It was my sister-in-law
“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
“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
“You never told me about Paul.” I brought up the subject again on the
“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
“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
“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
“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
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
“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
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
“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
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
“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.