Update: How swimming in [m]y underwear got me a handjob, a threesome, and solo sex with my friend’s girl[f]riend

Hey guys and gals!

I’m back with another fun (and looong) update. Andy (u/dinerwolf) ended up posting the last update about our latest threesome, but Melissa and I just had a great night together just the two of us, so I’m posting about that here. Here is my last post (https://www.reddit.com/r/gonewildstories/comments/8ojeli/update_how_swimming_in_my_underwear_got_me_a/) which has links to my previous posts so that you can get the whole background on what’s been happening.

So after that recent “surprise” threesome he and I set up for her, they were apparently excited to get right back into it which was good to hear, because before the threesome there hadn’t been any action between us for a bit. I was hoping I’d get to fuck her more regularly so it’s looking like that’s happening, which is fantastic. The day after the last threesome, I texted Andy and told him I had a great time and thanked him for for everything, and he texted back that they had a great time too and he thanked me for “fucking her silly” lol. I told him it was truly my pleasure and to let me know when he wants to send her over to my place again. He told me they were talking about it and they want to do it soon, and I felt the blood rush to my cock at just the thought of it. I had some fun things in store for her and I was ready to try them out on her. I’ve been thinking of ways to explore the domination/submission stuff more, but I don’t think she’s into whips and ball gags or stuff like that. She just likes being sexually dominated, trying new sexually adventurous things, obeying orders and things like that. I told Andy my goal was to make her my personal sex toy and he loved the idea and relayed it to her and she loved it too, so that’s the route I’m taking. He also told me that they discussed scrapping the condoms and both came to the conclusion that as long as I keep getting tested and as long as she stays on her birth control, we could go raw, which was music to my ears lol. He said he’s developed a “breeding” kink after I got her pregnant that first time we had sex, and I know that she finds it hot that I knocked her up because she told me so personally. I’m just relieved that there are no lingering hard feelings about the pregnancy incident and it’s actually the other way around now. Creampies are now on the menu!

OK back to the other night- I asked him to drop her off with her wearing an outfit that she thinks would please me the most.. I left it up to her. I wanted to see her try her best to arouse me and told her if I like the outfit, she gets a reward. So when he dropped her off, I opened the door to see her blushing in this button-down top that was tight and partially unbuttoned revealing some delicious cleavage, which was tucked into a short skirt that hugged her in all the right places. Before I let her in, I told her to turn around for me, and when her back was to me she gave me a little butt wiggle; I said I liked it and let her in. We waived goodbye to Andy and shut the door. I immediately picked her up and threw her over my shoulder and slapped her on the ass and told her she looks naughty and that she looks like she wants to get into some trouble. She gave me a cute “I do”, so I slapped her again on her ass as I carried her to the bedroom. I tossed her on the bed and she asked if the outfit passed the test, and I said I think it does (It wasn’t THAT revealing, but it was sexier than I’ve ever seen her dressed in public). She said “well I have something else to show you”, and rolled up the skirt to reveal that she wasn’t wearing any underwear! She started laughing and was clearly embarrassed and couldn’t believe she did that, and I told her that it was amazing and she did a great job, and she looks so sexy. She said it was actually Andy’s idea. I leaned and kissed her on her forehead (Andy banned kissing on the lips) and told her she did well. She asked if she gets her reward, and I told her she does, and started unbuckling my pants. I said I have a present for her, but first, she’s gonna get fucked for looking so sexy for me. I pulled my pants and underwear down and she grabbed my cock and started stroking it, and then sucking it. I told her to get herself ready for me and to play with herself, so she started rubbing her clit. She took a break from sucking though and said “I think I’m already ready!” which was so hot. I was really horny and I could tell she was too, so I stopped her and told her to get on her back but leave the skirt on and rolled up.

