Every month my friends and I try to get together, have some drinks, and make dinner. It's usually just us guys but this month my GF came along because her plans fell through and I felt bad leaving her back home alone. She was happy to come, knows all my friends, and we're all very comfortable with each other so there were no problems amongst the group with her coming along. We've been together for quite a few years now so it's not strange for her to be around my friends and there's no 'getting to know each other' stigma.

We try to rotate who's house we do this at and who's cooking so it stays pretty fair. This month it fell on my friend Jack. He lives in an apartment with his GF so we figured she'd be there anyways so my GF would not be the only woman there. Now even though we meet up monthly, we don't all talk regularly or text, with the exception of some memes shared to each other daily. We use the monthly get togethers as out talking points and time to catch up since we all have busy lives. Jack is one of the newer friends in the group, who's been around for about as long as my GF and I've been together. Not saying much as it's been years.

We showed up and we were the first of the group there. I always try to show up a little early incase whoever is hosting needs help cooking or preparing. After getting settled in, my GF and I noticed Jack's GF Nicole wasn't there. We also noticed that a few decorations were missing, and the pictures they had of each other were no longer on the wall. We asked the question that we knew the obvious answer to and confirmed that Jack and Nicole had split up over the last month. She moved out and she'd been gone for two-three weeks. They were together for years before we met Jack so he wasn't feeling the greatest and we gave him a chance to vent, which he took very easily letting everything pour out. We told him we wouldn't say anything to anyone else and we'd let him bring it up if he felt comfortable as the wounds seemed pretty fresh.

Fast forward a few hours and we're all a few drinks in, not getting drunk or over indulging. Just relaxing, enjoying company, and having good conversations. I pulled my GF aside to tell her that when we get home we needed to make some time for us to have some fun. She dresses conservatively but in a sexy way. She was wearing Converses with high waisted ripped denim shorts that were short but not to the point where they exposed her, and a crop top that was an inch or two shy of her waist band. So nothing 'slutty' but when she moved the right way it gave me that 'tease' that when accompanied with my horniness made her difficult to resist.

She giggled and suggested we run to the bathroom for a quick one to hold me over. Jack's apartment only has one bathroom and with seven of us eating and drinking, I didn't think it was the best idea, so I suggested our SUV. We excused ourselves to go have a chat in private, not anything that would raise suspicion. What was supposed to be a quick hook up, turned into us intimately having sex for over an hour in our back seats. That plus the time for her to clean herself up took well over an hour before we walked back into our friend's apartment. This time she looked the exact same, less her bra that we used to wipe her down after I finished on her chest. To which I had some worry about the guys noticing as her nipples weren't softening up since I think she was still very aroused about what we just did.

To our surprise when we walked back in, three of our friends had already left for the night. Jack and another friend were sitting on his balcony talking. As soon as we came back that friend took it as his que to head out. Feeling guilty for leaving everyone hanging for a hook up, we offered to help Jack clean and pack everything up, also because we felt it'd be rude to just head out then.

Jack and I pretty much just put stuff away and cleaned up the common spaces and the bathroom while my GF packed up all the food and cleaned the kitchen/dishes. An obvious topic came up of what my GF snuck off to talk about and if everything was okay. As every guy does, I assured him things were okay and proudly said we just needed to sneak off to have some us time *wink*. In a sad laugh Jack stated that him and Nicole hadn't done that for about eight months as they were having problems and he missed doing that, but had hesitation of getting back in the 'hook up' scene. He seemed really distraught about it and openly stated his bent up and tense sexually feelings that he just needed to release.

That was kind of the end of Jack and I talking about sex, and we had a few candid topics we covered after that, mainly just to change the tone. It was hard for me to think of anything else, thinking 'wow, here he is struggling while I just wave my wins in his face'. Jack being a good friend, I was trying to think of some ways to help with his situation but, I don't know many single women. Even the few I do, I don't know to the extent of hooking them up with a close friend. I noticed myself glancing at my GF constantly while thinking about this and decided to be bold and came up with a rather extreme idea.

I grabbed my GF and asked her to help me walk the trash to the dumpster. I presented her with the idea of her giving Jack a handjob and letting him grope/play with her due to his situation. While she felt the same sympathy for him she didn't feel as keen to the idea of hooking up with him to help. Neither of us are into this kind of stuff and we've never discussed it before. I didn't do much to talk her into it as I felt the alcohol may have been talking more than my brain. I only stated the boundaries of; no kissing, her shorts stay on, and she just takes her top off and jerks him off. I didn't feel like I needed to go into any more detail, but after the very slow walk back to the apartment she offered at the base of the stairs to do it.

