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"Well you know why Lisa dropped Paul?" It was my sister-in-law, Susan offering me a tidbit from my wife, Lisa's past. The three of us were eating dinner one evening and we had had a few beers.
"Susan!" Lisa said it almost as a whine. She looked alarmed. Naturally I was intrigued.
"Paul wanted to do it with Lisa with himself dressed up as a woman!" I giggled, but stifled it quickly when I glanced at Lisa. She was blushing and obviously embarrassed about it. I tried to hold a straight face.
"Susan, you didn't have to bring that up!" Lisa had recovered enough to protest verbally. I glanced back at Susan and realized she was watching me closely, out of the corner of her eye. She quickly moved her eyes.
"You never told me about Paul." I brought up the subject again on the way home.
"I.., it isn't *that* weird," Lisa was obviously having trouble talking about it. I don't know why I tortured her.
"Weird enough for you to drop him?"
"Please, can we drop the subject?" Lisa had found her assurance again.
"OK by me." I added, innocently, I hoped. I still couldn't believe that old-fashioned Lisa had been in a situation like that! I could believe it of Susan--she was something else. She was a flirt and a definite cock-tease: whenever Lisa wasn't looking, she seemed to be seeing if she could keep me panting. She was definitely a looker, with long dark hair and a small, but hard body, and she did get me hard often enough, but I knew her type.
Well, two nights later, when Lisa was at work, Susan showed up at our front door and invited herself in when I opened it. Now when Susan and I are alone, she always teases me all the more. So I was wondering what she would try this time. One thing: she was dressed to kill, in tight-fitting jeans and a tight body-suit. Oh, I could just reach out and touch...
And she wasted no time showing me what I was in for--as soon as the front door was shut, she grabbed my cock! This was way beyond anything she'd done before!
"Are you interested?" I was definitely hard. She was grinning at me and rhythmically squeezing my cock through my pants. I was afraid I wouldn't be able to control myself. I reached for her, but she immediately fended my grope with her other hand, dropping a bag on the floor in the process. In seconds, she had my hands in hers, and she was holding my hands against the sides of her hips. She was still grinning at me. She raised my hands so they came up to the sides of her body.
"I've got something for you to do," she said, and she put my hands back to my side and picked up the bag. She still had this sly smile. Then out of the bag, she pulled a dress. For a second I was confused. Then my jaw dropped.
"I believe you guessed wrong," I returned. But she had dropped the dress and immediately had my cock in her hand again and was squeezing and massaging it again. I was going crazy.
"Come on, just try it!" She taunted me. "It'll be fun just to see what it looks like on you!" She didn't stop working my cock and I was afraid I might come in my pants. She rubbed her hands up my chest and started unbuttoning my shirt. She was still smiling at me and she was undoing my pants in seconds, and was pulling down my shorts! She had me sitting on the couch and had my shoes and socks off. Then she had some panties from her bag and she started putting them on me. I couldn't deny that the silky feeling against my skin was erotic.
"This'll be great, you'll see," she added. She put the dress over my head. It was black and obviously made to cling, but she seemed to have my size. Then she pulled some high-heels out of the bag and proceeded to put them on my feet. "I got your sizes from Lisa so I could buy you clothes for Christmas," she said with a giggle. Then she pulled me to standing and pulled and adjusted the dress. Then she pulled a wig of long blond hair out of her bag and soon had it on my head.
"This'll work great," she said and she pulled me over toward a mirror, almost toppling me since I had no idea to handle the high- heels. We got to the mirror and I looked at myself and I was in awe. "Just a little bit of makeup, and you'll be perfect!" I hate to say that I have a feminine face, but the truth is, I could see right there that I would have no trouble passing as a woman. And I hardly recognized myself! She put a bit of makeup on my face and then wanted me to try the shoes, practicing walking back and forth. In a little while, I was doing a bit better. In fact, that is how we spent the next hour, Susan coaching me on walking and movement.
