Lisa Learns to Love
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Lisa Who Almost Was free porn video
Lisa Who Almost Was
This story is based on a girl I went with. I have thought about her often,
but she wasn't the one. She would never give up her ciggies, for one
thing. But there were aspects of her I fondly remember. And if she had
been willing to make some different choices, ...
-------------------
I was spending the weekend with Lisa. She had said that she needed a pair
of black shoes, and since I had commented that I wanted to see her in
higher heels, we agreed to take her shoe shopping on Saturday. I had found
a pair of black patent leather pumps I really wanted her to get. She had
resisted, saying that they were too plain, but when I offered to buy them
for her, she relented.
When we got back to her apartment, she put her new shoes on and we sat
together on the couch. We were seriously making out and both really horny.
I asked to touch her shoes. She made a comment about my fetish -- not the
first time I heard that from her -- but it was halfhearted, and as I held
her foot I saw the look of pleasure on her face. She was wearing a black
sweater with a color block print and a black skirt that went just past her
knees. I moved one hand up her skirt and she became more excited. She
said, "Let's go to bed," and I accepted the invitation.
Lisa was an enthusiastic lover, and sex was thoroughly enjoyable. But
after we were done, she had to have her cigarette. She knew I can't stand
the smell, so she went out on the balcony. I called to her that she could
have stayed in the kitchen, but she was trying to be accommodating. Being
a smoker, she doesn't realize that the whole apartment stinks of them, so
she wasn't gaining anything for me going outside.
When she returned, she wanted to lay and cuddle. I knew she would, which
is why I remained in bed. The stale peanut butter smell of the cigarette
was on her, and I wanted to focus on something else. So I asked her what
her sexual fantasies were.
"I want to be fucked in the ass."
"Anything else?"
"Men who dress as women really excite me."
This was not the first time she had mentioned this. It made me think hard,
because I wanted to dress up and I wanted a woman who would accept me. At
the time I owned a few pairs of high heels and a pair of fishnets.
Sometimes I would make a wrap skirt for myself out of a towel and a safety
pin. But I had never admitted this to anyone. It was very risky. I always
visualized a woman getting angry after a breakup and telling the world
that I was a crossdresser. Was she really serious? How could I get a
deeper understanding of what she wanted?
Finally, I asked, "What about that is exciting to you?"
"I don't know, it just turns me on to see a man in women's clothes."
Here goes. "Are you saying you would want to see me in women's clothes?"
She lit up. "Would you do that?"
I still wanted to be guarded. "Possibly. What would you have me wear?"
She sat up and looked at me. "Your legs would be really hot if you shaved
them. I'd have you wear a houndstooth mini to show them off. A really soft
white cashmere sweater. And, since you're always on me to wear high heels,
a pair of patent leather pumps like mine, but with higher heels."
I was trying to come up with an answer that kept the options open, that
indicated I was willing but didn't give away that I really wanted her to
dress me up like that something fierce. I needed to buy time, so I said,
"I never see you in a miniskirt."
"I'm way to self-conscious at my current weight to wear a mini. But I
could put one on you. I'd love to get you wearing all the clothes I'd
never wear, like frilly dresses, slit skirts and super high heels with
bows."
By now I could barely think. If she had been holding my cock when she said
that, I would have been so busted. I turned practical: "Where would you
find clothes like that in my size?" This was before the internet.
"Oh, I bet we could find something for you in New York."
This was really hard, to hit the right note and not give myself away too
soon. Then I had an idea that would let me position this as an exchange.
"Lisa, I have a deal for you. You quit smoking and I will let you dress me
up the way you want to."
That hit her hard. "I can't do that."
But the more I thought about it, the more I liked the idea. If she wasn't
going to give up smoking, we weren't going to last very long, and I didn't
want to come out to her if I didn't think we were for keeps. So I pushed
further, saying, "You can if you really want to see me in a dress."
