Chapter III

I couldn�t believe it. This was so surreal. I stood in shock for a 
couple seconds and stuttered out a �Yeah I�m Matt.�

�Good, I was hoping you were cute and you turned out to be. You 
wouldn�t believe how many boys from there turn out to be not so great 
looking�Not that I meet a lot of guys, I�m not a whore or anything---Do 
you wanna grab a seat?� She stated.

I was still in shock. I couldn�t believe that one of my professors was 
a sugar momma. I also couldn�t believe she didn�t know I was the same 
kid she kicked out of her room earlier that day. Then again, it�s a 
lecture hall of 350 students.

�What�s the matter Matt? You look like you�ve seen a ghost or 
something.� She asked.

We ordered our drinks and seated ourselves at a table away from the 
bar. She was right, the place was very nice. Hopefully it wasn�t as 
expensive as it looked. I mean, I did have four more weeks with my 
Dad�s money, but I should probably ration it out in case this doesn�t 
work out. Then again, once I get a couple drinks in me I don�t care 
about money. My guitars and video games are evidence of a night with a 
couple beers in me and my credit card at my side while I was online 
shopping. I decided I wasn�t going to tell her about me being a student 
of hers. I wanted to see where the night headed before I made that 
confession. Or maybe a couple martinis would loosen my lips, and 
hopefully hers.

�Oh nothing�s wrong. You�re just prettier than I thought you would be. 
I mean, it IS Craigslist. Thank you for not robbing me by the way.� I 
stated.

She started to laugh.

�You�re making me blush. So you�re cute, charming AND funny. Those are 
some good qualities Matt. You�re winning points already.� She started. 
�So tell me, what�s a boy with said qualities doing on Craigslist? � 
She asked.

The dreaded question. I didn�t know how to answer it honestly, so I 
lied a little.

�I should be asking you the same thing. You�re gorgeous. But I find the 
standard dating sites a bit too boring. I like to take my chances in 
the shark pool. Craigslist is a game of Russian roulette when it comes 
to anything and right now, I�m taking the spin.� I stated.

She looked at me impressed. I then slammed the rest of my martini and 
called the waitress over for two more.

�Very interesting theory, it�s also one of the main reasons I�m here as 
well. That and no one really wants to take a 30 something divorcee and 
single mother out. Most men my age are doing the same thing I�m doing 
by going out with younger women. Not that it�s uncommon in this 
generation, but to find someone I can relate to and connect with is a 
bit tricky.� She stated.

I was now starting to feel the effect of both the martini I slammed, 
and the current work in progress. It was pretty strong, even for a 
frequent drinker like myself.

�I hear ya with that. I think it�s an obstacle in any relationship. So 
many people are in relationships for all the wrong reasons these days. 
It�s a bit sad how quickly people take the dive �cause they�re scared 
of being alone. So cheers to that.� I replied.

We held our glasses up and met them in the air at the rim. This led to 
another slammed drink by me, and a sip by her.

�You make the funniest faces when you slam your drinks. Like it�s your 
first drink or something.� She said.

�Oh wow, I hadn�t noticed. I don�t usually look into a mirror when I 
drink. Except when I try to talk some sense into myself in the bathroom 
attempting to sober up, with a beer in hand. It�s also mostly because I 
don�t normally drink hard liquor.� I replied.

�Oh yeah? What kind of sense do you try to talk into yourself? You seem 
like you have your head on your shoulders.� She said.

The liquor was slowly starting to take control. I realized that I had 
to pee, but not before I ordered us another round of drinks. She was 
still working on her one. I probably had to slow down, because I 
usually start to do stupid shit by the fourth drink.

�Well not necessarily. I have been slacking off a lot in school. I 
guess that just comes with the territory when your father pays for 
everything.�

By mentioning that I was in school actually opened up a can of worms. I 
was trying to avoid the subject, but it was a little inevitable.

�Oh yeah? What are you studying?� She asked.

So far so good, nothing asked about the school I attended.

�Music Production. I actually have a home studio I�m working on right 
now with one of my Columbia classmates.� I responded.

I thought by mentioning Columbia would avoid the question of what 
school I go to.

�Oh wow, that�s impressive. I would love to see it some time.� She 
said.

�I actually have some pictures of it on my phone.� I stated.

Her comment about potentially coming over to my place flew right over 
my head. I busted out my phone and went to the photo album. I showed 
her the workstation and the makeshift vocal booth, which doubled as my 
closet.

�That shirt really compliments your condenser mic.� She laughed.

This was odd seeing this version of Ms. Wendy. She actually seemed fun 
and less professional. I mean you could probably say that about anyone 
and the career they choose. You don�t necessarily see a garbage man 
take his work home.

