Update: How swimming in [m]y underwear got me a handjob, sex, and now a weekend away with my friend’s g[f]

Hey guys and gals! Been a while since I’ve written something about the fantastic situation I am in with u/dinerwolf and his beautiful girlfriend, Melissa. Before I start, here’s my usual list o’ links for the whole history ;)

Here’s the pic I posted right after I went swimming with friends in my underwear that fateful night:https://www.reddit.com/r/Bulges/comments/5xhjqr/just_swim_in_your_underwear_they_said/

The recap of the handjob Melissa gave me and the leadup convos with Andy:https://www.reddit.com/r/gonewildstories/comments/6py2nr/how_swimming_in_my_underwear_got_me_a_hand_job/

My recap of convo with Andy where he told me he is thinking about letting me fuck her:https://www.reddit.com/r/gonewildstories/comments/77eche/update_how_swimming_in_my_underwear_got_me_a_hand/

Andy’s first reddit post where he asked for advice:https://www.reddit.com/r/Hotwife/comments/78r5i1/may_let_my_gf_sleep_with_a_male_friend_advice/

His recap of the threesome we had:https://www.reddit.com/r/Hotwife/comments/7d4t9d/update_to_my_previous_post_about_letting_my_gf/

My quick recap of the threesome we had:https://www.reddit.com/r/gonewildstories/comments/7dli32/update_how_swimming_in_my_underwear_got_me_a_hand/

His update about how she got pregnant from when my condom broke:https://www.reddit.com/r/Cuckold/comments/7nvuml/disaster_please_help/

His update about how they recovered from it and decided to continue on with me:https://www.reddit.com/r/Cuckold/comments/8ecqbj/update_on_situation_with_my_girlfriend_and_our/

My update on aftermath and first proposition of solo sex:https://www.reddit.com/r/TrueBigDickStories/comments/8hofe3/update_how_swimming_in_my_underwear_got_me_a/

First time I had sex with her without Andy there:https://www.reddit.com/r/gonewildstories/comments/8ojeli/update_how_swimming_in_my_underwear_got_me_a/

His recap of our 2nd threesome:https://www.reddit.com/r/Hotwife/comments/8y1qdn/another_update_on_my_situation_with_my_girlfriend/

Our 2nd time fucking alone and when I had her wear booty shorts in public:https://www.reddit.com/r/gonewildstories/comments/93qd4d/update_how_swimming_in_my_underwear_got_me_a/

His post about when I came over for a game night:https://www.reddit.com/r/Hotwife/comments/9azome/another_update_on_situation_with_my_girlfriend/

His update on how they’re doing:https://www.reddit.com/r/Cuckold/comments/9epopm/quick_update_on_situation_with_gf_and_hung_friend/

He verified himself here:https://www.reddit.com/r/Hotwife/comments/9f86ve/verification/

I verified myself here:https://old.reddit.com/user/craiggyb/comments/9nwr7e/verifying_myself/

The time I came over and we had the contest to see who could make her cum the fastest:https://www.reddit.com/r/Hotwife/comments/9pafvu/update_on_situation_with_gf_and_hung_friend_he/

We had some wild sex after a Thanksgiving party: https://www.reddit.com/r/cuckoldstories/comments/a34hox/update_on_situation_with_my_gf_and_our_hung/

His update on how he’s enjoying being cuckolded:https://www.reddit.com/r/Cuckold/comments/adyisg/another_update_on_situation_with_my_gf_and_our/

Another update from Andy about how he watched me dominate her: https://www.reddit.com/r/cuckoldstories/comments/benklc/another_update_on_situation_with_my_gf_and_our/

His latest update about how we went to the beach together and Melissa got topless:https://www.reddit.com/r/cuckoldstories/comments/bzt9iv/another_update_on_situation_with_my_gf_and_our/

And to help visualize, here is a [photo](https://www.google.com/search?q=keri+russell+hot&client=ms-android-verizon&prmd=ivn&source=lnms&tbm=isch&sa=X&ved=2ahUKEwjCzdzQmeXiAhUDheAKHdyBD-wQ_AUoAXoECAwQAQ&biw=360&bih=612#imgrc=fs0Nv2ePlRaA6M) that Andy thought looks like Melissa if you were to add 5 lbs and with bigger boobs, and I agree.

