Sexy Redhead


Yes. I know she's only eighteen. 	

Yes. I know I'm forty-two. 

Yes. I know other applicants had better qualifications. 

Yes. I know I was thinking with another head. 

...but it's just a data-entry job after all. 

I was talking to my secretary, Gen . Gen  is 47 and 
has been with the company almost the full fifteen years 
we'd been in existence. That was when Lily walked in. 
She was tall and striking. Most of all she was a 
redhead. There is something about redheads that just 
drive me wild. Especially attractive redheads. There's 
something completely intangible that just strikes me 
against my head and says "Look!" 

"Hello," Lily said to Gen . "I'd like to apply for 
the job opening." She wore nice blue jeans and a light 
pink blouse. I still remember intensely what she wore 
that first moment I saw her. If her intention was to 
look dressed up and yet casual at the same time, it 
worked. 

I noticed the resume in Lily's hand was pretty 
sparse. Of course, how much experience can an eighteen 
year old really have? I was mildly impressed that she 
thought to have a resume. 

"We'll call for an interview in the next couple of days 
if we're interested in you," said Gen . 

"Thank you," said Lily very politely and turned and 
started to walk away. 

Damn! The curves of her butt filled her jeans mighty 
nicely. Her red hair lay loosely on her back and just 
below her shoulders. My dick twitched. It was her 
definitely her butt that caused that. I momentarily 
fantasized about entering her pussy from behind. 

"Miss...?" I called out. 

She stopped and turned and looked at me. 

"I'm Jacob Anderson, the owner. If you have a moment, I'd 
like to go ahead and interview you now." 

"Sure!" said Lily with a big beautiful smile forming 
on her face. 

She was truly gorgeous. I twitched again. 

"What about...?" said Gen  as she pointed to a couple 
of sheets of paper on her desk. 

I knew that this was something that needed to be taken 
care of just as Gen  knew it. I'd work late today, I 
quickly decided. 

"I'll take care of it," I told Gen . 

Gen  looked at me and then the girl. 

"In here," I told Lily as I went into my office. "Go 
ahead and close the door." 

I sat in my chair. Lily sat in one of the two chairs 
in front of my desk. She chose the one on the right. 
The left chair was partially blocked by the computer 
monitor on the left side of my desk. She sat quietly as 
I scanned her resume. Lily. Very respectable 
high school GPA, sales clerk for The Wap, before that 
worked at Super Pizza. Going to school at State 
University, business major. 

I looked up from the paper. 

"So Lily, what is your major?" 

"I'm a business major, Mr. Anderson. I'm undecided 
whether I want to be in the financial market or if I 
want to be running a company. I want to know the ins 
and outs of business." 

I though she handled the question very well. She knew I 
knew the answer to my question. 

"Have you done data entry before?" 

"No, but I know how to work a computer." 

"How fast do you type?" 

"I don't know. I've never taken the test." 

"Mr. Anderson...?" her voice broke in. 

"Uh..." I realized I was staring into her eyes and had 
gotten lost.  

"Uh...you can call me Jacob. We're all on a first name 
basis here." 

"Um..." 

"That will let me know if you'll fit it." 

"Okay...Jacob," she said with hesitancy. 

I picked up a pen. I twiddled the pen back and forth 
with it held between my index finger and thumb. "Now, 
tell me about...oops!" The pen "accidentally" flew out 
of my fingers. It bounced on my desk and onto the floor 
in front of her. 

She bent over to retrieve it. I smiled as her blouse 
hung slightly open. I saw her cleavage. It looked like 
she had some decent-sized tits. I averted my eyes as 
she came back up. 

"Thank you, Lily," I said as I took the pen from her. 

"You're welcome." 

I put the pen down. 

I looked into her eyes, smiled, and leaned back in my 
chair. "Tell me why I should consider giving you a 
job." 

"Well, Mr. Anderson..." She paused when I wagged my 
finger. She began again. "Jacob, I am a hard worker. I 
stick to my tasks and get them done. I am a fast 
learner and I think you'll find I can do a lot more 
than data entry." 

I tried not to go "there" in my thoughts after hearing 
her say "do...more", but I went "there". 

"I get along with everybody and I can work well in a 
team. You won't regret hiring me." 

Except for my constant case of blue balls, I didn't 
voice. 

"Sounds good," I said. "The job is 4 hours a day, 20 
hours a week, Monday thru Friday, from 4 PM to 8 PM. 
You'll also be expected to be receptionist from 4 to 6. 
Gen , our secretary, leaves at 4. We stop answering 
the main phone at 6." 

"I can do that," she replied. 