�Yeah well sometimes I like to get dressed and sing at the same time. 
It�s a great way of mutli-tasking.� I responded.

She started laughing again. I had a feeling I had her now. Just then I 
realized that the liquor was starting to almost take full effect.

�What about you? You mentioned you�re a mother. I have a couple little 
cousins myself. No kids, yet. I love kids though. What�s his name?� I 
asked.

�Oh yes I do. He is quite the handful. His name is also Matthew, or 
Matty for short. He�s two.� She replied.

�Now that�s a great name!. You should get him a drum set. I wish my 
parents would have gotten me started earlier on an instrument.� I said.

�That�s a good suggestion. I�ll have to pick one up this week for him,� 
She replied

�Glad I could be of service! Do you have any pictures of the boy with 
the greatest name in the world?� I asked.

�Unfortunately not. I need to import them from my old phone.� She 
responded.

Now I was a bit confused. I remember talking with Alyssa earlier about 
her having a kid. The fact that she didn�t have a picture of her kid in 
her wallet was a little shady.

�Once I get him the drum set, I�ll send you a pic. He�s quite the 
cutie.� She said.

�Well with a name like Matt, it comes automatically. I replied.

Well since I was now a couple drinks in, I found it was time to say 
something stupid.

�Now I don�t remember you pregnant at all. If you were you hid It very 
well.� I said.

You�ve heard the expression �Loose lips sink ships?� Yeah, grab a life 
preserver. She now looked very confused.

�Uhh well considering we just met about an hour ago, I don�t know how 
you would be there to experience my pregnancy.� She said as she let out 
a laugh.

I couldn�t believe I just asked that, then again I couldn�t believe I 
did most things when I was drunk. Now I have to explain myself to her.

�You�re a teacher right?: I asked.

She looked more let down than shocked, like this has happened to her 
before or something.

�Yeah, I am� I take it that you�re one of my students then?� She asked.

�Yes. You actually kicked me and my friends out of your class earlier 
today.� I replied.

�Now I know how you look so familiar. It figures that this would happen 
to me.� She responded.

I don�t know why she was so surprised. I mean it�s a city of millions 
of people, but if you plan on meeting someone college age a couple 
blocks from the campus, chances are they probably in college.

This is the part where I usually get up and leave. I started to stand 
up and put on my jacket.

�Oh now you�re leaving? Great.� She said,

She looked really upset. So I sat back down.

�Oh I thought you could get in trouble for going out with a student.� I 
responded.

�You�d be amazed at how many girls your age are under their professors 
desks blowing them right now.� She said as she took a sip from her 
glass.

I started to relax back in my seat. I was surprised at her response. 
Especially a woman of her stature. I don�t see how she could be risking 
her job at the hands of a hook-up with a student. Unless she had some 
sort of hidden agenda or something. I know she�s my teacher, but it�s 
still Craigslist.

The night was starting to die down and people slowly started to leave 
the bar. I was starting to get more comfortable with her as our 
conversation continued. I found that we actually had a lot in common, 
or maybe I was lying and just agreeing with her because I was drunk. We 
were at the back corner of the bar, the teacup candle flame reflected 
off our faces from the center of the table. It was actually a pretty 
romantic atmosphere once I realized it.

As I was getting more comfortable with her, she was getting more 
comfortable with me. Evidence of this was shown with her hand on my 
knee. I could feel the blood in my body circulating to a certain 
member. There was no way of hiding this by the tightness of my jeans 
and the boxers I was wearing. I realized she soon noticed and produced 
a huge smile and her hand slowly started to move up my thigh.

I tried to put my mind on something else, but the dress she was wearing 
the sexiest outfit imaginable. It was a strapless black cocktail dress 
that ruffled at the bottom. She filled the dress perfectly; her breasts 
looked perky and amazing, I never saw this side of Ms. Wendy. I then 
realized that she never answered my question earlier.

�Claire, you never answered my question about your son. How come I 
never noticed you were pregnant? If you were, you hid it very well.� I 
asked.

�Well I never was pregnant. I adopted him after my divorce from my 
husband.� She responded. �And please, call me Ms. Wendy.� She said in a 
sexy tone as she fellated the martini olive with her mouth.

Now that made more sense. That cleared up the question Alyssa and I had 
earlier. I started to feel a tingle in my bladder and realized I never 
went to the bathroom.

�If you excuse me, I�ll be right back. I have to use the washroom.� I 
stated

She slid her hand up my thigh making contact with my crotch and made a 
slight grab. I could have died right there. My eyes made the familiar 
trip to the back of my head and I felt a little death attempting to 
explode out of my body.

