Is It Wrong to Sleep With Two People in One Day?

0 Posted by - September 22, 2010 - Relationships, Love & Marriage

I have a confession to make: I’ve had sex with two women in the same day. I know how bad that sounds, but it wasn’t my fault.

See, what had happened was…

This was back in my youthful days and I had made plans to hang out with two lovely ladies on consecutive days. Bachelorette No. 1 we’ll call Malika, and Bachelorette No. 2 we’ll call Sandy. I’d had intimate relations with both of them in the past, but wasn’t tied to either one presently.

Malika and I met up on a Friday night for dinner and drinks. As we conversed over cocktails, there was plenty of flirtation and reminiscing on our past physical chemistry. As the night drew to a close I threw out an offer for one last fling “for old time’s sake” and Malika bit. So we journeyed out to my bat cave and recreated the magic we remembered in the bedroom.

Now, I knew I had a date with Sandy the next day and there was a strong possibility that our Saturday night could end in a similar fashion, but I was banking on the 24-hour difference (give or take a stroke) being enough buffer between booty calls and I could avoid being labeled a “nasty, dirty dick muthaf*cka.”

Malika had other plans.

I awoke the following morning to Malika’s hands exploring the contents of my boxers. My mind was telling her no, but my body, my body was telling her yes.

I found myself in a moral conundrum. My date with Sandy was in several hours and there was a strong possibility that I might end up getting some, but here was a half-naked Malika (with socks on) primed and ready for an early morning quickie right here and now.

Decisions, decisions…

I tried to weasel out of taking it there, but Malika was the kind of woman that really didn’t take no for an answer. Plus, I was hard as a rock and there was no way she was going to let something as precious as that go to waste. Besides, who was I to deny her one final stroke of the magic stick. So I grabbed another condom from the nightstand and did the dirty deed.

Once Malika left my apartment and took her walk of shame, I showered thoroughly, trying to wash the familiar smell of sex and guilt off. A few hours later I was at the movies with Sandy and then off to a nearby restaurant for dinner.

The date was going well and seemed to be heading in a similar direction as last night’s outing, but I really wasn’t trying to go there. I’m all for guaranteed pucci but I just never wanted to be one of those guys that slept with women back-to-back. Still, Sandy had her heart and womanly parts set on being satisfied by yours truly that night and, once again, who was I to deny her.

It’s not like I could just come out and say, “Hey, can I get a rain check because the other girl I was screwing last night wanted a morning session so I’ve filled my pucci quota for the week.” Something like that would get me slapped and probably get my coochie coupon forever revoked, so against better moral judgment I slept with Sandy, condom in place and minus any oral activities.

Although three assisted nuts in 24-hours was a pleasurable experience, this definitely wasn’t one of my proudest moments. To my knowledge, neither woman ever knew about the other’s proximity to the same penis in such a short time span but I did and it’s been my dirty little secret ’til now.

My life, your entertainment.

How would you feel if the person you were sleeping with had sex with someone else within 24 hours of seeing you? Would you be more upset to find out they had sex before or after sleeping with you? Would you rather be the first or second? Would it make a difference if it were two days apart? If you had back-to-back dates and got lucky on the first would you still have sex with the second dater or make an excuse to reschedule?
Would your ego be hurt if you were trying to have sex with someone and they refused? Would you rather know the reason was because they had sex for the day already or think they just weren’t into you? What would you have done in my situation?

Speak your piece…

  • da ThRONe

    As long as your clean and if we arent in a relationship what you do when your not with me is your business. No it’s not wrong a little excessive but not wrong(ofcourse that if your not cheating).

  • MzWoods

    I have been having this same discussion with a friendly somewhat ex for the last week. His opinion is that it is dirty/nasty/trifling etc that I may of had other encounters even a few days before engaging in anything with him. My response was that we were not in a relationship (he didn’t want to make it “official”) so how can he get mad because I was having fun with other people? What it seemed to all boil down to for him is he can now not trust the fact that anything that we did was special or meant anything because I was doing things with other people at around the same time. This leads me to wonder if that is what the main problem people have with this type of situation…not feeling like they are special.

  • Tre Spade

    I have to agree with NWSO, if you’re a stand up guy, having this occur is a bad feeling. In college, this happened on a few occasions and was never something i was proud of. Even seeing two different women in the same day, feels wrong. But how do you realistically get out of it and sve face? When this happened my seeing of anyone for at least of week happened. Had to atone.

  • Kaye Michele


    Gotta say, I wasn’t expecting that one.