I was standing at the edge of her bed, so when she was lying down, I pulled her legs toward me and started slapping her wet pussy with my dick. She closed her eyes and grabbed one of her boobs over her shirt, and she looked so friggin hot. I pushed the head of my cock in a bit, but wanted to tease her first- I pulled out quick and then pushed the head in and pulled out again. She moaned and called me a tease, and that’s when we had some good dialogue; I said “yeah? how bad do you want it?” and she said “so bad, come fuck me”, and then I said “what if I just kept teasing you?” and she said “don’t you dare!”. I kept teasing her with shallow insertions and then she said sort of quietly “I need it..”. I said “yeah, how bad?” and she sad “really bad, give it to me, please!”. “Please” was the magic word, but I also like that she said she “needed” it instead of “I want it”. So I slid in about halfway and she gasped and grabbed the sheets, and then it was off to the races. I started fucking her steadily and deeply and she sounded like she was in heat. I told her how good it feels without the condom and she agreed. The squishing sound was amazing and I also loved that she still had the skirt on, which was now hiked up to her belly button. It made me want to cum all over it to leave my mark, but it looked like a nice outfit and I didn’t want to ruin it lol. When I heard that we could go bareback and that I could cum inside her, I edged for a week without cumming so that I had a huge amount of cum for her. We kept at it like that for a bit, and I would sometimes bottom out and kind of swirl around a bit which drove her insane. She really likes when I poke her cervix (but obviously not slam into it). When she told me she was close to cumming, I decided to tease her one more time and pull out just to see what she would do. She let out a “no!” with this tone of despair and reached for my dick to pull it back into her. I started fucking her again and she shook her head at me for being cruel, but she was quickly overcome by her orgasm and came all over me.. I felt her legs trembling against my chest and felt her pussy clenching on me.. it was amazing. Instead of pulling out, I left my dick inside her and scooched her back a bit and crawled onto the bed on top of her and kissed her neck with her legs lightly wrapped around my waist. She kissed my neck too and I felt how wet her pussy was.

I had purposely not turned the AC on in my room so that it would get all hot and steamy, and I already felt myself starting to sweat and bit and she was starting to get sticky too. I would occasionally give a slow pump to remind her that I was still hard inside her and she would moan with each pump. At one point she told me “your penis is magic” and I laughed and said “do you wish Andy had one like mine?” (which I kind of immediately regretted saying since I didn’t want to sound like I was insulting him), but she said “oh god, I don’t think we’d ever leave the house!”. I laughed again and tried to recover by saying “he seems like he fucks you well though”, and she said he does, but paused for a few seconds and said “but lets just say your dick is different”. I left it at that and started fucking her again, slowly. My arms were under her shoulders and her arms were around my neck, and her legs were around my waist. I was giving her slow, long strokes and I wanted to kiss her but didn’t want to break any rules. We we just having really hot sex. I picked up the pace and started fucking her faster and the moans and yelps increased. She grabbed onto the back of my hair, and that’s when I could tell she was going to cum again. I began to start up the dialogue again but not about Andy- I asked her if she missed this dick and she said “yes”. I asked her if she wants to cum again, and she “yes.. please”. I liked that “please” a lot. I asked her if she was ready to fuck all night long and she just let out a guttural moan and started cumming again.. I thought she was going to pull the hair out of the back of my head! She grinded her hips into me throughout the orgasm and sounded like she was giving birth, it was nuts. When she was done, she let her arms and legs go limp, caught her breath, and told me she thinks her vagina needs a break before I “destroy” it. I slowly slid out and she let out a moan, and without thinking about it I just put my face down and started licking her. She was about to stop me but I must have hit a good spot and she started moaning and began running her fingers through my hair as I went down on her. I took my time because I knew she just came twice, but licked with passion and purpose, and kept licking and slurping and tongue-fucking her until she came again. I kissed the inside of her thighs and rubbed her legs and just watched her breathe and recover. At this point my balls are aching to cum, but I know she needed a break so I didn’t push anything.

We laid next to each other and she turned to me and shook her head and said “you sir.. you are quite the stud in bed.” and she asked me if I there were any other “lucky ladies” in my life. I told her not at the moment and asked her if she had any friends she wanted to hook me up with. That made her laugh and she said she has a few girlfriends who are pretty uptight and need to get fucked, but she doesn’t think she wants to share me. I thought that was sweet. I kissed her on the forehead and she smiled. I asked if she thinks anyone knows about what we do, and she says no and actually brought up reddit and said something like “you boys and your online diaries may get us all exposed!” but in a joking way. I asked if she wanted us to stop writing and she said no, it was fine. I asked if we should stop having sex, and her eyebrows shot up and she went “NOO!” and we both laughed. I told her I’m gonna get her addicted to my dick and she said she thinks she already is. That was good to hear because eventually I want her to do things for me and the reward will just be sex with me. But that thought reminded me that I did have a reward for her for coming over in the sexy outfit.

