A man plays around with cross-dressing because his pretty sister-in-law persuades him

“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.

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