    How would you feel if the person you were sleeping with had sex with someone else within 24 hours of seeing you?
    Depends. If they’re a jumpoff, then truly, how angry could I actually be? I’m not going to be thrilled…but…*shrug* If they’re my man…then oh shit…good luck…*braces for really nasty break up*

    Would you be more upset to find out they had sex before or after sleeping with you?

    Ehh. My ego says probably the after. But that’s just ego talking.

    Would you rather be the first or second?

    I’d rather not be either. *cues Beyonce featuring Kanye*

    Would it make a difference if it were two days apart?

    If it was a casual dating situation with no ties, then it might make a difference…who am I kidding? It really doesn’t…oh. Y’all don’t really know me. Lemme just answer the rest of these questions…

    If you had back-to-back dates and got lucky on the first would you still have sex with the second dater or make an excuse to reschedule?

    No comment.

    Would your ego be hurt if you were trying to have sex with someone and they refused?

    Momentarily it would be. I’d get over it.

    Would you rather know the reason was because they had sex for the day already or think they just weren’t into you?

    I don’t think it’d matter to me.

    What would you have done in my situation?

    No comment. =oD

  • paulette_bajan_gal

    Lmao…I had the bestest 3some ever with 2 men.Was one of my most memorable sexual experiences ever.I highly recommend trying it at least once.I am definitely a one man at a time type of girl right now but that ish was worthy of an award on my wall.lmao.

  • sunshyne84

    I’m sure this happens more often than people would care to admit. lol I would hate to find out a guy I was seeing just had sex with someone else. I would be question a guy turning down sex. It all depends on the relationship with said guy on how upset I would be. If it were an old fling I hooked up with I wouldn’t care as much as someone I’ve been dating exclusively.

  • TC

    Lmao…I had the bestest 3some ever with 2 men.


    Those dudes were gay lol. Very gay.

    Look here.

    Malika I had broke up and were actually not really even speaking. Distance. She had her new guy (who recently just got some other chick preggo behind her back but that’s another NWSO day) and I fell off with this part-timer Sandy just to fill the pain (and bedspace) I admit I had.

    Now Malika comes over in the middle of the day—job hunting—to say hi and actually have lunch. I was in the midday routine and ending up taking a shower while she was in the living room watching TV. I get out of the shower and not really thinking about it (but I was) and she walks by my bedroom not really thinking about it (but she was). Next thing I know, she’s helping put lotion on me and taking her pants off. Fucked her like a man possessed and she loved every second; it had been 3+ months and she kept yelling “why didn’t you remind me how good this feels.”


    I didn’t do much that day; it was a Friday I remember exactly. Sandy was a fuckin’ busy body. Always kept a man and reserve player. Just so happened I was the one coming off the bench that spring. Whatever. I thug/fuck/love/leave those types—as should you.

    She was going to the club that night and wanted to get ready over my spot since it was closer to her girl’s spot or maybe she was ducking her nigga—I don’t know. Anyway, she brought all her shit: curling iron, loofas, bullshit. Now this time, I honestly wasn’t thinking about it, going to the bathroom to make sure she knew what was where, not even knowing she was already naked. She was. Looked at me looking @ her breasts, she shot up 8 degrees instantly. Reached in my pants and kissed me.

    Instantly we’re in the bedroom—in the exact same impression Malika made in the mattress several hours earlier. If the wall could talk, it would say “get your fuckin’ left leg off me, yo.” Both had their backs arched, arm titled on the headboard, mouth open. Honestly it was on my brain at the time and I didn’t enjoy Sandy as much. After we finished, she showered, her girl came and she went to the club. I saw pics of her on Facebook from that night, smiling away like she just didn’t get stabbed up and belonged to someone else. SMH. Like I said, busy body hoe.

    How do I feel about it? I mean it happened. I wanted to get back with Malika truthfully. She had plenty of shortcomings and anytime a chick tells you that you can do better than them, you should probably listen but I was bent on sitting on my well-worn sofa, nah mean? We were actually close to it happening but Sandy ruined that shit (another NWSO lol)

  • Maurice Garland

    i did this once and felt disgusting afterward. crazy thing is, i didnt realize what i did until immediately after the second one. all that kept running through my mind was that im nasty…and that one of them is possibly nastier because if im a dude doing this….a woman is definitely capable of it too.