I really love her body and think she would look super hot in booty shorts, but know she would never wear them in public. I had an idea though. I decided to buy her some booty shorts (I tried to include a link but my post keeps getting auto-rejected) and they luckily arrived at my place in time before she came over. I told her to close her eyes, and I handed her the shorts. She pulled them up and laughed and asked if this was another outfit that she only wears for me at my place (like the swimsuit), but I told her no, she’s going to bring them home with her. I told her I wanted her to wear them out at some point- it didn’t have to be for a whole day, or in front of friends, but I wanted her to wear them in public. It could be just to run a quick errand or to walk her dog or whatever, but if she does, she gets another reward the next time she comes over. She laughed and blushed and said “i dont knowww” and I told her to put them on and show me how they look. She took off her skirt and pulled the shorts up and tucked her shirt into them. She looked outSTANDING! I knew her butt would look great in them and it definitely did. I smacked her and rubbed her ass while she looked at her butt in the mirror, and I told her “don’t you see how sexy you are? how hot you are?”. She blushed again and said she doesn’t think she could pull them off, but I assured her that she could and that she will. I also told her to get ready because she and I are going to walk down the street in them right now and go to the store and come back. She thought I was kidding but I told her I would be with her and it would be a quick errand- to go to the corner store and buy a pack of magnums. I wanted to do this for a couple reasons: 1) I wanted her to get comfortable wearing them outside, 2) I wanted her to see the young guy at the corner store salivate at the sight of her, and 3) I wanted her to buy magnums so that it gave the message of “I’m hot, and I lured a big dick because I’m hot, and I am about to get fucked by a big dick because I look incredible in these shorts”. As I said before, my goal is to turn her into my slut, but part of that is getting her comfortable with her sexuality, and I knew I’d have to work at it. (I ran all this by Andy beforehand FYI). I wasn’t going to force her to do it, but was hoping she would agree after a little convincing. At first she told me she thought that I was crazy, but I assured her I’d be with her, it would be quick, and I’ve seen people in public wearing more revealing outfits, and that I’d “take care of her” when we got back. She thought about it for a bit but eventually agreed! I was pumped.

This activity may sound weird to some, but the goal was to get her more comfortable in more revealing clothes and to push her comfort zone a bit. I threw on some clothes, grabbed my keys and wallet, and guided her out the door. She was a little nervous, so we both peeked out the front door to see that there weren’t a ton of people around (I also live far enough from Andy and Melissa that there is a near zero chance of anyone we know seeing us). That seemed to comfort her, so we headed out to the store. I kept peeking behind her and checking out her ass, and she kept telling me to stop and was blushing the whole way. She looked so fucking good in those shorts but could tell she was shy. We got to the store and walked in and she giggled a little bit at me and her nerves were obvious. She asked the cashier (who was a guy in his 30s probably) for some condoms which were behind the counter, and he smiled at her and said OK. He walked back and asked if she had a preference and she said “magnums please” and burst out giggling. I laughed too and the guy smiled but didn’t say anything. I noticed him looking her up and down though. I paid for them and we left, and I saw him checking out her butt on the way out. I think she noticed too. She kept laughing outside and I gave her a good smack on the butt and told her she did great. She said I was “ridiculous” but I could tell she was on an adrenaline high. As soon as we got back to my house I pulled her into my room and she pounced on me! She was just really frisky all of a sudden which lead me to believe the activity was a success!

We ripped off our clothes and got straight to fucking (seeing her walking in those shorts had me at a perpetual semi) and it was with more gusto and intensity than earlier. It felt so good to be without the condoms and I mentioned that to her while I was fucking her doggy on the bed. I told her “you feel so fucking good without a condom on” and she said “oh my god you feel amazing”.. I was so worked up that I just wanted to explode inside her and had no interest in holding out- I needed to fill her up with my cum. I told her “I’m gonna pump you full of my cum” and she moaned loudly and said “give it to me..”… I gave her a few more deep thrusts and then buried my cock as deep as I could inside her which made her feet kick up and her heels hit my ass as she yelped. I came so damn much.. I just kept pulsing and shooting more and more inside her and I could tell she felt each rope because she would yelp with each one. I grabbed the back of her hair and pulled her up to my face and put my hand around her neck while I kissed her neck and rubbed her breasts. She put her hand over my hand and kind of pressed it into her neck, which lead me to believe she might be into some light choking next time. I eventually bent her back over and slowly pulled out and the cum just started oozing out of her.. it was a beautiful sight. She flipped over so she was leaning back on her butt to looked at her pussy and played with the cum a little with her fingers. She said something along the lines of “damn! how much did you cum??” and I told her I was saving up for her which made her laugh. She said she was going to clean it out but I told her to leave it in there for a bit and enjoy it. We kissed each others necks and laid in the bed in bliss.

At this point we started chatting again, and it mostly revolved around how I just came inside her. She said she hopes her BC is strong because I really shot it deep inside her, and she commented on how much she felt it shooting out of me and that she hadn’t felt anything like that before. I made some comments about knocking her up again and she said that she didn’t think Andy would be too thrilled with that. I noticed that she said Andy but didn’t say “Andy and I” wouldn’t be thrilled with that, so I asked her what SHE would think if I got her pregnant again. She said she wouldn’t be thrilled either. I teased her and said, “nah, I think you be turned on”. She said something like she shouldn’t let being turned on affect major life decisions, and I said I guess she’s right- but it’s still hot. She then said “it’s definitely hot” and then laid on my chest while I was laying on my back. It was definitely an intimate moment and I was concerned about Andy’s feelings towards this, so I excused myself to use the restroom.

