Cougar Taking My Virginity

When I was about sixteen, I did what most other horny young boys did: I searched
naughty, sex-related websites. During my conquests, I came across numerous adult chat
sites. I created a profile (ModernRomeo), listing me as an 18 year old male, on my
favorite site.

I started talking with women of various ages, working on becoming competent at cyber
roleplay. I was finally able to virtually live out a number of my fantasies.

About a month later, I did a roleplay with KatieBelle34. Her profile said she was a 34
year old divorcee. I played an innocent young boy (which was very easy for me to do),
and she played an experienced older woman. We continued this scene for nearly an hour.
By the end, my fingers were sore from typing, but I was rapidly stroking my dick.

The last message she sent to me was: “Thanks baby 😉 I had the most wonderful orgasm.”

This sent me over the edge, and I sprayed cum all over my hand. I logged out and
cleaned up, thinking sadly that I wouldn’t talk with her again, since part of the
allure of these sites is in meeting new, random people.

The next day, I came back from school horny and ready to roleplay. As I logged on, a
message popped up. It was from Katie (her actual first name). She asked me if I wanted
to roleplay again, and what time I was free. I quickly replied that I was free all
night, and waited anxiously for her reply.

I was right about to start getting ready for bed when a message from her popped up on
my computer.

“Sorry, I was busy today. Tomorrow?”

I sent her a message, saying, “Alright! How about 5?”

She did not reply for an hour, and by that time I was in bed fast asleep. But when I
woke up, I saw what she said.

“Sounds good. I can’t wait to show you all sorts of ways to please a woman!”

Needless to say, I was so horny during school I could barely focus on my classes. I
got home, sprinted to my computer, and started watching porn until she logged on.
Again, we had an amazing roleplay that (I imagine) left both of us panting after our
orgasms.

We talked quite often, sometimes roleplaying three or four times a week. But one
morning, after an extremely heated session, I awoke to a message saying: “Here’s my
number babe. Text me the next time you’re horny ;)”

Well, I got horny right then and there. But I didn’t want to get too turned on before
school. Luckily, it was a Friday, so I would have the entire weekend to myself. I put
her number in my phone as “Katie”, and I went off to school to fantasize the entire
day.

After the last bell rang, I sent her a message.

“Hey, its James.” (I had given her my real name.)

She replied almost instantly, saying, “Hey James! I was looking forward to your text!”

We started off having a nice conversation. I found out she was a secretary (and was
texting at work), and I told her I was a student. She asked if I was in college, but I
grudgingly admitted that I was only 16 years old.

She did not reply for a couple of minutes. I began to think that she never would. But
she said, “It’s all cool. I have a thing for younger guys anyways ;)”.

We started talking about where we lived. After I sent my city, she said, “No way! I
live just like 30 minutes from there!”

Its a small world, I guess.

That night, we texted each other a steamy roleplay involving me sneaking into her
house. I orgasmed fairly quickly, because in my horny state, I could vividly fantasize
it actually happening.

I continued to text her throughout the weekend. That next night, instead of
roleplaying, we decided to swap pictures. The first one I received of her was a
headshot, showing her brown hair and eyes, and her smiling face. I sent one back.

She said, “Aww! You look so cute ;)”

I took another of me, shirtless, and she told me she liked my body. I hoped for one
from her, but I didn’t expect to get one. But I opened her next message to see a perky
pair of C cup breasts.

I kept repeating how amazing they were, and how I would love to suck on them.