I’ve been waiting for the right thread to share a few stories but this one seems to get traction from time to time and doesn’t have a specific subject so I’ll start here.
We’ll call her Emma. We started dating after meeting in a class at community college. We were both 20. She’s a brunette with a nice figure. Wasn’t into working out but was trim with nice hips and a round ass and beautiful b cup breasts. She had sort of a deceivingly sweet face which I found so hot when we met. She looked like a girl you’d take home to mom but she had such a dirty sense of humor. We ended up in the same social circle and eventually started dating. It lasted 8 years when we agreed to break up. We were just in different places. Anyway that’s the boring stuff you guys don’t care about.
I had only had sex three times albeit with three different girls. Three one night stands. Emma had had a couple longer term boyfriends and several one night stands. Needless to say I was clueless and she knew how to fuck. It was intimidating at first but she “trained” me so to speak. She constantly swore I was the best she ever had and I believed her because her other partners were young and dumb too.
We had hypothetical conversations often. About other people we were attracted to, expressing fantasies of threesomes and stuff like that. It became an ongoing thing. We had an in-joke on whether our friends or coworkers “could be a third”. But it was all talk… until one day.
We were drinking in our apartment. I’d say we had been together for two years at that point so we were both 22. My friend James had stayed with us for a week after a bad break up. He had found an apartment now but was stopping by a lot as he was lonely. This came up in our convo and I said how I felt for the guy. I mentioned to her that I couldn’t imagine going from living with a girl and having sex daily to being alone would be so hard. Emma sort of jokingly quipped “well I always thought he’d make a good third.” My stomach dropped. But there was zero jealousy. I recall I got a full erection immediately. Not just the idea of her with another guy but her being bold about it. It turned me on so much. I said back to her, in a joking manner in case she was totally kidding, “well maybe we should call him.”
She shot the idea down. We were drunk. But I sort of kept at it. Not talking her into anything, just asking questions. She confided that she’s always thought he was good looking and that in sexual conversations with his ex she knew he was good in bed and that he had a big dick. Now jealousy started to pop up. I’m not small but average. I’m 6” which is plenty from my experience. And she said that in her experience it wasn’t that bigger was better as far as how it felt but that she just thought guys looked better naked with big dicks so she had fantasized and wondered what he looked like naked. In a weird way the injection of mild jealousy only made it more arousing to me.
For a week or so we’d see him almost daily. And after he’d leave I’d make remarks to her about him. “He looked good today” “I wonder what he would’ve done if you just grabbed his package”. Stupid stuff like that. She’d laugh it off and tell me to shut up. I suggested to get one day that we play a drinking game. He was coming over that night. I asked her if she would be comfortable if during the game I dared either of them to remove clothing. We had a specific game with loads of house rules with dares and making people do things. She sort of couldn’t commit but said maybe.
I already detailed this night in another thread here: EDIT: it won’t let me share the URL but if you look at my post history it’s from the thread “Has anybody exposed their wife’s body (in person)?”
But now you have a little context to that night. The story doesn’t end there however. A couple days later I was with James at a bar and he brought up that night. He said it was the most action he’d had in weeks. He then immediately back tracked saying he didn’t mean to imply it was sexual between him and Emma. I eased his concern and said it was all in good fun and that Emma had a blast. He seemed relieved. The conversation turned back to his breakup and man the guy was miserable. Just so lonely and regretful. So I invited him back to the house.
I called Emma to give her a heads up. When we got to the apartment I could hear the shower on. Which was unusual for Emma to shower unless she had worked but she was off that night. I immediately connected that she wanted to be fresh and clean and looking her best for James. I was a bit buzzed and jealousy was no where to be found. I immediately decided to try to steer the course of the night to some kind of sexual activity. I gave James a beer then took one to the bathroom for Emma. She was out of the shower in a towel. She looked so sexy. I gave her the beer and quietly told her James was in a funk and needed some cheering up. Feeling bold, I said maybe you should give him a blowjob. She rolled her eyes and I shrugged and said “I mean if it comes up in the drinking game, rules are rules.” And left.
She eventually joined us. She had on pajama shorts and a t shirt. Normally she’d be braless but she had one on since we had company. Regardless I could tell she put extra thought into her attire. She looked so sexy. We made small talk and then started the game.
Eventually there we were, yet again, half naked, drunk and having a good time. I suggested a new game. I had one that my uncle had bought me as a gag that was WAY too risqué to actually play. It was a dice game where you would roll and it would make you strip, touch, perform oral, etc. We always joked about playing it but never would. It was too far even for us. But that night, feeling drunk, and pity for James. Knowing how down he was and that we had all bonded so close I suggested it and Emma actually agreed to “try it”. James was unaware of how far the game goes.