  • me me

    I was kind of in a similar situation… But it allowed me and the guy I was dating to be less intimate. We did everything else except have sex. Kiss (just tap kisses, goodnight) etc. Becuz I always felt like their were other women in the picture. So I personally think that’s why he wasn’t having sex w/ me anymore (we had sex once) but yet he always came around and wanted to chill. It was weird. I’m pretty grossed out. Thinking about a guy being w/ me today and laid up w/ the next female tomorrow. I don’t know. That sort of thing isn’t for everyone. I try to avoid those situations. P.s I’m on my berry. Excuse typos. Having a hard time trying to go back & edit.

  • Miss Malorie

    Eh. *shrugs* What’s your business is your business. What you (or he) doesn’t know (as long as it’s safely done and not completed a mere five minutes before seeing you or him, lol) won’t hurt you.

  • Miss Malorie

    By the way, I’m referencing singles, not people exclusively dating/in a “committed” relationship. That definitely changes things.

  • The Duchess

    LMAO!! I like…

  • The Duchess

    I am surprised to read that most guys find this disgusting :D:

  • NWSO

    What exactly do you like? lol

  • MsPrincessKey

    This may be a little unsettling for the “germophobe” in me but the fact of the matter is you were single at the time. No condemnation should fall upon the man/women who gets lucky more than once in 24 hours.

  • Preachthecomedian

    Call that a no go…can’t be mixing and matching different juices…mess around as create a new STD..gonaherpes or something
    plus it’s a recession and all that washing and rewashing sheets adds up at the laundry mat

  • R.e.D

    I am soo confused. NWSO are you writing the above or is TC writing that, or are you TC? what am I missing here?

  • Rastaman

    What’s that old saying, “things even out”. I think 2,3, 4 women back to back is life’s way of making up for all the other “drought” time’s you just not getting any for whatever reason. Why curse one’s bounty of booty?

    This particular scenario has happened to me on more than one occasion and I rationalized it by going with the flow because the truth is it was an unplanned, spur of the moment booty bounty and who am I to frown in the gods’ face.

    As for someone else, it’s DADT (Don’t Ask Don’t Tell). Folks that is why its called No Strings Attached, plus if no promises are being made or broken why the guilt?

    We need to stop feel guilty about sex. to quote D’Throne, “…cheating is not about the sex, its about the lying..”

    I classify this kind of thing as WINDFALL. Yo, if I win the maga-million lottery, I am not gonna feel guilty for being suddenly rich. No need for anyone to feel guilty about being popular; for a majority of people these are not everyday occurences. There are folks, some I know whose weeks are filled with multiple sex partners but they are usually on some other sht. If that is what you do, do you!!

  • Rastaman

    Folks sex is not nasty, I know for some that is part of the turn on but it really is not. It’s prety good cardio and greatly helps the nervous system. Yeah, there are a lot of nasty STIs out here but if you practice safe sex you are highly likely to avoid them. The Puritans and Victorians have been gone for centuries its too bad their demonizing of sex still lives on among so many.

    Sometimes a good Fck can be a good thing to share!!

  • bogart4017

    lmao @ preachthecomedian!
    I’ve never been in a situation like that because i’m usually exclusive but i don’t think it would have bothered the 20-year-old me. Once you’re older you tend to be more conscience-driven. For me its not what people think about me its what i think about myself so these days i would have a problem with it.
    If i’m in a non-exclusive relationship i really don’t care who else you’re sleeping with or when because if i was trying to “write my name on it” i would find another way to do it.

  • B. DuB

    My exact thoughts lol

  • Mr. Dose of reality

    Yo nwso the reality of it is these things do happen. As long as your being responsible(protection) it’s not sumthin 2 lose sleep over,these ladies weren’t in a committed relationship with you so you don’t owe it 2 either of them by having a grace period over how soon you can use your manhood! I’ve been in this situation a few times,its not liked you planned it that way. Hav fun,b careful,live ur life!

  • B. DuB

    Call me conservative but I had a hard time kissing one guy upon leaving him and kissing another upon meeting up with him. Sooo I don’t think I’d be comfortable with having sex with 2 in one day. Can’t say I’d automatically decline… But I couldn’t make it a habit.

  • Deka

    multiple partners in same day, sound great but is a bad idea because of STD’s. Well you wouldn’t know where the person has been. Not to be funny but, you got to think about the bodily fluids etc. A guy or girl goes down on someone, then kisses and goes down on the next person within 24hrs period is not a good look especially if no one showers or uses a antiseptic mouth wash. And not many folks are getting head with a rubber on. If you’re not a sex addict, don’t do it. Not worth the risk!

  • Social Butterfly

    This is on my bucket list. But so far no guy wants to participate. I think the double standard is funny.