�Hurry back now.� She said in a sexy tone as she released my now 
throbbing erection.

I was now trying to figure out a way to the bathroom without anyone 
noticing my erect member. I didn�t even know if I could urinate 
anymore. My penis had a mind of it�s own now and peeing was the last of 
it�s concerns. I started to concentrate on inanimate objects to soften 
my erection. As soon as I got it to a neutral semi-soft state, I got up 
before she put her hands on me again. While I was in the bathroom, I 
noticed I got a text from Alyssa.

�Hey Matt, sorry I weirded you out earlier. It was probably some sort 
of coincidence anyway. Hopefully you�ll still come with me to babysit 
next week. � Alyssa�

That was the last thing I expected from her. She seemed like she was 
some sort of �No Regrets� punk chick. I was more weirded out that she 
was apologizing. I hit the respond button and texted her back

�It�s all good Alyssa. I�ll still come with you. Let me know if you 
want to do something before that though. I�m free whenever.�

I was quite surprised at my composure and grammar in my drunken state. 
I usually just slur a text out when I�m this drunk, but I�ve started to 
become quite the perfectionist when it comes to grammar, so now I have 
to go over the text 4 times before I send it.

After I was done urinating, I stumbled my way over to the sink and 
started to wash my hands. I looked up in the mirror and caught myself 
before I started to talk some sense into the audience of me. I didn�t 
walk away from the mirror without high fiving myself for pulling this 
stunt with Ms. Wendy. I then felt my phone go off letting me know I had 
a new text. It was from Alyssa.

�That sounds good. Are you free tonight? Or is it too late. I just 
can�t sleep and don�t want to be alone. We could watch a movie or 
something.�

That sounded like a �Can you just come over and fuck me?� more than it 
did a movie invite. What to do? What to do? I have a guaranteed lay in 
the next room. I bet I have to work at Alyssa before she starts to give 
it up. Then I started to think about the reason I was here. I needed 
this more than I needed a conventional girlfriend. I then texted Alyssa 
back

�I would love to, but I just got to my buddies house up in Wilmette. 
Sorry! - Matt�

I then left the bathroom and walked back to the table. Ms. Wendy was 
signing the receipt for the drinks. She looked up at me and smiled.

�You don�t have any type of heart condition do you?� She asked.

The question caught me off guard a little bit, but I answered �No.�

�Good, drink this and let�s get out of here.� She responded as she 
handed me a shot of some sort of yellow tinted mixture.

We toasted again and slammed the shots. It tasted like lemon vodka, but 
it had some sort of weird after taste. Like chemicals.

�There�s that face again. It makes sense you would make it after you 
taste what I slipped in there.� She said.

Oh great, the crazy bitch roofied me! I knew this was too good to be 
true. I immediately tried to make myself puke.

�Relax Matt, I noticed you were starting to display an interest in the 
way my hand stimulated its way up your leg. I just want you to last all 
night for me� She said as she moved in towards my ear and whispered 
�Momma is going to take real good care of you tonight.� As she backed 
away, I felt the tip of her tongue make contact with my ear. The blood 
in my body made it�s way back to my crotch region. This was going to be 
a good night.

Chapter IV

She handed the waitress the check and grabbed my hand then headed for 
the door. I�ve never heels click across the floor so fast in my life. 
Her grasp made me feel like I was a misbehaving 4�year-old being led to 
the corner by their mother. She would look back every so often to make 
sure I was still there, but she would tease me by sweeping her top lip 
with her tongue.

We stopped outside the door and she handed valet the ticket. One of the 
attendants jumped into action and went to get her car. As we were 
waiting, she put both her hands on my right shoulder with her fingers 
interlaced and then leant in to whisper.

�Forgot about all your troubles Matt. I�m going be taking real good 
care of you from now on� She whispered in the most compassionate way. 
Not the kind of compassion lovers would display. But the reassuring 
kind that a mother would give to their child after they fell and hurt 
themselves. The kind that I rarely got out of my mother.

My trust in her statement was established once I saw her car pull up, 
It was a Mercedes G Class I wasn�t sure of the year, but I know that 
it�s a 100 thousand dollar car. I couldn�t believe it; I�m not sure how 
much college professors make, but she had to have been banking to 
afford a car like that. The attendant got out of the car and Ms. Wendy 
walked in front of me. He opened the door for her, not without giving 
her the up and down first. He then looked at me and gave me a 
congratulatory thumbs up all while mouthing what looked to be �Dayumm.�

I semi-stumbled to the passenger side and opened the door, I got in and 
attempted to take a seat but there was a scattered pile of papers 
blocking me from doing so. They didn�t look like school papers, they 
looked like blueprints for some sort of machine or structure of some 
sort. They could have been for a mailbox for all I knew. My vision was 
obstructed by the alcohol and god knows what she slipped me.

�Sorry about this. I didn�t know if I was going to be taking your cute 
ass home or not.� She said as she looked down at my crotch. �Well I can 
see the Viagra is working.�

�Oh so that makes sense why you asked if I had a heart condition. Ok.� 
I responded in a sarcastic tone.

�I didn�t want my star pupil getting a heart attack before finals.� She 
said.

I had a feeling that I probably didn�t need to worry about grades with 
Ms. Wendy for this semester. Now if I could only make the rest of my 
professors my Sugar Mommas/Daddys.

She threw her car into gear and starting driving northbound. I had no 
idea where we were headed, but it was most likely out of the city. This 
was confirmed once we hit the expressway. We drove for a good fifteen 
minutes before I could feel the Viagra really starting to work. I was 
starting to get antsy, like I had to pee or something. I couldn�t find 
a comfortable spot in my seat. Ms. Wendy soon noticed this.

�What�s the matter Matty? Do you have to go potty?� She asked in a baby 
voice. She realized it wasn�t her son she was talking to and laughed it 
off �Oh my, I�m so sorry. I�m so used to asking Matty if he has to 
potty. He�s still in diapers though; he�s not ready for the big boy 
potty yet. Are you Ok though?�

I quickly got control of myself and responded.

�That�s cute. Yeah I�m fine, it�s just the special medicine you slipped 
into my shot is starting to take full effect.�

She got a big smile on her face, and gently whispered �You�re lucky I 
know how to drive stick shift� Then I saw her lift her right hand from 
the 2 position on the steering wheel and make the familiar trip to my 
thigh again. This time she started to undo my belt. I could feel the 
rush of arousal circulating through my body faster than it�s ever been 
before. By the time she got to unzipping my pants, I could have 
exploded. Feeling her finger tips softly brush the surface of my 
freshly shaved pelvic region was like the first time I heard The 
Beatles. When she finally got her hand around my throbbing erection, I 
felt like I was in heaven. Her soft grip combined with the gentle 
stroking synced to the sound of the transmission switching gears would 
keep me at ease until we got to her house. She didn�t lie about knowing 
how to drive stick shift.

It actually wasn�t long before we got off at an exit. I was a little 
bit familiar with the area. It was one of the highest income cities in 
the Chicago area. My aunt lives in the next town over, and me being the 
inexperienced highway driver, had gotten off at this exit all too 
often. Of course I had immediately turned around after I had realized 
my mistake, but I was still somewhat acquainted with the town. Mostly 
thanks to my frequent bored Wikipedia visits in the middle of class, 
coincidentally Ms. Wendy�s class.

�Just a few more blocks and I�ll take care of your situation� Ms. Wendy 
said.

Oh the situation you induced? I thought. It seemed like she had a 
Florence Nightingale thing going for her, that or she just had some 
weird case of Munchausen syndrome. Either way I wasn�t complaining, but 
I had enough liquor in me to not need the help of some enzyme. She took 
her hand out of my boxers as soon as we approached the gate to her 
neighborhood. I let out one last pant as she let go of my dick and I 
started to zip my pants back up. I started to reach for my belt,

�Leave it unbuckled. I�m going to have it off in a couple minutes 
anyway� she said.

I didn�t say a word. I just sat back and braced my self for what was 
going to happen next. I looked out my window at the surrounding houses. 
They sure were pretty damn gigantic. We pulled into her driveway and I 
looked up at her house. It was probably the biggest house on the block. 
She probably got it after her divorce. I don�t know what she needs with 
such a big house; I thought it was just her and her son. I would have 
personally downsized to something smaller. I don�t like all that space. 
Even the guesthouse was too big.

�Here we are.� Ms. Wendy said as she pulled into the garage. She 
started to get out of her seat. �Can you grab my purse from the back?� 
She asked.

I got out of the car and opened the back passenger door and grabbed her 
purse. I looked up and saw Matty�s toddler car seat. It still had the 
tags on it, weird. You�d think she�d take them off so the kid didn�t 
choke on them. I looked to my right through the windshield and noticed 
Ms. Wendy standing at the door waiting for me.

�Are you coming? Or do you want me to get started without you?� She 
said as she swept her hair back with her fingertips.

�You can get start without me, but try not to finish without me� I said 
jokingly as I let out an awkward laugh.

