Update: How swimming in [m]y underwear got me a handjob, sex, and one sexy (and safe) with my friend’s wi[f]e

It’s been a while, hasn’t it? Feels like forever and a day. If you’re not familiar with all the history between my buddy Andy and his wife Melissa, here’s a bunch of links to previous posts, but the long and short of it is that a couple years ago I had gone swimming in my underwear with friends, and Andy and Melissa were there. She had noticed my size, and Andy eventually gave her a hall pass to give me a handjob since she had never been with a big cock before. This has progressed to say the least! Here’s the rundown of events:

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:

Quick update on situation with gf and hung friend from Cuckold

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:

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:

Update on situation with my gf and our hung friend. We had a frisky Friends-giving! from cuckoldstories

His update on how he’s enjoying being cuckolded:

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

Here is my update on how I took Melissa out on a Valentine’s “date” and Andy watched:

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

Another update from Andy about how he watched me dominate her:

Another update on situation with my gf and our hung friend. I got to see him dominate her (long text post). from cuckoldstories

His latest update about how we went to the beach together and Melissa got topless:

Another update on situation with my gf and our hung friend. He got her to go topless at the beach! from cuckoldstories

My post about my romantic weekend away with Melissa:

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

I stayed over their place for an epic week and Andy recapped each night:

Update on situation with ny fiance and our hung friend who is sleeping over this week. Nights 6 and 7 recap! from cuckoldstories

Andy’s first post after he and Melissa had gotten married:

Update on situation with my wife(!) and our hung friend. Our first play time with him as a married couple! from cuckoldstories

First time we played after they got married:

Update on situation with my wife(!) and our hung friend. Our first play time with him as a married couple! from cuckoldstories

When she and I started our “boyfriend/girlfriend” relationship:

Update on situation with my wife and our hung friend. They are going to start having a bf/gf relationship! from cuckoldstories

Megathread of updates:
https://www.reddit.com/user/Dinerwolf/comments/f7hr4g/megathread_for_craig_and_melissa_bfgf_updates/

First time playing since quarantine:

Update on situation with my wife and our hung friend. We had a wild weekend together! from cuckoldstories

There are also some pics of Melissa in Andy’s profile that you will most certainly enjoy! OK, so now that you’re caught up, I wanted to tell you about my weekend with Melissa, which will be the last time we have sex until she and Andy get pregnant.

Andy wanted me to sleep over their place the first night so he could watch and participate, and then I’d take her to my place for two nights for some alone time. To prepare, I had not cum in 5 days so that I had a nice big load for her. I know how much she likes my cum, so I even edged a bit before I went over so that she had plenty to enjoy. I got there, we had a beer, and pretty much got right to it. Andy usually nudges us to start messing around, but this time we were in their living room and Melissa stood up and said we should get down to business and grabbed my hand and led me to the bedroom. She immediately started unbuckling my pants and jerking my cock. She said that she knows she usually sucks me first, but she wants to have me inside her as much as possible this weekend. I told her that was sweet, but instructed her to get on her knees and suck me anyway. She looked me in the eye, smirked, and dropped down to her knees while maintaining eye contact.

Andy was watching at the door and was liking the view. I let her suck me for a few minutes and then clutched her face, rose her up to her feet, kissed her, and told her to get undressed. I knew that sucking me would have gotten her plenty wet and I was right. I laid on my back on the bed and she climbed on top of me and let out a huge moan as my cock sunk inside her. Andy told her to enjoy the big raw cock because we don’t know the next time she’ll have it. A sad whimper slipped out and she pouted a bit. I asked her if she was going to miss it, and she said, “oh my god, you have no idea”. I told her to seize the moment and do anything and everything she wants with it. She sunk down on top of me and grinded away. Her pussy just felt incredible. Andy left the room (I asked him later about it and he told me he left so we can talk freely). She came from this position and I felt her tremble while my hands were on her back. We started up again and I asked her where she wants me to cum once I’m ready. She said, “baby, you better not cum anywhere except inside me. I’m gonna miss that feeling so much”. We stayed in that position for a little while longer and I then flipped her over onto her back and had her spread eagle so she could rub her clit as I came deep inside her, and she came from the combo of me cumming and her playing with herself. I fell into her and she wrapped her arms around my neck and her legs around my waist and we kissed with my cock still inside her.

Andy came back in and I was going to pull out but she held me tight and whimpered “no, I don’t want it to spill out, I wanna keep it inside me”. I smiled and kissed her and we stayed in our embrace. Andy said that was hot, but then suggested that she not keep it in too long because he doesn’t want her to get a UTI. She said she knows, but just wants to keep it in a little longer. I was completely soft, but I was regaining some bloodflow down there and thought if we kissed a little longer, I could begin fucking again. I told her that and said that I could pump another load into her but sided with Andy and told her that I didn’t want to risk her getting a UTI. She sighed and agreed and I pulled out. We watched the cum spill out of her before she got up to pee.

