So this story turned into a mini novella. I did not want to shorten it. I feel like I would be doing everyone in it a disservice. Plus this is my personal life and how it went down. I always liked the chase or challenge as much as I liked the act itself. Hopefully someone finds it hot.
It was the next night after Syd and I [Jake] had our fun with Dana. The two of us were driving around. We had not talked about what happened. I knew it was coming though. Things were a little awkward between us and I really did not know what the hell to think or do about it.
Syd suddenly broke the silence.
“Jake we are friends right?”
“Yup”
“We can tell each other anything right?”
“Yup”
She was staring out the passenger window.
“I DO NOT want to fuck up our friendship.”
“RIGHT” -SHIT!!! Friend zone time…UGGH.-
She looked at me. (Oh boy) I thought, here it comes.
” I do not want to be in a relationship”
“Yup”
“Kate mind fucked you and I have my own issues.”
“Yup” -my hand tightened on the steering wheel- “So what now?”
“Well..I have an idea. What if we just…you know. Did that again?”
“Uhh. Did what? Share Dana again?”
She said, “Yeah sure share Dana. But like other…ones…too???”
“Other ones?”
“Why not?”
“How would that work?”
“Not sure. I mean. We could get girls together I guess?”
“So you don’t like guys anymore?”
“I will always like guys Jake” “But maybe WE shouldn’t?” “Did you like what we did to her?”
“Yeah that was pretty awesome!”
She laughed as I pulled up to her house. “Yeah Jake that was awesome.” She gave me a peck on the cheek and got out with an “I will call ya”
Fast forward a couple days. My friend Ben who I played ball with in college was over. It was a tuesday night and we were bored as hell when the phone rang. It was Syd. They were at her friend Jane’s house with some girl named Tina celebrating Jane’s birthday. Syd invited us over. Jane was cool I guess. I never really thought about her as being sexy. Never occurred to me. Mainly because I was busy being mind fucked by Kate up to that point. She was 5′-10″ and thicker than anyone I had been with. She always seemed awkward to me, but Ben and I were bored so we went.
We drove out to her place at about 11 pm. She had her own trailer on her parents property. We were from a small town and that was common. I thought it was cool she had her own place. We entered and greeted the three girls who all had on jogging pants and hoodies. Fuck-this is going to be LAME….
They were blasting some Fems and everyone but Tina was drinking. She had to work the next day. I guess she had a jealous boyfriend also who would not approve of me and Ben being there. We started playing drinking games and it was not long before Ben said we should play quarters. I chimed in “strip quarters” half jokingly. Jane shot me a look and said sounds good to me! Tina got her shit and left.
Now Ben was a cool guy, but we had not hung out a ton. I remember the girls all looking up at him towering over me as we walked in. He was a little gawky at 6′-10″ but that seemed to just spark the girls attention. Especially Syd. Ben sat at one end of the table. I was on the other end. This left the girls both side chairs. Jane was close to me and Syd was by Ben.
We began bouncing quarters into the shot glass. A miss was a shot. A second miss was a piece of clothing. Ben and I were good. Too good in fact. It was not long before the girls had removed each shoe, hair band and sock before we started to get to the good stuff. The guys had only lost shoes and a sock or two. It was Syd’s turn. A miss. Shot. And another miss. “DAMN!!” “THIS IS NOT FAIR” She somehow undid her bra and was able to somehow reach up her sleeve to pull it out without us ever seeing anything. On Jane’s next turn she did the same thing. LAME…
It came around to me. I made it clear I missed on purpose twice. Drank my shot and took off my shirt. Sure I had socks on but fuck it. Ben opted for his last sock when Syd purposly made him miss his bounce. It went to Syd who only had to do a shot. LAME. Jane was up next. She missed again and did her shot. Missed again and started complaining about how unfair the game was. And that we cheated.
Syd said. “OK. you can have another bounce”
“NO FUCKING WAY!” “Pay the piper” Syd looked at me and smiled. I knew she had this. I almost started to feel bad for Jane. Almost…
“Here is the deal.” Syd said. “I will bounce for her. If I miss you have to take her over to the couch and remove her panties” Jane covered her face with her hands. She finally popped her head up, I guess trusting Syd would somehow save her ass. “OK” she replied. I nodded my approval to my wingwoman.
