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I Had Sex With Another Man

Personal Stories, Advice, and Support 113 People

    And I'll Do It Again.

    Even though most of my life I was totally heterosexual (at least I always thought so) I was also a cross dresser. And eventually I wondered what it would be like to have sex with me playing the part of the woman. So eventually I just had to try it (I was in my 50's by then). And...
    RayanneA RayanneA 56-60, M Nov 19, 2013

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    I Had Sex With Another Man

    I had sex with another man, but I feel like women, because I was fully dressed with fully make-up, etc...
    CDIrene CDIrene 36-40, T 5 Responses Jun 26, 2008

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    First Real Man.

    I say first real man because i had been with trannys before, but this was the first time with a real "man".  I met him online and we agreed to meet, this was the second time we had set up a sex date.  The first time i got to his house but his boyfriend was out front, i got...
    Garterguy Garterguy 31-35, M Jun 7, 2010

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    My First Sexual Experience With Another Man In Absence Of My Husband By: Me

    I am a housewife and my husband had been always busy with his work and gave less time to me and spared maximum days out of home. I had never cheated but was getting very frustrated especially since my husband had become too ridiculous to even speak. It was my first time cheating...
    gruchikalove gruchikalove 31-35, F 1 Response May 17, 2013

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    I did since I have cross dressed from being a

    preteen I have been a hetrosexual but found myself attracted to men and others who dressed. I dated girls had sex married had kids but still wanted more in my sexual life. I finally made a friend and had sex finding out part of my sexual life that was missing. I now live...
    alexiswcd alexiswcd 56-60, T Jun 21

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    Joe

    i couple of years ago we had a gay bloke called joe staying at the guest house. he was a couple of inches shorter than me slim and obviously gay. he had numerous peircings in his face, his tongue and nipples and as i found out a prince albert and peircings in his balls. he seemed...
    Cyclopes66 Cyclopes66 51-55, M 2 Responses Aug 8, 2012

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    More Than One

    I first had sex with another man about 30 years ago, I've done it many times since (even with a couple of other men at the same time), and I look forward to doing it again.
    Dragon56 Dragon56 56-60, M Aug 22, 2009

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    Just The Other Night.

    I had sex with another guy just the other night. He was just some random guy i met online. We sucked each other, we wanked each other and he ****** me. I'm going back this weekend for some more fun with him and his boyfreind.  
    weebos weebos 31-35, M 1 Response Nov 4, 2009

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    I Did

    I have had sex with another man. Well i say man it should actually be men. I reckon i have been with 14 single guys and 2 gay couples.  
    weebos weebos 31-35, M 1 Response Jan 9, 2009

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    Related Experiences

    Okay I live in Michigan I was 17 now 18 at the time and the age to consent to sex is 16 I'm guessing that's with any age but below 16. Anyways this 42 year old police officer who...
    cupcakes38 cupcakes38 18-21, F 2 Responses 5 days ago

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    I had sex with over 200 girls before my 18th Birthday...
    Raddaddy Raddaddy 41-45, M 1 day ago

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    Before I start, this is going to be long. You have to know the beginning before you can understand the end. KARMA is a big word here so pls keep that in mind while reading...
    arwhap13 arwhap13 31-35, M Jul 17

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    I think about my wife flirting, kissing and having sex with other men.
    Stky2001 Stky2001 36-40, M 7 Responses Jul 1

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    I fantasize watcjing my wife making love to another man.
    Secretdzires Secretdzires 31-35, M 6 Responses Jul 13

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    Would love to find a friend with benefits situation. Not interested in having my significant other. As a matter of fact I think it might be a welcomed relief to not have to worry...
    ria972 ria972 41-45, F 1 Response Jul 14

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    There's this guy on tinder, he's older, nearly double my age, he's not that hot but decently attractive I'm looking for more guys on tinder but don't know if it would be too bad to...
    hardcoregay hardcoregay 18-21, M Jul 5

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    Not sure if I'm bi or just bi-curious but I've known four guys in my life that if they wanted me to suck them off, I would. How do you bring that up with people that are definitely...
    zacktr zacktr 41-45, M 4 Responses Jul 8

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    I've been with my husband for 8 years... and officially married for only 1yr. He joined the military 1 yr before we got married and he's been away in another state for the past 3...
    sh3rylanne sh3rylanne 31-35, F 1 Response 1 day ago

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    I think of this all the time. After reading "50 Shades" and many more related story's my wife told me she'd like to be submissive. So, I started boning up on Dom material. We've...
    Kandainnc Kandainnc 41-45 5 Responses Jun 29

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    Me and my bf have been together for 2 years now he is called liam so we have snoged and kissed and that it but my mother was out with her friends I told her I would be fine and she...
    emytink1 emytink1 22-25, F 6 Responses Jun 28

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    I had to stay late after school and my teacher had get megan tightly crossed i asked get if she was ok and i saw her run to the toilet. I heard a plop plop and accidently opened...
    reddeath11122 reddeath11122 18-21 1 Response 5 days ago

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    My husband has been abusive for 21 yrs. We've been married for 18. He has a friend that expressed a interest in me 2 yrs ago and I've been seeing him ever since. He is so sweet and...
    ginahunt3 ginahunt3 41-45, F 1 Response Jul 3