"Do you have any questions?" 

"The hours work great for me, Mis...Jacob. Is there 
flexibility for when school semester terms happen?" 

"Yes. If you're a good worker, we'll want to keep you 
and we can work something out." 

"Good." 

"Oh...wages. It's just minimum wage." 

"That's okay. I just need money to put gas in my car, 
buy some food, and go out with friends. 

I decided to take a slightly improper vector in my 
interview. "So you're a freshman, Lily?" 

"Yes," said Lily. "Jacob," She added. 

"You have an apartment?" 

"I'm in the dorm." 

"You have a boyfriend?" 

She hesitated at first. She didn't expect that 
question. "No." 

My heart warmed inside. I spoke something else. "Well, 
I'm sure the guys will be fighting to ask you out. 
You're very pretty." 

She slightly blushed and I could tell I made her feel 
awkward. "Thank you," she said with a little shyness. 

"Well, Lily," I said as I stood up. "You are an 
impressive young woman. I was impressed on how well you 
remained calm when I asked you some personal questions. 
That shows you know that a business is like a family. 
You've already shown some trust. I'll decide on the job 
in the next day or two." 

She stood up. "Thank you for seeing me, Jacob." 

I smiled. 

I waited two days before I had Gen  call her and offer 
her the job. 

On Monday, I was distracted at work. I couldn't help 
thinking about Lily. She was starting today. 

"Do you want me to stay late and help train her?" asked 
Gen . 

"That's okay. I'll do it." 

I didn't know how transparent my excitement was to 
Gen . I'd never been this way before. Maybe she 
plainly recognized a horny male in her presence. 

Four o'clock finally came. 

Gen  ducked her head into my office. I usually keep 
the door open. 

"The new girl is here," she said. "I'm going home." 

"Thank you, Gen ." She was so reliable. 

I sat patiently in my seat. I didn't want to be too 
eager. I heard a door close and I knew Gen  was gone. 
Off the floor, hidden behind my desk, I picked up a 
vase filled with flowers and walked out. 

"Welcome, Lily," I said holding the vase. 

She looked at the vase, then to me, and then back at 
the vase. 

"These flowers are just something for you to take home 
as a way of welcoming you to the company." 

She smiled. "Thank you." 

I put them on the desk. 

"Come," I said. She followed me down the hallway to a 
small office with two desks in it. 

"Lily, this is Carol," I said introducing the 27-year 
old blonde woman. "She is one of two accounting people 
here. She'll take care of payroll. Carol, this is 
Lily. She just started. When, she's all done just 
send her back down to my office. 

"Sure, Jacob," said Carol, smiling at Lily.  

"Hello?" Lily's voice came into my office twenty 
minutes later. 

"I can tell you right now you need to learn to use my 
name," I instructed with a smile in my voice. 

"Carol's all done, Jacob." 

"Good. Can't have employees not getting paid. They 
don't seem to like that." She smiled. I liked that. 

I went back out to the front desk and pulled up a chair 
next to her and for the next thirty minutes, I walked 
her through the computer screens and showed her what to 
enter in the fields from the paper copies.	These 
were updates of customer data or orders and other info. 
It wasn't a whole lot to do, but I was only paying 
minimum wage and there was filing to do and the 
ubiquitous "other duties as assigned." 

"If you get stuck or need help, don't be afraid to 
ask," I said as I got up and returned to my office.

I had barely sat down when she needed help, but the 
interruptions became less and less frequent as she got 
the hang of the program. 

"Hello, VideoMax. This is Lily." I heard her voice 
say after the phone rang. My phone rang. "A Mr. 
Beaver, from Beaver Screens for you, Jacob," her 
lovely voice told me. Beaver sold aftermarket TV 
screens for automobiles. "Thank you, Lily. Put him 
through." 

That evening, I tried hard not to think about Lily 
too much and I was mostly successful. At least, I 
didn't hover at her desk. 

"Hello, Jacob," Lily greeted me on the next day when I 
returned to the office at 4:30. 

"Hello, Lily, you're looking very lovely." 

She returned a shy smile to me. "Janet would 
like you to call her." 

"Thank you." I went into my office to make the call. 

"Hello, I'm Don," I later heard my plant manager 
introducing himself to Lily. 

I couldn't make out much of the conversation. 

Just before 6:00, I came out. "How are things going?" 

"Okay, Jacob," she replied. "I didn't realize I was 
working at dinner time. Yesterday, I was so nervous I 
didn't notice. Today, I'm hungry. Working only four 
hours, I don't think I get a meal break." 

"No, but I don't mind you eating at your desk if you 
work at the same time." 

