Date: Wed, 16 Feb 2011 10:40:57 -0600
From: George Pearson <george3130@gmail.com>
Subject: Adult Theater Fun-2

This is a continuation of the Adult Theater Fun story posted here at Nifty.

So there I was, riding home with an older man that I barely knew...wearing
only a bra and a thong. Jack had said that he lived close, but what he
really meant by that was he lived about a half hour away. This gave us a
chance to talk. We talked a bit about our lives and who we were, where we
were from, etc. Though I was afraid it would be a bit weird, I found it
really nice to get to know the guy who I was making love with. Jack used to
be a construction contractor, but a higher level manager, not just a
worker. At 62 (I think...I'm not 100% sure), he was retired and just lived
out in the countryside. His wife had died years before, so he lived
alone. He said that it could get lonely, but he had friends in town and
living alone gave him the opportunity to explore more "romantic" interests.

He had his hand on my thigh for much of the ride and it made me feel so
warm and happy. I would rub his thigh as well and periodically rub his cock
through his pants. I seriously considered giving him a blowjob in the car,
but I was worried he would get distracted and well...I had no intention of
dying in a car crash that day...especially not wearing what I was wearing
for my family to hear about.

We finally reached his house and turned into the driveway. It wasn't a
mansion, but it was far from being humble either. It was two stories and
probably a 4 or 5 bedroom house. I commented that I liked the house and
after we went inside, Jack gave me a quick tour. Upstairs, one of the
bedrooms was pretty feminine and I wondered if his wife had decorated it
before she died, but I didn't have the nerve to ask. Jack told me that I
could use this room and the connecting bathroom to "freshen up." He told me
there were razors and make-up in the bathroom and I should help myself. I
gave him a seductive smile (as best as I could), said "thank you" and gave
him a big wet kiss. He left and closed the door.

I went into the bathroom and sure enough on the counter was a pretty good
supply of make-up...more types than I really knew how to use. I began to
wonder if he regularly brought sissy boys home to take advantage of. I
didn't find out until much later, but the make-up was actually a
combination of some of his wife's left over make-up and his (17 year old)
niece's who would periodically visit. He had bought his niece new make-up
once when she visited because she had forgotten hers, so she just left it
there.

I took off my bra and panties and removed the handkerchief in my ass (by
this point, it was pretty nasty). I turned on the shower and grabbed a
razor and some shaving cream. Though I am not an incredibly hairy guy, I am
far from the hairless guys who traditionally make good crossdressers. So,
starting with my legs, I slowly shaved my body. The legs took a while and I
did cut myself a few times, because I had never shaved my legs before. I
shaved all around my cock and balls and did my best on my balls, but found
it really difficult, so I ended up leaving a little of that short, thin
hair on my balls, but it was hardly noticeable. I shaved the little hair on
my ass. I then shaved my chest and my armpits. I waited until after I got
out of the shower to touch up my face.  I took a bit of time in the shower
trying to make sure that my ass was clean and there was no cum about to
leak out at any moment.

After I got out of the shower and shaved my face, I dried myself off and
examined my hairless body in the mirror. It looked pretty good. I wasn't
sure if you were supposed to put on makeup or clothing first, but clothing
made a bit more sense to me, so I went out into the bedroom and found my
new clothes there (Jack must have brought them up). I started slipping on
my new pink and black lace-lined panties and they just felt so smooth and
amazing on my freshly shaven legs. I had a lot of trouble getting them
positioned, because I had a raging hard-on. If I were at home, alone, I
just would have jacked off so I could easily get the panties on, but I
wanted to save my cum for Jack, so I just did the best I could.

I then put on the bustier. It took a bit of time, because I had to put it
on backwards and clasp the dozen or so bra-type hooks. Once I got it on, I
slid it around and up my body so the cups covered my breasts. Thankfully,
clasping the hooks took long enough and was frustrating enough that my cock
had a chance to settle down for a little. It easily fit inside the
panties. However, once I look at myself in the mirror with the panties and
bustier on, I started to get hard again. The lingerie really did give my
body a sexy, feminine, look. The panties did contain my cock this time and
it didn't end up poking out. I slipped on the thigh high stockings, but it
took me a few minutes to attach the garters (from the bustier) to them. It
is far from an easy task, especially with the back garters. However...just
as I finished putting on the garters, I remembered something. I had once
read that you should put your panties on OVER the garters so you could
easily take the panties off to go to the bathroom or well...do other
things. So I undid the garters, removed he panties, redid the garters and
slipped the panties back on. This was a pain, but would probably be worth
it.

