Jessica and I had been friends for over 10 years. Shortly after meeting her she married a man named Matt. He was easily 10 years older than her. He wasn't what you'd call a small man either. She was, however. She stood 5'2", maybe 115 pounds. He easily doubled her weight which made the combination even odder. I knew why she married him - she'd focussed on her career for so long that she woke up one day, mid-30's and panicked. She never wanted kids, that wasn't the issue, but it was clear she did want a husband. So, she settled.
For the past 10 years we were basically best friends at work. We worked in the same department at a large university so we saw each other a lot. She was really outgoing, super cute, and always dressed professionally with a slight sexy twist. She loved to wear stiletto high heels and tight skirts. For her size she had rather large breasts, but she always downplayed them, which I teased her about all the time. She just didn't care who found her sexy and who didn't.
We constantly talk trash with each other. Well, at least I do. She'd always play along. One Friday morning she sent me a message through our chat, "Let's do lunch". I replied "Sounds good. 11:30. You pick the place". She replied "K".
I always drove to lunch so 11:30 I rolled around to her side of the building and out she came. She had on a short black mini skirt, black pantyhose, and black high heels. She had a white blouse that flowed off of her arms. She carried one of her ridiculously large purses. The one thing she knew how to do really well was walk in heels. Nothing worse than seeing a woman wearing heels that can't walk in them. Trust me, even with her short legs she could. Everyone looked at her and she loved it.
She plopped down into the carseat and off we went to lunch. She almost always picked this local pub that had great sandwiches. We sat, ordered and started the normal course of bitching about people at work. The food arrived and I dug in. She didn't, which was odd. She was a tiny little thing but she could eat. She'd get this huge veggie sub and devour it in the time it took me to eat my half sub.
"I want to ask you a question. Do guys really like the thought of their girlfriend or wife having sex with another man? Have you ever fantasized about that? Does that turn you on?" she said. Interesting conversation starter. Now we talk about sex and such all the time. Mostly my sex life because hers wasn't really that exciting. Matt apparently liked sex but it was jump on, ride, jump off. Jessica complained about it but I got the feeling she was just happy performing her wifely duties for her man so she didn't let it bother her.
"You know, I'd say many do. Maybe some like the thought of watching or just knowing their spouse can turn on other men. I suspect most could never go through with it, if push came to shove. I know there are literally millions of cuckolding videos out there so apparently someone likes them" I replied.
"Is that something that would turn you on?" she asked.
"Not particularly. I'm too jealous for anything like that, although I would consider swinging. I'd never cheat on my wife, if I ever did get married, but if I really wanted someone else I'd think swinging may be the way to go." I replied.
"Yeah, as if you'll ever marry" she replied, we laughed.
That was pretty much the end of that discussion. We finished lunch and went back to work without much else happening.
Monday I got a text from Jessica. "How about drinks after work? Matt working late shift. My treat."
"Absolutely. Where?" I replied
.
"Tank House. 6:00?" she replied.
"K. See you then." I answered.
I got to the Tank House just before 6:00. I saw Jessica's Land Rover in the parking lot. She was sitting in a booth with a drink already in front of her. "Hey, been here long?" I asked.
"A little while." she replied.
I sat and ordered a Crown Royal and Ginger Ale. Jessica ordered another Manhattan. She slammed down the rest of the one in front of her. The girl could eat and drink, no doubt, but it was a little strange even for her. The waitress returned with our drinks. We were talking about her and Matt getting a new boat. They literally spent every waking moment on the water - fishing, sunning, cruising. They had a nice boat already but apparently wanted something even better. That girl was tan almost all year round.
"Matt told me that he has a fantasy about me picking up a total stranger and fucking them. At first I wasn't sure what to think. It's been eating away at me for weeks. He's brought it up several times already, in like a roleplaying scenario. He even said that thinking about the guys I previously slept with turned him on. Yesterday afternoon, we were fooling around, and he said he really wants me to do it. He even wants pictures of it!!" she just spilled this out. I don't think I made a noise or moved a muscle.