A man walked into the office carrying a sack. "I'm 
looking for Jacob Anderson." 

"Here," I said. I pulled out a twenty from my wallet. 
"Keep the change." I took the sack. 

"Thank you!" the delivery man said with a big smile and 
then left. 

"Voila! I have dinner for us." 

"Oh, I couldn't." 

"I have too much food here." 

I could tell she was thinking about it. The Chinese 
food did smell good. I pulled up a chair and started 
taking the containers out of the bag. 

"Thank you," she finally said. 

"We're all here for each other." My mind screamed with 
excitement. 

I made small talk and asked her how school was going. 
It was only three weeks into the semester. 

"I quite enjoyed your companionship for dinner," I 
said. "I'd like to do it again tomorrow." 

"But..." 

I quickly interrupted. "If you're going to say 
something about money, don't. I have lots of money. I'm 
just paying you minimum wage. Consider it a perk." 

"Thank you," she said again in her polite manner. 

Over the next two weeks, I learned about her family and 
her likes and dislikes. She learned I was married once 
for only a year when I was twenty-one.  

"So what do you like about a guy?" I asked her. 

"He has to show he cares about me. Not just pretending 
he's listening to me, but shows it by doing things that 
show he listened. Someone who can make me smile and 
feel warm and comfortable about. Trust is important." 

"What to like about a girl?" she countered. 

"Well since I'm a guy, I think about physical 
attributes first, but I like a woman who'll be there 
for me even when I make mistakes. Someone who's willing 
to stay around if times become tough." 

"What do like physically?" she asked. 

"Well..." I was on the spot. "I like a woman who's in 
shape. She doesn't have to be a model or an athlete. 
She just shouldn't have let yourself go. I like women 
in lingerie. I like the peek-a-boo quality that 
lingerie provides. I like to think 'Did I see what I 
think I just saw?' One other thing that I have to 
confess..." I looked into her face to see her 
expression. She was intently listening. "One of the 
reasons I hired you is that you are a redhead. I like 
redheads a lot. Of course, these last two weeks I've 
discovered you are much more that just a redhead. You 
are a completely charming woman and you are a hard 
worker and I know I made the right choice in hiring you 
even if my reasoning was strange." I paused. "I hope I 
haven't offended you." 

I could tell she was a little surprised. 

She smiled. "Well I'm glad my red hair was good for 
something. It makes up some for being teased as a kid." 
She laughed. 

I released my breath. I just noticed I was holding it. 

I stood up. "Thank you, Lily," I said and put out my 
arms for a hug. She was tentative at first but then 
embraced me. 

Damn! She felt good in my arms! 

On Monday, when Lily got in I asked her if she could 
stay late for an hour. She said she could. At 5:00, I 
headed out to the parking lot and found her car, a ten 
year old Taurus. I put on some overalls and some 
goggles. I crawled under her car and opened the oil 
plug. The oil poured out all over the asphalt. I 
tightened the oil plug back up. I disposed of the 
goggles and overalls in the green dumpster. I kept back 
a few data entry forms and gave them to her at 8:00 and 
told her I needed these in today. She cheerfully 
obliged. 

At 8:40, she poked her head into my office. "They're 
all entered, Jacob." 

"Thank you, Lily." I picked up my coat. "Let's get 
out of here. It's late." 

"Sounds good," she replied. 

"Uh-oh!" I said as we walked up to her car. I bent down 
in front of it. 

"What?" she said with a little anxiety in her voice. 

"Looks like your engine lost all its oil. You can't 
drive it." 

"Oh, no! Are you sure?" 

"Yes." 

"Ohhhh! I can't afford to fix it or get a new car." 

"Lily, let me drive you home. I'll pick you up 
tomorrow. I'll check your car out in the daylight. It 
might be a simple problem." 

"Okay," she said. I could see the worry on her face. 

"I'll take care of you," I assured her. 

I drove her in my Lexus to the school. When we stopped 
in front of her dorm building, I leaned over and kissed 
her softly on the cheek. "See you tomorrow. I'll pick 
you up. Don't worry about the car. I'll take care of 
it." 

Lily's hand touched the cheek I kissed. She got out 
of the car. and looked back at me. Her hand was still 
on her cheek. 

I waved and drove off. In my rearview mirror, I saw a 
small return wave. 

"Good news, Lily!" I exuberantly said when I picked 
her up. I leaned over and kissed her on the cheek 
again. Her hand went up to her cheek again. "The oil 
plug on your car just fell out. I put it back in. I 
made sure it won't fall out again. I went ahead and put 
oil back into the car." 