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    I am trying to convince my wife to sleep with someone else and then tell me about it. I hope I don't regret it.
    ewcmfa ewcmfa 36-40, M 5 Responses a week ago

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    I would love for this to happen oddly enough. If anyone has encouraged their partner to do this and it happened, how did you do this. Please feel free to message me your ideas
    Jamie444 Jamie444 41-45, M 3 hrs ago

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    One thing I want to try is getting ****** while I **** a guy. That sounds mind blowing...
    hardcoregay hardcoregay 18-21, M Jul 5

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    I want to suck a guy so badly.
    zacktr zacktr 41-45, M 1 Response Jul 6

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    it was super kinky... and i liked it alot
    bobsaget10175 bobsaget10175 18-21, M Jul 10

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    it was super kinky... and i liked it alot
    bobsaget10175 bobsaget10175 18-21, M 2 Responses Jul 10

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    And just loved it. But afraid if my husband comes to know
    samohot22 samohot22 22-25, F 2 Responses Jul 14

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    Okay in theory yes I suppose I can guess why they do. However in practise I can't for the life of me, understand how a loving man could be happy doing this? Nor how a wife could be...
    Mmmcherries Mmmcherries 46-50, F 6 Responses Jul 13

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    We are married for 1.5 years. My wife a bengali sexy lady who loves sex very much. After a long nagging i hav managed my wife to get her shared with another man. I wanna try. If u...
    smazumder1984 smazumder1984 26-30, M 10 Responses Jul 14

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    Okay I live in Michigan and the age to consent to sex is 16 I'm guessing that's with any age but below 16. Anyways this 42 year old police officer who lives in Canada came over the...
    cupcakes38 cupcakes38 18-21, F 3 Responses 5 days ago

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    Kinda family: when i was 12 we went abroad to visit family and i had sex with 4 of my male cousins (distant cousins) at the same time, in a field near their house.
    Julieloli13 Julieloli13 13-15, F 17 Responses Jul 1

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    I've never had sex without a condom before . But I heard it's so much better . Idk I'm nervous about that kinda stuff .
    oabutler oabutler 18-21, F 19 Responses Jul 7

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    My dog is the first living thing I've ever had sex with, she was tight, but then I let my friend borrow her and he ripped her a new *******. But moral of the story is, does anyone...
    Guuuu Guuuu 18-21, M 4 Responses a week ago

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    So I'm 16 I've been with this guy for about 2 years nd he's older than me nd we had sex about many times by now (10-20) but the thing is I find it still soooooooooooooooo painful...
    kungfuf kungfuf 16-17, F 2 Responses Jun 27

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    I always wanted to have sex with Ariel and many of the Disney princesses. I use to ********** to this idea late at night in my bed and imagine myself being in different positions...
    heartgun heartgun 26-30, M Jul 5

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    I have been in a relationship with this man for 7 months. It started off as all relationships do. All nice and loving. Now he screams at me , calls me names, and just recently...
    jon0517 jon0517 36-40, F Jul 2

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    It must be so enjoyable to be on a walking trail with another naked person. Nothing sexual 0 just pure enjoyment of being in nature as nature intended us to be - NAKED
    wantonwanker wantonwanker 61-65, M Jul 3

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    I want to have sex with a big women so I could sexually pleasure her hit me up
    dmedina513 dmedina513 36-40, M Jul 4

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    Yesterday, I had sex in the woods with my male cousin and a female cousin. It was so hot!
    LilyOrlovsky LilyOrlovsky 13-15, F 6 Responses Jul 5

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    I love sex without protection! I'm 18, I've had sex 4 times during the age of 14. never used a condom. loved it!
    jessicatooreal jessicatooreal 16-17, F 11 Responses 3 days ago

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    I had sex all night with my guy...literally 2 feet away from my sleeping best friend and her guy...it was super hot.
    orangecrayons orangecrayons 18-21, F 20 Responses Jul 7

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    This year, I had a extremely attractive chemistry teacher. He's sweet, and has vibrant blue eyes, short blonde hair and a perfect body. Every time that I would look at him, I...
    Jeanpocket Jeanpocket 13-15, F 3 days ago

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    Sex without love is empty feeling. Without emotions, it's simply just an physical act that i'm not interested in. The connection and bond you have with someone you love is what...
    evesss evesss 18-21, F 2 Responses Jul 6

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    Well, I started highschool, I am much more mature than the rest of the high school. I just keep to myself and focus on the future, I've had an unbelievable past for someone of 15...
    DreamLurker DreamLurker 13-15, F 1 Response Jul 12

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    Hi my name is Jan I am 21 and have sex with lots of guys. I work at a bar and always bring guys back to my place after work and have sex with them. I have a no condom rule. I want...
    jantheslut jantheslut 18-21, F 7 Responses a week ago

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    Right after I lost my virginity I got on birth control. It didn't take much to talk me into sex without condoms. It's super messy to clean up and I'm scared of getting STD's but it...
    cuteshyginger cuteshyginger 16-17, F 21 Responses 6 days ago