She was all over me the whole night, it was really sweet. We were holding hands when on the couch, kissing a lot, caressing each other. and Andy was loving it. Since Andy wouldn’t be with us the next two nights, I wanted to give him a great show and make sure he gets off properly, so she was sitting on his face a lot and she was verbal in the ways he loves. I was fucking her missionary and going as deep as I could and when I bottomed out, I asked her who’s spot that was. She told me “it’s all yours, no one has ever reached that spot and no other man ever will. You’ve planted your flag there . It’ll be yours for the rest of my life”. I literally said “WOW!” out loud! I was so flattered and blown away. I leaned in and kissed her and told her she was amazing and she said, “no, YOU”RE amazing” while looking me in the eye. It was intense and so fucking hot. Andy was just wide-eyed, smiling while stroking himself.

Another thing that Melissa does that Andy enjoys is tell me how hot she thinks I am. Since day 1, Andy has been telling us how hot she and I look together, and she would defer to me and say it’s because I’m so hot, but I tell her she’s insane and she’s the hot one (she really is). As her self confidence has grown, she’ll look at the two of us together in the mirror sometimes and admit that we look pretty hot together. I remember one time the three of us were talking and we had asked Melissa if she’s loving life right now, and she had said that she was “married to the man of her dreams, but also gets to have amazing sex with a hot guy with a big dick” and that her life was perfect. She has always flattered me, but this night she poured it on pretty thick despite me trying to deflect it back onto her. Andy loved it.

The wildest point of the night was when she had guided my hand onto her neck as I was fucking her while I was on top. I was all hot and riled up and asked her if she trusted me. She nodded yes. I turned to Andy and asked him if he trusts me, and he said yes. I then applied firm pressure to the sides of her neck, while carefully avoiding pressure on her windpipe. I then began really pounding her pussy hard. Her face started getting red and her eyes got watery, but her body was completely relaxed. Her hands remained by her sides on the bed, and even though her oxygen was being obstructed, she didn’t even flinch to stop me. I glanced at Andy and he was watching intently. It wasn’t enough pressure to actually choke her, but it was more than I usually apply on her. She made a slight gurgling sound but just kept her eyes locked into mine, and when I saw them roll back a little, I released my hold and she gasped. She would have let me keep going, and had completely submitted to me. It was the biggest compliment she could have ever given me; her complete and total trust. I held her head and kissed her and asked her if she was OK, and she nodded and we started kissing as she wrapped her legs around my waist. It became extremely tender and intimate and went from rough, hard fucking to slow love-making just like that. We were lost in the moment and were saying how much we appreciated each other. She turned to Andy and asked if he was OK, and he said yes and asked her if she was OK, and she nodded. He leaned over and kissed her, and I thought that they should have a moment of connection, so I slid out of Melissa and told Andy to take the bed, and gave them the room.

The three of us went to bed together and she woke me up with a blowjob in the morning (I’m so spoiled). We had breakfast, she packed a bag, kissed Andy goodbye and off we were off to my place! In the car ride over she had told me she was really horny and I asked her if she wanted me to treat her like a slut, and she shyly nodded. As soon as we got inside my place, I ordered her to her knees. I took my pants off and put my dick in her face, and as she leaned forward to start sucking it, I pulled it back and teased her with it. I started backing up towards the bedroom and she followed me on her hands and knees. She asked me, “can I have your cock, please?” Once we got to the room, I told her to get completely undressed and get back down onto her knees. I let her take my cock in her mouth and she began moaning as she tried to throat me. She always swallows my cum but I surprised her this time by pulling out and cumming on her face. I told her she could wipe her face and suck the cum from her fingers, but if any drips onto her body, she needs to leave it there for the day. She collected the majority that was on her face and licked her fingers clean, but a decently-sized dollop dripped onto her boob, and kind of dangled off of it. We were both watching it to see if it dripped off her tit and I told her how hot it looked and proceeded to tell her how slutty she was on her hands and knees, sucking a big cock, covered in cum. She smiled and said “it’s fun to be slutty”. I told her she was a perfect slut and told her to get on all fours so I could spank her. I kneeled down and proceeded to spank her after asking her several questions:

I asked her, “Did you just suck a big cock and drink cum?”

“yes…”

<spank>

“Did you just crawl on your hands and knees and beg for dick, while your husband was at home?”

“yes.”

<spank>

“Do you dress slutty for me because I have a big diick and fuck you so well?”

“Yes”

<spank>

“Does the thought of my cock make you wet?”

“Yes!”

<spank>

“Did you walk with me to a corner store in booty shorts to buy magnums so the cashier would know you’re about to get fucked by a big dick?”

“YES”

<spank>

“Did you flirt with boys with your tits out at the beach?”

“YES”

<spank> (she’s now whimpering after each spank)

“Would you do whatever I say because you want me so badly?”

“YES!”

<spank>

“Are you addicted to big dicks now?”

“YES!”

<spank>

“Are you about to suck and fuck for two days straight?”

“YES!!”

<spank>

“What does all that make you?”

“a slut…”

<spank>

“A what???”