She didn�t laugh back, she just approached me with a stern look on her 
face and grabbed me by my tie and yanked me inside. She turned away 
from me and led me through her kitchen by my tie. I noticed the 
highchair by the table also still had tags on it. Either all the baby�s 
equipment was new, or she had a death wish for her kid. I was sincerely 
hoping it was the former. Judging by the size of her house and car 
type, I imagine she probably buys the kid new stuff all the time. I bet 
the kid has Pampers made from goose down too. We had stopped at a door 
and she pressed a button outside of it. I heard a dinging noise and she 
opened the door to what looked an elevator. I looked at her confused, 
like �why the hell would you need an elevator for a two-story house?� 
She noticed my facial expression.

�It was in the house before we moved in. The old owner was an inventor 
who was also paraplegic. I feel like it�d be a waste if I didn�t make 
use of it. Besides, I want you to preserve your energy for the 
bedroom.� She said as she led me in. �Do you want to press the button 
honey?� She asked me like I was a toddler just experiencing an elevator 
for the first time. Of course I would have wanted to press the button 
anyway. I�m a control freak like that.

�Don�t mind if I do,� I said with a smirk on my face.

�You�re such a big boy, press floor two� she said in an ironic tone.

My smile came full circle and I pressed the button for the second 
floor.

�You�re too cute Matt.� She said.

The elevator started to make its slow ascent to the next floor up. It 
seemed like forever and before the awkward elevator silence had time to 
develop itself I started to make conversation again.

�Where is little Matty anyway? I don�t want to wake him up with my 
drunk stumbling,� I asked.

�He�s already up. Don�t worry. He�ll be here soon errr�I Mean, My 
sister probably has him up. She spoils him. He�ll be here in the 
morning, after you�re gone. I�ll make sure of that,� She said with what 
looked like to be an evil grin on her face.

Now the awkward elevator silence starts. Luckily we were saved by the 
ding of the elevator when we had reached the second floor. It was like 
we didn�t have a break for conversation. She immediately grabbed for me 
again, this time she gripped onto my unbuckled belt. I felt the belt 
loosen and start to be pulled out of the loops with every step we made 
towards her bedroom. By the time we had gotten to her bedroom, she had 
the belt completely off and she made a 180 and now faced me. She backed 
away and started to take off her dress. I started to mimic her action 
by finishing taking off my pants but was stopped by her.

 �I told you I was going to take care of everything from now on� She 
said as she pushed me back to the edge of her bed.

I thought I was a control freak; this woman wouldn�t even let me take 
off my own pants. I started to say something, but she just lightly 
pressed her finger to my lips to hush me. I was impressed, I liked 
that. As I sat at the edge of bed, she proceeded to pull my pants and 
boxers down to my ankles. When she had gotten them completely off, she 
had shifted to ripping open my shirt and whipped my tie across the 
room. After she threw them aside, she leant in and gently brushed her 
lips against my own without kissing. Then backed away slightly, and 
with one hand, pushed me onto my back. I lifted my head and watched her 
finish taking off her dress. Now stripped down to her black bra and 
matching lace panties, she approached me again.

I felt like I should say something sexual before she jumped on me, but 
knew I would fail miserably when all I kept thinking of saying was 
�let�s get physical� Luckily she prohibited me from speaking, at least 
I think that�s what it means when someone pushes her finger against 
your lips.

Soon I would be relieved of this tension growing in between my legs, as 
Ms. Wendy proceeded to kiss me downward from the neck. I felt her wrap 
her lips around me, and I slightly gasped for air. It felt like I was 
slowly drowning in a sea of ecstasy. I managed to keep my panting in 
sync with her head advancing toward my pelvic region to help me last 
longer. Then she threw her tongue in the mix and all bets were off. The 
tip of her tongue slowly glided from the bottom of my shaft to the head 
and back down again in a wrap-around fashion.

I didn�t know if I could last any longer, my heart rate was through the 
roof at this point. Ms. Wendy had me completely overwhelmed with 
pleasure. Her hand was firmly pressed against my abdomen and she 
slightly dug her nails into my skin. It was like she was getting off 
without me touching her. My Father spoke of Women like this, I thought 
it was all a myth, but I was in the mouth of the living, breathing 
legend. I could smell the desire in her sweat from where I was laying. 
Then she stopped thrusting her head down. She placed her hands back on 
my pelvis so that both index fingers and both thumbs met each other to 
form a teardrop shape around the bottom of my shaft Ms. Wendy then 
lifted her head up so my tip was slightly in her mouth. I felt like 
music should kick in, �cause something epic was about to happen. It was 
like my entire body concentrated itself inside the space between my 
thighs. Then, she unlocked her position, and thrust full force towards 
the bottom of my shaft. I could feel the tip of her nose gently poke my 
pubic bone as I took in one last gasp of air before I released into the 
back of her throat. She pushed up a little so she had room to swallow 
down what she had worked so hard for.

