Chris, a friend of mine from college, was the most forward guy with women. I met Chris in first year when went to the same school. I was an awkward kid, tall and lanky. Chris was already about 6 foot and fit, not muscular like he went to a gym but more like he had always done real work to stay in shape. He was average looking, mostly because of his big nose, although that never seemed to slow him down.
Even in first year, he would relentlessly hit on every girl around. He had no fear of rejection. He would hit on girls in our dorm, girls in upper years, graduate students. I even remember him hitting on this professor one time with no hesitation. He was confident and witty. Most of the time it went as well as you would expect. The woman would laugh but quickly just say no. He just kept asking. I was always skeptical about how often he claimed it worked.
We would hang out at a party. He would just walk up to a woman and say something to her, and they would just leave together. I remember when he got a car in third year. It was nice to be able to go off campus to grocery shop or stuff like that. One time we were just driving by this middle-aged woman who was walking home in the rain. Chris pulled over and asked if she wanted a ride home. When she said yes, we drove her back to her house and she invited him in. It was awkward and I had to take the bus home.
Chris was an easier friend to hang out with when there weren't girls around. Worse, it was always a bad idea to have him around any of your girlfriends. Without fail, Chris would start with being charming and interested and push the limits. It would be pointless to tell him not to. You just watched as he hit on your girlfriend. You could ignore it or leave.
It happened a few times at parties in college. I would bring a girl to a party with Chris. He would make jokes and flirt. Then if he could get them alone, he would make a move. Most of the time, the girl just came back offended. One time in fourth year the girl did not come back at all.
After that I just stopped hanging out with Chris whenever I had a girl around. Unfortunately, this meant I disconnected from that group of guys a little. Still, it just wasn't worth the frustration.
At first, I was just disappointed about the whole situation. So, I was surprised when the ideas worked their ways into my fantasies. I would find myself thinking about the girl that left with him, topless sucking him in a bedroom at the party. I would think about him rubbing his cock on her tits, her sucking him and him cumming on her face and tits. I would also think about following them into the room. Instead, I imagined her sucking him off on a bed while she sat right next to me. I would imagine her topless tits swinging as she sucked. I imagined playing with her tits, eating her from behind and even taking her head and gently guiding it up and down on his cock.
After college when I had my first job and got into some more serious relationships, I was still hesitant to bring girls to meet my college friends because of Chris. My most serious girl from before I met Laura, was named Jen. She was extremely conservative. She was definitely the kind of person that would not go for him. So, when I finally took her to my small college town, I accepted his invitation for drinks. On the way I knew I needed to warn her. "Jen, I know we are older, but Chris is Chris. He has always been a great friend to me when women aren't around. You should know he will hit on you."
"Oh, you're being ridiculous. That was college, I am sure he isn't like that anymore. I want to meet the guy from the crazy stories."
"You don't know Chris, I promise he will try to get in your pants tonight. He will start friendly and just push the line until he sees how far you will let it go." I said. "I trust you. I just don't want you to get offended. It is just how he is."
Jen smiled at me, "I can just ignore him. It will be fine. I won't get offended." With that we headed to his place for drinks. My town was small, and Chris had stayed in the small college town for work. Real estate was cheap there, so he already had his own small townhouse.
Sure, enough it was about 15 minutes after we got to his place when he started. "You are really hot!" He said winking as he handed us some drinks.
"Oh, no thank you." Jen replied. He started to take the drink back. "I'll still take the drink. Just not the comments on my looks." Jen said. It was interesting though. Jen really wasn't insulted.
"So, you are still taking...." Chris said with a pause. "The drink I mean of course."
We all laughed it off and settled in. Jen sat in an armchair and encouraged me to sit on the arm. Her body language was clear, and Chris seemed to back off. "You really just hit on all girls like that." Jen asked.
"Hey, it works. Many women find it charming, or I guess they are interested too. I think it is sad that so many guys never have a chance because they just don't ask." Chirs was Chris he never apologized. I imagined he would never stop.
"I guess if they are open to it. You do listen and take no for an answer?" Jen asked at him raising her eyebrow.
"Hey, I am not an ass. I might be a bit of a slut." Chris said trying to sound charming. He hadn't given up yet. "Be honest, if you weren't with such and upstanding gentleman, you might have thought twice about it." I was shocked when Jen didn't answer. "In fact," Chris continued, "There are some women and couples that would say yes regardless." Again, with that unapologetic grin. "It also might be that some girls know that my nose isn't the only extra-large thing about me."
"Alright enough of that." I said. The conversation shifted to talking about old friends and past shenanigans. Chris seemed to finally drop it. While he wasn't the best to have around your girlfriend, he was an old friend. He knew where everyone was, and all the latest news. It was good to hear about many people I hadn't thought of in years.
