This is based on a true story. All the names have been changed to protect their
It all started my sophomore year of college. I had been dating my high school
sweetheart going on three years and things were going well for us. In high school, I had
taken a lot of heat because Sheryl was younger than me. In those days, age mattered
when dating someone. Now that I was in college, it really didn’t matter any more. The
distance was tough at first, since Sheryl was still in our home town, but we managed to
adjust and find a routine together. I’d make as many trips home as possible to see her,
but it was definitely more fun when she came to visit. Debating between a college town
and a trip back home wasn’t difficult with the usual weekend festivities in college
towns. Since the drive from our home town to campus was about four hours,
depending on who was driving, convincing Sheryl’s parents was often difficult. One
occasion, however, went farther than my wildest dreams could ever imagine while
asking Sheryl’s mother if she could come visit.
Then, cell phones weren’t nearly as dependable and advanced as they are now, and
with the expensive minutes, we spent most of our time communicating via MSN since
it was free. It was a typical Thursday afternoon and I was done with classes for the day.
My roommate played baseball for the university so his afternoons were spent at
practice. It was pretty rare to get some “me” time in a dorm room that resembled a
prison cell; it was so small. Sheryl’s mom, Cindy, was online so I decided to hit her up
to give Sheryl permission to come visit this weekend.
“Hey Cindy, I don’t mean to bother you at work, but I’ve got something to talk to you
about if you’ve got a minute?”
It took her a minute, but she responded as if she was honestly excited to hear from me.
“Hey Scott…How are you?”
We bullshitted awhile about school, grades, mid-terms coming, etc. but it was all just to
warm up to her. My real intentions were to win her over so I could nail her daughter all
weekend long. I’m just being honest. Finally, after thirty minutes of ass kissing I
decided to finally just get right to the question. Cindy was a little hesitant, at first, but I
could tell she was thinking about it. After all, the weather was going to be good so what
was there to really worry about?
“I don’t know Scott, it’s a long way for a young girl to be driving alone….I know you
guys don’t see each other much so it’s really hard for me to say no” she says.
“Cindy, I’ll do anything you want…anything…you name it…” I pleaded.
Minutes, which seemed like hours, went by with no response. Did I push too hard? Is
she pissed? These were questions racing through my head. I was trying really hard not
to come off desperate, but in all honesty, I was. Cindy finally responded, which made
me relax, but it was the response that I couldn’t believe. It was life changing, exciting,
dangerous, and could she be fucking with me? There were thousands of emotions
flying through my head, both heads. Let’s understand one thing first; I’m not the kind of
smooth talking guy that’s good with words around the ladies. Moments like these
typically made me choke on my own tongue. This time was different though. I didn’t
have the confrontation of a face-to-face conversation. I was daring and brave behind a
computer screen, though, and this was an opportunity to turn on my alter-ego. And,
worst case scenario, I could deny, deny, deny. I could possibly get my roommate to
cover my ass and say it was him on my computer fucking around in the chat rooms.
That wasn’t uncommon, nonetheless, that was my story and I was sticking to it.
“Hmm...I would do anything is a pretty bold statement to make to a lonely house wife,
Scott...think you could handle it?”
“You name it, and it’s done. No questions asked” I responded.
Innocent reply, but yet, open ended enough that she could take it however she wanted
to. Her requests were simple, yet dirty enough they could make me cum instantly.
Cindy wasn’t the hottest MILF in town, but I certainly wouldn’t have kicked her out of
bed unless she wanted to fuck on the floor.
“Every time you cum for Sheryl, I want you to think about me…every time you
masturbate…I want you to cum fantasizing about me” she said.
That’s it? I thought. I could just tell her what she wants to hear. How in the world would
she know if I actually did it?
“You’re requesting something I’ve already been doing, Cindy. Are you sure this is what
a lonely house wife needs?” I said optimistically.
If she was as turned on as I was, she had to have been soaked. Just one touch to my
cock and I would have blown my load right then.
Cindy demanded confidently, “I want you to fantasize about me first…maybe one day if
you’re lucky…I’ll make those dreams come true”.
This was a double victory in my book. Not only does Sheryl get to visit this weekend,
but, I could possibly get lucky with Cindy, too! My imagination went wild and the
fantasies were never ending. The only problem was could I actually pull this off?
The weekend with Sheryl went great. We had a great time partying and going around
to the different bars. Since neither of us was twenty one yet, the selection of bars we
could actually get into was slim pickings. Nonetheless, we made the best of it and
enjoyed our time together as usual. Dorm room sex was always a little difficult, though.
Having a roommate sl**ping eight feet from you tends to limit your options a bit. If it
was up to me, I wouldn’t have any shame with him sitting there listening and watching.
Sheryl, on the other hand, was a little bit more modest and lady like and would never
go for such a thing. I wouldn’t be a guy if I didn’t try though, right? I can’t be called a pig
and not try to live up to it! Even with Sheryl there keeping my attention all weekend, I
couldn’t help but think about the deal I made with Cindy. It seemed awkward at first, but
the more I thought about Cindy the more I yearned for her.
Monday was here, Sheryl was gone, and back to the grinding wheel again. Typical
Monday classes and then it was on to the lunch room for the weekend gossip fest with
the usual suspects. Like usual, the afternoons meant no class and the dorm room to
myself. After the busy weekend, a cat nap was in store for me as I made my way to the
dorm. All alone and some wonderful imagery to reflect back on from the weekend
made it a great time for some self satisfaction first, though. Although, there was one
woman I couldn’t get out of my mind. Cindy. Was it the off limits status that she carried
that made her so intriguing? Was it because she was my girlfriend’s mom? I couldn’t
figure it out, but all I could think about was being on top of Cindy and giving her the
submissive boy toy sex slave she wanted me to be. Thinking of a woman her age was
a hot fucking turn on. She was experienced, sexy, demanding, and most of all, she
couldn’t get pregnant. “No condom” to a college student has the same excitement level
as a “fat k** in a candy store”.
I laid down in my bed and closed my eyes, pulled out my cock and started stroking it
while thinking of lying in between Cindy’s legs. She was a shorter woman, dark brown
hair, green eyes, and maybe a little on the thick side. I wouldn’t call her fat by any
means, though. Her breasts were large enough for a handful and her legs we sexy and
fit. I may not be a typical guy, but long dark hair and some nice legs will snag my
attention all day long. Mmmm…damn! It didn’t take me long to cum, but I sure did cum
long and hard.
One piece of the puzzle that never dawned on me was having the first opportunity to
cum inside a woman. I had never had this opportunity before, or at least, not one
without taking the risk of getting the chick prego. Just thinking about this made me
It was moments later, after I had finished cleaning myself up from the afternoon
activities, that I heard my MSN “nudge” coming from my computer. It was Cindy.
“Hey Scott…how was the weekend?”
“You were amazing” I responded, with a smile on my face.
A voice in the back of my head told me to be careful because you never know who is
on the other side of a monitor, then again, that goes both ways.
“I actually just got done fantasizing about you… the thought of having your sexy legs
wrapped around me…unleashing my cum into your pussy… made my cock explode
like a volcano.” I responded boldly.
“…omg…Would you really consider doing that?” she asks.
I eagerly responded, “Absolutely! You’re definitely MILF material…”
“I had some alone time this weekend in the tub and couldn’t help but imagine your
young hard cock pulsating in my pussy as you came in me….we need to set this
up…Scott, if ANYONE ever found out about this our lives will be ruined” she said.
“It would be worth it, Can you call me?”
To Be Continued…
Posted by adel5000 3 years ago Views: