Let's Play Dress Up

One afternoon, James, whom I had met on a job he was also contracting on, stopped by. He and I were hanging out in my garage and I started poking around some of the boxes. I came across the boxes in which my wife's stuff from when she was a teenager had been stored, and much to my delight, came out with a bra. It wasn't fancy, or lace, just a plain white bra, but it was a kick to know that she'd worn it. I dangled it in front of James, "Look what I found," I said, and held it up against my chest, my shirt on.

He laughed and said to give it to him. I tossed it across to him; he looked at it and said, “Hmmm, 34B, she had nice boobs back then, still does from what I can see.” Then he did the same, holding the bra cups against his shirt and throwing his chest out in an exaggerated way. It was funny, and we didn't think too much about it. He asked me where I'd found it, and I showed him. We dug through it, coming up with armfuls of her old clothes, stuff she probably couldn't or didn't wear anymore, but which she hadn't had time to give or throw away. By then it was getting late, and he headed home.

The next day, he came over again, and the routine was pretty much the same. We were hanging out in the garage drinking a couple of beers and smoking some really stinky weed. We ended up poking around in the box of my wife's clothes. I pulled out the same bra again, and looked at it more closely. It was about my size, and I mentioned it to James. "Put it on," he said. "No way," I said. "What're you, chicken?" he said. "It's not a big deal."

"If it's not a big deal, then you do it," I said. He shrugged and got up, going to the box. He dug around until he came up with another bra, a little nicer than the one I was holding, pink lace and pink satin. He held it up and then slipped his arms through the straps, holding it against his chest, over his shirt. He tried to reach around back to close it, but couldn't, so he stood there with the back trailing off. "See? No big deal." I noticed that his shorts were sporting a tent as his cock got hard.

I did the same, but it was looser because I was a little smaller; I also had my shirt on. "Go ahead," James said, and I took off my shirt, putting the bra on over my own skin. He did the same. We couldn't figure out how to get it on and close it, so first he closed the one I was wearing, loosening in a bit to fit around my shoulders and back, and then I closed his and helped him adjust the straps. It felt... funny. Tight, but I found I liked the tightness of it. It smelled of my wife's perfume from when we were dating.

That is as far as it got that day. We joked around a lot, looked at each other and in the mirror, and after a while, he went home. The next day, when he came over, it was as if a decision had already been made, even though it had never been discussed. "Let's do it," James said. He rummaged through the boxes and pulled out the same bra, now with a slip, plaid skirt, and blouse. "I don't know if this is a good idea," I said.

"It's okay," he said, "I took a pair of her bra and panties home with me last night,” he followed, “It's fun wearing Misty's panties, bra; I got so excited I even jerked off with them on." That got me excited knowing he was jerking off while wearing my wife's clothing, and from when she was a teen! My cock got hard immediately.

In a minute, he had pulled off his shirt and yanked off his shorts and was pulling the clothes on, though he kept on his own underwear. There was something sexy about it, watching him put them on. I hesitated for a moment, then decided what the hell, and shucked my own Levis and shirt, though also keeping my boxers on. My cock tented my underwear so I turned slightly away at first.

While he got into the clothes, I rummaged around in the box until I came up with a plain bra, a pleated, checked skirt, a bright green blouse, and a slip. It all went on fairly quickly, and we turned to look at each other. It was almost funny; neither knew much about dressing, neither of us had made any real attempt at femininity, we were just wearing my wife's clothes, as prosaic and straightforward as that.

We both admitted that it felt funny, but it also felt good, in a strange kind of way. We really didn't know what else to do now that we'd gotten this far, and lapsed back into our usual routine of hanging out, but this time in Misty's clothes, and occasionally trying on something else from one of the boxes. When we got down to the layer with the lingerie and panties, we both hesitated. James picked up a pair of light green panties. "You first," I said.

"Okay," he said, yanking off his boxers. His cock was hard, a good 8 inches, with a pinkish-purple head, white shaft, and brown pubes; I watched him, closely, as he stepped into the panties. I did the same, neither of us turning away. I was hard by now, and he was the same, and we felt funny about letting each other see that. Both of us are well endowed; he was a bit longer than me with a nice 8-inch straight cock. I have brown skin, so different from his white skin. I could see his balls hanging below and his crotch was covered in brown pubic hairs.

I pulled on a pair of plain white panties, which matched the bra and slip. They felt snug and soft, and held my cock tight. Looking in the mirror I could see my brown-skinned cock pushing out against the white material, my balls were hanging out from each leg hole, and my brown pubes strayed above and out the leg holes.

I could see James pushing down at his crotch to try and keep his erection down, without much success. "You think this is what girls feel like?" he asked. "I guess," I said. His cock pushed out the panties and the head peeked out at the waistband, I could see his pubes spreading over his crotch and around the leg holes, and saw his large balls hanging out through one leg hole.