Later in the evening, I was a little drunk and Jen had slipped upstairs to use the bathroom. When I looked up, Chris was gone. I was drunk enough, and I trusted Jen enough, to not rush up the stairs. Still, I didn't want him harassing her. Just as I was about to get up Jen came down the stairs flush. I looked at her trying to decide if there was any chance something had happened.
Later at our hotel room, she explained they had a little banter that was all. "He just kept talking about how hot I was. He asked if I had ever thought about a threesome. When I said no, he moved like he was going to try to kiss me and said to think of him if I ever change my mind." Jen didn't seem put off at all. "You were right he seems to be the same guy he was when you were in college. Maybe he should have moved out of this town."
I started to go down on her. She was a little hesitant. "God you are soaking already." I commented as my fingers easily slid into her pussy.
"Your fingers feel so good." She interrupted.
"I thought you said he didn't touch you." I lifted my head up looking her in the eye.
"He didn't touch me." Jen responded pushing her pussy down onto my fingers. "Are you going to eat me or not." This was serious dirty talk from Jen.
"Did he get you horny talking about a threesome?" I asked playfully.
"Just fuck me. I don't want to talk about it."
As I fingered her, I looked up at her. She was bucking her hips against my hand. Even if she didn't want to talk about it, it was clear she was still thinking about it. "Hey, you never answered him, if you were single, would you have considered letting him fuck you?" I asked then I started to lick her clit.
She grabbed the back of my head and jammed it into her pussy. She came hard on my face. I kept licking as her legs squeezed shut on my head pulling me away. "You still didn't answer." I said as she held me off her clit as the orgasm passed.
"I don't know." Jen admitted.
I climbed on top of her and started to pull my cock up and down on her slit. "Just fuck me." She said.
I went slow teasing her with my cock. "I want an answer," I said teasing her. "Do you think you might have let him fuck you if you were single?"
"Maybe" she moaned. "Now fuck me."
"Close your eyes." I suggested as I pushed my cock into her. As I started to pump her pussy, I noticed she did. She bucked on my cock. I fucked her thinking about watching her with him. Holding his ass as he pounded her. Imagining his cock moving in and out of her cunt. She reached her hand down to her clit. "Are you thinking about fucking him?" I asked as I felt her pussy squeeze tight on my cock. I knew she was close to cumming.
"Oh God yes." She shouted. We both came hard. Then we remembered we were in a hotel room and got a little embarrassed. Hotel sex was great. You didn't need to worry about the noise. But that was loud.
This is where my fantasy of watching my partner get fucked moved from confused to a real fantasy. It was the best sex Jen and I had ever had. Unfortunately, it was also the last time she would talk about anything like a threesome. Jen returned to being very conservative. I became increasingly frustrated and eventually we broke up.
When I finally met Laura, my adventurous side was set free. Early in our relationship, we had a lot sex. Unlike with Jen, it was imaginative and playful. We played with all kinds of toys. We were both more mature and we were much more aware of our fantasies. We played at our fantasies through roleplays and toys. Like me, Laura had a threesome fantasy. She often liked to watch porn where there was one woman with many men. I loved to talk to her about watching someone else fuck her while fucking her with her vibrator.
A few years later we married. Everything was going well when Laura suggested we go to my small college town so I could tell her about the old days. Her college was in the town where we both worked. We had been to her college, and I had met lots of her old friends. She said it was my turn to share even if it was a bit of a drive.
Laura and I had been getting more into the threesome fantasy. I also knew I had told her about Chris. I started to wonder just how serious she was about the fantasy.
I thought about setting up drinks with Chris. Unlike Jen, Laura was open and adventurous. She liked to play at things like threesomes. I wondered if she would deny him the way Jen had. I wondered if I wanted her to. I remembered the night of incredible sex with Jen.
Introducing Laura to Chris was a danger. Once he started to press, she might be into it. If I didn't want that, things could get out of hand quickly. On the other hand, for years I had thought about him and Jen when I masturbated. His relentless, but kind, attempt to get with every woman available was weirdly hot for me. Also, the idea that we could do this and never see him again was appealing.
As we drove the 4 hours, I thought about it. Chris would start with engaging her with a little risky conversation. I would enjoy this. He would then find a second alone. He would see how she reacted when he tried to touch her. I wondered if he really had managed with Jen all those years ago. She had been so wet. She insisted it was just the talk. With Laura he had a much better chance.
When I thought about it my erection swelled in my jeans. Thinking of her pressed against the wall making out with him as his hand explored her body. The more I thought about it the more I realized that I really wanted this. As long as they didn't leave me out.
I was curious to find out what Laura wanted but was a little worried about just asking directly. I had told her about Chris so I just asked if she thought it would be fun if I tried to set up drinks with him. I thought either she could tell him no and it would be fun to fantasize about it back at or hotel room. Of if she was in, well it could turn out to be one of the hottest nights ever.
