I’ve been a political activist since the age of eighteen and over the years, I’ve worked on several political causes which is how we first met. The Chicago Police Department had a long history of brutality and violence particularly against minorities. Several high profile cases took place with unarmed suspects being shot to death that sparked public outrage in the late 1990’s and one evening there was a message on my answering machine from a political friend inviting me to a meeting the following Saturday to discuss starting an organization to deal with the issue.

When I arrived at the progressive bookstore only three blocks from Wrigley Field, there were already approximately twenty others already there including several long-time colleagues of mine. As we waited for the meeting to begin, the door opened and a young woman with a slight physical disability entered the store and took a seat after pouring herself a cup of coffee. There was something about her that drew my attention immediately. She was androgynous looking and reminded me of the famous Mexican artist and activist, Frieda Kahlo. By the time the meeting began there was an eclectic and racially mixed crowd of thirty five people in the room.

The first several people to speak were relatives of young people who had been killed by Chicago police and their anguish was heartbreaking to hear. At the conclusion of the three hour meeting, a vote was taken to start a new organization to not only confront the epidemic of police violence but also attempt to support the families of those who had lost a love one to it. I was asked to be on a committee so while some people left to go home, we remained for another short meeting. One of the other activists on my committee was Barb who during a brief personal introduction go around to others in the group stated that she was sixteen years old and a student at the most progressive public high school in the city.

Over the next few months, we planned a dramatic nonviolent protest in downtown Chicago to kick-off our campaign. When the day of the protest arrived, we had almost one thousand people present to participate along with legal observers from the National Lawyers Guild and a group of street medics in the event that something went awry. During the march, the police attempted to keep on us on the sidewalk but when the opportunity presented itself we flooded onto the street despite police attempts to stop us. About two blocks into the march, four policemen made an attempt to arrest one of our organizers (George) whose unarmed son had been shot to death on his prom night. We halted the march, as our layers attempted to intervene, the police became physical aggressive with him and Barb charged into the scene shouting at them to release him.

One of the cops threw Barb onto the street and started to handcuff her. I started to intervene when one of our other organizers, Toby stopped me and she said “Let me do it or she’ll be in jail with nobody to protect her!” She then managed to intentionally get herself arrested in order to safeguard Barb in jail. As they were put in police cars, some of our lawyers left in an attempt to gain their release and we resumed the protest. After the march ended, our legal team informed us that the police were attempting to stall them by moving them from one police station to another. Barb, Toby and George were not released until the following afternoon despite TV news coverage of their arrest. This incident proved to me that Barb was someone willing to put herself at risk to protect others which is something you don’t find very often especially if they’re only sixteen years of age!

I worked with the organization and Barb for the next two years before leaving for reasons not relevant to this story. We lost track of each other for about three years until one day I received a friend request from her on Facebook. I eagerly added her as a friend and made several comments on her photos regarding how attractive she looked before signing off for the day. The next morning when I looked at Facebook, there was a message from Barb which gave her phone number asking me to call her once I had read it. I called her immediately; we caught up with each other during the twenty minute call. As we were about to end the call due to the fact that she had to leave for one of college classes, she asked if I’d like to meet the following afternoon for coffee at the Mexican Jumping Bean in the Pilsen neighborhood of the city. I accepted her invitation and was excited about seeing her again.

When I parked in front of the coffee shop, she was seated in a window seat and she waved at me as I got out of the car. When I got to her table, she gave me a hug and a kiss on the lips which surprised me. We talked for almost two hours before she asked…

“Do you want to come over to my apartment so we can play?”

My response was to pick up the check, pay it at the register before walking her to my car. My sense of anticipation had made my cock hard but it was about to get better. During the short drive to her place, she said…

“I’d really like it if you could spend the night with me and do anything you want to me. I also want you to allow me to do anything that I want to you.”

It should be obvious, I told her that was absolutely fine with me and then she started rubbing my cock as we pulled up to her apartment building. As we walked up the three flights of stairs, I watched her sweet ass and she explained only three of the six apartments were occupied because the owner was very selective when it came to tenants. As soon as she locked her apartment door, we literarily attacked each other in a state of primal lust. I dragged her to the sofa as she said…

“Be rough! I want you to use me like I’ll use you later!”

I immediately asked her if she had a ‘safe word’ in the event things became too intense and she wanted to stop whatever might be taking place. She told me “Red means stop and yellow means slow down.” For over twenty minutes we engaged in foreplay that would have had others either running out of the door screaming or calling the police. As we French-kissed each other, both of my hands were locked around her throat as she urged me to choke her harder and I complied with her needs. When I turned my attention to her small tits they were slapped hard, pinched and bitten as she moaned while she fingered herself.

I ordered her into the doggy position and told her to stay in place to remove the heavy leather belt from my jeans. For the first few minutes, I used the belt to deliver moderate strikes to her ass but then I picked up the intensity until her ass was a bright red. When I was satisfied with the way her ass looked, it was time to rim her asshole deep as preparation for it to be fucked hard. As I tongue fucked her she kept moaning and saying “deeper!” The deeper my tongue went the sweeter it tasted.

When I thought she was ready, I positioned my cock then without a word being said shoved it balls deep into her asshole as she let out an animalistic growl issued from between her lips. I just allowed my hard on to fill her ass for over a minute until she started yelling…

“Fuck me hard! I want your cum in my ass!”