It felt like I had been resuscitated when she relaxed her lips and 
lifted her head away from my hips. A sigh of relief escaped my chest 
and I sank further into the bed. I wasn�t the only one who was failing 
victim to a little death. It was like the air surrounding Ms. Wendy was 
affected by her slight orgasm. I was absorbing the vibrations pulsating 
from her body and they quickly started to overcome my senses. A tingle 
raced down my spine as I choked on her aura,. The only thing that held 
it in was the grip that my teeth had on my lower lip.

Ms. Wendy backed away from me and let her climax come run it�s course 
as she too bit her lip to keep up with it�s intensity. The vibrations 
were getting stronger the longer she held it in to savor it. Just as 
she moaned in satisfaction, I held the sheets beneath me with a death 
grip. A wave of ecstasy filled the room and pulled me under with her.

When Ms. Wendy pulled her self back together, she approached me again 
and noticed that I was still standing tall.

�Well it looks like I�m going to have to take care of this too.� She 
said with an excited tone.

Chapter V

I lifted my head up and looked down my chest. It look like what she 
slipped me was surely doing its job, She wasted no time taking off the 
rest of her clothes either. Her panties were the first thing to slide 
off. Her bra soon followed its way to the floor where the rest of our 
clothes had been scattered.

As she stood unclothed in front of me, her arousal was quickly given 
away by the way it seemed to glisten in the faint light of the room. 
She then crawled on top of me and softly kissed my lips before lowering 
her hips down on to mine. I inhaled quickly upon entering her tight 
lower lips, and slowly let it out as she thrust vigorously. We went at 
it for about five minutes before I started to bite my lip again. She 
was quick to notice what this meant for me, and took it upon herself to 
thrust faster. Although it was awfully nice of her to let me cum before 
her again, I would have thought she would have wanted a part in this as 
well. Before I could over think it anymore, that familiar tingle made 
it�s way down my spine and concentrated all its energy in my pelvic 
area again. The more I resisted it, the harder she�d thrust. It was 
like she was milking me dry for some odd reason. I finally gave in and 
found myself back sunken into the bed again.

I didn�t feel right anymore, once I was no longer inside of her, I felt 
drained of more than energy. She was quick to roll off of me too, like 
she got her 8-hours in and was done for the day. Usually if this were 
to happen to me I�d hear a �Are you seriously done?� before she got off 
of me. I heard nothing from Ms. Wendy except a �Goodnight� as she hit 
the light switch making the room completely dark.

Now both on opposite sides of the bed, Ms. Wendy and I soon found our 
way under the sheets. I stared at the ceiling confused at what just 
happened, but once my eyes were closed, it was like morning came as 
fast as they shut. I awoke to the familiar beating of drums in my head, 
which indicated a hangover. I then let out a yawn and sat up to look 
around the room. The shades were wide open and the sun light was 
beating the shit out of me. As I walked over to close them, I noticed 
that Ms. Wendy was no longer in the bed.

�Weird, I�m usually the one who leaves before they wake up. But this is 
her house.� I said out loud as I picked up my clothes from different 
spots in the room.

Once I had all my clothes gathered, I proceeded to put them on. I then 
started to head for the bedroom door but almost ran into Ms. Wendy.

�Oh great. You�re up. I made you breakfast, come with me to the 
kitchen!� She said as she grabbed my hand.

This wasn�t the usual exit strategy I had grown accustomed in the 
morning. No one had ever made me breakfast after a night of drunken 
hookups. Then again, most of the girls I hooked up with didn�t think 
outside of their inebriated vaginas. Which didn�t say much for me right 
now, because I couldn�t help but stare at her ass as she led me 
downstairs. The way it looked in her tight low-rise jeans was better 
than most girls I went to school with.

When we had eventually made our way to the kitchen table, I had noticed 
that Matty�s highchair no longer had the tags hanging on it anymore. It 
looked cleaned and ready to use. She led me to the next spot over, 
there was a placemat down with a plate full of various breakfast foods. 
The one strange thing about the setup she made for me, was all the food 
had been cutup already.

�Eat up, you got a big day ahead of you.� Ms. Wendy said as I sat down.

