My girlfriend (well, fiance now) and I have long had an alternative relationship, starting with exhibitionism/candaulism, and leading into some sharing and hotwifing, which I have posted about in the past. She is 24, a graduate student in an engineering field, Asian-American, 5’3″ and 115 lbs. She is a cute thing — not the type to turn heads or have thirsty posts on Instagram, but more the type you bring home to mom and dad. I just proposed to her a couple weeks go, and my family couldn’t be more thrilled that she is going to be in our family.
Anyway, I just returned to my office a few weeks ago after a long pandemic layoff in which we all worked from home. It’s great to be back among my fellow co-workers. After I got back, I was chatting with a somewhat younger guy named Chris who just started with our office in a low-level position. Chris was telling me that he had a date scheduled for that weekend, and he was really nervous because he hadn’t been on a date since before the pandemic started and he knew he would be rusty. He mentioned that the girl was 24, and Korean-American.
I don’t know why I did this, but I just blurted out that if he wanted, my girlfriend could help him prepare. Chris had never met her before, so I showed him a picture of her and said she is super chill and would probably enjoy getting out of the house anyway. He thought she was cute and said he could use the help. So I called my girl, and she agreed it would be fun to go on a date night with him and teach him how to be a gentleman.
We agreed on him going out with my girlfriend on Friday night, because his first date was on Saturday night. I gave him my girl’s number, and let her take it from there. He offered up taking her to dinner, and she quickly corrected him — dinner is too formal for a first date, lets just get drinks instead! He agreed, and it was on. As she got ready Friday evening, I sat there watching, and she was clearly a bit nervous. She pulled on some skin tight jeans and a little black tank top — nothing too scandalous but she looked cute as hell, especially because she really put some time into her hair and makeup. Right before he picked her up, she told me to watch my phone.
A couple hours later, she texted me his address, and said to meet them there. She told me (I knew about this beforehand) that she wanted to give him practice on ending a date the right way too, but she would feel more safe if I was there, just in case. So I jumped in my car and drove over to his apartment. They got there just before I did, and he let me in. The place was small, not especially clean but not awful either. He thought the “date portion” of the night was over, but my girlfriend and I both told him to just continue to act like he would on a date, I would just be a fly on the wall. So I sat in a chair opposite of the two of them on the couch.
They chatted for a little bit, and sipped on some wine, and then my girlfriend just said “ok this would be the time to make a move.” He just laughed and was like “ok, got it.” And she said “no, but seriously, you need to practice. Try leaning in and kissing me.” He looked confused and looked over at me, and i just said “she is the boss, do what she says.” He still looked nervous and kinda leaned in but didnt really go for it, so she bridged the gap and kissed him. He was shocked, but obviously excited, and they made out for a minute or two. Then she pulled back and said “you should probably touch my breast at this point.” Again, he looked over at me and I said “Seriously dude, whatever she says, goes.” So he touched her breast through her tank top. She continued to play along like it was a first date, saying how glad she was to have met him, and how much fun she had. She was definitely enjoying the fiction.
At this point, my girlfriend shifted gears, and I knew she had made up her mind on what was going to happen. She pulled off her tanktop, then said “take my bra off.” Chris kind of fumbled with it, so she instructed him on the proper way to unclasp the back. And all of a sudden, there was the love of my life, topless with my coworker she just met. Then, she started unbuckling his jeans. He helped, and pulled off his jeans. I could see he was rock hard through his boxers. Then she stood up and pulled her jeans off. Then I heard her say “I don’t mind fucking on the first date.” The look on Chris’s face…he looked very very hungry. She slipped her panties off, and did a little twirl for him while grinning at me while she turned. Probably not shockingly, I saw that she had freshly shaved her pussy that evening, so this was obviously planned all along.
Then she pulled his boxers down, and out sprung one impressively large cock. I have now watched my girlfriend fuck/suck five different guys, and this guy was clearly the biggest. She looked over at me and kind of raised an eyebrow, and bit her lip like “ohh fuck, this could be difficult.” Then she sat down on the couch next to him and started stroking him a bit. She even used to hands and then smiled at me and said “look, its a two-hander!” Thanks, sweetie.
While she was doing that, Chris was fingering her, although I could tell he was not doing it effectively. He then tried to push her back to lay down so he could go down on her, but she stopped him and said “its good you want to do that, but that’s a second or third date type of thing.” Then she leaned over and popped his cock into her mouth, slobbering all over it for a few seconds before pulling off, and then declaring “ok, I think it’s time for me to fuck you!” She stood up, and started moving to sit on his lap. He said “wait, I have condoms in my bedroom!” She said “I am so proud of you for saying that. Do that tomorrow night too. But honestly…you can fuck me without one if you want…I am clean and on the pill.” He definitely did not mind.
She then got up on the couch, facing away from him, staring at me as she slowly lowered herself onto his cock. Seeing that massive thing spread her open was one hell of a Friday night surprise for me, and the look on her face — pleasure, pain, mischievousness — was magnificent. She fit almost all of it, and started bouncing up and down on it. I could see his hands on her ass, spreading her cheeks, and realized that my coworker was almost certainly staring at my girlfriends virgin asshole as she milked him. He didn’t last long though…after maybe 45 seconds, he started to moan, and she grinded on his dick as he blew his load inside her. She let him finish, then slipped off him, his cum dripping out of her and making a mess. She told him to go get her a towel, because thats what good men do. He scurried off, dick flapping, and she smiled at me, and said “your turn.”
He returned, and handed her a towel so she could clean herself up. She told him he did a great job, but it was time for the date to end. She put her clothes back on, and we left. In the car she told me it was super arousing to have such a big cock inside her and that it was the biggest she had ever taken, but he wasn’t very good otherwise, and she was nowhere close to orgasming. She also made it clear that it would be my job to take care of her when we got home. No problems there…
From what I heard, Chris’s first date went well on Saturday, and he got another date with her. Work on Monday was DEFINITELY awkward, but I assured him that we have an open and unique lifestyle and that as long as he didn’t tell anyone, it was all good. Christmas party with significant others is going to be awkward as hell this year though…
tl;dr: My girlfriend helped my work acquaintance prepare for a first date by doing a dry run, and she ended up fucking him at the end of the date while I watched.
Source: reddit.com/r/gonewildstories/comments/nzpbag/my_coworker_practiced_for_a_date_with_my
You’re a good man
Your fiancee is a godsend. I love that she offered herself bare to him. Do you know what happened on Chris’s first 2 dates?
Your GF is sweet but I have to disagree: if things have progressed to that point it is absolutely appropriate to go down on the first date.
You and the gf are very generous, I would love a date prep like that as someone who has only been on one awkward date. Do you think she will want to do your coworker again?