With NYE coming up I got to thinking about my craziest NYE ever.
A few years ago I was in my early 30’s and just coming out of a 7year relationship. We had lived together and were planning on marriage, kids and a life together but it fell apart. I was pretty depressed and was just planning on staying home in my jammie pants watching TV for NYE.
I got a text at about 10pm from a friend of my ex (Jillian) asking if I was planning on coming over to their NYE party. I had received an earlier invite on a FB message but I assumed it was just a group message and that they hadn’t heard about our breakup. I had ignored the message assuming that I was not welcome in their social circle any more.
Jillian was a hard bodied blonde, originally from England. Her and my ex had met through work and we had spent some time with her and her husband Trevor on a few dinner dates. Jillian was a marathon runner and was extremely fit and toned. She was a successful business owner and had a classy, dominating women with her shit together kind of vibe. She was always flirty and fun, and the accent helped take it to another level. I had always thought she was hot AF but of course never acted upon it. Trevor had been in a wheelchair as long as I have known him. He was a quiet guy and was at least a decade older than Jillian. He was an IT security professional who maintained several smaller companies systems from his home office. We had done some low level sports bonding, but we hadn’t ever really been close.
I texted Jillian back saying I was just hanging out at home and not planning on going out. She told me to get the fuck off the couch and get over here. I quickly showered, threw on some clothes and made my way over to Jillian and Trevors place by about 11pm.
Jillian met me at the door with a big hug and a kiss on the mouth. She had obviously been drinking and was dressed to kill. She had a tight black dress on that showed off her figure and had an open back down to her butt that showed the muscles in her back. I broke off the kiss first, thinking that everyone might be watching.
The party was hopping. Lots of couples and people there, all dressed up and drinking. I was a late arrival and was several drinks behind everyone. Jillian kept her hands on me, holding my hand or touching me as she maneuvered around her house. She introduced me to a bunch of people and I knew a few. I felt a little self conscious having the married hostess talk to others with her hand on my ass, but I wasn’t about to tell her to stop.
I talked to a few people, had a few drinks and nodded towards Trevor when I saw him watching me from across the room. I made my way over and said hi. We made work small talk for a few minutes and then he looked up at me and said “She really likes you. Do you know that?”. I didn’t know how to respond and he wandered off.
Jillian managed to be beside me when the ball dropped, she grabbed me by the back of the head and just made out with me. Mouth open, tongue the whole bit. It lasted for about 20 seconds and I felt the stirring of an erection. There were people all around us hugging. I finally pulled away, again feeling self conscious about the public display. She gave me an evil smile and moved on to straddle her husband in his wheel chair, passionately kissing him. I was a little light headed, confused and drunk. I moved off to mingle a little more.
By 1:30 the party had emptied out with only a few people left behind. I told shook Trevors hand and said thanks for the invite and then told Jillian I was on my way out. She looked alarmed for a second and then said “You can’t possibly drive in your condition, why don’t you lay down on the couch until you sober up?” She gave me a comically big wink. I wasn’t all that drunk, but I had a pretty good idea where this was going, and did as I was told.
I was on my back with my eyes closed, napping on the couch when I felt a presence beside me. Jillian was kneeling down on the carpet beside the couch. She told me that everyone was gone. Her hand was on my thigh and she moved it up to my crotch while looking me in the eye. She told me that she had always wanted to fuck me and she was really excited when she heard that my ex and I had broken up. I didn’t say anything, just laid back with my hand on her tight ass.
She undid my zipper, shuffled my pants and underwear down so she could pull out my cock. Now semi hard she was holding the base and waving it around. She started talking to my dick, telling it how big and beautiful it was. She had laid her face on my thigh and I could feel the hot breath on my balls. She was slapping my cock against her face while complimenting and kissing it. The contact, her accent plus the rock hard ass was really working for me. I was very quickly fully erect. I looked down at her and she just seemed off in dreamland. So happy to have a dick in her hand.
