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This work is copyrighted to the author © 1997.  Please
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Dress
By Deirdre (address defunct)

***

A man plays around with cross-dressing because his 
pretty sister-in-law persuades him to. But things soon 
escalate beyond his wildest dreams. (MF, MM, tv, bd, 
d/s)

***

"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.

"No way."

"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.

"What?"

"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 waistband 
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."

"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.

END

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than
a trusted partner. You only have one body per lifetime,
so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
Kristen's collection - Directory 29