Hey everyone! I’m back with a really exciting update. In case you want the background, here is the [initial incident](https://old.reddit.com/r/TrueBigDickStories/comments/6ngmcz/how_swimming_in_my_underwear_got_me_a_hand_job_by/) that kicked everything off last year, and here is the [update](https://old.reddit.com/r/TrueBigDickStories/comments/7dlhnm/update_how_swimming_in_my_underwear_got_me_a_hand/) about the threesome we had, which was fun but [something happened](
https://www.reddit.com/r/TrueBigDickStories/comments/8hofe3/update_how_swimming_in_my_underwear_got_me_a/) which caused them to pause everything for a bit.
So after some delays and some more talking it out, Melissa and Andy finally decided to go for it and have her come to my place for some solo fun! Pics and videos were banned, but we face-timed Andy a couple times during the fun. Below is a (long!) recap:
Andy dropped her off at my place and waited in the car out front until I opened the door and she got in safely. I had told Andy to have her come wearing these yoga pants that she looks great in along with a form-fitting top. When I opened the door, she was wearing the pants along with a tight tank top, looking fantastic. I quickly scooped her up in my arms and told her to wave goodbye to him. She did, and I kicked the door shut behind us. As I carried her over to the bedroom, I kissed her on the lips and we said hello as she giggled. Once I got to the bedroom, I tossed her on my bed and told her to undress. I wanted to be dominant with her because I could tell she likes it- she’s successful at her job and I can tell she wears the pants in the relationship with Andy (he would admit this as well), so being dominated is a nice change for her and turns her on.
Anyways, she did as I said and pulled the tank top over her head to reveal her perky b-cups in a low cut bra. I climbed onto of her and started kissing her chest as she grabbed onto the back of my head and then we started making out. After a minute or two of intense necking, I told her to stand up and show me her body. She did so, and she gave me a little twirl while she giggled again and started to blush. Her butt looked great in the pants and I couldn’t keep my hands off her any longer. I got up and stood in front of her and started kissing her again and grabbing her ass while she started unbuttoning my shirt and then my pants. Once my shirt was removed, she pulled down my pants and started rubbing my cock from the outside of my underwear. Literally right as I was about to tell her to get on her knees, she drops on her knees and starts peeling down my underwear. My semi-hard cock sprung out and she softly said “fucckk” with a smile as she started to stroke it. I asked her if she missed it, and she nodded and said yes. “Then suck it”, I said. She quickly put it in her mouth and started sucking me passionately. It felt amazing, and she would occasionally let out these little “mmhhm”s throughout. I grabbed my phone and facetimed with Andy so he could see. I pointed the phone towards Melissa as she went to town on me, and he just said stuff like “wowww, I need to pull over”. She got kind of embarrassed and uncomfortable and would shy away from the phone, so I told him we’d call him back later and he said OK. She went back to her passionate self after the call was over, and when I was rock hard, I pulled her up and threw her on the bed again. I peeled off her pants and saw she was wearing a thong underneath, so I asked her to roll over on her stomach. She gave me a little wiggle and giggled again. I crawled to her on the bed and rubbed her ass before giving it a few hard smacks. I then rolled her over on her back and started rubbing the tip of my cock against her pussy over the thong and made out with her some more. She whispered that she wanted me inside her, and I asked her how bad she wanted it. She said “so bad”, but I wanted her to tell me more. I asked her if she’s been fantasizing about it, and she said yes. I then asked her what she would do if I just put it back in my pants right now, and she laughed and said “I think I’d explode”. I told her we didn’t want that, and I peeled her thong off. I nestled my head between her legs and started licking her, and she was already SOAKED down there. She tasted great and moaned loudly while I licked her. I eventually slipped a finger in while I licked, and then a second finger after a couple more minutes, and after 5 minutes or so I was able to bring her to climax.
After some recovery time (during which I kissed her all over her body), I asked if she was ready for me, and she nodded yes. I grabbed a condom and had her unwrap it and roll it on for me (she laughed about how hard it was to roll onto me). I climbed on top of her and started rubbing my cock against her wetness. After a bit of teasing, I slowly slid in which made her gasp. I eased myself in further stroke my stroke and she let out a “fuck, you’re so huge”. I slowly built up the pace as she stretched to accommodate me. It felt fucking AMAZING. We went at it missionary for a while and she eventually came again. I told her to turn around and get on her knees and she did so like a good girl. I slid in from behind and started pounding her, grabbing her hips. I then took a fistful of her hair and grabbed it and pulled her head back- not too hard, but hard enough for her to feel it. That’s when the guttural moans and screams came out. I saw her grabbing the sheets of my bed and could tell she was close to cumming again, so I took the opportunity to open up the dialogue again: I asked her if she likes getting fucked hard by my big dick, and she yelled “fuck yeah”. Then I asked if anyone has ever fucked her this good and she said “no fucking way.” I wanted her to not just answer my questions, but say what she was feeling with her own words, so I just said “tell me more”. She then said “your dick is amazing” I replied “yeah?” and she said “yeah.. it’s so fucking thick.. and deep.. fuck!”. She then started grunting and cumming.. her legs trembled, it was nuts. Once she came down, I slapped her ass and pulled out, and she collapsed on the bed. We laid on the bed as she caught her breath, and after a little while I told her I’d give her a break for a minute. That’s when I went to the bathroom and took off my condom and got her ready for the deepthroat challenge.
