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                 K R I S T E N' S    C O L L E C T I O N
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This work is copyrighted to the author © 2008.  Please
don't remove the author information or make any changes
to this story.  All rights reserved. Thank you for your 
consideration.
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The Challenge 
by AndoverBlonde (andoverblonde@hotmail.com)

***

I haven't written any stories or accounts for a long 
time, but a very sweet friend of mine recently 
challenged me to write another. The challenge arose 
after he commented that he enjoyed my writing because I 
was not very graphic. He and I disagreed on this point 
somewhat, but I understand his position. So my goal in 
writing this story is to take it up a notch. That does 
mean, however, that this is a story, and not an actual 
encounter. (MF, exh, intr, rom)

***

Hi Readers

I haven't written any stories or accounts for a long 
time, but a very sweet friend of mine recently 
challenged me to write another. The challenge arose 
after he commented that he enjoyed my writing because I 
was not very graphic. He and I disagreed on this point 
somewhat, but I understand his position. So my goal in 
writing this story is to take it up a notch. That does 
mean, however, that this is a story, and not an actual 
encounter.

Although just a fantasy, I will try and keep 
descriptions as accurate as I can. So, yes, that means 
that although this hasn't happened, the characters are 
real. What I do not know about them (him!) I will make 
up to fit the story, and hopefully to meet the 
challenge!

Sandra (AKA AndoverBlonde)

PS – Previous writings are in directories 31, 33, and 
36

***

Life has been very good to me and I am generally a 
happy person. It's my belief that a happy positive 
outlook influences the direction of one's life, and I 
believe this holds for both emotional and physical 
wellbeing. I have a job that I enjoy, coworkers that I 
love, and a daughter that I cherish. I also have a wild 
streak that instead of ignoring, I respect. And you 
cannot deny or abuse the things that you respect.

Now being able to express one's wild streak openly can 
cause problems not easily fixed. Because of this you 
must carefully choose your spots, but you also cannot 
let exceptional opportunities slip through your 
fingers. Finding that balance can be challenging, but I 
truly believe your heart can help find that balance. 
Because of this I do not easily dismiss my crushes. And 
those that I have crushes on are not always 
predictable.

My crush on Anthony would have been predictable if 
everything was completely different! Anthony is 20 and 
I'm 46. Anthony is black and I am white. Anthony is an 
athlete and I just wish I could be! Forgetting about 
age and color, however, we would be a good fit. He is 
tall, kind, confident, and beautiful. For someone his 
age, he is surprisingly articulate. His worldview is 
not self-centered and he truly seems to care about 
those around him. 

I am around Anthony two days a week. He is an intern 
here, a hard worker, and a joy to have around. We 
became fast friends and chatted while he worked, and 
eventually began to trade emails when he wasn't here. 
We discussed everything and, although I could not deny 
my attraction to him, I felt very much like a maternal 
figure – especially when giving my opinions on 
politics, classes, women, etc.

Given my perceived role in his life, I could not have 
anticipated his request. In a very short email, Anthony 
asked if I would pretend to be his girlfriend. When I 
realized he was serious, I told him we needed to meet 
to discuss this request. The meeting was better than I 
thought.

It was a guy thing. It turned out that a few of his 
friends from home were visiting, and he thought he 
could impress them by dating an older woman. Yes, an 
older, attached, white woman. He explained that this 
was a game, that he meant me no disrespect, and that he 
would understand completely if he had made an 
inappropriate request. When he assured me that he 
expected nothing more than to make his friends jealous, 
I agreed. How could I say no? My heart told me that 
helping him out was just the right balance of risk and 
reward.

I did make a single demand – that he allowed me to plan 
everything. He happily agreed. I asked for, and he 
provided, photos of his friends and some basic 
information about them, and photos of his apartment 
with a description of its floor plan. With this 
information I could pretend as if I had been there 
before, and that Anthony and I had discussed his 
friends. We agreed that our 'date' would occur Saturday 
afternoon between 3 and 7. Although he wanted details, 
the time I would spend with him was all I told him.