  • Glendon Cameron

    Yes, I have done it and would do it again. Did not feel guilty in the least. I like Rastaman’s theory of the universe making up for “droughts” LOL

    If you are not in a relationship, nope I do not see anything with a little bump and grind x 2. On the real unless you have hella game, hella fine or rich. This is not the normal man’s experience. I say suit up and jump in!

    I have told women I was dating or trying to date,about my lucky drought breaking experiences. I swear the fact that I could sex two women so quickly sealed the deal! Woman are a lot cooler to deal with when the feel that you are honest.

  • menluvmysmile

    da ThRONe – I totally agree, it happens, we aren’t perfect, we’re human!

  • da ThRONe

    People need to understand that there is no template on life. You have to do whats right for you. If you are an adult that enjoy sex and you arent under any false pretenses about the act(and your safe ofcourse) there’s nothing wrong with it.

  • Slim Jackson

    I’ve done this too in my younger days. Almost made it 3…then realized that would be downright OD.

  • Preachthecomedian

    I’m a firm advocate on celibacy if not with a mate… Too many diseaes and potential soul ties…my faith says wait until the wedding but that’s easier said than done…like my pastor says if your gonna do something dumb don’t do nothing stupid…keep it classy…

  • AD

    Co-sign Preachthecomedian….”keep it classy”. Hell knowing me it will all blow up in my face (no pun intended) and it will NOT be a good thing. So I’ll just read about NWSO’s and TC’s lil escapades!

  • AD

    Rastaman….I guess you moto is “Gettin’ while the gettin’ is good” cuz you never know when the opportunity will come again? LOL

  • beekayman!

    I agree with da THRONE. I have done this and it happened in a similiar way to NWSO’s sexperience. As long as no hearts are getting broken and protection is being used, it’s on. And when it’s on, it’s definitely on. Follow your own path people!

  • Paulette_bajan_gal

    Yeah…the double standard is alive.Most men claim they do not want another d*ck in the room cause he’s not gay.Yet the woman has to deal with another vagina in the room.I’m not gay either.The 2 guys were gentlemen…one was my lover for about a year before we did it.So I felt really comfortable.Hope you get to experience it.

  • Ninjagaiden78

    I’ve done it before and although it is exciting at the time, I’ma be honest as I have become older a bit more mature, I wouldn’t do it now. When you are young it is all about spreading it around but as you get older, you want to pick the right one. Looking back at it now, its one of those things you notch down as being a young man. It’s the classic quality vs. quanity. That’s my piece.

  • R.e.D

    I just lost my sntire comment. It was long too. Just wanted you to know. I am not re-writing it.

  • Vanessa

    Well, at least you had a number of hours. I was on a date with one guy who and didn’t know we would end up having sex. I knew I had a date with another guy who I was seeing the next evening. But, after a very long night with the first guy who was still in my bed at 6 am. I got a call that morning from the guy I was dating who said he was at the subway station 6 blocks away. I got the first guy out of there so fast, and from the window I could see them pass each other as one entered the building and the other left. I let second guy in and quickly jumped in the shower. He said he worked really late and since he was still up, he couldn’t wait to see me. I thought damn, he wants some pucci now!?!?!?!?!? I was still hurting from the first guy. He wanted to go down on my but I didn’t let him, and he asked why, I told him some lie. He wanted to put it in without a condom but I insisted he did. I couldn’t come up with a lie quick enough to avoid having sex with him. He saw me come out the shower and he could see I wasn’t menstruating. I just wanted it over with!!!! I was in so much pain, the both of them were huge. But, I felt so disgusting and dirty after that. I couldn’t be with either of them after that day. And I have never told this to anyone, so now anyone who reads this will know.

  • Vanessa

    @Rastaman, I like how you think.

  • LilMissStrange

    Im just thankful you had the good sense to wash your balls before getting down with the second chick.

    If you didnt…I would have to talk about ya.

    Of course, if the tables were turned and I aired out similar “laundry”, I would be called the “ultimate hoe” (washing or 24-48hr waiting period or not)

  • Sherell

    If your truly single and take precautions, then its cool.

  • The Duchess

    I like the way it was written.. It made me laugh

  • QuoteMan

    I’m a dude with a touch of arrogance (not cocky), and true to form I don’t need help in the bedroom; I’m a one man army and so are most dudes. So, there will always be ONE plumber laying the pipe – and that’ll be me – alone. Lol

    As for the double standard, y’all always tolerate being around each other semi-nude or even naked in some cases. I remember when we used to go club hopping, you could see 2 to 3 chicks coming out of the bathroom together, and y’all was OK with that. Now, if 2 dudes were to come out of any bathroom together, rest assured that place is getting shut down!!, for the night at least. My homegirls used to be around each other in just their bras and panties with no problem; dudes, we never let that shit fly. So, I don’t think it’s a double standard, just that naturally, it’s more acceptable to y’all than us.