OK so the last thing Andy wrote about was when we went to the beach together and she wore a thong and got topless, which was an AMAZING day. If you knew her, you’d be shocked that she did anything like that, so Andy and I are psyched that she’s come this far. I think it did wonders for her confidence too, and those dude flirting with her helped a lot. She was also the hottest of the topless girls on the beach, and I’m not just saying that. We made sure she knew that too. Anyways, we went to my place after the beach and she slept over, and it was a real fuckfest. I’m not writing about that though (although feel free to ask me anything you’d like to know about it). What I’m writing about is a night a couple weeks after that where she and I went away for a weekend together, just the two of us!

This was the first time we ever did this, and we worked up to it for a while. Andy was going to be away for the weekend for work, so Melissa would have been home alone otherwise. He and I were hanging out and I joked that I could keep her company for the weekend while he was away, and he liked the idea. The two of them talked about it privately and decided they were both into it. I rented a really nice airbnb that was almost 2 hours away from us with a pool and amazing view. I showed it to both of them and they both approved, so I booked it. I was afraid the place would be too romantic, but they both liked how romantic it was. I was really excited leading up to it. I packed some clothes, wine, whiskey, and lube, and picked her up that Saturday morning. The drive was nice and conversation flowed really well. She mentioned how she was a little nervous because she obviously has never done anything like this with a guy while having a boyfriend (like everything else she’s done with me thus far) but she was more excited than anything. She kind of felt bad that she was so excited because Andy was missing out. We talked through it and she understood that he was excited for us too, and we’d be calling him a lot and checking in. The talk went well. She even rubbed my cock over my shorts during the drive which was incredible! Her hand lingered there for most of the drive actually.

We were both floored when we got there because the pictures didn’t do it justice. It was a really beautiful house with tasteful furniture and nice subtle touches. We both rushed outside to see the pool and it looked great. The view was gorgeous as well. It was hot out so I suggested we jump in the pool right away. The house was completely private so I told her that we were going skinny dipping. She turned red and said OK with a shy smile. I grabbed some towels and jumped in first, followed by her going in very slowly because the water was cold. Her nipples were popping and she had goose bumps all over her body. I resisted splashing her and instead swam up to her and wrapped my arms around her. We locked eyes and started kissing. I’ve been with her enough times to be able to tell by her breathing that she was really horny. She straddled me while I stood in the water and we continued to make out passionately. I picked her up and sat her on the edge of the pool with her legs still in the water, and I immediately started going down on her while I was standing in the pool. She leaned back and started moaning. She looked like a fucking goddess while she was leaning back on her hands, water glistening off her beautiful body, dripping wet in more ways than one. I took my time and was enjoying myself. I must’ve eaten her out for 20+ minutes. She kept telling me she wanted me inside her, but I told her no, I’m not done tasting her yet. She came twice from it, and as her third orgasm was building, I got out of the pool with my heavy dick hanging between my legs, and laid a towel down. She instinctively laid on it, and I got on top of her and slid inside.

It must’ve looked like a scene from a porn, I would’ve loved to watch it from afar. We were both really into it and making plenty of noise since there wasn’t another house close to us. We fucked in several different positions, and she came another 2 times. I knew we had a long day and night ahead of us so I didn’t try to hold out as long as possible. I let the pleasure take hold of me and came deep inside her while in the doggy position. We laid together on the towel by the side of the pool and kissed as my cum slowly leaked out of her. I have to say it was some of the best sex I’ve ever had in my life because it was so passionate and in such a beautiful setting.