I rinsed off my dick and went to the kitchen to get the whipped cream, and she laughed when she saw me walk in the bedroom with it. I told her that I was going to put a dab of cream 3/4 down my shaft, and if she can engulf it in her mouth, I would give her a present. She made jokes that I was setting her up for failure, but I encouraged her and told her I thought she could do it. I had her jerk me a bit to get me fully hard again, and once I was all ready, I sprayed the whipped cream where I thought she could get to after a little work. I told her to ease into it and I caressed her hair as she started sucking me. I remembered Andy again at that point and facetimed him again. He was home and looked like a ball of nerves to be honest. I told him we’re having fun, Melissa waved and said hello, and I told him the challenge was underway. He asked what we’ve been up to and I told her she came 3 times already, and he goes “shit! damn!”. We chatted for a bit and told him we’d call him again later and Andy and Melissa exchanged I love yous and we hung up. After a few minutes she got pretty damn close! Her upper lip eventually got half the cream so I agreed with her that it was a victory and she was psyched haha. It was really cute. She asked what she won and sat on the bed in adorable anticipation. So I had initially planned on buying her [this](https://i.imgur.com/Dfd16kQ.gifv), but the black has been out of stock so I got her the same one in purple. She took it out of the box and started laughing and blushing like crazy. She goes “you expect me to wear this shoelace?” and I said “yes! But it stays here and you only wear it for me”. She kept inspecting it and laughing so I told her to put it on. She did, and she looked INCREDIBLE. It was perfect for her. She spun around checking herself out in the mirror and shook her head in embarrassment, but I could tell she knew it looked good on her. I told her she looked hot and kissed her, and she thanked me. Now it was time to fuck her in that thing. This is when I told her about the “10 minute challenge” where if she can make me cum in under 10 minutes, she would get a full body massage from me. Challenge was accepted. I also mentioned that I wanted her to surprise me and do some things that she’s never done before. She looked nervous and unsure of what to even do, but I had faith in her. I set the timer on my phone, put on another condom, and we were off!
I had her get on top of me and pull the bottoms to the side and ride me to start. She looked so sexy in the swimsuit and I had a great view. She would switch from looking at me to looking at my cock sliding in and out of her. I loved when she would watch it for some reason. I said “look at you taking that big dick”, and she said “I can’t believe it fits in me, it’s insane.”. I told her how sexy she was and how she deserves to fuck a dick like that, and she smiled at me. After a few minutes of her grinding on me, I grabbed her hips, pulled her up a little, and started thrusting upwards at a fast pace. There were a lot of “oh fuck”s, and she changed it up by moving to a squatting position, and I resumed the thrusting. This is about 5 minutes in now, and after all the sex we’ve had so far, I could have probably cum, but I was trying my best to hold it in – I wasn’t going to just let her win the contest. If she was able to make me cum with me trying not to, then a victory is a victory, but I wasn’t going to let her win. I wanted her to really work it and do whatever she thought it took to make me cum, and I wanted to see what she thought it took. I wanted her to go all out.
She came again from the squatting position and then collapsed on my chest while she recovered. I picked her head up to make out with her again and told her the clock is ticking. She then took off the outfit and turned around to ride me reverse cowgirl. That’s one of my favorite positions so I was in trouble. She starts by riding me leaning forward on her knees, but then she leaned back and pointed her knees up and put her weight on her hands so I could plow her from underneath again. I reached around and started rubbing her clit as I thrusted and after the 8:30 mark she came again, hard. I let her catch her breath for a bit before reminding her that she had one minute left. She said something like “I don’t know if I..” and then hopped off and rolled my condom off and started sucking me. She was really going for it and tried to deepthroat me again and gagged a few times while trying. I was really close to cumming, but … the timer sounded off and the 10 minutes were up. She pulls her head up and says “fuck!” with a smile, and kept stroking me. I can tell she’s competitive. I told her she was really close and she did great and it felt amazing- and that she should keep going. She did, and after another minute I couldn’t hold it anymore and I warned her that I was gonna cum. She then put her hand on my chest as if to hold me down and kept sucking! I tried to pull out a little bit but she wasn’t having it. I yelled out that I’m cumming, and she kept sucking me as I flooded her mouth with my cum. I watched her and saw her throat move with every swallow- I couldn’t believe she was swallowing it! She kept sucking up and down and a little cough came out, but she managed to keep most of it in her mouth and gulped it down. When I was done, she popped off with her lips and breathed heavy with a proud look on her face. All I could say was “wow!” and that’s when she said she had never swallowed before. I asked her if that was really true, and she said she swore. I was shocked, but after thinking about it more, I wasn’t really shocked knowing how sexually reserved I heard she was prior to our encounters. I was really impressed with her and really turned on. I asked her how it tasted and she said “not bad actually!”. I got up and got her a glass of water and a towel and we sat in the bed together with our backs against the wall . We chatted for a while, so I don’t remember every word that was said, but here are some of the notable things:
– She said how she’s never had sex like this before and didn’t really know she could orgasm like that. I asked her if she’s ever squirted before and she said no, so I told her that was next on the list of things to try to make happen.
