had always had their share of ups and downs, but this divorce really got messy, so messy in fact that from the first night 3 months ago when Gina stormed out of the house, she practically left her entire wardrobe in the closet. She said that Denny could do what he wanted with the clothes because she "would take him to the cleaners so many different ways that when it was all done, she would have 10 new wardrobes with change to spare.
So here we were tonight like the last 5 nights, sitting on the sofa watching some game, and basically just passing time. Denny looked over at me during one of the commercials and told me out of the blue. "You know it really sucks what she did to me man." I knida of half watching the commercial and half listening said, "what?" Listen Glen for just a minute will you, I was talking about Gina! "She really left me in a bad way, no warning or any kind of reason, just up and left. We weren't even sleeping together for almost 3 months prior, but I stayed faithful."
Now it's been another 3 months and I'm really in need, "in need of what?" I said. "You know I have got to get laid, and soon or I'm going to explode!" Well why don't you go out to a club and get yourself a lady? I can't I'd be comparing her to Gina. I can't even get rid of her clothes. You got it bad man. I guess I do, no matter. We better get something to eat. While Denny was reaching over to grab the phone book so that we could order something to eat, I noticed that he had really gotten a boner, I mean he must have been at least 8 inches under his sweat pants. I wonder what it looked like fully erect.
I caught myself staring, but was jolted back to reality by the loud beeping sound of Denny's pager. Oh great! What now? He said as he picked up the phone to call his supervisor, "I don't believe it!, Can't Steve or Mike handle it?" The look on his face let me know that the only one who could address this problem was Denny. Well here's another problem to add to my growing list, a risers out at the factory, and I'm going to have to look at it before one of the mains floods. Well as I glanced back over at his pants, I noticed that his problems weren't the only thing that was growing. I better get changed and get over there. No problemo Bro, I'll hang around, I said and basically went back to the game. When Denny left to go to work I couldn't really get into the game much because of what I was thinking about. Basically all that Denny had said, but 2 things really stood out, first he hadn't had any sex for 6 months, and second that he couldn't get rid of any of Gina's clothes.
I looked at the clock and seeing that Denny would be at least 2 hours getting back from his job site, I thought I would explore a little of his private domain. I quietly went into the bedroom and looked around. It didn't really look much different from the way it had when I helped to move him in 3 years ago, very fashionable furniture with the definitive touch of a woman having been present. Despite Gina's firery disposition at times she was still a very attractive and intelligent woman.
Looking into her side of the closet that fact was made more evident by what appeared to be a truckload of beautiful dresses, skirts, blouses, jeans and heels. She had an outfit for every occasion including those when she wanted to wrap my brother around her finger. Then I saw it a silky little black cocktail dress, that must have looked dynamite on Gina! She was a little larger than many women but it was always proportioned in the right areas. She must have easily filled out a d cup bra, but she had a tiny little waist, supported by full not fat, sumptuous hips. Gina's legs were lean and smooth, and I had caught myself eyeing them on more than one occasion.
By this time I had really had a field day going through her closets, I saw everything from the shortest and sheerest of skirts, to jeans so tight that the Surgeon General would have to put a warning on the side. Then I went over to her dresser and opened the top drawer, where I was treated to the most daring lingerie I had ever seen up to that point. I'm not sure why I did it, but subconsciously I held up a black full slip to myself and looked into the full length mirror imagining what Gina must have looked like in it.
Next I found a various assortment of stockings, panties and then the motherlode! Gina's shoe collection, again a shoe for every occasion including those sexier moments when she no doubt wanted to drive my brother crazy. I then had the craziest of thoughts, what if just for a joke I dressed up as Gina and fixed Denny a nice dinner when he came home. He was so used to getting a nice meal and having pretty company to come home to it would be nice just to see what his reaction would be. I figured that if he did like it there would be no problem in pulling it off with all of these clothes. If he didn't, I could always say that I did it just to mock her for leaving him - with no other intention.