This was too exciting!

I knocked on his door Saturday at exactly 3:00. He 
opened the door, smiled, and let me in. After entering, 
I kissed his cheek and walked over to the two young men 
in the living room. "Hi, I'm Sandy. You must be Frank," 
I said to the shorter of the two, "and you must be 
Mike" I said to the other. "Anthony has told me so much 
about you! How do you like the community college, 
Frank? And are you still thinking about moving to 
California, Mike?" They nodded and we shared some idle 
chitchat.

"Anthony? Would you please go down to my car and bring 
up my bag and the package on the back seat?" He agreed, 
I gave him my keys, and he hurried on to get my things. 
I was enjoying this immensely! Clearly his friends were 
shocked by the situation. For my part, I just acted 
like this was normal in my life.

It wasn't, of course, but that was the beauty of it. 
For example, I never go business casual on a Saturday. 
But here I was, in a ginger colored Ashford jacket 
dress with matching slingback sandals. My hair was 
pulled back, my make-up was very conservative, and my 
tone very professional. I appeared much more like a 
college admissions person than like the date of a 20-
year-old college student. I deeply enjoyed this seeming 
disconnect!

Anthony came back into the apartment with my bag and 
package. I called to him, "Hey Babe, will you open the 
wine from the package for me, and I brought the beers 
for you and your friends. I hope you guys like Sam 
Adams." I took the bag from Anthony and reminded him, 
in words that everyone could hear, that I needed to 
leave by 7:00 to get home on time.

"Please, pour me a glass of wine, Babe," I said, "I'll 
let it breath while I change." And with that I took my 
bag and went to his bedroom. "I'll be out in a few 
minutes, you should put on some nice music." I 
disappeared to transform from the admissions woman to 
his date.

Once in his room I undressed, took from my bag a 
metallic gold Venus Cowl dress, and pulled on the 
spandex outfit. I love the way the dress works with my 
slightly asymmetric figure, it simultaneously downplays 
my (unfortunately!) flatter butt while accentuating my 
fuller breasts. Using his mirror I traded my gentle 
matte finish blackened cranberry lipstick for light 
gloss classic fire engine red, then added eyeliner, 
mascara, and shadow to match my hazel eyes. Finally, I 
let my hair down and put on my 4" open toe black pumps. 
"Now," I said to myself, "I look the part!"

Exiting the room I can see that I have made my point. 
The 3 boys gazed at me for longer than was polite, and 
I said, half jokingly as I turned around for him them 
to see, "Do you like this outfit, Anthony?" "You're 
gorgeous," he replied, and I kissed him on the cheek 
again as I walked to the kitchen to collect my wine. 
"Any of you boys need another beer?" I asked, and all 
of them said yes.

The next 45 minutes or so were fun! The boys were all 
polite, kind, and flirty. For my part, I jokingly 
rebuffed the comments by Frank and Michael, but happily 
accepted those from Anthony. Finally when a slow song 
was on the radio, I asked, "Hey Babe, are you going to 
ask me to dance?!" Anthony did not waste a minute.

Dancing with him was spectacular! Even with my heels my 
nose only came to his chin and I felt surprisingly safe 
in his arms. Pulling him close, I whispered in his ear, 
"you know that this is a game and that we are only 
playing it one time, right?" He nodded his 
understanding, so I continued, "then you better make it 
believable, Babe." With that we shared our first real 
kiss – deep, passionate, and loving. Absolutely the 
best first kiss I had ever had. "Wow – that was 
fantastic, Anthony! I'm certain we've convinced your 
frien..." his second kiss didn't let me finish my 
sentence.

"Hey guys, I'm sorry! I hope you don't mind PDA's!" I 
said to his friends after pulling away from my date, 
"but I just don't get to see Anthony as much as I need 
to." They laughed, said it was ok, and that they 
understood. Anthony looked as proud as a man could 
look! Clearly he felt that he had impressed his 
friends. I excused myself to go to the bathroom.