  • NWSO

    You’re missing TC telling his own story using my same bacheleorette names for confusing consistency.

    He wasn’t in the room when I was with Malika or Sandy. Now THAT would be a completely different post. Maybe Paulette Bajangal’s version. Lol

  • Ronnie6676

    so very late but I just had to say I love that bottom picture

  • KittyKat

    I agree too. U werent in a relationship, and single ppl can mingle. Lol



    hopefully you changed the sheets. too many juices flowing for me.

  • Womanofyr

    Fluid mixing, hairs, etc. Say no.
    That 2 men at once thing sounds interesting. But no, too much germs cooking.

    But if you want a moralistic, right/wrong answer. I would ask.. If you told the person you had some already, would the second partner still agree. If they did agree, would you still want it.

  • SimplyHazel

    LOl @ gonaherpes.

  • Justmyopinion

    Just had to comment.. ME personally I would rather be the first rather than the last person to get it.. Never had the sex thing happen to me but just kissing 2 dudes in the same day is not that appealing to me.. Especially if you haven’t known them all that long.. As you can see from this post you dont know where and on who their mouth has been..

  • Maria

    @Rastaman, I agree with you.

  • Spinster

    Never did that before. Must be nice? :-|

  • Koolikedat

    Been there and done that. Kim was a sweet girl in grad school who pursued me after we initially met. On our 2nd date she told me she’d had a sex dream about me. A day or 2 after I hit it, Kim called and I mentioned I had a slight cold. Later she called again to say she was on her way over. Kim brought food and get well ballons. I soon realized she wanted more than a mere ‘thank you’ for her efforts. I took some NyQuil and broke her off. The next morning, a Friday, I did feel better, so I took Kim in the shower w/ me for some sexual water sports. I knew I had a date w/ Sonya that night, but my Dad always said, “There’s a first time for everything.” :-)

  • Dash

    How could you afford all those dates in your younger days? Geez. Could have ended badly…herpes infested AND broke?

  • Dash

    Ok, I have to be honest here. This comment really disturbed me. “I couldn’t come up with a lie quick enough to avoid having sex with him.” Uhhh how about it’s your body and you can say no if you want to. You decide what YOU want to do with it. No is reason enough. And no condom? Who are these men you’re dealing with? Please stay safe. “I just wanted it over with!!!! I was in so much pain, the both of them were huge. But, I felt so disgusting and dirty after that.” Sex should never make you feel like a lowlife. YOU call the shots on your body. This is just….

  • TJ

    I just think it’s funny how this situation is taken so lightly for guys, but how I know what a conundrum this is for a female.

  • baw

    Just wanted to celebrate cause I’ve now achieved this… for the third time. Got two guys within five hours of each other last night ;-)

    I don’t see why anyone should feel bad about it. Though sorta felt like a waste to me, since I’d rather have spread them out and enjoyed them separately. Basically I called up a guy I hadn’t seen in a while for a booty call late that night, but then got a call from a hottie asking me on a date that afternoon. Didn’t think the date with the latter guy would go so well, but I guess we had a mutual attraction. :-)

    Maybe it’s evil of me but I enjoy getting 2 guys in one day (of course only when single!!!). Sorta makes me feel like I’ve got some good game going, and that I have this funny secret either guy will never know.

  • loverIdonthavetolove

    Well, its interesting. If a female were to do that, the majority would label her a slut, whore, etc.. but sense it was a male he can get away with it, and even get praise for it. Im a female, Ive had sex with 3 different guys in the same day. (Two i have had sexual encounters with before, one was a total stranger.) None of them found out about each other. Im an adult and like sex, judge me if you want, but im always safe and make sure to get checked out regularly. I dont like having sex with multiple people in one day is wrong as long as you dont do it often or with “nasty” people.

  • anonymous

    Im a female and have done this today. Im single and both are guys ive slept with before. Not sure how I feel about it. Part of me thinks it’s ok but there is part of me thats disappointed in myself like I’ve behaved badly.

  • today

    I’m going to do this for the first time, today… I don’t feel bad about it. I’m single and want to do this as I’ve never had two guys in one day before, so why not?