No that would be stupid! What would he think of me if I did this? I was taking a big risk, but I figured he would probably be cool with it. It might not phase him a bit. Was I wrong about that. Very wrong.
I started by gathering the things that I would wear, while I was selecting a nice bra and panty set, I noticed that my cock was as hard as a rock. When I looked at it I started to wonder if was the thought of dressing up for my brother that was arousing me. I looked at the clock and realized that I had about an hour and 15 minutes left to pull this all together, so I had better worry about my own cock later. Just then I started to think again about Denny's and how like mine it had been really hard before he left. I wondered how long it would be when he returned.
After dismissing the thought I went to the shower and then carefull shaved my legs, arms and chest. Then after stepping out of the shower I sat down on the edge of the bed, and carefully rolled the black stockings that I had found earlier up my now smooth legs. With every touch of my fingers as I pulled the stockings up, my cock twitched up and erect. The sensitivity of my legs was incredible, and I was starting to feel very different, not bad not good just different. Next came the silky panties, and bra which since I was about Gina's size fit just fine, although trying to fasten the bra took some doing.
Next came the time for me to look at the preliminary results at the vanity table, very nice legs, accentuated by the black panties and stockings. If all I was looking at was my legs, I was hot, but I wanted to give Denny the full effect, so I sat down at the vanity, and looked for Gina's makeup. Voila! Rouge , Blush, Powder everything except.. ahh yes the final touch, lipstick.
I slowly took my time trying not to add to much, or too little. After my third attempt I finally accomplished a look that I felt good about, but that I felt Denny would like too. Why was I subconciosly working so hard to present myself as a woman that he would like? My time was ticking away so instead of trying to answer that I decided to keep working on my look. I stood up and walked over to the bed, where I had laid out, the black mini full slip, and of course the hot little black dress. I slowly let the slip fall over my arms and slide down my body, then I slowly smoothed it out uttering a little sigh because of how good it felt against my skin.
Next came some balloons which I filled with shaving cream, don't ask me why. But I couldn't stand the idea of water all over that dress. Besides I was pleasantly surprised to see how realistic the balloons felt if squeezed, and as they bounced. I quickly put them inside the cups of my bra, then came the little black dress. The final touch was the hair, there was no way that I could style my hair before Denny got back so with some more searching and being in the right place at the right time, I found a beautiful shoulder length auburn wig. After teasing it a little I found that the image presented before me in the mirror was no longer Glen, but rather Glenda. A very, sexy Glenda who could have almost any man she wanted at her feet. Feet!! I nearly forgot the most important thing shoes!
I tried on several pair before deciding on a pair of 2 and half inch sling backs, black of course! Wow what a transformation and I still had at least 15 minutes to try and make something to eat. Well after tottering a little I was able to shift the weight to the balls of my feet which I found made walking much easier. Out to the kitchen as I came out I froze in my tracks like a deer in headlights, there was Denny just closing the front door on his way back from work. Silence, nothing but long cold silence. This lasted for what seemed to be hours but in actuality was no more than a few seconds. Thankfully Denny broke it by stating that he was able to fix the riser and by making an adjustment save a lot of time. Then he looked at me and asked me my name, in my best falsetto I said: "Glenda". Denny then asked if there was anything to eat because he was starving, I replied that I could probably whip something up a few minutes. This seemed to satisfy him for the time, and since he is so much bigger than me, I figured I better not rile him at this point.
After I put a Lasagne into the oven to reheat, I noticed that Denny had gone to his bedroom and was showering. He asked if I could bring him a towel which I quickly brought in to him, of course by now he was shampooing his hair, so I had to hand the towel to him in the shower. Turning my head the opposite way I reached slowly into the shower to grab his hand instead he turned around and I accidentally grabbed his now fully erect cock. I'm so sorry I said as I dropped the towel and headed for the living room.