The panties over the garters didn't look quite as sexy as under them, but
it honestly didn't make a big difference, so I didn't worry about it. I
slipped on the maids outfit over my lingerie. Amazingly, none of the pink
showed. The maids outfit was one of those stereotypical french maid dresses
that is made to look like a corset in the front. It had shoulder straps, so
it covered the bustier and my garters were actually black, so none of the
pink showed. Now, if Jack looked up my skirt (which wouldn't be
particularly difficult), he might see a bit of pink, but I don't think he
would have minded. The outfit came with a sexy black and white choker that
nicely covered my adams apple and it can with small white hat that I
actually ended up forgetting to put on.

I had little experience with makeup, so I just did the best I could. I
don't think I've mentioned this before, but I wear glasses, but I decided
to go without them for a few hours just for Jack. I slowly and carefully
put on lipstick...a somewhat dark pink color. I then put on eye shadow
which wasn't hard. I then put on eye-liner, but this took me forever and I
didn't do a great job. It was weird poking something so close to my eye. I
put on a tiny bit of blush, but not much. I briefly put my glasses back on
to see myself in the mirror...I was sexy. I didn't have a wig or fake
breasts, but overall, I still looked amazingly feminine. I was sure I would
make Jack happy.

I wished I had some sort of heels or other sexy footwear, but all I had was
my sneakers, so I just decided to go downstairs in my stockings without
shoes...it seemed like the sexiest option. I headed downstairs and found
Jack reading a book in the living room (I don't blame him...I had taken
well over an hour). He put the book down on the night stand and looked up
at me. He didn't say anything for awhile, he just stared at me and
eventually said..."wow." "You like?" I asked. He stuttered for a second and
then said "Jessica...you are the sexiest girl I have ever seen." Now, I was
clearly far from the sexiest girl ANYONE had ever seen, but...he was being
incredibly sweet and it made me really happy. I imagine that I blushed a
little bit, but I'm not 100% sure. I slowly walked over to him (he was
sitting on the couch) and I straddled him in his lap. I just sat there for
a bit. We stared into each other's eyes with lust and affection.

I leaned forward and started kissing him. We must have deeply, passionately
made out for at least fifteen minutes, maybe even much longer. He put his
hands on my thighs and slowly started to feel my body all the way up to my
shoulders, eventually running his hands through my hair. He grabbed my ass
for a bit, but didn't linger too long, because it wasn't a great angle. I
would periodically rock a little bit not only to keep the blood in my legs
circulating, but also to get and keep him hard. I could feel his manhood
under me, but there was no real way I could reach it. He started massaging
my breasts through my dress and bustier and it really did feel good and I
could tell he liked it as well. He would periodically stop and passionately
kiss me on the neck. The first time it happened, I gasped in immense
pleasure. I was in absolute heaven. Jack really knew how to turn me on.

I slowly slipped off him, running my hands all over his body. I got down on
my knees below him and slowly unzipped his fly. His cock didn't quite
"spring" out, but he was already pretty hard, so his cock came out pretty
easily. I wanted better access to his shaft and balls, so I started pulling
his pants off. Of course he was sitting down, so he did the awkward thing
where you get off your butt a little, just enough to slip the pants down a
little, but then you have to keep adjusting to get the pants the rest of
the way off. So eventually, with my help, his pants were laying on the
floor.  I got in close to him and held his cock in my hand while I kissed
the entire area around his cock. This definitely turned him on and his cock
got completely hard.

I leaned forward and just licked his head. I just went around and around
the head of his cock a few times with my tongue. His head was already
covered with precum, so I got to taste his wonderful juice. Now I don't
know if cum and precum actually taste good, but whenever I try them, I am
already incredibly turned on and they just seem to act as an aphrodisiac. I
pushed his cock up a little and just slowly licked the underside of his
cock from base to head. He moaned. I slowly licked a little bit of his
balls and tried to get as much of them in my mouth (with my teeth covered
by my lips) and just licked them a little. I gave his shaft one more, long,
big lick and stopped for a second and just looked up at him with lust.