She gave me all the excuses about how stressful her job was, how all her
friends smoked, how she needed a cig in the morning, the whole sequence. I
wasn't buying. And she knew how much money she was burning through on her
habit. Finally, after much debate and a lot of soul-searching on her part,
she agreed. "But you have to keep your end of the deal," she said. "I'm
not quitting until the day I see you in drag."
It was late, and we were both hungry, so we went out into the kitchen to
make dinner. Later on, when we were in bed, I asked her to describe for me
again how she would dress me up. This time she added a faux pearl necklace
and earrings. She was so turned on that she didn't notice how much she was
exciting me by telling me this.
Sunday around noon, I needed to leave for home. When I kissed her good-
bye, she said, "Remember, we have a deal." I had expected her to be
pushing to get out of it to defend her habit, but she wasn't. She had a
look on her face like she had a plan.
Wednesday, she called me and told me she wanted me over for the weekend.
"We're going to New York on Saturday," she added. It was hard to focus for
the rest of the week. I had no idea what to expect, and the anticipation
was overwhelming.
Friday night I went over to her place. Lisa was waiting for me, wearing a
pretty dark green dress and her black patent pumps. We had made plans, but
we started necking and never got out the door. I really wanted to ask her
to wear her shoes to bed, but I didn't want to mess up whatever she had
planned for tomorrow, so I held back.
Saturday morning, after breakfast, she said, "The first thing we are going
to do is to shave you."
"Completely?"
"No, just your legs. You know men with bald chests creep me out."
Lisa walked me to the bathroom and put me in the tub. I turned the shower
on. "Soap up your legs real good," she instructed. She got her razor and
wet it. She began at my thigh. I started feeling her breasts, but she
said, "Pay attention to how I'm doing this. You're going to be doing the
other leg."
She worked her way down one leg, then I did the other under her
supervision. We finished showering together and dried off. Then we went
back to the bedroom to dress. She put on in a red sweater, her black skirt
and her pumps. She asked me if I was ready to do some shopping.
"Find all your cigarettes and put them on the kitchen table."
Ten minutes later we were looking at a small pile of half-consumed
cigarette packs. I asked for a trash bag.
"Wait! Can't I have one last smoke?"
"It will be easier on you if you don't."
"Well, what happens if we get to New York and you weasel out of your end?"
"Then you buy more cigarettes."
She looked down at the floor for a minute. "OK, fine, throw them out. I
will meet you at my car."
"Oh, no. I know you have more stashed in the car. We're getting rid of
them, too."
I swept all the cigarettes into the bag. We walked out to her car together
and I held the bag open while she disposed of four more partially consumed
packs. Then we walked to the dumpster together. I handed her the bag and
held the lid open. Lisa took a deep breath and threw the bag in. Then we
went back to the car and got in. As she started driving, I asked where we
were going. She just smiled and said, "You'll see."
We went through the Holland Tunnel into lower Manhattan. She found a place
to park and led me through the streets by the hand. We were down below
Fourteenth Street, where the streets cease to have the reliable grid
pattern that helps you navigate. I had bought my high heels in New York,
but the stores were not around this part of town. I had no idea where we
were going, but Lisa did.
We walked for several blocks. Finally, she led me to a rather large store
that seemed to specialize in clothes for crossdressers. "How did you find
this?" I asked. Her answer was, "Ask me no questions, I'll tell you no
lies." She had a smile on her face like the cat that ate the canary.
I was amazed at the selection they had. There was an entire wall of
beautiful shoes! I saw other men there picking out merchandise. That would
have normally freaked me, but between Lisa being there and the
purposefulness of the whole thing, I was more relaxed than I thought I
would be. We started looking at clothes, although I was stealing glances
at all those lovely shoes. I asked Lisa how to know what size I am, and
she held up some clothes to get an estimate. "It's not like mens' clothes,
though," she warned. "You can't just grab something off the rack that's an
18 and know that it will fit. You have to try it on."