When I returned to the room I mentioned that I only had 
another hour or so, and handing Anthony one end of my 
black thong that I just removed, asked if I could 
borrow "my man" for a few minutes. No one said anything 
as I used the thong as a tether and led Anthony to his 
room. I didn't say anything when he left his door 
slightly open.

"Don't say a word, Anthony," I whispered, "we can make 
this one time game truly special." I was aware that his 
friends were watching as we kissed, and although I have 
never been an exhibitionist, I had no intention of 
changing this dynamic. With Anthony facing the door, 
and my back to it, I could pretend not to know that we 
were being observed.

I undid his belt buckle, unsnapped his jeans, and 
pushed his zipper down as we kissed. I pulled his 
underwear down with his pants, and he stepped out of 
both. I then broke our embrace, and just smiled at him 
as I undid the buttons to his shirt. Finally, I knelt 
in front of him and pulled his socks off. Anthony was 
now totally naked in front of me, and he was the most 
perfect man I had ever seen. He was much more muscular 
than I had thought, and much more of a man than I had 
previously experienced.

I pushed him backward to rest against his desk, and 
while kissing him again I took his penis into my hand. 
He was hot, and hard, and perfect. He was too big for 
me to close my hand around and that realization was as 
sexy to me as any that I have ever had. I stroked him 
for just a few moments before I pulled away from his 
embrace – I pulled away so that I could feel him in my 
mouth. 

He was perfect – he smelled clean, he was gentle with 
me, and he let me explore him. I used two hands to 
stroke as I worked as much of him as I could into my 
mouth. The excitement of the moment was getting to me! 
I repositioned to his side, kept him as secure in my 
mouth as I could, and pulled him with only one hand. 
With my other hand I began to masturbate. I knew that 
is friends could see everything, and that excited me 
even more. I am very sensitive, and it took only 
moments before my first 'public' orgasm. 

It wasn't long before Anthony was going to cum. I could 
hear the pace of his breathing, and the rocking of his 
hips had become much more driven and rhythmic. I felt 
him harden, and just before he exploded, I pulled my 
mouth away and held my hand over the head of his penis. 
I stroked him as hard as I could while he came in my 
hand.

I knew he was a little disappointed that I didn't let 
him cum in my mouth, but I also knew he wouldn't be 
disappointed for long. With him looking down at me, I 
licked the remaining sperm from my hand as I gazed at 
his cum covered cock. It was beyond beautiful, and the 
contrast between the milky color of his sperm and the 
deep blackness of his penis was intoxicating.

I pushed him back on the desk, positioned his hot and 
wet penis, and pushed down onto him. While working 
Anthony into my body, I came again, and then again. 
Anthony understood that I would not be able to maintain 
balance, so he pulled me down onto him, forced himself 
in the rest of the way, and then held my hips as he 
stood up. He made two small steps toward the bed, 
rested me down upon it, and began to make love to me. 
He was perfect! Anthony took it slow at first so that 
our bodies fit perfectly, then made love to me like a 
machine. I was in a state of almost continual orgasm, 
for which he showed me no mercy. Finally, when I 
thought I could take no more, Anthony pulled back, 
lifted my left leg, and without ever leaving my body, 
he rolled me over.

"Sandy?" he whispered. "Yes" I gasped. "Are you ready 
to get fucked?" He didn't wait for an answer. We made 
aggressive love doggie style for 10 minutes, and just 
as I could feel him getting ready to cum, he pullout 
out, twisted me around, and pushed himself into my 
mouth. I didn't hesitate and I made sure he knew that I 
wanted this as much as he did. He let out a happy 
boyish laugh after he came, and after I finished 
enjoying him, I giggled too.

"OK Sweets," I said, "I need to get into the shower." I 
showered, dressed in my original cloths, met the three 
boys back in the living room, kissed Anthony deeply, 
and said goodbye.

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. 4-million people around the world 
contract HIV every year. You only have one body per 
lifetime, so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
Kristen's collection - Directory 59