Sitting back on the couch we checked each other out, looking at the other's hard cock pushing out against the panties. "Feels good," he said, again pushing down at his erection, but the more he tried to make it go away, the harder it got. He pushed is over so it was at an angle pointing towards his hip. The head and shaft were exposed with just a strip of cloth running across the head and down the shaft.

I was in much the same situation. I tucked my cock down slipping it through the leg hole and between my legs to hide my cock, now it looked like a pussy behind the panties. James looked at me and moaned, “That is so hot, just like a pussy.” I ran my fingers under my panties like I was playing with my “pussy”. After a minute, the temptation got to be too much; he was touching his cock, rubbing it through the panties. He looked at my panties and then reached over and slipped his hand into my panties. I felt his fingers slide through my pubes and rub against the base of my shaft still tucked down between my thighs. He was jacking his cock as he touched me; sliding a hand under his panties he grasped his cock and pumped. “Oh fuck, it is like I am playing with Misty's pussy,” he moaned.

We didn't talk, didn't say anything at all during this. He pulled down his panties so they were snug under his balls, his hard cock stood erect, the purplish-pink head leaking juice. I left mine on as he played with my pussy. I watched him jacking off as he played with me, his hand sliding through my pubes and down along the base of my hard cock. He was creating a lot of precum that lubricated his cock. After just a couple of minutes, he gasped, and came. “Oh Misty,” he moaned out my wife's name as he shot his load. I watched him pumping his cock as he shot his load onto his stomach, it was so hot to watch another guy cumming. Without touching my cock I did the same, letting my cock slip free from my thighs it bounced up and I was cumming all over the panties.

We were both embarrassed and excited. The first thing we did was yank off the panties and dump them into the washing machine; I'd take care of them later. Walking around nude with him was exciting and we didn't get back into our regular clothes, though; instead we dug out fresh pairs of panties from the boxes.

We talked about it for a minute, how good it felt, catching occasional glimpses of each other in the mirror. Finally, I said, "Wait," and opened another box. I pulled out some magazines I'd bought years ago and stashed for my jack off sessions. I also pulled out a wig that Misty had worn; it had long brown hair that she'd worn with a costume. I put it on and we started to flip through the pages, me still dressed in my wife's clothes, looking at the women and men fucking. It was a strange situation to be dressed in a girl's clothes and looking at the pictures from that perspective. As if it was us.

James was fascinated by one picture of a couple fucking doggy style. The picture wasn't very good, but we looked at what they were doing it. "Get down," he said. "What?" I said. "Look, you're dressed like a girl, you have the long hair, let's see. It's just pretend."

I hesitated, then finally agreed. By this time I was so excited that my resistance was down. I got down on all fours on a rug on the garage floor, my skirt hanging down around my knees. Holding the magazine, he got behind me, between my legs, wearing his own skirt. He kept shifting forward until his crotch pumped up against my butt. Even through two pairs of skirts, slips and panties, I could feel his hardness. I shifted forward a little. "Keep still," he said, and moved forward again, pushing against me. He pumped back and forth a few times, looking at the magazine, both of us still completely clothed.

"I can't feel anything," he said, disappointed. Then he reached down and lifted my skirt up over my hips, the slip coming with it, and leaned in again, grinding against me. With my skirt and slip out of the way, I could feel the shape of him more pronounced through his skirt and my panties. He put down the magazine and started pumping against me rhythmically.

As if that weren't enough, between bumps he unbuttoned and dropped his skirt so it fell around his knees. Now we were just separated by the two pairs of panties. Checking in the mirror I could see his cock was sticking up hard at an angle, pushing out the panties, the head poking out a good two inches from the waistband, he was pumping into my butt through our panties. He must have pumped it wrong, because he shifted and now his panty-covered cock slipped between the crack of my ass, stroking me through my own panties, and poking me along the crack.

By now we were both breathing hard. I could feel he had pushed his panties down off his cock, but didn't say anything. I looked in the mirror again to see his exposed cock rubbing along my ass through the panties. His bare cock was free and sliding along the crack of my butt through my panties, sometimes dipping below and slipping between my legs.  When it did, I brought my legs together to give him something to shove into. The contact between my bare legs and his bare cock seemed to excite him even further; I know it did me. "Ahhh," is all he said. I reached under my skirt and touched his cock head when it pushed through my closed thighs. “Ahhh, yes,” he moaned, so I did it some more, feeling his cock and cock head with precum dripping from the slit.