Then she had me just stand in the middle of the room. She went around behind me and reached around my body and started feeling it as I just stood there. Her hand went down to my cock and rubbed it. She started lifting the dress off me, and soon had it off. She told me to step out of the shoes and then she pulled the panties down to my ankles and told me to step out of them and she lifted the wig off my head. Then she reached around and stroked my cock, in long slow strokes, until it was hard as a rock and sticking a straight out.
"Just a minute," I heard her murmur. The next thing I heard was the front door and I realized she was gone! I looked around immediately. The dress was gone! I stood there feeling like a fool, grabbed my clothes, peeked out the front window to see her driving away and waving, and headed for the bathroom for you-know-what. I spent the rest of the night amazed at what I'd done and wondering what I'd do the next time Susan and I met. I couldn't believe I'd let her do that to me.
The next night, Susan was back, and I wouldn't let her in. I told her I wasn't interested and I knew her games and she should go home and forget it. She insisted on showing me something and handed me a photograph. It was me in the dress. But without the wig and it was obvious that it was me.
"Where did you get that?" It was a stupid question to ask, I admit. I let her in.
"Doesn't matter. There are more." She watched me. I was thinking furiously.
"Strip." She had obviously waited until she figured I had thought things through and knew what the score was.
"Listen..." I started.
"No talk, just strip." I hesitated. Then I got undressed. She wordlessly handed me the bag in her hand and I put on the outfit. She got out some makeup and started putting it on my face.
"Let's see some more walking, honey," she said when she was satisfied. She kind of drawled it. "Aren't you cute," she added and she patted my ass. Then her fingers edged down the crack of my ass. I couldn't stand it. "OK, we're going out," she said.
"Look in the mirror. You're ready. You'll pass easily."
I looked. She was right. "But why?"
"Oh, just for kicks."
"I'm not interested in those kind of kicks."
"Oh you're not?" She sounded like she didn't believe me. "Well, you don't really have a choice, do you?" I thought of the photographs. "Just a walk around the neighborhood, that's all." We walked. I was afraid of people looking at me. I was afraid of people recognizing me. I was afraid of falling. It seemed like forever. Finally we were back inside. Her hand was immediately on my cock. "Looks like you are pretty hard." She smirked at me.
"I.., I can't help it if I respond to sexy women."
"Oh, I'm sexy? Why thank you!" That drawl again. "But I think you got hard from walking around like that." She kneaded and squeezed my cock and I was in danger of coming. In fact I did come.
"Oo, you messed up your clothes. You'd better get them off and clean up!" There wasn't anything else to do. Soon I was naked and I went into the bathroom. When I came out, she was gone and so were the clothes. I got dressed again.
Susan was there again the next night and took me for a walk again. Then she told me to tell Lisa I had to go away on business for a couple of days. She wouldn't let me refuse and she held those photographs over me. I ended up lying to Lisa, that Sunday telling her I was off to the airport to fly off to Boston. Really I drove to Lisa's. After letting me in her front door, she immediately had me in a dress and had me practicing. I slept that night in a sheer nightgown... on the couch. The next day she told me to practice while she was at work. She took my regular clothes with her. That night, she told me we were going out to a bar.
"No way," was my automatic response. I should have known better-- there was no stopping her. Soon we were downtown, sitting at a table, drinking beers when in walks Lisa. I almost choked. Susan waved to get her attention and soon I realized that Susan had set this up. She introduced me to Lisa as Jackie and sat there and grinned. I tried to keep Lisa from getting a good look at my eyes, but even when I gave up trying, she didn't show the slightest sign of recognition. We had a few more beers and Lisa and Susan gossiped, leaving me out of the conversation. Lisa apologized a couple times to me, for the two of them conversing without me.
Finally, Susan said: "Guess what." She was talking to Lisa.
"Jackie is a man."
"Stop it!" Obviously Lisa took it as an embarrassing joke. She looked at me a little.
"Here!" said Susan, grabbing Lisa's arm. She pulled her arm over her own lap to me and pushed her hand right to my crotch. Lisa looked shocked at what Susan was doing, but Susan managed to get her fingering my cock. She didn't lose her look of shock.