We quickly decided how we'd suggest/offer it as we walked up the stairs. By the time we got to the door we both exclaimed how nervous we were and that our hearts were pounding, which was difficult to concentrate on while only noticing my GF's hard nipples protrude from her thin crop top without the coverage of her bra.

We had decided on sitting him down on the couch, us sitting on the adjacent one together and kind of both offering it. I'd explain the boundaries and if he accepted, she'd move to the other couch to sit with him and go for it. As soon as we walked in we both got tunnel vision on finishing the cleaning. Jack's apartment isn't that big and there wasn't a huge mess, so we had already basically gotten to everything. All three of us cleaned up and I suggested we sit down and chat a little before we call it a night.

Jack sat on the big couch, my GF and I sat on the adjacent smaller couch. I started by sharing my sympathy for how hard it might be to be in the position he is. I offered a few ideas hoping he'd take to once and I wouldn't need to offer my GF. Unfortunately he didn't. Which a sigh, trying to release my nerves, I offered that my GF and I would be willing to let her give him a handjob in hopes that it'd release some of his frustrations and maybe make him feel a little more positive. Jack wasn't too quick to hop on the idea and I think he felt we were either testing or messing with him.

You could tell he was fighting to not just say 'yes' no matter how badly he wanted to. I suggested to my GF that she go sit with him and maybe help him feel a little more comfortable. She sad down facing him from the side and was explaining that while this isn't something we're into or normally do, that we'd still be okay with it this one time. Still struggling with saying yes, but with the ability to say that he really wants to, just doesn't want to jeopardize our friendship or our relationship.

My GF then took it upon herself to run her hands on the inside of his thighs while telling him that we already discussed it and we were comfortable with it. Still just a hair shy of saying yes, my GF gently grabbed his hand and slid it up her shirt. The second he felt her bare breast he immediately said that he'd like to.

I took the time to explain the boundaries, that groping was fine as long as her shorts stayed on, it would only be a handjob, no kissing, and that I'd stay in the room to make sure she felt comfortable. He happily agreed to them and immediately pulled her shirt off to ask if he could kiss her body. My GF and I looked at each other and shrugged thinking we'd both be okay with that. Once we said 'yes', Jack immediately started kissing her breasts and nipples.

I didn't know if I should watch or what so I kind of just sat there silently looking at my phone, glancing up from time to time. I noticed Jack slide his pants off and my GF looked shocked noticing the size of his penis. It was around 8", thick, and veiny. She did as she always does with me and teased around his cock. She even bent over a few times to kiss the inside of his thighs, getting very close to his cock, and looking up at him and glancing over to me making sure I was okay with it. As she did this my heart raced with the worry that she'd just go for putting it in her mouth. Seconds later you could see a stream of pre-cum dripping down his cock, which my GF gathered with her hand and spread around.

She started out slowly rubbing his cock, talking dirty to him, telling him what she liked such as being choked. He took right to that and turned his attention from her bare breasts to her throat as she continued to talk dirty, straining to talk through his hand around her neck. This just increased everything as she started to jerk him off faster. He bent her over so he could play with her ass, and rub her pussy through her shorts. Not too long into this I could hear his shock about how wet she was and that she already soaked her shorts.

After a giggle from her she got up and grabbed me, pulling me to the hallway. She told jack she'd be right back and to keep it hard for her. Once in the hallway she aggressively started making out with me and said that when we get home she NEEDS me to fuck her. I laughed and told her to make this quick so we could. Before we walked back to the living room she asked if I'd be okay with him fingering her and her shorts coming off. With a short thought, I justified it since it was the exact same thing she was doing to him. Being on the same page we walked out and as she kneeled onto the couch she slipped her shorts down and guided his hand up her leg to her dripping pussy.

Jack looked at me with shock and I said, dude it's the same thing she's doing to you, go for it. I sat back down and now couldn't look away as he rubbed her clit and as she gasped and moaned he slipped his fingers inside of her making her scream. She bent herself over with her face in his lap, sticking her ass up for him to play with her pussy and have a great view. You could see her knuckles turn white as she stopped jerking him off and just held on to it, with her face inches away. Moaning, screaming, and gasping left her mouth open constantly, again inches from Jack's cock.

Out of instinct she put the tip in her mouth to pacify herself as she always does with me. I froze and both of them kept building the intensity. I didn't know what to say, what to do, so after I came back to and unfroze myself I shouted 'babe'. The two of them immediately came back to reality and frantically apologized. I tried to play it off and say that everything was okay, but in the coming minutes you could tell that I ruined the mood. They struggled to get back into the heat of things and it just started to feel awkward. After what felt like an eternity I decided that it already happened and if I just say I'm okay with her blowing him that this would probably be over faster.