Syd grabbed the quarter and bounced it. Missed by a mile. Was not even close. Jane took a shot grabbed me by the hand and led me to the couch. She sat down legs together. Her hoodie was long enough to cover ass. I got to my knees. Placed my hands on her knees and spread her legs. I moved my hands slowly up to her hips as my head moved toward her black panties. I was wondering if I was taking it too far. Waiting for her to clamp her legs on my head to stop me. I would have stopped. But she did not. Instead, she slid down a little and grabbed my head as she opened her legs wider. I nuzzled her panties with my nose as my hands moved up to her chest. She started breathing harder as my tongue tasted her now wet panties. Her breasts were really nice. Much bigger than I was used to. Not LAME. I then slid my hands back down to her hips finding the top of her panties. I also moved my mouth up and grabbed them in my teeth. As my head pulled them down she lifted up allowing me so slowly slide them down. I caught a glimpse of between her legs. She was trimmed nice and neat. I pulled them completely off her legs and slid my body on hers up near her face with them in my mouth. “I Think you lost these”. She took them from me and put them in her front hoodie pocket with a sly smile. This was turning out to be a fun night…
Syd led Ben over and sat down sat between the two. Jane threw a cover over them. I kinda stood there. The girls were giggling. Syd looked at me.
“Don’t just stand there dance for us!!”
What the actual Fuck??? Sure I could dance. But???
Fuck it. I started dancing. It got weird for Ben real quick when I started unbuckleing my pants. I think his exact words were “I DO NOT WANT TO SEE HIS DICK!” I was also relieved. But fuck it we had two hot girls!!!
The girls looked at him laughing. Syd said “Well here look at this instead. She put her hand between Jane’s legs. -Now I do not know how many of her friends she had played with, but I was finding out quickly it was alot- Ben’s attention had quickly turned to the girls. And he soon accepted an invitation under the covers to explore Syd a little more. She gave me a nod and I continued dancing. The girls eyes were fixed on my movements. I could not tell what they were all doing under the covers but had a good idea. I turned around and let them watch my ass as I slid off my pants exposing my silk boxers -Mid90’s remember- and let them hit the floor. I continued my sorry ass sexy dance and slowly turned around. Full wood poked my boxers out. The girls started laughing. Ben must have been getting hot and came up for air. He made the mistake of looking over. “What the Fuck dude?” The girls got up and walked down the hall laughing. I just put my pants back on. “SORRY MAN”
The girls were gone a while. I have been in enough trailers to know where the hall led. I told Ben “C’mon”
When we walked into the bedroom. Syd was making out with Jane on the small bed. When they noticed us they both stopped. We walked over and I started kissing Jane and Ben Syd. Jane started getting really turned on and basically pushed me to the bed and before I knew it had my pants down and my cock in her mouth. Ben noticed this and said “NOPE” and led Syd back out to the couch. I was glad. I was going to need more room anyway. Jane was masterful. Almost too masterful. And certainly aggressive. She pulled her hoodie off and came back up for a hard kiss. I rolled her to her back and kissed her back hard. I could hear Syd and Ben starting in the other room. Jane put her hand on my head and forced me down between her legs. She let out a hot moan as I began to taste her. I used my tongue and fingers as well as I knew how. I did not want to be out done!!! Her legs wrapped my head holding me in place as she came for me. She reached over into her nightstand and grabbed a condom. She kisses me hard as I rolled it on. She pulled me down onto her and I slid in easily. She wanted it hard and fast and we quickly set a rigorous pace. She bucked her hips back up into me like a crazed animal as I thrust down inside her. She told me she had thought about this for a long time. I rolled her onto all fours as we regained our frantic pace. She reached for the bed post as the feeling started to be more than she could take. I pulled her hair as I drove deeper into her each time. I let go of her hair and she fell forward she pulled a pillow to her face, screaming into it before she started to shake. She had had enough and bucked me away. She quickly turned her body around and pushed me back onto the bed. She pounced on me removing the condom, taking me into her mouth. Her hand wrapped around my base as she worked the top with her tongue. Her breasts swayed from her movements. I began to feel it welling up inside me and knew I couldn’t hang on much longer and told her I so. It did not stop her. She kept on and on until I lost it and took all of me in. Wow. Now I was shaking. We caught our breath and the intensity of the moment faded. Later. we got dressed when Syd walked in.
“What’s up guys?” “You hungry?”
We were and piled into separate cars. It was now about 7 am and light out. We drove to a local truck stop. I bought everyone breakfast. It was the least I could do. The girls left afterwords. Ben said we had to hang out more often!!! Lol. Yup.
Two nights later I got a call from Jane at 2 am. She was kinda going on about how she always wanted to have sex with me. How I had the second biggest dick she ever had. Thanks??? Shit got weird with her quick. I told Syd and she must have straightened her out. That was the last I saw of Jane.
Hope everyone liked it.
Source: reddit.com/r/gonewildstories/comments/gmtjh5/mf_and_mf_mid_90s_fun_and_friends_2