I was now a bit confused, how did she know what I had planned for the 
rest of the day? I actually didn�t have anything planned except to go 
home and smoke a bunch of weed while I played XBOX. I just responded 
with a �Uhh thanks� and pulled my seat up. She sat across the table and 
sipped from her coffee cup. I started going to work consuming the 
toddler-sliced pancakes and breakfast sausage. As I was clearing the 
plate, I noticed that there was some sort of graphic slowly being 
revealed underneath. With my last couple bites, the final image of a 
little kid�s show called �The Backyardigans� had shown through.

�Oh cool, my favorite show.� I said jokingly,

�I take it all the other dishes were dirty?�

�Yeah, something like that.� Ms. Wendy said with an awkward laugh.

Just as she looked to be getting comfortable, the atmosphere soon 
changed as Ms. Wendy answered what seemed to be a frantic call from her 
sister. In the mix of all the sporadic �oh no!�s the call was ended 
with an �Linda calm down, I�ll be there in ten minutes.�

 My eyes shot over to the other side of the table. She seemed 
surprisingly calm after she hung up. It was kind of an odd reaction 
based off the content of the conversation.

�Hey Matt, I gotta go pick up Matty. He threw up at my sister�s. You 
can stay here and I�ll take you home when I get back.� Ms. Wendy said 
as she grabbed her car keys.

�Oh that�s fine, I can actually have my aunt come pick me up. She lives 
a couple miles away.� I responded.

Now she looked caught up, like I had ruined her plans or something.

�Oh. Well she�ll have to pick you up outside the gate. I don�t know if 
she can get in,� she said.

It wasn�t that big of a deal, so I just finally agreed with her and 
told her I�d wait �til she got back.

�Ok. I�ll be back soon. Help yourself to anything in the fridge. The 
remote should be by the couch.�

She then kissed me on the cheek and walked out to the garage. As she 
was opening the door, I saw her reach for her cell phone and call 
someone as the door closed behind her. It was probably her sister 
again; I was more questioning the fact that she let me stay at her 
house alone. I know I�m one of her students, but I could rob this bitch 
blind if I wanted to. As I was pondering my criminal thought, I was 
interrupted by the sound/vibration of a text message in my pocket. I 
reached to grab my phone and read the text message Alyssa sent me:

�I get to see you soon :)�

I just let out a sigh, walked over to the couch and put my head in my 
hands. I can�t stand clingy girls. Alyssa seemed like she might be one. 
I normally don�t get the smiley face until I�ve hung out with a girl 
for 3-4 times, anything before that just plain turns me off. Then I 
thought of how easy it would be to bang her and let that thought 
process overpower the former. A smile lit up my face as I kicked my 
feet up on the coffee table and put my hands behind my head in a 
relaxing position.

Looking around the room, I didn�t see any pictures of Matty. Which was 
extremely odd to me, considering new moms take a thousand pictures of 
their kid making the same damn face at a different angle.

�Well she did say he was adopted, maybe she just hasn�t gotten around 
to taking pictures.� I said out loud giving her the benefit of the 
doubt.

I just brushed it off and flipped the TV on. iCarly was on, I secretly 
watched the show but I decided I�d rather watch something else. I 
flipped the channel, it was Noggin this time. I flipped it again, Nick 
Jr. She must�ve had some child lock on, �cause I was getting nothing 
but kids channels with shows aimed for Toddlers.

�That�s not an accident that you�re not finding any big kid channels� I 
heard a woman voice behind me say.

My heart nearly jumped out of my throat as I stood up and turned around 
quickly to face the voice. There stood my Psychology teacher Ms. Evans, 
she was a short young red head that I didn�t give much credit to beauty 
wise until now. Although she was dressed in a lab coat and an apron, 
her perky breasts looked like they wanted to escape the shirt beneath. 
I couldn�t help but stare and get a slight erection.

�I thought she said she drained you.� Ms. Evans said as she approached 
me all the while snapping on a latex glove.

�What the hell are you talking about?� I said.

�You just hush and let me relieve you.� She said as she began taking my 
jeans off.

I didn�t say a word, this was like the plot of some amazing porn. 
Except it wasn�t a porn, it was real life! If it were a porn though, I 
would name it �Teacher-Fuck Fest 2010.� Well that�s just a working 
title, I would use it until I thought of something better later on. I 
couldn�t think much now, I was too busy watching her squirt baby lotion 
into her hand and getting to work. Just then I felt my phone vibrate 
near my foot as I was about to cum. My eyes rolled to the back of my 
head and I reached to grab my phone out of my pants on around my 
ankles.

�Are you fucking kidding me Matt? I need to get you drained or this 
isn�t going to work right� Ms. Evans said as I looked at my phone 
screen.

�No I�m not kidding, I have to answer this text, it could be my dad. 
And why the hell do you keep saying �drain� you know that�s not turning 
me on right? And get what to work right? � I replied.

