Well, That Was Awkward


Monthly visitor be damned, I finally got my orgasms.

After our get together the other night I was unsure if I would see him again this week. Mainly because we are both busy and I was still on my period.

I had a meeting that ran a little late last night so by the time I got home I was a little tired and looking forward to showering and curling up in bed with a glass of wine. But after I showered I saw my Russian had sent me a text. We were talking back and forth like this:

Him: “Whatcha doing?”

Me: “Just got out of the shower, you?”

Him: “Just got a massage. Talking with my buddy right now.”

Me: “Well that must be nice!”

Him: “Feel like watching one of those movies tonight?”

(He recently bought a few new movies)

Me: “Hmmm I would say so”

Him: “Put on some jeans and get over here”

Me: “Lol I’ll get dressed now. And jeans? It’s hot!”

(I always forget he likes me in jeans)

Him: “Not in my house”

Me: “Fine, but only because you asked :)”


Well I finished getting dressed and made my way over to his house. I’m not sure where my ex was but I really just wanted to see the Russian. I get there and see him standing there in just jeans and no shirt on brushing his teeth. Holy shit, I almost jumped him right there. He puts a shirt on (to my disappointment) and makes us drinks. I look through the movies he bought and picked one out for us to watch.

As he’s fixing us drinks he mentions to me that the guy he was visiting with runs a local business that I go to fairly regularly for lunch and he tried to suggest setting my Russian up with me. The Russian said, “Yeah he told me about you and asked if I knew you. He said you’re really pretty, seem super sweet and have a great job. And that he didn’t see a ring on your finger. So he was trying to think who he could set you up with and then he realized we worked together so he thought of me.” He jokingly said he told him hell no, and then told me, “I gave him shit at first because I’m single and one of his best friends but I wasn’t his first thought to set up with you. Then I told him you were the one I had been spending time with. He couldn’t believe you were the one I had been talking about.”

Well, there’s another person who knows about us now. To what extent, I’m not sure but the Russian is becoming more comfortable with telling people about us it seems. I also tell him about what happened to my lip and that I’ve never had that happen before. It finally went away but I made him laugh when I said, “How would I even explain that if someone noticed? Oh yeah, I just was sucking some serious dick and he bruised my lip??!” He literally almost fell over laughing. He said that’s one thing he can scratch off his bucket list. I smacked him for that.

Once he makes us drinks we start the movie, it was decent but we talked a lot throughout it. We also really played with each other a lot. I think I’m becoming more comfortable with him again so it allows me to be silly and joke with him more. I also opened up about some of my own personal weird tendencies and he seemed okay with it. He actually told me stuff about himself so it made me feel better about my own weirdness. We really just had fun with each other during this movie, talking and joking with each other. He would be a smart ass with me and then he would be sweet on me. Which is something I really like and I do that too.

Once the movie officially ended we just turned the TV to regular satellite and put it on a random channel. At some point he asks me if I have a problem with his bathroom. Now, I just have an issue with using the bathroom at a guy’s house in general. I don’t really feel comfortable with it, plus I can normally hold it for a long time if necessary. Well he goes on to tell me he wishes I would be comfortable enough to use his bathroom and he always makes sure it’s clean when I come over. And I will say he has an immaculately clean bathroom so that always impresses me.

After we talk for a little bit more I start to kiss on him and rub his dick. I love when he dirty talks too, it is super sexy. After we do this for a little while he asks if I will put him to bed. I laugh and tell him yes.

We walk to his bed and he lays down with me on top of him. We start to kiss deeply and I continue to rub his dick. Doing so immensely turned me on. At one point I just say “Fuck” out loud and he asks me what’s wrong. I tell him that I just want him so bad, he asks if it’s still a bad time and I say yes. He reminds me that he doesn’t care about that and we can just use a towel. Now, I’m still not comfortable with that and I tell him I’m afraid I wouldn’t be able to relax enough. Well after some coaxing on his part I grab a condom from his drawer, lean back and go to the bathroom.

When I come back he tells me to grab a towel and he puts it underneath him. I pull his pants off and start to suck on his dick. He then start to undo my pants and slides them off of me. I reach for the lube he keeps and he pours some in my hand. I rub it onto his cock and then he opens the condom packet and slides it onto himself. I position myself on top of him and slowly slide him inside me. It has felt like weeks since we’ve had sex so I had to take it slow at first, but we fell into a rhythm rather quickly. He made me cum several times and managed to take control a few times while I was on top. He still holds onto my throat and pulls my hair when I’m on top which drives me crazy.

Probably my proudest moment was the fact that I did make him come while I was not only on top but also that it didn’t take me a long time to do so. It probably had to do with the fact I made him come a day and a half ago. I pulled out my best girl on top move and I guess he couldn’t resist it. I try not to bring that one out because I know it will cause a guy to come fairly quickly. He came inside me, with a condom on mind you, and I rode him the entire time. Afterwards, I almost passed out with him inside me. He pulled me to one side of him and laid me on his chest. We passed out like that and I loved it. He normally gets up right afterwards and doesn’t do the post-sex cuddle. He has lately though.


After a few hours I start to try to see what time it is and he does his usual squeeze me tighter and not let me move thing. So I just lay there with him for a little while. I can’t wait till we can really spend the night with each other and not worry about time.

Eventually he gets up to go to the bathroom and start to get dressed. He’s just in his t-shirt and nothing else which is super sexy. We kiss and hug goodbye then I leave.