At that point, I launched a full scale anal assault on her shit hole for over five minutes before shooting my loan into her bowels. As soon as I pulled my cock from her rectum, I began slurping, licking and sucking the cum from it until she was clean. I repositioned my semi-erect cock in front of her mouth ordering her to suck it clean so she could enjoy the taste of her own asshole which she was eager to do.

We then both collapsed onto the sofa, panting and covered in sweat. We laid there holding each other tightly for over ten minutes until she attempted to excuse herself to take a piss. I informed her that she would be pissing into my mouth since piss shouldn’t be wasted but rather recycled which made her break out into a loud laugh before she said…

“Come on, I’ve never done it before but I’m willing if you’re really that thirsty!”

I followed her into the bathtub, knelt down in front of her as she pulled my head into her crotch and released a flood of her ‘champagne’ into my open mouth. I was able to swallow most of it and loved it. After the fact, I licked her pussy clean and thanked her with a long French-kiss so she could taste herself from my tongue.

She then retrieved a beer for each of us from the refrigerator and we sat on the sofa to chat for awhile. She asked me if I was really willing to relinquish power to her so she could do whatever she pleased to me and I assured her that I was prepared to let her control the action as long as we could go out for a nice Mexican dinner later. Once we had finished the beer, she told me to go out to the back yard for about ten minutes because she needed time to prepare things.

I sat down on one of the chairs in the back yard to have a few cigarettes and thought about how lucky I was to reconnect with Barb. I lost track of time so I hurried back inside. As soon as I opened the door, Barb slapped me hard across my face a few times and told me to follow her orders in the future! It was then that I realized, she was wearing a strap-on dildo along with knee high leather boots which got me aroused.

She ordered me to lean over the high table in the living room as she secured both my wrists and ankles to it with rope before stuffing her panties into my mouth. No sooner than that she disappeared into the bedroom then reappeared with a leather flogger in one hand. There were no words of warning before she began flogging me hard across my upper back, ass and legs! It was the first time that anyone flogged me but I was determined to endure whatever she had in mind for me. The flogging went on for at least ten minutes and I was relieved once she stopped. She then removed her panties from my mouth.

She then began to interrogate me while squeezing my balls hard from behind…

Question: Are you straight or bisexual? Answer: I’m bisexual.

Question: When was the last time that you had sex with a male? Answer: About two years ago.

Question: When you first met me did you want to fuck me? Answer: Yes!

Question: What stopped you from moving on me? Answer: It was only because you were only sixteen. (which made her laugh)

Question: What’s your dirtiest sexual fantasy? Answer: ***censored*** (Her reply was “If you’re a good slut, it might happen someday!”)

Question: Of our mutual friends from when we first met which ones were you sexually attracted to the most? Answer: Toby, Arriba and Lena.

Question: Have you ever had a threesome? Answer: yes, several.

Question: Have you ever had a foursome? Answer: Not yet but I’d love it.

Question: Would you like to meet some of my friends from school? Answer: Yes, of course.

Question: Are you OK with interracial sex? Answer: You already know the answer to that!

Question: I’m fucking around with another bisexual guy, are you alright with that? Answer: No, not unless I’m allowed to join in or at least watch!

Question: Do you want a monogamous relationship with me or would you be willing to share me? Answer: No, I’m willing to share you but I’d want to protect you.

Question: So would you like to be my “Daddy”? Answer: Fuck yes!

Question: Do you like to watch others have sex or do you like to have others watch you having sex? Answer: Both! (Her reply was “It’s the same for me!”)

Question: Since I’m in a private college which is expensive even with scholarships, if I had to raise funds for tuition and rent, would you help me to become a sex worker? Answer: Of course, if that’s what you wanted.

All of a sudden, she stopped asking questions and then I felt her hand lubing my ass heavily. Within two minutes, the head of her strap-on dildo was entering my ass and it felt good. She paused for less than a minute then eased the artificial cock all of the way into my ass and it was truly intense once she began to furiously fuck me. Within ten minutes, my cock erupted shooting cum onto the wooden floor. As soon she withdrew from my ass, she cut the ropes securing me to the table and ordered me to suck the dildo clean which I did without question while she smiled down at me.

Then each of us drank some beer as we talked and it felt like I had finally met my dream lover. We took a hot shower together before going for a very long walk around the neighborhood prior to a large Mexican dinner at her favorite restaurant. Over dinner, she flirted in Spanish with the waitress who flirted back and told me she had a surprise for me in the morning before I left. The remainder of the evening was very romantic, intimate and loving. When we awoke in the morning, she asked me if I had to piss and I said yes. She led me to the bathtub then dropped to her knees and then swallowed my recycled beer from the previous evening.

Over coffee, she told me that Toby would be staying at her apartment for a four day visit in a few weeks and she divulged had played with each other several times over the years beginning with the night that they spent in Cook County Jail. She asked me when we could see each other again and I said. “As soon as possible but I’m heading to Kentucky in five days for a seven day pro wresting stint with a nice guarantee in terms of cash.”

She replied. “Could you spend this Friday, Saturday and Sunday here with me?”

And I said. “Yes!”

***to be continued***