I asked them to stop and explained that since it already happened to just go for it. I just asked that they try to make it quick. Jack said he had already been so close when it happened and if she was okay with giving him a blowjob too, that he'd probably be done in a few minutes. We all agreed that it was okay and moved on.

She looked so passionate sucking his cock, struggling to fit it all in as it's the biggest she'd been with. Three minutes passed, then ten, then fifteen and at twenty you could tell she was getting tired. Her jaw and hands were sore, but as she pushed herself harder you could tell she was getting more and more turned on. Any time Jack took his hand away from her pussy she immediately returned it, now constantly saying things like, 'think about how badly you want to be inside of me'.

Not much longer she pulled her head up to get air and looked at me. I looked tired, she was tired, and Jack didn't show the enthusiasm as he did in the beginning. She suggested we just call it a night. I noticing Jack's face when she said that, asked him if he'd actually finish quickly if we just removed the boundaries. Jumping to answer he excitedly said yes. My GF shocked asked me if I was really okay with that, which blandly I agreed. I told her I could tell she wanted to with what she was saying anyways, even though she just tried to back it up as playing a role, I told her to just go for it.

After some short hesitation from my GF she got on top of Jack and started to vigorously make out with him, rubbing her still soaked pussy against his cock. I couldn't look away from the size comparison of his 8" dick to her 5'1", 105lb body.

The next ten minutes or so were like I didn't exist. They got right back into the enthusiasm they had prior and more. I watched as my GF got fucked harder than I ever could do, with a penis much bigger than mine, by a friend mine. She came multiple times, and in the end when he pulled out while on top of her sprayed her with more cum that I thought possible outside of porn. He covered her face, chest, stomach, and got multiple strands in her hair.

Even though at this point my heart was racing, my nerves were topped out, and I didn't know what to think of what happened my dick was rock hard in my jeans. Throbbing and begging to be touched. Since things were over I didn't even think to pull it out and join or play with myself. That was until my GF got up, out of breath and walked over to me, she wanted to tell me we'd go as soon as she cleaned herself up until she noticed my bulge. She looked at Jack who was sitting down, also panting and asked if he'd be okay with us using his couch. Shocked he quickly said to of course do whatever we want, it was the least he felt he could do for what we just gave him.

I tried to tell her we could just wait as looking at my GF glistening in sweat and covered in another man's cum threw me off. She insisted as she unzipped my pants and began to give me the sloppiest blowjob she'd ever given me. Soon after she was climbing on top of me, taking my shirt off, and laying me on my back, hugging and kissing me as she slipped me into herself. I couldn't take my mind off the cum now sticking to my body and my face, but was overwhelmed my how sensitive my dick was going into her until I realized she was nowhere near as tight as she usually feels.

She rode me so aggressively as I just tried to wrap my mind around everything that I just saw and now what I was feeling. It wasn't long until I felt myself building the pressure of being at the edge of finishing. I told her that I was about to, not ten minutes after her starting. She immediately laid on her back and asked me to get on top and cover her once I was ready. After a few thrusts I had to pull out to add my dainty amount of cum to her already coated body. I wasn't even able to cum past her neck, let alone cover her like he did.

I kind of just stood over her, looking at how used she looked. Covered in fresh and dried/smeared cum. Clumps in her hair, eyelashes destroyed, makeup running. She pulled me down to kiss her and said, 'thank you'.

We all go cleaned up, her and Jack kissed goodbye. I awkwardly said goodbye to him and he said that he'd see us soon and we should do this again, to which my GF happily agreed.

Going home was awkward for me, she kept talking about how great he felt and such. We didn't discuss it much over the next few days until she came to me with a snap from Jack. It was a dick pic with a caption saying how much his missed her body. She pled her case, that she wanted to sext with him and maybe be able to have threesomes, where we're all involved. Which after not much of a fight from me we ended up trying later that night. It was awkward and even though she liked the DP aspect, I just kept getting in the way, and I could tell she much preferred Jack's size to mine.

That was the first and last time we'd have a threesome. A few weeks later after letting the two of them hook up without me around, she told me that they we're having a friend of Jack's over that I didn't know. One who also had a larger cock. I now feeling defeated just let it happen.

Now, months later, she has a key to Jack's apartment, goes over constantly, and they regularly have other guys join. She's sent me pictures, videos, and tells me all the stories and how proud she is that her new record is a 10" cock and how she wants to try bigger.

I'm lucky to get what I'd call a pity fuck once a month. At least she's happy.