"Oh, wonderful," said Lily with excitement. "Thank 
you." She looked relieved. 

"No charge," I quickly added. "It cost nothing." 

I pulled into my reserved spot. We went over to her car 
and I had her start it up. It roared to life. After 
all, I only gave it an oil change. 

"Thank you, thank you," she said happily and bounced 
out of the car. 

She hugged me. I wrapped my arms around her and held 
her tight. 

Finally we began to separate. 

"You're welcome." I kissed her softly on the nose. She 
became bashful and nervous again. "We better get into 
work. I know that boss of yours can be a real asshole 
if you're not in on time." 

She laughed at my joke. The joke broke the sudden 
awkward tension. 

For the next couple of weeks, I kissed her on the cheek 
to and say "Thank you," for basically her just doing 
her job. I noticed she became more relaxed about it. 

One evening as I left her desk and walked back into my 
office I sighed, "I wish she'd show a little bit more 
cleavage."  

I turned and she was right behind me. "Uh...Jacob?" she 
said, "Don called. He won't be in tomorrow. Car 
problems." 

"Uh...thank you, Lily." 

My mind raced. Did I mutter that under my breath? Did 
she hear it? 

My stomach did flips. 

"Did he check his oil?" I quickly said with a joke 
attempt. 

She didn't smile. She turned and went back to her desk. 
The phone rang. "Carol?" I heard her say, "I'll 
transfer you." 

I sat at my desk. I could feel sweat trickle down my 
body. My mind was in a blur. Before I knew it she was 
standing in front of my desk. Her purse was in her 
hand. "I'm going now," she said. 

"Have a good night," I replied. I looked down and tried 
to look busy. 

"You need to thank me?" 

"Huh?" I looked up at her. 

"Mandy is teaching me the accounts payable system, 
since she's been working a little late this week." 
Mandy worked with Carol. "Here's a check from Harrison 
Electronics." She put in on my desk. Harrison was a 
company that was behind in payments. I picked it up. 
The check was for at least half of what they owed us. 
It was a very good start. "I called them and pretended 
to be a lawyer." 

"Lily!" I said, my voice getting animated. "You can't 
do that. 

We'll get in trouble." 

"But I got the check..." she protested. 

"I'm glad," I said, "just don't pretend to be a lawyer 
again. Okay?" 

"Okay." 

Lily left and so I averted a future lawsuit against 
my company. 

I often didn't come out to see Lily until after five. 
It wasn't until after five that the business day 
started to wind down. The next day, it was Lily who 
came into my office for our first contact of the day. 
She came into my office just before five. My mouth 
slightly gaped. She wore a scoop-neck shirt. 

"Jacob...?" she said. I heard something girlish in the 
way she said my name. "Oops." 

It almost felt like it was in slow motion. I can so 
clearly recall this event in my head. I watched as the 
pen slipped from her hand and fell to the floor. She 
bent forward at the waist. Her shirt hung open and I 
could quite clearly see her tits. 36C's I quickly 
guessed. She wore a white lacy bra with sheer sections 
that gave it a peek-a-boo quality. My dick twitched. 
She picked up the pen and slowly, too slowly, raised 
back up. 

She walked around to my side of the desk. I felt 
nervous. My dick strained against my pants. 

"You never thanked me for getting that Harrison check," 
she said. She sat in my lap, wrapped her right arm 
around my neck, and presented her right cheek to my 
face. 

I was sweating and breathing hard, but I knew what to 
do. I kissed her cheek. "Thank you, Lily. I 
appreciate you very much." 

"And I want to thank you," she said. She turned and 
kissed my cheek. 

"What's that for?" 

"For being such a good boss." She got up but ended up 
squishing my dick doing so. She looked down at my 
pants. Was she eyeing my erection? "See you at dinner." 
I could have sworn she was wiggling her butt on purpose 
when she walked out. Well, maybe not. I was in a 
heightened state of arousal after all. 

Things didn't move any further the next few weeks. She 
would kiss me on the cheek now and that was nice. Plus 
every so often, she wore something a little more 
revealing and there was always a time during those days 
that she would turn or bend and I could look down her 
shirt into those beautiful tits. On those evenings, I 
always ended the work day in the bathroom to relieve my 
painful blue balls. 

I called Lily into my office one night, about fifteen 
minutes before she was to go home. "Lily," I said to 
her across my desk, "I never notified you that you 
passed your one month probation period." I stood up and 
walked around my desk and sat on the edge of it. "You 
have more than surpassed my expectations of you as an 
employee. Thank you for being so dedicated." I leaned 
down and lightly kissed her on the lips. I heard her 
shiver. I slowly backed away. She looked disoriented.  

