Here we were in Chicago, my best friend Jimmy and me. Jobs and an apartment checked off our list. This was such a contrast from the dairy farms that we grew up on. As far as we were concerned it was the Gwen and Jimmy show and the rest of the city passed around us.
Jim was strikingly beautiful with a chiseled jaw. A light brown complexion with wavy black hair and hazel eyes. His body is muscular but lean, and 6 feet tall. I thought I was plain, 5'5", auburn hair, big blue eyes with long lashes, with ample breasts, and no curves elsewhere.
Our first big outing, after we settled in, was to the famous Boystown neighborhood, we found no shortage of bars for our pleasure. We were like animals, at the clubs between the alcohol, drugs, and sex. Especially the sex. We would laugh saying Jimmy's percentages for getting hit on or hook-ups were about 99.9% with men, while mine was at 49.9% to meet women. This first time at the clubs was no exception to those percentages. The guys were all over Jimmy.
When Jim would entertain his male friends, he'd leave his bedroom door ajar. I stood in the hall listening or peeking into his room. The sounds of moans, slurping, sucking, and whimpering made my blood rush through my body. Bodies in motion working in unison with pelvises, hips, and penises grinding or thrusting in/out over and over again. Men on all fours, asses in the air as Jimmy would fuck them hard and dirty. Sometimes he would be on his back, hand foundling his hard cock, a man entering his hole and pushing in with slow strokes. He knew I was watching because he was watching me too. It wasn't until I saw Jim's mouth swallow a guy's dick that I finally admitted to myself, I wanted to try that.
Jim's new steady boyfriend stopped by many times a week for the last few months. Sometimes they go out and sometimes they stay in. When the new boyfriend, Jeff, is around, Jim's bedroom door is always closed. Jeff and I see each other passing in the hallway or the lobby of our building. Only one time did he speak to me and that was because I said hello and introduced myself.
One afternoon, Jimmy asked if we could have a heart-to-heart talk. "Of course," I answered. "Gwen this is hard for me to say to you, please let me finish before you speak. We hide in the shadows watching each other. You turn me on, I like seeing you naked and I have been thinking of you not as my best friend. I want to touch you and have you touch me." Jimmy confesses. I stopped breathing, "What the fuck, Jimmy!" and I walk away. My mind is freaked, he always liked men, and we have been friends since grade school. This is not my best friend.
Jimmy yells out, "There's more, please talk with me." We go and sit down on the couch, he holds my hands in his. "I was wondering if you would sleep with me, but with Jeff there too. He's slept with women and I'd be more comfortable." he expresses shyly. I've had enough but before I go I light into him. "What if you hate having sex with me and I love it." I stormed out and slammed my bedroom door.
The next morning, Jeff was at the kitchen table with two cups of coffee. "Where's Jim?" I ask knowing he is at work. "Is this your idea? Do you need pussy and dick? You two are crazy!' I blurt out before even tasting my coffee. He grabs my wrist and begs, "Please, Gwen, please sit." With his other hand, he holds out my coffee.
Jeff continues, "He's in love with you. You are all he talks about. Sometimes I feel jealous so I did suggest this to him. Honestly, with everything he tells me, I think I'm a little in love with you too." I smirk, "Well that changes everything." He goes on, "Maybe we could take baby steps, kissing, cuddling, touching over clothes." I look him in the eyes, "I have to think, do not bother me with this again. I will let you two know what I decide."
It wasn't long before I made up my mind, although I did not want to admit to the lingering doubts. I put a big sign on the coffee machine one morning, ready to talk at 10 pm tonight. I not only got a confirmation text from Jim but from Jeff too. Going off to school and then work, when I returned home they were on the couch with the TV on. Their eyes were on me as I walked to my room. It wasn't 10 pm. I took a shower and put on my comfy nightgown, robe and slippers. Right at 10 I walked into the living room and sat down to talk, someone turned the TV off.
They both looked at me with puppy dog eyes and it was adorable so I smiled. Jimmy jumps out of his seat, "She says yes!!!" I nod as they make room for me on the couch right between them. They immediately start touching me over my clothes, kissing my face, lips, and neck. Jim takes my hand and tells me "Thank you." Jeff puts his hands to my face, "This makes us both so happy." I feel like I'm going to faint because my emotions are running so high.
Then they both got up, I thought they were leaving, but they stood right in front of me and started to undress each other. "This isn't baby steps, guys," I complain. Hard and flushed their bodies start to grind on each other frotting their cocks. I'm beyond excited, trembling I stand up, not knowing what I'm doing. Jim touches my face and I go to my knees, my mouth opens, my tongue hangs out, and I take his hardness into my mouth. My body is aroused as I start to lick and suck his cock it is an unbelievably powerful feeling. I love it! I don't want to stop but Jim pulls out and Jeff replaces him in my mouth. I'm wet and so horny.