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

Hello there! It’s been a while since I last wrote an update myself. Before I start, here’s a link history of my and my friend’s posts if you wanna catch up on the whole background, but the quick summary is that my buddy has been sharing his girlfriend with me because I am well endowed and things have been progressing quite nicely:

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:

Another update on situation with my girlfriend and our hung friend – game night got a little frisky! from Hotwife

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 also 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:

Update on situation with gf and hung friend – he slept over. Massive text post. from Hotwife

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 latest update:

Another update on situation with my gf and our hung friend. More sex but she cockblocked him at a party. from Cuckold

SO- even though Melissa hasn’t come over to my place by herself in a while, I’ve been going over to their place sporadically. As you can probably sense by reading his last few recaps, Andy has taken a liking to the whole willing cuckold thing and we’ve been going more that route than we used to. Stuff like; only I cum inside her and he has to pull out, him doing more licking than fucking when I’m there, he asks her to tell him how much bigger/better I am, etc. My man gets off to it like nothing else which makes me happy! She’s into it too and is finding her groove with the whole kink. We still talk about anything new that we wanna do or say beforehand, and the latest thing Andy told me about is how he wanted to role play more with me and her. That time where we had the contest to see who could make Melissa cum the fastest is one of his favorite moments and wants to do more stuff like that. The other time where we played strip bullshit and truth or dare were favorite moments of theirs as well. I told him I’m down for whatever, and Melissa said the same once she understood how much of a turn on it is for him. She’s riled up by it too because it’s all new and exciting and scandalous to her. She’s just really careful about not hurting his feelings which I respect, but she likes the idea of roleplaying and likes being submissive with me.

He recently told me about these dreams and fantasies he’s been having that involve me taking her places as my date and he’s there watching from afar. He watches us laugh and kiss and dance, etc., and eventually go home together. So for Valentine’s Day, we decided to make his dreams come true! They said they wanted me to take Melissa out for cocktails on V-Day and Andy would be there too, observing. When they brought this idea up to me, they told me they don’t celebrate Valentine’s Day at all because they think it’s commercialized BS, so they weren’t sacrificing a special day of theirs for this, but at the same time it also makes the fantasy more hot. The plan was to have a cocktail or two and then take her home to my place, where I would leave the door open so he could walk in soon after and watch us fuck. I told them I was down for it and asked some more questions about what they want me to do with her in bed (they said “just do your thing”). We settled on a place and a time and got excited about it.

I was texting with him on the 14th and he was telling me how they were getting ready and she was shaving for me the way I like (the “V” triangle above the clit). He said she had some red lingerie she was going to wear under her dress, and she was going to look real hot for me. My dick grew in my pants just imagining it. I got dressed up too with a nice button-down, pants, shoes, and I handled my manscaping. The plan was to meet at this nice bar at 8:00pm and he would come in a minute or two later. It was a bar that was far from us so there was a near zero chance we’d bump into someone we knew. If we did, we would play it off like Andy and Melissa were on the date, and they just bumped into me.

So 8:00 comes and I got there first. I found two open seats next to each other at the bar and sat in one and put my jacket on the other. I kept my eye on the door and was elated to see Melissa walk in, looking GREAT, with a cute blushing smile. She had on a tight black dress that hugged her perfectly, and her hair was done and she had makeup on (she doesn’t normally wear a lot of makeup). I stood up and took her hand, said hello and how amazing she looked, kissed her on the lips, and took her jacket off her. We looked at the cocktail menu and each ordered one. We saw Andy come in probably a minute after she did and he sat at a hightop table behind us. He had a pretty clear view so we were pumped that it was working out.