"Thank you," she said in a whisper. Her face was flush 
with perspiration. She stood up. "It's hot in here 
today," she said almost to herself. "I better get back 
to my desk." She stumbled into the chair. "Oh." She 
walked a little unsteadily back to her desk. 

I smiled. 

In early December, Lily came into my office at about 
six and sat down in the chair. 

"Jacob?" 

"You look stressed," I said. She did. And tired. 

"I'm caught up with everything," she said "and I was 
wondering if I could go home early." 

"Is there a problem? Are you okay?" My heart ached in 
concern for her. 

"I just have term papers to finish and finals to study 
for. The couple of hours would help." 

I stood up and came up behind her chair. 

"Sure, sure," I said. I put my hands on her shoulders. 
She moved slightly from the surprise touch of my hands 
but then relaxed in a sign of trust. "Let me try to 
massage some of that tension out of you first." 

I began to squeeze her shoulders and then began to rub 
and press on her upper back. My hands moved to the back 
of her neck and I squeezed. 

"Is it too hard?" 

"No. It feels good." 

"Good, good." I continued her massage. 

"I'm going to go a little softer now," I told her. 
"This will help you relax more." 

I bent down and lowered my lips to the back of neck. I 
slowly and softly kissed her neck. 

"J..." she said. 

"Shhhh," I interrupted. "Take in the sensations. 
Relax." 

I persisted to kiss both sides and the back of her 
neck. Her breathing slowed to where it nearly matched 
the gentle pace of my kisses. I smelled no perfume on 
this eighteen-year old beauty. I liked that. 

I was getting a little tired but I carried on. 
Sometimes I would return to rubbing with my hands and 
then come back to kissing her neck. I kept an eye on 
the clock. After fifteen minutes, I stopped. 

"Go on home, Lily. I hope you feel better." 

"Thanks, Jacob. That felt good." 

As she went out, I realized I need to start closing my 
door. No one is usually around after 6 PM, but why take 
the chance. 

The next day, I didn't come out to the front desk until 
the Mobile Waiter brought dinner at 6:00. 

"Let's have dinner at my desk." We sat in the two 
chairs in front of my desk. I also closed my door. 

"So how are you feeling?" I asked. 

"Better. That massage really helped me relax. I fell 
asleep when I got home. Maybe I needed sleep more. But 
I felt refreshed and was able to get some stuff done 
during the break between my classes." 

"Wonderful," I said. 

When dinner was concluded, we stood up. I leaned over, 
held her upper arms lightly in my hands and gave her a 
soft slightly lingering kiss on her lips. I saw Lily 
close her eyes. 

"Thank you for being such a good friend to me," I 
whispered softly. 

Her breath became a little harder. I kissed her softly 
on the lips again. 

"You mean so much to me," I said. "It's good to have 
someone you care about." 

One more time I softly kissed her lips. 

"See you later." I put the excess dinner into the trash 
and sat down at my desk. 

Lily walked out but several times, before she reached 
the door, she stopped and looked back at me. 

Dinner time ran that way from now on. In my office with 
the door closed. I gradually kissed her a little 
firmer, a little longer, and a little more often. 

The following week, we were eating dinner and she was 
unusually quiet. 

"Are you okay?" I asked. "School okay?" 

"Yeah, yeah, school just finished for the semester." 

I waited as patiently as I could, but after a couple of 
minutes of silence I had to speak, "Please tell me, 
Lily? I'm your friend." 

She looked at me. Moisture formed in the corner of her 
eyes. 

"I...I think I love you," she finally said and then she 
stood up and burst out of my office. 

It took every ounce of will I had to not go after her, 
but I didn't. 

I knew she needed to be alone. 

At about 7:00, she came back into my office and sat 
down in the chair. I came out of my executive chair and 
sat in the other chair and waited for her to speak. 

"I think I need to quit," she said with a trembling 
lip. 

"What if I told you I think I love you too?" I said. 

She looked at me with surprise. Maybe the thought 
hadn't occurred to her. I decided to continue. 

"Lily, every day I look forward to when you come in 
to work. It takes a lot of effort for me not to be 
waiting at your desk at 4:00. I want you in my life. I 
know I'm a lot older than you, but the way we get along 
with each other, it's almost as if we were made for 
each other." 

"Please don't go," I added. 

She looked into my face. I think my words had some 
effect but I wasn't sure. I stood up and outstretched 
my arms. 

"I want to hold you," I said. 