I knew I was just teasing and driving him crazy and he said "Jessica,
Jessica, please suck Daddy's cock!" I pretended to think for a second and
said "Okay Daddy" and gave him a big smile. I gave his head one more quick
lick just to tease him a little more and then I steadily put his cock in my
mouth lowering my head until his head was almost in my throat and I could
almost stretch my lips down to the base of his shaft. He shouted "Oh!" I
stayed there for a second and pulled back a tiny bit and started playing
with his cock with my tongue. After a few seconds of this, I started
bobbing my head up and down. I would sometimes go as far down as I could,
but not always. I would periodically take my mouth off or go all the way
down and stop for a second or play with his cock with my tongue. I started
speeding up and he started moaning. Much of this time, he had been running
his fingers through my hair, but after I sped up for a bit, he would
sometimes push me down on his cock with his hands. It got a little
forceful, but I was getting used to a cock deep in my mouth/throat, so I
didn't mind. After a while, he started thrusting his hips too, but he was
sitting, so it wasn't too intense. After a while, my drool was dripping all
over the place and I could see he was in ecstasy. Even though he was
forcing his cock in his mouth, the once or twice I wanted a few second
break, he let me. I didn't want him to cum, so I pulled off and gripped his
cock with my hand and stroked it a little and got up (still holding his
cock) and kissed him.

After a few seconds, he calmed down a little and suggested we go up to the
bed room. We went up to his room and started kissing again. He pulled my
dress up and we took it off. He just stared at me again and grabbed me in
lust and started kissing me again. As he kissed me, I was stroking his
manhood. Eventually, I slipped of his shirt and started slowly kissing down
his body, giving particular attention to his nipples. I got down on my
knees and started sucking his cock again. This time though, he held my head
and just fucked my mouth. It wasn't really violent or anything, but at very
first it was a little jarring, but after a little bit, I got used to it.

He told me to lie down on my back and I did, not sure what he wanted to
do. He got behind my head and straddled my face with his head towards my
feet. He slowly lowered his cock into my mouth and started fucking it
again. This time however, the angle was much better, so I could take most
of his cock and it really didn't hurt. After maybe five minutes of this, he
slowed and pulled my panties down a little bit. He started sucking my cock
as well and he stopped thrusting, so I started working his. We stayed in 69
for a while. It felt so great! My cock hadn't had any attention since the
theater, but it had been excited for so long. After maybe 10 minutes of
this, Jack got up and said "Thank you so much Jessica. You are such a good
girl. Not many girls would be okay with me being so forceful with your
mouth and I usually wouldn't want to be, but you just look so amazing and I
don't know what came over me." I said "It's okay daddy, I like your cock in
me!" He smiled and got down and sucked my cock for a bit longer.

He stopped and slowly kissing every inch of my body. He started at my feet,
kissing and rubbing my stockinged toes and feet and he slowly made his way
up. With his mouth, he would use just the right amount of tongue and
suction and it drove me CRAZY. He went up my legs, but went right next to
my cock, not actually touching it. I wanted him to kiss it so bad. Because
I had the bustier on, he started kissing my hands (he couldn't kiss up my
stomach). He sucked and licked my fingers one by one and slowly moved up my
arm until he got to my shoulder. I was so aroused. He then took my bustier
straps and pulled them down off my shoulders and folded the cups of the
bustier down so he could have access to my breasts.

He lightly rubbed my nipples with his hand and a small shock went through
my body. He started kissing my neck and then slowly moved down to right
between by breasts. It felt amazing. He then slowly kissed around one
breast, started on the outside and slowly spiraled he way to my
nipple. Once he got there, he intermittently flicked my nipple with his
tongue. My nipple was already super hard. He slowly went down and put his
mouth on it and played with it with his tongue. He sucked it a few times
and then gave me some light nibbles. I always thought it would hurt, but it
truly felt amazing and I'm sure I moaned a bit. He gave my breasts
attention for a while and then slowly worked his way over my neck and my
ears and eventually just kissed me on the mouth.