– We talked about how crazy all this was and how we can’t believe the progression of events, but she said she was “very happy” that it’s happened, and wants to keep it going.
– We talked about how Andy is doing with all this and she said they are in a good place and the reason for the delay is because they were being extra careful and talking it out 100 times, and I told her that was a good idea.
– It took a bit for the pregnancy to come up, but it did when she kind of blurted out “I can’t believe you got me pregnant!” and gave me a playful slap on the arm. I agreed that it was a crazy situation, and she explained again her reasoning for not taking the Plan B in time and I told her that it was OK. I said something like “it’s kinda hot to think about though, right?” and she agreed. She said she couldn’t believe I got her pregnant so easily, and then she said “I guess I’m not surprised with that equipment you’re packing.” She then talked about how thick and white my cum is and how much I cum and that she’s glad she’s on birth control now even though I wore a condom because I could “probably sneeze and get someone pregnant”. We laughed and I told her how sexy she would look with a baby bump. She said “yeah?”with a smile and started rubbing her belly. I tuned to her and kissed her on the neck and whispered in her ear “does it turn you on that I knocked you up?” and she whispered “yeah..” in a really sensual way as I kept kissing her neck. Before I could ask her another question, she said “you ripped through his condom… it was too small for you…. so fucking hot..” I felt the blood rushing to my cock so I climbed on top of her again but she said she thought her vagina needed a rest and it might hurt. At that point I remembered she deserved a reward for doing something she’s never done, so I told her she could have that full body massage after all, which made her smile and lay on the bed on her stomach, readying herself.
I got out some massage oil I had and squirted some on her back and gave her a nice 20 minute massage. I was thinking of slipping it in during the massage but held off. I kissed her on the shoulder when it was over and she thanked me. At this point it was getting kind of late, so we talked about what she should do. She said she kinda wanted to sleep over, but I told her no; she would go home to Andy now. I did this for a couple reasons:- I wanted to be in charge of the situation and tell her what was going to happen, and I also wanted her to go home to Andy to make sure he was OK. I felt bad we didn’t face time much but he didn’t call either. Regardless, I wanted to make sure he was alright. I also told her to work on making this happen again and if she’s successful, there could be a sleepover. She agreed, and I called her a cab after she got dressed and freshened up. When the cab arrived, we kissed and I slapped her ass and told her I better see her again soon. She smiled as she walked into the cab and waved goodbye to me as they drove off.
Sorry this was so long! I just didn’t want to leave any details out because it turned out so well there was nothing I really wanted to delete. It sounds like Andy was OK with everything and he told me they had great sex the next day which made me happy. If it happens again, I want to go heavier on the dom/sub thing and work on turning her into my personal slut (Andy finds the idea of her being slutty with me but not with him hot). Hes not into humiliation, but he likes that she’s getting these sexual experiences that he can’t provide her (which he would also admit and has told me). I’m also going to get her to keep trying new things. Hope you enjoyed the recap and I will be sure to update again if/when another visit happens!
Source: reddit.com/r/gonewildstories/comments/8ojeli/update_how_swimming_in_my_underwear_got_me_a
God damn this is so hot. Totally wish she would let you share pictures
Sounds like you had a great night. And your writing it’s very detailed.
Quick question though if Andy wanted you two to stop but she didn’t want to stop what would you do?
Really hot update. I do feel a bit bad for Andy though.
Best GW Stories series since the Uptight Roomate saga. Sexy af but there’s an undeniable sweetness there too. Hope there’s more and I wish all parties involved the best.
What a hot body she has. I bet he goes crazy thinking about you fuckinf her with your bigger dick. It’s even crazier that she swallows for you but not him. That is so hot.
This reads like a fantasy.. not sure I’m buying it. Especially without any pics/vids.
I feel like this is a commited fake story. This guys writting and andy feels like one person. Specially that “yadda yadda” shit. It comes up in both their story.