She rushed into my arms and we held each other tightly 
and my lips found hers and she kissed me back for the 
first time. Our lips passionately sought each other 
out. Finally, we parted and I just held her in my arms 
for the longest time. She laid her head against my 
shoulder. 

We ended our next couple of dinners kissing and holding 
one another. On Tuesday, of the next week, just a week 
before Christmas, I came out to her desk right before 
it was time for her to go. I had a gift bag in my hand. 

"What's this?" she asked with surprise and delight as 
she took the bag. 

"Open it when you get home," I told her. 

During dinner the next day, I asked her how she liked 
her gift. 

"I'm glad you asked me to open it at home," she said a 
little bashfully. 

I smiled. 

On Friday was the company Christmas lunch and party. I 
let everyone go home at noon and Lily made the party. 
I'm glad Lily socialized with the other people. It 
would have certainly been awkward if she had been 
hanging on my arm or if she was always right by me. 
People finally went home and I looked around and 
noticed Lily had left too. I wanted to give her a 
secret kiss good-bye. I went to my office to get my 
briefcase. 

When I opened the door, Lily was sitting on my desk. 
She wore a teddy. It was the same color red as the 
color of her hair. The top was sheer and lacy with 
little gaps. A very arousing peek-a-boo. I could see 
her right nipple. She stood up. Now I could see some 
red pubic hair just above where the cloth covered her 
clit and pussy opening. 

She looked damn good in the Christmas present I gave 
her. No. She looked hot! 

I closed the door and started to run toward her and 
then in what I'm sure looked rather silly and comical, 
I turned around went back to the door, locked it, and 
then turned back and ran toward her again. 

I wrapped my arms around her and bent her back. My 
mouth went down and my lips kissed just above her tits 
and then went down into her exposed cleavage. My tongue 
darted in between. She hissed as I went between her 
tits. 

"Oh, Lily!" I exclaimed. 

I straightened up and my hands went to her bare butt. I 
squeezed the two firm round globes. My pants-enclosed 
cock ground against her nearly naked pussy.  

I finally separated.  

"You're beautiful," I said. I kissed her lips and that 
set off another round of our hands roaming each others' 
bodies. I took a step back. I had to. I couldn't keep 
my hands off her. 

She watched me as I began to unbutton and take off my 
shirt. 

"You know," she said, "Having a thin piece of cloth in 
between my butt cheeks is not very comfortable. This is 
definitely for a guy's enjoyment because it's 
uncomfortable for me." 

"Definitely," I said as I undid my pants while I kicked 
off my shoes. 

"Definitely." 

My pants fell down and Lily's eyes went to the bulge 
in my underwear. 

"Wow!" she said as my erection came into view. I 
slipped my feet out. 

"If that's uncomfortable," I said eagerly, "I could 
take it off for you." 

"I'll do it," she said pulling her eyes away from my 
cock. 

She undid the crotch snap and extracted the material 
out of her crack. The spaghetti straps slid off her 
shoulder and she pushed the teddy down. It dropped to 
the floor. 

There was a moment when it seemed like neither of us 
knew what to do next. 

"I want to suck on your tits," I announced to her. 

I stepped forward and bent my knees and took her tits 
into my hands. 

Lily's tits were firm. Despite their good size, they 
did not sag. The joys of youth. I put my mouth on her 
right nipple. She stumbled a step back, but then she 
was steady against my desk. 

"Oh," she moaned. 

I released her very wet tit and went to her other tit 
and nipple. 

I alternated between them. Sucking on her nipples. 
Kissing. Licking. 

My tongue running in the valley of her hills. 

I felt her hand around my dick. I straighten up. 

"Lay back on the desk," I said. I positioned her butt 
on the edge of my desk. We couldn't go length-wise on 
the desk because of the computer. Her head went over 
the side. 

"Be right back," I said. I slowly opened the door and 
looked around. I ran naked to the guest couch. I pulled 
out the three seat cushions and came back in. Yes, I 
made sure I relocked it. I raised my executive chair as 
high as it would go and put the cushions on it. It was 
perfect! It actually tilted her head forward slightly, 
so she could see better. 

"Thanks," she said. 

"My pleasure," I replied. I was happier than I'd ever 
been in a long, long time. 

I lifted her legs and pushed them apart to the sides. 
My heart felt like it just stopped. There it was. 
Lily's beautiful pussy. The wonderful red pubic hair 
was trimmed for wearing a bikini. There was another red 
area that particularly grabbed my attention. 

Lily moaned and her body arched as my tongue flicked 
over her clit. 

I began a slow, deliberate licking, kissing, and 
sucking on it. 

"Oh!" she moaned. 