Conversation was flowing well, and I made a point to have a hand on her lower back as much as I could. She would occasionally peek back and give Andy a quick smile, and I did the same here and there. He was smiling every time I looked at him. I held her hand at one point and kept it on my leg. We definitely looked like a couple, which was the idea. She felt a little shy and funny at first but that wore off and she got into it. I leaned in and asked her if she thought he was rubbing himself and she looked back and giggled and said maybe. I told her to start rubbing my dick while I kissed her neck. She got a little embarrassed and shy and I assured her he would love it and no one else would see. So she slowly slid her hand to my crotch which had a bulging semi at the time and she raised her eyebrows when she noticed it. I leaned in to her and kissed her neck and whispered how badly I wanted to fuck her. I was kissing the bar-facing side of her neck so that she was able to turn to Andy and look at him while this was happening. I felt the vibrations of her giggles and then her sighs on my lips. I stopped and told her I needed her in my bed right now and it was time to leave. I gave a nod to Andy so we could pay for our drinks, and I put her coat on her and held her hand as we left the bar. Andy left and followed us in his car to my place. In the car, Melissa and talked about how fun it was and how much it must have turned Andy on to see. I asked her if it turned her on too since that is just as important, and she said it did, and she felt “outside herself in a good way” and “sexy” and “naughty”.

Before I left my place for the bar, I set up some candles with a lighter nearby so I could light them quickly when we got there. When we arrived, I took her jacket from her and told her to go to my room and take her clothes off. I met her in there and was floored by how hot she looked in the red lingerie. It was a bra and panty set that I had seen before, but she looked incredible. I kissed her and heard Andy coming inside, so I told her to undress me. I closed the door most of the way and left it slightly ajar. She took my pants off as I took my shirt off and she wasted no time in putting my throbbing cock in her mouth. As she sucked me, I heard Andy tiptoe in and close the door behind him, and I saw his shadow in the hall outside the bedroom door. She peeked and saw him and smiled and I told her to pretend he’s not there. She was playing with her clit as she sucked me (as per my previous instructions for her) and moaning a lot. I couldn’t wait to be inside her so I brought her up, kissed her passionately, and laid her on her back on my bed. I teased her and made her tell me how badly she wanted it as I took her panties off. I slid in and started slow, and she was VERY vocal. Louder moaning than usual and was saying how much she loved my huge dick. I didn’t know if she was playing it up for Andy or she was just really into it, but I didn’t question it. She came in a couple minutes which is fast for her considering she usually has to warm up and allow herself to stretch a bit to accommodate me. I kissed her as she came down from the orgasm and she peeked out at Andy. I whispered asking if she saw him and she said yes, and that he was jerking off. A success in my book!

We fucked some more (reverse cowgirl and then doggy) and she came again and I told her I was going to cum soon. She told me to cum inside her, and I told her to say it louder. She did, and I told her to go even louder, and she did I asked her “what do you say??” and she yelled PLEASE! I asked why, and she said I NEED IT! I buried myself to the hilt and unloaded inside her and she moaned loudly with each pump. I pulled out and she collapsed on her stomach. I opened the door and walked out to a smiling Andy and told him “she’s all yours”. He walked in on her with my cum oozing out of her pussy and she rolled over and they started making out passionately. I went to clean myself up.

When I got back, they were still kissing and he was rubbing her and I could see he was rubbing some of my cum on her clit, but wasn’t sure if it was intentional or not. They were saying I love you’s and looked to be having a real intimate moment so I left and hung in the kitchen for a while. After some more time, I peeked and they were still kissing but she had a fistful of his hair and she was whispering something to him in between kisses that I couldn’t make out. I left again and decided to wait until they called me. About a half hour later they did. They said they had great sex which I loved to hear!

We all slept in my bed together that night and had an early morning threesome. They left hand-in-hand that morning and said they had so much fun and thanked me for spending my Valentine’s Day with them. I said it was my pleasure, which it truly was. I’ve followed up with him since and he said they have been fucking like rabbits! I didn’t ask when the next time we could meet up would be, but I hope it’s sooner than later. I’m sure he or I will do a write-up when we do!

Source: reddit.com/r/gonewildstories/comments/at4smv/update_how_swimming_in_my_underwear_got_me_a