Believe it or not, we didn’t have constant sex that Saturday afternoon. We just hung out, talked, and had a good time. I feel like I got to know her more, and she got to know me as well. We don’t have much in common, but we are both open-minded people (obviously), so we can still converse and enjoy each other’s company. There was still a lot of kissing and fooling around though. We made lunch at the house and cracked open the wine. At one point in the early evening when she was sitting on my lap on the balcony, I asked her if she was developing any feelings. She turned the question back at me before answering, and I told her that although I’m very attracted to her and sex with her is phenomenal, I think we have a good thing going as it is and I don’t fantasize about us being bf/gf or running off together (she knows I would never ever do that to Andy). She agreed. She said it’s the best sex she’s ever had, but she has feelings for my dick but not me personally which made us laugh.

After our talk, she said she wanted to do something for me, and she proceeded to take a pillow off the chair, lay it on the ground by my feet, and pull my shorts down. She kneeled on the pillow then gave me a very long and sensual blowjob. She really edged me and was extremely erotic about it. She was talking dirty during it too, saying things like how amazing my cock is and how good it makes her feel, and she thanked me multiple times for making her feel so good and for teaching her how great sex can really be. Some of the stuff she said surprised me, like about how often she masturbates thinking about me, and how often her and Andy bring me up during sex. She played with herself the entire time and came from blowing me at around the 10 minute mark. The sun was setting as this was happening and I was in heaven. We both were. Whenever I told her I was going to cum, she stopped and would either kiss my inner thighs or would come up and kiss my chest so that I lasted longer. I warned her that my load was going to be too much for her to swallow, but she challenged me to try her. When I finally came, not only did she drink all of my cum without letting a single drop fall, but she moaned while she swallowed and kept sucking until she got the very last drop. I was utterly spent and completely satisfied, and she looked quite satisfied as well.

As soon as I came back to my senses, I picked her up and carried her to the bedroom. We made out and kissed each other all over our bodies and I went down on her again until I was hard. We had really slow and hot sex in the bed as the sun set and the sky turned dark. We didn’t leave that bed again for the rest of the night and fell asleep in each other’s arms. We forgot to even eat dinner.

I woke up the next morning to her blowing me. She was wearing lingerie that she must have put on when she woke up. I told her how incredible she looks, and she said she just wants to look pretty for me and please me as much as possible. I told her she’s doing a great job. She got on top of me and rode me and we had another long session. I came deep inside her once again, and afterwards she realized she forgot to bring her birth control with her on the trip. We both remained calm though, and after we left the house, we went to a pharmacy where she got a Plan B. On the drive home, I asked her what she thinks Andy would do if I had gotten her pregnant again. She said he wouldn’t be happy, but she thinks there is a part of him that wants it to happen. I asked her if he ever told her that, and she said they role play about me getting her pregnant and it turns him on big time. She admitted that she finds it hot too. And then I admitted that I sometimes fantasize about impregnating her again. She blushed and told me she thinks her uterus is the devil on her shoulder that tells her that she should get inseminated by me because she has had dreams about me knocking her up. I was rock hard from this talk and she noticed. She gently unzipped my pants and blew me while I drove, which admittedly is dangerous but we weren’t going to fast at the time. She swallowed, once again not letting a single drop escape.

I dropped her off and she invited me in. Andy wasn’t due to get back for another couple hours, so we had sex again in their bed. I really didn’t want to leave, but I thought Andy deserved to have her all to himself once he got home, so I excused myself and reluctantly went home. Before I left though, I had her put on the booty shorts that he loves as well as a tank top with no bra. She looked so hot, I knew he was going to go wild on her as soon as he got home. We kissed for a while at her door and I departed.

Anyways, that’s the long and short of it! I would love to do it again and maybe take an extra day next time. We’ll see how it goes!

Source: reddit.com/r/gonewildstories/comments/cb1qxa/update_how_swimming_in_my_underwear_got_me_a