Oh, God. I hadn't reckoned with that. I'm out in public, and I'm going to
go into a changing room as a man and come out as a woman? I must have
visibly turned pale or something, because Lisa came up to me and put her
arms around me, saying, "It's gonna be OK, baby. Nobody's watching you.
Except me, of course." Then she gave me a kiss and grabbed my ass.
We started going through the racks. Lisa found a beautiful tiered red
dress (I miss the 80s). As soon as I saw it, I knew I was going to be
heartbroken if it didn't fit. I found a beautiful black pinstripe skirted
suit. I wanted it, but it was just a jacket and skirt; I couldn't see how
I could wear it. Lisa came over and said, "You like that?" I wanted to
avoid that question, so I showed her the V neck and said that I couldn't
see wearing it with chest hair.
"What you need is a shell under it," Lisa explained, and found an opaque
white shell that looked like it would fit me. She handed it to me, and
walked me toward the changing rooms. "Oh, look," she said and stopped
suddenly. She pulled out a black skirt slit to about mid-thigh. "You would
look hot in this." She went into the changing room with me. She helped me
into the red dress. There was no hiding my reaction now, because my
erection was obvious in the dress.
Lisa put her hand on my cock and said, "You like this, don't you?"
"What was your first clue?"
"Well, we can't have you walk out with a big tent in the middle of your
pretty dress. Let me help you." She adjusted me so that I was presentable
and led me to the mirror. All I could say was, "It's beautiful."
Lisa helped me as I tried on the other clothes. She also ducked out and
returned with package of stockings, which she opened. They were thigh-high
and had seams up the back, with elastic at the tops to stay up. She helped
me get them on without ruining them. I couldn't help admire my nyloned
legs in the mirror.
Lisa asked me what I wanted to wear trying shoes on. I selected the suit.
I walked out in my suit and stocking feet, carrying my boy clothes. I
asked Lisa what to do with my wallet and keys. "I'll hold on to them for
now," she said as she dumped them in her purse. "Obviously you need a
purse of your own."
When we got to the shoes, I was making a last stand to hold down my
enthusiasm. I had never before seen heels this high that I could wear. I
asked Lisa how many pair I should get. Her reply was, "How many pair do
you want?" That was the first silly thing she had said all day. I wanted
every pump they had in every color and heel height, but I said two or
three.
First we picked out a black patent pump. It was like hers, but the heel
was four inches high. "Perfect," Lisa said, "your heels will be higher
than mine." Then I saw a lovely white pump with a bow and a cutout in
front of it. It also had a narrow four inch heel. When I picked it up, I
felt how incredibly soft the leather was. I damn near came in my skirt.
Lisa found a bright red leather pump with a five inch heel and showed it
to me. I had dreamt of having shoes like those. We got sales help to bring
out the shoes we had chosen in my size.
The first pair I tried on was the black pair. When I slipped them on and
walked in them, I was in heaven. I felt the height of my heels as I walked
over to the mirror. When I saw myself in my black suit and patent pumps,
the last wall came down. I pointed my toe so I could see the patent
leather glow in the light. It was glorious. I turned my back toward the
mirror so I could see the seams down the backs of my legs disappear into
the pumps with their sexy thin heels.
Lisa called me back to reality, since I had more shoes to try on. She had
me sit next to her, and she was holding one of the white pumps in her
hand. "I've never felt shoes this soft," she said. She slipped the black
patent pumps off me and fitted the white pumps onto my feet. I felt like a
total princess when she waited on me like that. I looked down at the
gorgeous white pumps. They were on my feet in a public place. The cutout
in front of the bow showed some of my toe cleavage. I walked over to the
mirror and moved around. I felt absolutely beautiful.
As I walked back to Lisa, she said, "You need to take a shorter stride
when you wear heels." She stood and walked with me. "Now," she continued,
"I want you to put one foot slightly in front of the other." She put one
hand on my ass, which made me aware of the movement of my ass from side to
side. "Feel that? The higher your heels are, the more I want your ass to
wiggle. Now let's go for the big prize."