“A SLUT!”

<spank>

“Who’s slut are you?”

“YOURS!”

<spank>

“Who else?”

“NOBODY ELSE!”

<spank>

“Does it feel good to be my slut”

“YES!!”

<spank>

“Good girl”. I then took her face in my hands and kissed her and we made out on our knees on the ground. I had spanked the cum off her tit.

I laid her on the bed and told her how amazing she is, and poured on the positive affirmations to remind her that we’re just talking shit. We laid in bed together and kissed and chatted as the sun poured in through the windows. We talked about everything: our whole journey, her sexual awakening, their upcoming pregnancy (hopefully!), and life in general. I learned a lot of things that I hadn’t known about her, like how (Andy OKed me posting this BTW):

– She was a straight-A student all throughout school

– She’s a Dr. Mario whiz

– Boys used to chase her around sometimes when she was in grade school and she didn’t realize it was flirting

– She still plays Pokemon Go

– And this is my favorite: how one time when she was single, she was out with girlfriends at a bar and this handsome businessman in his 40s with a Rolex and Armani suit chatted her up. He was so smitten with her that he offered her $1000/week to be his companion. Like drive around with him, have dinner with him, pretty much the whole girlfriend experience. He told her they didn’t even have to do anything physical if she didn’t want to and she could stop at any time. He wanted to spoil her and buy her jewelry, designer clothes, gifts, etc. She said she felt like she was in Pretty Woman. She didn’t have the confidence she has now so she thought the guy was fucking with her, plus she was embarassed because her girlfriends were there and watching them together from a distance, and even internally worried what her family would think if they found out, so she turned him down. She said that he was so smooth and handsome that she masturbated thinking about him when she went home that night. I CANNOT believe that was my first time hearing that story! I gave Andy shit for not telling me, but he said she asked him not to tell anyone, so I respect that. But damn, what a fucking story. I asked her if she thinks about what her life would be like if she had said yes, and she said she has, and she’d probably have a lot of material things but wouldn’t have Andy and that’s the end of that. She’s such a sweetheart.

We must’ve talked for a good two hours, naked and caressing each other on the bed. Afterwards, we had some of the most tender, slow, and passionate sex we’ve ever had. Our lips barely separated, and there was no dirty-talking or spanking or rough stuff. We were in complete sync and I held her close to my body and kissed her neck as she came. She kissed me and kept her legs wrapped around my waist when I came inside her. We kissed some more, she got up to pee, and then came back into bed and laid in my arms. We drifted off into a blissful afternoon nap.

When we awoke, we made some food and watched a little TV. As much as I wanted to fuck her over and over again, I also didn’t want her to be too sore the next day, so I was happy just hanging with her for a while. We Zoomed with Andy and caught him up to speed. We tried to watch a movie that night but ended up fucking on the couch. When we went to bed, we 69ed until we each came.

We slept LATE the next morning. I made us pancakes and coffee and she sat in the kitchen with me as I made it. She was wearing this tank top that her boobs look huge in, and I admit I was quite distracted by it. After breakfast I pulled it up and just sucked on them for a while. She pushed me back into the couch, said “my turn” and got on her knees on the floor in between my legs and gave me a fantastic blowjob, but told me to tell her when I was close to cumming. When I did, she got up, put her panties to the side, and sank down on top of it so I could cum inside her.

The rest of the day was a whole lot of sucking and fucking. We mixed it up and went fast, slow, rough, gentle, kinky, and vanilla. My bed sheets reeked of sex and cum. I had a belt around her neck for a while and walked her around my place on her hands and knees and fucked her doggystyle on the floor like an animal. There were two separate cum puddles on the floor that I had to clean up with the Swiffer Wet Jet. She had dried cum all down her inner thighs from creampies that dripped out, it was so sexy. The only time we left the house was to walk around the block while she wore just a sports bra, booty shorts, sneakers and a mask (with the dried cum on her thighs!) We got pretty tipsy that night and broke a glass and knocked over a plant when we were having some sloppy sex. We chatted about how when Andy gets her pregnant, she’ll wear sexy maternity lingerie for me and continue to suck my cock on her knees and be my personal slut. We even looked up some maternity outfits she could wear for me. I cannot emphasize enough how hot she would look with a big pregnant belly.

We passed out on the couch and I woke up at around 2:00 and picked her up and carried her to the bedroom. We slept late again, took a shower together, and had sex one last tme before I dropped her back off at their place. We were both pretty sad that we wouldn’t be having sex together for a while, but we talked with Andy a bit more about it and we were all comfortable with oral until she gets pregnant. It’s just too risky, especially considering how I had impregnated her after the condom broke that time.

It was an incredible weekend, and while I’m sad that we won’t be fucking for a while, I’m just really happy for them and excited that they’re starting a family together. They are going to be AMAZING parents. I’m sure Andy will let everyone know when it happens!

Source: reddit.com/r/gonewildstories/comments/hdzbl0/update_how_swimming_in_my_underwear_got_me_a