At this point he and I were in boxers and Emma was in her bra and underwear. I rolled first and it declared I had to make a player undress. Not remove an article at a time but fully undress. Like I said the game was risqué. So I nodded at Emma and she rolled her eyes but didn’t say a word. She stood and unhooked her bra and let it drop to the floor then slid her panties down and stepped out of them. She was fully shaved and her lips looked delicious in the dim lighting. The thing is she must have shaved after I called to tell her James was coming. I knew she had stubble that morning. She didn’t hide herself. Not at all. She sat with her legs together but didn’t make any attempt to cover her tits.
I can’t even recall the exact order but soon I was naked. I sat forward to hide my hard on. It was James turn to strip and he stood up revealing his cock was hard under his boxers. “Sorry. Can’t help it” he said and Emma blurted out “no need to apologize James”. The way she used his name turned me on. He slid them down and yeah. His ex was right. He was at least 8”.
Now this was the only night we played this game so I can’t really recall the rules but I have a series of pictures that have helped me keep the story pieced mostly together. The dice dictated that Emma had to touch his cock. And it was a source of discussion. Both kept at me making sure I was ok with it. I kept saying it was the rule so we had to and they kept feeling like I was unsure. When Emma finally reached over to his crotch she wrapped her fingers around it slowly and held her hand there for a moment and as she pulled away it was a slow hesitant release. She didn’t seem to want to let it go. I was throbbing down below. I wanted to just suggest a threesome but I resisted.
The game dictated that I suck on Emmas nipples. Then she sucked on mine. Then James sucked on her tits. Watching Emma’s face as he leaned over and flicked his tongue on her nipples killed me. Her eyes closed and she bit her lip. After ten seconds he pulled away and she made eye contact with me and had a look of arousal I’d never seen. We were in new territory and it was so exciting.
All of our drinks were empty and Emma decided to go get more. We both watched her beautiful butt sway into the kitchen. There we sat together. Naked and vulnerable. Both hard as a brick. But it was like we had achieved another level of friendship. I broke the silence. “You know it’s not a big deal. It doesn’t bother me. It’s all in fun and I know Emma is mine only. This stuff is just physical.” He asked if we’d ever done this stuff before and I said no. But we felt comfortable with him and we also knew it could help him move on from his ex.
Emma returned with another round of beers and was almost giddy that it was her turn. With us being alone both of our erections had subsided and we were both at half mast. “Aww where’d my little buddies go?” Her dirtiness was at peak form and I loved it. She smiled ear to ear and picked up the dice. She rolled them and the conclusion of that roll was sucking James’ cock. A lump formed in my throat as I looked to James’ cock and could see it stiffening in real time. Emma looked to me for one last nod of approval which I happily gave. She got to the floor and crawled a few feet towards him. My dick stiffened up as well. She placed her hands on his thighs and slowly leaned her head in. She was looking up at him and he down at her with an expression of pure excitement. She pressed her lips to his cock and slowly took him a few inches down then back up, teasing him a bit. I knew Emma and she was a person that if you were gonna do a job you had to do it right. So she wanted to show off for him. Maybe outperform his ex. She flicked her tongue along the head before finally taking him deep into her mouth. The bottom inch or so was too much. She could deep throat’s me but he was just too big. She added a hand to the mix stroking him from the base up while sucking the top half for about 20 seconds. He moaned a couple times and then she slid her lips to the tip and gave one little smack and was done. The game dictated these acts were to be done for ten seconds but we kept going s not beyond that.
He let out a deep breath and said he probably wouldn’t have lasted much longer. The next roll had me using my hand on Emma. As I slid between her legs she was dripping wet. I stroked her clit then slid two fingers inside her. James was watching and holding his dick. She locked eyes with him as I fingered her. Then I stopped. The next roll had James eating her out. He got between her legs and flicked his tongue against her wet shaved clit and she immediately moaned.
At this point we abandoned the dice. I moved over to them and kissed Emma deeply before moving my face to her tits and started sucking on her nipple while groping her other breast with my hand. She wrapped her hand around my head and gripped my hair. I looked down as she moaned into my mouth as we kissed and saw James had inserted two fingers while he sucked on her clit. Again I knew her well I and I knew she loved that and was approaching orgasm within a minute. She started to quiver and her moans turned to screams as she came hard from his work. She pushed his head away as she gets very sensitive right after an orgasm. He wiped his mouth which was covered in her wetness.
She caught her breath as none of us spoke. Then she got up and sat James down next to me. She looked from my eyes to his and back as she started to stroke both of our cocks kneeling in front of us. She then took my dick deep in her mouth and sucked me with passion and in about twenty seconds I came. The whole night was just too much more me. She swallowed every bit. I laid back breathing heavy as she shifted focus to James. She took more time with him. She sucked his dick and he reached down and played with her nipples. After three or four minutes he stiffened up and groaned and filled her mouth with cum. It dripped down the sides of her chin as she tried to swallow it all. Then she sat back against the coffee table all of us catching our breath. Naked in the early hours of the morning.
More to come if there’s interest.
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