It wasn�t my dad texting me, It was fucking Parker. I hadn�t heard 
anything from him since yesterday.

�Hey Man, you OK? I saw you make off with that bitch who hit me and I 
took off. Hey when you get a minute call me, there�s some weird shit 
going on at the school. Someone�s fucking baby got onstage in the cafe 
and started screaming shit. It wasn�t like a baby voice though it was 
trippy.�

Although I was quite busy getting a hand job from my Psychology 
teacher, I opted to respond. With my pants around my ankle, and my 
teacher standing there with her arms crossed, I started texting Parker 
back. I looked like the cockiest son of a bitch in the world. But I 
felt the need to let Parker know what my last 24 hours had consisted 
of.

�Hey Man, I�m OK. I�m totally gonna fuck that Alyssa chick by the way. 
Also, I fucked Ms. Wendy last night and totally came down her throat in 
her fuckign bed! and I�ll call you after I�m finished getting a hand 
job from Ms. Evans, she said she has to �drain� me or some shit 
hahahaha wtf right? I�m dead fucking serious dude, This is the greatest 
day ever!!!!...�

After I hit send. I put my phone back in my pocket and looked at Ms. 
Evans.

�Uhh I�m ready� I said in a cocky tone.

�You know what, fuck this.� Ms. Evans said as she got a cloth out of 
her pocket. �You�re getting what you deserve little boy� she then 
shoved the cloth in my face.

�Hey that smells like chloroform�.� I said as my knees buckled and I 
fell to the floor. I heard a distant �nighty night� before I blacked 
out completely.

To Be Continued...



 








Rate This Story:


good
4
3
2
1
bad

Click "Submit" at bottom when finished.
"4" = highest rating
(The following information requested is optional, though your participation is highly encouraged.)
Name:

Age:



<8
8
9
10
11
12

13
14
15
16
17
18-20

21-25
26-30
31-40
41-50
51-60
>60

I am a/an:


--Please select one--
Young boy (ages 8 and under) who wears diapers
Young boy (ages 8 and under) who does not wear diapers
Preteen boy (ages 9 to 12) who wears diapers
Preteen boy (ages 9 to 12) who does not wear diapers
Teen boy (ages 13 to 17) who wears diapers
Teen boy (ages 13 to 17) who does not wear diapers
Young adult male (ages 18 to 25) who wears diapers
Young adult male (ages 18 to 25) who does not wear diapers
Adult male (ages 26 to 35) who wears diapers
Adult male (ages 26 to 35) who does not wear diapers
Adult male (ages 36 to 45) who wears diapers
Adult male (ages 36 to 45) who does not wear diapers
Adult male (ages 46 to 55) who wears diapers
Adult male (ages 46 to 55) who does not wear diapers
Adult male (ages 55 and over) who wears diapers
Adult male (ages 55 and over) who does not wear diapers
Young girl (ages 8 and under)
Preteen girl (ages 9 to 12)
Preteen girl (ages 13 to 17)
Young adult female (ages 18 to 25)
Adult female (ages 26 to 35)
Adult female (ages 36 to 45)
Adult female (ages 46 to 55)
Adult female (ages 55 and over)

Your diapers



If you are a boy or adult male, select all that apply:
Cloth diapers
Disposable diapers
Multiple underpants
(6+ pairs)

I wear this diaper type:




I wear this diaper type in plain white:




how many of this diaper type I wear at a time:


0
1
2
3
4
5
6
>6


0
1
2
3
4
5
6
>6


0
1
2
3
4
5
6
7-9
10-12
13-15
16-20
21-25
26-30
>30


Are you pantsless at home while in diapers?

Always
Usually
Sometimes
Rarely
Never
I do not wear diapers

I was often in diapers and pantsless as a boy (ages 12 and under)
How do you use your diapers?

Pee
Poop
How many older sisters do you have (boys only)?

None
One
Two
Three
More than three
How many younger sisters do you have? (boys only)

None
One
Two
Three
More than three
If you are a girl or adult female, indicate what your relationship is to the diaper boy who read this story:


--Please select one (leave alone if a boy)--
Younger sister
Older sister
Same-age sister
Younger girl cousin
Older girl cousin
Babysitter
Girlfriend
Wife
Mother
Aunt
Grandmother

Who else in your family has read this story?

Mother
Father
Older Brother
Younger Brother
Older Sister
Younger Sister
Your comments:

Parents' comments:

Brothers' comments:

Sisters' comments:



   
CAUTION!!! Pressing "Reset" will delete ALL of your data entered!