Now this part is somewhat embarrassing and if you can relate, let me know so I can feel better.

As I’m driving back I get a text:

Him: “Where did the condom go? I got up and tossed it?”

Me: “Yeah you did…or I thought so??”

Him: “Shit…I remember cumming but not tossing. Apparently I did lol”

Me: “You can’t find it? Lol I thought you did toss it at some point”

Oh but he didn’t. I get to my house and realize why I was feeling weird. Yes, that’s right, the condom was still inside of me. That has never happened before so I was slightly freaked out and didn’t know if I should tell him. I didn’t really want to but decided it would be best.

Me: “Ummm I found it.”


I sent that and passed out. Then bright and early this morning he sent me a text back.

Him: “No way. That crossed my mind”

Me: “Yeah well that had never happened before but it crossed my mind so I thought I’d check”

Him: “Kinda defeated the purpose! Unless the end was out”

Me: “Lol! I just was not expecting that at all”

Him: “I’m guessing that means it wasn’t….”

Me: “No it was!”

Him: “Oh lol that’s a plus”

Him: “So you were just carrying around a little baggy of…good thing you didn’t get a full cavity search!”

Me: “Why would I get a full cavity search?! And yep, I knew I felt…kinda weird but I just thought well it had just been a little while lol but that’s what that feeling was apparently”

Him: “You would get one if I pulled you over. Wow lol.

Me: “Hmmm that would be fun lol”

Him: “Perve ;)”

Me: “You know you like it ;)”

Him: “Yes I do”

Me: “:)”


I will say that made me feel a lot better that he wasn’t acting weird or grossed out by it. But still!! I did not know what to do or think about that. But I guess it’s all progress. He’s more open with me now and I really appreciate it. Let’s just see how it all goes this weekend.

What about you? Ever have a condom left behind inside you or someone else? Was it awkward explaining it? Or even finding it?! I’m up to hearing your embarrassing stories as well!


10 responses to “Well, That Was Awkward

  1. Just another reason why it’s a good idea to use the restroom right after sex… LOL. I would feel uncomfortable to do a #2 in a guy’s bathroom if I didn’t know him that well, but going pee isn’t too embarrassing. 🙂 It’s not good to hold it in after you have sex. Nothing worse than getting an UTI! :/

    I think I may have had a condom get stuck inside me many years ago. It’s more common if you’re on top. I know you were embarrassed, but it’s not the most embarrassing thing that could have happened. 🙂 The only bad thing about it is maybe having to deal with him teasing you about it from now on. LOL

    Soon you’ll be in your own place and you won’t have to worry anymore about having to leave late at night. 🙂

  2. While some lube before putting on a condom feels really good, it is also more likely to have it slip off. A suggestion is to grab the base of his cock and the band of the condom then pull out. Even if her has gone soft, it will pretty much insure it will stay where it started and not where it ended up. 😉

    I had a FWB. She calls me at like 5:30am freaking the fuck out… The guy she hooked up with that night left one inside her, and she couldn’t get it. So I grabbed my speculum, flashlight and forceps. Had it out pretty quick. The bad and embarrassing part was her roommate walked in on the “procedure” which was taking place on the kitchen table… “What the hell are you doing to her!?!?!?”

    • I’ve definitely learned to be more aware of this now! Once he has finished coming I will shift myself and just lay next to him. Better safe than sorry!

      If I wouldn’t have found it I would have had to call someone to come help! That had to of been so embarrassing for you two, especially having to explain what the hell you two were doing!!

      And thank you for the advice, I’ll give it a shot next time! 🙂

      • Honestly I’m surprised more women don’t keep a speculum and something to reach inside and grab things. I have heard/read about so many girls losing something. Amazon sell it all too.

        I was talking with a pot SB and asked her the most embarrassing thing she had ever had happen… She starts to tell me about masterbating when she was 16 with a barrbie doll. The head came off during. She panicked and told her mother, who got her father with a pair of pliers. Apparently the pliers were too short and he had to go buy something longer. Yeah that has to be the worst.

      • I have never experienced that before but I’ve heard about it and thought “How does that even happen?!” I definitely learned though.

        And poor girl, that would be absolutely mortifying. I do wonder what she was thinking of using a Barbie doll though? Doesn’t seem like it would be that pleasant to use.

      • She is a kinky girl that is a bit of a pain slut.

      • Ah, then that makes sense! Still very embarrassing for her! I still remember when my mom walked in on me masturbating at 17 and was just mortified. We can laugh about it now.

      • When I was in my 20’s the apartment building I was renting a place in burned down, leaving me and my best buddy homeless. So we crashed at my parents place in the basement. We went out and got hammered and I bought a friend home for some play and my buddy hooked up with this crazy bitch. Somehow they ended up upstairs and woke up my mother. She went off on them and kick em out for the night. So what happens next? She needs to vent to me… It took her a good 5 minutes to realize the lump under the covers was Wendy. So here is Wendy who just froze when she came downstairs and I just pulled the covers up, her head between my legs still in her mouth. Thankfully she didn’t jerk the covers off. We laughed about it many years later. 🙂

      • Lol! That’s great! It makes things so much better when you can laugh about it later. 🙂

  3. I’ve been following you for a while now and I always enjoy the insights of your post as well as the genuine manner in which you find yourself blogging about your choices, decisions et. al.

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