After I was thoroughly aroused, he slowly slipped down and pulled off my
panties. He stroked my cock for a minute or two and then lightly wrapped my
panties around my cock. This excited me, but I wasn't sure where it was
going. He then told me to lie on my stomach, but as I rolled over, he put a
small pillow under my cock. This forced my ass to stick just a little bit
up in the air. He went over to his dresser and pulled out a bottle of lube
and a condom. He spread my legs and then my cheeks and worked up to three
fingers in, but this time with lots and lots of (real) lube. He then put on
a condom. I had no idea why, but I figured his cock would probably feel
just about the same in my ass either way. Even though it was already a
lubricated condom, he put some extra lube on it just to make sure we
wouldn't need any more.

He slowly lowered his weight and put his manhood in my ass. It hurt a
little again. I was mostly flat on my stomach, not on my knees so the angle
wasn't quite as productive for deep penetration, but the additional lube
did a world of good and I was overall much better off than the time before.
He just laid there for a while, the whole of his weight on me and his whole
cock in me. It actually made me feel so good and so safe and I loved
feeling him on and in me. My stockinged legs felt SO good against his and I
could feel his hot breath against my upper back/neck. It was amazing. While
laying there, he told me how beautiful he thought I was and how glad he was
that he met me. He started slowly pulling back his hips and thrusting into
me, but his upper body barely moved. I couldn't move an inch, I was
completely pinned down, but it made me feel so amazingly submissive...and
somehow feminine.

He slowly quickened his pace, his cock going in and out of me, his front
slapping against my back. He was thrusting hard, slamming his cock into
me. It hurt, but more than that, it just felt amazing. The thrusting made
my body move a little and made my cock slightly slip in and out of the
panties Jack had put around it. Even without my sexy lover fucking me, the
panties alone could have gotten me off. I was in heaven. He fucked me like
this for a long time, but I'm not sure for how long. Eventually he told me
to turn over. He moved the pillow and started to fuck me missionary
style. I now truly felt like a girl. He leaned forward and kissed me as he
continued to fuck me. After a bit, he sat up a bit and started stroking my
cock with the panties on it. It couldn't have been more than two minutes
before I blew my load all over the panties.

He threw the panties halfway across the room and just continued fucking me,
somewhat speeding up his pace. After maybe 5 minutes of this, he got up,
pulled off the condom and straddled my head and started fucking my mouth (I
then realized he used to condom to keep his cock clean for this). He only
lasted a minute or so before he blew his load. It exploded, spurt after
spurt. There was so much that I had to swallow multiple times to make sure
I didn't waste any of my man's juices. It tasted SO great. I used my mouth
and hand to help milk every last drop out of him and when he finished, he
laid down beside me, holding me close and said "I love you Jessica." And I
responded with "I love you too daddy!"

We cuddled and kissed for about 10 minutes, but I then realized how late it
was. It was almost 9pm and I was supposed to reach my family (who lived
about 5 hours away from Jack) at about 9. I told him my situation and when
he looked sad when I told him I had to leave, I promised him I would visit
him on the way back. This seemed to satisfy him. I ran to the room where I
had changed and stripped out of my lingerie. I went into the bathroom to
wash off my makeup, but this was no easy task. I found the makeup remover,
but it took me 10 minutes or so to get it off. I looked around for my
clothes, but then I realized that I only walked in wearing a thong, bra and
my shoes. My pants and shirt were in the car. I found the thong and slipped
in on and I grabbed the bra and my shoes. I figured I could pick up my new
clothes when I came back to visit Jack. Jack and I got into the car and
drove off. In the car, I put on my clothes, but left the bra off. Jack and
I didn't talk too much on the ride back to the theater. Once we got there,
we exchanged numbers and said goodbye.  I started to walk away, but
suddenly realized that I would miss his attention. I ran back and gave him
a big kiss and then ran to my car.

I called my family and told them I was already a couple hours behind and
then I had stopped at a rest stop and fallen asleep for a few hours (though
it seemed like a stretch, it didn't seem too far out) and they bought it. I
ended up getting in at about 1:30 (I made good time). The whole drive
however, I just thought about my time with Jack...and about my next time
with Jack.


Thank you so much for all the wonderful feedback after the 1st chapter. If
anyone has any questions or comments or just wants to chat sometime, please
feel free...even encouraged to e-mail me at George3130@gmail.com.