I would sometimes dart my tongue in between her lips 
and penetrate into her pussy. Her juices started fast. 
I drank them up as if it was the rarest of nectars. 

"Ooooooh!" she moaned. Her moan was changed. More 
aroused. I sucked deeper on her clit. I licked her 
firmer and she was also very aroused when I licked 
along the outside of her lips. She arched her back and 
pushed her pussy into my face. 

"Aaaaaaaaah!" she cried out and I felt her come. 

I stopped. 

"Oh, wow!" she said. 

I waited about a minute. My aching cock needed relief. 
I stood up and stepped up. I grabbed my cock and lined 
it up with her pussy. I inserted it into her delicate 
folds. 

I looked at her face before I pushed into her. I was 
perplexed. She looked almost...scared? I watched her 
facial expression as I slowly pressed my cock into her 
pussy. I felt her warmth as her body opened for me. I 
was very surprised to find resistance inside her. 

"Are you...are you a virgin?" I stammered in surprise. 

"I wanted to wait for the right one," replied Lily in 
aroused sensual breath. "You are the one." 

My head spun. I was no longer just a 42-year old man 
having sex with an 18-year old woman - a girl 
essentially. I was having sex with a virgin, I was 
deflowering her, I was the first one ever to fuck her 
cunt. Needless to say, no matter how I said it, it was 
extremely exciting for me. 

"This might hurt a little," I cautioned. 

"I know." 

I swear when I broke her hymen that she made the exact 
same sound a mouse makes when it gets stepped on. 

"Stop a second," she said as she waited for the pain to 
subside. 

I happily obliged. I was partially inside her! It felt 
good. 

"Okay," she said a few seconds later. 

I gradually pushed the rest of my cock all the way 
inside her pussy. 

She felt so good. She was warm, she was tight. It was 
pure ecstasy. I slowly pulled back out with just my 
cock head inside her and then bit by bit pushed back 
in. I heard her exhale with my every entry. Over time, 
I began to speed up inside her. Her tits jiggled and 
grabbed my attention so I grabbed them in my hands. I 
held on to her tits and squeezed them as I leisurely 
fucked her. 

After a couple of minutes Lily said, "Climb on top of 
me. I want to feel your body against mine." 

I had no problem with that. 

Lily had to scoot a little. I needed to get at least 
some of my legs supported by the desk. We pushed my 
chair back. She lost a little back support but she was 
in no risk in falling. She pushed her tits up and I 
pressed my chest against them. My cock easily re-found 
her pussy and slid back into her like it was home.  

In hindsight, it would have been more reasonable for us 
to lay on the carpet. However, this turned out to be a 
wonderful first time and so I lasted much longer that I 
would have normally. It was difficult to thrust into 
her. I had little leg support. I used one of the 
visitor chairs to hold up my feet. As strange as it all 
seems, all of it just made that first time with Lily 
even the better. 

"I never imagined you'd feel so big inside me," she 
said. There was awe in her voice. I didn't mistake this 
statement for saying she thought I had a small dick. 
She was a virgin. A tampon was the biggest thing ever 
put inside her. In fact, I was a very respectable seven 
inches. 

Even at the slowest sex pace, the sensations build. 
Also, the very fact that I was causing those erotic 
moans coming out of Lily's mouth was very stimulating 
for me. After fifteen minutes, I groaned with every 
short, hard thrust into her pussy. My orgasm was 
becoming imminent. 

She ground her clit against me and moaned out, 
"Aaaaaaaah!" She was coming.  

I pressed harder and harder. "Unnnnn!" I groaned and I 
released. I felt a hard squirt shoot out. It was so 
hard it almost burned. Then several other squirts came 
until there was no more. It was a lot of come. I hadn't 
been in a pussy for ten months. Only masturbation. 

"You are so beautiful, so wonderful, so special..." I 
said as I laid kiss after kiss after kiss on her face. 

"It was even better than I imagined," she said. "Sex is 
all they say it is and more." 

"Merry Christmas," I said. 

"Merry Christmas." Lily kissed me. 

"What are you doing for Christmas?" I asked. "You're 
not going to stay in the dorm all alone?" 

"I'm going to my parents." 

"Oh," I said with disappointment. After such a 
fantastic first time, I just wanted to do it again and 
again. 

The week between Christmas and New Year's I close the 
office, so on the Tuesday after the holiday, I finally 
saw Lily again. She surprised me. She was wearing a 
skirt. She always dressed very nicely, but it was 
always with jeans. 

"Good morning, Lily," I said with a big smile as I 
passed by the desk. My heart thumped and my cock 
started to fill with blood. 