She changed me into the red pumps. I stood up, but wasn't used to heels
that high. I could barely move, but was totally smitten looking down at
the pretty red triangles at the ends of my legs. Lisa asked if I needed
help walking over to the mirror. "I don't need to go to the mirror," I
replied. "I want these."
Lisa changed me back into the black patent pumps, saying, "Let's pay and
go home."
"I need to change."
"Into what? I want you dressed the way you are."
"I can't go out into the middle of Manhattan dressed like this!"
"Why the hell not? Nobody knows you here. Besides, I can't stop looking at
you like this, and I want to take you out and turn heads." She pulled me
close to her and filled my mouth with her tongue. I nearly melted then and
there.
I agreed to leave wearing my suit and pumps, but asked her to put the
clothes on her charge card. I promised to write her a check when we got
home. We showed the tag for my suit and the wrapper for my stockings. All
our loot was bagged and we walked out the door.
And then I heard it -- the sound of my stiletto heels clicking on
pavement. I got another erection, and Lisa had to stand in front of me and
work my cock back between my legs. Well, I could have, but I'd much rather
have Lisa touching me. It was unseasonably warm for that late in the year
and everything was perfect. I couldn't help looking down at my pumps
shining in the sunlight as I walked.
When we got back into the car, Lisa pulled me close to her. Guiding my
hand up her skirt, she said, "I have been going crazy at the sight of you.
I need you to give me some release right now or I'm gonna explode." I
kissed her neck as I threaded my way into her panties and began to finger
her clit. She began to moan, which grew into almost a howl as she
climaxed; she put one hand behind my head and pressed my face into her
collar.
After she had time to collect herself, she started the car and headed back
for the river crossing. In the tunnel, she put her right hand up my skirt
and began to feel my cock. I had assumed we were going home, but she
turned north on the Parkway. I asked her why she was going that way.
"We're going to a mall to get you some things. You need panties, nylons
and a purse."
"I can't go into a mall like this!"
"Yes, you can. It will be miles from where we live. No one will know us.
And I can't wait to show you off." She reached her fingers into my
underpants as she said this and I felt her warm hand on my cock. She could
be really persuasive.
We pulled into a mall in Paramus. I didn't want to admit it, but it was a
rush to walk across the parking lot in my skirt and heels. Lisa led me by
the hand into a department store and picked out some panties for me. We
also found some clip-on earrings. She selected a gold circular pair. She
also found me a simple black purse, not too small nor too large. We also
found some thigh-high stockings, a mix of white, nude and coffee. As soon
as we left the store, she had me put my earrings on.
I wanted to leave, but Lisa wasn't through. She led me down to the food
court and we got some coffee. While we waited, she pressed her body
against mine. She was looking around and often directed my attention to
someone who was staring at us.
When we got back into the car, Lisa pulled my underpants down and had me
put a pair of panties on. I transferred my wallet and keys from her purse
to mine. All the way back to her apartment, she told me about all the
people she saw at the mall who couldn't stop looking at us.
After we got into her apartment, she pushed me against the front door. "Do
you like feeling the height of your heels?" she asked. I told her I did
very much. She got on her knees and put her head under my skirt. She
pulled my panties down and I stepped out of them. She took me into her
mouth and gave me a sensational blowjob. I shot a massive load into her
mouth and she swallowed it all.
I could barely stand up after that, so she helped me into bed. She
undressed me and changed me into the red pumps. She started to take off
her pump, but I said, "Please let me do that." I removed her shoes and she
took her stockings down and undressed. I replaced her shoes on her feet,
kissing each pump over her toes so she could feel it. She pushed me
backward on the bed and mounted me.
"How do you feel in your fuck-me heels?"
"Incredibly pretty and sexy."
"I've been waiting for this all day," she said as she started to ride me.
We spent the rest of the day in bed.
It felt so good to have her acceptance of who I really am. I married her a
year later. She has me dress up every evening when were home alone.
Clover
- 12.01.2022
- 19
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