"What do you think?" asked Susan. Lisa looked closely at me. I just knew she was going to recognize me, but even though she was inches away and staring right into my eyes, she showed no sign of recognition.
Finally Lisa said "I'm going."
"No, you're not," returned Susan, laughing. Lisa stayed. I think she let Susan push her around. There was an awkward silence. Lisa looked nervous.
"She likes to have her cock sucked." It was Susan talking to Lisa! "Take her out back and do it." She stood up and pulled Lisa up and brought her over and put my hand in hers. We stood there. "Go!" Lisa pulled and I stood up. "Take off all your clothes and kneel in front of her." She was still talking to Lisa! "And put these on, behind your back." She handed Lisa a pair of handcuffs!
I couldn't believe it, but Lisa did it. She led me out back and into a dark corner. She had everything off in seconds, and knelt in front of me and lifted my dress and pulled my cock over the top of my panties. She didn't say anything--just did it, exactly like Susan told her to. Then she put the handcuffs on one wrist, handed me the key, and stood and turned around with her hands behind her so I could fasten the other wrist. As soon as I did, she was on her knees again, and had my cock in her mouth. I couldn't believe it! My wife, kneeling and sucking my cock. She never did that! Did she know it was me? There was no indication that she did. She looked so desperate, sucking as hard as she could. I couldn't help it. I had my hand behind her head and pushed my cock in. She didn't mind a bit, but seemed even more excited. She kept sucking and sucking. She was so excited you would have thought someone was fingering her... or eating her. Soon I was coming. She swallowed every drop and it seemed like she couldn't get enough.
I undid the handcuffs and she got dressed and we went back in. Susan was talking with some guy. She immediately split with him and told us it was time to go. I just sat there thinking when she drove me home.
That night I slept in a nightie again, and the next day she had me practice more. She got home again and after supper we went out. We stopped at Lisa's and my house and picked up Lisa. She was wearing a tight sexy outfit that I didn't remember seeing before. We drove to the local high-school which was just about deserted that night. Susan took us to the football field. It was empty and dark.
"Take her in there and strip, lie face down on the ground, and let her push her cock into your ass." Susan was telling Lisa what to do again. She handed me some K.Y. Jelly.
We walked to the middle of the field. Lisa didn't say anything. She wordlessly stripped and lay down. I looked down at her. I had never done her rear before. I knelt beside her, covered my finger with lubricant, and pushed it into her. I heard her breath catch. Then I covered my cock and lay face down on top of her. I lifted my dress and pulled my cock over the waisteband of my panties. I pushed my cock right against her rear hole. She was holding her breath. The head entered. Suddenly she was breathing hard. She started pushing her rear up against me. She reached her hands behind her and pulled my rear down against her. I could tell she wanted me to fuck it. I couldn't believe it. Lisa! I fucked and fucked. She moaned, louder, and finally came. I came in her at the same time.
We lay there for a minute. She didn't complain at all that I was laying on top of her. Finally I stood up and straightened my dress. She got dressed. Susan was waiting at the car when we got back, with a grin on her face. Lisa never said a word as we drove her home.
That night and the next day was much the same. When Susan got home, she changed me to another sexy outfit and was really careful with my makeup. Then we just sat in her living room.
Finally my curiosity overcame me. "Are we going to see Lisa tonight?"
"Oh, no--Lisa is gone."
"She went to San Francisco, looking for Paul." My jaw dropped.
"But I'm supposed to be 'back' *tomorrow*." She just shrugged. I couldn't believe it.
"Paul is married now," added Susan, "but he said he'd take Lisa in if she's willing to serve his wife too." She had stood up and was behind me. Suddenly something was in my mouth and fastened around my head. A gag! I stood and she immediately had my hands fastened behind my back. She pushed me over an ottoman and had my legs tied together. Then she was raising my skirt and pulling my panties from down over my ass. I felt fingers going to my rear hole.
"It's time for you to find out what it *really* means to be a woman." I heard more noises in the room. I looked around. A guy was there. He was muscular and huge. He was taking off his pants. I couldn't stand up--Susan was holding me down.