I went to grab us some waters, and after I got back, she was laying on her stomach and looking at me in this cute way. I looked her up and down and leaned over her head and smacked her ass. As I was leaning over, she grabbed my cock and slipped it into her mouth. She began sucking me sensually, while I was standing on the side of the bed. I ran my fingers through her hair and told her how beautiful she looked, and the corners of her mouth curled up in a smile while she continued to suck. It wasn’t long before I was rock hard again my hair caresses turned into grabbing a fistful of her hair. I gradually got more and more forceful, but was never what I would consider “rough”- just a firm grip of the hair without pulling it hard, and thrusts into her mouth without going too deep. I told her “lets see how far down you can go”, and right away she started going deep- still wouldn’t consider it a true deepthroat, but she is definitely making progress. When she bottomed out at a certain point, I would thrust a tiny bit to get another centimeter in there. She would cough or gag and sometimes stop to take a breath, but she was determined. I was really proud of her. She was definitely coughing and gagging a lot less than she used to. I started to feel myself get to the point of no return, so I pulled out her mouth,told her to flip around and lay on her back and suck my balls by the edge of the bed while I stroked the cum out of my cock and shoot it all over her. She did exactly as she was told and took a ball into her mouth while I stroked my tip and shot ropes of cum onto her chest and stomach. One of her hands made it’s way down to her pussy and she started rubbing her clit which I found really sexy.

When I was done cumming I told her to keep sucking my balls and keep playing with herself until she cums again. I let my cock go limp on her chin and she grabbed it and squeezed some last drops of semen out of me while she sucked each of my balls and rubbed her clit. I said “my cum turns you on, doesn’t it?”. She didn’t say anything, just a moan of acknowledgement while she kept sucking. I decided to keep going; “you like making big cocks cum.. you like when I fill your mouth and pussy with my thick cum… you like getting covered in it and filled with it.. ” I was keeping an eye on her fingers and the more I spoke the faster she would rub herself, and I also saw more of my cum from before start to leak out. “I’m gonna send you home to your boyfriend filled and drenched…”- that was the line that did it. She let out a yelp and started cumming. I pulled away to watch and at that moment was amazed at how far this whole situation has gone.. my friend’s girlfriend is on my bed with my cum all over her chest and stomach, and it’s dripping out of her pussy while she plays with herself. I just reflected on how lucky I was and how lucky Andy was as well to be with a girl as sexy and open-minded as Melissa. I guess we’re all lucky.

I sat next to her on the bed and she looked at me and kind of hid her face in her hands and said “haha, oh mannn”. I asked what was wrong and she said nothing, just that she doesn’t know what has gotten into her and she can’t believe what a difference a year makes. It was pretty much what I had just been thinking as well and told her so. I asked her if she has any regrets and she said no. I reassured her how hot I think it all is and how proud I am of her. She then said something along the lines of how she still can’t believe that I fit inside her, and we chatted a little about my size and how she hadn’t been with anyone that came close to my size, and said she had no idea that she would enjoy size as much as she does. I called her a size queen and we laughed. We chatted for a bit more and I realized it was getting late. Andy had told me that she could sleep over if she wanted, so I asked her what she wanted to do. She said she kinda wanted to sleep over, but had a feeling she might feel bad about it in the morning. I told her if she thinks that, then maybe we’re not quite ready yet for a sleepover, but I was looking forward to when everyone is ready for it. I said if she is going to go home, then I wanted her to not clean up so that Andy could pick her up and see the mess I’ve made of her. She laughed and said she thinks he’d like that, so she texted him and told him she’s ready to go home.

She didn’t come over with underwear, so she put the skirt back on and put her bra and top back on but was sure to keep it partially unbuttoned so that the drying cum on her chest was visible. She asked for some tissues just in case it keeps dripping out of her pussy, so I gave her a wad. Andy came to grab her and I walked her down to the car. He asked if we had a good night and we both said yes. I didn’t bring the cum to his attention because I wanted him to discover it on his own. After chatting a bit, we said our goodbyes and they were off.

It was really an amazing night and I can’t wait for our next time together. I plan on introducing some light choking next time (I’m hoping there will be a next time), and I also have some other fun ideas up my sleeve. I also gave her a some homework assignments to work on besides wearing the shorts – I told her to refer to me as her “big boyfriend” when speaking about me with Andy, and to starting planning the next outfit she’s going to wear over to my place. Can’t wait to hear if she wear the shorts out! Will definitely keep you guys posted.

Source: reddit.com/r/gonewildstories/comments/93qd4d/update_how_swimming_in_my_underwear_got_me_a