I now sat down on the sofa and nearly cried, what else could possibly happen? Well I soon got my answer when Denny now clad in a pair of dockers, and a polo shirt came out and sat down next to me. Then he asked :"What in the hell are you doing dressed like that?" I told him that I felt really bad that he had not come home to a pretty looking woman or a hot meal in so long and thought that I would surprise him. He seemed to take that in stride, but I was totally unprepared for what he said next.
You know I really miss Gina despite her attitude, and everything else. What I think I miss more than anything was the tenderness. She was so passionate in her kisses, and caresses. I looked at him as he was saying these things and before I knew what I was doing I had leaned over and kissed him very softly on the lips. I'm sorry Denny, I said resting my hand on his thigh, I don't know what came over me.
It's alright he said, I'm just glad I didn't tell you what a great blow job she could give. I quckly turned away blushing, but then when I had regained my composure I noticed a tell tale bulge in Denny's slacks. There was no hiding it, I started to feel very flattered that I was having this effect on my big strapping brother. So I decided to play with it a bit, Really? I said leaning back onto the sofa so that I could cross my legs nd check his reaction,yes just as I expected. His eyes were riveted to my thighs which this dress howed off very nicely. with y hand still resting on his thigh I began to slowly run my fingers back and forth across his leg, while asking him how Gina sucked him off.
He told me that sometimes she would just sit down next to him and start stroking his legs much like I was now doing and then slowly unzip his pants to massage his cock, until it got erect. that's some technique I said as I started to unzip his pants. Then what would she do I said? she would hold it and it would grow in her hands while she stroked it, like this I asked? Yesss, like that. Denny began to slur his speech and I knew what I needed to do. I couldn't let him know but I was getting to the point where I had to put something into my mouth and I decided that it would be him!
I looked at him and then leaned over for a kiss, this time a little more deliberate, and rested his hand on my thigh. Then I slowly leaned over and placed a soft little kiss on the tip of his cock which I had just freed from his dockers. It was growing and I had never seen anything like it, it had to be 7 inches and it wasn't even fully erect yet. I looked up at him one more time and watched as his head went back and my head went down. I very carefully licked the sides and the tip as this monster grew under my touch. then came the moment that I had waited for, I traced little rings on his balls with my tongue, and then slowly working my way up the shaft to the tip parted my lips, and took him inside.
Ohhh he started moaning and I did too, he was so warm and slick, I gripped his shaft with my fingers and worked them up and down his cock as I sucked more and more inside. The rhythm was perfect my mouth was sucking deeper and deeper, then he gently held my head and pulled me so far that I nearly choked, but then I remembered to breath andlet him fuck my mouth. He started calling me his little cock slut, I moaned yessssss baby!!!
Then I could hear his moaning start to get louder and longer, and I knew what must be coming soon. HIM! My new lover was going to fill my mouth with his sticky juice, and I was going to take it all like a good slut should. Oooohh yess Denny give it to me, give it to your slut, yes baby! Then like a cannon he EXPLODED IN MY MOUTH PUMPING LOAD AFTER LOAD OF THICK SWEET CUM DOWN MY THROAT!!!
He was moaning and sighing with pleasure, I had one hand on his cock while in my mouth, and one hand under my dress frigging my wet hard clitty. Oh baby yes yes I'll cum on you baby! OOOOOOHHHH , YESSSSSSSSS , I'M CUMMING Denny baby oh yes I'm cumming for you darling. Then I pumped my hand full of sweet cream and then broght some up to my mouth and let Denny watch me lick it. OOOOOOOHHHH, YESSS.
Glenda you sucked me much better than Gina ever did, I would very much like to continue our little chat in the bedroom care to join me?? I stood up proud that I had taken care of my man and said, after dinner darling let's eat then I'll give you dessert. I licked my lips still wet from cum and he nearly melted, I like this I thought to myself can't wait to give him something else later.
To be continued...
If you like this story, and would like to hear more about Glenda, send a discreet email to: c112233TV@excite.com, with your email address, and opinions. We'll see what happens next. I will respond to all emails!
CiaTV