She started sucking it from the top. The tip was in her mouth as she worked around the head with her tongue and created a sucking vacuum. Her hands were stroking the shaft and rubbing my balls. She kept this up, focusing all of her technique right on the tip. The sensation was almost too much. I hadn’t had sex in months. I put my hand on the back of her head and pushed it down. She gagged and pulled back.
“Not used to that” she said smiling.
She went back at it. Lubricating and going deeper with each stroke of her mouth. She eventually pushed all the way down until my cock was fully down her throat. I could feel the tip of my dick push past the muscles in her throat. I could feel her gag reflex kick in but she kept her face buried all the way like a trooper. I was getting close already.
She pulled up with a deep breath and laughed
“I did it honey” she called back over her shoulder loudly.
I hadn’t even thought about Trevor. I had been distracted by the blow job.
“Where is he?” I asked
“Watching, on the cameras.” She motioned her hand up in the air and waved it around “He likes to watch!”
We moved into the bedroom. Trevor rolled out into the bedroom to meet us from his attached office. He explained that in the car accident he was a T5 and had lost the ability to feel anything below his ribs. He couldn’t enjoy penetrative sex anymore. He told me he was a committed voyeur now and encouraged her to explore as long as he could be a part of it.
Jillian said it took a long time for her to take him up on his offer. They had tried some arrangements with a few other guys, but it hadn’t worked out for various reasons. It’s not often you can bang some ones wife while they watch and feel like you are doing them a favor, but here I was. Ready to help a friend out and do my part.
I turned to Jillian and we helped each other out of our clothes. I pushed her onto the bed and stood at the foot. She had her head positioned over the edge as she laid on her back. Her mouth was open and I guided my cock into her throat. Trevor had wheeled up beside her head, watching from close up as I jammed my stiff cock into his wifes throat. I pushed all the way in until her chin touched my pubis bone.
Trevor reached out and felt Jillians throat as my cock bulged it up. I started stroking and Trevor kept his hand in place, feeling my cock slide in and out of her esophagus. She had one hand on my thigh, ready to push back if she couldn’t handle it and one hand wrapped around her husbands collar, pulling him in closer.
I leaned over and grabbed her tits as I built up speed and power, I was really feeling it and started throat fucking her hard. She pushed me off, gasping for air. Her eyes were watering and she had spit and precum all over her face. I was going to give her a few seconds to recover, but Trevor pushed me back in.
“Fuck her face” he said excitedly. She nodded and opened her mouth. I rammed it back in and kept stroking. Trevor was pushing my ass from behind and giggling. Telling me to go harder.
The pressure was building for me and I told them I was going to cum. I told Trevor to grab my dick when it came it out and aim it at his wife. He looked up at me and I knew I was probably pressing his boundaries. I nodded and told him it was ok. I pulled back right at the last second and Trevor grabbed my dick by the base, aiming it at his wife. I shot several long ropy rockets of cum all over her face, neck and tits. It had been a while and I had a big one saved up.
I collapsed on the bed, spent and breathing hard. Jillian flipped around onto her back and hung her legs over the edge. Trevor wheeled in close and buried his face into her pussy. We were side by side on the bed. I watched Trevor lick her for a minute and then laid back beside Jillian. She was quickly working towards orgasm. She reached out and grabbed my floppy cock as she built up. Squeezing it tight in her grip. Her face and tits were still covered with my cum as she arched her back, wrapped her legs around her husbands head and pulled him in while moaning.
I got up after she had finished and started putting on my clothes. They both asked me to stay longer, but my brain was pretty fried. As I was leaving, Jillian escorted me out in her robe and asked me if I would come back again. I told her to text me in a few days after I had thought about it. As I walked to my car, I was pretty sure what my answer was going to be.
Source: reddit.com/r/gonewildstories/comments/kne8zo/fmm_new_years_after_party_helping_out_a_friend
Please write and post more! I love the way you write.
Great story ??