After a while, he developed a rhythm, between my legs, then up along my ass, then back again. He was gripping my hips to hold them still while he stroked. My eyes were closed, savoring the sensation, particularly when he slid between my legs, because then it was skin on skin. Gradually I became aware that he was sliding my panties slowly down over my ass until they came off and dropped down to my knees. His cock now rode along my bare ass, and I could hear him sigh with pleasure. My ass was getting drenched with pre-cum, making it easier for his cock to slide along it.

On one stroke, he pulled back further than usual, and I felt his cock bump against my asshole. I jumped slightly. "Hey!" I said.

"Sorry," he said and went back to what he was doing... only to bump my asshole again a minute later.

"Cut it out!" I said. "That's enough."

"It's okay," he said, pointing to the picture. "Look, they're doing it that way."

I said I didn't want to do that.

"C'mon," he said, "let me do you."

I thought about it, his cock still sliding around between my legs and along my ass, and it was so hot, so exciting, that finally I nodded without saying anything. He backed up and again pumped his cock against my asshole, which was already slick with his precum. He tried twice to find the right angle, and slipped off. He grabbed my hips as he rubbed his cock full length against my butt crack; holding onto my hips as he again moved forward.

His cock found my asshole, and moved around a little, trying to find the right angle. After a minute he found it, and he pushed slowly, easing in a little. It hurt, but not too bad, and I closed my eyes, trying to relax. He shoved a little more, and with a sudden pop he was inside me. Slowly he pushed in filling me with his hard cock, stopping, he would pull out a bit and then push in again until he was all the way in. “Oh Misty, yes,” he moaned. The feeling was intense, amazing. I tried to look back between my legs but the front of my skirt hung down, cutting off the view. Looking to the side I saw in the mirror leaning against the wall our reflection. I had never been so excited than at that moment seeing James behind me fucking my ass. I looked like a young girl, her bare ass exposed while James was behind, his hard cock sticking out and sliding in and out of her pussy. I watched his cock, hard, white, surrounded by dark brown pubes and his balls dangling beneath, going in and out of my ass.

He pulled back, and pushed in again, slowly at first, then faster. I looked down to the magazine open beside me, of the woman being fucked by a man behind her, and imagined myself to be Misty, dressed in my skirt and blouse and bra. By now James was pounding hard against me, fucking me fast and hard. The only sounds in the garage were our gasps and the sound of our skin slapping. “Oh Misty, your pussy is so tight,” he moaned. “Fuck me Ricky,” I moaned, thinking back to our days when we first started having sex. Watching James fuck me in the mirror was too much and suddenly I felt my cock swell and release, shooting cum onto the skirt hanging from my waist. With each thrust a shot of hot cum released until I had squirted 4-5 times. My ass ring tightened around James's pumping cock as I came.

He shoved it in harder and deeper into me with every thrust, holding onto my hips to pull me back hard. “Ahhh, yes, oh fuck Misty, I'm cumming,” he cried out. Suddenly he got even harder inside me, and straighter, and seemed to fill me even more as he cried out and I felt something warm shoot out of him into the depths of my ass. He shoved it all the way in and held it there as he spasmed, gasping and grinding. I came a little more when I felt his hot cum release into my ass.

After a few moments, he pulled out with a wet sound and sat back on his feet. "Wow," was all he could say. "You okay?"

"Yeah," I said, my ass sore but not too bad. He was still breathing hard. He went to the bathroom to cleanup. When he got back he stripped off the clothes and sat back naked, his cock was still semi-erect and the head glistened with his cum. Seeing him naked  got me excited wondering about what it would feel like, even taste like. I suggested we look at the magazine again knowing that it showed the girl sucking the guy.

We flipped through some pages and when it got to the page with the girl sucking the guy's cock I lingered. As we looked at the pictures James said, “Dang, I bet that would feel good.” As we scrolled through a few more pages we came across another spread of blowjob pictures. “Man, I want that too,” he groaned, “Hey, you want to try that since you already let me fuck you?” I glanced at his cock and he was hard again. Without a word he got up to kneel next to me, his cock pointed toward my face. “Suck me Misty,” he moaned, using my wife's name for me. He leaned closer until his cock rubbed along my cheek, when it touched my lips I opened my mouth and his cock slipped in. “Oh Misty, yes, suck my cock,” he groaned, pushing his cock deeper into my mouth.

His precum was leaking from the tip and it tasted good. I wrapped my lips around his cock and sucked. James started pumping my mouth as he held my head. My tongue swirled around the head and along the rigid shaft as he fucked my mouth. “Oh Misty, I'm going to cum in your mouth!” he cried out. His balls bounced off my chin on every stroke and his pubes would tickle my nose. After only a couple of minutes James was huffing and then groaned as I felt his cock swell again, this time in my mouth. His cum blasted the back of my throat and then oozed onto my tongue as I sucked his spurting cock.