"Good morning, Jacob," she replied with an equally big 
smile. "It was the best Christmas party I've ever been 
too. Here's your phone messages." 

I took the small stack of about five. "I'm glad you 
enjoyed yourself." 

I sat at my desk. As usual, my top customers were 
trying to reach me after the holiday. The last message 
caught my eye. It said: 

"Plan on working late." It was unsigned. 

Lily wouldn't let me even kiss her during dinner. 
When I tried to find out more information on the last 
message, she acted coy and innocent. "It might be 
helpful if you weren't wearing any clothes," she told 
me. 

I was too distracted to do any work. I got naked 
already by 7:30. 

I phoned Lily.  

"Did I get any additional messages?" I asked. 

"No," she said. 

"Are you sure?" I practically whined. I was too 
excited. "Maybe it might start a little earlier?" 

I saw Lily peek her head around the door while 
holding the phone. 

She giggled and then hung up. 

I was impatient. I had a very hard hard-on. I kept 
having to stop myself from absent-mindedly stroking my 
cock. I didn't want to get aroused too fast. 

Fortunately, she didn't make me wait much longer. She 
stepped into my office and closed and locked the door. 
She whipped off her shirt and flung it in my direction. 
If fell well short. She reached behind and undid her 
bra. That flew even less. She shook her body. Her tits 
jiggled for my pleasure. 

"I need to thank you," Lily said, as she walked 
toward me. 

"What for?" I said playing the game. 

"You've been such a good boss. You've taken care of me 
and..." She climbed up on my lap. Her legs straddle me. 
She reached down and took hold of my cock. She sat down 
and I was surprised as I slipped right into her pussy. 
"...and you've filled my every need. Mmmmmmm, Ohhhhh!" 

My first surprise was that she had no panties on. She'd 
been out there with no panties on all that time. The 
first surprise facilitates the second surprise in that 
my cock entered right into her warmth. 

Lily began to bounce up and down on my cock. Her tits 
shook right in front of my face. I did the natural 
thing. I sucked on them. I smothered my face within her 
cleavage. She gratified me by pushing her tits together 
around my face. 

It felt so good and then she stopped and got off me. I 
looked at her in frustration. She undid her skirt and 
it fell to the ground. She then turned around and bent 
over the desk. She spread her legs open. An invitation. 

"Here's your chance to fulfill every male boss's 
fantasy," Lily said. 

"What?" I said truthfully. 

"Every man wants to fuck some girl bent over his desk. 
Here's your chance. Fuck me." 

I was shocked. Foremost by her language. I'd never 
heard her talk like that before. It was exciting yet a 
little repelling at the same time. After our first time 
of sex, I could she was no longer the quiet young 
woman. That person was gone. She was now a sensual, 
erotic woman who had no problem voicing her physical 
needs. Secondly, yes indeed it was a fantasy to have a 
woman bent over the desk, but I never thought I'd do 
it, nor did I even try. 

I stood up and inserted my cock back into her open 
pussy. 

"Don't be afraid to fuck me hard," she said. "Live your 
fantasy. Or do it however you want. I love you." 

I slowly moved back and forth inside her. 

"Oooooh, it feels different this way. It's hitting 
just..." She paused as sensations hit. "...the right 
spot." 

Her moaning was too provoking for me to hold back and I 
began to thrust into her in earnest. I could hear her 
boiling toward orgasm and I remembered her words, so I 
chose to fuck her hard. My hands held her waist and I 
now pounded into her. Just a few moments after I 
started to fuck hard, she cried out and came. I 
continued to fuck and slam hard into her pussy. I could 
feel my cock building and building. 

"UNHH!" I groaned and shot my come into her. 

"I can feel it," she moaned. "I can feel it shoot." 

Damn, she was hot! 

Just before 8:00 every night was the start of very fun 
times for us over the next few months. When the school 
year ended, she quit. She said she wanted to work full-
time somewhere. Make more money. I'd been giving her 
$200 a month out of my own paycheck since we started to 
have sex. My only stipulation was that at least $50 of 
it had to go to buying lingerie. I offered her full-
time work over the summer. It wasn't about the money. 

The college boys had become interested in her and she'd 
become interested in them. It didn't come as a shock. 
Our relationship latest longer than I expected. I still 
miss Lily. My beautiful redhead. Maybe she'll show up 
sometime just to relive some old times. You know what I 
mean. 

Yes. I know I'm forty-three now. 

Yes. I know I shouldn't hire part-time help with the 
hope that I can one day fuck them now. Sorry, I mean 
have sex with them. 

But here's an important fact. Even though I'm getting 
older, the college freshman girls are still eighteen.