"Wow. Ok......" I started to speak.....
"The problem is that I want to do it. But there is a huge catch." she said. I was sort of shocked but as it sunk in, knowing her past, I sort of was at ease with her saying it. She had a really wild past which is part of the reason I never saw her settling down with Matt. "I'm not letting some stranger fuck me in some motel. If this is what he fantasizes about then I'm going to get something from it more than just doing it for his pleasure." she said sternly.
"Well, that could be fun, for you. Let's face it - you've always been way out of Matt's league." I said.
"Again, I'm not looking to fuck strangers or get back into the dating scene. But I wouldn't mind some additional excitement in my sex life, especially if my husband approves of it" she stated.
"You little slut....." I said jokingly. We both laughed. The waitress swung by and dropped off another round.
"Ok, so you think it's ok if I do this, with the wrinkle that I'm doing it on my terms? If he's ok with me having sex with another man I just won't tell him it isn't a total stranger. How I do this should be up to me, right?" she asked. I could see this was actually bothering her.
"Absolutely. I replied.
"So yesterday, while fooling around, he says it's ok to get a hotel room out of town, like the Hyatt in Atlanta, and I can hang around the lobby bar and if I get lucky I can take this person up to the room and have sex with them. He's clearly thought this out. It was making him more excited as we talked about it. I told him that I wasn't sure it would be that easy for me just to pick someone up, I'm not 20 anymore, so it may not work. He was ok with us trying it to see what happened. We discussed some basic ground rules, while we were having sex. It was extremely odd but he liked it and I think I may have as well." she confided in me. She proceeded to explain that there were only two basic rules that they came up with: Jessica said no black guys and they both agreed that he had to wear a condom. In fact Jessica said she'd also use spermicidal lube as well.
"I couldn't help but feel like a naughty girl. It was actually exciting. Let's just say we both finished quickly after that" she said.
Without noticing I had downed my entire drink. "So, are you going to do it?"
"Yes, yes I am. Absolutely. With you!!" she said directly.
Now I'm not the sharpest person alive, but it took for whatever seemed like an eternity for my brain to actually process what she said. I felt like I was sitting there for minutes looking off into blank space waiting for the light to go off. I stared at her and it was clear that she was not kidding. "What?" I finally blurted out.
"Look, if I'm going to be with someone else, I want it to be someone who offers me things Matt doesn't. There is only one person in my life I'd even consider doing this with - you. You and I are like best friends. We know everything about each other. You're great looking, your body is amazing, and I know the sex won't just be great but it will be really adventurous. There are so many things you've told me over the years that I would love to try. I fantasize about you or your exploits all the time. Now I can have you, guilt free. Don't tell me you've never thought about us doing it?"
My brain again lagged behind for like 20 seconds. Did she just say that she's always wanted me? She thinks of me like that? We have always flirted but I seriously always thought she was out of my league. Something in my brain started to become skeptical about all of this. "Wait, is this for real?" I questioned her.
She grinned, grabbed her phone and showed me a hotel reservation for the Hyatt Convention Center, downtown Atlanta, for the following Friday and Saturday nights. I could feel my pulse racing. "Seriously?" I said still thinking this had to be a joke.
"Yes, if you want to. I have no intention of telling Matt it's you. That's our secret." she said. I kinda just sat there processing all of this. Another round of drinks came and went. I was absolutely flattered, turned on as hell and scared shitless at the same time. A thousand questions raced through my head but none were verbalized. "You ok? You don't want to do this, do you? God, I feel like a fool!" she stated with fear in her voice.
"No, no, I really want to. Trust me. I never thought you thought of me this way, but I can assure you I have wanted you for the longest time". I answered. Her eyes were wide open - clearly she was happy to hear this.
"I wish we could go straight there now!" she said. "I have lots to do before the weekend. I'll text you Thursday with the details. I need to get home now. I'm so excited you can't imagine. Thank you so much. I seriously can't wait!" She threw down a $50 bill, kissed me on the cheek and bolted for the door.